This is a true story of my first experience with a man. It happened not so very long ago and was one of the most amazing nights of my life. The names have been changed to protect the innocent.
I am a very shy, tall (6' +), slim man with a less than masculine build. I have enjoyed experimenting with women's clothing for the better part of my life, and have often had very vivid fantasies involving my feminized self and very masculine, if not downright hunky men! However, I am getting a little ahead of myself and really should give you a little background...
I had a fairly normal upbringing, nothing too out of the ordinary. I grew up in the suburbs of a medium sized city in Alabama; nice family, a loving mom and dad, an older brother and a younger sister. Our neighborhood was quite nice, friendly people, I had plenty of friends, played all the usual sports that growing boys play, had a part-time job, all the normal things one might expect from a suburban upbringing in the late 20th century.
During high school and college, I dated several girls and enjoyed my fair share of sex like most other guys my age. You might say that I was the All-American Male, except for one minor detail. I had a proclivity for wearing women's clothing, anything soft and silky, sheer and pretty was a huge turn-on for me. Like most young and budding crossdresser's I couldn't get enough of pretty, sexy panties, pantyhose, stockings, slips, bras, skirts, etc., you name it and I wanted it to feel it against my body. The feelings associated with dressing in something feminine was absolutely divine, and anytime I could get a few moments alone I was dressing up and feeling sexy. Typically these little forays with my girlie self concluded with a little clitty teasing that were ripe with fantasies of sex with cute boys or handsome men until I would erupt with torrents of warm, gooey cum all over my belly and chest.
Also, like many young crossdressers, especially us GRITS (Girlie-boys Raised in the South) by relatively religious parents, I would go through periods where I felt terrible guilt (due to my faggot desires) and purge whatever small stash of pretty, feminine attire I might have accumulated. I also had my fair share of "close calls" when someone would come home unexpectedly and nearly catch me being a cute little sissy!
When I went away to college I had a little more freedom to explore my desires to be a girl, but still not what I would have liked - since I did chose a southern university where a lot of people I grew up with attended. When I did find the time it was bliss!
Right after college I met and fell in love with the woman I would marry. We were very happy for a short time, and then she decided to play the field a little too carelessly and I found out. We tried to work things out, but to no avail and after four years we divorced. While I didn't completely stop dressing during our time together I could count on one hand the number of times I was really able to bring Jenna out.
Shortly after our divorce, once again living in my hometown city I began to amass a beautiful feminine wardrobe, and every night I would get home from work let Jenna out of her closet, so to speak, and be free to pursue my feminine desires. I still had friends but found myself wanting to spend more and more time alone - as Jenna. Also, my fantasies involving a very feminized me, and a really cute guy intensified.
At this time I also started seeking others with similar interests via the internet, both other girls like me and our admirers. And this brings me current in the story. One night I met a man named Charlie in a local chat room online. We hit it off really well, and he knew just what to say to make me feel pretty and wanted. After several weeks of chatting and several pictures had been swapped, Charlie told me would like to get together. This was what I had been waiting for, a man that wanted me as Jenna! I was extremely flattered, but also very nervous, I knew I didn't want to give out my locale just in case he wanted more than I could give. Well, Charlie solved that dilemma by inviting me over to his place, but he said I had to arrive as Jenna! What I get pulled over on the drive over? What if my car breaks down? What if someone reads me?
Charlie assured me that everything would be okay, nothing would happen and no one would discover my secret since I am quite passable as long as I am sitting down. Once I stand up, however, it is easy to tell what I am - a sissy boy! We finally agreed on a Friday night that was convenient to the both of us, and Charlie asked me to wear something special for our first night.
Finally, after what seemed like forever the day finally arrived. I left work a little early because I wanted everything to be perfect. On the way home I stopped by the mall and did a little last minute shopping. I bought some more foundation - MAC, a girlie's best friend, A bottle of BEAUTIFUL perfume (my ex-wife's favorite - go figure!), and a bra and panty set complete with garter belt and stockings from Victoria's Secret, all in virginal white. I went home unloaded the car and went inside to get ready.
I took a long hot bubble bath and shaved everywhere, except for a cute little patch of trimmed hair just above my clitty. I soaked in the tub for a quite a while to allow my skin to become as soft as possible and then put a nice creamy cocoa butter lotion on all over. I put on a cute little kimono and began to get ready. First I did my makeup, foundation powder, a little pink blush, lavender, pink and silver shadow, full thick (FAKE!) lashes, a pretty, soft pink lipstick with two coats of shiny lip gloss and voila! My face was ready, next I donned a shoulder length brunette wig (my natural color). And when I looked at the completed product in the mirror I was very satisfied.
Next I painted my toes with two coats of pink polish to match my lips, then came the silky, shimmery thigh-hi stockings, donned the gorgeous white garter-belt and attached the garters. I slid into the delicious satin Body By Victoria boyshorts (seemed rather fitting - giggle), fastened the matching Body By Victoria full coverage bra and inserted my very realistic breast forms and the foundation was complete. I had chosen a gorgeous pink chiffon dress that fell to just above the knee, it had cute puffy sleeves and pretty ruffled trim. I sat back down at my bureau and attached my nails and applied another two coats of the same pretty pink polish as my toes. I chose simple jewelry a dainty chain with heart shaped pendant for my neck, a pretty heart shaped watch and a simple silver chain for my other wrist, a couple of rings and I was almost ready. I slipped my feet into a pair of beautiful, pink anklewrap sandals with a four inch heel (nothing quite like a tall girl!), applied my new perfume to all the right places and I was feeling sexier than I ever had before. I slipped a few essentials into a cute pink clutch, packed a little maribou trimmed babydoll, with a few day clothes (who knows, right girls?) and I was ready for my destiny!
I called Charlie when I was ready and told him I would be right over, he told me the door would be unlocked and to just come right in. With trepidation I went into my garage, climbed into my car and hit the electric door opener. I backed nervously out of my drive and started the journey to Charlie's house and my first night as a true sissy!
When I got to Charlie's I took a few deep breaths, slid my legs out of the car and stood up, the butterfly's in my tummy were unbelievable. I minced my way up his walk, placed my pretty hand on the door knob and opened his front door. Charlie greeted me in the hallway with a dozen yellow roses and a sweet hug. Now, Charlie is considerably shorter than I, especially in my four inch heels and I absolutely LOVED it!
"WOW! You are gorgeous!," Charlie said.
"Blushingly, I replied, "Thank you, you are rather dashing yourself!"
He led me into his den and poured us both a glass of wine. "To a wonderful evening!" Charlie toasted.
We drank several glasses of wine, and talked for quite a while. We talked about my desires, the fact that I had never been with a man and Charlie told me how honored he was to be my first. He was such a gentlemen and felt very relaxed, he ordered in some Chinese food and we ate. After dinner while drinking more wine, Charlie put on some soft music and we snuggled up with one another on the couch. When Charlie finally kissed me it was the most electric moment of my life. His strong lips pressing against mine, his tongue pushing its way into my mouth, me willingly succumbing to him, while emitting a soft, feminine moan. I knew I would give myself to him this night, and I could not wait.
Charlie rose and led me into his bedroom, it was very simple and very masculine and felt like the most appropriate place in the world for me to finally become a sissy. Charlie removed his shirt and I got my first look and his hairy and very manly paunch. Next Charlie removed his shoes and socks but left his pants on!
"You will have to take off everything else to get at what you want," he teased.
Smiling I knelt before him, running my hands all over his chest and stomach. I leaned forward and kissed him on his stomach, basking in his scent. I lowered myself onto my bottom, with my legs to one side and ran my hands down his stomach and over the bulge in his pants.
"Mmmmmmmm," I moaned.
"Do you like that?" he asked.
"It feels wonderful," I replied, smiling up at him and licking my lips.
I undid his belt and pants button, then slowly slid the zipper down. I pushed his pants to the floor and helped Charlie step out of them. There he stood his masculine hairy legs and stomach framed his white cotton briefs. He looked good enough to eat and that is exactly what I intended to do! Leaning forward I went to kiss his bulge, when he moved just out of reach.
Smiling at me he said, "Look at you! A sissy boy desperate to get at my cock! Do you feel like a little faggot, Jenna?"
"Oh yes!" I cooed, "I am a little sissy, faggot and I so badly want your cock!"
"Kiss it!: he demanded. Which I readily did. Would you like to set it free, I nodded my head yes, moaning with desire, as he instructed me slide his briefs down his hairy thighs. I did as instructed and then asked if I could touch it.
"Of course, baby," Charlie smiled. Wrapping my fingers around his hard, 7.5 inch cock was electrifying. "What would you like now, Jenna?"
"Mmmmmmm, I wanna be a cocksucker!" I moaned, as I leaned in a flicked my tongue across the head of his cock.
"Oh, Jenna, " Charlie admonished, "You've always been a cocksucker, you just never had a cock before. You were meant to be a little sissy and you realize that, you weren't made into a faggot, you were born a faggot."
I stared into his eyes, mesmerized as his cock rubbed against my lips. " A real man would never dress the way you do and beg to be a cocksucker. Only a little prissy fairy would act like you, now open your mouth and welcome what a man like myself has to offer you, Jenna." I willingly parted my lips and allowed Charlie to slide his cock into my mouth.
"Mmmmmm, that's feels so good baby, you like it don't you?" I nodded my agreement unable to speak with my mouth so full. "This first time will be pretty quick Jenna because I have been saving myself for you tonight. But we will have plenty of time for you to get me hard and have sex all night long, ok?"
Whimpering with delight I shook my head yes. Charlie pulled his cock out of my mouth and began to stroke himself. "Would you like for me to cum for you? Cum on you?" Charlie inquired.
"Oh yes baby! Cum for Jenna! Cum on Jenna! I want to feel your hot, gooey load! I want to taste you!" I screamed.
After a few more strokes Charlie's cock began to twitch and then thick, globs of cum shot out from the slit, splashing onto my tongue, up my nose, across my cheeks and chin. "Mmmmmmmmm!" I groaned.
"You like that baby? Are you a real cocksucking faggot, now?" Charlie teased as he rubbed his cock on my face smearing his cum everywhere.
"Oh, yeah baby! I'm your cocksucking, cum eating, little sissy!" I cooed.
Smiling down at me Charlie exclaimed, "I can't wait to take your virgin ass in just a little while!"
I smiled and moaned, wagging my pantied bottom in anticipation of my imminent deflowering by this gorgeous man!
If you like the story so far, please email at mailto:jenna_shannon2003@yahoo.com and I will tell you about my first foray into anal sex, and take you to where I am today.
Huggs!
Jenna