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Crossdressing Vignettes (True Story)

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Crossdressing Vignettes (True Story)I went through a period in the ’80s and ’90s when I was very much into crossdressing and being a bottom. I didn’t write these events down at the time, but I wish I had. As the events come to memory, I’ll write and post them. Here’s one such story:In the ’90s, I was married, and my wife didn’t (as far as I knew, anyway) know about my bi or crossdressing interests. I loved her very much, but I had these other desires I never shared with her. I kept a small bag of lingerie, condoms, and lube tucked down in the spare tire well in my car, a place I knew she’d never look. Occasionally I would tell her I was going out for a drink in the evening by myself, just to ease up from the day, and go play. My job at the time was fairly stressful, so it was understood I would want to unwind occasionally, plus we had a small c***d at home, so someone had to stay home.We didn’t have a home computer in those days, and I don’t remember now how I found him, but I made contact with a guy not too far from our house who was a top into CDs. I contacted him, and he was interested and available to host. We set a date for one evening during the week, and I told the wife I was going out to a bar for a couple of hours. I drove out towards his place and found a dark parking lot where I could change into my lingerie in the car. I put on a matching black bra and panties, plus black stockings, then put my boy clothes back on. I drove to the address, parked around the corner, and walked to the house. The door was answered by a slightly chubby, hairy guy about my own age bahis siteleri (late 30s), and after nominal greetings, he led me to his bedroom.A porn tape was playing in the VCR, feeding to a TV at the foot of the bed. The lights were dim, so the main light came from the TV. The video was straight porn with the sound turned down low. He started to undress, and I followed his lead, stripping off my street clothes down to the black lingerie beneath. As I bent over to pull my jeans off and revealed my black-pantied ass, he whistled his appreciation and I smiled at him.By the time I had stripped, he was naked, and my eyes went straight to his crotch. He was hairy there too, but a nice half-hard cock was making it’s presence known. I’d had dildoes inside me, but not too many real cocks at that time, and his looked to be just the right size to fill me without hurting. He lay down on his back on the bed, and with no preliminaries I dove onto his rod, sucking it deep into my mouth. I took his balls in my hand, caressing and gently squeezing them. The moaning of some chick getting fucked on the video was our background music.He got hard pretty quick, but I kept at it, sucking hard, stroking him, kissing his balls. I lifted them up to run my tongue across his hairy perineum, and he moaned along with the girl on the video. At full size it was about 5″, and not so thick that I was scared to take it. I was feeling like a slut, dressed in black lingerie, lying across a strange man’s bed in the dark with his dick stiffening in my mouth.I could have kept going and made him cum in my canlı bahis siteleri mouth, but (as I had hoped) he wanted to fuck. He had condoms and lube at hand, so mine stayed in my jeans pocket. He got up to get ready, and I moved to the side of the bed, my ass right at the edge, laying on my back. The bed was tall enough to put his hips right at that level. He came back to me with a condom on and the lube in his hand. I lifted and opened my legs until my thighs were close to my chest (I was more flexible in those days), and waited.He put some lube on his fingers and opened my hole, probing with one finger and then two. It was my turn to moan as the pleasure in my ass spread through my body. He finger-fucked me until he thought I was ready, then lubed up his still-hard dick and pressed it to the opening. I was still a little tight, and I could feel him stretching me. It took several very pleasant lunges by him, but finally I felt his wiry pubes against my ass. We both moaned at that point, and smiled at each other. He leaned down and kissed me, and we swapped tongues for a moment, then he stood upright again and started fucking.I loved it. There’s some kind of switch that goes off inside me that turns me instantly from he-man to submissive cunt at such moments, and his cock sliding in and out turned me to a cock-craving pussyboy. He squeezed my non-existent tits in my A-cup bra, then pulled it down to pinch my nipples. We were rocking back and forth together as he slowly fucked my tight pussy-ass. My moans overcame the sounds from the TV as I reveled in my feminine canlı bahis side.We kept going like that for about 10 minutes, with him caressing and fucking, occasionally leaning in for a kiss. I encouraged him to fuck me, told him I loved his cock inside me, told him I was so glad we met. He held my legs down and I pulled his hips to ram his cock into me. He began pumping faster as I proved able to take all of him. His eyes closed and his head raised as he concentrated on feelings in his prick, then began really pounding. My voice went up as I begged for cock, told him to spray me (well, the condom) with cum. Finally I felt him tense and he slammed into me, once, twice, then a third time, and held my hips as he spurted into the condom. He leaned down and kissed me once more, and we stayed like that for a minute as his orgasm subsided. I hadn’t cum, but that wasn’t the point.Finally he got off me and went to the bathroom to clean up. I lay there until he returned, luxuriating in the feelings of having been fucked. It was almost as if I could still feel him inside me. After he came back, I went to the bathroom, wiping carefully to remove all traces of lube. I took off my lingerie, then padded back into the bedroom naked. He was lying on the bed, his soft cock laid out across his thigh, as I got dressed. We talked about how good it had been, and I stuffed the lingerie in a plastic bag I had in my jeans pocket. Then he walked me to the door, kissing me one last time as he squeezed my ass and said thank you.I walked back to the car and put my “getting fucked” bag back into its hiding place, and left. I stopped by a bar on the way home for one drink for appearance sake, then went back to my comfortable happy married life. As I recall, we met one more time for a repeat performance, then lost touch.

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