Young Fantasy - First Time I CrossDressed And Was Barebacked

He was not the first guy I had been with.

When I was 1 -6teen I had been scouring ads on Craigslist for months, looking for a guy that could help me dress as a cute slutty girl. At the time I was 6’2” thin athletic body cute butt and essentially hairless and shaven everywhere else. I had seen some crossdresser and trans porn a few months earlier and just had to try dressing myself. I finally got enough courage to email a few guys and I set up a meet with this guy on the following Saturday prior to the meet he asked my body dimensions weight etc. when I arrived at his condo he invited me in and gave me a big extended hug and a kiss on the lips he was very handsome and in shape mid 50’s dressed great and complimented me and said how happy to finally meet as I agreed we talked then we headed to his bedroom as he said he had gotten a few things for me.

He had bought a lot of clothes. Lingerie bras thongs short skirts dresses wigs high heels you name it he had it mostly sexy tighter fitting clothes. He said shall we start and at first we would pick and outfit out and I would go in the bathroom and try it on but after that he said just change here. By the 4th ish lingerie outfit I really liked and I’ll never forget. Hot pink thigh highs and thong (loved the way my ass looked) hot pink garter and hot pink underwire bra (he put some tissue in it). I had black high heels on was really hard to walk lol. I said yeh this is it then I started trying on clothes after. Tight dresses little skirts tube tops and blouses. When I tried on the purple slutty school gurl outfit I new it was the one with a tight blouse a purple plaid choker and short purple plaid skirt that you could see the bottom of my cheeks. After I was all dressed we did wigs and ended up with long blond hair then he sat me down and he did makeup for me including hot pink lipstick eye lashes everything clip on earrings. I looked beautiful so sexy and hot I felt like I was on top. I loved the way the clothes hugged my body tight yet light. By the time I was all dressed hours had passed. So we took a break and went to his living room he made himself a drink and asked if I wanted one he made me a vodka sprite. He asked if he could take pictures and I happily said yes anything thank you so much. I posed for him in various positions with some items like glasses, teddy bears, books, butt plug, and dildos etc. (this was not my first) I kept thanking him the rest of the evening.

During pictures of him posing me against the bar we kissed for the first time so passionately. I kissed him back reaching down cupping his pants we ended up making love. He was so turned on his uncut cock was precumming a lot. I was already lubed from the photo shoot. We didn’t do any foreplay really except kissing and touching it was right to sex against the bar. He pushed my little skirt up and pulled my thong to the side as entered grabbing my hips. We were moaning together he was clothes to my skin as we made love I was reaching back pulling him to me. He felt amazing as he was making passionate love to me my hard cock was precuming. He pushed hard thrusting till he stopped and started kissing my neck as he finished I finally felt complete. His warm Dick stayed inside me till he fell out soft.

I saw him for the next 5 years until I went to the army. After that we lost touch. He always bought me new slutty clothes and encouraged me to dress. He thought me so much and I am so grateful to have met him. He was and is an amazing man. I wish I could see him again.

Since him I have always been into older gay guys and uncut is a major turn on. And I usually cum from sex.