This is a true story, told as closely to how it actually happened as my old memory will allow.
Back in the mid-1980s, I was newly divorced, beginning to explore my bisexual interests, and very, very horny. I had seen some TV film loops in adult bookstores (usually while getting my cock sucked through a gloryhole), had bought and enjoyed TV stroke books, and had done a little crossdressing in panties. I loved the silky feel, and enjoyed fucking my ass with a small dildo while watching TV porn videos in my living room.
I was on a business trip to San Jose CA, just down the road from San Francisco, and as usual on these trips, was touring the sex businesses and looking for fun. In one of the adult bookstores I picked up a copy of The Spectator. I don't know if they're still in business, but in those pre-internet days they were the San Francisco version of Screw Magazine, with stories, ads for adult businesses, and ads for prostitutes of all types. I read through it back at the hotel, and found some very interesting ads from TVs, Transexuals, and crossdressers. I was really excited, and jerked off looking at the ads.
The next night I took the Spectator and headed out for SF to see what I could find. Using the ads as a guide, I hit a couple of adult bookstores, stroking myself to the movies in the video booths. I got a couple of offers from guys, but wasn't interested in a quick suck in a small booth. I stopped at a little bar to have a drink or two to gird my courage, and perused the ads in the back of the Spectator. There were a couple of TS ads that looked promising, and I got some change from the bartender and went to the phone in the back of the bar. I'm sure he knew what I was up to, and I'm equally sure he didn't care. I made a few calls, said thanks, but no thanks to ones that didn't seem to have the attitude I was looking for. After a few tries, I talked to one "girl" (I'll use the feminine from now on) that seemed like just what I wanted. We talked for a few minutes, I mentioned what I was looking for and asked about location and rates. She gave me directions to a convenience store a short ways from her place and told me to drive there and call again.
I had another drink while I made up my mind to go through with this, paid my tab and headed out. Getting in my rental car I drove to the directed place and called again from the pay phone in the parking lot (remember, this is pre-cell phone too). She answered immediately, and gave me directions to her place, only a block away. She said she'd be watching for me to let me in. I was too excited to drive the short distance and risk not being able to find a parking place, so I locked the car there in the lot and walked the rest of the way. I stood in front of the building, and heard a voice call - "Are you ____?" Looking up, I could see her leaning out of a third story window. "Yes, hello", I called back. "Catch", she called, and I saw something falling towards me. I missed the grab, and a set of keys fell to the pavement at my feet. She told me which one opened the front door, and what apartment number to go to. I went up the stairs two at a time, my heart in my throat. I knocked on her door, and it opened.
My dreams were answered - she was just shorter than me, with a cute face and a nice feminine body. She was wearing a lace body stocking, through which I could see a black bra and panties. She wore a robe over this ensemble, open to display her charms. I handed her her keys, she invited me in, and I followed. The apartment was kind of a shotgun arrangement, a long hall with a bath, kitchen, and small bedroom off it. At the end the hallway opened into a large room overlooking the street, originally the living room but now her place of business. There was a large bed, with mirrored tiles all along the wall next to it, so you could watch yourself. There was a coffee table next to the bed. She sat on the bed and asked me what it was I wanted to do. I'd been thinking of this speech for some time, and, sitting on the edge of the coffee table, rattled it off: "I'm not gay", I said, "but the idea of a woman with a cock excites me. I also like to crossdress and be feminine. If you have some lingerie I could wear, that would be great, I want you to dress me up and fuck me like a woman."
She smiled and said that would be no problem. She told me the fare for the ride and I counted it out and put it on the coffee table, including a sizeable tip. As I recall, it was about $60. (Ain't inflation a bitch?) She told me to get comfortable while she found me something to wear, and went to a closet near the bed. I got naked quickly, and she returned with a matching pink bra and bikini panties, and some black thigh-high stockings. Sitting on the bed, she helped me step into the panties, then I slipped the bra on and she hooked it for me. I sat on the bed and slid the stockings up my legs. "Just relax", she said, "I'll be right back" and she disappeared down the hallway. I lay back on the bed, looking at myself in the mirrored wall. I caressed my ass, whispering to myself, "You're going to get fucked!"
A few minutes later she came back. The robe was gone, as were the panties. A nice, flaccid cock stuck out through an opening in the bottom of the body stocking. I complimented her, and she stood next to the bed, saying, "Help me get hard" I slid over to her and took my very first cock in my mouth. It tasted wonderful, and I couldn't get enough. My heart was pounding as I sucked harder, reaching under her to caress her balls. I asked if the body stocking could come off, but that wasn't on the menu.
She leaned over me and caressed my cock through the panties, then lay over me, and we got into a 69. Her mouth felt wonderful on my cock, and I could have stayed like that sucking her hardening cock for hours. Reaching through her thighs, I rubbed her perineum and asshole. Sticking a finger in my mouth for wetness, I penetrated her tight ring and fingerfucked her ass while we sucked each other. My cock was hard enough to pound nails, and hers felt the same way in my mouth. I sucked as much of it into my mouth as I could, enjoying the taste, the feel, and her wonderful aroma. (It was about 6", not the 8" her ad promised, but at this point truth in advertising was the farthest thing from my mind.)
Finally she got up off me, and moved around to between my legs. "Are you ready", she asked, and I could only look at her, smile, and nod. I started to get up on all fours, but she told me that on my back would be more comfortable for a relative newby like me. I lay on my back and pulled my legs up while she moved closer between my thighs. She skinned the panties off me, and I lay back, my stockinged legs in the air. She pulled a condom and lube out of a drawer, opened the condom and began to skin it onto her cock. Once it was all the way on she lubed it, and pressed some lube into my asshole. As she slid forward, I asked if she could use the lube on my cock too, and she smiled and complied. She slid forward and pressed the head of her cock against my hole, and I was in heaven. Pushing harder, the head slipped into me. It hurt a little, and I put my hand against her hip to slow things down, reminding her I was a beginner. She pressed forward slowly, then began back-and-forth, going deeper with each stroke.
Oh, it was wonderful! The pain began to subside, replaced by a wonderful full feeling. Finally I felt her hips against my ass, and I knew she was all the way inside me. Then she began fucking me. There were long slow strokes, then a few short sharp ones. I loved it all. Taking my lubed, diamond-hard cock in her hand, she stroked me in time with the motions of her cock in my ass. All too soon, I felt myself moving towards orgasm. My hips bucked involuntarily, pressing my ass and my cock against her. God, it was the most wonderful feeling ever! Finally I came, spurting high in the air, my cum falling on my belly and chest., my whole body tensed for the greatest orgasm I'd ever had. My cock became so sensitive I couldn't stand any more, and I reached down to hold her stroking hand still. Her cock moved in my ass a few more strokes, then she withdrew. My hole felt stretched and empty. I lay back on the bed a few seconds, just enjoying the feelings.
After a while, she told me I could clean up in the bathroom down the hall. I padded down in my bra and stockings, and used a wet washclothe I found there to remove the cum and lube from my body. I returned to the bedroom and dressed, as she sat on the bed and I complimented her and told her how wonderful it felt. When I was dressed, she walked me to the door. She had put her robe back on, but not the panties, and her softening cock hung between her legs. She put her hand on the doorknob and turned to me to say goodbye. Impulsively, I dropped to my knees, and holding her hips, placed a big kiss on her cock. She giggled, and as I got to my feet I told her I had wanted to thank the organ that gave me such pleasure.
We hugged, she opened the door, and I went out into the night. I fairly skipped back to the car, my mind filled with the pleasure I had experienced. I got the rental car map out and figured out how to get back out of the city. Along the way I stopped at a little neighborhood bar. I stopped down and ordered a triple shot of their best vodka. I lit a cigarette and sat back to enjoy the drink and my own feelings.
I was reminded of an old joke, about a guy who walks into a bar and orders 6 martinis. The bartender pours, and asks, "What's the celebration?" The guy says, "My first blowjob" The bartender says, "Well, that's something to celebrate, but 6 martinis?" and the guy answers, "Gotta get the taste out of my mouth."
Getting the taste out of my mouth was the last thing I wanted......