My little secret

My crossdressing started in Jr. High. When I started to get curious about girls, and also about other boys. I started crossdressing with my moms things, and slowly started to collect my own. By the way, I’m Mat… or Ashley as i’m known. I’m 17 and I guess you could call me Bi-Curious. Although after this story you could call me purely Bi-sexual.

I have a friend, Katelin is his girl name but everyone knows him as Jake. He’s the same age, and we’ve been good friends for quite a while. We found out about each other last summer. When a pair of panties I thought I had hidden, suddenly came out into the open. Before I could react, he grabbed them and started asking me all kinds of questions. “Whos are these, what are they doing here, How did they get here”. Finally after 20 minutes of him bugging me I finally came out and said it.

“There mine…” I said with my head looking down.

He started to chuckle then realized that I wasn’t joking. “But why??” he asked with a strange tone.

“I dress up like a girl, and then just wack off” I said. “Its just a thrill I have and I like doing it”.

This struck him as odd as he started to get up off of my bed. “How long have you been doing this” He asked with a scared tone.

“Since Jr. High, I started with my moms stuff and now I have my own.”

“Theres more??” He asked very suprised.

As I walked to my closet I pulled out a very familiar backpack to him. It was his old one that he was going to throw out. I used it for my baseball gear at first, then just kept it in my room after the season was over. As I opened the backpack you could see a little of everything that I owned. Stockings, Garters, Bras, Panties, and more. Even some fake boobs I had ordered off of the internet.

He stood there speechless, looking at me then at the backpack full of my things. I saw him swallow hard before he spoke. “So you just do this to get off right??”. “yes” I said as I nodded my head along. His next comment shocked me, “could I see you dressed up??”. A wave of fear and excitement came over my face and body. I had never been seen by anyone before, much less even told anyone about my dressing.

As I moved to the side of my bed, I picked out a pair of pink frilly bikini panties, A pink lace bra, and a pair of white stockings. As I made my way to the bathroom my heartrate jumped up quite a bit. For once I didn’t have to dream anymore, someone was going to see me for who I wanted to be… Ashley. Before I closed the bathroom door I said “Give me a few minutes ok??” He nodded and went to sit down on my bed. I closed the bathroom door and started to get undressed.

Taking off my pants and underwear, I pulled up my panties and tucked my tail behind me. I just loved the look of a female crotch on my body, and it was making me hot just by looking at it. I took off my shirt and put on my bra that I grabbed. Of course I can never forget my stockings which climb up my legs ever so sexily. As I started to exit the bathroom, I saw my moms ruby red lipstick sitting on the counter. I decided to try it, and put it on decently. I took a sheet of toliet paper like I saw my mom always do, and blot my lips.

As I opened the bathroom door, I told Jake to shut his eyes. As he did I walked into the room and sat down beside him on my bed. After taking a deep breath I said “Ok you can open them”. On those words Jake opened his eyes and saw Ashley for the first time. As he looked me up and down his jaw started to drop, and I could tell he was getting excited. “Speechless” I blurted out breaking his concentration. “No” he replied “but you are looking very sexy”.

Looking me up and down again he could tell I shaved everything, and how he didn’t notice before I’ll never know. He wanted to admire me more so he grabbed my hand and pulled me up to a standing position. He twirled me around like a ballerina, making sure to take in every inch of my body. As I had my back to him, he took his hand and placed it on my side and dragged it accross my back. This sent tingles down my spine, as Ashley got her first touches by a man, a real man.

This started to be a weekly thing between Jake and I. He would come over and I would dress up for him. We would touch each other, feel each other, and try the ever so risky kiss or make out session. As things started progressing more and more, He started calling me by my girl name “Ashley”. We went further and farther testing the limits. Untill one day I was caught completely off guard.

“Ashley, Would you give me a blowjob??” I was in utter shock, I wasn’t sure what to do. “I guess I could try” I said with a shaky voice. I made my was down to his shorts, kissing his chest and stomach on the way. As I undid his belt I started to get really nervous, but yet its like I knew what to do. I pulled his shorts to his knees and briefly stared at the bulge in his boxer briefs. Removing his underwear the scent of a male crotch hit me, it was so intoxicating.

Looking at his cock it was a nice thick 6 inches easy. Cut and wanting to be touched and sucked. As I grabbed his shaft with my right hand, I moved my mouth close to his head and licked it. Jake gasped and let out a relaxing sigh. I gathered more courage and licked around his head, making sure I took my time and soaked his throbing head. I continued further by dropping down to the base of his cock, and licking all the way up the shaft. I kept doing this untill his entire rod was soaked.

As I came back up to the head of his cock, Jake looked down at me in amazement. He knew what was about to happen, and he wanted it even more than I did. I opened my mouth and positioned myself over the top of his cock. Slowly I lowered my mouth and started sucking on his cock. A soft moan escaped his lips as he brought his hands to the back of my head. Sucking on his cock must have gotten him very excited, he was trying to push down my head too much and I started to gag.

I dug my fingernails into him and he relaxed again, allowing me to suck his cock normally. Trying to pick up my speed I heard the slurping sound I was making on his cock. That sound started to turn even me on, as I took my free hand down to my panties and to my tucked rod. Rubbing it, Touching it, and getting it harder. Hoping that I could cum in my panties, just like a real girl.

Sucking on his cock for 10 minutes, my jaw started hurting. Although his cock was swollen thick and ready to explode. “Ashley” jake said with a breathy voice “Let me cum in your mouth” I took my mouth off of his cock and smiled at him. “ok” I said to him keeping my eyes locked with his as I took his cock back inside my mouth. As I sucked further down his cock I started to turn my head from side to side. Making a corkscrew and swirling feeling on his cock. It didn’t take long for him to start moaning much louder as his orgasm approached.

I was continuously rubbing my crotch in hopes I might cum as well. Inside my panties just like a girl during her orgasm. As I approached my own orgasm I started trying to take his cock deeper in my mouth. Trying to make him cum harder than he ever imagined. Rubbing myself still I realized I was going to cum, I could feel it building it was just a matter of when. I removed my hand from my panties and brought it up to his rod. I reached both of my hands behind his ass and pulled him forward and pushed my head down onto his cock. Deepthroating a man for the first time.

As I pulled back to keep from choaking, I felt him explode in my mouth. Gush after Gush of hot sticky white sperm in my mouth. Filling my mouth completely, and giving me the shock of how much he just came. Realizing what was in my mouth, I opened it to show jake. I then closed my mouth and swallowed. It was a odd taste but I was sure to get used to it. Getting up I realized that the whole underside and ass of my panties was soaked from my own cum.

After we had relaxed on the bed, Jake got up and proceeded to get dressed. He gave me a kiss on the cheek and headed out the door. That night I wondered what he was thinking, about what had happened and what the status of “US” was.