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Sam told me how fascinated and excited she had been when she saw me in the bar that first night and realized that I was wearing lingerie. She confessed that she frequently wore men's underwear because something about doing so excited her. She said that she had barely been able to contain herself the first night that we met as she had dashed home after work to change. Sam giggled a little as she admitted that she had allowed her hand to creep down to the crotch of her jeans that night as she had driven hastily back to the hotel. We both laughed as we realized how perfectly matched we were.
Sam wrapped her arms around me and pulled me toward her. Our mouths met again, each of our tongue's exploring the other's mouth. Finally, Sam pulled away, looked into my eyes, and said, "I love fucking you, but I also love being fucked. I hope you will be my girlfriend again, and again, but right now I want your cock in me."
I quickly pulled her to me and kissed her deeply. I couldn't believe it. I realized that Sam was the woman of my dreams. A beautiful woman who understood and shared my crossdressing urges and who could take me to incredible heights of orgasmic satisfaction with her dildo. And, a woman who also wanted to experience my cock buried in her pussy.
Samantha crawled out of my embrace, pulled my baby dolls over my head, and unfastened my bra. My fake breasts tumbled out onto the bed and, with a laugh, Samantha gathered up the accoutrements of my femininity and discarded them onto the floor. Then she climbed on top of me and gave me a deep, long kiss. Breaking the kiss, I was able to get my mouth down to her breasts. They were small, but from my standpoint more than adequate, and I softly licked and sucked her hardening nipples. Samantha's legs were splayed on either side of mine and she ground her pussy against me. My cock immediately sprang back to attention and Sam quickly guided it home. Her pussy was already moist and easily engulfed me. The feel of her pussy around my cock was almost as nice as having her dildo jammed up my ass.
It did not take long for the gentle rocking of our coupled bodies to give way to the hurried thrusting of our hips together as each of us rocketed toward orgasm. I felt the cum welling up in my balls until I could hold it no longer. Samantha continued to pound her pussy against me until I felt her body tighten and she let out a soft moan. As the spasmodic throbbing in my cock and Samantha's contractions around it began subside, I felt her body slowly relax down onto mine, my cock still embedded in her warm pussy.
As we lay together in bed, Samantha told me that she didn't think that she was really cut out for life in a big city. She said that she had grown up in a small town and now realized that she liked a lower pace away from the city. I pondered what she had told me and mustered up the courage to say, "Sam, you know, if you moved in with me, you could fuck me more than once a month."
Samantha quickly responded with a smile, "And you could fuck me more than once a month."
