The Crossdresser's Club

by Tammy Richards

 

CHAPTER 2 – THE SHOPPING TRIP

 

"What would you like to do today?" John asked. It was late on Saturday morning and John and Natalie were relaxing at the kitchen table, enjoying a second cup of coffee. It had been two months since Natalie had first discovered his stash of women's clothes in the attic. In that time, she had had a chance to get to know both Jennifer, John's feminine alter-ego, and Yvette, her new maid intimately.

Fridays were set aside for Natalie and Jennifer. Each week they tried something different. One week they had both dressed in long gowns for an elegant formal dinner. On another week, Jennifer had posed in several outfits while Natalie took pictures with their digital camera. They had then had a great time editing the photos on the computer. There had been make-up nights and hair nights and girls night at the movies. The previous night had been particularly exciting. They decided to have a contest to see who made the best-looking hooker. Jennifer had donned her black leather skirt with a see-through chiffon blouse and black patent leather shoes with 5" metallic gold spike heels. Under her skirt she wore satin thong panties. A garter belt held up her seamed stockings. The thong left her with a rather obvious bulge in the front of her skirt. She painted her lips bright red and added 1" red fingernails. False eyelashes with heavy mascara and eye shadow had completed the look.

One look at Natalie and it was clear that, in spite of her efforts, Jennifer had lost the contest. Natalie was wearing a black miniskirt with high-heeled black boots and thigh-high stockings. Her wonderbra pushed her tits up and almost out the front of her low-cut red blouse. The effect was stunning. Her make-up also made her sexual intentions for the night very clear.

The rest of the night was filled with steamy sex. They took turns bringing each other to a climax orally before raising their skirts and completing their union. By the time they had finally fallen into bed exhausted, it was nearly 2 AM.

Now as they sat enjoying the last remnants of their breakfast, Natalie looked out the window. "It's a beautiful day. I can't see spending it around the house. How about going shopping?"

"Sounds like a good idea to me. Where would you like to go?"

Natalie thought for a moment. "Why don't we go to Bridget's Boutique? You've told me about it, and I know you've gotten a lot of your clothes there. Maybe we could find you a new outfit."

John's mouth dropped open in shock. "Are you serious? It would be fun to show you where I shop, but I wasn't sure what you would think of it."

"I'd really like to see it. However there's one caveat. If we're going to shop for a sexy new outfit for you, you'll need to be properly attired for the trip."

"Whoa. I'm not going outside in a dress. What if somebody saw me?"

"Don't worry. Nobody would ever recognize you. Besides, since Bridget's is a store for crossdressers, I would assume that a lot of the customers wear their feminine clothes while shopping."

John nodded. "If you think it will be OK, I'm willing to give it a try. You'll have to drive though. I'd have a hard time explaining things to a policeman if we got stopped."

Natalie gave her husband a big hug and kiss. "It'll be fun."

They headed for the bedroom to get ready. "You should probably wear something conservative, so you don't draw too much attention to yourself," Natalie suggested. "How about your gray skirt suit with a white blouse, and your low-heeled pumps. It's a very attractive outfit and it makes you look very feminine." John nodded in agreement.

For herself, she selected a navy blue knit dress and mid-heels. The dress really showed off her figure. She wanted to make sure that people's attention would be drawn first to her, rather than to Jennifer.

When they were ready, they headed for the car. "I'm really scared," Jennifer confided. "What happens if someone makes me as a man. I'd die of embarrassment."

Natalie reassured her. "There's no way that anyone would detect that there's a man under the clothes and make-up. I'll be with you all the time, and I won't let anything bad happen."

They climbed into the car and headed for the store. It was about 45 minutes drive to a neighboring city. While they drove, Jennifer practiced her feminine voice and Natalie offered her pointers. When they got there, Jennifer directed her to a parking lot near the store.

"Are you ready?" Natalie asked.

"As ready as I'll ever be. Let's go before I loose my nerve." They got out of the car and headed for the boutique, two beautiful women out on an afternoon shopping trip. Once inside Jennifer began to relax. She showed Natalie around the store. Natalie was amazed by the large selection of dresses, lingerie, wigs, shoes, cosmetics and jewelry. She was also surprised by the large number of customers. She had never realized that there were so many crossdressers. She noticed another couple shopping together. Both were wearing dresses, and she suspected that they were a couple like she and Jennifer.

They passed a display of silicone breastforms and Natalie stopped to examine them. "There so lifelike," she said to Jennifer. You really need some new ones. Yours aren't very realistic and it limits what you can wear. Why don't you try on a pair?"

"They look great, but they're very expensive."

"After the commission check you just received, I'm sure we can afford them."

Just then a saleslady walked past. Noticing Natalie and Jennifer, she approached. "If you would like to be fitted for a pair, we have a private fitting room and a specialist who can help you."

Jennifer looked at Natalie. "Go ahead and try them on," said Natalie.

Jennifer followed the saleslady to the fitting room where she was introduced to the fitter. She removed her jacket, blouse and bra. The fitter measured her chest and checked her skin color. She then had Jennifer sit back in a reclining chair. "Given your body size, I would recommend a pair of C-size forms. They'll look the most natural. She brought out a pair in the right size and color. "Let me show you how these can be attached to your chest so that you can see what they look and feel like."

With Jennifer's OK she applied adhesive to the forms and carefully attached them to Jennifer's chest, explaining the procedure as she went along. She then showed Jennifer how to use make-up to blend the breastforms into her natural skin. When she was done, she helped Jennifer into her bra. "What do you think?"

Jennifer stood to examine herself in the large mirror. "They're unbelievable," she said, admiring her new bosom in the mirror. "They look so real."

The fitter smiled and handed Jennifer her blouse. "Why don't you wear them for a while to see what they feel like." Jennifer thanked her and got dressed. When she returned to the shopping area, she found Natalie talking to another woman. "Jennifer, this is Elaine. She's here with her girlfriend Stephanie."

"It's a pleasure to meet you Jennifer." Jennifer mumbled a greeting, her face turning red under her make-up.

"How do they fit?" Natalie asked. Turning to Elaine, she explained, "Jennifer has just been fitted with new breastforms."

"They look great. The fitter told me to wear them for a while to see what I think."

"Well I'd like to see them too." She handed Jennifer a burgundy knit dress with a scoop neckline that she had been holding. "I found this dress. Why don't you try it on and let's see what your new cleavage looks like?"

Reluctantly taking the dress, Jennifer headed for the dressing rooms. As she entered the dressing room area, she saw Elaine's girlfriend going into another dressing room with a beautiful silk cocktail dress. Jennifer slipped off her suit and stepped into the knit dress. Zipping the back, she examined her reflection in the full-length mirror. She had to admit that the effect was spectacular. The dress hugged her body, ending about 3" above her knees. But it was her bosom that captured her attention. Protruding above the neckline was a very feminine cleavage. Jennifer thought that it would be nearly impossible to tell that her breasts weren't real without a close inspection.

Summoning all of her courage she left the dressing room and headed back toward Natalie and Elaine. As she approached, she noticed that Elaine's girlfriend was already there. She seemed very relaxed as she modeled her dress for the girls. They all turned as Jennifer arrived. "Wow!" Natalie exclaimed. "That dress looks incredible on you. I think those breastforms might give you a better cleavage than I've got."

Taking Jennifer by the hand, she turned toward the other two girls: "Jennifer, this is Elaine's girlfriend Stephanie."

Stephanie took Jennifer's hand with a very feminine motion. "It's nice to meet you Jennifer. I have to agree with Natalie. You look lovely in that dress." Her voice was soft and sultry, suggesting that she had had a lot of practice speaking with a feminine voice.

"It's nice to meet you too, Stephanie. You do a good job of filling out that dress you're wearing also."

"Both of you look great in those outfits," said Elaine. Turning to Stephanie, she said: "Yours will be perfect for next month's party."

"That dress was made for you," Natalie told Jennifer. "I definitely think you should buy it, along with those beautiful breasts." Jennifer nodded in agreement.

Having decided on those purchases, Elaine and Natalie suggested that they try on some other outfits for future reference. For the next hour, Jennifer and Stephanie took turns modeling various dresses and gowns for their wives. Jennifer even got up the courage to try on a pink satin maid's uniform. "I've already got one of those," Stephanie whispered to her.

"I'll bet you look cute in it."

When at last they paid for their purchases and were heading for the door, Elaine turned to Jennifer. "Stephanie and I are going out to dinner now. Would you two care to join us."

"I don't think so. This is the first time I've ever been out of the house dressed in women's clothes. It took all my courage and a lot of support from Natalie just to come here."

"Don't worry," chimed in Stephanie. "We're going to a restaurant that we visit frequently. The lighting is low, the owner knows us, and we always get a nice booth towards the back of the room. You're a very nice couple and we'd like to get to know you better."

"It sounds like fun Jennifer," said Natalie. "I don't think there would be much risk. What do you say?"

"Well, I've gotten this far. I guess it would be OK." Elaine gave them directions and they headed to their cars.

When they got to the restaurant, they found Stephanie and Elaine waiting for them. "We called ahead," said Stephanie. "Our table is waiting for us."

When they entered, the owner came forward to greet them. "It's nice to see you again. You both look lovely as always." Turning to Jennifer and Natalie he said, "I see you've brought some friends. Welcome to the Hideaway Restaurant. I hope you'll enjoy your evening with us. Your table is all ready. Please follow me."

He led the way into the dining room and seated them at a secluded table near the rear of the dining room. "May I take your drink orders?"

When they had ordered, Jennifer surveyed the room. It was large and richly decorated with wood-paneled walls and dark green velvet cushions on the chairs. The lighting was low and many of the tables were filled with couples. No one seemed to be paying the least bit of attention to them. She began to relax.

The drinks arrived. Stephanie raised her glass to propose a toast. "Here's to our new girlfriends. May this be the first of many encounters."

Jennifer decided that it was time for her to get into the flow of the evening. "When we left home this morning, I never would have guessed that we would be dining with new friends tonight. Here's to both of you for helping us make this a great day."

Over drinks and dinner the two couples chatted. Elaine and Stephanie were fascinated by Natalie's story of how she had discovered John's secret. "I'm amazed that you have been so accepting of the situation," said Elaine.

"I'll admit that it was very difficult at first. I didn't understand why John would want to dress in women's clothes, or if I had in some way failed him. I wasn't sure I could face seeing him dressed that way. It wasn't until I had met Jennifer that I understood how important this was to John, and that I could be a part of this side of his life as well. As surprising as it may sound, discovering John's feminine side has been the best thing that ever happened to our marriage."

"I don't find it at all surprising," said Elaine. "Living with both Stephen and Stephanie has been wonderful. Like you, it took me a while to get over my initial reaction to the discovery of Stephen's feminine side. It's been almost 10 years since I first met Stephanie, and I've never regretted it."

Listening to this exchange between their wives, Stephanie turned to Jennifer. "Have you ever thought about trying to find other couples who share your interests in beauty and femininity?"

"We've never talked about it much. I wouldn't have any idea how to go about making connections with the right people. There's no way we would ever consider visiting places like gay bars where we might meet other crossdressers. I think it was an incredible stroke of luck meeting the two of you today at Bridget's."

"There have been a lot of times that I would have given anything to be able to talk to someone else who really understood what I was going through," said Natalie. "Unfortunately it's not the kind of subject you can discuss with just anybody. Why do you ask?"

Stephanie and Elaine looked at each other. Elaine nodded imperceptibly. "We may be able to help you," said Stephanie. "For the past five years, we've been members of a crossdresser's club. There are 11 couples in the club. All of us are very happily married and devoted to our spouses. Like you, we have no interest in visiting gay bars or other places where crossdressers might congregate. But we all enjoy dressing up and we like to do things with friends who share our interests. The club also provides emotional support to each other. It sounds like you both appreciate how important that can be."

"I think we'd both appreciate having a group of friends that we could talk to," said Jennifer. "How does the club work?"

"The men meet once a month," explained Stephanie. "We try to act like a sorority group. We are each working to improve our feminine persona. So we practice a variety of feminine activities. Periodically we make appointments for private visits to one of several women's stores where we are known and our business is appreciated."

Elaine continued, "The wives also meet once a month. We share our experiences and help each other when we encounter problems. We also talk a lot about what we can do to help our spouses. We have all become very good friends."

"We have a party on the last Saturday night of each month for the whole group. Each party has a theme and we go all out to make each one special. Our schedule includes a Valentine party and a Halloween party. There's the Christmas party where everyone dresses in holiday gowns. We have a couple of gourmet dinners each year. For each one, half of the men's group joins the wives group in beautiful dresses while the other half prepares and serves the dinners in their maid's uniforms. The highlight of the year is the annual spring prom. We get to don our prom dresses and high heels while our spouses rent tuxedos. We then dance into the wee hours of the morning."

Natalie and Jennifer were stunned. "I would have never guessed that a group like yours existed," said Jennifer. She looked at Natalie and saw her smiling. "Would it be possible for us to join your group?"

Elaine replied, "If it was up to us, there would be no problem. But, as you can understand, we are a small and very close-knit group. Everyone gets a vote on any new members."

"If you're interested, we'll set up a meeting with the whole group," said Stephanie. "It will give them a chance to get to know you and vice versa. If everyone agrees you'll be invited to join the club."

Jennifer and Natalie looked at each other. It was clear that both wanted to do it. "Please set it up," said Natalie. "We'd love to meet the rest of your group." They gave Elaine and Stephanie their phone number.

As they were leaving the restaurant the owner came up to them. Handing a business card to Jennifer, he said, "I hope you enjoyed your meal. Please come back again soon. You're welcome any time. Just call me and I'll arrange to have a table waiting for you."

"Thank you," said Jennifer. "It was a wonderful dinner and a great evening. We'll definitely be back."

With hugs and kisses all around, the couples headed their separate ways. As Natalie and Jennifer drove home, they reminisced about the day. "I was amazed by how well you did at the restaurant," said Natalie. You seemed to really relax and enjoy being one of the girls."

"Once it was clear that no one was paying any attention to us, I was able to focus on our conversation and forget that there were other people around. Watching Stephanie act so comfortable as a woman made it a lot easier. They really are a nice couple. What do you think about joining their crossdresser's club?"

"I think it would be very good for both of us. It sounds like they have a lot of fun. But only if you want to do it."

"I do. I think it would be great also. Hopefully they'll call us soon."

When they got home neither one of them was tired. "Let's put on our negligees and have a nightcap," suggested Natalie.

As they undressed, Natalie couldn't help but stare at Jennifer's new breasts. She fondled them. "Not only do they look real, they even feel quite natural."

Jennifer pulled back. "Quit playing with my boobies."

"Fairs fair. You're always playing with mine." She planted a big kiss on Jennifer's artificial nipple. "Hmm, that tastes good."

Jennifer put on a nightgown with a built in bra to hold her new breasts in place. She slid a pair of thigh-high stockings up her legs and stepped into her high-heeled pumps.

Natalie admired her feminine endowments. "You look very sexy in that outfit. I'm getting hot already. Why don't you get us a brandy while I finish getting changed."

When Jennifer returned to the bedroom with their drinks, Natalie had turned down the covers, plumped up the pillows and lit the candles. The atmosphere was very sensual. They lounged on the bed and sipped their drinks. Gently they kissed and caressed each other's bodies. Slowly their passion began to build. Every touch added to their stimulation. When at last they achieved their release, a feeling of total contentment settled over them.

Later as they cuddled together with their breasts touching, John smiled at his wife. "Thank you for a wonderful day. I consider myself the luckiest guy in the world to have you for my wife."

As he drifted off to sleep he heard his wife murmur: "Life couldn't get much better." John smiled in agreement.

  

  

  

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