Worst Sexual Experience?

[The_Ghost_Man]

Some of these stories are just... painful!

I have had plenty of two thumps and done sex (so bloody frustrating) but I think the worst sex would have to be when I had sex with a friend of mine as a teenager.

I was 17 and quite experienced but still in that shy stage where you don't really want to say what you want and you certainly don't want to embarrass the other person.
He was 20 and a virgin.

So... when it comes to doing the deed (missionary) he does not lie on top of me but DOES FUCKING PUSHUPS in and out. He does not just do this for a bit but the whole time! (No, it was not that long, but still). And of course he starts sweating and it is dripping from his forehead all over me...

No, that was not very sexy

LOL. Maybe that's why my 16yo son is doing 200 pushups every night. He figures he's about to get lucky!

 

[bibethhotwet]

Being in a hotel room with several other couples..one guy was pretty excited and went to get up when his foot got caught in a sheet and tripped smashing his head on the night stand..gave himself a bad concussion.

 

[ChibiFangirl]

I was a freshman in high school and my brother is three years younger than me. I wasn't sexually active but I knew more about the birds and the bees, STDS and healthy sexual relationships than he did. It was spring break and our parents had taken us to Hawaii, where my brother and I had to share a room. I used to write erotic fanfiction and my brother walked in on me doing so and took my laptop from me and read it to himself. He was impressed how good I write. (Looking back at that fanfiction, its probably the worst I've ever written. its so bad it got removed from Fanfiction.net) It was late and I wanted to go to bed. I usually masterbated every night to help me calm down before I sleep. And I was crazy horny and so I told my brother that I needed to do a nighttime ritual. He wouldn't leave the room and asked if he can witness the ritual. I'm a pillow humper, instead of a finger user and I still own that pillow. He never touched that pillow because he knows its covered in come....you thought this was gonna be an incest story, didn't you?

 

[Calliesdad2010]

i was speaking to a woman on the net,

she invited me over to her house

i wasn't attracted to her at all,

either psychically or mentally- which is important

but we continued and had really bad lame sex

 

[a75]

I met the university sweetheart at a reunion, three years after our break-up. The shy girl had turned into a sexy young lady. Although we didn't spend much time with each other, at the end of the night she asked me politely if I could drive her home. Then she asked me to come upstairs. Then she asked me to penetrate her without foreplay. She came within 2 minutes. Then she thanked me and asked me to go.

 

[mewandrer63]

gave a younger woman a ride home from the bar i drank at ...her friends encouraged her to go with me. got her to my house and into bed. she was so high and drunk it was like fucking a raggety ann doll... when I finished fucking her I took her home(she lived with her parents)... did take her home again when she wasnt soo drunk...she still wasnt very "active"

 

[tightmedicine]

I think mine was the night of the sex that wouldn't end.
Now in theory that would sound good, no, great, right?
Wrong!
I hadn't been overly in the mood that night but I wasn't going to turn it down but he had been drinking a little and usually this has the effect of wilting a hard-on but that night it was like he just couldn't cum. After literally minutes upon minutes of futile thrusting - certainly long enough that I was getting raw and chafed at that point I had to beg him to let me give him a hand-job, or something.

He was never great shakes in the bedroom anyway and I usually had to make my own pleasure but that night was just not enjoyable.

 

[NickCarraway12]

Getting a handjob from my drunken girlfriend who proceeds to tell me that her ex was hung like a maglite.

 

[writerperson]

I was invited to a fivesome kinda last-minute. I got there and everyone looked completely different from their pictures. It wasn't really a problem - I'm pretty open with who I'm attracted to - but it threw me off a little and I was wondering if they were planning to skin and eat me or something, and the atmosphere felt a bit dead.

We all got a bit drunk then moved to the bedroom, but people were acting like they'd never had sex before, just sort of floundering around. I was taking this girl from behind for a little while, then she rode me until she came, then I just about managed. Then someone tripped on a step and fractured their elbow and we all ended up in A&E. I didn't go back there.

 

[Chandeliertears]

It has to be a very drunken (on his end) encounter with a former boyfriend. I picked him up from a bar one cold winter evening and quickly discovered he more than a little buzzed, let's say fall down inebriated. He was insistent on getting on top of me rather than sleeping it off. After several attempt to line himself up and enter me, his thrusting became haphazard, eventually evolving into rapid jack-hammering.

 

[Inspire8]

*****

 

[Asian_Flower]

My teenage years.

 

[Sheana_V]

I tried doing "normal" dating for a while in my 20's. So I started seeing this guy and went on four or five dates with him. I really enjoyed him and I enjoyed our time together, when we were apart I fantasized about him. On our last date I finally took him home and was incredibly excited to get him into bed. We made out for about 10 minutes, which was fine because I was painfully horny. Then he got on top of me, and suddenly it felt like I wasn't there. His body mechanically thrust into me for about five minutes until he came. He then rolled off me and took a shower.

Boo. That was our last date.

 

[Interested_Girl]

One of my exes....we had a really good relationship, because we were both funny and took a lot of things in stride. One night, he was super horny, you know how it goes. You're standing washing the dishes and from behind someone is taking their spatula and poking it into your theigh or butt.

Anyway, we hadn't had sex in about a week because I had gone home to see my family. So, seeing (feeling) his need I was like...ok...high ho. High ho it's off to bed we go...

He was super horny, the kind of hard where a guy thinks he is going to pop out of his skin, which feels amazing
...except when your tight girlfriend hasn't been fucked in a week and we forgot to buy lube.

So, I'm on top and of course he can tell im not 100% comfortable but i didn't say stop, so he doesn't. Then he flips me into missionary...when he does this he throws my legs over his shoulders to get deeper, which was quite painful, but before i could say no stop...he came. I didn't. And he knew that. He apologized. I was a little pissed. Then he jokingly said..."babe...did you start your period?"...and I just looked at him, slapped him and went to clean up. When he realized what he had done he was quite apologetic and made sure it didn't happen again....but no orgasm and super sore for the next few days....so no sex.

Fuck I was mad.

 

[Swgopro]

The closest thing to something being considered "worst" for me would be the girl that was HORRIBLE at blow jobs. The only time that she ever swallowed was when she sucked me off for awhile until I was in the neighborhood of getting off. To get over the edge, I had to stop her and jack off into her mouth. Really wasn't worth it.

For Mrs. S....she has basically no sexual history before me. She has told me many times about the guys her mom set her up with. She let him go down on her and I don't think he had ever done that before. I know she'd never had someone there before. I don't know how long he was down there, but she ended the night with teeth marks on her clit and obviously didn't get off...nor did he.

 

[wickedangeleyes]

My worst was while in college, my friend was going out with a marine and he came to visit and brought a buddy with him... We had all been hanging out and things got hot and heavy between my friend and her guy so his buddy walked me back to my room. I wasn't really attracted to him, he was super skinny and a bit boring but I let him cop a feel and give me some sloppy kisses... I figured what the hell.. And let him undress me, then he unzips his jeans and I swear he had the smallest cock I had ever seen before! I couldn't even see it when I wrapped my hand around it. I thought at first he wasn't hard yet but realized when I touched it that he was, it was probably 3.5 inches (maybe) and really skinny. It struck me as really funny looking at this guy with a bird chest and this tiny little prick and I had to try so hard not to bust out laughing and hurt his feelings. I started on a blow job but it was so small it just wasn't very effective, eventually he started moaning and told me he wanted to fuck me. I hadn't had a lot of experience at this point but I couldn't even feel him in me at all.. He pumped away until he finally came. I didn't even try to fake it, he was so caught up pumping away moaning and groaning he didn't even notice. I felt sorry for his future wife.

 

[UrbanBohemian]

When I was 19 my girlfriend at the time was very selfish and just wouldn't put any effort into it. She dead fished it and just didn't really care about getting me off. One day we were fucking and I was close but she had just cum and decided we were done so she suggested I jack off while she watched. I got pissed and yelled at her. I'm told I can be a little bit scary when I'm angry so I didn't hold back. When I called her a dead fish she started crying so I made her leave. I just told her to get the fuck out of here with that shit. She spent months not giving a shit about anything but herself and now she wanted to get all weepy and apologetic? Nope. Fuck off with that. Selfish lovers suck. Nothing worse than that shit.

Luckily a co-worker at the radio station I was cutting ads for at the time had a crush on me. I told her what happened and she said "What a bitch! I'm glad you got rid of her. You deserve better than that." Yep. I sure did. So I asked her if she was planning on going to the remote that Saturday night. (it was a fairly big show) She said she was, though I don't think she was actually planning on it since she only went to like two remotes the whole time we worked together, so I think she just wanted to hang out with me. She asked me if I wanted a ride so I of course accepted and we went to the remote and had a bite to eat after that, and then I was totally over DeadFish McSelfishBitch. I don't know whatever happened to her and I don't care. She's probably with some loser working a dead-end job with a kid or two. That's my guess.

 

[carlsnake]

My future wife and I had been dating for a couple of years in high school,and I had her naked on every date, fingering her to orgasm. One night in the car, I had her naked, fingering her to near orgasm when she unzipped my pants and took out my stiff cock. She had never done that, and just the fact that she did it was so hot that I immediately shot my entire load as soon as my dick cleared my pants. Fortunately, I did better after that.

 

[droopy1]

Worst was in a brothel she only allowed missionary sex. she held her hands around her vagina so i could not get full penetration. I got a bad vibe before we ever started so I should have went with my gut feeling and left. She was a good looking little shit though.

 

[Lia Monde]

I dressed in a sexy outfit. I bought dinner. We exchanged banter and teasing foreplay. I gave him a blowjob until he exploded. Then I brought out my strap-on and he ran out cursing. What a wimp!

 

[cliteatingman]

I dressed in a sexy outfit. I bought dinner. We exchanged banter and teasing foreplay. I gave him a blowjob until he exploded. Then I brought out my strap-on and he ran out cursing. What a wimp!

Clearly you sucked!! LOL

 

[Karhukissa]

[Karhu writing] My first experience wasn't really the worst, but it took me a good 8½ years until I got close again. We were classmates, just a few days shy of turning 15, and had been hanging out after school at her place for some weeks, exploring each other and doing some light petting. Then we decided to lose our respective virginities. I had got hold on a condom, and we stripped. Thing was, she didn't get wet, so no amount of poking or prodding got my cock inside her. It ended up with some heavy petting instead.

Then, as someone mentioned earlier, was another bad sexual experience: the teenage years. It wasn't until I was 23 that I got lucky, but that relationship was over after four months. Fast forward 16 years. I had been single for three years. The same woman wrote me, I called her, and we rekindled our relationship. We lived quite a bit apart, though, so we decided to meet up halfway, in Stockholm.

We met at the station Friday evening, bought a salad each to bring to the hotel, and got inside the room. She had checked in earlier, and there were wine, roses, candles... We had some wine and salad, then she went down on me, and then I on her (my first oral!). Then we fucked for the first time in ages. It was all pretty good, apart for her old handicap - that she couldn't achieve orgasm together with someone else. Well, it didn't deter me...

...until I began to feel queasy. Was it the salad? Was it some psychosomatic reaction to a situation I wasn't prepared for? Suddenly, I had to reach for the wastepaper basket. I threw up violently, and that put an end to that night of passion... My body wasn't finished with me, though. I threw up some more, and then my insides thought diarrhea was a good idea.

So there I was, feeling like shit, having doubts about the whole affair, and ashamed for having both our hopes up. I wasn't much better next day. No puking, but had the runs. Told her "it wasn't her, but me", and was miserable until Sunday morning, when I mustered enough energy to make it back to the railway station. She wasn't a happy bunny.

We did see each other once more a few weeks later. We had some OK sex, but that was it. A year later, my old friend Kissa told me she loved me. We met, had the best sex ever, and married less than ten months later.

 

[gracie920101]

Never had complaints before!

During a hot and heavy session, I'd had my fun and was trying to help him cum. I was mortified when he to be told me to be quiet and be still because he couldn't come with me moaning or moving underneath him.
Needless to say, this turned into a one night stand because I wouldn't see him again.

 

[DewMee]

Worst... my ex husband waking me up in the morning stuffing his cock into me and cumming after three or four thrusts, climbing off and heading to work. I got nothing out of it.

 

[talkeasy5813]

My worst experience was with a guy I dated years ago. I was giving him a hand-job and asked if he wanted to touch my breasts and he declined saying he's not interested in breasts. Considering my breasts are one of my best physical assets that most guys seem to like I was surprised and my ego was a little bruised.