tagTranssexuals & CrossdressersAnal Addiction Ch. 03

Anal Addiction Ch. 03


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.


It was after 9PM when I got home from work. As I walked in the front door of my apartment and set my keys down I thought about Nina. It had been two days since we had gotten together and I hadn't heard from her since. She had said that she would text me and I knew that two days wasn't a long time but after she had fucked me on Saturday night I had been thinking about her a lot.

Being with Nina had solidified something in me that had changed that night at Wendy's apartment: I was addicted to receiving anal sex from a girl. The role reversal of being on the receiving end and the feeling of Nina's cock sliding in and out of my ass proved to me that I needed something more than a genetic girl could offer. I needed girl cock. And after one night with Nina I felt like I had found that and a whole lot more.

I felt my cock begin to get hard as I thought about Nina. That seemed to happen all the time over the last couple days but now that I was not in public or at work I just decided to go with it. Unzipping my pants and fishing my semi-hard cock out I sat down on the couch and let it lay against my leg. As I looked down at it I thought about how much longer and thicker Nina's cock was even though I had a respectable seven inches.

I suddenly had an idea. I slid my phone out of my pocket and typed out a text message.

Me: Hey Nina, how are you?

I quickly pressed the green send button.

Laying back on the couch I took my semi-hard cock in my hand. As I gently began to massage it I thought about my night with Nina. I thought about how attractive she was. About how natural our sexual chemistry was. About the way she looked at me while she fucked me. My cock was almost completely hard when I felt my phone buzz. I looked down to see a text message reply.

Nina: Hey handsome! I'm still at work but heading home soon. How are things with you?

Me: Things are good with me. I was just thinking about you and all the fun we had on Saturday. ;)

Nina: Mmm, yeah, that was really fun. You are such an enthusiastic bottom!

Me: Hehe, I guess I just couldn't help myself. And speaking of my bottom... I'd love to get together again soon.

Nina: Me too! I'm really tired tonight though. It's been a long day and I'll probably only have the energy to jack off and pass out when I get home.

Me: Oh I didn't necessarily mean we should get together tonight. This wasn't a booty call or anything. But the thought of you jacking off is a real turn on. :)

Nina: Oh really? You'd like to watch me stroke it?

Me: That would be hot! Although I'm not sure I could just sit back and watch. I would definitely want to put it in my mouth... and my ass.

Nina: Mmm, I'd love to lay back and have your lips wrapped around my cock right now!

Our text message conversation was really turning me on. My cock was now hard as a rock. Maybe I could convince Nina to get together with me sooner rather than later.

Me: I'm more than willing to swing by your place tonight...

Nina: That's so tempting! Unfortunately I don't really have the energy to entertain tonight. I really just want to get off quickly and go to bed.

I didn't know if it was my extreme horniness or if something had changed in me but suddenly I just needed her cock. I wanted it in my ass but I would settle for whatever I could get.

Me: You are more than welcome to stop by my apartment on your way home. I promise to do all the work and make it quick!

Nina: Really? That would be amazing!

Me: Yes really. I'll text you my address.

Nina: You are a God-send! I'll head out from the office in about 15 min.

I texted Nina my address and then waited. Did I really just offer to please her sexually with nothing in return? I shook my head in disbelief that I would be excited to suck her dick without something more happening. Reaching down I took my hard cock in my hand and smiled as I felt it pulse with my heartbeat. A few minutes later I got a text.

Nina: On my way. Be there in 10.

I got up and walked around. I was really excited. Pacing back and forth around my apartment it seemed like no time had passed before I got another text.

Nina: I'm out front. Should I park or do you want to just come out?

I had assumed she would come in but from her question it was clear that she wanted to do things as quickly as possible. Besides, I was too horny to wait even a second longer than necessary.

Me: I'll come out.

Tucking my hard cock back into my pants I practically ran out the front door. Exiting the front gate of my apartment complex I saw a black sports car stopped right in front of my building. Walking over I opened the passenger side door and climbed in.

Looking over at Nina I smiled. "Thanks for coming by," I said.

"Thanks for inviting me!" She replied enthusiastically. "Your texts were really turning me on! Check it out," she said as she grabbed my hand. "I'm already hard."

She placed my hand on her pants and I could feel the bulge of her large, hard cock.

"You're not the only one," I said with a small chuckle.

"Yeah, I noticed," Nina commented with a smile. "You had a tent in your pants just walking towards the car."

She reached over and placed her hand on top of my hard cock. Giving it a quick rub she smiled at me seductively. Suddenly I wanted her cock in my mouth as soon as possible.

"Why don't you head over there," I said as I pointed down the block. "There is an alley behind that building where we should have a little privacy."

She nodded and put her hands back on the steering wheel. Driving down the street she pulled into the alley I had indicated and then turned the car off. As soon as she did I leaned over and put my lips to hers. She immediately responded by pulling me closer. Her mouth opened and her tongue swirled with mine. Chest to chest we kissed like we were long lost lovers reunited at last.

Meanwhile I moved my hand off her cock and attacked the button of her pants. A few seconds later Nina reached down and assisted me with getting her pants undone. Breaking our kiss she leaned back and lifted her ass, sliding her pants and panties down to her knees in one quick motion. With Nina's smooth hard cock now bare in the moonlight I smiled at her and then I leaned my head down.

I swiftly took the head of Nina's cock in my mouth as she moaned above me. Swirling my tongue over it I slid my mouth down and sucked in the first few inches of her shaft. Pulling my head back up I wasted no time getting into it and in seconds I was bobbing up and down on her cock. It tasted good. More musky than the last time we were together but that just meant more of Nina's feminine scent. With my saliva making her cock slick I increased the pace of my sucking.

Using one hand to play with her balls I brought my other hand down and rubbed my own cock. As the volume of Nina's moans increased I unzipped my pants and let my hard cock out. As I stroked it I started to take more and more of Nina's cock in my mouth. With every down stroke I took another half inch and after a minute or two I had almost the whole thing in my mouth. It pushed against my throat with every downward thrust and Nina gave me encouragement.

"That's it," she breathed between moans. "Take that cock."

Her words stoked the fires of my lust and I drove my head down harder into her lap. Relaxing my throat muscles I pushed down steadily until I had to come back up for air. Repeating the motion a few times I was able to take more of her cock than ever before. The increasing volume of Nina's moans above me told me I was doing well which only turned me on more. Before long I found myself moaning as much as she was.

The loud sounds of my slurping her cock echoed through the car. I focused on keeping my lips tight around her shaft as I slid my mouth from the head of her cock down to the base. After a few seconds Nina began lifting her hips to meet my mouth and from her increased breathing I knew that she wouldn't last much longer. She quickly let me know that she was close.

"I'm almost... there," she moaned. "Stroke it baby."

Placing my hand at the base of her cock I squeezed and slid it up. Using my tongue on the head of her cock I milked her shaft with my hand. Up and down I went, using my saliva to provide lubrication. I furiously pumped my own hard member as I stroked and sucked Nina's cock. Nina began to buck her hips in rhythm with my mouth and then she let out a loud moan.

Nina's cock exploded in my mouth. Her warm, sticky cum flooded into me with force. With each beat of her heart I felt more of her seed splash against my tongue. I continued to pump her cock with my hand as her warm cum filled my mouth. It took a while but slowly the flow began to subside and I worked my throat muscles to swallow everything in my mouth. It must have been a big load as it took me multiple swallows to get it all down.

As Nina collapsed back in her seat I slowly removed my mouth from her cock and then kissed the tip. Leaning back in the passenger seat I smiled over at her. "How was that?" I asked.

"Amazing," she said with exhaustion. "You are very orally talented!"

I surged with pride at the compliment. I even felt my cock twitch in my hand. Nina must have noticed too because she looked down to see it standing up in my lap.

"Sucking my dick turns you on that much huh?" At a smile from me she continued, "Can I watch you finish yourself off?"

"Right now?" I asked.

"Yeah, I want to watch you jack off after taking my full load."

I smiled and then started stroking my hard cock. As I did I looked over at Nina to see her intently watching my hand slide up and down. She had a small smile on her face. Looking down in her lap I saw her large, semi-hard cock laying across her leg. It was still shiny from my saliva and I focused on it as I increased the pace of my stroking. I couldn't believe that just looking at Nina's spent cock would be such a turn on.

Nina leaned over and opened up the glove box. Pulling out a few tissues she handed them to me and then leaned back to continue watching. No one had ever watched me masturbate before but I found it strangely exciting. The interested look on Nina's face as I stroked myself thrilled me. I began to pump my cock faster under her watchful eye and I quickly reached a point at which I needed one more thing to get me to orgasm.

I quickly unbuckled my pants. Then I pulled my hard cock back through the hole in my underwear. In one smooth motion I slid my pants and underwear down to my knees and immediately went back to stroking my cock. I brought my other hand down past my balls and began rubbing my asshole. I let out a moan as I quickly pushed a finger in and felt my anal ring tighten around it. With a finger penetrating my ass and my hand sliding up and down my cock I felt myself rapidly approach orgasm.

I leaned back in the passenger seat as I came. My ass tightened around my finger and my whole body jerked as spurt after spurt of cum filled the tissues on my stomach. I didn't cum as hard as I did on Saturday night but it was definitely a bigger load than when I masturbated alone. I kept stroking my cock until I felt the last drops of cum leak out. When I was done I collapsed back into the seat and tried to catch my breath.

"That was hot!" Nina said beside me. "I love that you wanted something in your ass."

I smiled at that even as I had wished for it to be her cock filling my ass when I came. A few seconds later Nina pulled up her pants and started the car. I pulled mine up too as she turned the car around. Stopping in front of my building I leaned over and gave her a kiss.

"Thanks again for coming," I said.

"Anytime," She replied with a smile. "And let's get together at my place again soon. I gotta get more of that sweet ass!"

I laughed and said, "You got it. Talk soon."

I headed inside and collapsed on the couch. That was amazing. I had never done anything like that before but it was a great experience. I never would have guessed that I could get so turned on sucking dick. I would have rather had it in my ass but the grateful look on Nina's face after I swallowed her full load was worth it. I couldn't wait to see her again. Walking back into my room I went to bed happy that night.

The next couple of days passed slowly. I wasn't that busy at work so I constantly found myself daydreaming about Nina and her large cock. One day I even had to go home on my lunch break to masturbate and relieve the pressure. Every night after dinner I watched transsexual porn while I pumped my dildo in and out of my ass until I came. My anal obsession seemed to grow by the day.

On Friday I got home from work around eight. As I walked in the door I felt my phone buzz in my pocket. Fishing it out I looked down to see a text message from my friend Mike.

Mike: Hey man, want to grab a drink tonight?

I smiled. Mike and I had been friends for more than ten years and even though we lived down the street from each other we rarely hung out anymore. I figured that he must be single again if he wanted to go grab a drink.

Me: Sure, when and where?

Mike: How about now? The Corner Bar?

Me: I'll be there in thirty.

I grabbed a quick snack from the kitchen and then jumped in the shower. The Corner Bar was a short five minute drive from my apartment and in no time I was on my way. Pulling up to the bar I smiled at the same old faded sign out front as I entered. Looking around I saw Mike waving to me from the other side of the room. As I walked over I saw Mike pay the bartender for two beers and then pick one up. He handed it to me and then picked up his own.

"To women," he said with a smile as he touched his glass to mine and then raised it.

I laughed. "To women," I repeated and then I took a swig.

After Mike had taken a drink he looked over at me. "Judy broke up with me," he said as an explanation for the sudden invite to drinks. "Said I wasn't putting in the effort anymore."

"Is that true?" I asked.

"Yeah, probably" he said with a shrug. "OK, definitely. We just lost the spark somewhere along the way. I mean, when we first got together we fucked like rabbits." A smile crossed his face. "Every position imaginable. It was unbelievable! But we just don't do it anymore."

"So it was just about sex?"

"No, yes, I don't know. It was everything really." He paused and looked me over. "You look like you're getting laid."

Was it that obvious? "Yeah, here and there," I said nonchalantly.

"Tiffany right?"

"Oh no, we broke up a couple weeks ago. This is something new."

Mike smiled. "What's her name?"

I smiled back. "Nina."

"She sounds hot," Mike said jokingly. "Is it serious?"

"We just met."

"Good," Mike said as he turned and looked around the bar. "Because we are both getting laid tonight!"

I couldn't help but laugh at Mike's comment. As I followed his gaze around the bar I saw that there were a number of cute girls there already. I saw a good looking brunette standing with her friends about twenty feet away and I smiled. She was definitely my type. Then the next thought that popped into my head was 'I hope she has a dick.' I almost dropped my drink.

I had never had that thought about a random girl before. I guess being with Wendy and then Nina had unlocked a desire inside me that I didn't even know was there. I looked back over at the brunette. It felt so weird to fantasize about her having a cock. To imagine being on my knees sucking it. To imagine looking back at her as she fucked me from behind. I shook my head to clear those thoughts.

"Everything OK?" Mike asked.

"Yeah," I said distractedly. "So who do you have your eye on tonight?" I asked him so I could change the subject in my head.

"That brunette is cute," he said as he nodded towards the girl I had been looking at. "Anyone else in that group look interesting to you?"

I looked at the group of girls. There were four of them standing together talking. "I'll figure it out as we go," I said.

We walked over and Mike quickly struck up a conversation with the brunette. I ended up talking to a short, blonde girl for a while and although she was attractive we didn't really hit it off. I found myself glancing over at the brunette from time to time and going back to my original thoughts about her. She would definitely be perfect if there was a dick hiding under that skirt.

After about thirty minutes of general small talk I excused myself and headed back to the bar. I bought drinks for myself and Mike and then I returned to the group to hand him the beer. After that I just walked around the bar for a while. I struck up a conversation with an attractive older woman for a few minutes but when her friends returned from the bathroom they all left.

As I circled the bar again I suddenly thought about Nina. We had been together twice now and the sex was unbelievable. I don't think I had ever been that sexually compatible with someone. Her playful personality and her sexual aggressiveness were the perfect combination. The more I thought about her the more I had to hide the growing erection in my pants.

On my third lap around the bar I felt my phone vibrate in my pocket. Pulling it out I saw that it was a text from Nina. Speak of the devil.

Nina: Hey handsome!

I stopped next to an empty booth and composed a reply.

Me: Hey there! How are you?

Nina: I'm good. Sitting here talking to a friend about you.

Me: Oh yeah? What about?

Nina: I was telling her about last Saturday night. Then I started telling her about how you sucked me off in the car the other night. It's making me super horny. Any interest in coming over right now?

Me: Yes! Your friend doesn't mind?

Nina: Not at all. She told me she is getting wet just hearing about it.

Me: Sounds good to me!

Nina: Great! Hurry over and just come in when you get here, the door will be unlocked.

I walked over to let Mike know I was leaving. He looked at me questioningly but I could tell that he just wanted to keep talking to the brunette. I reassured him that everything was good and then I left. It took about ten minutes to drive to Nina's place and when I got there I took the back staircase. At her door I knocked once to let her know I was there and then I pushed it open. Letting my eyes adjust to the low light of her apartment I slipped my shoes off and looked towards the couch.

Nina sat at one end of the couch and her female friend sat at the other. They were both looking over at me since they had been expecting me. Nina was wearing a tight t-shirt with no bra and had a blanket draped over her lap. Her friend was wearing a thin-strapped tank top over jeans. She had curly brown hair that was tied up in a messy bun and from where I stood she looked pretty attractive.

"Thank goodness you are finally here!" Nina said with a smile. "We have been talking about sex for the past hour and I'm so horny. Do you want to sit on my cock?"

Before I could answer she threw the blanket back to expose her hard cock standing up in her lap.

"I'd love to," I said with a chuckle as I walked towards the couch. I couldn't help but focus on Nina's big, beautiful cock as I got closer. It was standing straight up and there was a glistening bead of precum on the tip. I couldn't wait to have it in my ass.

As I passed her friend I extended my hand and introduced myself. She told me that her name was Brittany and now that I could see her up close I realized that she really was as attractive as I had initially thought. The high cheekbones in her slender face brought the focus to her beautiful blue eyes. With a ready smile she told me how much she had heard about me.

"OK, enough small talk," Nina said as she looked at me charmingly. "You should really take those pants off." She gave her dick a little shake to bring my attention back down to her cock.

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byTallnhard1© 9 comments/ 40806 views/ 76 favorites

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