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Your worst sexual experience

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After the thread on "bad sex" I'm wondering what everyone's worst sexual experience was. This is open to men and women.
Alpha Blonde
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Event: Losing my virginity
Location: On a blanket on the floor of his basement
Time: Just before Christmas

I was very nervous and so was he. He was not even close to being a virgin but was hyper paranoid about causing me pain. The entire process took forever, because he kept backing off...which actually ended up causing even more (prolonged) discomfort for me.

Then, once he was completely inside me, I barely had enough time to even register that "oh wow, I'm actually having sex", before he came. The whole thing was over almost before it began.

I didn't want to do it again because after the first round, I was still sore.

Sooo.. I went back to my house, made myself a bowl of candy-cane ice-cream, and called my girlfriends to tell them the exciting news. The news mostly amounted to "so THAT'S what all the fuss is about?".

Sadly, sex never did get any better with him. He was a minute-man no matter what we tried. But hey, I didn't really know any better at the time, and didn't want to complain.

The time to complain is later, when you finally know better...
Lurker
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Haha, I'm starting to wonder if any female has ever enjoyed he "first time"
Constant Gardener
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Event: Mary, 40 year old avowed lifelong lesbian (virgin to men)
Location: Sofa, my house.
Duration: Fortunately all of two minutes (if that).
Time: Just before Christmas, 2004

Mary had answered my AFF ad, shortly before Thanksgiving. I checked out her profile, her photos were vague as they were scanned. She was the volleyball coach for the same local high school she'd graduated from. I noticed her profile stated she was lesbian but curious about bisexuality.

Mary had developed a relationship with an opposing team's volleyball coach, fifteen years older than she, during her own senior year in high school. This relationship cemented while she attended college in Lawrence, KS...just 40 miles from her home area. The two women began living together in an open yet committed relationship after Mary graduated university.

Mary's lover was stricken with muscular dystrophy in 1997, and Mary had been pretty much her caretaker only - for the previous six years. Mary had missed being held, loved and caressed...more than anything else. She felt ostracized, lonely and alone. She had never kissed a boy or a man. She was also, pretty damned good looking...for a forty year old or a thirty year old, she was foxy.

We had conversed for almost three weeks, several nights a week via email, and chat. Escalated to phone conversations a week before I agreed to meet her in person, while I was out Christmas shopping. Against my better judgement, quite possibly alcohol influenced, as I was frequently pickled during this span of time, I agreed to meet her at a Bed, Bath and Beyond.

She walked up on me as I was pushing my loaded cart out of the store and I was standing in front of a large picture window in front of the next door - Target Store, admiring their lighting display. We were talking on the phone, so Mary knew exactly where I was standing.

I'd since seen three recent photos of Mary and amazingly, she looked even sexier in person. Beautiful smile, radiant brown eyes. Wheels started spinning in my head, 'This might not be so bad at all, dude.' 5'7" and 120 pounds of toned, fit female with gorgeous blonde, shoulder length hair and a firm, athletic ass. Very pretty, very feminine facial features. Classic lipstick fem. I was slightly stunned, and not surprisingly, sporting wood.

I had thought I made it clear to Mary, what AFF was all about, to me. She had insisted that she felt a connection with me and she wanted me to be the man who she surrendered her virginity to. She'd slipped out to meet me for a few hours after ensuring her lover was resting as peacefully as possible.

She helped me load my vehicle and I asked if she'd like to go grab a cup of Starbucks or a cocktail at the bar and grille across the parking lot.

"I just want to get right down to it, like I read in your stories."

"Follow me, sweetheart."

Twenty minutes later, I was pulling into my garage and Mary was parking behind me in the driveway.

Two minutes later, as I was hanging my coat in the hall closet...Mary jumped on my back like a panther and started biting my neck.

Biting.My.Neck. Growling. (maybe your kind of girl, Damon)

I managed to shake her off of me and as gently as possible - onto my sofa and she began to rip off her jeans as I felt slick warmth on my neck, with my fingers and softly said: "Please babe, no more biting."

By the time I had kicked off my jeans and removed my sweater...Mary was butt-naked and she had assumed the face down, ass up position on all fours and in the semi-darkness of my living room...I could tell, she was very well built. Small breasts, but slender and what an ass!

Foreplay? Almost zilch...she couldn't kiss worth a damn, in my opinion. And she was not lubricated. She was definitely 'primed up' in her mind, but her body wasn't reacting.

Saliva helped some, but then she was so tight, I could barely get myself in. After half a dozen slow strokes...she began to scream and cum and something...some women will say she gushed or squirted...I don't know.

I've been with 'squirters' before and I'm not a fan...but Mary cut loose and before I knew it...my sofa was pooling.

On the next deep stroke, I felt her already tight vagina literally spit me out as Mary lurched forward, her arms splayed out and she passed out shivering and quivering on her belly, on the sofa seating...I stood up...lost my erection, walked to my kitchen to get a paper towel to wipe my thighs and shins dry, then went back out to the living room and put on my jeans, leaving my briefs wherever I'd tossed them.

I lit a smoke and thought to myself: 'You did this to yourself, dude.'

Forty or so minutes, and almost four cigarettes later...Mary woke up, I'd placed her clothing neatly in a pile at her feet and she noticed them and began to dress. I left the living room to give her privacy and was wrapping gifts on my dining room table. She sidled up behind me, her hands reaching for my crotch.

"Oh my god, that was even better than I ever expected it to be...You are quite the big boy...I'm so sore now."

We lightly kissed each other's lips and she proclaimed, "My goodness, I need to get home, I've been gone nearly two hours!"

I walked her outside, not wearing a shirt - to her sports car, asked her if she knew how to get out of my neighborhood to the next main road...and she assured me she did. And then she was gone. I didn't even feel like jacking off. Wrapped all my gifts, received a call from Mary on my cell - to let me know she'd made it home.

I went to bed two hours and nine beers later. At least I copped a buzz so the night wasn't totally blown.

I came home from the office the next evening about 8pm, as I'd stopped to do some more shopping...and I saw four little metal and plastic reindeer (with the little twinkling light display) set up in my front yard...with a note attached to Rudolph's nose.

I saw you admiring Blixen and his crew and knew they would look so good in your yard, here by these evergreens. What a lover you are, talk to you soon, you handsome Big Boy!

Oh fuck, what had I done?

I loosely stayed in touch with Mary til the following February, shortly after her partner had passed away. She'd finally gotten subtle hint number 17 - which I had been beaming to her since I thanked her for her reindeer gifts...and she met another man on AFF and decided to take him for a spin too.

He lived 190 miles away in Omaha. He quit his job, divorced his wife, moved to Kansas City and he and Mary were supposed to get married in March, 2005. I don't know if they did or not. He didn't want her talking to me anymore.

Thank gawd.

Poor girl deserved better than me.
The same GQP demanding we move on from January 6th, 2021 is still doing audits of the November 3rd, 2020 election.
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Mine was in college. It was 1986 and he was a visiting poet whose work focused on the urban black experience. He was a sexy black man in his 40's and even wore a beret. I thought his poetry was passionate and revolutionary and that he was hot. During the after party we gravitated towards one another and hit it off. Our conversation moved to a local bar and we talked for hours. Somewhere in that time he took me back to his hotel. That's when it got weird. We smoked a joint and as we started getting physical, he started telling me how he loved "rich sexy white bitches" and began to call me his "pretty little white slut" as I went down on him. He was my first black lover and I thought he was just being kinky. Quite frankly, I enjoy some nasty talk in bed and it was adding to my experience. But then it changed. He was about to penetrate me when he started going on and on about whether I could handle his "big black dick." I didn't want to say the truth - that it was one of the smallest penises I had seen - so instead I giggled a little (mostly out of nervousness) and said something equally stupid: "Don't worry - I've handled bigger." He knew he was my first black lover and I guess the fact that I had been with white men with bigger penises was more than he could handle. He became explosive and began berating me. I quickly dressed and his insults became worse. Luckily he was angry enough to throw me out of his hotel room rather than hurt me. I used the hotely lobby phone to call my roomate, she picked me up and we went home and laughed and cried as I told her what happened. But the image of my naked revolutionary black poet screaming at me with his shriveled up little dick bouncing around is still fresh in my memory.
Active Ink Slinger
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I can honestly say that I have only ever had one bad sexual experience. I think pretty much all sex is good and some is fucking fantastic but there was this one guy. He was a competition middle weight class body building champion with a body you just could not believe. Unfortunately the size of his penis was unbelievable too. I mean like maybe a little over 3 inches completely hard. Head hitting the headboard of the bed and still where the hell is that tiny thing!!! UGH Yep that was my last date with him. He never called and neither did I.
Bunny12


Bunny Rabbits cute and fuzzy they want to love you but they have razor sharp teeth - don't piss them off!
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About a year ago I was this chick. We were on my roommate's bed. She informed me, as I was sticking it in, that this was her 2nd time ever to have sex. She eventually got used to it but then started clawing my back. Not a fan of that, at all. I could not get off because of it. Eventually I stopped and went to the bathroom until she left. Haven't heard from her since then lol.
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Quote by Remington
About a year ago I was this chick. We were on my roommate's bed. She informed me, as I was sticking it in, that this was her 2nd time ever to have sex. She eventually got used to it but then started clawing my back. Not a fan of that, at all. I could not get off because of it. Eventually I stopped and went to the bathroom until she left. Haven't heard from her since then lol.


Yeah, on 3 separate occasions I've been a girl's 2nd time. Not great. Makes me wonder why so many men have a thing for virgins.
Artistic Tart
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Quote by Remington
She eventually got used to it but then started clawing my back. Not a fan of that, at all. I could not get off because of it. Eventually I stopped and went to the bathroom until she left. Haven't heard from her since then lol.


Did you ask her to stop clawing your fucking back, or did you leave her wondering what the hell happened when you locked yourself in the bathroom until she left?


The clawing was probably a sign that she was enjoying herself, if as you say it started after she got 'used to it'. Poor girl probably wonders what she did wrong and doesn't know. Her future partners can now thank you for her issues with sex.5mX6xYwM8NKvdB3R
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Quote by LadyX
Quote by Remington
She eventually got used to it but then started clawing my back. Not a fan of that, at all. I could not get off because of it. Eventually I stopped and went to the bathroom until she left. Haven't heard from her since then lol.


Did you ask her to stop clawing your fucking back, or did you leave her wondering what the hell happened when you locked yourself in the bathroom until she left?


The clawing was probably a sign that she was enjoying herself, if as you say it started after she got 'used to it'. Poor girl probably wonders what she did wrong and doesn't know. Her future partners can now thank you for her issues with sex.eGKIUHZb1WPuwJcT



This is actually one of my hubby's triggers. If I ever want to push him over the edge all I need to do is run my nails on his back with a little dirty talk and he is there!
Artistic Tart
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Quote by Alissa


This is actually one of my hubby's triggers. If I ever want to push him over the edge all I need to do is run my nails on his back with a little dirty talk and he is there!


I've been with a couple of guys who really get into it too- and it's a sure sign that I'm loving what he's giving me. That, and I want to mark him.vhKpRnm0qr5aE5GF
Active Ink Slinger
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Quote by DamonX
Quote by Remington
About a year ago I was this chick. We were on my roommate's bed. She informed me, as I was sticking it in, that this was her 2nd time ever to have sex. She eventually got used to it but then started clawing my back. Not a fan of that, at all. I could not get off because of it. Eventually I stopped and went to the bathroom until she left. Haven't heard from her since then lol.


Yeah, on 3 separate occasions I've been a girl's 2nd time. Not great. Makes me wonder why so many men have a thing for virgins.


I've wondered that myself too. Most of the time the girl becomes clingy. Not saying that all girls get that way and sorry if I offend any girl.
Go check out my new story - How Did This Happen? - John's Story
Active Ink Slinger
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LadyX,

I should not have been so vague about the situation. First, she wasn't the type I usually date or sleep with. Second, she kept going on about how sex is overrated and not made out to be like everyone says it is. She annoyed me from the get go, but was persistent to get into my pants. Looking back on it now, I never should've even put myself in that position. Oh well, guess we learn from our mistakes lol.
Go check out my new story - How Did This Happen? - John's Story
Constant Gardener
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Quote by Remington
She annoyed me from the get go, but was persistent to get into my pants. Looking back on it now, I never should've even put myself in that position. Oh well, guess we learn from our mistakes lol.


I've got some t-shirts with that saying, inked on the front and back, if you're interested.
The same GQP demanding we move on from January 6th, 2021 is still doing audits of the November 3rd, 2020 election.
Constant Gardener
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Quote by Kyle
There was a topic on bad sex. Here is one of mine. I was having casual sex with a woman I met at a convention. I wanted to tell her to shut the fuck up, I found her constant dialog so distracting. I just had to stop it. There was no point, there was no connection between us and the chatter was a substitute. I would have had a better time going to my room alone, putting on a pay-per-view porn movie and masturbating.


Reminds me of a woman I used to bang, who would occasionally, out of the blue - while I was trying to get her off via penetration...start rambing about two or three previous casual lovers of hers.

"Gawd, he was hung like a horse."

"He was so big, I would come the moment he stuck that ten inch monster inside my wet cunt."

"James literally used to fuck my brains out all over this bed, his cockhead would both hurt and yet pleasure me like no other man, before...or since."

I'd want to retort: "Well, that explains why my seven thick inches are barely making a dent, and why it feels like I'm fucking a tepid bowl of pudding. Keep your t-shirt on babe, your stretchmarks gross me out."

Alas, I kept my mouth shut, closed my eyes, thought of someone I really once loved, pulled out and shot my loads all over her inconsiderate face. Wiped my dick off on her curtains, went to her bathroom and peed in her sink.

*just kidd'n about the last part, everyone.
The same GQP demanding we move on from January 6th, 2021 is still doing audits of the November 3rd, 2020 election.
Active Ink Slinger
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You're well capable of doing that though wmm.

Little story of my own. A one night stand where I was eating a girl out and she got her period during it. That kinda killed the mood and my erection lol.
Insert typical super smart ass comment courtesy of thepainter here.
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Quote by thepainter
You're well capable of doing that though wmm.

Little story of my own. A one night stand where I was eating a girl out and she got her period during it. That kinda killed the mood and my erection lol.


Yeah that would've ended me as well.
Go check out my new story - How Did This Happen? - John's Story
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Quote by WellMadeMale
Quote by Remington
She annoyed me from the get go, but was persistent to get into my pants. Looking back on it now, I never should've even put myself in that position. Oh well, guess we learn from our mistakes lol.


I've got some t-shirts with that saying, inked on the front and back, if you're interested.


Preferably with a spelling error or two.
Lurker
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Quote by DamonX
Haha, I'm starting to wonder if any female has ever enjoyed he "first time"


i loved my first time!! had an awesome g spot orgasm!! but thats not the topic at hand.

my worst experience was with a boy in high school who drank A LOT of mountain dew and it made giving head just awful! in fact it ruined me from swallowing altogether! and not only was it bad to have him cum in my mouth he never reciprocated and let me cum in his!! lol!
Lurker
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Quote by LittleMissBitch
Quote by DamonX
Haha, I'm starting to wonder if any female has ever enjoyed he "first time"


i loved my first time!! had an awesome g spot orgasm!! but thats not the topic at hand.

my worst experience was with a boy in high school who drank A LOT of mountain dew and it made giving head just awful! in fact it ruined me from swallowing altogether! and not only was it bad to have him cum in my mouth he never reciprocated and let me cum in his!! lol!


MountainDew? Really? I've never heard that before. Note to self...Don't drink Mountain Dew.
Active Ink Slinger
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Quote by DamonX
Quote by LittleMissBitch
Quote by DamonX
Haha, I'm starting to wonder if any female has ever enjoyed he "first time"


i loved my first time!! had an awesome g spot orgasm!! but thats not the topic at hand.

my worst experience was with a boy in high school who drank A LOT of mountain dew and it made giving head just awful! in fact it ruined me from swallowing altogether! and not only was it bad to have him cum in my mouth he never reciprocated and let me cum in his!! lol!


MountainDew? Really? I've never heard that before. Note to self...Don't drink Mountain Dew.


I don't drink Mountain Dew so I'm fine
Go check out my new story - How Did This Happen? - John's Story
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Here's one of mine....

I met this red head at a country bar. (Why are red head's always crazy?) She drove us to my house (even though she was way to drunk to be driving). After watching a movie, we started making out on my bed. After a few minutes, I realized that she was fingering herself. I thought that was cool...until she gave herself an orgasm and thrashed so violently that she knocked me out of the bed. I fell out, smashed my head on my night table and shattered my alarm clock into pieces. When I climbed back into bed, she said that she was too tired to do anything else, although she promised that she would "pleasure me" in the morning. I laid there, horny and awake for a few hours before I finaly fell asleep. While I was sleeping, she got up and snuck out, stealing a hundred dollar bill on her way out.

Damn red-heads.
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Quote by DamonX
Haha, I'm starting to wonder if any female has ever enjoyed he "first time"

I enjoyed mine immensely! Having a considerate, kind man might have been the trick though.
Ugh, my worst was a well hung guy. I'd heard rumours that the new guy at my work was supposedly hugely hung and several co-workers and I were curious to see who could find out the truth of it as it had been reported by a guy who'd gone to the gym with him. He asked me out, and while I'm not exactly a prude, I usually spend a bit of time before I go to bed with a guy. Unless of course, I'm drinking vodka. On the second date it goes to the bedroom, and I discover that he is indeed well hung, nine inches plus, and he has no idea whatsoever how to use it. Nor does he have any other skills to fall back after he comes in less than two minutes! He's rough, rushes me, takes no time to make sure I'm comfortable with his larger size and finishes in record time? When my request for some cunnilingus was rebuffed, I threw his ass out of my apartment and told him I'd had far bigger and far better (better, yes, bigger, no) and that he needed to learn how to last longer than that if he ever had any hopes of pleasing a real woman. Luckily the next guy was pretty good, and the guy after that turned out to be hubby, who was fantastic from the get-go.
"A black cat crossing your path signifies that the animal is going somewhere." - Groucho Marx
Alpha Blonde
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Quote by castlequeen
Quote by DamonX
Haha, I'm starting to wonder if any female has ever enjoyed he "first time"

I enjoyed mine immensely! Having a considerate, kind man might have been the trick though.
Ugh, my worst was a well hung guy. I'd heard rumours that the new guy at my work was supposedly hugely hung and several co-workers and I were curious to see who could find out the truth of it as it had been reported by a guy who'd gone to the gym with him. He asked me out, and while I'm not exactly a prude, I usually spend a bit of time before I go to bed with a guy. Unless of course, I'm drinking vodka. On the second date it goes to the bedroom, and I discover that he is indeed well hung, nine inches plus, and he has no idea whatsoever how to use it. Nor does he have any other skills to fall back after he comes in less than two minutes! He's rough, rushes me, takes no time to make sure I'm comfortable with his larger size and finishes in record time? When my request for some cunnilingus was rebuffed, I threw his ass out of my apartment and told him I'd had far bigger and far better (better, yes, bigger, no) and that he needed to learn how to last longer than that if he ever had any hopes of pleasing a real woman. Luckily the next guy was pretty good, and the guy after that turned out to be hubby, who was fantastic from the get-go.


You go girl!! I love that story! Well done!!
Lurker
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Tough to make these kinds of posts....things we don't like. I had a gal friend who I was always infatuated with and luckily, she with me. We finally got hooked up
once and went to bed. I couldn't keep my hands off her beautiful body. We had such a great mental connection...but when we got naked she changed. She offered
little in return to the experience and I felt like my caresses, kisses and touches were met with little pleasure. I was shocked and confused. All the message were there
for a wonderful naked union. But, it was flat, and uninteresting. To this day, I still don't understand it and feel bad for her if her sex life remained that uninspired.
Rookie Scribe
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Event: First time with the object of my desire first year at Uni
Location: Her new flat
Time: Just after the end of the first year

She was a real cute little indie-chick with a northen accent (sounded just like Cheryl Cole to my untrained southern ear). I made it clear I was interested right from the start, but she wouldn't date me as we were in the same flat. Finally relented after we moved in to separate houses. Big first night comes when I go back to her place. Turns out she wouldn't do doggy ("coz that's how homos do it") and wouldn't let me go down on her as it was "dirty" and made no noise whatsoever in case anyone heard her having sex. Absolutely gutted, total let down. Thought I'd done something wrong, but a mate who slept with her in our final year reported the same thing. Didn't last long thankfully. Weird.
"I like pornography - who doesn't?" Moby
Story Teller
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well...the sex was ok, but I ended up getting pink eye from him...LOL...He didn't tell me he had pink eye.
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Quote by PassionFlwer74
well...the sex was ok, but I ended up getting pink eye from him...LOL...He didn't tell me he had pink eye.


Did he cum in your eyeball?
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Quote by PassionFlwer74
well...the sex was ok, but I ended up getting pink eye from him...LOL...He didn't tell me he had pink eye.


Pink eye comes from fecal matter. Was your eye in his ass?
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