tagTranssexuals & CrossdressersThe First Night Ch. 01

The First Night Ch. 01


He was excited...this was as scary as it was arousing. He was about to do something he had fantasized for years. He took a look into the mirror and studied his features; he may never see this again. His minded drifted a bit as he stared...going back to stealing his sisters panties as a boy, drooling over Victoria's Secret catalogs, dressing up in private all the years he was married. Also the day his divorce was final and he made the decision not to hide anymore. His wife had left him for another man, one who was more 'pleasing' and by that she meant rich. That day he started his transformation...tonight it would be complete. He had begun to run daily, dieting and working on his body. He had made himself very slender and he thought as he ran his hands over his body, very feminine. He felt his facial and body hair, probably for the last time. He smiled, and then blew himself a kiss good-bye. It was time to focus on tonight. He unzipped his jeans and let them drop to the floor. He turned and started the bath water...his 'date' wouldn't be here for a few hours, but he needed his time.

As he lowered himself into the tub, his cock was hard as a rock. He sat and soaked for a few moments, thinking tonight would be full of all sorts of new sensations. He slowly stroked himself imaging someone else's lips around it, someone else who was probably doing the same thing about now, only with the help of 'her' wife. He gently stroked himself and could help but cum right away...feeling more excitement and relief.

He had met his dates tonight online nearly a year ago. A married couple, a little younger that he was, with a man who wanted to be dressed and have sex with another man the same way, two slaves for his 20 year old wife. He imagined if she was teasing him. The thought brought a smile to his lips...tonight he would do a little teasing.

He softly hummed to himself as he began to shave, first his face, then legs and any other hair below his head. He had been growing out his hair there and it was quite long, he had also learned to style it.

As he got out of the bath he studied himself in the mirror once again. It was a full length and he could see his whole body. He was shaking with nerves. He was smooth as a baby's butt. He started to massage perfumed lotion all over; it was a mix of lilacs and jasmine. Once again his cock started to grow, this time he decided he better save it for later, for 'Sara'.

He moved from the bathroom to the bedroom, where today's shopping spree was laying on the bed where he had left it. He stared with the garter belt first, clasping it around his waist. Then sat down and grabbed the stockings. They were very sexy, black with a spider-web pattern and a wicked seam up the back. He rolled them up his legs, slowly, making sure they stayed smooth and straight. Oh god, his cock was throbbing. After hooking the garters to them, he walked over to the mirror. Mmmm. He was pleased. Long smooth legs wrapped in black, his 7-inch cock standing proudly. He couldn't help but picture Sara on her knees in front of him, slowly jerking and staring up with her deep green eyes. He had to jerk again, he stood there stroking in the mirror. One hand on his cock, the other alternating between his freshly shaven balls and his nipples, which were rock hard. Within moments, he came again...squirting all over the floor. Oh well, he thought, I will clean it later. He mind went back for a moment as he thought of how many times he had done that exact same thing with his sisters or a girlfriends panties through out high school...and tonight, it would finally be reality, not fantasy.

He went back to getting dressed. He slid his black silk and lace panties over his legs and pulled them in place. His cock was now soft enough to actually hide in them. They were bikinis; he preferred them to thongs or g-strings. The ass was made entirely of lace and this sent chills up his spine and down his thighs...he was now giddy with excitement! He pulled the negligee over his head and straightened the straps on his shoulders, this was also all silk and lace. Very sexy. He was starting to feel like a little slut! He then picked up his new little black dress. It was simple. More like a sundress but not see-though. It was thick enough to cover up his negligee, but was short enough you could just barely see the tops of his stockings...perfect! If he twirled back and fourth, it flared out and rubbed against his thighs. He was very pleased. He stepped up to the counter and pulled his hair back. Slowly and steadily he applied foundation, eyeliner, eye shadow, mascara and a hint of lipstick. He had practiced this forever and was very satisfied. He grabbed his blow dryer and brush and started to style his hair. It was dark brown, but it looked very nice with his blue eyes. He looked at himself in the mirror and smiled slyly. His hair was just above his shoulders and was now wavy and very flirty. "I would hit on me" he thought and giggled, making sure to try and keep it as girly as possible.

He examined himself in the mirror one more time. Just one more thing. He stepped back out into the bedroom and the last item was there on the bed. He sat down and put on his 3 inch heeled thigh boots and zipped them up. He stood, put in some small simple earring, and little heart pendant necklace and returned one last time to the mirror.

What he saw was better than he could've imagined a few hours ago. The image in the mirror was no longer the skinny unkempt man, but was now a slender, dark-haired woman that would make the pickiest of men consider her worth pursuing. The image in the mirror was different than the person looking into it. He was no longer himself...he had become "Lacey", the woman he always dreamed he could be.

"Her" heart jumped as the phone rang...she grabbed it and almost jumped for joy...her date was here. With a little spritz of perfume that complemented her outfit she stepped down the hallway to meet her date at the front door.

She opened the door to another amazing site. There was Sara, wearing a plaid skirt, knee boots, a while silk blouse that showed just of a touch of the black lace bra underneath and those deep green eyes shining over her smile...

Yes, it would be a good night....

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