For as long as I can remember, I have always been drawn to wearing women's clothing. When I was 4 years old, my mother would take me shopping and I would throw tantrums if my she didn't take me to look at the girls clothes too. I would try on pants but only on one condition: I got to look at the dresses when we were done!
When I was 5 years old, I wanted to be Princess Leila for Halloween. My mother thought it was adorable and was more than happy to buy me the costume. The following year, I was Snow White. Crossdressing for Halloween became a lifelong tradition.
When I was 8, my mother took me to a Thanksgiving parade. It was cold and I wanted to leave, but my mother wanted me to see Santa Claus in the parade. I was wearing a sweater and pants, but my mother was wearing a short skirt. I was freezing and I couldn't understand how my mother wasn't cold. I asked her and she said that her pantyhose kept her warm. "Pantyhose, eh?" I thought. For 6 years, this was my little secret...until...
I was 14 years old and my family had gone to visit family members in a nearby state. I had two female cousins...Caitlin, who was 16 and Kayla, who was 14. It was a Friday night, around 10 pm, and Caitlin was getting ready to sneak out of the house for a date. Kayla and I watched as she plastered her face with makeup. Her blouse was so tight and low that her little breasts were practically bursting out of her top! And her skirt was scandalously short :-)
She left, leaving Kayla and I alone. Kayla was angry at her sister because her parents had told her (Kayla) that she wasn't old enough to wear makeup. So we got into her sister's makeup and she started playing dress up. She said that it was hard to paint her own face and asked if she could practice applying the makeup on my face. She painted me up...and I looked like a street-walking whore! I told her that, since I had let her paint my face, now I got to paint hers. When I was done with her, she looked even sluttier than me!
Then we started putting on Caitlin's clothes. Kayla took off her shirt and quickly pulled on one of Caitlin's tops but before she did, I managed to get a glimpse of her training bra :-) She took off her pants and quickly pulled up a skirt. Then she put on a pair of suntan pantyhose. Then, she told me it was my turn!
I took off my shirt and Kayla helped my get into a dress. Once the dress was on, Kayla reached her hands under my skirt, and pulled my pants down. To my surprise, she grabbed my underwear and pulled them, along with my pants, down in one smooth motion! I was incredibly aroused and had a raging hard-on and was trying to hide it from Kayla. But she pulled the black pantyhose up my legs, she was soon face to face with what I could not hide :-)
She took out some of Caitlin's shoes and she pulled out the two pair with the highest heels. We both put on a pair and practiced walking in heels. Then Kayla said, "You know what we should do?...Drink tequila!" The girls' room was in the basement of the house and the parents, and the guest room that my parents were staying in, were upstairs. Kayla took off her heels and left. She came back with a bottle. We each took a swig and started talking. Kayla told me that she had only kissed one person. I told her that I had never been kissed. We each took another swig. Things get blurry, but Kayla and I began kissing each other. I had been erect for almost 2 hours and was on the verge of cumming...and she hadn't even touched my penis! When Kayla asked me if I knew what a French kiss was, things got really wild :-)
Caitlin had become a master at sneaking in and out of the house and while Kayla and I explored each others mouths with our tongues, the door quietly opened and we both heard three words..."What the fuck?" It was Caitlin, and we had been caught red handed! Kayla immediately started crying and begging Caitlin not to tell their parents. Caitlin made us both stand up. She just looked at us for a minute. She approached me and lifted up my skirt to reveal my erect penis under my pantyhose. "Just as I thought," she said with a smile. She got down on her knees, looked at her sister and said, "Come here." Kayla kneeled next to her sister as Caitlin pulled down my pantyhose and began stroking my cock. All I can say...is OMG! After a few strokes, Kayla said, "Can I try?" Caitlin took my shaft into her mouth and Kayla started licking my balls. I didn't last long and blew my wad all over my stomach. Caitlin told Kayla that if she wanted big boobs, she needed to lick up as much cum as she could while she was still developing. Both girls greedily lapped up every drop from my stomach ;-)
While that had been the most amazing and exhilarating experience in my life up to that point, it was only the second night of a seven-day visit with my cousins. And it only got better!
