tagTranssexuals & CrossdressersChristy's Fantasy Come True Ch. 05

Christy's Fantasy Come True Ch. 05


Chris had been busy while Jim was away on Business for the week. He had come to the conclusion that he wanted to dress full time as a woman when he wasn't at work and start a business to help men get in touch with their feminine side. He even had his first customer, Paul. They had met at a lingerie store and Chris took him home to dress him and fuck him. Even better, the whole event was on tape for Jim to see when he got home. He couldn't wait to see the look on Jim's face when he saw it.

By the end of the week Chris had printed out flyers about his business to post , set up a web site, placed some ads in fetish and adult weeklies, and had begun to contact companies about selling their TV and CD products on his website. If his business took off like he thought it would he was going to quit his job and do this full time. All in all he had been a busy man this week.

Friday after work Chris went home to change clothes and go through his now nightly ritual of shaving, putting on makeup and slipping into some sexy lingerie and a dress. It felt so natural now to dress like this. He went to Jim's place and let himself in. Jim wasn't due back until later that night and Chris wanted to surprise him. After slipping the tape he made earlier in the week into the VCR, he started cooking dinner for the two of them.

A couple of hours later he heard Jim come in through the door. Chris ran from the kitchen to meet him.

"How was your trip hon?" Chris asked.

"It was okay. Nothing to get to excited about."

"Have any fun while you were out of town?"

"None. " Jim replied.

"Did you try to?" Chris inquired.

"Yes, I hit the bar in the lobby of the hotel but nobody looked like they were out for some action."

"That's to bad honey. I have some thing to tell you though."

Jim looked at Chris with a slight smile on his face. "Oh, and what would that be?"

"Well," Chris trailed on "I went out shopping the night you left and met a guy in the lingerie shop in the mall. I bought him some lingerie he was looking at, we had dinner, and then I brought him home."

"You didn't!" Jim said incredulously.

"Yes I did. And I have it all on tape."

A look of surprise came across Jim's face.

"I thought rather than tell you about my first exploit without you I would show you."

"You little devil."

"Let's have dinner and then we can watch the tape together."

Over dinner Chris filled Jim in on what he had been up to while he was away. Jim was amazed that Chris was able to put all that together in a little over a week.

"You've been busy while I've been away."

"Well I had been giving this some thought long before I brought it up to you. If it takes off I think I'll quit my regular job and do this full time, including dressing like a woman."

"You're kidding right?" Jim asked in disbelief.

"No. I would dress full time as a woman, be as feminine as I can be. You'd have to call me Christy all the time then."

"Are you sure you want to take that step?"

"Yes, I feel more at ease like this than when I am dressed as a man. This is the way I want to live my life."

Jim couldn't believe he wanted to go through with this. He always liked Chris dressing for him but wasn't sure about him doing it full time, day in and day out. Not to mention how this new business venture would affect their relationship.

Chris could see in Jim's eyes that there were some doubts about everything he just said.

"Don't worry Jim. This will all work out. Like I said, I won't quit my job unless this new venture pans out. This past week I have been dressing up and going out every night, loving the feel of being dressed as a woman. This is what I want."

Jim looked into Chris' eyes and could see him looking for some sort of conformation that this was the right decision. Jim just sat there for a few minutes letting it all sink in. He didn't want to lose Chris. He wasn't sure where this would all lead. In the end he decided he would support Chris in whatever he wanted to do.

"Alright, if that is what you want. I just don't want you getting hurt, or our relationship falling apart. I love you Chris, er Christy."

"Oh thank you Jim." Chris gushed." Don't forget, you will get to help me with this little business when needed. I might need a more masculine touch from time to time."

After dinner was finished they got some drinks and sat down in the living room.

Grabbing the remote Christy looked at Jim. "How about watching my little movie?"

Without waiting for a reply Christy hit the play button and the show started. Jim saw Chris all dressed up and moving sensuously on the bed for a few minutes. The next thing he saw was Christy with another man he assumed was Paul. As they watched the tape Jim's cock became harder and harder. He was incredibly turned on watching Christy help Paul with his makeup and lingerie. He began stroking Christy's hair and neck as they continued to watch the tape. At the point where Paul and Christy were making love Jim was rock hard and playing with Christy's' tits through her dress. Christy took the cue and began playing with Jim's erection in his pants.

After the tape was over Jim looked at Christy. "That was incredible. If that's what you are going to do when I'm away I'm all for it."

He pulled Christy closer to him and began passionately kissing her. The rest of the night was a blur. They never made it to the bedroom and ended up making wild passionate love in the living room all night long. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ That was three months ago. Since then Christy's business had picked up and exceeded both their expectations. He had enough clients and others showing interest that he quit his regular job and was doing his new business full time.

Christy had approximately 20 different clients. Most of them single men, some married, who were interested in cross-dressing but never knew where to turn. He met with them on a weekly basis. Some just wanted to learn how to properly dress in lingerie and others wanted help with how to apply makeup. A few wanted to take it all the way and dress like women and even get fucked. Christy would help with that too. Sometimes he would teach them himself and other times he would show them what to do with Jim taking part.

After the week marking her third month in business, Jim decided to take Christy out to celebrate. A night out on the town seemed in order, dinner and dancing. He made all the arrangements and told Christy of their plans for Friday night when he called her.

"Sounds like fun honey. Maybe we could have some fun while we are out." Christy intoned

"What do you mean Christy?" Jim asked.

"You'll see. We'll just have to wait and hope something unfolds."

Friday Christy had a fairly open schedule. Only two clients were scheduled for appointments that day. Both appointments were to teach them how to apply makeup correctly so they would be short and leave her the rest of the day to take care of some internet orders and tidy up.

By the time she was finished it was four in the afternoon. Jim would be by to pick her up at 6:00, which left her enough time to get ready. Hopping into the shower she freshened up for her night out. After drying off she slipped into a short silk robe and rummaged through her lingerie chest to find something sexy to wear.

After ten minutes she decided on a maroon strapless bra, matching lace bikini cut panties, garter, and nude hose. Shedding the robe she slipped on the lingerie and headed for her makeup table. Sitting down she pondered what wig to wear. She settled on a blonde, wig with curly hair that came down to the middle of her back. Once the wig was in place she finished at the table with her makeup. Satisfied with the way she looked in the mirror she strolled over to the closet to pick out a dress to wear.

Looking through the closet, she took out a few options. She wanted to look her best for Jim tonight and wanted to try on a couple of dresses to see how they looked on her. First she tried on a calf length skirt with silk blouse. She didn't like to look of that, to business like. It was fine for her daily work but not good enough for a night on the town. Next came a short one piece with an open back to it. Slipping into it she looked at herself in the mirror. Looking at herself she frowned. 'I look to much like a hooker' she thought to herself. Slipping out of that dress she then picked up a dark red dress that came down to just above the knee and was hemmed at and angel that cut up to mid thigh. The back was open and the front had a nice plunging neckline to show off her cleavage. Slipping it on she looked at herself in the mirror. Twirling around she thought 'this is just right, sexy yet not to slutty looking'.

Satisfied with her outfit she finished with some diamond stud earrings and a couple of rings to match. She checked her watch, it read quarter till 6:00 and Jim would be there any minute.

The doorbell rang and Christy answered the door to find Jim carrying a dozen red roses.

After kissing Christy on the lips he looked her up and down.

"You look beautiful tonight. Here are some beautiful roses for a beautiful woman."

Christy blushed.

"Thank you for the compliment, and the roses. They are gorgeous."

"Well shall we head to dinner? I'm hungry and anxious to get the night started. "

As they walked out to the Jim's car Christy saw her neighbor, Tony, mowing his lawn next door. She waved to him and he waved back. Tony thought she was Chris' sister and was house sitting while Chris was away on business in Europe. At some point she would have to out himself to his neighbor or move to another part of town where they would only know her as Christy. She would dwell on it later; right now she had other things on her mind.

Jim opened the passenger door for Christy and she slipped in. Jim hopped in the driver's side and they were off to dinner. Jim drove just out of town to a new authentic Mexican restaurant they had wanted to try.

Pulling up to the restaurant a valet came out and opened Christy's door for her. She exited the car, taking the valet's proffered hand. The valet looked Christy up and down, pausing at her chest. Christy caught him looking at her and smiled. She even blew him a kiss. She liked being looked at, it reinforced the fact she was very effeminate in her new persona. The valet blushed when he realized he had been caught staring.

After handing the car keys to the valet Jim took Christy's hand and led her into the restaurant. It was a quaint little restaurant with a fireplace in the center, authentic Mexican paintings and decorations, and a mariachi band moving from table to table serenading couples seated in the dimly lit dining room. The whole place had a very romantic feel about it.

The hostess seated the two of them near the wood burning fireplace in the center of the restaurant.

The waiter arrived soon after they were seated and took their order. Christy was flirting with him as he took their dinner order. She could tell it was having an effect on him because he asked them about their order twice over and when he brought their drink order he got it mixed up.

"That's okay." Christy cooed as she blew kisses at the waiter." "We'll take what we have here."

The waiter blushed.

"You just love teasing don't you?" Jim asked.

"Yes I do. And you love it when I tease."

"Are you looking for a repeat of the first time I took you out in public all dressed up?"

"Not tonight."

Christy thought back to the night she went out as a woman for the first time. All dressed up and incredibly feminine. After teasing the waiter at dinner she gave him a blowjob in Jim's van that night as Jim watched. The waiter never knew the secret she was hiding. It had felt so incredible being dressed as a woman and having everyone look at her. It still felt incredible, but now it was even better since she had perfected her look.

As they ate dinner Christy teased both the waiter and Jim. She slipped a foot out of her heel and teased Jim by rubbing it in his crotch under the table where no one could see. Jim was squirming in his chair throughout dinner. She would tease the waiter by fawning all over him when he came by.

When dinner was finished they headed downtown for some dancing. After finding a parking spot they walked along the riverfront to their favorite bar. It was known for being a hangout for women, men and men dressed like women. Just the sort of place the two of them would feel at home.

After standing in line for twenty minutes they had made their way into the club. Jim paid the cover charge for both of them and they went upstairs. The club was packed for being early. People were on the dance floor bumping and grinding to the beat of the music. Men with men, women with women, and any other combination you could think of.

Christy led then to a dark corner of the bar and found a table.

"Why don't you order us some drinks Jim?" Christy asked. "I need to go the little girl's room too freshen up."

She turned and sashayed her way to the bathroom. Once she got to the bathroom she almost turned and walked into the men's room. Catching herself she turned and headed for the women's restroom giggling to herself, thinking about the first few times she went out in public dressed up and turned and walked into the women's restroom, found a stall and stood up to pee. Luckily there were no women in the restroom at the time but from then on she had to remember to sit down to pee lest her secret be found out.

After taking care of business she went back to the table where Jim was sitting. He had two drinks waiting for them. Sitting down she took a sip.

"Thanks baby."

"You're welcome. I got you your favorite, a margarita."

Taking a sip of her drink Christy looked to the dance floor and watched everyone bumping and grinding against each other. Watching them was getting her worked up. She reached over, put her hand on Jim's thigh, and began squeezing it, slowly working her way up to his crotch.

"Mmm, what are you doing Christy?" Jim hissed as he was taking a sip of his drink.

"What does it feel like?" Christy cooed.

"It feels like you are trying to get into my pants right here in the club."

"Very observant baby. Watching all these people dancing is getting me horny."

Without saying a word she hopped off her stool and moved over to Jim. Facing away from him she wiggled her ass in his crotch. She felt him harden as she did.

Looking over her should she said, "I see you like what I am doing."

"Yes I do. If you want to bump and grind why not get out on the dance floor?"

"Good idea."

She grabbed his hand and dragged him out on the floor. Working their way to the middle of the floor she pulled him to her and began doing a slow grind to the beat of the music. Jim got into it and began moving in sync with Christy ands soon they were bumping and grinding on the floor like they were doing a dry hump.

Christy turned her back to Jim and pulled him close. She pushed her ass into his groin. She could feel hi getting harder by the second as she bumped into him with the beat of the music. Jim grabbed her by the hips and started directing here how to move as he moved.

"You are so hot Christy." Jim hissed as she ground into him. "You are getting me all turned on."

"Good that was what I wanted. "

Christy reached behind her and pulled Jim tight against her ass, his cock rubbing up and down her tight ass cheeks as they did a dry hump on the dance floor. They ground into each other for song after song, bumping and grinding their crotches and ass together, making love with their clothes. After twenty minutes of non stop dancing Jim was ready for a break.

"How about we take a breather?" Jim asked Christy.

"You go ahead Jim, I'm just getting warmed up." Christy smiled back at Jim.

Pulling Christy close to him, Jim whispered in her ear. "Don't wear yourself out to much. You've got me so turned on I'm going to take you home later and fuck your brains out."

"Don't worry honey, I've always got energy for that."

Jim left the floor and Christy went back out to the middle to claim some space to dance by herself. As she danced a woman worked her way through the crowd and began dancing in front of Christy. Christy smiled at her as they continued to gyrate to the beat of the music.

The woman was about five foot ten with long blonde hair, her breasts were nice and round and looked like they were about to pop out of the one-piece dress she was wearing. Moving lower Christy noticed she was wearing 3" heels that accentuated her long, toned legs encased in sheer nylons.

The woman moved closer when she noticed Christy checking her out. She reached out, put her hand on Christy's hip, and pulled her close. Christy let out a gasp as she was pulled forward. She fell in step with the woman as they continued to dance. It felt good to have another woman's hands on her. She was getting turned on more and more as they continued to bump and grind. Suddenly the woman leaned in and kissed Christy, slipping her tongue into Christy's mouth. At first Christy was shocked that this woman she didn't know kissed her but then she responded in kind, kissing her back. When the music stopped for a moment they separated and Christy smiled.

"Um, hi." Christy stammered.

"Hi there. I saw you dancing out here all by yourself and thought I would join you."

"Well, actually I'm here with my boyfriend."

"Well where is he? Shouldn't he be out here with you?"

"He had to take a breather." Christy replied.

"I'm Simone."

"Christy." She replied, offering Simone her hand. Simone took Christy's hand and instead of shaking it brought it to her lips and kissed it ever so gently.

Christy looked back at their table and noticed that Jim was gone. He must have slipped off to go to the bathroom.

"Would you like to get a drink?" Christy sighed.

"Thank you, yes I would."

Christy led them to the bar and bought a drink for each of them. She then led Simone back to the table that Jim and she were occupying. Jim was still nowhere to be seen.

"So what brings you out here tonight?" Christy asked.

"I'm home alone for the week and wanted to get out and have some fun." Simone replied.

"Home alone?"

"My husband is out of town for the week so I decided tonight to get out and have some fun if you know what I mean." Simone winked at Christy.

Christy smiled at Simone, she knew full well what she meant and since she was here she must have a pretty open mind. Christy decided to probe a little further.

"So you're looking for a little action tonight then?"

Simone just nodded slowly and grinned at her. Christy moved her chair closer, slipped a hand on her thigh, and squeezed. Simone let out a soft sigh and smiled.

Leaning in Christy whispered into Simone's ear, "Do you like your women with a little something extra?"

Simone leaned back, looked at Christy and gasped.

"I had no idea you were actually a man. You look so sexy and move like a real woman."

Christy blushed at the compliment.

"I've never had an experience with a CD before." Leaning in she whispered, "Are you fully functional?"

Christy giggled and said, "Yes, these are implants but everything down below works fine."

"Mmm, this could be fun. Would your boyfriend be up for some fun with us?"

"I think I could get him to play along."

"Play along with what?" Jim asked as he came up behind Christy, eyeing both her and Simone.

"Where have you been Honey?" Christy asked

I was watching you dance and wanted a drink. I headed up to the bar and ran into a friend I hadn't seen in a while. Are you going to introduce me to your new friend?" Jim queried, as he looked Simone up and down.

His gaze moved from her deep blue eyes to her full, red lips and down to her ample breasts. Stopping there for a moment he envisioned them with nothing holding them back. Moving lower he drank in her round hips and long smooth legs. She was beautiful he thought.

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