What Age Did You Bottom For The First Time?

15

18. The guy didn't know what he was doing. Ow! I felt like one of those straight guys on satyr.com who don't know what hit them.

13. It was with this really hot neighbor guy.

I was 10.

41

15- my high school romance. His name was Pat.%0D

The night of my 21st birthday. A (straight) buddy took me out for my first legal drink and stuff happened.

19 - just moved to New York for college. Went out clubbing and a very handsome older man with salt and paper hair (late 30s?) approached me and we went back to his place. He was very tall and had an anaconda dick so it was a fun and painful (in a good way). It didn't hurt that I was rip roaring drunk so I was able to relax enough to let him inside me. Other guys had attempted to fuck me in the past but I was too tight-assed (figuratively and literally) for it to happen then. Before that I was just doing oral stuff here and there with the closet cases in my high school.

Never.

25

with my 1st boyfriend. Hurt like Hell and he stopped. We tried four months later and it was heaven - did it twice in a Row it was so successful

31. I waited a long time. I still hate it.

How did some of you guys wait so long. I was 13 and practically begging for it. I turned into something of a little whore, letting just about anyone stick it in me. I guess I was just born to be a bottom.

The Saturday after my 16th birthday, when I got my driver's license and headed in to the big city alone.

72. Didn't like it much, but you do what you have to.

20. Got picked up at the "frat" bar on campus. Took me to a Comfort Inn, where we split the $18 room rate. Screwed me with no lube, just spit. Came inside me with no rubber. Didn't bother to help me get off (or even help me realize I could just help that along myself.) Still loved every minute.

25....I knew I had no interest in it, but I figured I should try it before I wrote it off. He was not particularly big, so it wasn't painful and was in fact fine, but as I suspected it was much like playing with my nipples. Perfectly pleasant but does nothing for me. I have since bottomed only 4 other times, at the request of my boyfriend of 20 years. He didn't much like it either but we did it to shake things up every and then, but it always ended with us flipping back to what we like best.

The orgasm of a bottom is much stronger than that of a top. Something about hitting the prostate that does not compare.

THAT'S because being submissive means being in total control

Do thermometers count? Because if so, I was about 6 mos.

R18 please explain more, I just don't get that. Sincerely, how does being submissive mean that you are in total control?

15. I lost my ass cherry to Doug during a sleepover at his house. He plunged it in hard and fast and showed none of the customary mercies. I thought "Do I REALLY want it to be like this?" but a second later it was over. It had been like that whether I liked it or not.

Tried it several times since I was 20 (I'm 43). Everytime it hurt like hell and I felt weird the day after, as if my bowels had been "re-arranged" in the wrong order.%0D %0D Not for me, thanks!

19. I was in college and went with a friend and some of his friends to a movie. Afterward we had a gathering at the apartment of one them. We had a few drinks. The host was a 30 year old graduate student/teaching assistant. We hit it off and I stayed when everyone else left. Later on in bed I turned over and presented my hole to him. His cock was average and he was gentle so it was a good start for my first time. I was very eager for it and have enjoyed it MANY times since.

I was 24. I was housesitting for my boss, and thus had the opportunity to have an overnighter. I met him at a local gay bar near closing time. He was in his late 30s, blond, and a very muscular letter carrier (build like 'Rocky' from the Rocky Horror Picture Show).

I've never bottomed. I've topped once.

17. He was 27, hairy Italian with a cute mustache.

More bottoming, please

20 - His name was Chris, my first real boyfriend, he was beautiful and had a great cock. Still one of my favorite memories.

Let's just say that if it hadn't been for the hung meth clown and the Twinkies, the shoot for Dawson's 50 Load Playgroup Weekend would have been rough.

18, a guy I'd been seeing casually slipped his tongue in my hole and I forgot pretty much everything until his cock was buried in me. Took 2 years to try it again. Still prefer to top.

[quote]casually slipped his tongue in my hole%0D %0D Lol. Cute.

What's a "meth clown", R29?

You don't want to know

I was 17 and on spring break during my senior year of high school. The graduate assistant coach (early 20's, hot) fucked me. He was also seriously hung (8.5 easily), so it was quite an introduction to anal sex. I thought it meant something, but it didn't. At the next practice, the coach acted like nothing happened and that I was no one special. I wonder if he did any thing with any one else. This was in the early 80's at a large upper-middle-class suburban high school.

18

20

18 or 19, in college. A graduate student was the culprit; he was about 5, I think. A quiet guy, to be sure -- but hung like Man O'War. Hurt like hell (he liked it lube-less, and I was so green I didn't realize that lube would have been a valid request -- I wanted to pleaaaase him), but got to where it felt incredible. My favorite position was sitting on it, riding up and down. I always came very vocally, but he never did...so silent I never knew if he was through.

at 5 as I was dodging bullets in Darfur.

My buddy and I must have tried it at 15. I don't remember thinking it was that great because it wasn't something we did much. I came out at 30 and let my second boyfriend fuck me. He was a bottom and huge and it was awful and still is.

Er, I meant to say "he was about 25..."

16

How are we defining this? The age I actually had another man's dick up my ass? 27. The age I first stuck a finger or other phallic object up my ass? About 15 or 16.

I think I was about 30. I came out late. It was pleasurable, but guys I dated wouldn't let me fuck them because they thought my dick was too big. "Oh no, you ain't comin at me with that."

I didn't know having a big dick was a good thing, and really developed a complex about it.

THEN, I met a guy who loved it. I'd never fucked anyone before. Katie bar the door, he still loves it.

18 - with one of my fellow freshmen (who then became my fraternity brother). We fucked like rabbits (taking turns - in our dorm rooms, in the woods, in my bedroom at my parents house - he even jacked me off when I was in the hospital recoveding from eye surgery!) and sucked like there was no tomorrow (even while I was driving). He has a nice slnder long dick - cut.

In my sister's bathroom in the 10th grade. I was 15 and my friend wanted to fuck me. We were supposed to be watching "Hello, Dolly!" in the den while my dad was grilling out back. We weren't watching "Hello, Dolly!", my friend was plowing me up against the sink.

36.

And part of the reason was that I had no idea how the entire ass/clean, ass/shit thing went. Not a clue and no one to ask.

Was everyone's first time miraculously clean? I'm serious. Were you all just lucky?

Not that clean, but not a filthy mess either

I thought that this was about bottoming for the fist time!

12. But I leave it off my resume.

Late 20's--I hated it--didn't try it again for a couple of years-now I'm just a big ole bottom. Poppers helped.

I bought a vibrating dildo at age 18 and I've never Looked back

24

19. I was dating an older guy (among others) who was well hung and was patiently warming me up to anal without pressuring me. Then one night I went out with someone else, got a little drunk and ended up bottoming for him.

He had a short little dick and no finesse, so the experience was all jibbity-jabbity, jibbity-jabbity. Ecch.

The older guy I was seeing later showed me that bottoming could be a pleasure, but I've never really taken to it, and rarely do it.

16

19; he really took advantage of me, but I couldn't say no either.%0D %0D It hurt; I asked him to take it.%0D %0D I was looking for intimacy and friendship; not necessarily to get fucked.%0D %0D

26. He was a bottom but I made him fuck me. Not very memorable.

Last night

18. A senior fucked the hell out of me, on request; smokin' hot. Thanks, ML!

15-- my high school boyfriend who was a year older.

Some gay couples in a top/bottom relationship take the gender roles too seriously..

Like this couple for example..

They are cute though...

19. I was a sophomore at a small college in Ohio. I was "closeted" (asexual virgin) and knew of only 2 gay guys on campus. One was my roommate and another was a guy that my roommate met through the campus's very, very small LGBT support group.%0D %0D The guy was a walking orgasm. Blazing hot and country bumpkin-style sweet and friendly. A few weeks after meeting him, I practically threw myself at him after a game of (dorky, I know) drunken Truth or Dare. %0D %0D He had a single room so we went there to fuck. I topped, too. Wild and unforgettable night. %0D %0D Only later did I learn why he had a single dorm room--mental issues including uncontrollable rage. Which turned out to also be wild and unforgettable, but not in a good way.

19, attempt. 19 1/4 - what is the big fucking deal (pun intended)? 19 1/2 - third times a charm. 19 3/4 - starting to really like this... - 20 - rocket to the moon!

when I came out later in life

14. His name was Ed. It was 1977 so we barebacked. It wasn't clean. Both of us ended up with shit on our dicks, pubes and ass. The next time we did it we washed up first and used condoms I stole from my dad.

22.%0D %0D Last time was 30.%0D %0D I'm 46 now.%0D %0D

5. (yes. really.) he was 6.%0D %0D Have been a bottom all my life, and I've never looked back... (oh, you know what I mean.

55. Never again.

r67, 5 and 6 years old????????%0D %0D Baby perverts!

I was 19 in my date's dorm room with his room mate on the other side, separated by a few tall bookshelves, which is why I didn't scream from the initial pain.

I was flat on my stomach, not knowing anything. The guy lubed me up with some sort of strawberry flavored de-sensitizing cream and probably some coke (he'd been rimming me, which sort of shocked me with disgust but felt pretty good).

The cream didn't work for me, but kept him fucking me all night to the tunes of Bette Midler, who I knew nothing about. Bette Midler's eyes from several wall posters were watching me. I had been introduced to him at dinner in the dinning hall after complaining to a friend I'd known since grade school that I was gay and bored, so he said "hey! I know a gay". After a while it felt OK, but mostly I liked the intimacy of a warm body on me.

The next morning everyone got up, had breakfast and walked to Calculus class together, as if nothing unusual happened. I just sat there thinking how I'd been fucked all night by a Bette Midler queen.

Several boyfriends later, I discovered the pleasures of bottoming.

I was 8 he was 16 i had no idea what I was doing. It hurt at first but i don't remember hating it. my second time i was 13 he was 14, it hurt but i enjoyed it! I knew then that I would be fucked for the rest of my life and so far I do. love it, love it, love it!!!

It was Bruce. He was rough with me. And kinda cold afterwards, but he bought me a motorcycle.

NEVAH!

21. It was my first time going to a gay bar - alone, even. And I went home with this muscular older guy - in his early 40's, I think. He gave me a good 2-hour of foreplay, with lots of hot bj and rimming to work me up. Then he pulled out the lube and slided it in. He was as hung as a horse (at least 9, for sure), and that was my first time, mind you. It was very, very painful and at the same time, pleasurable. We dated for a couple of months after that.

15. With a much older guy (32). He was very sexy, tan and hairy. He was a waiter at my parents' Country Club. Spent a few weeks warming me up, and then the rest of the summer fucking my brains out. Loved it. Very sweet, caring guy. Taught me all about being safe and responsible (this was 1985). Last time I saw him was the summer after my freshman year in college, we had a thee-way with his long-time partner where they both fucked me. Fond memories.

18, 19, 20, 21, 22, 23, 24 and then I just couldn't hold a straight face claiming it was my first time.

21.

21, on my Birthday! But, bottomed very few times, and haven't bottomed for many years.

Just to add somethig:

That experience is somehow seared into my memory and psyche, so much so that I enjoyed bottoming. I think it was because of him and of course, that experience. To this very day, I top only at request, or when the vibe is right.

It was called Browning in my youth, and those who did it were called Brownie queens. I never did it for the first time, I just told everyone it was my second time.

I am having my cherry popped for the first time as I type this

I'm cleaning my bathroom bowl.

Fourteen. BIG prefect using California Poppy for lube. In my twenties it got to the stage where I never even bothered to turn round in an orgy to see who was thrusting in there. Then used to go out dancing with it seeping. Good times! Yes, I was a whore, darlin. Still HIV neg.

I had an experience at 19, but it wasn't good. %0D %0D The first time I really enjoyed it was years later when I went for a massage; I was petrified of AIDS (this was in the early '90s) and so I chose a guy who was clothed in his ad. It read: Legit. No Sex.%0D %0D I figured I'd go and be touched and relaxed... we have a long talk about safe sex and all but the next thing I know he's got me TOTALLY relaxed and manages to open me up. He put on a condom and entered me slowly, patiently and I loved it.%0D %0D It spoiled me ever since.

31. I lost my virginity at 18, but I was terrified to bottom. I still hate it.

Another 16 yo.

I'm saving myself for marriage.

I'm saving myself for Daddy

30

It happened in 1985, and I was 24. I was out barhopping in DC, and ended up at the Frat House. Usually I just stood in the corner watching the people and the videos and left before closing time. But that night I was house-sitting for my boss and knew that I could stay out all night if I wanted to. I was still closeted and living in a group house.

A hunky, shorter muscular blond guy in his late 30s chatted me up. His was a postal worker, and I could tell he had a great body. Kissing became groping, and I invited him over. I did not have lube/rubbers, but did locate some butter in my boss's fridge (very Last Tango in Paris). I got fucked that night, and again in the am. Fortunately, he was not well-endowed.

But I will always remember that night.

18 and I got paid $200 to do it. I didn't care for it much, still don't, but I sure liked having the $200.

Never

Just two weeks after my 13th birthday. He was huge, my age and buddy from school, and I've been a size queen ever since.

19. I picked up a stranger at a bar (I had fake ID) and we went to his car. He wasn't particularly hung, but it still hurt. I just wanted to finally do it, and I bottomed a lot for a few years after that. I'm mostly a top now though...it's been probably 5 years since I bottomed.

16 and I felt like it was a lifetime. I wanted it when I was 13 or 14

None of your business, OP. If you had been curious at that time, you wouldn't be asking me this question today. Suffice to say, "I survived without you."

It was Jim, the HS jock, dream boat, minister's son. All the girls loved him and he loved all the girls. I was 13, he did not want to play, just wanted me on my belly with my pants off. He had a big cock and it hurt. He fucked me every now and again all through high school. No talk, no gay shit, get on your belly, spread your cheeks he always said and yes he greased my asshole.

15

I was 14 and I had to ask my buddy to do it. He wasn't really into it at first but shortly decided it was a ride he liked. He pestered me for the next three years.

17, but didn't bottom often until about 25.

17. He was 19. Did it in the basement of the First Baptist Church in my hometown. PTL!

19.He was forty

15

19, snuck into a local gay bar with a very obviously fake id. Bartender kept serving me heavy pour drinks. That night, after close, on the pool table.

18 in college with a guy on the swim team.

13. He was 15 and a total god. We did it regularly for 5 years. He was always great in bed and he sucked me off after each time even though he was "straight". When I was 19 I ran into him when I was home from college. He'd gained weight but was still cute. And of course I knew he still had a huge 10". He came over that night And we had an actual date, I made dinner, he dressed up a bit. It was funny. We fucked for hours and he slept over. My folks were out of town. The next night I took him to mans country in Chicago. He was quite popular and loved the attention. Never saw him after that.

24--it's a long story that few would understand......

7, actually.

I was 17 & he was 21 & a semi-famous, then & now, TV soap/movie/music celebrity. I was on a vacation with his family on a cruiseship. He got married to a woman 10 years older a few years latter & has 2-3 kids now. i think I was his first & last gay adventure. He currently appears on an ABC TV show.

15 with my boyfriend. I think because it was the first sex I had, I enjoyed it although not so much in a directly sexual way; more about having a man inside me. In the small town I lived in, AIDS was a rumour from the US, so we didn't use condoms and it did feel different. Conversely to what many poster have said, I can get the prostate stimulation, but I hate cumming with a guy inside me- the orgasm doesn't really happen.

R45 said:"In my sister's bathroom in the 10th grade. I was 15 and my friend wanted to fuck me. We were supposed to be watching "Hello, Dolly!" in the den while my dad was grilling out back. We weren't watching "Hello, Dolly!", my friend was plowing me up against the sink."

R45...FYI, watching Hello Dolly in the family den when you're 15 is way gayer than being anally penetrated.

And the reason you can't give his name r109?

[quote]And the reason you can't give his name [R109]?

R109 gave his hole. What more do you want.

My first cousin Terry would try and fuck me from about 9 on whenever we got together. I lived on a farm so was easy to get away for a few minutes among the farm buildings. He would get my pants down and climb on top of me. His penis was hard but very small, we had not hit puberty yet. I didn't feel much and don't think he actually penetrated.

My bf had a country cousin trying to fuck him too. Sheesh, what's with you people?

Why are you all so intent on the distinction between top and bottom ? Are you straight, or something?

Yes, r116, we're all straight.

I bottomed for the first time at 18, when I was playing Clue with a friend. He did it to me in the drawing room with a candlestick.

I'm 41 and I've never bottomed,I've never enjoyed any kind of ass stimulation,I've been rimmed and it was Ok but that's about it.

15 and he was 15. We took turns bottoming. he had the most beautiful cock and silky pubes that felt wonderful smashed against my butt when he was in me. We did it over the next 2 years as often as we could.

Never that, dude

18

15

17.

I bottomed for the high school quarterback. He was incrediably straight. Girls spread for him just by simply walking down the hall. He was the most popular guy in school. The hottest too. You couldn't get any straighter, but me, being as hot and desirable as I am, he had to have me. He lusted after me, of course. It was incrediable. It was in the back of his Chevy. I recall his hair smelling like Vitalis. That was back in 1950.

You claim to be 60 R124 but your math skills need some work. If you were 17 in 1950, you're pushing 80.

I was 23. Gave it up to my ex-long-term partner. He was very patient getting it in. It definitely hurt but didn't last long because I was so tight. The next day it was like I could still feel him inside me. The next time we did it, it was much better. Then I wanted it all the time. I'm not with him anymore but I'll always remember that first time. I was glad I waited to do it with someone who really cared about me.

13, by 2 hairy older bears in public toilets, both fucked me bareback and I have been a slut bottom ever since

I was 15 and I was camping out with a friend from school. He was thirteen and later I found out he had been fucked by his two older brothers since he was about 9 or 10, so I guess he must have learned how pretty well, because I loved every minute of it. He pretty much fucked me all the time after that until I went away to college. So it was the late 70's, and now I'm thinking that being 15 and getting fucked by a 13 yo now, woudl be absolutely apalling. Does that mean I'm getting old ? lol

And yes I still love to bottom, and no haven't even seen him for probably 20-25 years, and he still hadn't lost any of that farm boy sexiness.

I was 16. My best friend was sleeping over. We were in a tent in the backyard, and we started kissing and touching each other. Before I knew it, I was on my knees and his dick was in me. It didn't really hurt ( maybe because we were high--just smoked some weed) but my insides felt weird afterwards. We fucked around for a year or so, switching off pole / hole. After awhile, I began to prefer topping. However, sometimes I just gotta have my ass fucked.

And for clueless tops: 1) put some lube on your finger and massage his crack area; 2) more lube and insert your finger slowly into his butthole; 3) wiggle your finger around in there nice and long to get things all loosey-goosey; 4) insert two well-lubed fingers and repeat #3; 5) grease-up our dick (preferably sheathed in a condom) and enter slowly at first; 6) keep re-lubing as needed, and pump away.

I was 24. This guy came over to me in a bar, asking if I'd like to meet his friend, who thought I was cute. So I met the guy's friend, plus a third guy. When the guy who'd first talked to me asked me if I wanted to go home with his friend, I said, "I'd rather go home with you."

So that's what we did. He had the biggest dick I (still) have ever encountered. He really wanted to fuck me, and I figured I might as well start out with the biggest.

I ended up having a relationship with the guy who originally thought I was cute that lasted a winter and part of spring. We didn't fuck--just very effective sucking. He was a big drinker. I wasn't, not yet, so I left him.

Getting fucked hurt so much, I didn't do it again until a year later, with the first gay guy I actually fell in love with. He introduced me to my first hands-off orgasm.

I stopped bottoming in 1984 or so. Somehow, I had not become HIV+, though I don't know why. I decided to keep it that way.

I was ten when I was plowed two big dicks

18, the night I graduated from high school. I've forgotten how we hooked up but I drove my "new" car (graduation gift) to his house. It hurt like crazy and I didn't enjoy it. But I was too stupid to realize that I could tell him to stop. I still don't like it much, 36 years later.

I was like 23yo.

I was not gay, but love to top shemale whores who were cheap and easy to find. One night I picked one up She was tall and skinny and when she pulled her panties off she had thick 9 incher. it was hard and strong. I was turned off and could not get hard, but was drunk. She kept slapping my drunk ass and I always wanted to try, but was to embarrased to submit to a another guy so I lubed up and took it. it was amazing and she made me cum soft as I could not take the pounding for too long. After that I was trolling XXX and online sites for dick like a whore. It took years to get my fill before getting back to topping. Every now and then I get a craving and bottom for a while. Usually it takes a good ripping or some bad experiences to set me back.

Never. Never really wanted to.

I was 12 he was a friend of my brother a high school senior Jock hung 9 inches, God I loved him.

25

Boyfriend at the time

Wow, you kids were ballsy! I'd never have fooled around with a guy in hs out of fear that the entire school would find out. I waited til college.

11

I was 18. I had been communicating by phone with an older guy (probably late 50s) who ran a Gay Information phone line out of his home. We arranged for me to come to his house in DC. He knew that I wanted to lose my cherry and was more than ready to oblige my urge.

When I entered the home, he started rubbing my crotch through my pants. I asked to use the bathroom, and when I came out I was wearing just a jockstrap. He asked if I wanted to go upstairs to his bedroom and I climed the stairs in front of him and wiggled my bare ass seductively. Upon entering his bedroom we both got completely naked and I laid down on my back on the bed. Knowing I had a virgin hole he went right for it with his tongue. I brought my knees up to my chest as he expertly rimmed me. After a short while, I was ready to suck my first cock. We 69ed for a bit, and then I lubed up and impaled myself slowly on his 7 hard inches cowgirl-style bareback. I rode him for a bit that way, and then I asked if he wanted to do me doggie style.

We started doing it doggie and I moaned loudly at one point and he asked "Are you cumming?" and I said "No it just feels good." When I finally did start to cum hands-free I told him and he pulled out and swallowed my load. It was an awesome introduction and did not hurt at all. I visited a couple of times in the years following that initial encounter. mmmm....memories.

you're a little whore, darlin'

Never. Not my thing, bruh.

10

9, My older brother and my cousin both one after another. I wasn't so happy at first with the pain but something about laying underneath them as they pushed me felt so good. My cousin continued this throughout high school and I cherished every moment of it. I still have a secret love for him and probably always will. After that it has been an empty feeling if I am not with a man. Something about pleasuring a man the way he wants is a feeling I cannot shake. It is as if I was meant to do this and feel this way.

R130: The definitive pushy, controlling power bottom.

'Bottom'? Oh dear. Really, do we need this language/ aping straight sex. Fucking/ getting fucked is just one of a range of sexual activities. I certainly wouldn't define myself by it.

I was 11 he was 25 it really took a few times to handle his 9 inch cock . I grew to crave it

I was 22 and an undergrad. He was 26 and a graduate student. He was amazing. Sensual and rough, but gentle, if that makes sense. We were a bit stoned. He said, "You're so fucking tight " I told him I'd never been fucked, which really turned him on. He held my arms down at one point until I begged to touch my cock. He covered me with cum. Years later, I've still never experienced someone who shot the volume and amout he did. It was on my face, chest, stomach, everywhere.

5 or 6 I think ~

30, but I hated it. i'm better now but mostly top.

17. I had already done stuff with guys (including topping a friend who asked me to stop because he said it hurt), but the first time I bottomed was with another friend. He was so cute and sexy and we had given each other handjobs before. But one afternoon after school, he was really teasing me and we ended up taking a shower together. It's the first time we kissed, the first time we blew each other, and also the first time we did anal. I topped him first, and then he topped me. Best thing I ever felt in my life.

21. It was my very first time at a gay bar and the very first time I had ever done anything with a guy. He was 30, tall and had a hairy chest. We went back to his place, kissed, traded blow jobs, he had a pretty think dick and I dont think I was doing a very good job giving him head. I asked him if he wanted to fuck me and he did, hurt at first but also felt pretty good, he came huge inside of me, he kept his cock stuffed in side of me and jerked me off, I remember leaking cum all over his pubs. My hole was pretty sore the next day, but I was back at the bar the next Saturday and ended up back at his place again getting fucked.

25. It was so fucking painful, I couldn't believe anyone did this for pleasure. I tried it once more another time--and never ever again. It's too painful. I hate it. Don't miss it, and don't want to do it. I have now made it through a lifetime of not fucking and couldn't care less.

I was 17 the first time I attempted, and in my early 20s the second time I attempted. Never tried it again. I just can't handle bottoming. I'm very grateful my ex was perfectly happy to be the bottom in our relationship, and never expressed any interest in fucking me.

I was 16 he was 21

I was 33. I thought I would never bottom in my whole life...until I met this really handsome 40 year old lawyer. And meth.

A little bit at age 12 - me and a friend were playing around, didn't go far, but his dick was in my ass for a minute, so I guess that counts.

Again around 14 - almost similar situation

By 21 or so, I had done it a few times, then realized I'm more of a top.

I was 19 and my best friend/roommate had fooled around before- we had sucked each other numerous times and I had topped him several times and one night we were fooling around and I told him I wanted him to fuck me and he did. He put a lot of effort into it but he was destined to be a bottom.

Early 20’s went back to his place from a bar. Both smashed we fooled around then went to sleep. Next morning he rolled over grabbed my ankles pushed my legs back and entered me. I said no but he didn’t stop. He was handsome, muscular and hot so I let him do it. My first and last time bottoming.

After some unsuccessful attempts earlier, I bottomed for real having just turned 17. I was living in London and could see across a guy across the mews fucking from time to time from my window. I finally caught his eye and he motioned for me to come around to his block. I did and we fucked that night and the next. That started a long career of bottoming which eventually ended. However, I loved it for all those years. Getting fucked was for me nirvana.

The first time I successfully bottomed I was 19 and it was with my boyfriend. He had tried topping me before but he had a big cock, 9 inches and pretty thick and it hurt too much it felt like he was trying to shove a pop can up my ass. This time we were drinking and getting pretty drunk and he started fingering me and before I knew it he had loosened me up and was inside of me. We ended up fucking almost everyday for the next year, and once I got a new boyfriend I was kinda disappointed to learn that not every cock was that big and really missed that feeling of being totally filled up.

Fun to see this thread pop up again and realize i had already commented on it years ago.

19. He was 6'5" and gorgeous. Just peachy.

25. .

36 when I was married, by another married neighbor guy.

18, my first bf. I took to it like a duck to water.

I was 24. It was with my first long-term partner (we were together 13 years). We were together about 6 months and did oral, j/o and frottage. Then he started playing with my ass a lot, so I asked him if he was signaling he wanted to fuck me. He said yes but was afraid to rush it. I decided to try it. I started out by sitting on it. It hurt a lot that first time but I followed through. He came really fast because I was so tight, so it was mercifully short in duration.

The next day, it was like I could still feel him inside and I kept getting woodies over the thought of doing it again. When I got home that night from work, we started messing around and I said I wanted to do it again. We did it twice that night and I came both times. After that, it was all about being a bottom for me. I'm glad, though, I did it with someone I cared about, and he was really gentle and careful. I've heard horror stories from friends about their first time bottoming where guys were merciless and uncaring.

27, also first-time long-term relationship. I was the top mostly, but he was versatile and I wanted to know it felt like having him inside of me, to be closer. I think so many guys are uptight about it hurting that they tighten up. If you want it and prepare for it, it can be amazing.

I was 18 when I first got fucked. In college, way back in the '70's, I shared an apartment with a friend in a small gayborhood in a minor midwestern capital. Four apartments on the first floor of the eight unit building, and all occupied by gay tenants. If you stopped by on a Saturday afternoon, you might find all four front doors open as we moved about from flat to flat, all of us enjoying the freedom of hanging out together with other gay people. It wasn't quite communal, but we certainly had each other's backs. One night, that was especially true for me.

The man directly across the hall was an older guy, twice my age. (36. Ack!) He also performed in, and sometimes won, drag competitions in local bars. From the perspective of an 18 year old, this was very bold and gave him a prominent spot in the gay demimonde of my imagination. One evening, we were hanging out in his apartment watching something on television and the conversation went right to sex. Not too long after it did, I was on my back with my legs in the air, receiving instruction in anal sex from an award winning drag queen. Who was hung. It was like a lecture demo. He took me through it from start to finish, including advice on lube, warming up the hole, relaxing, taking a load,, and washing up afterwards.

An unusual introduction, to be sure. But after reading this thread, it seems a great way to start.

16. He was 35. We met at a local cruisy park and would meet up occasionally for me to blow him. Hot man with a fat 8" dick. After a few hook ups he wanted to fuck me. It hurt like a motherfucker but once I got used to it, I loved it. We fucked around until I was 18 and left for college. I felt so grown up having this "relationship" with an older man. 30 years later I find he's on the sex offenders list for statutory rape of a minor.

The number of guys commenting on here who got fucked by 8 or 9 inch cocks their first time out is very out of proportion to the percentage of 8 or 9 inch cocks in the general population.

I'm probably not going out on a limb by saying it probably felt a lot bigger than it was because it was your first time.

Well, aren't you the boner killer, R171.

Just an editor for NIFTY, R172

I’m hoping this is a bunch of made up garbage. 11 with a 25 year old? I hope he’s either in prison or dead.

33

22 but was unprepared and it turned into a complete shit-geyser.

30.

18. Exactly six weeks into my freshman year at college. He was my art history instructor. Late 30's, tall, blond, muscular Danish guy with a large, uncut dick. I had never seen an uncut cock before. It felt amazing. He was terrific in bed and taught me a lot. I thought we would spend the rest of our lives together. We fucked constantly - at his house, in the car between classes (a Fiat convertible!), in the men's room of the school library.

Alas, a month later I was replaced with another wide-eyed novice. I wonder how many of us he had? I've no regrets - it was a great introduction to the art of sex. The same year I met someone who could fuck me and make me cum hands-free.

A perianal fistula in my 20's put an end to my bottoming. I haven't bottomed in years. But I remember what I learned as a bottom and try to be a great top.

15, he was my 7th grade history teacher - I was a horny teenager and wanted him, but as I look back it was predatory on his part.

He was arrested for molesting another student the next year while class was going on.

21 with a guy who picked me up at a gay bar, he popped my cherry. I dont remember it hurting, I guess because I really wanted to get fucked.

29. It hurt like hell the first time. He kept asking if he should stop. The feeling was intriguing enough for me to say, "Don't stop!"

It was two tops later that I found someone who topped me so wonderfully and passionately that I finally understood what the hullaballoo was all about.

I'm 46 and have never bottomed, I've just never enjoyed having my ass played with.

R12 is the only person on this thread that I'd date.

I was 93 last week and I did it when I was 87.

I was a sophomore in high school and had just turned 15. Michael was captain of the school's football team and a senior. He was cast in a lead in the school's musical production and asked for my help with the two songs he had to sing (I played piano). I was accompanying him at his house and he was standing behind me reading the lyrics and he pressed against me. It was obvious that he was turned on. We were in bed within 2 minutes and he was inside me within another minute. For the duration of the production (about 6 weeks), our code word was "Wanna rehearse?" He was President of his class, dating a knockout cheerleader and had a gorgeous body and huge cock. We never talked about it, and only nodded if we saw one another at school. He graduated a few weeks after the production and went off to college, got married and has been happy ever since from what I hear. It was, however, the best fuck I have ever experienced and may have only been so because of the secrecy of what we were doing or because our Catholic School would have disapproved but...make that butt!!

I was 24, he was 21 and in college.

I think the more interesting question is "what age did you bottom for the last time?" I'm hoping i can continue doing so during all my eldergay years, but i'm curious of other guys give it up, either because of their own issues or that their partners can't keep it up long enough anymore.

12, the other guy was 14

^ my guy stills it up. Thick and hard.

stills = still gets

19. With my therapist.

Around 25. I’ve only had sex with one guy.

Recently I've been chatting online with a guy who claims to be an anal virgin. He hasn't had any luck getting anybody to change that. Here are the reasons why:

1. No real foreplay. He doesn't want to do oral to me or to him.

2. No kissing or touching.

3. Just stick it in. With a condom of course.

4. No pot, no alcohol, no poppers, no other drugs.

5. Stop at any time if he says to.

6. He's Asian.

I've declined as the others have, but he keeps talking to me trying to get me to do it. He has a great body and a decent face. I don't mind the Asian part. I do mind the no-kissing, no-touching, no-sucking part. I tried to explain to him about topping from the bottom but he didn't get it.

R34 I’m not a troll. He’s not the guy you’re trying to make him out to be.

I think you’d be all over him if he looked at you twice but you’re too busy virtues signaling. Go to Jezebel and be with your own kind.

11! I win!

18 with a guy a year older but he didn’t believe me when I told him I’d never done it before because I enjoyed it so much.

r196 slut!

17. Senior year high school. Went to gay bar downtown picked up a blond 26 year old. Went to his place, talked to his elderly landlady - intimidating to a not out teenager- and went to his top floor apartment in an old mansion. Hurt like hell and told him to get off. Couldn’t even do anything after that- I was so traumatized. He took me for ice cream - but couldn’t get out of there fast enough. Bled for weeks. And it was the height of AIDS- so I assumed I was positive for 4 years until I got tested. 8 years later tried again with my older bi boyfriend. Liked it. Find I like it more as I get older. (As the population of potential tops gets smaller😕

R171, those are DL inches, so subtract a couple, for the actual size.

10, Father O',after mass and many sips of altar wine,,,,

My first attempt at bottoming was at 25. I had fooled around with other guys in college, including topping them but never bottomed. There was a fear there - not so much about the act but more about what it would say about me, what it meant - you guys know what I mean. I also chalked up all of that play to “experimenting” - I know, the things we tell ourselves!

Anyway, there I was at 25 in one of those old AOL chat rooms, started having direct convo with one guy who turned out to be a guy from another college I knew - our clubs used to play rugby - and yes we had fooled around after matches. I’m excited as he was pretty hot - hairy, thick muscled redhead. We make plans to meet up at a gay bar down in the Village, and we’re all over each other from the get go.

All very familiar territory until he starts paying attention to my ass - he’d never done that before but I liked it. All this play continues as we have some drinks and talk. I remember thinking “holy shit! I think he wants to fuck me!” and while excited at the thought, was nervous both as a virgin and because his dick was/is super fat. Later on we’re making out and his hand slips down my shorts and undies and his finger starts stroking/rubbing my hole - at that point I just broke the kiss and asked if he wanted to come back to mine.

We went, get naked and we’re on my bed reacquainting ourselves with our naked bits for awhile. When it came time for the main event, he asks about lube, condoms. Having not had any gay sex since the “experimenting” in college, I had no lube! I remember him giving me this sexy smile and saying “don’t worry, I’ll get you ready” and he proceeds to rim the motherfucking life out of me! I am literally begging for his dick now and he obliged.

Yes it hurt going in, but I was so keyed up I didn’t care. Eventually the pleasure started to overcome the pain. We fucked a few times that night, I can still picture him on top of me - our hairy chests all sweaty and tangled, his thick bush against me, making out and moaning into each other’s mouths. It was a wonderful night and it was thanks to him I got over my fear of bottoming. He and I continued to play on occasion and actually wound up playing with different rugby clubs which always included some after match play - usually in his truck before the drink up.

Most guys still wanted me to top (I’m 6’3” good looking hairy blonde jock with a fat piece) but thanks to my buddy, I could now add “bottoming” to my repertoire. But the more I did it, the more I wanted it!

It was about 6 years later, I had been playing with a new buddy - tall really muscular smooth Latin who was into hairy white guys and was all top. He did not have a huge dick as one might think a Latin would but what he had, oh my did he know how to use it! It was thanks to him I experienced my first hands free cum and my first cum when soft. My interest in topping waned with him and I enjoyed being a bottom. I still would top, but always made it clear I much preferred it on the bottom.

Now at 47, I’ve experienced a good variety of men as hook ups, friends with benefits, and boyfriends. I can tell you bigger is not always better - it’s all about the skill of the captain vs the size of the boat. I’m happy being a bottom and now a daddy and am thankful to be able to report there are plenty of guys out there who want a daddy bottom. And no, these are not paid companions.

So, first time bottoming at 25, last time bottoming at 47 - last weekend with a younger friend with benefits who loves daddies who bottom. Who am I to deny him?

18, at the insistence (or rather, persistence) of my first boyfriend, who was 22... he fucked me seven times (yes, I kept track, LOL) over the course of our ultimately ill-fated relationship, and I hated every second of it, but was willing each time to forgo a little discomfort in order to please and pleasure the man I loved. Years later, at age 27, my then-boyfriend (who was at the time pretty much a dedicated bottom) ended up topping me one night, and much to my surprise I found it quite pleasurable... my next boyfriend (early 30s) turned out to be pretty much a total top, and by that point I'd truly discovered the joys of bottoming, and we happily submitted to each other's desires. Now 51, totally vers, and totally into whatever happens (top/bottom/whatever) with whichever boyfriend who next comes my way... :)

Mmmm, R201, LOVE hairy bottom dads... wanna flip?! :)

18, drove up to P-Town in the winter for a weekend alone and met a beautiful artist who was 24. He was very sweet and gentle and it was amazing. I can still smell the paints and brush cleaner to this day.

R202 - I’ve done that, and also bottomed out side by side with a buddy for a pair of tops if you’re game! ;-)

Hehe, sign me up!

I had my anus removed before I had the chance to give it a go.

16. There used to be a downtown hotel that had a bathroom in the basement where gays use to meet for sex. I use to go there and suck duck all the time. There was a guy in his early 30s that I would meet and give him a blowjob. There was like a little room in the parking garage that people would go to for whatever they wanted to do. He asked me if I wanted to go in there so I said yes. We went in there, and he asked if he could fuck me. This was the middle 70s so we didn't know anything about AIDS then so I said yes. So we proceeded to do it. He was pretty big but he managed to get it In without it hurting much. It didn't take him long to cum cause he said I was so tight.after we were through he proceeds to tell me he was gonna move to California the next week. I think of him and wonder whatever happened to him. My first crush, he was so handsome.

Oh, no. Don't suck duck, R209. That's not nice.