Yes, I think I'll start with that!
This is a true story! Although it might sound fake!
The thing is, I was always a shy guy, had a few crushes in high school just as anybody else! However, being extremely afraid or rejection, well, I still am, I was very afraid to move on forward sexually with the girls I was dating. Because of that, I graduated from high school and got into college still a virgin!
But you guys know College! Its a very unique period of our lives! One day, I was looking at porn on the internet and mistakenly got into a shemale website. Although I was never attracted to them, I just lingered there to see what it was about! The thing is, I got Hooked! It was addicting and soon after I could only masturbate to shemale porn! I was never worried about my sexuality but this carried an extra element of excitement: The Taboo or a Forbidden element!
So, one day, coming home from a party, i was driving (little buzzed, I'm ashamed of confessing) through a street full of shemale hookers. I was curious and very excited and decided to stop!
This one was not particularly pretty of 'passable' as they say, but I was not going to back up! We agreed on a price, and we drove to a dark street close by (Yes, on the street!). There I just went with the flow and had set in mind I was going to do everything I dreamed of when watching shemale porn!
First, she reclined the passenger's seat and laid flat (really weird for me!). I just went on and pulled her dick off of her tiny skirt. She was already hard! I than started sucking it! VERY clumsy and not knowing what I was doing! But, at this point, who cares????
I was in in my own world there! So naive! lol
So, After a few minutes, I asked her to stick it into my as! I REALLY had no idea what I was getting into! She had no lube! So I put a new condom on her dick, pulled down my pants and underwear, and just got into my flanks, looking at the street outside the already steamed windows! I don't know how it worked! But when I felt the tip of her dick, in the vicinity of my asshole, I was in ecstasy! I grabbed my but cheeks and spread them apart!
When she started pushing it in, it was really weird! I though it would hurt a lot more than it did! Maybe I just wanted it too much, or maybe her dick was not that big! I can't really tell! But finally she was full in!
The weirdest part of it is that I never considered myself gay, bi, or anything, but it felt sooooo good! She was pushing and pulling on a rhythm so good I was in heaven!
After a few minutes, she pulled it off, I think she came because she was getting soft again! So she asked me if I wanted to fuck her. I was like, "OK", I really didn't care, I was already satisfied! lol!
So she got on her knees, in that really tinny space and I fucked her as for no longer that a couple minutes, and came! lol.
I drove her back to where i picked her up and left home to dream (and masturbate) about this night for a few weeks before I had the guts to do it again! lol!
I don't know about you guys, but one upside of this was that the friction burn was not painful, but it let me remind myself of that moment! lol, feel stupid thinking this, but it was awesome! It was only a couple years after that that I had sex with a woman for the first time! It is a very diverse experience! in one case I let myself be led and the other one I'm the active part! Both incredible but with its own benefits!
Today, I really enjoy anal sex, but since I'm married (to a woman) I don't get to have this type of experience again! That is why i'm sharing mine with you!!