Kinky Sex Stories

Woman Who Loves To Cross Dress And Feminize Man.

My girlfriend Cinthia, and I had been living together for about 6 months when she first caught me in the bathroom wearing her lingerie.

“That is so disgusting Nathan, are you some kind of freak or something? If I ever catch you wearing my panties again, I am going to break up with you.” My girlfriend told me.

I felt horrible after that and vowed to myself never to wear women’s clothes again. But I just couldn’t help myself. I loved the way it felt to be all dressed up like a girl, and it turned me on more than anything. I had always been confused about this, and wondered at times if I was gay. But I was never attracted to men; I only enjoyed sex with women. However every time I would tell my lover about my secret fantasies, I would lose them. And it looked like I was going to lose Cinthia now too.

I began to go to the mall after I got off work and hang around at Victories Secret. Most of the time I would fantasize about how I would look in the sexy nothings, teddies, garders, panties, bras. I loved them all. After an hour of so, I would buy something for Cinthia and go home. Sometimes I gave her the lingerie, sometimes I kept it for myself.

I hung around the lingerie shop so much, that the manager, Sandy, got to know me and we would chat.

“You must have a very lucky girlfriend Nathan.” Sandy said. “You always buy the sexiest garments and the hottest outfits.”

“Yes, my girlfriend is very special, and I like to please her as often as I can.” I said.

“But you know Nathan, I am very curious about something. Sometimes you purchase the petite size, and sometimes the large size. It’s none of my business, but I know your little secret, and want you to know that I think it’s wonderful and nothing to be ashamed about.” Sandy said

“I don’t know what you mean.” I exclaimed.

Sandy took my hand firmly and looked deeply into my eyes and said, “Nathan, I have seen you trying on some of the lingerie in here. Personally, there is nothing so sexy as a cute guy wearing women’s clothes. If my husband would allow me to dress him up, I think we would have a much better marriage. I envy you and your girlfriend for being able to share that experience together. There is no reason to be embarrassed.”

“Sandy, you are right. Half of the sexy clothes I buy at your store are for me. You are very wise, and I feel a little silly for being caught.” I said.

“It’s perfectly fine Nathan, in fact, I think it’s wonderful and wish there were more guys like you out there.”

“I wish my girlfriend felt as you do. I have to hide the lingerie for me and if she catches me again, she said she will break up with me.” I said.

“Well Nathan, that is such a shame. Follow me, I want to show you something.” Sandy said and took my hand and led me to the back of the store to her office.

Sandy showed me a picture of her husband and he was a very masculine guy, very muscular, and very big.

“You see, when I was younger, I thought that this was the type of man I should marry. A strong man and very masculine. However almost from the start of our marriage, I realized that we could not connect on many levels and I began to fantasize about finding a younger, more sensitive man. When I took over this lingerie store, I began to find myself fantasizing about every man in here, and wanting to dress him up in the lingerie that he purchased. It has been going on for about 10 years now. I love my husband very much, but ultimately, he only has one gear for love making. It’s a good gear, but not very versatile. I would never want to do anything to hurt him, and I could not live with myself if I cheated on him. But I can not stop the fantasies that I have every single day. Do you understand?”

“I do understand Sandy. Perfectly. I am sorry to hear that.” I said honestly.

“I knew we would get along, from the moment I saw you. I have been watching you for some time now and have been fantasizing about dressing you up in sexy lingerie. How would you feel about it if I did so right now?”

“Sandy, I am very flattered. You are a beautiful and intelligent woman and I the idea of you dressing me up excites me a lot. But I don’t want to cheat on my girlfriend either.” I said.

“Well Nathan, it’s settled. I get to dress up you, and neither one of us cheats. Ok?”

“Ok Sandy, what do you want me to do now?”

Sandy gave me a big hug and we held each other for several minutes. She was about 9 years older than me, slightly taller than me, and smelled like a classy hotel. She had short dark hair and I had semi long blond hair. There was so much chemistry between us that we didn’t have to say anything. We knew exactly what our roles were and we played them out.

Sandy undressed my man clothes and as I stood naked, she walked around me several times looking me up and down. Then she went into the stock room and came back with a whole bunch of new lingerie. She went to work slipping on various panties and taking them off. And when she settled on something she liked, she left it on me and moved on to the next item. After about an hour, I was dressed in frills and lace.

“There, now this is just the first time Nathan and it will only get better as we go. What do you think?”

“It’s a work of art Sandy. I never knew I could look so sexy. You did a fabulous job.” I gushed.

Sandy took me by the hand and paraded me around the office, looking at me from every angle. I have never been so spoiled with attention in my life and was worried I would quickly fall in love with this amazing woman of my dreams.

“Sit down, let me do your hair and makeup now.” Sandy commanded.

I sat down and Sandy ran her hands through my hair. We spoke about everything and anything and I was hers totally. It certainly felt like cheating to me, as I imagine it did for her, but no fluids were exchanged, so technically, we were being faithful to our partners.

As time went on, I would go into Sandy’s store, and she would dress me up, then I would get undressed and go home and masturbate. This went on for several months until Sandy asked me over to her house. Her husband Sam was going out of town and she wanted to cook me dinner. I agreed and as usual, Sandy dressed me up but this time, we spent many hours together, both walking around in sexy lingerie and drinking wine until it was time for me to go.

“Nathan, don’t go home just yet. All I can think about anymore is having you in my bed. It’s what I want more than anything and I don’t care who it hurts anymore.” Sandy pleaded.

“I feel the same way Sandy, you are all I can think about anymore too. I masturbate about you everyday, and during sex with my girlfriend, all I can think about is you.”

Sandy wasted no time and grabbed me and kissed me. We made love, both dressed in lingerie, all over her large and luxurious house. I called my girlfriend and told her I could not make it home because I had to visit a friend in the hospital. She was not happy with me and I think suspected something. I didn’t care.

Sandy and I made love, took a nap, took a shower, ate, got dressed up again, and made love again. It was the best sex I ever had and I told her so. She confessed the same.

For awhile, it was pure bliss. We both had the best of both worlds. We had our steady relationships, and got to live out our fantasies too. But we both began to suffer from guilt and searched for a way to rid ourselves from it.

Neither one of us wanted to leave our partners. After all, we did love them and they were able to satisfy our every need, except for this one sexual desire. We would both lose a great deal of security by leaving them, and decided to stop seeing each other. But that did not last and only intensified our craving.

Finally, we came up with an idea. What if our partners were attracted to each other? They had similar sexual tastes afterall. My girlfriend liked straight sex with a strong man, and Sandy’s husband liked straight sex with a submissive woman. Would it hurt us knowing they were having sex with each other? It might, but if it made them happy, and we were allowed to continue our sex too, then everyone would win.

Sandy devised a plan. I was to dress my girlfriend up in sexy clothes and then Sandy and her husband would pop over to our place for a surprise visit. We would make up a story that we were old friends from childhood and that Sandy used to be my babysitter and that we ran into each other at Sandy’s store. I had invited them over and forgot to tell Cinthia. Sandy was to tease her husband and get him horny before they arrived, and I was to do the same with Cinthia.

I dressed Cinthia in the tightest swimsuit I could find. A white number with pull strings on the side. She was out on the deck sunbathing when Sandy and Sam arrived. When I introduced them to Cinthia, I could tell immediately that she was intrigued by Sam. Sam too could not stop looking at her in her tight white bikini. I told them to get to know each other while Sandy and I made diner and caught up with each other. We spied on our partners and they drank cocktails and chatted.

To our shock, Sam reached over and kissed my girlfriend and she kissed him back. His hands were all over her and she did not try to stop him. Perhaps our plan was working too well. We made some noise and went back outside. They heard us approaching and stopped before we could catch them.

We all ate dinner and acted like nothing had happened. After diner, Sandy pulled me aside and told me of her idea. She suggested we go out to get ice cream and rent a movie and leave them alone while one of us spied on them.

I went for the ice cream and the movie and when I came back, Sandy informed me that Sam had made love to Cinthia, quickly and forcefully and that Cinthia did nothing to stop him and had enjoyed it. This news hurt me a little, but of course I was not innocent.

We entered the house and found our partners on the couch acting as if nothing had happened.

“Sam, Cinthia, lets all be adults and mature for a moment. I just watched you two have sex. I am not upset, but I do have a proposition. Obviously you two are attracted to each other, and Nathan and I are very attracted to each other also. In the interest of keeping our relationships alive and healthy, perhaps we should exchange lovers for awhile. We could all still stay together, but would be allowed to have sex with our new friend.” Sandy explained.

Shockingly, we all agreed. At first I struggled with knowing that my girlfriend was having sex with another man, but Sandy assured me that Sam was not as good as a lover as I was. And so long as Cinthia kept wanting to live with me, then I should be fine. And indeed, even Cinthia said that I was a better lover than Sam but that he offered her something that I could not, and was grateful that I was open minded about understood.

Sandy and I took our love making to a whole new level. We tried everything that felt good. Sometimes, Sandy would dress me up as a woman and we would go out for drinks. It was all very erotic to me. We experimented with strap on dildos and anal sex. Sandy said that sometimes, my ass looked so good in her panties, that she just had to fuck it. Over time, I began to enjoy anal sex very much and worried that I might be gay, but she assured me that so long as I more attracted to women, that I was not gay.

Overall, I thought Sandy and I were getting the better deal. But I think our partners thought the same. They were confused by what Sandy and I did together and didn’t want to know the details. It was beyond their scope of understanding and they found it disgusting and strange. But we found it wonderful and liberating.