Who took your anal virginity?

It was surprise anal during a massage.

Teenage neighbor boy when I was around 5 or 6.

69 and still waiting ...

K. Y. Dildo

Hot guy in a bath house, yes we used a condom, yes he was really cool, yes he made me cum without touching myself, yes his body was amazing...Why did I do it there, to get it over with and not have the hassle of knowing the person. He was a lot older than me and he was really cool about it.

I was 18 and a few weeks into my freshmen year at college. He was my art history professor. It was amazing. Besides getting my cherry popped, I got an A in the class.

With an A in art history you can write your own ticket!

Friend - freshman year of college. We were both virgins. We did it many more times that year.

I was molested

Was 14. A hot set builder from a theater company probably in his late 30's. He took me for a ride on his motorcycle and fucked me on his picnic table. Cool guy, lots of crisco :)

I was 28, he was 38, a patent attorney who died about 6 yrs later. It was really nice, though I had to stop, I felt like I had to go to the bathroom (I didn’t) & it was a bit painful even though he was average size. I spent the night, then we had oral sex in the shower in the morning, & went straight home & voted in the 1998 election.

Dildo and lube.

[quote] I got an A in the class

And a D in the ass, R6.

I was 19. He was 47, French, beautiful eyes, masculine voice and big, thick, intact dick. He licked my ass first and I couldn't believe how nice it felt. Then I almost had a prostate orgasm when he was fucking me. It was so intense that I had a kind of emotional meltdown and cryed after. He was amazing and my one true first love. We stayed together for 5 years. He still write each other. And I still sometimes jerk off to that moment. I feel lucky but then never had someone like him ever again.

R2 I'm so,so sorry. Do you know what ever happened to him? I can only hope he got his comeuppance.

I think he got his come, not sure about the uppance.

R16 I actually thought before I posted that someone was going to make that joke. Then I thought, surely not, considering the subject matter. Once again, I overestimated the DL.

I did not know about anal until I came out and a number of guys wanted to fuck me. I was 24 at the time, and I would just say no. And then a little before Thanksgiving that year, I brought home a guy who had the biggest dick I'd ever seen. And he was so goodlooking. He wanted to fuck me, so I said yes, thinking I might as well do it with someone this well-hung.

It wasn't any fun, though. I continued knowing the guy, however. I was dating a friend of his, who had a much smaller dick, and though he asked if he could fuck me, I never wanted to do that ever again.

The following year, I met the first gay guy I fell in love with. We would have sex that included everything but anal, and I was perfectly happy. A couple of months into our relationship, he wanted to fuck me. I said I would let him, and on maybe the sixth or seventh attempt, he finally made me cum hands free. I was thrilled.

A couple of months later he dumped me for another guy, one who fucked him. I think I've been disillusioned about gay relationships ever since.

This thread is giving me a lot to pray about!

Daddy.

And then my older brother.

My wife, Mother, of course.

I was 19, he was 33. A big burly man's man. It actually took me a few attempts to take him. But was heaven once I could. We stayed together for seven years.

Miss him dearly over 20 years later.

First a gypsy.

Then a tramp.

Then a thief.

The hood kept me from seeing.

My first serious boyfriend. I was 18, he was 25. He had the smallest dick you’ve ever seen, so I thought it would be a breeze. Hurt like hell. And after two years of letting him fuck me, it still hurt like hell. Constant, irritating pain.

My next boyfriend was extremely well hung and I was REALLY hesitant to let him try. Wouldn’t you know, it felt great!

I was 17 living in South Kensington, London. I had seen him in his apartment through the window, looking at the back of the buildings on the interior of the square, fucking someone. We flirted through the windows. He motioned for me to come over. I walked around the block and he met me in front of his house. He took me up to his apartment and fucked me. I don't remember any sucking. I must have liked it because we did it again the next night. He seemed much older, but he was probably all of 25. This was in 1974.

I was 20. His name was Chris. We met at a bar. It was wonderful.

He told me his name was OJ.

I'm a top.

Kevin Spacey

I was twelve. His name was Palo. We were both in the Legislative Youth Program. He was a few years older than I… very cute… dark curly hair… dreamy eyes.

I was about 21, living in London, with an Italian boyfriend. I was really inexperienced and wanted to at least try everything once. His dick was the perfect size - about 7" and thick - and it wasn't easy but I managed to learn to enjoy it with him. I've only let 4 guys fuck me in my life, I think.

My first serious boyfriend, who I wound up moving to CA for. I was 25.

It was awesome. He definitely knew what he was doing. Early enough in the Midwest not to use condoms, although that changed very quickly that year (1985).

Sean... Sean.

A liar. He said what he had to convince me to bottom for him. We'd been dating for two months and I agreed to let him fuck me. We used a condom and he came inside of me. He began ghosting me the very next day.

Lesson learned.

My horse hung father, donkey dicked brother and micro dick'd grandpa. Was a long night.

I was 24 and it was the first night in a two night stand. He was from Venezuela and on a student visa. We met at the White Horse Bar in Oakland. He was extremely hot. The fuck was almost painless because I was so turned in by him. I ejaculated while he was fucking me.

r35 = the saga of every straight woman everywhere ever since the beginning of time.

Meh, some schlub I was dating on and off. Not a bad guy. But nothin' special. Used a rubber. I was surprised it didn't hurt, guess he was small. All I remember is that I was 19 and it was the week before sodomy was legalized in the state of Texas, haha. Didn't think too much of it either way, kind of a "meh" experience. Was mostly a top for years. I'd bottom every now and then, just to be nice, if the guy I was playing with wanted to after I'd topped him. Didn't learn to enjoy bottoming until I got surprise DP'ed by a married couple of doctors many years later. Now, I'm vers all the way.

As of this writing, absolutely no one, at 58. I may or may not fuck a 20-something tomorrow night though. When it comes to anal sex, ‘tis better to give than to receive.

13 year old

Wait, I was also 13 at the time. So glad I did not hit POST before adding that.

Dad..

nonconsensual, 14, he was late 30s

#43/Aaron, did Bruce buy you a nice gift afterwards?

Me, 18 and just out of the closet (in Dallas). Met a hot guy at a bar. Naturally, he lived out of town.

We didn’t screw that night…I went to visit him in Houston and he was very careful and considerate, but his average unit hurt like hell.

I’ve been mostly a top ever since.

Wow R43, I’m sorry that happened to you.

I was 40! By a well-hung good looking Marine. But he had a bad ticker, I thought he was going to die on me. Worse off IN me.

R44 go fuck yourself

Hot r6!

Brian Williams. Yes, that one.

A somewhat older and much more experienced black guy I was dating one college summer. I liked having sex with him but wasn't too interested in anal - but he really wanted it and I was at least curious. But he had such a huge cock that my tight virgin ass just could not handle. I wasn't prepared for how incredibly painful it would be and for years after I couldn't even dream of doing it again.

Well, I never OP. Discretion is the better part of valor.

It wasn’t so much taken as lost.

My uncle .. when I was 4 or 5 🤦🏻‍♂️

R53 well that explains why you are a fat mess.

It was savage. A brutal fucking. They dragged a filthy old mattress into the yard and fucked me on it. My best girl-friend was getting it at the same time on the hood of a car in the garage. It was a dual Rape, a ‘gangbang’. We were both getting wrecked, ruined.. my cherubic blond curls sweated to my bright red flushed face. A grimace of agony as a new, bigger cock went in me. They taught me to ride that night. I rode 7 different cocks.

Colonel Mustard, in the Conservatory, with the Lead Pipe.

R7 lololol.

With a friend (both 11 years old) in his mom's station waggon. We tried on two separate occasions. Wish we knew about using lub.

R57 at least it wasn’t Mrs. Peacock!

Nobody "took" it. I gave it. And gladly.

Oh that’s what you call it??

My cousin when we were both teenagers. He cornholed me on his mama’s king-size bed.

I was 18. It was a fuck buddy, so it wasn't a big deal. It was good, but it took me A LOT to open up. I did cum pretty quick though (almost instantly). It was good overall.

[quote]station waggon

Oh, dear.

[quote]I got an A in the class.

So, clearly not the only student who got "fucked" by that teacher.

I was 18. In my dorm room at the Start of winter break my freshman year in college before heading home but after my roommate and most guys on my hall had left. The guy had graduated the year before. It was 1988 in the Midwest and one of the few times I got fucked without a condom u til starting Prep a few years ago. Not really anticipating it. Had no idea about sourcing though it didn’t get messy thank god. We only had Jergans hand lotion so not the best lube. It hurt. He came fast. He ended up giving me crabs. So all in all, terrible.

Meant douching not sourcing in R67

A friend in a moment of horniness. The worst, most talentless fuck of my life. Almost turned me off it.

Edmund White's memoir about losing his virginity... as a teenager in Cincinnati, roaming a park at night, talking to an older "traveling salesman", who invited him back to his hotel for sex."

"He said it would hurt but I would like it.

It did.

I did."

I was 18 and had kind of failed in my attempt to move to another city but my cousin had let me stay in his room while he was away for 2 weeks. On the last night I had a guy from craigslist come over, a chubby hairy guy from Sri Lanka I think in his late 20s. I’d never fucked a guy before and it just slid right in and felt amazing. I came inside him. Then he wanted to fuck me but I’d kind of lost my horn by then. He was pushing his cock against my hole but hadn’t used any lube or even spit so I figured it would be impossible and he’d just give up, but he actually pushed hard enough that he managed to go in completely dry. I got an internal hemorrhoid after that (perhaps partly also due to opioid use followed by food poisoning) which has never completely gone away and so anything in my ass hurts like hell to this day.

I also had a sprained tongue muscle the next day from rimming him for so long. Also I’d planned on washing the sheets before my cousin got back the next day but he woke me up at like 5AM and I had to move to the couch... the guy had only left at like 3AM

You really painted us quite a picture of that dalliance R71. I feel like I was there. Oooof.

It was a guy named Paul. I didn’t particularly enjoy it. Average cock, with a condom. What made it special was the location

I was 29 and he was 40, a hot lawyer. Meth helped. Fun times!

Fat fingers at R73. Here’s the location

Cheap motel fetish. Although detox kinda works

Does a softball bat that I shoved up my ass at 20 years old count? Completely Dry! Very strong orgasm.

I was in the army at the time.

Pool balls stolen off the company pool table also worked wonders.

A hot 28-year old Hispanic guy with a thick, uncut cock. He was a reference librarian at the university library. He came to a Christmas party given by my boss who ran one of the branch libraries on campus where I worked as a student page. When he arrived he immediately began flirting with me. I was 21 and had never seen such a huge jar of Vaseline. They don't make 'em in glass anymore.

A cute blond guy, about 30. I was 21. It hurt like hell...but it was interesting

My first long-term partner when I was 24. He was 41, tall, dark, handsome and hairy, which I love. I was pretty inexperienced at that point, which he and I had discussed. I'd only done oral and frottage with the guys I had been with, which wasn't that many. When I met my first partner, I fell in love. I had fantasized about getting fucked many times. We'd been together a couple months when he started probing around the outside of my hole one night while we were messing around. It got me really excited and I had an intense orgasm due to the sensation. After I came, I asked if he wanted to fuck me. He said yes, and asked if I ever fantasized about it, which I admitted.

I had to leave the next day for a trip. We talked on the phone when I was gone and we discussed me bottoming for him when I got back. That first time, there was so much anticipation on both sides. He was very experienced and guided me through it. He had me sit on it and ease down on it. He was a thick 7 inches and I had a very tight hole. It was uncomfortable and it did hurt. He came pretty fast because I was so tight.

I wasn't sure I ever wanted to do it again. Then the next day, my ass was a bit sore but in a good way. It made me very horny and I had to hide my on-and-off hard-on at work that whole day. I couldn't stop thinking about him fucking me, and I knew I wanted his cock back inside me. That night, I asked him to fuck me again. This time, he put my legs on his shoulders and did a very slow entry. It hurt a bit, but I was very excited. I was hard as a rock by the time he started fucking me in a steady rhythm. I was jerking off while he fucked me, and I came pretty quickly, and then he came right after me. We did it again a bit later that same night in the same position. My second orgasm that night with his cock inside me was incredibly intense. I'd never had an orgasm like that before. After that, me bottoming was pretty much the main focus of our sex life.

I was with him 13 years before I broke it off with him. I'm glad the first time I did it was with someone I loved. I know everyone is different, but for me sex with someone I love is far more intense and satisfying. After breaking up with my first partner, I was single for 9 years but have been partnered for nearly another 9 years. I love getting fucked by my current partner, whom I consider the love of my life.

And other times, people have it off, sweetie.

Bump

[quote] I was with him 13 years before I broke it off with him.

Why did you break up after so many years, R80?

I was 19 and the dude I think in his 30s, he had a small dick so it was nice but it still hurted a bit.

"hurted"

R85 English is not my first language mary, feel free to correct me, I like to learn.

Hendo.

It appened befoor moi 26th burfdae, in the showahs at Wemblay. He called me a slut and I sooked him off furst. The rest of the taym caim in aftah n watched uz. Oi looved it!

R83, I loved him but he turned out to be a mess. He had problems with his finances, he lied about all kinds of things big and small, and was kind of an emotional mess. I caught him cheating on me twice. Our agreement was monogamy and it wasn't forced. We discussed it thoroughly and he said that's what he wanted.

After the first time I caught him cheating, we went to couples counseling. I told him and the counselor I was ok with an open relationship if that's what he wanted. That would be better than the deception. But he insisted he wanted monogamy. Turned out what he wanted was for me to be monogamous while he got to play on the side. He actually admitted that after getting caught the second time. After trying to get over the first cheating (or first time he got caught is probably more accurate) then finding out he did it again, that was it for me.

After that, I dated but never found someone I wanted to partner with until nine years later. I met a great guy and we've been together nearly nine years now. He's honest and trustworthy. We had the same talk about what kind of relationship we should have. We landed on monogamy, but I've told him I'd rather have an open relationship if he feels the need to stray. I don't like the lying and deception. But if we do that, I get the benefit of it, too.

R22, thanks for trying, but I can’t stand Australian accents. Aussies all sound mentally retarded.

Oops, wrong thread.

told this a few times my dads bff was the first...the second would not be until I moved to LA. Met him on a local BBS (this is early 2000s BBS were the grindr back then) His screen name was HNGTOPn2Cops. It was the first time I had ever seen a dick that scared me., Skinny good looking guy with a fucking baby arm for a dick. He introduced me to poppers it was glorious.

It was so long ago, but it must have been one of the men who visited Momma and Daddy's bar, the Sanitary Cafe in Central, South Carolina. The little song and dance shows that I put on to entertain the patrons -- and I was darn cute if say so myself -- always made me attractive to a certain sort of Southern gentlemen who showed me the way.

The first man I fell in love with and had a relationship with. He was 27, I was 22. I remember thinking he wouldn't like me naked because I had a small cock and was not circumsized. He thought (I discovered later) that I wouldn't like him because he was quite big and also not circumsized. First time naked, we discovered we loved each others bodies. Whenever it was that first time he fucked me, I remember it didn't hurt at all and felt quite good and enjoyable. No pain whatsoever.

R93 did he prep you?

This fictional accounts are generally 1/10

I was 11yo, he was as old as my dad, and he took something from me I didn’t even know that I had

Naval officer in San Diego. I was enlisted. We met at an after hours bar. His penis was really small. I found out later when I got pounded by someone who had a really big dick.

Certain secrets are not to be shared.

[quote] what he wanted was for me to be monogamous while he got to play on the side.

Never understood this as a desired relationship model. What does it do for someone? Is it just a power trip?

The guilt and the unfairness of it would eat me alive, from either end of the seesaw.

In the Rectory.

I know this sounds like a made up story, but every word is true. I was a new college freshman, and I had heard about this park “where the perverts go.” Well of course I was intrigued as any young horny boy would be. I waited until twilight and sat in my car for an hour before I got out and started walking around. I saw a few older men but was scared to approach them and didn’t make eye contact. Then I saw a park restroom and went in to pee. Of course I noticed the big hole in the side of the stall, and just at that moment a big thick cock came through! I was paralyzed then a man’s voice said “suck it, boy,” so I did! I knew it was wrong but it felt so good. After a few minutes he said “turn around and drop your drawers.” Of course I obliged and put my hole up against the hole! I can’t believe how brave I was at that age, not knowing what could happen. A wet finger slid up inside me and I instantly got hard. I knew he was prepping for what was coming next. I thought it’s way too big! But he took mercy on me and inserted just the head and let me adjust. Then came the thrusting and I touched my dick and shot cum in like 20 seconds. He finished inside me not too long after and I sat down and squirted it out, thinking I was safe from any diseases. As soon as I cleaned up and walked out, standing just outside was my Economics professor! He didn’t know who I was because the classroom auditorium held 100 students. After that I requested a meeting in his office and ended up getting hard while sitting there in my soccer shorts. He saw, grinned, closed the door and started rubbing my cock. Of course I squirted again and he kissed me. We had several more encounters over the term, and of course I got an A in the class!

R80 Very hot post.

I love that sore ass the next day feeling too. It always gives me a hard on as well.

Tried for a while with my boyfriend. We did not know about douching. I was always so disgusted that even now that I know about hygene, it still turns me off.

R26, I, too, lived in South Ken, but you must have been in a less-respectable area than I was in.

For my first time I used the same reliable delivery service my parents had contracted with. No peeking through dirty windows at slobby strangers fucking with no curtains closed.

Are you sure you weren't living in Shepherd's Bush?

It was during my first week of internship at Witt/Thomas/Harris Productions. My father knew someone who got me in. I was really nothing more than a gofer. One day, Bea Arthur called me to her dressing room...

Too many too remember

Mid 1970s, Pennsylvania, best friend, I was 11, he was 12. It all starts with the game “Trust Me” where you put your hand on someone’s knee ask them, if they say yes, you move up an incremental bit and repeat. Eventually, you go down their pants, or in this case bathing suit, and touch and fondle their junk.

Fooling around goes on for years going further and further. Eventually I decide to try the information I’ve read about anal sex in the book called “Twins” based on the real life story of twin brothers who were both gynecologist, and secret lovers that ended in a murder suicide. It was made into the movie “Dead Ringers” with Jeremy Irons. But there was detailed information enough about fucking that I knew enough to lube with Vaseline Petroleum Jelly, so I’m guilty of being the instigator. Thing was, it was just one more step in fooling around and I’m sad to say I have no distinct memory of losing my virginity at all.

We continued doing it for years, basically every other week. We were friends, but it lacked any kind of romance or being boyfriends to it. I guess my first relationship was basically as fuck buddies. At 16 I pulled back and we stopped. I wouldn’t have sex again until I was nineteen in college. Though between then I was almost abducted, tortured, raped and murdered by a child molester in the woods.

I've given my anal virginity away so many times I feel like a Catholic orphanage.

No one took my anal virginity. I conceived immaculately.

I thought it was an audition, but bottom was the only part I got out of it.

Broom handle in a juvenile detention center.

College; I'd just been sexually assaulted by three guys and shortly thereafter this guy has his arm around me telling me everything's going to be okay.

Seriously, and then the dude seduces me.

Fucked me up for years. Probably still now.

Happy it worked out for the best, R88! 🤍🤍

This place is infested with fat lying bottoms.

There's a hilarious scene in the recent mini-series "It's A Sin" (set in the 80s) where newbie Ritchie is about to lose his virginity to the more experienced Ash, when Ash bolts telling the naive Ritchie, "You need a good wash!" Years later when the friends hook-up again, they laugh about it.

R2 I'm so sorry to hear that. What kind of mental case sees a 5 year old and wants sex??

R35 what was the lesson learned?

R116 um...that men will say anything to get you in the sack, genius.

20. A marine that had a really fat one. Not long but pretty thick.

Felt like a red hot fireplace poker going up inside me. He said he was really sorry and he would go slower.

He did go slower and that's when it started feeling good. We came three times each that night.

[quote] I wasn't prepared for how incredibly painful it would be and for years after I couldn't even dream of doing it again.

Post Traumatic Stretch Syndrome

This will garner shrieks and accusations of being a Frau, but I feel it needs to be said—it’s quite heartbreaking and grisly how young some of you were, and how violent your first experiences turned out to be.

Kids & very young teens getting raped or coerced by older men or boys really isn’t alright, and would do a number on anyone’s psyche. I do acknowledge that 12 or younger may not be young to begin a sexual life in some cultures, but to me that is somewhat too young; I expect an 11 year old to spend time playing or gaming or out riding bikes and having adventures like a Goonie, still (maybe trolling for their first kiss or sneaking looks, at the most). But I suppose times have changed, now, and so many young kids are or have been looking at porn before their own genitals even come in.

There’s no getting around the fact that real-world (and cyber) physical intimacy of any sort is an important matter of trust that ideally ought to be handled with care by responsible people, or at least people with basic levels of humanity intact—all too rarely, though, we hear and see that this is not the case.

Those of us who had our first times later in life (or at least when we were older than 11 or 12 years of age) and/or in loving safe circumstances with a partner we could trust really have been fortunate.

R120 I don't entirely disagree. My first time was at 12, with another 12 year old. We were just messing around and one thing led to another. We had "fun" on and off until I left for college.

But in some aspects, I'm glad it happened the way it did. I had sex before I was old enough to have anxiety about it, and homophobic teasing didn't bother me because I was getting laid and they weren't.

R121 Very well said, there was no anxiety about sex and I remember in 7th grade explaining (straight) sex to all my classmates in very clear, almost clinical terms and them being completely clueless. I almost got in trouble, but when I repeated what I said and that there was no misinformation I was giving they basically had to back off and not punish me. They may have been calling me a faggot in school, but I’m sure out of everyone I was the last person that they expected was getting laid on a regular basis. It acted like an armor, when they said things, I could think in my mind “If only you really knew what I was doing!”

I arrived at college very sexually experienced and the whole idea of the complications of being fucked the first time didn’t exist for me, while just about every gay man coming out it did. And frankly one of the really good reason it happened like that was I was able experience unprotected sex for years before going into the lockdown of safe sex, I was one of the few of my friends that age who experienced it.

R120 is a perfect example of why woman shouldn't be allowed on Datalounge

[quote] How old were you? Who was it? How well did you know him? How was the sex?

13. My best friend, J.C. Very well. Good if not a little awkward -- it was a sleepover and his mother nearly caught us. We did oral and anal, both versatile and no condoms. We were virgins, and it was 1980.

I'm sure 15 year old Bryan Singer would have creamed himself watching.

A smoking hot med student who was working as the janitor of a gay cafe. I was a cute 13 yr old blond so desperately horny I thought I’d explode. I wasn’t particularly precocious. By 14 I was so horny I could barely think. That’s why I now think much of what is written about the sexuality of adolescent youths — particularly by women, who have no conception of the male mind — is utter tripe. Society still can’t deal with it honestly - it causes brain fuses, particularly amongst parents, so it peddles one-note lies that there are only victims and predators, and suppresses any nuanced discussion, because there are no easy answers. It’s an impossible discussion, so is shut down. However I’m sure that will eventually change. I tend to think that in some ways the Victorians were more honest than ourselves in the matter of acknowledging it.

It’s not fair to call out R120 on a frau-basis, she’s sharing her thoughts as much as the rest of you are your experiences. So thank you for all that.

It should not go unnoticed that not that many people here have expressed regrets or hurt from getting their asses taken across a spectrum of ages and situations. But yes, for the ones who were raped, lied to, treated shabbily afterwards, that’s awful.

This is incredibly more than I thought I’d type for a post. I just opened this thread to see if any of you bottoms mentioned me.

R126 ok Nancy

The first time I had gay sex, the guy fucked me. It was not romantic, or fun.

[quote] I expect an 11 year old to spend time playing or gaming or out riding bikes and having adventures like a Goonie,

That's just the current norm. But is it a desirable norm? 120 years ago most kids were thrown into adult worlds at 12 when they went to work -- and worked 12 hours. Here's a provocative question: do today's childhoods go on far too long? I know I thought mine did, and was frustated both experientially and sexually because it did. By around 14 I was fed up with it and wanted the adult world. Would children be better adults if they experienced more hard knocks and slapdowns at an earlier age than the extended cotton wool pampered existences they have now?

What can I say? I am a caring (and curious) top!

R129 interesting question. Really, it’s hard to come down on one side or the other.

YMMV, but IMO most people aren’t really capable of becoming mature, responsible or conscientious until they’re at least into their twenties, and usually it takes even longer than that. And relationships between people who haven’t developed the aforementioned qualities are usually a toxic disaster, meaning that by the time the young adults do reach maturity they are jaded and damaged and out to hurt people. In this respect, it’s actually healthy to let kids & teens be young and stay out of sex & intimate relationships for many years, as it prevents the pain and fallout of hormonal selfish drama (which can be fatal in a lot of instances).

There again, perhaps as you say people become wiser and more empathetic with experience gained sooner rather than later. Maybe through mollycoddling, people aren’t experiencing enough growth in their youth and thus aren’t reaching a place in adulthood where they’ve become ‘emotionally-3D’ so to speak. Sheltering could be a form of deprivation as well as protection.

It’s a tricky road to walk. I’m relieved that I don’t have children to raise in these times, because I wouldn’t know what to do. This world seems a much more shadowy place than the one many of you grew up in, but how much of that is real and how much created in our minds?

^^^if it helps to know where I’m coming from with that argument, I stand in stark contrast to everyone else posting here—-one of those hyper-sheltered late-blooming virginal types who was very protected (as well as uninterested) in sex growing up. Sex to me always seemed like something not worthwhile to pursue or for which to take risks, plus I was dissuaded from pursuing it, so I just didn’t. It’s hard to say whether this has been the cause of trouble and setback and stagnation in my current adult life (there are different more obvious causes IMO, but I appreciate others would disagree), but I can admit that it did isolate me from others in my teens and probably protracted a selfish childlike world too long. But I had a very colourless domestic life and a fairly unhappy scholastic life, so I felt I needed the fantastical escapism and security of innocence into which to retreat. It was a coping mechanism that worked for me at the time, but perhaps works against me now. We all have different paths to walk.

The actual first resulted from too much alcohol, I was quite a lush in those days. He was a farm boy from Boise and from what I can remember, he gave it to me and I really liked it. Then there was the planned one with a man I was smitten with, but that sex was awkward and mechanical. I really loved him, but I went a little crazy and drove him away.

I was 14, he was in his 30's. We met in AOL chatroom and he wouldn't send pictures, only these stories about a knight and a prince that were very romantic. We went on a date to the movies and he picked me up in an old limousine. He was hideous, obese, tiny penis, and some kind of awful eczema all over his back. After the movie we made out in the back of the limousine (which was being driven by some old guy that I think was either his dad or roommate) and he took me back to his place and fucked me to Brian Williams' Everything I Do I Do it For You. I was very shocked at how much it hurt, considering how tiny he was. Afterwards I was quite ashamed and never spoke to him again. Didn't have sex again either until I was 17.

[quote] He was hideous, obese, tiny penis, and some kind of awful eczema all over his back.

So a DL’er?

It gets better!

LOL

It was the back of an SUV parked off the side of a highway and I kind of bossed him around and told him to do it and it hurt but I was super ready to have it done and finished. It was mind over matter type of deal. I didn’t understand what the fuss was about. I was a top ever since then but it’s not that it’s unappealing to me, has to be the right guy.

Carrot Top

I was 21 and determined to lose my assginity. I met him in Boots and Saddles on Christopher Street and we walked to his apartment. It was a sparsely furnished and dank studio. He wasn’t particularly attractive and had an average sized dick but I was determined to be fucked that night and too impatient to wait around for Prince Charming. I don’t remember much pain (Crisco for lube: late 70’s) but after a few thrusts he stayed still in my ass for what felt like an eternity. I was too inexperienced to know what was going on but, in actuality, he had let himself go flaccid and peed up my ass. After pulling himself out, I began to sit up and he went batshit crazy: he was afraid that I’d wet the bed. By that point, I lost patience and blurted out, “if you’re that freaked out about dirty sheets, you shouldn’t pee up other people’s butts.” I made it safely to his mildewed bathroom and emptied a buttload of stale beer. It was not a night of magic but, as they say, it only got better.

He was a boy, just a boy, and I was a very young girl.

R34 Thank you for that

I got fucked first in a bathhouse. Poppers helped a lot (still do). It was okay. I just wanted to experience getting fucked and it did the job.

It took a few tries before I met a guy who bottoming for was a great experience. He was a hookup. He had a log of a cock and deep kissed me into a trance. It was amazing. After that, I only bottom for guys who have those two attributes

I’m saddened by the hoes who lost their virginities in bathhouses.

Call me a romantic!

A married, wealthier older guy. I was 19, he was late 30s maybe? He had a humongous penis. It could barely fit in my mouth. He got mad at me halfway through because I was moaning so loud he was afraid it would wake up the maid upstairs.

[Quote] I’m saddened by the hoes who lost their virginities in bathhouses.

I did a lot of fun firsts in bathhouses.

The problem is, after a while, you lose the ability to combine sex and emotion. You begin to see every man as a sex object, and you don’t understand the nuances of dating and relationships. I loved bathhouses In my youth but they do mess with your mind.

R139, for years I wanted to experience doming peeing up my ass. Now, with PrEP, I was able to be have someone do it.

Meh

R2 Sure Mr NAMBLA. In your dreams.

Sorry, but isn’t what R26 wrote basically the plot of the film CLAPHAM JUNCTION?

Worth pointing out that there is a world of difference between a 13 year old having sex with a 14 year old peer and a 13 year old having sex with at 40 year old man.

My first fuck was when we were fumbling 17 year olds. It wasn’t until a 47 year old fucked me me a long while later that I understood the pleasures of anal.

I’ve been a daddy fan ever since . They’re just such better at fucking

On the flip side - now that you’re an elder gay - are any of you out there hooking up with 19 year olds? Because I can’t imagine it and so many lost it with much older men. Now that I’m that age, the thought of a teenager is nauseating.

Here's how it's done right (NSFW).

[quote] if you’re that freaked out about dirty sheets, you shouldn’t pee up other people’s butts.

I ❤️ u!

I'm pretty sure I've told this before on here, but whatever.

I met a man online while I was still living at home with my parents before I went away to University. I was 18 and he was quite a bit older but we really hit it off. One weekend when my parents were away I invited him round and we had sex multiple times, on the sofa bed in the lounge. He had a big dick and I bottomed first and although it wasn't painful (being older, he knew what he was doing I guess) I didn't find it very pleasurable other than the psychological enjoyment of finally being devirginised. My dick wasn't even hard throughout.

However, we then moved on to me topping and that's when I realised that was more my thing! He was sceptical that I was a virgin as apparently I was a natural at it (yes, I'm bragging there, sue me). That man became my boyfriend for the next couple of years. He was predominantly a top before he met me but we ended up being fairly evenly vers with each other and I did get more comfortable with bottoming and learnt how to enjoy it, but it was always second-fiddle to topping. Eventually we stopped using condoms and I actually found taking a load to give bottoming an extra bit of a thrill, although unlike a lot of tops I never had an issue with using a condom to top and fucking raw wasn't the massive boost I had been led to believe.

[quote]are any of you out there hooking up with 19 year olds?

I saw an amazingly cute one fucked hard at the sauna the other afternoon by a guy who must have been at least mid-70s. Built like a tank with a huuuuge cock that was ramrod stiff. They seemed to know each other because the older guy did him like a spitroast in a spit second. I'm never surprised by anything. Not since the day I saw a breathtakingly beautiful Russian looking kid go into a room (in what was obviously a pre-arranged meet up) with a 5,000 ton slab of waddling fat. I can understand daddy chasers, and chubby chasers, but a Jabba The Hutt chaser really blew a brain fuse.

I wonder if the type attracted to old daddies as teenagers ever turns into the type attracted to young ones once they reach old daddy status.

R156 NnnnAAAAAANNNTS!!! InnnGONyaMAAAAAA!!!!! BagiTHI baBAAAAA!!!!....

Did you guys practice stretching yourselves or use dildos or something before getting fucked in the butt that first time?

I can't imagine having zero anal experience and then having a dick up there and it all going well.

I remember my doctor putting a finger up there once in my teens and being sore for like a day afterwards.

r1158 it is not really a matter of stretching but relaxing. Not to be gross but when you poop that hole is wide open so we all can do it.

R158 I would definitely recommend some solo exploration in advance of getting fucked for the first time, ideally a decent dildo that you build up to after you are comfortable with a finger, then two. It is a very weird feeling to start with and if you're not completely comfortable, the internal muscles inside your ass will automatically tighten and it is likely to hurt (feels like being stabbed in the ass with a hot poker) and by practicing on your own before hand, you're much more likely to have an enjoyable, or at least not painful, first experience. Go slow, use plenty of lube, take it out and wait a minute or two before continuing if it's hurting. You don't want to go too fast/deep too soon and cause any damage which will really put you off in future.

"Did you guys practice stretching yourselves or use dildos or something before getting fucked in the butt that first time?"

No. No one knows that when you're naive. Not even the tops, who should know better.

I imagine it's the same with women and that first big plunge.

Neighbor boy. I was 12; he was 13. It was the usual kids-fooling-around stuff. We did it off and on for a couple of years. We didn't do it to completion at first; that happened later. In the beginning, we would just take turns putting it in for a few minutes. That was probably a good way to get used to it.

I found a dildo and vibrator in my father’s top drawer and practiced with them both before I did anal. I was very well versed about having something up there by the time I had the real thing. One time the vibrator, while on, slipped completely inside me. I was terrified I was going to die or even worse, need to go to the ER and have to explain what happened, where I got it and undergo some horrible procedure. Eventually I was able to use my internal muscles to expel it, but it scared the hell out of me.

I learned the truth at seventeen that anal was just for beauty queens.

R155, was the sauna in Troy, NY?

#LoversReunited!

I was 18 and working as a bellhop at a Holiday Inn in Virginia. Some guy wanted his sheets changed but housekeeping had left and they sent me. As I was moving around the bed bending and stretching, he soon had me bending and stretching in ways I never knew possible.

I left my high school ring in his room and had drive my sore ass back to get it later that night. Turned out he was an advertising executive from San Francisco. Four years later, after college, I was working as an advertising account coordinator in San Francisco. Never saw him again.

We don’t believe r167’s lies!

“Never saw him again”?? Didn’t need to when you’d already whored your way to the top!

R168, he whored his way to the middle...

Another bathhouse deflowering here.

R170

I'd think a bathhouse would be terrifying. Total strangers who clearly sleep around and are likely to give you an STD/STI or HIV....no quick way to leave when you're walking around naked...possibility of running into someone in your community...lack of privacy if you do find someone you like...

At least with an online hookup person you can do it at a house or something...and without an audience....

I guess the bathhouse first timers were in the 70s?

The HS football team behind the bleachers.

R171, I am one of the bathhouse queens you are talking about and no it wasn't in the 70's...it was in the early 2000's and we didn't have Grindr.

We also didn't have an audience...like most people who probably did what I did, we had a private room.

Meeting someone on line can still open you up to an STD, to someone crazy and to someone more likely to murder you

You sound stupid.

R171, Mary!

No one forces you to do what you don’t want in a bathhouse. If it’s not working for you, you just leave the room. Tons of privacy. Yes, you might meet someone you know, but guess what, he’s there too! It actually has only happened to me once in my many years of bathhouse patronage.

Condoms prevent HIV and STIs—I’ve never gotten either

r173 and it is not like any random can fuck you. Typically a guy with a room would hang out in his room, the guys interested would walk around check you out, and ask if you wanted company. Make out, reach under the towel and see if the good are going to ring your bell.

[quote]r173 I am one of the bathhouse queens you are talking about and no it wasn't in the 70's...it was in the early 2000's and we didn't have Grindr. We also didn't have an audience...like most people who probably did what I did, we had a private room.

^^ Grace Kelly

I have never been in a bathhouse (I know, smell me...) but I can see a certain advantage to there as opposed to an online hook-up. In a bathhouse you would see the human, body/movements/attitude/speech, and engage them... and if it wasn't working, the understanding in bathhouse would be "thanks, but I'm moving on now." Online hookups would seem to put more pressure on moving forward after you've met... even if there wasn't a great connection.

Am I rite?

I'm not stupid...I just don't see how you can quickly disengage with a guy at a bathhouse if you've only got a towel on and are clearly there looking for sex (and therefore not likely to say no, in the eyes of some pushy guys). What happens when some guy gets creepy and doesn't take the hint? What if he starts following you even after you said no?You go back to the locker, spend a few minutes changing and trying to leave? That's not a fast exit. If you meetup in the real world, you can scope things out a bit before taking your clothes off. And - god forbid - if he gets crazy or rough with you, you aren't "some slut parading around naked at a bathhouse" trying to file a report...but a nornal person who met up with someone for a date to possibly have sex, and then found themselves in a dire situation.

I know, I know - Mary! - but how do you protect yourself in a sex club?

I've had random guys follow me and get huffy with me when I tried to avoid them in the real world...while I was clothed and out in the open.

I'd like to think all the guys in a bathhouse are sex positive, gentle souls who have respect for each other above all else....but it just seems like a really risky environment where you could easily get raped, cornered, coerced, stalked, robbed, stabbed and then told "well...you were asking for it!"

*never been to one and yes, I'm not a big risk taker*

My first regular boyfriend in his dorm room during our sophomore year on our second night together. The first date was in my studio apartment off campus (oral only). 1981.

I specifically remember that he lubed me with a strawberry scented numbing cream while I laid on my stomach in his single, dorm-room bed. It ranged from me thinking, "this kind of hurts, and I feel like I might need to take a dump," "I like another warm guy laying on top of me... but the fact that his straight room mate is probably awake... a few feet away, separated by a room divider/tall bookshelf is kinda unusual... why are we doing this here and not at my place? Is he trying to prove something to his room mate? (he was). Does the room mate -- who went to high school in a wealthier burb next to mine -- enjoy The Manhattan Transfer as much as J. does?". "This feels kinda nice, oh wait, ouch! Hope he finishes soon!".

The giddy, secretive, subversive, warm, naughty, 'we're breaking the rules' homosexual intimacy aspect was wonderful.

Felt a bit sore but satisfied and proud and goofy walking from class to class all day on campus the next day. Colors looked brighter. We lasted as a couple for the semester, but I never really got into bottoming until decades later (the AIDS epidemic would be just a few years ahead) and then did so with a spectacular vengeance.

I'm with the other guys on this R178 - actually, hooking up with a stranger at a bathhouse, I think would be way safer and more controlled than meeting up with some random guy online. When I was much younger I used to chat to a guy online and go round to his place without anyone knowing where I was, and I fucked BIG guys who were much bigger and stronger than me, nothing bad ever happened but if they had been wrong'uns it could have been a different story.

In terms of your questions, what happens if a guy gets creepy/doesn't take a hint - you loudly reject him and if that doesn't work you go to the front desk and report him for harassment to the staff at which point he gets chucked out. Can you do that if you go to someone's house? No. I have had a few occasions where a guy was too persistent with me and I have the confidence and physical ability to tell them in very clear terms that if they don't fuck off I will knock them out, if you don't feel comfortable with that just report them.

Absolute worst case scenario you can scream for help if someone is actually abusing you too.

It's also much better for checking someone out before you decide if you actually do want to have sex with them, because you can usually see them completely, and in person you can check if you have chemistry. I've met men online before that I was up for having sex with and then in person I wasn't as keen but I felt obliged to go through with it anyway - that wouldn't happen in a bathhouse.

Saunas are FAR safer than meeting up online. It’s not like yr the only two people there FFS. But you don’t just have to go for sex. I go mainly to swim and catch a movie, but then I’m not in the US, & the facilities are superb.

The follow up thread to this should be “Who hurt you?”

May I confess to being amused by a debate about whether it's better to be deflowered in a bathhouse or on a Grindr hook-up?

R167 No doubt he dead of the aids. sad.

Let's see I was 24 and he was this cute Latin mix with a huge cock. Found out I could take it without issue. Kind of suppressed it for many years.

r185 why would you supress that? You are a unicorn!

I am equally amused R183

I can tell you a bathhouse or sauna is so much better than an app. It's like grindr live. Before covid I hit one in LA. I had a room and was just laying back checking the parade. A guy stops in my room, short thinner with a really nice body but reallyt thick glasses. He asks to come in and I smile an say sure thinking I am going to fuck this cute little guy. He leans down and we start making out i reach under his towel and before i get an inch past his knee I hit cock. Holy shit this kid is packing. Like a fucking baby arm. One of the best fucks I ever had. I asked him if he wanted to back to my place and he said yes, that I was the only one here he wanted to have sex with. Still a fuck bud.

The best things about a bathhouse are the variety of men, the quantity--so you can from person to person if you want, and the safety.

...what safety though?

That's the part I don't understand. You're naked surrounded by naked guys....no weapons, no wuick exit. If there even is someone working there willing to assist you in a crisis, how exactly are they going to intervene to protect you? Run out into the communal area and grab the guy you point at by the dick and toss him out in the street?

Are there two armed Pinkerton guards?

I'm not saying everyone definitely gets raped or stalked or whatever but if you do get hurt, robbed or filmed or whatever...nobody in the real world is going to support you. You think a judge is going to convict someone of attempted rape or assault because you go to court and say "that's just not how I expect to be treated in a gay sex bathhouse your honor!" Their reaction will be "you are an indiscriminate whore" and "you left yourself in danger".

To me, its like stripping naked and throwing yourself to the wolves, fingers crossed.

Maybe it practically never happens and 99% of the time, its just horny guys who are decent about it...but don't homeless men go to these places to shower and sleep for the night? Don't addicts? People hiding out?

I could just as easily be asking this about straight sex clubs too. It just seems like you're in such a vulnerable position in the hopes that someone hot finds you hot too. I'll bet the less attractive people really struggle in that kind of situation, ass hanging out, no nice clothes to hide behind and gym queens parading around sneering at them.

Or maybe they're paradise. I don't know LOL.

What if the whole bath house population turns on you in a drove and forcibly gangbangs you??

That is my fear.

Are there that many violent predators at bath houses?

r190, I have never encountered a violent or threatening man at a bathhouse, or even somebody who was mean or unpleasant. The worst I've encountered was a cross look to say, no, I'm not interested in you.

Given that bathhouses are dying out what is the point of arguing their merits?

[quote]R192 Are there that many violent predators at bath houses?

Yes! I saw a non-consensual bathhouse gangbang in a movie once!

I'm not keen on strangers moving in my bowel.

R190, just that fact that there are many people walking around prevents people from threatening you. It's not like you're alone in an alley somewhere or even alone in some stranger's apartment.

I had been sucking guys off and getting sucked and topping guys for about a year.

This guy kept coming by my workplace and talking to me.....eventually he asked me out. On the second date I went to his house and he fucked me. He was average sized and it was very nice. Of course as soon as he was done, I wanted to do it again....but he couldn't.

We dated for a few months and I was the top.....he wasn't interested in fucking me again. So that's been the pattern.......I get fucked and I like it but the guy doesn't want or can't do it again the same night.

So I just keep topping and hoping someday I can find a guy who will fuck me twice in one night.

I was 15. I called up Billy the queenie guy everyone made fun of at my high school. I figured he'd know what to do. I couldn't get out the words so he said, "people call me for two things: pills or sex," and I said "the last one." He told me to come over to his house. His parents were there. We went up to his room, I took off my pants, got on my stomach, he lubed me up, and pushed it in. It didn't really hurt but was uncomfortable. When it was over, I asked him not to tell anyone. The next day, of course, it was all over school but nobody confronted me about it. A girl I knew let me know Billy told everyone. I never got used to bottoming (except for a couple of times with poppers) and morphed into a top by the time I was 18 and never went back.

[quote] morphed into a top

I am imagining OP's muscles growing, his frilly overly fashionable pastel color clothes turning into Nike basketball shorts and a tank top and his gelled frosted hair turning into a backwards baseball gap.

Sort of like how the Hulk used to transform only gayer.

30 years old. He was a co-worker. Secret office romance. He pursued me, wore me down, fucked me, dumped me a few days later over email. It was a torrid, tortured 3 year mind fuck of a relationship. He was very well endowed and I remember him saying I took it like water off a duck’s back. Called me a natural. I can’t imagine I was a great lay. Would love a night with him now. Years later, I think I would blow his mind.

R191 What if the whole bath house population turns on you in a drove and forcibly gangbangs you??

That is my fantasy.

Can I just say that I have never set foot in a bathhouse? I came out circa 1990, when they had fallen out of favor because of the AIDS crisis. All I knew were bars and house parties. Plus, being in the military, bathhouses were off limits…they even had shore patrol checking them out allegedly. Always was curious though. I almost went to one after I got out of the service, but I never built up the nerve.

Grow a spine, R178, and get over your delusions about bathhouses.

Ive never really been sure who popped my cherry. When I was 12 ,my brothers best friend who was 14 ( I had been sucking his dick for a year) stuck it in and pumped about 4 times and came. He had a nice sized dick but it was so brief it didnt even hurt. I didnt even try it again (though I kept right on sucking dicks) until I was 14 ,and the 32 year old neighbor of mine who looked just like Desi Arnez jr Really showed me what anal sex was all about. First time I ever came hands free. I was obsessed with him and getting it again,but I think he was so freaked out that he did it he moved. Thanks to him I knew all about lube,cleaning out etc ,so I started getting fucked quite often by neighborhood boys then . I aslo quickly realized boys fucked like bunny rabbits but men knew how to really throw it,so I pretty much from that point on slept with older men.

1972. I was 18. It was my college roommate. He was gorgeous with an amazing body. I figured anyone that beautiful had to be gay. I flat out asked him if he wanted to fuck me. He didn’t hesitate. He had an average sized cock. It didn’t hurt, and it only took a couple of minutes before he shot his load in me. That first time was terrible memorable. We got better. Turns out he was also of average intelligence and dropped out after one semester. But that one semester was fun.

Bump

First time was in a bathhouse, either the St. Marks or the one down on 2nd Ave. I was like 19, freshman year in college (NYU), 1982. It was very dark, in one of those giant black-naugahyde-mattressed common rooms. It was an older black man. He couldn't have been that well-endowed, however, because I remember thinking "Oh! I think there's a dick in my ass!" It was a little underwhelming.

The first time was a blond kid in college. It hurt like fuck but it was interesting enough to try again…much later. The second time as with a guy in NYC. He gave me poppers, which helped a lot. It didn’t feel like much but just doing the act was fun. The third time was a guy about 20 years older with a substantial cock. He first lick my ass until it was warm and supple. I was begging for it. That time, it finally felt amazing. He was a FB for 2 years.

I still favor older guys because the sex is so much more passionate

[quote]R208 First time was in a bathhouse… He couldn't have been that well-endowed, however, because I remember thinking "Oh! I think there's a dick in my ass!" It was a little underwhelming.

Please do not put this in the “I Want to be Underwhelmed “ thread. We will lose it!

[quote]What if the whole bath house population turns on you in a drove and forcibly gangbangs you??

Well this guy had heart attack in the TV room at my local sauna, and the cleaner found him next morning on his knees bent over a couch. They believe he'd been given several loads while in rigor mortis. Isn't that adorable. Heavenly Love. Literally.

When I first came out, many guys tried to take my anal virginity but it hurt too much. I vowed never to have a cock up my ass. I enjoyed being a top for a good decade.

Some meth up my ass changed that really fast. The guy who first offered me the meth fucked me. After we were done hours later, I was still so horny (yes, meth is a relentless drug), I went to the bathhouse and got fucked by about 10 guys for the rest of the weekend because I was so intrigued by this new facet to sex.

I did meth every month for about a year and then stopped cold turkey. It just wasn’t doing much for me at that point.

In the naughts, the bathhouses used to be filled with methheads. And then people stopped meth as they understood how destructive it was. Others turned to the apps.

Fun times though before we all realized its price.

Meth...up your ass??

Like you smoked meth and then it was easier..? Or you physically put meth up your....huh?

.....so confused...

A Marine during a Labor Day weekend in 2000. I was so uptight about that night, he was unable to penetrate me. And he was really buzzed. But that next morning, he made me straddle him and sit on his dick. Hot sex. He was my first white boy too. He had a wife too, with a couple of kids. She was Asian (!) and knew that he was bisexual. As long as he took care of his family financially, she didn’t care.

I was 16 and he was 24. He was really beautiful and sexy. His body was amazing and he had a big dick. I had messed around before but always as a top.

Anyway, I said yes and I hated it. Hated it so much I didn’t bottom again for a decade. Anyway, I thought it’d be pleasurable from the beginning and it wasn’t. It hurt so much. He wasn’t being rough either but I also didn’t want to say no thinking he’d lose interest in me. After that he did lose interest cause I didn’t want to bottom anymore.

I did eventually learn to enjoy bottoming. Still more of a top though.

18-year-old Morrocan rentboy, outdoors behind some bushes.

r216 low rent.

*Moroccan

You don't know him, OP.

R217 had his in the darkness of the back of a box at the opera. High rent.

R213, it’s called a “booty bump.” You stick meth crystals directly up your ass (some dilute the meth first and shoot it up your ass). It makes you an insatiable bottom.

Was a dude on crutches who was half italian and half german in Toronto. Came on his sheets while he fucked me with his fat dick. Felt incredible.

Hot R222. Did he know he made you cum hands free?

I think I wasn't really a man until I went to the bath house for the the first time. It felt kind of like losing my virginity in the sense that the scales were removed from my eyes and I saw it was no big deal at all the way I had thought it was.

19,

Bartender

Pool Table

After bar closed.

[quote] I was 18 and a few weeks into my freshmen year at college. He was my art history professor. It was amazing. Besides getting my cherry popped, I got an A in the class.

Wow, you really did get a well rounded and quality educational experience. Money well spent.

R226 But did he woe him by sending him copies of Michaelangelo’s love poems that he wrote to different youths without properly attributing them.

Erna took mine then I shat in her mouth.

Bump

It was that summer we spent in Paris

Remember, he was a waiter named Jean-Luc!

Nobody took it. I gave it away.

My harvested large cucumber crops!

Carl Meny.

Big Big

Big BIRD

Streisand.

My much older brother beat and molested me as far back as I can remember. In college my professor and his roommate (both prominent organists). I was at his apt at the rectory after my lesson. Three students left me alone as I waited for my train. They offered me lemonade and the next I knew I awoke on a sofa, my clothes asunder. I left in a daze, walked to Lake Michigan to a restroom and sobbed as I tried to clean up (I was bleeding).

However I count my husband as the first to penetrate me in a non-aggressive way. He taught me to love.

My neighbor took it, I asked for it back.

Que es un "prominent organist" por favor!

[quote] I got an internal hemorrhoid after that (perhaps partly also due to opioid use followed by food poisoning) which has never completely gone away and so anything in my ass hurts like hell to this day.

You don't have a hemorrhoid, you have an anal fissure. See a doctor and it will go away.

I'm not sure who counts.....

I had a really hot wrestler as a roommate in my freshman year. Well, he had sort of an odd face and Luke of Luke and Laura hair, but he had a hot, wiry body. The last week of classes he asks me if I'm gay (this is circa 1988) and then was like, well, you can suck me off any time you want. Which I did, a lot, wishing we'd had that conversation 4 months earlier.

His dick was nice, if a little on the short side, and he shot a lot. Then the last night we were there, he wanted to try fucking. He got the head inside, but literally as soon as he did he started to cum. (And yes it was bareback but we were both new to it) It was a big load but I didn't think I'd really been fucked.

A few years later when I was 21 I met a guy at the bar in his late 30s. Beautiful short Persian/Iranian guy with a bit of a British accent. Looked like he stepped out of a 70s porno movie. Covered in thick fur, perfect dick for a first time, not too big or small. He was a great fuck for the true first time. Took his time the first actual time, but also really slam fucked me another time and showed me different ways it could be done. Also taught me how a top can be tender and loving, how before and after is as important as during.

R56 = Dawn Davenport in an alternate universe

An MCC Denver deacon. I was 20 or 21yo. He was early 30s. I was active duty military at the time and visited Denver MCC because I had finally accepted I was gay and now had questions about God, afterlife, etc. We had a long discussion. Evening rolled around so I visited Tracks (gay bar). A guy sat next to me and offered to buy me a drink. I didn't recognize the deacon immediately since he had switched to street clothes. We talked for half hour or so. He invited me back to his apartment. I felt at ease and was oblivious to any sexual interest he was showing. We chatted up a storm. It was late so he offered to share his bed. I accepted. He was kind of huggy, which I really needed at this particularly stressful time in my life. We started kissing, fondling, etc. At one point he was rubbing his cock against my butt. I told him I had attempted anal sex 3 times and found it was way too painful. He said he would be gentle. He was so sweet I gave in. He was very gentle. And OMG, it felt so fucking good I came without touching myself.

My stepbrother. We were 13 or so. Bred me in about 15 seconds. Still jerk off to that fuck.

Steve, at a Comfort Inn in Champaign, Illinois. Our eyes met in the frat boy bar on campus, and we agreed to meet later by the statue of the Alma Mater on campus. We had nowhere to go, so we split the $18 cost of a hotel room. We were too clueless to know what lube was, so we just used spit. I still jerk off to that fuck.

The coach.

R245 I quickly read that as a statue of Alma Mahler, which sounded so romantic and progressive for a college campus to have.

In grad school; I was 23. I was in the campus bookstore and saw this guy who looked to be an undergrad. He was blond, tall, and had very hairy legs. We made eye contact and sort of followed each other around the store. Eventually I checked out, but waited for him outside the entrance. When he came out, he motioned for me to follow him. We went upstairs to a men's restroom. At the urinals, we touched each others dicks. I told him I was not comfortable there, and he asked me where I lived. It was a ten minute walk to my apartment. So we went to my place, made out for a while, sucked each other, then he maneuvered me onto my back, pushed my legs up, and started poking my hole with his dick.

I vaguely remember the fucking part, I was so excited and he was so gorgeous – I could not believe he wanted me. We showered together afterward, he dressed, and left. But he wrote his name and phone number on a piece of paper before he left. I never called him, but ran into him on Spring Break a few weeks later in a club in Fort Lauderdale. He was there with another hot guy. We nodded to each other, but I knew he was playing on his level with the guy he was with. I was a few levels lower, and I was okay with it. I still jack off thinking of that fuck, all these years later.

R237 that is fucking hilarious. Biggest laugh I've gotten from the DL since the horse threads about Centaur SJP.

R248 is an absolute zero. Her story never happened.

No one took it. I gave it away.

R249, what was the funniest part of R237's story? When he got molested by his brother or raped by the organists?

R252 IT. NEVER. HAPPENED. Just the sad fairy tales of Elder gays who haven't been fucked since Nixon was in the WH.

R241 hot

A lot of you still "jack off to that fuck"

R243 very nice

A handsome hung cuban polo player and banker, from Buenos Aires and London. I knew him well and liked him. He was fun. He was 10 years older and he seduced me over a few dates knowing exactly what he was doing. It was good sex! I would have stayed with him longer but he was antisemitic and superficial.

R257 WTF! Did he put a few jews in the oven whilst you were visiting? I hate when people do that. Jesus.

A guy I met in an AOL m4m room when I was 25.

It hurt like hell. At some point, he said something like "don't you know what you're doing?" as a joke. I told him I didn't. And he seemed to be too into the fact that it was virgin ass territory.

Dang. One user blocked and the negativity disappeared from this thread.

R2 Sure Mr NAMBLA. In your dreams. Who took your anal virginity?

R167 No doubt he dead of the aids. sad. Who took your anal virginity?

R237 that is fucking hilarious. Biggest laugh I've gotten from the DL since the horse threads about Centaur SJP. Who took your anal virginity?

R248 is an absolute zero. Her story never happened. Who took your anal virginity?

R252 IT. NEVER. HAPPENED. Just the sad fairy tales of Elder gays who haven't been fucked since Nixon was in the WH. Who took your anal virginity?

R257 WTF! Did he put a few jews in the oven whilst you were visiting? I hate when people do that. Jesus.

{quote] One user blocked and the negativity disappeared from this thread.

Sure did, after you were blocked (you and your sockpuppets)

So many lying fucks here.

R260 is disgusting, an obvious troll, and should be banned.

Well, it was good while it lasted (this thread, not my virginity).

Now that the This Never Happened trolls have shown up, I guess we should just call it ...

Thread Closed.

98% of all postings "never happened". This site is faker than Pete Burns' lips.

Oh, r238, like a cup of sugar? Bad manners.

Yeah, I'm sick of the You're A Troll! / insult posts.

My friend lost his in a mens bathroom at....16? I think. Something like that.

Took?

I'm still selling it every time!

I had to google "MCC Denver" from R243s post

Seems it is a gay church there, possibly part of a chain of gay churches.

I was in LA on business, late '70s. Went to a bar in West Hollywood, met a hot Latino guy. Went back to his place and he fucked me hard. I can still remember how thick it was. He was almost apologetic to find out that he was my first. As though I was supposed to save it for someone special? He seemed special enough to me.

Satan, literally.

Bump

Father Williams, I was 10.

[quote] MCC Denver

MCC churches are nondenominational churches that are welcoming to gays.

Rev, Troy Perry founded the church - linked to his Wikipedia page below.

While some liberal churches have allowed gay members at the local level, MCC was the first to come out and be open and affirming for gays and lesbians, and state that at the organizational/institutional level. It took liberal churches like the UUs and United Church of Christ until later to support us.

Honey, nobody “took it.” I gave away

I didn’t just give it away, I paid for it and I even had to mop up the vomit afterwards

My wife.

Bump

Hump

Pump

Dump

Rump

Clump

[quote] I remember my doctor putting a finger up there once in my teens and being sore for like a day afterwards.

That wasn't his finger. 🍆

The Holy Ghost 👻

I'll have to get back to you on that.

A hobo on the train car I ran away from home in. God I miss his scabby cock.

I was 20. He was an older guy (23-24) in my fraternity. We weren't close friends. I lived in the house and he lived off-campus, so we hardly interacted. Anyway, I was in the process of coming out to the guys I felt comfortable with, and one night he was hanging around the house and ended up in my room. We were watching TV and drinking and I came out to him and he was cool with it (this was like 1994, so coming out was a big deal). Anyway, after a few drinks, I just said "Do you want to fuck?" And he said OK. And he fucked me. And then he avoided me for a few months after, and we never spoke of it, and it never happened again. I found a regular FB (also in my fraternity) soon after.

A friend I'd mess around with. Part battering ram, part epileptic fit. It hurts to think about it.

[quote]I was 20. He was an older guy (23-24) in my fraternity.

LOL.

Got high in my friends basement, we ended up watching porn. He was a wrestler so he was always shirtless in gym shorts. He had a hard-on from the porn and it was impossible to miss. I said your dick is huge or something like that and he looked at me with a goofy smile. Wanna see it? Fuck yes I did. That lead to want to touch it, want to suck it and the next thing I knew we was pushing it in me. He used a ton of Vaseline so it slide right in. He even kissed me as he fucked me. We hooked up all through his senior year until he left for college.

Ah 291 ,your story took me right back to my early days of seducing all the hot and horny teenage boys in my neighborhood. I was a teen too so dont call me a pedo. After the initial first few ,word must have gotten around as I was sucking and fucking them ALL by the age of 14-15. In fact my family moved because some bitch overheard her 2 sons talking about me and it was quite the scandal. My straight redneck father about killed me.

R288 hot. Did he kiss you while you fucked?

R291 Hot!

R292 HOT!!!! What did your dad say?

r291 it was very hot. We were basically a couple, people just thought we were bffs. He enlisted in the army, I got to see him a few more times before we just lost touch.

Bump

Dad did. My 18th birthday. I came home drunk. He spanked me - wait! I think that was a porn i watched.

I believe I was in my teens and he was my first boyfriend. I don’t remember exact age.

R298 Betty White wasn't even born yet. No doubt.

First time I really enjoyed it, though, I was in my mid twenties. I had an older boyfriend who I actually left my first boyfriend for, and he was a VERY skilled fuck.

[quote]Betty White wasn't even born yet. No doubt

Says the DLer who is likely older than I am, since you are all Boomers and Silents.

[quote]Satan, literally.

R271 = Rosemary Woodhouse

It happened to me in a dream. The most vivid, unimaginable, inexplicable experience ever. What a dream! Nothing like any dream I've ever experienced before.

R303 who was the dream about?

Some poof we met at the local pub.

R303 is Max Gail involved?

Bump

I gave it to Bruce

We were both nineteen. We were both ugly. He had a dick like a pencil.

College boyfriend at his parents house on the pool table while everyone was sleeping.

In retrospect, how we managed to not get any fluids on the felt is beyond me.

r310 umm you didn't I still need that 300 dollars for the re-felting of my table.

It's kinda amazing that you had a college boyfriend and that his parents had you over...never even mind the sex part.

Jealous.

R310 that’s so hot. How was it? What became of him?

I've had very few anal experiences; some bad, some okay/good.

The best one was probably this massage therapist who spent 40 plus minutes getting my whole body relaxed. He was gentle. It was nice.

Another time, I was making out with this guy. Bigger in every sense; like 6'4" 250 lbs. and I'm a much smaller guy. I told him I was ready to be fucked and he chuckled, kissed my forehead and said, 'Buddy, I'm not going to fuck you.' He was a top but he knew I wasn't ready for it. Being with someone who knew me better than I knew myself was a huge turn on. I think about him all the time.

To the best of my recollection, it was Colonel Mustard, in the conservarory, with the candlestick.

R314 that would have made me want him even more! Hot!!!

An incubus did it.

R312 and R313 - it's not as sunny of a back story as you think. It was in 2002, his parents were hyper Catholic and I was just spending the night as his "friend" since he was still closeted to them. His mother was effectively on end of life care and immobile and his father was passed out drunk upstairs.

He's now living a semi-closeted life (from his US based family) in Europe with his European boyfriend of many years.

18, the night I graduated from high school. Took the car my parents gave me as a gift and went to a local cruising spot. I hated it. He was too big and wouldn't slow down or stop when I asked him to. It didn't occur to me that I could be more forceful about making him stop. I still don't enjoy it 45 years later.

I was 18. Perry put on ELO'S Out of the Blue album. He massaged my back and gave me poppers. When he slid it in, it wasn't as bad as I thought it would be but when he pulled it out, I was afraid I was pooping.

r314 Was that at that the Columbus Eagle? Because if it was I am that guy :)

R319 bossy bottom

R321 and r314 true love reunited after all these years? ❤️❤️❤️❤️

R318 well you took all the fun out of that story

Still haven't lost it...though until recently I never really wanted to. I hear it's a pain in the ass.

I was 18. He was a married man. It wasn’t what I had hoped for. He was clumsy and made no effort to make sure I was comfortable and aroused enough to be fucked. I was a total innocent, and had no experience to draw on. I didn’t have the confidence or assertiveness to stop him. I can’t say it was rape because I really wanted it, but it was painful and quite traumatic.

My hymen is perfectly intact

r327 You don't even poop?

A 1,000 years ago, it was my second boyfriend. He jammed his cock into my ass, and he wasn’t gentle. It was so painful and I asked him to stop. He did so. The relationship was brief. I tried bottoming on numerous occasions and I felt nothing. I’m just not into it. I’m a top and I’m more than fulfilled with it.

[quote]umm you didn't I still need that 300 dollars for the re-felting of my table.

He's lying.

Your boyfriend's mother paid to have the table re-felted.

She didn't want to have to explain to her husband what the two of you did in the Family room.

[quote]My hymen is perfectly intact

The palace will need a letter to that effect from your doctor.

And we reserve the right to have our own physicians examine your vag.

1) 21 2) Future husband 3) 6 months 4) Not very good (we’ve perfected it since then)

Pastor Matt, I was 10.

My best friend's older brother Tommy. He was a senior in HS, I was a freshman. his brother Dave and I were bffs, he lived just a few streets over and I hung out with him and his family all the time. We went camping once and I forgot my sleeping bag. I shared one with Tommy because his was the biggest and I woke up that night he was spooning me. I should have figured it out lol. Anyway. I go over to Dave's house but only Tommy is home. He says Dave is out with his mom and Dad and I can hang out till they get back. We go to his room. He asks if I want to get high. Never have. He lights up his bong and offers me a hit, yup I am coughing and hacking it up. He laughs and says I can shotgun it to you. I say what is that. He takes a big hit and holds my head right up to his and puts his lips on mine and blows the smoke in, except he does not let go. Next thing I know his tongue is in my mouth, we are making out and he is undressing me (which was not hard I was wearing shorts and a t-shirt). He has me spread eagle and is fingering me in no time. He grabs some vaseline and smears it on me and his cock and is fucking me in record time. I dunno if it was because I was high or confused or just it happened so quickly but it did nto hurt. He kissed me the whole time which helped. He came inside me and pulled out and cleaned up. He told me to go take a shower before his parents came home. I was like a robot and did what he said. Then he came in the shower and fucked me again. Turned out his parents and Dave were gone for the day looking at colleges, He knew that he had me all to himself. It only happened a few more times after that, he enlisted in the marines, and Dave and I drifted apart in HS.

That was hot, R334!

R334, comes across like a pedo

R334, doesn’t make sense. You were best friends with Dave in HS and he and his parents were out looking at colleges but then you drifted apart in HS?

Did that all happen in two months?

"It wasn't 'taken'. I 'bestowed' it on all the husbands and boyfriends of my best girlfriends, because that's how I roll."

R 337, you really need to know the months that this happened...don't ruin a perfect hot story with needing to know the details...next you'll want to know what soap that used in the shower and what finger he used to finger him

It was stolen from me by an acquaintance when I was 53.

R340, did you call the police?

I was raped as a teen.

True.

An ugly blonde pooge took my V-card.

pooge An older butch lesbian who holds a preference for younger femme females.

I was 16, and went to visit my brother in college for a weekend. I ended up getting fucked by a couple of the guys who lived in his dorm. (There may have been drugs and booze involved.). I thoroughly enjoyed it, and whenever the opportunity to visit my brother at college came up, I was all over it! It was the start of my life as a whore, darling!

You are all the whoreth of all the heavanth and planetth in the entire Univerth!!!

My best friend actually ended up in the hospital after his first anal. The guy apparently moved a certain way and it ripped my friend's anal entrance.

R346 YIKES

R346 LOL. Ripped her beef curtains in half.

I was 17 and visiting Disney World with my family. A very handsome man (Raul, Cuban late 20s) at the hotel courtesy desk took a liking to me and would call me over and chat with me each time a passed the lobby. One evening I was swimming in the pool and he was by the poolside and we chatted a long time and he invited me to the a game room in the back which I didn't know the hotel had. We had sex on the pool table.

r337 We were freshmen. I played football he was in wrestling then quit sports. He became somewhat of a loner and we just sort of stopped hanging out by senior year.

R350 Why would your friend already be making college visits as a high school freshman?

R351, why is it important to find holes in someone's story? Does the anonymous message board that is Datalounge have a high journalistic standard that MUST be maintained, and pursued, at all costs?

Cute neighborhood friend. He would call it a gay phase at the time. He's married with children and grandchildren. Took a blanket into the alley behind our houses at night and he fucked me. It hurt at first but I enjoyed most of it. He had a big one compared to myself at that age. It was the only time we were together.

^we were both 13.

My first boyfriend.

I was a freshman in college.

Unfortunately it wasn’t memorable at all.

This guy I knew years ago told me he lost his in a mensroom. I found that quite sad.

R352 this is one of the things I find most obnoxious on DL. We can’t prove either way whether someone is telling the truth or lying. Why spend so much time and energy proving they are lying? It is more fun to play along sometimes.

R334 fucking hot.

R357 Because I'd rather imagine reality than someone else's fantasy.

The OP's question was an invitation to reveal interesting factual information, not make stuff up to try to titillate.

[Quote] This guy I knew years ago told me he lost his in a mensroom. I found that quite sad.

Gay men don’t usually wait for love

R360 I tried to and finally gave up and lost it to a rando when I was in my mid-20s. He was a very eager and capable 19 year old, so at least I picked the right guy.

r351 - They were going to see his cousin I guess? It was his father's college and he really wanted Dave to go. His father would do that all the time, just pop a surprise day trip on them. If you think I am lying, fine, call me a liar and move on.

I didn't call you a liar, R362, and you've provided a satisfactory explanation to my question.

Hot story.

No one … ‘‘twas a miracle!

My father. I was 8. It was painful, degrading, humiliating, and not consensual. I got hard though, and I still sometimes get hard when I think about it. Yes, I had therapy.

R365, I’m sorry. That sounds horrible.

A neighborhood boy. I was young -- 12 maybe? He was a bit older, maybe 15.

R365 I’m so sorry. That’s horrible

Bump

The family dog

a dude named Jimmy used to run up in me

Night time pissy drunk off the Henny and Rémy

I didn't mind it, when he fucked me from behind it

Felt fine, 'specially when he used to grind it

He was a trick when I sucked his dick

He used to, pass me bricks, credit cards and shit

Suck him to sleep, I took the keys to the Jeep

Tell him, "I'll be back," go fuck with some other cats

Flirtin', gettin' numbers, in the summer, ho hop, raw top in my man's drop

Then this homie Jimmy, he's screamin', "Gimme"

Lay me on my back, bustin' nuts all in me

After ten times we fucked, I think I bust twice

He was nice, kept my neck filled with ice

Put me in Chanels, kept me out nice

Called suckin' his dick, "rockin' the mic"

It was somethin' about this dude I couldn't stand

Somethin' that coulda made his ass a real man

Somethin' I wanted, but I never was pushy

The motherfucker never ate my pussy

R371, That's a whore's song

Too bad that girl didn't recite that poem at the Inauguration.

[quote]R351, who has a low tolerance for bullshit

... says a loser who trolls the Datalounge looking for factual accuracy.

I'm not proud of my first time. This isn't an excuse, but as an explanation, I was an ostracised and bullied teen who didn't really grow into his looks until 19/20.

When I came out at 20, one of the first friends I made in the gay community was this guy, let's call him A. I was never attracted to him, we just became friends who would go out, and he helped introduce me to the community. A had a boyfriend at the time, let's call him B. B was a very flirtatious, probably hyper-sexual come to think of it, and charismatic guy. One of those dark haired, pale skinned Irish guys. We'd hang out and B would flirt with me all the time, in a way I just assumed was fun. While I hadn't done anal at that point, I was sleeping with guys (or at least, letting them suck me off behind the club) and it was a small community and it got around that I had a larger penis. This fascinated B and he'd always be talking about it. A never seemed to care.

I couldn't believe that anyone would want me at that time, because of my past, and was always surprised to be approached, and for many years let probably 80-85% of the guys who asked me have me.

Anyway, B and I were pretty good friends then, and after a few months, he and A broke up. During this time I barely saw A and I was kinda hurt because I thought he was cutting me out. On reflection, he was trying to keep away from B, and doing the whole "living my best life without you" thing, and as B was always calling me up and hanging out with me, A would keep his distance.

They still lived in the same house, and one afternoon I went over. It was just B there, and we're sitting out the back, and he starts saying all these sexual things. He knows that I've never been fucked, and he starts suggesting he could help me out with it. I was conflicted between not wanting to do that to A, but also really finding B attractive and wanting to do what he wanted (as I said, low self esteem). He kept grinning at me and nodding his head towards the bedroom.

Finally he wore me down. He got me to stand against the wall, pulled my pants down, put on a condom (I remember it was black) He must've lubed me up, but I don't remember. I do remember him pushing into me, and how intense it felt. Unlike most stories above, it didn't hurt, in fact it's never really hurt me. But it is intense, and all the pressure on my bladder at this time made me feel like I needed to pee too. I remember as he got in he then grunted in my ear, in that tone boys get when they're hugely turned on and thinking of nothing else: "I'm gonna start riding you now, ok?"

He did and it was amazing. I loved it, but it was really intense, and after a few minutes I made him stop and instead he sat on a chair and I straddled him. I was so turned on and yet terrified one of the other housemates, particularly A, might come home. I don't think B cared at all. So after a bit more, we sat next to each other on the couch and jerked each other off, with him licking all my cum up.

I've never really been able to enjoy this memory, I felt like the worst person in the world. B was casual about it: "Sure, we can keep it a secret if you like", and I never really saw him again as he moved out. Funnily enough, A and I are still friends and he doesn't give a shit. But I felt awful. Since then my numbers are up in the hundreds and I must've fucked a number of guys in relationships/married, just by the laws of average, but I've never known beforehand.

I've only been fucked up the arse five times in my life though. It felt good (got a few hands free cums even), but my body didn't seem to warm to it too much, and in my mid-20s I started bleeding, and ended up, after many years of doctor's fobbing me off that it was normal and would heal itself, having an operation for a fissure. And now I just don't want to risk opening it all up again. And I kinda prefer topping anyway.

So, yeah. That's my story.

Hooked up with a guy at a bar. I fucked him first and let him fuck me.

R375

As someone who hasn't yet and doesn't discuss it with friends, thanks for that honest story. I totally get why you'd feel ashamed. Glad A didn't hold it against you.

Can I ask how the fissures happened though and why you needed surgery? That seems serious....but you said you had no pain during anal so....how did fissures happen? And what did the surgery do?

[quote] ... says a loser who trolls the Datalounge looking for factual accuracy.

Says a brainless idiot

[quote]Can I ask how the fissures happened though and why you needed surgery? That seems serious....but you said you had no pain during anal so....how did fissures happen? And what did the surgery do?

I wish I could tell you, but I don't actually know. My doctor did say he didn't think it was from anal sex. A couple of things, we grew up fairly poor and meals were often plain pasta, stuff like that, you know. We did eat vegetables, but a lot of stuff was not that full of fibre. Then in my early 20s, some sort of food allergy cropped up. Every time I would eat out, and sometimes at home, I would be hunting for a bathroom. I think it was lactose - only improved when I started going to the gym for some reason. But day after day I would go between having the runs and then being really blocked up. I think maybe this created the problem. Then doctors wouldn't take it seriously. Just: "eat more fibre and it will heal", but it didn't. Eventually I got a good doctor and he sent me to the surgeon. The surgeon was like: "I do these surgeries ALL the time, it's common" and I went in, had the op, and after a healing period (admittedly long), it got much better. No bleeding now, nor that horrible sharp, slicing pain when going.

And yeah, never any pain during anal, but who knows if I weakened something? And then the allergies made it worse? I only did anal about five times and this was before the allergy cropped up, so who knows?

Marcio. Portuguese software something or other. We had been speaking online for a while and he knew I was a TOTAL virgin. Anyway, one day I was going through a rough patch (adulthood before you lose your virginity is by definition a rough patch, perhaps, looking back) and he suggested that I come to his house and we have sex. I didn't feel remotely taken advantage of or whatever. I think my inexperience was a little bit frustrating for him and he hurt my hip at one point with all the moving about. Yes, it felt a bit like I was pooping but not as much as my second time (with a mixed-race guy). Before I left, he gave me a little kiss (he said, "Always kiss someone after you have sex with them", which was a bit corny, but sweet) and told me not to fall in love with him. Not that I would have anyway, frankly.

R375 and R377, I had an anal fissure, too. I also had doctors fob me off for years. In fact, it was 8 years and I didn't have anal sex that whole time. I heard the same thing--eat lots of fiber and it will go away. It never did. It usually would reemerge after traveling when I'd become constipated. I think that's how it started because I wasn't really having much if any anal sex when it first began. I had broken up with my ex-partner and my job required me to travel a lot. I was constipated all the time and had to strain when I had to go.

Anyway, I finally went to a colorectal surgeon who said all the other doctors should be ashamed of themselves as a fissure that hasn't healed in a couple years, much less 8 years, needs surgery. The surgery was no big deal, it took 6 months to heal, and then I finally had anal for the first time in 8 years. Damn, I had forgotten what I was missing. No recurrence and I've been having regular anal sex about 3-4 times a week for the past 9 years with my current partner.

I was 17 and had moved to London to study, I was the nervous, shy, small town boy from Scotland who started finding themself in the big city. Anyways, I got on grindr, yes I was a year under the legal joining age fuck off, and of course I looked young and cute so had quite a few hits straight away from mostly creepy older guys, one guy seemed sane and funny and so we started messaging, long story short I went over to his one night, he was a well built, black copper and we made out on his couch before he put me over the back of the couch and started eating out my ass, then he brought out the lube and started slowly fingering me and before I knew it I felt his thighs against my ass and I realised i was being fucked and that was how I popped my anal cherry.

R26 “ I was 17 living in South Kensington, London. I had seen him in his apartment through the window, looking at the back of the buildings on the interior of the square, fucking someone”.

Was it Lord Mountbatten and Prince Charles again?

This sounds terrible, but I honestly don’t remember.

I believe it’s my first boyfriend in college, but I’m not entirely sure…

My partner, in a hotel in Atlantic City, he was 28 and I was 33. We used lube, but I still bled and it hurt. I'm and old pro at it now and it feels great to cum while getting anal!

R381, I hate that you had that experience, but it was at least comforting to read someone else had pretty much the same experience as I did. I haven't been brave enough to try anal again though.

between many and a few years ago, I was with a guy who pushed every last button. I was deathly afraid of anal because a) AIDS and b) it HURTS.

But I was making out with this one guy who really knew what he was doing; he got 'me. ' in a way nobody has or since.

I said to him in the throes of passion 'okay; let's do it. I'm ready.'

He let out a little chuckle; kissed me on the forehead and said, 'oh, baby. I'm not going to fuck you.' He knew I really wasn't ready and knew me better than I knew myself. THAT is more intimate than a fuck.

I wish I could see him again.

One of my first partners, Les, ventured up there, after we established some trust. I sat on him, and passed out from the pain. I felt so badly for him: he thought he had killed me. That was a long time ago, and I still don't bottom, but I think I was too afraid back then to embrace the moment.

bump

one of my older brothers friends, 2008 It was summer before I started high School. My mom told me to go down the street and get him. I went to his friends house to get him. He wasn’t there i started talking to his friend and it happened. Consensual he was older I was 14 he was 19 ish. He walked me home. I felt so disgusting and ashamed I took the longest bath ever.

His name was Emory and he lived on the adjacent property to ours when I was growing up. It was our 16th summer and he invited me into his room and offered me sweet tea and the comfort of his feather bed.

He had a pecker like the branch of a mighty oak tree and once he had lubed both it and my unmolested brown eye, he slipped his appendage inside. I was a natural from the very first. He was balls deep by the 3rd or 4th thrust and soon my prostate was pulsating, sending waves of ecstasy through every nerve in my body.

We both spent ourselves and lie naked in each other’s arms, tenderly kissing and caressing in the hazy afterglow of our lovemaking. Two months later, he was sent up the river on a morals charge. I never saw him again.

My husband of 50 yrs. He showed me the rapes at the hands of my sibling and his disgusting best friend were not the same as making love with someone who loved and cared for me. We learned together to have an extraordinary live life.

I don't have to read all 400 posts to know y'all started hoing young.

R394 lol, nope never

I was 17, he was 38. It was wonderful, but I ended up the top.

R393 Racist. Clearly he was black.

R392, Calm down there, Miss Lindsey.

bump

I'm a side.

Bruce

I took one guy’s virginity. I was living in Berkeley in the 1980’s and this cute kid picked me up at the White Horse. We went back to my place and fooled around and did oral. He showed up at my place three weeks later and asked if he could crash for a fed days. He was homeless and out of work but thought that in a few days he could stay with another friend. He was a dancer and do that explained his homelessness. I told him he could stay if I could fuck him. He told me he was a virgin but he took my cock like a pro. He stayed three days and I probably fucked him twice daily.

R392 made me laugh

I was 23 and at a party in Portland. A handsome blond guy with a decent body (or so I thought at the time; I had been drinking) a few inches shorter had been making eyes at me the whole night and eventually hit on me (which felt really hot). He later told me he liked tall, Eastern European-looking guys, hence his attraction. He said he was 21 and had served a few years in the Navy (or Marines, can't remember). But, he was nelly af, so he didn't really come across as a "military type" to me (but I had never served, only formed impressions from movies). We ended up at CC Slaughters (or the bar across the street, Scandals?) and cuddled and flirted. We went back to his place and made out and fooled around the whole night in his studio apartment (it had a "pull out kitchen," wild). I had been with a few guys before, and only had been digitally penetrated (which was weird). I was pretty inexperienced and naive. We would take naps and then make out again until dawn. It felt extra special because he had been playing Tori Amos' Little Earthquakes the entire night from his limited music collection and it just so happened that I had been listening to it for a month non-stop (the album had been out for five years or so). He also had a single of an extended version of Underworld's "Born Slippy" that he also played, which was another strange coincidence, because I had seen Trainspotting multiple times at Cinema 21 within that year and was obsessed with that film, particularly the finale where Renton delivers an ironic monologue about submitting to capitalism and consumerism as the only alternative to drug addiction (which is set to "Born Slippy"). So, there were all these "signs" that night was "meant to be." In the morning, I finally gave him my ass, because it felt right and important that I do and being with him the entire night had somehow justified it (lol). I don't even know if he wanted to. He seemed like a big old bottom. But, he asked me if I was sure, and I said yes. I don't remember much, other then I was face down, he wore a condom, and it probably hurt (I don't remember it being pleasurable). No idea if I was even clean down there. We took a shower together later and then sat down and watched The Frighteners on VHS (Peter Jackson movie with Michael J. Fox right before he did LOTR).

We saw each other one or two other times. I hung out with him and his friend Israel once on the Waterfront. They had ambitions of "running the town," whatever that meant. I'm not sure how far they got. But, I think they wanted a threesome, or Israel wanted to hook up with me and I wasn't interested. I think they were both probably into the drug scene at the time, and I wasn't very attuned to it. I didn't have a lot in common with them anyway. That was it.

His name was Matt Beasley. No idea what happened to him. Another coincidence is that I had just saw my "best friend" for the last time unknowingly just a month before. We had been "best friends" (according to him, and I would have agreed) for three years and then he ghosted me. I was certainly hung up on Matt for a little bit, just because I had over-romanticised what had happened between us in my head. But, it was my best friend who had thought of way more of the time.

It's a weird period to look back on. I had had a really terrible time in college, actually was a few credits shy of graduating, due mostly to depression. I had moved to Portland from where I was to finish my degree, get myself out of debt, get counselling, and, I guess, come to terms with my sexuality. I'm not sure how well I did with that last one. I was so young and clueless and was really trying to do my best. I graduated and left Portland a year later, I guess, to close that chapter in my life and move on. I wish I hadn't been so clueless about everything, myself, and the world at the time, but I could only work with what I had, I guess.

Buddy Ebsen and Charlie Ruggles

I think I've told this story before on here. I was in a fraternity and started coming out to a few friends I trusted. One night I came out to a few guys. One of guys ended up in my room and we drank beer for a while. I just said "Do you wanna fuck?" and we did. He didn't talk to me for a while and never talked about it, but he had a really good dick and knew how to use it. He was "straight" but told me he was gay (while his dick was in my ass). As far as I know he's still "straight" but this happened 30 years ago and I keep in touch.

I was 50, he was a porn star. I paid him 300 bucks to fuck my ass. It was great! No pain- he was knew what he was doing.

*haven't kept in touch*

R406, hot. Frat stories are so fucking hot.

My best friend from high school. His parents were away, and he kept beating around the bush(so to speak), bringing up sex and making comments about the size of his dick. Then he told me he had a Speedo and would I like for him to try it on. Suddenly reality set in and I was getting really excited, even though I was never with a guy before. He walked out of his bedroom for a minute, then returned wearing a blue speedo. His ass and bulge made me hyperventilate. Then he grabbed my hand and put it on his ass. Within a few minutes we were in the shower, rubbing each others bodies, all soaped up, jerking each other off. He took his cock and started frotting my ass, and then entered my hole. Hurt at first, but then felt magical after a few minutes. After he shot a load in my ass, I turned him around and did the same to him. After entering his anus, I came in about 2 minutes. Hot as fuck. That experience made me gay.

R404: Full names? Really?

R392 Is Blanche Devereaux posting from beyond the grave.

R410 "But then felt magical"

Uh-huh

Who the fuck puts a real name here?

A hung Irish/German guy I met on IRC.

I came handsfree on his sheets.

I was 20. He was about 34. Met him at the Met Opera House (ABT). Went back to his apartment and he fucked me and I fucked him. He had a small dick so it didn't hurt. I came twice: once when he was fucking me (rubbing my dick on his bed) and once when I fucked him. He wasn't the greatest lover but it was a good start.

I'd tried a few times during my HS years with a friend, it never quite worked and it would end up being, well, frottage close to my hole....

I was fucked for the first time at 21-22 by Jay, a guy I was introduced to in a gay bar. Handsome older man, late 30s. He was Iranian. This was mid 90s but he had a very handsome sort of 70s shaggy look to him. When I saw photos of a young Cat Stevens years later it made me gasp, Jay looked just like him. Soulful eyes, very passionate kisser.

His dick was a perfect "Goldilocks" dick for my first time - not so small as to be disappointing. nor so big I needed surgery for my prolapsed anal cavity later. We only hooked up once after that. He was a sweet guy and a perfect guy for a first time experience.

[quote] entering his anus

How clinical

Very hot, R410.

I should've killed myself when he put it in me. After the first time, before we were married, Ralph promised never again. He promised, and I believed him. But sin never dies. Sin never dies. At first, it was all right. We lived sinlessly. We slept in the same bed, but we never did it. And then, that night, I saw him looking down at me that way. We got down on our knees to pray for strength. I smelled the whiskey on his breath. Then he took me. He took me, with the stink of filthy roadhouse whiskey on his breath, and I liked it. I liked it! With all that dirty touching of his hands all over me.

R420 I didn't get more than 3 words into your post before the convulsive laughter started.

Of course Margaret would chime in.

You guys.

R1

How much of a surprise...? Did he climb on top unexpectedly or something....? Or slowly build up to it...

Some guy I picked up at a bar. Took him home and he fucked me. Loved it so much, he fucked me again. And again and again for the next two years that we were together

I was 23, and had met him for a first date. He was French, 12 years older than me. Wined and dined me first.

R407 is real

I was 68 and he was 21. We had so much fun for only $100.

I honestly can't remember, which says more about me than I'd like to admit.

I knew a gay. His name was Paul. And Paul was so nice. But he only like two tings. Fisting me and filling my asscunt with jizz.

Bump

Some rando hookup from a gay bar who lived in the neighborhood. Texan guy named Steve. Fucked him first then I let him fuck me. Bareback

R430 can’t believe you wasted it on a vers guy. Yikes.

Does getting fisted count?

Bump

When I was 19 almost 20 with who I thought was my bf at the time....I shot over my head....I just turned 50 and we still talk on Facebook....

Betty

Jimmy Joy

R432 Yes indeed. Anytime a body part is shoved up an ass your cherry has been popped.

Some guy I hooked up from a gay bar

The Marchioness of Cholm-...

OOPS! I mean... actually, I'm anally inviolate!

There is no such thing as “anal virginity.” And only women can be virgins anyway.

The definition of a virgin is a woman who has never had sexual intercourse, which is a penis entering a vagina.

Oh Mary :gasp:

I was 21, and it was a boyfriend I thought was the guy that I'd marry. He bore a strong resemblance to Robert Downey, Jr.

His cock, although aesthetically lovely, was rather unimpressive in size, and he ejaculated before it even got all the way in.

It didn't work out.

^Are you married now?

R444 Yes, but not to him.

I grew up in a town in the Midwest, the county seat. Every year a traveling carnival came through. I loved it. When I turned 16 I worked it for the "five days and four nights" it was running, selling cotton candy. They had the old spinner and I loved it. One of the barkers was about 21 and he'd come around and we'd talk. He asked if I was going to work again the next year and I said yes, and he grinned said something like, " Good cause the corn'll be tasseling by then." I remembered because I thought it was strange, because the carnival was in mid-June, before corn gets to that point.

So the next year came and he was working the funhouse, which was a fold-out, built-up affair from two big rigs. He got me more hours and I'd work there from about 8 until closing, and then we'd clean up. Now I see he was getting friendlier and friendlier.

We made out a few times and I about died the first time he kissed me. I jerked off with some classmates a few times but that was just that, and I didn't even look at them doing it. But this guy was everything I found I liked. So yada yada we did it on some blankets he threw down in the hall of trick mirrors. It was amazing, I thought. And after that year the carnival was a county over and I went, but he wasn't working there any more. I've never felt used and if he'd made a move the first year I would have run away.

Sweet story. Funhouse mirrors though? Can't imagine that made the scene more romantic....

bump

Some guy who also gave me gonorrhea

R447, romance was the last thing we were looking for and neither of us were looking at the mirrors.

Obviously you've never been a teen in a funhouse having sex for the first time with someone you really liked and were beyond happy about what was happening.

And not it's too late, alas. Unless you get a job with a carnival and take the other role.

I was in 10th grade, and he was a senior. He was captain of the school's basketball team, class president, and gorgeous.

I was helping him with a class project he had, and he was standing behind me while I was writing on a table at his parents' home. He kept pressing against me and I could feel that he was erect.

He was very direct in telling me that he wanted "...to be deep inside you..."

To this day I love that kind of talk and within 30 seconds we were naked, in his room and he was inside me. He was quite large, but I was so turned-on by his pressing against me and what he'd said, I didn't really feel much discomfort. For about 3 weeks, we fucked every afternoon after school. Nothing since has compared to those first sensations.

Donald @ 19.

Bump

Some of these stories are hilarious if you read them in Wealthy Woman’s voice (especially R375 and R417).