Close Encounters of the Third Gender Kind?

[TSFantasia]

Just curious to know how many of you guys have had a true "tranny surprise" experience that wasn't planned or payed for? Maybe it was at a night club, meeting someone through an online site, or travelling to exotic locations (I don't know if travelling to Thailand isn't a planned t-girl event..lol) ? Did she tell you as you were chatting her up, when you started to make out, or you found out when you reached into her panties?

[merelypink]

I wish that would happen!!!!!!!!!

[aguyoutthere1]

My very first encounter was with a Transsexual that I had no intentions of having sex with. Met her on AOL and I did know she was a tranny, and she was so close to passable, I found myself aroused and had to investigate.

We went to dinner, and she was dressed as a total slut. She was getting stared at a lot and I was not sure if people could tell or not. I've written about it before. We were in the middle of dinner and I asked what she wanted to do later. She said I want to go home and fuck you. It scared me, aroused me and I found myself saying. "CHECK PLEASE!!!!!!". Got back to her place, started to make out in her doorway and she pushed my head down and demanded me to suck her cock. The rest is history, hooked ever since.

Not a real tranny surprise, but actually not hesitating to go through with it was the surprise.

I always wanted an experience like Barbie described once. In a changing room at a mall or something. That would be so hot.



KC

[TSFantasia]

That sounds hawt KC! I've been tempted to give lots of guys the tranny surprise but guess always a little afraid of a violent or negative reaction. I usually try to feel guys out on dating sites to know they are very bi-curious or even bisexual before I agree to a date.
Here's the closest to one for me I was out at an Irish Pub on St. Patty's Day this last March with my BF at the time we ended up joining in with a group of 5 other guys who my BF knew a few of from an opposing soccer team. He had to call it an early night as he had to help his daughter with homework and worked the next days. The guys were all puppy dog eyes asking me "Awe your not going home already are you?" I said No i was sticking around for awhile. (Big smiles..lol). A few rounds of shots later and the one very good looking east Indian guy was getting really close chatting me up. When I said i was going to the bathroom he suggested he follow along for some cubicle sex! I said I don't think my BF would appreciate me doing that . When I came back he apologized for being that forward but said "How about just a St.Patrick's Day kiss?" I said sure I could do that. Ended up being a long french kiss my hand on the back of his neck his on my waist and squeezing my upper arm.
He said I should hang with them he had my drinks all night as we headed to the busy side of the pub. Kind of lost them in the crowd on and off as a string of guys came by to chat me up or just give me the "Hey how you doing?" routine. Saw Raj at the bar so went over to ask for a drink "Sure no prob" he said then he leaned over and said in my ear "Can I ask you a personal question?" I said "Depends what it is" He said " This has nothing to do with how you look cuz your fucking gorgeous but have you ever been a guy at some point in your life?" YIKES I just looked at him with a stunned look and said "Why would you even think to ask me a question like that?" He said "It was just when we kissed there was something different about it! You can tell me the truth Im your friend no matter what." Well I thought for a minute I don't think it was the kiss I think it was he was holding my bicep and they are rock hard when I flex (damn muscle memory..lol ). I said to him "Yes I am transgendered" He said "Thats totally cool I'm straight but you are damn sexy!" I said thanks and went on my way with my beer....

[CDN_guy]

Oh gawd! I wish it would happen to me.........................!

[aguyoutthere1]

Well that was a pretty boring non-story Fantasia. LOL

Now go out there and pickup some unsuspecting guy in the mall, bring him to the bathroom, suck him off and get him so hard there is not turning back, and then tell him to suck your cock. If I was that guy, I'd dive bomb down so fas



KC

[TSFantasia]

LOL your righti will stick to my diary entries

[Gentlemen J]

.......Now go out there and pickup some unsuspecting guy in the mall, bring him to the bathroom, suck him off and get him so hard there is not turning back, and then tell him to suck your cock.

Mmmm let me know where and when you're going shopping Fantasia

[TSFantasia]

Mmmm yes in a dressing room, in a bar or restaurant bathroom, on a bus, in a taxi, at a theatre, museum or art gallery much more interesting places to have sex then a stuffy hotel room.... Good ideas for a fantasy date night though !

[aguyoutthere1]

Mmmm yes in a dressing room, in a bar or restaurant bathroom, on a bus, in a taxi, at a theatre, museum or art gallery much more interesting places to have sex then a stuffy hotel room.... Good ideas for a fantasy date night though !

Theatre, definitely a fantasy. A porn theatre and all the patrons join in. (Well maybe not). I picture 5 Pee Wee Herman types. LOL.

The more public ones, bus, taxi, etc. would be amazing to see the look on peoples faces when a hot girl pulls out a cock and I suck it. WILD.


KC

[Rantsalot]

...

i would not, could not in a tree.
Not in a car! You let me be.
i do not like it in a box.
i do not like it with a fox.
i do not like it in a house.
i do not like it with a mouse.
i do not like it here or there.
i do not like it anywhere.
I do not like to grandstand
i do not like it, Rants-i-am.

[OnTheRoad]

I was young, very early 20's, not very experienced with the ladies either at that point. I am from Regina but went with a friend to Winnipeg. He had plans with family, so I went out on my own solo, cruising around, not familiar with Winnipeg at all, but young, inexperienced, and looking to get lucky lol. Ended up finding a streetwalker, picked her up and went for a drive, first time ever doing that, figured might as well try it in a different city. So we found a quiet place to park, made a deal on oral fun, then started making out. She was gorgeous. We're kissing like teenagers (lol, guess I pretty much still was one at that time) I'm feeling up her average sized rack, she's rubbing at my crotch... hey, this is awesome... I'm trying to get a feel on her crotch but she shifts her hips away from me and is really insistent that she wants to go down on me... okay, no problem-o... I love blow jobs! So away she goes to town on me... it's great, but I also get pleasure out of giving a woman pleasure too, so I really want to get into her panties, and am persistent, but not pushy or rough about it, just trying to flirt, convince, bribe, lol, but I really want to rub her pussy... but she stops me, and says she'd rather just take care of me. And I'm like, don't you want to feel good too? She's like, yes, she'd like to, but she's a little different that most girls... and that really didn't make sense to me, I figured it was a matter that she was shaved or bushy or who knows, but I was puzzled... and I'm like, what do you mean by that? she asks if I'm open-minded... and I really have no idea what is coming next, but say yes, I am open-minded... at that point in my life, I only thought there were two genders, and this was obviously a beautiful woman. She says, are you sure? I say yes, so she grabs my hand and puts in on her crotch, and there is a bulge, and she says she has a cock. I'm like, no way, seriously? Yes. Okay.... (both wondering what is coming next).... so I ask, can I see it? Uh, sure... so she pulls it out. Well, I'll be damned if this girl that is smaller than I am has a bigger cock than I do! I'd never had any male contact before, but I really wanted to touch it, so she let me, as she continued stroke me. Then she asked if I wanted to suck her cock. It was one of those moments that, very conflicted, I was very curious, and thought to myself, what the hell, why not? so I did... she was so sexy... I can hear her soft girl moans as I sucked her hard girl cock... it really got me excited, and her too... that soon she said she was going to cum and told me to take my mouth off or she'd cum in my mouth. Well, I'd gone that far... so decided to let her cum in my mouth (really, when was the next time I was going to suck a cock, right? might as well get the full experience), but it was my first time and too much, so took my mouth off and she kept shooting, on the dash, on the windshield... and all of that made me cum as she stroked me... what a mess in the car, and careful clean up to make sure I didn't miss anything, lol, but well worth the experience... I couldn't believe it, and just kept playing it over and over in my mind the entire drive back to Regina with my buddy the next day. And I've been bi ever since. I've never told anyone that story before, so thanks for posting the topic Fantasia.

[TSFantasia]

And In Winnipeg of all Places!!

Thanks for sharing your experience! I think that's the first REAL "tranny surprise" shared on this thread so far..and happened in Winnipeg of all places. I was thinking Vancouver or TO would come up with lots of "surprises" . Glad you enjoyed your "Walk on the Wild Side" so much that you decided to stay

[TSFantasia]

WTF No Balls!!! LOL

I have these experiences all the time sometimes its after having a few dates with a guy and some times the "surprise" happens even before the first date. It usually goes something like this meet on a dating site (POF) or hookup site (AFF, TSD) and the guy is "OMFG you are so hot I want to meet with you for drinks anytime you want!" Me "Sure what night?" Them "I'm free every night just pick one and time and place and I'll be there!" So time and date and place is chosen and communication continues til the night before. "Ok text or email me when your done work what time is that?" "About 5 o'clock and will do " Next day 5:30, 6:00, 6:30 no message . So I send message "What's up?" 7:00 then 7:30 . Then come the excuses ... "Oh had to stay late for work, oh broke my leg, got into an accident, my mother is dying , brother's car broke down 2 hrs out of town going to help him out....." Hmmm I've just had my "tranny surprise" I thought I was talking to a man with balls but apparently NOT! So definitely something that should show up on IDs : MHB (Male Has Balls) , MNB (Male No Balls).