I'd been living in my house for about 5 years and had got to know my neighbours, the Andrews family, really well in that time. What they didn't know about me though was my growing fascination with their younger son Kevin. In truth he looked more like a girl than a boy. He was quiet and studious but had grown his hair long, complimenting his thin frame and feminine ass.
I'd been studying images of young shemales for years and was dreaming of young Kevin completing such a transformation and of me being the one to complete his metamorphosis by bedding her. It was a nice dream but highly unlikely to ever happen; after all, I was friends with the family and didn't want to put that at risk.
It's funny how things work out though. Over the last summer, the Andrews family went away leaving Kevin at home by himself. Although he was 17, I was asked to just keep an eye on him, which I readily agreed to.
One Sunday I went over to the Andrews' house to check on Kevin. He answered the door and invited me in. A quick polite exchange revealed that we was coping perfectly well on his own thank you very much. While he made us a drink, we continued to talk. In fact, it was probably the longest we'd ever spoken alone as normally I'd be chatting with his parents. He had a soft almost feminine voice that matched his figure. Just listening to him made me picture him dressed as a cute girl. My visions were making me bolder. I knew I had to try and tempt him.
I left the house with a plan beginning to form in my mind. I had invited Kevin to dinner that night which would allow me to start to plant the seeds. In my living room I left a lingerie magazine out and put a porn DVD in my machine. The first part of the plan was to at least get him thinking about the possibility of being a girl.
Kevin duly arrived at 6. I made him a drink and we sat and talked for a bit. He clocked the lingerie magazine and began to flick through. I told him I liked the sight of cute girls in sexy clothes. He seemed riveted by what he was seeing.
I made my excuses, as I had to carry on cooking and told him to feel free to watch TV. As I left the room, I could hear the machine go on which meant he would see the menu of the DVD I'd left in - My Perfect Panty Boy. I had my fingers crossed that he'd be curious enough to play one of the scenes and sure enough he did. He'd chosen a scene with a young girly-boy of his age stripping out of her elegant evening wear and climbing into bed with a muscular young man. There she began to kiss down his body until she wrapped her lips round his cock and began to suck him off.
I moved back to the crack of the door to see Kevin engrossed in what he was watching. In the film, the man had now positioned the cute young thing on her hands and knees and was about to enter her. You could hear Kevin's breathing growing heavier, very promising. I went back to the kitchen and continued to prepare dinner. When I returned a few minutes later, Kevin was still watching as the girl was crying out in ecstasy as her lover humped her with increasing fury.
So far, so good. I left Kevin unaware I knew what he was watching and headed back to the kitchen. When the food was ready, I called him from there so not to embarrass him. I needed to take my time with this one.
Kevin came in looking a little flustered and sat down ready to eat. He was struggling to make eye contact with me. We talked a bit over the meal but nothing was said about what he'd just seen. I returned to the conversation to the lingerie magazine
"So anything in it that took your fancy?" I asked.
"Um, um. well I guess the pink babydoll was really nice. Er, I mean the chick in it!" He replied.
Yes of course that's what you meant Kevin I smiled to myself. This was beginning to look promising.
"Yeah, that was good," I offered, "but I liked the girl with the red stockings on. She had really cute legs"
"Did she. I um.. must have um. missed that."
"Tell you what. Why don't you borrow the magazine?" I offered, "You can have a look at that girl. It might give you some ideas."
I knew just the sort of ideas I hoped it would give him! Off he went with my magazine. I'd give him time to digest the night's events and then make my next move.
A couple of days later I was doing some shopping when I spotted Kevin going into a department store. Intrigued what he might be looking for, I followed him in. To my delight he headed for the ladies wear floor and was looking at panties. Keeping my distance, I watched him purchase a few pairs. Now was the time to make my move. As I was in the store I made a few purchases that would fit Kevin and headed for home.
On getting back, I saw Kevin was in and knocked on his door. He invited me in but appeared a bit agitated and seemed keen to get rid of me.
"Is everything ok Kevin? You seem a bit tense."
"Well, I've uh got a few things to do that's all."
I decided that the time had come to be a little more direct.
"Oh, I thought you might want to try on your purchases!"
"What d..do you mean?" He stammered.
"I saw you getting those panties earlier on. I thought you might want to be wearing them."
Kevin went red and flustered. I saw tears welling up in his eyes. He tried to deny it all but lying wasn't a strong point. I put my hand on his arm.
"Hey it's ok. I'm not going to tell anyone."
"You won't? Oh thanks Paul. My parents would be devastated if they knew. I'm sorry but when I saw those pictures at your house, I just wanted to try them."
" So are you wearing them now?"
"Oh God, erm..yes"
"Can I see them?"
At this point I thought he might freak but to my astonishment he pulled down his trousers to reveal a very girly pink pair of panties with a flowery trim. They were tented at the front - he clearly enjoyed wearing them. I felt the material with my fingers then placed the palm of my hand on the side.
"They feel really nice. They suit you so much." I commented.
Kevin blushed but didn't move to get my hand away. I slowly moved my hand around to cup one of those cute girly cheeks. He sighed at the attention.
"You know these fit you so nicely, I wonder what you'd look like dressed totally as a woman. Would you like to find out?"
"Oh yes I would. This feels so nice"
"Well, I've bought some things that I think might suit you. Why don't you come round to my house and you can try them on?"
He hesitated at first but a quick squeeze of that heavenly cheek and he agreed. I couldn't believe things were going quite this well.
We headed back to my house and I directed him to the spare bedroom where I'd laid out my earlier purchases. I'd also arranged a make up table. I wasn't sure how far Kevin would go at this stage but his eyes bulged at the clothes. I left him to get ready and went downstairs.
About 20 minutes Kevin came down totally transformed. He was wearing a floral summer dress with white stockings showing and a pair of high heels. His face was totally made up with crystal heart shaped dangling earrings clipped on. Wow. He looked so feminine and very, very hot.
"Oh my God you look amazing" I exclaimed.
"Thanks Paul. I can't believe how good this feels. It's just so right. I feel like a woman."
I got up and gave him a hug. His arms wrapped around me while mine wandered across his back and inevitably to that oh so sexy ass.
"If I didn't know better I'd think you quite liked my butt." he giggled.
"I've always dreamed of seeing you like this" I confessed, "but you look even hotter than I ever expected"
"I'm not sure I should really be here Paul". It was the first sign of nerves I'd seen from Kevin. I was too close to being denied now though. I placed my hands on his chest and began to stroke his nipples through the material of his dress. He groaned at the touch. I brought my lips to his and began to kiss him; my tongue parted his lips and began to explore his mouth. My teasing of his nipples and kissing must have had some effect as he responded with a passion I hadn't expected. His hands began to explore my body, moving beneath my shirt and caressing my torso. My cock felt like it would burst with the excitement.
I broke our embrace and took his hand to lead him to my bedroom. All resistance was gone now. I made Kevin sit on the bed while I removed my clothing. His eyes bulged as he saw my cock spring out of my boxer shorts. I moved towards the bed and kissed Kevin passionately. While we kissed, Kevin nervously touched my shaft and began to stroke it. His soft feminine hand felt wonderful.
I broke the kiss and guided his head towards my cock. He looked up at me smiling broadly and began to gently kiss the tip. His tongue then darted out and began to lick it, slowly moving down the sides. This was heaven. Then finally he began to feed my tool into his cute little mouth and use his lips as a beautiful pussy to fuck me. While he did this, his hands began to stroke my legs and ass. My hands meanwhile were now firmly placed on his head guiding him as he continued his oral assault. Soon it was all too much for me and I unleashed a torrent of semen down his throat. Kevin greedily swallowed as much as he could while the rest dripped down his chin onto the dress, He happily cleaned my cock, looking up at me while he did so. His eyes were ablaze with lust.
I pulled Kevin to his feet and kissed him, pulling his fragile figure close to me. I began to unzip his dress and pull the straps over his shoulders. He stepped out of it to reveal a truly a stunning body clad only in heels, stockings and panties. His legs were so smooth and girly while his nipples were small and puffy.
I began to kiss his neck and slowly down his front. I teased his nipples with my tongue and began to gently bite them with my teeth. He sighed with pleasure at my touch. I moved him onto the bed and began to tease his back with my tongue while my hands worked on his stocking- clad legs.
I turned my attention to that cute ass. I massaged the cheeks and slowly moved my fingers between them, pulling his thong to one side. I started to caress his tight hole and eventually placed a finger on the opening. I pressed inwards causing Kevin to groan in pleasure. I began to gently finger fuck him, inserting a second finger after a while and then a third. Kevin was now beginning to get very aroused, pleading with me to go faster. I leant over and kissed his neck and face. "It's time I made you a real girl darling," I whispered to him.
"Oh please Paul. Anything. It feels so good."
At that point I had to let him go so I could lube my cock. He cried out in frustration as I withdrew and looked round to see what I was doing. I could see a mixture of fear and lust in his eyes.
I moved back to his body and guided the tip of my cock to his hole and began to push forwards. Kevin cried out in pain at first but the cries soon turn to pleasure as I fully entered him. I began to withdraw and then moved forward beginning to generate a rhythm. He was so gloriously tight - this was beyond my wildest dreams. Here I was gazing down at this sweet girly-boy and giving him/her what she most desired.
I rolled Kevin over so he was on his back whilst staying inside his as I did so. I was now able to kiss that beautiful made up face and play with those puffy nipples. Kevin was squealing with delight and shot a load of goo all over his stomach without having touched himself. The sight just turned me on even more and I upped the pace of my thrusts into him.
I could feel my own orgasm building and soon I erupted deep inside him. I was utterly exhausted by our passion and barely had the strength to roll off Kevin, pulling him into my arms so I cradled his head on my chest.
"Kevin that was fantastic. You're an amazing girl"
"No Paul, not Kevin. I'm Clara now. You've made the woman you thought I should be"