Christy's Fantasy Come True Ch. 07

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Christy dresses up Tony.
8.5k words
4.67
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Part 7 of the 10 part series

Updated 10/22/2022
Created 04/24/2005
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Christy could not believe what had just happened. Her day started out like normal until she met with a new client for lunch. It turned out to be Tony, her neighbor. She confessed to him her secret and arranged for a meeting the net night. Then she met with Sheri, Tony's husband and found out that she did had an idea of what was going on but didn't know the whole truth until Christy told her. Now they both knew Christy secret. Jim wasn't going to believe this. To top it off she ended up having sex with Sheri.

Sheri went home to clean up before Tony got back from work and Christy set about straightening things up for tomorrow night. She needed to get out her old wireless security systems and set it up in the office to capture her and Tony's session while Sheri watched in the other room unbeknownst to Tony. She wanted to get it all on tape.

It took the rest of the afternoon but she was able to get everything set up in the office. Three cameras, at different positions, somewhat hidden to capture the action in addition to the digital camera and video recorder. Looking at the clock she realized Jim would be over soon after gettgin off work. She rushed upstairs and took a shower, shaving and cleaning herself up for him. She was hot and horny and wanted to play tonight.

As she was finishing up in the shower Chrsity heard the front door open.

"Christy? Are you home?"

It was Jim.

"I'm up here honey, in the bedroom."

She heard Jim climbing the stairs, as she got dressed. When she had finished slipping on her tee shirt Jim was at the door.

"So how was your day off?" Jim asked.

"You won't believe what happened." Christy gushed.

"What? Did you have a bad day? Something not go right?" He quizzed her.

"Not exactly."

Jim gave her a puzzled look.

"I don't usually take appointments today but I got a call, and the voice on the other end sounded familiar. Giving in to curiosity I set up a meeting at my usual place. When I got there you'll never guess who was waiting for me."

Who?"

"Tony!"

You're, kidding Right?" Jim exclaimed. He couldn't believe it. He always thought Tony was a straight shooter.

"No I'm not! I didn't believe it myself." Christy filled Jim in on the conversation she had with Tony, telling her about his love of lingerie and his fantasies and revealing that she was actually her neighbor Chris.

"And how did he take that news?"

"Pretty well. He didn't believe it at first but he came around. Since you have poker night tomorrow night I set up and appointment for then."

"Why then?" Jim asked.

"Sheri doesn't know, or at least didn't know, about Tony's little fetish."

Jim gave her a questioning look. "What do you mean, didn't know?"

"Well, he said, as far as he knew Sheri didn't know. So I invited her over to chat, asked some vague questions and it all came out. She knows everything now, including who I am. She was a bit peeved at first but was turned on at the same time."

Christy moved closer to Jim and kissed him then leaned in to his ear. "We ended up making love in my office."

Jim gasped. "She wasn't turned off by you?"

The thought of Sheri and Christy together excited Jim. Especially now that Tony knew her secret.

"No. She confessed it was actually quite a turn on. She wants me to tape the whole episode tomorrow night. If this is what Tony wants then she wants it on tape. To quote her 'There will be some changes in his life now'."

"Good, then I can watch too." Jim exclaimed." Maybe I should skip poker tomorrow night and watch the whole thing unfold. Sounds like it will be hot." Jim had thought Tony was good looking and had been more than a bit interested to see what he was hiding in those pants.

"Oh no, no, no." Christy scolded him. "You need to keep your plans and act as if you don't know anything. If you see Tony tomorrow you tell him that you'll see him at the poker game. Besides, you'll get to watch it all on tape. Who knows maybe some day we can have a foursome, and I'm not talking golf." Christy giggled.

"Tonight though, I want to play with you. I'm so hot and horny I can barely contain myself." Christy said while squeezing Jim's crotch. It felt like he wanted to play too. While cooking dinner together they could barely keep their hands off each other. While Christy was trying to fry some chicken Jim would come up from behind and rub her ass, grabbing her hips and grinding his cock into her, making her moan. Christy would retaliate by kissing Jim passionately and sliding her hand down his pants to stroke his hard cock. On and on they went through diner.

Leaning back in her chair at the table Christy sighed. "That was good, but now I think I'm in the mood for some dessert."

"Oh? And what did you have in mind?"

"You." Christy replied as she got up from the table, took Jim by the hand and led him upstairs.

"I was hoping you'd say that."

Not wasting any time Christy pulled off her tee shirt and let her beasts fell free. Then she undid her jeans, kicked them off and hopped on the bed. Rolling on her back she spread her legs and fondled her hardening cock, all the while staring at Jim with a lustful look in her eyes.

Taking a hint, Jim quickly tore off his clothes and climbed into bed with Christy. They fell into a sweet embrace, rubbing each other's bodies, exploring with their fingers while kissing each other. Christy let a low moan escape her lips when Jim began to squeeze her ass. Responding to his ministrations she ground her hips into his, their hard cocks rubbing each other.

Christy leaned over and began kissing Jim's nipples, getting them wet and hard. When she was satisfied with her work she began biting them gently, making Jim cry out in ecstasy.

"You like that lover?" Christy asked while looking up at Jim.

"Oh you know I do baby." Jim hissed as he slipped a finger into Christy's ass, making her moan.

"Mmm, Please tell me you'll replace that with your cock."

"I will, but first I want to feel your mouth around me. And I wan to taste you.."

Christy lay on her back and Jim straddled her face. His 7" cock was dangling right above her face, it's thick veins bulging and the head glistening with precum. She couldn't wait to taste is. Grabbing his cock by the base she guided it to her mouth. Jim lowered himself to her lips while moving closer to Christy's cock. They engulfed each other at the same time and began bobbing and sucking. Christy slowly thrust in and out of Jim's mouth until he had taken her whole length. It felt so good to be deep-throated by Jim. As Jim bobbed on Christy his hands were roaming over her ass and balls, massaging each in turn. The feeling was overwhelming and she moaned her approval around Jim's cock.

"Ohh yes Jim, take me deep."

"Gladly." Came the muffled reply from between her legs.

Jim liked hearing Christy moan with pleasure, especially when his cock was buried in her throat. The combined sensation of her humming and her hot, wet mouth made Jim even harder. Sliding off of Christy's cock he laved her balls, one at a time, sucking and licking them, feeling their weight, heavy with cum. His hands massaged Christy's ass and slid their way to her tight puckered hole. Once there he licked one finger and slowly slipped it in her ass. Again Christy moaned in response.

Christy loved the feel of Jim's finger in her ass and his mouth on her balls. It made her hard as a rock as Jim worked his magic on her she ground her hips up and down on the mattress, her cock bobbing in the cool air. It felt so good. Taking Jim's cock from her mouth she slipped it between her tits. Slick with her saliva Jim sawed in and out of her cleavage. Every time he moved back Christy would give his ass a lick, causing him to moan.

They kept at their oral ministrations on each other for almost twenty minutes, rolling over on the bed and switching positions numerous times. In the end Christy was on her knees in front of Jim. He had her head in his hands and was fucking her mouth like a pussy. Christy writhed in pleasure as she stroked her cock and had her mouth filled. She puckered up and sucked deep, creating a vacuum for Jim's cock, pulling him in with each thrust. Looking down a the edge of the bed she spied a pair of her silk panties and grabbed them, an idea hit her.

She grabbed the panties, wrapped them around Jim's cock, and began stroking him.

"How does that feel Jim?"

"Feels great baby. You know I love the feel of silk on my cock." Jim groaned as he thrust in and out of Christy's hands.

Christy continued to stroke Jim as she stood up. "Maybe I should start buying panties for you."

Jim's reply was a long low moan. She took that as a yes. Maybe she could get him all dolled up one of these days too, but right know she had other things in mind. While continuing to stroke Jim she leaning in and began kissing his neck. She kissed and licked her way up to his ear and whispered in it.

"Are you ready for me baby?"

"Oh yes." Jim replied enthusiastically.

Christy lay down on the bed and held her cock high for Jim. He straddled her and slowly lowered his waiting ass over her cock. Christy eased into Jim's tight hole, feeling his warmth envelope her steely shaft.. Jim took every inch of her in his ass and ground his hips while he adjusted to her thickness.

"Your cock feels like heaven in my ass Christy." Jim gasped.

He leaned forward and licked Christy's nipples sucking each one in his mouth and nibbling on them to get them rock hard. The result elicited a moan from Christy.

"Oh yes baby, bite them, squeeze them. You know I like it a little rough." Christy exclaimed.

With that encouragement Jim began to bite harder on her nipples and roughly massaging them as Christy sawed in and out of his ass faster and faster.

"Mm baby yes, fuck me faster. Cum in my ass."

To move her even closer to cumming Jim squeezed his ass tight around Christy's cock with each thrust.

As Christy began to saw slowly in and out of Jim's wet hole. He squeezed his sphincter to milk Christy with every thrust. Her paced quickened as she came closer and close r to cumming. Not being able to take it any more she groaned loudly, grabbed Jim's hips and buried her length in his ass and shot spurt and after spurt of cum into his ass, filling him with her sticky fluid.

"Ohh yesss. Now it's your turn Christy." Jim said as he slipped off of Christy softening cock, her cum dripping from his freshly fucked ass.

Christy got on her hands and knees and wiggle her ass at Jim in invitation.

"Come and get it baby."

He climbed behind her sweet round ass and reached between his legs. Jim took some of Christy's come dripping out of his ass and lubricated his cock with it.

"Here is comes Christy. That ass looks so inviting I don't know if I'll last to long."

Jim grabbed her hips and slid into Christy in one thrust causing her to moan as she was filled with his thick cock. She began to buck as Jim held her and rammed his cock in and out of her ass. She milked him just like he did to her, wanting his cum in her ass too. Jim reached around and fondled her breasts as they fucked. Eventually Christy sat up and leaned back into Jim letting him penetrate her as deep as he could.

Jim ran his hands up and down Christy's taught stomach as he bucked into her, on the edge of exploding.

"Oh baby, I'm going to cum. I told you I couldn't last long."

"Give it to me. Fill my ass with your cum!" Christy demanded.

Jim needed no more encouragement. He slammed into her and exploded in a violent orgasm, moaning with each hard thrust as he shot load after load of cum deep in her ass. They collapsed on the bed bodies tangled together and fell into a deep sleep, their lust for each other satiated.

Jim woke before Christy the next morning and kissed her lightly on the cheek as he shook her awake.

"Honey, it's time to get up."

"Christy rolled over and kissed Jim.

"Ohh my. You wore me out last night honey." Christy whispered. But it was so good."

She sat up, hopped out of bed and headed into the bathroom to take a shower. She had a big day ahead of her. Tony was coming over tonight for his first appointment to be feminized. Unbeknownst to him, his wife was going to show up to and watch the whole thing on TV. Stepping out of the shower she toweled off and the scent of bacon and eggs wafted in the room. Jim was downstairs cooking breakfast. Good, she was famished.

She dressed in the same pair of jeans and boy shorts she had on last night and grabbed a zip front sweatshirt for a top. She needed to go shopping today. Tonight was a bit special so she wanted some new lingerie for herself.

When she came downstairs Jim had breakfast served up and ready to eat.

"I'm going to head out shopping to get ready for tonight if that's okay with you." Christy said between bites of scrambled eggs.

"Sure. I've got things I need to do back at my house before the poker game tonight anyway. I still can't believe what you told me yesterday. You are going to have one wild night baby. I can't wait to watch it on tape."

"Oh, don't worry, you will. I'll fill you in on all the details too."

She finished up her bacon, kissed Jim and headed out the door to go shopping. "Don't forget to lock up when you leave."

Christy headed to the mall to her favorite lingerie shop. The girls there knew her on a first name basis by know since that was where she did all her shopping, and they knew her little secret.

Walking in the front door she waved hi to Gabrielle, a hot little redhead with a curvy figure. "How are things going Gabby?"

"They're going great Christy. I haven't seen you in a while. Looking for something special?"

"Yes, I've got a hot date tonight and wanted a little something sexy for later in the night if you know what I mean." She grinned.

"I've got just the thing for you." Gabrielle said as she led Christy to the back of the store.

She pulled out some silk boy shorts with garter straps on them and laid out a few different colors for Christy to look at. Christy flipped through all the colors as Gabrielle pulled out corsets to match and thigh high hose.

"Wow, these look great." Christy exclaimed. "Where did you get these? I think I need to put them up on my web site."

"We got them in yesterday from a new supplier. I'll give you the information before you leave."

"I think I'll try on a couple of different colors if you don't mind."

"Of course not hon."

Christy slipped into one of the dressing rooms at the back and stripped. She slipped on a pair of purple boy shorts and tucked her cock into place. She looked in the mirrors and liked the way they hugged her hips and ass, but wasn't sure about the color. Next she slipped on the matching hose and smoothed them out. She tried to pu the corset on next but was not having any luck. She called out to Gabrielle.

"Gabby, Could you come here for a minute. I need a hand."

"What in the world would you need a hand with?" She asked as she headed into the dressing room.

"I can't get this corset fastened." Christy said as she stood there, half naked inn front of Gabby.

"There's a trick to getting it on. Here let me show you." Gabby took the corset from Christy and showed her how to fasten it by herself.

The corset squeezed her waist and pushed her breasts high and close together giving Christy a sexy hourglass figure. Gabby looked her up and down and whistled.

"You look great in that Christy. Good enough to eat." She said with a grin on her face.

"Thanks baby. Do you think it's my color though? I'm not real wild about it."

"Try on the royal blue one and let me see."

Without waiting for Gabby to leave the room Christy stripped down and slipped on the entire outfit while she watched. She could hear Gabby's breathing getting faster as she dressed.

"You like what you see Gabby?" Christy inquired.

"Um, well," Gabby stammered. "Yes."

Christy leaned in and gave Gabby a peck on the cheek. They had never done anything together before and Christy didn't have the time to right now.

"Maybe sometime I'll invite you over and we can have a little dress up party."

Gabby blushed at the thought. "Sounds like fun."

"But right now I need to take care of some other errands. So what do you think of the blue?"

"I thik it looks better than the purple. Go with that one."

Christy stripped and gave the lingerie to Gabby so she could wrap it up while Christy changed back into her clothes. She finished up and paid, paid for the new outfit and gave Gabby as parting kiss on the lips, telling her to call sometime for that dress up party.

Christy finished up the rest of her errands and headed home. When she got home she had a couple of hours to get all dolled up for Tony's arrival. Hurrying upstairs she turned on the water to fill the tub. She wanted to be all nice and clean for Tony. While the tub filled with hot water she rubbed depilatory cream on her chest, back and ass to take care of any stray hairs she had growing in. Wiping herself down, she slipped into the tub. The hot water felt good and she relaxed, letting the hot water relax her. After soaking in the tub for a while she lathered up her legs and carefully shaved them to get rid of the stubble that was growing in. As she did the same for her arms Christy thought it might be a good idea to go in for some laser hair removal treatments so she wouldn't have to do this all the time It was becoming a bit of a hassle, not to mention expensive to do this all the time. Making a mental note of it she finished shaving and rinsed off.

There was one last thing to do before she got dressed for the nights activities. She dried off and rubbed a little talcum powder into her skin to give it a nice smooth, soft feeling. She then dabbled on a little perfume that drove Jim wild. She figured it would have the same affect on Tony.

Heading to the bedroom she slipped on her purchase from the lingerie shop. After getting the corset cinched up like Gabby saw her she took a look at herself in the mirror. Gabby was right, the royal blue did look better on her, but there was something missing. Shoes! That was it. Rummaging through her closet she found the perfect pair of shoes. They were black leather boots that came up to mid calf with a 4" heel. These would be perfect.

Sliding into them she went downstairs to put on makeup. Sitting at the makeup table Christy applied some light red rouge to bring out the color in her cheeks. Satisfied with that she found the perfect color of eye shadow, purple. It would go nicely with the color of the lingerie. To top it off she put on some glossy ruby red lipstick.

Now that she was satisfied with the way she looked it was time to make sure everything was functioning correctly. She turned on the cameras and checked that they were aimed correctly and there was a signal to the TV in the living room for Sheri. Then she made sure the digital camera and video camera were set up and charged. Everything was set, all she had to do was wait now.

The doorbell rang shortly after 6:30. Christy threw on her robe and went to answer the door. When she opened it Tony was standing on the other side.

"Come in before your wife sees you standing out there Tony."

"Thanks." He said a little sheepishly. He still couldn't believe he was doing this. Much less that it was his best friend, Chris/Christy who was going to help him do it.

"Don't worry, I'll be gentle." Christy joked.

"Um, thanks, I think." Came the reply.

Christy led Tony into her office and had him sit down. He tool a seat on the settee and Christy sat next to him.

"So where would you like to start tonight Tony? You already told me you wear your wife's lingerie so why don't we get you into something of your liking. Then I'll help you with makeup and a wig. Sound like a plan?"