Anal Addiction Ch. 01

It was after midnight by the time I pulled up in front of her apartment. Putting the car in park I sighed and then looked over at my girlfriend Tiffany. She was sitting in the passenger seat with her legs tucked under her and her eyes on the cell phone in her lap. Glancing up she looked at her apartment building and then over at me with a disappointed look on her face.

"Home already?" she asked as she began to unbuckle her seatbelt.

"Yep, home already," I answered with a knowing nod. "You know you could have just stayed the night at my place. I'm sure we could have had some more fun tonight," I said with a smile.

Tiffany gave a lighthearted laugh. "Oh really? You were ready for another round huh?"

"Definitely!" I exclaimed as I unbuckled my own seatbelt and leaned towards her. "There are so many more fun sexual activities to try."

"Like what?" she asked in all seriousness. "We basically did everything tonight: You went down on me, I went down on you, and then we had sex in every position I thought possible. What is left to try?"

I smiled conspiratorially. "We didn't try the back door."

She rolled her eyes. "Ha ha very funny." She leaned forward and brought her lips to mine, kissing me gently. Leaning back she smiled. "Goodnight lover boy, I'll see you soon."

"Goodnight baby."

Tiffany exited the car and walked towards her building, swaying her hips in a way that made me want to follow her inside and have another round of hot sex with her. And maybe this time I could convince her that my anal sex comments were not a joke but were sincere attempts to actually do it. Instead I just sat in my car and watched her beautiful behind swing back and forth until she rounded the corner and was lost from view.

I drove the five miles back to my apartment lost in thought. Tiffany and I had been dating for about six months and things had been going really well. I enjoyed spending time with her and she had this slim, petite body that I found incredible attractive. She looked great naked and the sex was amazing but I still hadn't found the right way to impress upon her that I really wanted to do one thing more than anything else: Anal sex.

For as long as I could remember I had been obsessed with anal sex. From my virgin days watching porn to my experiences with anal sex in real life, just the thought of fucking a girl in the ass got me instantly hard. I loved how it felt when the tight ring of her ass gripped my cock and milked the cum out of me. At some point I thought that I would get over my obsession but if anything it's only gotten worse with time.

I could still vividly remember the first time I had ever had anal sex. It was in high school and I had finally convinced my girlfriend to try it. Pressing my hard cock to her tight rosebud I thought there was no way it would fit. Holding onto her hips I pushed slowly but firmly until the head of my cock slipped into her ass. It felt so amazing that before I even began thrusting I immediately came. It was such an amazing feeling that I was instantly hooked.

I was brought out of my rumination when I pulled up in front of my apartment. Parking the car I quickly headed inside and started getting ready for bed. It was already late and I had to work the next morning so I turned out the light and climbed into bed. As I lay my head on the pillow and closed my eyes I thought about what it would be like to fuck Tiffany in the ass. Something told me that it would be an amazing experience that I would never forget.

With thoughts of anal sex playing on repeat in my mind I found myself still awake ten minutes later with a raging hard on. Opening my eyes I reached over and grabbed my laptop off the side table and opened it next to me in bed. I immediately clicked on my porn collection and opened up my favorite porn folder marked 'Anal'. There were countless video files in the folder but I found a favorite of mine and double clicked on the icon that read 'Young Girl Tight Anal.avi'.

My eyes were glued to the screen as a young, eighteen year old girl sat on a couch in a large, beautifully furnished room. I knew from watching the video multiple times before that it begins with the girl talking to the guy behind the camera for a few minutes. I was so horny that I immediately skipped ahead to the part where a guy with a big dick comes in. I watched a few seconds of their early interaction and then I once again skipped forward to the part I wanted to see most.

When I saw that the couple onscreen was in the doggie style position I let it play. The guy had just stopped pounding her from behind and he was pulling his large cock out of her pussy while he fingered her ass. Removing his finger he pressed his slick cock to her backdoor and began to push forward. The camera zoomed in to give a close up view of his cock as it began to penetrate her ass. My own cock was already rock hard and I began to stroke it.

As her ass swallowed the head of his cock I wondered, not for the first time, what that must feel like for her. What did it feel like to have someone's dick in your ass? Could that possibly feel good? It must feel good to some people because I had dated girls who liked it. I also knew that anal sex was common for gay men but since I didn't know anyone who was gay and I wasn't interested in men that thought was quickly forgotten.

The guy now had his entire cock in her ass. He began penetrating her with long strokes that started slow but were quickly increasing in pace. If she was faking her enthusiasm for that particular sex act her moans fooled me. As he began fucking her ass in earnest I increased the pace of my own stroking. The slapping of flesh on flesh from the video matched the sounds I was making as my hand slid up and down my cock.

After a few minutes in the doggie style position they switched. The guy sat down on the couch and the girl climbed on top of him and slid her ass back down on his cock. She brought her legs up and spread them so that her pussy was on display as she bounced up and down. She had a joyous look on her face which only turned me on more. I increased the pace of my stroking as I imagined that it was my cock deep in her ass.

Since I had seen the video multiple times I knew it was time for the cumshot when she climbed off of him. As she went to her knees in preparation I increased the pace of my stroking so that I would cum at the same time as the guy in the video. As he stepped up in front of her and began to stroke his large cock in her face my cock erupted in my hand and began to cover my bare stomach in semen. Through half closed eyes I watched him shoot his load all over her face.

I sighed contentedly and closed the video file. Knowing that I had to get up in a few hours for work I quickly cleaned myself up and put my laptop back on the side table. Laying my head down on the pillow I quickly drifted off to sleep in a state of deep relaxation.

It was tough to wake up the next morning but by the time I got up and got to the office the rest of the day seemed to fly by. I left work around 6:30PM and since I knew that Tiffany had dinner plans my night consisted of making dinner for myself at my apartment and then watching some TV on the couch. It was about 10:00PM when my phone rang and I saw that it was my girlfriend calling.

"Hello?"

"Hey baby, it's me," Tiffany said in an excited voice. "Whatcha doing?"

Her energy was infectious and I found myself lifted by it. "Nothing much, just watching some TV. How about you baby?"

"I just got home after having dinner with Monica. She is dating this new guy so she wanted to tell me all about it."

"That's cool. Anything I should know?" I asked with a smile. Monica was Tiffany's best friend from childhood and they told each other everything, including juicy details about their sex lives. Tiffany loved to tell me all about it.

She laughed. "Actually yes! Monica was telling me about how much amazing sex she has been having with him lately. Then she mentioned that they had a little slip up last night."

"A slip up?"

"Yeah, apparently while they were having sex his cock accidentally slipped out of her pussy and went straight into her ass."

I felt my cock immediately come to life. "Umm, I doubt that was an accident."

Tiffany giggled. "That's what I said but Monica swears it was. She said she was on top of him and she was really wet. Apparently she twisted her body on an out stroke and that caused his dick to momentarily slip out of her pussy. Then she immediately sat down and it accidentally lined up with her ass instead."

My cock was instantly hard. I reached down and rubbed it through my pants as I asked Tiffany, "So did they stop or keep going like that?"

"They stopped. Monica said she likes anal every once in a while but she wasn't in the mood for it last night."

Tiffany had told me a lot about Monica's sex life, more than I wanted to know to be honest, but this was the first time I had ever heard about Monica having anal sex. I continued rubbing my hard cock through my pants as I tried to figure out a way to roll this topic into a conversation about me and Tiffany having anal sex. "Wow, so have you ever had a slip up like that?"

Tiffany laughed again. "Nope, and I would know that it wasn't an accident if it did happen."

Tiffany liked to laugh off my anal sex comments like they were jokes but now was the time to see if there was any hope of anal sex for me in this relationship. "Any interest in having it not be an accident?" I asked and then I waited on baited breath for her answer.

"Not really. I mean, I can't imagine it would actually feel good."

My heart sank momentarily but there was a glimmer of hope in that it wasn't a definitive no answer. "Well, clearly some people like it or no one would do it," I said, clearly grasping at straws. "Even Monica said she likes it sometimes."

"True, but I just don't think I would like it." Tiffany paused for a second and then asked me a question. "I know you like to make comments about it all time but how would you like it if I shoved my cock up your ass?"

I laughed. "You don't have a cock."

"No, but if I did would you let me shove it up your ass?"

"Of course," I answered without hesitation. "I would at least try it to see if I liked it."

"Yeah right," she responded. "You are just saying that so I'll do it."

Was I that transparent? "Ok, you're right. I have no idea if I would do it because the fact of the matter is that you don't have a cock. But here's the deal, I want to have anal sex with you," I said earnestly. "And I would do anything to make that happen. Absolutely anything."

She let out a big sigh of exasperation. She didn't say anything for a few seconds and then she said, "Ok, I'll remember that."

After that we talked about how each of our days went and what our plans were for the coming weekend. We made plans for a dinner date Friday night and then talked about a few more mundane topics before we said our goodbyes. I wished her a goodnight and then hung up the phone.

After work on Friday I came home and got ready for my date with Tiffany. I jumped in the shower to clean up and then picked out an outfit to wear. Buttoning up my shirt over my tall, thin frame I checked my hair and then headed out the door. We had planned to meet at a restaurant that was close to her apartment and I was already a few minutes late.

I got to the restaurant and saw Tiffany sitting at a table with her back to the door. She was talking to a good looking brunette next to her and they seemed to be laughing about something. As I approached Tiffany saw me out of the corner of her eye and turned towards me with me a smile. Standing up she hugged me, gave me a quick peck on the lips and then quickly turning back towards the girl she had been talking to.

"Wendy, this is my boyfriend I was telling you about."

I stepped up and introduced myself, shaking her hand with a smile. Wendy had a cute face and a thin, feminine figure. Even though she was sitting down it was clear that she was much taller than Tiffany but with a smaller bust. Her long, dark brown hair fell in waves across her shoulders and down her back as she greeted me warmly.

Tiffany turned back towards me and said, "Wendy is a friend of mine from LA. She recently moved here so I thought I would invite her to dinner with us."

"Sounds good," I said as I sat down at the table.

We ordered food and drinks from the waiter while Tiffany and Wendy told me how they knew each other. They hadn't seen each other in a long time and they had lost contact for a while before recently reconnecting. As they regaled me with stories from their time together in Los Angeles I started to get the feeling that they just happened to be in the same group of friends and weren't necessarily that close to begin with.

Even though I was a little confused about why Tiffany had invited someone who was just an acquaintance to dinner with us on date night I was enjoying our conversation. Wendy was funny and charming and she had a relaxed way about her that instantly put me at ease. At times during dinner Tiffany seemed a little preoccupied but Wendy was outgoing and gregarious and at times even a little flirty. It was fun.

When dinner was done and I was in the process of paying the bill Tiffany asked us both, "What do you guys want to do now?"

I was a little surprised by the question but since I was enjoying the company I had no problem keeping this going. When Wendy suggested that the three of us could hang out together at her apartment Tiffany and I both readily agreed. Standing up we grabbed our coats and headed out the door.

I left my car at the restaurant and the three of us walked the four blocks to Wendy's apartment. Wendy unlocked the front gate and we took the elevator up to her apartment on the third floor.

"Make yourselves at home," Wendy said as we entered. "Can I get either of you something to drink?"

"Sure," I said as I headed towards the couch. "I'm not picky so whatever you got is fine by me."

"I'll help her make drinks," Tiffany told me with a smile as the two of them headed towards the kitchen.

I sat down on the couch and pulled out my phone. As I checked my email I could overhear Tiffany and Wendy discussing what kind of drinks to make from the kitchen. They discussed everything from wine and beer to mixed drinks but by the time I finished reading my email I realized that I could barely hear them. It almost sounded like they were whispering. After a few seconds they abruptly stopped and then came out of the kitchen together holding glasses.

"Sorry about that baby," Tiffany said as she approached the couch. "We couldn't figure out what to make."

"No problem," I replied as she handed me a glass with clear liquid. I took a sip of the strong gin and tonic and then smiled as Tiffany sat down next to me.

With Wendy sitting on the other couch we picked up our conversation from the restaurant. We started out talking about things like movies and TV shows but as the night wore on, and we had more to drink, I noticed that Wendy's flirtatious nature had infected all three of us. Tiffany began casually dropping in references to our sex life and Wendy seemed to play along and even encourage that kind of talk.

From there it didn't take long before our conversation veered into overt sexual topics. We talked about past sexual partners and kinky situations and by the time Tiffany started telling Wendy about the interesting places that we had had sex, I had to adjust myself because of my massive hard on. With the sexual energy in the room ramped up I looked back and forth between Tiffany and Wendy a few times before I suddenly had a thought: Could this be leading to us having a threesome?

"Wow, you guys have done it a lot of places considering that you haven't been dating that long," Wendy said with a smile. "So what's the most fun sex act you guys have done together?"

My cock threatened to break out of my pants as I answered nonchalantly, "We haven't really done that many crazy things yet. Mostly just normal sex stuff right baby?" I asked Tiffany as I turned towards her.

Tiffany smiled. "Yep, just normal sex stuff so far." She paused and then looked over at Wendy. "Although he wants to try anal sex more than anything. He won't stop talking about it."

"Oh yeah?" Wendy asked as she looked over at me. When I shrugged she said, "I love anal sex. I think it feels great."

I smiled and turned towards Tiffany. "See?"

Tiffany rolled her eyes at my comment and then said to Wendy, "He said that if I had a cock he would let me fuck him in the ass."

Wendy smiled at me. "Is that so?"

"Sure," I said with the confidence of someone who had had a few drinks. "You don't know if you like something until you try it."

I saw Tiffany and Wendy share a smile and then Wendy stood up. "Let's all go my room," she said.

I practically leapt off the couch. With all the innuendo I was confident that we were going to have a threesome now. Tiffany and I hadn't really talked about doing this before but as she grabbed my hand and led me towards the bedroom I silently thanked her for what was about to happen. With a good buzz going I crossed the threshold into Wendy's bedroom.

"Why don't you take a seat," Wendy said to me as she motioned towards her bed.

With giddy anticipation I sat down on the foot of the bed. It was soft and inviting but after a few seconds I realized that neither my girlfriend Tiffany nor Wendy had joined me. Tiffany sat down in a chair next to the bed while Wendy leaned back against the dresser by the door.

They exchanged a look and then Tiffany said to me with a smile, "Why don't you get naked?"

"What about you guys?"

Tiffany gave a slight shake of her head. "Why don't you show Wendy what you got first?"

I looked over at Wendy and saw her watching me with a small smile on her face. "Ok," I said as I started to take off my shirt. Sliding it off my shoulders I stood up and undid my belt. Unbuttoning my pants I let them slide to the floor and then stepped out of them. My hard cock made a tent in my underwear and I looked back over at Tiffany to confirm that she meant for me to get completely naked. At a nod from her I put my thumbs in the waistband of my underwear and slid them down.

My hard, seven inch cock stood out proudly from my body. Much like me my dick was tall and thin and ready for action. I could already see a small bead of precum at the tip. I smiled at Tiffany and then I looked over at Wendy as I sat back down. She was unashamedly checking out my naked body with a hungry look in her eye. No girl had ever looked at me like that before and it was an incredible turn on. My hard cock twitched in my lap.

"Ok, I'm naked now," I said as I sat back on the end of the bed with a smile. "Who is next?"

"I think Wendy should go next," Tiffany told me. "But first I need to know that you meant what you said on the couch." At a confused look from me she added, "The part about anal sex."

"Of course I meant it," I answered reflexively. I looked over at Wendy to see her smiling at me.

"Great!" Wendy exclaimed.

She reached down and pulled her shirt up and over her head in one smooth motion. She then undid her black bra and let it slide off her shoulders and fall to the floor. Making eye contact with me she ran her hands over her small breasts and gave them both a light squeeze. She let her arms fall to her side and then paused before going any further to let me admire the way her soft skin and small bust looked on her thin frame.

Wendy reached down and undid the button of her jeans. She hooked her thumbs in the waistband and began to slide her pants down her smooth, statuesque legs. Standing in the center of the room wearing only a small, black thong, Wendy resembled a lithe dancer with slender limbs and a budding chest. With one hand blocking the view of what was between her legs Wendy began sliding her thong down with her other hand.