Panty Boy 18byDawns©
I recently turned 18, the age when I could legally enter an adult only chat room. The web sight that I had been visiting for a year has rooms open to all ages. Now I wanted more. All ages chat about sports, rock music, and movies was becoming dull.
I'm a frail boy of 116 pounds, and very little muscle. Some would even say I look a lot like my sister. The head shape is an exact match and facial features are very close.
Maybe it's just my girlish features or perhaps a brain anomaly but I love to cross dress. I generally wear Jacquelyn's clothes. My sister is always happy to provide an outfit.
Jacquelyn had always been supportive. Maybe it was because she did wish I was her sister. Maybe it was just because I gave her nice gifts for her birthday and Christmas. In any case I felt gratitude for the support.
One evening, not too long ago, I went on the PC and logged into the site's adult chat section. I wanted to be dressed.
"Jackie, do you have anything I can wear. I'm going on line."
My sister nodded.
"I think I have something for you Stephen, and it would look very pretty on you."
She brought out for me a Covington belted silky stretch blouse in the colors orchid smoke, white, black.
"I love this!"
"You're welcome to it."
This is really awesome I thought.
"Should I wear some mascara?"
"I would," she replied, "with some earrings, and lipstick."
I put on the blouse, a pair of my own denim shorts since they fit better than hers and a pair of her high heal shoes.
"Stephen let me put some makeup on you. You'll really look pretty."
Jackie began applying her makeup to my face. She began with my eyes, applying eyeliner then red lipstick. She applied a base, brushed it out and a flesh tone make up. It all blended in.
"You look so pretty!"
In her clothing I could pass very easily. In fact so easily that I actually had gone out in public and was mistaken for female. At a high school dance during my senior year Todd James had asked me to dance. Since I am attracted to boys I accepted but then had to, for safety reasons, refuse him a date.
A chat room name change meant that I had to delete the existing program and reinstall. I did this and chose the screen name "Panty boy 18"
The first thing I did was make a profile that held nothing back. It read, "Panty boy 18, membership date October 11, 2007."
"I am a boy who loves to dress fem. I love to meet new people. Sex with that special guy would be great if it ever happens for me.
I love heavy metal blues music, movies, and a good book. I am 18 years old."
Recently I had the occasion to go out dressed. This time was really fun.
As it turned out I had been chatting with New York Boy since my first night on line. After four months of small talk he wanted to meet.
"That would be great."
Excited, I rushed to tell Jackie.
"He wants to meet me!"
"Really, who, where?" she replied.
"In the park. Should I go dressed? He 's bi."
" I think you should go dressed. He's never seen you in your boy clothes. Why start now?"
My preference for boys was something I could only admit while drag. Someday I might be more bold, more open I thought but not now.
Saturday afternoon was sunny and warm when I came out to Central Park and waited. I looked around at the scenery there. I knew how I would recognize him.
He came up that path that served sometimes as a dog walking trail. He was just what I expected to see, a guy five foot ten, wearing a Yankee ball cap.
He came walking along and called my name or at least the name I gave him in chat.
"Hello Stephanie," he said.
"Hi Mark," I replied happily.
He approached to hand reach distance.
"I think it's cool that you came dressed."
I giggled. He flirted placing his hand on my lower back. We walked and talked. We engaged in a friendly chat about movies, music, rock bands, sports. He talked about playing baseball and watching it. In my life time I had only watched it. I also enjoy figure skating and talked about that. We talked about his brother, my sister, his friends and my friends.
What was surprising was our apparent age difference. He looked to be close to thirty and I am 18. Still, I wanted to have sex with him.
I wore the Apostrophe 3/4 sleeve jeweled knit top, with slacks and Apostrophe Tress red shoes. Under the blouse there was a bra. I had on some C cup false breasts that I had just purchased at a cross dress specialty shop.
We had walked a few more feet then he took me in hs arms. He pulled me against his body. For the next several seconds as passions welled up inside me we kissed with open mouth.
"You look fucking hot in those clothes baby. You can be my bitch!"
Beautiful intelligent thing causing hard-on I thought. My own cock was starting to stiffen and throb.
"I would love to be your bitch."
We kissed again.
The chat moved on to deeper things.
"Have you ever been with a girl?"
"No," I said, "I prefer boys only."
He pulled me close again and again we french kissed. His hand went down to my buttocks and his other hand went to my crotch.
"We should go some place private."
"Name the place babe," he said.
"My bedroom," I answered.
Some time later in semi privacy of my bedroom I pulled off my top, the bra and my false breasts. He opened my slacks and pulled them down then pulled down my panties. His hand closed around my penis and my hand closed around his. My tongue slid across my upper lip then the lower lip as his member stiffened. Going to my knees I licked him from the head down to his large balls and back before closing my lips around his throbbing man meat. As my tongue continued to work him my lips slid slowly down the shaft. He moaned softly and whispered to me.
"Babe suck my big cock! Suck me!"
It was heaven. If heaven really exists this is it I thought. I lay on my side with one leg up over him as he pushed his cock inside me and hammered me with it. I moaned softly. The sensation was indescribable pleasure. My muscular friend continued hammering me with his cock for a few more minutes.
When he finally finished he rolled onto his back just to rest. I lay my head on his chest. Gently he placed his arm around my shoulder.