In the spirit of Hawking and Quickblade...post your worst sexual encounter story

[Mars]

is there a problem?

[mass 04]

"So, Mars. You just wanted to talk. Is that right? Explain the whisky, 5 boxes of condoms, and ball gag then."

[Mars]

"im sorry sir.. are you a cop or something?"

"we will come to that in a minute, i want you to ask some questions first"

[Board_SHERIF]

not my worst but my weirdest:

went to a gang bang that was organized by the chick who was going to get banged, on the phone she sounded like a 45 year old white trash fat.  I was going to pass on it, but it was only 5mins from my house.  I went to the motel and knocked on the room door, her  fat boyfriend answered and told me to come in.  There on the bed was a 20ish tanned hot chick getting poked from behind while sucking another guy, this chick was like something out of a porn movie - tanned, shaved, implants, the whole works.  I got in there and she was sucking me when all of a sudden she starts shooting "stuff" out of her pussy, I thought it was piss - but it had a "sweet" smell.  I was there for 45 mins and she "shot" this stuff out 5 times, I thought chicks squirting cum was fake - it was pretty weird.  Anyway she licked my arsehole while I jerked and blew all over her face, as I was leaving her boyfriend said "hope you enjoyed my slut" - I was like "arrh yeh it was good".

[Smokincrazy]

not my worst but my weirdest:

went to a gang bang that was organized by the chick who was going to get banged, on the phone she sounded like a 45 year old white trash fat.  I was going to pass on it, but it was only 5mins from my house.  I went to the motel and knocked on the room door, her  fat boyfriend answered and told me to come in.  There on the bed was a 20ish tanned hot chick getting poked from behind while sucking another guy, this chick was like something out of a porn movie - tanned, shaved, implants, the whole works.  I got in there and she was sucking me when all of a sudden she starts shooting "stuff" out of her pussy, I thought it was piss - but it had a "sweat" smell.  I was there for 45 mins and she "shot" this stuff out 5 times, I thought chicks squirting cum was fake - it was pretty weird.  Anyway she licked my arsehole while I jerked and blew all over her face, as I was leaving her boyfriend said "hope you enjoyed my slut" - I was like "arrh yeh it was good".

I wonder how he feels when he kisses her goodnight?

[disturbia]

One time I "hit" the wrong hole....

(her naval, girl weighted 450lbs, imagine how deep and moist it was...)

are you serious? 450? cmon now

[big14]

 this is really gross
From the OT

Under the anonymity of the internet I have decided to tell the world my deepest darkest secret. This is something I have never told ANYBODY before and I usually tell everybody anything.

I haven't told anybody because of how they will react or what they will think of me in the future or if i have some type of disease.

I was 16 years old. I had just gotten my driver's license. I was just driving around real late at night and I saw this woman walking along the street. I kept looking at her and we made eye contact. I said "hey girl whats?" and she just waved and walked into a restaurant.

I continued to drive around and after about an hour I decided to head back home. Driving around that same part of town I saw that woman again. She was walking closer by this time so i asked her if she wanted a ride. She hopped right into my car and at this moment I began to realize something was wrong. In the deepest voice I have heard come from a woman, she asked me,

"so what do you want?"
My voice trembled as I told her "You're cute and i was just wondering if you wanted a ride."
"How much you got?"

As a 16 year old virgin, I just realized that right now I had a hooker in my car. After a little bargaining we settled on $9 in cash, the change in my ashtray, and the rest of my starbucks frappuccino .

She immediately undos my zipper and pulls out my penis while i am driving and starts to jerk my off. She then asks me, "So what are you into?"
"I'm into everything." I told her as my voice cracked.
"Are you into trannys?"

Right now i am extremely nervous, I am a 16 year old boy and I have a what looks to be a 32 year old man/woman jerking me off in my car while I am driving. I figured I was all ready in this far and this was a pretty awesome handjob so I told him/her "yeah baby."

At this point this he-she bends over onto my side of the car and starts sucking on the tip of my penis. This was the best feeling I have ever experienced. She then asks me if I want to go someplace more private. I was really worried at this time, but I was thinking with the little head and I told her sure. She tells me where to go and we pull into this real shady looking apartment complex. Her neighbors are standing out side looking and she tells me not to worry about them and that they are meth heads.

While i'm walking into her apartment the only thing I can think of is why i agreed to do this and that i was going to be killed/ raped by some other people in this apartment or by this shedude itself. We get into the room and she locks the door behind her and goes into the restroom. I am left standing in the living room now know what to expect next. Then this manwoman comes back out and tells me to get comfortable and she pulls down my pants and procedes to give me (what is still in my mind) one of the best blowjobs I have ever had. I look down to watch him sucking on my piece and I see she has her own dick out and she is masturbating while she is going to work on me. This man/ woman then starts to rub her dick on my leg as she blows me. I just close my eyes and try to imagine this is a woman while this tranny takes the whole thing and even swallows my seed.

As i am putting my pants back on and he/she is washing out her mouth she says next time i come back he's going to let me put it in his butt.

I leave and the whole ride back I am crying and I can't believe that I just wasted my first time with a transexual man. Then i start wondering what kind of diseases i could have gotten and the nervous start to get to me and I have to pull over an vomit. When I got home i scrubbed my whole body and sat there crying. For the next couple years I spent my life thinking I had HIV or full blown AIDs.

[spinnis]

Easy.  I would frequent this night club a lot and there was a cute as hell bartender that worked there.  She'd always flirt but it was hard to pick her up at the bar.  One night I saw her at the club on an off night and we started chatting it up.  She was looking sick hot.  She invites me back to her place.  We continue drinking and start making out, we head to her bedroom and I slip off her pants and stick my fingers in, when I bring them back up it just stank.  Stank as foul old cans of tuna sitting in the sun.  Just nasty.  My fingers are soaked in this nasty juice.  I wipe it all off on her pillow without drawing attention.  We fuck but at that point I was not as horny, it was more of a blue balls forced fuck to ensure I blew my load.  I left right away.  The entire drive home I can smell this stank on me.  My hands, my crotch area, just nasty.  Even scrubbing in the shower I couldn't seem to scrub this shit off.  It was shitty because she was a gorgeous girl, pretty face with nasty hygeine.

been there done that,

the girl I was with was a clean girl though, probably some fucked up PH pussy levels though

[Parker]

not my worst but my weirdest:

went to a gang bang that was organized by the chick who was going to get banged, on the phone she sounded like a 45 year old white trash fat.  I was going to pass on it, but it was only 5mins from my house.  I went to the motel and knocked on the room door, her  fat boyfriend answered and told me to come in.  There on the bed was a 20ish tanned hot chick getting poked from behind while sucking another guy, this chick was like something out of a porn movie - tanned, shaved, implants, the whole works.  I got in there and she was sucking me when all of a sudden she starts shooting "stuff" out of her pussy, I thought it was piss - but it had a "sweet" smell.  I was there for 45 mins and she "shot" this stuff out 5 times, I thought chicks squirting cum was fake - it was pretty weird.  Anyway she licked my arsehole while I jerked and blew all over her face, as I was leaving her boyfriend said "hope you enjoyed my slut" - I was like "arrh yeh it was good".

So it was a cuckhold gangbang...her old man couldn't please her.

[spinnis]

this is really gross
From the OT

Under the anonymity of the internet I have decided to tell the world my deepest darkest secret. This is something I have never told ANYBODY before and I usually tell everybody anything.

I haven't told anybody because of how they will react or what they will think of me in the future or if i have some type of disease.

I was 16 years old. I had just gotten my driver's license. I was just driving around real late at night and I saw this woman walking along the street. I kept looking at her and we made eye contact. I said "hey girl whats?" and she just waved and walked into a restaurant.

I continued to drive around and after about an hour I decided to head back home. Driving around that same part of town I saw that woman again. She was walking closer by this time so i asked her if she wanted a ride. She hopped right into my car and at this moment I began to realize something was wrong. In the deepest voice I have heard come from a woman, she asked me,

"so what do you want?"
My voice trembled as I told her "You're cute and i was just wondering if you wanted a ride."
"How much you got?"

As a 16 year old virgin, I just realized that right now I had a hooker in my car. After a little bargaining we settled on $9 in cash, the change in my ashtray, and the rest of my starbucks frappuccino .

She immediately undos my zipper and pulls out my penis while i am driving and starts to jerk my off. She then asks me, "So what are you into?"
"I'm into everything." I told her as my voice cracked.
"Are you into trannys?"

Right now i am extremely nervous, I am a 16 year old boy and I have a what looks to be a 32 year old man/woman jerking me off in my car while I am driving. I figured I was all ready in this far and this was a pretty awesome handjob so I told him/her "yeah baby."

At this point this he-she bends over onto my side of the car and starts sucking on the tip of my penis. This was the best feeling I have ever experienced. She then asks me if I want to go someplace more private. I was really worried at this time, but I was thinking with the little head and I told her sure. She tells me where to go and we pull into this real shady looking apartment complex. Her neighbors are standing out side looking and she tells me not to worry about them and that they are meth heads.

While i'm walking into her apartment the only thing I can think of is why i agreed to do this and that i was going to be killed/ raped by some other people in this apartment or by this shedude itself. We get into the room and she locks the door behind her and goes into the restroom. I am left standing in the living room now know what to expect next. Then this manwoman comes back out and tells me to get comfortable and she pulls down my pants and procedes to give me (what is still in my mind) one of the best blowjobs I have ever had. I look down to watch him sucking on my piece and I see she has her own dick out and she is masturbating while she is going to work on me. This man/ woman then starts to rub her dick on my leg as she blows me. I just close my eyes and try to imagine this is a woman while this tranny takes the whole thing and even swallows my seed.

As i am putting my pants back on and he/she is washing out her mouth she says next time i come back he's going to let me put it in his butt.

I leave and the whole ride back I am crying and I can't believe that I just wasted my first time with a transexual man. Then i start wondering what kind of diseases i could have gotten and the nervous start to get to me and I have to pull over an vomit. When I got home i scrubbed my whole body and sat there crying. For the next couple years I spent my life thinking I had HIV or full blown AIDs.

hahahahahahahahaha

[tbombz]

this is really gross
From the OT

Under the anonymity of the internet I have decided to tell the world my deepest darkest secret. This is something I have never told ANYBODY before and I usually tell everybody anything.

I haven't told anybody because of how they will react or what they will think of me in the future or if i have some type of disease.

I was 16 years old. I had just gotten my driver's license. I was just driving around real late at night and I saw this woman walking along the street. I kept looking at her and we made eye contact. I said "hey girl whats?" and she just waved and walked into a restaurant.

I continued to drive around and after about an hour I decided to head back home. Driving around that same part of town I saw that woman again. She was walking closer by this time so i asked her if she wanted a ride. She hopped right into my car and at this moment I began to realize something was wrong. In the deepest voice I have heard come from a woman, she asked me,

"so what do you want?"
My voice trembled as I told her "You're cute and i was just wondering if you wanted a ride."
"How much you got?"

As a 16 year old virgin, I just realized that right now I had a hooker in my car. After a little bargaining we settled on $9 in cash, the change in my ashtray, and the rest of my starbucks frappuccino .

She immediately undos my zipper and pulls out my penis while i am driving and starts to jerk my off. She then asks me, "So what are you into?"
"I'm into everything." I told her as my voice cracked.
"Are you into trannys?"

Right now i am extremely nervous, I am a 16 year old boy and I have a what looks to be a 32 year old man/woman jerking me off in my car while I am driving. I figured I was all ready in this far and this was a pretty awesome handjob so I told him/her "yeah baby."

At this point this he-she bends over onto my side of the car and starts sucking on the tip of my penis. This was the best feeling I have ever experienced. She then asks me if I want to go someplace more private. I was really worried at this time, but I was thinking with the little head and I told her sure. She tells me where to go and we pull into this real shady looking apartment complex. Her neighbors are standing out side looking and she tells me not to worry about them and that they are meth heads.

While i'm walking into her apartment the only thing I can think of is why i agreed to do this and that i was going to be killed/ raped by some other people in this apartment or by this shedude itself. We get into the room and she locks the door behind her and goes into the restroom. I am left standing in the living room now know what to expect next. Then this manwoman comes back out and tells me to get comfortable and she pulls down my pants and procedes to give me (what is still in my mind) one of the best blowjobs I have ever had. I look down to watch him sucking on my piece and I see she has her own dick out and she is masturbating while she is going to work on me. This man/ woman then starts to rub her dick on my leg as she blows me. I just close my eyes and try to imagine this is a woman while this tranny takes the whole thing and even swallows my seed.

As i am putting my pants back on and he/she is washing out her mouth she says next time i come back he's going to let me put it in his butt.

I leave and the whole ride back I am crying and I can't believe that I just wasted my first time with a transexual man. Then i start wondering what kind of diseases i could have gotten and the nervous start to get to me and I have to pull over an vomit. When I got home i scrubbed my whole body and sat there crying. For the next couple years I spent my life thinking I had HIV or full blown AIDs.

lol!! funny. kind of hot too 

[myt1]

lol!! funny. kind of hot too 

 

[WingedLion]

jesus fucking crist !

am I the only straight guy here

[WingedLion]

 

big 14 is a dude who was making fun of me ..jesus

[Quickerblade]

big 14 is a dude who was making fun of me ..jesus

I dont think its his story, its from another forum

[WingedLion]

I dont think its his story, its from another forum

riiight

so he says 

[Stark]

"So, Mars. You just wanted to talk. Is that right? Explain the whisky, 5 boxes of condoms, and ball gag then."

Its called a "Snooker ball" .... shit I said to much

[Board_SHERIF]

So it was a cuckhold gangbang...her old man couldn't please her.

Yes, he took pics - I guess he jerked off to them later my himself in a dark closet.

[Stark]

I was 15.
Meet a girl and soon I was real hocked, I mean with 16 you don't think straight when there is a slight chance of pussy.
My parents had a close eye on me since they came one day early from holidays and found me with a girl in bed - I stacked up all the National Geographic under the doorhandle so my brother wasn't able to open the door - well guess what my mom had no problem opening the door...
Anyways I really wanted to see her bad - so I climed out of the window when everybody was asleep in my house, and off I go - take the train and I think an hour or so later she lets me in her basement room, nice house, family had no idea.
So we kinda make out and I thinking boy you're going to get laid.
Next thing I hear is somebody coming down the steps and banging on the door, I have no shoes and no socks on a T-Shirt no jacket.
She litterlay pushes me outside - it was cold - night winter frost and a little snow - she quickly closes the door and I am hugging the outside wall.
Her father asks all kind a questions and then leaves.
After like 5 min the door opens again and she gives me my stuff - says her father is real suspicious and I have to leave.
So of I say okay I try to see you tomorrow we kiss and she closes the door again.
Now I am standing with my dick in my hand - in the fucking freezing night trying to get my Rangers back on - they are like Dog Martins just with steel caps - you cannot just slip them on they need to be properaly laces.
So I am trying to get my shit on and all of a sudden I see a cat come around the corner of the house - Cat looks at me - I look at the Cat - Cat keeps walking ... and all of sudden I see the fucking cat RUN!!!!
It took a second or two for me to realize - FUCK ME SOMEBODDY IS COMING !!!!

So with my Rangers and Bomberjacket half on I start running like fuck - I jump over fences and trip the lights on other peoples propery and I can hear the dad shout - I see you again I fucking kill you

I've never seen her again

[Bobby]

Ya.....smelly pussy is a turn off. Hmmmm.......worst encounter,i think the only worst/embarassing encounter is probably letting the cannon balls loose too early, Two pump chump. The funniest sexual encounter i had, was pretty much once in a lifetime. This broad was so hammered, she got up to use the bathroom, couldnt even walk, walked right into her tv stand, with a dvd player on top, that came crashing down on her head, hahaa . Went to the bathroom, 5 min goes by, and shes still in there, i go in to check on her, shes passed out, sitting on the toilet buttnaked, i wake her up, and as soon as shes stands up she falls face first into the door, soo i help her back to the bed, threw a condom on and got to work as she was sound asleep she did not wake up I nutted then grabbed her thong for a souvenair, to remember her. Fuckin hilarious.

fixed

[Bobby]

this is really gross
From the OT

Under the anonymity of the internet I have decided to tell the world my deepest darkest secret. This is something I have never told ANYBODY before and I usually tell everybody anything.

I haven't told anybody because of how they will react or what they will think of me in the future or if i have some type of disease.

I was 16 years old. I had just gotten my driver's license. I was just driving around real late at night and I saw this woman walking along the street. I kept looking at her and we made eye contact. I said "hey girl whats?" and she just waved and walked into a restaurant.

I continued to drive around and after about an hour I decided to head back home. Driving around that same part of town I saw that woman again. She was walking closer by this time so i asked her if she wanted a ride. She hopped right into my car and at this moment I began to realize something was wrong. In the deepest voice I have heard come from a woman, she asked me,

"so what do you want?"
My voice trembled as I told her "You're cute and i was just wondering if you wanted a ride."
"How much you got?"

As a 16 year old virgin, I just realized that right now I had a hooker in my car. After a little bargaining we settled on $9 in cash, the change in my ashtray, and the rest of my starbucks frappuccino .

She immediately undos my zipper and pulls out my penis while i am driving and starts to jerk my off. She then asks me, "So what are you into?"
"I'm into everything." I told her as my voice cracked.
"Are you into trannys?"

Right now i am extremely nervous, I am a 16 year old boy and I have a what looks to be a 32 year old man/woman jerking me off in my car while I am driving. I figured I was all ready in this far and this was a pretty awesome handjob so I told him/her "yeah baby."

At this point this he-she bends over onto my side of the car and starts sucking on the tip of my penis. This was the best feeling I have ever experienced. She then asks me if I want to go someplace more private. I was really worried at this time, but I was thinking with the little head and I told her sure. She tells me where to go and we pull into this real shady looking apartment complex. Her neighbors are standing out side looking and she tells me not to worry about them and that they are meth heads.

While i'm walking into her apartment the only thing I can think of is why i agreed to do this and that i was going to be killed/ raped by some other people in this apartment or by this shedude itself. We get into the room and she locks the door behind her and goes into the restroom. I am left standing in the living room now know what to expect next. Then this manwoman comes back out and tells me to get comfortable and she pulls down my pants and procedes to give me (what is still in my mind) one of the best blowjobs I have ever had. I look down to watch him sucking on my piece and I see she has her own dick out and she is masturbating while she is going to work on me. This man/ woman then starts to rub her dick on my leg as she blows me. I just close my eyes and try to imagine this is a woman while this tranny takes the whole thing and even swallows my seed.

As i am putting my pants back on and he/she is washing out her mouth she says next time i come back he's going to let me put it in his butt.

I leave and the whole ride back I am crying and I can't believe that I just wasted my first time with a transexual man. Then i start wondering what kind of diseases i could have gotten and the nervous start to get to me and I have to pull over an vomit. When I got home i scrubbed my whole body and sat there crying. For the next couple years I spent my life thinking I had HIV or full blown AIDs.

high class prostitute/transwhatever