Embarrassing Sex Moments

ChefChiTown

The secret ingredient? MY BALLS
When I was a junior in high school, I got my first shot at anal with my girlfriend. We had anal probably about 2-3 times before this and decided yeah lets have some anal sex tonight, sure why not?

No...no, you didn't.
 
There was this one time when Stan was elbow deep in me and Greg while Blue took him from behind. We had talked about experimenting with Voltaire's glove, but Stan tried begging off - He was still sore from then Plasma made him ride a parking cone. After the scalding coffee enema, we talked him into it anyway, and once we were in there, he was pretty happy. Turns out his discomfort was caused by the parking cone (it was still in there).

Things went very, horribly wrong when we got to Blue and he confided that all he had eaten for three days is whimsy's bacon-flavoured man chowder and several dozen bran muffins.

I don't know if you know this about Blue, but he's like a human thermos. Once we pried open his tasty bung hole we all got sprayed with hot, whimsy flavoured coffee enema.

I don't have to tell you, I felt pretty silly with coffee on my face in that situation!
 
I had a feeling that was coming. Anyway..

When I was a junior in high school, I got my first shot at anal with my girlfriend. We had anal probably about 2-3 times before this and decided yeah lets have some anal sex tonight, sure why not? So here I am railing my girlfriend in her ass standing doggy style, with her over my bed, feeling good, lasting long, and overall just enjoying the hershey highway. My parents were usually home when we were fucking, but never decided to bother us until of course this rare time I'm banging my girl in her ass. So of course my mother decides to not even knock and just straight up open the door... and as my mother screamed "Oh my God!" And as I'm yelling "Mom, get the fuck out!" I suddenly heard a loud fart as my girlfriend dove into my bed sheets. As I recollected myself, I realized an awful smell was lingering, and of course, yes, my girlfriend shit. It wasn't just a shit though, it was a spray shit, complete with lube, all over my leg and down my foot. My girlfriend had also shit on the floor, and on herself, and gotten some of it on my bedsheets as she dove into my bed. I then decided it was best my girlfriend went home, as I spent the rest of the night cleaning my room from the shit stains she left everywhere. That was the last time I ever had anal sex with that girl.

Maybe not embarrassing for me, but when your room smells like shit for a week straight and your girlfriend comes over to visit within that week, and the smell is still there, its a pretty fucking awkward time.

There was this one time when Stan was elbow deep in me and Greg while Blue took him from behind. We had talked about experimenting with Voltaire's glove, but Stan tried begging off - He was still sore from then Plasma made him ride a parking cone. After the scalding coffee enema, we talked him into it anyway, and once we were in there, he was pretty happy. Turns out his discomfort was caused by the parking cone (it was still in there).

Things went very, horribly wrong when we got to Blue and he confided that all he had eaten for three days is whimsy's bacon-flavoured man chowder and several dozen bran muffins.

I don't know if you know this about Blue, but he's like a human thermos. Once we pried open his tasty bung hole we all got sprayed with hot, whimsy flavoured coffee enema.

I don't have to tell you, I felt pretty silly with coffee on my face in that situation!

This is better that most of the joke threads :rofl2:
 
It was my first time going down on this new girl. She was asian and had the tightest body and tightest ass. I fucked her little petite body, and she was a squealer, and within minutes felt that I was close to cumming.

So I pulled out and decided to give my dick a rest and eat her out. It was the worst taste I've ever experienced. It was a combination of sour and bitter. After one lick I gagged. I was a little embarrassed not only for myself, but for her because of the nasty smell and taste. So I kept going. And kept dry heaving. Before I knew it, the dinner I ate about 30 minutes before was all over her legs/stomach.

She screamed and got mad but I told her it was her fault because of her nasty pussy. Needless to say, I broke up with her.
 
hahaha...good for her, thats what she gets for having a stinky puss.
 
This isn't that bad, or maybe it is I don't know...
I just posted the below in a thread about the OP going to a hooker to lose his virginity.


A long time ago when I was still a virgin and a little older than the OP I came to the same decision........ but it didn't go so well.

First, I decided drive to Reno because I wanted to go where it was legal. It was over 8 hours but well worth the peace of mind. When I arrived at the brothel I sat in the car for at least 15 minutes trying to stop my hands from shaking. I rang the bell to go in and was greeted by the madame. She called out the girls for a line-up and I was shocked. Now I was expecting a bunch so-so girls because this was not a high class brothel. I figured If I was lucky, I would just have to pick the least ugly of the bunch, but it must have been an odd day, because there were 7 or 8 extremely hot girls. every single one of them was fit and pretty. I was a little overwhelmed. I picked slender dark haired girl with nice perky tits and a sweet ass. She looked a lot like Tiffany Taylor (I'll come back to that).

We go back to a very nice room and she starts talking more money than I make in a month. she immediately can tell by my face I"m not that type of customer. So then we go back to what can best be described as a miniature dorm room , it was the room where she would stay in for her shifts, probably 6 ft x 9 ft or so. There was a bed. and a little washroom attached. We negotiate a price for a half hour and I'm still nervous so I'm thinking well let's get this over with. This wasn't like a date where you are joking around and talking. At least with this girl it wasn't.

So then she proceeds to do a STD inspection and she is lifting it up, shifting it left and right and looking at it with all the stereotypical "studious" faces one could imagine. Now, one would think that with a really hot girl messing around in my pants, I would be rock hard by now. I wasn't. And there was also a longer than comfortable silence while she was seemingly composing her thoughts. "sweety" she said, I think you need to go to a Dr to get these red spots checked out, you might have something". I told her that's impossible, I'm a virgin. She looked again and said no she couldn't do it. I asked that since we are using condoms, how but a just a quick fuck then. I think she thought I was lying about being a virgin just to get her to do it, because she had an answer and it wasn't proceeded by "sweety"

Well of course the answer was no. (but in a much greater number of not so nice words)

So there I was more than a little disappointed and for lack of a better word, humilulated, after being turned down by a hooker.

I remember being so down that night in my Hotel I couldn't even beat off.

You would have had trouble convincing me this at the time this happened, but life goes on. And thankfully it did for me too.


And about Tiffany Taylor.... I don't know how old Tiffany Taylor is, but This was a few years before Tiffany Taylor was a porn star and of course I didnt' know who Tiffany Taylor was at he time. But several years later when I first saw Tiffany on the internet immediately thought that she could have been her twin sister or her. But I'll never know.


And I think I should get 20,000 rep points just for having to go through that.
 

vodkazvictim

Why save the world, when you can rule it?
I remember the first time I went to bed with one girl she had forgotten that she had her tampon in.
I pulled gently on the string to remind her and she was SO embarrassed. But sex is like that and you have to learn to laugh, which means that even though from that moment sex was obviously out of the question, we still had a lil kiss and cuddle. Eventually we worked things out and got things goin long term and that woman is the best ever!
No other woman has made me cum in her mouth with a BJ without me helping. No other woman has made me cum in a condom. No other woman has let me cum in her arse unprotected.
She's the best.


As for myself - I did fall asleep during sex once (after about 4 hours into the session, which started after a night of heavy partying), the lady concerned that time was suitably unimpressed.
 
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