Crystal's StorySite


My Husband Tammy

by Tammy Richards


My name is Danielle and my husband Tom is also my best girlfriend Tammy. Let me tell you how this happened.

A few years ago, Tom lost a bet to me on the Michigan Ohio State football game. As a result he had to dress up in a maid's uniform and serve lunch to me and three of my girlfriends. They all encouraged me to dress him in a very feminine, sexy outfit. I'll have to admit it sounded like a good idea to me also. Tom is a very handsome guy, about 5' 10" with a slim body that he keeps in shape through regular workouts. I thought that if I got him the right outfit and did a good job with his makeup, I could turn him into a very attractive woman. As my friends told me, this would probably be the only chance I ever had to get him into a dress so I better make the most of it.

The first problem was to find him a maid's outfit. On Sunday afternoon while Tom was watching a football game, I got on the Internet and started searching. I was amazed by the number of web sites that were selling woman's clothes to men. There was everything imaginable dresses, shoes, lingerie, wigs, even maid's uniforms. I discovered a web site that had a retail store less than 15 miles from our house.

After work on Monday, I headed for the store. It was located in a small strip mall. The store looked a lot like many other woman's stores, except that the clothes were much sexier and the customers were all men, a couple of them dressed in woman's clothes. I approached the saleslady (sorry salesman in a dress). "Can I help you?" he asked.

"I hope so. My husband lost a bet to me last weekend and his penalty is that he has to dress up in a maid's uniform and serve lunch to me and three of my friends."

The salesman burst out laughing. "That's great. It will be something to see. I'll have to say your husband is a very good sport if he's willing to go through with this. Let me show you what we have." He led me to a rack holding a large number of maid's uniforms in a variety of styles and colors. "Do you know his size?"

I handed him a piece of paper with Tom's measurements on it. "This is incredible," I said looking at the selection. "You must sell a lot of these."

"It's one of our biggest sellers. You'd be amazed how many men like to get dressed up in one of these outfits."

After looking through the inventory, I selected a black satin uniform with white lace trim. I thought it looked very sexy.

"I'd also recommend a full white petticoat to wear under the skirt. Let me show you what we have," he said leading me to another part of the store. After I picked out a petticoat he led me to the shoe department. "Has your husband ever worn high heels before?"

"Certainly not," I said, blushing.

We have high heels that go up to 6" in height, but if you want him to be able to work in the shoes, I would recommend a heel height of no more than 4". He showed me a pair of beautiful black patent leather pumps with stiletto heels. "He'll need to practice with these but he should be able to get used to them."

"I'll take them."

"Is your husband going to be dressed for most of the day?"

"That's the plan. Why do you ask?"

"Since he hasn't had much experience in high heels, his feet are going to get very sore. I'd suggest that you consider buying him a pair of low-heeled shoes to give his feet a rest. I've got a very nice pair with 1" heels that are on sale.

This was starting to add up but I figured that since I was in this far, I might as well go all the way. "What else do I need?"

"I assume he'll need panties and a bra, unless you're going to have him wear yours." He showed me a pair of white satin panties with ruffles across the rear and a very sexy black lace bra. "How about a pair of breastforms to fill the bra?" he said, pointing to a display.

I took one look at the price and decided I could find something else to fill out the cups. "I'll take the panties and bra, but pass on the breastforms."

"Do you want him to wear stockings or pantyhose?"

"Let's go with stockings, they're much sexier."

The salesman showed me a pair of sheer black back-seamed stockings. "These will make his legs look very sexy. I'd suggest getting a corset to hold up the stockings. That will also allow you to give him the proper feminine figure." I agreed. "Will he need a wig?"

"That's one thing I think we can do without. I have a very nice shoulder length blonde wig that he can wear."

Taking my selections to the counter he said: "I think you're all set unless you need any makeup or jewelry."

I picked out a pair of gold clip-on earrings and a set of artificial nails that were sized for men's fingers. "I think this will do it," I said taking out my credit card. The bill came to nearly $300 (he gave me a discount). "I sure hope this is worth it," I said as I signed the credit card slip.

"I'm sure your husband will look beautiful in this outfit."

When I got home, I hid all of the packages in the back of my closet. I could hardly wait for Saturday to see Tom in his uniform. Over the next several days, my girlfriends pestered me unmercifully trying to find out what I had bought for him to wear. I just smiled and told them to wait and see.

I won't bore you with the details of Tom's day as Tammy the maid. Suffice it to say I succeeded beyond my wildest dream. Once he was dressed and made up, he looked like a beautiful woman. There was no way that anyone would guess that it was a man under the dress. I think Tom was also amazed by his appearance. When he first saw himself in the mirror, he just stood there checking himself out from all directions.

Tom was a real sport about everything. After some initial shyness and embarrassment, he really got into his role. Watching him sashay around the house in his short skirt and high heels got me very turned on. By the time my friends left, I was so horny that I thought I would go crazy. As soon as the door was closed I kissed him passionately and slid my hand under his skirt to massage his throbbing manhood. Leading him to the bedroom, I helped him out of his uniform and then took off my skirt and blouse. He looked incredibly sexy standing in front of me in his lingerie. Pushing him down on the bed, I climbed on top of him and rode him like there was no tomorrow. It turned out to be one of the most satisfying afternoons of lovemaking we had ever had.

I knew I wanted to see more of Tammy. To my surprise, Tom also indicated a willingness to dress up again. While I was thrilled by his comments, I wasn't sure if he meant it or if it was just the sex talking. Therefore I spent a lot of time over the next few days thinking about the best way to proceed. I decided that the first step was to see how willing Tom would be to get dressed up again in a non-threatening situation.

Friday night after dinner, Tom sat down to watch some television. I excused myself and went to the bedroom where I changed into my sexiest black satin nightgown. I also put on a pair of thigh high stockings and my high-heeled pumps. I carefully applied my makeup sprinkled on some perfume, and combed my hair into a sexy style. Then I set a pretty pink satin nightgown on the bed for Tom to wear.

When I returned to the family room, Tom's eyes practically popped out of his head. Taking my hand he pulled me down onto his lap and kissed me passionately. "It looks like you're ready for some fun tonight."

I ground my ass into his groin and said in a sultry voice: "I'm ready but you're not. Why don't you go slip into something sexy also. I left something out on the bed for you to wear if you're interested."

His face lit up with a big smile. "I shall return," he said and headed for the bedroom. While I waited I turned down the lights and put some romantic music on the stereo. I then got us each a glass of chardonnay and sat down to wait. I was curious if he would put on the nightgown and, if so, whether he would put on any of his other female clothes. As the minutes went by I decided that he must be getting himself all dolled up.

Finally I heard the tapping of high heels as he walked across the kitchen floor. Entering the family room, he did a pirouette in front of me. "Do I look OK?"

I stood up and hugged him tightly. "You look beautiful." I was surprised and pleased. Not only was he wearing the nightgown but he had put on his stockings and high heels. He was also wearing my blonde wig and had made a pretty good effort to apply makeup to his face. What really surprised me were his fingernails he had painted them a pretty pink. I picked up my glass of wine and handed the other one to him. Clinking his glass I said: "I love you, Tammy."

He smiled and kissed me. "I love you too."

We snuggled together on the couch. For the next half hour we sipped our wine and chatted like two girlfriends. Tom tried hard to play the role of a sexy young woman. Looking at him I could feel my juices starting to flow. When we finished our wine I leaned closer and kissed him tenderly on the lips. "I'm getting very horny. Why don't we adjourn to the bedroom?" As we walked to the bedroom, I could see his erection poking at the front of his nightgown. "It looks like you're pretty horny too."

We lay down on the bed and began to kiss and fondle each other. As our passion grew I rolled on top of him and began to kiss my way down his body. Kneeling between his legs, I grabbed the hem of his nightgown and pushed it up around his waist. Taking his erect penis in my hands, I lowered my head and began to kiss and lick the head of his throbbing shaft. I slid it in and out of my mouth going a little further each time. Tom lay on the bed moaning in ecstasy. I could feel his penis start to pulsate and then he exploded, shooting his cum deep into my throat. I swallowed some but kept the rest in my mouth. Then I moved forward on top of him and kissed him passionately, allowing his juices to flow back into his mouth. His eyes opened wide with surprise and then he smiled and hugged me tightly.

"It's your turn now," he said, rolling me over onto my back. Gently he pushed the top of my nightgown out of the way so that he could give his attention to my breasts. He kissed and sucked each nipple until it was tingling. Then he turned his attention to my love nest. I spread my knees apart and he went to work, using his tongue to stimulate my clit. I was in heaven as I lay there on the receiving end of his magical mouth. My body was wracked with one powerful orgasm after another. Just when I thought I couldn't take any more, he paused to raise his nightgown and then he slid inside me. It didn't take long before we both exploded in one last orgasm.

He rolled off me and we lay side-by-side trying to catch our breath. "My God," he said. "I think that was the most awesome sex we've ever had. I hope you enjoyed it half as much as me."

"I loved it and I love you for being willing to play these dress up games with me. It's clear that both of us get turned on by wearing feminine, sexy clothes."

"We sure do. I had never even thought about dressing in women's clothes before last weekend and now I can't wait to do it again."

Given Tom's enthusiasm for dressing up, I decided it was time to pay another visit to the store where I had purchased his maid's uniform. The salesman (still wearing a dress) recognized me as soon as I walked in. "Welcome back. How did your husband do as the maid?"

"He did very well and he ended up enjoying the day." I took a couple of pictures out of my purse. "Here are some pictures of my husband Tammy."

"Wow, he's beautiful. He would have no problem passing as a woman anywhere. So what can I do to help you today."

"First I'd like to purchase the breastforms you showed me last time, and then I'd like to see about buying him a sexy dress or skirt and blouse to wear."

"It sounds like he's discovered the joys of beautiful clothing. Do you have anything particular in mind?"

"I was thinking that it might be fun to buy him a leather miniskirt."

"That's a great idea. Let me show you what we have," he said leading me to a rack of skirts.

I looked through the rack and picked a straight black leather skirt that was mid-thigh length. "Would you happen to have one in my size also?"

"Here you are," he said handing me another skirt. "Are you thinking about getting matching outfits?"

"I thought that might be fun to do."

"Let me show you our blouses," he said leading me to another rack. There were a wide variety of choices. I selected a sheer white blouse with a ruffled front and plunging neckline, again purchasing one for both Tom and myself.

"Those skirts look great with leather boots. I can show you what we have." I followed him to the shoe department where he showed me a pair of knee-high black patent leather boots with 5" stiletto heels. "I know we have this style in both his size and yours."

"I'll take them. Would you mind if I tried on my outfit to make sure that everything fits."

He led me to a dressing room where I quickly stripped out of my clothes and put the new clothes on. Checking myself in the dressing room mirror, I concluded that the outfit was really sexy on me. I stepped out of the dressing room to try out the shoes. They fit perfectly although it would take some practice to get used to walking in heels that high.

The salesman came up to me. "That outfit looks great on you. I'm sure it will look almost as good on your husband."

"Thanks, I'll take it. I'll also need to get Tammy some pantyhose. I want him to look sexy, but not like a slut."

He handed me a package of sheer black pantyhose. "Anything else?"

He'll need a white bra to wear under his blouse and a panty girdle to hide his bulge.

"If you want to give him a feminine front, it might be better to get a gaff than a girdle. The gaff will hold his manhood back between his legs."

I thought about that for a moment. "That sounds like it could get pretty uncomfortable. I think I'll get the panty girdle for now."

"OK. I'll ring up your purchases while you're getting changed."

Needless to say I put another major dent in my credit card but I knew for sure now that it was worth it. I decided to wait until the following weekend to give him his new clothes. On Saturday afternoon while Tom was watching a football game, I went out to the video store and rented a couple of chick flicks. When the game was over I walked into the family room carrying the movies and a couple of glasses of wine.

I sat down next to him and handed him a glass of wine. "I got a couple of movies for us to watch tonight."

He glanced at the titles. "Those are chick flicks." Then he stopped and his face broke into a big smile. "Are you thinking that Tammy might like to watch them with you."

"That's what I was hoping. I even bought something new for you to wear."

"That sounds great. What did you buy me?"

"Come and see," I said taking his hand and leading him to the bedroom. There I handed him a big box wrapped in pink paper. "This is a special present for my new girlfriend Tammy."

He tore into the box like a little kid. The first things he took out were the breastforms. "Wow these are beautiful," he said holding them against his chest.

"They'll probably give you a better cleavage than I have."

Next came the skirt, blouse and boots. "I'm really going to look sexy in this outfit. I can't wait to try everything on. However, I think I better take a shower and shave before I get dressed."

"Why don't you take a nice hot bubble bath? It will put you in the right mood for this evening. I can get it ready while you're getting undressed."

I had the bathtub full of hot water and bubbles when Tom came into the bathroom a few minutes later. He stepped into the tub and slid down under the bubbles, allowing them to caress his skin. "Just relax there for a while. I've set out some powder for you to use when you're done. Give me a call when you've got your lingerie on and I'll help you with your makeup."

It was about 45 minutes later that I heard Tammy's voice calling from the bedroom. When I got there he was standing in front of the mirror admiring himself. He had put on the bra and inserted the breastforms. He was also wearing his panty girdle, pantyhose and the high-heeled boots. He struck a seductive pose: "How do I look?"

"Like a real hot chick. You've got a figure that most women would die for. Let's get your makeup done so you can see the complete package." I noticed that he wobbled a little as he walked to the vanity. "How do the boots feel?"

"They fit perfectly but I'm going to need to practice walking in them. The heels are much higher than my shoes."

I spent a lot of time doing his makeup so that it would be perfect. I explained every step as I went along so that he'd be able to do it himself in the future. When I had finished his makeup and placed the wig on his head, I handed him the skirt and blouse. Watching him get dressed, I marveled at how beautiful and sexy he looked.

When he was dressed I led him to the full-length mirrors. The smile on his face as he stared at his reflection told me that I had done the right thing in buying him the clothes. "Wait there for a minute. I need to get a picture of this." I quickly got the digital camera and took several pictures of him in different poses. It was clear that he was really enjoying himself.

"I need to put on something a little sexier also. I've got the dinner started. Why don't you make us a salad and set the table while I get changed?" Tammy headed for the kitchen while I stripped off my clothes and went into the bathroom to get cleaned up. After a quick shower I put on my makeup and then dressed in my identical outfit. When I entered the kitchen Tammy was standing with his back to me, mixing us a couple of Cosmopolitans. I posed and said: "How do I look, Tammy?"

When he turned around, I thought he was going to faint from shock. His eyes widened and his jaw dropped. "My God, you bought us identical outfits. You look beautiful." We moved toward each other as fast as our high-heels would allow.

I put my arms around his neck and looked into his eyes: "I just thought it would be fun to wear matching outfits."

He kissed me. "I think so too. What a great idea."

The rest of the evening was fantastic. I thought of Tom as my girlfriend Tammy and he did a great job of playing the part. We had dinner and relaxed on the couch watching the movies. By the middle of the second movie we were taking much more interest in each other than we were in the TV. We snuggled closer together and began to kiss and fondle each other. I slid my hand under Tammy's skirt to play with his nylon-covered thigh while his hand slid down the front of my blouse to massage my breasts. We got so hot and horny that we ended up making mad, passionate love on the family room floor.

It was late and we were both exhausted when we fell into bed. When I woke the next morning I was surprised to find that Tom wasn't sleeping beside me. He usually likes to sleep in on Sunday mornings. I rolled over and noticed a bell sitting on my nightstand. I couldn't believe my eyes. I sat up in bed and rang the bell. A moment later Tammy walked into the bedroom, wearing his maid's uniform and carrying my breakfast on a tray. "Good morning Mistress Danielle. Did you have a good night's sleep?"

"I slept like a log." I looked down at my breakfast. "This looks like a wonderful breakfast, Tammy. What's the occasion?"

"I just wanted to thank you for last night. It was a wonderful evening and I really enjoyed being your girlfriend. Today I'm going to be your maid. I'll be happy to do anything you want me to do."

He was true to his word. I took a bubble bath, read the paper, surfed the web and even watched a little TV. Tammy cleaned the house, did the laundry and cooked us a delicious dinner. Needless to say, I rewarded him enthusiastically at the end of the day.

Since then Tammy has become a member of our family. Tom usually dresses up once or twice a week although he often wears nightgowns to bed and also likes wearing feminine panties under his male clothes during the day. We have expanded Tammy's wardrobe significantly. Tom has become comfortable dressing up and going to the mall with me, as long as we go far enough away that we won't be recognized. We have also gone out as girlfriends to dinner or the movies.

There has been one other nice side benefit of Tammy's arrival. Tom is much more thoughtful and sensitive. He frequently brings me flowers and other presents that he has picked up while shopping. I still find it hard to believe that a chance bet on a football game has led to such a dramatic change in our lives.





2004 by Tammy Richards. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.