Amanda and Me Ch. 08

This story contains sex between a transsexual top and a male bottom. If you do not like stories where a man gets fucked by a transsexual please stop reading.

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The alarm on my phone woke me up while it was still dark outside. I reached over to turn it off and then sighed heavily when the buzzing stopped. I was too tired to get up yet and the warm, naked body pressed against my back was incentive enough for me to stay where I was. Amanda had shifted slightly when I reached over to turn off my alarm but now she settled back into me.

I laid there listening to Amanda's breathing. With her small breasts against me and her legs tangled with mine we were as close as we could be physically. But I also felt an emotional closeness with Amanda that was stronger and deeper than I had ever felt with anyone before. I had never enjoyed spending time with someone this much and I was actually disappointed that I had to leave her and go to work.

A few more minutes passed before I finally found the will to extricate myself from our entanglement and climb out of bed. I quickly slipped on my clothes before leaning back over the bed. Pressing my lips to Amanda's cheek I kissed her softly and whispered, "Have a good day." I got a sleepy mumble in reply and I smiled to myself as I picked up my bag and left.

I got to work a little earlier than usual. Sitting down at my desk I started to log into my computer but before the operating system could come up I felt my phone vibrate in my pocket. Fishing it out I looked down to see a text message from my friend Chris.

Chris: Good morning! It was nice running into you last night. Do you still want to grab lunch today?

I was glad to hear from him. I hadn't been sure if his invitation to lunch was sincere.

Me: Good morning. Yeah, that would be great. Want to meet at that new sandwich place on Main?

Chris: Sounds good. I've been meaning to try it. Noon?

Me: See you then!

I put my phone down and smiled. I was looking forward to catching up with Chris. We had chatted briefly at the fantasy football draft the week before but I looked forward to hearing about what else was going on with him. I still felt bad about him mistaking Kim for Amanda but I looked forward to finding out if he meant what what he said about her. Kim had certainly seemed thrilled when he said she was gorgeous.

I worked for a few hours until I got another text message. Unlocking my phone I saw that it was from Amanda.

A: Good morning baby!

I smiled and quickly responded.

Me: Good morning! Someone was pretty sleepy this morning when I left.

A: Yes I was. I guess you just wore me out yesterday. Hehe.

Me: It was my pleasure :)

A: So I talked to Kimmy this morning and she told me about running into your friend Chris yesterday.

Me: Oh yeah?

A: Yeah. Kimmy said he was cute and she was flattered by his comment about her. Is he a good guy?

Me: Definitely

A: Do you want to play matchmaker?

Me: Haha, sure. I actually have lunch plans with Chris today so I'll bring it up and see if he is interested.

A: Awesome! And I'm sure you don't need a reminder after our conversation about "trans" stuff yesterday but just don't mention anything about her status.

Me: Don't worry, I won't.

A: And probably not a good idea to mention that you had sex with her either. Straight guys can be weird about that kind of thing.

Me: Yep, mum's the word. I'd rather not have to explain to him how much I enjoy getting fucked in the ass anyway.

A: Lol. Speaking of me fucking you in the ass... What are you up to tonight? :)

Me: Haha, no plans.

A: Want to come out to my kickball game tonight and then go drinking with my teammates afterwards?

Me: Sounds good to me!

A: Great! My game is at 8 so I'll swing by your place at 7:30 and we can head over there together.

Me: I look forward to it. See you then!

I put my phone down and smiled. Now I just had to get through the rest of the day so that I could hang out with Amanda again. I was so glad that she invited me to her game and I looked forward to hanging out with her and her friends afterwards. Taking a deep breath I went back to work before I started missing Amanda even more.

About twenty minutes before noon I got up from my desk and headed out of the office. It was a bright, sunny day outside and I enjoyed the short walk to the sandwich shop. Chris was already waiting out front when I arrived.

"Hey, long time no see," I joked as I approached.

Chris laughed as we embraced in a friendly hug and then headed into the shop. There were only about five people in front of us and we chatted about the menu as we waited. After we each ordered a sandwich we grabbed a booth and sat down. The conversation immediately gravitated towards running into each other so I asked him how he knew about that Chinese place.

"My ex-girlfriend Monica loves that place," Chris said. "We used to get take-out from there all the time." He paused and then added, "I used to think it was a hip place but now that I know you go there I guess it isn't."

I smiled. "Ha-ha, very funny. I didn't even know that place existed until last night. Kim and Amanda made me choose a place and that sounded interesting."

Chris' face lit up. "Kim was the girl you were with last night right? She is roommates with the girl you are dating?"

I was so happy he brought her up. "Yeah. At the fantasy football draft I told you about Amanda but I didn't think to mention her roommate Kim."

Chris paused thoughtfully for a few seconds before stating, "She's really cute. Is she single?"

I thought getting to that would take a while but I was glad to see that I was wrong. "Yep, she's single." At another thoughtful look from Chris I asked, "Want me to set you up?"

"Yeah," he replied. "Is she nice? What do you know about her?"

I spent the next few minutes talking about Kim: The food she likes, how she knows Amanda, her playful disposition. I left out all of our sexual interactions and just focused on her personality. Chris was soon sold and he couldn't wait to see her again. I suggested a casual double date later in the week with me and Amanda and he agreed.

After that we talked about everything from fantasy football to our group of mutual college friends. He spent more time with them than I did so he caught me up on what everyone was doing. When our sandwiches came we ate unhurriedly and continued talking. By the time I glanced at my watch it was time to go back to work. I told him that I would touch base with Amanda and Kim and then text him about making dinner plans. He said he was available most nights.

I headed back to the office and worked through the rest of the day. I left work at a decent time and got home shortly after 6PM. I cleaned up like I usually did and then I ate a small snack as I waited for Amanda to arrive. In no time I heard the buzzer for the front gate. Buzzing Amanda in I peaked out the front door just as she approached.

"Hey sexy!" Amanda said as she walked towards me. She was wearing white athletic sneakers and a pair of black shorts that showed off most of her long, smooth legs. Her red t-shirt was emblazoned with her kickball team's name and her hair was tied back in a ponytail. Even with no makeup on and a tomboy look Amanda was sexy. I briefly considered asking her to skip the game so we could just get naked together immediately.

I smiled and met her in the doorway. "Hey baby," I said as I took her in my arms. I brought my lips to hers as she pressed her body against mine. Her unique feminine scent washed over me and I once again got lost in a simple kiss. When our lips parted I took a step back into my apartment.

Amanda followed me in and set her bag down. Giving me a big smile she asked, "So how was work today? Miss me?"

"I always miss you," I answered honestly. "And work was fine. I just tried to get through the day so I could hang out with you."

"Aww, that's sweet," She said as she reached over and gave my back a quick rub. "How did your lunch with Chris go? Anything to report?"

I smiled. "Well, Chris is definitely interested in Kim. He brought it up before I even got the chance and he asked if she was single."

"That's good," Amanda said.

"Yeah, so I told him that she is and I asked if he wanted me to set them up. He did." At a smile from Amanda I continued, "I suggested a double date with me and you this week just to make things more casual."

"Good idea," Amanda said as she pulled her phone out. "Let me text Kim and find out when she available."

As Amanda texted Kim I picked up my keys. After I put on my shoes I was about to tell Amanda that I was ready to go when she looked up from her phone and said, "Kim says she is down for dinner tomorrow or Thursday night."

"Ok, I'll let Chris know," I said as I pulled out my phone. After texting Chris I turned back to Amanda. "So am I gonna be bored at your kickball game tonight?"

"No way," Amanda answered enthusiastically. "You get to watch this hot ass run around for an hour," she said playfully as she turned around and shook her behind. "And then we get to drink!"

I laughed. "Well when you put it that way."

We headed to the field. It was only a few blocks from my apartment so we arrived after a short walk. A number of her teammates were already there including a friend of Amanda's named Jen. I was introduced to Jen and her boyfriend Mark, who was also on the team, as well as the other players. We all joked around for a few minutes until it was time for the game to start. I turned around to go sit down.

"Where are you going?" Amanda asked.

"Umm, the bleachers," I said with a little bit of confusion.

"Come on," she said as she grabbed my arm and pulled me in. "You can sit with us."

I smiled as I sat with her and her teammates on the bench. When the game started her team was in the field so I was by myself in the dugout but when they were "batting" I was in the middle of the action. Everyone was quick with a joke and they seemed to be having a good time even if they weren't good at kickball. They all encouraged each other and there was lots of clapping and slaps on the back. It was a fun atmosphere.

After about an hour I felt my phone buzz in my pocket. Taking it out I saw a text from Chris. He said that he already had plans on Thursday but he was available on Tuesday for dinner. I showed Amanda the text and she smiled. Typing out a response I let Chris know that we were all good with that and I would text him again the next day to let him know where. At the same time Amanda pulled out her phone and texted Kim that we were on for dinner with Chris the following night.

A few minutes later the game ended. As everyone gave each other high fives I overheard Amanda ask Jen where everyone was headed for drinks. I didn't hear the response but then Amanda asked her, "Can we get a ride with you?"

Amanda and I accompanied Jen and Mark to their car. When we got to the car Amanda and I hopped in the backseat as Jen tried to explain to Mark why she didn't catch the ball on that last play.

"Didn't you see the way it was spinning?" Jen asked her boyfriend. "It was impossible to catch."

Mark smiled. "Ok honey, if you say so."

"No really it was," Jen replied as Mark started driving towards the bar. "It was flying at my face and I panicked."

There was a pause before Mark teased, "I thought you liked it in the face." Then a mischievous smile crossed his face.

Amanda laughed as Jen playfully hit Mark in the arm. "Not in front of them," she said with an embarrassed smile and a nod towards the backseat. "I'm sure they don't want to know every detail about our sex life."

"Don't worry Jen," Amanda said reassuringly. "You're not the only one in this car who likes a good facial."

Jen and Mark both laughed as Amanda leaned over and playfully poked me in the ribs. I laughed because I knew Jen and Mark thought Amanda was talking about herself.

We pulled up to the bar a few minutes later. When we walked in we saw a group of Amanda's teammates pushing some tables together. We helped gather chairs and then we all ordered drinks. Talk quickly turned to the kickball game as everyone recounted various plays and jokes they made. The fun vibe from the field immediately carried over to the bar as everyone began drinking and laughing.

Amanda and I chatted with everyone from the team but we mostly sat with Jen and Mark. Once we had consumed a couple of drinks I asked them to tell me some embarrassing stories about Amanda. Sadly they didn't know any but Jen and Mark did tell embarrassing stories about each other and in no time they had me and Amanda cracking up.

Suddenly Amanda leaned over and whispered in my ear, "I really want to suck your dick right now."

I jerked my head back in surprise. I felt my limp cock twitch in my pants as I glanced over to see her smiling at me. I studied her face for a few seconds and then leaned in to whisper back, "Here?"

"I'll take that as a yes," she said with a laugh.

Amanda grabbed my arm and started dragging me away from the table. "We'll be right back," she said to Jen as we made our way through the crowded bar. I thought she was going to pull me into the women's bathroom like she had done a few nights earlier but she didn't. She kept going and pushed open the back door of the bar. As we exited into the empty alley she looked around to make sure the coast was clear.

Amanda's mouth met mine as she pressed me back against the building. I loved the feeling of her soft, feminine body against me and I returned her passionate kiss with vigor. My hands went to the back of her head as hers went down and began rubbing my cock through my pants. In seconds I went from semi-hard to fully hard and I wondered if she meant what she had said in the bar.

A few seconds later Amanda broke our kiss. I let my hands fall to my sides as she squatted down in front of me. Grasping the zipper on my jeans she quickly dragged it down. She then reached her hand into my pants and began feeling around for my cock. I looked around nervously to make sure we were alone and then I helped Amanda by adjusting myself. Once she navigated her hand through my underwear she pulled my cock out into the open.

I gasped as she immediately took me in her mouth. My cock was enveloped with warmth as she pushed her face forward and inhaled all seven inches. When her nose touched my jeans she quickly pulled her mouth back until just the head was inside. She looked up and made eye contact with me as she slid her mouth back down to the base. It felt so good that I threw my head back and moaned.

As Amanda slid her mouth back and forth on my cock she reached around and grabbed my ass. At first she used her hands on my butt to pull my midsection towards her and take my cock deep in her mouth but after a few seconds she started rubbing my hole through my jeans. I moaned at the stimulation and I knew I wanted more so I quickly loosened my belt. Amanda immediately understood and she slid her hand down the back of my pants.

She immediately pressed her index finger directly to my hole. I let out a loud moan that would definitely have alerted someone to our presence had anybody been nearby. My cock twitched as her finger pressed into me. Pulling it out and pushing it in Amanda fingered my ass while she continued sucking. Her slurping sounds and my moans echoed through the alley.

With her finger in my ass and her mouth on my cock I knew I wouldn't last long. The pleasure hit me in waves and I looked down to see Amanda looking up at me. She had a look of pure lust in her eyes as she sucked me. I loved that look and the fact that she was clearly turned on by giving me pleasure pushed me over the edge.

"I'm cumming," I said hurriedly moments before I felt myself pass the point of no return.

Amanda clamped her mouth around my cock and sucked harder. She pushed her finger further into my ass and kept it there as I came. I moaned as my whole body convulsed due to the force of my orgasm. I felt my ass clamp down on Amanda's finger as my cum began to spill into her mouth. With my eyes squeezed shut I rode the wave of pleasure until I had given her every last drop.

Amanda pulled her mouth off my cock with a pop. Taking her finger from my ass she stood up and smiled at me before pressing her body against mine. Bringing her lips to mine she opened her mouth and I felt my warm cum flow in. Swirling my tongue with hers I let the salty flavor of my seed roll around my mouth as we made out.

"There you guys are!"

Amanda broke our kiss and we both looked over to see Jen peaking out the backdoor.

"Sneaking away to make out huh?" She asked with a smile. "Come on, we're gonna do shots!"

Amanda nodded and I swallowed the cum in my mouth. Jen didn't move so I turned away from her and tucked my softening cock back in my pants. Amanda had been blocking Jen's view of it since our bodies were pressed together so Amanda hesitated for a second to give me cover. Once my dick was put away and my belt was tightened I kissed Amanda on the head and said I was ready to go.

We followed Jen back inside to find a row of shots waiting on the table. Seconds later the entire kickball team gathered around and everyone grabbed a glass. We all said cheers and then downed the strong alcohol. I made a grimace as I set my empty shot glass down and looked over to see Amanda making the same face. We both laughed as we reached for the cup of limes.

Amanda and I hung out for another hour. Everyone was feeling pretty tipsy so it was a good time. Finally Amanda asked if I was ready to go and I nodded. She pulled out her phone to open an app and then she typed in the address of my apartment. Finishing her ride request she turned to Jen.

"I think we are going to head home," she said.

"Awww," Jen said dramatically. "But we were just getting started."

"It's a Monday night," Amanda answered patiently. "Unfortunately we both have to work in the morning."

"Ok," Jen relented. "Get home safe." She hugged Amanda but didn't immediately let go. She was whispering in her ear for a few seconds before she finally let go.

"Don't worry, he does," Amanda answered as they separated.

We said goodbye to Mark and the rest of the team and then headed out the front door of the bar. Standing on the curb I put my arm around Amanda while we waited for our ride. Suddenly a thought occurred to me and I asked, "So what did Jen say to you when she hugged you goodbye?"

Amanda laughed. "Oh, just that she was excited for me because she could see how happy you make me." I smiled down at her as she added, "Then she told me to make sure you treat me right. At least that's what I think she said. I don't know, she was pretty drunk."

I laughed and said, "That's sweet that she wants you to be happy."

"I am happy," Amanda replied and then she leaned in for a soft, gentle kiss.

A few seconds later our ride pulled up. I opened the back door for Amanda and then I climbed in after her. She sat in the middle seat and then exchanged some pleasantries with the driver as he began driving back towards my apartment. After I buckled my seat belt Amanda leaned her body into me and I placed my hand on her bare leg. I was not surprised that it took only seconds for me to get turned on by how close we were sitting.

Without a word I slowly began to slide my hand up her leg. Amanda's breathing increased immediately and in seconds my hand slid up and began to caress her inner thigh. Her reaction to my touch turned me on too so I lifted up my hand and placed it on her shorts. I began slowly rubbing her soft cock through the fabric and in seconds Amanda placed her hand on top of mine. As she pushed my hand down to create more friction I glanced up at the rear view mirror but the driver didn't seem to be paying us any attention.