Tranny Tales Stories of an amateur cross-dresser's fantasies and true adventures
The Entrepreneur
I had a long day of business meetings and I was so anxious to dress up and get out and visit some sex shops and gay bars. I was on my own for the night in the city on the other end of the turnpike. So, I grabbed a motel room and dolled up for the evening. It was mid-winter and definitely not mini-skirt weather. So, I wore my long, black, tightly tailored skirt that went down to mid-calf. It was the kind of skirt that was so tight that it was a challenge getting in and out of a car! Walking was another challenge. But, in taking short steps, I navigated rather well swinging my hips in a most provocative way. For my top, I brought my bright red zipper-front sweater that fit me nice and tight accentuating my breasts beautifully. Rounding out my attire, I wore a red scarf, matching my sweater, my favorite long, black curly wig and supported by my 4-inch black pumps. Yes, I turned a few heads as I left my motel room and "wiggled" to my car!
I visited the usual bars scattered around town. It was mid-week and there wasn't a lot of activity. My next stop, after visiting a friendly neighborhood bar, was a popular sex shop located downtown. So, fortified with a little beer, I parked nearby, strolled about a block to the entrance, and confidently entered. I love browsing in sex shops looking at the variety of toys, she-male mags, dvd's and occasionally checking out the video booths. But, my real purpose in visiting such places is to find an attractive daddy-type. I've learned over the years that men go to bars for the purpose of drinking and maybe sex if the prospect looks attractive enough through the lens of bottle. Gay bars can be a safe, accepting place for a cross-dresser. But, many if not most gays are interested in other men, more or less like themselves. Now, a man going to a sex shop is interested in sex, not drinking. So, prospects are much better in attracting a man for sex at a sex shop and maybe he'll like sex with a tranny, particularly if he considers himself straight but with just enough curiosity.....
Anyway, I walked over to where the tranny mags were placed and was immediately attracted to a gorgeous middle-aged man, nicely dressed in a gray suit and tie. He was a little on the husky side with a beautifully trimmed and thick beard. From the way he was dressed it was clear that he was wealthy or appeared so. The attraction seemed to be mutual as he approached me and started asking all sorts of questions as to where I was from, did I dress up often, what were my sexual interests and so forth. I eagerly fielded his questions liking everything about him and hoping we could hook up for the night. But, from out of nowhere, the store manager interrupted and coldly informed us that we were not allowed to interact as it was against store policy. We were both surprised by the rude interruption and quickly separated but not before we at least exchanged names. His name was Dirk which seemed to fit him well.
Now that we were split up and under the watchful eye of the store manager, we lost track of each other and a bit of a comedy ensued. The sex shop was compact but with tall shelving units making it difficult for us to find each other. Unbeknownst to me, Dirk purchased admission tickets to the video booths and went inside, perhaps expecting to get at least a blow job from me if I followed him in. I wasn't aware of his booth plans and not being able to find him, I assumed he was waiting for me outside and left the store. By now, he was in the video booth expecting me to join him while I was outside, trying to spot him in the parking lot. Needless to say I was surprised and disappointed thinking he got away. Not wanting to re-enter the sex shop and risking another lecture, I went to my car and waited before proceeded down the one-way street taking me past the store entrance. No sooner than I passed the entrance, there he was, crossing the street to his pick-up truck. I quickly rolled down my window and apologized for my part in getting us both in trouble with the store manager. Dodging traffic, he immediately walked over to my car and asked me where I was going. My true destination was another gay bar just on the other side of downtown. He told me to wait and he would follow me. So, I waited before proceeding to the bar with this gorgeous hunk, with his heavy beard, wearing a high dollar suit and driving a brand new pick-up truck hot on my tail.
It only took a few minutes to get to the bar and all eyes were on us as we entered! We were quite the couple, nicely dressed and hand in hand. Dirk immediately ordered drinks, wine for me and a beer for him. With eyes still on us, we grabbed a table giggling like two kids over our separation and almost miraculous reconnection outside the sex shop. Our drinks arrived and we settled down to our life stories. He told me he was from Canada and moved to the U.S. several years ago. He told me about his divorce and the custody of his sons that prevented him from inviting me home. He was a wheeling-dealing investor in lots of ventures, most notable aircraft. He bought and sold them to large corporations for executive travel. I know a little about aircraft and was able to follow him for some of the conversation. I told him my life story, that I loved to cross-dress, enjoyed sex with men whether I was dressed as a woman or not, and loved the submissive, feminine role. The answer must have delighted him as I felt a hand stroking my thigh and a foot, with the designer loafer slipped off, working its way up my long skirt. I have no resistance to the advances of a horny man and it was obvious he was very horny. Yes, I enjoyed the roaming hand as it worked its way up to my sweater!
He proceeded to tell me that while he lived a straight life, he absolutely loved cross-dressers and was immediately attracted to me, my looks, style and poise at the sex shop. He dated cross-dressers on and off over the years and loved that we appreciated sucking cock and getting fucked in the ass much more than real women did. He told me that he had dated a local "tranny". But they drifted apart months ago. As if to re-inforce his interest in me, his need for me, he moved closer to kiss me much to the amusement, maybe envy, of some of the patrons. I was instantly seduced wishing we could be regular lovers and not separated by two hours of turnpike. My imagination went into overdrive fantasizing about being a special "woman" for a wealthy man and all the fun it could be. But, at least for the moment we had each other and we had the night ahead of us. While we finished our drinks, I gave him my motel location and room number in case we became separated. It was clear to me that this would be a very memorable night!
The geography was a bit of a challenge. But, Dirk managed to follow me all the way to my motel. We arrived together and he waited while a retrieved a bottle of wine from the car and the room key from my purse. I wasn't exactly tipsy. Rather, it was just that I was in another world, a world where boy meets "girl" with the prospects of lots of fun play! Once inside, we embraced. He squeezed me hard and I could feel his firmness, his hardness pressing against me! We slipped out of our shoes and immediately started undressing each other. While he unzipped and removed my sweater, I pulled off his suit jacket and unbuttoned his shirt, finding that his chest was a delightful forest of man fur. Next was my skirt countered with his slacks. The bulge in his boxers was now so very noticeable and I started caressing it as he removed my bra. He then leaned over and started kissing my little pink nipples which grew immediately attentive as he licked and nibbled. I could have stood there, clad only in my corset and gartered hosiery, allowing him to nurse on my breasts. Oh, but a delicious delight awaited me under his boxers!
I went to my knees pulling his boxers down and was greeted by a gorgeous semi-erect but already very thick dick that seemed so eager for some oral attention! I kissed the head and slowly and methodically licked his crotch and balls ignoring his dick which seemed to stiffen on its own wanting my attention. I quickly treated it to the warm and inviting confines of my mouth as my tongue teased it. His dick wasn't overly long. Oh, but it was so thick that I knew I would enjoy having it penetrating my sphincter, my boy pussy, and filling my rectum to the brim! For now, I took delight in feeling his hard and slick dick dart in and out through my lips and then back in, all the way to the back of my mouth, banging against the back of it, wanting to go deeper.
It was obvious that Dirk knew his way around a she-male and he obviously liked where we were going and that destination would involve the bed! He lifted me back up and gently kissed me while slipping his hands into my panties, caressing and then squeezing my ass. He then pulled my panties down and gently kissed my pelvis, around my "clit" before gently taking it into his mouth. I could have cum right then. Oh, it was so tempting. But, I wanted him to cum. His completion would be my completion. He sucked me for several minutes and then pulled my panties completely off before escorting me to the bed. He got into bed first, on his back inviting me to get on top of him. I eagerly complied resting on top of him as we kissed. I then worked my way back down, kissing his nipples, his navel and then re-focusing all of my attention on his dick and balls.
Oh, but the real delight happened next when he instructed me to straddle him with my ass against his face and his dick in my mouth. Oh, I've had my "pussy" eaten before. But, this would turn out to be the sensation of a lifetime. His tongue rimmed me before plunging into me, past my sphincter and licking inside me as far as it could reach! But, what really surprised me, shocked me and teased me was his bristly whiskers tickling, scratching and caressing the tender skin of my ass and around my pussy! The pleasure intensified as he pressed his face against my ass, probing even deeper into me while the tickling, scratching and caressing intensified. Ok, I'm not a real female. But, the sensation had to be close to what a real woman experiences during cunnilingus! Then he started to nibble me, gently biting me and making me squeal with delight. I was so engrossed with his oral attention to my derriere that I almost forgot the luscious dick just inches from my lips. So, we engaged in old fashioned boy-girl 69-ing! No words could adequately describe the pleasure of having my pussy "eaten" while enjoying the silky smooth hardness of a good dick in my mouth! Oh, I wished it would never end as I couldn't get enough of his mouth probing, teasing and abusing my pussy!
I realized however, that as much as I liked this bristly brush teasing my ass, and as much as I enjoyed taking this awesome cock all the way into my mouth, I wanted him to fuck me. I wanted this wonderful evening to reach a climax that could only come with his seed deep inside me. I was as hot as he was horny and I was very determined to be fucked. I slowly stopped sucking him and turned to face him, straddling his body with my ass against his nice, thick dick. Dirk made no objection as I slowly inserted it into my very wet and very hot pussy. The shock of his thickness penetrating my sphincter surprised me and I let out a brief but loud scream! But, once he was in me, I quickly adapted and immediately enjoyed the pleasure of his thick dick as I thrust up and down, twisting and turning, wiggling and pumping harder and harder feeling the initial pain evolve into intense pleasure as his dick popped in and out of me while he squeezed my breasts and pinched my nipples.
The pleasure was indescribable as I reversed position, facing away from him, giving him a nice view of his dick sliding in and out of my ass. I was nearly complete. All I needed was his orgasm, his cum streaming into me and I would be his! I gradually squeezed his dick with my ass, increasing the friction of pussy against dick. He could have finished right there with me on top. But, he made it clear it was time for him to ride me. So, we changed positions with me on my back, my legs up in the air and firmly in his hands while his dick found my pussy for penetration. This time it was less painful and much more pleasurable as he pounded against me as if he wanted to drive me into the mattress. I again wiggled, squirmed, squeezed and played the receptive, submissive role to the utmost! He continued to fuck me harder as he started moaning, moaning louder and louder until I could feel him shudder, almost convulsing as he pumped his cum into me. I released the pressure of my pussy squeezing his dick while he continued to slide slowly in and out of me enjoying the last moments of erotic bliss.
Satisfied that he was through, I rose to gently lick his still stiff dick nice and clean. I then went to the sink, rinsed a wash cloth with warm water and soap, grabbed a towel and returned to gently wash his dick and balls. I then came back to bed snuggling next to him surprised to realize he had no intention of leaving. Instead, he was choosing to cuddle me, comfort me and talk. If I could fall in love with a man in one night, this would be the man and this would be the night. We cuddled and talked for another hour, sipping wine and enjoying each other's company until it was time for him to leave and return home to check on his sons. I helped Dirk gather his clothes and kissed him goodnight as he left but not without exchanging phone numbers.
Oh, I was still so hot, so excited that I literally jumped for joy from such a sweet experience! And, I wasn't done! I returned to bed still feeling his warmth where he laid next to me, feeling him, feeling his dick in my mouth, his scratchy beard against my pussy and then his dick inside it. I relived the experience, with one hand gently caressed my dick-clit between my legs as though it were a real clitoris. With the other hand I started tickling and caressing my nipples. I then reached for one of my dildos and gently inserted it inside my pussy, still lubricated by his cum. It was just the right combination of stimulation as I easily climaxed and would cum yet again later that night.
The following day would be busy with a plethora of business appointments before I would get back on the turnpike for the drive home. I reached for my phone and his number. With some anxiety, I dialed hoping he would pick up and wondering if I would be just another one night conquest. But, on the third or fourth ring, he answered! I could tell that he was instantly pleased that I called and promised we would meet again and again. And we did, several times over the years on both ends of the turnpike. Each time would be as fun and as enjoyable as the first. Regrettably, he would relocate to the west coast and we would lose touch. But, I will never lose touch with the memory of him and that scratchy beard!
Greetings all!
While my tranny name is Tricia Louise i go by Timi these days. If You got this far, i hope you enjoyed my story. While i'm a little more into "retirement" these days, i still enjoy "femming up" a little and visiting friends, bars and sex shops occasionally.
I'm married. But, I have some great Daddies who enjoy my services. I do enjoy corresponding with Men who appreciate us along with other like-minded "demigirls".
Sweett53@zohomail.com
You'll find me very responsive, caring, and friendly. I love swapping photos and stories and enjoy writing about my adventures, thoughts, feelings and fantasies.
Please be safe!
Love,
Tricia/Timi