Your most shameful sex

0/10 EST. Go eat some chocolates it's Easter hun.

Well I never...

OP is a WHORE!!!

OP expects us to workshop her Nifty tales.

OP is Renée Zellweger practicing for Bridget Jones III. I can hear her heavy fake-Texas drawl coming through her fake-British writing.

A homeless guy from the street. 6’7” ex basketball player - likely on drugs - with a solid 10+” dick. Largest I ever saw. Multiple times. I was a size queen. And a whore.

A trainer/manager at my old gym. Wasn't really attracted to him but saw his dick on the showers and I had to have it. Beautiful fat cock and heavy nuts. He'd pop in the showers every time I went to the gym so had to cancel my membership.

[quote]He'd pop in the showers

Now we know why the youngsters don't shower at the gym!

Also a hot homeless guy. I enticed him with drugs and a nice shower. His jealous street boyfriend - whom we didn’t know existed until then - followed us with threats all the way to my home. I had security and doorman so that stopped the boyfriend.

The sex was great (after I cleaned him up). He left happy and with new clothes/underwear. I stayed, thinking to myself “you’ve hit a new low, good deed and all...”

What happened after, OP?

OP, your boss took his clothes off twice? First he took off his shirt and pants. Then, a few minutes later, he ripped off all his clothes? How many pairs of pants had he been wearing?

Ex boyfriend I knew was seeing someone else. I realized that I’m really good in bed when I’m angry and vengeful. I also realized that feeling like a whore and home wrecker is not fun.

I'm sure I've told this story on here before. When I was living in LA, I hooked up with this hot Latino guy and we went back to his place because I was high and stupid. In the living room was a woman and a toddler watching TV. I'm not sure who she was, maybe his girlfriend/wife/sister.

We went into a room with just a mattress on the floor and he fucked me. He said he didn't have any condoms but he said he was clean, so I let him bareback me. The toddler walked in the room while he was fucking me and just kind toddled around the bed where I was getting railed. Then the woman came in to get the toddler and the guy never stopped plowing my ass.

She scooped up the kid and they started arguing in Spanish, which I do not speak, but it sounded like the kind of fight a couple would have. He pulled out of me and they argued in Spanish some more and then he pushed her out of the room. Then he came back, like nothing was wrong, and started plowing me again. I told him not to cum in my ass because we were barebacking, but he slapped my ass and did it anyway.

Afterwards I got up, got my clothes and was expecting for him to take me back to Silverlake. But he went into the living room, still naked and cock dripping, and sat on the couch next to the woman and picked up the toddler and started bouncing the toddler. I came out of the room and the woman was just glaring at me and then they started fighting again and he said that he couldn't take me back home and I couldn't wait in the house.

I had to call someone to come get me. So I waited outside, ass full of cum, in a neighborhood that I was unfamiliar with, for what seemed like an eternity for my ride. This was before Uber.

Wow, r13. You homewrecker!

The next morning, anytime I did poppers. I stopped doing them after the fourth or fifth time. The walk of shame was just too shameful.

I wasn't doing great work in an elective I took during undergrad. I didn't like the class and did not care about the subject.

The professor was gay, and none too attractive. But I let him fuck me a couple of times and my final grade was much improved.

The only part I really feel shameful about is that after the class was over... so was he. Ah, well.

A few years ago, my partner and I broke up, after I found out he'd been cheating. So, I went wild and super slutty. I had a month of PTO to blow, so I traveled all over and hooked up with lots and lots of guys. It was fun, but very stupid. I feel no shame about the sluttiness part, but a few of those hookups were pretty shameful.

Well? Tell us about the shameful hookups, you cocktease!

R13, with time (if not already) that story will be one of the funniest you’ll have in your archive of anecdotes.

Back in the 11th grade I had a P.E. teacher named Miss Seboka, she looked just like Anne Murray which was a HUGE turn on for me as I had posters of Anne all over my bedroom wall. Miss Seboka was the coach of the Volleyball team and I was her star player. One night after an away game, my dad didn't show to pick me up. I called my mom who told me that he was working late and if there was anyway one of my teammates could give me a ride. Well, all of my teammates were gone and the only person left was Ms. Seboka. I asked if she could give me a ride and she responded with an emphatic yes. We get into her car and the whole front seat was covered with Janis Ian, Indigo Girls, and Michelle Shocked tapes. I knew then that this lady was definitely into some hot gal on gal action.

I asked her if we could stop off at the Wendy's because I was totally famished. I got a frosty from the drive thru and then she asked what time I was expected home. I told her it didn't matter (It did and my parents would be furious, but who cares when I was going to get a taste of her pink taco!) so she asked if I wanted to come over and watch a movie.

We got back to her place and ate some trail mix and watched "Personal Best" which I had never seen. Boy did it get my juices flowing. Next thing I know my purple nylon workout pants were around my ankles and Ms. Seboka was going to town on my pork chop sandwich like an Ethiopian at an all you can eat jumbo fried shrimp buffet at Shoney's. I was loving every minute of it, although I could have done without her sticking her index finger up my butthole, but what are ya gonna do?

Then it was my turn, I slid her black fitted stirrup pants down around her white tube socks and black half boots. The minute I stuck my face down there I knew something was very, very wrong. She smelled like wet hay mixed with diarrhea. I gagged repeatedly, but still tried to keep going, the final straw was when a substance with the consistency of Campbell's Cream of Potato soup and the color of metal started pouring out from inside of her. I wound up vomiting all over her lap and ran out of the house.

I walked home that night and it was about seven miles. I got a lot of shit from my parents as well. Things were never the same with Ms. Seboka again and I dropped off the volleyball team two weeks later because I was so uncomfortable.

Moral of the story: Sometimes your fantasies are not all they're cracked up to be.

I went through a phase where I was madly in love with this fuck buddy of mine, but I knew he was seeing all sorts of other guys so I realized that two could play at this game and I started hooking up with a lot of the same guys he was hooking up with and finding creative ways to mention this guy's name to see if he was more serious with them than he was with me. I even hooked up with this one guy who was obviously a bottom, but the time came to fuck and he wanted to fuck me. He pulled off his pants and he had the tiniest cock I've ever seen in my life. I don't even think it was as big as a thumb and I felt bad so I let him fuck me. I couldn't feel a fucking thing, but moaned with pleasure, hoping he'd feel like a king.

I also had a thing with a much older guy who'd always turn out all the lights in his house and fill it with candles every time I'd come over. I think he was ashamed of his face and/or body. I'd feel so sleazy after I'd pumped my load into him, but he knew how to suck a dick.

R20 yeah sure bro.

Shameful? More shameful than sex was actually DATING a handful of losers.

I’ve never had sex I am ashamed of. The people I had the sex with were the problem.

That said, they were 8s to 10s, even by DL’s standards, so there is that. However, that, on its won, doesn’t make up for having relationships and sex with several dudes who were total losers. And by losers, I don’t mean that they were broke, I mean that they were morally and/or ethically corrupt or compromised.

Also, I know someone who married a homeless guy, and he turned out to be a person who was down on his luck when they met, yet a decent person. Gorgeous too. She lucked out. As far as I know, they’re still married!

Too numerous to list for me. Yes, I'm a whore.

OP, you don’t rim someone at 1am after a day at a conference and then dinner and drinks all evening. Ok, so maybe he showered before going out for dinner. But even so, that was probably a funky hole by 1am and you’re a nasty ho for eating it.

R25 Who the fuck are you? Julie Andrews? You don't decline a bit of boss rimming just because it's 1am!

Where's the 'dats da suck job!' guy?

at Parliament House in Orlando. I wasn’t particularly ashamed (it’s P-House, that’s why you go), but my roommates took care of the shaming for me.

This never happened. But I bet it would make it into Penthouse Letters.

There should be more bad sex, more recriminations, more tears, it it is indeed truly shameful sex.

I once hooked up with a gorgeous short guy who had the biggest dick I had ever seen. I was enjoying blowing him even if I was gagging a lot, and then I threw up all over his lap. He was horrified. I was horrified. I left. But within a few minutes I was laughing maniacally in my car because, I mean, it’s kinda funny, too.

I went to a foam party once in college at a club called Nation in DC. I had a lot of fun playing in the suds, etc. I was dancing and some guy came up behind me and was dancing with me and then he jerked me off and I blew a load right there in the middle of everything. And suddenly I realized I was in the growth medium of a petri dish and I got the hell out of there. I won’t say I am ashamed but I do feel dirty to this day. Blech.

I guess I kind of felt ashamed (actually just very depressed) when I blew someone who I had had a big crush on for years and after a while he told me “no little boy like you could ever make me cum.” It was just weird and shocking and insulting and he said it suddenly in a very matter of fact way, not in a vicious way, and he put his dick away and that was that. (I made him cum many times in later years and he texted me several times over the past few years and said he always loved me, so there’s no lingering shame/insult. But he’s mentally ill.)

Fuck off R22, R20 is a DL legend.

Wow, R20. I guess that's a lesson we all have to learn once.

@r20, que rico!

I fucked a married guy once who picked me up in his car and there was a baby seat in the back seat and I thought to myself I'm a gross pig and I will never fuck a married guy Ever again.

R35 Oh I've done the married men thing loads. And seen the baby seat in the back of the car. The worst one was the session with the guy who kept stopping and calling his girlfriend as she thought she might be in the very early stages of labour!!

Some of you people are such ... whores.

A girls gotta make a livin!

I found out later that the married guy with the car seat was also a right-wing nutjob so that only added to my shame and strengthened my vow.

R39 But was he hot though?

[quote]A homeless guy from the street. 6’7” ex basketball player - likely on drugs - with a solid 10+” dick. Largest I ever saw. Multiple times. I was a size queen. And a whore.

Oh.... I think I know who this NBA player is! Delonte West?

No, he was fat and rude and even though he was apparently a total bottom with men he didn't know how to clean out properly, thank God I always wear a condom for anal.

A guy that I met through the personal ads in the late nineties. Barely attractive, but I was lonely, needy and going through some personal issues. I saw him several times before he ended it. I think that he caught on that I wasn’t really into him. He did us both a favor.

R43? And that is your most shameful sex? That is most of my sexual encounters!

The train my meth dealer and his thug buddy's ran on me last summer. We called it Tuesday.

I once went home with a guy who turned out to be a virgin. He said nothing until after I’d done everything possible to prove what a whore I was. I still blush scarlet at the thought of ruining his innocence. It should have been nicer.

No comment.

R46 please elaborate

R44, the only one I am admitting to...

So many. The worst would have had to have been when I went home with this guy and when I went to get condoms he passed out and I couldn’t get back in. I was so horny I picked up a guy from the street and he sucked me off in the entrance and we got caught by the neighbor. I went out and caught up with a friend and stayed at her house. I went back in the morning as my wallet was still there and fucked him. He then texted me on the following Monday and said not cool. I knew what he was referring too and made up it was someone I had picked up from the club and not from the street! Haha. I don’t feel too bad as the arsehole passed out and had left me out the street but felt ashamed about being caught by the neighbor.

I hired a local moving company when I bought a new house across town. They sent two workers, one of whom made instant eye contact with me. As they schlepped things around, he and I kept eyeing each other, without saying anything. When we got to the new house, the other worker was busy reassembling the bed and I joined the hottie in the truck to help him with a large box. I was standing maybe a foot behind him and he suddenly backed up. I simultaneously held out my hand to keep him from running into me, and inadvertently grabbed his ass. We both froze. As I started to squeeze his buttock, he turned and kissed me. The whole thing was completely spontaneous. "Come back when you get off work," I told him. "You know where I live." And he did. He proved to be a fantastic fuck.

The "shameful" part was standing inside a moving truck in the middle of a quiet residential street in the middle of the day, kissing a mover while grabbing his ass. I really don't usually act like that.

R48, I can’t without reminding myself of who I was at that time. I don’t recognise myself.

Oh Jesus, r52. If you can't be bothered to give details, stay the fuck out of these threads.

R46, you gave him a crash course, it might not of been as nice as one dreams of in the movies, but I'm sure checked a lot of his boxes

might not have been...

Ahhh a gay.com chatroom hookup. He was "Blond with 8 inches." True, he forgot to tell me he had cerebral palsy, Even worse than Cousin Jerri. Let him suck my dick, he wanted me yo fuck him. Nope. Later, I was with coworkers at the grocery store, and they made comments about the retard corralling the carts. I looked up, it was him. What could I do, say I messed around with him? Hung my head in shame for that pity suck.

Ahhh a gay.com chatroom hookup. He was "Blond with 8 inches." True, he forgot to tell me he had cerebral palsy, Even worse than Cousin Jerri. Let him suck my dick, he wanted me yo fuck him. Nope. Later, I was with coworkers at the grocery store, and they made comments about the retard corralling the carts. I looked up, it was him. What could I do, say I messed around with him? Hung my head in shame for that pity suck.

your coworkers sound like real gems, r56/r57

My CP opportunity chickened out on me. He had family issues.

R51, you is a ho.

R56 You sound like a nice piece of work. Why should someone who has cerebral palsy be regarded as a shame fuck? Even worse, what kind of vile people would then laugh at someone with the condition who works in a supermarket?

[quote][R51], you is a ho.

Oh, to be sure, but not usually that shamefully.

R61..Amen.. r56/57, your coworkers are fucking pricks.

[quote] I once went home with a guy who turned out to be a virgin. He said nothing until after I’d done everything possible to prove what a whore I was. I still blush scarlet at the thought of ruining his innocence. It should have been nicer.

Baptism of fire! Was he responding to your whoredom or just lying back enjoying the carryings on or what? This is hilarious. BTW, I don't think you traumatized a gay, but you may have made a hetero, probably now with kids.

When I hooked up with this guy, got drunk (not like me) at a bar with him, took him home, slobbered all over his mouth, tried to suck him, nearly passed out, he had to put me to bed; he sat on the side of my bed asking me if I was gonna be ok before quietly letting himself out of my apartment. There is a lot to be ashamed of in that episode; not least the attempted suck off without consent; he did not tell the cops. He was a nice guy, a bit older than me (I was then in my 20s) and he deserved better.

R56 here. True they were pricks but...the guy purposely did not tell me...I get there, he's in a wheelchair...

Sad tale, R66. How do the disabled get sex?

R20 I loved that story.

My body does not tolerate alcohol very well. I can only drink very, very lightly, or it makes me sick.

I was at a big party years ago, at a retreat center where a weekend long event was held. I went to the party dressed in a gingham square dance dress. I had a glass of red wine. That's all.

Things began clicking with a really hot man attending the weekend. He took me back to his room and we did it. Totally unexpected. At one point, while I was still in my square dance dress, he bent me forward over the bed and he stood behind me and fucked my ass. The wine, the fucking, and the being bent forward with my head low on the mattress was a bad combination. All of a sudden, I barfed all over the guy's bed. It was unfortunate.

Thank God, I didn't get any red wine on my square dance dress!

R69, are you male or female?

R6 A DL male obviously. Gingham dance dress. Get it? Possibly a broad white belt too.

Sorry meant r70 not r6.

R66 He was in a wheelchair? In the original story you said:-

"I was with coworkers at the grocery store, and they made comments about the retard corralling the carts. I looked up, it was him"

How does this lay of yours manage to corral the carts whilst in a wheelchair?

R70, I'm a male. The gingham was lavender. My wig was a bouffant.

Wow, so turns out you're all bottoms. Who knew?

The one that springs to mind for me, was a guy who had hit me up many times online for a few months and was really keen to meet but really wasn't my type (he was younger than my usual, mid 20s (which was older than me at the time still) and a dancer with a dancer's body - lean rather than built. I'd always been nice to him but rejected any of his attempts to meet.

However one night I was feeling really horny and alone and he hit me up and I thought, fuck it, I'll go and fuck him. So I went to the station near his place to meet him and didn't really find him attractive in person (he was good looking, just not my type as I said) but I thought, well I'm here now so I went back to his place and we chatted for a while, eventually he kissed me and it was not good - like, lizard-kissing (stabbing his tongue in and out of my mouth repeatedly) so I thought the only other option to get him to stop kissing me was to get him to suck my dick instead, which he did - and was surprisingly very good at it!! He also had a fantastic firm round smooth arse which I rimmed for a while, and a big thick cock that I sucked for a while. He then rimmed me for a bit and that lizard-tongue technique that was so unappealing for kissing felt much better going in and out of my hole. I rimmed him a bit more and then he said he wanted to be fucked so I went to put one of his condoms on and I don't know what happened with it but I literally couldn't get it on my dick so I tried another one and the same thing happened, really awkward but luckily I was a boy who came prepared and I had brought my own so I got one of mine on and fucked him for about an hour in multiple positions. Because I wasn't super attracted to him I could keep going for a while and because he was a dancer he was very flexible. It was actually very fun sex, just not mind-blowingly hot. After we had both came we fell asleep and I woke up the next day in the early afternoon. In the cold light of day I wasn't up for a round two so I made a hasty retreat.

The shameful thing is he continued to hit me up many more times after that for repeat visits, saying it was the best sex of his life etc and after the first couple of non-committal replies from me I just ghosted him. So although the actual sex itself wasn't that shameful, it was a lesson for me in future to only fuck guys that I was really into and to not just treat them like a takeaway to pass the time when I'm bored and horny, because to them it could be something more and that's unfair.

Yeah, you really turned that bragfest around with your saintly empathy, UKGuy.

To your credit, you did tip us off when you started off by talking down to the bottoms.

Did you make your point? I hope so. Seemed kinda desperate. But if it makes you feel better......

I have more stories, but if I post them, it would be triggering.

Paying trade in 3rd world cities their going rates when I could easily pay 5x - 10x more.

R78 = badman robin

R79 he probably buys their shitty drugs and that's it.

Don't ask.

Back in my drinking days I went home with a fug. I remember talking to him in the club and thinking, this guy is not so pretty (I am no beauty myself, but he certainly wasn't). Next thing I know, I'm waking up next to him, it's a Thursday morning at 11am, and I am supposed to be in work. I cringe now!!

^^^Most of my sexual mistakes were done under the influence of alcohol. Now that I am sober, I cringe at some of my hookups.

Back of Chinese restaurant

The hottest most shameful sex involved a gym steamroom filled with close to 16 guys jerking and sucking one another. The least sexy one was when I met a guy at his apartment and when I went to blow him his dick reeked of smegma. I prefer uncut, but clean uncut. I was feeling so unattractive and desperate that I still gave him a fast blowjob while trying to minimize breathing through my nose. Ugh

I was really broke one time and thought I would offer my services as an escort on Gaydar. I found a punter and said I would fuck him for $100. I went to his home (he owned a bar, he had a flat upstairs). I was about 27 at the time and he was probably about 50. But I really didn't find him attractive at all. I managed to blow him but just couldn't bring myself to fuck him. I then owned up and said I was sorry, I couldn't do it. I told him to keep the money, but he was sweet and said let's go halves so he gave me $50. I then chatted to him for an hour. The strange thing was, he would then text me offering me another $50 just to go there after he shut and talk to him. But I refused to do it.

The whole incident gave me a huge amount of respect for escorts who can fuck on demand and fuck anyone. When I was really skint and put in that position, I just couldn't do it.

I have had my share of sex in video booths at X-rated bookstores. It was sleazy of me, but I'm not ashamed. I liked it. Great sex, act like a slut. Shoot my jizz all over with a stranger. Well, those days are over. I don't think there are video booths any longer, at least not where I live. Plus, it's too scary these days.

I went to the mensroom in a local gay bar, stood at a urinal next to another guy, checked out his cock. It was by far the ugliest cock I had ever seen, I took him home to get a closer look, turned out to be great sex but damn that cock was ugly. Nice size but really mutalated during his circumscison

I used to be morbidly obese. Came out in college. Lost the weight. Had to play catch up because I had no frame of reference for dating, hooking up etc. My school was in a small town. Nearest gay bar was 40 miles away. Being new to the scene and fairly cute (who isn’t at 19?) I got more than my share of attention. Friends wanted to leave. I wanted to get laid. Guy offered to drive me home. I was a horny, sure! That’s a great idea. On the drive home I realized he was an idiot. Still felt like I had to go through with it to justify his driving 80 miles out of the way. Sex, horrible. Uninspiring. He had a great body, but no idea what to do with it. I let him stay because it was late, long drive, blah, blah, blah. Wake up. Sunday morning. His damn car won’t start. He calls a friend who offers to pick him up later that day after church & a baptism. I have to spend the day with him. Horrible conversation. Started thinking the sex couldn’t have been that bad. Surely it had to be better than the conversation. Did it again and it was worse. He worked at a paper bag factory. I always ask for plastic now.

Cigar. Oval Office.

17. Local cruising spot in the country. An older guy wanted to hook up with me, I was hornet - like every 17 year old - but he was ugly and unappealing. I decided if I’m going to do it, I should at least make some money. Asked for like $20. He was taken aback but gave it to me for a BJ. It was my only foray into prostitution - but I realized I’m not cut out for it. Didn’t enjoy it and felt kinda skeevy.

I later learned that every job in corporate America is basically prostitution. Doing something you don’t like for money.

[quote]I was hornet

Hope losing that $20 on a mediocre bj didn't sting too hard.

^^ Since this occurred "in the country," it's a safe bet he was a WASP. ^^

Shameful, all of you!

I spent my 16th summer being the fucktoy of four country boys. My father sent me to work at a farm for the summer "to make a man of me" and that's what happened. No more summer sissy, he thought. Ha.

What was shameful was at the start the guy at the farm where I was staying kept trying to get me to "do things" with him because he was soooooo horny. I was an innocent. He said he'd give me a twenty dollar bill as a sign of friendship. For some reason this made sense, even though I was being whored. So then the summer started in earnest.

At the end of the summer as I was packing the farmer - the guy's father - came in and said he knew I had stolen money from his son. Choking, I said I hadn't and all the money I had was mine. He said his son drew a mustache on every bill and to show me my wallet. He pulled the twenty out and sure enough there was a mustache on Jackson. I hadn't looked at it before. So not only was I a whore and fucked by kids who laughed at me, I was called a thief and delivered back to me parents in silence. It was horrible.

When I was still in high school I had a crush on a security guard who was working at the local strip mall. He was in his early twenties and just working the job for some extra cash, as he was Mormon and going to leave the States do some mission work in the Fall. Anyhoo, I was following him around while he was working his late night route and being kind of flirty with him, trying to get a better read on the guy. I’m not exactly sure how this happened, but I went for it and he and I started kissing and full on making out. I immediately dropped to my knees and sucked his cock. It was so strange, he seemed to have no idea what I was doing to him. He actually asked me if I was blowing on his dick. I mean...are Mormons that clueless?? So, I continued to suck him off until he blew his load in my mouth (and on my shirt). Afterwards he ran away and decided to pray. He was all cryptic and weird about it. He even cried. Then his boss was driving around the parking lot looking for him so I had to duck out. I felt embarrassed after the fact because it made me feel like a thirsty whore. He was cute, but he was also a huge dork. My girlfriend still gives me shit about this hookup twenty years later.

R96 are you bi?

R97 I’ve experimented with women in the past, but I don’t consider myself at all to be, “bi”. When I was referring to my girlfriend, I meant my female bestie from high school. We used to hang out at the strip mall and look for cute boys. I grew up in a rural town where there was no real gay scene. She knows all my dirty little secrets. Haha

After that delicious cock you went to pussy? No man, just no!

R99 I have only ever been with three women. Every single time there was a cock involved. They were threesome or group situations. I could never do a one on one with a woman. Nope.

Oh r100 thank God!

R20: gee willikers, that’s quite a testament! Maybe you should consider writing fiction...

You didn't go back for more, R96?

R103 I tried, but things were weird. He was Mormon. So, he was fucked up already from religious brainwashing. He didn’t really want much to do with me after that. I think he was weirded out and not sure how to feel about what happened. I didn’t force him into anything. He was completely compliant and his raging boner was proof that he was just as into it as I was. I just figured he was afraid of his sexuality, whatever is may have been.

I had to laugh r98 😂

... sorry I meant r95

I went to the Mineshaft in the summer of 1981. It was the most depraved debauchery ever. I loved it. Jizz everywhere all night...two nights in row. My summer of '81 minus the beach and Jennifer O'Neill.

I moved to San Francisco in the early 70s which is where I came out. One day as I was walking on (Upper) Castro Street which is up the hill south of the heart of the Castro District. In those days I was a total whore and would have sex with anyone. I was looking at the beautiful Victorians as i was was walking up the hill, and I noticed a naked man in his window on the 3rd floor of a building. I stopped and watched as he was rubbing his crotch, and realized he was showing me with his fingers, his apartment number. I went up to his apartment and he had his son there in the apartment, crawling around on the floor. The guy was quite a bit older than me (I was like 19, he was like 35-45). Next think I knew he pulled off his toupee and had me fuck him on the floor while his kid was crawling around on the floor.

There was a cruising park near my house (mid 90s, just before the internet ruined park life!) that my teenage self was at every chance I got. Hot married guys were my thing back then. So it was a slice of heaven for me. Usually the sex entailed jacking off in a car off the beaten path. But this one guy wanted me to go home with him. I drove to his house. We enter. Start going at it. He's sucking my dick and doing a great job. We were in his living room. I look up and I see a family photo of a girl I went to high school with. Even worse, we were both in AP classes and our last names started with the same letter. I literally sat next to her from 7th grade until senior year and now who dad was sucking me off.

So I came in his mouth and hightailed it out of there.

I don’t know what’s wrong with you I love being a home wrecker and fucking people who are taboo. It somehow makes it hotter.

Maybe leaving work for a two hour lunch break so I could Suck off a married client. I did that a few times.

In the late 90s I was in a program with a real estate company where they taught "classes" and at the end if you passed/were interested they would sponsor you to get your selling license.

Anyway, I knew about halfway through it wasn't for me but I was so into the hairy daddy that was my mentor that I stayed in for a while. I was so obviously into him that I ended up blowing him in a client's house.

We did it three or four times and the last time was the real walk of shame. I pre-lubed and told him I wanted him to fuck me, and he did. There's a new build house in Wisconsin that was christened with some ass babies and a lot of Astroglide.

[quote] turns out you're all bottoms

welcome to Datalounge!

Back in the day, the Kaiser Center on Lake Merritt in Oakland, California, had the cruisiest tea rooms. The building got a major overhaul in the early 90s and a number of floors were unoccupied as renovations were being done. The elevators still opened on those floors. There was just nobody there but us cocksuckers. It was busy every day. I even had a memorable three-way in one of those (otherwise) deserted men's rooms.

I’ve had a lot of shameful sex. I fucked this leather guy from Utah in his dorm room. He was about 40 and in grad school. After a long fuck session, we talk. He’s from Utah. I ask if he’s Mormon, said he was. I immediately asked if he was on the dl and he admitted he was and he had a wife and five kids. Even though I really found it despicable, I fucked him all weekend. He was really handsome, he looked like Harrison Ford.

I had a fuck buddy I met online that wasn’t my usual type. He reminded me of Shaggy from Scooby Doo. I had just moved to LA. He didn’t really seem gay at all but he bottomed like a pro except he wasn’t very good about cleaning himself. There was always residue and it was like a crime scene on the sheets after we were done. I had an embarrassing conversation with him about it and he seemed sort of cavalier so I wrote him off for a few weeks. One night, I was drinking and went online - he was online too so we agreed to hook up. When he came over, I noticed he had a butt plug inserted. He said I was a bit too girthy for him and wanted to stretched out his hole before hand so he could take it easier. We have our usual foreplay. I remove the butt plug and there was a shit storm like you wouldn’t believe. All over me, him and the bed. When I moved out, I found a spray of it dried up behind the dresser. I was pissed!! I forcibly threw him in the shower and I berated him as I cleaned us off. He was apologetic and maybe a bit scared, I can be vicious when I drink. I don’t remember who initiated it but I fucked him raw in the shower and again on the floor of the bathroom. He left with his head hanging low and I felt extremely guilty. We hooked up one more time after that (yeah, he was gross but a really good bottom who didn’t just lay there) and, sure enough, I pull out to switch positions and there was a mess. No words were spoken, he put his clothes on and left. You’d think that someone who went through the effort of getting a butt plug to enjoy sex as a bottom would be more thoughtful about their anal hygiene.

shameful sex is a way of life

Two rough-looking H/D riders saw me standing in the station and offered me a ride. I was roared down the highway to a garage-like stable, stripped, blindfolded with a rubber section over which a gas mask was placed with a tube going into my mouth. My hands were chained to beams overhead, and I was whipped with belts on my back and butt and felt liquid pouring down the nozzle into my mouth. I realized it was piss and voices told me many more bikers were now present. Leather and chains with weights were attached to my sex parts, and I felt hands pulling the hair under my arms, around my cock and rectum. Then an intense tingling heat made me realize my hair was being burned off. Several times my legs was raised, and I was fucked. I must have had several quarts of beer piss forced into my mouth. A sharp pain shot through my ears as they were pierced and rings inserted. My tits were pierced and rings put in and thumb tacks studded my ass prior to intense beating with studded belts.

I awakened next morning to find a fine looking boy ready to take me to L. A. on his H/D. Only later did I see the words MALE and WHORE branded on each side of my butt. When he dropped me off, he said, 'We know your name, address and employer, and we have pictures of last night, so don't try anything ever against us.' The brand gradually wore away and my tits healed. From time to time I am sold for sex by one or the other of the several who send someone through town. An odd experience for a Phi Beta Kappa who had planned to be a priest and is a sedate college professor! But I am advertised by these guys as a supreme peace of ass. At least six have sold me at times. One has made over $7,000 on me. For a full professor to be sold to anyone at any time is degrading, yet exciting.

R95 I’m sorry that happened to you.

The time I stayed with my boyfriend after he drugged and raped me. Granted, I was dating him and didn't think it was rape because we were dating. But he had begged me to bareback and I had refused. When he drugged me, without my consent or knowledge, he barebacked me. It bothered me because he didn't admit he drugged me but I knew he did.

I later found out this was his MO. I was so disturbed but he was hot asf.

The feeling of being drugged is awful.

R115, why didnt you just give him a fleet enema or something, you could have done done the inserting and let him flush out in private...

R116 Amateur. I had all that but it took place in a palatial tent in the Arabian desert. And camels were involved. Also I was in high heels and did it all backwards. Finally I am now sold and flown from my post as a professor at an illustrious Parisian university to be used as a sex slave on 5 of the largest super yachts in the world.

My most shameful/embarrassed encounter was a hot daddy that sat next to me on a quiet train after we made eye contact. Before long, we were groping each other, and before long, I creamed my pants. Had been a while and the guy was my type to a T, but I was very embarrassed that I could only last a few minutes of this hot man touching my dick. Had to run to the restroom covering my crotch so I could clean up.

Did they laugh at your puny cocklet, R116?

DID THEY LAUGH AT YOUR PUNY COCKLET?????

R120 has never been to he.

[quote] He worked at a paper bag factory. I always ask for plastic now.

MARY!

Shameful bump.

I was about 18 and met a guy on AOL. An older married DL Staten Island daddy type...my favorite at the time. So I get to the guys house and quickly realize he's my former neighbor/friend of my parents who had moved (with his wife!) away from our neighborhood a few years prior. I let him fuck me in the finished basement of his Staten Island McMansion, noting the framed pictures of his kids (that I used to play with when they were our neighbors) while he had me bent over his couch. I didn't want to say anything and I wasn't sure if he recognized me, since the last time he saw me I was 13. As I'm walking out the door he says "oh by the way how's your mom and dad doing?". I hadn't though of him in years but just learned the other day (from his daughter's social media) that he died from COVID. I guess his little secret was never found out.

R116 how do they make sure you don’t become fat and undesirable? Is there a punishment for that? Do they put you on the discount hoe rack?

I was a men's room cocksucker and cum swallower. No shame in my game but lots of cock.

I had sex with a creepy old man that was a psychiatrist in his car, it was just oral and jo but he insisted on kissing me and his teeth looked like dried out corn and his breath was as bad as you would imagine but I was a shy and fat and had pretty much no self-esteem and also he'd driven us to an old abandoned cemetery so I was afraid if I did anything to piss him off he'd kick me out of the car and leave me there to walk miles back home. Oh, And it turned out he was a freak that liked to shove stuff inside his cock while using an e-stim...while in his office where I assume he saw his patients.

Shit I wish a trick would take me to an abandoned cemetery

[quote]...a creepy old man that was a psychiatrist in his car...

It's been one of those days when an awkward phrase like this just makes you sit and laugh.

[quote]...a creepy old man that was a psychiatrist in his car...

Does he hang one of those metallic signs on the side of his car: "The doctor is in"?

I've been vomited on during sex. Not once, but twice, while being deep-throated. Really gross.

After the first incident, which was back in 1995 with a guy I'd been dating, I was so disgusted that I got up to take a shower and left him there pouting. He said he was going to leave, and I told him he'd better not go without cleaning up his entire half-digested Yankee pot roast dinner off my couch. We never had sex again and broke up soon after that.

Ten years later, it happened again, but with a different guy I was seeing. Only this time, it was Christmas, and I'd sprung for an expensive trip to a favorite ski village; we were staying in the executive suite of a posh resort. He'd eaten too late, hot wings or something else greasy. Still, he was always, ALWAYS horny, and he seemed embarrassed but undeterred. I'd really been looking forward to fucking our brains out all week there and decided my holiday wasn't going to be ruined by someone's silly old gag reflex. So, I just stripped the pukey sheets off the bed, balled them up and tossed them in the closet, dragged him into the shower with me, and fucked him hard in there against the shower wall. We both came pretty fast. I shut off the water, toweled off and went to lie down. He brushed his teeth before coming to bed and asking me to fuck his mouth again, and during a tight 69 while I was eating his ass and stroking his cock, we both came a second time on the bed. When I ejaculated, he managed to swallow all of it, and then we both passed out.

There are some truly disgusting tales in this thread, but I think R20 wins on that score. R13's story was the best, to me.

When I was 18 and in college I met up with a couple in their 30s and let them drive me 45 mins from campus for a threesome. One guy was skinny and not much to look at, the other was fucking gorgeous. We drank at their place and got to know each other, and eventually got down to it.

I finally get the hot guy’s dick in me, and the boyfriend has a jealousy-induced psychotic break. He starts accusing the boyfriend of abusing him, molesting their kids, and stealing from him. He called the cops to report DV, and they show up and talk to us while we’re all in our underwear. The ugly guy turns out to be bipolar and off his meds, and the one cop tells me they get calls from these two all the time. Eventually the cops leave and by this time it’s 3 am, and I can’t get a cab home (this was before Uber) and I’m too closeted to call a friend. So I slept on their couch while crazy slept in the bed and hot dude slept on living room chair.

In the morning the hot guy wakes up and goes “oh, you’re still here?” and tells me he can’t drive me home because the car is in the boyfriend’s name and he’ll report it stolen (I laugh at this excuse in retrospect). So he calls his sister and invites her over under false pretenses before asking her to give me a ride. She says she will for 20 bucks, so I pay her. We go out to her van and she’s got two toddlers in the back seat, so I climb into the third row. I tell her where I live and she goes “I don’t know where that is” so she makes a quick detour to pick up her husband. They drive me back to campus in complete silence, and when I get back to my dorm room I have a text from the hot guy going “hey, I hope I didn’t ruin my chances with you.”

The most shameful part? I hooked up with him again after this.

Back in my drug days (about two decades ago, don't touch it now) I met a guy in an adult book store. We connected with our coke and decided to hang out together.

We ended up sitting on a filthy NYC sidewalk under one of those construction scaffolds. It was Third Avenue. So I started sucking his dick and an old lady walked by and said "that's disgusting!"

I kept sucking.

You win R136!!

More!!!

God these are some great stories. Especially because they are so real and unique - except for the posters who think drafting erotic fiction is funny, it’s not. We are sex aficionados many of us. But look at all the life’s adventures we experience as a result - memories of risks taken.

During my short meth period, I met lots of very sketchy men in apartments that had been cleaned in monthS.

It was so gross and a major reason I stopped.

When I was in college, a man who lived in my apartment building would constantly hit on me. And I always turned him down. He was not entirely disgusting. He held a job, he bathed, he was of some average middle age. But he made himself a nuisance. At least as I was concerned.

Then one day, late in the semester, when my money was running out and I was wondering how I would get through the semester, he offered me $200 to fuck me. In the 70s, that was more than a month's rent. So I sucked his dick and let him fuck me and I got a month's rent and grocery money.

I never did it again, but I never liked that I did it. I can't find anything wrong with it, but it doesn't feel good.

DAT’s da SUCK JOB!

A close older gay friend passed away suddenly when I was in my twenties. That night I had a lot of mixed emotions and got drunk at a bar. I brought a nice guy home who I knew had a crush on me and we fucked all night based on all the condoms I found in the morning. I blacked out and don’t really remember it. I felt badly about it because I used him and it seemed to mean something to him.

Our landlord was trying to help Dutch, a homeless guy who would hang out in our neighborhood. When homeless, he looked like the Unabomber dude. After a haircut and a shave he was handsome, wavy black hair.

The landlord owned a gym and tanning salon and one of our other gay neighbors had seen Dutch there and said that they'd seen him changing and wow, he was packing. But could anyone imagine actually playing with him???!!!????

My upstairs neighbor and I had repairs Dutch was working on. He asked for a beer and we were both there, staring at his crotch as he worked. He got the hint and unzipped to show us and indeed, he was hung.

My upstairs neighbor chickened out on action, but I wasn't passing up a true 9 inches, and fat at that, so I sucked him off while my neighbor watched (and sucked him too).

Sadly Dutch didn't stay on the straight and narrow. Saw him on the street a few years later and by the time I had realized who he was he was gone. But a beautiful man under it all, for sure.

No you did not rim him, liar.

I regret my 3 way with Oprah and Gayle! Those girls are rough when they peg 😰

R146 = Robin Roberts.

R146 = Diane Sawyer, who never passes up a chance for some BBC