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Unexpected Delight

"A first encounter with a totally passable cross-dresser"

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I posted an ad in my favorite hookup list seeking a sister cross-dresser to come over to play with me. I had no real expectations that I would receive even a single response. None of the dozens of ads I had placed before had received a single response. At the time, I more or less assumed that cross-dressers generally regard other cross-dressers as competition rather than as sisters.

In my ad, I gave a thorough physical description of myself and included several photos. I explained my appreciation for the bodies of men and women but that my aversion to body hair gave me a preference for more feminine bodies regardless of sex. Lastly, I explained that I am almost exclusively a bottom and probably would not be able to function as a top unless highly stimulated. I, therefore, offered sex of a more lesbian-like nature as an alternative to intercourse.

Since I had also posted ads seeking men, I was already in the process of dressing and putting on makeup. As is my custom, I periodically check my E-mail in between phases of getting dressed. Much to my surprise, I discovered a response from a young cross-dresser Krystal. The two photos included with Krystal’s response to my ad were of a gorgeous, sexy, feminine cross-dresser. Krystal’s reply explained that she would not be able to come till after midnight, so I replied with my address and phone number. I explained I would be watching a movie downstairs in my theater when she arrived.

I retired to my theater, queued up a movie, and curled up in a girlie position to watch. My excitement was indescribable because I was anticipating something new. I had been with so-called cross-dressers before, but none were close to passable; few had either long hair or wigs. Krystal, on the other hand, at least from her photos, is a totally passable, cross-dresser far cuter than me.

I had nearly finished a two-hour movie when the doorbell rang which startled me because I was expecting a phone call to precede Krystal’s arrival. I sprang up, answer the door, and found the cutest little trap girl standing in the light from the porch lamp. She was wearing a nice cream-colored blouse, a matching skirt, and tasteful eye makeup. Krystal was wearing no lipstick but with her face, none was needed.

I greeted her into the foyer and we walked up the stairs holding hands. It is my custom to escort my visitors to a Victorian-era theme room for play but I took Krystal to my bedroom. My bedroom has a lot of feminine flair including pink rose petal bead spread, ruffle, and pillows. The white and brass head rail (not headboard) has, hanging above it three cherubim. The two end cherubs hold banners in a hand extended toward the center while the cherub in the middle plays the harp.

We sat in the middle of the bed embracing, making out, and caressing each other’s bodies. The kissing was deep, wild, and filled with mutual passion. We fell to the bed rolling first with me on top of her and then with her on top of me. Even though we both remained fully clothed the passion if our kissing and caressing seemed to increase. This was amazing, making out with Krystal was everything I dreamed an encounter with another cross-dresser would be like.

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We had been making out for a little over an hour when something unexpected and amazing happened. I had not even noticed that Krystal had lifted my skirt and moved my panties to the side. In an instant, she had popped my dick inside of her without my even having been aware I had an erection. The most amazing part was how natural it felt despite my aversion to topping biological makes and a complete lack of ability to achieve an erection during sex with biological males.

I don’t know how but somehow Krystal was able to keep me deep inside her and do all the physical work while still making out. She continued gently pumping while kneeling over me with our lips together exploring my mouth with her tongue. Then she assumed a more upright squatting position increasing both the rate and amplitude of hip motion.

I gently squeezed her waist with my fingers with my palms resting on her hips. I watched the expression on Krystal’s face which was one more of determination than passion. She seemed to have a goal in mind which I took to be the elusive G-Spot orgasm. Both of us were as quiet as mice and the only sound was the ticking of a clock and a soft creaking of the bed frame.

I would alternate between squeezing Krystal’s waist, firmly holding her chest just below the armpits, and caressing her smooth tummy with my hands. We kept fucking for about another half hour and then it just seemed to end naturally. I do not know if she achieved her orgasm nor did I perceive that I had had one but my erection had faded. I did feel that I had just experienced something amazing.

We lay together in a kind of afterglow for about another hour embracing and occasionally kissing. Eventually, Krystal sat up and said she had to go; it was nearly 3AM. We exchanged a final hug and a kiss at the door where I had greeted her hours before. Although we have remained in touch that was our only face-to-face meeting so far. Since then Krystal’s body has become far more masculine while mine has not changed.

Krystal continues to cross-dress and despite the changes in her body, I will be as excited to see her again when we meet as I was the first time. We do remain in touch but our availabilities never seem to coincide. I think of Krystal often and fondly just as I am while writing this.

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Written by KimberleySlut
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