What started it all (true story)

I had just started hooking up with men. A late bloomer, it was like a spark had ignited within me and I had not care in the world with any repercussions that followed.

I had met a very burley masculine fellow who wanted talked a big game and wanted me to put on his ex girlfriends lingerie. I obliged. He pushed me down to the floor and asked me to suck his cock. I felt inch by inch go down my throat and his cock pulse at the base. It was both arousing and terrifying. It was maybe the 4th or 5th cock I’d ever encountered. He flipped me around and without hesitation put every inch inside of me. I was not ready and I knew it then I wasn’t. So I squirmed away while he insisted I not run away. I was scared. So I quickly gathered my things and ran.

It took a while till I had courage to meet anyone after that. But one evening feeling a little lonely. I decided. Why not. I had been talking to a older guy (Tom)I was 20, he was in his late 30s. He said he was straight and wanting to explore. He said he was generally interested in trans but happy to meet and chat.

I rocked up at his house, again, nervous. But he ushered me in. Sat me down and asked if I wanted a drink. I obliged. We chatted for a bit about our experiences and I told him my last experience.

He stared into my eyes, crept in closer and put his hand on my thigh. I held a glass of water between us shaking. He guided the glass to set it down and pressed his lips against mine. I stopped shaking and he held me close and said “sorry that had to happen”.

He said “I kind of like the lingerie part though” and I said “oh really? I’d happily put some on for you”. Tom went into his room and pulled out a bunch of lingerie. He said he dabbled but it wasn’t for him. I undressed in front of him as he picked out a little red number - a laced body stocking. He helped me out it on and laughed that I was getting hard. “A bit unfair that you’re still wearing clothes”. Tom laughed and undressed showing a very impressive cock.

He said he’d never been with a cross dresser or a guy. We were both new to it and just continued to kiss. Tom getting harder as he ran his hands down my body feeling my body stocking.

I got on my knees. Looked him in the eye and put his throbbing cock into my mouth. I slowly put my tongue and warm mouth up and down his shaft and he said (slightly embarrassed) that he wanted to cum. When I asked where. He said “stay right there” as I looked at his body and cock showing some attention to his nipples he blew what seemed like a never ending load over my face.

We laughed. He guided me up and gave me a gentle kiss. My body was shaking. I had never been treated like a cum rag so gently before and he wasn’t afraid to kiss me. He said “cum for me babe” and just like that. My body tensed up and I came into his hand. We laughed and he guided me to the shower where got cleaned up.

As I prepared to leave he said “well… that was new. Lets do it again sometime.”

I smiled and said “sure” and went on my way.

It went silent for a few months and he reached out. He had apologised and said that he felt a bit guilty after that as it was his first experience. But he wanted to try again.

And that started a journey of cross dressing. We had met several times over a few years before I started having the confidence of dressing for others. Perhaps I’ll share more.