A T-Girl and a Tomboy Pt. 01

I laugh. "Really? You're gonna laugh at me."

I hold her tenderly as she curls into a ball and looks up at me expectantly.

"I once saw a video of a bunch of cheerleaders who were teasing for the camera in their uniforms. They were gorgeous and all over each other, but half way through, one of them pulls a real cock out from under her skirt and they all fuck each other's brains out."

"That sounds fun. Do you want to fuck me in my uniform?" Jena lets go of me, steadies herself and stands up. She turns off the shower and reaches for a towel, bending forward with her backside to me.

I've got a perfect view of her perfect little asshole and her perfect flower-like pussy, a heavenly flower—a 'Leilani'?

"In your uniform? We've done it a lot in my imagination," I admit, without mentioning that in my fantasies I'm a girl too.

"You've fantasized about us?" Jena asks, drying herself with a towel. "I've been fantasizing about us too, but in my fantasy... In my fantasy dreams, I'm the boy and you're the girl."

My head spins.

***

Girls Undercover

Jena sighs. "I was sad that you were gone so much, but I was happy for you that you got to do all that traveling. When Sandy seduced me I thought I was going to be a lesbian forever. I love playing with strap-ons, but you're like a girl with a real dick. Can we get in your bed? You can play with mine if I can play with yours."

"This is fucking crazy...it's crazy, right?" I ask, in disbelief. Everything is feeling strangely limitless.

"Yeah, and it's crazy...and about effing time." Jena laughs. She grabs another towel and pulls me to my bedroom.

Half dried-off, we dive naked into my bed, wrapping around each other like snakes. We explore and experiment, prod and poke, lick and suck and everything nice.

She whispers, "Do anything you want, I'll let you know if it's too much, but I doubt anything will be a problem."

"Yeah, you too. I'll share everything I have."

"Everything?"

"Everything."

My body is rushing and my heart is completely open.

A stray thought crosses my mind. "Hey Jena, I know I've already had these feelings. Is this all real for you, or is this just the ecstasy talking?"

She laughs. "Oh stop."

She's all over my cock and I'm all up in her—we can't get enough. She's tugging and stroking, while I'm slipping around in her tender pink folds. I keep trying to catch the nodule tucked under the hood at the front of her slit. I've fantasized about having all of these girl-bits, but this is my first time touching them.

She's stroking my cock and rubbing and pulling at my taint. Her other hand pinches and caresses my nipples.

I nibble her ear and neck, amazed by the reactions I'm triggering in her body. I flutter my fingers inside where I understand her G-spot to be, and she tries to swallow her own clenched fist.

"Pussies are amazing! This is so much nicer than I ever imagined. Everything I do radiates to your toes."

She's barely breathing.

"Are you okay?" I ask, letting her relax so she can catch her breath. It seems like it could be dangerous to get her so turned on. Could she have a stroke from an orgasm? It takes a moment for her breathing to slow down.

Jena's eyes are cloudy. She says, "I'm so into you and what you're doing to me. I really want to taste you."

I borrow her tongue for a sweet moment before laying back on the bed to make myself available to her.

She kneels beside me and puts her hands my cock, holding it lovingly, like it a confined a bird—so its wings can't get loose to fly away. Her tongue explores the sides of my shaft and her squeezing hand milks a drop of pre-cum onto her fingertip. A thread like spider-silk hangs there between my tiny slit and the drop on her finger. Moving on it instinctively, she takes the cum-drop with the tip of her tongue, then follows the silky strand to its origin. She licks my slit and kisses the head of my cock before tentatively putting her lips around it. She kisses and sucks me, getting a little more boy-juice for her trouble.

She sits up, her expression seeming to consider what she's just done. She's surprised with herself—not ashamed. Bringing her hand to her mouth she licks her fingers.

"I never wanted to do that before," she says more to herself than to me.

I'm throbbing and fascinated watching her. "Have you ever been with a boy, Jena?"

"I've had a few times that were kind of like your deal with Sam, but I'm the one who ended it. I went farther than I really wanted to on a couple of dates and got them off with hand-jobs, but it still was my choice. I've tried to like guys. I haven't gone out with a guy since Tonya, Raven and I went with three guys to the Winter Ball, but we ended up having to ditch our dates."

"Really? I can't imagine the three of you would have trouble finding good boyfriends..."

"None of us were looking for boyfriends. I think we all went to the ball with them because of tradition. It's like that's what high school seniors are supposed to do. I should have known better. I'd already discovered girls."

"Sandy opened that door for you?"

"At one tournament, Sandy and I were watching and noticing how tight and affectionate Liz and Jess are. We could see how they were more than just best friends. We started talking about how lucky lesbians are—girls are usually so much sexier than guys, when she leans over and gives me a quick kiss on the corner of my mouth. It just sat there. I could feel it aching all night. I was thinking, 'I kissed a girl and I liked it...' We had a long drive back home in the back of your mom's van. After that we were at it whenever we had a chance. It was fun while it lasted...until whatever happened to Sandy happened."

Jena trails off then says, "Can I play with your ass again?"

Gulp.

She laughs at my expression and reaches under me to stroke a finger across my pucker.

Trembling, I say, "The shower was my first time—be gentle."

"Don't you ever use sex toys?" she asks.

"You mean like dildos?"

"Dildos, vibrators, butt plugs. Never?" She's surprised.

I giggle and blush and say, "Are you about to show me?"

She beams with a smile and says, "Another fantasy come true. I'll right back, babe." She wraps a towel around herself and leaves the room. When she returns less than a minute later, she has a duffel bag with the squad logo on it.

"This is the 'G-bag', it belongs to the squad. It's like the free-box for sex toys."

I'm nervous. The bag looks heavy.

"Do you know anything about this stuff?" she asks. "Let me show you."

The bag is filled with rubber, leather and vinyl and it all looks kinky and intimidating.

"There are different kinds of sex toys in here; dildos, hand-tools, plugs, double sided dildos, various vibrators and harnesses..." She pulls several items out of the bag and describes them as she lays them on my bed.

"Strap-ons are made for anatomically correct fucking when you don't have a penis. There are 'hand-tools' or dildos with handles for fucking yourself or a friend without needing someone to play the guy role. Plugs are things that you insert and keep in for a while, sometimes you have to wear something over them, like panties or a harness so they don't fall out. Then there are double-sided dildos, so a girl can fuck herself while she fucks someone else with the other end."

The variety is astonishing.

I say,"I've seen some online but I never actually touched one. Some of them are huge! Have you used all of these?"

Jena laughs. "Some were given to the squad as a joke I guess, we just throw them all in the G-bag."

She grabs two leotards taken from the free-box. They are the cool weather uniform long-sleeve hoodies with thumb-loops, black with a red stripe across the shoulders and down the sleeves.

"Here. I think you're going to like this," she says, handing one to me.

We both step in and pull one on. These are some of my favorite items from the squad uniforms. The hoods have a secretive feeling—they can help hide my face, and the long-sleeves with thumb-loops make it so when I extended my arms, the leotard tugs at my crotch. I could get all worked up in it just by doing yoga or sit-ups in one.

Jena opens the duffel bag and pulls out a small butt-plug and a plastic bottle of lube. She lays down a towel and gets on her knees. Slathering lube on the plug and pulling the crotch of her leotard aside, she runs a lubed finger into her own ass.

"I bet you haven't done this before either, have you?" She hands me the slippery rubber sex toy and says, "Plug me."

Trembling with adrenaline I put the soft pointed tip into her tight little pucker. Her ass opens around it as I push the tip into her, the first bit sliding right in. I'm nervous to push the rest in until Jena holds my arm and rocks back against the plug, pushing it into herself as I hold it for her. The tapering plug is larger in the middle and then gets skinny again for the last inch. She moans with delight when the widest part slips into her and the whole thing settles up inside of her with the t-shaped base nestled deeply between her cheeks. She pulls her leotard back over the base of the plug and sits up on my bed.

"Hmm... thank you, babe. Ooh, it feels so fucking good...Do you want to be penetrated?" she asks, as she clambers about on my bed, cloudy eyes rolling around in her head. She shivers and gets back onto her knees. She shuffles to the G-bag and picks out another plug like the one in her.

"Your turn?" she says, holding the butt-plug for me to inspect.

It's a ridiculous looking thing, you'd know exactly what it is even if you'd never seen one before.

She has me get down on all fours, pulls my leotard aside and lubes me generously. She spends a delicious minute doing this, dragging her digits in and out of me several times each.

"Shh, it's okay, babe."

I'm so rapt with anticipation that I didn't notice how loudly I was groaning.

"Relax and let me do it," Jena whispers in my ear as she pushes, working it in bit by bit. I feel my hole stretch as she drives it up to the thick part. I know it's small like hers but it feels huge, taking my full attention, as the wide part pops through my inner-ring and the t-shaped base settles between my cheeks. I'm still coming to terms with what has just happened to me when she pulls my leotard back over the plug, pulling it into a wedgie and practically lifting me and making me stand next to my bed.

Jena is strong. She swings her legs off the bed and stands behind me, bending me forward onto the mattress with my feet still on the floor. I can see our profile in the wall length mirror. From behind, she presses her pelvis to my ass and humps me like she did in the shower.

"You want to get fucked by a girl?" Jenna asks, putting pressure on the plug inside of me.

"Yeah, ugh...huh." I'm throbbing and sweating and can barely talk.

"Yeah? I'll do you with a strap-on later, but let's save that for tonight. We can have an epic night of firsts, including my first ride on a real cock," she says, humping me rhythmically.

"Uh-huh, Ooh-ka-yay-ay." I'm drooling.

I'm getting humped from behind with a plug in my ass, I'm dressed in a leotard and being done like a girl. I love that Jena wants to fuck me.

"Oh-oh, Fu-uck Me-e!"

She grabs my ponytail and pulls my head back. The rough treatment surprises me and my body responds with a rush of dopamine.

"Yeah? I'm going to fuck your ass you little fairy-boy." Jena growls and bites my ear.

She's getting me up all worked up, humping me harder and faster, the plug poking impertinently at my insides. Everything is throbbing; she's triggering whole new sensations and all I can think about is how good it feels to be done by her—the best ever! She gets angled just right and the pleasure grows with every thrust. My ass is pinned between her hips and my bed. Looking sideways at the mirror, I watch Jena's lustful expression as she grinds her pelvis against my ass.

Suddenly, there is no mistaking as I'm overcome by a throttling orgasm. I expect that I'm about to make a seminal mess in my bed but I'm shocked that I don't ejaculate—I'm having an orgasm in my ass! I'm making lots of pre-cum but my cock isn't even fully hard.

My mind is blown again!

I ride the climax with Jena's thigh pressed against me and collapse onto the bed. I roll over onto my back, far off in cosmic space. Minutes pass as I lay there in the after-glow.

Jena, herself recovered, is looking me over thoughtfully, tracing the curves of my face. "That was beautiful, girlfriend," she says, brushing my hair aside and covering me with sweet kisses.

"Thank you, boyfriend," I say.

It felt right. Something clicked into place when I said it. We lay there for several minutes, just looking into each other's eyes in wonder.

When my breathing returns to normal, Jena says, "We definitely have to do more of this but right now we should get you ready for the party." She helps me sit up and says, "First we should fix your hair. It's all trashed from sun and salt water, but it's long enough to have some fun with it."

She untangles from me, climbs out of bed and tosses me a skirt and a pair of long black socks with red stripes.

"Here, get dressed, I'm going to get some help," she says. She puts her skirt on over her leotard and leaves the room again.

I've privately worn leotards and skirts countless times but I'd never added thigh-high socks to the combination. I pull the striped socks up over my knees, really liking the look and how it feels. I remember a study I once read about that said some women orgasm more easily and more intensely while wearing socks or stockings. Hmm...?

I watch the 'girl' in the mirror. 'She' is cute and I want to stare at 'her.' I'm very turned on by the idea that 'she' has a plug in 'her' ass.

Thinking about it draws my focus back to the sex toy. I'm still penetrated. I reflexively clench and grip it. It may be one of the smallest things in the G-bag but the way it grabs my attention is huge. I can't imagine taking a cock the size of my own. Sam would have split me in half!

Jena soon trounces back through my doorway, practically dragging Raven. The air in the room seems to change when she enters.

Raven is stunning, with her dark complexion and her red-satin bikini with gold rings at the ties. Her long black braids are tied into soaking-wet pigtails.

Raven protests, "Hey! I'm dripping all over the place. Why did you drag me out of the hot tub? Who needs the emergency..." Raven sees me and understanding spreads across her face. "Oh, okay... So you're the emergency makeover?"

***

Trifecta

Raven grabs a towel, dries off and goes out to her car to get her professional theater-kit for makeup and hair. She comes back with it rolled up like a yoga mat with a strap so she can carry it over her shoulder.

"Alright, 'Miss' Alex," she says. "Most of G-squad just got here and the rest will be here soon. What are we going to do with you? Your hair is trashed and we don't have time to do extensions, do you want a pixie cut?"

"Can you keep it long and fix it?"

Raven lays out her kit and sets to work combing and detangling.

"I guess it's not a bad as I thought. I can probably work with this. I've got to trim enough to get rid of the dead ends. Are you sure you don't want it short? Some girls look really cute with short hair, but then again, some of them look like sexy little trans-boys." She chuckles. "We have some handsome young men at school that were all born girls."

"That's some wicked irony," I say.

Raven laughs and pulls a comb through my hair.

"We're looking for something that brings out your female side. How about I give you some classic braids, you can't get much more girly than that. Braids can make hot guys look androgynous, but you're already effeminate."

Raven takes a pair of scissors from her kit. "You're very pretty, Alex. You look naturally comfortable as a girl. Sit straight and look at the mirror."

Standing behind me, she combs and snips and fusses about. A few minutes later I have two French braids.

"That's it. Very basic but it works."

She's right, it does work. I look even more like Tonya, braids are her regular thing. They feel snug around my head and I like the way the ends brush my shoulders and swing about when I turn my head. Raven rubs her hands down my hair, continuing to my chest, touching me appraisingly.

"You barely have any facial or body hair. Do you shave for swimming?"

I can see her in the mirror, standing behind me with a warm, amused smile. This is all a series of firsts. Beautiful exotic Raven has rarely ever spoken to me, certainly never opened up, and now here she is, pressed up close behind me in red satin, doing my hair and asking about my grooming habits.

"My senior project is training for the iron-man. So yeah, biking and swimming are great reasons to shave."

Jena laughs. "I didn't even notice! It just seems so natural that you'd be all clean shaved!" She rubs my legs finding no stubble anywhere. "Wait a minute..."

"I used some of Tonya's Nair earlier today," I say.

Jena smiles and gives me a sisterly hug.

Raven tugs at my ear lobes and says, "You should get pierced tomorrow at the pier at the earring store, their selection is huge. They pierce things besides ears too in case you're interested."

The talk about piercing reminds me that my previously virgin asshole has a very distracting rubber plug in it. My leotard with thumb-loops is pulling it firmly up in me with every move I make, and one of the prettiest girls I've ever met is doing my hair and admiring me, giving me advice on piercings and how to pass a female, Jena have just gotten sexual with eaxh other in a very kinky way...

"Are you okay, Alex?" Raven puts down her comb.

I squirm. "I'm sorry, I'm kind of distracted right now. It's hard to talk." I look desperately to Jena.

Jena says, "Hey Raven, did you have any of Sandy's sports drink?"

"Yeah. Why?" Raven asks innocently.

As she says it, I feel rushes coursing through my body. "I had some too." I say.

Jena explains, "Yeah, I'm all aching to cuddle. I think Sandy's drink is spiked with Molly."

Raven looks scared for a moment. "Molly? You mean ecstasy? Shit, you're probably right. Damn it! She should ask first." then looks at me and Jena. "She got both of you too, right?"

We nod.

"Well I'm okay then. I guess the party is getting off to an early start." Raven looks thoughtful for a moment then shrugs it off and smiles at us. "This could be fun. What's distracting you, Alex?"

Jena laughs. "Alex is deliciously distracted the same way I am." She points to the G-bag and moves her hips suggestively. "Would you like to be distracted too, Miss Raven?"

"Both of you?" says Raven, her beautiful green eyes asking a million questions.

We nod.

Raven gathers herself and straightens her posture. She strides to the G-bag and peeks into it like it's full of adorable puppies. She pokes around, picks out a small plug with a shiny jewel in the base and hands it to Jena.

"Dear sister, will you do the honors?" she asks.

"My pleasure." Jena smiles as she opens the lube.

Raven leans forward onto the bed, feet wide apart on the floor. Jena pulls the satin bikini bottoms down around Raven's knees.

I am completely awestruck by what's happening here in my bedroom. Jena is generously lubing Raven's ass, working it up inside of the beautiful girl, finger by finger. Raven's expression is feral. Her lip quivers and she steps into a wider stance.

Jena lines up the plug and pushes the tip into Raven's beautiful little hole. The gorgeous girl rises to her toes and balances there, back arched, hands and forearms on the bed. She braces to take the rest. She moans deliciously as Jena drives the plug in the rest of the way and lovingly pulls Raven's bikini bottoms back up, tying them tighter around her hips.