What has been your awkward sexual moment?

For example, mine was when I was when I lost my virginity. I told her I wouldn't cum inside her, because she requested that i didnt, even though she was on birth control. but I did...

 

I was getting fucked nice and hard while on my back, and my man went to pull me up so I'd be on top. I didn't know he was going to do this, so when he grabbed me, I wasn't able to pull myself up properly and I slipped and fell off the bed. It was awkward for about a second before we both started laughing our asses off and went right back to fucking.

 

Got to be when my girlfriends twin brother walked in on us...

 

Oh dang. That is pretty awkward...


I had a checkup with my female general practitioner one week, and my girlfriend at the time thought it'd be funny to get me all worked up before I went, and text me dirty while I was there, needless to say I had a rock hard hardon when the doc asked me to drop my pants... That was awkward.


The doc played it cool though, even joked about it, saying " I guess we don't need to make sure that's working huh?"

 

Shot a load up a girls nose once, wasn't good in any sense of the word.

 

Was doing some bondage play with a girl I had met a few days before and went into the next room for a couple minutes.. except I fell asleep. Woke up a few hours later, assumed she had gone home, I got dressed and went to class.

My roommate found her.

It was his younger sister.

Needless to say that relationship ended.

I lost a roommate too.

 

This sounds like it was more deliberate (or fake) than awkward. There seems to be some holes in this story too. You kept your clothes in a different room? From your story it sounds like she was tied up, but you assumed that she already left? Sounds a little off.

 

Not so much awkward as funny

This is not so much a story about an awkward moment, but more a funny thing that happened one night. I had never seen a woman having a full-on, screaming orgasm until I was 22 years old. I met up with my dad at a bar one Sunday for a couple of beers, and he was talking to a few people he knew, including a woman who worked part time as a receptionist for one of his friends. My dad left after a while, and everyone else kind of melted away over time, so we were left talking together. I found out she was 45 years old and divorced, and to cut a long story short, we ended up back at her place, and she took me to bed. I had only been to bed with three other girls up to that time, and I guess I hadn’t made them cum properly, so none of them had really gone to town the way she did that night, and while we were going at it, she threw back her head, cried out, and clenched her fists across her chest, and started gasping and groaning, as though she couldn’t breathe. You have to understand that at 22, a 45-year old seems a lot older than she really is, and for a brief moment, I thought she was having a heart attack, and my heart sank as we screwed. Then, I realised she was cumming, which of course made me quite pleased with myself, but for that few seconds, I thought she was dying.

Afterwards, I couldn’t bring myself to tell her what I’d thought.

 

my awkward situation occurred when I was about 17. I was fucking around with this hottie from work. I was laying on my back and she was giving me a pretty decent blowjob. so after a bit, she must have sensed that I was close to cumming. she took me out of her mouth and started jerking me off with her hands. my orgasm hits, and the next thing I know, two huge wads of cum hit me directly in the mouth! everything at 17 is embarrassing, but she handled it well. I fucked her the next night

 

I'll bet for her it was not an awkward moment. She did come back for more. I'll bet that for her it is now a cherished visual memory. I hope you handled it well also.

 

not wrote up that well - my fault.

To clarify --

My clothes were in the washer (closet off the kitchen). So no need to go back to my room

I fell asleep on the couch following some liberal use of alcohol and pot (which always caused me to crash hard).

We had gone out a few times since her brother introduced us (not as a "date my sister", but just as "this is my sister") but she had never stayed over because of her brother (she was the baby sister,and said it just felt weird). So due to the drink/pot hangover I wasn't thinking too clearly and just assumed she had left at some point like every other time. I didn't really think about the bondage, because we hadn't done it before. It was kinda a kink thing to try when we got stoned.

Wasn't the greatest moment of my life.

 

I came and farted real loud at the same time and it stank. And I was so fucking embarrassed.

 

The first time my aunt sucked my dick. I was 12, and awkward as hell

 

My most difficult was making love to a transsexual, we were hot on the bed and I didn't know if "playing" with her cock was part of it so I offered and the sex sort of stopped! I slept with her in the bed and in the morning we talked, she went on to explain that her cock was not something that she felt was a part of her and most guys "used" her to fulfill a fantasy of a chick with a dick? By the end of the conversation she understood that my offer was more of me trying to be the best lover and not what she had come to expect out of "some" guys!

 

loooooooooooooooool

 

My wife and I were on a trip with my mother for my cousin's wedding. My mom was staying across the hall in a guest house and walked in on me and the wife making love. Luckily she couldn't see much because a) we had the blankets pulled up and b) she didn't have her glasses on. Killed the mood quickly though.

 

My mother walking in my bedroom when I was in the middle of a sixty-nine with my girlfriend. After a pause she just said "SORRY!".

When we sheepishly came downstairs some time later she was making the biggest pile of ham sandwiches you have ever seen.

Nothing was said.

Thinskin

 

I was16 yrs old girlfriend and I going at it on the living room floor and her uber conservative mom catches us as I was cumming. That was awkward

 

Awkward. I was doing a porn film here in Central America. The girl the supplier brought had the same body type as my x-wife. I went totally limp during filming in front of the camera and everyone there.

 

Was doing my ex doggy style and she stopped me and wanted in her ass, mind you we had no condoms left and the bathroom was occupied, so dirty hole ahoy.