Oddest Sexual Offers

swingfun

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Mrs. Swing fun and I were talking a couple of days ago and I asked her how her ex boyfriend and her had met. She always talks about what an ass he was so I was curious. She said that before him she was a bartender at a club in her hometown. It was the home base for a large oil company. Anyway there was a guy there that worked for said oil company and the Mrs. was the side piece for this guy. The guys wife was starting to get suspicious so she came to the bar one night and confronted her. The Mrs. said she had no interest in her husband and she already had a boyfriend. The husbands wife said good I'm having a party this weekend bring him over. So she approached her friend and said that if he would accompany her to said party and pretend to be her boyfriend at the end of the night he would get a unforgettable blowjob. She said it took her several years to shake him off after that. So have you ever had and odd sexual requests?
 

stretch8888

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Had a friend several years ago, cute little thing and i was totally into her but she made it clear she wasn't interested and things soured a bit but we smooth things over and remained friends, she was 28 and had never had a serious boyfriend in the time i'd known her, from what i could tell her only serious boyfriend was her high school bf which ended when she was 20.

Anyway she lived out of town, she was coming to her moms for christmas and i guess her family was ragging on her as her sister and brother had families and such yet she didn't seem to even try. seeing as i lived near by she dreaded staying at her moms so she asked to crash at my place AND if i would go to dinner as her boyfriend and just lie to her family, i didn't really want any part of it, she made a couple offers like money or a christmas present of my choosing then she finally offers an "offer i can't refuse" ,which was a blowjob, i figured why not and told her i expected it beforehand.

She came through with some serious oral skills and even swallowed. We ended up fucking later that night and agreed to a casual thing seeing as she lived out of town. After a few months and a few hook ups though i found out why she never had male companionship, she was batshit crazy, cyber stalking kind of crazy, asking why other women liked my shit on social media or why i was in pictures with other women.
 

Player_01

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Anyway she lived out of town, she was coming to her moms for christmas and i guess her family was ragging on her as her sister and brother had families and such yet she didn't seem to even try. seeing as i lived near by she dreaded staying at her moms so she asked to crash at my place AND if i would go to dinner as her boyfriend and just lie to her family

It's like Hallmark movie.

After a few months and a few hook ups though i found out why she never had male companionship, she was batshit crazy, cyber stalking kind of crazy, asking why other women liked my shit on social media or why i was in pictures with other women.

If Hallmark made horror movies like "Fatal Attraction". o_O
 

MilfBanger78

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I do webcams, chaturbate. Lotta fun stories there. Most gay/bi dudes watch n tip me, but i get some females.

One married chick that watches me.. in her late 30s, wants to get a motel room with me when shes in the Tampa area and have me knock her up then have the hubby unknowingly raise it as his. lol. Im not gonna do it of course but shes fun to talk to and pretty hot. Plus a good tipper lol.
 

SamMann75

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Sorority in college has this annual party at a function room off campus. Every sister has to invite 2 guys, regardless of if they have a boyfriend, and it's a semi- formal affair.

My girlfriend invited me and a frat brother of mine who had a huge crush on another sorority member because I asked her to.

So all the guys get loaded onto two busses at campus in their suits and ride 20 minutes to the function where the girls are waiting in their dresses. There is a sit down dinner with the girl sitting between the two guys she invited then dancing and drinking all night.

After everyone pile into whichever bus and me and my girlfriend are sitting with this guy neither of us know. We chat about the night, I'm wishing he'd get the dynamic and me mentioning she's my girlfriend a hundred times and find another seat so I can kiss her. As we pull back onto campus he says so we're going to have a 3sum? I said hell no, your lucky I don't want to get the sorority in trouble or I'd kick your ass. My girlfriend giggled and said sorry he's a tad defensive. She looked at me, put her hand between my legs and said we can at least have him back for one last drink and maybe her roommate didn't bring anyone back from the event.

3 drinks later I'm kneeling in front of my girlfriend on the ground, she's squeezing my cock but not sucking it as she moans how deep he is as he pounds her doggy style and her roommate comes through the door with another guy.

By the time we fell asleep, the roommate's guy had fucked both girls, our "new friend" made her roommate moan about how deep he got before making my girlfriend moan it again, and my girlfriend jerked me off on her chest while going round 2 with our "new friend".


More odd then that, after my wife and I had several kids without trying, a friend of her's told us her and her husband were having difficulty conceiving, then her husband offered to pay us if I would "have intercourse" with his wife. My wife was shocked that I politely said no thank you faster then she could tell them where to put that money.
 
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deleted5791141

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I was asked if I would mind if he wrapped his cock with my hair once. I didn’t mind cuz I was also curious about it. I let him and could hear him moaning as he was seemingly jacking off with it. I made him stop though because it was starting to hurt when he pulled on my head.
 
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jtheimpaler

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With an ex years ago we attended a swinging party, an older mature guy fit guy joined us and put in an a rate performance ….

he text us a week later asking if he could wear a nappy, suck on my exes tits, poop in his nappy be cleaned and then get fucked with a dildo…..
 

Fishsqueezee69

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I broke up with my boyfriend but he had no place to go so he stayed at my place for several months. He slept in the living room amd I slept in the bedroom.

One night, he brings his new BF. We sort of hit it off and had some chemistry but anyway, I went to sleep. In the middle of the night, I heard a lot of commotion so I woke up. I kept hearing noises so I got really mad that I couldn't sleep. I went to pee and when I got out of the bathroom, I saw my ex fucking the guy he had brought in. The guy, in all fours, smiled and said, "do you want to join us?". I hesitated but then said, what the heck. I jumped in and had the guy give me a great blow job.... we even kissed!

It was fun. ;)
 

Fishsqueezee69

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With an ex years ago we attended a swinging party, an older mature guy fit guy joined us and put in an a rate performance ….

he text us a week later asking if he could wear a nappy, suck on my exes tits, poop in his nappy be cleaned and then get fucked with a dildo…..

Did u do it? Lol
 
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Mount Phalic

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I broke up with my boyfriend but he had no place to go so he stayed at my place for several months. He slept in the living room amd I slept in the bedroom.

One night, he brings his new BF. We sort of hit it off and had some chemistry but anyway, I went to sleep. In the middle of the night, I heard a lot of commotion so I woke up. I kept hearing noises so I got really mad that I couldn't sleep. I went to pee and when I got out of the bathroom, I saw my ex fucking the guy he had brought in. The guy, in all fours, smiled and said, "do you want to join us?". I hesitated but then said, what the heck. I jumped in and had the guy give me a great blow job.... we even kissed!

It was fun. ;)
I can see that in my imagination. The visitor was a lucky man.
 

Fishsqueezee69

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I can see that in my imagination. The visitor was a lucky man.

Lol. I am married man, now but I have a feeling that if I walked in on you, you would ask the same question and I had be very tempted to say yes ;)

My only regret about what happened is that I never got to fuck the guy too. But oh well, I guess that getting a blowjob from your exbf current bf while the exbf watches is hot enough!

True story: this happened AGAIN with another guy. Same exbf. Different guy. And the exbf is still with the same guy, 14 yrs later!

I will tell that story in separate posting in this thread.
 
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SirFroak

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With an ex years ago we attended a swinging party, an older mature guy fit guy joined us and put in an a rate performance ….

he text us a week later asking if he could wear a nappy, suck on my exes tits, poop in his nappy be cleaned and then get fucked with a dildo…..
I honestly lol'd reading that.
 
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Motion-of-the-Ocean

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I wouldn't call this 100% sexual since I wasn't asked to participate, but once had a co-worker ask if I would be interested in handling the camera while he and his wife made a porno. Although I declined, I found out later he apparently had been making the rounds in asking several others as well, but had no takers as while some of the guys told me that they saw a picture of his wife and she was smoking hot, but none of them were enthused with seeing him naked, I sentiment I concurred with :laughing:.

There was also the matter of being as how this was in our pre-swinging days, I was certain my wife would not be ok with this if I had said yes as well as he was quite the strange bird in other ways too, so I couldn't help thinking there might be something more behind his request.

I also had a similar request after we did get involved in the Lifestyle as one of the couples wanted to take pictures of all of us together, but since we had just met them we were not comfortable about someone else having unedited pics or video of us. In retrospect, I mildly regret it as we became good enough friends with them eventually and I would have loved to have photos of the guy's wife to remember all the good times, but they never brought it up again and we forgot about it too.
 
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Mount Phalic

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Lol. I am married man, now but I have a feeling that if I walked in on you, you would ask the same question and I had be very tempted to say yes ;)

My only regret about what happened is that I never got to fuck the guy too. But oh well, I guess that getting a blowjob from your exbf current bf while the exbf watches is hot enough!

True story: this happened AGAIN with another guy. Same exbf. Different guy. And the exbf is still with the same guy, 14 yrs later!

I will tell that story in separate posting in this thread.
You bet I would ask you to join us and If you said yes, I’d be rock hard with anticipation.
 

goldscorpguy

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I dated a girl way back in my twenties who had a slightly weird obsession with cum. She would always insist I wore a rubber when I fucked her, but after I'd finished she would slide it off me and, being careful not to spill a drop, suck all the cum out, even rolling it up like a tube of toothpaste so as not to miss any. She greedily swallowed it all and licked her lips. Again, if she was giving me a bj I always had to cum into the palm of my hand and she would then lap it up with her tongue like a hungry puppy.
 

Hungstraight

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A few spring to mind:

Took a girl home and she seemed totally vanilla - when we got to mine we fucked and were about to fall asleep when she asked if I would wake her up in the night by shooting a load on her face... I obliged ;)

Pulled another chick at uni who asked me to cum on her face and take a photo so she could send it to her ex bf. Again, who was I to deny her request?

Had a long time fuck buddy who, the first time we had sex, asked me to pee on her. I didn’t think I’d be into it but soon changed my mind.

And maybe the weirdest was going back to a girl’s flat and then having her ask me if I minded her 2 roommates watching. I naturally hoped it was going to turn into a foursome but it didn’t :(