Chronicles of a Crossdresser 1
This story is property of the author. Don't repost without my consent and don't read if it is illegal to do so. These are true stories about my sexual adventures and crossdressing. The sex always is between consenting adults.
Chronicles of a crossdresser
First experiences
I started out like most every other crossdresser I guess. First seeing my sister's thongs in the hamper and being fascinated by them. I was a freshman in high school when I first got the courage to try them on. She had come home from college for the weekend and brought all her clothes home to wash. My family was going out to dinner but I pretended like I wasn't feeling good just so I could stay home and play dress up. I tried on every combination of clothes I could, knowing it could be quite awhile before I would get the chance to play dress up again. I really began to like the slutty look. Luckily, my sister being a sophomore at a notorious party school had an abundance of slutty clothes for me to wear. Short skirts, thongs, booty shorts, really short shorts, tops that showed off my midriff were all a big part of her wardrobe. Looking in the mirror, I really noticed how well I filled out these clothes. Sure I had to stuff the bra to fill it out, but I had to admit with my lean and tall figure, I looked pretty good. I was young, but still tall and naturally smooth with almost hairless arms and fairly smooth legs. The little hair I had on my legs bothered me but I was not about to shave it. I was not out of the closet to anybody.
I pretty much knew I was gay in Jr. High. All of my friends were starting to notice girls. They'd talk about what so and so was wearing and how short her shorts were that you could almost see her ass. They'd talk about how they heard she would give you a BJ after a couple dates. Actually, nobody really dated then. You just hung out and if you were part of the cool kids you'd eventually make out with a girl and call her your girlfriend. The really lucky ones got blowjobs from them. I had friends in that group but was never part of it. I was always more interested in guys. I loved looking at girls, but mainly at what they wore. I'd look at Victoria secret catalogs and wish I could buy what they were wearing. I'd watch porn too but mainly love to see the oversize cocks and look at how the girls sucked them and tried to learn techniques. I wasn't really interested in getting fucked yet, I just wanted a cock to play with. I had to wait for my senior year for that to happen.
Brian moved to our school during my junior year. We were in a lot of the same classes and quickly became friends. He was outgoing and became pretty popular fairly quickly. About 6'2 with a pretty darn good body, he became the starting safety on our football team, partly because our team wasn't that good. He was one of those kids whose parents had a lot of money, both worked a lot of hours as lawyers, and kids who didn't know him may have assumed he was stuck up or spoiled. Anyone who talked to him knew he was a good guy. He started giving me rides home since I didn't have a car and my tennis practice let out the same time as his track practice most days in the spring. Sometimes we'd hang out at his parent's house. His house was pretty big with a pool and he had the latest video games and big screen TV to play them on. His parents did buy him a lot, mainly because they were rarely home. He was usually left home alone as his sister had left for college a couple years before and his brother was almost 30 and had been out of the house for awhile.
I started hanging out at his house a little more and could not help being attracted to him. Of course, I could never say anything; it was obvious he was straight. He had a girlfriend and a not bad looking one either. Sometimes I couldn't help it though and I'd initiate some wrestling with him. One day while we were playing a video game after school he just blurted it out:
"It's ok if you're gay you know" followed by a silence. "I don't care at all"
I was taken back. Wondering how he knew but not wanting to admit to anything. I stammered "I'm not gay." in a soft voice. "Why would you think I'm gay?" In a little louder voice to not show weakness.
"No reason." He replied. "Well actually, it's just that you've never had a girlfriend and you almost never talk about girls. If I say a girl is hot, you always just agree and you change the subject fairly quickly. It's cool if you are and if you're not I didn't want to offend you, I just wanted you to know it doesn't matter either way." I was kind of taken aback and didn't say anything. I was glad when he started talking again until I heard what he had to say.
"Some people at school just said something and it made me wonder a little." He started to say.
"People at school think I'm gay?" I replied nervously.
"Just a couple guys asked me if I knew if you were gay. I said you weren't but I thought I'd ask." Brian informed me.
"Well thanks for telling me and for sticking up for me. But I'm not gay" I said, trying to sound casual. He told me it was cool either way and he was sorry for bringing it up. We played for about another 10 minutes and then I told him I had to go home.
I went home that night and had some trouble sleeping. I just told myself to act like nothing had happened and it would go away. I tried to have everything back to normal the next day and I could tell Brian was too. We went to his house the next day and were hanging out at the pool. What he had said the day before was gnawing at me and I had to say something.
"Brian," I started out "I am gay. I'm going to hold you to what you said yesterday though about it being cool either way." He told me it was definitely ok and that my secret was safe. He then started asking me questions like: when did I know? Junior High. Was I attracted to girls at all? Not really (I couldn't tell him I liked transvestites). Did anyone else know? Nobody.
Things went back to normal pretty much. He would tease me about being gay when we were by ourselves. If he beat me in a video game he'd tell me that I suck as bad as I want to suck a cock or if we wrestled and he was winning, like he pretty much always did, to watch out because I was going to take it in the ass for the first time. Honestly that stuff turned me on as I was obviously attracted to him. I would kind of brush his leg quite a bit as we wrestled and even "accidentally" brushed his cock with my hands a few times.
One time he said "that's the second time you tried to grab my cock. Are you trying to tell me something he said with a smile?"
"Maybe." I replied with a smile, immediately regretting what I said.
He was ok though and didn't get upset like I thought he would. He just asked "Have you ever done anything with a guy before? Like sucked a dick or just kissed a guy?"
"No, of course not." Was my response. "Who am I supposed to do that with? I don't know any gay guys except a couple at our school and it would definitely get out all over school if I tried to do anything with them. Besides I'll just wait when I go to college in 4 months. People will probably be more understanding and my parents won't know." Surprisingly I didn't feel that awkward. I was 18 and had just told him I had never even kissed anyone but I felt totally comfortable around him.
"But you want to suck a dick right?" he inquired.
"Of course." Was my reply as I really got turned on by the idea and started imagining what his cock looked like.
"What about having your dick sucked? You have to want that." he asked me.
"Not really. Honestly I get more turned on by the thought of a dick and pleasuring a guy." I said as my horniness led me to shift positions on the floor. "Is it that good, getting your dick sucked." This time it was me asking the questions.
"I wouldn't know yet" He said to my surprise.
"What! Come on! I know you're fucking Kimberly. You mean to tell me she hasn't given you a blowjob?" I was actually pretty astounded. I thought most high school girls suck dick
"Nope. She says it's icky- her words. She won't even try it. I've been trying to get her to do it for the last year but she won't. She's starting to get mad at me even when I bring it up." He informed me.
"Too bad for you!" I laughed. "Maybe when you get to college."
"Maybe before then was his reply." I knew what he was getting at but I was pretty shocked and tried to remain calm. "I know you're attracted to me. I see you try to look at me out of the corner of your eye and how you always find a way to brush against my cock when we wrestle. You said you wanted to suck a cock, why don't you try it?" He was always pretty forward like that.
What if he was kidding around? I didn't want to take a chance but I was getting hard just thinking about it right now. "You're joking right?" I asked.
"No." He replied simply. "I know you find me attractive and you want to suck a cock" he repeated. "I really want to know what it feels like. Other guys tell me its better than sex. If I find a girl at school to do it, it might get back to Kimberly and she'd break up with me. I know you wouldn't say a word because people would know you're gay.
"Are you sure?" I asked with my heart racing.
"Absolutely." He assured me. "I just don't want to suck your cock and I don't want to kiss. If that's still cool with you."
"Sit on the couch and take your jeans off" I commanded. I couldn't believe this was happening. This was a dream scenario. I could suck off a hot guy and knew nobody would find out. He couldn't tell anyone anymore than I could. Plus, I knew he was clean so I could do it bareback and I actually really wanted to taste his cum. Sure he didn't want to kiss, but that was ok. I was going to get some cock!
He sat on the couch in just his boxers and tee shirt. I told him "I'm not only going to suck your cock but I'm going to swallow every drop" as I dropped to my knees in front of him.
I pulled his cock out of his boxers and examined it for a second. It wasn't as big as the cocks I'd seen in the pornos, maybe 6.5 inches, but I kind of preferred that. How the heck was I supposed to fit one of those 9" ones in my mouth anyway? I started by licking up the shaft and looking up at him. He was staring at the ceiling. I guess he was pretending I was Kimberly. He still had his boxers on so I told him to lift his hips so I could take them off. How could I give his balls the proper service with his boxers on? Then I started sucking and tonguing his balls. I looked up and he was still staring at the ceiling. "It's ok" I thought to myself. "Keep pretending I'm Kimberly. I'm the one with your hot cock in my mouth."
I then went after his cock. Licking up the shaft, I engulfed his cock in my mouth. I started bobbing my head up and down. It was a little sweaty tasting as we'd been at school or wrestling on the floor all day but I thought it was delicious. I thought to myself "Here goes nothing," as I tried to deep throat him. All that happened was I was introduced to my gag reflex and a couple coughs.
"Are you ok?" He asked in concern.
I smiled and said reassuringly, "I'm fine. Just no deep throat this time I guess."
With a little laugh I got back to my duty. Sucking and slurping on his cock gave me the biggest erection I could remember. I wanted to reach down and jerk off but I knew he was picturing a girl sucking him off so I didn't want to ruin the illusion by whipping my hard on out. I planned on sucking his cock many more times. Little did he know that the thought of being dressed up as a slutty girl would have been a big turn on to me as well.
I hadn't been sucking him that long when told me to get ready for it because he was going to cum. "Get ready for me to nut in your mouth baby" he said. I thought it was a little weird, him calling me baby, but I didn't care. This was the part I had been waiting for. I started sucking harder and he put his hand on the back of my head and exploded in me. He had warned me but it was still a shock as I wasn't expecting it to come out that fast. Spurt after spurt filled my throat. I tried to swallow it all but some started dripping out my mouth. I swallowed as much as I could and licked the rest off his cock. The actual taste of his semen wasn't good but something about it made it delicious. Tasting his cum on my lips I stood up and asked teasingly "are you sure you don't want to kiss me."
He laughed and told me "go wash my cum off your mouth gay boy."
I wanted to tell him "look who just got sucked off by a gay boy" But I knew he was kidding. Besides I wanted the same experience tomorrow. I washed his semen off my face in the bathroom and noticed I had the biggest smile.
When I went back out to the living room he said "same time tomorrow?" He then asked "things are still cool between us right?" I assured him they were, I mean we both got what we wanted, but I still needed to get home. He gave me a ride. And I played with his cock on the way home. I lived pretty close but he was hard again by the time we got to my place.
"How about another quick one?" he asked hopefully.
"Not in front of my parent's house." I laughed. "Go home and jerk off like I'm going to do. Or better yet, save that load for me tomorrow." I went inside and immediately jerked off. Craving the taste of cum, I even licked some of mine off my hand. Not bad, but not nearly the same.
That's the first installment. I'll add more. Most of the rest involve crossdressing as now I am only with men while dressed. Hopefully you liked it.