I [M] went from getting orally serviced by one of our team’s water girls, to discovering she’s trans [TF], pounding her in the shower and then upwards from there ?

I play competitive soccer full-time for most of the year. It’s a very good gig, all told. There’s a small group of all-purpose team helpers who do stuff like getting water, collecting towels, running “go-for” errands and stuff. All of them are college-age. Two years ago, a new girl started – Leslie. (Not her real name, obviously.) Real pretty, 23 years old (I’m a little over ten years older), short, curly blonde hair, green eyes, and an amazing rack. I noticed her right away.

Everyone on the team is really friendly with the “gofers,” since they’re around all the time. Even the girls are often in the locker room while the guys are in various stages of undress. It’s just how things work. In part for that reason, there are supposed to be strict rules about no fraternizing with them or other team staff. But… that rule goes ignored pretty frequently, which is pretty common with sports teams.

Leslie noticed me, too. She would cheer me on the field, give me eyes off of it. I realized, later on, that she mentioned her hotel room to me a couple of times on away games, and that I should’ve realized what she was hinting at.

So one evening after practice, I rinsed off real quick and then hit the sauna. I heard a knock at the door, and then Leslie is there, poking her head in. Asked if I needed anything – or if I’d like some company. I said… sure. To my surprise, she strips off her shirt – she had a sports bra underneath – and comes in. (She was wearing running shorts too.) She said most folks had already gone home – it was pretty quiet out there. Seeing her getting flushed in just her sports bra had a definite effect on me in my towel, as you can imagine.

To cut to the chase, just a few minutes later, after some pretty heavy flirting between us, she peels off the towel from my lap, slides down to her knees and is sucking my cock. She even pulled her tits out of her bra for me – almost D cups, they’re spectacular – while she did her thing. She is very good with her mouth. Lots of wide eye contact, moaning and working my shaft with one hand and balls with the other. Deep throated my whole cock without any gagging. It hardly took me any time to blow in her mouth, and she swallowed everything with some incredibly hot little whimpering.

Then, she got up, kissed me on the cheek and let me go get cleaned up.

After that, Leslie managed to find me after nearly every practice to suck my cock. She called it part of her duties as supporting the team, which I thought was pretty cute. She sucked me off in the team auxiliary room, twice in the locker room when folks weren’t around, in the little office next door. This went on for several weeks I tried getting into her pants but she always made excuses why not.

Finally, on this one away game trip, she came clean. She was nervous but finally came out with it after some liquid courage: it turns out, she had a dick.

I was blown away. I figured I could always *tell* stuff like that but… nope, no way, not for a second. But honestly, knowing her, it didn’t make me want to fuck her any less. A few minutes later, she was naked on my hotel bed and I was thrusting away in her “pussy.” It was fucking incredible. She is truly an amazing fuck. Later, she let me fuck her tits, bobbing the head of my cock into her mouth as I went.

It turns out, Leslie had gotten surgery about a year before she started with the team. Had lived as a woman and been on hormones for a few years by then. She also won the genetic lottery and naturally looked very feminine – though she spent a lot of time making herself up, too.

After that, she didn’t stop sucking my cock around the locker room – but occasionally, I’d pull her into the shower block if no one was around, and she’d wriggle out of her little running shorts and let me pound her against the wall. It got her off like nothing else, she said, to feel my big cock deep inside her. (She doesn’t like me touching her “clit,” but will sometimes help herself to get off.) She would occasionally wear some particularly cute panties and flash me when she could, and I’d spend all day with a half-chub because I couldn’t wait to make her moan later.

So anyway, eventually we started dating and just had to keep it very under wraps, though a bunch of our friends on the team knew. (Very few knew she was trans.) Her landlord upped her rent at some point and she couldn’t afford her place anymore – she made very little money with the team and supplemented by waitressing – so I told her she was moving in with me. Great move. Turns out, Leslie is super domestic. Makes me breakfast each morning, bakes cookies for the team, that sort of thing.

They cancelled our whole season this year – thanks COVID! – so Leslie and I decided to just ditch the secrecy and make it official. I married her two months ago. Her parents were a little suspicious at our age gap but decided they liked me when Leslie assured them that I treat her well and we make each other very happy. The guys in our condo complex always eye her whenever she lays out in her bathing suit and I sorta do a fist pump. I scored!

Source: reddit.com/r/gonewildstories/comments/ht2ywl/i_m_went_from_getting_orally_serviced_by_one_of

102 comments

  1. Th is is the most wholesome thing I’ve ever heard, I love it and am so proud of both of you!!!

  3. I may prefer them with their dick (no homo). A year ago I hooked up with a trans girl who kept her dick. It was fun. Anyway. How’s fucking her? Is it very different than a normal pussy? Does she cum? Congratulations btw!

  22. Wow best story on here!! Congrats at having a partner who makes you happy!

  31. aww this is too cute! i hope you two live a happy life together!

  32. Congratulations, and thanks for the really cute story! I hope the two of you will always be happy!

  33. Bro this is so adorable. I’m super happy for the both of you. Seriously this is great!

  34. This is fantastic and took a turn i didnt see coming. Congrats to you both!

  35. Serrrrrriously wholesome! I love this so much! Congrats to you both!!!!

  36. If there was a “wholesome boner” award then you definitely would have earned it. Congratulations my friend.

  40. Dang this should be reposted to /r/wholesomesexstories! Hot and sweet!

  42. Turns out my kink is wholesome happy endings. Thanks for sharing your hot stories and blubber inducing twist.

  43. r/WaitAMinuteThisIsWholesomeContent

    I came here to touch myself now all that was touched is my feelings

  44. I’m not trying to be insensitive I’m just curious, when you mentioned Leslie had urgery and also mention that she had a dick, by “pussy” did you mean her rear or her vagina?

  47. Thats what i want so bad! I wish i could find a trans woman to make my bride!

  49. This is one of the best stories I ever read. Happy for you two, and hope it works out long term! Congratulations!

  51. I don’t support transsexual (religious reasons) but it hurts me to hear her rent got upped because she was a transsexual. You may not wanna hear sorry from me, but I am sorry to hear that.

  67. That is a sexy wholesome story. I wish you a prosperous lifetime together.

  68. Wasn’t expecting the cuteness and damn bj in the sauna what an exercise

  70. This is the most wholesome way I’ve ever gotten turned on. I LOVE THIS.

  73. I mean… Its so hot but so cute and wonderful. Thank you so much for sharing!

  77. So wholesome ♥️ If you have any sex stories wirh your wife, dont hesitate to post them ?

  79. Awwww it ended with you getting married?? So cute!!! And thank you so much gor your understanding with her, many cis people would claim its somehow a trick or hiding something you deserve to know and gotten angry when she revealed she was trans, and im so glad you didnt. People like you give me hope!

  80. I read “I’m nearly over ten years old” instead of “older” and read the whole thing very freaked out

  81. Gonewildstories says Trans Rights

    Congrats you crazy kids, hope you have a great life together.

  84. Am I allowed to still masturbate to this wholesome story. I’m so confused

  86. Hot and wholesome, great story. A bright spot during covid feels really good.

  92. I don’t want it to sound offensive but how could she have both a dick and a vagina? Educate me please.

  96. As a reminder of Rule 4. Please keep it civil. Negative or shaming comments will be removed and may result in a ban.

  99. For real I can’t even beat off to this.

    It’s too fucking wholesome. What a great story.

  101. Awwwww….. Congratulations to you both!!!! ????

    Wishing you a great life ahead

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