I 'm Dylan and got my first introduction to sex when I was 12. I had been playing with myself for years, and learned to cum, quite by accident, but it was a very happy accident indeed. After that I tried to repeat it as often as I could, and finally got it right.

I had long hair, about shoulder length. My mother used to enjoy brushing it and often told me that I was pretty. That wasn't something I liked at first, but over time I began to wonder if I really was. I studied myself in the mirror and had to admit that I did look rather girlish. Some guys would do their best to avoid that, but I liked it.

It actually aroused me to think of myself as a girl, and one day while I my mother was brushing my hair I asked her if I would look prettier in makeup. That caught her by surprise, and she paused while brushing me. Then she continued and said we could give it a try.

"You know I love you, don't you, Dylan?" Mom asked.

"I know," I replied.

"I've always wanted a girl, which is why I encouraged your long hair," she continued, "And now I really like you this way."

"I like it too," I agreed, "But could I wear something that suits me better this way?"

Mom smiled and said she would get me some girl clothes and said this was going to be great.

I wore the makeup the rest of the day and every time I passed by a mirror, I stopped to admire how I looked – I had to jack-off a few times because it aroused me so much!

The next day Mom brought me some girls clothing, including a pink bra and panties, along with a pretty dress. She told me to get undressed and she would help me get ready. I quickly stripped down and stood naked in front of Mom. She looked at me and saw that I was hard and said, "We'll have to do something about that."

I was afraid I'd done something wrong, but quickly knew I hadn't when Mom took hold of my small cock and began to stroke it. It felt so much better than when I stroked myself! Soon I came, and Mom caught it all in a tissue. She told me I should always have tissues with me.

Once I was soft again Mom helped me into my first set of panties. She tucked my soft little cock under, and they fit perfectly. Then she showed me how to put the bra on. It buckled in the back, but Mom showed me how to put it on backwards at first, buckling it in the front, and then slipping it around so the cups were in the front, then putting my arms through the straps. Then she took a box out of a bag and showed me two very realistic looking breast forms. She slipped them into my bra cups and I looked like a hot little girl!

She helped me put the dress on and then some shoes. "You aren't ready for heals just yet," she said, "But when you are we'll get you some."

She stood me in front of a mirror and I couldn't get over just how nice I looked! Nothing boyish about me, and I liked it that way. “Now walk for me,” she said.

I took a few steps and she stopped me. After explaining my mistakes I practiced walking like a girl, and I liked how it made my hips roll – no wonder guys notice a hot girl’s ass! I practice for nearly half an hour before Mom said I was ready – but for what?

"Okay, let's go to the mall," Mom said. This caught be by surprise – I didn't think I was ready to go out in public, but Mom assured me it would be okay.

I nervously got into the car, and we drove to the nearby shopping mall. As we got out of the car she said, "Now remember how I taught you to walk." I hoped that my practice would pay off and boys would notice.

As we walked through the mall I was terrified, but soon calmed down. Nobody was looking at me funny, though I did see a couple of boys smiling at me. After a while Mom said, "I have to go to the lady's room, care to come with me?" I wasn't ready for that and declined, so I sat on a bench awaiting her return.

As I sat there a boy approached and asked if he could sit next to me. I had no idea how to act, but just nodded, and he sat down. His name was Jim, and he seemed really nice. Since I was only beginning puberty, my voice hadn't dropped yet, so I sounded like a girl, but I didn't say much, mainly because I had no idea what to say.

Mom returned and rescued me. As I got up to go with her, Jim asked if he could have my phone number, but I said it wasn't a good idea just yet. Jim seemed disappointed but said he'd see me around.

My heart was racing – I was feeling confused – a mix of fear and excitement! Mom asked, "How did you like being with a boy?"

"It was kind of scary, but nice too," I replied. I wanted to see Jim again but was afraid – what if he found out I wasn't a real girl?

On the drive home Mom asked if I wanted to be a girl full-time or just occasionally. I told her I'd spend the rest of my life as a girl if I could. Mom smiled and said she would help be do so. At the time I thought it would simply be continuing to dress and act as a girl, but soon I learned that it was much more. Mom took me to a doctor who specialized in transgender issues (that was a whole new world to me). He prescribed female hormones so my body would become more femme, including growing breasts. He also prescribed a testosterone blocker, which would prevent my developing any male features. This was entirely new to me, but I was thrilled! I was currently on summer break from school, which would be resuming in another six weeks. Mom notified the school that I was transitioning to female, and they made a record of it. Apparently, this was becoming fairly common, and schools were prepared to deal with it, including preventing bullying.

I read about people who were gender dysphoric – born into one body but with the brain (or mind) of the opposite gender. That didn't seem to fit me – I just liked the idea of being a girl – it seemed like so much more fun! The fact that Mom liked it made it all the better!

Mom took me back to the mall several times and I always looked for Jim. She suspected, and asked me if I was interested in him, and I confessed that I was. Finally I saw him and he spotted me. He came over and Mom suggested that I go with him and meet her at the food court in about an hour. I nervously went with Jim, excited, but unsure how I should act.

"I'm sorry, but I don't have much experience with boys," I said, "I want to be with you, but I don't even know what to talk about."

"It's okay," said Jim, taking my hand, "There aren't any special rules – let's just get to know each other."

We walked past the many stores and came to one that was being renovated. There were papers all over the windows, and Jim said, "This would be a good place," and he pulled on the door handle. To our surprise it wasn't locked – someone must have forgotten to do so. I nervously entered with Jim, and he turned to me and pressed his lips to mine. It was amazing, and I hoped I was doing it right.

After a time we broke off and I said, "I'm pretty new at this."

"Then we better practice a more," said Jim with a smile. We resumed kissing. I was getting aroused and slipped my tongue between Jim's lips and he opened his mouth and we had our first French kiss! It was electrifying – no kiss is quite like that.

As we kissed my hand brushed across the front of Jim's trousers and I could tell he was aroused as well. I nervously placed my hand on him and squeezed his cock through the cloth. "Is that okay?" I asked, hoping it wasn't a mistake.

"You can do that all day long," said Jim, and I continued squeezing him, feeling his cock grow. I had a lot of experience playing with my own cock, but I had never touched anyone else.

"Would you like to see it?" asked Jim, and I eagerly agreed. He unzipped and took out his cock. I gazed with great interest at his hard cock and took it in my hand. It was warm and soft to the touch, yet firm. I gave it a few more squeezes and Jim pulled me to him and kissed me deeply. I knew I wanted more of this – in fact, I wanted to make Jim cum, but that also was new for me. The only way I knew of was jacking-off, so I stroked him and soon he said, "I'm gonna cum, better get out of the way!"

I stepped to the side as Jim shot four big squirts of cum on the floor. I felt really proud of myself – Jim thanked me and promised to return the favor. That stunned me – so far, I got by pretending to be a girl, but it wouldn't take much for Jim to discover my secret, and that could be a disaster!

I heard how some men beat up and even murdered crossdressers. I had no reason to think Jim would react well once he knew. Jim had his hand on one of my fake breasts and was gently squeezing it. Mom must have spent a lot on them, to be so realistic, but Jim didn't know the difference. Before he tried to reach into my panties I had to stop him.

Suddenly we were interrupted when a couple of construction workers entered and called out to us, "You kids aren't supposed to be here! Better get out before I call security."

Jim apologized and we quickly exited. "That was close," I said.

"Sure was, but I love what you did for me," Jim said, "And it won't be forgotten."

I told him that I needed to get to the food court to meet my mom, so he walked me there.

Mom was waiting as we approached. Jim asked for my phone number and this time I gave it to him, really wanting him to call.

"Did you have a nice time with Jim?" she asked. I told her I did, but didn't go into any detail, not sure how she would react.

I was so excited I had to cover myself so Mom wouldn't see my arousal. When we got home I went right to my room and began to jack-off. To my surprise, Mom tapped on my closed door and pushed it open, catching me in the act. I thought she would be mad, but just apologized for interrupting and asked me to come see her when I was done. When she closed the door again it didn't take long to regain my arousal and soon I came.

I went to see Mom as requested, feeling a little embarrassed that she caught me. But she was cool about it and asked if I had a nice orgasm. It sounded strange hearing that word from Mom, but I nodded in agreement. "I know this is very personal," she said, "But what were you thinking about when you were doing it?"

She was right – that was VERY personal – I wasn't quite sure what to say – having no good response ready I just said, "I was thinking about kissing Jim again."

"Again?" she said with a sly grin, "I guess you did indeed have a good time with him."

"I did," I confirmed, "But I'm really nervous about it, and a little afraid he'll discover my secret."

"I think you know how important it is for it to remain a secret," Mom said, "But I think it's time you learned about sex, and I'm not the one to teach you. Let me see what I can set up."

I lived alone with Mom – she divorced my father when I was much younger and he moved to another state, so the only other men in the house were Mom's occasional boyfriends. She didn't have any at the moment, so I had no idea what she may have in mind.

The next morning I found out. "I'm going to send you to visit your Uncle Bill for a couple days. He'll teach you what you need to know."

I was excited, but unsure about this. Uncle Bill was a really nice man, but how would he respond to find that his nephew wears girl clothes. I thought I should go back to boy clothes but Mom assured me it would be alright.

I arrived at Uncle Bill's and he welcomed me in, and Mom returned home. We visited, but nothing was said about anything sexual. I wasn't sure how much he knew. Finally he said that I was very pretty, and soon all the boys will be interested. He also told me I should choose a girl name, since Dylan wouldn't do. I chose Darla, and he said he liked it.

I was hoping that we would go on to explore sex, but that's as far as he took it. At bedtime I changed into my nightie and kissed Uncle Bill goodnight. I went to sleep, but sometime later I heard Uncle Bill entering my bedroom. I pretended to still be asleep as he lifted the blanket and reached his hand under my nightie. He pulled down my panties and took my cock into his mouth. What an incredible feeling! I continued to pretend sleep as he sucked me and I came!

Uncle Bill quietly withdrew and left the room. I felt completely drained and soon drifted back to sleep.

The next day Uncle Bill took me shopping at a local lingerie shop and bought me some sexy undergarments. The store clerk asked if I wanted to try them on, but I was really nervous and hesitated. Uncle Bill urged me to try them on, and she said she would help me.

I was terrified when she entered the changing room with me – soon I would be completely exposed.

"Now don't you worry about anything," she said, "I've seen it all, and you have nothing to be concerned about." She helped me undress, and commented on the quality of the breast forms. I told her that soon I would be growing my own, and she said that would be even better. When she removed my panties my secret was now completely out in the open.

"Have you been with a boy yet?" she asked.

"Just kissing," I said, "And a little more."

"Then you have a great adventure ahead of you!" she said, "I hope you meet the right kind of boys."

She helped me put on the lingerie Uncle Bill had picked out for me, and then led me out of the changing room. I had so little on that I was nearly naked, and very relieved that nobody else had entered the store. Uncle Bill approved and said we would take it, so the clerk took me back into the changing room.

I really didn't need her help, but it was clear that she was enjoying the experience. "Your Uncle Bill is a really great guy – I hope you are a very good girl for him," she said. I nodded and wondered just what being a "good girl" would mean.

We returned to Uncle Bill's house. We went inside and I turned to Uncle Bill and thanked him for buying me the nice undergarments and said I wanted to show him my appreciation.

"And just how did you wish to do that?" he asked.

"The way a girl is supposed to show a man her appreciation," I said.

"You know how to do that?" he asked.

"No," I replied, "But hope you will teach me."

Uncle Bill smiled and whistfully murmurred, "Where to start?"

"How teaching me how to do what you did last night?" I suggested.

"I thought you were asleep – you must have been pretending – though it would be difficult to sleep through that," he replied.

Uncle Bill led me into the bedroom, where he undressed, and sat on the edge of the bed. He invited me over and I knelt before him, taking his cock in my hands. It was delightful to feel it growing as I handled him – he was much bigger than Jim. As Uncle Bill grew erect I leaned forward and licked the head, as he moaned with pleasure.

"Take it into your mouth," he urged me, and I did. It felt so right in my mouth – like it belonged there. I felt so at home with Uncle Bill, and wished I lived with him.

As I sucked, Uncle Bill taught me how to move my tongue around and make swallowing motions. He was much too big to swallow, of course, but the motions really got him going, and soon he came in my mouth. Of course I knew that would happen but I was so consumed with sucking that it caught me by surprise. It was really strong tasting – unlike anything else but I was happy to taste it, giving me a real feeling of accomplishment.

"You can swallow right away or hold it in your mouth for a while," Uncle Bill said. I held it in my mouth, savoring the singular taste.

After that Uncle Bill put me on his lap and kissed me – his tongue probing deep into my mouth, no doubt tasting his own seed.

"Your turn now," he said, and had me stand on the top of his legs as he sat there. He pulled down my panties and took me into his mouth. I felt so wonderful about how my life was unfolding. I steadied myself by holding on to Uncle Bill's head and finally came in his mouth.

I kissed him, this time tasting my own seed. Uncle Bill was a really good kisser, and I practiced with him as often as I could. This visit with him was only for the weekend, but I told him I wished I could see him a lot more often.

"How would you like to be with me two weeks out of four?" he asked me, and I quickly agreed. He said he would work it out with Mom, and by the time she picked me up to take me home it was already arranged. On the way home I reflected on how much I'd learned from Uncle Bill. I now knew how to handle another guy's cock well and do a pretty good blowjob – I knew with practice I'd do even better. I also did a lot of kissing and was much more confident now.

I thought about Jim. Would he like a blowjob? I sure wanted to try, but I didn't know when or where I could ever do it. Jim called my cell phone while I was at Uncle Bills and asked me out on a date at the mall Friday night to see a movie. After checking with Mom, I accepted, and eagerly awaited my very first date.

On Friday night Mom dropped me off at the mall at 6pm and told me she would be back to pick me up at 10pm. I was thrilled to have that much time with Jim and hoped we could do some special things together.

We walked around the mall for a bit and held hands the entire time. Hand holding was such a small thing, but it seemed so wonderful – it kind of told the whole world around us that we were a couple – that I was Jim's girl, and I sure liked that!

As we entered the movie theater and looked at the movie listings I saw that we would have at least an hour after the movie was over, so I suggested, "Could we maybe find a private place to visit after the movie?" Jim smiled and said he'd like that. I wasn't looking for a private place to talk – I wanted a private place to take his cock out. I hoped he would want a blowjob, but if not I was prepared to just jack him off. I really wanted Jim to like me, and I was prepared to do whatever I had to.

We got our tickets and went into the theater. There weren't a lot of people so we had a good choice of seats. We sat in the middle toward the back, where we wouldn't be seen by very many – that would make it easier to make out. We held hands as we watched the previews, but when the movie started Jim reached over and put his hand on my breast, squeezing gently. I was glad for his interest but wished that I had real breasts for him to feel. If I am his girlfriend long enough he'll be feeling the real thing. I wished that he would touch me in other places as well, but I didn't dare let him! I really liked being his girl, but I don't think he would take kindly to me if he knew the truth.

We kissed for a while and then he slipped his hand up my skirt. I froze, and quickly snapped my legs together, stopping him.

"I'm sorry Jim," I apologized, "But I don't think I'm ready for that yet, but I want to take care of you – after the movie, okay?"

My cock wasn't very big, and I was able to tuck it in my panties, so there was no bulging, but I didn't want to take any chances – if Jim rubbed me there it might be a problem.

We continued to make out and as I felt more comfortable with Jim I wasn't paying attention and let my guard down. I had relaxed my legs, and Jim managed to slip his hand all the way up without touching my legs. I felt him rubbing his fingers on my panties and I began to get hard. I knew I should have stopped him, but it felt so wonderful. He continued to rub and I got harder, though still tucked away. I feared that if he did it much more my cock would spring free and my secret would be out.

I should have stopped him, but it just felt so good I couldn't bring myself to end it. I was very lucky that I didn't spring free. He pulled his hand back and I breathed a sigh of relief – I really shouldn't let him do that again – I shouldn't have let him this time. He had me so darned aroused I thought about blowing him right in the theater, but there was a couple with kids just further down our row, so I couldn't. I knew he had to be really horny and I wanted to take care of him as any good girlfriend would.

When the movie ended, we left the theater. My heart was racing – I was much too careless and had to do a better job of guarding my secret. I risked losing Jim, or worse yet, things getting violent. I was still aroused but got control of myself. We walked though the mall and approached the store that was being renovated. Jim checked the door, and it was locked. We went for a walk outside, looking for a place with privacy. Then Jim spotted a spot – there were a couple of trash dumpsters that were dark because a nearby light was burned out. We checked it out an found plenty of space behind it to make out in relative privacy.

We began to kiss, and soon I was squeezing Jim's cock through his pants. "Can he come out to play?" I asked in a playful manner. Jim responded by unzipping and taking his cock out. I took him in my hand and stroked him to erection. Once he was hard I got on my knees and began to suck him.

"I can't believe you're doing that!" he exclaimed, "This is every guy’s dream-come-true!"

That was the last he said anything, but he did a lot of moaning before he came. He had a really big load – more than Uncle Bill – I supposed that horny teenage boys were always ready to cum. Jim was really appreciative and reaffirmed his promise to return the favor. As much as I'd like that, I knew it could never happen.

We went back into the mall and talked until Mom arrived to take me home. That night I jacked-off recalling Jim's blowjob.

I really wanted my relationship with Jim to go further, but knew that it couldn't. Thankfully I could be more open with Uncle Bill, knowing that he liked me being the kind of girl that I was – he said I was a "special" girl, and told me that some guys preferred girls like me – if only I could find one!

When I was with Uncle Bill it was like I was his girlfriend, and he made me feel like the most important girl in the world. He taught me about anal sex in a wonderfully kind way. He started out by just touching my hole with his finger, then using some lube he slipped in, always going slow. Sometimes I had to tell him I was ready for more – he was so kind and gentle with me. After awhile he used dildos on me, and then butt plugs and anal dilators. I begged him to slip his cock into me, but he explained that there was a very fine line between exquisite anal pleasure and intense pain and wanted to stay on the right side of that line.

I patiently went along with it until the night he said we would do it. It was a magical night that started with a romantic candlelight dinner and some wine. He treated me like an adult woman he might date – I felt really special. When he took me to bed, he lay on his back and asked me to get him hard, which I had no difficulty doing. Then he said he wanted me to lube up his cock, and my hole, and then sit down on his cock – but to do it slowly – I could control the speed of entry and avoid pain that way.

I knelt over Uncle Bill, with his cock head pressed against my hole. As I pressed down it felt wonderful to slowly open up to recieve him. I wanted more and pressed down but was hit with a blinding pain! He could see my distress and said, "Just hold there until you recover, then go slowly."

I did, and was rewarded with the full feeling I'd been longing for! Uncle Bill told me that when I was ready I could lift up a bit and then sit down again, riding him. I did, and it was a wonderful ride indeed. He stroked my little cock as I rode him, and soon he made me cum, squirting all over his belly. Cumming made my ass tighten around him, and that triggered his climax as well, I fell forward, collapsing on Uncle Bill, and we drifted off to sleep.

We awoke a short time afterward and found that my sticky cum had dried on us, making my skin stick to his as I got up. We showered together and I felt more completely feminine than ever before.

Don't get me wrong, I know full well that I'm a boy, but I'm doing a pretty good job of being a girl, and loving every moment of it. I was Uncle Bills lover when I was with him, but when I was back with Mom I'd think a lot about Jim. He would call me every night, even when I was at Uncle Bill's.

I loved being with Jim, and wished I didn't have to keep secrets from him, but was sure I would lose him if he ever found out. On my next date with Jim, we walked to a nearby park and sat at one of the picnic benches. We found that if he sat with his legs under the table and I sat next to him, facing the opposite direction, that it worked out really well for making out. We kissed for a while but then stopped when Jim said he really wanted to discuss something with me.

"You aren't like other girls," he said.

"You mean I am special to you?" I asked, knowing there was a dual meaning for the word "special."

"Yes, you are VERY special to me," he said, "And I want us to be as close as a couple can be."

"You mean you want to go all the way with me?" I asked, "Isn't that what all guys want?"

"If I denied that you would think I'd lie about other things as well," Jim affirmed, "Yes, I'd welcome that, but it's not what I mean."

"What exactly do you mean then?" I asked.

"You have a secret that I really want you to share with me," he said, "It will bring us closer together."

"I'm not sure I know what you mean," I responded.

"I think you do," he said, "And it feels like you don't trust me enough to share it with me."

"Jim, I trust you completely," I insisted, "What do you want me to do?"

"Hand me your panties," Jim said.

"Oh, so you're a panty collector now?" I said with a grin. I reached under my skirt and slipped my panties down to my ankles, and over my feet. I handed it to Jim, and he brought it to his nose and sniffed.

"Not just a panty collector, but a panty sniffer as well," I said.

"This is more intimate that I've been with you," Jim said, "So this will have to do."

Jim stuffed my panties into his pants pocket and we continued kissing. Jim felt my breasts as we did, but then he caught be completely by surprise when in the middle of a French kiss he slipped his hand up my skirt and took my cock in his hand. He squeezed it, and I kissed him more pationately – it was like he had control of me. We continued to kiss for another minute and then stopped.

"Isn't this a lot better when we share your secret?" he asked.

"I'm sorry," I said, "I didn't know how you would react."

"That was smart of you," Jim agreed, "Some guys would really freak out."

"But you didn't," I observed.

"Darla, I really LIKE girls like you," he explained, "I've dreamt about them for the longest time, and now you are the girl of my dreams!"

"So where do we go from here?" I asked.

"I have a promise to keep," said Jim. He lifted the front of my skirt, leaned over and sucked me, not stopping until I was spent.

From that point on Jim was my true boyfriend. Uncle Bill knew about him, but Jim didn't know about Uncle Bill, and I had no reason to tell him. Boyfriends can be really possessive and jealous, and I didn't want to ruin things by telling him about it.

I also didn't tell him that I had a group of college boys I blew regularly. I didn't dare mess with guys in my school because I didn't want word to get around. But I think it helped my relationship with Jim. I was getting plenty of variety from guys who just needed to cum, and that was enough for me. When I was with Jim, I could give myself totally to him. In Jim I found sanctuary – a loving guy who always treated me with respect.

Special thanks to my online friend, Justyne, for inspiring this story.

  To be continued . . .

Feel free to contact me with your comments or requests.
    –Bill Beaumonte (oral_guy_2000@yahoo.com)