Ron and I were friends for a few years. We met through work and hit it off immediately as a result of common interests. I didn't have many friends, so I really did appreciate our friendship.
One day he came over to my apartment to help me fix my computer. As he was going through the file system, he came across a picture of me all dolled up in pantyhose, high heel pumps, and a skirt-suit. I was really embarrassed because I hadn't told anyone about my crossdressing, let alone my only friend.
He said "Wow, who's this? Is this an old flame? She's hot!" I blushed. While I could have lied and said it wasn't me, I didn't want to, especially since I really valued him as a friend and didn't want to be dishonest. So, I told him that it was actually me. He looked up at me, and then back at the picture, and asked "Are you serious?" I told him how I've been crossdressing for years in private. I thought we would be nonplussed and surprised, but he wasn't. Instead he seemed curious.
He asked about the dressing and I answered all of his questions. He then said that there was no way that I could be the 'girl' in the picture, and then asked me to prove it. I went in the bedroom, and for an hour, got dressed up. I put on black pantyhose, black bra with my breast forms, a charcoal fitted mini-dress, and black high heel pumps. I did my make-up and fixed my hair, and then emerged from my bedroom in my femme self. He smiled big and said "wow, you look awesome!". I blushed again and thanked him for the compliment.
He got up and circled me, and said I looked great again. He suggested that I stay all dressed up for the rest of the night. We went to our favorite sports bar and he pretended that I was his date for the night. All the men were staring at my legs and ass, and smiling at me. I think he liked the attention that I got, because he made sure they knew that I was supposed to be with him. After a few drinks, I felt his hand on my knee, and then I felt it slide up my hosed thigh, his fingertips touching the hem of my fitted mini-dress right at the upper thigh. He asked "You really look a lot like a real woman - do you know how much?" I shook my head. He took my hand and then slid it under the table and onto his crotch. I could feel a huge, hard shaft pulsating under his slacks. I was really turned on. I never felt this way towards a man before, but then again I never felt so much like a woman before either - that feeling would reach its ultimate climax later that night, little did I know.
We took a taxi back to my place. I walked up the stairs in front of him, and I could feel my tight dress sliding up the sides of my thighs and hips, the pantyhose sheering over my ass and crotch. By that time, after wearing pantyhose all night, and with being so turned on, my crotch was wet. I heard my heels on the stairs, and I purposely stuck my ass out a little, and walked up with a flirty saunter in the hips. I knew he was staring at my ass and legs. He reached up and felt my ass and gave it a nice grab. It startled me and I softly said "hey!". He smiled and laughed.
When I was trying to open the door to my apartment, I bent over slightly to slide the key in, and he came up behind me and pressed his crotch against my ass. I heard him groan "mmmmmm". I could feel his cock completely swollen under his slacks, and it was pressed up against between my ass cheeks, which was slightly visible due to the tightness of the dress I was wearing. He felt up my pantyhose legs and asked "Do you also taste like a woman down there?"
I then said "Ron, what do you think you're doing?", with a slightly flirty tone. He kneeled down behind me and hiked up my dress to expose my pantyhose covered ass. He pushed against my back with one hand, and with the other gently held my knees, making me bend over only at the waist, with my legs straight and my lower back curved to push out my ass. He smelled me and said I smelled like a woman ready for naughty sex. I told him he had too much to drink, and then he started to probe my crotch and butthole through the pantyhose, using his hands to spread my ass and caress my thighs.
I closed my eyes and moaned with sexual pleasure. He got up. and then we went into my apartment. I placed my purse and keys on the counter, and when I turned around, he was right in front of me smiling. He held me by the waist, and gently pushed me down onto my knees and said "I'll really make you feel like a woman tonight". I was then face to face with his crotch, staring at his zipped up slacks, with a tremendous bulge. "Unzip it and gently take it out". I unzipped his pants, and slid out his cock through the hole. I pulled gently on the shaft, and when it found the hole, it sprung out. I couldn't believe how big he was. It was huge, and it was incredibly hard - so much so that the shaft and head of his cock was throbbing and pulsating. "Now put it in your mouth gently." I did, and he moved my head gently with his hands, making me take his shaft in and out of my mouth with my lips stretched around it. Juices consisting of my saliva and his precum dribbled down the sides of my mouth and down my chin.
He moaned, and started to move his cock in and out of my mouth a little faster, like was getting impatient. He then looked down and pulled me up rather quickly. He took me by one arm and threw me against the back of the couch so that I was bent over, with my hands on the couch holding me up, and my crotch against the back of the couch. I let out a startle, and he came over and hiked up my skirt and pulled my pantyhose down enough to expose my asshole. He probed my hole with his tongue, and then got up. I felt his cock between my ass, the head of it throbbing right above my hole. "Let's see if you can be fucked like a real woman." I said "Wait, Ron, please...". He cut me off, saying "No waiting - if you're gonna look this much like a hot woman, get ready to be fucked like one...". "But..." I said, wanted to express my concern about never being taken in the ass before. "But what?" he asked, "I'm gonna fuck you like the woman you look like, and since you don't have a realy pussy, I'm gonna pump you in the only hole that you have." He slid it down and it found itself snuggly on the outside of my hole. He then pushed and slide his cock into me and let out a moan. "ooooh, that's real tight." He then just started fucking me, first with just small thrusts with just the head of his cock, to tease me and to tease his cock, and then finally with long strokes in and out. I moaned in ecstasy, and he said "You like being fucked like a woman, don't you. I always knew you were a little sissy faggot."
He ravaged me for hours that night. He kept telling me how good it felt putting his cock inside me, about how snug and tight it was, and how he loved feeling his balls touch mine and seeing my hard stick wave up and down in synchrony with his thrusts in and out of me. That night, an old friend became a new friend, both him and me.
