Picking up a hot woman at a bar that turns out to be a man and does you.

[ForgottenSecret]

This is a fantasy I've always had, going to a bar and getting tipsy, finding a gorgeous woman there that you flirt with, she likes you and invites you back to her house. You make out, and fondle each other for a bit before she pushes you onto the bed. She takes off your pants and gives you and amazing blow job right up to the point where you're about to pop but doesn't finish you yet. She then moves her mouth down and spreads your legs and gives you a rim job while stroking you. She then puts a finger in your ass hole and fingers your good while she Jacks you off harder and makes you cum. You're in so much pleasure you ignore the finger in your ass. Then she gets up between her legs and starts pushing something thick and hard into your hole, and she fucks your ass good and hard. You think she put on a strap on when you weren't looking until she moans louder and is yelling out that she's cumming. You feel warm splashes flooding your virgin hole and realized you're getting fucked by a guy. But you look at her amazing body and her beautiful face and once again choose to ignore that your ass was violated. You then spend the next few hours getting put into different positions and she has her way with your little hole. When you wake the next morning she gives you her number and says "If you want another hot night like last night give me a call, I enjoyed being inside you." As she smiles and gives you a kiss.

 

[turbocs37]

Fuck yes. This would be awesome. I would be more into sucking her all night long but getting fucked would be hot too.

 

[Astroman72]

I think I could go along with that.

 

[jackstud]

me too

I could play too

 

[CD_admirer]

That's a wonderful fantasy.

 

[bill3901]

L-O-L-A Lola...

 

[dacoach44]

Well now

Fuck yes. This would be awesome. I would be more into sucking her all night long but getting fucked would be hot too.

Just do both, like I do. Fluff up the cock, and then lay back and spread your ass wide open and let him make U his bitch.

 

[turbocs37]

Just do both, like I do. Fluff up the cock, and then lay back and spread your ass wide open and let him make U his bitch.

Sounds like fun.

 

[LostBabygirl3489]

Well the title of this post is a bit too transphobic in my opinion but there's nothing wrong or weird with your fantasy. Trans people are hot. It's okay to like trans people. I'd love it if I got with a trans guy or trans girl. A transwoman is still a woman, though, regardless of her genitalia.

 

[roc23]

I'd be UP for that.

 

[Anchor_4966]

.......

 

[UnderMyKilt]

Picking up a hot woman at a bar that turns out to be a man and does you.

This is a fantasy I've always had, going to a bar and getting tipsy, finding a gorgeous woman there that you flirt with, she likes you and invites you back to her house....blah, blah, blah

So your fantasy is just like that stereotypical scenario depicted in about 80% of all "Shemale" porn on the market.

Imagine that?

 

[FlaBullet]

Something VERY similar happened to me.

I went in the service at 17 and this was shortly after I turned 18. After an evening of partying with my friends in town, I was heading back to base. I was just leaving a rural area walking (mode of transportation when your low ranked and can't afford a car) back towards the city area to catch the bus back to base. As I was entering this area there were very, very tiny homes and it was an area that the prostitutes usually hung out. As I passed this older uglier woman, she said "hey Marine, want to get lucky?". I was walking pretty fast so I didn't miss the bus but I clearly heard her. I replied quickly not looking at her as I passed her that "I don't pay for pussy"! She sharply said I didn't ask you for money. I did the fastest to the rear march I had ever done and replied ok.
She was literally standing in front of her house and walked me right inside. I told her I needed to take a piss real bad and she pointed me to the bathroom which was just feet away from the front door. While I'm pissing I was thinking to myself how lucky I got. As I said she wasn't a pretty woman and easily in her 40's, but a young man with constantly full balls doesn't really care about such things and only cares about getting off with a real live woman. I pissed as fast as I could and exited the bathroom and she was right there and quickly yanked down my pants down and immediately sucked my cock in her mouth (first time my cock was in anyones mouth). I was thinking she has my dick in her mouth and my dick is still dripping piss. These thoughts ran through my head quickly as my cock hardened in seconds and it was only seconds later that I had cum in her mouth. It happened so fast not believing this woman was putting my cock in her mouth with such energy and enthusiasm, the warmth of her mouth and stroking me, the feelings were so strong that I came almost immediately. I could not believe she took my cum in her mouth and was swallowing it and making these little mewing sounds and showing me she loved my cum. My first blowjob ever and it was the best in my life.
As I slightly softened in her mouth, my knees got weak and I was struggling to hold still and not fall from the sensitivity. She was constantly looking up at me with a happy satisfied look in her eyes. She let my cock fall from her mouth and asked me if I could get it up again? Being 18 and just experiencing my first blowjob, (even if it was only 20 seconds) there was no doubt in my mind that I could get it up again and replied "oh hell yeah".
She smiled as she stood up, grabbed my hand and said let's go to the bedroom. As I entered the small bedroom, she closed the door behind her and I immediately took note that this was the darkest room I had ever been in, and I mean it is was completely 100% blacked out.
She came up to me and started kissing me and taking my clothes off. I was instantly hard again and she was focused only on my hard cock. After she had all my clothes off, she said "I want you to fuck me". I could not believe how lucky I was in hooking up with such a horny woman that was so forward with her wanting a hard cock to fuck her.
She pushed me down on the bed and straddled me while still kissing me. She grabbed my hard cock and started applying lube to me. She then rolled me over on top of her and guided me into her pussy and never stopped kissing and moaning. I started fucking her very slowly as I was afraid of cumming in her to fast. At this point in my life my cock had very little experience being in a hot pussy as I had only fucked a woman twice in my life and both were with prostitutes (don't judge me, I was in the service as a young inexperienced country boy and girls were scarce and the need for a woman was just to strong). I lasted about 5 minutes at most and when I started cumming in her and she kissed me even harder and her moans were more intense.
I was still laying on top of her and we were still kissing but much slower and more relaxed. She then flipped me over on my back and went right down of my cock. I could not believe this woman! She went down on me right after I pissed and now she was sucking me after I fucked her. I knew she must be tasting her own pussy. The thought of how wild this woman was, had me rock hard cock again in seconds. She continued to suck me and varied her techniques. Fast, slow, deep and didn't once take my dick out of her mouth. Now I had already cum twice in a short amount of time and I was not in fear of cumming to fast. She continued making these little sounds which clearly told me she loved sucking me. After several minutes I started to feel like I was going to cum again. She seemed to sense that I was getting close to cumming and doubled her efforts and her moaning was louder. This sent me right over the top and I started cumming in her mouth. As I was cumming in her mouth she made even louder moaning sounds that let me know she was enjoying me cumming in her mouth.
I could NOT believe my luck on happening upon this sex crazed woman. She did not take my cock out of her mouth and had me rolling on the bed and moaning due to the sensitivity. My cock had only slightly softened just a bit and she did not stop sucking and moaning with an almost pleading sound. She then quickly came up and lied down on top of me and started kissing me and continued to moan with even more enthusiasm. I was like OMG, WTF, eeeewwwww, this woman's kissing me after I came in her mouth. But I was still caught up in the moment of this woman laying on top of me rubbing against me and kissing with so much passion I just went with it. I was thinking this woman is just a wild and crazed sex freak.
I was again rock hard. She again rolled me over on top of her again and lubed my cock again before placing my cock against her pussy. She was really into it at this point and became very vocal about fucking her harder. I don't know if she kept that bottle of lube in her hand but she was constantly reaching down and soaking me in lube. Of course I thought older women must like that wet feeling and didn't think much of it. After already cumming 3 times I was much better at holding off and continued to fuck her and kiss her. She had really nice fake boobs and in that day fake boobs were something guys talked about but probably never experienced. I went from kissing her to sucking her tits. My staying power did not fail me and I fucked her for a long time. As I started getting close she immediately sensed it and was encouraging me to cum in her. Not to disappoint I started fucking her really fast and hard and started filling her pussy yet again. Before I was completely done cumming in her, she forcefully flipped me off her on to my back and went down on me again sucking my still spurting cock. I was like, holy fuck this woman is unreal. She is so sex craved and not shy about wanting to eat my cum.
She quickly came up and lied on top of me and starting kissing me again. I was more relaxed about her putting her cummy mouth on mine as I figured it must be her thing to get me to taste my own cum. Her tongue and wet lips with my cum. She continued to lie on top of me kissing me and then sliding up and having me suck her tits and back down to kiss her.
I'll cut to the chase. I came a total of 8 times (yes I was counting and it is a record and has never been repeated) and it was pretty much the same thing the next few hours. She would suck me until I was hard again and lay down on her back for me to fuck her again, again and again. I only fucked her once doggy style as she liked being on her back while being fucked.
When I hit the finish line, she asked me to go down on her. I was like oh hell no, I came in this woman's pussy how many times? There was no way I was going to eat her messy cum filled pussy. My sexual energy started to wane and I could not go down on her. She asked again so nicely that I felt compelled to try and return the favor. This woman was by far the best thing an 18 year old, sex starved kid could ever want. We continued to kiss and getting hard again just wasn't happening. I was done! She started to plead for me to please go down on her and let her cum like I had. I felt compelled to try and make her feel good. As I was moving south and holding onto a tit I found a cock! I was panicked, alarmed and downright scared. I told her "I can't do this right now and I had to get back to base". She seemed okay with me being panicked and told me to please come back and see her again. I assured her I would definitely come back and please her as well.

I would love to tell you I went back to her and got sucked and fucked and sucked her cock and swallowed her cum, but I was so shocked and scared of my feelings that I never returned.

I have beat off to these memories 100's of times over the years. I've always thought what would/could have happened if I didn't freakout and run away. I have never been with a guy (with knowledge), but always turn back to this event for the best jack off material that I have in my past. I've thought back wished she was a little more forceful on her wants and pushed me down with the same insistence of kissing me with cum in her mouth.

This was going to be a quick reply but I started typing and reliving it all over again. Also, this took place when there was no chance of catching a STD that a Dr couldn't fix.

 

[lazar4441]

Very hot sounds like the perfect evening.

 

[rae121452]

i had a friend who had a similar but entirely different experience. while in DC for work, he went to a gay bar he'd heard about. he's 100% gay.
anyway, there was a cute young guy that he hit on, one thing led to another and they went back to his hotel room. after making out for awhile, the cute young guy confessed that he was FTM, with the original plumbing. my friend was pissed off at first but they wound up making out some more, one thing led to another, and..............
my friend said it was the hottest sex he's ever had, they both went away happy and he says he'd repeat the whole experience any time.

 

[Naughtyboy31]

More like this scene...

https://m.youtube.com/watch?v=n6fgPX3NjyA

 

[JackOffer]

I done that years ago while stationed in Thailand, but I knew it was a guy all along and didn't care. In fact it made it more exciting.