Tammy's New Girlfriend

by Tammy Richards

 

"Danielle, I need your help!! It's Jim. I don't know what to do."

It was Saturday morning and I was sitting at the kitchen table enjoying a second cup of coffee when the phone rang. On the other end was my friend and neighbor Linda Peterson. It was clear from her voice that she was distraught and had been crying.

"Relax Linda. I'm sitting here having a cup of coffee. Why don't you join me?"

"Oh, thank you Danielle. I'll be right there."

Three minutes later she was knocking at the front door. When I opened it she rushed in and hugged me tightly. "I had to talk to somebody. I'm so upset I can't think straight. My life is ruined."

I patted her on the back. "I'm sure it's not that bad. Let me get you a cup of coffee and then we can talk." I led her into the kitchen and poured her coffee. "Now sit down and tell me what's going on."

"I think Jim is gay!"

That got my attention. "Why do you say that? What happened?"

"I was supposed to go out last night with some friends from the office. We were going to dinner and then to a movie. Jim told me it was OK. He said that he would just fix some dinner for himself and then watch TV. Partway through dinner I began feeling sick to my stomach. I rushed into the bathroom and threw up. It was awful. I decided that I had to go home right away. When I walked into the house I got the worst shock of my life. There was Jim sitting at the kitchen table eating his dinner wearing a dress and high heels. I couldn't believe my eyes. He had a long brown wig on his head and makeup on his face. He actually looked rather attractive. Oh, Danielle! All this time I never realized that I was married to a pervert."

"Calm down, Linda. I don't think Jim's a pervert. What did you do when you saw him?"

"I went ballistic. I screamed and cried and called him all sorts of nasty names. When I ran into our bedroom I saw a box filled with his women's clothes lying on the bed. I threw them out into the hall and told him he wasn't sleeping with me any more. He could just sleep with his girly things in the spare bedroom. After that I slammed the door on him and just lay on the bed until I cried myself to sleep."

"You poor dear. It must have been a terrible night. What did Jim say to you?"

"He kept saying he was sorry and he didn't mean to hurt me and it wasn't what I thought. He tried to hug me and comfort me but I just pushed him away. When I slammed the bedroom door on him, he actually started to cry. I just don't understand it Danielle. Why would he do something like this?"

"Trust me, Linda. This is not as bad as you think it is. I don't think that Jim is gay or perverted. He just likes dressing up in beautiful, feminine clothes. You'd be amazed at how many men do it. They're called transvestites. The vast majority are heterosexuals. They have no interest in becoming women or having sex with men. They just like to dress up and look pretty."

Linda looked at me strangely. "How do you know so much about this?"

"I've actually done a fair amount of reading on the subject. Do you remember last year when Tom lost the bet and had to dress up as a maid and serve us lunch?"

Linda actually smiled. "I sure do. He really looked cute in that uniform. But what's that got to do with Jim."

"I'm going to tell you a secret but you've got to promise never to tell another soul." Linda nodded and I continued: "I really got turned on watching him serve us in his sexy uniform and high heels. As soon as you were out the door I grabbed him and led him to the bedroom where I practically ripped off his clothes. I can't explain it but it was thrilling making love with both of us wearing sexy lingerie."

"I can't believe it."

"It's true. What I discovered that day is that Tom also enjoyed making love while dressed as a woman. Over the next few weeks we tried a few other dress up games and found that Tom really liked dressing up as Tammy and playing my girlfriend. I also discovered that I really like having both a husband and a girlfriend in the same body. Over the last year Tammy and I have done lots of things together. Not only does Tom dress up here at home but we also go out together as girlfriends.

"You've got to be kidding me. I just can't believe that Tom likes dressing up as a woman. He always seems so macho."

"Let me show you something," I said. I went to the bedroom and retrieved a special photo album that Tom and I had put together. Returning to the kitchen, I set the album in front of Linda. "Take a look at my macho husband Tammy."

Linda opened the cover. The first page had several pictures of Tammy in her maid's uniform. Linda smiled remembering the luncheon. She turned the page and gasped. "My God, Danielle. Is that really Tom? He's absolutely beautiful." She continued to leaf through pages showing Tammy in a variety of outfits. There was even a picture of Tammy and me in our matching leather skirts and stiletto-heeled boots. "This is amazing. I would never have guessed that you and Tom were doing something like this. Do you really like seeing Tom dressed like this?"

"I love it and Tom loves it. Tammy is a great girlfriend and Tom is a wonderful husband. Since I met Tammy, Tom has become much more considerate. He loves to bring me flowers and presents. He also enjoys dressing in his maid's uniform and helping me around the house. Honestly Linda, discovering Tammy has been the best thing that ever happened to our marriage."

"You make it sound great. I sure would like to have Jim help me more around the house and it might be fun to have a girlfriend. I'm not sure what I should do."

"Let's talk about it. Would you like another cup of coffee?" Linda nodded as she took out a handkerchief and dabbed at her eyes. As I poured the coffee I asked: "Where is Jim now? Did he go out to play golf with Tom and the guys?"

"I assume so. He wasn't at home when I woke up. I think he snuck into the bedroom early this morning to get his clothes. When I went downstairs he had left me a note telling me again that he was sorry and that he loved me and would do anything for me if I would forgive him."

"That sounds pretty good. Did you check out his wardrobe?"

"I was so upset that I didn't pay any attention to what Jim had in the box. When I went into the spare bedroom this morning the box was sitting on the floor of the closet."

"I think it's time we see what he has in his box. Are you game?"

"If you think it's all right." She smiled and said: "Actually I'm curious to see what kind of clothes he has. Let's do it." We finished our coffee and walked to Linda's house. We opened Jim's box and started to pull out his clothes. He had a larger wardrobe than Tammy. There were several dresses plus skirts, blouses and a suit. He had four pairs of high-heeled shoes and a pair of boots. He also had nightgowns, bras, panties, stockings and a very nice pair of breastforms. On top of the pile was his brunette wig. "Wow, he must have spent a fortune on all this stuff."

"Obviously he's been dressing up for a long time. This is clearly something that's very important to him." I held up a beautiful long black beaded evening gown. It had a V-neckline and a slit in the front that would show off a lot of Jim's leg. "I'll bet he would really look beautiful in this."

"I think that's prettier than anything I own."

"How would you like to see Jim wearing it?"

"I'm not sure. After last night, I'm afraid that I might react badly. I need your help, Danielle."

"I have a suggestion. How would you like to have Tammy and me come over for dinner tonight? We'll both dress in evening gowns. You'll need to dress in one also and get Jim to wear this dress. It will give you an opportunity to get to know Jim's feminine side with Tammy and me here to give both of you moral support. It will also be very interesting to see what happens when Tom and Jim see each other wearing dresses."

"What a great idea. I'm not sure I could spend an entire evening alone with Jim wearing a dress. Having you and Tammy here will make it a fun evening."

We spent the next half hour working out all of the details for the evening. We then put everything back into the box and put it back into the closet. I gave Linda a hug. "It's going to be a great evening. Give us a call when Jim starts getting dressed and make sure you find out his femme name."

"Thanks very much for everything, Danielle. I'm actually starting to get excited. It will be different."

I couldn't wait for Tom to get home so I could tell him about our plans for the evening. As soon as he came into the house I gave him a hug and kiss and led him to the kitchen table. "We need to talk. How was Jim this morning?"

"I think he may be sick. He barely spoke to any of us and I don't think I saw him smile all day. What's going on?"

"How would you like to get all dolled up and go out to dinner tonight?"

Tom smiled: "I'm game. Where are we going?"

"To Linda and Jim's house."

"You must be kidding. You're asking me to dress up as Tammy and go to dinner at our best friend's house. Are you out of your mind?"

"What if I told you that Jim will also be wearing a dress?"

"Why would Jim wear a dress?"

"Because he's a transvestite."

Tom's eyes opened wide and his jaw dropped. "This is unbelievable. You need to back up and tell me the whole story."

I gave him the story including the gameplan for the evening. By the time I was done, he was smiling. "So we're going to dress up in evening gowns and have dinner with Jim and Linda who will also be wearing evening gowns. It should be an interesting night. Do you think I should wear my pink satin gown?"

"Absolutely. It's the most beautiful, feminine dress you own. I think it's very important that Linda and Jim see how much fun we have as girlfriends."

"If I'm going to wear the pink dress, I'll need you to help me glue on my breastforms so that the seams are hidden." Tom stood up from the table. He was clearly excited. "Maybe I should start getting ready now."

"Relax Tammy. I don't expect Linda to call before 6 or 6:30. We've got plenty of time." For the next few hours Tom puttered around the house. I could see him watching the clock waiting for me to say it was time to get dressed. Finally we headed upstairs. We climbed into separate bubble baths to relax and prepare for the evening. Once we were clean, shaved and powdered, Tom put on a new panty girdle that I had recently purchased for him. It had padding on the hips and rear to give him a more feminine figure and a split crotch so he could pee without taking it off. He slid a pair of sheer stockings up his legs and attached them to the garters of the panty girdle. Then he lay down on the bed so I could glue on his breastforms. Once they were in place he used a special makeup to hide the seams. When he was done he stood in front of me with beautiful, natural-looking breasts.

"Could you help me with my corset?" he asked. It was a pink full-length satin corset. Tom positioned his breasts in the cups, hooked the front and stood so I could tighten the laces. When I was done, I stood back to admire his voluptuous figure. The padding had added 4" to his hips while the corset had taken 4" off his waist and pushed his breasts up to create a spectacular cleavage.

"You really do have a fantastic figure."

"Thanks. It just shows what some padding and the right lingerie can do for a girl."

We sat next to each other at the vanity to put on our makeup. As I worked on my face I periodically checked to see how Tom was doing. It was amazing to watch him. When he was done, I was staring at the face of a beautiful woman. "Could you help me with this?" he asked, handing me his wig. I carefully positioned it on his head and brushed it out. Then I leaned over and kissed his shoulder.

"Would you like to wear diamonds or pearls tonight?"

"Could I wear your diamonds?" I opened my jewelry cabinet and took out my diamond heart pendant along with a pair of diamond stud earrings and a tennis bracelet. I hooked the necklace for him while he put on the bracelet and earrings. While I finished putting on my makeup, he went to work on his nails. After gluing on a set of artificial nails, he painted them with two coats of pink polish. Checking his reflection in the mirror he said: "I think I'm ready for my dress." It was a long pink satin gown with a straight sheath skirt that ended at Tom's ankles and a walking slit in back. It was an off-the-shoulder style with a low-cut front that showed a modest amount of cleavage. Tom stepped into the dress and slipped his arms into the short sleeves. He then turned his back so I could zip it up. The gown fit him like a glove. Even with the walking slit, he would be constrained to take short steps. He sat down and put on his shoes. They were pink patent leather pumps with 5" stiletto heels.

"You really look gorgeous tonight, Tammy. I'm already getting hot for your beautiful body." While Tammy stood admiring herself in the mirror, I put on my dress and shoes. I wore a cream-colored gown with an open back and a thigh-high front slit, and a pair of white sandals with 4" heels. We stood side-by-side, a couple of beautiful women ready to party. "Let's have a glass of wine while we're waiting."

Linda called a little after 6 PM. "You can come over now. Jim is finishing his shower. I gave him some depilatory cream and told him to make sure he removed all his body hair."

"Tammy and I are ready. We'll be there in a couple of minutes." I handed Tammy her purse. "Let's go. Jim is in the shower."

We climbed into the car, opened the garage door and backed out. "How are we going to get into their house without being seen?

I smiled. "Linda loaned me their garage door opener. We'll just pull into their garage and close the door before we get out of the car."

Linda was waiting for us at the back door. She was wearing a beautiful green velvet gown with a long full skirt and a plunging neckline. It really accentuated her small waist and ample bosom. "You girls look lovely tonight. That's a beautiful dress, Tammy. It fits you perfectly."

The three of us hugged. "How are you doing?" I asked.

"I'm really nervous. I couldn't do this without you two. Thank you so much for being here."

Tammy smiled at her. "I can't wait to meet my new girlfriend. By the way, what's her name?

"Jim told me that he thinks of himself as Jamie when he's dressed." Linda led us into the kitchen. "I was just fixing a casserole for dinner. Tammy, could you set the table for us while Danielle makes a salad?"

"I'd be happy to, Linda." Tammy walked into the dining room and went to work while Linda and I stood side-by-side at the kitchen counter talking in whispers as we worked on the meal.

"I'm amazed, Danielle. Tammy really looks like a beautiful woman. Aren't you at all jealous?"

"No I'm not. Tammy works very hard to look pretty and I enjoy helping her do it. When she looks like she does tonight, she's happy which makes me happy."

"She acts so feminine. If I didn't know it was Tom in the dress, I would never guess."

"Well she's had a lot of practice in the past year. I'm willing to bet that while Jamie may be a little awkward and uncomfortable at first, by the end of the evening you won't be able to tell that she's a man in a dress."

When we were finished preparing the meal, Linda excused herself to check on Jamie. When she came back to the kitchen she said: "Jamie said she would be ready in about 10 minutes. I'll put the casserole in the oven now and we can wait in the family room."

Tammy and I sat down on the couch while Linda busied herself turning on some music, adjusting the lights and lighting several candles. There was a vase of roses and a tray with champagne and four glasses sitting on the coffee table. A few minutes later we heard Jamie's high heels clicking on the floor. Linda stood in the doorway watching her new girlfriend progress across the kitchen. "You look beautiful in your dress, Jamie. Turn around and let me see how it fits." Jamie did a pirouette. "It looks lovely on you. Come into the family room," she said taking Jamie's hand. Jamie was focused on Linda as she walked into the room and didn't notice us sitting there.

In her most feminine voice, Tammy said: "Linda's right. You look lovely in that dress."

Jamie spun around, a look of shock and terror on her face. "What the …!" She recognized me and then looked at Tammy and did a double take. "My God! Tom, is that you?"

"Tonight it's Tammy, not Tom." We stood up and Tammy approached her, taking hold of her hands. They stood staring into each other's eyes as Linda and I watched with smiles on our faces. "It's a pleasure to meet you Jamie. We've been buddies for a long time but I never thought we would also be girlfriends."

A tear rolled down Jamie's cheek. "Oh Tammy, I've always wanted to have a girlfriend." They hugged each other.

"Hey, what about us! We're your girlfriends too," I said. The emotional moment lightened. Everyone laughed as they broke their embrace and put their arms around Linda and me.

Linda said: "I think it's time for a toast." She popped the cork on the champagne. I held the glasses while she poured. We stood together and clinked our glasses. "Here's to a wonderful evening and an opportunity to get to know my two newest girlfriends, Jamie and Tammy."

"Sit down girls while I check on the dinner and get us some hors d'oeuvres."

Jamie and Tammy sat side-by-side on the couch while I took a chair on the other side of the coffee table. Jamie looked very pretty and feminine in her long black gown and high-heeled sandals. "You both look lovely tonight. I need to get some pictures," I said taking my camera out of my purse. The two of them posed as I clicked off several shots.

Linda returned with the hors d'oeuvres. "It will be about 30 minutes until dinner is ready. Help yourself to some appetizers and some more champagne." We sat sipping our champagne and chatting together. As we talked, I watched Linda's reaction. As the conversation continued and Tammy and Jamie sat side-by-side looking, acting, and sounding like women, Linda began to visibly relax and enjoy herself.

The kitchen buzzer sounded. "It sounds like dinner is ready," announced Linda. "Danielle, perhaps you could help me get the food on the table while you two girls light the candles and pour the wine."

When we were all seated with a wineglass in hand, I proposed a toast to the first of many evenings together as girlfriends. We continued our conversation over dinner. Eventually my curiosity got the better of me. "I don't want to pry Jamie but I'm curious about how you got started dressing up."

"I had three older sisters. They started dressing me in little girl's clothes when I was 7 or 8. As I got older they dressed me in their fancy dresses and high heels. They even dressed me in a prom gown one year for a Halloween party. I was the hit of the party. When they went away to college, I continued dressing in their clothes whenever my parents were out for the evening. I loved the feel of satin and lace against my body. When I went away to college, I had very few chances to dress up until I met Linda."

Jamie looked at Linda and smiled shyly. "After we got married, I tried on your clothes a few times when you were out but they were too small for me and I was afraid that I would rip something. A few years ago, I started ordering clothes for myself over the Internet. I knew that sooner or later you would discover my secret but I couldn't stop and I couldn't tell you for fear that you would leave me. When you came home and found me dressed, it was the worst night of my life. I thought for sure that I was going to lose you. I couldn't believe my ears when you told me this afternoon that you wanted me to dress up in this gown and spend the night as your girlfriend. This is turning out to be one of the best nights of my life."

"You have Danielle and Tammy to thank for tonight. If I hadn't talked to Danielle this morning, I probably would have reacted very differently. She's the one who convinced me that I needed to get to know your feminine side. When I discovered that Tammy and Danielle have been girlfriends for the past year, I knew it would be OK."

Linda looked at Tammy. "Danielle told me that you never dressed up before you lost the bet on the football game."

"That's right. My first experience with women's clothes was as Tammy the maid. I discovered that I loved the feel of the clothes against my body. I also found that I liked to dress up in sexy outfits and show off my feminine charms. I think both Danielle and I have been amazed by how much we enjoy being girlfriends. It has brought a whole new dimension to our marriage. If you give it a chance, I think you two will also find tremendous happiness."

"You know, Tammy," said Jamie. "I was really jealous of you when you lost that bet. I would have loved to be the one to dress up as a maid and wait on the ladies. Unfortunately there was no way I could take your place."

"At the time I would have been happy to let you."

It was a wonderful dinner. When we were done, I helped Linda clean up the dishes while Tammy poured coffee and Jamie mixed us after-dinner drinks. It was nearly midnight when Tammy and I finally said our good-byes. It was sweet watching Tammy and Jamie hug and kiss each other as girlfriends.

When we got home we headed straight for the bedroom. Both of us were incredibly horny. I took Tammy in my arms and kissed her passionately. As we kissed we unzipped each other's gowns. We stepped apart and let them drop to the floor. Then we lay down next to each other on the bed and continued our foreplay. My loins were getting hot and my juices were flowing. Tammy rolled onto her back, spread the split crotch of her panty girdle and eased her manhood out of its elastic prison. It stood at attention, pointing at the sky. I tore off my panties and climbed on top of her, positioning myself to take her throbbing erection in my mouth as she kissed and sucked my aching vagina. Our moans of ecstasy grew louder as we brought each other to a powerful orgasm. When we had both been satisfied, we slipped on our nightgowns, cleaned off our makeup and went to sleep in each other's arms.

It was nearly 9:00 when I woke up. Tom was still sound asleep beside me. I reached under the covers and began to fondle his penis through his nightgown. He opened his eyes and smiled at me as his erection grew. He slid his hand under my nightgown and found my love button. He pushed his finger deep inside me and began to stimulate me. It wasn't long before we were both ready. I rolled on top of him, impaled myself on his love muscle and rode him to a satisfying climax. As I sat there with him still inside me, I smiled down at him: "Now that we've had some early morning fun, what would you like to do today?"

"Since I went to the trouble of gluing on my breasts and fingernails last night, would you mind if I spent the day as Tammy?"

"I wouldn't mind at all. In fact I'd love it. Are you going to be Tammy my maid or Tammy my girlfriend?"

"Do you have a preference?"

"Well there is some ironing that needs to be done. Why don't you wear your maid's uniform this morning and then we'll change clothes and go to the mall after lunch?"

"That sounds like a great idea. Why don't I make some lasagna for us? Then we can just heat it up when we get home."

With our plans set Tom headed for the bathroom to shower and shave while I filled the tub for a bubble bath. After bathing, I dressed in a skirt and blouse and headed for the kitchen, where Tammy was hard at work preparing our breakfast. After breakfast she went to work on the ironing while I relaxed with the newspaper.

It was about 11:00 when the phone rang. "Hi Danielle, it's Linda. I was just calling to thank you again for last night. It was a fantastic evening. It was so much fun getting to know Tammy and Jamie. I still can't believe how beautiful and feminine they both are."

"Tammy and I enjoyed it at least as much as you did. So tell me, did you and Jamie have fun after we left?"

"My God, Danielle! It was the wildest night of sex we've ever had. We really did some kinky things. So what are you two doing today?"

"Right now Tammy is doing some ironing for me. We thought we might go to the mall later."

"How would you like to see a fashion show instead? I've told Jamie that I'd like her to model the rest of her wardrobe for me this afternoon. I'd love to have you join me and I'm sure that Jamie would like to show off her clothes for Tammy."

"That sounds like great fun. In fact, Tammy was planning to make lasagna for dinner. I'll have her make enough for four and we'll bring it with us."

"That would be great. Why don't you come about 2:00? Do you think that Tammy would be willing to wear her maid's uniform this afternoon? I know that Jamie would love to see what it looks like on her."

"I'm sure she'd be happy to wear it. We'll see you later."

I walked into the kitchen to tell Tammy about the change in plans. She was ecstatic. "I can't wait to see all her clothes. I'll bet she has some very sexy outfits."

"Linda asked if you would wear your uniform. Jamie would really like to see you in it. I told her that I was sure you would love to do it. I also told her that I would have you make enough lasagna for all of us."

When Tammy had finished the ironing and made the lasagna, she sat down at the vanity to touch up her makeup. It was clear that she was excited about seeing her new girlfriend again. At 2:00 we climbed in the car for the short trip to their house. Again we pulled directly into their garage and lowered the door so Tammy could get out of the car without being seen.

Linda ushered us into the house. "You look lovely in your uniform, Tammy. Jamie is dying to see you in it. Let's go into the family room and wait for the show to start." A few minutes later Jamie entered the family room wearing her first outfit. It was a beautiful black satin cocktail dress. It had spaghetti straps and a tight, straight skirt that ended several inches above her knees. On her feet was a pair of black patent leather pumps with 5" heels. She strode back and forth across the room, twirling to show off her clothes.

Linda smiled at her girlfriend and said: "That dress looks stunning on you, Jamie. I didn't realize you had such good taste in women's clothes. I'm also impressed by how well you walk in those stiletto heels. I'm not sure I could walk in heels that high."

I laughed. "I can tell you from experience that they definitely take some practice to get used to."

Jamie turned to Tammy. "I see you wore your maid's uniform. Stand up and turn around so I can see what it looks like." Tammy stood up and did a pirouette and then curtsied. "I love it Tammy. It really looks sexy on you."

I looked at Linda. "It sounds like Jamie would like to have one for herself. I can give you directions to the store where I bought Tammy's."

Jamie laughed. "There's no need to do that. I've shopped for clothes in the same store myself. I've even tried on a couple of uniforms but I was always afraid to buy one."

Linda chimed in. "I definitely think we need to see about buying you one."

For the next couple of hours, Jamie modeled a variety of skirts, blouse and dresses. They included some outfits that were frilly and feminine, others that were sexy and provocative and a few that were quite conservative. While Jamie modeled, Tammy fixed appetizers, served cocktails and prepared the dinner. At last Jamie announced that she only had two more dresses to model. "Why don't you come upstairs with me Tammy? We can each model one of them. Then we can have some dinner."

They left to get changed. "So what do you think about your new girlfriend, Linda?"

"The last two days have been incredible, Danielle. I would never have believed that I would spend an afternoon watching my husband model his women's wardrobe. I'm not sure where this will all lead, but I'm looking forward to spending more time with Jamie and Tammy and you."

A few minutes later Jamie and Tammy walked into the room arm-in-arm. They were both wearing sexy, knit mini-dresses that showed off their feminine figures and beautiful legs. Tammy's dress was black and Jamie's was red. They took turns walking across the room and back, swinging their derrieres in a most provocative manner.

Linda and I applauded the show. "You girls are really hot," I said. "If you walked out in public in those dresses, you'd have the men falling all over themselves."

"I think dinner is ready," said Linda. "Grab yourselves a glass of wine and let's eat before it gets cold." We all sat down to another enjoyable dinner as girlfriends. After dinner, we helped Linda and Jamie clean up before heading for home.

Late that night after another awesome session of lovemaking, we lay side-by-side in bed. "How do you like Jamie?" I asked.

"I think she's wonderful. It was a shock to discover that Jim is a transvestite, but after last night and today I can't wait to spend some more time with my new girlfriend.

 

THE END

  

  

  

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