A Teenage Boy's Journey to Self-Discovery

Jenny's First Night Out


I had just turned 15 yrs old a month ago but have been dressing up for almost a year now. I buy most of my clothes in thrift shops saying they are gifts for my sister. Hard part is finding shoes my size. That and makeup I splurge my money on at the local discount store in the city.
I live in a small burb just on the outside of the city.

So going to stores where I'm not recognized is easy for me. LOL I live for the shopping part of dressing. I'm sure I don't fool every sales clerk but they don't care a sale is a sale. Someday I hope to go shopping when dressed.

My dad left us when I was 6 and mom and I have been fending for ourselves ever since.
I work in a local grocery store on weekends and make some money helping neighbors with yard work or other light chores after school. The real money maker of course is mom. She works as a saleswoman for a large company. Which works for me since she has to travel on occasion usually for a couple of days.

I love buying the more slutty looking outfits like denim skirts tank tops. And of course heavy eye makeup. Being thin and only 5'5'' and letting my hair get long I can easily pass for a young girl when dressed.

Like any 15yr old I've discovered jerking off. Its way more powerful when fully dressed up. Just putting my hands in my lace panties gets me instantly hard. I imagine its a man feeling me up and running his fingers up and down my small cock.

At first I had wish my cock was bigger then its 4 inches but then I noticed it doesn't show through my clothes. Even hard unless I wear something skin tight I can pass for a girl there too.
The more I dress up the more I think of sex as a girl and not as a guy.

My mom is out of town for three days and I'm all caught up on chores and school work.
So I've decided to try exploring my boy pussy. My mom's hair brush seemed like a good choice. The handle is about 6 inches long and narrow. The only real lube I could find was a jar of Vaseline. Not a preferred choice but good enough.

I've dressed up in knee high nylons, pink panties, training bra, see through blouse and a knit skirt. I love my tiny heels but still need practice walking in them. After spending well over an hour playing with the war paint my face is now feminine. Or at least passable enough in a slutty way.
My hair is long for a boy but just short enough to pass for a short hair girl if combed out enough and slightly flipped. I'm ready to try playing with boy pussy.

My bedroom has a long mirror on the closet door perfect for watching myself.
Getting down on all fours and pulling my panties slightly down I look into the mirror. I look hot. I look ready for sex. I put my fingers in the Vaseline jar to lube them up and then started to rub my ass and pussy hole. It really feels nice rubbing the lube around my hole. Then I slowly entered my hole with my middle finger. It was tight but it went in without any pain. It felt awesome. Soon I was sliding it around inside and loving every second of it.


I knew I had to have that hair brush handle in me. So I lubed that up and tried to push it inside. I was a little over eager because it did hurt. Not a lot but enough to slow me down. I pulled it out used more lube and tried it again. This time slower and more gentle was the key. Once I got it in fully I waited a minute and then began to pull it almost out then pushing it back in again.

It didn't take me long to get a real fuck rhythm going. I was made to be fucked. I reached my cock with my other hand and matched my rhythm with the brush. I was in heaven. To me this was what fucking was all about. My boy pussy was full and taking every inch of that handle. Before I knew it I was going faster and faster..

I didn't even notice my other hand jerking my 4 inch cock. All I could think about was being fucked by that hard brush handle. It was driving me towards an orgasm and all I could think about was more and more, faster and harder. I wanted that handle to fuck me like I was meant to be fucked. Before I knew it my cock was shooting off in my other hand. I didn't care I just wanted that handle to finish me off. Slowly I collapsed on the rug with the handle still in my boy pussy.

Once I came to my senses I got up and went into the bathroom to get cleaned up. I needed to get that brush cleaned and back to mom's room before I forgot it. Even though mom probably already has some suspicions about me there was no need to arouse her. I felt great after having fucked myself and knew I would be doing that more often.

I also wanted to know what a man's cock was like. I knew I wasn't ready for a real cock up my boy pussy but was curious about sucking one. The guys at school were jerks. Word would get out in a heartbeat if I even tried anything sexual. Plus the fact I wasn't interested in their cocks. I already had a small cock I didn't want sex with one too. Not having a father around made me feel the need for a real man to be with me. And I knew just where to find one.

Just inside the city was a small gas station . It didn't do much business because gas is cheaper in the burbs. Its big draw is it caters to truckers. It has a large parking lot and big clean bathrooms. Best of all it has a glory hole between the men's room and the ladies room. Once my mom went there for gas and when she found out she forbid me to ever go there and never drove there again.
Its the perfect place far enough from home that no one there would recognize me there and close enough to walk to even in heels. All I needed was it to be dark outside. Tonight was a moonless night too. Even the stars were in my favor.

So I cleaned myself up took one of my mom's smaller purses put the Vaseline in the purse along with some money and other items and headed out the back door. Soon I was there. Since it was just after 10pm there wasn't a lot of cars or people around. I did my best to strut past the trucks and into the ladies room. Hoping some trucker would see me. I locked the bathroom door and found the stall with a hole in it. Sure enough it seemed to be at eye level when sitting down and cock level when standing. There wasn't yet anyone on the mens side of the wall.

I didn't have long to wait. Soon I heard a guy enter and then go into the stall. He never pissed or sat down. So I put my face closer and looked inside. He had already pulled his pants down and was stroking his cock. It looked huge to me. Must have easily been 8 inches hard and three times as thick as mine. I heard him whisper is this what you're looking for ? I squeaked out a high pitched yes.

Just like that it came through the hole. Well go ahead then suck it he said. For once I was a tad unsure. It was one thing to fantasize about being a girl and sucking and fucking men its another to actually do it. Yet here it was right in front of me. I was drawn to it. I had to have it in spite of my misgivings. As I touched it I was surprised at how warm it was. It was rock hard yet felt like velvet. I stroked it like it was my own. Well don't just rub it girl I can do that myself he said. It was now or never.

I slowly put my lips on it. I kissed the tip and felt the head slide past my lips and into my mouth. Did he push it in or did I go down on it ? It didn't matter because at that moment I knew this was what I really wanted and needed. I was now a girl with a real cock in her mouth. I would never again be that unsure boy wondering about his sexuality. I knew what I now was.

Just as the hair brush had just hours ago slid into me this cock was now sliding into my mouth. With each bob I tried to get more inside my mouth but my inexperience showed as I could barely get just over half in my mouth. Come-on work that tongue he said. I didn't even realize that was part of what sucking was about.

I swirled my tongue around the tip each time I came up and soon found I could swirl it somewhat around the cock too. Just as I started to get the hang of it I could feel the cock throb slightly. Was it about to shoot ? But it was only precum coating my lips and mouth. It did make sucking easier and I loved the taste. I sure hoped cum would taste this good too.

He started moaning and telling me what a great cocksucker I was. That helped to encourage me even more to suck harder and faster. As I sucked I became comfortable enough to go deeper. I couldn't get all of it in but I was deep enough that he was now picking up speed too.

I was being face fucked for the first time in my life and enjoying it. I knew I could make this guy come inside my mouth. But was I ready for it ? Could I handle it ? Would it taste good or bad ?
I didn't have long to wait. His cock was starting to throb and shake in my mouth. Without any warning from him I felt the first blast of cum hitting the back of my throat.
It never seemed to stop. I took blast after blast until it flowed from my mouth and down my chin.

Usually I just have two small blast and a few dribbles. This cock had about ten blasts and a lot of cum in those blasts. I never tasted anything as sweet as that cum before. I always heard it was salty or worse. But this cum wasn't like that. It was mild and sweet.

Very warm like his cock. I loved it and wished he would get hard again. He was already getting soft and pulling out. He thanked me and said I was a good cocksucker and if I kept doing it I would be great in no time.

As he zipped up and left I wondered what I should do. If I stayed there probably would be another cock in the hole soon. If I walked outside past the trucks I might now get more noticed. Or I could slip out and around the gas station and take a longer way home.

It was late out. I easily had time to get home but if I stayed there was no telling when I would get home. Or what else I would do. What I did know was I loved being a girl.
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