Anal Addiction Ch. 02

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I break up with Tiffany.
8k words
4.79
72.9k
157

Part 2 of the 4 part series

Updated 06/07/2023
Created 05/20/2015
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This story contains sex between a transsexual top and a male bottom. If you do not like stories where a man gets fucked by a transsexual please stop reading.

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I had been pacing back and forth for about ten minutes before I finally sat down on the couch. Looking at the phone in my hand I considered the call I was about to make. I should have known it would come to this at the end of that night two weeks ago. I should have just broken up with her then. But I didn't so here I was, ready to finally call her and end our relationship.

It had been two weeks since that night at Wendy's apartment. The night my girlfriend Tiffany decided to trick me into getting fucked in the ass by her transsexual friend. I still couldn't believe that she had set me up like that. It was true that I didn't necessarily have to go along with it but my pride and curiosity got the better of me. And besides, it just wasn't fair to put me in that situation.

After that night my love life had come to a screeching halt. Tiffany had pulled back from me emotionally and we weren't connecting in the way that we did before. I had lost all trust in her and she seemed to feel the same way about me. Our interactions had become awkward and the thought of being intimate with her just made me upset. I didn't know how to put things back the way they were even if I wanted to. And I didn't want to.

I sat there staring at my phone for a few more minutes before finally pressing the green call button. Listening to it ring I took a deep breath.

"Hello?"

"Hey Tiffany, it's me," I said in a short, clipped manner. "We need to talk."

"Yes we do," she replied curtly.

The tone of her response caught me slightly off guard. I paused for a moment but then I said what had been on my mind for weeks. "I've been thinking a lot about what happened that night at Wendy's apartment and I'm just not sure this relationship is going to work out because of it."

There was silence for a few seconds before she responded. "I agree. This isn't working for me anymore either."

"Ok," I said with a mixture of relief and exasperation. "Because things changed between us that night."

"Yes they did," she responded with an edge to her voice. "In ways I never expected."

What did that mean? "Look, Tiffany, you know that what happened wasn't my idea. It was your idea and then you got angry at me for doing it."

"I didn't think you would actually go through with it!" Tiffany took a deep breath to calm herself. "The fact of the matter is that I didn't want to have anal sex with you. I figured that if I pressured you to do it first then you would back off. Clearly I was wrong because you agreed to do it. Not only that, you loved it!"

I did love it. It felt weird to say it but I really did love being on the receiving end of anal sex. I wasn't going to admit that to Tiffany though. "I wouldn't say that I loved-"

"Oh please, it was obvious how much you loved it. Wendy even told me later that she had never seen a guy cum that hard before. Now whenever I think about us being together I just think about the look of bliss on your face when Wendy's cock was in your ass."

I didn't know what to say to that statement. Instead I addressed her earlier comment. "You should have just told me that you didn't want to have anal sex in the first place. We could have talked about it."

"No we couldn't. I could tell how badly you wanted it and talking about it would have just made it worse."

"That's not true..." I trailed off. This conversation was going nowhere. And ultimately it was pointless. Our relationship was broken and it was ending anyway. I took a deep breath and then said, "Whatever. It doesn't matter now. It's over."

Tiffany responded, "Yep, turns out I'm just not the right kind of girl for you."

That wasn't fair. What happened was her fault. "I guess not," I said angrily and then I hung up.

How dare she try to put our breakup on me. It was true that I had wanted to have anal sex with her and that I had mentioned it a few times but she was the one that took things too far. She was the one that put me in a compromising situation and then got upset when I made the "wrong" choice. Standing up I resumed pacing back and forth while I took a few deep breaths to calm down. I reminded myself that it no longer did me any good to be resentful because the relationship was over.

I was mad about how things ended but another part of me was sad. Sad because at one point I thought we had a great relationship. The first six months Tiffany and I had dated were fantastic. I had been really happy. But that night at Wendy's had changed me. The amazing feeling of a girl's cock in my ass had opened my eyes to a world of sexual possibilities that I didn't even know existed. Breaking up was disappointing but at the same time exciting as I looked forward to seeing where my newfound sexual interests took me.

I put my phone down and walked back through my apartment to my room. Opening up the bottom drawer of my dresser I lifted up the stack of t-shirts and reached underneath. Grabbing hold of the hard, silicone object hidden at the bottom of the drawer I pulled it out and looked at it. I never thought I would own a dildo but there I was holding one that I had bought only days before from a local sex shop.

I had always been obsessed with anal sex but suddenly my orientation to it had shifted. Where I once obsessively fantasized about my dick in a girl's ass, now all I thought about was a girl's dick in my ass. Of course that required the girl to have a dick so I was quickly becoming obsessed with transsexuals. I thought about the only transsexual that I actually knew, Wendy, and I wondered if she wanted to fuck me again.

Sitting down on my bed I thought back to the night that changed my life. When that night started I would never have guessed that I would have ended it naked on Wendy's bed. I would never have guessed that I would agree to Tiffany's deal. I couldn't help but smile as I thought about the look of confusion that must have shown on my face the moment I saw Wendy's cock. Then I thought about the look of confusion on Tiffany's face when I said that Wendy could fuck me.

As I thought about the events of that night I felt my cock begin to stir. Setting the dildo down next to me on the bed I unbuttoned my pants and slid them off. My underwear quickly followed as I lay down and closed my eyes. In my mind I replayed the moment of taking Wendy's cock in my mouth. Then the moment of her first penetrating me. Then the moment of her realization that getting fucked was making me hard.

As I reminisced I reached down and began lightly stoking my cock. I thought about the way it felt to have Wendy's hard cock sliding in and out of my ass. I was so turned on that I reached down with my other hand and began rubbing my hole. A low moan escaped my lips as the nerve endings responded to my stimulation and my cock hardened in my hand. Pushing a finger in caused me to arch my back slightly and breathe heavily through my mouth.

Removing the finger from my ass I reached over and picked up the dildo. Opening the drawer next to the bed I pulled out a small bottle of lube and quickly coated the sex toy. Spreading my legs and lifting my ass off the bed I gripped the slick dildo in my hand and brought it over to line it up with my hole. I applied firm pressure for a few seconds and then gasped as I felt the head push into me.

I was so horny that it took only seconds for me to slide the entire dildo in. Pulling it back out I began to get a rhythm going while I continued to imagine that it was Wendy's cock filling me up. I thought about being on my back and looking up at her as she thrust into me. I loved watching her devour my body with her eyes and then put all of that desire into driving her cock into me over and over again.

I knew I was going to cum when I thought about how it felt when Wendy finished. Thinking about her cock spasming in my ass as she came caused my cock to explode. I moaned loudly as the first jet of cum left my cock and sprayed across my stomach. I continued to fuck my ass with the dildo as spurt after spurt of cum covered my torso. When I finally finished cumming I slowly removed the dildo and collapsed back on the bed.

That must have been the fifth time I had done that since I bought the dildo a couple days before. It seemed like every night I masterbated to thoughts of Wendy fucking me. But for some reason things felt different all of sudden. Maybe it was the fact that I was finally single but something had definitely changed. I could feel it. Shaking off that thought I decided to get up and get ready for bed. Sliding off the bed I headed towards the shower.

A week went by and I had been thinking about Wendy even more than usual. I really wanted to contact her to see if she was interested in getting together with me again. There was only one problem: I didn't have her phone number. In fact, I didn't have any way to get in contact with her what-so-ever and I didn't even know her last name. The only thing I knew about her was her first name and where she lived.

It took a few days to work up the courage but I finally found myself standing in front of Wendy's apartment building at 8PM on a Thursday night. I didn't have the code to her front gate so I waited until I saw someone approach and then I casually followed them in. I took the elevator up to the third floor and walked towards her apartment. Standing outside her door I was suddenly nervous. Would she think I was a crazy stalker for showing up like this? Before I could think about it too much I knocked on the door.

About ten seconds passed before the door swung open. When it did Wendy stood there wearing black workout pants and a tight fitting cream-colored top. She had clearly just come back from the gym as her hair was disheveled and she had a light sheen of sweat across her forehead. Wendy made eye contact with me but it seemed to take a few seconds before she recognized me. When she did a slow smile crept over her face as she stood in the doorway and sipped her coconut water.

"It's about time. I've been expecting you every day since I talked to Tiffany last week."

I smiled mischievously and shrugged.

Wendy laughed. "Come on in."

I followed her into her apartment. It looked exactly the same as it did when I had been there a month prior. I felt an unexpected thrill walking in to the apartment where I had had the best sexual experience of my life. Wendy motioned to the couch so I took a seat opposite her. She looked as beautiful as I remembered and I couldn't help but take a peak towards her crotch to see if I could make out a bulge there.

"So here you are," Wendy said when I sat down.

"Yep, here I am," I answered.

"What took you so long?" She asked playfully.

"What do you mean?"

"When Tiffany told me last week that you guys weren't dating anymore I knew you would try to contact me. It was just so obvious how much you loved it when I was fucking you."

I didn't really know how to respond to that. It was true that I loved it but I hesitated in answering.

Wendy smiled at my hesitation. "So I assume you are here because you want to do it again?"

I was glad she stated the obvious. "Yep," I said with my most convincing smile.

Wendy leaned back against the couch. "It was really fun last time wasn't it?" She had a small smile on her face and she seemed to be looking inward and replaying it in her mind. "Your ass was so tight it was like a dream."

Her comment took me back to that night and I immediately felt a stirring in my pants. "Yeah, it was amazing," I said as I looked over at her. "I never knew that anal could feel so good."

Wendy looked over at me. "It's too bad we can't do it again."

"What? Why not?"

Wendy's eyes pinned me where I sat. "What do you mean, why not? First of all, I'm friends with Tiffany and it wouldn't feel right to do that to her. Second, as much as I enjoyed fucking you I'm not really a top. I'm versatile but I prefer to bottom so even if I didn't know Tiffany you wouldn't really be the right guy for me."

I was not expecting that response. I had actually been hopeful that she would want to jump back into bed with me. "Hold on a second," I said clearly grasping at straws. "What if Tiffany didn't know? And I love giving when it comes to anal sex so that would totally work for me."

She smiled with just her mouth. "No, I'm sorry. It's just not going to work for me." She paused and then continued. "And you may have enjoyed anal sex with genetic girls but I saw you on my dick. You love it. You would be asking for it all the time."

Deep down I knew she was right. Her reasons made sense but I couldn't help feeling massively disappointed. All I had thought about for the last month was getting fucked by Wendy again and suddenly I knew that it would never happen again.

Wendy saw the resignation on my face and she leaned over to pat my knee. "Don't worry, I'm sure you'll find someone else."

I nodded. "Yeah but I doubt I'll find someone as good looking as you with the right... equipment."

Wendy laughed. She paused and thought about something for a second. "Tell you what, I do have a friend you might like. Would you like for me to set you up with her?"

I looked at her. "Does she have the right... equipment?"

"Yes."

"Then yes!" I exclaimed.

We talked for a little bit more and then I headed home. Before I left I gave Wendy my cell phone number and thanked her profusely. She said she would make no promises but that she would talk to her friend in the next few days and if her friend was interested she would pass on my number. Wendy didn't know if her friend was currently single but she knew her well enough to know that I was more or less her type.

The next few days were the slowest of my entire life. I was excited about the possibility of meeting Wendy's friend but I knew there was a chance she wouldn't be available or interested. I tried not to dwell on it too much but it seemed like I was constantly fantasizing about someone I didn't know. Thursday night and all day Friday went by as I made sure my phone was always close at hand just in case.

On Saturday morning I got up and went for a run. Even though I had been masterbating like crazy for the last two days I still felt sexually frustrated. All week I had been gearing up to get fucked by Wendy but when that didn't happen I felt stymied. After returning from my run I showered and sat down on the couch to watch TV. It was a few minutes after 2PM when I got a text message from an unknown number.

Unknown: Hey, this is Nina. I'm a friend of Wendy's.

My heart caught in my throat. I had been thinking about getting contacted by Wendy's friend for two days straight and now it was actually happening. Picking up my phone I let my fingers hover over the keypad while I thought of what to write back.

Me: Hi, how's it going?

Nina: Good. Do you have some time to chat?

Me: Sure.

Nina: Great, I'll give you a call in a few minutes. In the meantime can you text me a picture of yourself?

Me: Sure, no problem.

I sent a picture of myself from a few months earlier and then waited for a response. About thirty seconds later I got a text message reply from Nina that consisted of a picture and the text "Nice! Here is me." The picture was a selfie taken in the bathroom mirror. The brunette girl in the photo was wearing a light blue top with a plaid skirt. She had a cute face and a nice body. I was suddenly thrilled that Nina looked like any other cute girl that I would try to talk to at a bar.

A few seconds later my phone rang. It was Nina so I slid my finger across the bottom of the screen and held the phone to my ear.

"Hello?"

"Hi," said the feminine voice on the other end of the line. "How are you?"

"Good. And you?"

"Excellent. Yeah, I got a call from Wendy yesterday and as we were talking she mentioned you as someone I might be interested in. I'm usually pretty picky when it comes to guys but from the picture you sent and Wendy's account of your time together I think we might be a fit."

I wondered what Nina meant by 'Wendy's account of your time together' but if Nina was happy about it that was good enough for me. "That's good. Yeah, you look really sexy in the picture you sent."

"Thank you." She paused for a few seconds and then said, "So I guess I'll cut right to the chase. What are you up to tonight?"

"Nothing really."

"Want to grab a drink later?"

"I would love to," I answered quickly. "What time?"

"Umm, I have to run a bunch of errands this afternoon but how about nine o'clock? There is a good bar just down the street from my apartment that I haven't been to in a while."

"Sounds good to me."

"Great!" Nina said with enthusiasm. "I'll text you the name and address of the bar when we get off the phone and then I'll see you there at nine."

We said goodbye and I hung up the phone. Standing up off the couch I did a little fist pump celebration. Even though I knew basically nothing about Nina her picture was cute and she sounded really nice on the phone. She also said that she thought we would be a good fit sexually so my mind immediately raced with all the things that could happen. When I felt my cock start to swell I had to take a deep breath and tell myself to calm down as there would plenty of time for that later.

A few minutes later Nina texted me the name and address of the bar where we were to meet. Doing a quick search for it on my phone I saw that it was a modest bar with both good and bad reviews. Most of the complaints seemed to be about the service but I was hoping I would be too focused on Nina to notice. Setting my phone down I went back to watching TV.

A few hours later I decided to start getting ready. I walked back to my room and opened the closet door. Reaching up I grabbed a box from the top shelf and brought it over to my bed. As I did I thought about the fact that the dildo wasn't the only thing that I had bought on my trip to the sex shop. The cute, blonde employee had also recommended that I buy the enema kit I was currently holding.

I had used it a few times already but I was suddenly excited because this time I would be using it and then I would get fucked for real, no toy. Carrying it into the bathroom I set it down on the counter and began to fill the basin with water. Priming the nozzle with a dab of lube I assembled the kit and then bent over the bathtub. Bringing the tip to my hole I pushed it in and let the water flow.

After cleaning myself out a few times I took a shower and cleaned every inch of my body. After that I made myself a small dinner and then got ready to go. Since we were meeting at a bar I didn't want to get too dressed up but at the same time I wanted to make a good impression. After selecting some dark jeans and a collared shirt I glanced at the clock. It was time to head out.

I pulled up to the address Nina had provided a few minutes after 9PM. I parked down the street and then walked towards the brick exterior of the bar. Pushing open the door I stepped into the dimly lit interior. I paused for a second to give my eyes a chance to adjust as I looked around. It was pretty crowded so I just started walking around the bar. In the back I saw someone in a small booth wave at me.

I immediately recognized Nina from her picture. As I got closer I got a better look at her and I smiled. She was really attractive! Even though she was dressed down in a button up black top over a tight pair of jeans she made it look good. Her body looked thinner than in the picture she sent which only increased my attraction to her. Below her long dark hair she had a cute face that smiled at my approach. I felt like I had hit the jackpot as I got closer and saw her more clearly.