A Femdom’s Crossdressing Guided Masturbation Story


The day my boyfriend and I graduated college was one of the happiest days of my life. Not just because of graduating, because I still had at least 2 more years of school ahead of me, four if I decided to go for my Doctorate. Honestly, it just marked the end of another semester for me, granted one where I got a shiny piece of paper, but still, with so much school in my future, I was little reluctant to celebrate. But this was a different story for my boyfriend. He just got his diploma and was accepted into a large accounting firm which shall remain nameless as he still works there and has gained more than a few promotions. Of course, no one knew under his cap, gown, and clothes were a chastity device, bright pink panties, and a matching bra which did not have its usual breast forms. Oh, I may have neglected to mention my boyfriend was my crossdressing submissive. But, that night, things changed, and we moved to a new phase of our lives, one that involved a lot more crossdressing guided masturbation fun! 


Graduation, in all of its many forms, is a time of change, and three major ones were on the agenda that night. Neither of us knew the other one was planning something special to take things to the next level, but fate has a funny way of taking things to a different level itself. As he prepared a special dinner for me at home, complete with rose petals and candlelight, I was out at the leather goods store. The owner had become a friend of ours, and we found out he and his wife were lifestylers as well, she his collared slave. So, when I had placed my order a week ago, he knew exactly what was on my mind. When I walked into the store, he produced a lovely black leather case, along with a smile. I was confused at first, and when I opened it, my jaw dropped. Inside was the most exquisite black collar, lined with faux, hypoallergenic fur, with a D ring attached, made out of brass polished to a mirror shine. But there was also a silver chain, one you would see with some form of diamond encrusted heart or a charm. I looked up at him, and he smiled. “Well, he can’t go out in public with the leather one, can he?” I hugged him, tears welling behind my glasses.


A Night To Remember For Mistress


I put the box in my purse and caught a cab back to our flat. I was so nervous. I wanted tonight to go off without a hitch. I had forgotten he asked special permission to have male clothes on tonight, and even be out of chastity. So, when I opened the door, and he was sitting there on one knee, in a suit, with a box raised, in the middle of flowers, my heart stopped. Time stood still, and I could not believe what was happening. His eyes shimmered, as he asked the four words I had wanted him to say for at least two years… “Will you marry me?”


I could not speak, I nearly fainted, and I finally managed an excited yes. We embraced, and my purse fell, the leather box sliding on the floor. We did not notice at first, anyway. We were too busy making out, passionately. When we finally separated, he walked over to the box, and asked what it was. By this point I had already sat down at the table. I turned my chair and smiled at him. “Open it,” I said, happy at the coincidence. He gasped at the collars, and looked up at me, and a strange sense of deja vu swept over me. He came over to me, and I instructed him to kneel. I placed the collar around his neck, and offered him a lock, saying if he chose to lock it in place, there was no going back. He would be my slave forever. And, before I could finish the final sentence, the lock snapped shut. That was when I noticed my mail in front of me.


The Chance Of A Lifetime For This Femdom


The joy him becoming my fiancé, and my slave, was stifled a little. I had opened my letter of acceptance for a college overseas… Only one semester, but it was the chance of a lifetime. Three months later, I was gone. We talked every day. He wanted to remain in chastity the entire time, but I told him not to. Not because I was not planning on coming back, far from it. See, I was also a phone sex Femdom, and I had a few plans for him. We would talk on webcam, and he would be dressed in his usual housewife clothes. But he would have to do what I said, when I said it.


And that is how, for almost six months, my crossdressing slave fiancé engaged in guided masturbation. I would watch him play with himself, telling him how fast, how slow, telling when to start and when to stop. Sometimes, I would make it last for hours, just to mess with him. During that time, I started having him participate in coached cum eating. We still do it when one of us goes out of town, and it is always just as hot as that first time.


I also gave him instructions to serve our friends at the leather shop, so he would not get out of practice. They were not allowed to use him sexually, of course, but they could do other things. When I got home, we had two ceremonies. One for all of our college friends, the traditional marriage. The other was more intimate, just close friends in the lifestyle. I will never forget how wonderful he looked in his wedding dress that day.


Nothing Keeps A Sissy Happy Like Crossdressing Guided Masturbation! Ready to try? Call 800.730.3507