Anal

Anal

By

Thomas E. Scott

 

            I leaned over, digging my nails into the silken couch, feeling my girlfriend, Abbey German, ram her massive rubber cock inside me over and over. The intensity of her thrust pushed my head up against the back of the couch. I was lucky that my head was banging on the soft, cushioned, furniture and not the wall or I would’ve seen stars. Wait a minute. I guess I should start at the beginning before I continue.

 

Abbey and I have been dating for almost six months. I’ve made love to her in so many different ways I can’t even count. There was one moment where she was sitting on the couch sucking me off when I felt her fingers grip my balls and squeeze. The intense pleasure of her gripping my gonads in the power of her hand made me squeal.

“You like that,” Abbey asked rubbing the head of my cock around her soft,  pink, lips as she looked up at me seductively, “You like it when I play with your balls, baby?”

I looked down at her with a delighted smile. “Oh yes, you know I do.”

“Do you want me to keep going?”

She didn’t have to ask to get an answer from me, but I answered anyway just to play along. “You know I want you to.”

Abbey went back to swallowing my cock and I went back to daydreaming how I wanted to just blast my cum in her mouth and all over her face. But something weird happened. Her other hand released my balls from her grip and slid in between my thighs making me spread them apart. I didn’t know what she was doing at first until I felt one finger on my anus. I looked down at her angelic looking face with my cock in her mouth surprised. Her eyes looked up at me confident in what she was doing.

“Oh shit!” I cried feeling a nail pierce through my tight hole, then the other finger.

“You like that baby?” Abbey asked again. “You like it when I play with your ass?”

I paused when she asked me that question. I’ve dated many women before Abbey but none of them have ever went that far when giving me good head. But I guess her balsy attempt to pleasure me in other ways is what I liked about her.

“Yes,” I answered, “give it to me baby.”

My permission made her push her finger deeper inside my asshole. I tightened my fists and grind my teeth so hard feeling the stab of pain spreading throughout my ass. Half of me wanted to reach behind me and pull her finger out of there before she goes any deeper. The other half told me to leave her alone and take it like a man. Instead I grabbed her auburn hair pulled her head towards me, deepening my dick in her mouth. If she was going to shove her finger up my ass, then I was going to shove my dick down her throat. Surprisingly she loved it. Didn’t fight back one bit. Abbey sticking her finger up inside me while she was sucking on me hard. It was a combination of pain and pleasure I’ve never experienced before. I wanted to tell her I was coming but after her attempt of brutality on my asshole, I decided to surprise her. I held her head still letting the cum shoot into her mouth. I left my dick in there making damn sure she sucked up every last drop. After I was able to recover we went to fucking like rabbits on the same couch.

After that amazing experience I was curious of what it was like to be fucked in the ass. Not just be fucked by anybody. Just Abbey. We were eating out at this fancy restaurant when I brought up the night we fucked.

“Abbey remember last night?” I asked cutting into my steak.

“Yeah that was fun, why?”

“Well remember when you did that thing to my ass with your finger?”

Abbey blushed as she ate her steak. “I remember, why?”

“Well I was wondering if you and I can take it to the next level?”

Now I got Abbey curious. “Like what?”

I leaned over the table making sure the only people to hear my crazy idea was me and her. Abbey’s eyes shot up in surprise.

“Are you serious?” Abbey asked. “I mean, you really want me to do that?”

“Well just this once. Just to see how it feels.” I placed my silverware on my plate and wiped my mouth with my napkin. “Listen, tomorrow we go out to an adult shop and we’ll check out some toys. You can pick the one you like and I’ll buy it.”

Abbey looked down at her meal and back at me. Her expression was something like she was unsure of the idea. “Are you sure you want to do this?”

I stared in her eyes unblinking. “Positive.”

 

So we were at the adult store. We were checking out some of the toys in the adult toy section. We looked at one of the major dildos in all shapes, colors, and sizes. Pretty beautiful and creative if you ask me.

“So which one are you interested in?” Abbey asked.

“I don’t know. It’s your choice.”

“It’s your ass.”

She had a point. I searched through the variety of dildos wondering which one would fit inside me perfectly. Of course I know that since this will be my first time, all of them would hurt. But for some reason I was prepared. Besides, this wasn’t some tall, well endowed, man about to give it to me. It was my girlfriend. And if it gets too out of control, I could tell her to stop anytime. With her, taking it like a bitch was worth the risk.

I looked at the dildos in all shapes, sizes, and colors. Though admiring penis shaped models was not my cup of tea, I had to admit they were very artistic in some way. I thought I would be here forever until I spotted the one dildo that was just perfect for me and Abbey. It was blue colored and five inches long. There was no testicle shape model underneath. Just one long stem pointing upwards. Plus there was a prod on the other end that is used to enter Abbey as she was entering me. Win, win.

“This one.” I said.

“Are you sure?” Abbey asked. I can still hear the uncertainty in her voice.

“Positive.”

I walked into the club nervous. I’ve never been in a place like this before. Never thought I would walk in a place like this. But here I am. I pass through the crowd of men dancing and grinding up against each other. I head and sit at the bar thinking if this is a good idea.

“What will it be?”

I look up to see a tall bartender. Handsome blonde spiked haired man. With light blue eyes and clean shaven skin smooth to the touch. “Heineken thank you.”

“Com’in right up.” He turned his back to me to reach for the beer behind him. He popped the cap off the bottle and placed it right in front of me. “Three-fifty.”

I paid him and drank my beer. I looked out in the crowd of gay dancers. After all I have been through I didn’t feel like I belong here. I must have sat at the bar for at least an hour until I finally met the person of my dreams. She was tall, short black hair, and tanned rosey cheek skin. And just my luck she happened to sit next to me at the bar. I turned back to the bar casually ready to make my approach.

“A green apple martini please.” She asks the bartender.

The bartender nodded and fixed her her drink. “Four-fifty.”

The woman was about to reach in her purse to pay the man but I took out a five dollar bill and held it between him and the woman. “On me.” The bartender smiled and took the five. “Keep the change.”

“Well aren’t you the kind gentleman.” The woman said with a delighted smile.

“Well thank you. A beautiful woman like yourself deserves to be treated as such.” I said.

She giggled. “Charming too.”

This was the time to introduce myself. I reached out my hand. “My name is Ron.”

The woman shook my hand. “Samantha, but you can call me Sam.”

 

I asked if I can do Abbey anally. She specifically told me “No” which was alright with me. I was able to give it to her from behind without having to do her from behind. After I was done we both lay on the bed side by side breathing in the fresh air that escaped from our bodies.

“So you still want me to do that to you?” Abbey asked seriously.

I faced her with a smile. “Yeah, let’s do it.”

Abbey got the scissors and cut the plastic to release the dildo from its package. She carefully put it on and grabbed the lube we bought from the adult store and lathered it on.

“Okay Ron,” Abbey said standing in front of me with the dildo pointing out of her crotch, “assume the position.”

I happily turned around and got on my knees on the floor. I leaned on the bed taking a big deep breath and letting it out. Instead of closing the tight nit in my ass, I tried to open up hoping Abbey’s protrusion would be easier.

I felt her presence behind me getting down on her knees. I felt the pointing end of the dildo squeeze between my ass cheeks. I grunted just a little when the tip broke through the barrier in my ass awakening every nerve in my back.

“Are you okay sweety?” Abbey asked in concern.

“Yeah, keep going.” I grunted.

Giving her the okay, Abbey continued pushing herself into me but slowly enough not to hurt me too much. The pain was sharp like a thousand needles stabbing the inside of my ass all at once. When the dildo was halfway through, the pain suddenly subsided making it easier for Abbey to go too town.

“Wow.” Abbey said.

“Is it all the way in?” I asked hoping to hear some good news.

“Yeah.”

“Good,” I sighed in relief, “I guess you know what to do?”

I felt the dildo escape my ass and back in with a slow push. Then she did it again. And again. And again. At first I didn’t think of anything of it until I felt my prick stand on end. Abbey was having a field day behind me. Pushing me forward on the bed as her pelvis slapped against my ass cheeks. Just thinking about her taking over my ass made me cum uncontrollably.

That night was not the only night we played with our little blue friend. Every night we took turns fucking each other. I would do her and then it would be my turn. It seemed like a pretty good exchange. But I soon found out that some good things come to an end.

 

“So Ron this is your first time?” Sam asked while taking a sip from her apple martini.

“How can you tell?”

“I come here all the time. Meet a lot of people. Remember familiar faces. But I don’t remember seeing you.”

“Well I guess today is my lucky day?” I proclaimed with a smile.

“I guess it is.” Sam smiled back while sipping some more of her martini. “So what brings you to a gay bar? You don’t look the type to be interested in this lifestyle.”

I chuckled. “That obvious huh? Well I just got over a bad break up with someone very dear to me.”

“Girlfriend?”

“How did you know?”

Sam shrugged. “Got one of thoughs gifts. So the breakup was that bad that you had to come to a gay bar?”

She had a good point. A gay bar is the last thing I should’ve of come to. But after thinking about what Abbey told me after the breakup, I had wondered a lot.

“I’m here looking for a special type of person who can fulfill my needs.” I explained.

“What type of person are you looking for?” Sam asked catching her curiosity.

“Well…someone like you.”

Sam placed her hand on her chest and gave a light gasp. “Me?”

“Yes. See I have a type of taste in a woman that needs to be satisfied and I thought a person like you could satisfy that hunger.”

“And what type of taste is that?”

I leaned in close. Close enough to be face to face with her breasts. Those voluptuous breasts I wanted to grab and squeeze into my mouth so badly. “Let’s just say that I like to meet a woman who likes to be dominant and me the submissive.”

Sam’s eyes widened intriguingly. “Really?”

“Really?”

“So what do you want a woman to do to you dominantly?” She asked.

“Anything you can think of baby. Do you think you would be interested in helping me?”

Sam took a sip of her martini and placed it on the bar. Then she looked at me. The once curiously wanting female changed her expression to serious now. “There is something I need to tell you.”

“Shoot.”

“I’m not who you think I am.”

“And who are you?”

“I’m a tranny.”

I shot back in surprise looking her up and down. Her height was a dead giveaway but the rest of her body showed me something different. She had the smooth skin and lips of a female. Her breasts were about the size of my head in her blue, silken, dress and she had a slender frame with wide hips. If it wasn’t for her height she would have passed off as a woman any day. I came into this bar believing that I was looking for something different. And now I think I’ve found it.

I moved in closer. “Well now I’m intrigued.”

“So you are not disappointed?” Sam asked.

“Not at all. Matter of fact you are just what I’m looking for.”

“Oh really?”

“Really.”

I decided that I needed to end this on a higher note. “Sam, would you mind accompanying me somewhere nice and quiet?”

Sam leaned in closer to me. Close enough I thought she wanted to kiss. “Your place or mine?”

 

Abbey and I met at our favorite restaurant, The Flame. Abbey wanted to meet because she said she had something very important to tell me. I wondered what it was but by the sound of her concerning tone in her voice, it wasn’t good.

I sat across from Abbey hoping the news wasn’t too bad. The waiter asked if we needed anything, but Abbey only asked for a glass of water. Which meant she was not staying long.

“Ron, how long have we been going out?” She asked in her calm voice.

“A little over a year why?”

“Listen, I like you I really do.” Oh-oh, that didn’t sound good coming from her. “But I think maybe we need to see other people?”

My heart sank. I couldn’t believe what I was hearing. “What do you mean, “Other people”?”

“Other people of our interests.”

“I don’t get it.”

Abbey swallowed hard but composed herself in giving me an austere look. “Let me put it clear this way. The sex we’re having has to stop.”

“Why?”

“Look, it was fun at first. I mean I tried it with you because I was curious. And I wanted to make you happy. But now it’s like you can’t get enough. I’m fucking you more than you are fucking me.”

“But baby,” I placed my hand on hers to show her my sincerity, “I thought you enjoyed something like that. I only did it for the both of us.”

“No Ron, you didn’t do it for me. You did it for you. And that’s the problem.” Abbey pulled away from my hand and it disappeared under the table. “I just…to do something like that. It just doesn’t seem normal for a man. And that’s what I want, a man.”

“And I’m not the man you’re looking for?” I finished her sentence but sorrowfully.

“I’m sorry Ron, but I think there is something about you that you need to discover for yourself. And I’m not it.” Abbey grabbed her black purse and stood up. “I’m sorry, I hope you find what you are looking for.”

And that was it. She left me there all by myself alone in the restaurant.

 

I stood naked looking down at Sam’s work on my cock. First she would circle her pierced tongue around the head making it grow bigger. Then she would trace her tongue up and down my shaft strengthening the body. After lathering my cock with her tongue she swallowed the whole thing with her mouth. A gasped feeling my stiffened prick being swallowed up in the dark, wet, cave of her mouth. To make things more interesting she cupped my ball sac in the palm of her hand and gently squeezed and pulled. I thought something so physical would be painful but it felt pretty good.

“Oh shit, I’m cumming.” I told Sam ready to bust.

Sam kept on sucking faster as if helping me release myself in her mouth. Gasping and crying out in pain and pleasure I came in her mouth. But instead of letting go of my cock and spitting my junk out, she kept on sucking. Her lips stopped at the head of my cock and she started slurping up all my spunk and gulping it down. Abbey would never do that.

Sam stood up and wiped her mouth. I kissed her hard even if some of my stuff was still in her mouth. I gripped both of her breasts in my hands and started caressing them with my tongue. I took one nipple in my mouth, pulling and nipping at it with my teeth, then massaging it with my tongue. Then I do the same to the other. Her breasts were voluptuous and craving.

After making her feel more like a woman, it was time for her to fulfill her end of our deal. I looked her in her eyes as she looked into mine. “I want to see it.”

Sam smiled delightedly. She pushed me back making me fall on the couch. She stood confidently in her black panties with a big bulge in side. I watched in anticipation as she pulled off her panties kicking them across the floor with her dress. There it was in all its nine inch glory. It was even bigger than the dildo me and Abbey bought together.

“Impressed?” Sam asked standing confidently.

“I’m more than impressed,” I answered.

“So are you ready to do this thing?”

I didn’t give her an answer. I turned around on the couch and got on my knees with my ass in the air. Sam went into her purse and took out a condom and some lube. She put the condom on and squeezed some lube on the long shaft of her cock. Then she rubbed it all over making it wet, slick, and ready to fit. I heard her walk over and kneel behind me. I took and deep breathe and tried to relax. I can remember the first time I got my ass handed to me when it was Abbey. The sharp pain from the inside of my ass going up my spine. The pain numbed after a few strokes and we continued playing that game over and over until Abbey decided to say stop. Now Sam was going to take her place but with the real thing.

I tried to relax my ass, trying not to tighten up out of nervousness or fear. The head of Sam’s cock made it between my ass cheeks and to the small hole. The first push was not bad. Since I’ve been through this before I should be used to it by now. Then half the body slowly made its way inside. Not too bad. I took about that half when Abbey was behind me. But then more of the body pushed forward making my nerves jump. I buried my head and nails into the couch trying not to cry out in pain.

“Are you alright sweety?” Sam asked concerned.

“Keep going.”

Sam did exactly like I ordered starting with slowly pulling out leaving the head still inside and slowly pushing back in. She did this repeatedly three times until the pain went away. Sam pulled out and pushed back in with force making me gasp. She gripped onto my hips as she thrust herself in and out of me in a nice rhythm. The fucking began to be intense. With her spewing out words like, “Fuck yeah”, and, “You like this don’t you bitch?”. My cock grew hard again ready for another round. Numb to the pain and urging to get off, I gripped my stiff prick stroking it as hard as I could wanting to cum before Sam did.

“I’m cumming baby,” Sam warned speeding up the process, “I’m cumming.”

I wanted to cum before she did, so I sped up the process in beating my meat like she was beating my ass. I could feel the cum rising out of my balls and making its way through my shaft.

“I’m cumming,” Sam repeated still pummeling me with her nine inch dick, “here I come.”

Just as the condom was filled up with her cum I too bursted out all over the floor. Sam collapsed on my back as I collapsed on the couch. Both of us drained.

“God that was intense.” I finally spoke glad that it was finally over.

 

After we were done fucking we laid on the couch together resting our bodies. The next morning we got dressed and I drove her home. We ended the morning with her giving me her number. After that day I called her and we would talk on the phone about ourselves and our lives for hours. Sam told me my last girlfriend, Abbey, was stupid to ever dump me. Which made me feel a little better. We went on dates eating at my favorite restaurants and now they were hers. After our feast we would go to my place and continued fucking each other. First I would do her. I thought it would be difficult since she wasn’t really a man. But it was pretty easier than I thought. Then Sam would turn it around and do the same to me. We would fuck after every date making it official we were boyfriend and girlfriend. And oh yeah, I got rid of the dildo. With Sam around I didn’t need it anymore.