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: Chapter 2
More fun with Brian
I had a lot more fun with Brian. I sucked him off every day after school that week. Then we got more into a routine of a couple times a week, usually after school. A couple times he called me and told me he was picking me up to go to school and I gave him a BJ on the way. I even sucked him off one time in his car at the school parking lot after school because we were too horny to wait till we got home. We both agreed that that was too dangerous and not to do that again. It was enough for me to know though that I loved the thrill of possibly getting caught and public sex. Brian was a little more reserved about that though.
Because he was a little reserved during sex, I didn't want to tell him about my crossdressing. I had gotten a few articles of clothing, pilfered from my sister. When she came home and brought laundry, she would usually leave the last pair of panties or outfit at the house. I slowly accumulated a few sets of panties and bras and a short skirt and top I loved to wear. I went online to learn how to put on makeup and practiced with a lot of trial and error. The only thing I was lacking was a wig. I really wanted to dress for Brian, I thought he would probably even like it, but I couldn't muster up the courage.
It was fun having a hot guy to regularly suck off, but I kind of wanted more. I tried to get him to fuck me once but that was a little farther than he wanted to go. It wasn't really gay to him since he was the one getting a blowjob and he never touched my penis. Fucking my ass would have been a little too far. I really wanted it but I knew it was either that or nothing. He was really good about it too. He always asked if it was ok that he never played with my dick or kissed until I reassured him many times. As long as I can play with both of our cocks, I was fine. I actually preferred him not touching my penis. I wasn't really attracted to a strong man going down on me. It was the opposite of what I wanted. I wanted to pleasure and go down on a big strong man. Even though I was naturally smooth, I always kept my butt crack shaved, just in case he ever wanted to stick his cock in there.
Brian was stilling dating Kimberly and I was fine with that. I knew girls are what he was attracted to and I was basically a warm hole to put his dick. He would still tell me what he did with her on their dates and it honestly seemed kind of boring. They made out a lot and when they had sex it was almost always in the missionary position. I was jealous of her but was pretty happy with getting a warm load of cum every few days.
That summer it was harder for us to meet. We both had jobs and at different hours. We were going to different colleges so we wouldn't see each other a lot after the summer. One afternoon after not having blown him in a week, I was particularly horny. I was already half dressed, wearing only my swim trunks. After sucking him for a couple minutes and feeling his hard cock in my mouth I decided, what the heck. I got up and tried to climb on his cock and straddle him. I don't know what I was thinking, I mean I hadn't even put any lube in my hole!
"What are you trying to do? You know I can't fuck you." He told me.
"Come on. You know you want to" I replied. "You can't tell me you don't want to know what its like to fuck a virgin ass. Besides, I'm so horny right now I really need to get fucked."
"I already told you that's a little too far for me. Besides, you don't even have any lube in your ass retard." He laughed. "Do you have any idea how much that will hurt?" He then went on "I know it's not really fair for you to get me off all the time and I don't reciprocate. Do you want to stop our arrangement? It's cool if you do."
"Of course not Brian. I love sucking your cock." I assured him. "It's just a little frustrating. I get pretty horny thinking about it, and then I hadn't seen you in a week. I've never even had anything up there except a couple fingers and I just wanted to try it."
"I've got an idea." He said and took me upstairs. We got online to a sex shop and he told me to pick out a dildo. After looking for a couple minutes I realized I was more interested in his cock and told him:
"Pick me out the one that looks most like your cock," and got on my knees to blow him as he completed the transaction. He picked out a lifelike 6.25"dildo with flesh colored skin and a suction cup base. He put it on his credit card, lucky to be a well off kid with a credit card and the house to yourself, and even had it delivered next day to his house with a bottle of lube. I couldn't wait to practice deepthroating on it and to feel it in my ass.
I rushed over the next day after work to try it out. I had even worn a thong underneath my clothes for the first time outside. It may sound kind of sad, I mean I had a guy letting me suck his cock but wouldn't fuck me, and I was all excited a bout a dildo. But I was excited! I got there and he had the box sitting on the couch. He told me he had another present, flavored condoms, and to try out the dildo. I didn't really feel like trying it out in front of him so I took it upstairs to one of the bathrooms. I ripped it out of the box, tore off all my clothes but the thong, and got even harder when I looked at the dildo. It even looked lifelike! It was a little slimmer than Brian's cock but other than that they looked very similar. I quickly rolled a strawberry condom on it and started sucking it. It tasted pretty good, but not the same or as good as a real cock. I pulled my thong down to the back of my knees and admired my ass in the mirror. It kind of looked like a girls ass it was so smooth and I had a tight hole. I quickly squirted lube on it and continued sucking the dildo. Working the lube all the way in my ass, I couldn't wait any longer. I needed to feel it inside me. I put the suction cup side down and watched as my saliva ran down the side. I took my thong all the way off and lined up my tight hole with the tip of the dildo. Remember when you first put something in your ass? I sure do. It burned at first and I gave a little yelp. I squirted another shot of lube on my ass and another one on the tip of the dildo and tried again. This time it sank in much easier. It got in about half way in before I stopped to get accustomed to it. Squatting over the dildo I lost my balance and the dildo slammed into me! I gave out a little shriek but quickly got used to the dildo in me. I guess most accidents do happen in the bathroom. I started moaning as I bounced up and down on the dildo. There is nothing like a real cock in your ass and as I wasn't going to get that for awhile, but this was doing nicely. After a couple minutes I shot a load up in the air. My legs were tired from the exercise but I cleaned up and headed downstairs.
"I could hear you liked that present" Brian said with a smirk. He greeted me a naked body and a flavored condom on as I arrived downstairs.
"It was awesome Brian. Thanks a lot." I told him
"Man you were moaning and squealing louder than Kimberly when I fuck her" He laughed.
"Don't talk about that little slut" I scolded him, pretending to be mad. Honestly though, I was always a little jealous of her.
"Don't be mad and come get those warm lips around my cock. I hope you like banana?" he joked.
"What are you talking about? I already got off. Why would I want your cock in my mouth now?" I teased and headed for the door.
Sounding worried he said "You're not actually leaving are you? I was just kidding." and ran after me. Right at the doorway he put his hand on my shoulder and I swung around, dropped to my knees and engulfed his cock in my mouth. There was no way I was leaving such a beautiful and stiff hard on unattended to! I really went at it, slurping and sucking his cock. My ass had a just fucked feeling from the dildo and it made me even hornier. I bobbed my head up and down and sucked like a vacuum. I was on a mission to make him spurt. I grabbed his hips and used them as leverage to really get as much of him in my mouth as possible. He took the hint and started grabbing my head and almost face fucking me. He came in and instant and filled the condom with his gooey cum. I quickly rolled it off his cock and, to his surprise, poured his cum into my throat and gobbled it down. It was a little cold from hitting the air in his cool air conditioned house, not quite as good as straight from the tap, but still delicious.
"Wow! That was hot. I didn't expect you to slurp up my cum like that" He said with an exhausted smile. I just gave a little laugh and went home.
One of the best weeks we had that summer was when his girlfriend went to Hawaii with her family. Every night that week, since his parents were home nights, we went to he and his girlfriends make out spot and I would go down on him. Doing it in a car has always been a big turn on for me. I had practiced a lot on the dildo he got me and had learned to deep throat. He always loved that. Actually our most exciting time was yet to come though.