1. Carolyn Makes Her Way (Part 1)


    Date: 3/5/2016, Categories: Crossdressing, Author: tvk3983, Rating: 3, Source: LushStories

    car of some guy who had pulled up. So I knew you at least were a crossdresser, and a very pretty one to boot. And it also looked like you were going out on a date. After you left, I drove home and thought about you for a long, long time. At work you didn't give any indications of your private life but I started looking closer. The way you walked, more like a woman than a man, said a whole lot. Some of the things you said were more feminine. Small things at first but they were all there and now I could see them. And every night after work I'd go home and fantasize about you and, naturally, jack off.” “So did I meet your expectations last night?” “And then some,” he whispered and kissed me. I met his kiss with as much, maybe more, urgency and need as I felt from him. Ten minutes later we were on our way to his bed, peeling off clothing from one another along the way. The urgency remained but the was a whole lot of tenderness as well. When he was deep inside me, in the missionary position, his lips locked onto mine and we slowly made love. Three times I reached orgasm, my legs locked behind his back, before he began filling me with his hot sperm, and in none of them did my dick do anything. A little over an hour later he was working on my leather pants and I was watching him from across the table. When he was working like this Mike preferred to drink tea so I made frequent trips to keep him well supplied. While he worked, I looked at some of the things he had already made but I ...
    kept coming back to the leather cuffs and finally slipped a pair of them onto my wrists. Almost immediately I felt myself as a submissive and imagined that what it would feel like to be dominated. My mind went back to some porn I'd seen on the internet and my heart pounded hard in my chest. I looked around and found a paddle of sorts; there was a handle for gripping and then a long, maybe two feet, piece of leather about three inches wide. I'd wondered what it would feel like on my bare ass when I saw it being used and now I could find out. Bending over to stretch my butt tight, I reared back and slapped myself hard with the leather. There was a loud snap when it landed and my mouth opened with sensual pain. Mike looked over at me and smiled. “Turn around, Carolyn, and do it again so I can watch,” he laughed. I did as he asked and gave myself another hard smack on the ass. This time I yelped in pain and Mike laughed. “Gave yourself a red stripe that time.” “Ouch,” I replied and rubbed myself. “Even when I was growing up I never felt a belt or anything like that.” “What did you think about it?” “It hurt but in a sexy way. I can see where someone might like it as a form of foreplay,” I answered. “How about if you bend over and let me give you, oh, say about five swats just to see if you like it when someone else does it to you in an uncontrolled way?” “Five swats?” “Yes, just five, but you have to count out loud with each of them. Is five too many?” “Nah, I'm a tough broad,” I ...
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