While I was growing up, me best friend from down the road had talked me into sucking his cock. Between the ages of 13 and 18, when we graduated high school, I must have sucked his cock hundreds of times. One thing he didn't know about me during that time though was that I loved the feel of women's lingerie as it caressed my body.
I had a small stash of lingerie and stockings building up throughout my high school years. When I had a chance, I would dress up in panties, stockings and a bra and jerk myself off. Because nobody knew my little secret, I had to bring my stash with me when I headed off to college. I was fearful that my new roommate would find them, so I kept them hidden in my suitcase under my bed.
This worked fine for a while, I would dig them out on the weekends when he went home and not have to worry about anyone coming in on me, so I was starting to spend a lot of time on the weekends in sexy lingerie as I studied and stayed around the room. Every once and a while I would wear the panties and stockings under my pants all day on a weekend, knowing nobody would see them. I loved the feeling of the nylon on my legs and cock.
While I was in college, I was unable to add to my collection of lingerie I had built up, but I now had a black lacy bra, fake breasts, 2 pair of lacey panties, one red and one black, and a lot of different stockings and pantyhose. I figured by keeping this in my suitcase under the bed, I wouldn't need to worry about anyone finding the stuff, but I was wrong.
My college roommate was new to me. I went to school far from home and did not know anyone there, so on move in day I met my new roommate. He was about 5'8", 150, brown hair and brown eyes. He actually looked a lot like my friend from home, whose cock I sucked back home. I was pleasantly surprised. We spent the weekend getting to know other people in the dorm and the lay-out of the campus before classes started. He lived close by, so he was going to go home every weekend, so I knew I would have time to dress up in my lingerie I had.
When classes started, we had some of the same classes, but we also had separate classes. I worried that he would rummage through my stuff when I wasn't there. I figured that he may look through my drawers, the desk, etc., but I never expected him to look into my suitcase. Let me explain how that day unfolded and how we went from being just roommates to being intimately involved.
The day had started out the same as the first few weeks. It was Monday morning and we had the same first class together and we went to class. After that class I had another class, and he was able to go back to the room until later that morning. So off I went to my class and off he went back to our dorm room. While I was in an English class learning how to write papers and do research, he was back in our room doing some "research" of his own.
After that class I headed back to the room and when I entered, it didn't seem as if anything had happened. It appeared that he had come back after the first class and started to watch TV. Later that night I would find out what he was really up to during that time. He later went off to class and I stayed back at the room. After his class, we met at the Cafeteria for lunch. We then each had an afternoon class, then our days would be complete. He went his way, I went mine.
After watching some TV to pass the remainder of the afternoon, we went off to the Cafeteria for dinner. We ate and talked like we had the past few weeks, like nothing had changed. After dinner, we studied some and hung out with other guys on the floor and watched some TV. We decided to get ready for bed around 10:00 that evening and that is when everything changed.
When we were both ready for bed and he had climbed up to the top bunk, I shut off the light and got into the bottom bunk. We exchanged small talk like we usually did before going off to sleep, only tonight he wanted to talk about sex. He had a girlfriend and was telling me how he loved when she gave him blowjobs. I thought nothing of this, he asked me if I had ever had sex and I answered yes. Really though, the only sex I had growing up was giving blowjobs to my neighbor down the street, but I didn't want him to know I was a virgin, so I told him yes. Then he told me that he had been looking for something today and happened to look in my suitcase and was surprised to see women's lingerie. I tried to tell him that it was from my girlfriend, but he knew that they were mine. After wearing them so many times, you could see cum stains where I hadn't washed them good enough after shooting my load onto them. I was found out!
I was so afraid of what he was going to say or do to me. I am the kind of guy that is laid back and don't want to bother anyone and just go on with life. I hate to say no to anybody. He climbed out of the top bunk and sat on the edge of my bed. My mind was racing. What was he going to do? What was he going to say?, etc. He said that he didn't believe that I wore women's lingerie. He said that as long as I went along with what he said, everything would be fine and nobody would know. I was a bit relieved by that news, but what did he have in mind? I was soon to find out. He wanted me to dress up for him right then and show him what I looked like as a woman.
Nobody had ever seen me in the lingerie, now I was going to put it on in front of my roommate as he watched. He grabbed my suitcase from under the bed and opened it up for me and told me to get dressed. So I took off my boxers I was sleeping in and put them on my bed. Of course, I was extremely excited to be naked in front of another guy, but this was different than all the times with my friend from home who I blew so many times. This time the attention was on me. I had a huge (for me) boner of 5 inches sticking straight out at this time and he asked me if I enjoyed this. I didn't say anything, but my cock spoke for me.
I first grabbed the black lace bra and strapped it on my body and proceeded to stuff them with the fake breasts to fill them out. I then grabbed the black lace panties and slid them up over my extremely hard cock, encasing it in the smooth panties. I sat down on the bed and grabbed a pair of stockings and slid them up my leg into place and finished my transformation. He then asked me to stand up, which I did. He walked around me looking me up and down. He kept saying that he couldn't believe that I wore women's lingerie. At this point, I was so turned on by being in these clothes, that I had started to leak some cum and it was visible through my panties and then he asked me how long I had been doing this.
After telling him that I had loved women's clothing for as long as I can remember, he just shook his head in amazement. That lead to the next question of, did anyone else know about this, which I replied no. He then asked if I really had ever had sex before, and I came clean and told him no, not really. He then asked what I meant by "not really" and I told him that I never had sex with a girl, but I had sucked my friends cock many times throughout high school. At this point, I figured he knew I liked men, so what was the big deal. I told him that I sucked cock throughout high school, but he didn't know that I wore this lingerie.
He was stating to relax a bit as he continued to question me about why I did it, if I liked it, what it felt like, etc. I also at this point was a little more relaxed, but my cock was still stretching the front of my panties. This is when he asked me if I would suck his cock. He said that he never had a guy do this before and that he wasn't gay, but his girlfriend hadn't sucked his cock in a long time. He said that he was getting horny and that he needed to be relieved, so I was more than willing to suck his cock.
He removed his shirt and boxers and I was amazed by the size of his cock. It had to be at least 8 inches long and 2 inches wide. Compared to my cock, this thing was a giant. I got out of my bed and on my knees in front of the bed and he walked over with his cock bouncing up and down with each step. He was a little hesitant at first to let me touch his cock, but I reached up and took his huge cock in my hands and began to gently stroke his shaft with my hands. It had been a couple of months since I sucked off my friend from high school, so I was glad to have a cock in my hand again. What was even more exciting this time though was the fact that I was able to suck cock in my lingerie. After spending some time stroking his cock and playing with his balls, I decided it was time to get down to business.
I took a hold of his cock at the base and stuck my tongue at the base of his shaft on the underside and slowly licked towards the tip of his cock. As I was doing this, I could tell that he was feeling more and more comfortable by the moans escaping his lips. I repeated the step one more time and licked my way from the base of his cock to the head. I then opened my mouth and took his cock head into my mouth and began to lap at his cock head with my tongue. I pulled back from this and wrapped my hand around the base of his cock and brought a nice load of pre-cum to the tip of his head. I licked that from his slit and savored the taste of cum once again. This one was saltier than my friend from home and tasted a little better. I then took his cock in my mouth and tried to swallow as much of this monster as I could take. I think I was able to get about three- quarters of this giant in my mouth. I slowly started to bob my head back and forth over this cock, as he moaned his pleasures from above. After a few minutes of sucking his cock, I pulled off and started to stroke his cock again for him. Slowly at first, then picking up speed. This was really turning him on and he was lost in the moment. I started to suck on his cock again, while at the same time stroking his cock. As I pulled back on his cock, my hand followed my mouth up his cock and as I descended on his cock, my hand went down his cock. After a few minutes of this I could tell he was breathing harder and was tensing up, so I knew he was close to shooting his load.
I stopped sucking on his cock and replaced my mouth with my hand stroking him ever so gently at first, then faster and faster. I took my tongue and once again licked the underside of his cock from the base to the tip and that drove him wild. A few more strokes from my hand and the next thing you know, he's shooting a huge load of cum onto my face and "breasts." I think he shot at least five good loads of his hot sperm onto my face before he was finished. When he finished, he looked down and was amazed at how much cum he had shot. I scooped some from my face as he watched and tasted the salty treat. I then again grabbed his now softening cock and placed it in my mouth being sure to get the last drop sucked from his cock. When I was done, he put his boxers back on and sat down and told me that I gave him the best blowjob he ever received. I grabbed a towel and cleaned as much of the cum from my face as I could and sat on my bed again.
We talked a little more about this before heading off to sleep that night. He couldn't believe that I sucked cock and wore women's lingerie. He did mention that my secret was safe with him as long as I was willing to service him whenever he wanted. Of course I told him yes. My favorite thing to do was to suck cock and make the man happy and satisfied. He climbed back into bed and I stripped out of the lingerie and put it back into the suitcase and laid back in bed naked. My cock was extremely hard and aching for relief, so I figured since I just sucked his cock, he wouldn't mind if I jerked off. So as I stroked my cock, I replayed the nights events in my head and before long, I was shooting my own load of cum onto my stomach and chest. I grabbed the towel and cleaned myself up as best I could and went to sleep.
That night was the first time another man had seen me in lingerie and turned out to be the beginning of a good four years of college. Whenever he wanted his cock sucked, I was there for him. If he went home for the weekend and he and his girlfriend did not have sex, then I knew that Sunday night when he returned, I had a cock to suck. We stayed together as roommates all throughout college and nobody else expected anything.
There were more memorable nights that we shared together in college and even a few since then, but the first time was best. If you would like to hear more of my time spent with my college roommate and my lingerie, write me at jeremyrogerson@yahoo.com. I look forward to hearing from you and writing about another night we shared.