What is the strangest sexual encounter you ever had?

I was thinking this morning about some of the experiences I've had over the years. I know most everyone has that one thing that has happened too them that stands out above the rest.

Okay so here is mine. About 23 years ago I was friends with a married couple. They were really nice and we got along great. They lived about 25 miles outside of the town I lived in. I was working evenings at the time, one evening my buddy calls me, and says his wife was in town and had a bad headache. He asked me if she could lay down at my apartment for a while till she felt better. I told him that I would put the apartment key in my truck and she could come by and get it. Didn't think any more about it finished my shift, headed home. I got to my apartment and that's when things got weird. I go into the bedroom and she is still in my bed covered up. She said she was feeling much better. I said that's great. I get to the edge of the bed, she pulls back the covers to reveal to my surprise She was naked! She asked me if I would like to fuck her? Before I had time to think the truth came rolling out of my mouth. "hell yes" I said. I asked her what about her husband? She says Oh don't worry, I will tell him that I m going to hang out and talk with you for a little while. So I get naked and she kisses me then goes down and starts to blow me. Next as I'm In Daty land I hear her say " I just sucked his dick and now he's eating my pussy." I ask her who she is talking to? She lays the phone down and says shhhh. She pulls me up on top of her and I go to town pounding her. She is moaning loudly and talking really dirty too me. After I blew all over her chest, she picks up the phone from the bed and says, " He was great, see you in a few" then hangs up the phone. That is when I realized it was her husband that was on the phone the whole time! Was the most awkward thing I've ever experienced.

Lol my question is, was he in on it? Or she was doing it out of spite? Crazy story nonetheless lol

I was living overseas about 10 years ago and I met a married couple online. After a few weeks of communicating, I pulled the trigger and invited them over to my place to have some fun. We talked and got comfortable. I was a little nervous because this was my first MFM. We made it to my bedroom and the fun began. This is where is started getting weird.

At one point the wife is laying on the bed and she giving me a BJ. I look over and her husband is fingering her but he was moving his wrist like he was beating eggs for an omelette.

After a few switches of activities/positions, he blows his load. He goes and sits over by the desk in my room. I’m pounding his wife for another 10-15 minutes or so but I couldn’t orgasm so I called it quits. After I washed up I realized he had been using my laptop looking at porn while I banged his wife.

The couple then stuck around well past their welcome and eventually I just had to tell them I had dinner plans and needed to head out. When leaving, they asked me if I wanted to meet again next week. I said I had plans but would get back with them.

It was just awkward and I started to ignore their calls and emails. I eventually received one where the husband said his wife really liked me and complained that I was ignoring them. I didn’t respond but got a kick and ego boost from their email.

Fast forward a few months, I received an email from the guy at my work address asking for help in searching for a job. He must have grabbed a business card while he was over at my place.


A few years later, I receive an email from him and he complains that his wife left him for a guy with a 12 inch dick.

Sparomer!

That whole story just turned me on! It would've been even more amazing if he were actually there watching you two with out you knowing!! I'm a voyeur myself so this was a treat for my dirty mind =]

Lol my question is, was he in on it? Or she was doing it out of spite? Crazy story nonetheless lol Originally Posted by Cheyenne Ryder

Actually I never had the balls to ask him. She never mentioned my name through the whole thing. So I just acted like it didn't happen. About five years ago after they had long been divorced. (go figure) I became friends with his current wife. I couldn't take it anymore so I told her about the whole thing. She told me that his ex used to do that to him all the time. So I think she just had a evil control issue or something. Its been 25 years and it is still seared into my brain frame by frame just like video.

About 4 years ago I was commuting to work in dallas and had a sweet walkable area apartment. Met a smoking girl at the pool, realized she was married and within a few weeks met her husband - cool guy and we golfed every other weekend. Two months into it were a bit tequila’d up and she’s coming on to me and we fuck. Don’t see them for two days. Next week at golf he brings it up and says they have an open marriage. I’m not into dudes or didn’t have a girl to bring to the party. He says , no she just wants to fuck you a couple times a week and he’d rather know who she’s fucking. Moved out of the place three months later but fucked her couple times a week for two years.

I remember meeting a girl and her inviting me to her place. We started making out and feeling each other’s bodies. She invited me into her bedroom where we both got naked and got on the bed.

More making out and touching and feeling all over. When I I tried to get on top of her she said “we can’t fuck” I chuckled because I thought she was joking, but she was serious. She said that since she had just met me she wanted to get to know me first. What the shit? That was pretty strange. I consider it a sexual encounter because I touched all of her naughty parts.

The hottest thing that I have had lately was about a year ago I was at RELAX and I paid violet to use a strap on with me. We played for a while, It was pretty great. She had her strap on, it felt really good for a while.....I could hear a lot of the girls in the hall chatting, it was very distracting for me up on all fours getting banged. Finally Violet tells me she need to go get something she leaves . Comes back 10 mins last and tells me she has surprise in a good way. turns out all the girls that work theree wan to watch.
next thing you know I've got 4 beatiful girls watching me gettin.g plugged by violet. some for them probs quit after that LOL but it was fuck

In college, dead asleep, my roommate come home with his girlfriend and her friend who I have never met, and did not know at all, and I wake up to this complete stranger sucking my dick. It was pitch black, not telling what she looked like, she was rather thins and long hair, we fucked like two alley cats that night. To this day, I don’t know her name or what she looked like or who she was.

Was about 26 years old moved to a new city in an apartment, its a Friday night couple weeks there just out the shower hear a knock on the door. Wrap a towel around and open door cute little milf blond there says I think this is your mail she was in 102 in was in 202. Mail was trash flyer said thanks she went on her way.
2 weeks later Friday night knock knock same lady more junk mail. This time she cranks up a conversation. We talk for bout 30 mins about everything.
2 week later knock, knock her again.
This time out of nowhere she explains she is going thru a divorce, husband has child every other weekend.
She has a cum fetish and would like to play with my cum.
For the next 6 months just about every other Friday, Saturday and Sunday she would spend time masturbating, sucking my dick and playing with the cum, rubbing on her body, in her ass, eating it. Would never let me fuck her because she was still married! When I got relocated and told her i was moving, she asked if i could j/o in a container and mail it to her!
WTF

Not so strange but hot for me and memorable. I was stationed at Hahn airbase in Germany in 1990. Got some kind of special duty off-base and there where about 20 of us working there. We were having some kind of briefing and all of a sudden I felt somebody rubbing my back. Really didn't think too much of it but I thought I would test it out and so as we are working I started to brush up against her ass and progress to running my finger over her pussy on the outside of her pants from behind. Not another word was said but when we got back to the base for lunch without asking she followed me to my room. When we got there I started kissing her but as I was starting to loosen her pants she said to stop because it was that time of month. She wasted no time dropping mine and giving me a great blowjob swallowing everything. When she finished she said "I just wanted to do that". We had sex on a regular basis for two or three months after that until it was time for her to leave Germany.

My Strangest Hobby Encounter was about ten years back. My Burb had a non-asian Massage Parlor. Crazy Idea hunh?

The only problem with this place was the "shop" policy of the providers taking 3-4 visits before you found out what they going to do for you. This was before I evolved to a Suck It or I am Outa Here, No Tip Policy. That or cut the bullshit, tell me what you will do...
Anyway, there was several months of enjoying several ladies or various ages, physics and races in a very much YMMV situation. For some weeks I had been enjoying visits with a Country MILF, blue eyes, sandy blonde short hair, in decent shape with a little mommy wear and tear. Nice figure. She got on the mutual touch, kissing and BBBJCIM plan pretty quickly, so we were good.

Then there was my last visit with her. I come in expecting a little shoulder massage and a lot of head. Nope, not this week. We had had a nearly(probably) double digit number of visit and she chooses this particular one to go all LO Legit Massage thearpist with me.
Not really wanting this to turn into an offended girlfriend discussion, I anyway ask her politely "What the hell is Up." She says, No Shit now...

"I have a boyfriend and have started going back to church, but i need the money from this job until I find a real one and that'll be hard because...."
I am already gazed over at this point...wtf? I want a blowjob and I am far from her therapist or social worker...

We get to a point at where she says she is only doing HJs now. Great...

"I can do that myself."

She's looking more and more a combination of distraught and put off. I'm thinking she had not thought this thru. "No, I don't do that anymore..." That works real well in face of a hard cock.

Then out comes the kicker. "I'll fuck you for $$ more than usual." she says.
Upsell city and a bunch of bullshit...

To wrap this up my counter is "If you won't do the usual, I'll fuck you, but No rubber."

"Okay, but don't cum in me." she says. Oh, sure...that'll work...

More whining later, I have her leaning over the massage table, pants around her ankles and a damp open pussy winking at me...I slide in and she starts chanting, "Don't cum in me! Don't cum in me!"...etc.

I tune for that out for the several minutes I almost decide to dump in her, but I don't...
The time to cum did not happen soon enough. I was so pissed from all the chanting that I pulled out and caulked from just above her asshole to her taint and frosted her pussy lips.

She lays there, one stink eye looking up and says 'What did you do?"

"I didn't cum in you"...

Was on a trip to Hawaii and stepped into a same bar with no one there was about to leave and a Japanese couple came in and sat next to me at the bar, her next to me him on the other side of her. That was a bit weird, whole damn bar to sit at. I said hi and then they started talking Japanese to me and I'm not following anything, out comes the pocket dictionary (his). Pretty soon we move to a booth and again she sits with me, chatting away. He gets up and goes to the bathroom and she starts rubbing my leg (Hawaii...shorts) He come back and she keeps rubbing my leg and he puts some money in the jupe box and asks me to dance with her (slow) fuck why not, so I also figured I could get some squeezing in also so I go full on butt cheeks rubbing. Soon we are back in their hotel room and things are moving on pretty good, I can only guess he told her to strip for me (in all fairness she was a bit of a mousy pale lady but...) anyway I pull out the one eyed monster and while I believe him to be good size it's not huge but the look on both their faces made me thing this might have been a gig um to them. Got her to suck me ate her and fucked her before leaving but made a "date" to meet again the next day.
I was early so I went to the international market and what do I see but the wife, I walked up behind her to hear her talking to the clerk in perfect English! Turned out they were both from northern california! Just adding some spice, yes I was the first BWC for her and no I never told her husband I knew the truth, fucked her in front of him for several hours (yes we took breaks),

Back in the early 90s I was at a club with a friend of mine in Dallas Alley in the West End. Anyone remember that place? In walks a tall slender redhead with hair all the way down to her ass. I couldn’t stop looking at her. She busted me looking at her and smiled. So me and my buddy walked over and started talking to her and her friend. The redhead and I hit it off pretty good. The next thing I knew, we were off in a corner making out. Then she asks “you know what I feel like doing?” What, I ask. She replies “I want to go fuck!” I was a little stunned. I was so used to having to play the game and work so hard to go home with a woman. I said sounds good to me but I have a couple of roommates at my place and I didn’t drive. She said she could take me back to her apartment. Sweet, let’s go!

She’s driving, and I’ve got my hand up her dress rubbing on her panties. She tells me to pull my pans down and starts giving me a handjob. We’re driving on I-35 around midnight. Remember, she’s driving. She asks if I could grab the wheel and steer. I do and she leans over and gives me a blowjob. This is crazy! We’re on the freeway going 65, she’s in the drivers seat bent over sucking me while I’m trying to steer! The BJ felt great but I was terrified at the same time. I saw traffic up ahead and had to stop her so we didn’t die! We made it back to her place alive and fucked until the sun came up the next morning. Later she told me that she had been separated from her husband for the last 3 months, and that was her first night out and was horny as hell. I was just at the right place at the right time. We remained fuck buddies for the next 6 months. She was perfect for me at the time. I wasn’t looking for a serious relationship, and all she wanted was to get fucked a couple times a week.

Mine isn't strange...but it is wild...

I was fresh out of the military.

Now working for a local freight company...buddy of mine and I were headed to Bachman Lake to hang out but stopped at the car wash first to clean up my car.

This woman...Thick and fine...smh...came over and asked if either one of us would make her car look as good as mine...He and I looked at each other and said...HELL YEAH...

Washed AND waxed her car...then she was like...

What are you two doing later tonight??

Ummmm...NOTHING...what you got up??

Ya'll come by my apartment later tonight so we can sip on something and hang out...

About 8pm we're in Grand Prairie at her apartment...

She wants to get in the jacuzzi...He and I didn't have swim wear so we get in with our underwear on...She's in a 2 piece and we are on her like to crazed dogs....lol

She stopped us and this is when we knew it was ON & POPPIN...

If ya'll buy my daughter a pizza I'll go home with you...SHIITTTTT....HEY DOMINOS

Daughter got the pizza and Mom got the curfew....Jumped in my car and rolled out...

Now were on Great Southwest....He's in the passenger seat and she's in the back...

She pulled her tits out and started fingering herself...

Buddy reached back and started helping her...Next thing I know he's in the back seat getting head as I'm driving and tryin to watch AND not have a damn wreck...

Make to my apartment and she wanted to shower to get the chlorine off of her...All 3 of us can't fit so I go to the other bathroom, shower and come back to find them fucking in the shower...then we all get on the bed and it was One in Front and the other in back...I'm getting head while he was thuggin her out doggy style...then we switched...

Put her in MISH and he's FF'ing her....She mounts him for CG and I'm behind her and DP'd her...She had a big ass and I wanted to go GREEK but she wasn't with it...

We fucked her every which way but loose until 4AM...

All 3 of us had to be at work the next morning

2 weeks later I ran into her at Dennys....lol

She came by and fucked me again and in the midst of this session she told me that she wanted to be my woman and she fucked both of us because she thought that's what it would take to get with me....(mind you we just met at the car wash)

After session #2 I cut all comms with her and never saw her again...

That was a wild night...