My First Forced Feminized Sissy!

My first transformation in college was not a boyfriend but instead the jerk boyfriend of my roommate Cathy. Instead of the usual first year in a dorm I managed to find an apartment that I shared with two other girls, Cathy and Julie. Cathy was really alot like me in that she enjoyed life but still studied hard to make good grades. Julie on the other hand was the quiet type that took getting drunk before she could loosen up and really have fun. Julie had a boyfriend back home and Cathy dated a guy from one of her classes. The first time Cathy brought Jeff over for us to meet I could not believe how cocky he acted. He acted like he was god's gift to women and even had the nerve to actually hit on me while Cathy was in the bathroom. I immediately disliked the jerk but he was Cathy's boyfriend so I kept my mouth shut.

Over the course of the next few weeks Jeff would pop in by surprise even when Cathy was at work. He would just make himself at home and comment about how hot he thought I was and that we should get up with one another sometime. I asked him what about Cathy and he actually responded what she didn't know would not hurt her. What an ***!! It was right then that I knew I had to do something about this jerk and I needed to do it quick before Cathy found him screwing with some other girl.

The following weekend I knew Julie had plans to go home to her parents and Cathy had to work both Friday and Saturday night at her waitress job. This was my chance. After class on Thursday I went to the mall and did a little shopping. I kept it pretty simple with some nice lingerie with consisted of a bustier, panties and matching black stockings. I went by a shoe store and found a nice pair of high heel ankle strap sandals in size 9 womens. I had slipped a look at Jeff's shoes and found he was a size 8 mens. The size 9 would have to do because it was the largest size they had in stock and I really wanted something with a high heel for my little plan!
On Friday morning I saw Jeff talking to his friends outside the building for my next class and went over to say hello. I asked him if he had plans for the evening and suggested he come over and hang out because I was going to be so lonely all by myself this weekend. Sounds good he said with a smile on his face, what time? I suggested he come around 7pm if he could. I knew Cathy had to work until 1am so it gave me plenty of time to get my little trap set. That evening I went home and showered, did my hair and makeup, then dressed in one of my best slutty mini skirts, tight sweater top, beautiful gray lace garters, bra, and panties. I slipped on a pair of tan nylon stockings and my gray stiletto heeled pumps. Right on time 7pm and the doorbell rang. Jeff's eyes popped out of the sockets when he saw me. Wow, you are hot as hell he exclaimed! I invited him in and he produces a bottle of Jack Daniels telling me he though we should do some shots. Sure I agreed and proceeded to the kitchen for a couple of glasses and a couple of cans of Pepsi! While sitting on the sofa he couldn't keep his eyes off of me. I kept noticing him looking at my legs so I made sure that my skirt slid up just enough to see my stocking tops and a bit of the garter. It was pretty easy to see his erection through his jeans and it didn't take him long to make his move.

After about three shots Jeff proceeds to put his hand on my leg running his fingers up to the edge of my mini skirt. Do you like my outfit Jeff I asked? He told me he really liked what he was seeing and wanted to know if I would show him some more. Not just yet Jeff sweety, lets have a few more shots and then talk about it. Jeff was taking three shots to my one and pretty soon began to get quite wasted. I had long since stopped drinking and he didn't even notice. Jeff honey, how about coming with me, I said? I took his hand and led him to the bathroom and told him I wanted to ***** him and put him in the tub for a little bath. I ran a tub of water and made him a bubble bath while he ******** down to his birthday suit. Once in the tub I took the wash cloth and soaped him up nicely then took mt razor and proceeded to shave him starting with his legs. Hey, what are you doing he exclaimed? Just a game so sit back and relax. Don't you want to play with me, I asked? Sure but why are you shaving me he said? Because it's a game and I promise you will like it. It took about 30 minutes to get him nice and shaven all over but finally he was as smooth as a baby's bottom. I got him out and had him dry off while I fixed him some more shots to drink. Jeff was really getting wasted by the time I got him in my bedroom. I laid him back on my bed and took out the pair of handcuffs that I kept in my night stand drawer. I handcuffed Jeff's hands behind his head around the bed post and you know what happened next. That's right, I started cross dressing him. I took out the bustier and slid it up from his feet over his waist and up to his chest. I had to release the handcuffs to get his arms through the straps but once it was on the handcuffs were once again clamped to his wrist. Next I slid on the panties and next came the stockings. Jeff didn't make too much of a fuss and seemed to be enjoying himself. He even had the gall to ask me if I was going to let him screw me. I told him to just wait because if he were really good I would have a big surprise for him. Next I strapped the high heels to his feet and then I went and did a crude makeup job on his face with foundation, powder, blush, eye shadow, eye liner, and bright red lipstick.

Finally I got up from the bed and went over to turn on the overhead light. Wow Jeff, you look just like a little ****! Almost as good as me! I then opened my dresser drawer and took out my Polaroid camera to get some photos. Jeff struggled and didn't like the fact that I was taking photos but oh well, what can he do now? I got some great shots and showed him so he could see for his self. I then got up and went in to the living room at which point I hid the photos. Finally I came back in to the bedroom and sat down beside Jeff to tell him what I really did. You see Jeff, you are now a sissy boy and I have photos to prove it. If you try anything with me I will show everyone starting with Cathy right down to all of your friends. Jeff was furious but in reality knew he was totally screwed. Oh, he tried to be tough telling me he would get me for this but I told him if he tried anything so much as a threat I would show the pictures all over the campus. Also, since you want to play tough I am going to let you keep your girlie clothes you are wearing because if I ask to see you in they you will do it or I will use the photos to make your life a living hell. Do you understand me? I could tell in Jeff's face that it was finally hitting home and his tone changed from hateful to forgiving and pleading for me not to do anything. Jeff, I am going to let you loose but I swear if I have to I will show everyone what you really are, a sissy boy. I then removed the handcuffs and told him to clean his face. I would not however let him undress and made him wear the lingerie home.

For the next three years Jeff was my little slave sissy. About twice a month I would bring him over, dress him, tie him up, and spank his *** as I saw fit. After breaking up with Cathy I showed her the photos and told her what had happened with Jeff hitting on me and all and why I did what I did. Cathy quite enjoyed the fact that I feminized Jeff. I always wondered if Jeff continued to dress up. I still have the photos to this day and sometimes look back at them and smile. Maybe someday we will see one another again. Then I can use those pictures and have a little fun!