It was an exciting time. Finally going to college. I got a nice dorm room, and a roommate that seemed nice. And finally I'll be able to explore my hobby better, out of sight from my mom and better even, from my siblings.



My hobby started innocently enough, a few years ago. Somehow one of my sister's nighties ended up in my clean laundry, and for fun I tried it on that night. Never will I forget that sensual feeling, how it was clinging to my skin, the smoothness of the material, and the enormity of my orgasm after finally wanking off.



After that I managed to redirect more of her stuff into one of my drawers. One of her underwear. A bra. A pair of stockings. A crop top. And finally a skirt. And each piece brought more thrill and a desire for more. One time I was a week by myself, not going on vacation with the rest of the family. That week I went all out. Learning to walk in heels. Applying makeup. I found a wig at a goodwill store. And I practiced my voice.



It was just for fun. I had no interest in going out. No interest in "attracting a man". I may have made a few pictures. But only to see if I could pass. And the more experienced I became, the more I looked like a real woman. And I wanted my own clothes.



Finally leaving the family home gave me an opportunity. But I was a bit worried about my roommate. And I figured I better be upfront about it, so we could potentially switch roommates if it was a problem for him. I sent a message to ask if he was okay with me wearing female clothing once in awhile. He messaged back asking if I was gay. When I replied no, he was fine with it.



I was a bit disappointed though. The gay question suggested he was probably homophobic and probably not very accepting of alternative lifestyles. But we'd see where it would go.



It turned out Ben was an awesome guy and we quickly became friends. It took about two months of getting used to the new school and all the studying, combined with extracurricular activities. But eventually he asked me what the deal was with the cross dressing.



I told him I'd show him. My mail order dress had come in, as had my breast forms, and I was eager to try it all out. I put my wig on and did my makeup, then stepped in the dress. I either oversized the boobs or undersized the dress, but I couldn't get the zipper closed. So I asked Ben to help me.



I saw him eying me in my leather look dress, and when he zipped me up, I could feel his hands shake. And when I saw myself in the mirror it was clear why. The dress was perfect and I looked sexy as hell. When I stepped in my heels I could hear a loud breath escape from his mouth.



At some point he asked if I'd go out with him, and I explained I'd never gone out in public, nor had I any intention. That's when I noticed he had a hard-on.



In all my time of wearing female clothes I felt very pleased looking as good as I did. But seeing a man getting horny from me dressing in front of him did give an extra kick. Again, I wasn't gay, but I was thrilled with the power I felt over him. And just to exercise that power, I told him to come closer.



When he stepped towards me I told him to drop his pants. And just like that he stood there with his flagpole at full attention. Not sure what I was thinking, but I grabbed it and squeezed it. I could feel it expand,  feeling his heartbeat in my hand.



I gave it a little pump and he actually moaned. I figured I give him some pleasure, so he'd associate me dressing up with fun for him as well. I squeezed some more while pumping him up and down and in less than a minute he shot his load in my hand.



I was proud I had so much control and that I had given him an orgasm. I went to wash my hands in the sink, cleaning his warm goo from my skin. But I figured I better take the dress off now, and go in small doses. I hoped I could take the dress off without his help, as he still stood there naked, his dick already twitching again.



But the zipper wouldn't budge. As a matter of fact, something was attached to the zipper that prevented me from pulling it down. Feeling it better I could only imagine it was a small lock. When I looked back at Ben, he smiled.



You won't get that dress off without my help, babe, he said. And I enjoy it too much to help you right now. Why don't you walk up and down a bit, and twirl like you're on a runway?



I was stunned. Not quite sure if he was joking, but he seemed dead serious. So I walked back and forth, swishing my skirt, and spinning right in front of him. When  I stopped I gave him a smile and asked, you like? Would you mind unlocking my zipper? How did you lock it anyway?



Oh, it was simple, he said. I saw the dress yesterday in your closet, and I pinched a small hole in it so I could connect the zipper to the leather. I have had fantasies since, how you would suck my dick while wearing that dress, but I had no idea how good you would look overall. I'd like to see this every night.



I don't mind wearing it for you, I said, but I'm not gay. I have never sucked a dick.

I don't see a guy here, he replied, and girls do suck dicks, so you better prepare for that. What's your name anyway?



It's Elise, I answered, like the classical music. I like that, he said. From now on Elise, you do what I say, or I will expose you. You can start by cleaning this place up.



Still hoping he was playing me, I started on the little kitchen area. I noticed he was making pictures and touching his dick. When I had made his bed and folded all his clothes, he finally stopped me, and pointed at his now rock hard member. I saw no way out.



So I swallowed my pride and sat on my knees in front of him. I'd given him a handjob already, how much worse could this be? So I grabbed his monster and carefully licked it with the tip of my tongue, before I closed my lips around it. With a little push he filled my mouth deeper and I had to hold it back a bit so he wouldn't choke me. I bobbed up and down and was surprised how much I controlled it. I could make it thicker with some sucking, or relieve it by blowing a bit.



No matter what though, his sounds and moves became more urgent. And just when I thought he might cum, so I started pulling away, he held the back of my head, and suddenly he shot his load, his cum hitting the back of my throat. I thought I'd choke, instead the slimy stuff just slid down into my stomach. The taste wasn't horrendous so I swallowed the rest, so it wouldn't drip from my mouth. And when he pulled out I kept my lips tight, essentially cleaning the goo from his shaft.



He was happy. He had a smile on his face and I thought everything was good again. He even said how well I did that for a first time. But then he said I needed more practice as well.



Before I could think what he meant by that, he had me stand up and lift my skirt. Now he was sitting on his knees in front of me, grabbing my own dick, which was very tiny from the whole humiliating experience. For a moment I thought he was going to show me how it was done, but then I heard a click and he pulled my panties back over my member.



That will make sure there's only one male cumming in this room, he said. Now let me help you with that dress. And he turned me around and I heard another click, and then he pulled the zipper down. I let the dress drop to the ground and stood there in bra, panties and heels. I wanted to know what he'd done, so I tried looking past my breasts, as I pulled my panties away. It was like a shiny black rubber tube was covering my member and when I pulled it I felt pain in my balls, somehow the tube was connected to my scrotum.



His explanation was simple. There's no need in this room for a second dick, so your cock is locked away. No more hard-ons for you, no masturbation, the tube will be in the way. From now on you'll have to sit on the toilet, or you'll make a big mess, just like all other girls. I expect you to wear your dress each night, and give me at least one blow job. Is that clear?



I was stunned again. I wanted to fight him but he was already making more pictures and I knew it wouldn't end well. So I nodded. Is that a yes? he said, his voice raising. Yes, I whispered. Very well. As long as you do what I say, I won't expose you. But in return I expect Elise to become sexier and sexier. Can you do that? Yes, I whispered again.



It took a few days of getting into a routine, but getting used to the blow jobs I slowly started enjoying the power it gave me again. I was Elise from early evening until I had to get ready the next day to take my classes. Ben bought me some very sexy lingerie to sleep in, and soon I spent my nights in his bed. He liked to cuddle and I didn't mind it either.



But with the initial horror of the situation behind me, the enjoyment of dressing and acting as a woman came back. And with that my hard-ons came back and the desire to masturbate. Both failing, thanks to the cock lock. And how the tube at first hadn't bothered me, now I started needing some sort of relief, which did not come.



Apparently I had finally reached a point where he had wanted me sooner, and he started making small promises of releasing my dick, if I would do this or that, and I believed him each time and did exactly what he wanted. Which included a shopping spree, during which I bought a serious amount of sexy clothing. All weekend dressed up. More severe makeup and a number of piercings in ears and bellybutton. A tattoo that enhanced the look of my cleavage. And then there was this little pill that he wanted me to take every day. A vitamin that would soften my skin, he said. But my guess was it was some hormones, as I could not only feel my skin soften indeed, but my nipples under my breastforms started getting larger and small bumps forming under there.



But never did he really let me out. And it was so confusing. I did all this stuff to look better, to please him, and in doing so I got more and more in touch with my female persona which triggered more excitement in my male persona. And that excitement was still thoroughly stopped by the cock cage.



Until one night he changed the routine. By now I would clean the room wearing a vinyl maids outfit. And when I picked up one of his socks from the ground next to his bed, my skirt popped and showed my privates in full view, as I was not wearing any panties as instructed. This had happened before and I ended up giving a quick BJ, but this time he pushed me on the bed, with my butt still in the air, and suddenly he was pushing his dick into my rear.



He must have used some lube, as it went in relatively easy, although the pressure on my internals was enormous. I shook my butt a bit, trying to relieve that pressure, resulting in his dick suddenly sliding in deeper. I tried to stop it, but I was pushed with my face in his pillow, as his hands were holding strong on my hips. And then he hit something inside me that sent a wave of pleasure through my body, and I couldn't stop a moan from escaping.



It was enough for him to know he was onto something and he started moving back and forth over my hotspot. Each time the pleasure in my body increased and I moaned out loud now, unable to stop. I could feel my dick straining in its cage, but unlike before, when the pain would start and essentially stop the pleasure, now the pleasure was so overwhelming that I couldn't even feel the pain anymore.



In seconds the pleasure overloaded my system and suddenly an incredible release rocked my body. It must have been an orgasm, but so powerful and so different. In different spots inside me, and spreading out to my fingertips and the tip of my toes. I think I screamed, muffled by the pillow, as my whole body was shaking now. I felt a wetness on my legs and with a slight nod of my head I pushed up a bit, so that I could see the underside of my body. I saw a thick string going from the tip of my cage down to the wetness on my leg, and I suddenly knew that my balls finally got some relief.



I couldn't celebrate for long, as Ben got his motion going again and I was unable to ignore the new wave of pleasure hitting me. My body reacted pretty much the same but when I hit my high, I could feel him spray my insides, and this time it was his massive grunt that I could hear.



It took a few minutes coming down from my high, that I realized I had lost my virginity, and that I had come twice while this happened. I guess I was really a woman now, except my own dick suggested otherwise, as it had squirted even more goo. No, let me take that back, it had dripped out from my soft, constricted member. But clearly, enough was pushed out to relieve that built-up tightness in my scrotum.



Ben disappeared straight in the shower, as more goo was now leaking from my rear. I used a dirty towel to catch all of the cum and clean it up, to keep his bed as clean as possible. When he got out of the shower he told me to get clean as well, and I was mighty thankful.



The next day Ben gave me a device with instructions how to use it to clean my insides. He told me to always be clean and ready for more penetration. And as much as I didn't want to admit it, I couldn't wait for it to happen again.