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Your strangest surprise

Starter: RogueLeader Posted: 15 years ago Views: 12.3K
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#4105935
Lvl 8
lol nerph...
#4105936
Lvl 13
I dated a foreign bird for a while and we took things slow in the beginning - I met her mom on our third date and they were conversing in her language which i didnt understand at the time. Next thing i know the mother starts ranting and raving at her and im thinking the mother is not happy that she is dating a foreigner.

Turns out the mother was screaming at her for not having fucked me yet as she felt that my attention would start to wander if i didnt get laid soon.

We had awesome sex that night and the mother was very happy to see me the next morning, I ended up dating the bird for two years.
#4105937
Lvl 7
When I was stationed in Hawaii, I met this girl that was on vacation from Italy. She was cute and I was young so I started showing her all the sights. After a few nights before she was supposed to leave we went back to her hotel room. She took off her pants (she always worn pants or ankle length skirts) and her legs were hairier than mine. She took her top off and she had a lot of armpit hair too... A big unshaven bush is one thing but hairy legs and armpit hair is another. Now I watch out for European women.
#4105938
Lvl 12
OK, here it is again. I meet a girl at a bar on a very cold Chicago nite, she has a supe3r cute face and I'm hooked. We drink a lot and go to her place. She takes off the scarf, the giant coat and bulky sweater, and, wow, she's got some big boobs! We drink a lot more at her place, and head to the bed room. The door closes and the room is pitch black. She jumps in the bed, and I slide in, not knowing my way around the room.
We make out for a while and.....uh-oh, those big boobs are fake....and they've hardened. It feels like theres big wads of silly putty under her skin. She's the fresh faced natural type, so I figured she had had a double mastectomy or something like that, and just act like I don't notice. I'm a nice guy that way.

OK, I've told the tale of ol' Silly Putty Tits four or five times here, but I never told the whole story...
We make out for a while, I pretend the boobs are fine, she grabs my cock and goes down on me. I find my way to her pussy, and go down on her. That was a very nice pussy, going down on her was simple, and she quickly gets all buckie-cummie, super wet and ready to go. I get in the ready position, she says "Here." and presses a condom against my chest, I put it on and work it in. I pump maybe eight times, and she says "Stop...stop, I didn't want you to do that."
What the fuck?
I'm in no mood for whatever bullshit reason she has, I go to the bathroom, pee out all the Old Style and Black Label, flush the condom, go back to her room, plop into bed and pass out. Wake up in time to go to my apartment, pick up my final paper for English, and go to school. Lucky for everyone, we just handed in our papers and class was over, cause I must have stank of beer, cigarettes and pussy.

Making me look even more like a jerk, I was cheating on my girlfriend! She was insistent on the phone that night that I don't go to the bar.










the strangest surprise was that I got an A on the English paper.
#4105939
I've had my share of odd sexual experiences. There was this chick on the floor of my co-ed dorm freshman year of college that grew her pubic hair out to just the right length to make it spiky as hell. Why? Because she was a nympho and wanted guys to last longer and you couldn't concentrate on cumming when you were rubbing yourself raw on her spikes of death. There was the chick that only wanted to fuck when we were both dosed up with Zanax. The list goes on...

However, my weirdest sexual experience was right before I graduated from high school. It was Spring semester and I was done with football and was basically messing around every afternoon because I only had class until like 1 or 2. My buddy and I pretty much spent every afternoon getting wasted and high. It was great. Anyway, he worked nights at the shitty K-Mart in our shitty little 15,000 person town. Being the spoiled, well to do, upper middle class asshole I was, I didn't need to work at fucking K-Mart, but he begged me to so we could fuck around and shoot the shit. I said fine, and before you know it I was the best damn cashier K-Mart had ever seen (not hard to accomplish, trust me!).

Anyway, it was a blast. We fucked around, routinely stole MASSIVE amounts of alcohol (oh, the wonderful days of no security cameras), and basically did whatever we wanted. It was also great because I met several chicks that didn't go to our school and ended up sleeping with them, etc. Well, this was back in my raging puberty hormone days when I'd basically screw anything that walked. If they were cute and had the correct amount of fingers and toes, I'd give them the dick. Other chicks that weren't so cute? I still let them suck me off all the time. Unfortunately, one of these so-so ugly chicks that I let give me some blowjobs turned out to be kind of psycho. Like, tell everybody we had sex and she got pregnant type of psycho. The other unfortunate part? Her white trash mom started working at K-Mart a couple of weeks after I signed up there....

So, one night as everyone was cleaning up the store after closing, this lady tracks me down, corners me in the toy section, and gives me a piece of her mind. She accuses me of sleeping with her daughter, getting her daughter pregnant, etc. and so forth. I was scared shitless because I didn't want this lady running to my folks and telling them all this utter bullshit, and I vehemently tried explaining to her that I didn't do anything with her daughter (lie) and that I hadn't had sex with her and knocked her up (truth). This lady, however, just isn't having it. She tells me that she wants to see me after work in a few minutes out at her car and that if I don't show up I'm in deep shit.

By this point, I'm freaking out and I'm also pissed off because I'm thinking that this shit wasn't worth the couple of mediocre blowjobs her ugly daughter gave me. However, I man up and go out to her Mustang. She tells me to get in and I ask her why. She promises that we aren't going anywhere and that she just wants to "talk." I'm a bit skeptical, but I say fuck it and climb in anyway. She gets this no-bullshit look on her face and asks me again to tell her the truth. Supposedly her daughter had shown her these "letters" that I'd supposedly written to her talking about us having sex, getting pregnant, etc. She shows them to me, I laugh my ass off, and tell her that isn't my hand writing and that no, none of that shit happened. I suppose I was feeling a bit relieved at that point and I admitted to her that yeah, her daughter had gone down on me, but that I wasn't interested in dating her and that actually, she looked a lot better than her daughter did (which she did, this lady was a straight MILF) and that in reality, her daughter didn't give very good head.

To this day I don't know why I said that, since it was completely out of character for me to EVER speak to an adult in that way, but it was one of the best decisions I ever made. This 30-something year old MILF looks at me, tells me she'll show me how it's done, gets topless, and then proceeds to give me one of the best blowjobs of my life right there in the K-Mart parking lot. She went at that dick like a champ and swallowed every drop. It was glorious. Afterwards, she told me she was sorry for climbing up my ass and that I was never to speak about it to anyone. I only spoke to her a few times in passing at work after that, and a few weeks later I was gone to college. Ironic part? Her daughter really did end up getting knocked up like 4-5 months later by some random asshole that she supposedly never saw again. Life's a bitch, ain't it?
#4105940
Lvl 37
Quote:
Originally posted by franklin

...

I would not have let fucked that dude if you were hangin with me that nite. Sorry.


Where the hell were ya, man?!?!?!

Seriously, though... It's not like the girl fazerix described... She just had a humongous bush... at least she shaved her legs and underarms. And it wasn't exactly a one night stand, either. We were actually dating for quite some time and were talking long term... I just couldn't talk her into letting me shave it. Oh well... she was a gold digger anyway.
#4105941
Lvl 7
When I first started dating my wife......she went out of town with her family. One of my friends asked to hang out and I was like ok.....not really thinking nothing of it .....We are chillin' at my place and I get on the computer. The next thing I know in my bedroom is my friend and she is naked, fingering the hell out of herself.........and I'm like wtf do I do now lol
the story goes on.........

but to this day.....I can't help to think.......dam, that girl did not care.......she stripped down and went wild lol
#4105942
Lvl 28
Quote:
Originally posted by Honda_X

...

Well, some of us can tell the difference between a vagina and an asshole. You're going to have to lose that pesky virginity before you start making comments like that sir...but one day you'll understand how silly it was.

Don't worry though, I'm sure there are all sorts of older chaps like yourself who just happen to still be virgins. Maybe join a Star Wars fanclub? It could double as a support group.

kthxbai.
did someone mention the darkside.... we don't only have cookies, but we have cool cars...
#4105943
Lvl 24
Atoms are neat, but I'd prefer a different car.
I mean, I'd take one without complaint, cause they're super neat. But yeah.
#4105944
Lvl 37
Quote:
Originally posted by Bangledesh

Atoms are neat, but I'd prefer a different car.
I mean, I'd take one without complaint, cause they're super neat. But yeah.


hey, hey, HEY! There are no cars on WBW!!!
#4105945
Lvl 37
Damn it! Did I kill my own thread???

Come on WBW! I know someone out there has an embarrassing story to tell!
#4105946
Lvl 20
Quote:
Originally posted by wtwhizz

I've had my share of odd sexual experiences. There was this chick on the floor of my co-ed dorm freshman year of college that grew her pubic hair out to just the right length to make it spiky as hell. Why? Because she was a nympho and wanted guys to last longer and you couldn't concentrate on cumming when you were rubbing yourself raw on her spikes of death. There was the chick that only wanted to fuck when we were both dosed up with Zanax. The list goes on...

However, my weirdest sexual experience was right before I graduated from high school. It was Spring semester and I was done with football and was basically messing around every afternoon because I only had class until like 1 or 2. My buddy and I pretty much spent every afternoon getting wasted and high. It was great. Anyway, he worked nights at the shitty K-Mart in our shitty little 15,000 person town. Being the spoiled, well to do, upper middle class asshole I was, I didn't need to work at fucking K-Mart, but he begged me to so we could fuck around and shoot the shit. I said fine, and before you know it I was the best damn cashier K-Mart had ever seen (not hard to accomplish, trust me!).

Anyway, it was a blast. We fucked around, routinely stole MASSIVE amounts of alcohol (oh, the wonderful days of no security cameras), and basically did whatever we wanted. It was also great because I met several chicks that didn't go to our school and ended up sleeping with them, etc. Well, this was back in my raging puberty hormone days when I'd basically screw anything that walked. If they were cute and had the correct amount of fingers and toes, I'd give them the dick. Other chicks that weren't so cute? I still let them suck me off all the time. Unfortunately, one of these so-so ugly chicks that I let give me some blowjobs turned out to be kind of psycho. Like, tell everybody we had sex and she got pregnant type of psycho. The other unfortunate part? Her white trash mom started working at K-Mart a couple of weeks after I signed up there....

So, one night as everyone was cleaning up the store after closing, this lady tracks me down, corners me in the toy section, and gives me a piece of her mind. She accuses me of sleeping with her daughter, getting her daughter pregnant, etc. and so forth. I was scared shitless because I didn't want this lady running to my folks and telling them all this utter bullshit, and I vehemently tried explaining to her that I didn't do anything with her daughter (lie) and that I hadn't had sex with her and knocked her up (truth). This lady, however, just isn't having it. She tells me that she wants to see me after work in a few minutes out at her car and that if I don't show up I'm in deep shit.

By this point, I'm freaking out and I'm also pissed off because I'm thinking that this shit wasn't worth the couple of mediocre blowjobs her ugly daughter gave me. However, I man up and go out to her Mustang. She tells me to get in and I ask her why. She promises that we aren't going anywhere and that she just wants to "talk." I'm a bit skeptical, but I say fuck it and climb in anyway. She gets this no-bullshit look on her face and asks me again to tell her the truth. Supposedly her daughter had shown her these "letters" that I'd supposedly written to her talking about us having sex, getting pregnant, etc. She shows them to me, I laugh my ass off, and tell her that isn't my hand writing and that no, none of that shit happened. I suppose I was feeling a bit relieved at that point and I admitted to her that yeah, her daughter had gone down on me, but that I wasn't interested in dating her and that actually, she looked a lot better than her daughter did (which she did, this lady was a straight MILF) and that in reality, her daughter didn't give very good head.

To this day I don't know why I said that, since it was completely out of character for me to EVER speak to an adult in that way, but it was one of the best decisions I ever made. This 30-something year old MILF looks at me, tells me she'll show me how it's done, gets topless, and then proceeds to give me one of the best blowjobs of my life right there in the K-Mart parking lot. She went at that dick like a champ and swallowed every drop. It was glorious. Afterwards, she told me she was sorry for climbing up my ass and that I was never to speak about it to anyone. I only spoke to her a few times in passing at work after that, and a few weeks later I was gone to college. Ironic part? Her daughter really did end up getting knocked up like 4-5 months later by some random asshole that she supposedly never saw again. Life's a bitch, ain't it?


Possibly best story ever. And you tell it so well. With such enthusiasm.

Srsly. Fine story.
#4105947
Lvl 37
Quote:
Originally posted by hydrahead

...

Possibly best story ever. And you tell it so well. With such enthusiasm.

Srsly. Fine story.


yeah, but what about YOUR story???

Come on folks! I'm sure there are more folks here that have embarrassing stories!
#4105948
Lvl 21
Quote:
Originally posted by monsterk

I dated a girl that said she was a virgin and was holding out for marriage.
She also sad that didn't mean we couldn't fool around. One thing led to another and she's suckin' my dick. Good. I mean real good. I said if she was a virgin how did she know how to suck so well. She said her brother had a huge porn collection that her and her girlfriend would watch. Then she goes back to work, hitting all the good spots and cramming as much as she can get into her throat. When I tell her I going to release she stops and takes the load right in the face! She then looks at me with my spunk on her face and asks if she did it right.


Thats awesome "did i do it right?" ... gold!


Iv been with a few girls that wouldn't take their shirts off... everything else but not the shirt.

That's about all i can think of right now...
#4105949
Lvl 3
So a few years ago between my 1st and 2nd deploymnent. I meet this girl at a a friend from works house party. I had proceeded to get fairly shit faced. Talking about all sorts of crazy shit when she asks why everyone who lives at the house keeps making me do shots for as they walk by. I tell here aobut the fact that in a couple of short weeks I leave for training followed by a year or more in Iraq. So we get tlaking about how my plan is to have as much fun doing everything I like to do as possible. Basically drinking, fishing, off roading and and having as much sex with basically anythign female with a pulse. She says she is totally fine with this and takes me back to her place. She turns out to be a whole lot of fun and dirty. SO we play around off and n while I am home. We start trying some things a little of this and some of that. But she is swears up and down that she will never take a dick up her ass. But I had noticed that when I grabbed her ass to give it hard she woudl always end up squirming just so that the waste department would get some stimulation. So I played with it more and more and eventually got to slip it in. Was amazing turns out this chick was a total butt slut to the pot she woudl orgasm so hard she would just keep orgasming making her screams louder and louder which was ok with me cuz I knew the girls who lived above her. But thats a whole nother story from when I had first gotten back from Afghanistan. The suprise though wasnt that she was a total butt slut but the fact that she was bat shit f%##ing insane. She started ot attack my friends and my roomates g/f's to cap it all off she filed a false domestic abuse report after I told her to fuck off cuz I was sick of her crazy ass shit. Thankfully there were other people in the apartment o veify the only contact I had with her that nght was her pounding on me. To make it even extra fucked and add an extra unwanted suprise the next fall I was home on leave from Iraq go to one of my old roomies bachelor parties in a completely differant city than this happened in. She walked in just as I am about to leave the bar with a sexy older woman who wanted to make sure I enjoyed my time home. She starts screaming at one of my buddies who was close to the door so the rest stand around and block me from sight. as we got out of thereas fast as we could. The worste part is I found out that night the "friend" who intorduced us knew she was a phsyco and didn't say anything figuring I would be out of the country before she turned fully ape shit .
#4105950
Lvl 8
this happened last year. it's somewhat mellow but it's the weirdest so far for me..

i'd been rubbing elbows with this girl in project meetings. she's cute but not my type. she's just too girlie and too sweet, yech! anyway, our team went out for drinks one night. she sat next to me and whispered that she wanted a one-night stand with me. so i thought, that was cool and agreed. as we were getting it on, she'd insist on being on top and controlling the action. that was fine so i let her. after we're done, she plopped down and immediately fell asleep. no snuggling and stuff i'd expect from a girl. worse, at 4AM, i was awakened by her loud snoring. it sounded like my grandpa's snore. the next morning, she took me to this classy brunch place, paid for our meals, and said this was a 'thank you for my services' as a joke. true story.

it just felt like i had a one-nighter with a dude in a female's body.

(and yea, she never called me again, lol)
#4105951
Lvl 4
When I was at college the first year I stayed in student accom. This was mixed and there was about 16 students in the corridor, I'd say the split was ten male and six female.

One girl, was an all out northern nympho, as the year progressed, we would get updates on how many of the ten she'd bedded, she wanted to work her way through them at least! This would lead to huge inquests as to who the next man was, what she did and how he rated! Only two of us resisted her charms for the year! And there was a definite case for one of the women. Thinking back, face...not bad, body...pretty good, BJ...excellent, sex...nothing she wouldn't do, accent...northern monkey!

For those of you in the US, the english northern accent was never designed to be sexy!
#4105952
Quote:
Originally posted by SgtShish

So a few years ago between my 1st and 2nd deploymnent. I meet this girl at a a friend from works house party. I had proceeded to get fairly shit faced. Talking about all sorts of crazy shit when she asks why everyone who lives at the house keeps making me do shots for as they walk by. I tell here aobut the fact that in a couple of short weeks I leave for training followed by a year or more in Iraq. So we get tlaking about how my plan is to have as much fun doing everything I like to do as possible. Basically drinking, fishing, off roading and and having as much sex with basically anythign female with a pulse. She says she is totally fine with this and takes me back to her place. She turns out to be a whole lot of fun and dirty. SO we play around off and n while I am home. We start trying some things a little of this and some of that. But she is swears up and down that she will never take a dick up her ass. But I had noticed that when I grabbed her ass to give it hard she woudl always end up squirming just so that the waste department would get some stimulation. So I played with it more and more and eventually got to slip it in. Was amazing turns out this chick was a total butt slut to the pot she woudl orgasm so hard she would just keep orgasming making her screams louder and louder which was ok with me cuz I knew the girls who lived above her. But thats a whole nother story from when I had first gotten back from Afghanistan. The suprise though wasnt that she was a total butt slut but the fact that she was bat shit f%##ing insane. She started ot attack my friends and my roomates g/f's to cap it all off she filed a false domestic abuse report after I told her to fuck off cuz I was sick of her crazy ass shit. Thankfully there were other people in the apartment o veify the only contact I had with her that nght was her pounding on me. To make it even extra fucked and add an extra unwanted suprise the next fall I was home on leave from Iraq go to one of my old roomies bachelor parties in a completely differant city than this happened in. She walked in just as I am about to leave the bar with a sexy older woman who wanted to make sure I enjoyed my time home. She starts screaming at one of my buddies who was close to the door so the rest stand around and block me from sight. as we got out of thereas fast as we could. The worste part is I found out that night the "friend" who intorduced us knew she was a phsyco and didn't say anything figuring I would be out of the country before she turned fully ape shit .

tldr
#4105953
Lvl 10
Atually,my bigest surprise was when I first saw a shaven girl.I was dating a girl since i was 16 and we broke up when i was 19.She had a completely untrimmed natural bush,but i had never seen anything a less.when we broke up,the next girl i slept with,was completely shaved and it was a shock for me.
#4105954
Lvl 7
Quote:
Originally posted by fazerix

....A big unshaven bush is one thing but hairy legs and armpit hair is another. Now I watch out for European women.


I always get upset when americans think europeans are not shaven... because if anything, its the other way around. i can claim that because i go to nude beaches and spa's alot for recreation and checking out those chicks no better place to be than flirting naked and knowing what you get.

so there i was in harbin hotsprings, napa valley, california for !!3 months!! its clothing optional which means that pretty much anyone is naked and i have NEVER EVER seen soooo much bush in my whole life. i'd say only every 10th person no matter if male or female was shaved.

in germany where i go to a nude spa almost weekly in fall/winter to load up on the warmth of saunas and hot pools, its the other way around. not to shave is filthy, at least in germany. you are kinda right about italian girls though. i have been there a couple times too and there were alot of bushes!

but i know americans think that... i have been living in minnesota for 3 years and almost a year in nyc and that belief seems to be common. just don't like it cos its simply not true and i get upset everytime because in my time in the states i got so dissapointed very often with a hot date turning out to be a hairy something downstairs *gg*

never ever happend to me in germany. even as a guy in germany it is not only "normal" but WANTED by the girls that you at least shave your dick/balls, armpits and chest, otherwise "you are gross"... seriously!

i mean it is gross especially with women bush and oral sex, not to mention how much bacteria can live in that woods ...hehe


@topic
surprises on dates.. hmm... i had a couple of girls who said that they would like to wait with sex but then jumped on me and the first or second date already ^_^ otherwise no real surprises i guess. i am a real fan of going to public places were nudity is allowed and in germany its allowed at pretty much any lake or public pool/spa so i see the girls naked before i even flirt with them
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