The Beginning of Winter

When Winter met Rebecca he instantly fell in love. Her assertiveness, confidence, intelligence captured him more than her beauty. She wasn't a run way model, more girl next door. Yet he was very attracted to her. And firmly believed she was the most beautiful woman he had ever met.

Rebecca viewed Winter as a very shy individual who she thought had some true potential. She liked how he was always willing to try new things. And he wasn't hard on the eyes either. He was smart and he made her laugh, two things she valued more than appearances.

They had started dating and eventually moved into a house together. Like all new couples they spent a great deal of time with each other. Doing things mundane and exciting. They shared intimate details about themselves, their darkest fears and hopes for the future.

When it came to sexual fantasies they both kept an open mind and a promise that if ever the opportunity, they would seize the moment. They watched porn together to get ideas and even tried some of the acts the stars performed.

Rebecca was preparing for a night of continued sexual exploration by previewing some movies when she came across a video of a girl explaining how she feminized her husband. This intrigued Rebecca.

The idea of being with a girl was a fantasy she had always had. Especially after her once childhood friend and her had fondled each other one summer. She didn't think that Winter would agree to dressing up for her but decided to ask. He was always up to try new things.

Winter had never given any thought about being with other men. He didn't find them sexually attractive at all. But watching his girl Rebecca with another girl? That excited him. When she brought up the idea of him dressing as a girl for her he thought why not. Not like anyone will know.

Rebecca one Saturday afternoon set out some clothes for Winter to wear. He was currently in the shower and was shaving what little body hair he had. It was the middle of autumn so it's not like he would be wearing shorts anytime soon. She left the room to start making dinner for their date night in.

Winter was wondering if maybe shaving was going a bit far. He did it anyways because she asked. When he was done and dried off he walked into the bedroom to get dressed. His freshly shaved legs gave him a rush that was exhilarating. And when he pulled the silky panties Rebecca left for him up his legs he was immediately aroused. The jean miniskirt and white camisole were a little too tight to be comfortable. But he managed to get them on.

Rebecca was nervous. She hoped she didn't push Winter to hard about dressing like a girl for her. Sure she wanted to try having sex with a girl, but could she pretend he was one enough to satisfy her craving? She wasn't surprised that he agreed. He always did what she asked.

Winter is a little bigger in shape and size than Rebecca but he found that he could wear the clothes and shoes she left out easily enough. It was different walking in heels and he spent a few minutes practicing in the bedroom.

Walking into the bathroom to see how he looked he spotted Rebecca's make up bag. Not exactly sure what to do he decided that he would stay on the safe side and only use her mascara, eye liner and lip stick. Those are the items he saw her apply most often and felt confident he could do a decent job.

Rebecca had set the table, lit the candles, and touched up her make up. Dinner was almost done and she was beginning to wonder if Winter had decided to not get dressed up for her after all. When their bedroom door opened and she saw Winter her heart skipped a beat. He looked cute as a girl.

Winter stumbled a step and blushed a he approached her. Her pussy was already wet from the planning and her imagination. But she thought she could probably wring out a bucket full from how wet her panties are now. A couple steps away and Winter spun in a circle so Rebecca could see the entire outfit.

Winter liked the look of lust in her eyes when he got near her. His cock was so hard that it was almost painful. He drank in her eyes, the way her hair cascaded down over her shoulder. How her dress hugged her curves. It all made his dick throb. Each throb sending a tiny spurt of semen to leak out.

Rebecca was impressed at how well he applied the little makeup he was wearing. He has such nice skin, so smooth and without a blemish she thought to herself. One thing she always liked about him, he was never scruffy. She had to concentrate to keep her breathing slow. "You look fabulous, are you hungry?" she asked.

"So do you, but you always look great," Winter replied and took a seat. Rebecca went into the kitchen and brought out their meal while Winter poured the wine and as they ate they talked. Rebecca was getting more excited as time went by because she sensed that Winter was getting more comfortable.

After dinner they turned on the radio and danced in their living room. Winter had to sit down on the couch after a couple of songs. His feet weren't used to wearing heels and his calves were on fire. They laughed and started getting real intimate with their touches and kisses.

Winter finally couldn't take it anymore and knelt down on the floor between Rebecca's knees. He pulled her ass to the edge of the couch and buried his head between her legs. Her scent kicked up his desire and he pulled her panties to the side. He needed her like never before. Diving his tongue between her labia in search of her clit, he ran it up and down. Hungrily he licked and sucked her. The lipstick he was wearing smearing all over her inner thighs and his face.

Rebecca gasped when he started worshiping her. His tongue finding her clit and entrance with expertise. She was already so turned on that her climax didn't take long to overpower her senses and make her legs tremble. The bliss his long tongue was providing her with kept her orgasm going. One minute, two minutes, three minutes. She couldn't take anymore, she had to push his face away from her overly sensitive and dripping wet sex.

Winter was so charged with need that when she pushed him away he fought to go back down. She resisted his effort and instead she lifted up the skirt he was wearing and pulled him into her. His cock had already forced its way out of the panties and was drawn directly to her pussy like a moth to flame.

Rebecca moaned when he entered her. She wrapped her arms and legs around him keeping him stationary. She needed a second but his cock sent her into another orgasm when she felt it throb inside of her and his hot seed filling her.

Winters body stiffened and he let out a loud moan. He had never been so turned on that the second he entered her he was cumming. This orgasm was the most intense he had ever had. What also surprised him was he was still rock hard, no where near satiated. He needed her, craved her with what felt like undying intensity.

Rebecca felt the last throb of his cock inside of her and was finally on the tail end of one of the most explosive set of orgasms she had to this point of time ever experienced. As she relaxed her grip a little the sensation of his rock hard cock slipping from her made her moan. Reaching down to his ass with both hands she pulled him back into her.

Winter rested his forehead against hers looking her in the eye. His lips parted as she pulled him in tight against her. Slowly he began to move his hips and stuck his tongue between her lips. Putting more pressure to her lips with his, desire deepening his kiss. Her returned kiss flamed his passion from a feeble flickering flame to a bonfire. Faster and faster he moved his hips thrusting his rod in as far as he could.

Rebecca lost herself in his deep brown eyes, the feel of his lips, his dancing tongue and his long thick cock deep inside of her. Tiny whimpers of pleasure vibrate her lips. Each thrust of his cock inside of her burning the fuse of her climax. The fuse was already short and would only take one thing to set her over the precipice.

Beads of sweat popped out on winter's forehead from the exertion of his control. He didn't want to cum yet. Wanted this moment to last eternity. At this moment he was one with her. But he was walking a razors edge and knew that he was about to slip.

"Oh god Winter, cum in me now," Rebecca cried out. She needed, demanded release. Her climax burst and she wrapped her whole being around him as she felt his load fill her.

His breath caught in his throat as his body contracted using every last muscle in his body to ejaculate inside of her. Winter groaned when he was finally able to expel his breath. Shuddering as he took in a needed lung full. Searching for her lips he kissed her deeply holding tight to her body.

Rebecca kissed him all over his face before her lips met his. She loved these moments. And soaked in the heat he radiated. "Wow, we didn't even get our clothes off," she said after taking deep refreshing breaths and giggled.