tagTranssexuals & CrossdressersTina Takes My Heart Day 01

Tina Takes My Heart Day 01


Day One

The rain was pouring down; the endless sheets caused deep puddles on the shoulder of the highway. I had already been driving for four hours and staring through the rain was really starting to bother my eyes. Up ahead in the road I saw a poor hitchhiker just soaked to the core, the way the rain was coming down it was hard to guess how long she had been out trying to get a ride. The highway I was on was not the busiest and I hadn't seen another car in the last twenty minutes. As I got closer I decided to pick her up, the company would be welcomed, the only stations I was getting on the radio had been religious zealots spewing their same old rhetoric.

She saw me and her eyes got big, I could see her face light up as I signaled to pull over. I unlocked the door and she got in.

"I'm so sorry for getting your seats wet but I am so glad you picked me up. I have been out there for more than an hour." She said to me in a very sultry almost husky voice.

"No problem, I could use the company anyway!"

"My name is Tina, and thanks again." She said. Tina was a gorgeous brunette with long dark brown hair almost to her waist. She was very shapely; she would never have a problem turning men's heads.

"Well hello Tina, my name is Joe. So where ya headed?" I asked the girl. I noticed the rain had soaked her so much her shirt was almost transparent, her dark nipples strained through the shirt. I felt my groin respond to the sexy sight in front of me.

"Well Honey anywhere you are at this point!" She said, "But eventually I want to end up in Vegas!" Since that is right where I was headed I told her I would gladly take her all the way there. It would be three more days drive without too many stops but if she could stand me she was more than welcome to stay for the entire trip.

"So what waits in Vegas for you Tina?" I asked just making conversation.

"You really want to know?" She said to me.

"Sure I have been around the block a few times, not too much can shock me!" I told her.

"Well Joe incase you haven't guessed I am going there to entertain. I am a transsexual and I heard they have plenty of opportunities for stage performancers. I hope that doesn't freak you out or anything?" She said to me in a worried voice. "When the trucker who gave me my last ride heard that he pulled over and made me get out."

"Well I am shocked! You are so hot I never thought you were a dude. But that trucker was an asshole. Just because you live a different life style doesn't mean you still couldn't have used the ride. And besides why would he even care unless of course he was going to try and jump your bones!" I laughed a bit to ease his/her tension.

"You're a sweet guy Joe, very open minded for sure and no I wouldn't have let him jump me even if I was a full fledged lady, he was disgusting!" She said.

We chatted about everything under the sun, politics, religion, movies we covered just about everything but we eventually ended up back to talking about her different choices.

"So and don't take this the wrong way, but you do have a cock right?" I asked.

"Yes, I'm a preop tranny but my cock still does work. Well at least till I make enough money to get that fixed properly too." She said. I really enjoyed her openness.

"I hope this doesn't offend you but, you can still have orgasms right?" I asked, she really had me interested in her and I had plenty of questions.

"Nothing offends me Babe, but ya I can still cum. Enjoy it immensely too! But pickings are slim when you live a double world I am afraid. You either get some creep who just wants to experience a tranny but would never take you out on a real date, or some married guy who hasn't realized he is actually gay yet!"

Tina was most intriguing person I had talked to in a long, long time. Just the conversations and different points of view were very refreshing. The real nice thing was we didn't always agree on all things and our arguments were debated with tact and politeness. When we disagreed we would give each other our points of view and if neither of us changed our minds we would agree to disagree. I didn't have to be right, she didn't have to be right, we just thought differently. The more time I spent with her the more I really liked her.

Driving became hard as I was getting tired. I asked Tina if she minded if we pulled into a motel for the night and offered her a room by herself. I was gaining a real good friendship and didn't want to jeopardize it by seeming like one of the perverts she talked about earlier. Although the more I looked at her the more I would have easily made love to the sexy creature that was in my car. I already pulled into the motel parking lot when she answered me.

"I don't have that much money Joe and I wouldn't want to put you out. I would be happy to sleep in the car." She said.

"I won't be having any of that! I will get you your own room; it will be like a two for one because my company reimburses me for my motel stays." I told her.

"Well I will be having none of that either. You are not going to be spending any of your hard earned money on me but I have no problem staying in your room if it will make you feel better." She said to me. Here we were agreeing to disagree like we were an old married couple, it was kind of cute.

"That I can accept, I have no trouble sharing a room with such a beautiful lady!" I said to Tina.

"Thank you Joe." She said to me in the most sincere voice I have ever heard.

"Thanks for what?" I asked.

"Thanks for calling me beautiful but most of all thanks for calling me a lady, you really are a sweet guy." With that she gave me a hug and I couldn't help but feel a little conflicted. I was being nice because I truly like this person but then again I felt my cock stir when her breasts pressed against my chest.

"Well thanks for calling me sweet but how do you know I am just not doing this to jump your bones?" I said laughingly.

"Because I can tell." She said, "But then again, who said I wouldn't let you?" And she laughed her sweet laugh back at me.

Her comment really made my cock jump. I took in a breath and stared at the striking woman in front of me. All the conversations we had and our playful teasing had my emotions on overload. If I didn't know better I would say I was falling in love with Tina.

I went in and paid for the room and Tina was waiting for me with both our bags in tow. We went into the room; it wasn't too bad for a cheap hotel room. There was only one problem there was only one king sized bed and no couch. We both looked at each other and shrugged, we would think of something. I told Tina I wanted to go take a shower and went in, the hot water felt great as it washed seven hours of driving grime off my body. I put on my boxers and headed out to the room. I was greeted by a cat call whistle from Tina and my face turned as red as a fire truck.

"Shower is all yours." I told Tina. When she got up to go take her shower I watched her move her breasts swayed with her walk and my penis started to respond again. She took a quick glimpse and smiled at my predicament.

Tina came out of the bathroom after her shower and it was my turn to cat call. She had on a baby doll negligee that amplified her breasts; they were almost spilling out of the low neck line. She had taken some time and gotten her face ready and for the first time I actually noticed how pretty she was. There was no way she shouldn't have been born a girl. I was on top of the bed; even though we were indoors the temperature was still in the upper 80's so blankets were not needed. My boxers were tented out from looking at Tina but I decided not to even hide it.

"Do you mind if I take the other side of the bed?" She asked me.

"I would be honored to be in the same bed!" I told her and then she jumped up and sat beside me. She grabbed the TV converter and started going through the channels, when she got to a porn she stopped.

"This looks interesting!" She said and then looked directly in my eyes.

"Uhhh Tina, I am having a hard enough time keeping my hands to myself as it is. Putting porn on is not going to help matters any!" I told her.

"I don't remember ever telling you to keep your hands off me! In a matter of fact I was hoping you would have made your move along time ago!" She said then leaned in and kissed me. Sweeter lips I have never tasted as I took her tongue in my mouth. My hands went directly to her heavy breasts and caressed her nipples. Her hands went right down to my briefs and tore away my boxers.

I then started kissing her neck tenderly, lower and lower I went until I reached her tits. Taking a nipple in my mouth I hungrily fed. She moaned in response and began stroking my throbbing member. Her hands couldn't have gripped me better if they were my hands. I pulled the top of her lingerie off, finally I got to examine the perfect set of breasts she had. Again I took her nipple in my mouth.

By this time she slid her body around on the bed and engulfed my hard cock, her mouth was all warm and wet. I thrust my hips into her face and she eagerly accepted my prick. She lightly gripped my nutsack and massaged my balls gently. She took her other hand and moved it behind me and started flicking her fingers over my ass, the experience was a new one for me but a welcomed one. The tingles over my asshole felt amazing. I returned the favor and slid her bottoms off. My fingers quickly found her back hole and I teased right back.

I took Tina's mouth off my pole and brought her back up to me and kissed her passionately. We lingered there for what seemed like hours, our hands never stopped their backdoor exploration. Then she pushed forward with her fingers and inserted two into my rectum, I in turn did the same to her. Her rectum felt warm and wanting, my head spun with the thought of being able to drive my hard cock in such a hot hole.

We were moaning to each other, the lust was only surpassed by the want. I broke our kiss and for the first time in my life I bent down and took a cock in my mouth. The feeling was hot, soft and hard all in one. I could feel the thick piece throb in my mouth. Tina grabbed my hips and turned me around so she could take my cock back in her mouth. We were engaged in a sexy sixty nine when Tina started thrusting harder in my mouth. Then with one big thrust I felt the hot sticky juice hit the back of my throat. I swallowed every drop; it didn't taste that bad at all.

"Oh my God Joe that was spectacular! You sure you haven't done that before!" She said to me. She then got up on her knees and presented her ass to me. "I need you to take that beautiful piece of meat and fuck my ass!"

I went in behind her and aimed my prick at her tight rosebud. When I penetrated the unyielding hole the feeling was beyond explanation. I have fucked many women in my life, some even in the ass but none of them could compare to the talents of this amazing transsexual. I thrust as deep as I could and she took it all thrusting right back at me.

"That's it Baby fuck my ass. Oh your cock feels so good in my tight ass Joe! Oh yes keep fucking me!" Tina howled.

I almost forgot she had needs too but soon my mind escaped the pleasure for a quick minute and I reached around and found her hard cock and started stroking it. I soon gained a perfect rhythm with my hand and my thrusting. I picked up my speed and Tina let me know that my performance was top notch.


The feeling of Tina's hot cum dripping all over my hand sent me over the mountain and I thrust deep inside her ass, shot after shot of my hot cum exploded out of my cock.

We crashed into each other on the bed and started kissing again, the after play was as erotic and sensual as the foreplay. I pulled her face away from mine and looked deep into her eyes.

"What?" She asked me.

"I think I am falling in love with the most incredible human being on the earth!" I told her then kissed her again.

"You're so sweet Joe. This is going to be the best trip of my life. I think I am falling for you too!"

To be continued...

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