Here’s who popped my virgin tranny cherry!

First times are definitely best. Mine was with Peter, a retired man in his late 60s, white hair, broad shoulders impeccable manner.

He taught me to drive which was easy, I had been behind the wheel of any vehicle for as long as I could remember. But lucky for him, he was teaching me when I was first openly experimenting with my gender.

So a little skin cream or perfume, clothes a little too tight, effeminate colours…yeah I guess I was flirting. I always showered and washed my hair to look my best for him. I fantasised about what would happen and how iI’d react when he eventually put his hand on my knee, my heart raced and my cock went rock hard just thinking about it.

When it came, it was a complete surprise.

Not on a lesson, but when I was walking home from the train station after an afternoon in the city. I heard a horn bip and guess what, it was Peter, offering me a lift to my house. I couldn’t say no and I knew I had to think quickly and get him to detour, so I cooked up a story about a row at home. I was in no hurry and suggested the scenic route by the lake.

He still didn’t appear to take the hint, so when I asked him to pull over I started opening up about myself and about how I wanted to experience sex but with someone trusted. That was all he needed. He gently brushed my cheek with his hand, ran his fingers through my hair and I could feel the strength in his hands and his thick fingers. I thought my heart was going to burst it raced so fast!

He held my face gently and kissed me on the mouth, gently stroked my tan arms and just pressed his hands down on the solid bulge in my tight jeans. “Can I” was all he said. I could only nod “Yes”. If i wasn’t shaking so much I would have said “Yes, ride me like a bride on her wedding night, take no precaution, get me pregnant!”

He was expert and SO experienced.

All serous he unbuckled my belt, opened my jeans (yes, I did the Bridge – lifting my ass so he could take my pants down) Taking off my trainers and socks, getting my jeans off all the way so I could open my legs, then it started – no more Mister Nice Guy!

He rolled over on top of me, tongue down my throat, eating me. He drove his bulging pants hard onto my erection, I was literally shaking like a leaf when he went down on my and took my long, thick cock in his mouth just saying “Jesus fucking Christ I wanted this”. I moaned out loud, I had wanted this since the day my balls dropped!

He sucked my balls one at a time, wedged his head between my legs inhaling the heat. I loved that sight – looking down on a white haired man with his head between my legs, a sight I have seen so many times since.

Then he stopped and just as carefully took off his polo shirt, pants and jocks and invited me to kiss his hard nipples, kiss his chest hair, kiss his soft fat belly and FINALLY my dreams come true, kiss and suck and lick his pissy, pre-cummy stiff cock. Divine! His precum webbed around my mouth, he held my head and rode my mouth and then I heard it for the first time – the stop-start breathing of a man about to cum. A flash of heat in my mouth and I swallowed every delicious drop of his load, sucking and coaxing out every last drop. He was gasping for breath and I was afraid he wouldn’t do me, but ever the pro, he put his hands under my tiny ass to lift it up and made love to my cock. My orgasm was quick and off the scale in its intensity, bullets in the roof of his mouth that he aggressively spat back onto my pubes, then nibbled off the cum and swallowed it, bit by bit.

I was born again, spent, drained, exhausted, sweating and in total lust.

Then he just started dressing like this happened every day, so I did too. We made a date to meet in his house the next Saturday while his wife was out and I went, knowing that he would ride me that day and my transition to a woman would really happen. He told em the exact address, time and instructed me not to masturbate after Tuesday night – torture! But I did hold it back and it was worth it…I’ll tell you in my next story.

Oh and I did pass my driver test first time. Success!

Leave a Reply

Your email address will not be published. Required fields are marked *