Who is the most unlikely person that you would hook up with?

CarnivalBarker

Literotica Guru
Joined
Oct 15, 2013
Posts
5,591
I'm curious. Many of us have a type. Or at least others think we do. If people who really knew you were asked, who is the most unlikely person they would think of, who you actually would have sex with?

I got to thinking about this because a girlfriend of mine was talking about Taylor Swift. I don't really go for girls as a rule, but I would easily get with her for a night of fun. When she was talking, I was like, "I think she's attractive and have a girl crush on her," and my friend made the worst face! Anyway, that's who I'm saying.

Who is yours? Doesn't have to be anyone famous....just someone you would do, that others would never in a million years think you would do.
 
Lena Dunham.

She's a communist nutcase (BIRM), but I'd do her.
 
Melissa McCarthy. I think she is beautiful - would love to enjoy that wonderful BBW body of hers.
 
Melissa McCarthy. I think she is beautiful - would love to enjoy that wonderful BBW body of hers.

good answer!

but - i love older women and curvy women (Mrs. R is curvy :heart:) - I usually can't stand girls like Paris Hilton...

so her ... it would be interesting for a change.
 
TV's conservative commentator Laura Ingraham, if she were wearing a gag.
 
There are some female co-workers, and also some waitresses at my favorite hangout, who I would be with in a heartbeat if they were interested. And I'm sure that would shock some people who know me, primarily because of the age differences involved.
 
Jordan / Katie Price. Total air-head and celebrity parasite - but I'd fuck her
 
John oliver. He's not all that "pretty", but he's funny as hell and I think he'd have me laughing a lot. It'd be fun sex.
 
There are some female co-workers, and also some waitresses at my favorite hangout, who I would be with in a heartbeat if they were interested. And I'm sure that would shock some people who know me, primarily because of the age differences involved.

I assume they are much younger?

I one waited tables and loved that older guys always wanted us (waitresses and especially the hostesses, who were barely 18 and sometimes younger) so much. It would probably be a surprise how many I let fuck me....
 
I assume they are much younger?

I one waited tables and loved that older guys always wanted us (waitresses and especially the hostesses, who were barely 18 and sometimes younger) so much. It would probably be a surprise how many I let fuck me....

Yes. I don't have a hard age limit in either direction, but the people who know me well are probably much more used to seeing me around people who are older than me; often significantly so.

It might surprise them, then, to know that I do occasionally meet someone much younger than I am who interests me enough as a person that I would date her if the opportunity were there.

I will say, though, that the problem with so many young girls is that they're young girls... They may be smart, engaging and sensual, but it's surprising how often they don't even know that they don't know there own minds on certain points...
 
Hmmm... Anybody... or maybe I mean, everybody. It just seem unlikely... period.
 
Some conservative, ultra right wing, Christian southern bred, country music lovin young girl that has fuck all in common with me.

Chances are those girls are really wild just dying to break the shackles of their up bringing. Maybe tired of being a "good girl' and ready to be a "bad girl'.
 
Seems like most of you are going with "celebrities", but I'm gonna go a different direction...

First of all, I personally kind of reject the notion that there are "unlikely" sexual attractions between people. I think the mystery of the unfamiliar is a turn-on for most people, but whether or not they act on it is the difference. Because of this, I think the only people who would view a hookup as "unlikely" are those on the outside looking in. However, I get the point of this thread and I think it's an interesting topic, so I'll dismount my philosophical high-horse... now.

I actually have hooked up with my "most unlikely" person, and to this day it is the most sexually charged night of my life. I'd venture to bet that she would agree I was her most unlikely hookup as well. Although I'm a total perv, I'm a pretty clean-cut, "white-bread" guy who tends to date people that have a similar outward appearance/demeanor (I say outward, because I always wind up with an equally pervy partner behind the scenes). That said... A coworker of mine is this super adorable, super curvy chick with a nearly entirely tatted up body, pierced nipples & labia, and huge gauges in her ears. At the time, she was one of the only people I could share my less-than-traditional sexuality openly with. Her understanding, acceptance, and general curiosity of this created a LOT of sexual tension between us. We always talked openly and GRAPHICALLY at work about sex, and always joked about hooking up. She was on the verge of a divorce, though, so we didn't pursue it further.

I moved away about a year after we met, but we stayed in touch. During that time she divorced her husband, and I happened to be visiting town. She needed a ride home from the airport after a vacation, so I volunteered. Rather than taking her straight home after picking her up, she suggested we grab dinner and a drink(s) to catch up. As always, our discussion became highly sexual in nature and she decided she'd rather come to my hotel than go home. We picked up some vodka and sat in the hotel room talking and drinking for hours before we finally kissed for the first time (something we'd both wanted for a few years now). One thing led to another, and we ended up having the most passionate sex of my life. Completely uninhibited, freaky, and shameless. I haven't seen her for the past 2 years since, but we still talk about that night on the phone on a regular basis. I guess the point is... It was so hot for both of us because we knew that nobody who knew us could EVER imagine the two of us would have shared that experience.
 
A supervisor at work. I've never been very into legs on a guy, but damn has he got nice legs!
 
The Manager at our local Indian restaurant x he is dark, charming and to be honest, very sexy x x x also if I was fully into girls... maybe Nicole Sherzinger x x x
 
One of my emoplyees . She's a thin red head . Not my taste but we argue a lot so dominating her and fucking her to tears would be such a turn on .
 
Back
Top