Episode 64: Getting Jolly With Jazz

My next sexual escapade came the very next day after my usage of that stupid Chink Ling. I’d just finished breakfast and was checking out the women on the website. After a few moments of scrolling, I came across Christi’s old profile which had been marked as ‘NO LONGER WORKS HERE’. I had to admit that she was a top-notch fuck but she had to go and ruin it by being all clingy and wanting a relationship with me. Under any other circumstances I would have jumped at the chance to be in a relationship with such an unbelievably hot woman like Christi; but not when it affected my job at the hospital. Being the ‘Hospital Fuckboy’ was more important to me than any relationship that the women I fucked wanted.

The only exception was Ariadne and I knew that she would never be coming back to me. As I have said more than once, I am not opposed to falling in love again. But since Ariadne was taken away from me by my now bitch of a dead ex-boss, there had been no-one I wanted to be with as much as I’d been with Ariadne. The one possible exception to this was Dr. Hellruy; if she asked me to be her boyfriend then I would consider it most seriously. As I scrolled through the list of women who had only recently been added, I came across a girl called Jazz. I looked at Jazz’ profile and found myself thinking that she was actually a very hot girl. As I clicked on the ‘About me’ tab, I noticed something which caught my attention.

At the top of the tab there were three words written in all-caps:

I AM TRANS

I looked at the picture again and could not believe that such a good looking and hot girl could be Trans. I read the rest of her profile which stated that she wanted to get laid for the first time since her transition. I clicked on the ‘Make an appointment’ tab and did not have long to wait before the replied:

Office in 10 minutes

I smiled and as I got out of bed, I noticed that my cock had gotten rock-hard. “Guess I think she’s hotter than I initially thought” I said as I slipped into my sandals and grabbed my lanyard and put the iPad in the drawer. I also grabbed the condoms and slipped them into my pocket just in case Jazz wanted me to use them. And as always, when I left the ward, I could feel the nurses staring at my ass as I left, which was nice as it always is. I made my way down to the office and got there with 8 minutes to spare. I sat in the armchair and waited for Jazz to show up. As I did, I quickly realised that this would be a first for me being with a Trans girl who looked good.

I have to admit at this point that when I first read that she was Trans, I was somewhat hesitant to meet her but her picture looked so good I went ahead with it. I never had any kind of prejudice towards Trans people, it’s just that meeting Jazz would be the first time I’ve ever met or done anything sexual with one. I guess that finding Jazz to be good looking was strong enough to dissuade any kind of prejudice before it could take hold. I thought that this was similar to when I fucked a much older woman; my preconceived notions about being with a much older woman evaporated when I met her; I hoped that the same was true for Jazz. I got up from the armchair and got myself a soda from the fridge.

As I opened it and took a sip I repressed a yawn. I did not realize that I was as tired as I was. As I repressed another yawn, I made a mental note to ask Eliza about having a day off to just rest and sleep. I really did so very fucking much enjoy my job at the hospital, but having a day off just to rest and relax was just what I needed. I sat in the armchair and looked around the office. It looked good now that it had been personalised and looked more homely and comfortable. I sipped the soda and wondered how on Earth Eliza managed to get everything for the office without anyone finding out. However she did it, be it by legal or illegal means, I had to admit that she made the Office just right.

“Jay, are you in there?” came a voice from outside the door, shaking me from my thoughts. “Yes Jazz, I’m here” I reply as I stand up. The door opens and Jazz enters the room, closing the door behind her. She had ark brown eyes and black hair. According to her profile on the website, her measurements were 34-27-35 inches. She stood at 5’2 tall and her bra size was 34B. “You look so much better in person” I say with a smile “Though your profile picture was very hot”. Jazz smiles at me and replies “Thank-you Jay, you’re much better in person to”. I indicated the couch and said “Please have a seat”. Jazz stepped up to my and stuck her hand down my pajama bottoms and inside my boxer shorts

She smiled as she gently grabbed and gently squeezed my cock. “This feels good” Jazz says with a smile “Now let’s see how it tastes”. She pulls my pajama bottoms and boxershorts down and kneels down in front of me and says “You just stand there and try not to let your knees go weak”. I watched as she then parted her lips as she raised the head of my now-fully-erect cock to her mouth. She kissed the tip of my cock then with a wink, she pursed her lips into a bow and slipped the tight fleshy ‘O’ around the tip of my cock. Smoothly, she continued to skin down the shaft, taking the prong deeper into her wet maw to the accompaniment of my pleasured hiss. I groaned in pleasure as she took all of my cock into her mouth.

She looked up at me and I met her gaze with a lust filled one of my own reached out with a gentle hand to stroke her hair. I had to admit that Jazz gave fantastic head; a fact that I had to point out to her. “You suck cock real good” I tell her “This is real good head”. She stopped the blowjob and said “I’m glad you like it”. She then winked at me before she resumed the blowjob. After a few moments, I took hold of her head with both hands, not roughly, but firmly, and began to direct her movements. I closed my eyes and enjoyed the feeling of Jazz’ mouth moving up and down my rock-hard cock. As I enjoyed the oral workings of the trans-girl, I began to wonder if there were other trans-girls that were as good looking as Jazz was.

If there were other Trans-girls as hot as Jazz then I could not see a reason why I could not fuck them; if they were listed on the website. Even though she had my cock in her mouth, I still found it a little hard to believe that Jazz was Trans. If it had not said so on her profile then I would not have known. I looked down at Jazz and smiled at her as she looked up at me. This was so fucking hot having her look up and smile at me as best as she could with my cock in her mouth. “Oh god, I’m not going to be able to last much longer” I groan “Oh GOD I’m going to cum”. And just a few seconds later, that is exactly what I did. I groaned in pleasure as my cock shot its roping ejaculate directly into her esophagus.

I grunted in pleasure as my cum shot down her throat and towards its objective in her chubby yet still hot tummy. “Wow ... that was fucking amazing” I said as I leaned against the desk to steady myself, to which Jazz replied as she took her mouth off my cock “Indeed it was”. She gets up off her knees and asks “Do you have any water or a soda?”. I nod and point to the fridge and reply “Help yourself”. As she walks to the fridge she says “You can go ahead and remove your clothes”. I nod and reply “Sure thing”. I hurriedly strip out of my clothes as she gets a bottle of water. “Where would you like me?” I ask, to which Jazz replies “On the couch laying down if you please”.

I did as she said and laid down on the couch. She opened the bottle of water and took a swing. She rinsed her mouth out then spat the water into the sink. She did this a few times to make sure that there was none of my cum left in her mouth. “Can’t have any cum left when we kiss” she says as she uses the last of the water to rise her mouth out “Your cum is only for my mouth, ass and cunt”. She tossed the empty bottle into the trash and asked me “Ready for round two?”. I nodded and replied “I’m ready to go when you are”. She smiled then began to get undressed, and just when I thought she’d get naked, she stopped at her underwear, which was a plain black lace matching bra and panties set.