66mustang

I have always been curious about this topic. I have had some real surprises in my sexual history, and I am always curious to know...."Who have you had sex with that no one would believe it really happened?" It can be someone famous, or someone taboo for you, or just someone that there is no way that you should ever have been able to hook up with, but yet you did.

I have slept with college professors, and co-workers and bosses, and even total strangers of course, but the most amazing piece of rear that I have ever entered was the MILF mother of a former girlfriend. The girlfriend and I were pretty much like rabbits, tearing off a piece whenever and where ever you could find a second, and I guess her Mom heard us and had questions.

My girlfriend was out of town one weekend and I went over to mow the lawn or something like that, and her Mom made it clear that the landing strip was open if I wanted to. I was always horny as hell then, she was incredibly hot at about 40 at the time, and we just got busy. We did it 7 times that weekend in every combination imaginable, and never again, but I will certainly never forget those 3 days straight from heaven. In that case, her Mama knew what was best.

Jinn

Man, I'm vanilla. I've really only had sex with my current girlfriend..

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Giant Hamburger

It has always required a great deal of expecting, on my part at least.

KirStang

66Mustang must be a good looking stud. Random girls from across the hall, moms of girlfriends? You go, you.

Shadowex3

According to him he's stuck 10 inches in everything from Random girls, bosses, co-workers, a girlfriend's mom, to just about every female virgin at his college, often concurrently.

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ring

The most unexpected sexual experience?

Regaining consciousness after a head injury, I had a very intense orgasm/lifegasm?
'tis difficult to explain.

Charlatan

The most unexpected experience was having a woman I had a small crush on come up to me in a bar and say, "I want to fuck you". Totally unexpected.

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ellie

Well I guess this qualifies...

Met up with a guy from an online dating site. I knew he was tall and he was a big guy (which I've always been attracted to,) but had no clue exactly how big until we met face to face. He was about 6'8", 450-500lbs. Gigantic. Fat muscle, if that makes sense. Anyways, we had a nice time over some drinks. Next thing I know, I wake up in his bed wearing only a bra that was half way falling off. I look next to me and it looked like there was some astronaut in bed. Because he's so large, he has sleep apnea and sleeps with one of those masks. It was loud.

So he happened to wake up while I was stirring around trying to find my clothes. I was really uncomfortable and especially concerned as I've never had so much to drink that I blacked out like I did. He drove me to my car. I said 'thanks,' and just went home. He called later that day to make sure I got home ok. We started talking about the night before. I told him I didn't remember much. Started to tell me how wild I was and how I took control and did all this...erm...'forward' shit and all. Folks, this is not how I am lol. I'm submissive! I told him, 'What, did you drug me? lol' He says, 'Dammit, I'm always accused of that. I swear I didn't do shit.' That freaked me out, as he really got upset over it.

So to sum it up, I do believe he dosed me with a roofie cocktail. Like I said, I don't remember anything about getting to his house or doing anything in the house except for searching for clothes in the morning. I even held my pee in so I could hurry up and get back to my car lol. But there's no way I could have been so hammered after 4 vodka / tonics. I never called him again.

Plan9

...and she doesn't even let you keep ammo in the house.

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MrFriendly

Honestly, my biggest sexual surprise in life has been all the sex I didn't have. I was the first of all my friends to get laid and had it on tap for years, then, nothing, for like seven years. Funny how the mind works I guess. Can't say my life has been better or worse for it.

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jewels

And you didn't head straight for the police? They would have checked your blood levels to verify if you were drugged. Acting appalled at the suggestion that he drugged you doesn't mean he's not guilty. I'm so sorry this happened to you.

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66mustang

Kirstang, I wish I was a good looking stud. I'm on the ugly side of ordinary, but I know how to talk to ladies. As Shadowex3 made mention of, I am very well endowed and I have had a great deal of sex because of my size, but the majority of my mojo is the confidence a big cock has always given me. Co-workers, moms of girlfriends, total strangers, a girlfriend that treated me and my meat like an addiction that also liked bringing virgins home for me to spoil, as she called it, I have had an amazingly numerous and varied sex life. I have had a great number of opportunities for sex, a great number of repeat partners because of the way I treat the women that I am with, and I just know how to make girls mine when I talk with them.

ShadowEx3, thanks for noticing. Every bit of my posting is true. I've been blessed and very busy.

MSD

I think I remember this from when VH1 still played music videos.
I dunno, of my friends, the one who gets the most women (often with literally zero effort) is far from the most attractive.
I'm not saying she shouldn't have gotten checked, but the vast majority of people who think they've been drugged and get tested find out they just drank a whole lot more than they thought they did.

ellie

Oh, you're so sweet jewels lol.

I didn't wake up with bruises or burns or anything, so I just let it go. I mean, I was definitely creeped out some and concerned over the probability that no condom was used. But like MSD mentioned, there is that chance maybe I actually did just drink too much. I kind of doubt it but whatever.

Jewels, I'm not traumatized over it or anything, and I'm definitely not a drama queen - i.e. make a big deal and accuse him of the r-word. I'm ok. And I've learned the lesson that they teach women in their 20's --- if you're on a date with someone new, when leaving to go use the restroom, take your drink with you.

redwolf

Biggest shock for me was what almost happened. A good friend( whom is a guy) asked me (also a guy) If we could have sex just see how it is. For reasons I still don't know I almost said yes.

MSD

The big question is who mixed the drinks? I can't think of anything much better suited to accepting way more booze without much of a taste difference than a vodka tonic. Then again I'm pretty sure tonic water would cover the taste of GHB pretty well.

MrFriendly

Because you were naturally curious? Which is, you know, totally natural and fine :-)

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levite

Unexpected? I dunno. The couple of times I hooked up for a one-nighter were surprising, no doubt.

But honestly, I think the most unexpected was the first girl I ever slept with. I was very young. In retrospect, really too young to be having sex. But I was living in Minnesota, and there was nothing to do, so kids were having sex pretty young. And being an adolescent boy, it's not like I didn't want sex all the time. I just didn't think I'd be getting any.

I was a geek at that point (that changed later in high school). Chubby kid, read comic books and sci-fi, too smart for my own good, had a bad tendency to be a teacher's pet when I wasn't busy giving the finger to any kind of authority, tended to be a loner. Not, in short, the kind of kid who expects to be having sex any time soon.

I went to Hebrew school with this really cute girl. She was a cheerleader at her school, believe it or not.... Wavy brown hair, dimples, girl next door smile, all the right curves in all the right places.... Way, way out of my league. Maybe not even the same sport. Anyway, for some reason she had decided I was amusing, and deigned to hang out with me a little. She stuck with the amusement long enough for me to get over my shyness around girls that give me a terminal hard-on (shyness since overcome, BTW), and apparently she decided that smart and quirky and sensitive had their value, so we kind of became friends, and she would confide in me a little.

That was more than I expected. So I was more than shocked when she proposed that we have sex. In those days, there was no such thing as "friends with benefits," but that's essentially what she wanted. She had decided on me because I didn't go to her regular school, and so she felt comfortable having sex with me on the sly, so nobody would find out and ruin her reputation. At the time, of course, it never occurred to me that she was essentially using me for her own gratification, and that she would never have wanted her friends to know that she had sex with me-- that she would've been ashamed, not just of having her sex life revealed, but that she'd fucked a geek. But I just went along with the whole thing, where I wasn't her official boyfriend, and we didn't go on real dates, and she didn't want me calling her house, or showing up at her school.

I was living with my dad that year, and he was often away, so we just made regular times when she would come over to my place, and we would get it on. To be fair, she was quite hot, and very eager to explore her sexuality-- there wasn't anything I could think of at that time that she wasn't willing to try, in the privacy of my house. In retrospect, I probably should've valued my integrity over the sex, and not done it with her. But that's just not how adolescent boys think. So I shagged her rotten, and had a jolly old time doing so.

Lasted about eight or ten months. A lot of sex. Quality sex, considering our age and inexperience. And it was definitely unexpected. Social status and cliquism is never stronger than during that time of life, and yet...I spent the better part of a year fucking an alpha girl. She remains, to this day, the only cheerleader I've ever nailed.

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stevie667

The milf next door, whilst her kids were alseep upstairs. Still not entirely sure how i managed to pull that one off...

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thedoc

Not sure if this was the most unexpected, but my wife and I were traveling on the Pa. turnpike and several years before the T.P. had bypassed 2 tunnels and the old road connected with the new. We decided to stop and backed up into the old road, it was after dark and I can't remember why we stoped. We got out and I got her naked on the hood of the car and we made love. It was a cool night but the car was still warm so it was OK. The car was a '67 Buick Vista Cruser wagon, and we are still married, 32 years. I sometimes wish I still had that car, I'm glad I still have my wife.

uncle phil

two true stories...

i was working a bar in my hometown way back when, when a good friend of mine stopped in, fresh from 'nam. we had a couple of drinks together and i closed up early since he was the only customer.

went to this place in the big city, walked in, and T says, "let's grab a seat."

i said, "let's walk around the bar first and see if anybody wants to pick one of us up."

needless to say, i found a couple of empty barstools next to this babe and she proceeded to hit on me. we talked for a while then closing time happened. ended up me taking T to his place and continuing on to my place with said babe for a 'morning' of frolic and nastiness.

life was indeed good...

a few years later, i was working up in buffalo and stopped into my local watering hole on a friday after work. after a few dozen 'blues,' got to talking to this babe who worked a few floors up from me in the same building. things led to things and i offhandedly suggested that she come up to my place to view my etchings. (honest-to-god, that was the line...)

she did, and we ended up spending the weekend together and continued the on-again/off-again relationship for a few months until i got transferred to chicago.

life was good back in the day...

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thedoc

There is a saying, "If it sounds too good to be true, It probably is". Could that apply to this thread?

Shouldn't these posts be on the Humor thread?

jadangel

Back in my early 20's I had one hell of a sexual expierence. My friend & I were at the house of 2 guys that hung around our crowd... We were drinking and watching tv in the bedroom. All of us were laying on this huge ass bed .... The talk among us turned sexual and before I knew it I was being kissed by one of the guys. The other guy was touching me all over and shockingly my friend was touching me too. More shocking than that was the fact that I didn't mind her touching me....My clothes were taken off of me and hands and mouths were all over me. It was the most erotic thing I have ever been a part of in my life. I layed there and those 3 did the most amazing things to me....

The next morning as my friend and I were leaving their house, we joked around saying next time it would be her turn. Sadly we never did, but I will never forget that night as long as I live.....

redwolf

Totally......

MrFriendly

Text totally sucks with sarcasm, but to be clear, I was genuine before. Heaps for realsies yo.

I really don't have or see any problem with to guys getting it on in the name of exploration and curiosity or simply because they damn well feel like it. The way I see it, western culture either overtly or subvertly makes a lot of men think there's something inherently wrong with it or that it challenges their masculinity in some way. It's utter crap.

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66mustang

Doc, just because you may have led a boring and sheltered life, don't hate on those of us who have had experiences like these. Just because these things never happened to you does not mean that they never happen.

thedoc

Well my life has not really been so boring or sheltered, I 've hade my share but have no need to brag about them. I just find an experience with someone I'm close to, to be more interesting and exciting. I also do not see the need for you to be so defensive, Just why is that?

BTW, I don't hate you, nor do I envy any of you, I'm happy with my life as it is.

The_Jazz

Doc, you get my vote for "classiest response of the last 20 minutes". Well done.

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Lendari

lol @ this

curiousbear

Wow!!!

For me nothing unexpected so far

---------- Post added at 10:12 AM ---------- Previous post was at 10:10 AM ----------

That is way too naughty of yourself!
Did the girl ever knew about that?

Fire

My whole sex life has been pretty damn surprising to me- I was a geek in high school, but in the first year of college, learned the all important lessons

1- I am funny
2- Girls are just as horny as men, but tend to not be as forward about it.
3- A small penis is not intimidating, and skill makes up for any lack of length anyway

So pure balls and skills got me a remarkable amount of poon, especially for a fat white guy.... and continues to work for me to this day....

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blar

kudos to you for having good confidence and not letting having a "small" penis ( if you have one) stop you

Craven Morehead

Years ago, two young ladies picked me up in a bar one night.

Use your imagination. It won't come close.

troy512

my sister-in-law

snardius

Girlfriend and I are at a friend's lake cabin. He offers his Sunfish sailboat to us and we take him up on it. I'm sailing this little two person craft and my gal is in the stern. The next thing I know my swim trunks are around my ankles and my girlfriend is swallowing my very stiff pecker.

I spy a power boat across the lake whose skipper recognizes me and my friend's sailboat. He plots a course directly for our sailboat with the intention of turning at the last moment and hitting us with his prop wash. I am torn between the realization that I should tell my girlfriend that we're about to get hit with a wall of water and the very intense pleasure she's giving me. As I watch the boat approach, that old familiar feeling begins to overtake me and I wonder if I can get off and still warn her that we're about to get wet (to say nothing of the possibility of capsizing).

As nature would have it I didn't say a word and as the boat turned leaving a wall of water to wash over our tiny craft, I exploded down her throat.

We broke up shortly after that incident...but man, could that girl give head.

keymaker

I call on a plant and the lady I deal with is a lesbian who I flirted madly with. (I am single and she is hot!) One day I get an email asking me if I could have lunch with her on Friday. She offered to drive and she then took me to an isolated area and let me know that I was the special for the day...I have never been worked over like that before! When I asked about her orientation and this episode she said that "everyone needs the cobwebs brushed off from time to time"! I still see her twice a week and we talk shop...but we give each other a wicked smile ever so often. I hope this was not a one-time-deal!

Red and Black

I like that term "lifegasm" best describes what I felt.
My unexpected sexual experience took place with my ex-girlfriend. Back then I had my share of marijuana, and while I was under the influence I visited her and she was soo horny but we couldn't have sex because she was on her period. So she decides to gave me a spine tingling blowjob in my car. She was the only girl who was able to deepthroat me, and that was my first time feeling that leading her to giving me a "lifegasm." Indeed its hard to explain, very intense and not only did I feel my orgasm but I felt a "release" in my head which put me in ecstasy. This leads me to making a thread about having sex under the influence.

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Zeraph

2nd date. I was expecting a movie. She walks right in, takes her top off and just starts blowing me. I returned the favor and she insisted upon intercourse

Bonkai

After i got my first tattoo, a girl watching me get inked in the shop decide she wanted a quicky...she was pretty but the sex was pretty vanilla tho really unexpected!

Mountain Biker

An ex girlfriend and I were driving around the back roads, in the winter time, it was snowing. We stopped on the side of the road (backroad) , shoved the snow off the Jeeps hood and did it right there. Cold but a lot of fun! No other cars drove by, was a lot of fun!
Its great to be with laid back fun ladies, makes things so much more fun!