tagTranssexuals & CrossdressersAmanda and Me Ch. 03

Amanda and Me Ch. 03


The sudden ringing of my alarm clock woke me up at 6:30AM sharp. Rolling over I turned it off and then rubbed at my eyes as I began to wake up. Slowly the events of the night before came back to me and I smiled as I thought about Amanda and how wonderful another night with her was. We had great conversations and another round of mind-blowing sex and I wondered for a second if the last three days had all been a dream. Nope, looking down I saw that I was completely naked and I could feel Amanda's dried cum on me. The thought of last night actually being all an amazing dream made me chuckle to myself.

Dragging myself out of bed, I quickly showered and dressed and headed to work. Monday mornings were usually so depressing I had to drink three cups of coffee just to function but for once I had something to look forward to this week: seeing Amanda again. Had I been walking to work I might have skipped the whole way.

My great mood was quickly suppressed under the stressful work environment I walked into. I had managed to help the weekend IT staff mitigate some of their problems but now the real work began. Getting down to business I worked for hours without interruption until shortly after lunch when I heard my phone buzz with a new text message. Checking the screen I was pleasantly surprised to see a text message from Amanda.

A: Hey cutie, how's work going? :)

It was so nice to hear from her that at first I didn't know what to text back. I wasn't exactly an expert "texter" so I thought I would just keep it simple.

Me: Not bad for a Monday. How about you?

A: Same here. I still would rather have just stayed in bed with you this morning! ;)

Me: Me too! Thanks again for inviting me out to the show last night, I had a great time.

A: So did I and the show wasn't the best part of the night. And speaking of the best part of the night, are you sore this morning?

Me: Sore?

A: Hehe yeah. Your ass was tight and it felt like I stretched you out last night.

Me: Haha now that you mention it I am a little sore. It's a good kind of sore though :)

A: Don't worry the more we do it the less sore it gets so I guess we will just have to get together again soon.

Me: I think that would be best :) when might you be free again?

A: Well I can't get tonight because I have a kickball game and we usually go out drinking afterwards. Are you free tomorrow night?

Me: Tomorrow night works

A: Perfect! Why don't you come over tomorrow night and I'll make us dinner. My roommate has a date tomorrow so I will have the whole place to myself.

Me: Sounds good. Wait, can I trust your cooking? :)

A: Ha ha very funny. You'll like it I promise.

Me: I look forward to it. Have fun tonight.

A: Thanks, have a good one. I can't wait to see you tomorrow.

Me: Me either! See you soon.

Setting my phone down I looked down to see my leg bouncing up and down and I felt my heart pounding. We had two great nights together and I still felt nervous talking to her even over text message. Regardless, we had a date for Tuesday night and I could not have been more excited for it.

Walking in the door after work I headed straight to the computer as per my usual routine. I hit the power button knowing that I would be immediately viewing shemale porn again today. Going back to my favorite shemale site I once again searched for "Shemale Fucks Guy" and upon browsing the videos I again decided to view one where the man was sucking shemale cock and getting fucked by her. Finding a video of a thin transsexual feeding her cock to a guy that had a slight build like me I stood up and removed my pants.

Sitting back down in front of the computer I took my cock in my hand as the guy in the video was on his knees sucking the shemale's cock. Stroking my cock I studied his sucking technique as well as his fondling of her balls. After sucking for a few minutes the guy then got fucked in almost every position imaginable, including one where he was practically upside down and the shemale was fucking him from above. He was stroking his cock while she fucked him and all I could think about was that if he came while in that position he would end up cumming on his own face.

Reaching down with my left hand I began fingering my ass as the video continued. Finally with the guy on his back and the shemale in mid-penetration the guy began to cum onto his own stomach. The shemale kept firmly implanted in his ass until the guy finish cumming and then removed her cock and walked around until she was stroking her cock over the guy's face. With his mouth open and his tongue out she shot her big, creamy load, making maybe half of it into his mouth while the rest ran down his cheeks and chin. That visual was all I needed as I buried my finger deep in my ass and shot my load.

Catching my breath I continued watching the video. Was that what I looked like last night with cum running down my face? No wonder Amanda thought it was hot. Then the guy and the shemale shared a cum kiss before the video faded out. Smiling to myself I closed the browser and walked back to the bathroom to get cleaned up. After that I just continued with the dinner and TV routine until it was time for bed.

I turned the lights out shortly before 11:00PM and climbed into bed. Thinking about my date with Amanda the following night I was slowly drifting off to sleep when my phone buzzed with another text message. I smiled when I saw Amanda's name on the text.

A: Hey sexy, are you up?

Me: Yep, about to go to bed though. How was kickball?

A: It was really fun but not as much fun as the drinking afterwards. Hehe

Me: I'll bet

A: Want to talk?

Me: Sure

My phone rang a few seconds later.

"Hey" Amanda said in a slightly slurred voice.

"Hey there, sounds like you had fun tonight."

"I did. Although now I'm a little tipsy so I'm feeling frisky." She laughed. "It would be better if you were here right now."

Weird, I was just thinking the exact same thing. "Agreed, I totally wish I was there with you right now."

"Really? Mmmm, what would you do if you were here with me right now?"

"Well, let's see... Ummm I guess that depends on what you are wearing." I had to laugh at myself for asking perhaps the most clichéd line ever. I knew Amanda couldn't let it pass.

"What am I wearing huh? Very creative." Giggles. "Actually I'm so horny I got into bed with no clothes on. So what would you do now?"

"Ummm, I would definitely have to take my clothes off and join you in your bed."

"Mmmm, I like that. Then what?"

"Ummm, then I would... Ummm... I don't really know. Sorry, I've never done this before."

"It's ok baby. There are no wrong answers. Just close your eyes and imagine what you would do if you were here right now. Remember, you are naked and getting into bed with me."

I closed my eyes and tried to imagine the scenario described. To get into the right frame of mind I reached down and slid my own shorts off so I was naked too. "Ummm, I guess I would climb into your bed and slide over next to you. I would feel our naked bodies touch and then I would lean in and start kissing your neck."

"Mmmm." Amanda's voice was husky and if I had to guess I would say she was touching herself. "Feels so good."

"Then I would reach up and take your breast in my hand, slowly massaging it as I started kissing you."


"Then I would take my hand and move it down... to your cock, slowly stroking it as we made out."

"Oh yeah. Mmmm, stroke it baby just like that."

"Then I would duck under the covers and kiss your chest. Licking and sucking your nipples I would then kiss every inch down the length of your body until I got to your dick."

"Mmmm" Amanda purred. "Take that big cock in your mouth." She was definitely stroking now. "Use your hot mouth!"

"I would start by licking the head. Then I would place the tip on my tongue and slide my mouth as far down on your cock as I could. It's so big and thick but I would try to take it all. Maybe I would choke a little to get it into my throat."

"Oh baby, take it all." There was no mistaking her masturbating now, I could hear the faint slapping of flesh through the phone.

Without even realizing it I had taken my own hard cock in my hand and was stroking. "Then I will slide my mouth up and down your cock, my saliva making it wet and slippery."

"Oh... so... slippery." Her breathing was getting heavier.

"At the same time I would reach down and cup your balls, massaging back and forth as if I could coax all that yummy cum out."

"Oh yeah!" The flesh slapping was getting steadily louder. "Massage my balls, I love that!"

"I would continue to take as much of your cock in my mouth as I could, making slurping noises as I anticipate your full load in my mouth." I made sucking and wet slurping noises as I softly moaned into the phone.

"Oh... my... God... Are you ready for my cum baby?!?" The flesh slapping noises coming from her end of the phone line were loud.

"Oh yes, I can't wait! Give it to me, I want it all!" The pace of my stroking was nearing me to climax as well.

"Oh yeah. Here it comes baby! Get ready. Ahhhhh..." she trailed off as she came from her own stroking. I followed seconds after her, shooting my second load of the day all over my stomach.

We both lay there panting into the phone until I decided to make exaggerated swallowing noises. Amanda laughed and asked, "How was it? Tasty?"

"The best!"

"I can't wait to give you more tomorrow night!"

"I can't wait for tomorrow night either."

Her breathing slowed a bit before she said "Wow, that really hit the spot tonight. Thanks! And I have to say, for all the things you claim you have never done before you are awfully good at them."

"I don't know about that, I just know that you get me so turned on that it's very natural."

"You turn me on too sweetie." Amanda made another big sigh. "Alright sexy sucker, it's bed time. I'll see you tomorrow."

"See you tomorrow. Good night."


Hitting the 'End Call' button I quickly cleaned up and lay back down in bed. I couldn't believe that everyday since I met this girl was a new amazing sexual experience. And despite her compliments I wasn't sure I was that great at this stuff but I wasn't lying when I said it felt natural. Something about being the submissive cocksucker with her felt right and I never thought that giving someone pleasure could turn me on more than getting the pleasure myself. With that thought in my head I felt myself drift off to sleep.

Tuesday seemed to be the longest day of my life. I don't think a minute of work went by when I didn't think about having dinner with Amanda later that night. By the time I got home I practically ran up the stairs to my apartment to get ready for my date.

The first thing I did was get out the enema kit and start filling the bag. Climbing in the tub I did three cycles of water until I was satisfied with how clean I was. Then I took a long shower and tried to make the outside of my body just as clean. After the shower I dressed and groomed myself and then I was ready to head out.

Since I was ahead of schedule I decided to walk the five blocks to her apartment. Halfway there I ducked into the nearest corner market and I walked around until I came to the wine section. Since I knew absolutely nothing about wine I picked up a random moderately priced bottle of red and shrugged. Hopefully that would work.

By the time I arrived outside her building it was a few minutes after 7:30PM and I was starting to get a little bit nervous. Was the wine I brought ok? Would I be able to calm down and be comfortable at her place? Taking a few deep breaths to get myself to a more calm state I pressed the button for her apartment and started up the stairs when she buzzed me in.

Knocking on the door to Amanda's apartment I was once again blown away when she opened it. She had her dark hair down as usual framing her cute face and she was wearing tight fitting jeans that were snug around her legs and showed off her nice butt. She wore a loose fitting white top that left room for a little cleavage to show as well as a silver necklace and matching silver earrings. In short, she looked fantastic.

"Hey, come on in."

I stepped though the door and gave her a hug. Stepping back she playfully grabbed me by the front of my shirt and pulled me in for a long, wet kiss. I leaned into it as she parted her lips and let her tongue play with mine for a few seconds. Finally breaking the kiss she made that great "Mmmm" sound again as she straightened her shirt.

"Yummy. So glad you could come over tonight. You look great by the way."

"Thanks, so do you!"

"So yeah, this is my place." She stepped back and swept her hand over the living room to her right. "Well, me and Kim, that's my roommate that has a date tonight." She laughed as she said "she told me not to wait up for her."

"Nice place." Looking around the neat living room my eyes were drawn to the largest item in the room. "Is that your TV?"

"Yep, I got that 60-incher last year for the big game. I don't love sports but I love hosting get-togethers so I figured the best way to do that would be to have the best TV."

It really was a fantastic looking TV and it went with the nice furnishings as well. Looking down I remembered I had a bottle of wine in my hand and I held it out to her. "I brought you something."

"Oh you brought wine, so sweet. Come along to the kitchen and I'll open this for us."

I followed her to the kitchen where she opened the wine and poured us each a glass. Sipping my wine I sat at the counter and talked to Amanda as she shuffled around the kitchen and put the finishing touches on our meal. Dinner was a tasty chicken dish that Amanda said was her specialty. Being a horrible cook myself it was nice to see what a real meal was supposed to taste like.

We ate at the dinning room table and after dinner we continued chatting about TV shows, movies and basically just life in general. It was nice to be reminded how much we had in common. Reaching for the wine bottle to refill my glass I tilted it up only to see that it was empty. Masking my surprise at our having finished an entire bottle of wine over dinner I shrugged my shoulders and asked her what she would like to do next.

"Why don't we watch a movie on my awesome TV you were admiring earlier?"

"That sounds good to me." I helped her clean up the dishes and then we ended up on the couch in the living room. Sitting next to me with her hand on my knee she pointed to a bookcase filled to the top with DVDs.

"Take your pick, we have tons of movies."

I looked up at the overwhelming selection of DVDs and then back at her. "Are you sure you wouldn't rather pick? I'm your guest after all." To stall her response I leaned in and started softly kissing her neck.

"Mmmm, be careful what you wish for." A soft moan left her lips. "If you keep... doing that... I might end up..."

I stopped my kissing to whisper in her ear. "You might end up what?" Then I continued by nibbling on her earlobe.

She let out another moan. "I might... pick something... you don't... like."

Continuing my nibbling I replied, "Good luck."

"Alright... you asked for it." Amanda stood up and walked to the bookcase. Instead of reaching for one of the DVDs on the upper shelves she opened two small doors at the bottom of the bookcase and bent down to examine the DVDs in that cabinet. Finally finding one she liked she lifted it out and walked to the DVD player by the TV. Placing the DVD in the player she closed the drive and came back to sit next to me on the couch.

"What are we watching?"

"Close your eyes, it's a surprise."

I smiled as I closed my eyes and listened to her use the remote control to navigate the DVD menus. After a few minutes Amanda got it where she wanted it and pressed play. "Ok, you can watch now."

Opening my eyes I saw Amanda looking at me with a sly smile on her face. Not knowing what to expect I then turned to look at the TV screen. Leaning towards Amanda so that our bodies were once in contact I focused on the movie. It certainly wasn't a movie I had ever seen before nor was the only person onscreen familiar to me. From our conversations I knew we had similar taste in movies so I racked my brain to think of what it could be.

The woman onscreen was pretty. Actually she was hot if I was perfectly honest with myself. Thin body with long dark hair she wore a light cream-colored tank top and a tight dark skirt as she walked down a tree-lined dirt road. There was definitely something sexual about the way she was dressed and the way she walked but I couldn't quite put my finger on what it was. The strumming soundtrack played as she looked ahead with a small smile on her lips and a bounce in her step.

The camera panned back to show the woman walking towards a large farmhouse with a wide deck going all the way around it. An attractive man stood at the front railing and waved as the woman got closer. Waving back the woman started towards the front steps.

"What movie is this?" I asked as Amanda and I continued to snuggle closer. "I don't want to jump to conclusions but..."

The woman was slowly climbing the steps in front of the guy, her hips swaying as she reached the top step. Coming to meet her they hugged in a familiar way, pressing their bodies against each other.

"But what?" Amanda asked a little too innocently as the guy and girl onscreen began kissing. Of equal height their mouths met as their arms went around one another and their bodies pressed tightly together. Seconds later it was clear that their tongues were involved as the girl moved her hands behind his head.

"Is this... is this porn?" I asked incredulously.

Amanda giggled beside me. "That's what happens when you let me pick."

"I'm certainly not complaining." The guy now had his hands on the girl's butt, squeezing as they ground against each other. Leaning back slightly I took my eyes from the TV screen to look Amanda in the eye. "You know, this is the first time I have watched porn with another person. It's such a turn on."

"Clearly" she said as she smiled and reached over to pat my growing erection through my pants, "I'm getting really turned on too-" Amanda cut off as I pressed my lips to hers. Pressing back she immediately opened her mouth, pushing her tongue towards mine in a lustful kiss. Wrapping her arms around me she pulled me towards her until our clothed bodies pressed tightly together. The momentum of my movement towards Amanda pushed her back down onto the couch with me on top of her.

Further pressing our bodies together I quickly realized I wasn't the only one of us with a growing hard on. Amanda placed her hands on my butt and squeezed, pressing down on my butt so my hips and crotch ground down into her. Using the pressure from me she ground her cock even harder against mine. Taking her hands from my butt Amanda quickly attacked the button on the front of my jeans. I followed her example and reached down for her jeans, managing to unsnap the button and start to drag the zipper down at the same time she did mine. We slid each others pants down in unison, only being able to slide them down to the knees before mutual lust made us press our bodies back together. Now only thin underwear separated our grinding cocks.

Amanda's hands returned to my butt only this time she slid her hands under my boxers to grab two handfuls of flesh. Applying pressure and massaging my butt again I was thrilled when I felt one of her hands slide over and her finger brush against my crack. Keeping a firm grip on one butt cheek she used the index finger on her other hand to tease the outside of my hole.

Sliding her finger up and down my crack I was practically begging for it by the time Amanda started to apply pressure directly on my hole. Penetrating me to the first knuckle I let out a moan as she began to wiggle her finger and give me so much pleasure that I realized I was pushing my butt up towards her finger. Amanda used her other hand to make sure my butt stayed down and our underwear covered cocks continued to grind against each other.

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byTallnhard1© 6 comments/ 69456 views/ 68 favorites

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