Hampton Heights

"Jessica?" I asked, trying to gauge if I had the right girl and hoping I did and hoping I didn't as she would definitely be a girl I would ask out.

She turned to me with a small smile. "Are you Joe?"

The voice was all girl as there was not a hint of masculinity to it. Her breasts looked real from what I saw too. She showed some cleavage too as I tried not to look down, but they had to be a C cup at least.

"Yes. Sorry I am late."

"Oh you're fine. I just got here myself. Do you want to get a table?" She stated as I was making sure I stared at her eyes not looking down to gauge her breast size.

"Yes. Let me get a waiter."

I got a waiter and he walked us over to a table. I did the gentleman thing and pulled out her chair and then let her order her drink first. I then ordered mine and we just talked about the drive to get to this out of the way place.

She asked me what I did for a living and I did the same listening to how she was a model for a few independent agencies that did web ads. The entire time I could not tell she was anything other than a gorgeous woman. I was actively looking for hints too and just could not tell.

As the meal progressed I offered to take her to a bar or maybe some place else. That's when she put her hand up. "Look, I know Rick told you about me, but I really don't date too much. I am not going to let you take me to your place nor I am going to take you to my place for a quick fuck. I know guys just want some trans girl to fuck them to fulfill a fantasy but I am not into that."

I motioned with my hands that I was not being pushy. "Okay, okay. I had no real plans for after this and we can just call it a night. Rick just told me that you were picky and I assumed that this would be...well just this, a nice casual dinner."

She smiled as I could tell she did not want to offend me or make it seem that she was being bitchy. "Did he tell you about me? You know...all about me?"

"He did. I was hesitant about it to be honest. I just figured I would go out on a date with an attractive girl. He showed me your picture with Sarah and said you were single. I mean, we could go to the movies if you want something normal with no strings attached."

She smiled wide again and took a sip of her wine. "I am sorry, I just know Rick can be pushy about things. The movies after this is fine, I just haven't been to the movies on a date in a while. Most guys that want to take me out on a date only want one thing 'cause they have a fetish for it."

It was then that I had an idea. I knew my friend Greg works at the amusement park and always let me in at night when I wanted to hangout and ride on the rollercoasters with no crowds. I was friendly with the owner and did work for him and right now it felt like a perfect place to take her.

"Hey, I got a better idea. You like roller coasters? I can get us in at Fairview Park right now. I know the head engineer and the owner. There is nothing like being on a rollercoaster at night too."

"You serious?" Her face looked confused.

"Yea it will be fun. We can go on any ride there or just walk around and talk. After that we can go our separate ways so there is no pressure for anything else. We can just say no to anything else after now so you won't think I want anything more than to just have a fun time."

She then smiled and nodded her head. "Okay. That sounds fair."

I picked up the check without even looking at her for permission and then told her to follow me. It was only about thirty minutes away and I wanted her to drive so she knew she could leave at any time and there was no assuming that anything else had to happen. At this point I figured it would be just nice to talk to her and nothing else.

The entire ride there I just assumed I would be going home alone and would jerk off to some porn to end the night. I knew Jessica was smoking hot but also didn't want to think that I had a fetish for something I only watched a couple of videos of.

We got there and the security guard knew me and the owner was just about to leave. Since I always helped him out with repairs on his buildings for almost nothing, he turned on the lights and told me that the park was mine. The only thing we could not go on were the two bigger roller coasters that needed an attendant to turn on. The rest of the park was all ours though.

As we walked, I let her tell me about her modeling and then she delved into how she got started with her career. She showed me pictures and I got to see her in a bikini. I was just shocked that her body was perfectly fit for a string bikini. I didn't ask where the other parts went but whatever she did I could not tell that she had male parts.

As we walked around, we joked and laughed constantly. The few rides we went on she even reached for my hand. I treated her as any other date but knew that sex was off limits so I didn't try any moves. My needs would be met with my hand after this and I would not feel guilty that I tried something on a girl that didn't want it.

We got to one ride and as she slid into the seat and pressed against me the smell of her perfume got to me. It was a scent of fresh flowers and sex to my brain. I reached for her hand again and lost myself in the date as I felt like a kid again with her.

The ride was over and as we were walking out of the platform, she went the wrong way and her waist hit the turnstile stopping her abruptly. As her body stopped as I walked into her. She turned around quickly with a smile and I lost my ability to control myself. I knew I wouldn't feel right about myself if I didn't try to kiss her.

It was a leap of faith but I went for it. My head moved in slowly as I aimed my lips for hers hoping for the best. Jessica didn't move and before I knew it, I was kissing her. Her soft lips felt like heaven as I moved further and moved my tongue inside of her mouth. She wrapped her arms around me and were now making out like two kids would.

She then stopped quickly pushing me back softly and breathing deep. "I have to ask you something personal?"

I nodded and she gave a serious look. "Are you Gay or Bi? I need to know. If this goes further, I need to know what you are into."

I stepped back looking at her and only seeing a girl that I wanted to be with on any level. "I am not gay and have never been with a man or care to. Guys don't turn me on if that's what you're asking."

"Why did you want to go out with me then? Why are you pursuing this?"

"To be honest. I didn't know what to expect. I just thought I would go out on a date with a hot girl." I answered, smiling at her.

"You know, I have a penis and not a pussy. I am trans. That means you would be fucking me in my ass. I would want to fuck you as well...do you even know that?" Her voice sounded sincere as I felt she was thinking I was leading her on and teasing her.

At this point I stopped caring about what she had and that she was able to give me a prostate orgasm. I knew I had more fun with her than any other girl that I was on a date with in years. Her laugh and smile just warmed my soul and I just felt the urge to do anything with her, even if she had a dick between her legs.

"I knew that when Rick set us up."

Her smiles grew wide as she moved her hair away from her face. "Do you watch transgender...or shemale porn?"

I gave out a laugh as I really didn't watch any of that and only just saw two videos when Rick mentioned it. "I saw a couple of videos and it was only when Rick brought it up."

She moved towards me with a smile and then moved forward and I did the same as our lips met again. It was a fast kiss as I moved my tongue in her mouth before she pulled away.

"Let's go to your place then."

Driving back to my place with Jessica following me, my heart beat fast. All I could think about was that her girl dick was about to go into my ass. I had no idea a girl like Jessica could be so hot and interesting and yet have a real cock. A real-life cock was about to fuck me too I thought. Never once did I consider myself that kinky, that I would want someone to fuck me with a dick before and now i knew it was going to happen tonight. The entire way home I got an erection from the thought of her fucking me too.

Once inside we kissed like we were long lost lovers meeting for the first time. I guided her into my bedroom not breaking the kiss either. Once in my bedroom she pushed away and looked at me with the most heartwarming smile.

"I can fuck you if you want. If not, that's okay too."

I nodded my head. "Okay. But I want you to do what you want."

"Ohhh really. You do know I have a really bad kinky side." Giving a devious smile back at me.

"I don't care what you want. I just want to do this with you." I answered knowing I was fully honest and also knowing that feeling something in my ass was one of the best orgasms I ever had.

She pulled up her shirt revealing her bra. It was a small scantily clad bra that held her nice sized breasts. They seemed the perfect size pair of tits for her thin frame too. She then reached back undoing the bra showing me her uncovered chest and nipples that were erect and looked natural.

She cupped them and let them drop letting me see that they were all hers. "They are real too."

"Really?" I had to question it as all of the pictures I saw last night the girls had fake ones.

"When I was on hormones, I developed them. I just love them too." She smiled as I felt more and more that this was the right thing to do.

Her hands then reached for the waist of her mini-dress as if she was ready to reveal her real body to me. "Have you ever seen a trans-girl before?"

I shook my head being honest. She then pulled down slowly. "Please don't be upset if it's not what you were expecting. This is why I don't like people who have fetishes with girls like me. They have these expectations of what they see online."

As she pulled down her dress, I just saw her thong panties. She then reached for a clear elastic band that seemed to be holding something in place. She then looked down almost ashamed of what I might say. "I am not that big and my balls are little too."

As she pulled down her panties, I just saw a hairless void of where a dick would be of a pussy. She then pulled off a clear piece of tape and reached between her legs pulling out her junk. There was no going back I felt and no matter what I was committed to this sex act too.

Her girl dick was thin and long as it hung down as she had no pubic hair at all. Where her balls should be was just the elastic skin with a small curve to it. Her dick was skinnier than mine but about the same size of about seven inches. Her tip was nicely shaped like mine too.

I was never a connoisseur of dicks, but hers had a feminine look about it and I never knew it could be feminine. The way it was soft hanging there made it look harmless and cute to me for some reason. She was so hot looking standing in front of me and seeing her with a penis just made it almost baffling as it threw me off.

She then cringed as her hand tried to cover up her equipment. "My balls are really small...I know. I also don't get hard sometimes. Please don't be turned off. I can't do what they do in porn movies either."

As I was sitting, I motioned for her to come to me and when she did, I took a hold of her shaft instantly feeling how soft it was. It was like her skin was silk as it was so smooth too. The fact I was touching another dick went past me as I loved how hers felt in my hand too.

My brain felt like a runaway train unable to stop as I was about to do. I never once sucked a dick before nor even thought about it and yet my hand was on her soft member about to put it in my mouth. My heart pounded with the sexual tension I felt as I moved closer and closer to her member knowing it was going in my mouth.

I moved her forward a bit more and then the smell of her clean skin hit me like a calming peace of acceptance of what I was about to do. It happened so fast as I now wrapped my lips around her girl dick. It tasted a little musky but in an erotic way as it was mixed with her perfume. The feeling of her mushroom tip on my lips was adding to the moment too as I then moved further taking her all the way in.

She was soft and getting hard as I easily took her entire length in my mouth. I moved back feeling it expand in my mouth. She ran her fingers through my hair just as I took her deep once more. "Ohhhhh yess. That feels really good."

Once more I took her deep feeling the fullness in my mouth from her dick expanding. The act of sucking a cock seemed for foreign to me and yet I let out a soft moan loving the sensation of her girl flesh in my mouth as I was pleasing it. It was spongy and soft while tasting like clean flesh too. I just continued to slide my lips back and forth on her shaft and even licking the tip when I got to it. The thicker it became the more it sent in that I was sucking a cock.

"Mmmmm, yess. I love this." She moaned as I licked her crown and moved my tongue around the ridge of it before taking her almost all the way in my mouth. I then picked up my pace and even simulated fucking it with my tongue pressing the underside of her shaft.

Back and forth I went feeling her smooth shaft slide into my mouth. I was only going halfway but I pressed my lips against her cock and then would alternate using my tongue along the underside of it only to feel it pulse as a sign I was making her feel good.

She moved me away just as I was getting into it. "Let me fuck you now."

I was not going to say no and quickly undressed. As I got naked' she gave my ass a quick soft slap before I turned around. "Rick did say you have cute ass."

I then turned around and before I said anything she grabbed my soft member and looked at it. "Ohhh and you have a nice cock too."

"So you like my ass?" I asked, feeling the excitement building of what we were doing.

"You have a really cute ass. Now bend over and let me see it better." Her voice sounding sexy and yet demanding at the same time.

I got on the bed and bent over doggy style. I then heard her reach into her purse and listened to a bottle cap opening. "I will go slow at first. Let me know when to go hard okay?"

"Okay." I answered as I then felt the bed move before her hand was on my hip.

"I am not using a condom, are you okay with that. I can put one on if you want."

"I am clean." I answered not thinking straight and also not knowing what to fully expect. I thought back to Rick putting the toy into me and wondered if it was going to feel exactly the same.

Jessica then put her hand on my hip as both of her hands now had me. "Good, so am I. I really want you to like this."

"Ohhh...I feel that." I said as I felt her finger slide right into my anal entrance. It was quick too as she got her one finger in me quickly and without any pain.

"Let me just get you ready." Her voice calming as I felt her finger explore my anal depths now.

She was moving it in and out slowly and pulling out before pushing it right back in. The sensation felt good and I knew there was more to come too. Each time she pushed in, she curved her fingers as I felt it hit the spot that was going to make me climax too.

Her finger was out of me as I knew what was being inserted next. "Just breath while I fuck you. Don't struggle. Just lettttt....goooo, there you go." She said as I felt her tip seemingly pop in me quickly as she was not holding back either.

"Ohhh, dmmmmm. Ohhh shittt." I moaned, unable to hold back as I felt impaled by her girl dick. It felt different than the toy almost better as my anal hole seemingly became snug around it like it was form fitted for my ass.

The instant pressure was there as I felt her girl dick in my ass. My anal muscles were stretching from it as I realized that a real dick was in my ass. No toy, but an actual dick was now in my butthole and it felt amazing as I could feel this girl fill me so perfectly. The familiar fullness in my ass felt so good as she was not moving it but just letting my butt adjust to her girth.

My moral compass was now gone as I felt the girth of her cock slide all the way in me. My mind scrambled with the notion that this hot girl had a real cock and it was in my butt. It wasn't a strap on or some other toy she was using but a real cock to fuck me. I was letting myself be butt fucked by a transexual, and worse...it felt so good.

Her thickness was pushing open the walls of my ass letting me know that she was indeed deep in me. She was thrusting letting her hips bang against my ass bone as I felt the instant sensation of my anal hole being plugged away by her length. Each plunge of her trans cock was felt and even though her cock was thin, still felt big to me.

"Feel good?" Her voice cooed as I knew she was liking it too.

"Yesss. Oh shit, if feels good. Ohhh...wow." I softly answered as I felt so erotic that she had a real dick and it was shoved in my ass. Knowing it was only half of it too, as the sensation of it was overwhelming my senses.

"Your ass feels really good. Let me know if it starts to hurt though." She replied as I felt her girl stick now moving in and out of my anal hole slowly. I was being fucked, literally and I was liking it more than I realized.

I then felt her move her member in and out of my ass as every inch felt like a foot too. One long push followed by another as her rhythm was slow and steady as if I was being butt stuffed. Each time I swore I could feel every inch of her length too as she seemingly bottomed out in my ass. It was like an anal massage on my insides as my ass muscles stretched in a loving way to accommodate her size too. My own dick stayed limp and now began to swing from her thrusts.

"Ohhhhhh...fuckkkk." I moaned as the fullness was intense and I tried not to clench my ass muscles on her girth. It was feeling good and I stopped caring about admitting it now.

"Shhhh...relax. Breath and stay calm. Give into it. Just let yourself be fucked." She replied in a soothing voice slowing down her pace.

Then all of a sudden, her pace picked up steam. Her waist was hitting my ass harder as she was now full on fucking me. I felt her girl rod pierce through my anal cavity like I was just a hole to be fucked for her pleasure. I breathed and relaxed as I literally felt my ass hole expand and stay that way as her member pushed in and out of me. I knew my anal ring had given up like it knew that the fight was over and it needed to be just a hole for fucking now.

"Thats...it. Ohhh baby...you're really tight too. Feels really good." She moaned as I felt her waist hit my butt again and again as she was fully impaling me with each thrust now.

Back and forth she went until she was now plugging away at my anal hole. In and out in steady hard thrusts as the slapping of our bodies now filled the room. Each time her waist hit my ass bone confirming she was pounding her entire length on me making me know I was being butt fucked. I could feel her sliding in and out as my senses were a blur trying to keep up as she was going so fast now.

I relaxed as I remembered and then just let go, my mind only focused on staying calm as I felt my ass being fucked. I let go of all doubt, bad feelings, and misgivings about what was normal. I gave into the pleasure and relaxed my body in an almost zen state as Jessica plunged her girl rod in and out of me deep each time. It was like my ass was numb to it and yet I was getting a pleasurable feeling from her ass fucking me too.

Jessica moaned out as I felt her pounding away on me. "Ahhhh....ohhhh. Shit baby...feels so good."

My ass felt open and yet full at the same time, as each push in me made me want another. Her plunging girl member not stopping either as it used my ass for sexual release. I could feel the build up of my orgasm too as her girl dick hit my insides and rubbing my inner climax spot. I felt weak to her engorged member as it seemingly owned my ass for its own pleasure.