Anal Addiction Ch. 02

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Hi," I said as I reached her booth. "I hope I didn't make you wait long."

"Not at all," she said with a smile.

Sliding out of the booth she stood up and leaned forward for a quick hug. She was tall, only an inch or two shorter than me, and the first thing I noticed was how she smelled. It seemed to be a mix of perfume and her own scent and it was intoxicating. As she stepped back and began to slide back into the booth I asked her if she would like a drink.

"I would love one," she answered. "Gin and tonic."

"Coming right up," I said as I started to turn around and head to the bar.

"See the bartender at the far end?" Nina asked behind me. I looked over at the tall, male bartender pouring a drink at the far end of bar. "Go to him for faster service," she suggested.

Nodding to her over my shoulder I walked down to the end of the bar. There were a few other people trying to get his attention but after making a drink he looked up and asked me what I wanted. I told him my order and then got my wallet out. I received a dirty look from the two girls next to me as I handed him my credit card. He swiped it and handed it back to me, letting his hand linger on mine for a second. As I picked up my drinks he gave me a wide smile and told me to have a good night.

I returned to the table and set the drinks down in front of Nina. "That was quick service," I commented to her as I started to sit down. "How did you know to go to that bartender?"

"I used to come here all the time and I just happen to know that he's gay," she said with a smile. "I knew he couldn't resist helping a cute guy like you."

I laughed. "So he wouldn't have helped a beautiful girl like you?"

"Way to work in a compliment," she chided me playfully. "And no, he would have taken his time getting to me."

"Well cheers to gaming the system," I said as I held up my glass.

"Cheers," she replied as she clinked her glass to mine.

After we both took a drink I smiled and said, "I'm so glad Wendy set this up."

"Me too! When Wendy told me the story about what happened at her apartment I have to admit, I got really turned on," She said with a wink.

"Oh yeah? What turned you on the most?" I asked with genuine curiosity.

"How willing you were," she replied. "I don't know a lot of straight guys who would be willing to take it up the ass so quickly like that."

"Well, I had always been a little curious about what anal felt like," I said honestly. "But I'm not attracted to guys so I didn't really think it was possible."

"You had never heard of transsexuals before?" She asked.

"I had heard the term before but until Wendy revealed herself to me I had never really thought about it. I had certainly never considered receiving anal until that moment."

"From Wendy's description it sounds like you took to it right away. I loved hearing that because I am a total top in bed. And when she told me how much you liked it I almost creamed in my pants."

"She told you how much I enjoyed it?"

"Yep. She said that she was going to give you a reach around but when she felt how hard your cock was she wanted to see how it would play out. When she told me that you came without touching yourself I knew I had to meet you."

"I'm glad you did because just hearing that you got turned on turns me on," I said with a smile.

"Oh really?" Nina asked flirtatiously. "Like this turned on?"

She took my hand and placed it in her lap. I could feel her semi-hard cock through the thin material of her pants. Almost immediately I felt it start to grow larger as I slowly began rubbing it. We began talking about other things but I was mesmerized by her hardening cock. I wasn't sure of the exact size but it seemed to be long and thick. We had only been there for about twenty minutes when she asked if I wanted to head back to her place.

"Yes!" I answered enthusiastically.

We quickly finished our drinks. I exited the booth first and as Nina began to climb out I pretended to fall back so that I ended up sitting on her lap.

"Oh I'm sorry," I said theatrically as I ground my ass down on her hard cock. "I must have slipped."

Nina grabbed my hips and pulled me down against her cock. "That's ok, mistakes happen," she said with a smile. After a few seconds of grinding she leaned forward and whispered in my ear, "We better slow down or I might just take this ass right here."

I laughed and then I stood up. Helping her up we headed out of the bar.

I drove us the four blocks to her apartment. She lived on the second floor so I followed her up the back staircase. Fishing her keys out of her purse we quickly entered her studio apartment. It was small but clean with a minimalist look. At the far end of the room was a large, spacious bed next to a dark wooden wardrobe. Next to that was a living space with a couch and a large TV. A bathroom and kitchen completed the space as we removed our shoes.

"Would you like a glass of wine?" Nina asked as she walked towards the kitchen.

"I'd love one," I answered as I moved towards the couch.

Taking a seat I watched as she opened a bottle of red wine and poured two glasses. Walking over she handed me a glass and sat down so close to me that our legs were almost touching. We didn't exactly pick up where we had left off at the bar but we were still touchy. When she would talk she would rest her hand on my arm and when I responded I would put my hand on her leg. It was flirty and fun and it was an enjoyable part of the foreplay to talk and make advances in this way.

We had been talking for about fifteen minutes when there was a momentary pause in our conversation. Sensing an opening I leaned over and slowly brought my lips to Nina's. She returned my soft kiss as we both scooted closer to each other. The gentle kissing lasted only seconds as Nina opened her mouth and allowed our tongues to mingle. She pulled me closer to her and we began to kiss with more intensity.

In no time we were all over each other. Nina's hands were in my hair and I let my hand wander down. Feeling blindly across her leg I felt her jump slightly when my hand found her hard cock. As I rubbed it through her pants I felt Nina's passion ignite as she gripped a handful of my hair. She pulled my face to hers with force and her tongue probed every corner of my mouth.

After a few minutes I took my hand off her cock and brought it to the button of her pants. Blindly unsnapping it and sliding the zipper down I reached in. Nina had to adjust her position slightly but in no time I had my hand wrapped around her panty covered cock. I rubbed it as we continued our tongue wrestling. After another minute I was so horny for her cock that I had to tell her.

Breaking our kiss I leaned back. "I'd love to get your pants off."

She smiled. "I thought you'd never ask." She lifted her ass off the couch and slid her pants down. As they hit the floor she looked down at her large cock straining against her black panties. "Looks like you have woken her up," she said playfully. "Want to give her a kiss?"

"Absolutely!" I answered as I leaned over and put my head in her lap.

Taking a breath I breathed in her feminine scent. It was a combination of flowery soap and natural musk that inflamed my desire for her. Bringing my face down I planted a kiss on her cock through her panties. It twitched as I continued kissing up the shaft until I got to the head. Taking it between my lips I breathed out heavily which made Nina squirm. Smiling to myself that I was able to tease her so effectively I hooked my fingers into the waistband of her panties.

She lifted her ass for me so that I could slide her underwear down to the floor. Suddenly I found myself inches away from the largest cock I had ever seen. It was at least eight inches long and very thick. In fact, it was bigger than a lot of the dicks I had seen in porn. I don't know why but the sheer size of it was a huge turn on. It was much bigger than my cock and I involuntarily licked my lips and then brought my mouth down.

The head easily slipped into my mouth. I heard Nina moan as I slid my lips down, taking a few inches of her cock in one motion. Bringing my head back up I slowly began to bob up and down on it. At first I was only able to take three or four inches of it but as my saliva slicked her shaft I fit more and more in my mouth. I didn't think I would ever be able to get the entire thing in there but by using my hand on the base I was able to simulate taking it all.

I glanced up to see Nina looking down at me. "Wendy was right," she said with a voice full of desire. "You are a natural at that."

I never thought a compliment about how well I suck dick would make me proud. But it did. Redoubling my efforts I began going as far down on her cock as I could before sliding my mouth all the way back up to the head. While I did that I felt Nina snake her hand under me and start rubbing my cock through my pants. I was hard as a rock and sucking on her large member was only making it harder. Both of us began to moan as I continued sucking her.

After a few minutes Nina gently lifted my head off her cock. Looking down at me with a smile she said, "If you keep taking me so deep in your mouth I might cum. Why don't you take a break and let me see that sexy body of yours?"

I smiled back. "Sure," I said as I sat up.

Unbuttoning my shirt I slid it off my shoulders. Letting it fall to the couch behind me I stood up and began to remove my pants. As I let them fall to the floor I looked over to see Nina watching me like a hawk. I had never felt more like prey in my whole life and I paused momentarily before putting my thumbs in the waistband of my boxers. Stretching them out over my erection I let them go and then stepped out of them. Standing there naked in front of Nina I spread my arms.

"Like what you see?" I asked jokingly.

"I love it," she answered seriously. "Can I see the back view?"

I slowly began to turn around. Once my back was to her I began wiggling my ass and I let my hips sway ever so slightly. I wasn't a good dancer but looking back over my shoulder at Nina told me that my movements were having an effect on her. She had her cock in her hand and she stroked it while her eyes devoured my naked body. With that encouragement I began to move towards her bed which was only a few feet away.

Stepping forward I leaned over and placed my hands on the bed. Sticking my ass out towards Nina I rocked my hips back and forth. I then spread my legs and locked them at the knees. Putting my head down and arching my back, I gave her a clear view of my hole. Reaching back I began to rub my cheeks and slide my hands up and down my legs. I knew I had succeeded when I heard Nina get up from the couch.

"That's so hot!" She said as she walked towards me.

I looked back over my shoulder as Nina let her shirt fall to the floor. Her bra quickly followed and I admired her thin naked body as I stood up straighter and turned towards her. Not long ago I would have thought her large, hard cock looked out of place on her smooth, womanly body but no longer. It was at that moment that I realized the perfection of her transsexual body and how I wouldn't want it any other way.

Nina quickly closed the gap between us and pressed her lips to mine. With her small breasts pressed against my chest her tongue forcefully wrestled with mine. She was clearly ready for more because I felt her hard cock poking into my stomach. I gave it a few strokes and then Nina broke our kiss. Smiling at me with lust in her eyes she playfully pushed me backwards so that I fell on her bed.

"You really turn me on," She said. "Are you ready to get fucked?"

I smiled. "I thought you'd never ask."

Nina reached over and opened the nightstand drawer. She unsnapped the cap on a bottle of lube and poured some in her hand. Setting it down she turned towards me and began to rub her cock. The squishing sound of her stroking her lubricated cock filled my ears as I looked up into her eyes. A look of sexual hunger passed over her face as she drank in my prone, naked body. She stepped towards the bed.

Using her clean hand Nina lifted my leg off the bed. Following her lead I bent my knees and brought my legs up to my chest. Nina scooted me to the edge of the bed and then placed a pillow under my butt. She then brought her other hand down to my ass and spread some lube on it. She started by rubbing the outside of my hole but after a few seconds she slid a finger in. I moaned slightly as she pushed it in and out a few times.

"Are you ready?" She asked.

"Yes," I answered breathlessly. "I'm ready for your big cock."

She smiled as she removed her finger and bent her knees slightly to line her slick cock up with my hole. As she began to slowly push forward I felt my ass begin to stretch. Nina's cock was much bigger than Wendy's but Nina was gentle and she applied steady pressure until I felt the head of her cock slip into me. I moaned loudly as my hole stretched to accommodate her girth. Once my breathing steadied Nina pushed forward again, slowly sliding her cock into my ass one inch at a time.

I let out a big sigh. I couldn't believe something that big fit inside me. My hole was stretched tight around her cock shaft and I could feel the head deep inside me. It pulsed with her heartbeat as she waited for me to get used to her size. Twenty seconds must have passed before I felt the ring of my ass begin to loosen. I reminded myself to relax and once I smiled up at her Nina nodded and then slowly slid her cock back.

She began to fuck me with long, slow strokes. She would push all the way into me until her hips made contact with my butt, then pull all the way out until just the head of her cock was in my ass. At first it was a little uncomfortable due to her large size but she used a smooth, controlled motion that both relaxed and stimulated me. It took a very short period of time until it started to feel really good.

We were both breathing heavily and moaning as she fucked me. Nina slowly began to increase the pace of her penetration with her hands gripping the back of my knees. She leveraged her standing position so that each thrust into me was more powerful. With each slap of her balls against my ass I would get more turned on. I looked down to see that my cock was hard without having touched it.

Nina noticed too. With a glance down at my bouncing erection she said, "Wow, Wendy was right, you really do love this."

"Yes... I do," I managed to breathe out between her strokes. "And... you're so... big... it's amazing."

She smiled down at me and then she stepped back, letting her wet cock slide out of my ass with a plop. "Why don't you slide up a little bit so I can join you on the bed?"

Using my arms I slid myself backwards on the bed. I let my legs go straight for a second but when Nina climbed on the bed seconds later I brought them back up to my chest. I loved looking up at her while she fucked me and I wanted her to keep going like that. Seeming to read my mind Nina came towards me on her knees. Lining her hard cock up with my exposed hole she immediately slid back into me.

Nina brought her lips down to mine. I loved the feeling of her tongue in my mouth and her small breasts pressed against my chest while she fucked me. With my hard cock trapped between us it was like every part of my body was being stimulated at the same time. It felt so good that every movement forward and back got me a little bit closer to cumming. I didn't want to cum just yet so I was glad when Nina stopped for a second.

Taking her lips from mine and placing her arms around my back Nina pulled me tight to her. Rolling to her right she took me with her as she rolled over onto her back. Suddenly I was looking down at her while I sat on her cock. Taking a second to get my bearings I adjusted my legs so that I was in the cowgirl position. Placing my hands on either side of her head I began to rock back and forth.

I began riding Nina's cock. It felt great to be able to control the speed and depth of her penetration. At first I just moved up and down on her cock but then I began grinding down on it. That made me moan even louder and I could tell Nina was enjoying it too because she would contort her face in pleasure whenever I did so. I was also glad to see I wasn't the only one enjoying this position so much.

Nina's hands were all over me. She rubbed my chest and pinched my nipples. Then she put her hands on my hips and pulled me down onto her cock with every down stroke. Then she reached up and caressed my face as I ground down on her. I loved the feeling of her soft hands roaming my body until she reached out and took my hard cock in her hand.

"Wait, wait," I said breathlessly as I stopped bouncing on her cock. At a confused look from her I added, "No, it's not bad. It's just that I could cum any second."

She smiled. "Well don't let me stop you then." After a half second pause she added, "From what I heard you don't even need my hand to help you cum."

I had forgotten that Wendy had told her I came without touching my cock. I hadn't tried to do it again since that night but with how much Nina's cock was stimulating me I knew it wouldn't take long. Looking down at Nina I smiled as I began to rock back and forth again. I closed my eyes and focused on the feeling of her cock sliding and out of me. As soon as I focused on the friction of my ass clamped around her shaft the pleasure became overwhelming.

I squeezed my eyes shut and groaned loud enough for the neighbors to hear. I felt the first shot of cum rocket out of my cock as I continued bouncing up and down on Nina's large member. The second shot was right behind it as my entire body convulsed with pleasure. Each subsequent shot of cum was accompanied by a moan from me and a contraction of my anal muscles around her cock.

When I was spent I took a deep breath and opened my eyes. I looked down to see Nina smiling up at me with my cum all over her breasts and stomach.

"That was the hottest thing I've ever seen," she said happily. "You made yourself cum just by riding my dick. And the look on your face while you did it was pure ecstasy."

I wiped the sweat from my brow. "Yeah, that was the best orgasm I have ever had," I said seriously.

"It certainly looked like it." Placing her hands on my thighs she smiled and said, "Alright, why don't you lay down? It's my turn."

I raised my ass up and off her cock. Rolling over onto the bed I laid down as Nina sat up. She reached over to the nightstand and picked up a small cloth which she used to quickly clean my cum off her chest and stomach. She then used it to clean the lube off her cock before tossing it next to her and getting up on her knees. Turning towards me she swung a leg over my body and straddled my chest.

Nina looked down at me with her cock right in my face. "Want to give it a lick?" She asked.

I did. So I did. Sticking my tongue out I licked the head of her cock. There was a faint taste of lube on her cock but otherwise it tasted good. I sucked on the head for a second and then she slid forward forcing more of her cock in my mouth. In no time she was sliding half of her cock in and out of my mouth in short strokes. Her breathing quickly became shallow and she announced that she was going to cum.

She pulled her cock back and gave it a couple strokes. I had been expecting her to cum in my mouth so when she pulled back I left my mouth open. She moaned as most of her first shot of cum went straight into my mouth. The second shot painted my nose and cheek with a white streak and the third shot hit my chin and neck. By the time she was done the bottom half of my face was covered in her cum.

Nina looked down at me as her heavy breathing subsided. "You look really hot like that," she said with a smile.