by blacktopchaser

Gender: Male
Age: 53
Race/ethnicity: White
Current location: New York
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Accountant
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Curious honest slutty sensitive
How many sexual partners have you had in your life (including oral sex)? 25
How many hookup stories have you here posted before? 0

She Was Born a Boy By Mistake

How long ago did this hookup happen? 3 years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? FWB paid
Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? I saw “Eva” on a she male escort site and WOW!!! I had to call her. First and only escort I’ve ever been with and we’ve hooked up about 10 times so far. Tall lean leggy black she male and her face is cuter than cute and prettier than at least 90% of all the “real” women out there.

Shemales always intrigued me, but the concept always was hotter and much more sexually thrilling than the reality. If you’re somewhere around my age and you’ve seen the M*A*S*H series on TV, then you know about Corporal Klinger who dresses up like a woman to get out of the army – unsuccessfully. And he doesn’t look at all like any woman I’ve seen. He’s a short hairy not very attractive man with a huge nose wearing a dress. And he’s also the first thing I think of whenever I see a tranny in a porn scene or in person. Because they look more like men in drag than girls born as men. Almost all of them and to varying degrees. And most of them have fake tits that are cheap and ugly and also funny all at once.

Except for Eva. She’s drop dead gorgeous. With no exaggeration on my part. She has small but still hot hot titties that are her own and from her hormone therapy. With long thin nipples that make her dick hard in seconds every time I put them in my mouth.

She’s one of the prettiest girls I’ve been naked with but there are three things that make it obvious she was born as a guy. Her Adams Apple which every tranny has but I don’t see it on her long sexy neck. She’s at least 6 foot 2 and very few “real” women are this tall. And of course she has a dick. Not huge but not small and I’d say it’s bigger than average and big enough to be a big dick to the average dick loving girl and boy but not enough to be a really big dick. Mine is 8 inches which is a really big dick and it’s visibly longer and also much thicker than Eva’s dick. But Eva’s dick is still hot and beautiful and there’s more than enough dick in that dick to make me shiver from the sexual thrill I feel whenever I see and hold it and have it in my mouth.

But that’s not all. Eva is also a very nice and intelligent and good person. And she and I have great chemistry every time we meet up. Great sexual chemistry and also great non-sexual personal chemistry that we both felt and noticed and talked about together and it’s always there when we are together.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My place. Internet escort

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We’ve had multiple hookups. Here are some highlights. The first time was like most first time sex hookups that happen when two people have their first ever fuck. Yes this was a business deal which of course makes things different but the chemistry and vibes I mentioned above made our first hookup much different from the first hookup involving a professional. So we both took things slow. Talked a lot at first – both fully clothed which made us both very comfortable with each other very quickly. Which led to me asking Eva to strip down slow and sexy in front of me. Which then led to me getting naked as soon as she was. And then the touching and licking and mutual dick holding stroking which soon turned into mutual cocksucking in a hot hot 69 with her on top. And 10 minutes of that made me come from her making love to my dick with her mouth tongue lips and hands. She always requires every client to wear a condom over his dick and she made no exceptions for me – ever. Of course I’d prefer no condom but she and we and the sex we have together are all so fucking good and so fucking hot that a condom on my dick doesn’t matter at all. And she does’t use one on her own dick and if there has to be a condom on one of our dicks I’d put it on hers every time so I can suck her off the natural and so so hot and erotic way we all should be sucking every dick every time if STDs didn’t exist.

And one time was a sex toy party. I fucked her hot round ass with a dildo and a small and large size buttplug and with one two and for a while three of my fingers. She was on fire from the sexual thrill she was feeling the whole time but she didn’t prep herself in advance to get fucked and I wanted to fuck her with my own real dick as the grande finale of that hot sex hookup so much but it wasn’t gonna happen and I had no control over it anyway.

And the time she came over after we hadn’t seen each other for almost 5 years due to me having a girlfriend (and I don’t ever cheat on my partner if our thing is serious enough to be a can’t fuck anyone else but her kind of thing). She was only 21 that previous time so this time she was around 26 but she looked exactly the same to me. It was like a sex reunion of two former lovers who are thrilled to be together again for another hot fuck. Kissing with passion, sweet talking, hand holding, nothing rushed or forced or out of sync sexually. And groping jerking sucking and me coming with my dick in her mouth once again and then she wanted to stay and just hang out and talk and cuddle after that which is a sign of intimacy to some degree between sex partners when neither of them is an escort. So when an escort does that you’ve definitely got an interesting thing going on.

Did you have an orgasm? Did your partner(s)? I came every time that Eva and I have hooked up. In her mouth when she was blowing me (with condom as always) a few times. On her hot little titties once after some hotter than hot making out and mutual jerking off both at once. Once when I was on my back with my legs spread wide and her dick in my ass. Still haven’t done that with my dick in her ass for a few reasons but that’s on the agenda the next time we meet up.

I always ask Eva if she came when I think she did from what I see and hear and sense but I never saw her shoot her load and her answer is always “kind of” but my guess is she’s never had an orgasm when we’ve hooked up for sex. But one time we were hanging out on my couch, both naked and watching some porn on my laptop, jerking ourselves and each other off and making out, and she tells me she just came. The lead up right before that looked like she was about to come but I didn’t see any cum shoot out her dick or anywhere on her body or elsewhere afterwards. Maybe she doesn’t produce jizz when she comes anymore? I could have asked her that knowing she wouldn’t take it the wrong way due to our unique friendship but I didn’t ask her right then and the time for asking it was gone after that. It remains a mystery but one I don’t really need to solve.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms on me always and not on her except when she fucks me. And condoms over fingers and ass toys always too

What were your REASONS for having this hookup? I saw her on the internet and the rest was history

Were alcohol or drugs involved? If so, how much? None for me or her. Not ever

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? See above

To whom did you talk about the hookup? How did they react? Nobody

Was this a consensual and/or wanted experience for you? For your partner? Yes and also a business relationship.  See above

Do you regret this hookup? If so, why? What’s the total opposite of regret? That’s what I feel about each hookup and our relationship as a whole

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I learned there is at least one she male out there who is drop dead gorgeous. I’ve seen trannies who are attractive and a couple were more than just attractive but Eva is the only true hottie girl I know who also has a dick between her legs

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

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