In the previous installment I described my first erotic experience with a transsexual lady who I met while working in Houston Texas in 1999. This is a continuation that takes our experience from the initial meeting to a night on the town and her deflowering.
I was working as a construction manager for a national company at the time, with a territory that encompassed the western US along with Kentucky, Indiana and Tennessee. In future stories I will be relating some of the true things that happened to me on these forays into the exotic and erotic.
The story continues:
We rested together in each other's arms, savoring the warmth and sexual release we had experienced. Heather was cupped against me with her arms and legs intertwined with mine. Her hard prick had been pressing against my butt crack.for the duration of the time we rested, her hips slowly and continuously nudging forward into my ass. Her leaking pre-cum had made the area slippery as each successive thrust was held longer and longer. My cock was once again hard as she reached around with her smallish hand to gently grasp it and lightly trace her fingers around the base of the head. As she slowly manipulated the head, brushing ever so lightly around it, my hips picked up a rhythm of their own thrusting into her hand and then backing into her hardness. She whispered in my ear...
"Ted, will you grant me one last wish before you take me as a woman?"
"What is it?" I whispered back.
" I lived for twenty plus years as a man", Heather said, "I have a daughter and had a great wife until I felt uncomfortable in a man's body. We tried to work it out, but she couldn't take it, me wanting to be a woman, dressing and hiding so our friends wouldn't find out. Anyway, I just want to experience what a man feels one last time...would you..." Her voice trailed off and her hip pressed against my butt.
"I've never done this before", I said, "but I guess that since I am taking your virginity tonight, I can let you take mine."
With that she pushed against my hole, the pressure increasing, until, at long last, I felt her enter me. She was not very big, about the size of my thumb, but five or six inches long. I gasped as she entered and she stopped her movement. After a few seconds, she started back in, then pulled back slightly, then thrust in again-this time filling my ass to the hilt. I felt her bottom out and her balls slapped against my butt. She fucked me for about ten minutes...I would squeeze on her cock as she pulled back then relax as she pushed back into me. I could feel the head of her cock pressing on my prostate, eliciting groans of satisfaction that I was surprised to hear coming from me as she moved in and out with a tantalizing tempo. Suddenly her tempo increased and I could feel her cock harden more and grow inside me. She licked at my ear and bit my neck and shoulder as she made one final thrust upward into me and held it as if frozen in place. Her cock throbbed with each beat of her heart and then I felt the warm release deep inside me. After what seemed to be a minute, my cock began to throb and I let loose an orgasm that felt like it came from my toes, spraying cum all over the bed and side table.
We relaxed, kissing and fondling each other as we came down from our sexual high. I didn't feel like I had done anything taboo, just loved a beautiful lady who needed me and needed to be comforted.
After a while we got up and went to the bathroom to get ready for Heather's night out as a real woman. We hit the shower (together, of course) and spent the entire time soaping each other up as we became aroused again. I took the bar of soap and gingerly soaped the tips of her tits, making them stand out like little erasers. After I did her breasts my hands slid to her ass. I squeezed it and then moved lower to her asshole. Slowly I struck first one, then a second finger in her ass and sawed them back and forth like I was fingering a pussy. She backed into them and groaned, her mouth opening and straining to say something. She mouthed something, but no words came out, just a gutteral moan that gradually increased into a panting scream as she came. The sinews stood out on the insides of her legs as she seemed rooted in that one spot in the shower and shook with pleasure.
I don't know how long we were in the shower, but we were both pretty well 'pruned' up by the time we got out and dried each other. Heather went to the make up case and started to apply a fresh coat of eyeliner and "powder her nose." I looked at my watch and saw that it was now about 4:30 in the afternoon. I had no idea where the time went, but I sure did enjoy how we spent it.
Five thirty came and we got into my rental, headed east on the Katy freeway towards a club that Heather wanted to go to. She said it had a swanky restaurant, good food, and usually had a pretty good band. We drove for about ten minutes, then turned south for a few blocks. The club was tucked back off the main drag and had very little advertising out front. We parked the car and before we went in, kissed long and hard for a few minutes. Heather looked exquisite in her black dress...low cut in the front and back, about mid thigh length, and split on both sides of her torso from the waist to just below her breasts. Three inch heels and black stockings rounded off the ensemble, which made her stand about 5' 11 as we went to the door. Black tresses fell around her shoulders and down her back to complete the image. If I didn't know better, I would say that I had the most beautiful, sensuous woman in all of Houston on my arm as we entered the club.
Once inside, we were ushered to a booth in a dark corner. We were separated from the main floor by a serving station, so no one could see us. The tablecloth fell just low enough so you could look straight at the table and never know if anything was going on underneath. The waiter came to us and told us about the specialty of the house and suggested a very tasty wine. We ordered and I could not keep my eyes or hands off Heather as we sat together. My hand was rubbing up the inside of her thigh as her fingernails traced the outline of my cock through the leg of my trousers. We were slightly preoccupied when the waiter returned with the appetizers and wine. He smiled as he set the barbeque'd prawns in front of us, then, seeing our napkins still folded on the table, started to put them across our laps. He took a little time unfolding Heather's and as he draped it across her lap, she let out a surprised sigh, then smiled at the waiter. He came to me and with a flourish, placed my napkin in my lap, noticing the placement of Heather's fingers. Backing away from the table, he asked if we wanted more privacy. I said that we were OK, but to take his time in bringing the dinners. He nodded and with a knowing grin said that he would stretch out the dinner.
"I don't believe it" Heather stammered. "He copped a feel when he was putting the napkin in my lap" she continued "and I think that he knows our secret."
"I don't care if the whole world knows that I am here with you," I said "Because I am here with a divinely beautiful lady tonight."
My hand continued to trace circles on her inner thigh, eliciting familiar moans of pleasure as they worked higher. I reached the apex, and finding her cock tucked under, moved the panties aside and freed it from its satin clad confines. Ever so lightly I let my fingers trace delicate circles around the head, feeling her arousal seeping out again.
Our dinner arrived and we ate a sumptuous feast, following it with a marvelous crème broullet and some Irish coffee. When the band finally came on, we were feeling very loose. We danced several fast tunes, but spent most of the evening looking into each others eyes as we pressed our bodies together on the slow ones. I felt like the luckiest guy in the world as almost every eye (ladies too) was on Heather while we danced. Her lithe figure undulated to the music as she ground her pelvis against mine, her freed prick pressing against my crotch like a rapier in the skilled hands of a swordsman. Shehad her hands wrapped around my neck, looking longingly into my eyes, teasing my hair with her nimble fingers as we danced. All too soon, it was about 11:30 and we decided to call it a night.
We walked arm and arm out to our waiting steed and started an inexorably long drive back to Heather's place. Time seemed to stand still as we waited for several lights, then back onto the Katy freeway for the last dash. It seemed like an eternity, but we made it at last as the radio announcer said that it was midnight.
Heather fumbled with her keys as we tried to get the door open, laughing and kissing all the time. Once inside, we started taking each other's clothes off as we headed for the bedroom and the pleasures that awaited us. We tumbled into bed, our mouths seeking each other's and hands fondling whatever we could get hold of. Suddenly, Heather stopped and looked deep into my eyes while she held my head in her hands.
"I'm ready" she said, "take me and make me a woman. I want you desperately. I want you inside me. I want you to make love to me."
Her last words hissed out of her mouth and her eyes closed to mere slits as she pulled me to her, kissing me deeply and strongly. I took her in my arms and cuddled her hot body against mine.
"Your wish is my command" I said with a mock gallantry, my voice quivering with excitement.
I pushed her back into the bed as I trailed kisses over her forehead and kissed the tip of her cute button nose, pausing to give it a little nip. My hands lightly palmed her right tit and brushed over the erect nipple causing a rapid intake of breath. Heather moaned my name and I responded by moving my tongue to her ears and neck, whipping small circles of moistness on her skin. Her body arched upwards from the bed as if trying to spear some invisible being with her cock. I moved my lips down her body until I was between her legs, facing that darling little piece of flesh. Her cock seemed more like an oversized clitoris now, the tip red and poking out from her ball sac. I lightly kissed the very tip sending her over the edge into a loud, crashing orgasm. Her clit throbbed with each heartbeat, her hips stabbing the air, sinews on her legs taut and quivering as she came. I held on to her ass with both hands, squeezing her cheeks as hard as I could and taking her clit into my mouth all the way till my nose was buried in her pubes. With all the suction I could muster, I pulled back on it and let it slide out till I held just the tip in my mouth again. Using my teeth I nipped at the tender flesh causing her to scream again, this time into the pillow as her head thrashed back and forth-her long black hair flying in all directions.
"Ohhhh Gawd" she mumbled, "I just had the most intense orgasm I have ever had, but I didn't shoot. It felt like I was one mass pleasure being".
I licked lower then, pausing to push my tongue into her butt crack. The tip played with her anus slowly insinuating itself into the rosy bud. My finger soon followed, widening the hole lubricated by spit. I pushed it in to the hilt, then pulled back slowly and followed with a second finger on the next stroke. My tongue was back at her clit now, licking up and down the shaft and around the head, saliva dripping onto my fingers as I continued to bury them in her butt. I added a third and was rewarded with a long gasp.
"I can't believe the feeling down there, " she cried out in ecstasy. "It feels like my insides are churning and there is electricity in my pussy. My clit is on fire and, oh gawd...just take me. Make me a woman...NOW."
Slowly I left my place between her legs and worked myself back up her body till we were facing each other, my body pressed down on hers. My cock rubbed over the top of her clit, balls slapping against her ass.
"How do you want it Heather?" was all I asked.
"Oh gawd, I don't care,"she puffed in reply, her head thrashing from side to side on the pillow. "I just want you inside me...make love to me."
I reached down and hooked my arms under her legs, bringing them up towards her chest. Moving my turgid member towards her hole, I paused and took some lube from the side table, quickly coating my cock and letting some rip onto her puckered anus. I slid it back and forth a couple of times, wetting her crack and making it slippery, then put the tip at her opening. I paused, then started to apply pressure with a steady thrust. I felt her stop breathing for a second, then let out a long guttural wail as she pushed back against me. Suddenly I felt the sphincter muscle loosen and I slid inside aobut an inch or so, the tip basking in the boiling inferno. I paused and let Heather get used to the size, then continued a slow sawing back and forth until I was all the way inside her. The heat was incredible and it felt like a wet, velvet glove was gripping my cock. I could feel the head expand with each heartbeat and could also feel her muscles contract with her heart's rhythm. Heather looked up at me with a blank stare then slowly started to thrust back up at me causing me to start a slow fucking in and out of her. Her clit was caught up between our pelvises rubbing back and forth in my pubic hair as we danced an ancient dance of lust. We continued this dance for about five minutes, me trying to hold back my urge to cum and her craning her neck to watch me sliding in and out of her hole.
"Mmmmmm" she purred as she bit her lower lip, leaving red teeth marks from the pressure. "I'mmmmmm goooiiinnnggg toooo cuuuuuummm" was her raspy reply to my thrusting cock.
She arched her back and thrust upwards on my cock, impaling me deeper than I thought possible, and lifting my body off the bed. Holding the position for a few seconds, I felt her muscles milking the shaft and trying to suck me in further. I lost it. My cock started to throb uncontrollably as I felt the pressure build from my balls and race up the shaft. My seed spilled out in hot jets painting the inside of her pussy. I don't know how long I continued to spurt, but it seemed like an eternity as my hot jism filled her bowels, spilling out around the side of my cock as I continued my thrusting motion. Moaning now, Heather lay back, me still embedded in her and relaxed.
"Thank you" was all she said.
"My pleasure, m'am" the simple reply.
We fell asleep in each other's arms. I don't know exactly when, but I awoke with her tonguing my now deflated cock back to life. After she had me at full hardness, she turned her back to me and moved her ass against my cock, slowly putting me back in.
It went easier this time, a slow languorous session of love making that ended with the sun's rays splitting the drapes and birds waking us up with their music. We spent the rest of the weekend in her bed and on her couch and in every other room of the house, fucking like two lusty teens in heat. We kept in contact over the next few months, but then drifted apart as my work carried me to other parts of the country and other escapades. When I last heard from her, she was living full time as a female, working for a computer company doing specialty programming. And yes, she had a fiance... her wish now fulfilled. Heather had become a woman in every sense of the word.