Chapter 1

It was about a year ago when Kate was putting my dry cleaning away when she noticed ‘the box’ and that’s when the changes started. She found my secret stash of women’s clothing and made me explain in detail why I would hide this from her. Since the box contained every feminine item you can think of in my size along with size-9 high heels, there was no escaping a truthful answer.

With a heavy heart, I explained that I had been dressing in my sisters and moms things since I was very young and my need to occasionally dress up and express my feminine side to Kate hoping she would understand. After her initial rejection and contempt for my explanation she did some reading and research on the internet and came to understand my needs much better.

My wife always had a high level of sexual needs and loved to experiment so this gave her all kinds of ideas and ways to spice up our current sex life, which had gotten boring and infrequent. I knew she had not been satisfied with our love making and I was becoming concerned that she might start looking outside our marriage for some sexual satisfaction. Keeping her sexually satisfied was always difficult and over the last year our lack of intimacy made me wonder if she was having an affair since we rarely made love anymore.

After that night we didn’t discuss it again for several weeks and during that time we had no sex and didn’t discuss my dressing at all during that time. It was a tense time for me and very stressful as I could not tell what she was thinking or if our marriage was in jeopardy. Finally on Friday, three weeks later, she brought it up during dinner.

“Well baby, I’ve come to understand your need to dress up and I want to help you and be part of your fantasy. I’ve studied the topic for several weeks and chatted with other crossdressers and their wives online to get a better understanding. They tell me that along with the dressing you most likely have lots of other fantasies tied to this and now is your chance to open up and tell me everything. This can be something you and I embrace or this can be the end of our marriage. Your choice, but it everything depends on your total honesty, right now. When I first found your box of goodies I was deeply hurt that you kept that part of your life from me. I now understand what women feel like when their spouse cheats on them but I understand now and I’m giving you another chance to share all your desires with me, your wife. So tell me, what do you dream about when you’re all dressed up and pretty?”

I felt an instant hardness and realized for the first time I might have someone to share this with. Something I had always dreamed of but never thought possible and I just opened up to Kate that night.

“When I’m dressed up like that I feel pretty and at peace. It feels so natural, as if I’ve become a real female. My thoughts become all feminine and I think about make-up, what new outfits to buy on line, what it would be like to be out in public dressed up and treated like a girl. It makes me so excited and when I’m like that I wish I could just stay dressed for the day or weekend and live as a girl.”

“That’s so sweet, I love that. Thank you for being honest, baby. Being a woman is really special and I can understand your desires. When you’re in your girl mode, do you have a female name for yourself? I’ve read where that’s very common.”

“Well, I like the name Chloe and I use that when I’m dressed.”

“I like that name, it’s very feminine. Who do you use it with, darling?”

“Sometimes I chat with some people online and use that name.”

“Do you chat with men, online?”

“Yes.”

“I see. Do you fantasize about men as well?”

“It might sound silly, but yes. I really think of myself as a girl when I’m dressed and I try to act feminine and well, yes I like guys treating me like that. But I don’t want that, I only want you Kate.”

“I understand, John. It’s all fantasy. Sometimes I dream of other men as well and I’m sure that doesn’t bother you either. It’s only a fantasy.”

“Wow, what do you fantasize about with other men?”

“Sometimes I lay in bed and touch myself picturing a strong muscular man taking me in our bed. Sometimes I dream that you’re in the garage or in the other room and he’s fucking me hard in our bed and then he comes inside me. It turns me on when I think about you right there and not able to stop me from getting screwed from this guy. From now on, when I play with myself, I’m going to picture you all dressed up in the other room while he fucks me and I scream while you sit there knowing your wife is owned by some other man and there’s nothing you can do about it. Kinky, right?

There was nothing I could say since she now knew my secret desires and she was accepting me for who I was besides, it was just a fantasy.

She pressed me for more details on my fantasies and I told her things I never imagined I’d repeat to anyone. I told her I had dreamed of what it would be like to go on a date with a man, and what it would like to be kissed. I even told her I dreamed of having a boyfriend and doing all the things a girl does for her man. My face was very red now, embarrassed that I just told my wife I dreamed of being with other men and even being their girlfriend but all she did was rub my arm and encouraged me to continue.

I shifted uncomfortably in the chair as my cock was getting very hard from this conversation when she asked, “What else? Tell me baby, it’s OK.”

“I’ve even dreamed of you forcing me to go out on a double date with you and how I had to watch some guy kiss you and treat you like the sexy girl you are knowing there was nothing I could do and at the same time I was with this cute guy that was hitting on me, kissing me and giving into his desires.”

“Now that’s sexy, what else?”

“Sometimes I dream of being a bride and taking care of my husband. Being the housewife, taking care the house, dressing pretty for him when he comes home from work, and sexually satisfying all of his needs every night.”

Just when I said that, I uncontrollably started rubbing my hard on in front of Kate.

“Wow, honey. That really turned you on. I’ve read where that’s a common fantasy and called the husband fantasy, we’ll have to see what we can do for you, Chloe.”

That was the first time I heard anyone call me Chloe, and I loved it!

Fast forward 6 months:

My wardrobe grew and filled up the guest closet as I was now dressing every night and weekends. Kate taught me the fine art of make-up which she had me practice every day. I learned quickly and had a nice collection of make-up, false eye lashes, and wigs. We spent a great deal of money on my new clothes, shoes, jewelry, make-up, lingerie, and the complete wardrobe.

The result was that our sex life had gotten back on track and our orgasms were amazing. Kate seemed happy and I was loving my new life dressing every free second. One thing that troubled Kate was every time I was dressed I couldn’t hide my erection. Even wearing spanx, girdles, and everything imaginable, it always showed up when I was dressed in certain outfits. Kate is a perfectionist and she told me from the start that she would help me with my dressing but I had to agree to listen to her suggestions and act on her advice.

At this point I had a nice figure, waxed eyebrows, hairless body, expensive hair pieces, pretty eyes defined with the long eye lashes, and perfect make-up. I really was passable as her girlfriend except for the bulge that outlined some of my dresses and skirts. One night when we were in bed, she was browsing some sex sites, she came across a male chastity cage device that claimed to prevent erections. Since my cock was small when soft she determined that this device would prevent me from getting hard and help me pass as the woman she had envisioned for me.

“Baby, will do you wear that for me if I buy one? If you do then I can take you out and you can finally see what it’s like to be a woman in public. It also says it will heighten your sexual relief when I unlock it and how amazing the sex will be for you. What do you think, Chloe?”

I loved when she called me Chloe and I agreed. Besides the idea of being completely submissive to Kate was something I always fantasized about and I was eager to wear one.

A week later the package arrived and that night she had me stand in front of her as she examined the small pink device and instructions. After several minutes she slid the ring under my balls and then slid the device over my soft cock and into place. It was a little tight but Kate explained it was the smallest one they made and it might be a little tight but that I would get used to it. She said it will keep me soft and small, and that our secret would be hidden under my skirts. She then took the little lock and clicked it shut and just like that I was in chastity.

“Oh baby, it’s so cute! I have to admit, I really love how submissive you’ve become and how open you are with me and I love having Chloe as my girlfriend.”

She examined the device and adjusted it a little and then smiled, “It’s perfect, and exactly what I had in mind. Yes, I love it and I’m taking you out tonight and introducing you to the world, baby. It’s early so I want you to shower up, shave, and put on your make-up. I’ll pick out an outfit for you and tonight we are going out to dinner as girlfriends.”

That was a dream come true! Going out as Chloe with my wife, so fun! When I came out of the shower Kate had laid out my lingerie on the bed and a dress on a hanger. I finished getting dried off and slipped into a robe and then sat at the makeup table. After about 30 minutes of expertly putting on my makeup, Kate came in and helped me with my hair. She picked out one of my long blonde wigs and helped me pin in perfectly in place.

“Once you hair grows out a little more we can get you some hair extensions and we won’t need to fit you with a wig anymore. You really do make a pretty girl, I’m surprised I haven’t seen it before.”

She kissed me and said, “Tonight you’re Chloe and my girlfriend.”

I put on the thong panties and matching black padded bra and then opened the new package of pantyhose that Kate handed me. She explained that these were control top pantyhose and should help keep everything in place and hide any nasty bumps. She was right, not only did they keep my caged little penis tucked away between my legs but the pantyhose also made my legs look and feel super smooth and sexy. They were expensive nylons and felt so nice when I rubbed them together with my hands and legs. Kate just smiled with an expression of satisfaction on her face.

“The way those pantyhose keeps your cage hidden is perfect and from now on I want you to wear them at all times. I purchased several pair in different colors, all with the built in support panty. The combination of the pantyhose and your little dick cage will allow you to wear some cute outfits and never reveal our secret. Now slip into your dress and heels Chloe, while I finish getting dressed. I’ll meet you downstairs in about ten minutes.”

I took the dress off the hanger and carefully stepped into the silky material and zipped the side zipper all the up until the dress snugly pressed against my curves and padded bra. The outfit gave me a very curvy figure and an elegant look. The dress fell about six inches above my knee and was short but still long enough to keep its elegance. I put on some hoop earrings and rings along with some perfume and then stepped into my four inch matching black heels and admired myself in the mirror. Kate came in and handed me a diamond ring that resembled a wedding set and explained that of course it was fake diamonds but it will give the impression that you are married, just in case you get hit on and want to turn them down.” She knew my size and they fit perfectly. I just loved the idea of wearing a wedding ring and smiled.

I decided to grab one of Kate’s pearl necklaces and my purse to complete the outfit and then headed downstairs to wait for Kate.

My heart stopped when I saw her come down the stairs. She look so beautiful with her hair swept up and with a sexy makeup look I’d never seen on her before. Her dress was much shorter than mine and did not leave much to the imagination and along with her platform heels her legs looked spectacular. I found myself start to get excited and I felt my penis start to grow again but quickly stopped once the pain from the cage prevented it from becoming erect. This was a strange new feeling as I felt frustrated but turned on at the same time.

“Wow, you’ll turn some heads tonight in that outfit. I’ve never seen you look this sexy.”

Kate smiled and said “We will both get some attention but since it’s your first night out you will need to follow my lead. Only speak when spoken to and use that cute female voice you’ve developed. Try not to engage eye contact unless you want to start a conversation. Act shy and try stay close to me. Everyone will think we’re just two girls out for dinner. Remember, you’re Chloe, a girl. We are girlfriends out for dinner and you need to stay completely in that role no matter what happens. Do you understand, sweetheart?”

“Yes Kate, I will behave like a girl tonight and only think girly thoughts. I’ll be quiet and shy and follow your lead. I’ll make you proud,” I said in my female voice.

She laughed and said, “I’m sure you will baby, and with that voice nobody will ever know our little secret! Who knows, if this works out maybe I’ll just permanently turn you into my girlfriend,” she giggled.

As Kate drove to the restaurant the conversations turned to my chastity device.

“How are you doing with your chastity cage, honey? Is it very uncomfortable?”

“At first it was but I’ve gotten used to it for the most part. Dressed up like this I’m constantly getting turned on which makes me start to get hard but the confinement and pain immediately stops it from growing. It’s very frustrating but I can handle it to be out with you like this. When I saw you come down the stairs in that outfit I got excited again and it did become a little painful when I started to get hard. After a moment of pain my excitement went away due to the fact that I had to focus on the pain and it went soft quickly.”

“I did some more research on it yesterday and that’s one of the benefits. Wearing one will prevent you from getting hard and will make your sexual release that much more intense. When I unlock you and let you relieve your sexual tension, it will be amazing. I also read that some wives or girlfriends will control their spouse by keeping them locked up and only release them when they feel they deserve release. It almost becomes a training device or something like that.”

“I’ve read that as well and I also read it can be very frustrating and sometimes they become what’s called a cuckold. That’s when the wife makes the husband so submissive that she will have her way with anything she desires and the man willingly goes along with it to please her and finally get released.”

“Wow that would be fun. Would you like that? Do you want me to cuckold you, baby?”

“I’m not sure I could handle that.” I said as she pulled up to the valet stand. They opened our doors and I followed Kate into the restaurant where she gave them our names. We were escorted into the bar until our table was ready. Since it was going to be a forty minute wait, the hostess took us to a table across from the bar.

“You girls enjoy your evening and I’ll be sure to send someone over to take your drink order.”

Kate ordered two Metropolitans for us and said that a couple of these will help me relax. We sat there drinking and talking like any other normal girls out together. It was everything I dreamed about. Being out as Chloe and completely passable. I loved it!

“Chloe that dress looks darling on you and that necklace was a nice touch. Your makeup is perfect and all that practice over the last six months had really paid off, you’re really pretty. I saw an outfit that I think would look perfect on you at Nordstrom’s last week. I almost bought it but I thought we could go shopping together and you can try it on in the store this weekend. I was going to make an appointment to get my nails done as well, should I make an appointment for the both of us? You should treat yourself to a nice mani pedi.”

The waitress brought our second drink when I agreed to the nail salon and shopping together. Since I hadn’t had much to eat the first drink already gave me a nice buzz and I was now on my second drink as we continued to talk.

Our girl talk continued. “Do you think I should add some highlights to my hair, Chloe? I was thinking about a little change. What do you think?”

“I think you that would really be nice. I’d love it on you, Kate.”

“This is so fun, Chloe. I haven’t had a girlfriend to go out with for a long time and you’re just perfect. By the way, I love that lip color and you have such nice lips. Any girl would kill for nice plump lips like those. Guys call lips like yours blow job lips Isn’t that cute? Have you ever heard that expression?”

“I just found this color at Ulta last week, and I love it too. Yes, I know. I love my lips and with nice lipstick and gloss they really pop, don’t they?”

“Like I said, lots of us girls would kill for lips like that. The other thing we would kill for are your long legs. They look really sexy in those heels and to tell you the truth, when I saw you in that dress and those heels, I felt a little jealous. Now all we have to do is to find some outfits that accentuate your figure and your assets. You need a certain look and fashion that defines your personality and style. I’m thinking skirts and dresses that show off your legs. We can’t do low cut or sheer tops yet because your lack of breast but we can come up with some nice styles for you, I’m sure.”

“A style for my personality? Do you expect me to be going out more often? I thought I was just dressing up around the house.”

“Oh no, after tonight you will be spending much more time dressed as Chloe. In fact, I want to find a way to keep you in skirts all the time, if possible.”

After I finished my second drink I was feeling relaxed and extremely happy. Our conversation shifted to more personal girl talk.

“Chloe, I want see what type of taste you have in men. Scan the bar and pick out two guys that you find attractive.”

“Kate, I don’t want to look at men. I just want to be here with you.”

“Oh Chloe, you’re my girlfriend right? This is what girls do, don’t be a drag and act like that. I saw the stories you read on your computer and I know that when you’re a girl you like to be pretty for men and you love their attention. So stop pretending to be anything else with me. Now look over at the bar and pick two guys that you find attractive.”

I turned my head and looked at the crowded bar and saw a man in a nice suit at the end of the bar. He was extremely handsome with dark hair, tall, muscular, with a strong jawline. Then a few chairs down was a really big muscular guy with a nice smile that made me tingle inside. I pointed them out to Kate.

“Wow, nice taste Chloe. You like them big and manly and I can understand how you would find them hot. I like those two guys,” She said pointing over to the two men drinking a beer standing next to the bar. Both of these guys were well over six feet tall with rippling muscles and strong bodies. They looked like gym rats and clearly macho guys.

“Wow, they’re nothing like me,” I said showing my jealousy.

“Chloe, girl talk. You’re my girlfriend. Of course they’re not like you honey. Now that wasn’t so hard was it?”

“Actually it was fun. I’m really enjoying this time with you Kate. Thank you for taking me out tonight, I love being out like this with you.”

“You’re welcome honey, I think we will be doing this more after starting tonight.” Our hostess came over to tell us our table was ready. We had the bill transferred to our table and got up to follow her into the dining room. I followed Kate and the hostess and as we were leaving the bar I noticed a very handsome man staring and waving at Kate. My heart stopped and I felt fear race through my body. I was worried this was someone she knew and that I might be discovered. She immediately saw him and turned her head to me and said, “Go to the table and I’ll be there in a few minutes.”

I watched as he took her hand and gave her a kiss on the lips as I followed the hostess out of the bar. I didn’t want to look back or stare because I was afraid he would want an introduction, so I kept up with the hostess and sat at the table.

“It looks like we lost your friend. I’ll let her know where you are and I’ll have them bring you another drink.”

“Thank you,” was all I could say as I tried to look and see what was happening with Kate. I sat there alone for about five minutes worried and concerned about Kate as well as being alone and what was happening in the bar with that guy. She finally turned the corner and sat down with me at our table.

“Who was that, Kate?”

“Do you remember when I told you about the guy I dated in college, Ricky Carter?”

“Yes, you dated him for 3 years and almost married him, as I recall. Was that him?”

“That’s him. He just moved here a month ago and lives just a few miles from us. I haven’t seen him in years and now, just like that he lives right nearby.”

“Well you seem very happy to see him again.”

“He’s a great guy and I always enjoyed spending time with him. Are you a little jealous baby? Don’t be, remember you’re Chloe my girlfriend. Girlfriends support each other. Don’t worry, I’m sure we can find a guy for you too baby.” she said giggling.

“Not funny, Kate.”

“Oh just relax, its part of being a woman. Men will always be involved at some point and the sooner you realize that the quicker you’ll understand what really being a girl is all about.”

“I’m not sure I’m ready for that, Kate. Do you want to be with him?

“I understand that you’re scared but if you really want to be like me, a woman, then you will have to face the fact that at some point there will be a guy hitting on you or wanting to date you, Chloe. You already admitted that you like it when they find you attractive and it makes you feel warm and tingly all over. It will take time and I’ll be there to help you and yes, I think it would be fun to spend some time with him again. He asked me out for drinks sometime and I gave him my number so I might see him again, yes. You can understand my needs to be with man, can’t you honey? You do know I have needs too and you can’t be selfish with me, honey. Let’s change the topic. How long have you had your little cage on now?”

It took a great deal of effort to change my thoughts about Kate and Ricky but I did and said, “It’s been 4 days now, can we take it off tonight? I really need some relief. Every time I start to get hard the intense pain stops the erection and my balls are so ready to come. Can we, please?” I pleaded as I saw her smile.

“Well to tell you the truth, you’re begging, it’s making me wet. No, I think after you complained about Ricky hitting on me tonight that you will need to keep it locked for until next week. If you’re a good girl I’ll release you next Friday night. Now you have a little incentive to make sure I’m happy. If you please me this week then yes, next Friday will be your release date. In the meantime I think I want you in my bed tonight and between my legs. Between you dressed up like this and Ricky, I’m really horny tonight!”

Oh my god! Another week locked up like this? And what happens if I don’t please her or do something wrong? Does my date change? I’m not sure I like this, I said to myself.

We both had salads and finished our drinks as the topic turned back to fashion, hairstyles, makeup, movies, and gossip. Sitting there in my wonderful dress and feeling so feminine was beyond description. I was living a dream and was thankful for Kate and her encouragement. Without her I never would have had the courage to dress up daily, practice my feminine movements that she taught me, or even have the nerve to leave the house in my heels and this complete transformation.

“Are you having fun on your first girls excursion, baby?”

“I was just thinking how thankful I was to you for helping me become so feminine and how you gave me the courage to go out dressed like this. I love how it feels being out in a dress like this and how people are reacting to me, just like I was another girl. I love it. Thank you, Kate. I really mean it, you are really a special person.”

“Oh baby, you’re welcome. I’m happy I could help and bring out the girl you’ve kept hidden all these years. To be honest, I really enjoyed tonight and we will be doing much more of this, I promise. I want you to be completely comfortable as Chloe so that we can do all the girly things girls do and I mean everything, baby.”

The drinks had me giggling and smiling as I laughed and said, “I can’t wait, honey.”

“Good, because I’m quite certain that things will change for us. After tonight I’m even more sure of that.”

The waiter came over with a desert menu, “Would you girls like to order some coffee or desert tonight?”

Kate spoke up, “Thank you Sweetheart but we need to watch our weight, so not tonight.”

He flirted a little and said, “Oh you girls don’t need to worry about that, you both look gorgeous and don’t need to watch your weight at all.”

I blushed as he was looking at me and said, “Thank you, but we’ll pass tonight honey.”

He left and Kate giggled, “Honey? You handled that perfectly, just like one of us, Chloe. I think you’re going to well around men, sweetie.”

That night Kate had me between her legs and she had multiple orgasms as I strained in my cage begging her to relieve my swollen balls. I was in need of relief but Kate was starting to enjoy the power of being the key holder and explained that when I am finally allowed to have sex again, the experience will be heightened and better than ever. She said that it was only a week of waiting and that right now her happiness was all I should focus on.

My instructions for the week was to keep myself hair free, live as Chloe and dress full time. I was to please Kate whenever she demanded and if I lived up to her expectations come Friday night I would be released and I would finally be able to have sex and relieve all of my frustrations.

The following week I worked at home like I do every day but this week I was dressed perfectly all week. I remained on edge all week and didn’t want to displease Kate and jeopardize my release. So all week I took care of all the house chores, made dinner, kept myself looking perfect, and pleased Kate in bed each night. She would tease me and play with my cage and balls then watch me suffer as my cock tried to grow inside the chastity cage. She enjoyed the situation and laughed each time she saw my discomfort.

“Oh honey, I’m really enjoying this. Who would have imagined that such a small device could give us such pleasure and pain? I glad you agreed to this honey because in the end I believe you’ll be happy with the results.

Well tomorrow night is your release date and you’ve been such a good girl all week that it looks like you’ve earned your freedom. I have a project for you tomorrow and unfortunately it will involve you dressing back in your male clothes and being my husband again for a few hours. You have an appointment at the bank tomorrow afternoon to sign some papers regarding our Mortgage and Insurance. You are to meet with Jean Conner at 3:30 pm. After you finish the paperwork I will meet you at Clovers for some drinks and afterward I’ll take you home and release you from your cage.

I considered having you dress as Chloe for the appointment but realized that it would be too cruel but I still want you dressed. What I want you to do is wear your bra and panties along with your pantyhose under your man clothes. If you wear a suit jacket nobody should be able to see your padded bra pushing out from under your shirt. I want you as horny as possible all day and I think this will help enhance your night in bed. No arguments, so if you want your release tomorrow night you will do exactly as I’ve instructed. Do you understand exactly what you are to do?”

With my mouth wide open in shock, I nodded and said, “Yes.”

The next day I begrudgingly showered and put on a pair of dress pants along with my Oxford dress shirt over my lingerie. The pantyhose under my pants made my legs tingle and feel sexy but the padded bra was clearly visible in my dress shirt which made me very self-conscious but I did as Kate suggested and wore one of my sports jackets If I held it a certain way the padded bra wasn’t that visible. It would be a test of my will as I knew I had no choice but to as Kate instructed if I wanted to finally get my release tonight.

The paperwork signing and meeting went without a hitch and Kate was right, nobody noticed or cared that I was wearing a full set of women’s lingerie under my clothes. I drove over to the bar and got there at 5pm and waited for Kate at the bar and ordered both of us martinis as I knew she would be arriving shortly. I felt very self-conscious as I sat there with my padded bra pushing out my shirt under my sports jacket but nobody seemed to notice and once I started drinking my martini my confidence grew and I relaxed a little more.