Sex Disappointments: Tales Of Unfortunate Experiences (25 GIFS)

15 Nov 2023

"I was on a medication for a time which acted like reverse viagra.My former GF & I were having fun time and she refused to give up so she just kept on trying to “help” orally.

I had a full on orgasm without erection. Talk about a disappointment."

"Had a girl give me a blow Job literally tried BLOWING my dick, like it was a balloon"

"Finally got with high school crush 5 years after graduation. Tasted like an ash tray. Then told me about her fiancé afterwards"

"It would have to be the time a piece of broken condom came out of my fiancés vagina during sex. We hadn’t used a condom together for about 8 years at that point….so yeah pretty disappointing"

"Two very attractive girls invited me to their house to “hang out and have some drinks”, queue them kissing each other and me, dancing naked on the table in front of me together.

Maybe they were nervous because they both drank too much, and it went from sexy to messy in the matter of 5 minutes, with them trying to pull me into bed only for one of them to pass out on the bed and the other hanging over the toilet vomiting.

Anticipating three way, got vomit cleaning, hair holding and back rubbing."

"I had a crush on a gorgeous girl for years, seriously she was a 10/10. One night we ran into each other at the bar and went home together and long story short…. during sex she tried to make me throw up in her mouth"

"Was having some pretty great sex with a work friend. She was super into it and really good at everything.

We were having a blast, tons of positions, lots of enthusiasm, when all of the sudden we can’t find the condom.

She accuses me of intentionally taking it off and hiding it, suggesting maybe I put it up my ass (lol).

I honestly had no idea where it was and she was furious, damn near accusing me of assaulting her. She kicks me out despite my pleas that I had NO IDEA where it was, suggesting it might be inside her vagina. This only pissed her off even more.

Went home sad and confused. Woke up the next day to her voicemail profusely apologizing telling me that yes, it was in fact inside her. She had just found it.

We never hooked up again after that."

"14 years ago. We were both 20 at the time and had been co workers. He asked me out and I was super excited because we had crushed on each other for a while. We had am amazing date with great chemistry, and then we went back to “his place” where his “roommates” were sleeping (I guess he was staying with his friend’s grandparents, but didn’t tell me until we got there).

We go to his room and he puts Encino Man on… Few minutes in we’re making out and I’m getting excited to finally feel him. We’re down to our underwear at this point, when all of a sudden he flips me onto my side facing away from him, and starts dry humping my lower back through his boxers. This goes on for a very confusing and awkward minute and half, after which he finished in his boxers. I quickly got dressed and left, later told him we should just be friends.

Last year he matched with me on Hinge. I asked if he remembered me and he said ,”you look so familiar…” and I told him I could never forget him. He gave me a very cocky and flirtatious response, to which I replied, “Encino man” and promptly unmatched."

"Was my first gf and I was her first bc she wanted to give me head so I let her was okay for the first couple minutes then she tried to suck on my balls and she sucked it too hard and I fell over. She basically bruised my right testicle and it swelled up for a week."

"Was just leaving a party one night around 2am and I get a message from this girl I’d been snapchatting for a few weeks asking me to come over. She was a few years younger than I was but she was really hot and sounded super in to me and I was drunk and horny so I figured why tf not.

I show up at her place and we start making out on her front deck. It was getting pretty heated and I even took her titties out and as I started to suck on them her front door burst open and out came 3 of her flatmates. Cue the next 2 hours of sitting on her front deck talking with all her flatmates who wouldn’t fuck off, but they gave me a few drinks which enticed me to stay.

Around 4:30am she finally takes me inside and into her room – it’s a fucking pigsty, clothes and dirty dishes and rubbish all over the place. Fuck it, I’d already suffered thru 2+ hours of nonsense bull shit from her mates, I’m getting something out of this.

I then proceeded to receive the toothiest blow job of my entire life, which actually caused several cuts. She then tells me she’s on her period so we can’t have sex. It hurt to pee for over a week. We did not hookup again."

"90% of the “freaky girls” I’ve hooked up with just lay flat on their back or stomach the entire time."

"So I was 17. Convinced this girl who was drop dead gorgeous to come to my house she brought her friend who was also hot.(not as hot but hot) we were all hanging in my room watching tv me and the main girl starting making out the friend started undoing pants…

My little cousin 12m starts banging on my room door cuz he wanted to hang. (He lived down the street)

I said no go away. He started banging on the door then called my mom and told her I wasn’t opening the door. So my mom started banging on the door.

Night was over they said maybe next time. Then left. SMH. I still don’t like my cousin for that. Lol. He grew up and apologized but it still upsets me."

"Me and my mate bring 2 super hot girls to my place for an “after party” after meeting them in a pub.

I’m on the sofa making out with (think her name was Claire) and my mate was on the armchair making out with (lets call her Sally) my mate and Sally vanish to what I suspect to my bedroom (no problem, I’m cool with bumping uglies on the sofa), after a lil while Claire excuses herself to use the loo, 10 mins later I’m wondering if she slipped, fell and hurt herself or something so I go to find her, nope not using the loo but I do hear 2 girls moaning from the bedroom – my mate was having a wonderful time with Sally and Claire, when I tried to engage one of the girls (can’t remember who) told me to fuck off downstairs.

Not wanting to cockblock my friend I went to sleep on the sofa drifting of to dream land to the sound of the most wild sex I’ve ever heard in my entire life."

"How about being disappointed in myself. I got on top, flipped my hair confidently, put his dick in then realized I had no idea how to ride it. That was my first time and I never realized it’s not instinctual.

The guy tried to teach me for like 5 minutes. He said do it like I was twerking but I could not twerk for life. It was so embarrassing. In the end he just gave up and told me to lie back down"

"Was invited over to a beautiful woman’s house to chill when I was naive and stupid and young. She initially initiated some foreplay but soon realized just how inexperienced and innocent I was and welp, I was sent away.

Never even occurred to me what she really wanted until it happened and I froze like a deer in headlights."

"Finger up the bum. She never asked or said she was going to do it, she just pushed the full thing up there with no warning. Nearly blinded her in one eye with my willy"

"I worked hard for weeks to knock boots with the hot chick at work, finally the day came and she smelled terrible down there. I finished the job tho, and did it a second time to be sure and yea it was pretty bad the second time too."

"My wife came home from shopping one evening. For some reason I kissed her hello, which was unusual for such a short trip away from the house. I don’t think she expected that because I tasted cum on her mouth."

"Getting my clit bit."

"I had a man take off his pants and then start crying about being uncircumcised. I ended up comforting him for half the night. Very confused though because I didn’t bring it up or say anything. Guess it was just on his mind?"

"Back in the mid 90s I fell in love with a girl in 7th grade. She moved away and we lost contact. Reconnected in our mid 20s and planned a date. We drank, we ate, we had a great time. We go back to her place and we start kissing and undressing and what not.

Im about to show her what she’s been missing out on all these years when I went full whiskey dick. Never hooked up again."

"Eating whipped cream off genitals. Those are flavours that do NOT go well together."

"Guy had poor, naive, college-aged me convinced he was truly an amateur porn star. Bragging to my friends that he’s gonna pick me up and we’re gonna hook up, after weeks of him sending me his videos and telling me all the things he’d do to me.

Picks me up. Barely grunts a hello. Pulls into an empty parking lot, slips a condom on, tells me to get in the back, and just…slams in dry. Thank god for the condom or I think I would’ve had some serious vaginal tears. He came in less than 30 seconds and then drove me back to my dorm.

My roommate/best friend was SO confused on how I was back so fast, and after explaining it, we laughed our fucking asses off making fun of everything he’d said. We still laugh about it to this day."