Chapter 1

Throughout this story and any future chapters any transgendered, transvestite, or shemale/lady-boy characters will be referred to as “She”.

I always wanted to look like a girl. Now please note I never said I wanted to BE a girl and I didn’t and don’t. I like my cock and balls far too much. So I was around 9 going on 10 and puberty had hit me with unexpected hard-ons and my big kick, about the time I learnt how to jerk myself off, was to wear my sister’s clothes when alone in the house. This applied especially to my sister Marie who was away at university much of the year so I could plunder her things without any chance of her knowing. Mostly I loved wearing her silky sexy panties under my ordinary clothes and the feeling of huge excitement had me hard most of the time and getting myself off a lot.

Next I graduated to trying on complete outfits not just panties and as I was a fairly tall boy for my age and Marie was/is petite they tended to fit fine. The next stage was make-up. I’d seen Marie put on make-up plenty of times and now, when my other sister Gail was making up her face, I’d watch and ask her questions. At first it was either “what’s wrong with you” or “leave me alone” but pretty soon she realised I was genuinely interested. So she explained and showed to me how different complexions needed different cosmetics and got me to apply her make-up and even made me up one day. She made me clean it off well before my mother or father came home but I’m a quick study and caught on fast.

So by the time I was 12 or maybe 13 I could dress like a girl and put on flawless make-up. One day I decided I’d take a chance and do a crazy thing and go out pretending to be a girl. It was summertime so I put on panties and one of Marie’s tennis dresses after a little light make-up application, Marie had masses of stuff she’d outgrown but wouldn’t throw out, which was great for me. So I also took Marie’s tennis club membership card and made my way to her “Richmond Tennis Club”. Now handily entrance was by swiping her card through a reader so nobody checked that I was in fact Marie Carmine and not Leslie Carmine.

So I wandered around watching girls and boys and men and women practicing or playing tennis matches and nobody had the slightest idea I was a boy and not a girl. I did some ogling alright! By now I’d had sex and not just with my left hand. I mean I’d only had sex with a few boys as 14 year old girls aren’t that keen to risk getting pregnant by a 14 year old boy. So I ogled boys and girls and was glad my panties were sound enough to restrain my swelling hard-on. And that was the first time I met “Willow”! Her real name was/is Jamie Azaria which is handy, because like my name, Jamie can be a boy or a girl’s name just like Leslie/Lesley.

She was sitting on a padded bench, under a shade tree, watching two lithe and agile pre-teen girls volley and serve. I liked the look of her and greatly daring crossed over to sit next to her. Like me she was wearing a short tennis dress and I thought her legs were superb. I opened the conversation after nodding at the two girls on the court.

“Are they any good?”

She frowned and narrowed her eyes but replied friendly enough.”

“I dunno as I’m no expert but yeah I think they’re very good.”

She was shorter than me, I’m tall, and where I’m milky pale she had a deep olive skin with short silky dark hair. Also her voice was kinda husky and that was a turn on too. So we talked and I guess I was trying to flirt with her a tad and I was turned looking at her pretty face and curvy body when something sort of clicked in my head. I leant so my lips were close to her ear and whispered quite softly so nobody else would be able to hear.

“Well fuck me you’re a boy!”

She barely turned a hair and gave me a small puzzled frown.

“How could you tell? Nobody else has even found out.”

“It was a big, big; make your mind up decision time, so I “came out” in an odd way.

“Because I’m a boy too!”

She blinked and looked at me REALLY hard and then grinned.

“Well Jesus Christ so you are! What are the odds of this happening?”

So she told me her name was Jamie but for some reason she was called Willow. Apparently as a baby Jamie cried a lot so the family first called her “Weeping Willow” that then got shortened to just Willow. She was also almost exactly the same age as me. Right off we were really comfortable with each other and we were chatting and giggling enough for club members to be shooting the odd dirty look at us. So I invited her back to our home; and off we went holding hands and giggling some more. If we’d have looked like two boys we’d have been getting “Fucking little queers holding hands” but with two girls nobody said a word.

So when we arrived at my home Willow’s jaw dropped as she stared at the place.

“You live HERE?”

“Yeah sure I do; why?”

Because it’s amazing and humongous that’s why. How many of you live here?”

“Well when we’re all home, one of my sisters is at university and the other goes away to college soon, there’s five of us and that’s with me and my parents.”

“But twice that many could live here and things still wouldn’t be crowded.”

“Yeah we got lots of room here; come on!”

So I tap in the P.I.N. number that opens the gate to let us walk up the driveway.

“And nobody has noticed a pretty young girl coming out here and asked who you are Red?”

Now “Red” is my nickname for two reasons. Firstly I have copper red hair and secondly my family name, “Carmine”, is a strong red pigment artists use.

“You see Willow this place stands alone in its own grounds and our closest neighbours aren’t really close. Now if any of them spotted me leaving today they’d likely think I was my sister Marie going to her tennis club. I do look a lot like her you know? So how do you go out as a girl without being spotted?”

Willow gave me a wonderful grin.

“Carefully Red very carefully indeed!”

When we reached the front door I fished out from the ball pocket in this tennis dress my swipe card and passed it through the reader and then tapped in another P.I.N. number. There came a click and the front door opened to us. Once in I shut it to lock us in and we stood there in the huge hallway.

“Your family must be loaded Red?”

“Well yeah we’re not short of a few bob to be honest. How would you like the grand tour?”

So I showed Willow the swimming pool at the back and the huge gardens and then all around our palatial home ending in my own bedroom.

“Oh-My-God!”

That’s how she said it when she saw how it was furnished and equipped. Me? It never occurred to me that others might think the place was special.

“Why don’t we get comfortable on my bed and talk?”

Now my bed wasn’t just a double, which is four and a half feet, but six feet wide and super comfortable. We were lying side by side nattering.

“So you don’t want to BE a girl then Red you just want to look like one which is exactly how I feel.”

“Yeah look Willow I love my cock and balls but I also love looking like a pretty girl.”

“Me too so I really get it Red.”

I reached out towards her, hesitated, and then touched lightly what felt like a small breast bud.

“How do you get to have tits?”

She giggled like we’d been doing a lot since we met.

I’m wearing one of my sister’s bras with a bit of padding.”

Now I giggled.

“Me too! It’s a sports bra with some foam rubber packed into it.”

“You got great legs Red; nobody would ever think that you aren’t a girl.”

“You too Willow and I bet you got a great ass as well.”

“Do you want to see it? Then take off my panties.”

That was easier said than done because even when she lifted her hips up I had a hard time getting them down over her hard cock. I had to pull the waistband out a lot to get them off. Willow’s cock was erect and looked like it might be just a tad longer than mine though with the big upward curve it had it was hard to tell without measuring. Her cock though was surely no thicker than mine. Willow, like me, still had her foreskin.

Now when I got curious about boys and sex I did some research online to get clued up on the technical side of things. So a cock or a dick was actually your penis and your balls were your testicles and they manufacture sperm which we call jizm, or cum, or sponk. A cum was rightly an orgasm and as Willow’s foreskin slid back a bit I could see we shared something. Like me she didn’t have a round knob-end like some boys but her helmet, like mine, was sort of a long oval shape and almost purple. I also knew that knob or helmet it was really a glans.

“Fuck that’s a nice cock you got Willow!”

“I thought you wanted to see my ass?”

“I want to see both really!”

So she rolled over and she did have a great ass with a dimple in each cheek.

“Nice!”

Willow rolled back over to face me.

“So when do I get to see your ass and cock Red?”

Now I had as hard a time getting my panties off as I had getting hers off since my cock was up and hard like hers. So I lay on my back, lifted my hips, and managed to wriggle out of them. Willow liked what she saw then.

“Oh wow that’s a nice cock.”

Like I say my cock may be just a tad shorter than hers though not by much and it’s easily as thick. Mine though hasn’t a trace of a curve and it’s just straight and smooth. I obliged Willow with a roll over and she loved my ass too. Right about then though I was hot for her and couldn’t wait.

“Do you want to do it Willow?”

“Crap yeah so who goes first?”

“You can as you’re the guest; so what do you want?”

“How are you with blow jobs?”

“I’m good, really, really good!

And I am now and was back then though it turned out Willow is perhaps a bit better than I am at sucking cock though I’m still very good at it indeed!

So Willow’s on her back and my head is right where it needs to be which is right above her hard cock. I took it into my mouth and got down to the serious job of pleasing her by NOT getting her off to fast. With my lips tight on the barrel of her cock I bobbed my head smoothly and slowly at first before gradually increasing my pace. At random moments I’d lick her swollen helmet; or use my tongue tip to explore and tickle the folded back pleat of her foreskin and the underside of her helmet. Then it was back again to sucking and bobbing my head as I took her higher and nearer, held her poised, and then, as she gasped and clutched my head and her belly rippled, I took her over the top.

Willow was moaning and bucking as she shot her load of hot creamy jizm into my mouth and I savoured and swallowed every drop. When she stopped writhing I pulled my lips free of her cock with a wet popping sound and kissed her belly.

“You weren’t kidding Red you’re so good you’re nearly as good as me.”

I let that one pass by but later I found that Willow gives the best head of anyone who’s ever sucked my cock. At least Willow knew how much I needed to get off and went right to the point.

“You need to cum so what do you want because I’m good at everything.”

Well after seeing that round dimpled ass I knew exactly what I wanted but weirdly, hell I was just turned 14, so I was entitled to be a tad nervous with even this hot 14 year old boy/girl I’d just met.

“Well you do have this lovely ass so maybe... !”

When I trailed off Willow grinned at me and it was the sexiest and wickedest grin I’d ever seen.

“So you wanna fuck my lovely ass? Go for it Red baby!”

So I hopped off my bed and almost trotted into the en suite bathroom and as I did Willow called after me.

“You’ve got a great ass too Red!”

It registered later that both us boy/girls looked convincing as girls because we were already sort of equipped by nature to look girly. We both had round girly asses, we both had long smooth girly type legs and thighs, and we were both really pretty boys so we made really pretty faced girls too. When I came back I was holding a bottle of baby oil. It’s cheap but the cost isn’t important. What is important is that it’s a great lube for ass fucking; you can buy it anywhere, and I can buy a bottle at our local pharmacy without the staff, who knows me and my family well, batting an eye. I can buy the oil anywhere while I can’t buy a container of say “Liquid Silk “lube at all.

When I got back Willow had gotten naked and I soon followed suit. I slicked up my cock from helmet to the base of my barrel and dribbled some onto Willow’s taut pucker.

Yeah I’d checked that out online too and a pucker is really a sphincter. And when your cock gets inside you’re in someone’s colon which is sort of ridged and like scaly which is why your helmet feels amazing when you pump away in a boy or a girl’s ass. So now I got Willow on her hands and knees and eased my helmet up against her oily pucker. She was tight! Beautifully tight! But she wanted me in there so she didn’t tighten up like some newbie boys do when they’re about to be ass fucked. Under my steady pressure she slowly opened up and my long straight cock followed my helmet deep into her so smoothly.

I groaned out loud and gripped Willow’s hips as I thrust hard, eased back, and thrust again. My cock was sheathed tight in her colon and my bloated and sensitive helmet was grinding on those firm ridges as I fucked her fast and hard. Already the heat was building and boiling behind and then into my taut ball sack as I panted with pleasure. Soon I could feel the pressure and electric flares soaring up the barrel of my cock and I yelled out “Oh Fuck” as I pumped out wads of jizm from my throbbing cock.

Drained I eased back out of her and as I did a single bead of sweat dripped from the tip of my nose onto the back of her neck. I flopped onto my back and lay looking up at the ceiling as my heartbeat slowed down. Willow rolled over to face me and kissed me very expertly indeed. Right then I realised that was the first time we’d kissed though we’d both got each other off. So I kissed her back and I was and am also an awesome kisser. She rested her head on my belly.

“Wow you are some kind of young stud Red. Maybe you should be nicknamed “Stallion” instead?”

I stroked her silky dark hair.

“Nah I’ll stick with Red thanks!”

“Cool and when I’m up and ready again can I fuck you from the front?”

“You can fuck me anyway you want to baby!”

So we talked a while and kissed a lot. One thing I recall us talking about was girls over which Willow and I agreed. Yeah we’d love to fuck girls but it would be hotter to fuck girls not as a boy but as a girl with a cock