The Crossdresser's Club

by Tammy Richards

 

CHAPTER 1 – THE DISCOVERY

 

It was the Saturday before Christmas. Natalie was in the attic looking for boxes to wrap the last few presents, while John was running last-minute errands. As she dug through a pile of boxes in the corner, she happened to open a large box that had been pushed behind the rest. Imagine her surprise when she discovered that the box was full of women's clothes. There were dresses, lingerie, high heels, even a couple of wigs. Natalie was a perfect size 8, while most of the dresses were size 12. As she dug through the pile of clothes, the awful truth hit her – these clothes must belong to her husband John. Why was he dressing in women's clothes? How long had he been doing it?

Natalie and John had been married for nearly 5 years. John was a salesman. When he wasn't making sales calls, he worked out of an office in the house, while Natalie worked as the manager in an insurance office. In all the time that they had been married, she'd never had any hint that John might have a feminine side.

When John got home from the store, he discovered Natalie sitting in the middle of the attic with his secret stash spread out on the floor around her. "Are these your clothes?" she asked.

"Let me explain," John began.

Natalie screamed at him: "I don't want to hear any explanations. I just want to know if you've been wearing these clothes."

"Yes, they're mine. I like to dress up when I'm home alone working. I'm really sorry, honey. I didn't mean to upset you."

"Well you did," she replied as she threw a dress at him and ran from the attic crying. She went into the bedroom, locking the door behind her.

For the rest of the day, every time John knocked on the bedroom door to try to talk to his wife, she would yell at him to leave. Eventually he decided to fix dinner in the hope that a nice meal would reduce the tension. About 6 o'clock, he knocked on the bedroom door again. "Honey, the dinner is almost ready, and I have a glass of wine for you. Would you please come out and talk to me?" To his surprise the door opened. Natalie was standing there with her eyes red and swollen from crying. John tried to hug her but she pushed away from him and walked to the kitchen. John followed and busied himself getting the dinner on the table while Natalie took her glass of wine and went into the family room.

When everything was ready, John called her to join him at the table. She sat down and began to fill her plate. For the next several minutes they ate in silence. Finally she looked at him. "So, how long have you been dressing in women's clothes?"

With an embarrassed look, John admitted that he had been dressing up since he was a small boy. "I started out wearing my mother's lingerie and dresses. When I was home alone, I would go to my parent's bedroom. There I would strip and get dressed from the skin out in her underwear, stockings, dresses and high heels. I spent hours parading in front of her mirror. Several times I was almost caught, but I always managed to get things put away before they saw me."

"When I went away to school, there were very few opportunities to dress up other that the occasional Halloween party. Then I met you and we got married. I found myself surrounded by your beautiful and sexy clothes. I tried on some of your things a few times when you were out for the evening, but you're quite a bit smaller than I am and I didn't want to take a chance of tearing something."

"When I started working out of the house, I found that I had a lot of opportunities to dress up. After you left for work in the morning, I would get dressed in a skirt and blouse or dress and heels and spend the day working. At the end of the day, I would change back into my male clothing before you came home. Over the last few years, I've built up the rather extensive wardrobe that you found this morning."

As John talked, Natalie continued to eat her dinner. "Have you ever gone out while you were dressed?"

"Heavens no," John exclaimed. "I would be scared to death that someone might recognize me."

"I still don't understand," Natalie said. "Are you gay? Do you want to become a women?"

"Absolutely not. I love you Natalie. You're my wife and I want to be with you always. I have no interest in becoming a woman or having sex with anyone but you. I'm sorry that I didn't tell you about my crossdressing, but frankly I was afraid that you would leave me."

For the next hour Natalie continued to ask John questions as she tried to come to grips with his revelations. Finally she said, "Don't worry, John. I love you too and I'm not going to leave you. However this morning's discovery was a terrible shock to my system. I'm going to need some time to deal with my thoughts and feelings."

"I understand," John replied.

For the next couple of weeks, Natalie spent a considerable amount of time reading everything she could find about crossdressing. She discovered that the majority of crossdressers are not gay and have no desire to become women. They just enjoy the feel of silk and satin against their skin. They like to dress in sexy outfits and shed their male persona. Natalie found herself becoming curious about what John would look like as a woman, wearing a dress and heels, with his make-up done and a long wig on his head. At 5'8" tall and 140 pounds, she thought he would probably make a rather attractive woman.

Eventually Natalie made her decision. She loved her husband. If he wanted to dress in satin and lace, she would accept and support his desires. She then began to plan for her first meeting with John's alter ego.

She decided to have John's coming out party on the first Friday after New Years. To get prepared, she took the day off from work. When John arrived home from his sales calls, he found the table set for a romantic candlelight dinner and Natalie wearing a sexy black cocktail dress and her patent leather stiletto heels. "What's the occasion?" he asked.

"I think it's time that I met my new girlfriend," Natalie replied. "There's plenty of time before dinner. Why don't you go and make yourself beautiful."

"Are you sure?" John asked.

"Absolutely," she replied. "Now go and get changed, and don't dawdle." With that, John headed for the attic to select an outfit and then went into the bedroom to get changed.

John decided that if Natalie wanted to meet his feminine side, he would go all out to impress her. He started with a hot shower. Natalie had some depilatory cream that he used to remove his light body hair. He then gave himself a very close shave. Once he was dry and powdered, he put on a tight panty girdle to hide his male organ. Next came a lace-up corset that he used to pull in his waist to a slim 26". That was followed by sheer nylon stockings that were attached to the garters on the corset. John then put on a lacy red bra and inserted breastforms into the cups.

At this point John sat down at Natalie's vanity table to put on his makeup. He started with a creme foundation and powder make-up. He then dusted his cheeks with blush. Next came eye shadow and liner with three coats of mascara to lengthen his lashes. That was followed by a bright red lipstick that John applied with a brush to give his lips the right shape. The last step was to apply a set of fake fingernails painted red to match his lipstick. The face looking back at John in the mirror was that of a very attractive woman.

Once John was done with his make-up, it was time to finish dressing. He had chosen to wear his sexiest red satin cocktail dress for the evening. The dress hugged every curve in his body, ending about 3" above his knees. His shoes were a pair of red patent-leather pumps with 5" heels. Finally came the crowning touch – his shoulder-length blonde wig. He added a pair of gold clip-on earrings from his collection and a necklace that he borrowed from Natalie's jewelry case.

John was ready. He checked himself in the full-length mirror and then proceeded to the family room where Natalie was listening to a CD and drinking a glass of wine. She had heard the tapping of his heels as he walked across the kitchen floor, but she was still stunned by his appearance. "Wow, you're really beautiful. Come here and let me get a better look at you."

John walked across the room and did a pirouette in front of her. "Do I really look OK?" he asked.

"You look better than OK," Natalie replied. "If I didn't know it was you, I never would have recognized you. There's just one thing wrong."

"What's that?" he asked.

"Calling you John just doesn't fit with your new appearance. You need a more suitable name."

"How about Jennifer?" he suggested.

"I think that fits very nicely," she replied. "Well, Jennifer. Sit down and have a glass of wine. Dinner's not quite ready yet."

Jennifer poured herself a glass of wine and sat down on the couch. She crossed her legs and pulled the hem of her dress down as she had seen Natalie do so many times in the past. Natalie noticed this motion and nodded approvingly. "I'm really jealous of you," she said. "Your dress is sexier than anything I own. Where did you get it?"

"I got this and a lot of my other clothes from Bridget's Boutique. It a women's clothing store that caters to crossdressers. They have an extensive selection of dresses, lingerie, shoes, wigs and cosmetics – everything that we "girls" needs to look beautiful. The best part of shopping there is that I can try things on in their private dressing rooms. That way I'm sure it fits before I buy it."

"Well it fits perfectly," observed Natalie. They continued chatting as they sipped their wine. When dinner was ready, Jennifer lit the candles and turned down the lights while Natalie dished up the meal. When they were seated, Natalie held up her glass of wine. "I'd like to propose a toast to the start of a lasting friendship with my new girlfriend."

"And I want to toast my wonderful wife. Thank you for being willing to understand and accept my desire to dress up. You're really a special person."

Natalie had prepared a gourmet dinner for Jennifer's coming out party. As they ate and talked, both Jennifer and Natalie relaxed and really began to enjoy the evening. Before long they were talking and giggling like a couple of schoolgirls. When they were finished, Jennifer cleared the table while Natalie poured them each a snifter of brandy. They then sat down to relax and listen to the music.

Natalie moved closer and began to run her fingers up Jennifer's leg and under her dress. The feel of her fingers gently caressing Jennifer's stocking-clad leg was incredible. Jennifer's hand slid up to Natalie's breast and began massaging it through her dress. Their lips met in a passionate kiss. Jennifer felt her swollen penis pushing against the prison of her panty girdle, straining to get out. Within minutes, Natalie's panties were soaking wet from the flow of her love juice. "I think I'm getting a very unladylike bulge in the front of my dress," whispered Jennifer.

"Well then, we'd better do something about that," Natalie said as she reached behind to unzip Jennifer's dress. Their passion continued to grow as they slowly undressed each other. When they had stripped to just their stockings and heels, Natalie guided Jennifer down onto the family room floor. Positioning herself above Jennifer, Natalie began to fondle her throbbing cock. Slowly she eased her mouth down on it and began to suck. At the same time, she lowered her sopping pussy down to Jennifer's waiting tongue. Within minutes they had both exploded in mutual orgasms of titanic intensity.

After catching her breath, Natalie began working to bring Jennifer's now-limp penis back to life. It didn't take long. Once she had it standing at attention, she turned around and lowered herself onto it. Slowly and rhythmically, Jennifer and Natalie began moving together. The speed and intensity of their love dance began to increase dramatically. They seemed to go on forever before coming in even more intense orgasms. Completely spent, they lay on the floor in each other's arms.

"That was incredible," said Natalie. "If wearing women's clothes gets you this turned on, you can wear them whenever you want."

"You were pretty hot yourself. I've never seen you as passionate as you were tonight. I'll admit I really enjoyed dressing up and spending the evening as your girlfriend. But I think you liked it as much as I did."

"I'll have to admit that you're right. I wasn't sure what to expect or how I'd react to seeing you in a dress. When you walked through the door, I was really shocked. You had transformed yourself into a very attractive woman. That made it much easier to think of you as my girlfriend and not my husband. I've had a wonderful evening and I'm already looking forward to our next one."

John didn't have to wait long for his next opportunity to dress in his feminine finery. The next day being Saturday, John spent the morning working in the yard. He came in at noon, ready to sit down with a sandwich and watch some of the ballgame. "John, come see what I've done," called Natalie from the spare bedroom. When he went upstairs, he discovered that Natalie had moved all of his women's clothes from the box in the attic to the bedroom. His dresses, skirts and blouses were neatly hanging in the closet while his lingerie was folded and put away in the dresser. Natalie had placed his wigs on wig stands in the top of the closet while his shoes were on a rack on the floor.

"You have so many nice clothes," Natalie observed. "I would hate to see them get ruined in the attic. They'll do much better down here."

"Thanks very much. I appreciate you doing that for me."

"As I was putting things away, I noticed that you have a very sexy black satin maid's uniform. I'll bet you look stunning in it."

"Well, I'm not sure about that," he said sheepishly. "But I do think that when I'm wearing my fishnet stockings and high-heeled pumps, the uniform really shows off my legs."

"I've often fantasized about having a maid that would wait on me hand and foot. Are you interested in playing the role?"

"I'd love to try it," John replied. "It will take me a while to get everything ready though. Why don't you go shopping this afternoon? When you get home you'll find your new maid waiting to serve you."

Natalie headed for the mall while John took off for the grocery store. Since he occasionally fixed dinner when Natalie had to work late, he was comfortable around the kitchen. For tonight's dinner, he decided on baked fish with rice and a Caesar salad. Once he had made his purchases, he returned home to get everything ready for his wife's return.

When the table was set and the salad prepared, it was time for his transformation. He started with a quick shower and a close shave. He then put on a pair of white ruffled panties. He selected a waist cincher, rather than a lace up corset to give his waist the desired shape without restricting his ability to move around. He figured he would be busy tonight. He carefully pulled on his fishnet stockings and attached them to the garters on the waist cincher. He put on his bra and inserted his breastforms and then stepped into a full white petticoat. He took extra time to make sure his make-up was perfect. He selected a pink frosted lipstick and applied matching pink fingernails. Then he was ready for his maid's uniform. It was very form-fitting and always a little tricky to get the back zipper closed. It was a shiny black satin with white lace trim on the neck and sleeves. He tied the white satin apron around his waist. For tonight he decided to wear his brunette wig. It framed his face in a mass of curls. Finally he was ready. Stepping into his high-heeled pumps he admired himself in the mirror. He had to admit that he didn't look too bad.

It was nearly 6:30 when he heard Natalie's car pull into the garage. She came into the house carrying several packages. John curtsied. "Good evening, Madame. My name is Yvette and I'm your new French maid. May I take your coat?"

Natalie broke into a big smile at the sight in front of her. "Good evening, Yvette." She set down her packages and took off her coat. "Here you are. Thanks very much."

As Yvette headed for the closet she asked: "Did you enjoy your shopping trip this afternoon?"

"It was great. Why don't you bring me a glass of wine and I'll show you what I bought." With that she picked up her packages and headed for the family room. Yvette poured a glass of wine. Placing it on a silver serving tray along with some cheese and crackers, she followed her mistress into the family room.

Once Natalie was seated, Yvette served her wine and placed the food on a small table next to her chair. "This is for you Yvette," Natalie said handing her a package from Victoria's Secret." Yvette opened the bag. Inside were several pairs of lace and satin panties in various styles and colors. "I decided that you need to have something besides your white cotton jockey shorts. I'm really interested to see what you think of the thong I bought you."

"Thank you ma'am. I can't wait to model them for you." Natalie opened the next packages to show Yvette a new skirt and sweater that she had purchased for herself. "They're lovely," Yvette cooed.

Natalie handed them to her. "Please remove the tags and hang them in my closet for me."

"Certainly ma'am. What about the last package you have there."

"That's for later," replied Natalie. "You know Yvette, a nice hot bubble bath would really feel great. Is there time before dinner?"

"Absolutely. I'll go now and get it ready for you." Yvette headed for the bedroom. By the time Natalie had removed her clothes, everything was ready. Steam was rising from a bathtub filled with bubbles.

"Hmm, this feels wonderful," Natalie said as she slid down into the water.

Yvette busied herself hanging up Natalie's clothes. "What would you like to wear tonight, ma'am?"

Natalie pondered for a moment. "I think I'll wear my velvet jumpsuit. I'd also like to wear pantyhose tonight rather than stockings. And my black high-heeled sandals. Could you lay them out for me, Yvette?"

"Certainly, ma'am." When Natalie was done with her bath, Yvette was ready with the large terrycloth towel to dry her off. She then helped Natalie powder herself.

"It will take me about 15 minutes to get dressed and made up, Yvette. Why don't you go ahead and finish getting dinner ready. Make sure you set a place for yourself. I'd like to be able to talk to you while I'm eating."

By the time Natalie descended to the dining room, Yvette had everything ready. The salad was served and hot rolls were just coming out of the oven. Yvette held Natalie's chair for her and then poured her another glass of wine. "Don't be bashful, Yvette. Help yourself to a glass of wine also."

"Thank you, ma'am." Yvette sat down and began to nibble at her salad. Dinner was wonderful. Yvette had succeeded in preparing a delicious meal, and Natalie was very complimentary of both the food and the service.

When they were finished, Yvette cleared the table. "Would you like to have your coffee in the family room, ma'am?"

"That sounds like a great idea." While Yvette busied herself cleaning up the dishes, Natalie relaxed on the couch drinking her coffee and reading the paper. "Yvette, I think there's a little bit of ironing in the basket. Would you mind doing it for me?"

"I would be happy to, ma'am." As Natalie sat on the couch watching Yvette do the ironing, she decided that life couldn't be much better. She had a wonderful husband, a great new girlfriend and a maid who would do anything she asked. And they were all the same person. The possibilities were endless.

"I don't think I've told you, Yvette. You really are a lovely young lady. Your uniform fits you perfectly."

"Thank you ma'am. I'll admit that I enjoy wearing it."

When the ironing was done and Natalie had finished her coffee, she stretched. "I think I'm ready to retire to the boudoir. I'd like to wear my white chiffon negligee tonight. Could you get it out for me and turn down the bed?"

"Yes, ma'am." Yvette headed for the bedroom while Natalie turned out the lights and locked the doors. Joining her in the bedroom, Natalie turned her back so that Yvette could unzip the jumpsuit. She handed it to her maid to hang up and took off the rest of her clothes, which she dropped in the middle of the floor.

"Please take care of these, Yvette. And be careful that you don't run my pantyhose when you wash them out."

"Yes, ma'am." When she was done, Yvette returned to the bedroom. There she found her mistress lying on the bed in her negligee with her back propped against her pillow. As she approached the bed, Natalie pulled up the hem of her nightgown, raised her knees and spread them to expose her love nest. "Yvette, my pussy needs a good tongue-lashing. Could you help me out?"

"I'd love to." Climbing onto the bed, she knelt before her mistress and began to gently kiss and caress the inside of her thighs. Slowly she worked her way down each leg and then around her love mound. Yvette worked her tongue into Natalie's slit and began to flick it against her love button. Natalie moaned in ecstasy and ground her hips against Yvette's face. Time stood still as Yvette nuzzled Natalie's pussy. The aroma of her juices was heavenly. Natalie came again and again, each orgasm more intense than the last. When Natalie was at last completely spent she reached down and gently pulled Yvette's face to her own. Their lips met. Natalie forced her tongue deeply into Yvette's mouth.

"It's your turn now my love." She rolled Yvette onto her side and snuggled against her. She slid her hand under Yvette's petticoat and began to fondle her penis through her ruffled panties. When it was rock-hard, she eased Yvette's panties down her legs. Raising the skirt and petticoat above Yvette's waist Natalie lowered herself onto Yvette's throbbing cock. "Just lay there and relax," she whispered. "I'll take care of everything." She tightened her pelvic muscles, clamping Yvette's cock deep inside her and began to gyrate her hips. Slowly at first, and then with an increasing frenzy, she moved back-and-forth. The feeling was incredible. Yvette felt like she would explode if she didn't come soon. Suddenly Natalie relaxed her muscles. Yvette came instantly, firing her cum deeply into Natalie's womb.

"That was incredible," Yvette gasped when she had finally caught her breath. "Where did you ever learn that maneuver?"

"I read about it in a magazine." She slid off her maid. "Just lay there until I can get you cleaned up. I would hate to have you stain your beautiful uniform." She returned to the bedroom a moment later carrying a washcloth and towel, along with the remaining package from her afternoon shopping trip. After cleaning Yvette's limp penis, she handed her the package. "You did a superb job tonight as my maid. Here's your pay."

Yvette opened the package. Inside was a long silk nightgown in gold with spaghetti straps and a slit up the front. "It beautiful. Thank you so much."

"This will look much better on you than your male pajamas. Now go ahead and get ready for bed." Yvette headed for the bathroom to make the transformation back to John." When he returned to the bedroom several minutes later, the make-up and wig were gone. It was John, clad in the gold gown, but still looking remarkably sexy. "That looks lovely on you."

"Thanks sweetheart," John said as he slid under the covers. "I really had a wonderful time playing Yvette tonight."

As they drifted off to sleep, both Natalie and John were thinking the same thing: "Life couldn't get much better."

  

  

  

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