Although my favorite kind of sexy story is about first timers, you can only have one! Also, true first time stories are usually very awkward! After all, its a first time! rsrsrrs
I can say I'm a bit fortunate on this! My first time, as I tell the story [here] (https://steemit.com/sex/@caradebh/the-day-night-i-lost-my-virginity-spoiler-alert-to-a-trans), was absolutely fantastic! (maybe it was average, but how could I know at that point?) lol
So, I got instantly hooked on the shemale experience! Only thought of that, only jerked off of that (still mybe 90% of my porn interest)! I Slowly stopped watching regular straight heterosexual porn! All I needed was to gather some more courage, man up, and do it again! :stuck_out_tongue:
Image: Patricia Araujo, a Brazilian transexual!
So, there I was! full of plans, and heading to the same street, around 10 pm. I drove for around 1 or 2 Km until I saw her! She was absolutely gorgeous! very (as they say) passable!
I had to drive around the corner again, to reach her. I stopped the car, rolled down the window and she came to me. She asked what was I looking for. Funny enough, I couldn't say a word! My mouth was so dry, I was almost panicking! lol.
All I said was an almost silent, "wanna play?" Oh god! I was single, didn't owe anything to anyone, prostitution is no illegal here, so I wasn't doing anything wrong! How could I be so nervous? rsrsrsrs
Well, she got into the car and she said she lived close by. So we drove to her apartment. I cannot remember a single detail of her home! All I saw as a big bed, in a room, across the hall. Maybe there was a TV, and maybe there was someone else there watching it! That is how nervous I was! rsrsrsr
So she asked what did I want to do! I said, I wanted to bottom her! She was very nice about it and started caressing me, making me more relaxed! I was starting to enjoy it! She didn't kiss, which was ok, only hugging here and there, and running here hand on my body. I did the smae!
She was wearing a grey strapless top, a very (VERY) tight shorts, a smooth red lipstick and had a very long straight black hair! I remember she smelled like strawberries! Like a strawberry candy stick! Not my favorite, but it was fine! I remember she was skinny, with long smooth legs although I can't remember her shoes! (Common! It was around 2003)!
On a moment, I reached my hands to her shorts, she had a very bulky bulge there! I should have known that it was not always going to be easy as the first one! In my defense, I have not seen that many real life junks, and mine is just average, so I did not anticipate that! Otherwise, I could have asked to see it before hand and make an informed decision! lol
Well, it was too late for regrets! I wasn't sure I could take that, but I was too excited to back up now! So I let it flow!
Image: Vixxen Goddes! One of my crushes!
After a few minutes, she just stood up, and removed her shorts, she kept her top on, I believe she did not have yet a proper boob job, although i love a nice pair of boobs, i did not care a bit about that! So, she took her shorts off, she was wearing blue panties, dark blue, and there it was, her penis was there, big and hard! Waiting for me! I got a little scared!
Was it going to hurt a lot? was it fiscally possible to take all that in? was I going to get hurt? You don't usually imagine how many things run through your mind in these moments! Maybe I was exaggerating, maybe not! I was 21, only one sexual experience and have very tight ass (still do! :stuck_out_tongue_winking_eye:) !
She put me on my knees, I grabbed the pillow and tilted my but! I must say, she was very nice to me! She put on a condom (a absolute must!) and some lubricant or her dick. She then put some on my butt hole! it felt amazing! lol And she touched the tip of her dick on my butt! I must say, this is now, my favorite part of intercourse (being a top of a bottom, with a woman or a man! doesn't matter! this first few seconds, on which only the tip touches you!!!). She started forcing it in! Yes force it! It was VERY LONG and think! It was easily 20cm (~8 in). I felt like she was about to tear me apart in half! Oh Boy!
It hurt like crazy! but the pain did not last long! as She just waited a little before forcing a little more. And little by little she as full in! I swear I could feel her dick poking my intestines! lol, such a wired feeling! But I must Say, it was FANTASTIC! She started moving it in and out! and All I could do is twerk a little bit, and MOAN! Oh did I moan! lol
She fucked my ass for a long time! I can't say how long, precisely, but was a long time! and she grabbed me by my rips and just went on in that cray motion! I though I died and went to heaven! It did not hurt anymore! All I could feel was that think junk of meat fucking my tight asshole! So HOT!
Later we rolled over, and I was on my back, with my legs up on her shoulders, and she started again to fuck my tinny hole!
After a while, she asked If I wanted to fuck her too, I accepted and she stood on her kneed in front of me. I put on a condom, and som lubricant and started fucking her. But that was not what I really wanted. And A believe my performance was not that great as she turned over to me and said she liked my ass more! lol!
So she fucked me a little more until she cummed! After that I was satisfied! but she insisted I cummed too, so she started to give me a blow job. I nutted a a couple minutes and was done! lol!
I must say, if I have to go back and choose, from every experience I've had, the top 10, this would be on the list! She had a huge cock (not the thickest I've had, but easily the longest). I tried to get her again later on, but never found her again! sad!
Well, guys and girls, this is the story of one of my best times! Was the second time I'v had sex, and again, I HAD to bottom! I still dream about this night! :)
Thank you all for reading! I hope you enjoy it!
Doesn't she look a little bit like Bailey Jay??? Another crush of mine!
bye!
