CUTE LITTLE OUTFITS
by
Leslie

Yes. I admit it. I'm spoiled. I always get my way and my husband delights in it. I don't know why some women today look back at their grandmothers of the 1960's with disdain simply because they had the luxury to stay home and wanted to please their spouse and serve their families. Volunteering to serve your community is celebrated now while having a sense of commitment to a smaller, closer community; the family, is often denigrated. The real irony is that a stay at home housewife isn't put down by men, but by other women. Is it jealousy? Is selfless service to those whom you love really so horrible? Or is it just horrible for a woman but not for my husband? And, why has selfishness; "I want it all" become accepted as a feminine virtue? While some masculine traits are worth emulating, that's not the one I would pick.

I'm spoiled, but I'm not selfish. I delight in pleasing my husband. I'm just fortunate enough to have a husband who delights in serving me and derived happiness from pleasing me. Isn't that what all husbands should be? I'm not saying all couples should go as far as we do demonstrating the husband's sense of commitment, but when it comes to our treatment of other people; one's highest priority should be to one's spouse. Admittedly, I keep him in cute little maid outfits to remind him of the duties he has willingly assumed, but that is specifically because he sees the femininity of our grandmothers' generation as admirable traits to be emulated and celebrated and he wants to experience the satisfaction of serving a loved one in a similar fashion.

But, if you come to our house, please don't interpret his attire as a rejection of masculinity. It's not. If anything, it's his desire to understand more of the full spectrum of human experience by going beyond the traditional masculine-feminine boundaries. In his case, it's not a rejection of anything. It's just for fun, but his kindness and his consideration is genuine, as is our love.

It all started with a trip to Hawaii. I had worked with Mike for seven years and we had a very good professional relationship. We had spearheaded a project that was extraordinarily successful and our boss wanted to thank and reward us for a job well done by sending both of us to a convention in Hawaii for a week. At the convention, there would be interesting talks to attend and some professional development, but he made it clear that it was mostly just for us to have fun, so he wanted us to stay a few days longer to take in the sights.

We had a total of ten days. Unfortunately, his budget couldn't cover two round trip business class airfares from Boston to Hawaii plus two rental cars, two rooms in the high end hotel the convention was in, so it was left to us to find some cost cutting methods to allow both of us to attend. We opted to fly coach, share a room at a cheaper, but still nice, hotel and get just one rental car. I knew Mike well and was confident there would be no problem sharing a room with him. I was wrong.

We arrived and checked in to our hotel on Sunday afternoon, put our luggage in our room and headed over to register at the convention and to attend a welcome mixer on the beach complete with leis, hula dancers and a hog roasted on an open fire. We had a blast.

When we got back to our hotel late that evening. He turned the TV on and I started unpacking. I hung my clothes in the closet and emptied my suitcase onto my bed to move things into the draws. I guess he was watching me, but I didn't notice any particular interest while I was folding my lingerie and placing it into the draw. He did hang up the suit he had brought for the banquet that would be held on the last night of the convention and he hung up a sport jacket and pants, but other than that, he would just live out of his suitcase. He seemed to like the background noise of a TV and that background noise proved to be his undoing.

On Monday morning we were up early and we each showered and got dressed, but when it was time to go down to breakfast he said he'd rather watch the news, so I went without him. As I was leaving he said that he'd meet me at the car. I guess he thought I would take a long time to eat breakfast and go straight to the car, but we had never agreed to that. So, when I returned to the room after about twenty minutes, the TV was on and he didn't hear the electronic lock engage or hear the door open.

I couldn't believe it. It was the most embarrassing moment of my life and of his too. But I kept my composure and even took charge of the situation. When I spoke, he almost jumped out of his skin. I said, "What the hell!" As he looked up at me, he was mortified - and rightly so. The look of anguish on his face was something I had never seen before. I felt angry at his invasion of my privacy, but seeing the expression on his face, I felt sorry for him at the same time.

Then when I figured out more precisely what he was doing, I became more assertive, "Well, go ahead. You can't stand there on one foot all day. Put your other foot in and pull it up. You violated my privacy by getting into my underwear. You know you want to wear it, or you wouldn't be holding it that way, half way up one leg. It's not as though you're the first guy ever caught putting on a woman's underwear - pervert!"

I wasn't really that offended. "Pervert" was intended more as a joke. I found his situation more humorous than anything else, but a little bit disgusting as well. He hadn't bothered anything else of mine, just that one item. He was putting on my all-in-one girdle. In retrospect, when I was unpacking and had placed it on my bed, I do remember seeing an odd expression on his face as he glanced over at it, but I took it as disappointment at the discovery that I sometimes needed a girdle. I had brought it along with a nice dress to wear to the convention banquet.

"Was it your plan just to slip it on to see what it feels like and then put it back in my drawer? Or were you going to parade around the room in my shinny white all-in-one girdle?" I asked. "It's a good thing I opted for a light breakfast. When you said you would meet me at the car, I guess you thought I wouldn't come back up here. Were you going to stuff the bra so you'd have a set of boobs while looked at yourself in the mirror, or were you going to do something really disgusting in it?" I got more angry as that prospect crossed my mind and I lashed out. I was intentionally trying to demean him, an act of which I'm not proud, but he just stood there dumbfounded.

He now had both feet on the floor, having declined the chance to put his second foot through, but he was still standing there holding my all-in-one half way on. "You should have asked me. I would have let you try it on if you had just asked. I hope you weren't planning on wearing my dress too. Go ahead, put it on. Now! At least you're wearing panties under it, so it isn't totally unsanitary. But, come to think of it, those aren't my panties. Are they? So, they must be yours. You wear panties. Holy shit! You look like a girl. Where are your boy parts?"

As I talked, I walked over to him to get a better look at the spectacle. While I didn't literally have him by the balls, I did figuratively, and he knew it. "How often do you wear panties" I asked as I slapped his ass through his nylon panties. It was then that I discovered that I had unintentionally come dangerously close to literally having him by the balls. I was embarrassed by that discovery and he clearly felt humiliated and flinched, but still he said nothing.

I remember thinking "I hope he knows that was by accident", but it had the unintended consequence of driving home just how hopeless his situation was and that he was totally at my mercy. "Oh, I see" I said. "Doesn't that hurt? Cat got your tongue?"

His reply was, "That's none of your business!" That was the wrong answer for somebody in that predicament!

"You're standing there in my underwear and you have the nerve to tell me it's none of my business? You asshole!" was my reply. And, he suddenly became much more conciliatory.

"Oh God. What can I say Leslie? You've literally caught me with my pants down. I didn't think you'd be back. I thought you had left. I'm so sorry. Yes, it is your business. I simply meant that any discomfort I might experience from tucking my...Or, my choice of... Oh Hell, never mind. I..."

"Oh, shut up. You're only sorry because you got caught. I don't want any lame excuses. It's bad enough that you were going to use something that doesn't belong to you without permission, something of mine that is very personal, so don't insult me with lies. I'm not stupid, and when you lie to someone, you are saying that you think they are so stupid that they will buy it, or so inconsequential that they don't deserve the truth. Either way, it's an insult and I've done nothing to deserve such treatment from you. In all the years I've known you I have never known you to lie. Even when you should lie, you don't, which by the way is really obnoxious. So, don't start now." After I said that, I could see real hurt in his eyes.

"Now, you have my permission to wear it. We don't have time to fart around here. I didn't want to miss or be late for the opening address of the convention. We have to go. I'm serious, put the damn thing on. You wanted to wear it and that's exactly what you are going to do. You are going to wear it all day. But tonight you will wash it and hang it up to dry. Now get dressed! No wait! Here put these on first." I said, as I reached into my draw.

"Pantyhose?" he said.

"That's right" I said, "If you're in for a penny, you're in for a pound. And now you are in it up to your neck. So, this is what you skipped breakfast for? I guess sharing a hotel room with you was a mistake. You know I own you now. Don't you? From now on when I say "jump", you say "how high ma'am" and you jump. Got it? Just wait till tonight and see what cute little outfit you'll be sleeping in. By the way, you're taking me to dinner tonight, a very nice dinner at a very nice restaurant. And guess what you will still be wearing under your clothes at dinner?"

I must admit, it was a bit sadistic of me, or maybe I was just enjoying the power I held over him. But he deserved it, and he complied with my every command, so no harm - no foul.

He did offer some resistance when he had the audacity to say "No thank you." Then he continued, "Trying on your all-in-one is all I wanted to do. When I saw you unpacking it I just couldn't stop wondering what it would feel like to have it on. For some reason, I fixated on it, and it's all I could think about. I know it was wrong, to take it without your permission, but you can understand why I couldn't ask you because I wanted to keep my interest in such things a secret. I don't want to actually wear it though."

My reply was, "You should have trusted me and asked me to let you try it on then. Now I don't give a rat's ass what you want. This is not a negotiation, sweet cheeks. Sit down on your bed, put the pantyhose on and then put the all-in-one on over them. Do it now!"

Realizing his bluff had failed, he complied with my instructions. I did notice he put the pantyhose on effortlessly. He obviously was proficient at it and I wondered if he could hook a bra behind his back just as well. Time would tell (he can) but first things first.

"You will have to keep your sport jacket on all day at the convention of course, so your cups and bra straps don't show through. Having made the decision that you will wear it all day, I should tell you something. My experience with that garment is that it gets tighter the longer you wear it. I only wear it for church or for evenings out, relatively short periods. I brought it just for the banquet. And since I have the car keys, I know you won't be leaving the convention and coming back to the room to change for at least the next ten hours. Do you know what this is?"

"No" he said with a slightly perplexed expression on his face, "You just pushed on me ever so slightly. Why?"

"It's called a girdle check", I said. "To see if a girl was wearing her girdle her mother would pinch her butt or hip. You can't pinch through a girdle so the fingers just slide over it. I'm going to give you girdle checks throughout the day, to make sure you haven't ditched it. If you are tempted to ditch it, you better appreciate just how expensive they are, because you lose or damage it, you buy it. And that's an expensive one."

In the car, not a word was spoken. He was sullen and I was contemplative. I know Mike very well and the last thing I would call him is submissive. He would never submit to a bully, so I knew the "I own you" comment was hyperbole. I've seen him respond to bullying and it never ends well for the bully. In reality I could only milk this thing so far, but what the hell, we were there to have fun and tormenting him for a few days might just be fun.

My plan was to let him suffer all day from the mental anguish of wondering what will happen when "the other shoe drops". He can contemplate the long term consequences of being caught by a coworker in a work related circumstance. Let him stew!

Finally when we arrived at the convention site he spoke, "Leslie, I'm truly sorry that I violated your privacy and used your property without permission, but I'm even more sorry that you thought I was going to lie to you back there. I know you understand why I wanted to keep my cross dressing private, but I want you to know I was not going to lie to you and if you tell people at the office what happened, I won't deny it. I really am sorry that I abused your trust."

His apology disrupted my plan to let him stew. At that moment I had a life altering decision to make. Sometimes there are no second chances, no do-overs. The moment you speak you have chosen which fork in the road you will take and often you can't go back. Your words or actions reveal your true nature and others draw conclusions and formulate their own course of action based on it, even if for him it means looking for another job. I didn't want this to get out of hand.

This kind of thing can creep up on you suddenly. You can't plan for it. An hour ago I could not have predicted this situation and the next words out of my mouth would completely change our relationship in ways that can't be known. I could tell everyone, including our boss what happened and ruin him and he knew it. At that moment I had to declare myself as friend or foe. It was no more complex than that.

"Mike, do you really think I would humiliate you at the office? Don't you know me better than that? What really upsets me is your lack of faith in me and the lack of respect your action demonstrated. I will accept your apology, and your secret is safe with me, but you should have been more considerate. I will, however, demand retribution. You deserve to be punished for your inappropriate behavior and you must accept that I will be the one who determines how."

He admitted that I did have that right, but wanted to know what I had in mind. I told him that I was still thinking about it, but I won't let him off easy. "I intend to have some fun with you, for the rest of this trip. Admit that you are at my mercy and I'll tell you my decision after dinner. If you don't accept punishment, you are saying that you can violate me with impunity and for that; I'll never trust you again. But I promise that nobody at the office will know why."

"Leslie, nothing you can come up with would be worse that, so I agree in advance to whatever you choose. Losing your trust would be the worst possible punishment and would in my opinion far exceed the magnitude of my offense. I'll do whatever it takes to make it right."

I told him that we might both have fun with this, but make no mistake; it's my call all the way. Then I asked him the obvious question; "Why did you do it?"

He said he had cross-dressed since he was about five years old and stopped for many years then inexplicably started it up again. He didn't really know why other than the fact that he enjoys it and also out of curiosity. He always wonders what it would feel like to wear the various cute little outfits he sees girls wearing. He admitted that it doesn't make any sense, but said it was an obsessive or compulsive behavior and if he was going to be afflicted with a compulsive behavior, he was just grateful it was not a drug habit or alcoholism or some other harmful one.

An obsessive behavior that would cause a man to risk his career by doing something so stupid is something I just couldn't understand. It's got to be more than curiosity. Is it misplaced male sex drive? I would attribute it to that if it weren't for all the female teachers who ruin their lives getting involved with young students. At that moment, I was worried for my friend's future.

What if he gets arrested in a store? Or, if this had happened with another co-worker who doesn't know him as well as I do? He could lose his job and I could lose the best work partner I ever had, a partner who is so much in tune with me that we seemingly read each other's minds.

That evening to my disappointment he seemed none the worse for wear. In fact, the girdle made him look a bit better but I didn't say so. I also didn't inquire about his comfort and perhaps he would not have admitted to any discomfort out of obstinacy. Lucky for him, we are about the same size. If he had to wear an all-in-one that was too small he would have been in agony rather that the mild discomfort I wanted to inflict on him.

At dinner I asked him what cute little outfits he had tried on and which were his favorites and he spoke openly about his interest. He said he wore a Linda Carter style Wonder Woman outfit years ago that was his favorite and I smiled at the image that formed in my mind. He said he liked short skirts and a wasp waist like tennis or skating dresses and I immediately thought "sissy maid". With his wall of secrecy now down, we had wonderful conversations and said things neither would have said in a more guarded conversation. He seemed liberated. A special trust now existed between us. We had a lovely dinner during which I discovered that we both love lingerie. What's not to love about lingerie? It was fun being able to talk to a guy about it.

After dinner, over desert and coffee, I presented my plan for his punishment. Quite honestly, I think he was delighted with my proposal although he was being pushed a bit past his comfort level. I reminded him that he had pushed me beyond far my comfort level that morning. I told him that I wanted to know what clothes he owned at home so we wouldn't buy repeats and he was remarkably open about it. It was "mostly lingerie, a corset and a beautiful tutu" he said.

At that moment I knew I just had to see him in his corset and tutu. I asked if he would model them for me and perhaps let me try them on and he smiled and agreed saying "Why not? What's the difference between seeing me in a tutu and seeing me in pantyhose and an all-in-one?"

Being five thousand miles away from home seemed like a safe distance for him to explore his predilections openly. After dinner we went to the Ala Moana Shopping Center to buy some clothes and shoes for him. On the way we stopped by a shop called "Adult Treasures" I had found online and I had him buy some silicone breast forms to fill out the C cups in my all-in-one. I had him remove his jacket, unbutton his shirt and try them on right there at the counter. At that point he knew he was in for a rough week.

The pantyhose he had on came in handy when he tried on shoes and I carried the bag with the breast forms so they were available when he needed to try on blouses. To my surprise, it turns out that he liked wearing the all-in-one, I guess because of his quest for a wasp waist. So being in what is probably the only shopping center in the entire state where one would have a selection of them, I had him buy his own and take mine off. He put the new one on before he tried on other clothes since it would affect the fit of his new clothes. He didn't want a dress and that was fine. We found a little nightie that was so cute that we each bought one. And he got some very nice women's slacks that were long enough to cover his new high heels. Without my guidance he would have been dressed like a tart. His taste in woman's clothing definitely needed refinement. He also bought a small purse. I could provide any other accessories he needed.

I told him he needed a one piece bathing suit too. "The hotel has a swimming pool and you can wear a one piece bathing suit, and a bathing/swim cap and nobody can tell you're a boy with that thing you do down there." I wasn't making a suggestion, I was telling him, so he picked one out that he liked, tried it on and bought it. We stopped by a drug store on the way back to the hotel and got a bathing cap and chemical depilatory; because hairy legs and armpits definitely would not go with the look I was going for. We also got some makeup, large feminine sun glasses and a big floppy sunhat so a wig would not be needed. He thanked me for going shopping with him and told me it had been fun. "It was fun for me too", I said.

I must confess, that night he looked so cute in that little nightie that I couldn't resist a bit of role playing even though I was in my matching one. I couldn't keep my hands off of him and vice versa. It was a wonderful night and proved to be the first of many.

The next day we blew off the convention and went to the beach in our swimsuits. I don't know when I have ever seen such genuine happiness. After that we changed and the two of us walked around Honolulu, saw the Royal Palace and had lunch in Chinatown. He took to the heels like a duck to water and thanks to my influence he looked good in his new attire.

The next day we were back at the convention and after the convention was over we had fun taking in the sights and swimming. We returned to Hawaii for our honeymoon the next year. So, I can't say sharing a hotel room with him was really a mistake after all. So far, we have lived happily ever after. We were both embarrassed by what happened that morning but since then we have tried on many cute little outfits together and I have a sweet and loving sissy maid.

The End

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