tagTranssexuals & CrossdressersAmanda and Me Ch. 02

Amanda and Me Ch. 02


I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life.

As I lay there thinking about the night before I was surprised at how many new sexual experiences I had in one night. I sucked dick last night. Not only that but I got fucked too. I knew I wasn't gay but the fact that I enjoyed having her hard cock buried in my ass had opened up a world of sexual possibilities that I had never even contemplated. I wasn't sure what it meant but I knew that I would like to discover more it.

I was shaken out of my reminiscing by the sudden ringing of my cell phone. My heart skipped a beat as my first thought was of Amanda but looking at the caller ID I was disappointed to see that my work was calling. After a brief conversation with the frantic weekend IT staff I agreed to come in for a few hours to help mitigate their problem. Throwing on a t-shirt and jeans I quickly headed out the door.

Six hours later I walked back into my apartment and as usual went straight to my computer. The entire time I had been at work I was thinking about the night before. Since I knew it would be some time before I would actually call Amanda and set up a date, I instead decided to looking at shemale porn. I had only ever really looked at shemales by themselves before and although I had glimpsed shemale on guy stuff before I had never watched an entire video. However, now that I had experienced being with a transsexual I couldn't wait to relive that experience watching porn.

I went to my favorite shemale porn site and searched for "Shemale Fucks Guy" and got more links than I thought existed. It was amazing to me how many different videos I could choose from, everything from super dominant shemales forcing themselves on guys to videos of amateur shemale-guy couples making mutual love to eachother. I clicked on a video of a cute brunette shemale and a skinny guy because the description said "T-girl with big cock fucks guy".

As the action on the screen began to heat up I took my cock out and began to stroke it. The guy in the video started by going down on the cute brunette shemale and the title of the video lived up to it's name, her cock had to be eight inches long and thick. I couldn't stop thinking about how much it reminded me of Amanda's cock and that got me even more turned on. After sucking for a few minutes the guy laid back on the couch and the shemale began fucking him. Playing along with the video I slid my finger back to my own asshole and began to play with it.

After a few minutes of watching the video and fingering my ass, I began to think about the fact that I could only use my finger and didn't have anything bigger to put back there that would better simulate the cock in the video. I immediately opened another tab on my browser and searched for "anal dildos". I had never bought an adult toy of any kind so browsing through some online adult toy shops I was quickly overwhelmed with selection. Large and small dildos, buttplugs and anal beads, there were so many options that I knew I had to give myself fewer choices. Thankfully I knew just the place to go.

Everyday on my drive home from work I passed the same porn shop. "DVDs! Video Booths! Toys!" screamed the sign out front as I pulled into the small driveway. I parked near the back hoping that no one driving by would see my car and walked into the dimly lit store. It was my first time in an adult sex shop and I was so nervous that I almost tripped on the first step on my way in. Taking a quick look around I was relieved to see that the place was practically empty.

I put my head down and walked towards the toy section at the back of the store. Walking down the first isle I passed a few different types of dildos and buttplugs: rubber types then glass ones, some shaped like penises, others more rod-like. It being my first time looking I must have walked back and forth ten times examining the selection so I shouldn't have been surprised when I heard a femine voice ask, "Can I help you with anything?"

My cheeks immediately turned red as I turned to see a moderately attractive blonde standing there with a nametag that read "Megan". I shook my head and managed to squeek out a quick 'no' but thankfully she wasn't fooled. Coming over to stand next to me Megan pointed at the rather large silicone anal dildo right in front of me.

"Oh, this one is my favorite. As you can see it's thick and long and definitely would help stimulate your prostate."

At that I flushed an even deeper shade of red as it was that obvious that the anal toy would be for me.

Megan patted my arm and reassured me, "Oh, don't be embarrassed. I use that same toy on my boyfriend all the time and he absolutely loves it. Is this your first time purchasing a toy?"

I nodded my head and she picked up the anal dildo just below the one she had recommended earlier. It was the same length but more of a tapered shape so it was thinner at the top. She continued, "In that case I recommend this one so you can start with a smaller diameter and as you get more comfortable you can take more of it. Is that all you were looking for today?"

Still being mortified that I was getting help selecting an object that I would soon have in my ass I managed a quick 'yes' and started to follow her over to the register. She placed the dildo on the counter and looked at me. "Being that this is your first purchase can I recommend something? Before I do anal play with my boyfriend I make him clean himself out so that it's less messy." She reached behind her and grabbed a fairly large box. "This is an enima kit, it will walk you through the steps required to flush yourself out so that when you play with your new toy it will be clean."

I picked up the box and read the features. I can't believe I hadn't thought of this before. Does that mean it was dirty last night when Amanda had fucked me? I was suddenly embarrassed at the thought and knew I would be purchasing what she recommended.

Still unable to make eye contact with her I mumbled, "Ummm, yeah, I'll take it."

She smiled at me as I paid and she put my stuff in a black plastic bag. "Have fun!" she called as I practically ran out the door with my new purchases. I raced home and looked around as I got out of my car in the parking garage to make sure the coast was clear. Once I was safely in my apartment I took out my new purchases and marveled that as shy as I am I was able to get the right toy so I could try new things out for myself.

I placed my purchases on the table and started by opening the emina kit. I figured that if I was going to play with my new toy I might as well be clean. Spreading all the equipment out on the table I read through the easy-to-follow instructions and grabbed the things I needed. Heading into the bathroom I started to fill the bag with water while I hooked up the nozzle to the tubing. When the bag was full I assembled the rest and stepped into the shower.

Laying down in the tub I lubed up the nozzle and slowly pushed it into my ass. I turned the nob and let the warm water start flowing. While the enema wasn't purely sexual it was definitely a turnon and by the time I had emptied the entire bag of warm water into my ass my cock was half hard. Waiting as long as I could I emptied myself out before repeating the process two more times.

Now that my ass was cleaner that it had ever been I walked back to the table and picked up the silicone dildo. Opening the package I ran my fingers up and down the soft yet durable silicone and was amazed that I might be able to take this whole thing in my ass one day. I took the toy to my room and laid back on my bed. Applying a liberal amount of lube to the length of the dildo I placed it at my hole.

I slowly applied pressure to the back of the dildo and felt my ass start to stretch around the head of the toy. Just like the night before it took quite a bit of pressure to get it to finally pop in but once it was in I was able to steadily push. I was glad the girl at the porn shop had suggested a dildo with a smaller diameter tip as for the first minute or so I only able to take the first inch. As my ass stretched I was able to accomodate more and before I knew it I was able to take about half of the dildo in my ass. By then my cock was rock hard and was begging for attention. With my left hand I continued fucking my ass with the dildo while my right hand stroked my cock.

Because it was such a new sensation it only took about thirty seconds before I felt that familiar feeling in my balls. Slamming the dildo in I felt the first stream of hot cum leave my cock, landing in the middle of my chest. My second shot landed in my belly button as the rest quickly covered my hand in sticky white cum. I slowly eased the toy out of my ass as I lay on the bed catching my breath. While it hadn't been as great as last night it was by far the best solo session I had ever had.

After cleaning myself up I watched some TV and then turned in early. On Sunday I got up and ran some errands but by early afternoon I was dying to call Amanda. I didn't really know the proper etiquette about when to call but I just knew that I was dying to see her again and to have another amazing experience. It took me twenty minutes of staring at my phone at the table before I was finally able to dial her number and hit send.


"Hi, is this Amanda? We met the other ni..."

"Of course. Hey! I was hoping you would call, how are you doing?"

"I'm doing pretty good, how about you?"

"Good. It's been a pretty good day so far, I've just been cleaning up around here after some girlfriends came over last night. As for tonight... oh hey, so I'm supposed to go to this art show tonight for an artist friend and my girlfriend was going to go with me but she just bailed. I know this is last minute but, would you want to go with me?"

"Ummm, yeah, sure..."

"You sure you don't have any other plans or anything for tonight?"

"Nope, not that I can think of."

"Great! I'm not dying to go but I told him I would come so we don't have to be there for long. The only bad thing is that it takes about thirty minutes to drive there. I can drive so how about I come pick you up at eight and we can go to the show?"


"Perfect, I'll see you later then. Bye."


I tried to tell my heart it could stop beating at a hundred miles an hour but it just wouldn't listen. Was it really that easy to set up a date or had I just found the perfect girl? I stressed for a day and a half about what I would say when I called her but before I could say more than a few words it was done. This was fantastic and I couldn't wait until eight o'clock. The first thing I did was run into the bedroom and grab my enima kit.

After cleaning myself out three times I sat down on the couch to watch TV and waste the remaining four hours or so until eight o'clock. It seemed like every few minutes my thoughts would drift away from whatever I was watching back to Amanda. At 7 o'clock I started getting ready and finally at 8:15 I heard my phone ringing.


"Hey, I'm downstairs."

"Ok, on my way."

I took the stairs two at a time because I was excited and nervous. Walking out the front of my apartment complex I saw a dark colored hatchback of some kind parked right in front of my building. With the windows tinted it was hard to make out who was inside but it looked like someone was waving so I walked over. Opening the passenger door I saw Amanda so I slid in and shut the door behind me. She looked just as good as I remembered.

"Hey, thanks for picking me up."

She smiled. "No problem, it's good to see you again sweetie."

Amanda leaned all the way over into my seat and put her lips on mine. I thought it was going to be a quick peck but clearly she had other ideas. She placed her hand on the back of my head and opened her mouth, letting her tounge explore my mouth and swirl around my tounge. After a few seconds she pulled back and made a contented 'mmmm' sound as she shifted the car into drive and we drove off.

The half hour drive to the art show was nice once I got over my nervousness and just let the conversation flow. We talked about our families and living in the city and our various jobs. It was another great conversation that I felt lucky to be having. I didn't know if I should bring up the surprising sexual part of Friday night but Amanda managed to bring it up after about ten minutes when I mentioned that this would be my first art show. Amanda winked at me and said, "I guess it's a weekend of firsts for you then. But I think you like it." When I smiled and enthusiastically said "yes" she reached over and patted my leg.

Pulling off the freeway into an industrial neighborhood we drove a few blocks and then down a side street by a number of large warehouses. Amanda was looking around and reading the names on the buildings and must have found the right place because she parked at the rear of the small complex. Getting out of the car Amanda shrugged her shoulders.

"The show is in one of these buildings but I'm not sure which one. Let's take a look around." Grabbing my hand Amanda started through the maze of warehouses, peaking in the windows of any building that had light in the window. After checking three or four buildings we finally heard music coming from the next one.

Pulling open the door we stepped into what looked like an amateur rock video set in a warehouse filled with random junk and paintings. The music was blasting and the place was definitely a cooler event than I had ever attended before but Amanda just held on to my hand and led me towards the first sculpture looking thing in the middle of the floor. Standing in front of it I didn't know if what I was looking at was art or just welded together scrap metal that vaguely resembled an eight foot tall statue.

Standing to one side I used this opportunity to sneak looks at Amanda. She was wearing a cute black skirt with a light colored tank top and heeled boots up to her knee. It was casual and sexy but she wouldn't have looked out of place in fancier places. Her hair was down and once again I was struck by how beatiful her face looked and how I couldn't wait to kiss her more. Just as that thought crossed my mind Amanda was lifted off her feet by a six and a half foor bearded mountain of a man.

"Amanda, I'm so glad you came. You look great!"

"Thanks Mike, amazing stuff you got here! I can't believe you finally have your own show."

He laughed. "Yeah, it took a long time to finally put everything together but it's my life's work so hopefully it's halfway decent."

Mike glaced at me so I quickly extended my hand and introduced myself as Amanda's friend. I couldn't be sure but I thought I saw Mike exchange a questioning glace with Amanda which must have been confirmed by her nodding and smiling. Mike only stayed for a few minutes before seeing another group of people he needed to bear hug. As he left Amanda lead the way deeper into the warehouse.

Slowly making a circuit of the warehouse we chatted about Mike's artwork while we constantly flirted. From small touches to having our arms around eachother or even doing playful little pinches we couldn't keep our hands off eachother. In the back corner of the warehouse we stopped in front of a small room filled with spray painted old books. I stood behind Amanda and put my arms around her waist, leaning into her so that she could feel my half hard cock on her butt cheek. She responded by placing her hand on top of mine and sliding it down to rub the bulge in the front of her skirt. After a few seconds of rubbing she quickly spun around and pressed her body against mine. Kissing me passionately I could feel her cock press against mine. Not one to be discreet she ground her crotch against me in a circular pattern.

After a few seconds I started to get nervous that people might see but Amanda just wrapped her arms around me and kept grinding. Finally she pulled back and breathlessly asked, "Ready to go now?"

I smiled and nodded and then took a quick look around to make sure no one saw. Trailing Amanda to the door we quickly exited out into the night. Walking between buildings I could feel the sexual energy between us. Making a quick turn next to a dark, quiet warehouse Amanda put her back up against the wall and pulled me to her. Continuing our kissing and grinding like we did at the show Amanda used both hands to grab my butt and get more leverage to grind her now hard cock into me. I returned the pressure as I pressed her firmly up against the wall.

I broke our kiss to lean my head down and start passionately kissing her neck. Using my hands I rubbed her breasts through her tank top as I felt her reach between our legs and message our cocks. Amanda then reached down and hiked her skirt up to her waist so her cock was out in the cool night air. My first reaction was to look around and make sure no one could see us but once I realized we were all alone next to a dark warehouse I reaching down and took it in my hand as she massaged my cock through my pants. Once again I was amazed at how warm her cock was to the touch and the soft feel of it in my palm. Stroking it a few times I had this sudden urge to taste it.

Without warning her I bent my knees and lowered myself down until my knees softly touched down on the hard pavement. Continuing to stroke her cock I started licking the tip and was rewarded with a low 'mmmm' sound from her throat. Her precum tasted warm and salty and I couldn't wait to get more. I took her cock into my mouth and started sucking, working my mouth around the head then sliding down the shaft. Even though it was really only my second time sucking cock I felt like I was really starting to get the hang of it.

At first Amanda let me control the tempo of my sucking but soon she started moving her hips back and forth in rhythm. She bounced her butt off the wall behind her to match my motion and after a few minutes Amanda placed her hand on the back of my head and picked up her pace.

"Oh that's it baby. You're gonna make me cum!"

I thought she was going to cum in my mouth but right when I felt the first spasm of her cock she pulled it back out of my mouth and started stroking it. Her first cumshot went mostly into my mouth, hitting my teeth and upper lip and landing on my tongue. I looked up to see her "o" face as I felt her second shot hit me in the cheek and the side of my mouth. Her third shot hit mostly the side of my nose and my other cheek and then she quickly pushed her cock back into my mouth. Feeling her hot cum ooze out I tightened my lips around her cock and swallowed as quickly as I could.

Twitching for the last time I felt Amanda's body relax so I let her wet cock slide out of my mouth. I looked up to make eye contact with her and she had the biggest smile on her face that I had ever seen.

"Oh my god, you look so amazingly sexy with my cum all over your face. Did you like that?"

I swallowed the last bit of cum in my mouth. "Yes, very much. I didn't really know what to expect but after my first experience with it I think cum tastes good."

"Only mine sweetie. Here, let me help you with that." She used her finger to push the cum on my cheeks down into my mouth where I quickly swallowed it. What had gotten into me? On Friday afternoon I had never touched another person's dick before and now I was not just sucking dick but also enjoying cum. It was amazing what a sexy girl with a hard cock could do to me.

Smiling as I stood up I pressed my lips to hers. She returned the kiss passionately, even putting her tongue in my mouth. I was glad she didn't pull away from making out with me because I had always felt comfortable tasting myself on someone else and was glad she did too. Breaking the kiss she pulled her skirt back down and we turned and headed for the car.

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byTallnhard1© 8 comments/ 100403 views/ 99 favorites

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