Alexis

Story Info
Young crossdresser begins the transformation to a slut.
2.3k words
4.43
130.2k
51

Part 1 of the 5 part series

Updated 10/29/2022
Created 06/21/2008
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When I hear both of my parents starting to snore in the room below me, I quietly get out of bed and sneak over to my dresser. I dig past the piles of underwear in the top drawer until I find what I am looking for. I pull out the black silk g-string and slide it up my shaved legs, tucking my tiny cock back into the smooth crotch of it. Next, I pull on a black cami, a black lacey garter belt, and a pair of black, lacey stockings.

I look at myself in the mirror through the moonlight. From the shoulders down, I could definitely pass as a slutty teen girl. But in reality, I'm a skinny, not yet fully developed, eighteen-year old boy with more curves than muscle. My hair and eyes are brown; my cock about 5 ½ inches long and cut.

I climb back into bed and lay down. I let my hands drift across my body, touching my curves and feeling the smooth silk against my skin. My mind starts to wander. I start to think about letting a man take me, letting him use me as his little slut and have his way with me. My hands begin to drift over more sensitive areas of my body. I start to lightly rub my cock through the silk material of the g-string. It twitches at attention, and I start to rub the tip of it.

Bringing my knees up, I spread my legs a little bit. Without even realizing it, my hand drifts down to my asshole. I start to rub it through the string of my panties. My asshole twitches in anticipation.

I squirt some lube on my fingers and pull aside the g-string. I start to work some lube around my ass before easily slipping in two wet fingers. My hole clamps around them tightly, and I let out a sigh. Shivers run up my spine. I pull my fingers out to my knuckles, and then slowly work them back in. I start to work up a rhythm, and begin to fuck myself with my fingers. I work in a third finger with little effort.

By now, I'm thrusting my ass against my hand and biting my pillowcase to keep myself from moaning. This needs to end soon, before I'm let out a squeal and wake up my parents.

Reaching under my bed, I search around with my hand until it touches plastic. It's a sample sized shampoo bottle. I've been using it to fuck myself with for a while now. It's the closest thing I could get to the shape and size of a cock.

I slather lube onto it and press it against my accepting asshole. It slides in slowly, and for a second I feel a sharp pain. It's almost instantly replaced with pleasure though, as the rest of the bottle slides up into me. I start to pump it slowly in and out of my little hole, spreading my legs wider, just like a good little slut.

I imagine that someone is using me. I slam the three fingers that were in my ass into my mouth and lick them clean, sucking on the greedily. I want to be used. I want to be someone's whore. I want to be filled with cum all day and all night. My deepest desire is to be a walking sperm receptacle; to be ready for cock and expecting it at all hours.

With these thoughts, I begin to cum. I barely have to touch my cock, and already it's exploding warm sperm all over my stomach. I slam the shampoo bottle deeper into my ass as I cum, struggling not to moan. The orgasm finally subsides, and I let out a deep breath. I know what I have to do to be a good girl.

I pull the shampoo bottle out of my ass. It's covered in lube and ass juice. I bring it to my mouth and lick it clean. I scoop up the little pool of cum that's collected on my tummy and lick it from my fingers. I hold it in my mouth for a while, enjoying the taste of it, before swallowing.

I strip my lady's clothes off and climb into bed naked. I fall asleep a little after, tired and unhappy at the fact that I have to wake up for school in the morning.

This is an ordinary night in my life.

I'm sitting on the bleachers in the gym the next day during lunch, watching the class run laps around the court. My younger sister is in the class, and I find it funny that as I'm watching her run, she has no idea that I'm wearing one of her thongs under my jeans. She glances up at me and we make eye contact. She smiles and waves, and then continues her conversation with the girl she's running with.

The bell rings. I stand up and pretend to adjust my pants, but in reality I'm fixing my thong.

My sister stops running and comes up to me. Her friend is standing behind her. I catch her checking me out.

"Hey, I forgot to tell mom that I have practice tonight," she says.

"Well, mom and dad aren't home tonight. They have that retirement party to go to."

"Ok then...well I might just stay at Kelly's tonight then," my sister says. I nod my head.

"Alright. But make sure you're back in the morning, mom and dad will be pissed if they know I let you stay out," I warn. My sister smiles at me somewhat sarcastically. I roll my eyes and head to my locker.

In class, my mind wanders from Biology to more perverted things. I think about what I'm going to do when I get home. I decide which of my sister's outfits I'm going to try on first.

"Alex!" my teacher-Mr. Hughes-says. I look up and realize that he's calling on me to answer a question. "What happens during cellular replication?" he asks. I open my mouth to say something, but realize that I have no idea what the answer is.

I stutter for a moment, managing to say "I don't know." My teacher shakes his head.

"See me after class," he says. A few snickers echo throughout the classroom.

When the bell rings, I hope that Mr. Hughes forgot that he had asked to see me, and I try to sneak past him.

"Alex," he says. He motions for me with his finger. I approach his desk.

"What's up?" I ask. Mr. Hughes sits down, sighing. He opens a desk drawer and flips through a row of files, finally pulling out a test with my name on it. Next to it is a huge "E," written in bright red ink. I stare at the test blankly.

"This E just lowered your grade to failing," Mr. Hughes says. "And you're constantly late for class." I say nothing. He looks up at me and raises his eyebrows.

"I know. I just get distracted easily," I stammer.

Mr. Hughes holds his hand up to stop me.

"You know, I do offer an after school tutoring program. If you attended and showed some effort, I might be willing to be a little more open minded about your grade," he says.

I hesitate. The last thing I want is to have to stay after school to put up with even more of the subject that I simply hate.

"Of course, you can just stick with the E." Mr. Hughes smiles at me.

"When is it?" I ask.

"Right after school," he replies. I nod my head.

"Sure, I can stop by for a little while."

"Good. I'll see you then."

For the rest of the afternoon, I think little of my tutoring session with Mr. Hughes. However, I have no idea just how much it will end up changing my life...

At 3:00, I find Mr. Hughes in his classroom, sitting at his desk and typing something into his computer. I'm the only student there; it's obvious that the tutoring isn't something many students choose to take advantage of.

"Alex, you came. Have a seat," Mr. Hughes says. I drop my backpack to the floor and sit down in a desk that Mr. Hughes had pulled up to his.

"Here, fill these problems out. These are some of the questions that are going to be on the next test, so it'll help you if you study them," he says, handing me a worksheet. I rush through it, wanting to get home as soon as possible so I could dress up and be a whore for the evening.

As I lean forward to hand Mr. Hughes the worksheet, he says something that makes my heart stop.

"Nice color," he says.

It takes me a second to realize what he's referring to, but when I feel air against my bare back, I realize that he was referring to the strap of my neon green thong, which has risen up and is resting of my hip.

I feel my face turn hot with embarrassment. I quickly stand up and grab my backpack, slinging it over my shoulder.

"I need to go," I say. Mr. Hughes is just smiling at me.

"It's not that big of a deal Alex. I'm expecting you to stay here and earn your grade," he says. My heart begins to race as he walks over and shuts the door. "I know how dirty you've been," he says quietly. He slowly walks up behind me. "I can see your thong straps every once in a while. I can only imagine the thoughts that are going through your head."

I am at a loss for words. I don't know what to say. I'm not sure if this is a good thing, or if it's turning out to be something very, very bad. Mr. Hughes clears his throat.

"Have you ever been with another man, Alex?" he asks me. I swallow hard and shake my head. "Well, what if I told you that I could see to it that you pass my class with an A?" I look up at Mr. Hughes. I notice the obvious bulge in his pants. For some reason, this excites me. It brings out the entire other side of me; the bad part of me. I smile slyly at him. He gets the hint.

"Get up, now," Mr. Hughes says. I obediently stand up and follow him into the storage room. He turns the dim light on and shuts the door behind us. Without warning, he unzips his pants and frees what is a massive cock. It has to be at least eight inches long, and very thick.

I stare at my first real cock in a mixture of lust and confusion.

"It's not going to suck itself Alex," Mr. Hughes whispers. I smile at him and get down on my knees.

Using what I've learned from practicing on my dildo, I slowly lick up the shaft of his cock, flicking my tongue against the head of it. My teacher begins to breath heavier. I can feel myself starting to grow hard. It's turning me on so much to know that I'm pleasing an older man, especially my teacher. I work my lips down over the head of his cock, licking up his pre-cum and swallowing it. I let some of my saliva slip out of my mouth and down to the base of his cock, and use it as a lube to jack him off with one of his hands.

I get about half of his dick into my mouth, and we're working up a rhythm of him thrusting his penis into my mouth and me jacking off the base of it. Mr. Hughes reaches down and pulls the straps of my thong up around my hips.

"You dirty little slut. I always thought you'd make a good little boy-whore," he moans. I look up at him and make eye contact, staring up at him innocently. I moan a little "mmm hmm," and continue my sucking.

"That's a good little bitch."

I'm rock hard now, stroking myself through my jeans. Mr. Hughes is pushing almost his entire cock into my throat. I gag a little, but struggle to breath through my nose and relax my throat muscles. I'm making it my mission to give him some of the best head he's ever had.

His hands are pulling at my hair, forcing my head into his mass of pubic hair as his balls slap against my chin. I'm gagging with every thrust he makes, struggling not to vomit.

"Oh fuck yes. Oh god," Mr. Hughes moans. Without warning, I suddenly feel something warm shoot down my throat. It causes me to gag really hard, but when I go to pull my head away, Mr. Hughes forces it back down onto his cock. More of his cum shoots down my throat. It tastes warm and salty-kind of stringy. I gag again, forcing some of it to shoot out the sides of my mouth and down my chin. I swallow what I can, but there's too much, and a little bit more of it dribbles down onto the floor. Mr. Hughes' breathing begins to slow, and he pulls his slick penis from my mouth with a slurping noise. I'm gasping for air.

Mr. Hughes reaches down with his finger and scoops up the cum from my face, shoving it into my mouth roughly. I swallow it diligently. He smiles and zips up his pants.

"Keep that up, and you just might get an A," he says. I smile up at him naughtily.

"Can we do it again sometime?" I ask him. Mr. Hughes' smile gets bigger.

"Of course we can Alex. Maybe we can arrange for a study night at my place this weekend," he says.

"That'd be awesome!" I say. I gather my backpack from the classroom and smile over my shoulder at him.

As I'm walking home, I can still taste the saltiness of the sperm in my mouth. I walk the rest of my way home pleased with myself. I just whored myself out for a better grade, and I love it.

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6 Comments
cheapdatecheapdateabout 4 years ago

Good, hot, story. But I feel the moneyshot (in both senses) is a little rushed.

AnonymousAnonymousover 12 years ago
Loved it

Very hot story. I loved every bit of it.

damballahdamballahover 15 years ago
Awesome!

Great start! Can't wait to read the next few chapters in the series..

AnonymousAnonymousalmost 16 years ago
Fantastic Start!!!

I love it! It's so hot. I'd love to have gotten started like that, Being a whore for an older man. Please write the next chapter soon!!! I'm aching to read about what kind of depravity lies in the next chapter!!

AnonymousAnonymousalmost 16 years ago
Hot as hell!!

You are gonna be a great little cumslut! Keep writing. Can't wait to hear what happens next. Would like to gag you with my cock.

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