Sex Confessions, Sex with Strangers

Most Cringe-worthy Sex Experiences of Americans

Francis – “Rubbing a pillow on boobs”

It happened in a split of second. We defied the law of newton. Just a small action but a far greater reaction. And not to mention, the sex had to end abruptly.

So, we started the dance without the pants. The kissing started. It turned into undressing each other real quick.

We were in the middle of sex. We turned really aggressive.

Everything was going well.

Then suddenly, i decided to make it a little more kinky. God knows why!

In that moment, i took a pillow and put it right on her boobs and started rubbing them. Oh yes!

It turns out, she had to push me away and throw the pillow aside. That moment i realise what really happened.

She burst out in laughter and i had to hide my face.

Boy! That was embarrassing.


Ernest – “Never those panties again!”

When I was a late teen ager back in St Louis, Missouri, I worked at a local gas station pumping gas, driving tow truck, helping fix cars every now and then.

There was a large apartment complex back behind the station and this girl named heather would come in a few times a week for gas and cigs. I was about 17 and she was a year of 2 older than me. She would always smile and flirt with me when she came in.

At some point during one of our flirty conversations I mentioned to her that I liked the color pink. That it turned me on when a woman wore it.

Well, the next time she came in while I was working she was wearing pink everything…. I mean almost everything. Probably the only thing that wasn’t pink was her jean shorts. Man did she look hot, and what a hint. We agreed on a date the next evening I had off.

My next evening off I met her up at the gas station where I worked. She got in my car(1969 mustang fastback) and we zoomed off on our date. Once again she was dressed entirely in pink again.

I knew she was as good as in the bag being dressed like that knowing That pink turned me on. We went and grabbed a bite to eat, than cruised for awhile in the car. I then asked her if she wanted to go parking and she said yes, so I drove to my favorite little hidey hole to park the car and get my fuck on.

That favorite hidey hole was the St Louis airport. I’d pull into hourly parking, stay down on the ground level all the way back in the darkest corner. I’d back the car up to the wall so no one could look through the back window, and I could spot anyone walking towards the car. It only cost like 5 or 6$ per hour to park there. Cheaper than a motel room, and Me being 17, sex hardly lasted more than 5 to 10 minutes a session. Like I said folks….. I was just 17. No dick control yet.

We get to the airport and I park the car. We get into the back seat and start going at it. Hot and heavy…. kissing and touching…. clothes coming off left and right…. THAN….. she takes off her panties and just straight up lights up the car with this horrendous smell from her vagina. I mean she smelled just horrible.

I have always been obsessed with giving a woman oral sex, but there was no way I was Getting my face anywhere near that smelly thing.

Me being only 17 my cock got hard when the wind blew, so I went ahead and slipped on a jimmy and fucked her anyway Even though her pussy stunk to high heaven.

What can I say, there still was a hot looking chick naked in the back of my car. The sex definitely wasn’t anything spectacular, and giving our ages it really didn’t last very long either. We finished up, put our clothes on and rolled out.

I hung out with her a few more times but never fucked her again after that first time. The smell just turned me off so bad, I really had no desire to get her out of her panties again.


Now over the years(I’m now 46) I’ve come across some women whose scent was a lot stronger than others but nothing like heathers. That’s a ‘cringe worthh’ sexual experience I definitely will NEVER forget.


Brian – “Making out with a random girl in college”

My first night of college I was a hugless, kissless, never spoken to a girl virgin, same night, met some slut, went back with her. She told me to put 3 fingers in her, I panicked as I didn’t know how to do it and told her “do it yourself, I don’t want to catch anything”…

Oh lawd, I spent the next 5 minutes convincing her I was joking.

i’ve had many, many cringe moments like that. When will I learn.


Rolando – “Never buy cheap bed sheets again!”

Back when I was living in my first apartment, I thought it would be a good idea to get myself some silk sheets. The intention was to create an environment of classy sensuality for any young women who might spend the night at my house (without having to drop a fortune on things like champagne and chocolate-dipped strawberries). As I discovered, though, silk sheets are damned expensive… and given that I was a broke college student, I couldn’t exactly afford the top-quality bed-coverings.

Thus, I made the mistake of purchasing cheap silk bed sheets.

Anyone who has spent any time wrapped in low-quality silk knows how incredibly unpleasant an experience it can be: You start off feeling like the sheets should be soft and smooth, but there’s this annoying tickle that dances across your entire body. Rolling into different positions is a crap-shoot between sliding around between slippery folds and dragging them along with you. You start to sweat, and the material actually sticks to you a little bit, making your bed less of relaxing cocoon and more of a sweltering burrito.

There was one other issue, as well… but I didn’t discover it until I actually followed through on my plan of having a young woman sleep over.

After a particularly active (and unwisely long) session together, the girl and I passed out next to each other with nothing but those silk sheets between us and the hot night air. I got up once during the night, relieved myself in the bathroom, and went back to bed, which woke my partner from the depths of her own slumber. She apparently decided to emulate my actions… only instead of quietly returning from the restroom, she rushed in and shook me awake, demanding to know if I had any sexually transmitted diseases.

Now, I’ve always been careful about staying clean (and we’d discussed as much), so the accusations were more than a little bit jarring. When I asked what had prompted them, the young woman turned on the light and displayed her naked form to me… and I saw that much of her body had been dyed a light shade of blotchy purple.

A brief examination revealed that my own skin had adopted an oddly violet tint, too.

We eventually figured out that my cheap-as-hell, knockoff silk bed sheets had bled during the night, transferring their color to my paramour and me. Worse still, the stuff didn’t wash off as easily as I would have liked, and the two of us spent more than a little time in the shower together. It could have been an enjoyable evening, but mutual bathing just isn’t as much fun when the intention is actually to get clean.

I also had to change my bed sheets before we could finally pass out again.


Holt – “Definitely not a cat lover”

I was seeing this girl and we were FWB, the first few times when I stripped down and we got into it her cat would piss in my underwear. Then I started stacking my shit up high, and the cat pissed in my shoes.

So I bought two plastic totes I threw all my stuff in them when we got started. Then the cat would jump up on the bed and watch me as I was balls deep.

I threw the cat out a few times but it would cry and cry.

I hated that cat.


Steven – “Sex with my teacher”

“I had a one-night stand with my English teacher. We waited until after graduation, though we’d talked about it during my senior year.

She was very attracted to me, which I found flattering (and surprising). I thought she was cute and I was eager to lose my virginity in an actual bed and in a sort of no-strings-attached situation.

She was 30 at the time. We’ve stayed in touch. She lives 1000 miles away but a few years ago, my wife and son and I visited her when we were in the area. We spent a lovely morning catching up. She’s a very sweet person and I’m glad she and I shared that night together


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