Hampton Heights

Rick left quickly as I played on the couch trying to get my back right. It was sore but not painful as it was. I figured I had about terminated before he came back too. I pushed away the negative thoughts about something going in my butt with the idea Rick was going to be mortified about wearing something he hated.

Walking in the door I saw Rick carrying a small black leather bag. He smiled as he put it on the kitchen table. "Okay. First, I need you to shower and clean yourself. Then use the lube and then we can do this."

"We?" I asked, suddenly realizing that he was going to be involved in the toy being inserted in my ass.

"Ohhh yes. There is no way I am going to be strutting around in those hideous clothes without proper confirmation you tried it and did it correctly." He added standing firm and his tone sounding the same.

"Fine." I conceded, still hoping to get what I wanted out of this bet. I knew it was weird and more than I bargained for but I couldn't give up now.

I got up and saw the cleaning tool and went into the show to give Rick a smile as I left to shower. I was not about to let him win no matter what. I knew I wasn't giving up anything but still felt that I had to go through with it. What was the damage if I did? I asked myself as nobody would ever find out.

I was out of the shower all cleaned. I never did that before and it was strange but necessary. I knew I had to do this now as I had come this far. I saw Rick waiting for me as I stepped out with just a towel around my waist.

"In the bedroom. Let me get a towel too. I don't want you so cum on your sheets."

"Confident, are we?" I asked as I could hear it in his one that he knew he was right.

"I am. I also want a new walk-in closet if I am right."

"Okay. Fine. I can do that, but I am going to win." I replied knowing I had to win this bet, even though I knew I was probably going to help him with his closet anyway.

"Let's get you on your knees and then we can start."

"On my knees like I am being fucked." I asked wondering how gay this was getting and if there was another way.

"Doesn't matter to me. On your back works fine but that means you will be fully exposed. This way I won't really see anything."

"I don't care. You aren't going to do anything are you? I mean, you're not going to grab me or something?" I asked knowing that he was going to see my package no matter what.

"Oh, stop. I am not going to touch anything that you don't want touched." Rick joked back.

"Let's do this then." I said as I laid on my back. My soft penis flopping to the side exposed to another man in a sexual way.

"Mmmm, it is a very nice dick. I won't touch it. I swear, but I will make it cum. Now it might get hard or it might stay soft when I use the toy. Everyone is different."

I nodded my head as I watched him take out the curved toy and a bottle of Astroglide. The toy was a black plastic curved thing with a small bulge at the top. It was not overly thick and the tip had a ball shape to it.

"This is going to be cold and I am going to use my fingers to get you lubed. Don't freak out with me touching you."

I couldn't believe I was doing this and I felt like I needed to stop. I had gone so far and now I felt like I was doing some strange gay induction ritual now. I thought about saying no and having him leave but a part of me knew it would kill the friendship in some way. I didn't want to hurt his feelings and felt like I had to finish this even though I was not wanting it now.

The sensation of his fingers on my anal opening was beyond strange. He was using two cold fingers to circle my anal entrance with entering me. I then felt a finger slide in me. It just slipped in using the lube as a way to just glide in. It felt different and yet weird having something enter my ass.

"Relax. It's just a finger. I need to get your muscles lubricated and then adjust them for something bigger." He said in a soothing calm voice.

I nodded my head as I felt his finger go deeper, giving into a sensation of a slight dull pressure in my rectum that was not bad either. It then moved around my anal passage before being pulled out.

"This is so fucking weird. I can believe I am doing this." I commented, knowing that I was in for a penny in for a pound.

He put more lube on his finger and then I felt his finger slide right in me again. There was no teasing the second time as I just shoved it right in me. There was not a single cringe of pain either as his finger plunged in me making my ass its home while he explored my anal depths.

He then began fucking me with his finger. My eyes opened wide as I felt his finger sliding it and out of me like my ass was a fuck toy. I felt a twinge of fullness and yet no pain as it was like asshole was accepting of it. I could swear my ass was liking it slightly too.

"You're almost ready." He stated calmly as I felt a bit of pressure from his finger.

Pulling his finger out he wiped it clean on the towel and then grabbed the toy. "Now, relax when it's in. Don't clench your ass muscles at all. Let your body go limp and enjoy. No pushing either. You have to make sure you don't tighten your muscles no matter what."

I watched him add more lubricant to the toy and then spread it around. It was almost like being in the doctor's office and doing a test but instead of the test, I was about to get my ass fucked by a toy. I breathed in slowly, relaxing, steadying my mind and not tensing up. I kept my breathing steady and my nerves calm knowing that I had to not flinch or react as he put the toy in me.

The sensation of the tip of the toy at my anal ring was there as he put more pressure to enter me. It was like something not supposed to enter me trying to get in and there was nothing I could do as my lubricated anal ring was giving up without a fight. It was only for a split second before I felt this and fullness inside of me. An instant sensation of something large inside of my ass came to me. My whole lower waist felt an overwhelming sensation of pressure like I had something in me that I was supposed to push out.

Rick was not smiling as he had a face that seemed to be concentrating on something. "It's in. Now keep relaxed as I do this. Trust me, you will love it."

I nodded again as I felt the toy slide deeper and deeper and then stopped to retreat. It was weird as I swear, I could feel every inch and it seemed to be so much longer and thicker than it really was. It was like my asshole had a heightened sense when something was inside of it and responded with letting it bring pleasure.

The sensation to push was so overwhelming I needed to breathe deeply so I would not clench or push out the toy. The pressure in my rectum was so pronounced I felt like I was taking a shit that wouldn't come out. With all the senses in my ass going off like alarm bells, I felt the full numbness take over me and it gave me a sense of fullness in me that was calming.

"Going to go slow until you're ready." He cooed as I felt the toy now sliding in and out of my anal passage.

I was having a strange sensation as I was not in pain at all but feeling my ass respond to the intruder like it was enjoying having something inserted into it. The pressure and fullness of the toy was a strange feeling to get used to, but not unpleasant at all. It felt like a soothing sensation inside of me as he slid it in and out of me. When the tip went deep, I could feel my body respond to it. My cock was soft but I could feel the pleasure of something inside of me. It was an odd sensation of pleasure too as the tip seemed to rub against something that was making my climax sensors go haywire since my cock was soft.

My mouth opened as I wanted to say something but nothing came out. The bulbous tip of the toy was hitting something in me that I knew had to be my prostate. Each nudge he gave made my insides feel good too. It was like a buildup of sexual energy in my ass that needed something to rub it.

My soft limp dick just staying that was as I felt this toy just fucking me. Rick was not going fast but a steady slow pace which went deep each time. I could not believe that this toy was feeling so good too. It was like I was bound to it for giving me sexual pleasure too.

The steady in and out seemed to transform my anal muscles into something different now. It was nudging on something deep too. It wasn't every thrust he would hit it but when he did it was like something in me was going to burst.

"You feel it? Feeling good?" He asked, smiling as if he knew it would feel good.

"Yess. It...fuck...it feels good." I moaned, unable not to moan as the toy seemed to slide in so perfectly now. I was being ass fucked by it and accepting it too.

I had no idea that something in my ass could feel so good. It was like having dirty kinky sex while doing the most taboo things I felt. I want to say no, but my eyes closed giving into the enormous sensation of ecstasy in my rectum. He seemed to find the spot after a minute as each push of the toy was like hitting a button in my body that could only be reached with it being in my ass.

"Knew you would like it. Now let me make you cum."

He began going a little faster and then faster as I felt my anal muscles want to tighten up and push out but couldn't. I stayed relaxed giving into the fact I was having my ass fucked with a toy and the pressure to cum while soft was coming on fast. I felt like I had to piss and yet it was not hard at all. My dick showed no signs of life and yet I wanted to ejaculate badly as I felt the urge to cum. It was such an odd feeling of wanting to orgasm and not having an erection to do it.

The further he went the more I felt I had to piss. I closed my eyes enjoying this sensation when I heard him. "Ohh damm, you're leaking. Almost there."

My eyes opened fast as I just saw my limp member hanging to the side dribbling clear cum out of it like it was being forced to in the most pleasurable way. My anal hole felt like it was being fucked and the urge to tighten up was so strong too. I focused on staying calm as the urge to orgasm was there and yet I had no idea why I wanted to cum. It was like an urge to piss and cum at the same time.

The toy was nudging and rubbing something inside of me and then I felt it. My body began to shake as I looked at him with wide eyes shocked that I was feeling an orgasm.

"Yes...you're cumming." Rick announced smiling at me as I could not help but give into my body's demand for release.

"Ohhhhhhhh." I moaned not caring that he was hearing me accept that my ass being fucked with a toy felt good to me. It seemed involuntary that I moaned too as I felt my ass just loving the sensation of being fucked.

The immense pleasure of it was too much as my eyes closed from the intensity. I felt my orgasm rip through me and yet my soft dick just laid there helpless giving out my cum like it was being milked without some much as a gentle stroke. I pushed back unable to hold it any more as I wanted it harder knowing that the taboo act was more amazing that I wanted to admit. My whole body tightened up as I felt my body shudder and then shake from what was happening to it.

"Oh, my God...it's a lot. Wow, I never seen a dick cum so much from that."

I opened my eyes feeling weak, like someone stole every bit of energy my body had. I finally looked down to see my cum all over my leg and my waist. It was like I was drunk and tired at the same time. I only wanted to sleep I was so tired.

Feeling groggy I muttered out. "Guess, you win. I am going to clean up and take a nap."

"Okay. I will let you be. We will talk about my renovations later." He replied seemingly happy as I knew he was since he won the bet.

Rick left my place and I cleaned myself up in the shower. My ass felt numb and loose while I cleaned up too. It was not a painful feeling at all but a different feeling I never had before. I wiped myself of all of the lubrication he used and then finally passed out asleep.

***

I knew Rick was wanting to update his place and after a couple of days I was over to see what he wanted done. I walked in to see him smile and then after a talk about his place he showed me what he wanted done.

He never once mentioned winning the bet or gloated that he won either. I finally had to admit he was right. "You know, I never knew it could feel like that. Now, I am never going to admit it, but I did like it."

He waved his hand at me like it was no big deal. "Ohh, your secret is safe with me. I like doing it from time to time too. But I always prefer the real thing over a toy."

"The real thing feels different? Not that I am going to ask or try it...just being curious." I asked knowing that I did not find Rick at all attractive or would even consider having another man fuck me.

"Ohh, God yes. Way better...nothing like it in the world. Now I like to be on top, but I did let a few guys do me. I am sorry, I know you don't want to hear about gay sex."

I shook my head knowing that I was already down the rabbit hole and couldn't fault a Gay man for liking it now. I felt I didn't want to try with another man but could understand the sensations they felt.

"Oh, its fine. I don't mind at all now, but I am still not going to let another man fuck me. I draw the line at toys." I replied feeling that a girl using a strap-on would be the furthest taboo partially gay act I would do.

"Well, I can tell you that you feel everything and it is way more sensual and erotic."

I nodded my head and then began to take measurements of what he wanted done. It was not a big project but it was definitely a day and a half job that would have run him a little over a thousand. I didn't mind and he did win the bet.

I started the next day as I figured I had an easy week to do side projects. I only needed to show up to sign the checks for the guys I had working for me and help only if they needed me. It was an easy week for them, so it was like a week off for me.

The job went fast before I knew it the day was done and so was the project. He had a new closet and I also decided to install some extra features in his living room. When he came home he was ecstatic that the job was done so quickly and that it was better than he wanted.

I took him up on the offer to have dinner at his place and was soon treated to a nice steak dinner. Rick was our top grill guy for Saturdays and he knew how to make it like you were eating at a top place steak house.

As we sat down he sipped his wine and asked. "You know, I was thinking about what you said about your limits with just toys."

Thinking he was going to ask to fuck me I prepared myself to decline him in the most polite manner. "You know guys don't do nothing for me. I would be so turned off by that it wouldn't work."

He put his wine down. "I know, I know. It's not that. Have you ever seen a transgender?"

"A what?" My mouth almost dropped at the thought of some guy dressed like a girl wanting to bone me in the ass.

"You know, someone that identifies with being a girl. But don't worry about the man part. Jessica is all girl. She still has her stuff though, but that's the only thing that would give her away. She is the only trans girl I know that likes to top men."

"Are you serious?" My mind was wondering what I was getting into. I never watched shemale porn before but thought that this girl was some trans girl that looked and sounded like a man who dressed like a girl.

Rick gave a big gloating smile know. "Ohhh you will love Jessica. She is so freaking beautiful, I mean like super model beautiful. Once you see her, you will change your mind. She's a freaking model...you will love her."

"Does she look like a girl or a guy, or does she sound like a guy? I don't know about this."

Rick still smiling at me. "Ohh, she looks all woman. Like I said...she is a model and nobody questions her appearance. Jessica would be perfect for you. I have known her for years and she loves guys like you."

"Like me?"

"She is verse but prefers topping men. She also likes men that aren't necessarily interested in trans girls. I know it's weird, but it's her thing not mine."

The conversation seemed to be going sideways and I waved my hand to show that I was not interested in some strange girl that probably had the body of some neutral gender that sounded like man. "This sounds too strange."

Rick then got up and turned on his phone flipping with his finger on the screen. He then walked over handing me the phone. "Oh stop. Here. What girl would you think is Jessica?"

The picture was of two girls and they were both gorgeous. It looked like a picture taken by a modeling agency too as they had their makeup and hair done perfectly. The one girl was a redhead and the other was a tan with long black hair and striking blue eyes. The redhead was pale but not too pale and had a pixie cut that made her face look super cute. The girl with black hair had a face that was no way be considered manly. Both girls looked stacked in the chest department too as the shirts they were wearing clung to their perfect bodies.

I was at a loss since both girls looked like models and seemed to be the furthest thing from looking like a man. Studying their breasts and jawline I looked for signs of surgery but knew I had no expertise to spot it. Giving up I shook my head. "I have no idea."

"They are both trans. They are professional models too. Sarah has a boyfriend and wont top anyway, but Jessica has a kinky side. She got drunk one night and spilled the beans about what she likes. I will call her, she owes me a favor too."

My mind now wondered why she would be interested in me if she didn't want guys who liked what she was. "Are you sure this is going to work? I don't know about this."

"Trust me. I know what she likes in men, and you are her type."

"You want me to date her or just have her fuck me? I am confused."

"Well, she is not a hooker. She is also reserved when it comes to who she has sex with, but I figure it's worth a try." Rick was still animated with his hands.

I just moved the conversation not to sports not wanting to think about what he was trying to do. I finished up with packing my tools and soon found myself back at my place wondering about Jessica. I also decided to look up shemale porn. It was nice knowing that it probably felt good and some of the girls I couldn't tell if they were a guy at all. I figured I would try a single date with Jessica.

With a quick text to Rick he told me that he would get in touch with her and ask if she wasn't seeing anyone and would consider a date. I told him I was free Friday and possibly Saturday and Rick instantly said Friday as he wanted to watch the game with the guys.

The next day Rick called me up and said that Jessica said yes and that she would go out. I mentioned a bar and Rick instantly said that she wanted to go to a restaurant. Not one to argue, I agreed and told him that I would meet her at a high end steak house that I knew of. It had great food and was a nice fancy restaurant.

I dressed nice but not suit and tie nice. I even put on some cologne and decided to shave as well. The picture still ingrained in my head, I just feared that she was manly in some way or sounded like a guy disguising his voice.

Walking in, I saw a girl wearing a sleek black mini dress. Her long black hair nicely done in big curls as she had her back to me as she stood up near the bar. My eyes instantly went to her ass as the mini dress hid nothing and showed off a curve that no man could deny staring at.

In my mind it had to be her as there was no other girl at the bar and I was five minutes late. I just walked over next to her and motioned for the bartender then looked at her. Her makeup and jawline was all girl as was her chest from the side angle I had.