For as long as I can remember I've enjoyed dressing up in girls clothing and putting on make-up. When I was just a little boy, I started out by clomping around the house in my mother's heels and slinging her purse over my shoulder. Everyone thought it was cute and just a phase I was going through.
When I got a little older, around eleven or twelve I'd sneak into the bathroom and try on my mom's panties and bras and make myself up with lipstick and eye shadow. Sometimes I'd even give myself a beauty mark with mom's eyebrow pencil. I must have spent hours posing in front of the bathroom mirror dressed like that. I experienced my very first erections standing there.
Of course I was always worried about being caught and eventually I was, but not by my parents. My parents always reserved Saturdays as a "date night" and so they'd leave early and stay out late, sometimes not returning home til 3 or 4 a.m. On these occasions they'd hire my mother's nephew Ryan to babysit. He was a freshman at the local community college and incredibly good looking with jet black hair, clear blue eyes and a leanly muscled athletic physique.
I had a crush on Ryan and was always happy to see him pull up in his little AMC Pacer and climb out with his school work stuffed in a ratty old bookbag. Once mom would leave he'd usually spend time playing board games or video games with me and my younger sibs, then make us something for dinner and finally put the younger kids to bed before settling down to his school work while I got to stay awake an extra hour or two (or three if he was really engrossed in his studies and forgot about me).
I'd heard my parents talking about him once. It was night and I was in bed lying awake while they chatted in their own bedroom beside my own. My mom was wondering why a handsome young guy like Ryan never seemed to have a girlfriend. My dad suggested maybe he was queer. Mom scoffed at the notion and said maybe Ryan was just shy. And he was shy around most people, but never around us kids. In fact, kids were the only people Ryan seemed comfortable around. He could open up and just be himself around us. That was part of the reason I thought he was so neat.
So the night came my parents went out on their date and we were left home with Ryan. We did the usual stuff and pretty soon my little brother and sister were tucked into their beds and sleeping. Ryan clicked on the tv since for once he didn't have a lot of homework and told me I could stay up an hour or so. The show he was watching didn't really interest me, but sitting so close to him on the couch in the dark was making me horny. I could feel myself getting hard so I excused myself and went upstairs where both my and my parents bedrooms were. I snuck into mom's dresser and helped myself to her black lace panties, a matching bra and a pair of her sheer black pantyhose and an extra pair of black heels. Then I took her makeup kit and a bottle of her Jovan white musk perfume and went to the bathroom. Pretty soon I was out of my jeans and t-shirt and dressed in her underwear, with my face dolled up in blackcherry lipstick, a complimentary shade of eyeshadow and I even combed and brushed out my hair in a more girlish style. The illusion was complete. I'd been so wrapped up in the process I never heard the stairs creak or the bathroom door open.
"You look amazing."
I nearly jumped out of my skin at the sound of Ryan's voice.
I turned and stared at him leaning in the doorway watching me and paled. "I....I..." I stammered.
He quickly held up both hands. "No, it's ok really. I won't tell anybody."
I stood there, not knowing what to say flooded by emotions. I was embarrassed to have been caught, turned on still from my previous fantasies (and it showed, my mother's panties couldn't hide my very erect cock), and also happy that Ryan was seeing me - the real me, and not the person he babysat every weekend.
"It's ok really," he said in a soothing voice. "I think you're beautiful."
I felt warmth flush through my face and neck. "Really????????"
He nodded. "Absolutely."
I felt a small shy smile touch my lips. "Thanks."
"Turn around," he smiled back. "Let me get a good look at you."
I really did smile then and did a couple of turns.
He made a satisfied sound, almost an "Mmmm."
"Do you really like how I look????????," I asked. "You don't think I'm a freak????????"
"I really like you," he said. "No, I don't think your a freak. I think your really fucking hot."
I laughed, then "I really like you too."
He walked into the room, shut the door behind him and came to me. He caressed my face with one hand and then leaned down and kissed me on the lips. My cock started throbbing.
When he pulled away he looked me in the eye. "Want to make out????????"
"Yes," I sighed, still lingering on the sensations that kiss had produced.
"Let's go to your room," he said. "Privacy."
We gathered up my jeans and shirt and went to my bedroom where we locked the door. Ryan told me to get into bed and I did. I watched him remove his shirt, staring at his toned abs and flexing pectorals. There was a thin line of dark hair - a happy trail just below his naval, descending below his belt line. He kicked his shoes off and then peeled off his jeans. Although he kept his tidy whities on the bulge of his enormous cock was unmistakable. I guess my eyes must have widened or I stared a little too hard. He laughed and looked down.
"You like????????"
I nodded. "Can I see it????????"
He pulled his underwear down and showed me his cock. It was beautiful. I wanted to touch it, to rub my own against it. But these desires I kept to myself. He pulled his shorts back up and climbed into bed with me. We didn't have much room I only had a little twin sized mattress.
He pushed me back against the bed sheets and kissed me again, this time slipping his tongue into my mouth. I felt it probing around and sliding over and around my own tongue. I felt his hands run over my body and slip underneath the bra I wore. His thumb worked little circles over my nipple and I moaned the same way I heard my mother moan when she and my dad had sex at night and we kids were supposed to be asleep. Ryan began kissing, licking and nibbling on my throat, shoulders and collarbone and talking to me in a husky voice.
"Oh baby your so fucking hot, I want you so bad..."
He unsnapped the bra and flung it aside and began licking and sucking on my nipples, then pulling them almost painfully with his teeth. My cock was so hard it felt as if the skin would split it it got any harder. He worked his way down, planting little kisses on my stomach and licking and sucking on my naval as if it were a vagina. Finally, he pulled down my panties and hose and started sucking my cock hungrily. This time I really did groan, I couldn't help myself. I closed my eyes and arched my back slightly while his head bobbed up and down. I exploded inside his mouth, little tremors rocking my body for several seconds afterwards. I finally relaxed and turned to jelly. He rose and swallowed my cum and then pulled the hose and panties completely off of me. He then removed his own underwear.
"I want to fuck you," he said. "Is it ok????????"
I nodded yes.
"It might hurt a little," he told me. "First time always does. You ok with that????????"
I nodded again. At this point I didn't want anything to get in the way of our sex.
He smiled. "Good. I'll be right back, wait here."
He got up, threw his jeans back on and disappeared down the hall for a few minutes. When he returned he had a bottle of baby oil. He locked the door, kicked back out of his jeans and got back into bed. He slicked up a finger with oil and turned me over on my belly. I felt his finger slide slowly into my ass and work itself in and out several times, loosening me up. It felt good. I smiled.
"Here."
He handed me a wadded up sock.
"Bite on that if you have to."
I stuffed it into my mouth wondering if it'd really hurt that bad???????? Despite a growing sense of panic I was still much too turned on to want to stop. Behind me Ryan slathered oil all over his cock and then he climbed into position on top of me and slowly worked his cock inside of me.
I grunted and groaned and squeezed my eyes shut. He was big and it did hurt, a lot - but it also felt great. As he slid in and out of me and called me baby and leaned down to nuzzle my neck and kiss my shoulders and back I felt special, like I belonged entirely to Ryan. I wanted to belong to him. When he came inside of me, I wanted to exist in that moment of time forever.
But it wasn't to be.
Apparently the sex made Ryan feel awkward about returning and the very next weekend he made an excuse to not babysit, so a neighbor girl took over the job. And before long Ryan moved away completely (and to this day won't have a thing to do with me). I'm now the same age Ryan was then and a freshman in college. I still enjoy cross dressing at home in private, but like my cousin before me I've become a shy book wormish student who doesn't really register on the radar of either the guys or girls in class. My sex life consists primarily of masturbation and lots of Internet porn, but I'll always have the memories of that one night.