tagTranssexuals & CrossdressersAmanda and Me Ch. 06

Amanda and Me Ch. 06


The room was still dark when I awoke. Blinking the sleep from my eyes I sat up in bed and glanced towards the window where the faintest of light was beginning to creep in under the blinds. It was definitely too early to get up so I lay back down and closed my eyes, letting my mind wander over the last week of my life while I listened contentedly to the sound of Amanda's soft breathing next to me.

As the soft morning light began to creep into the room I realized that I wasn't going to be able to fall back asleep. I thought about rolling over and waking Amanda up with kisses but from her heavy breathing it was clear that she was still sleeping soundly. I decided to let her sleep awhile longer so as stealthily as I could I slipped out of bed. Grabbing some shorts off the dresser I made my way out of the bedroom and quietly closed the door behind me.

Since I was up early I figured I might as well get some of the work done that I had been unable to complete at the office over the last few days. Picking up the work laptop I had brought home I set it on the kitchen table and pressed the power button. As the operating system booted up I thought about the amount of work I still had to finish and sighed. I guess I was more distracted at work recently than I realized. Amanda was having quite an effect on me.

I threw myself into my work for the better part of an hour before I heard sounds of movement coming from the bedroom. I was about to get up when the door to my room opened. I looked up as Amanda came out of my room wearing one of my light blue dress shirts and nothing else. It was buttoned in the middle but open at the top and bottom giving me a view of the slope of her small breasts and her large limp cock respectively. As she walked towards me rubbing the sleep from her eyes, her cock swung invitingly back and forth beneath the bottom of the shirt.

"Good morning," I said with a smile as Amanda approached the table.

"Good morning sexy," she said as she gave me a quick kiss. "I hope you don't mind me borrowing your shirt."

"Not at all. I have to be honest though, it looks much better on you than it ever did on me. How did you sleep?"

"Good," she said as she stretched her arms over her head. The shirt rode up her hairless torso and exposed her lower body all the way up to her belly button. "I always sleep well next to you."

I felt a stirring in my shorts as I got a close up view of her smooth body. From her small feet up her statuesque legs everything came together at her beautiful cock. A few weeks earlier I would have thought a penis looked out of place on such a feminine body but after a week with Amanda I couldn't imagine my dream girl any other way but with a cock like hers.

Amanda brought her arms down and ran her fingers through my hair. I looked up to see her with a mischievous smile on her face. "Getting excited already?" she asked as she glanced down in my lap. Before I could respond she added, "Let me use the bathroom first," before walking away.

I looked back at my computer screen after Amanda shut the bathroom door behind her. I tried to focus on what I had written minutes before but it was no use, I was too distracted. In fact, my cock had gone from semi-hard to rock-hard in the time since Amanda had closed the door. I reached down and adjusted my shorts but all I could think about was Amanda's naked body.

I looked up as Amanda exited the bathroom. I was expecting her to come right back to the kitchen table but a few steps out of the bathroom she stopped. She was looking at the floor near the bed in my room and I saw a curious look come over her face. I watched as she bent down and picked something up. She giggled and then moments later she returned to the table with a huge smile on her face and her hands hiding something behind her back.

"Guess what I found," she said with a twinkle in her eye.

I was confused but her giddiness was infectious. "I don't know. Your clothes?"

She laughed. "Nope. Something much better than that." Swinging her arm around she held up a long, bumpy dildo and looked questioningly at me. "You wouldn't happen to know anything about this would you?" she asked playfully.

I colored slightly. "Oh, umm..."

My reaction only made her smile. "Don't be embarrassed, I think it's hot you have this toy." She paused, tapping her slender finger against her lips as she pondered something. "So... do want to show me how it works?"

"How it works? Obviously I just-"

"I said show me how it works baby, not tell me," she said with a wink.

I blushed again. "Oh, uh, sure. Here?"

"Why not?"

"Ok," I said uncertainly as I got up out of my chair. I really wasn't sure where to start so I smiled shyly as I took the toy from her. Setting it down on the table next to me I pushed my computer away to clear one end of the table. Turning back towards Amanda I saw a hungry look in her eyes as she leered at my body. Glancing down I saw the tent in my shorts that my hard cock made as it strained against the fabric.

Amanda's devouring look actually helped me relax as it made me realize that I didn't need to put on the show of my life in order to turn her on. All I really had to do was be myself and the rest would take care of itself. To that end I turned my back to Amanda and slowly began to slide my shorts down. It was a tease and I could tell it was working because her cock immediately began to swell and lift the bottom of the dress shirt she was wearing.

"Why don't you have a seat," I said as I motioned towards the chair I had been sitting in earlier. "You'll get a much better view."

She looked up from my half exposed behind and smiled at me. "Sounds good to me," she said with a giddy edge to her voice.

As Amanda took a seat in the empty chair almost directly behind me I continued. Inch by inch I slid my shorts down until my naked ass pointed directly at her. I let my shorts drop to the floor and then slowly ran my hands up the back of my legs until they came to rest on the cheeks of my ass. I gave each one a little squeeze, all while watching Amanda's face for her reaction. She had an almost laser-like focus on my hands and her hard cock stood up proudly between her legs.

After rubbing and squeezing my backside for a while, I glanced over at the dildo on the table. Reaching over I ran my hand up and down the bumpy shaft. Why was this on the floor of my room this morning? The last time I used it was Thursday night and... Oh, that's right, I was so tired that I just dropped it next to the bed when I was done. I remember that I had been imagining that Amanda was pounding my ass but I was too exhausted after I came to do anything but drop the toy next to the bed.

I realized I was gripping the dildo on the table and rubbing it up and down like I was masturbating a real cock. Glancing back over my shoulder at Amanda she had her cock in her hand and her eyes were filled with lust as she watched me stroke the dildo. Slowly picking it up off the table I brought it behind me and rubbed it up and down my crack. Looking around for the nearest lubrication I noticed Amanda's purse on the floor with a small bottle of lotion peaking out.

I stepped away from the table with dildo in hand and walked the few steps to where Amanda's purse lay on the floor. I bent over slowly, looking back as I did so to see Amanda increase the rhythm of her stroking. Snatching up the lotion bottle out of the front of her purse I turned and walked back towards the table with my hard cock bouncing in front of me. I quickly slid back around the table and pointed my ass at Amanda again.

Applying a liberal amount of lotion to the dildo I brought it around and lined it up with my hole. A moan escaped my lips as I pushed it forward, sliding about half of it inside me in one smooth motion. It felt so good as it went in, each successively larger bump in the dildo stretching me out a little more. With the pounding Amanda had given me the night before I needed little time to get used to it before I slowly pulled it back out.

I began moving the dildo in and out of my ass at an increasing pace. My eyes were squeezed shut in pleasure and my chest was flat on the table as I hammered my own hole. At first I was only able to take half of the dildo inside me but after a minute or so I could feel more and more of it penetrating me on each forward thrust. I was moaning and panting when I suddenly felt a warm hand on my back.

"Mind if I take over?" Amanda asked huskily.

I took a second to catch my breath and then glanced back at her. "I would love that," I said with a smile.

Amanda wasted no time replacing my hand with hers on the bottom of the dildo that was implanted in my ass. Taking over where I left off Amanda quickly resumed the rhythm of sliding the dildo in and out. It was clearly turning her on and I felt her large cock rub against the outside of my leg as she worked. Reaching back I took her hard cock in my hand and began stroking her as she impaled me with the dildo.

Amanda's breathing had increased since taking up her new position and after a minute or so she removed the dildo from my ass and quickly stepped up behind me. Pressing her eight inch cock to my well lubricated hole I gasped as she pushed into me. Amanda quickly bottomed out and then gripped my hips for leverage as she began pounding my ass with long, hard strokes. Reaching down I took my cock in my hand and tried to match her rhythm.

I closed my eyes and let my head rest against the table as Amanda fucked me. Her thick cock felt different than the dildo as it slid in and out of my ass. Where the dildo was bumpy and got thicker the more I took, Amanda's cock filled me completely at all times. I loved the feeling of my hole stretching around her enormous member and the more she penetrated me the better it felt. Every time her hips made contact with my butt I would moan with pleasure.

As Amanda's grip on my hips kept tightening I increased the pace of my own stroking. My cock was as hard as a rock and the feeling of Amanda's balls slapping against mine on every forward stroke only made it harder. We were both breathing heavily as the sounds of our naked flesh making contact filled the room. My moans increased in volume as we built towards a shared crescendo.

Just as I had the thought that neither of us would last much longer I felt Amanda's body convulse behind me as her cock spasmed. She dug her fingers into my sides, thrusting forward until she was deep inside me. She gave a girlie scream and moaned as she emptied her balls into me. The pleasure she was experiencing was like a tide that took me under with her and I felt my own cock spray the table under me with cum.

Amanda collapsed forward onto my back. With her cock still nestled deep inside my ass she rested her head on my back as we both tried to catch our breath. I reveled in the feeling of Amanda's naked body against me as she put her arms around me. After a few seconds she reached down and fondled my spent cock, squeezing the tip gently and scooping a bead of cum off the end. Bringing her hand up I heard her lick her finger and sigh contentedly.

Once we caught our breath Amanda stepped back from me and slid her spent cock from my ass. Stepping over to the chair she had been sitting in she retrieved the dress shirt she had discarded when joining me at the table. She gave me a playful smack on the behind and then headed towards the bathroom. Over her shoulder she asked, "Do you have any shorts I can borrow?"

"Sure," I said as I reached down to pick up the dildo. "Just give me a second and I'll find some for you."

Amanda cleaned herself up in the bathroom and then came out to see what I had found. She looked over the old gym shorts and small t-shirts that I had laid out on the bed and then waved me away. I headed into the bathroom to clean up. I washed my face and brushed my teeth but looking in the mirror I knew there was no hope for my hair. It had that great after-sex messy look that wasn't going away. I smiled to myself as I exited the bathroom.

"So, what do you think?" Amanda asked as she stood next to my bed completely dressed. "It's the best I could do with what you have."

She was wearing the same blue dress shirt of mine that she had worn earlier only now it was tied up around her waist so that it fit her more snugly. She had on my old gym shorts but they looked completely different with her shapely butt in them. I wasn't sure how she could take two articles of my clothing and transform them into such a sexy outfit. I was blown away and I realized after a few seconds that Amanda was snickering because I was just staring at her with that dumb look on my face.

"Thanks, that was the reaction I was going for," she said with a smile. Looking me over and nodding she asked, "So do want to go grab something to eat? I'm famished after our little workout session this morning."

"Sure. There is a cafe not too far from here that I have been wanting to try for a while, how does that sound?"

"Sounds great. Let's do it."

Hopping in my car we headed towards a cute little cafe that I drove by everyday on my way home from work. It was busy for a Saturday morning but after waiting for twenty minutes or so we were seated at a booth by the window. We were both so hungry that we didn't start having a conversation until after we had placed our orders with the waitress. At that point I reached my hand across the table and placed it on Amanda's as we chatted amiably.

We were talking about events in the local neighborhood when Amanda asked me, "Have you ever been to the theater over on 5th Street?"

I thought about it for a second. "I haven't. Is that the place that stages local theater?"

"Yeah, local theater and concerts. I used to go to shows there all the time with my ex-boyfriend."

Amanda and I had talked about dating before but she had never mentioned anyone in particular. I was suddenly curious so I asked nonchalantly, "Your ex-boyfriend huh? Was he in theater?"

"Actually he was a musician. He was in a local band and they really wanted to play a show there but they just weren't popular enough."

"Oh ok, have you dated a lot of musicians?"

"Nope, just the one. But we were in high school when we started dating and he was just a band geek back then."

"Ah, so you like nerds then."

Amanda laughed. "Yep, clearly," she said as she motioned towards me. "I guess I'm just drawn to intelligent conversation and if a guy can't stimulate my mind then he can't stimulate my... you know."

I smiled. "Yep."

I was about to ask another question but at that moment the waitress returned with our food. Not wasting any time we put our conversation on hold while we dug into our breakfast. The food was delicious and with my ferocious appetite I cleared almost my entire plate before I realized it. Looking over I smiled when I saw that Amanda was similarly focused on her plate. It wasn't until we put our forks down that we started talking again.

We talked some more about Amanda's dating history. She told me that she had had two serious boyfriends in her life, one in college and the aforementioned high school band geek. We talked mostly about the boyfriend she had in high school and how he was the first guy to show interest in her after her transition. She told me about how they had fallen in love and how lucky she was that her first boyfriend wasn't stuck in rigid sexual stereotypes.

"So enough about me," Amanda interjected after what seemed like my millionth question. "Tell me about your love life before we met."

"There really isn't that much to tell," I said earnestly. "I've really only had one serious girlfriend and that was back in college."

"What was she like?"

"She was very outgoing and extroverted. She liked going out and spending time with friends. I've always been shy but being with her actually helped me to open up socially and meet new people."

"What did you guys like to do together? Movies? Dancing?"

"Well, she wouldn't let me go dancing with her because I was so bad at it. But we both liked movies and we used to go to the theater when there was something good to watch."

Amanda looked confused. "Wait, she wouldn't go dancing with you just because she thought you were bad at it?"


"What a bitch."

"Well, I am bad at it so I kind of-"

"No, screw that. Last night it took all of five minutes for you to pick it up so she has no excuse. Please tell me the sex was amazing and that's why you were with her."

"Well, she was my first so I didn't have anything to compare it to but I thought it was pretty good."

Amanda shook her head. "Did she at least use your toy on you the way I did this morning?"

"No, but she couldn't have used that toy on me because I just got the toy recently."

"Really?" Amanda asked with curiosity. "How recently?"

"Last weekend."

A small smile began to form at the corners of her mouth. "Where did you get it?"

"From a porn shop right around the corner from here."

A full smile broke out on Amanda's face. "What do you say we get the check and then head over there so I can check the place out?"

"Sounds good to me," I said as I signaled the waitress.

We jumped in my car and headed towards the adult shop I had visited the week before. When I saw the "DVDs! Video Booths! Toys!" sign I pulled into the parking lot. The Saturday before I had parked in the back of the lot hoping my car wouldn't be recognized but today I just took the first available spot. It made me a lot more comfortable walking up to an adult shop with a beautiful girl next to me as opposed to walking up alone.

As we entered the dimly lit store I let my eyes adjust and then glanced around. The only other people in the store were standing at the cash register. A blonde employee was ringing up purchases for a tall, thin male customer. I actually tripped on the first step when I realized that the employee was the same attractive blonde girl who had helped me select my dildo the week before. I quickly looked away as I regained my balance and followed Amanda towards the toy section at the back of the store.

As we walked down the isles I was once again overwhelmed by the varied selection. I still couldn't believe how many different types of sex toys there were. From dildos to butt plugs to anal beads there were just too many items for me to focus properly. Amanda didn't seem to be having the same problem as she walked confidently down each isle, picking things up and examining them as she went. She had a perpetual smile on her face as she would pick up an item, look it over, look at me and then put it down.

"Hi there, can I help you guys with anything?"

I turned towards the sound of the unfamiliar feminine voice and looked right into the eyes of the attractive blonde employee. I immediately tried to look away from her but it was too late, she had recognized me.

"Oh, hey, welcome back," she said cheerily as she smiled at me. "How is that new toy working out for you?"

My face went red with embarrassment as I pretended to study the large selection of butt plugs that I happened to be standing in front of. I began to mumble a response but Amanda cut in.

"You didn't tell me you had help last week!" she exclaimed to me with mock outrage. Turning towards the blonde employee she smiled. "Don't mind him, he's just shy. But I can tell you that he loves his new toy. In fact, we used it this morning."

"Oh that's fantastic," the blonde answered. "I was telling him last week how much he would like it and how I use a similar one on my boyfriend all the time." She paused and looked at the nearby selection. "Is there anything I can help you guys find?"

"Umm, we are not really looking for anything specific at the moment," Amanda answered as she put down the dildo she was holding. "But considering how much he enjoyed the toy you picked out for him maybe we can find some more toys for that cute ass of his."

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byTallnhard1© 15 comments/ 35660 views/ 63 favorites

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