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My Oddesy 1 - Glen (here and gone)

A (mostly) true story of my first time dressing for another
"But mum. I'm too sick to go to school."

I give my best fake cough. It was late senior year and I had been busting my balls for months. I just want a day at home alone. She finally replies after a minute of withering glares.

"Fine. I'll call the school. But you're seeing a doctor Monday if this persists. I'll be back around five."

"Sure. Whatever."

I lay perfectly still until the sound of my mums car fades away. Then I throw back the covers and run down the stairs to the front door. The deadbolt slams shut and I literally skip back up to my room. Once I'm there I peel off the false trappings of masculinity.

I stand naked in front of a mirror. I wouldn't say I was fit. But I wasn't really fat either. The best descriptor would be slim. I must stand there for about half an hour, depression rising.

"This isn't me. It just isn't."

My eyes start to mist as I take a final look at masculine me. A sheet from my bed soon obscures it. I pad into the hallway. My hand scrambles across the top of the door until my slender fingers stumble into the key for my sisters room.

She had left for University last year but her room just sat there. Not a single thing had been touched. Except by me. It had become my playground.

A smile blossoms across my face as tumblers slide out of the way. The door swings open to reveal a world of feminine pleasure. Lace, pink, satin, chiffon. My face just lights up.

The first thing I do is crack open her cupboard. Clothing basically springs out at me. My sister had never been the most organized. The first thing I pluck out is a pair of plain black cotton panties. I rub my fingers together, feeling the fabric.

"Not sexy enough," I mutter to myself.

I dig further in and pull out a silky pink thong edged in lace.

"Much better."

I slide then gingerly up my legs and slip the back between my butt cheeks. My fingertips gently maneuver my balls back into my body. The lace nestles gently against the front of my stomach and hides my package quite well. My hand ventures back into the mound, groping blindly for a bra.

When it finally emerges I am grasping one of my sisters favourite bras. A purple push-up, padded, maximiser bra. In silk. A squeak of joy emerges from my lips. I quickly clip it on and stuff the c-cups with spare panties.

"And what to wear over this?" I muse to myself. "Stockings for a start."

I delve into the treasure trove of my sisters clothes and emerge with my prize. The smooth nylon creeps up my legs and the lace top stops smack in the middle of my thighs. I'm still spinning in a circle, trying to get a better look at the back of my legs, when the doorbell rings.

I jump into the air and scramble to the window. I crack the curtains and peer out hesitantly. An audible sigh of relief, its just the delivery guy. But I'm still dressed as a girl.

My mind races. I'll never get changed in time. My mum had given Glen, our delivery guy, a spare key for if she's not home. He'll be inside in seconds! Thinking quickly I snatch a thick woolen robe from my room on my way downstairs.

I just finish tying on the robe as the front door opens. A messy mop of red hair hovers in above a cardboard box.

"Hey Glen. What's in the box?" I pipe cheerfully. Glen always puts me in a good mood.

"Just some trinkets your mum bought online. And anyway what are you doing home? Ain't this a schoolday?"

"Yeah. It is. I'm sick."

"She fell for that."


Glen takes a long time answering and I notice him looking at my chest. I'd forgotten I still had c-cup tits. I cross my arms over them and cough pointedly.

Glen startles and begins to turn put the box down. As he bends I get a great view of his ass. I had always admired Glen. But I don't think he'd very much noticed me.

"Just sign here," He says as he hands over a clipboard. He looks down awkwardly as I scrawl a quick signature.

"Thanks for that. I'll be seeing you, sweetie." Glen's last comment makes little sense to me until he leaves the house and I realise he had been looking right at my stockinged feet.

I slowly untie my robe and drop it to the ground. I twirl slowly and whisper quietly to myself, "He likes me." I am so enraptured by this revelation that I don't notice the door opening again.

"Dang girl. Not bad."

I bend over quickly to snatch up my robe without thinking.

"And that is better. Mmmm."

A hand glides across my ass. I freeze in place.

"Turn around sweetie."

I slowly turn to face Glen. I knew it would be him. As I turn to face that adorably messy red hair his lips meet mine in a firm kiss. I swoon as his arms encircle my waist. As he pulls me in closer I feel the size of his package press against mine.

His hands fondle my bare butt cheeks as we kiss. Glen finally breaks for air and I almost launch myself back at him. He holds me back by my shoulders and whispers ever so gently.

"I've always wanted to do that. I just never thought you would look like this when I did. But don't change a thing."

He dives back in and jams his tongue down my throat. I return the favor. My fingers fumble on his belt clasp. I rip his belt from his pants with a flourish.

My hand ventures into his cotton boxers and closes around a thick rod of meat. Glen moans into my mouth as my hand squeezes. I free it from it's cotton confines and stare openly at it.

Glen runs his thumb along my jawline as I stop kissing. My knees slowly bend and I end up face to face with seven-and-a-half inches of man-meat. It bobs gently up and down in front of me.

I ever so gently wrap my hands around its base and kiss the head. My tongue snakes out to caress the sensitive skin under the head before slithering across the swollen bell end. Glen moans sweetly somewhere above me but my world had shrunk to just me and his throbbing member.

I slide forwards, lips gliding further down that delectable sausage. Being my first cock I only manage to get about four inches in before it bumps against the back of my throat. I gag lightly but begin to slurp vigorously. His rock-hard cock slides in and out my mouth on its own accord.

Glen is face-fucking me.

His hands entangle into my messy hair and pull me in closer. With my knees rubbing on the carpet and my hands now braced against his hips I am helpless. His speed increases and I relax my jaw further.

With each thrust he gets further in until my nose is pressed into his curly red pubic hair. We're both breathing heavily now and my dick strains to free itself from my thong.

"Baby. I'm cumming. Ohh man am I cumming!"

I pull back slightly at Glens proclamation. All this achieves is that his thick, gooey, tasty, wonderful cum starts flooding over my tongue. I swallow instinctively. Spurt after spurt flow forth until it tops my mouth up and sneaks past Glens penis, still lodged in my mouth.

Spent, he stumbles backwards. My mouth snaps shut and I swirl the cum with my tongue. I swallow with a sigh. I finally look up to see Glen running his hands through his thick hair.

"I can't do this. I can't. Never again."

I immediately rise to my feet and rush towards my crush. His hands fly upwards protectively.

"This can never happen again. It may have been great. But never again!"

Glen angrily storms out of the house, slamming the door, and leaving me dumbfounded.

I would see Glen again. But always at a distance. The next package I got was delivered by an overweight guy in his late 60's. Glen had swapped routes to avoid me
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