Dressed To Please Kate

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Husband and wife both enjoy the femme side.
7k words
4.51
195.2k
162

Part 1 of the 2 part series

Updated 06/07/2023
Created 06/20/2015
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jealouscuck
jealouscuck
2,564 Followers

My name is William Michael. I go by Bill. I know, stupid way to start a story. My wife is Caitlyn and goes by Kate most of the time. You will see why I started with names. Kate is thirty and I am thirty-one. We had been married three years when all this started. Kate is a very perky brunette, five-four, about 130 lbs. She has very little body fat and is athletic. She played soccer in college. Kate has a full B cup and is very sexy. She is very confident and was always somewhat dominant. I am five-eight, 155. I also have a five inch cock. Kate never had any problem with that while we were dating. We met in college during shared classes. It was an economics class and we eventually began talking after class and finally started studying together. I am an accountant and work out of an office. I am only somewhat athletic. Play a little golf on weekends, walk, ride bikes, etc.

Kate and I hit it off so well as friends that we just started hanging out together. As I spent more time with her, I spent less time with my guy friends. She was always playing soccer, training and travelling, so I had plenty of time without her. As we got closer to graduation, we talked about what our plans were. I was going straight to the accounting field and Kate was planning on becoming a physical therapist and possibly a part time trainer. One night after studying for exams, Kate asked why I had no romantic interest in her. I told her that I was shy and uncertain about her wishes. I did not want to ruin our friendship by taking things for granted and then getting shot down. I was not the jock type who I thought she might be attracted to. She was pissed and asked if I was that stupid to miss all the signals. I of course asked, "What signals?"

She then shocked me by kissing me firmly on the lips and placing my hand on her breast. The first make-out session was so good for me, that I came in my underwear. I did not even try to have sex with her and she easily guessed that I was a virgin. She said, "Bill, unless you have no desire to be with me, I can see we have a lot of work to do." I was a little unsure about myself but I did know that she was hot and sexy. I was not stupid enough to look a gift horse in the mouth. I was crazy in love with her already.

Three weeks later, we had sex. My first time, not hers. She taught me everything. Slowly at first. After I gained my confidence, nature pretty much took its course. However she introduced me to oral sex and mutual masturbation to name a few. With graduation looming and future uncertain, I decided to ask her to marry me. She quickly agreed, but asked if I felt cheated by not sowing our wild oats. I told her that I could not imagine finding anyone else that I loved so much. Also, I knew it was a step up for me to be marrying Kate. She said that I was going to have to get over that submissive streak if I was going to be a success in business.

Actually I was only sexually shy. I was a top notch student and got straight A's. I got a well paying job at entry level. Kate started looking for a career goal in the large city that I would be moving to. She found a great job with a major hospital and made contacts with the area youth clubs for a possible part time training job. The next spring we were married. Sex was great. Work was demanding. We spent as much time together as we could.

One evening Kate showered and got dressed in a very sexy white baby doll with a tiny g-string panty. After I showered, she began tantalizing me with her considerable feminine charms and sexy lingerie. I was turned on and my five inch cock was rock hard. She pulled down my unattractive boxer bottoms and began sucking my cock. During my blowjob, Kate kept spitting out my fine pubic hairs. She sucked me until I thought I might cum in her mouth. She then pulled back and lay down on the bed and told me to take off her panties and fuck her. This was a little more descriptive that we usually got, but I was already hot and ready to go. After we had sex, she told me that if I wanted more blow jobs, I should shave all my pubic hair. I asked why. She said, "Well, you should not to have ask why." Kate already shaved her pubic area and was as slick as a newborn down there. I thought, why not, so the next night I shaved all my hair around my cock and balls.

I few nights later, Kate went through pretty much the same routine except this time she wore all black. She again flaunted her charms and made a show out of seducing me. As she began to pull my boxers, she said, "I am all dressed up for you and you wear these frumpy old things." She pulled them off me and saw that I had removed my pubic hair. She squealed with delight and said, "Now if we can get you out of those ugly boxers, we might actually get somewhere." "What would you have me wear?" I foolishly asked. That was the last normal moment of my life. For Kate said, "Well, since you asked." She then pulled her tiny black g-string down and stepped out of it. She quickly picked it up, pushed me down on the bed and quickly slid the tiny fabric up my legs. The panty, as small as it was just barely covered my cock and balls. Kate said that I looked great and that shaving my hair was a very good move. She rubbed my cock and balls through the flimsy material and whispered in my ear to eat her pussy. I had never been so hard in my life.

There I was, expecting to get a blow job and now I was on my knees in her panties no less, sucking her delicious pussy. It all happened too quickly for me to resist. After I licked her to orgasm, she mounted me, moved the panties aside and rode my cock hard and fast. I came harder than ever before. When she rolled off my cock, she placed the panties back across my softening manhood. She said, "Damn, honey that was hotter than anything I have ever done." I did not ask any questions, but I had a million in my head. I started to ask what had brought all that on, but decided to wait. We made love again later. I was still in her panties and she was still in her baby doll top. Afterward, Kate insisted that I keep her panties on. I did, but I woke up frequently feeling very conflicted.

The following morning it was business as usual. Kate acted quite normal as if nothing out of the ordinary had happened. I waited until that evening to bring it up to her. Since we were so very open with each other, she shared that one of her work friends, Aubrey, was about our age and interesting. I asked her to define interesting. She said that for one, her husband, Devan, was an IT person for a very large company who worked mostly from his home office. Devan was very smart and made a lot of money. Aubrey worked mostly because of her family work ethic growing up. She did not want to be the submissive wife. As a matter of fact, she was quite dominant in their marriage.

I asked Kate why I had not heard of Aubrey before and by the way what did all that have to do with our sex life. Again, not wanting to hold anything back, she told me that Devan was actually a submissive at home when he was not working on a project. It seems Aubrey was more than just dominant; she was actually a Dom Wife. I did not know what that meant. Kate said that they were not into the true Dominatrix scene, but that Aubrey ran the social activities and the management of the household planning. Finally she said that Aubrey also ran their sex life. I asked what that meant. Kate said that she did not know all the details yet, but Aubrey had shared enough to get her curiosity up. In fact they had gone out for drinks after work and Aubrey had asked Kate if we ever played any kinky sex games. Kate admitted that I was a virgin when we met, but she was more experienced. Aubrey asked her if she thought of me as submissive. She told her that she did not think of me in that way.

That's when Aubrey asked her if she could get me to wear her panties. I was a little miffed that Kate would have such conversations with a relatively new friend. Kate said that she had told Aubrey that we would never do anything like that. Aubrey had told Kate to try it. She said we might like it. Kate said that she left it hanging there, but afterward, she got thinking about it and could not help but follow the suggestion. I asked Kate if she was going to tell Aubrey about this and she said, "Absolutely not, it was just kind of a lark on my part." I wondered about this new friendship with Aubrey and also what submissive meant in the context of sexual relationships.

Kate apologized to me for dressing me in her panties and said that we would never do that again. She stressed that she was a little turned on about her conversation with Aubrey and probably got a little out of line. I felt more conflicted than ever. I could not explain how I felt. The next time we made love was when I approached Kate after we had gone to bed on night. She was wearing another sexy baby doll. I began fondling her breasts and pussy through the very sheer material. This time she pulled her tiny panties aside and mounted me. She rode my cock until I exploded into her tight pussy. As we lay together afterwards, she rubbed my chest and face and told me how much she loved me. Again she apologized for putting her panties on me. I surprised even myself by telling her that it was the best sex I had ever had and that after thinking it over, she could put her panties of me whenever she wanted. She asked, "Are you sure?" I told her yes again. She then said, "How about right now?"

I told her it was okay. When she slid her panties down and pulled them over my legs and up my body, my hard cock was springing back to life. She sucked my cock into her luscious mouth and gave me the nastiest blow job that I had ever experienced. After I came in her mouth, she pulled the panties back over my softening cock and we went to sleep. I was just beginning to get used to the idea of wearing panties. I loved how they caressed my cock and balls. I felt free and airy when I wore them.

Little by little Kate began to mention her conversations with Aubrey. It was mostly girl talk, but occasionally she would mention Devan and Aubrey as a couple. Usually it was just something that they had done together on the weekend.

One night Kate told me that she and Aubrey wanted to take a wine tasting tour that Saturday. I was a little lukewarm about the idea. She then said that it was for all four of us. She said that we needed to make more friends anyway and this would be a great opportunity to meet Aubrey and Devan. I finally agreed and the next night Kate filled me in on the details. We met up with them at the winery and I was stunned to say the least.

Kate had apparently forgotten to tell me that Aubrey was a gorgeous redhead with a dynamite figure. She was about 5-8, small waist, really big breasts and a perfect ass. Devan was about 5-7, just a little shorter than Aubrey. Aubrey wore tight shorts and a scooped neck top. Her breasts rose magnificently above the thin top and you could easily make out the lace on her beautiful bra. Wow. Devan was slight of build much like me. He was very polite. Almost too polite. He spoke to Kate as if they were old friends already. He asked all sorts of questions during our tour and seemed interested in everything about the winery, and about us. By the end of the day we were very comfortable with each other as individuals and couples.

On the way back home, we decided to have dinner together and order some of the wine that we liked at the tour. It was a continuation of our friendly introduction to the young couple. Devan was very attentive to Aubrey and was always looking for her glass to be filled or anything else she might need. It seemed that he was a very generous, attentive husband. When we parted for the evening, Kate and I returned home and were very mellow from the wine and the delightful day we had experienced. Kate asked me what I thought of Aubrey and Devan. I told her that she could have told me that Aubrey was a bombshell so I would not have drooled on myself when I met her. Kate hit me on the arm and asked what I thought of Devan. I told her that he seemed like a great guy and so polite. Kate just smiled and thanked me for agreeing to go out with them.

The next week, Kate came home telling me that Aubrey and Devan were very appreciative of the weekend we had all enjoyed. She said that Aubrey and Devan were on their best behavior. I did not know what that meant. Kate said that Aubrey wanted us to come over to their house that weekend for dinner. She said that Devan enjoyed our company so much that he wanted to cook for us. It seemed a little out of the ordinary, but I readily agreed. The next Saturday, Kate and I arrived at their house at seven sharp. Aubrey answered the door in a black leotard cat suit and very high heels. Her makeup was very dark and quite excessive. The top was very low cut barely holding her gorgeous breasts. They had to be G cups or better. Her areolas and nipples were very prominent. She was so smoking hot that I got a boner just looking at those big round breasts and perfect ass.

Aubrey told us that Devan would be out shortly with our drinks. Shortly after the kitchen swinging door opened and out walked a pretty French maid holding a tray of wine glasses. She was about 5'-10" in her stiletto heels and had a very nice face and short brunette hair. I asked Aubrey where Devan was and she laughed. She said that Devan would not be joining us tonight, but "Devine" would be with us all evening. I was beginning to feel a little uncomfortable. I glanced back to "Devine" and suddenly realized that it was Devan in the pretty maid's uniform. I looked at Kate and she was smiling so wide that I had no choice but to follow her lead. Aubrey politely introduced us to Devine as if we had never met before. She said, "Devine, these are my friends, Bill and Kate. Guys, this is Devine my maid and girlfriend."

After serving dinner, Devine removed the dishes. I got up to help and the girls walked over to the living room. I asked Devine what was going on. She told me that Aubrey wanted to introduce us to his alter ego while she was in her element. He said that Kate already knew that Devan was going to be dressed as Devine and that they both wanted to see my reaction when I discovered her secret.

Devine said that Aubrey was so gorgeous and he loved her so much that he was willing to do anything she asked. He said that they had first gone the traditional route where supposedly the man took charge and the woman obeyed. Neither one of them felt fulfilled and after a few months, they started experimenting with some sexual variations. The thing that got them the most excited was when Aubrey started taking charge of their sex life. This finally transformed to Devan becoming the true submissive. After Aubrey dressed him in panties the first time, they were completely hooked on the role reversal.

Devan said that he loved the feel of her panties. He came more than ever when they had sex while he wore her panties. This finally worked all the way into him becoming her. Devine said they first started going out grocery shopping with him dressed in drag. They were not so glaring at first and she just made him up a little and had him wear casual female clothing. He loved it so much that it finally grew to the casual maid, then the French maid and finally to the full blown girlfriend. He said that sex was better than ever, but frequently Aubrey fucked him in the ass with a dildo. Other times she just made him eat her pussy like a good lesbian lover.

Devan/Devine said that Aubrey had told him about her talks with Kate and that she had eventually told her that she had put her panties on me. He/she agreed with Aubrey that we could be the like minded couple that they had become. Since we all had enjoyed each other so much on the wine tasting tour, they wanted to hit me up front with their "arrangement". He said that Aubrey and Kate had talked about how close we were and that they were also like that. He said that he knew that Aubrey could have any man she wanted, but she wanted both Devan and Devine.

I did not know how to take it all, but my little cock was starting to get hard the more I thought of Kate putting her panties on me. I had begun to feel less remorse after sleeping in Kate's panties. It was a lot to digest but I definitely did not harbor any disgust after talking to Devan. On the way home Kate and I discussed this openly. She asked what Devan and I had talked about in the kitchen. She said that she and Aubrey felt that I would not be repulsed by Devine coming out in front of me. Kate knew by then that Devan turned into Devine. I asked her why she had shared with Aubrey our panty secret. She said, "Honey, it is not such a secret and besides it is hot." I could not deny that the panties turned me on, but actually becoming a woman was not on my list.

The next night, Kate suggested that I needed some touch up grooming for my genitals. Since I had already been removing the pubic hair as a matter of course, I did not think too much of her suggestion. When I went to take a shower, she came in with some rubber gloves and a container of hair remover. She lathered up my pubic area and continued down my legs and back up to my waist in back. I am not very hairy and my hair is thin dirty blonde. Kate also rubbed it on my arms. When I came out of the shower, the only hair I had left was under my arms. My little cock was standing at full attention. Then Kate told me to shave my underarms.

Kate had laid out our bedclothes. A royal blue teddy and panties for her and a pair of lacy crotchless panties for me. Mine were pink and very frilly. She said that she wanted to try something else on me. She showed me how to put on silky white hose and a cute little pink garter belt. She topped me off with a very sheer shirt top which she buttoned all the way up. I did not resist any of her ideas and we made love. After I came in her pussy, she put her finger to my lips and told me to be quiet. She then slid up my body and placed her dripping pussy firmly over my mouth. I began to lick her delicious folds and opened my mouth and let the thick cum drain into my mouth. I eagerly swallowed our love nectar as Kate slowly pleasured herself on my mouth. She came with intense shudders and a combination of low moans and high pitched shrieks. Afterward, she lay beside me and kissed me while she let her tongue search for remnants of my cum load. She told me how sexy I looked in my lingerie. She said that it was the most intense orgasm she had ever experienced and hoped that I loved it as much as she did.

The next week we were both back to full time work. We were both very tired most evenings. Kate brought home very pretty sleep set for me. It was a very silky hot pink short and top set. I had to get used to buttoning the top up the opposite side. That was another subtle difference between men's and women's clothing. A couple of nights later, she brought home a pair of what she called sissy panties. They were mostly lace and thin material and had a small pouch in front for my cock. I got up Friday morning for another long day at the office. Kate was waiting for me when I got out of the shower. She suggested that I wear the sissy panties to work under my regular suit. I had trouble hiding my erection all day. I mostly sat at my desk, but the sexy material kept me aroused all day.

That night, Kate met me at the door with a drink in hand. After we visited for a while, she asked me how I had felt in my panties all day. I told her that I was aroused almost all the time. She was very pleased and gave me a big kiss and told me to go get undressed. When I was completely naked, Kate took me in the bathroom and applied shaving cream to my crotch and proceeded to shave the underside of my cock and balls. Then she applied the depilatory cream and had me wait for a time before I went into the shower and washed off all of my body hair. She told me that from now on I was to take care of all that by myself.

jealouscuck
jealouscuck
2,564 Followers
12