tagTranssexuals & CrossdressersAmanda and Me Ch. 01

Amanda and Me Ch. 01


I walked in the door of my one bedroom apartment and headed straight for the computer. Lately it seemed like I had the same boring routine everyday: get up early, work all day at my stressful IT job, go straight to the computer when I get home to look at porn and masterbate, then eat dinner and go to bed early. Unfortunately tonight was no exception.

As I waited for my computer to boot up I started thinking about how much porn I had watched lately. I had all different kinds of straight porn, from amatuer to anal to threesomes, but for some reason I had found myself increasingly drawn to shemale porn lately. The first time I came while jacking off to a shemale video I felt weird afterwards, like there might be a chance that I was gay and didn't know it, but after a while I realized that just because I liked looking at hot chicks with hard cocks that didn't mean I was gay, it just meant I was expanding my sexual horizons.

When the computer was ready I decided not to look at my straight porn and instead found a video online of a good looking shemale stroking her hard cock. Pulling my pants off I squirted a little lotion in my hand and began rubbing my already hardening cock. The shemale had a big cock, long and hard, and although it was longer that my six inch cock and definitely thicker I was turned on by her large cock. As she started to get close to orgasm I increased the pace of my own stroking and as always I tried to time my cumshot with the video. My timing was impeccable and I managed to shoot my load at the exact same time as the hot shemale I was watching.

As I watched her cum pool in her belly button I wondered, not for the first time, what it would be like to see a real shemale in person. What would it be like to touch a shemale's cock? Would I like it? I had only been with women before and with the exception of my college girlfriend occasionally massaging the outside of my asshole when we had sex I had never really been that adventurous in bed or willing to ask for something I wanted to try. In fact, the only reason my college girlfriend did that was because she said her ex liked it and she had heard most guys did.

After logging off the computer and cleaning up I ate a quick dinner and then retired to the couch for some tv before bed. About 9 o'clock I got a text about dinner on Friday night with some college friends and I gratefully accepted. Pretty soon it was time for bed and a chance to do it all over again the next day.

Thankfully the week passed quickly and Friday arrived in no time. When I walked in the door after work on Friday I went straight to my room to get ready. After a quick shower I dressed in a collared shirt and jeans for dinner at a new gastropub and bar which had just opened down the street from me. It was going to be good to see my college friends again. We had all graduated together about two years prior and were all single and working too much. Being the typical shy technical guy I had a hard time making friends at work but with my college buddies I felt like I was always able to relax and be myself.

I walked the three blocks to the restaurant and found my friends in a booth in the back. After some good natured teasing and catching up we had a nice meal. The food was good, the beer was excellent and after a few hours and a few drinks it was time to say goodbye. After shaking hands all around and everyone heading out I decided to make one last trip to the bathroom before my short walk home.

Standing at the urinal peeing I listened to the two guys at the sink have a conversation about their dates and which one of them was going to get lucky. Shaking my head at my predicament of going home alone I washed my hands and exited the bathroom. I pushed open the door and immediately ran straight into someone coming out of the women's bathroom across the hall. I didn't think I was moving that fast but when we collided, her and I and her purse went flying in all different directions. As I caught myself I quickly turned around to see if the woman I ran into was unhurt.

She had braced herself against the wall in the hallway so I quickly closed the space between us and extended my hand to her elbow to help steady her. As she got her heels back under her she turned around I got my first look at her. She looked to be in her early twenties, dark hair down to her shoulders cut to frame her cute face. With heals on she was tall, although still two or three inches shorter than me at 6'. With her thin frame and budding chest she looked like a dancer about to do a pirouette.

"Are you ok? I'm sorry, I didn't mean to come barreling out of the bathroom like that."

"Oh I'm fine," she answered with an off-handed flick of her wrist, "I've had worse."

Her answering smile not only seemed to reassure me that I would not be getting chewed out but it also lit up her face and made her that much more attractive. I smiled and bent down to pick up her purse only to realize that everything that was inside her purse before we collided was now on the ground. She bent down next to me to help gather up her things.

"So you run into a lot of girls here?" she asked as she playfully nudged me with her shoulder.

I did my best to keep the nervousness out of my laugh. "Nope, you're the first." After picking up her cell phone I quickly added, "I guess it was all just part of my plan to get my hands on the new iPhone here."

Taking it out of my hand and putting it in her purse she asked what kind of phone I had.

"A blackberry. Unfortunately my iPhone was having connectivity problems with the server at work so I had to switch."

"The server huh? What do you do?"

After standing and helping her up I started to explain about my IT job. After thirty seconds or so of non-stop talking I finally realized that if some random cute girl I almost flattened against the wall was asking questions about me and my boring job that must mean she was at least somewhat interested in me. Thankfully I had had a few drinks so I stopped mid sentence and summoned all the liquid courage I had.

"Can I buy you a drink?"

With that bright smile returning to her face she replied, "I thought you'd never ask."

I ordered us two drinks at the bar and we grabbed some barstools. I didn't have a lot of experience with girls so I just started asking questions. She opened up pretty quickly and I managed to get a good picture of who she was. Her name was Amanda and she grew up not five miles from where we stood. She still lived close by and had come to dinner here with a friend but her friend had just left because she had to work early in the morning.

Over the course of our conversation I came to realize that Amanda was funny, engaging, outgoing and kind of a flirt. The first time she brushed my leg with her hand I thought it was an accident but after about ten minutes she just placed her hand on my knee and left it there, slowly making circles with her fingers while talking. I was still too shy to make a move but thankfully Amanda wasn't and after about thirty minutes her circles had moved slowly up my leg. Once her finger even brushed against my hardening cock. I saw her glance down at my crotch a few times and get the beginnings of a smile on her lips before she would dive back into the conversation.

After an hour and a few drinks at the bar together Amanda leaned in close and whispered, "Would you like to get out of here?"

I couldn't answer 'yes' quickly enough and the next thing I knew we were exiting the bar and she had grabbed my hand. "Your place or mine?" I asked.

"Yours, it's closer and I have to pee."

We walked the three blocks to my apartment with my hand in hers. Unlocking the door I pointed out the bathroom and sat on the couch. As I listened to the faint sound of her peeing I couldn't believe my luck. I literally ran into a super cute girl at the bar, we had a great conversation and there we were back at my apartment. Were we going to fool around tonight? I was probably too chicken to make that big of a move but I was pretty sure from our conversation that Amanda was the type to dictate that anyway.

Amanda exited the bathroom and sat down next to me on the couch. Her hand immediately returned to my leg and I felt my bulge rising again. As I turned toward her she pounced, mashing her lips up against mine. Her kiss was soft and passionate at first and then slowly she began to be a little more aggressive. Her mouth parted and her tongue found it's way into my mouth. It had been months since I had kissed anyone and years since I had enjoyed it this much.

Her tongue swirled in my mouth while her hand slowly made its way up my thigh. It only took a few seconds before she was rubbing my cock through my jeans. As our tongues danced she got a firmer grip on my cock and began massaging the entire length of the shaft. After another minute of rubbing my cock Amanda took her hand away and started undoing the buttons on my shirt. After getting it open she broke our kissing to reach down and in one swift motion lift her own shirt over her head. Now in her bra and jeans she strattled my lap facing me and ground her ass down onto my hard cock.

She traced her fingers down my chest and then moved to the button on my jeans. She unsnapped it and slid the zipper down, giving my trapped cock a little air. Without a word from me she leaned back and undid her bra, allowing her small yet perky b-cup breasts to sit right at my eye level. Watching my hungry eyes devour her chest she asked, "See anything you like?" followed by that great smile again.

Amanda leaned back in and pressed her naked breasts against me and then slowly slid down my body. She kissed my upper chest then she licked and sucked each nipple. Going down she soon arrived at my unbuttoned pants. She hooked the top of my jeans with her thumbs and in one motion pulled them down and off. Tossing them behind her my boxers quickly followed and before I knew it she was knealing between my bare legs with my exposed cock inches from her face.

Taking my hard cock in her hand she planted a kiss on the head while making seductive eye contact with me. She licked the back of the cockhead and my dick twitched in her hand. Using her tongue to bathe the underside of my cock, she slowly slid my cock in her mouth inch by inch until she was all the way down. Sliding it back out she started to pick up the pace of her sucking. I can honestly say that I had never had a blow job like this before. With her hot mouth, swirling tongue and spit-smooth motion it's a wonder I didn't cum in the first few seconds.

While her mouth was on my cock her hand started gently massaging my balls. No sooner had I gotten used to her fingers tickling my sack she slid them down to my ass. At first she just teased the outside of my hole but in no time I felt her slip a finger in to the first knuckle. The moan that escaped my lips told her how much I enjoyed that so I felt her saliva lubricated finger push deeper. She bottomed out her entire index finger in my ass before slowly sliding it back out. The feeling was slightly uncomfortable at first since it was unlike anything I had ever felt before but after she finger fucked me for few seconds it started feeling good.

After working her finger in my ass and her amazing mouth on my cock for a few minutes I started to feel the pressure in my balls build up. I started to sit up to let her know that her amazing oral and hand skills were going to make me cum soon when she slowed her mouth and finger to a stop. Taking my cock out of her mouth with a pop she smiled up at me and then slowly rose to her feet. Looking down at me she grabbed the button on the front of her jeans and made eye contact.

"Do you like surprises?"

My first thought was that she had totally shaved public hair or something. With a stupid grin on my face I replied, "Oh, I love surprises!"

She winked and smiled and said, "We will see about that."

She undid the button of her jeans and slowly slid the zipper down. Swaying her hips back and forth she worked her skinny jeans down her legs until they were piled at her feet. Her body was amazing, I couldn't stop my eyes from traveling down from her cute face, past her perky breasts and flat stomach down to the black thong she was wearing. With the low light in my apartment it almost looked like there was a bump there but I just figured all the shemale porn I had been watching lately had gotten in my head.

As if reading my mind Amanda traced her hand down her stomach and let it come to rest on the bulge in her thong. I couldn't believe the bulge was real. "Have you ever heard of a transsexual?" she asked.

"Shemales? Ummm, yeah I guess." My nonchalance was betrayed by my cock springing back to full attention at her mention of transsexuals.

Looking down at my now rock hard cock she smiled and said, "I think he might be more familiar with them than you are. And it looks like he likes it."

I laughed and nodded my head. "Does that mean you..."

I trailed off as she hooked her fingers into the slides of her thong and slowly slid it down. Her semi-hard cock sprang out and stood at half mast not a foot from my face. I had never seen a cock in the flesh besides my own and although I had watched hours of shemale porn it was surreal to see a cock sprouting from between the legs of this beautiful feminine creature. I was mesmerized by her cock and even though it wasn't fully hard yet I knew her cock would definitely be longer and thicker than mine. I had also never seen an uncircumcised cock before but seeing her cock head hiding behind a thin layer of skin was a huge turnon.

I leaned forward and reached out, taking her cock in my hand. She gasped when I touched it but when I looked up she had pure lust in her eyes. I began stroking her cock and I felt it get harder in my hand. After a few pumps her cock was hard and had to be at least eight inches. A glistening drop of precum began to form at the tip of her cock and before I knew it I was leaned forward and extended my tongue, licking the precum off the tip of her cock. It was salty and warm and immediately I knew I wanted more. I moved the head of her cock to my lips and used my tongue to lick the back of the cockhead like she had done to me. I heard her moan as I took the head in my mouth.

The taste of her cock was unlike anything I had ever tasted before, it was earthy and warm but definitely tasted like it belonged on her hairless feminine body. I took as much of her cock in my mouth as I could before I had to slide it back out. After taking her cock in and out of my mouth a few times I felt her hands in my hair, lightly applying pressure to the back of my head as I slid my mouth back down on her cock.

"Oh yeah, just like that. You're a natural baby."

Her praise of my cocksucking made me even more excited. My rock hard cock bounced against my stomach as I bobbed up and down on her cock. As I continued sucking her moaning increased and I could taste more and more of her precum. The taste was amazing and if I had known that I would like it that much I would have pursued shemales long before that.

After sucking her cock for a few minutes Amanda put her hands on the side of my head and tilted my head back so I was looking at her face. "Do you want to take this to your bed?" she asked.

I took her saliva covered cock out of my mouth and nodded. With Amanda's hand in mine we walked through my bedroom door to the bed where she spanked me on the ass and gave me a playful shove onto the bed. Rolling onto my back Amanda came towards me, her hard cock swaying between her legs.

She laid with her body on top of mine and once again found my mouth with hers. Her tongue kissing was passionate and her still wet cock ground against mine. Our cocks slid back and forth against each other as my arms wrapped around her back and pulled her closer. Her breasts pressed against me and her hands held my head while we made out.

Amanda then lifted up off me and took her mouth from mine. Strattling my stomach she kept moving forward on her knees until her cock was right in front of my face. Grabbing a pillow and placing it under my head she smiled at me as I opened my mouth to allow her cock in. Placing her cock head on my tongue she rocked back and forth sliding her cock in and out of my mouth. Amanda had a hand in my hair and after a few seconds she was fucking my mouth in a nice rhythm. I enjoyed this position immensely as I could look up at her face while her cock was in my mouth. From the look of extacy on her face I was more turned on than ever just knowing I could give such a beautiful girl so much pleasure.

After fucking my face for a few minutes she took her cock from my mouth and backed up until my hard cock bumped into her lower back. "Aww, still hard as a rock huh?" she purred. "Let me help."

She slid down until she was on all fours between my legs and took my cock back in her mouth. Her finger returned immediately to my ass where she pushed it back in. She sucked and licked my cock and then moved down and started licking my balls. She took the first one in her mouth and the switched to the other one. After thoroughly licking each ball she spread and lifted my legs and started licking the path from my balls to my ass.

I gasped as her tongue made contact with my hole. I immediately felt a tingling in my hands and feet as the nerve endings in my ass went into overdrive and within seconds I was moaning for more. She used both her finger and her tongue to give me the most intense anal pleasure I had ever felt in my life. Before long one finger turned into two and although it took some getting used to it also started to feel really good.

Before her second finger entered my ass my only thought had been on the pleasure of what I was experiencing in the moment. After she penetrated me with her second finger I started to think about the possibility of her fucking me. The thought excited me and as her fingers moved in and out and I started imagining it was her cock.

Feeling me wiggle my ass into her fingers, Amanda could tell how much I was enjoying it. Smiling at me she winked and leaned over to pick up the lotion from my nightstand. She squirted some in her hand and rubbed it on her cock until it was glistening in the low light. Gently she removed her fingers from my ass, and rubbed her lotion convered fingers on my hole.

She positioned her cock at the entrance to my ass and looked at me for confirmation that I was ok with what was about to happen.

"Please just go slow, this is my first time."

She smiled and nodded and then began to press the head of her cock against my hole. Slowly I felt my ass stretch and strain to give way to her thick eight inch cock. I thought her fingers were uncomfortable at first but she would have had to get her entire hand in my ass to prepare me for her monster cock. I almost screamed by the time I felt the head of her cock finally pass the outer ring and pop into my ass.

Amanda exhaled and gave me some time to get used to her cock in my ass. What started out as painful faded to uncomfortable and then to stimulating. After thirty seconds it started to feel good and Amanda slowly began pushing more of her cock in my ass. Little by little with stops and starts she pushed until she had her entire cock in my ass. At first it felt like I had to go to the bathroom but after some time had passed it felt more and more right, like I was finally fulfilling a deep, unrealized lust.

Amanda leaned forward and brought my legs back with her so she stayed firmly implanted in my ass. Once her breasts hovered in front of my face she whispered, "Feel good?"

I nodded and smiled and kissed her with a passion I didn't know I had. Amanda slowly started fucking my ass while I wrapped my legs around her waist. As the pace of her fucking picked up so did the moaning from both of us. I reached up and played with her breasts while she reached down and started stroking my cock. At first it was a light touch but gradually she got to a pace that matched her fucking of my ass. After all her great oral treatment and the amazing sensation of having my ass fucked I knew I wouldn't last long with her stroking.

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byTallnhard1© 16 comments/ 171262 views/ 226 favorites

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