Most Embarrassing Sex Stories

Girl I was dating for a bit in undergrad was older than I was by a bit I was pretty used to sex and slutted around in college but wasn't "kinky" persay and she got me to try out anal. I really didn't know some girls really dig it.

We did anal a lot and the end was coming near some dirty talk happened she was gonna finish me off in her mouth. I'm inches away from her face and neither of us are thinking. No it's not going where you think it is, she had a brief second remembering wait A2M is bad... she looked at me "wait I can't!" burst into tears and ran into the bathroom.

Had to finish myself off and then went to check on her #niceguy. She was really embarrassed she almost did that and more so she left me hanging. Clearly like a gentleman I told all my friends this story, I didn't lose a nickname about it for years. :|

So yes, hows that an non scat ATM story. If anyone wants I have a few dozen more, as I said I was kinda a whore in college.
 
I'm like a 4/10 at best with a muscular frame, so I look for other 4/10s and chicks that look like they almost have physical disorders. I'm not ashamed or proud of this, it's just fucking survival for a guy that looks like me. Just make sure you're fit and hygienic, and for the love of god, get a haircut.

Anyway, there's this chick that looks like a real axe-wound, (I say that 'cause I'm not much better), and she's all gums with a fair amount of facial hair. I'm totally cool with this, because now I associate hideously ugly women with ejaculation. Technically all my sex stories are embarrassing, but whatever.

I met her at the library in my college. She dressed like your typical grunge-era girl, which is strange 'cause this was like two years ago and she was a year younger than me. Anyway, I commented on a book she was reading and we got to talking. I invited her to a little get-together I was having with some buddies, and she agreed. I'll gloss over how the party went, but we ended up in an intimate situation. I was a little surprised, considering it was just one date, but I happily agreed.

Well, we're getting into the thick of it all, and I realized I couldn't get it up. I had a lot to drink, so I guess the pipes just weren't running right. So, I immediately panicked, 'cause I don't want her to think it's her fault. So, in my desperation, I just start smacking my dick against her body in an attempt to get hard. In my stupor, I didn't realize how hard I was hitting her with it and how wildly inappropriate it was. So after about a minute of smacking her with my cock, I just gave up and went down on her. I noticed how shocked she looked after the experience, but I didn't want to draw attention to it. Eventually I managed to maintain a half-chub and finished up.

But that's not the worst of it. I was holding in my pee most of the time, but I was super exhausted. I ended up just falling asleep on her bed. I remember waking up in the middle of the night and staring at the bathroom for minutes, but I just couldn't find the strength to get to the bathroom. So, as I stared at the bathroom, I just started pissing. The kind of piss that actually hurts the tip of your dick from the force. Throughout all of this, she just didn't wake up. I was fucking soaking her bed, and she didn't wake up.

After the pissening, I went back to sleep. Call it divine intervention, or call it my brain's alarm clock, but I managed to wake up before her. I hastily gathered my things, wrung-out my urine soaked boxers, and just booked it out of there. And don't ask why I did it, but I left 20 bucks on her kitchen table. At the time I figured it would allow her to buy new bedsheets.

She never called me again and I never called her. I don't know if she knows that I pissed the bed, or she thinks that she did. Either way, I still wince when I think about it. That's the worst sex story I've ever had, but I have a few more that are still pretty bad. If there's interest, I'll write a few more.
 
OP doesn't state it has to be embarrassing for me..... As I said I was pretty bad a whore and a dick in college.

I swear there is guilt about this now, but only some. So there was a girl in one of my electives, tbh I forget what one. She was pretty into me, cute but insanely vapid. She'd always ask to hang out and I liked company to study so we often hung. I made it pretty clear I wasn't into her sorta had a g/f and she was wearing on my nerves. So I got social experiment on her. I tried distancing myself, politely to no avail. At first came taxes like bring me coffee and then breakfast to spend time.

She at some point could tell I was pretty much using her and she would step up her flatteries and the such. Now the building we were in was 4 floors, and the top had an empty area where the bathrooms were and some higher level classes (math iirc) only taught in the after noon but you had to get past the main block to get to the empty wing.

As I was eating my delivered breakfast, flirting was heavy, and I finally gave in after some loose offers. I said I want you to suck me off. But where? Parking lot was busy as it was like 11ish. I wasn't taking her to my place and she had roomates. Enter the wing. Now this wing had the only rest rooms on the floor. So I talk her into sneaking into the mens room with me.

She's blowing me in the stall (classy as fuck I'm aware) the evil of, Hitler, Stalin, Mao and Judas all over come my mind. I'm done with this as the head isn't good and unless I throw a nuke she will think we are married or something. I pull out splatter her face and grab my books yank my pants half way up sprinting "late for class gotta go". So I left her jizz soaked face in a mens room.

I have a few others I will write up.
 
Forgive the multi posting, I am in a writing mood and rather split the stories.

I was just coming out of a bad relationship, well as bad as break ups get for high schoolers. I took some time away from girls and was in school mostly being social a few hook ups.

I finally found a girl who made me melt. We met through a club but weren't local. So we met like 2 times in person but talked daily and AIM (dating myself here) we were falling as 19 year old do. I told her I wasn't trying to rush and really not ready for anything. She was coming over and this was the first time I've shared a bed in a while. It was going to be that, she said let's not tempt our self and I threw out all my condoms just so we "had" to not do it. Yet I'm writing this so you can see how good an idea that was.

Even though we hadn't spent a ton of in person time we meshed very well, watched some cartoons probably like sealab 2021 or Simpsons. Just talked and hung out. Time to snuggle and get to sleep. She tells me oh yea I know we aren't having sex but I sleep naked. OH. OH OK. So my crush/gf/friend just strips down in front of me and hops into my twin I go down to my boxers and climb in as well. Neither of us are very big people but twins get, friendly quickly with two in them.

At least a good night kiss? She asks. I lean in and her tongue goes down my throat. Her tongue went down, something on me clearly went up. We are kissing and she says, I'm ready and I want to be with you. The dry spell my emotions and hormones are all saying lets go. I roll on top of her and she says "I'm on my period that's not an issue right? We can just put a towel down" I'm a single man in college I don't have spare towels (I've since named all my sex towel's the towel of 1000 shames) So we get one of the two I own. and plop it down.

I roll back on top of her and aim for the goal. I freeze up as some part of my brain is getting enough blood to go, uh bassomatic, don't do this. Her eyes look up at me like a broken puppy. "what's wrong?" I uhh... it's dark I don't want to mess things up. The best lie I could cook up in the time I had. She grabs me and puts me in her, and says I think you know what to do.

Our passion filled love making is on going and it's almost time to finalize it. Now for those who are male, know at the 9.8 scale you become weaker than a low birth weight baby seal. "It's ok I love you" She grabs my ass and rows me into her till I blow. Then it gets better, "because I'm on my period we don't need b/c" WAAAAAAAAAT? You don't know how you work there and I just ... oh god oh god.... I felt dizzy from the orgasm but more so from her insanity, and mistake on her own bodies function.

At that point, we go to shower I figure plan B will work for two rounds as well as one and pop another in her in the shower.

How I'm not a father or with more STD's than Nurgle I'll never know.
 
Last one for now, promise forgive the awful forum behavior.
I was hosting a party at my apartment, rare for me even though I had my own place and lived alone.

Needless to say it was heavy drinking, playing cards a small get together but a few people I didn't know. This stunning red head who was friends of a friend was really digging me. We got to making out. I was past drunk, I mean even in early 20s I was gonna have a day long hang over drunk, I'm sure the diet of ramen, doritios and quad stackers (those were my jam back when I had a labor job) wasn't help my stomach when mixed with bottom shelf vodka and yuenglings till the cows came home.

Party was winding down and we all were crashing were we did, some people stumbling back to campus, others their places, few on my couch. Pretty standard. So the red head who was into me all night was clearly drunk (she had to be she liked me and thought I'm cute) she says she's staying in my bed I can sleep where I want. ( don't know how she knows I love aggressive women). So I jump in and we start fooling around. We exchange each and every kind of foreplay.

I reach in my night stand for a condom, and shes thankful as she was in need of the real "D"eal. My stomach lets me know this is not going to happen. I go green, BADLY. Thankfully it's dark or she'd see I doubled as a ninja turtle in skin tone instead of my albino's butt white normal. I tell her, I am embarrassed and I am not good at putting a condom on and had be dry for a bit or something, now my bathroom was attached to the bedroom. I sprint in and projectile vomit for a full minute (count to 60 if this doesn't seem long). Still being drunk to a stupor and with a raging hard on. I fumble with the condom so I was only partially lying.

The door pops open, I flush and say sorry I needed to pee too. Finally cover myself up and she grabs me and throws her tongue in my mouth. No brushing no rinse.... she doesn't know as she keeps kissing me. After the sex, I brushed my teeth and passed out I was too embarrassed to tell her and I wouldn't kiss in her in the morning. We kept in touch for a bit and I never told her.
 
One time I really wanted a ginger root up my butt so I begged one of my friends to put it in for me, but he refused because he's a stuck-up prude. After that I started crying because I wanted it so badly, but then I sort of forgot about it because he took me to McDonalds and then it was okay.
 
So here's one that actually happened and isn't just me being a dumbass uueen: I once accidentally switched up lube and Vicks Vaporub and proceeded to accidentally slap the latter all up in an ex's vagoo.

Edited to add: We're still very good friends and she occasionally jokes about the time I "improved her vagina's breathing", haha
 
Last edited:
Back