Marriage Made in Heaven

A Marriage Made in Heaven by Princess Pervette

It must have been the fourth time, at least, that I had asked my wife to dress me in her clothes.

This had been a fantasy of mine all my life. For as long as I could remember, I had had fantasies about being dressed as a girl. Not dressing up as one, but being dressed, put into girls' clothes by a woman. Not forced, not by a dominatrix, but by someone I knew--a girlfriend. Some girl who would just like to feminize me for fun. I had never had a chance to try dressing as a boy. I had had no sisters, and my mother's clothes had never held any attraction for me whatever. And I don't know whether I would have dressed up had the opportunity arisen; I was much more interested in being dressed.

And in fact, years before Sheila and I were married, I got a chance to live out that fantasy. Joan, a girl I was living with, decided one evening that she would like to dress me in her clothes. I said yes, eagerly; this was what I had always wanted to experience. But when she got me into her things, it felt terrible, as if I were doing something that was, at some very deep level, wrong. I was bitterly disappointed; I had expected to enjoy it; I had wanted to enjoy it; and I couldn't. So that one try was our last.

I never forgot that experience. I still had fantasies about wearing soft, lovely dresses and skirts. A couple of times after that failed experiment, when Joan was out, I tried again on my own, each time hoping that this time I would like it as much as I had expected to. I never did: there was nothing but that same wrong feeling. So I finally gave up and didn't come back to the idea until after I met Sheila.

I had another, darker fantasy, however, which I kept to myself. This one was about meeting a man who would dress me up and use me as his girl. I masturbated to that fantasy sometimes. I had never had sex with a guy and had never wanted to, in the ordinary way; but somehow the thought of dressing up like a girl and being treated like one... I was ashamed of that fantasy and kept quiet about it, never saying anything to Joan--or, after I was married, to Sheila. It was my guilty secret. I never had a chance to live that one out; I never met such a man. Never looked for him, in fact. Still, at odd times the fantasy would resurface and get me excited.

A few weeks after we had met, when I already realized I was falling in love with her, I learned that there was something special about Sheila. I happened to mention her in glowing terms to a mutual friend. He gave me a funny look and said, "Sheila? Watch out for her, Rog. She's a nice girl, but she has some weird ideas. She's gone through boyfriend after boyfriend, and they never last. She does...funny things...to them."

"Funny things...?"

"Really off the wall. I knew a boyfriend of hers, and you should see what she did to him. By the time she was finished with him, she had him mincing around in dresses like a regular fairy."

My heart leapt up. But all I said was, "You mean...?"

"She likes to put her boyfriends in her clothes. She gets off on that, I guess. If she hasn't tried that on you..."

"Well, no, she hasn't...."

"She will, sooner or later. Don't say I didn't warn you."

So she put her boyfriends in dresses! I was in love with her already; this put me head over heels. Would she want to do this with me...? It would be a marriage made in Heaven.

I didn't have long to wait. One evening, when we were at her place, relaxing after a good dinner and some drinks, she said,

"Rog, honey...I'd like you to do something for me. Something fun. Please say yes."

From the way she said it, I had a pretty good idea what she had in mind. My guess was that she hoped that the dinner and drinks would put me in a receptive mood. Soften me up. I played dumb and asked her what it was.

"I'd like to see how you'd look in my clothes. I think you'd look cute."

So there it was. Under the circumstances, I didn't see any point in concealing my own kink. I told her all about my fantasy--the one I could talk about, that is--and about my trial with Joan and its failure.

Her eyes lit up. "Oh, Roger, that's terrific! And I'll bet I could make you like it."

Well, as you can imagine, I was only too happy to comply. The trouble was that, once dressed, I felt awful, just as I had that time with Joan. She thought she could make me like it, but she was wrong. And, as with Joan, I thought that persistence might be the key, and, once we were married, it was always I who proposed a dressup session. And it always felt Wrong.

It was no better this evening. "I don't know," I said, once I was in her clothes. "I just feel it's a thing I should enjoy. They're such lovely things, and they look so nice, and I think they should feel so nice.... I know...I try it and then I feel like a damned fool wearing this stuff. And I look like a damned fool. And worse than that, I have this feeling that I'm doing something profoundly wrong. Something I have no business doing."

"Roger, we've been through all this before. You're internalizing Society's standards. And until you get over that, you're going to have problems with it."

"But why? I don't give a damn about Society's standards! It's my life, and I'll live it the way I please. So why can't I enjoy it the way I think I should?" I paused. "I feel somehow...cheated. Cheated by something inside me that's keeping us both from a pleasure I want and that I want you to have."

That was Thursday night. Nothing further was said that evening. Friday, I came home from work tired and late: it was my last day before a two weeks' vacation, and I had had a lot of things to get out of the way. So, although I had always imagined coming home after just such a day as this and putting on a dress to relax, I was just too fatigued to try. I didn't want to go to the trouble, especially since I knew I could only expect the usual downer. I went straight to bed right after dinner.

Saturday morning, I had just come out of the shower and was about to get dressed when Sheila stopped me.

"No, Roger," she said, "we're going to try something new.

"I've been thinking about our talk Thursday, and I agree with you. There's a girl inside you trying to get out. It's your kink. I know that, and that's why you keep asking me to dress you. I've got my kinks, too, and one of them is dressing guys up. Letting that girl out so I can see her and have fun with her. But you're fighting her and that's why it isn't working.

"So we're going to take drastic measures. You're on vacation now. Two weeks, starting Monday. Counting this weekend, that's sixteen days. And for the next sixteen days I am going to make you dress like a girl. All day, unless we go out. And all night, too."

"You mean," I said, "you're going to force me to dress." I paused, as I realized the full significance of what she had said. "Whether I like it or not."

She nodded. "That's it, Roger. Whether you like it or not."

"It sounds like...what do they call it?...feminine domination to me."

"You can call it anything you like, Dear," she said. "I'm not going to tie you up and whip you, if that's what you're thinking. But I'm going to feminize you. And you're going to let me do it. And if you feel like a damned fool, as you so sweetly put it Thursday night... well, that's going to be just too fucking bad. You'll be feeling like a damned fool for sixteen days."

"But...why?" I don't know why I asked. I knew.

"Roger, Hon, this is going to be kill-or-cure. By the time I'm done with you, you're either going to love being dressed like a girl, or else you're never going to want to do it again.

"Your problem is acceptance. Accepting yourself as a crossdresser. I know, you think you do already, because you keep telling me you want to dress, but I don't believe it. You said you didn't give a damn about Society's standards. I don't believe that, either. So I'm going to force you. That relieves you of the responsibility. You haven't asked me this time; I'm telling you to do it. You're going to do it, not because you want it, but because I want it."

"But you want it because you know I want it," I objected.

"Don't even think of playing mind games like that," she snapped. "Never you mind why I want it. I want it and you're going to do it. And that's that."

Sheila is a lovely wife. Better than I would ever have expected-- better even than what I had expected in the excitement I felt when we first fell in love. No matter how well you think you know someone, marriage always brings surprises. And the wonderful thing for us was that the surprises had always been pleasant ones.

But even in the happiest marriage, some things are out of bounds. Sheila and I have ways of insisting on things without having to quarrel about them. One of us just says something, and somehow, probably from the tone of voice, the other knows not to argue about it. And when she said, "You're going to do it and that's that," I knew this was one of those times.

She turned to my bed. She had laid out a day's outfit for me there. Panties, bra, garter belt, and nylons. The panties and bra were plain white, but satin with a touch of lace. Little bows at the front of the panties and between the cups of the bra. A pink slip with lace about the hem. A rather plain blue denim skirt with an elastic waist. A simple white blouse with a touch of lace about the collar.

"These are the most comfortable things I could find," she said. "If you're going to be uncomfortable dressed, I don't want it to be physical discomfort. I'm working on your mind, not your body."

I got dressed without much difficulty. I was used to it by now after all those previous tries. First the garter belt and nylons, rolling the nylons onto my legs and clipping them onto the garters.

Then the panties. I had the same silly feeling I always had when I put them on. This was always the first disappointment. I expected them to be sexy, and they weren't. You know--draw them on and BANG!...instant arousal. And that never happened. It didn't happen this time, either.

Then the bra. I fastened the closure, turned it around so the cups were in front, slipped my arms through the straps, and adjusted it for height--something a woman doesn't have to do, since her breasts sort of align it automatically. It was tight, and I felt the underwires dig into my chest. Not nice. Sheila handed me a couple of balled-up stockings, and I put them into the cups to give myself some boobs.

"I'm going to have to get you a bigger bra. And some proper forms," she said. "I didn't have time yesterday. These will do for the time being, but for sixteen days..." Why did she keep emphasizing that? Sixteen days--they seemed to stretch out before me like an eternity.

Then the slip, the skirt, and the blouse. No better than ever before. Inside me, something was saying, as it always did at this point, "You don't belong in clothes like these." I began to panic. This wasn't just for an evening's fun. This was going to be all day. And the next day, and the next...

She had gotten shoes for me, too. Very conservative pumps, with heels only an inch and a quarter high. I put them on.

I thought that was it. I had forgotten the makeup. "Not too heavy, Girl," she said. "Heavy makeup is for evenings." She sat me down at her vanity and began to apply the usual things: foundation, coloring, a bit of blush. Only the least touch of shadow on the eyes. Lipstick: subdued, not a bright red.

"Okay, that's it for to-day," she said. "I'm going to have to get you a wig, too. But for the time being you're just going to be a man in a dress."

That was what I was. I thought about all the crossdressing stories I had read. In those stories, whenever the man reached this point, dressed as I was, he felt a rush of joy, or of relief, or of arousal. Even if he disliked it, the author usually made him feel a covert sense of enjoyment. Not me. I just felt...well, like a damned fool, as I had told her Thursday night.

That was the longest day in my life. I moped about the house, tried to read, tried to busy myself. I went into the kitchen and helped her with the dishes. And all the time I was conscious of the ridiculous getup she had put on me.

I spent most of the afternoon at the computer, working on a programming problem I had set myself. I hoped that by concentrating on the problem I could manage to forget how I was dressed. I did, for short periods of time, but that only made it worse when I stirred in the chair and remembered what I was wearing. I didn't make much progress with the program, and I didn't make any progress at all with the clothes.

I found I had to avoid mirrors. If I didn't avert my eyes, I'd see what looked like a woman's body with a man's head--my head-- foolishly sticking out at the top. And whenever I walked into a room where Sheila was, I felt a lurch of anxiety. The fact that this was her doing made no difference: I felt exposed and conspicuous.

Sheila was out again that afternoon. She must be shopping, I thought. Shopping for me. Getting breast forms, I thought, and more bras. I shuddered. And who knew what else? Clothes enough for two weeks, probably. While she was gone, I dreaded the sound of the doorbell. Mercifully, nobody came by. When she came home, she was laden with packages. She put them away without offering any explanation.

When we got ready for bed that night, she had a nightie for me. Pink silk, with camisole straps.

"No PJ's for you, Girl. Seven days a week, twenty-four hours a day, remember."

That night I had a nightmare. I was at work, and I could hear the other guys in the office talking, apparently about me, but nothing they were saying made any sense--and then I looked down and saw that I was wearing nothing but a bra and panties, and they were all staring at me. And then they all began to grin.... I woke up in a cold sweat.

The next day was nearly as bad. The only improvements, if you could call them that, were a wig and breast forms. "This is a gamble, Roger. These cost a bundle. But if this experiment works, you'll get plenty of use out of them. If not...well, maybe I can find some other `girl' who can use them."

The breast forms were a surprise. They were heavy! I had never appreciated how much weight a woman was carrying about on her chest. I felt as if I was going to have to lean backward all day just to keep my balance.

The wig was pretty and long, and actually the way the hair curled was nice. But when I put it on after dressing, all I could see in the mirror was a guy in a wig as well as a dress. This experiment of Sheila's wasn't going to work.

The first three days went by like that. I had begun to hope: maybe this would prove to be an acquired taste, and maybe I would begin acquiring it. No sign of that so far.

The fourth day, I found I was getting used to the experience. Sheila had laid out a light blue dress with a pretty floral design on it, and, after I had put on underwear and hose, I slipped it over my head pretty much without thinking.

"Getting used to it, aren't you, Honey?" Sheila asked me.

"Yes," I admitted, "it's becoming a matter of habit."

"And you're coming to enjoy it, aren't you?"

"Nope."

"Hmmmm." She thought a minute, then said, "Lie down on the bed." I lay down. She lifted my skirt, pulled down my panties, and started to fondle me. "Maybe the association with sexual pleasure will help," she said and proceeded to give me the most fantastic blow job I had ever had. There I was, feminized from head to foot, having my cock sucked by the most wonderful woman in the world. Sheila has a talented mouth anyway, but she must have put everything she knew into that blow job.

It didn't work. It was terrific sex, but in spite of what I was wearing, not because of it.

The fifth day--Wednesday--brought an interruption. I was wearing a nice pearl-gray number and had just finished my makeup when the phone rang. It was work. A crisis had arisen, and they needed me. My boss was full of apologies.

"I know it's an imposition, breaking up your vacation this way. I'd hate it, myself. But you're the only one who knows the full picture, and..."

I cut him off. "Thanks for your concern, Jay, but don't worry about it. This afternoon soon enough?" He said yes and we hung up. The first thought that came to mind was that this would be a break from Sheila's forced feminization. Or so I thought.

"Okay, I agree, you can't wear a dress and heels," she said. "Or the wig, or makeup. But everything underneath stays on. Except the bra. You can put ordinary socks on over your nylons if you feel you need to."

So off I went, wearing garter belt, nylons, and panties under my suit. The crisis at work was worse than I had imagined. I ended up working all afternoon and into the evening. I phoned Sheila, told her not to cook dinner, and that, in fact, I had no idea when I would be back.

"This looks like being an all-nighter, Hon," I told her.

This kind of thing had happened a few times before, and Sheila was used to it. "Okay, if that's the way it is," she said. Then she laughed. "Just don't wear anything I wouldn't wear." Damn. In the press of work, I had completely forgotten what I had on under my trousers.

Around six PM, the other people went home, leaving only me and Bess, my assistant. Things had begun to get under control again, and, although we had a lot of work ahead of us, the two of us would be able to finish up alone. We decided that would be a good time to break, and after a quick phone call, Bess joined me for dinner--on the company, naturally. We talked shop over most of the meal.

It was nearly one in the morning before we got everything resolved and had written and e-mailed off the necessary information and memos. We didn't see to be any point in going home at that hour, so we decided to sleep over in the office. It wasn't the first time for that, either.

Now, you must understand that there wasn't anything going on between Bess and me. She was a gorgeous brunette with a terrific figure, highly intelligent, in her mid-twenties, and I liked looking at her. We liked each other, we worked well together, but that was as far as it went. So I didn't attach any significance to our sleeping over in the office. That had happened before, and it had always been understood, without either of us having to say anything, that there wasn't going to be any messing around.

I usually slept in my chair on nights like this, slumped over my desk or a table, but there was no free space this morning; everything was covered with papers. With a sigh, I finally took off my shoes and men's socks and stretched out on the floor. At least it was carpeted.

Carpet or no, it was hard and damned uncomfortable. Dog-tired though I was, I couldn't get to sleep. I tried lying on my right side, and when that didn't work, I tried lying on my left side. Then I tried lying on my right side again.

I had managed to fall into a fitful doze when a noise awakened me again. It was Bess.

"I'm sorry, Rog," she said, "I forgot my purse." Then, after a pause, "Hey!...what's that you have on your legs?" My trouser legs had ridden up. I drew up my legs, but it was too late.

"Are those nylons you're wearing?"

I didn't know what to say.

"They are! Rog, honey, do you wear those all the time? You can't. I would have noticed. What's going on?"

"Er...I...er..." I tried to think fast: hopeless in my groggy state. "I...I have this circulatory problem in my legs...."

"Roger, those aren't surgical stockings. Don't try to kid me."

"Bess, I just don't want to talk about it. Okay?"

"Come on, Rog. You know me. We've worked together for a long time now. You should know by now that you can trust me to keep quiet. You know that whatever it is, I won't blab it all over the office."

Eventually, she wormed the whole story out of me. The hose. The panties. ("Panties? You've got panties on, too?") The futile attempts to get used to wearing drag, to feel comfortable in it. Sheila's experiment.

"But that's wonderful! Let me see!"

Letting her see what I had on under my trousers was the last thing I wanted, but she wouldn't let up. Meanwhile, it was getting later and later, and I was going to have less and less time in which to catch up on my sleep. Finally, to get rid of her, I dropped my pants so she could see what I was wearing.

"Roger, I never dreamed. And I think it's wonderful. You know, I once dressed up a boyfriend for fun. He didn't like it, but I did. I think men look cute that way."

Another woman who dressed her boyfriends...! What was this, an epidemic? Did all women do this? But by this point, I didn't care how she thought men looked. I was annoyed--and sleepy. "Okay, Bess, you've had your little show. Now could I please get back to sleep?"

She got her purse and left, and I tried to get back to sleep. It was hot in the office with the air conditioning off, so I left my trousers off and in fact ended up stripping down to nothing but my panties and hose. Bess had seen everything, after all.

The next thing I knew, Bess was shaking me awake.

"Rog, it's almost eight. You're going to have to get dressed. People are going to be coming in soon."

As I started to dress, she went on. "You know, while you were asleep, I was watching you. When I came in, you were facing away from me, and I saw how you looked. You look great, you know. Just smashing. I never would have dreamed that you'd look so good that way."

She paused. I didn't say anything. I couldn't think of anything to say. Then she said, "No wonder Sheila encourages you. The way you look, if you were mine, I'd keep you dressed in women's clothes all the time." I gave her a look. "No, I'm serious."

"But both you and Sheila...!"

"Oh, it's more than just both me and Sheila. There are lots of women who like that. You just never hear about them. You hear about the failures--the women who divorce their husbands when they catch them in dresses. But you never hear about the successes. People would be surprised if they knew what goes on in the privacy of other people's bedrooms. Not just dressing up, either. All sorts of things.

"And you really look, well, gorgeous. I hate those cotton briefs men wear. So blah. And"--she smiled--"that satin really shows off the contours of your butt."

I wasn't amused. I turned to her.

"Bess, look at my face. Okay, imagine me all dressed." Was I really discussing this with her? "Imagine even that the skirt is full enough to hide my narrow flanks and that I've got boobs. Imagine all that, and then picture this guy's face sticking ridiculously out of the top. Even with a wig. I look like hell and I know it."

"But that can all be changed with makeup, Rog. You'd be surprised how much you can do with makeup. I've done theatrical makeup and I know. Let me come over and help you and Sheila. I'll show you just what can be accomplished. You're a natural, and with a little work you'd look terrific."

I went home. I had fixed their emergency for them, and I was still on vacation. But as I went out to my car, I was walking on air. Why? Why did I suddenly feel so good? Then I realized: I was enjoying what I had on under my men's clothes. Something had broken the barrier.

Driving home, I was looking forward to getting back into a dress. But that was nothing new; I had looked forward to that before, and the actuality had always been a let-down. But somehow I had a feeling that this time it wouldn't be. What had changed? Nothing, except that now Bess knew. Knew and liked the idea. Knew and hadn't laughed at me. Knew and wanted to help. Knew and said that in Sheila's place she would keep me in dresses all the time.

I wasn't sure. Maybe I was on the verge of this breakthrough anyway, and Bess's response had just provided the trigger. But why ask why? If this was really going to be the turning point, who cared what brought it about? It was enough to enjoy it and be grateful.

But when I got home, I didn't put on a dress. I was bone-weary. I told Sheila we had fixed the problem but didn't say anything about Bess. I didn't want to talk; I just wanted to get back to sleep. So I put on a nightie, which, I realized, was very nice, and fell into bed.

Part II

When I woke up, it was late afternoon. Sheila heard me stirring and was in the bedroom right away.

"Are you rested?"

I mumbled something.

"Okay, Girl, we're back to normal again. And you're back to your dresses again." She indicated underwear and a skirt and blouse she had laid out for me. "Clean yourself up and get into these."

I got up, wondering: Had the breakthrough really happened? I would know in a couple of minutes. I went through the usual morning ritual, shaving, showering, and so forth. Then back to the bedroom. I put on my garter belt, nylons, panties, and bra; struggled with the breast forms and the bra. Then a slip, and then a skirt and blouse. Then the wig. I stopped and took a breath. Looked down and took stock of myself.

It had happened.

I liked them.

They felt wonderful--wonderful as never before. They felt as if they belonged on me. As if they had been made for me--and I for them. And, wearing them, I had that amazing feeling of peace, of well-being, of contentment, that I had always dreamed of.

I grabbed Sheila, hugged her, kissed her, waltzed her around the bedroom. "It worked! I like them! I feel wonderful!"

"What `worked'? My, er, training? Or something else...?" She narrowed her eyes. "Just what went on last night at the office?"

I told her. Bess's discovery and her response.

"I don't know, Sheila. But I think maybe it was just that someone else knows. A third party."

"But I knew, Roger. I've known all along."

"Yes, but...well, you're part of me. I mean, your knowing isn't like someone else's knowing. And," I went on, "she liked the way I looked. I was sacked out on the floor, and she saw me in just my panties and hose. And she complimented me. Told me how good she thought I looked. She even said that if I were her husband, she'd keep me dressed all the time."

Sheila looked at me, considering. "You know, I told you the issue was self-acceptance. You thought you accepted it. You told me you did. But I think, at some level deep inside, you didn't. Down there, you were thinking about how you would look to other people. How they would laugh, or be disgusted."

"And Bess didn't laugh."

"And she wasn't disgusted. She liked you that way."

Then I saw myself in the mirror. Oh oh. The same revolting sight: a man, looking silly in a dress and a wig.

I looked away again. Looked down at my skirt--a striped number in blue and gray--and felt good again.

This was strange. Looked in the mirror, was appalled. Looked away and down at the dress, felt good. Back and forth.

Well, the solution was simple: don't look in the mirror. And for the rest of that day, I avoided mirrors. But the good feeling lasted.

Bess called just before dinner and asked for Sheila. They talked, I heard Sheila say something about just after seven, and after a few more words, she hung up.

"Bess is coming over after dinner. She's going to help with your makeup."

That, as it turned out, would be the least of it.

She showed up, all right, with a big shoulder bag, out of which she began to take all kinds of jars and tubes of stuff.

"You have to think of it as if it were theatrical makeup," she explained. "With the right colors, with shadows and highlights, I can change the shape of your face altogether."

She had me shave again. Chest, underarms, and legs as well as my face. Then they sat me down at Sheila's vanity and put a towel around my shoulders, and Bess set to work. She started by taking some funny red stuff and rubbing it into my face.

"Beard cover," she said. Then she examined me.

"Typical long male face," she commented. "Typical prominent chin. Well,"--she started fussing with various things from little tubes-- "it's easy enough to soften those." As she worked, she provided a running commentary, explaining just what she was doing and why, so I would be able to do it myself in the future. Finally, lipstick (and lip liner), mascara, and eye shadow.

"There!" she said after she was satisfied with my face.

"Bess, she looks great!"

"I think so. But that wig's the wrong shape altogether, Sheila. It makes her face look longer. You don't want to emphasize that. The makeup and wig work together, you know. I've pulled the hair back, and that helps a little. But what you really want is one more like this...." With her hands she made a shape in the air around my head.

"Oh, yes!" Sheila exclaimed. "I went for color and never thought about what shape I'd want."

"Well...we'll make do with this for now, but the next time you go shopping for her, you'll know what she needs."

I noticed that they were both referring to me as "she."

With a flourish, Bess pulled the towel off. "Voila!"

I had been facing the mirror all the time she had been working on me, but I had been concentrating on what she was doing. Now, for the first time, I saw the overall effect. I looked like a girl. Almost. And with the right kind of wig...I don't know whether I would pass on the street, but for once, when I looked at my reflection, I didn't see a man's head sticking out, the way I had described it to Bess in the office. For the first time I felt as if I was believable as a girl. And that, in turn made me even more comfortable in drag than Bess's acceptance had.

"Stand up, girl. Let's see how you look."

I stood up and had a look at myself in Sheila's full-length mirror. My legs looked good. I raised my skirt and looked again. I was shocked. No man had any business having legs as pretty as mine were in their hose. I had never noticed that before. But Sheila must have, because she said,

"Bess, don't miss her legs."

"Oh, my God!" Bess exclaimed. "Legs to die for!" She paused and looked me over. "Well. There's our girl. Now what do we do with her?"

There was something about the way Bess said that that made me feel a twitch inside my panties. Bess and I had never messed around, but....

Sheila put in, "Well...the main thing when you get a man in a dress is to have fun with him. With her, I mean."

Bess said, "I think she should find out how it feels to be a girl."

"You mean...?"

"You know perfectly well what I mean."

Bess went back to that big bag of hers and got something out. I had never seen a strap-on dildo before, but I knew immediately that that was what it was, and I knew, with a sudden tension, what was going to happen.

"I thought we just might have a use for this," she said. "We've made a girl out of her. Don't you think we should make a woman out of her, too?" She turned to me. "Lie down on the bed, Dearie. On your back."

I lay down, heart pounding. I was scared, but excited.

"Now," Bess said, "I think you should be the one to take her virginity, Sheila. She can satisfy me with her mouth, like the little dike she's going to be from now on, but I think it should be your privilege to be the one who makes a woman out of her."

Bess showed her how to put on the dildo. It looked pretty complicated to me. Sheila gave me a wicked grin.

"Okay, Girl." She hesitated and turned to Bess. "Let's see...I think we should give her her femme name now. This is the appropriate moment, don't you think? Roger...something beginning with an R, I think. Robin? Roberta? How about Regina?"

"How about Rosemary? That's more feminine than Regina. And we want her to be just as feminine as possible, don't we?"

"Okay, Rosemary." Sheila gave me a wicked grin. "You're about to be...christened."

My christening. Yes. As Roger, I would never have done what I did just then, but it was the most natural thing in the world for Rosemary: I lifted my skirt, pulled off my panties, and drew up my knees. Bess got some kind of lubricant out of her big bag and applied it to me and to the strap-on.

"Just relax and let it happen, Girl," she said.

I relaxed--and it happened. I felt the cold plastic of the strap-on on my butt. Then a gentle pressure as Sheila found the right place and began to work her way in. It hurt, then, as I felt her opening me up. I was being stretched, crazily violated, opened wider than I would have thought possible. It was a good pain, though. A happy pain, one that made me want her to keep on. "I wonder whether childbirth is like this," I thought. She did keep on, stretching me wider and wider, to the point that I thought something was surely going to tear...and then, suddenly, she began to slip in. I felt myself being widened inside, if you can imagine that. The pain was less, now, and I was distracted from it as I realized that I really was a girl now. Rosemary, being fucked. "Let it happen," Bess had said. I wanted it to happen. I wanted to be used as a girl. Sheila's girl.

She was thrusting hard, now, and I felt every thrust. Every thrust seemed to be pushing me further and further into womanliness. Every thrust was driving my manhood away, as if, every time she pushed in, she was making room inside me, not for the dildo, but for a new feminine nature that I was to receive. "Making a woman out of me..." As if what she was going to deposit in me, since it couldn't be semen, would be femininity, femaleness, girlhood, womanhood. As if, when she would finally withdraw, she would leave something behind: not just a smear of lubricant, but Rosemary's new personality as a woman. I imagined a kind of ejaculation from that dildo in which some magical, transforming substance would be injected into my body. And at that thought, I had a most unfeminine erection.

As if in a dream, I heard Bess's voice, far off: "Oh, look how she likes it!" But I hardly noticed it. I was too lost in the rapture of being fucked. Fucked, screwed, pronged, plowed, drilled, banged...the synonyms ran on in my mind.

Being opened up, too. Opened up for what...? I wondered: What if this were a real penis instead of a dildo? And I remembered that secret fantasy from years ago. Rosemary would want it. Rosemary would embrace and kiss her man and invite him in. Rosemary was a completely new person. And, realizing this, realizing that I was now Rosemary, I embraced and kissed Sheila.

Then it was Bess's turn. I was to satisfy her with my mouth, like the little dike I was going to be from then on. Strange...I had often admired her, and I won't deny that I had had fantasies of being with her, no matter how proper our relations were on the job. But never dressed as a girl, with my face made up by her. And although I love eating pussy, I had never imagined eating hers.

But I did. She was already dripping wet from watching us. And, like the little dike I was going to be, I pulled her down onto me, encouraging her to put more and more of her weight onto my face, to press her delicious pussy onto my mouth. I licked and probed, exploring her depths as far as I could reach, straining my tongue to get it further into her and wishing it were longer. She sighed and made little noises. I love it when a woman purrs that way; it tells me that I'm giving as much pleasure as I'm receiving.

And, as Bess approached a climax for what must have been the fourth time, I suddenly felt Sheila's lips on my cock. As excited as it was, I needed only that little touch, and I exploded.

Afterward, I washed up, put my panties back on, straightened my rumpled dress as well as I could, washed my face, fixed my wig, and went to get drinks.

As we sat there, coming down from the experience, Sheila said, "This was planned, you know." My jaw dropped. "Bess and I have been talking about your little...problem"--I turned pale--"and she volunteered to help. When she knew you would be working overnight, she called me and we agreed that it might be just the opportunity we'd been waiting for."

"So I conveniently left my purse behind...."

I stared at them. "You mean, you knew that that would make the difference for me? Her acceptance?"

"Oh, no," Sheila said. "That came as a surprise to both of us. We just thought it might help if she prodded you a little. It helped more than we ever dreamed."

"Well," I said, "I suppose I should feel as if I'd been tricked. Used, even. But all I feel is gratitude. If being tricked was what it took, I'm glad you tricked me. This has been absolutely the most wonderful day of my life. Being used? If that's being used, I want to be used again and again."

"So now you're going to be Rosemary? For good? Or just from time to time when you feel like being dressed up?"

"Er...well...not on the job, of course. Not externally. But yes, here at home, and inside me, I'm going to be Rosemary. Thank you for the lovely name, by the way. Whenever I have any feminine underwear on, at least part of me will be Rosemary. And"--I grinned--"that's going to be all the time.

"Making a woman of me, you said. You sure did. Maybe more thoroughly than you bargained for. Certainly more thoroughly than I would have dreamed."

Bess smiled at me. "I'm glad you've finally come out of your shell. Always Mr Clean at work, strictly business, always the gentleman, never a look in my direction. Sheila and I had wondered about setting up a threesome with you, but you never showed the slightest interest."

I was thunderstruck. I had completely misjudged the way things were between Bess and me. And between Bess and Sheila, in a way, too. I had always been a faithful husband and had never slept around except in my imagination. And now this. Talk about surprises after marriage...!

Sheila picked up Bess's remark. "Maybe a foursome, Bess. What about that friend of yours, Frank? Would he be...?"

"Interested? I think so." Oh, God, my secret fantasy... "He's pretty broad minded, or so he always says. We might just find out how broad minded he really is."

"Well," Sheila grinned at me, "we've got just the broad for him."

I had had one of my fantasies fulfilled; now it looked as if I was going to get my other, secret fantasy fulfilled, too. And with my wife's approval...

That night was the turning point. Suddenly those sixteen days--only eleven now, actually--seemed, instead of stretching out forever, to be cruelly short.

Sheila still selected my things to wear, so that I still enjoyed the pleasure of being dressed by her. She began to enlarge my wardrobe, too. She never took me shopping, but we went catalog shopping, and when we agreed on what was suitable, which was most of the time, we'd order it.

Dressing had finally become the experience I had dreamed of. It had miraculously stopped feeling wrong and now felt eminently right. As if I had been born for no other purpose than to be dressed up as a girl. As if this were my destiny.

Rolling on the gossamer-thin stockings, seeing my legs take shape and color inside this loveliest of garments, clipping the pretty garters onto their tops: suddenly the whole feminization process was just as ecstatic as I had always dreamed of its being. And panties...! Their smooth silkiness, the soft feeling as they slid over my stockinged legs, the way they concealed and almost denied my maleness...bliss! But especially the bra, which to me was the essence of femininity. The cups, so artfully sewn and shaped to hold the breasts I wished I had...the band, tight around me, so that I could never forget what I was wearing...the forms, so heavy that I never forgot them, either.

And what it did for me...! Even if I happened to wake up grouchy and out of sorts, the whole world became sweet and beautiful as I feminized myself. The only real tranquillizer. It made was a different person. No; Rosemary was the different person. A different me. I wondered, sometimes: was this whole dressing thing getting out of hand? But Sheila didn't seem to worry.

We spent a lot of time getting ready for the foursome, which was set for the last Friday evening of my vacation. Bess, now a full collaborator in what I had come to think of as the Feminization of Roger, had turned the strap-on over to us, and, to my delight, Sheila fucked me with it regularly. She had me practice sucking on it, too. Kissing it, licking it, taking it into my mouth, getting to know its contours. Getting used to having it in my mouth, learning how it felt on my lips and tongue. And thinking girly thoughts as I did this, preparing myself for the Real Thing. I remember lying in bed late one evening, playing with it until I fell asleep. I woke up in the middle of the night with my breast forms and lingerie still on and with the dildo still in my mouth. A sweet experience.

All this didn't supersede regular sex with Sheila. That went on as always, but better now, probably because a new dimension had been added to my sexuality. And maybe my experiences with the strap-on gave me an added appreciation of what Sheila felt when I fucked her.

For the Big Night, Sheila got me a slut outfit: black bra and panties, black vinyl miniskirt, fishnet stockings, stiletto heels, long acrylic nails. She applied my makeup for me, following Bess's guidelines but putting on entirely too much, exaggerating it. She and Bess had both gone for subdued colors before, but these were garish. By the time she was done I looked like a hooker.

But the Big Night was a washout. First, it wasn't really a foursome. It was just me and Frank, with the girls watching us. Second, I discovered that I didn't like sucking Frank off. I don't understand this: I had enjoyed playing with the dildo and having it in my mouth, but there was something about having a real, live penis in my mouth that was a turn-off. Perhaps the warmth; perhaps the taste of Frank's precoital secretions; perhaps the odor of a real man. Maybe just knowing that it was a man in my mouth. Somehow the entire fantasy as I kissed and sucked the strap-on had been just that--a fantasy. Feeling a real man in my mouth was...repellent. Disagreeable. Maybe even a bit disgusting. When I swallowed, I thought I was going to be sick.

This was a facer: where was Rosemary now? Where was the girl who had so looked forward to this? The girl who had loved her dildo? I concealed my distaste and pretended to be having a good time, but at the end of the evening I was greatly distressed at Rosemary's failure. We scheduled another party for the following week. I didn't say anything, but I had considerable misgivings.

Back at work the next week, I wore panties under my clothes all the time. Nobody would know. And Bess would occasionally tease me, covertly. My first day back, when people were asking me how my vacation had been, Bess said, with a look of wide-eyed innocence on her face, "Do anything exciting, Roger?"

That first "foursome" had been a failure, but the next week's made up for it. Abundantly. Sheila dressed me in nothing but a hot, sexy catsuit this time. At the start, the two girls just looked on as Frank fucked me like the girl I was and I squealed with delight. Sucking Frank had been no fun at all, but being fucked by him was divine. Sheila fed me the dildo to suck on while this was going on. Bess, watching me caressing it and bathing it with my lips and tongue, cried, "Look at her eat that thing!" But then, as Frank continued to plow me, I waved the dildo aside, wrapped my ankles up around Frank's neck, drew him close, and kissed him, hard, parting my lips, sucking his tongue in. Why did I like kissing his lips so much when I hadn't liked kissing his penis? And when Frank finally cried out and pumped his load into me, I thought I'd died and gone to heaven. Another giant step toward womanhood.

But then it turned into a real foursome. Sheila and Bess took turns using the strap-on on me. While Sheila fucked me, I ate Bess out, and then they switched places. For the grand finale, Sheila gave Frank one of her expert blow jobs and Bess did the same for me. It was a heavenly evening for all of us, but especially for Rosemary.

The next morning, as I was fixing my makeup, Sheila asked me, "How do you feel about being a girl now?"

"Oh, Hon, dreamy! I never imagined it could be that good." And I finally confessed my secret fantasy to her.

"You wanted to be some man's girl? Well, after last night, I can believe that. But you didn't enjoy giving Frank a blow job, did you?"

"I didn't think anybody noticed."

"Rosie, when you're having fun, there's no mistaking it. The noises you made with Frank last night...! And you weren't like that at all when you were giving him head."

Giving him head? I hadn't known Sheila knew such language.

"Well...I don't know. It just somehow wasn't the way it was with the dildo."

"Well, Rosie, practice makes perfect. And I guess you just need a little more practice."

Once the sixteen days were over and I was back to work, I dressed evenings, just for the sheer comfort and relaxation it gave me to do so, but I didn't generally make as much of a production of it. Pull on a pair of pantyhose, which, for me, were less trouble than the garter belt and stockings, and throw on a dress. Never mind makeup.

Nevertheless, over the months that followed, I found myself becoming increasingly preoccupied with femme things. The fact that Bess had introduced Larry, another friend of hers, to our games must have had something to do with that. I was becoming more and more of a girl. Especially with those two guys. I was getting the practice Sheila said I needed and gradually reconciling myself to giving blow jobs; and being shared by Frank and Larry, one at each end, was thrilling. And again I wondered whether things were getting out of hand.

I began to have girl-talk lunches with Bess. We'd talk about clothes, makeup, hair styles and things like that. We even talked about the other guys in the office: which ones were hunks, or cute. People in the office began to wonder whether there was something going on between the two of us, which--if you included Sheila and Frank, and now Larry--there certainly was.

One noon, however, the following Spring, I talked with her about the way this whole femme thing seemed to be taking over my life and how it had begun to worry me. "I can't think of anything else," I said. "It's getting to be an obsession. I'm a little scared. I think back to how I felt about all this just a few months before, and I wonder what's happened to me."

"Would you want to go back to the way you were then?"

"Oh, no, Bess! But there've been so many changes. In such a short time--and so disturbing. I can't walk past a women's clothing store now without stopping to look in the window. Looking and wondering how the clothes would look on me. How Frank and Larry would like me in them. It's worrisome. What did you do to me that morning in the office, Bess? Hypnotize me?"

"Of course not, Rosi...er, I mean, Rog. But if you're worried about this, you should be talking it over with Sheila, not with me. She's your wife. I'm just your, well, playmate."

That made sense. I should have realized that myself. And that evening I had a long heart-to-heart with Sheila. I told her the things I had told Bess: that I couldn't take my mind off being femme, that I was worried that this whole business might be getting out of hand.

"Let's talk, Rosie," she said. Well, that at least was an encouraging start: "Let's talk" usually presages a more pleasant discussion than "We've got to talk."

"I've been thinking about this, and I've got to admit, I'm worried about it, too. I never took any guy as far as I've taken you. Never was able to. So I'm a little out of my depth. I don't know whether we will be able to control this. I don't know whether we will want to. Whether you will want to.

"But Rog"--she switched to my male name and took my hand--"I know one thing: You're my husband. For good, and no matter what happens, you're mine. If, God forbid, we ever part, it will be because you left me, not because I left you."

Tears came to my eyes. I was crying more easily since our feminization program had taken off. It was nice, not having to hold it in the way a man has to. But the old Roger would have cried, too, hearing her say that. Anybody would have.

"This whole thing was as much my idea as it was yours," she went on. "And getting Bess involved was as much my idea as it was hers. It's all been my responsibility. And you're my man, Rog, as well as my girly toy.

"We haven't been very good about our marriage vows, have we? That business about forsaking all others, I mean. Playing with Bess, and Frank and Larry and...whoever else may come along. I like watching them use you as their girl. It's fun. And that's not going to change. Do you want that to change?"

I shook my head.

"But I'm going to be good about the business of until death us do part. That's the important one, isn't it? And even if you stopped being my man--I mean, even if you had surgery--I would still be your woman. I need you too much." She hugged me and kissed me.

What a woman! But the funny thing was that that hadn't been what I was worried about. I guess I had unconsciously assumed that we would stay together no matter what happened. What might happen: that was what I had worried about. But it was wonderful to hear her say that. I thought back to what Bess had said about the successes and the failures; this was success in anybody's book. I hugged and kissed her back, and we both cried a little.

In TG fiction, of which I had read a good deal by this time, women like Sheila were ruthless. Feminize him and dump him seemed to be the rule. Make him into a slut and then abandon him to the life of a slut. Make fun of his tiny cock and balls and then, usually, have them off. And then... Bye-bye, Sweetie! Well, mine weren't tiny, actually, but that's not the point. The point is, Sheila wasn't that kind of woman. What a lucky guy I was! What a lucky girl!

From that time on, there was no holding me back. Shortly after that, Bess discovered a swingers' club and got the four of us into it. I wore my slut outfit our first time there. As we walked in, Sheila gave me a little kiss. Then, smiling, she indicated me to the crowd and said, "This is Rosemary. She's my husband, believe it or not. But tonight she's all yours. If you want her, take her!"

They had never had a crossdresser in the group before, and the guys went wild over me. This was my secret fantasy fulfilled in spades. Any guy who wanted me had me. And they all wanted me. Some of the women did, too. They thought it was fun to have me eat them out right after they had been fucked. Little Rosemary, the star of the show! By the time we went home, my hose were in tatters and my girly little gut was awash in semen. I swear, if they had shaken me, I would have gurgled. (And I was the girl who had had so much trouble with sucking Frank last Summer!) And my ass would have been dripping all over the place if Bess hadn't had the forethought to provide me with a tampon.

There's no way to end this, because it's still going on. What will become of me? I'm going to see plenty of action, I know; this was only the beginning. We've talked about hormones a few times, and real boobs, but Rosemary, with her flagrant lifestyle, could never come out at work. Maybe once I'm retired. Maybe even an orchie then. Or surgery, so I can be a girl all the way through. Then again, maybe not. But whatever it is, I'm going to love it!

Princess Pervette August, 1999