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Meeting With My Ladyboyfriend

636 words | 4 |4.00
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Meeting with my older ladyboyfriend for my birthday

So I just recently turned 17 and was being wished happy birthday by a trans-woman I would frequently talk to on Kik, we live in the same city and would always chat and fantasize about eventually meeting up. Well considering it was my birthday, I figured there was no better time than now to treat myself with her.

We had a short conversation about how we would meet and just settled on meeting at a motel between our homes. I told my parents that I was spending the night at a friend of mines and drove 20 minutes to the motel I was told to go to and was giddy the entire drive.

Eventually, I arrived and met my lady friend in the parking lot, she was tall (like 6’0) and beautifully built, she was wearing a short sundress that revealed her meaty thighs and a slight bulge when she stood up straight, her hair was long and wavy and her eyes were shadowed. We hugged and she guided my hand to slip underneath her dress along her ass, it felt strong and soft at the same time.
“I figured I’d doll up for your birthday” she whispered.
My head was fuzzy at her voice, sweet and assertive.

I let her go into the motel and pay for a room while I waited outside for a few minutes before going in and walking to the room number she sent me. I opened the unlocked door and found her standing at the end of the bed fully naked with cuffs attached to each end of the bed’s headboard. I was already rock solid under my sweats, my shirt came off as she walked near me, her large member grazing her thighs as she approached, she grabbed the collar of my sweats and pulled me over to the bed, laying me down and locking my hands into the fuzzy cuffs assigned to me.

My lady friend put on a show, taking a moment to wish me happy birthday and compliment my length and stature begging to burst through my now revealed boxers, she grinded on my covered dick with her bear ass and balls and kissed me passionately, her acrylic nails tracing my chest making their way to the underneath of my balls already coated in pre-cum.

She pulled down my boxers and smiled at the eagerness of my dick, her tongue met my tip where a shiny drop of cum was ready to greet her, she then engulfed the entirety of my length in a single motion, her tongue tracing along my balls, her hand softly pinching and massaging them as she repeated the process again and again, sending shivers up and down my spine.

I would speak to her when I was about to finish so she could stop and let me rest with kisses mixed with spit, sweat, and cum. She would also take the opportunity to straddle my chest and let me take her member into my mouth with her ball’s hitting my chin, her laughter echoing in my ears at the sight of my rolled eyes.

Eventually, she moved to her purse and pulled out her favorite lube, something fancy. She lathered me how she wanted and wasted no time straddling me, my dick massaged by the tight walls of her hole more and more with each stroke, ending with rough fucking as she bounced on my hard cock for what felt like only a few seconds before I came hard inside of her, nearly passing out from the bliss.

When we rested and awoke the next morning we kissed goodbye and promised to do this again soon.

Hope you enjoyed my story:)
If anyone wants to chat I’m a 17m and my
Kik is: incognito.inc
And my Snapchat is: incognitoha

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4 Comments

  • Reply TARA ID:1e04lr5xxpf2

    I always had this fantasy of a beautiful Thai ladyboy all dolled up wearing a skirt or dress and nylon tights. fucking and breeding me doggy, while a straight guy is fucking and breeding her, as the three of us cum inside us at the same time !

  • Reply Scott ID:1crdunb9xpn0

    Great story I love dick . I have five brothers and I take care of all them.

    • Xzander ID:mzib7740

      Can we meet up

    • Bigcock12 ID:20pep01gzk

      Scott i have a big fat 12in cock for you and I want to suck your cock and fuck your ass you can fuck my ass and suck my cock i want you