tagTransgender & CrossdressersAlex and Tom Ch. 02

Alex and Tom Ch. 02



"Wow." Said Tom. "You are just incredible."

My heart was racing as I lay there next to Tom. He seemed to be lost in thought and just taking in the moment, his breathing was deep and relaxed, while mine was just the opposite. I was trying to breathe softly and control my heartbeat as my mind raced through what had just happened.

My eyes were wide open, although he couldn't see them as I was snuggled up next to him. Did I just have sex with a man? I had never even thought about anything like what had just happened. I actually thought up until today that I would never have sex with anybody. I was after all a terrible excuse for a man, even for a boy. Of course I had thought about sex and girls and stuff but it always seemed like something that would never happen to me. Girls never gave me anything but trouble and even if I was ever able to get a date, I was so ashamed of my body and tiny dick that I could only imagine them laughing at me like they did even when I had my clothes on.

What my mind kept going back to though, was that I had liked what just happened. I liked where I was right now, curled up with this man who had just...What exactly. Seduced me? Made me feel special and wanted and desired?

I felt Tom's hand as he stroked my arm. I felt his chest rising and falling as he relaxed. I felt giddy, excited and content. Am I gay? I thought to myself. I mean I had just had his cock in my hands and he came on me. He came all over my tummy and chest, I could still feel it drying on me. Should I be disgusted? What does all this mean?

I didn't care. I felt so comfortable laying there. I didn't care if I was gay. I wanted to be right where I was. I wanted to feel like this all the time, I wanted to leave my crappy life behind and feel desired and safe and wanted. The way he had looked at me and told me I was special had made me feel something I had never felt before. And his cock, the way it had been so hard, the way it had throbbed in my hand. It was the most exciting thing I had ever seen and I wanted more.

"Alex." Tom said. "That was truly amazing. I think I've been looking for you my whole life."

"Tom." I asked quietly. "Are you gay?"

He didn't answer right away. After a quiet moment he said, "I've never thought of myself as gay. But I guess I've always had a thing for pretty guys like you."

He called me pretty again. It didn't sting this time, he had made me feel pretty. My mind flashed back to the difference in our bodies, how manly he was and how girly I looked next to him.

"Up until recently I was married." He said.

I ignored that and asked the question that was on my mind.

"Am I gay?" I asked.

"I don't know, I don't think so. I mean, I guess it's complicated. Labels don't always fit you know."

We laid there in silence for a few minutes.

"I really liked what we did." I said quietly as I snuggled into him.

He rolled over and slid down on the bed so he was looking me in the eyes. "Alex", he said, "You are so amazing, I can't remember being turned on that much since I was in high school. You do something crazy to me. I think you are so beautiful." Then he kissed me, very tenderly on my lips. I felt butterflies in my stomach again and smiled into his mouth.

He kissed me for a few minutes, moving his hands over my naked body as I lay there feeling wonderful.

"I need to get some water." He said as he slid out of the bed and stood up. I watched him as he walked across the room, looking at his tight butt and his cock hanging down. He picked up his shirt and put it over his head as I stared at him, mostly at his cock, I really couldn't keep my eyes off of it. Then he found his boxer shorts and put them on. He opened a dresser and pulled out a t-shirt and laid it on the bed.

"Here, you can wear this until your clothes are dry." He said.

He turned to walk out of the room, but stopped after a couple of steps. He paused as if thinking about something. Then he turned back to me.

"Hey, Alex." He said. "Would you try something for me?" His tone was apprehensive.

"Sure." I said eager for the opportunity to do anything for him.

He seemed unsure of himself as he stood there. "I mean, you don't have to if you don't want to, but, I mean, well, if you did, that would make me very happy." He stammered.

I felt a lump in my throat like he was going to ask me to do something I shouldn't. Then he walked across the room to a different dresser and opened the top drawer. He rummaged around for a few seconds and then turned around.

"Would you wear these for me?" He asked. "It would mean so much to me."

He was holding a pair of pink girl's underwear.

"Please baby?" He said in a playful voice as I sat there looking at him. "For me?" He pleaded.

He was looking at me longingly, playfully. I really didn't know what to do or say. I just sat there on the bed, still halfway under the covers. He was smiling at me with kind of a devilish grin.

"Just try them on for a minute." He said, his grin getting bigger, more playful.

I picked up the t-shirt he had put out for me and pulled it over my head. It swallowed me as the sleeves came down past my elbows. I slid my hands through my hair pushing it back behind my ears. I slid my legs over the bed, and stood up, the t-shirt came down to my upper thighs covering my butt and crotch, thank god for that. I began to walk over to him. His eyes lit up and his grin broadened. His smile made me smile and I felt like I couldn't resist him. I wanted to do what he wanted me to do, I wanted to make him happy.

I took the panties from him and looked at them. They were soft with a little lace around the edges and were made of that slippery stretchy material. There was a little pink bow on what appeared to be the front of them. I manipulated them in my hands until I figured out how they go on and then bent over to put first one and then the other foot into them. Then I pulled them up, feeling the soft fabric on my thighs and watching as my little dick disappeared into the delicate material. When they were all the way up the t-shirt had moved up with my arms and I looked down to see they made a little pink triangle where my dick had been. They were so slippery and soft. I remember the way they felt on my butt, it was like they were squeezing it a little. I ran my hands over my backside and felt a little tingle while I stared down at the front, my little bulge barely noticeable. I looked up at Tom. He was looking at me with huge eyes, and his hand was on his crotch. I saw him give himself a little squeeze.

"Oh my god Alex! He said.

"Do you like it?" I asked.

I let the t-shirt fall down over myself. Tom just stood there and smiled at me. I blushed.

"Very much." He said. "Very much indeed."

"Turn around." He said.

I spun around with my butt facing him and felt him lift up the back of my t-shirt and then felt his hand on my fanny. He gave one cheek a deep squeeze and I felt the fabric tighten all over. I giggled because it tickled a little bit. He rubbed his hand over my backside and was kneading it and squeezing as he did. The thin slippery material felt amazing on my skin. I looked over my shoulder and he was looking down at my bottom with that same hungry look in his eyes as before, when we were on the bed.

"Mmmm, your ass looks amazing." He said. Still squeezing and massaging me through the silky material. He gave my ass a little pat and said, "Let's go get some water." He took my hand and walked me out of the room.

Walking down the stairs to the kitchen I was hyper aware of the silky material between my legs and the cool air moving over my bottom. I felt excited and a little giggly. This was fun I thought to myself. In the kitchen he got us some water which we both gulped down. He finished his glass first and said he was going downstairs to change my clothes into the dryer.

Standing in the kitchen i reached down and felt the panties on myself. I let my hands run over the back caressing my bottom and then to my hips on the sides feeling the lacy material. I tugged at the little bow on the front as I lifted the shirt to look down at the front of them. My hand moved down to where my little bump was and slid over my dick, which was sort of semi hard. It felt wonderful. I rubbed my dick lightly through the material and felt an electric tingle go all through my body. I pushed my hand into the bump, feeling my little dick push into my sack. The material was a little bit shiny and I loved the way the color looked next to the skin of my lower tummy and thighs. I heard Tom coming up the stairs and let the t-shirt fall down over my new panties.

He came up behind me, put his hands on my shoulders and kissed the top of my head. He slid his hands down the front of me, squeezing me just a little as they passed over my chest and tummy coming to rest on my hips. He pulled me into himself gently and I could feel his cock against the top of my butt. It was soft and hanging down, but still such a presence. I arched my back into it reflexively. He made a little grinding motion and I giggled again, feeling aroused.

"I want to show you something Alex." He said as he moved away from me and took my hand, leading me towards the stairs. When we got to the steps he put his hand on the small of my back and led me in front of him. Half way up he said, "Damn Alex, you have such a sexy ass." Then I felt him pinch me slightly on the bottom of my butt cheek. Feeling playful and excited by all that was happening, I stopped and pushed my butt out. He put both his hands on my butt, cupping my cheeks and squeezed. The angle with him below me on the stairs made it so that his thumbs were really close to my butt hole and as he squeezed my cheeks came apart causing the panties to bunch up in my crack. He did that like 5 or 6 times and the tingles I felt were magical, causing me to push my fanny towards him more. Then he sort of pushed me on to keep me moving up the stairs.

He led me down the hall, passed the bedroom and bathroom to a room at the end. It was an office with a big wooden desk and shelves stuffed with books and binders. There was a big computer monitor on the desk and a nice comfy office chair in front of it. He sat down on the chair and reached out, pushing a button on the monitor.

"Come here baby." He said, patting his right thigh. His legs were open and I moved in between them sort of half standing and half sitting on his leg. He put his arm around my waist and gave me a little squeeze just above my hip. The hairs on his thighs were tickling my butt cheeks just below the silky underwear as we watched the computer screen go through its start up.

"Thanks for wearing those for me." He said, moving his hand down slightly so that his fingertips were touching the side of the panties through the t-shirt. "Do you like them?" He asked.

"I guess so." I said. "I like that you like them." I said.

"Oh you special, special thing Alex. Do you like the way they feel?"

"Yeah, they are really soft, and they feel really nice on my butt." I said, kind of shyly, still a little embarrassed to be talking about it.

"What about here?" He asked as he moved his hand down to the front of them, lifting up the t-shirt slightly and exposing the pink silky triangle. I looked down and watched as his fingers caressed the material sending beautiful tickles through me.

I squirmed a little as he gently pushed on the little bump where my dick was.

"Yes." I said softly, feeling myself blush as my butt wiggled. "That feels good too."

The screen flickered as the computer came to life, breaking the moment we had drifted into and Tom's hand moved from my crotch to the mouse on the desk. He clicked away at some things. And then the computer made a bunch of weird noises. After a minute, he began clicking some more.

I was looking back and forth from the screen to him, watching him. He looked so intense when he concentrated. I thought to myself how much I liked looking at him.

"Here." He said. "I want to show you this."

I looked over at the screen. There was a picture on it of a pretty girl in a bikini. She had black hair, beautiful eyes. She was really hot. He clicked the picture and it changed to a different picture of the same girl. In this one she was sitting on the edge of a bathtub. Her butt was hanging over the side a little and she was turned around facing the camera. Her dark hair was flowing down her back. She was really sexy.

He clicked again and there she was sitting in the bath tub full of bubbles, her hands were on her chest, above her boobs. Her nails were painted a deep red, and her boobs were small but really pretty with pink nipples. He clicked again. In the next picture she was standing up in the bathtub.

"Whaaa..." I said. Staring at the picture wide eyed. "She has a dick?" I couldn't believe what I was looking at. This gorgeous woman in the picture had a dick between her legs. "Is that real?" I asked, starring.

"It sure is." I heard Tom say. "She's a very special girl, she's a transsexual."

"I can't believe it, she's so pretty. Did she have a penis attached to her, like by a doctor?"

"No, she was born a boy. But sometimes special boys like her find out that they are more girl than boy."

"But look at her boobs, and her curvy hips. She doesn't look anything like a boy." I said.

"She's very special Alex, Just like you."

He clicked again and she was standing there with her dick poking out in front of her, like halfway hard. It was kinda big, not like Tom's, but definitely bigger than mine. She was so hot. How is that possible I thought? She has boobs and a dick? And she's so pretty, like a girl from Playboy.

"Isn't she gorgeous?" Asked Tom.

He clicked again. A different girl appeared on the screen. She was wearing a pretty yellow sun dress and smiling at the camera. He clicked again, same girl, but now the dress was pulled down and she was in a bra, CLICK, now she had a boob out, CLICK, now both boobs and just her panties, CLICK, now her panties were pulled down in front and her little dick was sticking out.

Oh my god, I thought. It's like mine. "She looks just like me down there." I said to Tom.

"You're both very special people." He said. "Look at her skin, it's just like yours too. So soft, and pretty."

His left hand moved to my thigh as he continued to click. There were so many different girls, all of them with dicks. Some were really big, like Tom's. Most were bigger than mine, but some of them were just like me. There were girls with big boobs, little boobs and some of them had no boobs at all, just girly nipples, like mine. All the girls looked happy, some of them looked nervous, but when we got to the end of their "picture set" as Tom called it, they were all smiling.

Tom's hand was squeezing and stroking my thigh and his fingers were brushing against the front of my panties as he clicked through the pictures. I wasn't really excited as much as I was in awe. I had never seen anything like these girls.

Then on the screen there was a picture of a pretty girl and a man. They were kissing and he had his hand on her butt. The next picture was the same but she was naked except for her panties, they were really small tight black panties. In the next one he was naked and she was on her knees in front of him, his hard dick was poking out and she had her mouth open. He clicked away and the pictures showed her with his cock in her mouth in each one. Her eyes were closed and in one it was almost all the way in.

Tom was rubbing the front of my panties exclusively now, not my thigh anymore and I was getting excited. At some point he moved my hand to his crotch. He was very hard. I put my hand on his cock and squeezed, feeling the heat, but not taking my eyes off the images shuffling past my eyes. The last one in that series showed the girl smiling with cum all over her face as his wet cock hung next to her face. I felt his cock throb hard in my hand when this one came up.

The pictures progressed to more couples touching each other, kissing and sucking each other off. There was one I remember so well. It was a picture of a guy and a girl that looked really similar to Tom and me. She was on her back with her legs spread. She was really hot. And he was kneeling in over her on the bed holding his hard manly cock and her little dick was just sort of there between her legs. The comparison was like what I had seen on the bed just a little while ago. She was looking at him with so much passion. I remember thinking how pretty she was and how hot his big hard cock looked. I remember wanting to be her, wanting to be really pretty like her.

I was so turned on now, and Tom's cock felt so good in my hand. I had slipped my hand into his boxers at some point and I was squeezing it really hard and it was throbbing. His hand was pushing into the front of my panties and he was moving the fabric over my hard little penis. I was wiggling my fanny and pushing myself into his hand.

He let go of the mouse and put his arm around my waist, pulling me to him so that his cock was standing up against my butt. He shimmied me up onto his lap and reached under me, pulling his cock down somehow so that when he stopped wiggling, his cock was standing straight up in front of my panty covered crotch. I put my hand around it. It was so weird; it was like it was my cock, right between my legs. The panties were sliding up my but crack and the heat from his dick to mine through the panties was incredible. I squeezed my thighs together, pushing the shaft of his cock against my crotch and wiggled my butt a little, it felt so good nuzzled between my thighs.

Tom put his hand on his cock and pulled it into me. It was pushing hard against mine through the panties and I could really feel his hardness against my own. He began to move his hips and I watched, and felt, his beautiful hard cock slide up and down over my panty covered prick. I spread my legs and laid my head back. Tom put his thumb under the edge of the little pink triangle of my panties and put it behind my dick, pushing it into his with just the thin, silky material between us. Then he slid his right hand up under my shirt, rubbing me all over my chest and tummy. Pinching and squeezing my nipples and making me feel so sexy, just like the girls in the pictures.

My hips were rolling and thrusting on their own, I was so turned on, loving the feeling of his dick against me and his other hand exploring my body. I moved both my hands to his hand on top of his cock, pulling him into me harder. He slid his hand out from under mine and let me control the pressure. His hand went up my shirt and the other one went back to the mouse. He continued to click on the pictures. My hands were stroking the top of his cock as I pushed myself into it.

More pictures clicked on the screen, a girl sucking on a man's dick, looking up at him with big, pretty eyes, another one with a girl fingering her little pink butt hole, more girls in panties, more girls sucking on big cocks, Toms hard cock thrusting up and down in my hands, against my panty covered dick. My breathing was out of control, I was lost in this whole scene. I let out a squeal of ecstasy as my hips pushed and bucked into Tom's hot cock. He pinched my right nipple hard and I came. I squealed again and again as I felt my panties get wet with my warm fluid.

"Good girl." He breathed in my ear, massaging my nipple and slowing his thrust as my hips spasmed. "Such a special girl." He said squeezing my tightly to himself.

I was still holding his hard cock against my panties, my little dick softening in the sticky mess. He moved his left hand to my thigh, sliding it up to the edge of my panties, and slid a finger in. I could feel him move it around in my cum, rubbing it over my super sensitive, softening penis.

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