A Night with Sir

Rich was walking through from the music rehearsal room through the house to go back to his room when he passed Mark, his personal assistant.

"A package came for you, I put it on your bed," Mark told him in the hall.

Rich just finished with his vocal lessons for the day. That was all he had on his itinerary. Rick was away, having been gone for five days, which was nice in a way to have some down time to himself, but he was used to the man's presence, especially at night. But this did give him a chance to wear what he liked, like today, he wore his favorite oversized jeans, boots and tight t-shirt.

"Do you know when Rick is due back?" Rich asked. He knew it was today or tomorrow.

"No, I'll ask Brianna when I see her."

"Anything else I'm supposed be doing today?" Rich just wanted to make sure the rest of the day was his, which would probably be spent in front of the game system. He had gotten some new games and hadn't had a chance to play any of them yet.

"The rest of the day is yours," Mark announced.

"Good. See ya later."

He had been up since seven, getting with his trainer for exercising then dance coach. After taking a shower, he had breakfast and met up with his singing coach in the music room. Routine items now a days for him.

Going up to his room, Rich flopped down on the bed and saw a nice box on it from a retail store that he normally saw given to woman. Opening it he found a note then tissue paper.

Missed you Babe. I should be home tonight around eight. Please have this on when I come home. I'll be looking forward to seeing you in it. Hope you been missing me as much as I've been missing you.

Love R. xox

Putting the note aside, Rich opened the box to find several items of red lace. A bra, garter belt, g-string, petticoat and sheer hose.

Over time Rick had dressed him in women's clothing. He liked his young, fem looks and dressed him at times to look like a woman. He now shaved his legs on a regular basis to have a smooth look along with his groin. They had laser surgery done on his arms so he was now hairless in the arm pits.

Rolling to lay back on his bed, Rich couldn't help but put a palm to his now full cock. He never thought he would be like this, wanting sex at a drop of a hat. When Rick was home he would have him at least twice a day. Asking him to his office for a suck, or a morning wake up cuddle with Rick taking him. Rick even liked taking his cock in his mouth and sucking him to total orgasm. He was learning that sex is not something for behind doors but an open affair. The house was aware of what Rick liked and no one batted an eye if Rick wanted Rich.

Opening up his jeans, he pulled out his hard aching cock, not bothering with underwear since he was home, he started stroking his cock thinking about how he would be dressed up in all that lingerie waiting for Rick to come home. Rick was taking his curious thoughts, fantasies and pleasures and expanding on them each chance he got. He was almost in perpetual hardness because the man was at him whenever he could.

Little did he know that his activities in his room was taped from several angles and that the security was told to show all sexual activities and naked times of the "current boy/girl toy" to be saved for Rick's own reviewing.

Rich stroke his cock to completion, his spunk all over the front of this shirt. Rich pulled up the shirt and threw it in the direction of his dirty laundry basket. The maid would pick it up in the morning with the rest of things that made it somewhere towards the basket. Laying back again on this bed, cock hanging out of his jeans with no shirt on, Rich wondered what he was going to do to make Rick get a quick boner.

** **

After pondering what he was going to do, Rich sat up. He would play one of his new games on the XBOX then have an early dinner and start getting ready. Moving to sit on the edge of the bed, Rich took off his boots and threw them to the side. Taking off his pants he dropped them in the basket as he went into the closet to find a pair of shorts and loose fitting t-shirt. Finding his cell phone with its pager system, he paged Mark letting him know he would like to have his dinner in his room at six. He figured it would take him an hour to get ready for Rick and be in his room in time for his arrival.

Settling on the couch, Rich started into playing his game, losing track of time while he enjoyed his afternoon.

Mark walked in with a covered tray. He enjoyed working for Rich, he was an easy person to work for. He hoped that Rick would keep him for some time. Walking into the room, he wasn't surprised to see the slight mess here and there he created. Rich did seem to appreciate that he had people that worked for Rick to do some things. He wasn't anal like some always accusing people of taking things when it was their own stupidity of misplacing items. Rich seemed to be a young typical male.

Looking up from his game's action, Rich smiled. "It's six already?"

Mark put the tray down on the table before Rich and smiled. "Take it the game is good."

"Decent, could probably ace it in a few days if I didn't have practice every day."

"And we both know, you can't skip those."

"Especially if Big Daddy is back in the house." Rich had several nicknames for Rick. With the personal relationship between them, Rich was fond of the man. He was taking him down a life he only dreamed about and indulged him much of the time.

Moving to see what Mark had brought him to eat, Rich was surprised by the steak and potatoes that graced his plate. "Nice," he commented as he started to cut into his meat.

"I'll leave you be," Mark said standing. "Any special plans tonight?"

Rich pointed over to the open box on his bed. "Rick sent me a package to greet him with." Mark knew of Rick's whims and wouldn't be surprised what he would see in the box.

Mark did look in the box and gave a whistle. "Hot to trot."

Rich laughed. "He does have an affinity for red."

"Remember to take a selfie."

"Always do. I might even like this look." Rich was understanding more about himself with each encounter. He might act like your typical young man, he did have his own desires beyond that. In this case Cross dressing, or using his fem looks to make Rick a happy man. Rick was bi as he was, but he liked playing with his partners.

Rich knew he looked all of fifteen though he was nineteen when he met Rick. But he already had fem tendencies and Rick just showed him the rest of the way. He still could look like a boy when he wanted, but if he took the time, he did transform to more.

** ** At seven, Rich headed for the shower. Stripping down to nothing, he stepped into the large shower and started to wash. Again the thought of the night before him, his cock grew hard, hanging heavy away from his body. Taking himself in hand, he stroked himself to a quick climax. He knew it wasn't about himself coming off later for Rick, he was dressing and being there for Rick. Rick had been away from home for over five days, and spending time with Julia, which he could image was not fun. She was an older actress that was still under Rick's company. From what Rich could tell, she was stuck up and a big pain for Rick to manage. Even though Rick was probably having her in his bed on the trip, he knew Rick would come back to him.

Rich wanted to please Rick and be there for him to unwind. He had learned over time it wasn't always about him. He knew Rick would make it up to him later and he was good with that. Shooting his third wad of the day, for he took care of his morning hard on in the same shower just that morning, he would be good for now. Drying himself off with a large towel from the towel warmer, he draped one around his hips as he went to fix his hair for the evening.

Cut in short drifts, brushing his hair as he dried it with the blow dryer, letting it settle in different directions, but settling as he wished. Leaving the bathroom, he walked into his closet and opened a draw that held some of his sexual bondage and enhancement items. He didn't want to come too soon for Rick tonight, he looked through a draw that held cock rings and ball stretchers. Since he was wearing a lacy pouch, he found a red leather cock ring and ball stretcher. Rich wrapped the leather strap around the base of his cock and then wrapped around the base of his testicles. That would hold him till either Rick made him really need to cum or if he was released by Rick. As he thought before, this wasn't about him.

Rich closed that drawer and moved onto the jewelry drawers. Slowly he was gaining new pieces for his collection, gifts from Rick as well as making purchases of his own for his four areas of adornment. Changing out his studs in his ears, he picked up his ruby studs. Then he changed out the bars that were in his nipples to gold captive closure rings that Rick loved on him when he was in a mood to play. Looking down he changed out the plain gold bar bell for his navel, replacing it with one that had a ruby on the end. Rich then changed out the curved bar bell on his Prince Albert, that to would have a gold bar bell ending with a red ruby too.

Walking around the closet, Rich picked up his black silk kimono robe, a present from Rick when he returned from Tokyo, drawing it around his lithe body and tying the sash. He moved to the next to his make-up stand. Sitting down on the padded bench seat, he turned on the lights that circled the mirror and looked at himself. How two years had brought much difference for him. Learning to take care of himself, and know more about himself and allow him to explore all he was. Though he sang, modeled, and acted sometimes and was in front of crowds, it was the intimate moments with others that he found the most enjoyable.

Pulling out his foundation and brush, Rich brushed the powder over his face. One of the first things he learned under Rick's tutelage, was to get the right look. Learning about makeup, what to apply and how. Creating the look was the first rule. Finding the blush, he dabbed a light color on, shifting the look of his cheeks. Finding his eye liner, Rich boldly worked on his eyes to give them the bold look Rick liked. Finding a light color of eye shadow he colored his eyes with practice. The last item was lipstick. Picking up his red smudge proof lipstick, Rich applied the color that he knew Rick loved on him.

Rich opened a draw and pulled out a kit of press on nails of different colors. He pulled out the case that had red in it and worked on getting his nails covered by the red plastic.

Looking in the mirror for a moment, Rich admired his work on transforming himself into what felt like a different person to him. Sometime he wondered if he should gave this persona a name other than Rich, but deep down it was him. It wasn't that he had totally become a woman for he still had his cock and he used it and felt it when he was dressed in such clothing. He never lost that part of him. But the look, he would be happy to see Rick. But he would be on his back taking the man in to him and loving him all the more for it.

Standing up, Rich thought what else he would need for the evening. Going back to his drawers of sexual items, he pulled out a red leather collar and two red leather wrist bands. Opening another drawer, he found a medium sized vibrating butt plug, its transmitter and lube. Rick liked to have him ready especially on nights like this, but playing with him too. Then Rich went to find a short chain that he would run from his nipple rings. It gave a good look to hang from them and also came in practice as they made love to be pulled, pulling his nipples, which was always a quick turn on.

On his way out to his bedroom, he picked up his red heeled shoes. It would add to the final look.

Walking into his bedroom Rich dropped his items off on his bed next to the open box. Pulling the items out Rich started dressing. Taking off his robe, he laid it on the bed. Pulling the lacy see through bra from the pile, it had open slits to allow access to his nipples, it was a straight line bra that was perfect for his slight formed pecs. Rich added the chain to the nipple rings. Next was putting on the garter belt, he sat on the edge of the bed and drew up one red sheer hose over his hairless leg then the next, securing them to the garter. Moving a bit, he picked up the butt plug he had brought with him and smeared lube over it. He was now practiced enough to easily find his hole and slip it into place. Each movement of bending or walking would be felt against his pleasure spot. Pulling the thong on, it would run against the plug and held is cock snuggly straight against his body but the head was above the pouch, peeking out with the jeweled head.

Pulling on the red sheer petticoat up around his waist and letting it fall over his hips, he looked at himself in the mirror. Seeing his peaking cock head through the sheer material of the skirt. Slipping into the shoes, which added a few inches to his height, he went to stand in front of the full mirror to admire the look he created.

Rich turned to look to see where his phone was. Picking it up, Rich returned to the mirror to make a selfie pic of himself. Over the months he had dressed in different outfits and always took a picture of himself. He was thinking for Christmas he would make a calendar for Rick.

Rich picked up his collar that was held in place by Velcro. It was more show than anything. It held a tag to the front D-ring stating "Your Slut." Then buckled the red leather wrist bands in place. Sometimes it helped to secure his arms, adding to the submissiveness to Rick. He never knew what do with his hands anyway, especially when it was Rick in control.

Looking at the time it was almost eight. Pulling on his robe, Rich found his I-pod with ear buds, the remote to the vibrator and a hand held game console to play while he waited. Rich walked down to the Rick's bedroom. It was the next room down from his. Going into the room, Rich turned the lights on in different places to give soft lighting. Moving a soft chair around to face the pole, he knew that there would some type of show to show off what Rick had given his lover to wear.

Deciding to make himself comfortable for his wait, Rich moved to lie on his stomach on the bed, his ankles crossed in the air. Putting on his ear buds, Rich started playing his game and listening to his music to tick the time away.

** It was half past eight when Rick finally got in the door of his mansion. Still dressed in his grey suit. He was ready to tear the tie off in frustration of how the evening had went so far. The rain of the evening had made the roads clogged with people who had no idea how to drive in such conditions. He was glad to finally be home. Julia was on a shoot with Cindy in Rome. She was one of his more mature clients and though he had enjoyed her, she was now finding a relationship of her own. The movie was going to be a good mark on her resume. But he was ready to be home, ready to spend some time with his latest lover.

Walking up the stairs and down the hall to his bedroom, he opened the door and found Rich lying on his bed. The last few hours of travel seemed to disappear as he saw the red lace surround his lover.

Rich didn't notice Rick enter the room, his attention drawn to the game and his ears filled with music. He gave a start when he felt a cool hand touch his bare ass. Looking around his shoulder he saw Rick. Pulling out his ear buds, he turned off his I-Pod and game console and rolled on to his side. "You're home," he commented, smiling up at Rick.

"Yes, I'm home and I see you got my package." Rick leaned forward to give Rich a long, deep kiss. He had missed Rich. Rich was above the others the most submissive and trusting lover. Pulling away, Rick smiled down at the young man.

"Come on, I want to see it on you," he stepped away and found that Rich had already placed a chair for him. Going to sit, he was already getting hard thinking for watching Rich in his newest outfit.

Rich rolled off the bed and made sure the petticoat was down and walked over to the pole. He stood so the pole was behind his back, holding him straight. Making his legs spread apart, he stood to let Rick take in the sight of him.

Rick moved from Rich's face, which was made up to look delicate with red lips. He looked very much a boy but he had such features that Rick loved showing him off. Moving down to see the collar, the tag hanging saying "Your Slut," he had to smile. Yes, Rich was wanting and he liked that in him. Moving down to see the sheer bra drawn over his chest, the chain lay hanging from his nipple rings, he would use it in teasing the young man. Going down to see the red petticoat hang from Rich's hips, covering the garter and the head of Rich's cock that was held out of his G-string. The red hose running down his smooth legs into the red heeled shoes.

"Raise the skirt for him, let me see you," Rick told Rich. "Let me see that gorgeous cock of yours."

Rich reached down with one hand and pulled the skirt up to reveal his hard cock held against his body by the base of the G-string. Reaching to hold the bar behind his head by his free hand. He gave a pose to Rick.

"Such a slut," Rick remarked.

"I'm your slut," Rich replied.

"Any other surprises you have for me?" Rick asked.

"Maybe," Rich answered coyly.

"Come here," Rick ordered.

Rich moved slowly towards him, giving a little swagger to his step till he stood before Rick.

"Turn around."

Rich turned as ordered.

Rick looked through the petticoat and saw the G-string running up through Rich's ass crack and saw the butt plug.

"Where's the controller?" he asked.

"On the bed stand."

"Bring it here."

Rich walked over to bed and the table and picked up the small controller to the vibrating butt plug. It had several settings to it so he could be feeling it to the max if Rick was in a mood to see him squirm.

He returned and handed it to Rick. Rick again pulled him down to kiss, this time pulling the chain that in turned pulled on Rich's nipples.

"Go back to the pole and stand with your front to it, your side to me. I want to see you hump that pole while I watch you."

Rick watched as Rich moved to as he was told, his legs apart and his body leaning against the cool metal pole so there was friction between his cock, skirt and pole. Rich reached up to hold the pole. Turning on the vibrator, he started out slowly to see Rich move against the pole suggestively.

"How many times did you come today?" he asked as he watched Rich move against the pole, moving with his hips to caress himself against the smooth metal.

"Three times," he answered as he felt the sensation within him and as he moved against the pole as if dancing with it.

"When?" Rick asked turning up the speed a notch.

Rich's breath hitched when the speed increased. "Shower ... this morning," he started out. "On my bed when I saw what you ... sent me," Rich put more effort against the pole. He was making big dips against the pole. "And in the shower, before getting ready for you tonight."

Rick reach down to his own cock, running his hand over himself through his trousers. He wouldn't last long, but he had time to enjoy the young man for the evening. Unzipping his pants, he pulled his cock out and started stroking it.

Watching Rich dance against the pole, Rick knew he wouldn't last too long either.

Leaving the vibrator to medium he called to have Rich return to him. Rich walked slowly back a bit of stagger as he felt the vibrator move within in. "Kneel before me hon," he said with his master's voice in place.

Rich dropped to his knees and automatically pulled his hands behind his back per his training. "Very good. I seem to be in need of your assistance. Wrap those lovely lips around my cock." He watched as Rich walked on his knees towards him, without moving his hands forward. As he came close to Rick, he leaned over and took half of his cock into his mouth.