Maddie

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He must do what he's told or not get laid.
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Dawns
Dawns
103 Followers

I was outside that bright sunny fall afternoon taking pictures. My desire to photograph people as well as scenery had brought me to the track. On a day like this there would always be someone there whether a pickup game of football or just a lone jogger.

An average size, fit looking girl dressed in T shirt and blue shorts and wearing Nike running shoes came walking from the track toward me when I snapped the picture. The camera aimed at her got her attention.

"Hi there," she said.

"Hi," I responded.

"Did you get a good picture?"

"I think so," I replied.

"I'd like to see it."

"It's digital. I would have to e-mail it."

"My name is Stephanie by the way."

"I'm Steve."

"Nice coincidence," she remarked giggling.

She stood five six, weight shifted slightly to her left leg, and light brown hair falling to the middle of her back.

"Yeah it is," I said.

"My eyes are up here."

Taking her message I looked up.

" They're blue."

"Right," she answered, "and remember that."

Taking the camera from me she looked at it as if examining all it's features.

"I just have a small one. It's one of those point and shoot types. I use it for family gatherings."

"I do everything. I like scenery, sports, wildlife."

It was in my hands again after a few seconds.

A month later

Cross dressing, homosexuality, or transsexualism were all the same to me. They were all repulsive behavior to see in public. The park seemed to attract all types, normal and not so normal.

"Look at those two."

"So what," responded my liberal minded girl friend.

"A couple of guys are holding hands."

"We're all different. Just except that. They're not hurting you or effecting your life."

My girlfriend is a fag hag I thought. She must know someone in the family or a has a friend who is gay. That's why she is the way she is.

"Yeah yeah," I replied.

"You're being way to judgmental."

I wanted her to not focus on me. I would find out later that she had other ideas.

The sex between us had been pleasurable and frequent. I would usually initiate it because I was always horny and she could always satisfy my needs.

The following day was like any other Sunday afternoon during the football season. Relaxed in the sofa in front of the television with a bowl of fresh popped popcorn, I tuned in to the game. Never a passive viewer, it was always my nature to be emotionally involved in the game.

"That's not a pass interference penalty Mr. Referee!"

I continued watching, and nibbling at my popcorn. At that moment, as the third quarter began, I opened one of two bottled beers that I would drink that day.

The time was coming up on six. Steph would have been out of work an hour ago I thought. The stores close at 5 on Sunday. She'll probably stop bye.

I never bulked up the way most guys do when they reach their mid twenties. At 25 I still way only 135 pounds with a 30 waist. I could fit into a boy's medium T shirt though it was a tight fit.

Just seconds before six I heard the door bell. Stephanie stood in the open door holding a shopping bag by the handle.

"Come in," I said.

At my kitchen table Steph drew packages from the bag. She opened the first, a girl's top. It was a black graphic dot print cinched front top with short sleeves.

"How do you like it?"

"It's nice. It's pretty."

"That's your birthday present."

I chuckled then shook my head.

"You're kidding."

"You'll wear this if you want sex."

Was this an ultimatum? She knows how I feel about queers. There's no way I would put that on me except as a joke.

Steph was not laughing or even grinning. Her gaze locked onto me as she held up the top. She was serious. I would not get sex unless I put on that top and other articles.

She pulled out the next item, a Calvin Klein push up bra. How far was she going with this?

"Take off your shirt."

I unbuttoned the blue plaid flannel shirt, removed it and tossed it on the sofa.

"And your T shirt," she added.

After pulling that off I tossed it on the sofa.

"You need a lesson on how to put on a brassiere."

I guess this is her idea of a joke. I'll play along.

"How does one put on this thing?"

She proceeded to explain. "Lean forward, and put your arms through the straps. I would put the cups around my breasts. You're going to put them around these."

She held up a pair of false breasts. "Put this on before you try to put on the bra."

I stared at them. They looked and felt very real in my hands.

"They're self adhesive so just put them on. They'll stick."

By now I was becoming enthusiastic. How would it feel to live, act and think as a girl? I attached them. With a slight pressure they adhered instantly to the skin as least as well as a bandage. I fingered the nipples.

"Stop playing with yourself." She giggled.

"Secure the band below your shoulder blades and don't make the shoulder straps too tight. You don't want them leaving an impression."

After a brief pause she added, "Just let gravity pull the boobs into place."

It went on after a little effort. Then the top proved to be a good fit on me.

She pulled another item, tore the wrapper and showed me matching slacks.

"They'll fit better over these."

Hip pads are a nice touch I thought.

"Stephanie what's the point of all this?"

"I think you make a very pretty girl so live in our world for a while."

I put on the pads, then the slacks.

"The world of makeup, buttons to the right, and hairspray," I answered.

"All that and more," she replied.

"Sexy," I said.

"You and I are going out tonight just as girls."

Sarah James, an easy going girl with a quirky personality, had known my girlfriend since junior high school. For twelve years the two had been best friends and confidants.

By seven the look was complete. I was dressed and wearing makeup that Stephanie had applied. A pair of jade earrings adorned my lobes. The whole outfit was beginning to feel more and more natural on me.

"Let's go Madeleine, Maddie," she said.

"I like that name." I didn't care how she chose it.

"I figured you would. And wear something warm. Tonight promises to be quite cold."

The ride in her 2006 Saturn with standard shift was made entertaining by her selection of music. Through the satellite radio blues played at moderate volume.

After a few minutes we pulled up along side a red brick building on a country road lined with trees swaying in the wind. As we walked towards the door the wintry air chilled me more than it had before. At least I had never felt it so acutely before.

Stephanie rang the door bell. We waited perhaps just less than a minute before the door opened. I had never met Sarah before.

I found her to be extremely attractive, more so than Stephanie. Short dark hair parted high on the left flattered her heart shaped face. Full lips, a straight nose and pretty brown eyes enhanced her beauty.

"Sarah this is Maddie."

"Hey girl," she said.

I never really minded a chick flick though I would not have gone out of my way to watch one. Suddenly the three of us were watching Lifetime television for women. I was captivated by the movie, a romance.

What's more I was beginning to feel quite comfortable listening to the girl talk. I even found myself adding to it.

My hair grew out quickly. I became conscious of how I was styling it. Something else was happening over which I had no control. The false breasts, and the pad in my hips had become real flesh. Suddenly before my eyes, while I showered on Monday morning, my penis dissolved into my lower pelvis and was replaced by an orifice surrounded by pinkish skin with multiple folds .

Oh my God I just developed a pussy! This was Stephanie's plan all along. I was stepping out from my shower in a whole new body. It had become soft and curvy and lighter. A bubble bath seemed so appealing now. I'll just fill the bathtub and sit inside it.

Madeleine had taken over and had started me on a new life. Now the only problem was employment. Just a weekend ago I worked construction for a living. That morning my search for a new job had begun. I had hoped it would not be long.

When I first began dating Stephanie I didn't know if the affair had legs. I had even sensed that she seemed distant when we were having sex. Suddenly I realized that a girl could and sometimes did fake an orgasm. She had faked them. Stephanie's words came back to mind as I pulled my only female top from the dresser.

"You'll wear it if you want sex."

Even my attitude had turned 180 degrees. I could defy straight people to make remarks. I'm a lesbian! Do you have a problem with that?

The wardrobe closet of my youth would be mine again but different. Looking inside I knew that my condition would be permanent. Girl's denim jeans, tops, back zipper slacks, skirts and button blouses hung on the bar from end to end. Below there were open toe 3 inch wedges and flats aligned on the low shelf. It's like I was never a boy I thought. None of these articles had been there when I left home.

While I sat watching my HD tv, the door bell rang upstairs from me.

"Maddie," shouted my mother, "your friend is here."

Stephanie entered the house and walked down the steps.

"Hi girlfriend," she said and sat next to me on the futon.

Our lips touched lightly.

"I've been home for a month, and I've been searching for a job for a month."

"Cheer up girl. You'll find something."

As the evening wore on the romantic feelings welled up inside both of us. We could no longer contain our emotions.

Stephanie leaned in again, pressing her lips onto my lips. I returned the kiss. Her hands moved lightly on my back and down over the curvature of my waist. A kiss on my neck was followed by another, then another.

Slowly she pulled my tunic up and over my head then she reached behind me to unfasten the bra and push the shoulder straps. It fell onto my lap. As her hands moved lightly over my breasts then cupped them the areolas enlarged. Her finger brushed up and down over the nipple. Lips pressed together and mouths opened. Our tongues probed deep and licked.

Lesbian sex rules I thought. I never want to revert back to being a boy. Stephanie Flowers pleasures me. With a technique that was well practiced my girlfriend pushed the strapon dildo into my pussy and slid it back and forth repeatedly. My soft moans grew louder as wave after wave of muscle contractions overwhelmed my body. My skin grew flush and my heart pounded. Love juices flowed within me.

Driven to exhaustion by multiple orgasms I lay limp on the sofa. Stephanie looked down at me.

"Awesome sex," she said softly.

She had never used such a word with Steven.

Recovered I took her hand in mine and gazed into her eyes.

Dawns
Dawns
103 Followers
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