Nap Time

Gary clicked off the phone and rubbed his eyes. Glancing at the clock, he groaned. 10:14pm. Another 14 hour work day trying to bring the Northeast Division back to profitability. He’d been at it for three months and success looked likely, but it had been a great struggle.

He leaned back in the leather chair in his home office. He was stressed out but the last thing he wanted to do was go to bed. Drop off to sleep and wake up to head into the office again. He needed a distraction and a way to relax.

Going through these thoughts was a silly game, actually. He knew exactly what he needed and he knew he would get it this evening. He picked up the phone handset and touched his speed-dial.

“Well, good evening, Gary,” answered the sweet feminine voice on the other end. “It has been awhile since you’ve visited us. Will you be coming tonight?”

A slight pause as he decided to commit himself, then “Yes, yes, I will.”

“Wonderful. We’ll be ready for you.”

He hung up the phone and sat there. After a few moments, he stood and placed his iPhone on the desk along with his personal cellphone. He stepped to the bureau and unlocked the drawer. After withdrawing five one hundred dollar bills, he locked it up again.

With no further delay, he left his house, climbed into his Mercedes and made the twenty minute drive to the sprawling Victorian mansion in the exclusive King Street neighborhood. The drive was lit as well as the front of the home and its circular park.

The Mercedes ground to a stop on the gravel. He was beginning to feel nervous but with happy anticipation. Leaving his car locked, he walked up to the door.

Passing through yet another mental barrier, he rang the bell. After almost no wait, the door swung back and he was greeted by Maria. She was dressed in a frilly maid’s outfit with sheer stockings, 5″ high heels, and suggestive makeup. He gave her a warm smile and a kiss as she welcomed him inside.

Maria was very special, a former client of the home who had become a fixture. She and Gary had talked before and he knew that she had once been just like him: a high-powered executive who came to this house to relax. Maria had once been Mark but had been feminized enough to live as a woman.

“Welcome, Gary,” said Miss Belle with a smile, stepping into the front hall. She was wearing a dress that looked like it came from the fifties: a blue sheath dres with white dots, heavily starched and accented with a string of pearls.

Gary felt relief wash over him with just the sight of her. He gave Maria’s hand a squeeze and then followed Miss Belle upstairs. He didn’t say anything. He was already assuming his role.

They entered a room that looked like a small, but nice hotel room. There was a door to a bathroom that Miss Belle disappeared through. The effect was subtle, but if you looked hard, you’d realize the room and the bathroom were retro, like they were built in the 1960s.

Gary proceeded to undress, leaving his clothes folded neatly on the bed. When he was finally naked, he padded quietly into the bathroom. The air was warm and misty and he could hear the bathtub filling with water. Miss Belle was sitting on the closed toilet by the bathtub, testing the heat of the water.

“It’s ready. Get in, honey,” she said softly. Gary obliged, stepping in carefully and then sliding into the hot water. He sighed, feeling the heat seep into him, relaxing his muscles.

“Doesn’t that feel good, sweetie?” cooed Miss Belle as she took a bar of soap and lathered up a wash cloth. “We’ll get you all cleaned up and ready for bed.”

Gary reclined in the tub as she began to bathe him, working the washcloth up and down his legs and his arms. She worked slowly and sensuously so that when her washcloth reached his groin, he was fully erect. She washed it and moved on, cleaning his bottom and his torso.

“Let Mama take care of that for Baby,” she said softly, wrapping her hand around his penis and stroking him until he sighed and cum leapt out again and again. She continued to manipulate him until there was no more, and then cleaned him up with the wash cloth.

“Stand up, Baby,” she said, standing herself. He obeyed and enjoyed the feel of her hands toweling his body off. She helped him step out of the tub and finished toweling him.

Walking over to the mirror, she picked up several pink hair clips and gathered his hair into ponytails. He stood there happily receiving all of her attentions.

Once his hair was properly babied, they left the bathroom through a second door and entered the nursery. The whole room was pink, with designs of unicorns, flowers, fairies, and angels over the wall. The room was dominated by a large bed with pink frilly comforter and crib walls that could be raised. Gary saw stuffed animals in the bed, rabbits and ducks.

He stood by the bed waiting for her next instruction. Miss Belle’s heels clicked over to a diaper changing table where she picked up several things.

“Lay down in bed, Baby,” she said sweetly and Gary obeyed, enjoying the soft crinkle the plastic-covered mattress made under the pink sheets. He laid on his back. Miss Belle moved to his side.

“Baby had a long day, playing with her friends, going in the stroller. Time for a nap for you, Baby,” she said softly as her hands massaged Gary’s bottom, legs, and groin. He was already getting stiff again.

The smell of baby powder filled the air and he moaned slightly with pleasure. She massaged the powder into his bottom and groin. He squirmed a little.

Next he felt cool jelly massaging his bottoms hole.

“Just relax, Baby, so I can put in your pacifier…” Her finger kept massaging his bottom and then it slid inside. She pumped it in and out, lubing him up. Then he felt something larger than a finger pushing to slip into him. He moaned in pleasure now, his penis throbbing, and slowly he accepted it. It got wider as it went in until it suddenly got narrow. His bottom happily clenched around the narrow part, lodging the butt plug inside himself. Now every squirm was even more pleasurable.

He heard the crinkle of a diaper and sighed happily. She spread his legs and he helped by lifting his hips. The plastic wrapped around his waist and she taped it shut neatly. His erection was completely contained and he was feeling even more aroused.

“Sit up for your night-dress, Sissy,” she said happily. He complied and she pulled a frill-edged satin sissy dress over his head, “helping” his arms through the puffy-shouldered short sleeves. It barely reached his waist, but he loved it.

Next she pulled out a pair of ruffled pink panties. Again, she helped his feet through the openings and pulled it up snug around his hips. These were followed by satin booties, tied on with a lace around his ankles.

“Don’t want you doing naughty things,” she teased as she slipped fingerless satin gloves on his hands, again tying them on with a lace around each wrist. He moaned louder now in the pleasure of all the sensations.

“Hush now,” said Miss Belle, taking a big pacifier and teasing his lips with it. “Does Sissy want her pacifier?” Gary nodded with a grin. She kept teasing his lips even as he tried to capture the plastic in his mouth. Finally, she popped it in and tied it there with a ribbon around his head. He immediately began to suck it.

Next, a satin baby bonnet appeared, cradling his head softly. The sissification was so intense for him that he felt himself straining for release again, pushing against the diaper and panties.

Miss Belle began to sing a wordless lullaby and the lights in the room dimmed. She caressed his body with her soft hands, all around and then rubbed his panties. He sighed and moaned around his pacifier. His bottom trembled around the delicious butt plug.

“Let yourself go, Baby,” she said softly, stroking him through the panties.

He moaned louder and felt his pleasure build and build. Finally, in her loving grip he released again, filling his diapers in wet warmth.

“Good, Baby,” she praised, patting his panties as he softened. She turned on a music box and left the room quietly.

And Gary slept peacefully.