Buying Cucumbers Leads to Hot Tranny Sex

by Dave (Hamilton, NJ)

I really enjoy sharing my sexscapades on this site. I’ve shared intimate stories & how I love exploring all facets of the human sexual experience. Here’s one more.

Honestly, I was thinking about how the cucumbers in the basket at the roadside stand would feel in my ass. I chose a medium sized one and put it in my basket with some basil& tomatoes when a very hot younger woman said: “Excuse me. Oh the cucumbers look big this week.” To which I responded while checking her out:

“They just get bigger when they see you.”

She giggled then turned to face me telling me she uses a lot of cucumbers. It was then I began to suspect she was trans. I was very attracted to her, regardless of how she seemed to be 20 years younger than me. I decided to be bold and just go for it.

I asked her if I could pay her a compliment. She said Sure, so I said:

“I love your heels, they’re very sexy but how did you negotiate the gravel parking area?”

“That was tricky and I’m still getting used to wearing heels. I’ve only been wearing heels for about 6 months.” Then she winked at me.

I introduced myself and she told me her name was Claire.

“Claire, you’re very pretty I must say. I hope to see you here again.” To that she told me she was new to the area and was trying to make friends, but it’s hard. I told her I’d be her friend.

We walked out together and stopped at her car. She bent over reaching deep into her trunk. Turning around with her head still in there she totally busted me staring at her ass.

“Enjoying the view?” She asked

“Honestly, Hell Yeah I am. I hope you’re not offended”

“Since you were being honest here. I like it when guys check me out.”

“Cute guys or any guy?”

“Cute guys like you who are assertive.”

I gave her my card and asked her to call me if she wanted to go out. She asked if I was busy that night. I was but I said no. So we talked more standing there at her car.

She put her hand on my arm and I eventually had 2 hands around her hips and was about to grab her ass when she pressed her body against mine. Immediately we felt each other’s hard cocks. I moved my hand across her stomach and then down along her shaft.

“You ok?” She asked

I lifted my eyes to stare at her while I kissed her....

An awesome meet-up and casual encounter turned into a great ongoing relationship. We love to suck each other’s cocks wearing sissy panties. We’ve gone out together to pick up other trans and watched us with other partners.

We’ve had two 3-ways. The last one was with a girl. It was so hot how she watched Claire’s cock penetrate my ass. She commanded me to swallow her cum. Which is great because I love cum.

Last weekend, I watched Claire get fucked by a hot guy. I jerked off watching them wearing my white crotchless stockings, white heels, pink skirt and white satin top. The guy came in her ass and she pushed it out onto my face. Then she fucked my sissy ass and we made the guy swallow her cum from my ass.