I was 17 when I met Alan. He'd moved in next door to my parents and seemed nice enough. We said hello but nothing else. If I'm honest I never imagined how things would turn out.
At the time, I was a quiet boy struggling to come to terms with life. Emotionally I was a late developer and it had never quite clicked with the girls at school. I'd become a quiet, reserved figure who kept out of trouble. Privately I'd started to use the internet to look at adult sites - mainly sexy girls. Nothing out of the ordinary mind you, just your average teen boy kind of thing.
It was a dull April day around Easter. My parents had gone away on holiday leaving me with the house to myself for 2 weeks. I'd walked down to the shops for some milk and bumped into Alan on my way back.
We got talking. Small talk, nothing more when he suggested if I was on my own I pop round his house for lunch. Having been on my own for a few days, I was grateful for the company so thanked him for the offer and followed him home.
Lunch was fine but the conversation got a bit weird. We started to talk about girls and how they looked. I mentioned how I liked girls in sexy lingerie. A few minutes after I mentioned it, Alan piped up
"So is it the lingerie or the girls you like?"
"Sorry?"
"Is the attraction the lingerie?"
I must admit that got me thinking. I'd never considered that before and there was something at the back of my mind about the lingerie. It looked really nice and my mind drifted to the thought of wearing that sexy red lace babydoll and thong I'd seen on that cute teen red head.
"So it's the lingerie then?"
My daydream was abruptly interrupted by his words and I must've gone a thousand shades of red in embarrassment. It took all my efforts to raise my head to look at Alan - he was grinning at my discomfort. I tried to speak but nothing came out of my mouth. Thankfully Alan spoke to spare me
"It's ok. I'm not going to tell anyone. Besides plenty of youngsters like you try wearing women's clothes. "
"Really?"
"Yeah. Have a look online when you get home. Some guys just want to experiment while some go a bit further..."
The conversation mercifully switched after that and not long after I made my excuses and headed home. I just couldn't get Alan's words out of my mind though. What did he mean about taking things further? Needless to say, the first thing I did on getting home was to head for my computer. I started to search for boys in lingerie and was amazed at just how much I found. After a few minutes of looking, I found one page that really brought everything into focus. It showed a young boy of my age with long hair stripping out of his male clothes and putting on a gorgeous red bra and panties set and then getting into a flowing evening dress with a floral pattern. He then applied makeup at a table. Jeez he looked utterly stunning, as sexy as any girl I'd seen. My cock by now was rock hard and I couldn't help but jerk myself off. I was just so aroused at the sight and my mind was burning with two questions - could I look as hot a chick as that and if I could, what would I do then?
I didn't get a lot of sleep that night. I was imaging myself dressed in different girly outfits and strangely thinking of Alan. The next morning I headed out early to buy some beauty products as I'd decided that my little body hair had to go. I picked up the products I needed and headed for the food aisles but on my way through my eye was drawn to the women's clothing section. I noticed a pack of pink girls' panties with a floral trim. They looked sooo cute I though I just had to have them but I couldn't could I? By this point though so I was so turned on by the though that I just had to do it. Putting them in my basket I quickly got my food and headed for the self-service checkouts. What can I say? I was still dying of embarrassment but just couldn't stop myself.
I don't think I've ever got home so quickly as I rushed back. I got straight in the shower and began to shave my body from top to toe. Getting out of the shower, I applied some body lotion I'd bought. God, I felt so smooth and girly it was untrue. I opened the panties and put a pair on. They felt wonderful on my smooth skin. I was in heaven and before I knew it I was shooting a load on the bathroom floor. I was glad I'd bought a pack of panties as that was the first pair in the wash!
Once cleaned up, I headed back to my computer and sat in just my panties and went back to the girlyboy from the previous night. The page had a link to another site that I followed. There I found more shots of the same girl in different outfits. In one she was in a two-piece swimsuit that barely covered her aroused cock but still showed off her feminine figure to perfection. If only I could reach that level. It was at this point I went to the news page of the site that next week "Gemma" would be filming her first hardcore session for the site. Wow. That was a whole new line of thinking for me. Hardcore with whom? Female or even male? I really was very na‹ve!
Before I had too long to think about it the doorbell rang. Pulling on my clothes I quickly went downstairs to find Alan standing there.
"Hi Paul. I was out shopping earlier and I thought of you when I saw this. Don't open it now, I've got to dash anyway but maybe I'll see you wearing it sometime. Bye"
Ok now things were getting very strange. I had a strange feeling I knew what I'd find in the package. Opening it up sure enough it was a two piece set of a pink lace babydoll and matching thong. Utterly gorgeous and I couldn't wait to try it on. If felt even better than it looked. I felt like a girl and a very sexy one at that. There was one thought in the back of my mind - what did Alan mean about seeing me wearing it sometime? As I considered that question I began to spurt my juices all over the lace.
Part 2
The next day I decided to head into town to do some shopping. As I was leaving the house, Alan was in his front garden.
"Hi Paul. How did you like your present? Have you worn it yet?"
My reddening face answered for me!
"I suspect it's needed a wash already then?"
Now I was really struggling. I was uncomfortable enough knowing Alan had interest in me wearing lingerie but for him to know the effect it was having on my body was a bit much. I just couldn't being myself to look at him but when I finally did he was given me a strange almost lustful look. I don't know why but at that point I blurted out that I was going shopping in town for more clothes. I couldn't help myself. I was so caught up in the desire to become as sexy as Gemma looked online and Alan's expression was really having an affect on me.
"Tell you what" Alan replied, "if I give you some money to buy some pretty clothes would you model them for me? I'm away with work for a few days but I'd love to see you when I get back. I think you'll make a pretty stunning woman."
I would? Alan's words made me feel so good and I had to admit he looked pretty handsome. No hang on, what was I thinking? I'm a boy not a woman! Yet despite telling myself this, I knew what I really wanted was to be wearing a beautiful dress and made up like a million dollars. A show for Alan really wasn't going to be a problem. I agreed and Alan very kindly gave me some cash. He also offered to give me a lift to town, which I readily accepted. As we drove I could feel his eyes glancing towards me. I was growing curious. What could happen between us?
Alan asked me what I though I might buy and I told him about the evening dress from the internet. He said he liked the thought of it and suggested stockings and suspenders would go well with it and make me look a really sexy woman.
"I wish," I laughed.
"Why not?" He countered, "You've got a great feminine figure and nice hair. I think you're a lot closer to what we're looking for than you realise."
With that, the car pulled up at the shops and I headed off with Alan's words ringing in my ears. I quickly chose some clothes in the first shop I went into. I really didn't want to hang around and felt really uncomfortable looking at the racks. I chose a floral summer dress and an elegant red evening gown. In the lingerie section I picked up a white suspender belt and matching stockings, bra and panties. I was about to move onto the shoe shop when I caught sight of a stunning blue underwear lace dress. Wow, it looked lovely and I couldn't resist. I was growing obsessed with girly clothes!
A pair of heeled shoes followed and then I headed to the beauty store to look at make up. Now here was where things were going to get difficult. In all honesty I didn't have a clue where to start. I took my best guess of a few things and bought a bottle of perfume I'd seen advertised on TV. That was all Alan's money and a significant chunk of mine gone so I headed for home and the fun of trying everything on.
On arriving home I quickly showered and sat down to try my make up. I followed directions I found on line and in fairness for a first attempt it wasn't too bad. I put the underwear on and plumped for the evening gown first. I stared at myself in the mirror unable to believe it. I looked stunning. I actually looked like a girl and a pretty foxy one at that! It was time to try the shoes and practice walking in heels; not as easy as I though it would be but after a few minutes I was getting the hang of it and started to practice walking in a feminine way. I don't think I'd ever been as turned on in my life. I felt so girly and happier than ever before. Of course it wasn't long until my excitement exploded leaving me with a bit of a clean up.
The next couple of days were spent at home mainly dressed as a girl and enjoying the liberation of it all. I was aware that Alan would be due back from his business trip and wondered what would happen then. Was I ready to see my transformation? It was thinking of Alan's return that I remembered the promise of Gemma's hardcore session. I headed for my computer and headed to the site to see if it had been posted. Lo and behold there it was - a picture showed Gemma in a mini dress and whale-net stockings with high heels. She was wrapped in the arms of a muscular man with his hands around her waist as she turned behind to kiss him. My jaw dropped at the image and I clicked on the link to watch the video. It started with Gemma resting on the bed as the man came into the room. He sat beside her running his hands along the side of her body, paying attention to that cute butt. Gemma came to and sat up placing her hands on the man's torso and giving him a passionate kiss, her hands sliding under his clothing and feeling the contours of his muscles; the man's hands moved to Gemma's tiny breasts and began to massage the small mounds. The groans of pleasure from Gemma went right through me. This was so hot.
The man then removed his clothes exposing a large and very erect penis. Gemma's eyes seemed to widen at the sight and she began to kiss her way down his body. After what seemed an eternity she kissed the tip of his cock and then ran her tongue down the length of the shaft. She then placed the cock in her mouth and began to gently suck on it. The man placed his hands behind her head and began to force her to bob up and down on it at an ever- increasing pace.
By this stage my mind was blown. This was the hottest thing I'd ever seen. A few days ago I was staring at Gemma and wishing I could look like her and now I found myself going further. I wanted to be her. I wanted to be sucking that cock. She looked the perfect woman and that's what I truly craved. I began to wonder about Alan and if he was hoping his kindness would lead to me doing this to him. Or perhaps even more.
By the time the blowjob had finished I'd shot a load but was still hard. Now the man placed Gemma on her hands and knees and began to kiss her buttocks gently separating them with his hands as he did so. His tongue slowly moved across and into the gap separating them and began to dart around her hole. The camera focused on Gemma's face and the absolute ecstasy she was in. After a few minutes this tonguing was replaced by a finger as the man began to ease himself behind her and then finally he moved that large prick into the hole and began to fuck her. Gemma cried out in a mixture of pain and pleasure as he entered her but it was quickly clear that she was loving every minute of it. They switched positions several time until finally he removed his cock and shot a large creamy load all over her face and down the front of her dress.
The video had lasted about 18 minutes and by the end I was exhausted and in a very sticky mess. My mind raced to Alan. Is this what he wanted? Oh, I so hoped it was. I wanted to become a real girl and feel the joy Gemma had on screen. I'd do anything for him. But what would it feel like? I'd never had anything pressed up my butt before and was slightly nervous that Alan could be a big boy. Searching my room I found a marker pen and decided to use that as an experiment. Firstly I lubricated my finger and entered myself. It felt nice and I began to slowly finger fuck myself. A finger however just wasn't enough and tried the pen. I fucked myself for as long as I could until I orgasmed again at which point my body had reached the point of exhaustion. I feel asleep where I lay in my sticky cum soaked girl clothes.
Part 3
A day later Alan returned from his trip late evening. I'd made sure all the clothes were washed and ready for my display. I'd hoped he would call straight away but it was late and he must've gone straight to bed. I felt disappointed but looked forward to the next day.
I was doing some chores when the doorbell went the next morning. It was Alan.
"Hi gorgeous. Did you miss me?" "Hi Alan. How as your trip?" I replied, ignoring his previous question. Hey, I didn't want to seem too keen!
"Good thanks. I brought you a few presents back. Here's one. I've got more for you later. Why don't you pop round tonight for supper Lara?"
Lara? So that was to be my girly name was it. I was ok with that. It sounded dead cute to me. The present he handed me was a pair of clip-on hoped earrings. That was part of the look I hadn't thought of!
"Ok. Do you still want your fashion show?"
"That'll be great. I'd like to see you in all the things I've got you".
I took the hint on the babydoll and that removed any lingering doubts on Alan's intentions. I was overjoyed. I was going to spend the night with a handsome man who would make me the girl of my dreams!
The day dragged on for an eternity until it was time to get ready. I decided I'd actually leave the house dressed in my evening gown. I was a bit nervous about being spotted but was confident that nobody could be sure it was me if I was spotted. I packed the other clothes in a bag. My makeup done and the earrings in place, I headed out for my date with destiny.
Alan opened the door and his eyes bulged at the sight of me.
"Oh my God. Lara you look stunning. I knew you were a sexy princess but never that sexy"
He lent forward, kissed my cheek and put his arms around me. I gave him a gentle hug and thanked him. He poured a glass of wine for us and we started to talk about my shopping trip. Alan wanted to know the details of everything I'd bought. He then got out the next present - a really gorgeous gold necklace. He insisted on putting it on for me. He stood behind me and kissed the nape of my neck as he finished. I clutched his hand and thanked him for all he'd done for me.
"Ever since I moved in I'd imagined you as Lara. You've got such a great figure and just thought somebody needed to show you. I'm so glad it was me."
"I am too Alan. I've never felt so happy."
With that he took me in his arms and hugged me tightly. I could feel his cock growing and pushing against me. I was clearly having the right effect. He moved his hands along my back and pulled away slightly.
"You're so beautiful Lara. Would you mind if I kissed you?"
I didn't bother to answer as I tilted my head to the side and invited him with my lips. Our tongues touched and soon circled in an increasingly hot clinch. I moved my hands now across his back and under his shirt touching that manly skin for the first time. His hands moved downwards to my butt and began to cup the flesh. I moaned in delight. God I wanted him so badly now.
We broke apart and he took my hand and led me towards the bedroom. My heart was pounding now as Alan kissed me again. I felt so turned on but was still a little scared. He must have sensed that as he lovingly held and stroke me, telling me how beautiful I was. I began to move my hands to unbutton his shirt and run my hands over that chest. I moved my head to kiss him there as I took the shirt off. As I did so I could feel Alan undoing his trousers and kicking them to the floor. My hand brushed down and I felt his erect cock for the first time. My tongue continued to run along his torso as I began to stroke that lovely sword. God, I wanted this. Alan groaned in pleasure.
"Oh Lara, you're better than I had ever dreamed. You really are the perfect girl. Please darling, kiss my cock"
I didn't need any persuasion. I first smothered it with little kisses and then began to roll my tongue along the shaft just as I had seen Gemma do online. I placed his balls in my mouth and sucked on them. This was all proving too much for Alan who put his hands on the sides of my face and guided me to the tip of his dick. I slowly gobbled the shaft and began to gently suck on it, moving it up and down between my lips. Alan's hands kept me there - not that there was any danger of me moving. I was loving it. This was a dream.
"Darling, you're amazing, I'm cumming".
I hadn't actually considered that he would actually cum in my mouth (my only "experience" was the porno after all) but I'd determined quickly that I'd try to swallow his seed. It hit the back of my throat hard and fast and I had to keep swallowing, although plenty still escaped from the sides of my mouth. As Alan went limp I continued to clean his cock, swallowing the remaining sperm. He was wiping my face of the overspill and offered me his hand, which I also licked clean.
"How was that darling?" I asked.
"You're a very special girl Lara. I hope we'll have a lot more fun tonight"
"We will darling but I think it's time I got changed don't you?"
I knew Alan would want to see that babydoll and I was also conscious of the sticky patch in my panties. I hadn't touched myself but had still cum. Boy was I horny.
I made my excuses and headed to the bathroom. I cleaned myself up and re-applied some makeup. I removed the dress but left the cum stained panties, bra, stockings and suspender belt on. It was time to put on a show. I went back into the bedroom and found Alan lying on the bed. He sat upright as I went over and kissed him on the lips. I motioned for him to lie still. Slowly I began to strip out of my remaining clothes until I was totally naked. Alan was playing with himself and I couldn't resist going over and giving him a passionate tongue kiss while he lay there. His hands quickly left his erection and moved towards my butt and I felt his thumb pressing against my boipussy. I pulled way and went back to my show. Putting on the thong and babydoll then dancing seductively in front of him, squeezing my breasts. Then I turned away to give him a view of what I knew he really wanted. As I turned back there was nothing but lust in his eyes. I knew I wouldn't leave his house a virgin. I would be a real woman and I couldn't wait.
I made me way onto the bed and snuggled up next to him. We kissed and cuddled for a short while but I knew it wouldn't last long. Alan was a man on a mission and he wouldn't be held up for long. He began to play with my breasts, gently biting my nipples. I squealed in joy. He then put me onto my hands and knees and began to kiss my ass cheeks. I was pleading for him to tongue me; I've never known such desire. After what seemed an eternity his tongue touched my hole and began to tease the entrance. Slowly it began to enter my hole and I could feel him start to tongue fuck me. While he did this, he surprised me by placing his hand on my cock and starting to rub through the material of the thong. I soon cried out in joy as my orgasm hit. He took his cum stained hand and began to massage it into my hole, lubricating me for what was to come.
"Lara I love you. I want to make love to you"
"I love you too Alan. Please, I want you to be the one to make me a woman"
I gazed lovingly into his eyes as he rolled me onto my back and placed a pillow to raise my hips. Then he began to move forward bringing his cock to the tip of my hole. I felt the pressure grow until he began to penetrate my ass. Tears began to roll down my face as the pain hit but it quickly gave way to the most amazing pleasure. Alan finally rammed the rest of his rod into my boipussy and lay still for a moment, as I grew used to the feeling. Then slowly he began to withdraw then thrust forward. Wave after wave of ecstasy began to rush over me; my arms ran across Alan's back as I held onto my lover for all I was worth.
We kissed passionately and I hoped the moment would go on forever but I could feel that Alan was approaching his climax. He stiffened and shot his load up my pussy, collapsing on top of me in exhaustion in the process. Such was the excitement of his ejaculation, my own orgasm arrived on cue. We lay entwined in a sticky mess on the bed, his juice slowly trickling down my thighs.
We fell asleep in each other's arms. I drifted off wondering where things would go from here. My life was changed forever.