My name is Gayle. As you have probably surmised, I am a crossdresser. I have been dressing since I was little, beginning like so many others, by wearing my mother's panties. Over the years I progressed to my own wardrobe and began wearing makeup as well. Being tall at 5'11" I never thought I could "pass", but I always dreamed of the day I could go out in public.
Having grown up in the `60's I had grown my hair long. Much of the time it was below my shoulders and gave me a very feminine appearance when I would dress. For the longest time I wanted to know what it would be like to be with a man and be treated fully as a woman. I longed to experience all those things I had missed in high school...the dating, the making out in my boyfriend's car, you know, all the usual girl stuff.
By the time I was 21 I had discovered the wonders of the adult bookstore in my area. It afforded me a place to buy all the TV magazines I wanted and in those I found the classifieds. Through the ads I was able to contact admirer's and other "girls". I also found I could anonymously enjoy a stiff cock in my mouth now and then without the fear I had of a face to face meeting. What a glorious invention was the "Glory Hole".
Although I corresponded with many and fully intended to meet in person I always got cold feet. "What if" stopped me. What if it was someone I knew, what if someone saw me, and of course ... what if I liked it!
Some years later I happened back to that bookstore. I was wearing lingerie under my jeans and shirt as I did frequently. As chance would have it I wandered into this particular movie booth and there it was...scrawled on the wall above the coin slot. "Do you TV? Tall, mature man will treat you right...call...555-9145". Why I wrote that down I don't know, why I actually called I don't think I will ever know...but I did. Stranger yet was that I actually dialed the number the next day.
"This is Hank" the voice said..."I'm Gayle and I saw your ad on the wall at the bookstore" I said.
"Are you a TV?". "Yes, I am, but I have never met anyone and I'm really nervous" "...Don't be, I won't hurt you". Yeah sure, where have I heard that before I thought..."well, what are you looking for Hank" I said feigning confidence. "Just a pretty girl to treat right and have fun with, does that interest you Gayle?" I stammered yes and we proceeded to talk for about 20 minutes. Near the end we arranged to me in person and talk and see where things would go. While I had every intention of meeting him, I also knew my history of breaking such dates and that this would most likely be another in that string...but I made the date anyway.
A week flew by and suddenly it was do or die.
I underdressed as usual and drove to the appointed spot. I saw someone matching the description he had given me waiting by the fountain. Hank had said he was tall and that he was. At about 6'5" he was just what I had hoped for, someone who I could look up to even as I stood in my 3" heels. I walked towards him and said, "Hank?"...shaking all the while. "Gayle?" he responded. I quickly looked about to see if anyone had heard him call me by a girl's name. No one was there and I answered yes. He sat on the bench and motioned for me to join him. I did so, close enough to have a quiet conversation and not be overheard, but far enough away for my own security.
"I'm glad you came. Don't be nervous." "That's easier said than done, Hank, this is my first time meeting someone in person". Small talk ensued and as time went by I became more relaxed and at ease with him and my new situation. "Did you wear anything pretty for me today?" "Well, sort of. I'm wearing a white lace bra/panty set with nude thi-hi stockings. I wanted to feel more feminine since I wasn't completely dressed" "Mmm, I wish I could see them" he said as he shifted his position. I thought I could see a bulge growing in his trousers, but I was afraid to look directly to be sure. "It's a bit open here for that" I giggled. "And besides, I would prefer to be completely dressed before we got to that point" That's when I got the surprise of my life... "I have a room at the hotel over there, did you bring your things with you? We could go there, you could change and we could get to know each other better!" Before I could think I nearly shouted out "Yes!". Then I turned bright red and knew the time had come for me. Hank handed me a room key... "How much time do you need to make yourself pretty?" "About 45 minutes, maybe less" "I'll go to the lounge and have a drink while you take your time and I'll be up in an hour. Now go get your clothes and enjoy yourself"
Off I went, nervous as hell, but excited, anxious and horny all at the same time. This was to be my debut. Someone would finally see Gayle...and I would probably lose my virginity!
Gathering the suitcase from my car I headed to the entrance and up to the 3rd floor. Room 327 ... I'll never forget that number. As the door opened I saw it was a suite, not just a single room. I was impressed that he would go to all this expense for someone he'd never met. I locked the door and put my case on the king size bed. Taking a deep breath I opened my bag and began to undress, putting my male things in the closet and beginning my selection. First I attached my breast forms and repositioned my bra, then I put my hair in a pony tail and rummaged through my makeup case, then it was off to the bathroom. A quick rinse of my face followed by foundation, shadow, mascara, blush and eyeliner did the trick. I slipped into a rose colored ¾ sleeve blouse with covered buttons and a black A-line skirt. Then I chose my black sling backs with 3" heels. Grabbing my brush and lipstick I returned to the bathroom to finish.
It wasn't 2 minutes after that there came a knock on the door. Glancing through the peep hole I saw it was Hank and I slowly opened it to let him in. As he entered he was looking me up and down the entire time and smiling. This made me tingle and I returned his smile demurely. "You're very pretty Gayle" "You're too kind Hank" I returned, blushing. "Come in, after all, it is your room" I giggled... "Let me look at you" he said, taking my hand gently and urging me to turn for his viewing pleasure. "I'm glad you decided to come today and meet me, you look lovely" "Thank you kind sir" I responded and blushed profusely, "I'm so glad you find me attractive".
No sooner had I said that when Hank gently urged me towards him and took me in his arms. Smiling, he held me close and slowly brought his lips to mine. My first kiss with a man and I was already melting in his arms and pushing stiffly at my panties. I was getting so hot...why had I waited all this time to experience this? His lips parted and his tongue pushed against mine which opened in response. His tongue probed my mouth and danced with mine. My breath quickened and my arms tightened around his neck.
It seemed like an hour but it was only a minute and he pulled slightly back. My lips still parted, my breasts heaving and my face flushed all told the tale. I was burning with desire for this man, and he knew it! Hank kissed me again and as his tongue stabbed my mouth I dreamed of his cock invading my virgin pussy. His hands wandered and soon one cupped the right cheek of my behind, kneading the soft flesh while the other stroked my side and teased my left breast. My fingers stroked the back of his neck and urged his kiss to linger. Soon my moaning betrayed me and I began to kiss him harder and press my body to his.
His left hand slipped beneath my skirt and was caressing my panty covered ass, his fingers slipping under the leg band and teasing the head of my dripping clit making me ooze even more. Hank began to unbutton my blouse and touch my bare flesh. His lips grazed across my neck and the tops of my swelling breasts. I pulled his head back to me and kissed him voraciously as my hands unbuttoned his shirt and forced it off his shoulders. I kissed his hairy chest and toyed with his nipples. As he unzipped my skirt I reached for his belt, unfastened it and my skirt dropped around my ankles. My blouse fell to the floor as I kicked free of my skirt and stood before my man in my sexiest lingerie and heels. Strangely I wasn't embarrassed but I was filled with a feeling of femininity I had never experienced before. I was his WOMAN! It was my dream come true!
I kissed Hank again and my fingers fumbled with his zipper. I could feel his hardness and his length and became scared. Shortly this man would make me a woman and take my virginity. I felt like it was my wedding night.
Slowly I sank to my knees before him. The snap of his trousers opened and down they came revealing the outline of his manhood beneath his white jockeys. While not very sexy, it was extremely sensual for me. I leaned forward and planted kisses along it's length through the cotton. Traces of my lipstick outlined the object of my desire. Then at last I removed his shorts and saw it up close. Pressing it to his belly I tickled his balls with the tip of my tongue and then worked my way up to the swollen head. Parting my lips I took it in my mouth and savored my lover's taste and smell. It was a heady moment and I was lost in the act of sucking Hank deeply into my mouth. My lips closed tightly and pressed the soft flesh as it slid out then in again. Yes, this is what I longed for! This is what I needed! In and out it moved as I bobbed my head, all the while cupping is swollen sack and teasing the region behind them with my fingertip. I sucked the knob and flicked at the piss hole with my tongue. Soon, I hoped, it would open wide and flood my mouth with the delicious juice I loved.
Suddenly his hands grasped my arms and he had me stand. I kept stroking as he kissed me wildly. He pushed me back on the bed, my legs falling open with him between them. My panties slid down my thighs easily and my excitement sprang into view. Hank wasted no time slipping me into his mouth and raising my legs onto his shoulders. I felt a fingertip trace the outline of my pussy hole, then slowly probe me as his mouth descended on my clit. The invader searched and then left, only to return with a companion. He was making me wet and open for his cock. His lips left my clit and found my hole. A wet tongue replaced the fingers that had pleasured me and I squirmed beneath his licking. I had never had my pussy eaten and I wondered why I had waited so long for this delicious bit of sex. As he licked at me I reveled in all the sensations I was feeling, the heaving of my breasts, my nylon encased legs on his shoulders, his fingers and tongue teasing and probing. I was in heaven! My entire body felt alive and so feminine.
Lowering my legs as he pulled back Hank turned me onto my stomach and told me to get on all fours. I did as instructed and he parted my cheeks and again licked my pussy. This time his hand encircled my hardness and stroked me. I was dripping wet and aching to be taken by this man and I told him so.
"Put it in me, fuck me Hank! Take me now and make me your woman."
He knelt on the bed behind me and rubbed his cock around my opening, teasing me more. Then I felt the head press at my hole and I relaxed as best I could. Slowly, oh so slowly, the head slipped into my cunt. I gasped! He inched his rod deeper and I felt it rub my prostate and I almost came. A few inches in then he pulled back and inched forward again. I wanted it all and after a few minutes of teasing I pushed back as he began a new assault and buried him inside me. His balls slapped my cheeks as I wiggled try to get more in me.
At last I was a virgin no longer. Every second he remained in me made me more wanton. I was lost in the sensations of sex. I began my "pole dance" and his hands grasped my hips to control my movements. He pulled out till only the head remained in me and the jammed it all back inside. Then he'd pull out and rub his length between my cheeks and ram it back inside. Varying his pace he was driving me wild. I was dripping everywhere, I wanted to cum, I needed to cum. Most of all I wanted him to cum inside me. I wanted my first cream pie. I wanted to sleep in the wet spot of this man. I found myself wishing I could become pregnant from his seed.
Suddenly he pulled out, leaving me empty and begging for his cock. He flipped me over and again my ankles were on his shoulders and he mercilessly rammed his length into me. This was it...I could feel it. He was kissing me ferociously all the while fucking me with abandon. My ass humped in rhythm to his thrusts and my stiff clit rubbed against his hairy belly That was all it took and I almost passed out as wave after wave of orgasm swept through my body. I came as never before and felt as if my entire being was being pumped through that tiny opening. Hank kept slamming his cock into me.
He slipped his hand between us and scooped up my juices then brought it to my mouth. He smeared some on my lips and the rest on my face. Grunting loudly as he watched me clean his sticky fingers Hank thrust into me in hard short jabs and I knew he was shooting his load deep in me. I felt the warmth of his seed against my inner walls and I fainted away.
When I came around shortly after, I felt his hot cum dripping from me. I touched my pussy with a fingertip, scooped some up and brought it to my lips. At last I tasted him. Hank came up beside me and offered me his cum covered dick which I greedily sucked and licked clean. He tasted so good and I felt incredible. The acrid taste of our juices was on my tongue and the drying remains of our mating coated my face. Hank was beside me. I turned to him and he kissed me tenderly. We cuddled and drifted off to a short nap.
I awoke first and slowly as not to wake him I slid down the bed. His flaccid cock was too inviting and I took it into my mouth. I wanted to see if I could make him hard again while he was asleep. Sucking and licking I began to get a response. Soon he was nearly hard and that must have been what woke him. Looking down at me he smiled and said, "You really love that cock don't you Gayle?". Mmmmm was all the response I gave as I kept sucking and now taking his full length down my throat. His hands went between my legs and found my clit...then he urged me over him in a sweet 69. We stayed that way for quite some time until I pulled away, turned and straddled him. Grasping his member I guided the head to my pussy and impaled myself on that wonderful shaft.
I slowly worked my magic and we were both entranced. My hands caressed his strong chest and his grasped my hips helping my movements. After a bit he began stroking my clit as I became lost in a wonderland. It wasn't long till I screamed "I'm cumming, I'm cumming" and my cunt furiously fucked his engorged meat. He rubbed me harder and then it happened. My juices streamed from me, coating his had and chest. I became dizzy, but continued to jam that hard cock into my body. Soon he was bucking up to meet me and then he grabbed my hips and jammed me down on him, holding me tightly as I felt his cock pulse and spit it's load into me. I could even feel the ripples of cum course through it before they splashed the inner walls of my pussy.
When I felt the last jet I fell forward and kissed him wildly. We hugged tightly and gasped for breathe. Then I felt him grow soft and start to slip from my body. I tried in vain to keep him there, but soon the head slipped free and I felt empty and began to cry. Hank held me close and I sobbed, not knowing why, but feeling so many emotions I could not comprehend.
We drifted off to sleep, to dream, to awake upon a new day.
When morning came I awoke to the sound of the shower. I found Hank there and quietly slipped in to join him. We kissed and caressed and lathered each other up in more ways than one. Finally we exited and dried each other off. I had the day off, but he had to go. He told me to stay as long as I cared to as the room was ours till noon.
I dressed in my lingerie and redid my makeup. Sitting on the bed I watched as he finished getting ready. All too soon he came to me saying it was time. I said, "Yes, it is" and I sank to the carpet on my knees before him. Silently I rubbed his crotch, felt his cock grow hard and began to unzip him. He started to protest, but I just continued. His pants feel to his ankles and his cock found my lips. He didn't protest any longer. Cupping his sack I fondled his balls and licked the length of his shaft. I kissed and sucked at the swollen head and licked the pee hole making him squirm. Inch by inch he disappeared into my hot mouth until he was in my throat. His groans said volumes and I let him slip from my lips only to tease his balls with my tongue, lick my way up his shaft and then deep throat him again. I sucked the knob and used my tongue on the underside. He began to thrust into my mouth. I pulled back and stroked him as I said, "You can cum, but you have to cum on my face darling". He nodded yes and I swallowed him completely. Now in earnest I sucked his dick and he fucked my face. A few minutes later he moaned, "Now, Gayle, now". I pulled back and stroked him hard, aiming it at me. The pee hole opened and he gushed like Old Faithful spurting stream after stream of hot cum all over my face. It dripped from my eyelids and my nose and chin, but I managed to scoop some up and feed it to myself. When he finally stopped pumping and some was just oozing out I took him back in my mouth to suck the rest from his balls.
When I was satisfied there was no more I let him pull free of my lips. I helped him dress and he stood there looking at me.
"I want you to remember me this way till the next time. On my knees before you, covered in your hot cum. Now go to work and daydream of me like this."
He left, blew me a kiss as the door closed.
I lowered my panties and jerked wildly at my clit as I cleaned his load off my face with my fingers and tasted every drop. In short time the carpet was stained with my juice, and that's how I left it.
Hank called me a few days later. We met quite a few more times and he gave me some lovely presents over the next few years...till his wife found out, but that's another story...