My Wife My Partner Ch. 01-04

Story Info
Wife encourages husband to cross dress.
17.7k words
4.45
328.1k
139
0

Part 1 of the 3 part series

Updated 10/17/2022
Created 01/17/2006
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Karenkay
Karenkay
5,794 Followers

Jerry couldn't believe it had been six weeks since that dreaded night that his wife came home early from her usual Thursday night card game with the girls and caught him in that dreadful act.

How could he have been so stupid and let it happen so easily? It was something that he enjoyed doing since he was fourteen years old and now he had been caught by his own wife.

Tammy was so angry at him that night that she almost packed his bags and made him move out of the house that night but she didn't. He spent four weeks sleeping in their guests' bedroom and it wasn't until he had apologized to her numerous times and said that he would never do it again before she finally gave in and allowed him back in their bed again.

She still wouldn't allow him to have sex with her, not after that night. Jerry pleaded with her the other night, almost begging her to have sex but she was still too angry and hurt.

Jerry knew that Tammy had confided with her best friend at work concerning their marital problems and Jerry was upset. He felt so embarrassed and hurt that Tammy had told someone his little secret.

Jerry had overheard Tammy talking on the phone the other night to this woman whose name is Jean. It almost seemed as if they were planning something, maybe revenge or maybe this woman was trying to talk Tammy into divorcing him.

After all, it wasn't as if he went out screwing another woman. Why wouldn't she just let it go and forget that it even happened?

They had been married for seven years and Jerry loved Tammy with all his heart. He remembered meeting her on a blind date and how beautiful she was. They were both fresh out of college and both working in real estate.

They had met at the company Christmas party and were married the following spring. They began working as a team and were very successful at selling homes.

Tammy had long red hair and he loved redheads' and she was very slim with long legs but very well endowed. Her tiny waist seemed to enhance her bust size even more.

Jerry wasn't much larger than his wife, they were the same height and he had always been skinny. Jerry didn't think he weighed any more than his wife.

They were both going to turn thirty next year and they were so successful that they bought a million-dollar house and both had luxury cars. They just didn't have any time for kids right now, they were so busy trying to get everything they wanted before they settled down with children.

Tammy was talking on the phone that very moment with her friend Jean. Jean was another agent down at the office where he and Tammy worked.

Jerry had wondered how many of the other agents knew what he had done. He just couldn't believe his own wife would spill the beans to her best friend on him.

After dinner that night, he and Tammy had settled down and were working on a few updates on some listings together when Tammy stopped what she was doing on the computer and turned to Jerry and gave him a hug.

"Jerry. I'm really sorry I've been so hard on you these past few weeks. It's just that I was very hurt when I came home and found you the way I did that day."

Jerry gave her another hug and they kissed and Tammy looked into his eyes and smiled as she held his hands and knew she has something else to day to him.

"I've been talking to Jean and we had a long talk about what had happened that night and I think I've been very unfair to you. I think we should have talked about what had happened a lot sooner and got everything out in the open."

Tammy reached up and held his chin in her hand and kissed his lips gently. Jerry was beginning to feel so much better after all this time. Tammy was finally letting it go and moving on.

"Honey. I've decided to allow you to continue doing what you enjoy. I understand perfectly well how you feel and I don't want to deny you of your little hobby."

Jerry looked into Tammy's eyes knowing that she was being very honest and sincere and it caused him to smile back at her knowing that she understood.

That night was the first time that he and Tammy had sex in more than six weeks and she was being so much different that night. Tammy seemed to be concentrated on studying Jerry rather then enjoying sex with him.

She was treating him so much differently that it made him paranoid to what she was thinking. Tammy studied every inch of Jerry's body, running the palms of her hands along his legs and thigh's and feeling his slim waist and small shoulders.

Tammy even made him laugh that night when she compared his legs to her own legs, telling him how long and slim his were, just like her own and how soft his skin felt against her own.

They were laying in bed cuddling and Tammy was stroking his hair and looking into his eyes. Jerry knew she was thinking about something. He knew her very well.

She lowered her hand and began rubbing it along his chest and played with his nipples. She began to laugh as she thought about something but didn't share her thoughts with him.

They were both naked and there was only the dim light on in the room but Jerry could defiantly see something in her eyes that scared him a little.

Tammies jumped out of bed giggling and opened one of her drawers and pulled an article of clothing out and held it behind her back and leaped back into the bed and playfully smiled at Jerry holding the object behind her back.

"What's wrong? Why are you laughing and what do you have behind your back?"

"I got something I want you to try on for me. Close your eyes and let me put it on you."

I closed my eyes and waited for Tammy to put whatever she was holding on me. She was giggling as she lifted my feet, one at a time and I felt her pulling underpants up my legs so I lifted my rear off the bed so she could pull them up.

They were very tight and she playfully snapped the elastic and said, "OK. Open your eyes now."

I looked down to see what she had put on me, and was shocked and hurt when I saw that she had slipped a pink pair of panties on me. I immediately thought she was making a joke out of what happened but quickly defended her action.

"Jerry. I thought this would make you happy knowing that I'm willing to accept your cross-dressing activities. I just wanted you to feel comfortable doing it around me. There isn't any reason why you have to hide your secret from me. I love you and accept you the way you are."

I felt uncomfortable laying in bed with a dainty pair of women's pink panties on me. I looked down and saw that they were very tiny and well below my navel.

"Jerry. Why don't you stand up and go look in the mirror and see how they look on you?"

I was very hesitant about getting out of bed wearing something like this in front of my wife but she seemed to be interested so I got out of bed and looked at myself in the full length mirror.

Tammy got out of the bed behind me and adjusted the elastic around my hips and gave my ass a gentle squeeze than slapped it.

"Do you know that you can fit into my panties? We're almost the same size except up here?"

Tammy was pointing at her large tits as she walked over to her dresser and pulled out a black bra's from the drawer. She walked over and started to put the thing on me as I tried to resist her.

"Jerry. Don't be ashamed, we'll try it on you and see how it looks."

I allowed my wife to put the bra around my chest and waited patently as she snapped the hooks in the back. She helped me slip the shoulder straps in place and ran over to her dresser again and got a couple pairs of socks and stuffed them inside the cups of the bra.

Tammy was really getting into this as she stood back looking at me wearing the panties and bra. She walked back to the dresser and got out her tape measure and measured my hips and waist and than stood back giggling.

"Do you know that we have the same size hips? My waist is four inches smaller than yours and without the padding in the bra, we're no comparison."

Tammy was getting more out of this little dress-up game than I was as I watched her walk around me checking me out. Tammy ran to the closet and she came out laughing like a little girl with a pair of heels in her hands.

"Jerry. Give these a try and see how they fit you. You have small feet and we might get lucky."

I couldn't believe what my wife was doing as she gave me the black heels. I sat down on the edge of the bed and tried slipping one on. It was tight but I was able to twist the show enough until it slipped on my foot.

Tammy helped me tie the buckle and I slipped on the other heel and waited until she snapped that shoe. I stood up and tried to walk over to the mirror to see how I looked. The heels made me look much taller, they we spiked and opened toes and I loved seeing Tammy wearing them.

She had me turn in front of the mirror to see how good my legs looked wearing the heels. She tugged on the panties until she slipped them down my legs and rushed to the drawer and pulled out a black pair and helped me slip into them.

She was really getting into this and I was beginning to get as excited as she was and she knew it. I had never felt so excited in all the years I had been dressing up.

Tammy walked into the closet and brought out a black dress she hadn't wore in a couple years. She wanted me to try it on so she helped me get into it. It was made out of a satin material and clung to my body.

I never really realized how much that my body size resembled Tammy's as far as my hips and my weight. I got pushed around when I was a kid because I was built so small. Even my arms and hands were dainty and I didn't have big shoulders like most men.

Tammy had picked out this dress because it didn't show very much cleavage and since I wore a bra that was stuffed with socks, you really couldn't tell the difference. My wife had another surprise for me when she kneeled down and took out a box from under the bed. Tammy opened the small cardboard box and took out a blonde wig. It was the wig I had bought a couple years ago and the exact wig that she caught me wearing that dreadful day six weeks ago.

I had thought she had tossed it out in the garbage long ago but here she was smiling and getting ready to put it on my head. I helped her adjust the wig on my head and she picked up her comb and started to comb the hair.

It was long and the hair came down past my shoulders, Tammy fluffed it out and had me walk in front of the full length mirror. She seemed more thrilled with the way I looked than I was and gave me a little kiss on my chin and held her arm around my waist.

Tammy was moving her hand down to my ass and began rubbing her hand across the material of the dress. She gave me a very passionate kiss on my lips as we embraced.

I had never felt so relieved in my whole life, here I was standing next to my wife all dressed up and I felt good. So many years of hiding my secret from everyone and now my wife was helping me. I just couldn't believe my luck.

We talked about having me put on lipstick and other makeup but it was getting late so I started to take off the dress and Tammy stopped me. She gave me another kiss and a hug and smiled at me.

"I never had sex with another woman before."

I was so surprised to hear my wife say that to me but we got in bed with me still dressed and she straddled my face while I licked her pussy. She had a ver intense orgasm a few minutes later and after that she moved down and slipped off my panties and pulled the dress up around my waist and mounted herself on my cock.

We screwed so intensely for the next hour that I thought I was going to cry. My wife had made me so happy and she really seemed very pleased and excited herself. Tammy told me just before we went to sleep that night that she fantasized about doing it with another woman for years and I finally made her dream come true.

I thought about what she said as I fell asleep and realized that I was fulfilling her fantasy as well as my own.

I woke up late the next morning, it was Saturday so I really didn't have anything to do that day. Tammy was already up and I saw the clothes I had been wearing the night before laid out on the chair.

So it wasn't a dream after all, I felt so relieved knowing that I wasn't dreaming last night. I got up and used the bathroom and put on my robe and walked out to the kitchen to see if Tammy had made the coffee.

Tammy had made the coffee and I poured a cup and walked toward the front room. I could hear Tammy talking on the cell phone and could barely hear but wondered whom she was talking to so early in the morning.

A tip toed a little closer so I could hear Tammy and leaned against the wall near the hallway.

"Yeah . . . He did . . . No . . . Even the heels . . . I think I will . . . Do you think so? ..........Well you know he would problebly like that to . . . Yeah . . . Maybe I should . . . I'll give it some thought and I'll call you later . . . OK . . . Yeah . . . Bye . . . "

Tammy was walking in my direction and I pretended to just be walking into the room.

"Oh . . . Good morning sleepy head . . . How is my little girl doing this morning?"

I smiled at Tammy as she kissed my lips, I had many thoughts going through my head at that moment. She was actually joking around and calling me her little girl this morning. What I really wanted to know was whom she was speaking to on the phone and why was she sharing what we had done last night together with another person.

I had thought that we would keep this our little secret but I was wrong.

"Huh . . . Honey . . . Did I hear you talking to someone out here?"

"Oh . . . I was just talking to a client that wanted to see a house tomorrow."

I was feeling a little confused because I had heard Tammy talking about heels and I was sure she was referring about me. It was too early in the morning to get in an argument about something I really wasn't sure about and we had such a good time last night that I didn't want to ruin it now.

Tammy and I stopped by the office later that morning, things were slow so we returned home with nothing really planned. I was sitting on the sofa when my wife walked out of the bedroom completely naked and sat on my lap and kissed me on the lips.

"Why don't you get naked and we'll take a bath together?"

I smiled and kissed her and took her hand and followed her into the bedroom. I got my clothes off in a hurry and went into the bathroom where Tammy was waiting for me I was surprised to see her standing next to the sink with the stuff she uses to wax her legs.

"Honey. I thought we should get rid of that hair on your legs, you'll feel so much smoother when we make love and you'll be able to wear stockings or shorts."

I went along with it and found it very erotic and exciting. Here I was having my wife removing all of my hair on my legs so I'd be smooth as a baby.

Tammy even used her shaver on my face doing the delicate task of shaving me and using her hair remover in a few spots. She always laughed about my hair anyway. I was never able to grow much facial hair to begin with and we joked about it many times.

We took a bath together when we were finished removing all of my hair. Tammy sprinkled her bath oil in the water and both of us came out of the tub smelling nice and sweet.

Tammy had a bunch of idea's in her head and wanted to go out shopping for fake nails and new clothes that I could wear instead of wearing her stuff.

We even picked up a bunch of makeup and new high heel shoes that afternoon. I was actually a little overwhelmed by my wife's eagerness to help me dress so well.

We were so tired from all the shopping that afternoon that we just laid around the house that evening when Tammy got the idea of having me dress up the following day and we would go out and have lunch together.

She wanted to do the works on me and have me go out with her as a woman. I'd only fooled around at the house in the past and I told her I was too nervous to even try but she insisted and reassured me that she could do such a good job on me that nobody would ever know the difference.

Tammy spent two hours getting me ready that Sunday morning and when she was finished, I was a work of art! We both wore floral dresses and I had a pair of red high heels and a matching purse.

I let Tammy drive and ducked when we were backing out of the driveway on our way out. We drove to a large restaurant way on the other side of town and I was nervous going in because the place was full of people.

Tammy encouraged me and I felt more relaxed and we ordered lunch, I practiced speaking and gave the waitress my order without her even noticing anything strange. Tammy said I looked perfect and nobody would ever be able to notice and she was right.

We drove back home and when the garage door came down once we were inside the garage, I felt so relieved that we actually got away with it.

Chapter 2

During the next few weeks, Tammy and I played around the house with my new clothes and she showed me how to apply makeup and do my hair and we went out to lunch every weekend for lunch.

My only concern was that Tammy spoke to her friend on the phone every evening and I know she was giving that person a blow by blow description of what we were doing.

Tammy and I were getting ready for bed one evening and I could tell she had something on her mind to say and she surprised me just before I turned out the light by asking me a question.

"Jerry . . . Have you ever thought about doing it with another man? I thought . . . Since you like to dress up like a woman . . . You don't have to be afraid to tell me the truth . . . "

Tammy's question did catch me off guard and I looked over at her and said. "Tammy. I'm not gay if that's what you are getting at."

"Honey...I know your not gay....I was just wondering if you ever fantasized about being with another man and pretending you are doing everything a woman would do for a man."

I didn't know how to answer her question because I think I may have fantasized about it several times but how could I tell her it was only a fantasy and not something I really wanted to do.

I gave Tammy a kiss and put my hand on the back of her head, "It's only been a fantasy but I'm not interested in doing it."

We went to sleep soon after I answered Tammy, but I wondered if she was wondering if I had gay tendencies and really wanted to go there.

Several weeks had passed and I was getting really good at applying makeup and I bought another wig to wear with my ensemble. It has long red hair and matched Tammy's in color and length.

Tammy bought me breast forms through the mail and with the red hair and the breast forms, we could pass for sisters.

We were going out three or four times a week now, hitting clubs and restaurants and my wardrobe began to grow as well. It began to get more common for me to stay dressed in drag than being a man.

Since we worked together in real estate as a team, I decided to work mostly from our office at home while Tammy met the public, shaking hands and kissing babies. Our little setup seemed to be working fairly well and I would show myself at the office for our monthly meetings.

Lucky for us that our house set back off the street and our neighbors were several hundred feet away, so I was able to dress as a woman almost twenty-four hours a day.

Tammy actually enjoyed me staying home because I did all the house cleaning and cooking. One afternoon, Tammy walked in the door very excited and I thought she had won the lottery or something.

Once she calmed down, we sat on the sofa holding hands. "Oh Jerry. You'll never guess what had happen today."

She was smiling and so happy that I knew it was something really big. "Tell me. What happened?"

"Do you know that property along the coast? The one they were asking thirty million dollars?"

Karenkay
Karenkay
5,794 Followers