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I have been crossdressing for since I was in my teens. I stopped every now and then for various reasons, but the urge from deep inside me always calls me back. It is late 2017 when I start crossdressing again and this time it was very different. I was watching a porn video of this beautiful crossdresser being fucked and I felt this feeling like none other before. I realized that I would love to let a man have his way with me. I have been fucking myself with dildos for years and I now was intrigued about having the real thing. One evening I put together some sexy photos and posted them on Craigslist….( I miss that site ). Basically, I wanted to find a date for new years eve and bring in the new year as a woman. I received many replies but only a few stood out. Of the few there was one that made a great impression on me. He was single, 48, 6’1” and had a body type that I was looking for.Over the next few weeks we flirted and as the new year drew closer I began to get excited that this. He assured me that while he was probably inexperienced, he was well hung. Next up was a fairly religious football player named Mike Harris, a ferocious linebacker, who for obvious reasons, couldn't have his propensity for kinky sex known. He'd suffered silently, with his goody goody wife not having the slightest clue how to please him, and yet he still lusted for the fun he'd had back as a star in college. He was nearing retirement on the gridiron, but his well muscled body got my attention nicely. He was also an investor in my father's company. The religion was revealed to be a mere pose as he planned on running for office one day, with his loving wife's support. He'd been hard to convince of the discretion, but when I informed him of the electronics policy, he was in. The last was a fallen angel of sorts. Trent Howard, a one-time Wall Street wizard who'd made millions and had been quite the star with his homespun charm and his high school sweetheart. Turns out she was quite the.
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