Both Danielle and I tried to hook up again before she left town two days later but our schedules didn't align. We promised to stay in touch, especially if we were ever in the same town again, but now I was left with a freshly renewed desire that constantly danced through my mind and no one to play with.
I tried to dress up in my alone time but my girlfriends clothes didn't fit me very well, except her shoes and 90% of them were slutty "fuck-me" style pumps, which I couldn't be more happy about. I watched makeup tutorials and borrowed her vibrators too. I'll admit it was uncomfortable at first, but after a few tries my hole came to embrace its new role. Now if I could only find another beautiful chick with a dick to fuck me for the first time...
One day I was shopping around online for some slut gear of my own when I decided to wander into those fucked up corners of the internet known as craigslist and backpage. Wasn't much of anything to get my juices flowing, just ugly dudes with hairy legs in panties calling themselves girls. Gross. Until I came across a post featuring a picture of two provocatively dressed girls passionately making out in the corner of a club. The ad read something to the tune of, "transitioning male to female looking for other MtF or crossdressers to spend some girl time with. No men."
"Prefect!" I thought. I sent off an email to her and by that night we were texting back and forth. Her name was Heather and she was a very down to earth chick. Easy to talk to with a lot in common she wasn't looking to prostitute herself, just searching for an honest friend to explore the wonders of femininity with. She was also gorgeous to boot! Long, natural black hair with a cute nose and a forgiving smile. Even better she lived only a few miles away from me. Naturally, as the conversation went on, we took a turn into sexual waters. I told her I have lots of dirty thoughts. She said she did too, like how she never had a facial but wanted to try real bed. Then she asked to see my cock. So I sent her that infamous dick pic. She responded with a worried and a nervous laughter emoji. "That's pretty big." I told her she could do with it as she pleased. Her pic was a full body shot of her in a plaid skirt and black shirt with her dick hiding behind her fishnets.
[M] Trans Pool Party