Chapter 1 – Emotional Takeover

Please let me introduce myself. I am Jim, roughly 6 feet tall, dark brown hair, blue eyes, and a little chunkier than I would have liked. Ever since I touched myself for the first time, I’ve thought about women. I’ve only had one girlfriend by the age of 22. By now you’ve probably guessed – one girlfriend – “I bet he watches a lot of porn.” Yes, you would be correct.

One day I had been watching porn and stumbled upon a woman with a dick. Mind you, this was by accident because of the misleading title. At first I felt awkward, confused, and lost at many things. A woman with man parts? How could this be? After a few minutes, this concept began to greatly intrigue me. I suddenly found myself researching the tags of the video. Transsexual, shemale, tranny, t-girl, transvestite, ladyboy, all meaning about the same thing, if not in some way related to each other. While doing this research I became even more fascinated – it had opened up a whole new world to me.

Almost instantly regular porn took a back seat to transsexual porn. It was as if I could not get enough. I found myself masturbating even more than before because of all my heightened curiosity. Every day I would be watching a vast amount of videos, none of which could suffice my new found lust for a shemale. This is also the point at where I began to question my sexuality. I still loved women; however, I wanted to be with a ladyboy just as much. Occasionally a gay visualization or the likes would pop into my head, but I don’t think I would be able to follow through sex with another man. Transsexuals were my loop hole to this situation. They had dicks, but had the beauty of a woman. With these thoughts in mind, what do you think that makes me? Considering all the information gathered, my best guess would be a closet bi-sexual.

Being 22, you would say I’m still a youngin’ on the bar scene. In just one year I had visited many straight bars and never really had any luck. I couldn’t tell if it was my character, appearance, or lack of social skills, heh – maybe a combination of all possibilities. Whatever it was, it furthered my curiosity for a shemale. Finally, that curiosity built up so much, there was no tolerance left to hide those emotions. I headed to a bar for these ordeals.

Chapter 2 – Order Up

This bar looked just as every other did from the outside. Even its name was similar to your standard pub. It was a bottom floor of a downtown storage area, maybe some lower end apartments on the upper floors. The window was filled with the “It’s Miller time” and “Budweiser” neon lights, as well as the happy hour flyers. The only way you would know it was a different style of bar is one of two ways. Word of mouth or you ventured inside. I proceeded to enter.
Upon crossing the threshold, I looked around. It looked very similar to many bars, say for one exception. You had the tables filled with people having good times, more at the bar telling each other stories or mindless conversations, and a small lounging section. The closer inspection of my surroundings let me know this was a bar for many types of people. Those types included shemales, transvestites, and gays (both men and women.) The transvestites and gay people were easy to spot, once you had separated them; you had a good guess at the others.

Being the shy type, I found an open table away from the loud noises radiating from many groups. Who likes listening to those obnoxiously loud people at the next table over? Before I could fully grasp my surroundings, a woman came over to take my order. “Hey handsome, what can I get you to drink?” At first I found it hard to respond, this woman was gorgeous. She looked to be about 5 foot 6 inches with long brown hair. Her hazel eyes were almost glaring at me as I sized her up, but I could not help myself. Her breasts were about average. If you insist on a guess, they were probably 34C. Average did not describe this woman even though her tits were. She had the “hourglass” figure for sure if I ever saw one.

She snapped “Excuse me, can I get you a drink?” Suddenly I was brought back to reality and hurriedly apologized. “I’m sorry; I’ve had a rough day. What rum drinks do you have?” She responded by handing me a menu with them all listed. One drink stood out: Island Breeze. This consisted of some pineapple flavor with coconut rum. I told her that is what I wished to drink. Thinking we were done with our transaction, I continued my scan around the bar. That’s when she said, “You know this is a lady’s drink, right?” Not giving it a second thought I said, “That is okay, I like the sweet and nutty taste of the coconut.” She turned, as doing so; I could see the smirk on her face as she went off to retrieve my order. It was then I realized what I had said, but instantly got lost in the sway of her hips as she was walking away.

Chapter 3 – The Return

As she was concocting my drink for the evening, I continued you to watch her. Think creep all you want, but I found this woman absolutely and positively intriguing. At one point, she felt my gaze and looked up in my direction. Our eyes met in a deep stare, this was the moment I knew I wanted to know everything about her. What was her passion? What did she enjoy? How did she feel? How does she smell? How does her kiss taste? As our gaze softened, she went back to my drink. She did so with a smile that had me tingling.

She returned with my drink and said, “It’s on the house.” I responded with “Please, you must let me pay for it. I would feel bad not do…,” before I could finish she cut me off. “My shift ends in an hour. If you stay here, I will bring us drinks and we can have a conversation. Stunned with this woman’s interest in me, I could only manage one word – “Deal.” Too pass the time; I began to contemplate all possible outcomes of what would happen. These outcomes were the only thing racing through my mind, almost like multiple daydreams – the time flew by.
Out of nowhere, there is this sound – “Hey!” I proceeded to jump from being startled only to remember who it was. “I brought us drinks. Here, it looks like you could use some pick me up.” It then hit me; I forgot my manners and quickly blurted out, “I’m sorry, I didn’t introduce myself. My name is Jim. What is yours?” “I’m Janet, but all my friends call me Jan.” I followed up with “Well Jan, it’s nice to meet you, but it’s occurred to me – I know nothing about you. Why do you work here, with your looks you could be a model.” “Oh please, you are flattering me. I managed to get the job by chance. The “my friend knows the owner deal” and I took advantage. What is it you do?” “I do a variety of things with physics, but I really love languages, which I spend my spare time working on” She responded with a cool smile and “oh really, what kind of languages.” “Well, I enjoy both computer programming languages and the foreign languages.” “That is interesting, but it is over my head. You seem like a very smart individual.” “I would like to think so, but so often I find myself lacking.” “Sweetie, there is no need to be modest. I find smart and passionate people to be very… sexy.”

At that moment, something clicked in my brain. I must get this woman home and delve into her. She seems so innocent yet her words had a hint of seduction in them. I asked “Say Jan, why don’t we finish this conversation at my place. There is something I can’t put my finger on, but I find you irresistible. I want to know what makes you tick.” Her response was simple – “Likewise. Let’s go.”

The car ride to my place was full of conversation. It was as if our words were intertwined together. The words were previewing what the night had in store. We were so deep in conversation that neither of realized we had been sitting in the driveway for a few minutes now. Together, we got out of the car and proceeded in the house.

Chapter 4 – As we lay

I closed the door behind us as we entered my home. As soon as I did, there was no more conversation. We did not even stop to hit the light switch for the moonlight from the windows provided us with the perfect setting for this encounter. We began kissing one another. As the minutes passed the kissing would become more and more passionate. Our tongues became intertwined just as our words had previously done. We both kissed each other for a while; so long in fact, we had to catch our breath. We stood their smiling at each other, breathing heavily.
We kicked off our shoes and began kissing again. I started to pull her to the bedroom. While still with our lips almost continually embracing each other, we took off our clothes. Finally reaching the bedroom, I’m only in my boxers and her in some black bra and panties. We stopped for a few moments to size each other up. As we did so, our eyes met for the second time that night. This only furthered our lust for one another.

On the bed we lay, embracing not with our arms, but our lips as well. Being the man that I am, I slowly run my finger tips down her back to her bottom. I had never felt such a perfect ass. With each squeeze I became more and more intoxicated with this woman. She slowly runs her hand down my chest providing a tingling sensation. Her hand goes past my waist line, under my boxers and begins to feel me. She is now stroking my dick with the softest of hands. Our kissing is now accompanied by subtle moans from the pleasure of one another.

Our lips release and she looks at me and says “I’m going to give you the best night of your life.” The only thing I could do is smile at her. She slowly pulls my boxers off, taunting me with every second that passes. Teasing me still, she says “Somebody is extremely hard already; let me see what I can do about that.” She starts to suck my dick. While doing so she is looking up at me with such cute eyes I find it almost impossible not to cum. No more than a few minutes passed and “aaahhhhhhh, I’m going to cum.” She swallowed my load whole and stated “Now it’s my turn for some fun.”

She lay there as I began kissing her beautiful breasts. Her face let me know how turned on she was. I slowly started to make my way down her body covering every inch in order to pleasure her. I stripped her of her black panties and there it revealed itself. One of the best looking most intriguing woman I’ve ever seen has a 7 inch cock. Her cock was in fact bigger than mine. For a moment, I sat in a daze looking at it – undecided on what to do. I thought to myself, how could I have missed it, it was half hard when I made my way down on her. As soon as I had that thought, I remembered my desire for to have sex with a shemale. I had been watching porn with shemales, yet I was afraid to actually have sex with one?

I boosted my courage and went with it – my desire completely kicked in. I began to stroke her lovely dick as I gazed into her eyes. I used the knowledge just gained 2 minutes ago to use on her. I began to suck her cock like there was no tomorrow. She was moaning left and right. Jan told me to stop because she didn’t want to cum yet, but I was really getting into sucking her that I could not stop myself. She released into my mouth and I managed to swallow all of it.

She suddenly did a 180. She yelled at me for making her cum so soon. She said, “Now you’re going to be punished for making me cum earlier than I wanted too.” In a way I couldn’t explain, I wanted her to punish me. To make me feel wanted, to be inside me. She was already behind me before I could react. Even if I could react, I wouldn’t have. I wanted to know the answers to my questions and emotions.

Slowly I could feel my asshole begin to open. She was pushing her dick into me. At first there was nervousness and pain, but that quickly subsided for pleasure. She was fucking me all the way in until our hips would collide. This was driving me wild and she could tell – “You are enjoying this aren’t you, you bad boy.” “Yes, I love it.” was the only response I could must with so much pleasure being shot through my whole body.

I lost count of the minutes she was thrusting me. She turned me over and pushed my knees to my chest. She leaned on top of me so that her boobs were touching the inside of my knees and our gazes met once again. “I’m going to fuck you so hard. You will love it so much that you will never have sex with another person again.” By the time she finished her statement, I was already agreeing to what she had said. Her sweet cock driving in and out of me a furious pace had produced pleasure not only a physical, but an emotional level as well.

Again she said something while screwing me in a new position – “You are going to do as I say, when I say. I don’t care where we are, what we are doing. When I want to enter your ass, you will cooperate. Do you know how I know you will cooperate?” “Yes, I know I will because I love you being in my ass so much.” “Yes, you are correct.” This conversation during sex must have sent our senses to new heights because I came almost instantly because of the crazy seduction in her voice and her stroking of my cock. When I came, my asshole tightened up. She plowed my tightened ass. With a last thrust she moaned very loudly and shot her second huge load into my ass.

Her dick still in my ass she leaned forward to kiss me and said “I don’t get tired easily.” I was hard again in nanoseconds. We could read each other’s thoughts by this point. I didn’t want to stop and she had no intention of doing so. She continued fucking me into the night.

To be continued??
Yes or No? Depends on the feedback.
It was my first story, so please only constructive criticism.