FIRST TIME FANTASY
comments, criticism, come-ons to ashleigh0@home.com
I'd always fantasized about making love with another cross-dresser. Someone young and slim and sexy. The thought of going down on a CD didn't really appeal to me but I desperately wanted someone to pop my cherry. Well, a few weeks ago I finally got my chance.
I suppose I'm more fortunate than most CD's in that I can indulge myself whenever I want, which is pretty much all the time. I work out of my home and only ever dress as a man when I have to meet with a customer which is only once every couple of weeks, the rest of the time, I'm Ashleigh. I look pretty good too, if I do say so myself. I'm tall (6'l"), slim (145 lbs), and have really long, thick hair. As long as I don't open my mouth I can pass most of the time, I've never really mastered the voice. The neighbors probably think I'm insane or a pervert or worse, but they're always polite to my face so they can think what they want.
Anyway, I get a body wax once every two months and the last time I left the salon it started to rain, and I mean pour! I'd parked barely thirty feet from the salon but by the time I was back in my car I was soaked right to the skin. I felt like a drowned rat. I checked my mirror and realised I looked more like a drowned Alice Cooper. I fixed my makeup as best as I could and headed off, looking forward to a nice warm bath when I got home.
About three blocks from the salon I noticed a thoroughly drenched figure standing at a bus stop. As I got closer I realised it was a young man who lived just down the road from me. I felt kind of sorry for him so I pulled over and wound the window down.
"Want a ride?" I asked.
He just stared at me for a second, shrugged his shoulders and got in. I guess he was trying to figure out if he was better off standing in the rain or getting a ride from the the local weirdo.
"My name's Ashleigh".
"I'm Steve" he mumbled.
"What were you doing out here Steve?"
"..at a job interview".
I could barely hear him. He was either really shy or really nervous about being in the same car as a cross-dresser. I didn't want to make him uncomfortable so I just left him alone.
I pulled up in front of his house and he was just about to get out when he turned to me and blurted out "I do that too". This could be interesting.
"You mean dress?" I asked.
"Yes. Sometimes I sneak my mother's clothes but I don't get the chance very often. Besides, she doesn't have many nice things."
I looked him over for a few seconds. He wasn't quite as tall as me, maybe a couple of inches shorter but he was just as slim. His jet black hair was hanging down just past his shoulders. I thought he'd probably look great as a girl.
"How old are you Steve?"
"Nineteen" he replied. (Perfect!)
"If you like, you could come over to my house tomorrow. I've got lots of clothes you could try on and I could do your hair and makeup for you"
He positivley lit up.
"Can you be there at noon Steve?"
"Yes! Definitely! Yes! I'll be there!"
"I'll see you tomorrow then", I drove home and immediately got into my nice, hot bath and drifted off imagining all of the possibilities tomorrow would offer.
I'd just put the finishing touches on my makeup and was trying to decide what to wear when the doorbell rang. I looked at the clock, 11:30, put on my robe and answered the door.
"You're a little early"
"Sorry, I can come back later if you'd like"
"No, no, as long as you're here we may as well get started"
I marched him up to the bathroom, started a bath and asked him if he'd shaved.
"Twice" he said "I want my face to be really smooth".
"I didn't mean your face, I meant your body"
"Do you shave your body hair?"
"I have my arms, legs, chest, and underarms waxed every couple of months, my facial hair was removed permanently a few years ago. I do shave my crotch myself though."
He blushed when I said that, but I did notice the razor disappear between his legs while he was in the bath. After a few minutes I told him to call me when he was done and went to get dressed. I really wasn't sure what to wear, I didn't want to look to provocative or obvious, but I wanted to look sexy, just in case. I tried on several things before deciding on a white blouse with a tiger print collar, a suede mini skirt, and a pair of thigh-high black stockings, perhaps not ultra-sexy but I definitely looked good.
By this time Steve was out of the bath and towelling off. I handed him a rectangular piece of fabric with two elastic loops attached to it,
"It's called a gaff, it prevents unladylike bulges"
"How do I put it on?"
"Step into the loops and pull it half way up your thighs, now with one hand pull your penis between legs and with your other hand pull the gaff up and sort of push your testicles up into their body cavities... here, let me help"
After we'd got him into the gaff I gave him a robe, sat him in front of the mirror, and put my hot rollers in his hair.
"We'll let those set while I do your makeup".
First a little foundation, then I started on his eyes. He had beautiful big, brown eyes and I really wanted to highlight them. I put some dark brown eyeshadow on the inner eyelid, some lighter shadow on the outer eyelid, and lighter still above then blended it together. A bit of mascara and eyeliner and I was looking into a pair of striking, seductive eyes. A touch of rouge and some dark, blackberry colored lipstick finished the job. I started to remove the rollers from his hair... I should say her hair because emerging before me was a beautiful young woman. I brushed the curls out a bit and used a bit of hairspray.
"Well, what do you think?"
"Wow, I can't believe how good I look!"
"What should I call you? Nobody this pretty could possibly be called Steve"
"I've always liked Jenny"
"OK then Jenny, come with me"
I took her by the hand and led her to my bedroom. I opened all my closets and drawers and told her to have at it.
It was like watching a kid in a candy store. At first all she was interested in was my lingerie, but pretty soon she was trying on dresses, skirts, blouses, everything except my jeans. After about an hour and a half she picked out an all red outfit. Red lace panties, red garter belt, red stockings, and a red dress that came down to her knees. She couldn't get the stockings quite straight so, sitting on the edge of the bed, I told her to stand with her back to me. I straightened her stockings and decided it was time to make my move. I slowly started to run my hands up and down her legs, she stiffened a bit but I was determined to give this my best shot. I stood up and ran my hands up her back and then over her shoulders, brushed her hair back and started lightly kissing her neck.
"Do you want me to stop?" I whispered in her ear.
Her response was to turn around and kiss me on the lips, softly, but leaving no doubt about her willingness. We sat down on the edge of the bed and started kissing again, this harder and deeper. Our mouths open, her hot little tongue darting in and out of my mouth and her hands running all over my body. I loved the feel of hands on my thighs, under my skirt. I'd never been so turned on in my life. I was hot, horny, and very impatient. I ran my hand under her dress and started rubbing her crotch as she moaned into my mouth. I pulled her panties and gaff down just far enough to release her cock. She hardened in my hand instantly. Reaching over to the dresser I grabbed a tube of KY jelly, squirted some in my hand, and started rubbing it all over her cock. I wanted her in me right now, unfortunately, she was so excited just lubing her up caused her to cum. She could see the disappointment in my face.
"Oh, Ashleigh, I'm so sorry, I'm..."
I silenced her with a kiss.
"Don't worry honey, we've got all day"
We lay down on the bed and started kissing again, lightly at first, but soon we were locked in a passionate french kiss. Suddenly, Jenny broke off our kiss. I let out a moan of disappointment. I wasn't disappointed for long. She started kissing my neck and then kissed her way down my chest, unbuttoning my blouse as she went. She spent quite a bit of time kissing, sucking, and gently biting my nipples before she kissed her way down to my belly button and pushed up my skirt. First, she lightly kissed my upper thighs, then my panty-clad crotch, then pulled my panties and gaff right off and laid little kisses along the length of my shaft. She then took some KY jelly and rubbed it into my ass and then slid a finger into me and took my cock in her mouth. As her mouth moved up and down my cock, her tongue slid the length of my shaft and her finger pumped in and out of me. Then there was a second finger, and soon a third. The sensation of her fingers pumping in and out of me and of her hot little mouth sucking my cock sent me over the edge and I exploded into her mouth with the most intense orgasm of my life. I lay back, panting and sweating but she wasn't finished. She put some more lube on her cock and then on my ass, raised my ass a bit, and slid into me. It was a little uncomfortable at first, but her fingers had loosened me up and soon the sensation of her cock caresssing me from inside had me hard again. I wrapped my legs around her and pulled her into me, harder with every thrust, squeezing her cock tight with my ass muscles. She came with a loud moan, a moan from both of us, the feel of her hot load shooting into me was ecstasy. Still inside me, she grabbed my cock and pulled me to my second orgasm and lay down on top of me. She kissed me deeply for a while and then her hand wandered down to my crotch,
"So," Jenny asked, "What do you want to do now?"