What Henry Did

by

Pamela

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I was sitting in a bar by myself having a glass of Chianti after a hard day of work, when a woman sat down next to me. I reflexively glanced over to check her out and realized that she was stunning. Long very light brown hair to the middle of her back, an extraordinarily pretty face, and have I mentioned her figure? I could only see her from the side, but she was all woman. Her dress was slinky and sexy and I got a glimpse of her legs in stockings and high heels.

I told myself that there was no point looking any further. She's way, way out of my league. I'm not what is called handsome. Most accurately people would say that I'm decent looking. Presentable. I'm also not a great paradigm of masculinity. I don't have super broad shoulders with bulging muscles, or a six-pack on my stomach. My calves aren't those of an athlete of any kind. On the other hand, I'm no Barney Fife. There's some fitness to my body, just not a lot.

I'm mentioning this woman because she ordered a Jack Daniels on the rocks and when it was served she turned toward me and said, "I don't date handsome men or men with big muscles. Nope. Been there done that. The worst thing is a man who is full of himself and thinks he's God's gift to women. Handsome, muscle-bound guys are exactly like that. Boy am I sick of them. I don't let any man dictate anything to me. Just cause a man has a dick and I don't doesn't give him the right to tell me what to do, or to think he's superior to me. What do you think?"

I wasn't expecting a question, but I collected my thoughts and said, "Yeah, why should women allow men to boss over them?"

"I'm glad you said that."

"Thank you."

"What's your name?"

"Greg."

"Nice to meet you Greg. It’s nice to meet a man who agrees with me that men have no right to tell women what to do."

"I've never been that kind of man," I said.

"I'm glad to hear it. You will not be aware of it, but I noticed you having a drink here a couple of months ago and I was intrigued. Since then, I've watched you a few times and even followed you to see where you live and work. I studied how you interact with other people. A woman can learn a lot from just watching how a man walks and talks, and I like what I've seen."

"You were stalking me?"

"Not stalking, observing. I've been surveying men all over this part of the city for quite some time and when I find one that I might like, I put in some effort to watch them. Verify for myself that there is nothing about them that I wouldn't like."

"This is really sounding kind of creepy. Don't you think?"

"Perhaps, but that is not a concern of mine. You're a decent looking man but not what one would call handsome. You're also clearly not very strong and manly. So I can certainly believe that you wouldn’t attempt to be superior to women.”

I didn't know if I should be upset or not. I'm pretty sure a woman this beautiful had never talked to me before in my whole life. She was clearly quite aggressive and maybe she had some sort of plan to lord over me. That would be really hypocritical! Anyway, up to this point, no harm no foul. I smiled at her and said, "You're a very interesting woman, I must say."

"There’s one more issue that I have to clear up before we can go any further.”

“Go further?”

“Tell me about your dick."

"What? My dick?"

"Yeah. Tell me about it. Are you happy with it? How big or little is it? Describe it for me. That’s the one piece of important information that I haven’t been able to obtain from just watching you."

"Important information? Well, you’re really confusing me here.” I debated whether I should refuse to talk about my dick or not and finally decided that it wouldn’t hurt to talk about it. No other girl I had dated had ever been especially interested in it. “Well, I guess I'm happy with it. I never really thought about liking or disliking my cock. I don't think it's small. No, I'm pretty sure it's not small. I guess it leans toward the larger size. Not immense."

"Intriguing. Tell me more about it."

"Like what?"

"Is it long? How thick is it? What kind of glans does it have?"

"It's not short and it's not thin. What exactly is the glans? I'm a little fuzzy about that."

The woman laughed, "The end of your cock."

"It's a bit stubby, I think. Not pointy."

"Is the glans well-proportioned to the thickness?"

"Yeah, I suppose so. It's not a little tiny glans on the end of a fat penis, if that's what you're getting at."

"I'd be interested in looking at your dick, if you don't mind."

I laughed, and said, "You're joking aren't you? Is this whole conversation a joke?"

"Do I look like I'm joking?"

"No."

"Right, because I'm not joking. Now, can I see your dick?"

"Where would you like to see it?"

"Follow me," she said. She led me to the women's bathroom and I followed her inside.

"Am I allowed in here?" I said, nervously.

"Sure. There are no other ladies in it. Now let me see that cock of yours."

I undid my belt buckle, pulled down my zipper and let my pants slip down to my knees. Then I pulled down my boxers so my penis was visible. While I might have speculated that I'd have a boner, I didn't. The whole situation was too weird to have one.

The woman eyeballed my penis and said, "You were pretty accurate about it. It's got a nice basic length and structure to it, and it seems to be a bit on the thick side, which is always good. You have a nicely shaped glans that is well proportioned. Very good, Greg. Now I want to see it erect. Can you get me a boner so I can judge its excited length and thickness?"

"How do I do that?" I said.

"Do you really need me to show you?"

"Of course not. I'm just a little bit flailing here because it's so strange what you're asking me."

"Be that as it may, I would like to see what your boner looks like."

This was unbelievably weird but when a beautiful woman wants to see what your boner looks like, who's to say no? I held onto my cock and rubbed it a bit. With the woman watching me it got excited pretty fast and the next thing I knew I had quite a raging boner.

"Well, well, well, look at that," the woman said. "That is one fine boner. One very fine cock. You should be proud. It has quite a nice length and thickness to it. And a very pretty shape. I also like the coloration."

"Thank you," I said.

"Lift it up so I can see your balls."

"My balls?"

"You do know what balls are?"

"Yes, of course."

I lifted up my cock to show off my balls to her. She said, "Those are fine balls, Greg. You've definitely got some nice ones. Congratulations."

"I assure you that I had nothing to do with having nice balls."

"Well then give God credit for them. Get yourself fixed up and I'll meet you at the bar."

She walked out of the ladies room leaving me there to somehow get my boner back in my boxers and then pull up my pants. After a few minutes the blood left my penis and I was able to walk out of the ladies room without a big bulge in the front of my jeans. I sat down next to the woman and resumed sipping my drink. We were silent awhile and I couldn't stand not knowing what the woman was up to so I said to her, "Did I pass?"

"Pass?" the woman said and laughed. "Yes, it was an exam of sorts. Okay, let me level with you. Meeting you in person is the last step of my weeding out of potential men that are candidates to become my boyfriend. I now have verified that you don't have a wedding band, and up close I see that you're decent looking and not overly masculine and, very importantly, I checked out your dick to make sure that it's one that I could be happy with."

"What do you mean that I could be a candidate to become your boyfriend?"

"I'm in the market for a boyfriend but I have very strong ideas of what man I want. You've passed the basic requirements. I have found one other guy who passed them also. His name is Henry. So I have my Henry and now I'll have my Greg if you agree to become a candidate. I plan to enter into a relationship with one of you but not both. That's too complicated. I'm a monogamous woman. So now, you and Henry can compete against each other to see which one I want to go with."

"Why do you think I'd want to compete for you?"

The woman laughed and said, "Seriously? Under normal circumstances there's no way you'd ever get a woman who looks like me. I'm giving you a fifty-fifty chance of becoming my boyfriend. Those are better odds than you'll ever get in the real world."

The woman had a point. She was so beautiful that I couldn’t imagine giving up a chance to be her boyfriend without feeling terribly guilty afterwards for having missed an opportunity. I said, "Did you check out Henry's penis?"

"What do you think?"

"How does it compare to mine?"

"I'm afraid I can't divulge that information. Obviously I liked what I saw, but I also liked your cock."

"How do I compete against Henry?"

"So you're in?"

"Before I decide, I need to hear how the competition will unfold."

"Fair enough. Before I talk about that understand that if I choose you, you'll get unfettered access to my body. You'll be able to feel up my 36DD tits, you'll be able to suck on them. You can fuck me in any number of positions. I'll give you blow jobs, we’ll engage in 69, you can have lots of time sucking on my cunt. We can act out any and all fantasies that you and I have. Besides all that carnal fun, we'll have a rich intellectual life together. We'll read books, acquire wonderful friends, travel broadly. I won't even rule out a family if that's what we want."

"If I lose?"

"You'll never see me again."

"Wow! Henry has agreed to this?"

The woman nodded her head. I realized that I didn't know her name and I said, "What's your name?"

"Cindy. Call me Cindy."

"So what will I have to do for the competition?"

"It's about two main things. Proving to me that you'll do wonderful things for me and secondly that you’re fully desirable of being the kind of man that is most to my liking. That means a man who can relate to me in a way that I’m most happy and comfortable with."

"How do we know that we’re being the kind of man that you want and that you like what we do for you?"

"That's the essence of the competition. Figure it out. Be inventive. Use your imagination. As you discover what is useful for me and pleases me, do more and more of that. As you discover what kind of man I like, be more and more that man. You can chart your progress against Henry and he’ll chart his progress against you. I expect that you'll each try to outdo the other.”

"Where does it end?"

"After a month I’ll make my decision. I expect that there will be a clear winner by then."

"So you vetted Henry just like me?"

"Yes. Only the two of you checked off every box and I see a lot of potential in each of you to become my boyfriend."

"When would the competition start?"

"So you're in?"

"Yes, I'm in."

"In that case, the competition starts tomorrow night for you. Tonight it starts for Henry. I will see the two of you on alternate nights so you shall never meet. You will come to my apartment at 6PM tomorrow. On weekends come at noon. I'll give you the address. You can expect to stay until about midnight whenever you come."

Cindy wrote an address on a card and handed it to me. She finished her drink and got up and left. I watched her beautiful bottom walk away from me and I hungered for it. No matter what, I was going to defeat Henry and become Cindy’s boyfriend.

***

When I showed up at Cindy's apartment two days later she let me in and then sat on the sofa sipping wine and dressed in an untied satiny robe that let me see a bit of her bra and panty. As she had said, her body was quite beautiful. It was awkward at first to be in the apartment with a near stranger. I looked around and saw that it was well furnished and expansive. It had a view of a park. I said, "I'm ready to show you how much I can do for you."

"I'm glad to hear it."

"So what can I do for you?"

"The idea of the competition is for you to show me what you can do for me. Come up with an idea that pleases me."

"Can I ask you what Henry did for you?"

"Sure. It's important for you to keep up with Henry, just like it's going to be important for him to keep up with what you do. So last night, Henry baked me a lasagna. There's some in the refrigerator that you're welcome to have."

I opened up the fridge and looked at Henry's lasagna. Hell, I thought. I'm not a very good cook. I do know how to make lasagna, but making a lasagna to compete with Henry's would probably be a mistake. His looked to be very good. I looked around the kitchen and thought that it wasn't totally clean. I could see some tomato sauce had splattered on the stove so I said, "I'm going to clean your kitchen, Cindy. Make it shine. That's useful, isn't it?"

Cindy laughed, and said, "That's a great idea, Greg. I do like a clean kitchen."

"I was wondering, is it okay in the future if I call you up to find out what Henry did? I mean, it would help me prepare for what I want to do."

"Sure, Greg. If you feel that you need to call me before you come I'm happy to tell you what Henry did."

I set out with some cleaning supplies that Cindy gave me and I systematically cleaned every part of the kitchen until it shone. That'll teach Henry, I thought!

***

Two nights later when I returned I discovered that Henry had vacuumed the entire apartment and dusted off the pictures and everything else. To counter him, I cleaned Cindy's bathroom. I went out of my way to get the soap residue off the shower door and polish everything to perfection. Cindy was very pleased with my work.

When I went home I could see that between Henry and me we had cleaned her apartment so well that there would be no more opportunities to clean something in order to impress her. I wondered what I ought to do next. I would have to call Cindy to find out what Henry did tomorrow so I could top him the following day.

***

Before going to Cindy’s on my next visit, I called her and found out that Henry had built an array of shelves in her closet. There was now convenient and accessible space for her shoes, sweaters, and handbags. From the sound of Cindy’s voice she was absolutely crazy in love with what Henry had done. I felt crushed. I could barely hit a nail straight let alone build anything.

The more I thought about what I should do, the more desperate I felt. Henry had me stymied. Finally, it occurred to me that Cindy liked wine, so I’d get her a wine cabinet and some bottles of fine wine that I could place in the apartment. I rushed around implementing my idea and showed up at her place at six with a shopping bag of wine bottles and a box for a DIY wine cabinet. I could tell from Cindy’s reaction that this was not going over well. She liked wine, sure, but she didn’t need a wine collection. By the end of the evening I rushed out of her apartment feeling terrible. Now Henry had the clear lead. I didn’t have any idea how I could leapfrog past him. I expected he would spurt way ahead of me with his next opportunity to impress her.

***

I was amazed by Henry’s next stunt. He went through Cindy's dresses, pant suits, blouses and picked out the ones needing dry cleaning and then took them out to be cleaned. Cindy thought it was wonderfully sweet of Henry to have thought of something both useful and always close to her heart. She loved taking good care of her clothes. As I listened to her on the phone going on and on about how happy she was with Henry my despair grew to the point where I said, “How can I possibly do better than that? He’s done your clothes! What’s left?”

There was some silence and then Cindy said, “Greg, I can’t tell you what to do. You know that. All I can suggest is that you think about the accuracy of your statements.” With that thought we said goodbye. With just a few hours before I was due at Cindy’s I racked my brain trying to figure out what the flaw was in my thinking. Then it came to me. Henry hadn’t done anything about Cindy’s underwear! Sure he had looked after her dresses and skirts, but nothing about the clothes she wore underneath her outer wear! Not a thing. Cindy was no doubt implying that I should somehow clean her underwear. I looked on the web for information about the proper way of taking care of bras and panties and discovered that hand washing and air drying was the ideal way they should be treated. Excitedly, I decided that I would ask Cindy to point me in the direction of the underwear she had worn that week. I would gather it together and hand wash it for her. This was a fantastic idea that could change the entire dynamic of the contest because I would now be thrust into a more intimate relationship with Cindy than Henry. While I was congratulating myself, I realized that my celebration was premature. It was possible that Cindy would think I was taking liberties with her by insinuating myself into her intimate garments. This might backfire. However, my instinct told me that if I didn’t take a risk, I was surely going to lose to Henry.

When I showed up at Cindy’s apartment I said, "Tonight I want to hand-wash your lingerie. The lingerie that needs to be washed." Saying this out loud made what I was planning seem even scarier and riskier. I realized now that talking to Cindy about her lingerie was potentially violating rules of decorum that could cause her to be angry with me.

I waited, cringing, hoping that Cindy wouldn’t be upset by what I was planning to do, but instead of being angry she smiled at me and said, "Sure, Greg, that's a very thoughtful gesture. It’s really good for a girl’s bras and panties to be handwashed instead of put into a washing machine. It’s so nice that you want to take good care of my lingerie. Many men get weird if they’re asked to touch a bra or panty or even talk about one. I like that you’re comfortable with lingerie in the same way that girls are. We can consider this to be an important way in which we think alike.”

I was bursting with happiness and pride that I had taken this bold step that had turned out to be smashingly successful. Henry was toast. I was leaving him far behind in the dust. Cindy said, “You can find a half-dozen bras and panties in my hamper that need washing. Also a couple of slips, several pairs of stockings and even an all-in-one."

“That’s great. I’ll wash them in the basin and dry them on a rack. I am so happy to be able to be useful to you.” Inwardly I thought about how smart I had been. This was such a homerun. Poor Henry was going to be shocked to find out that I had made a huge step toward gaining intimate knowledge of Cindy's most personal clothing. I’ll be holding in my hand the very bras that had touched her breasts and the very panties that had been up against her vagina. It was truly magical. I wished I could see Henry's face when he found out what I had done! I wondered if Henry might just drop out of the contest.

I'm not an expert on lingerie, but I’ve always enjoyed women wearing sexy bras and panties. In fact, while I do enjoy looking at a nice breast or vagina, my preference has been to see a breast in a bra and a vagina in a panty. I think it has to do with the fact that there is nothing more exclusively female than the mind of a woman in the act of selecting her bra and panty to wear on a given day. At these moments a woman is fully aware of her breasts and vagina and how she wishes to contain them during that day. The lingerie a woman wears is a living record of these feelings. It's not a calculation that goes with manhood.

I went through Cindy's hamper picking out her panties and bras and other clothing that needed washing. It was loads of fun. Each bra I found made a beautiful statement about Cindy. Without exception her bras were elegant and sexy. Each one had lace designs and seemed to be well made. Many of her panties matched individual bras. Her slips were white and of high quality as far as I could tell. I held up her all-in-one that was a beige color with lace around the thighs and breasts. What a delightfully sexy garment it was. Her stockings were glorious things that I gently washed with the other clothing in a basin. After washing and rinsing each of her panties and bras I placed them on a rack to dry.

Up until this point in the competition I had felt that the actions I were taking were mostly superficial. Cleaning a bathroom wasn’t really getting me close to Cindy. Now, however, I felt deeply connected to her for the first time. Here I was, little ole me, intimately involved with the underwear of this beautiful woman. I felt I now had a real connection with her. It was a solid beginning of something that might grow to become love. I sure hoped it did!

When I was done with my task and Cindy’s underwear was drying I went to see her in the living room. She asked me to sit down and have some wine with her. We looked at each other. I could not get over how pretty she was. She was maddeningly beautiful and sexy. Any doubts I might have had about agreeing to the contest melted away as I gazed at her. But then, out of the blue, a cold fear ran through my heart chilling me to the bone. What if, by some unfortunate twist of fate, I lost to Henry? He would have everything I loved and fought so hard for. I would end up with nothing. I could not let that happen. No matter what Henry did, I would have to do more. I needed to be fearless in always outdoing him. As these thoughts flashed through my mind I wondered if Henry had the same kinds of thoughts. Maybe he would also be devastated if he were to lose the battle with me.

"What are you thinking about, Greg?" Cindy said. "I can see that there are a million thoughts running through your mind."

"To be truthful I was thinking about how beautiful you are. About how much pain I would feel if Henry won, and how I will do whatever I can to win."

Cindy chuckled quietly. "You're a sweet boy, Greg. I like you and I'm glad that I picked you."

I blushed and wondered if she was saying that I was ahead in the competition. "Are you allowed to tell me how I'm doing so far? You know that the competition has Henry and I flying a bit in the dark, not knowing exactly what it is that you would like us to do for you."

"As I said before, knowing how to figure out what I like is one of the talents that I'm looking for in you boys. So far, I'm pleased with everything the two of you have done."

"Washing your lingerie was a good idea?"

Cindy laughed gaily. “Of course, Greg. I’ve already told you that! I suppose I should admit to you that I love your insecurity. You’re a very vulnerable boy, Greg. You share this quality with many girls. I like that about you.”

I wanted to ask Cindy if she thought that Henry was insecure and vulnerable also, but held my tongue. It was best to not stir the pot more than necessary.

“Thank you, Cindy.”

“I told you at the start of the competition that I would be looking for ways in which you think like I do. I like the idea of feeling close to my boyfriend because we share the same feelings about things. Now I know that you and I both believe in the advantages of handwashing bras and panties. That’s really nice. It says to me that even though you’re a boy, you can think the same way that girls do.”

This was a lot of data coming in fast and I struggled to process it. It was clearly a valuable piece of knowledge that Cindy liked me to think about things the way a girl did. Besides washing bras, I wondered what other things might fall into this category. There were certainly many opportunities for me to exploit this insight to gain the upper hand over Henry. I would need to spend some time thinking about it. On the other hand, I should be careful about over playing my hand. She did seem to suggest on the day I met her that my cock was important to her. That might mean that at least some degree of masculinity is a necessary element in liking me more than Henry.

"Keep surprising me with such thoughtful gestures as washing my bras, and I will be very pleased with you, Greg."

I left her apartment that night feeling ebullient. I laughed to myself thinking how poor Henry will be agonizing over what he can do so that he doesn’t fall further behind.

***

After my lingerie coup, Henry got the idea of being Cindy’s French Maid. He came to her apartment wearing a frilly black apron over a white shirt and a little black tutu made of stiff nylon tulle over his black trousers. Though I did not see what he looked like, the costume seemed to be neither here nor there. Henry was hedging his bets. Yes, he wanted to be kind of womanly like a French Maid, but he didn’t want to be too overtly feminine for fear of risking Cindy’s displeasure. I strongly suspected that Cindy had no qualms about Henry and I playing the part of women if that is what we wanted to do to please her.

Dressed as a French Maid, Henry took care of Cindy. He cooked and served her dinner. He drew a bubble bath for her, but did not help her into the tub. I was glad for that. Judging from Cindy’s description of the visit, I don’t think she was very impressed. I decided that I would take Henry’s basic idea, which I liked, and run much, much further with it than he had. My next visit with her was on a Saturday so I would have the whole day to be with her. When I arrived at her place I said my plan was for her to go with me while I buy myself a French Maid’s outfit. “We’d be two women out shopping for the outfit. The focus is on the experience of shopping together for pretty clothes. It opens up a new area where I can show you that we think alike.”

Cindy was intrigued by my suggestion and I felt sure that I had hit another homerun. “I see what you’re saying Greg. We go shopping together for your French Maid’s outfit. That way I can see firsthand that you appreciate and enjoy buying pretty clothes the same way that I do.”

“Yeah, and also show you that I like the experience of shopping with a girlfriend.”

“Let’s do it,” Cindy said.

“I’ve done some research and I know where we can go to get the French Maid’s dress.”

“This is such a nice idea. I’m excited! I don’t know how you knew it, but I really love to go shopping for pretty clothes. And now this can be something we share together!”

I knew that I was falling in love with Cindy. Her voice was music to my ears. We seemed to be truly on the same wavelength. I started feeling a bit bad for poor Henry. He seemed to have no clue as to what really excited Cindy.

Cindy and I travelled to a small specialty shop that sold uniforms. Several mannequins were dressed in French Maid outfits. Cindy and I discussed each one in turn. We talked about how cute the skirts were and the aprons. One of the outfits stood out from the others. It was an especially cute dress with a black skirt and a white top that Cindy said gave a very sexy presentation of the breasts. Also included with the outfit was a black choker, fishnet stockings and black high-heel shoes. We agreed that it was perfect. The proprietor came over to assist us. The reality that the dress was for me awoke in my consciousness and I became apprehensive. It was true that I thoroughly enjoyed chattering with Cindy about the pretty dresses, but donning an actual dress in front of Cindy and the proprietor was a whole new ballgame. There was a serious escalation in risk that Cindy would disapprove. I had to remember that her philosophy was to have me steer the ship and she’d go along with whatever I did. That included running the ship aground by doing something she didn’t like.

Before I could say anything, the woman said, “I see you’ve gravitated to our prettiest French Maid costume.”

“Yes, we love it,” Cindy said.

“I’m guessing you’re a size 8,” the woman said. “Shall I bring one out for you to try on?”

Cindy laughed gaily and said, “Oh, you misunderstand. My friend Greg will be wearing the outfit!”

“Pardon me!” the woman said surprised. She turned to look at me and I was sure that she was thinking ‘weirdo.’ She laughed slightly and said, “In that case I better bring out a size 12. I’ll fetch that and you can try it on.”

As we stood waiting, I contemplated what my next move should be. I could end this outing at any moment if I wanted to. Once I put the dress on, it would be like a runaway train going down a mountain. I would not be able to stop what came next. Cindy said, “I hope it fits you. I know you’re going to be very pretty in it. Though, don’t you think that we have to get you a bra and panty to go with the outfit? Probably also some falsies or breast forms? As you can see from the mannequin, having a woman’s chest is necessary for the dress to fit well. What do you think, Greg?”

I could see that it was already too late to change direction. My little afternoon shopping event had taken on a life of its own. It was no longer a simple matter of shopping with Cindy as if we were two girls who loved to be out looking at pretty clothes. No. Now I was being transformed into a woman dressed like a French Maid. The reality of this came crashing down on my head. This could be a fatal blunder that would lead to Henry winning by default. Did Cindy really not mind me wearing a bra? It was true that she seemed eager for me to complete the underpinnings of the French Maid outfit. At no point had she acted like this was freaking her out. I said, finally, “I suppose you’re right.”

“Certainly the dress will fit you much better with proper underwear including some breasts.”

The proprietor came back carrying the dress and Cindy gave me a glance that suggested that I take charge of the situation. I said to her, “The dress looks very nice. I think that I have to get myself a bra and panty to wear before I put the dress on. Don’t you think so?”

“Yes, of course. To properly wear a dress you need to be like a woman by donning a bra and panty. Also, you need something to hold up the stockings. It could be a garter belt, or a girdle. An open bottom girdle or a panty girdle. Whatever you prefer.”

“Can I come back and try on the dress after I get those things?” I said.

“Of course. I’ll put it aside for you. Next door is a fine lingerie shop, Gabriella’s, in case you’re not aware of it. Gabriella is an expert bra fitter and she has a delightful selection of only the best bras, panties and foundation garments.”

“That’s kind of you to mention it and so very helpful,” Cindy said. “What would you like to do, Greg?”

“I guess we should go next door and I’ll get a bra, panty, and whatever else I need.”

“Splendid!” Cindy said. “This is so much fun!” Her energy and enthusiasm were infectious and I found myself enjoying the prospect of getting my first bra and panty. It was feeling less and less likely that Cindy was unhappy with me dressing up as a French Maid. I began to think that this might, in fact, turn out to be the best way to win the contest.

***

Gabriella’s was a wonderland of lingerie. A small shop that was filled with a thousand bras and panties of a wide range of colors from vivid shades of red to pastel shades of pink and blue. A close look at the bras revealed a multitude of pretty bows and intricate designs of delicate lace. On one end of the store I saw racks of all-in-ones and foundation garments. Elaborate and interesting panty girdles and garter belts of many different designs caught my eye. It was the kind of shop where a man could not help but lose his masculinity. He would see it drain away systematically, one sexy bra or panty at a time. For me, whose goal was to get a bra and panty, the loss of my masculinity had already reached an advanced place before I walked into the shop. I could see clearly now that it had been a price I had been paying to win the contest against Henry. If I won, I could honestly say that it was a price worth paying. If I lost, I’d probably need some long-term therapy to figure out exactly who I was.

Gabriella was behind a counter in the middle of the shop and she looked up and said to let her know if we needed help. I didn’t know where to begin searching among the bras, but Cindy lost no time by stopping in front of the first rack of bras and saying, “Greg, these are so pretty!” She picked one up and read the label. Then she held it by the shoulder straps and looked at it end on as if thinking what it would look like on her. “I love the soft, printed fabric.” Then she handed it to me.

I took the bra from her and looked at it exactly the same way she had including holding it by its straps to get a good look at the whole bra. “I love the shimmering embroidery,” I said, “and the way the embroidered trim at the top of the cups runs elegantly onto the straps.”

Cindy turned and looked into my face with a smile the size of Texas. If I didn’t know better I would have thought that my comments about the bra were giving her an orgasm. “You took the words right out of my mouth, Greg. I just love the way you have an instinct for talking about pretty bras the same way that girls do.”

We walked a bit further and I decided that do or die I couldn’t just let Cindy make the decisions as to what bras we wanted to look at. Afterall, the bra was to be for me. I saw another very attractive bra and said, taking it off the rack, “Oh, I like this bra, Cindy. See the stylish checked fabric and the heart-shaped padded cups. Oh and such pretty lace on the side panels creates a feminine look!” I was flying now. Bra talk was popping up all over the place inside my head.

“It is so pretty. I also like it’s high-gloss fabric,” Cindy said.

I felt like we were two kids in a candy shop. There were so many pretty bras and I loved discussing each one with Cindy. She said, “Before we look further, I think we ought to get you sized up.”

“Right.”

“Not every bra we look at will be in your size.”

“What size am I?”

“We’ll have to get you measured.”

I hesitated expecting that Cindy would say something to Gabriella and then I realized that she was deferring to me so that I could take the lead. I walked over to Gabriella and said, “Excuse me.” When she looked up at me I said, “I need to buy a bra, I mean a bra for myself, but I don’t know my size.”

“You need me to measure you for a bra?”

“Yes, if that’s not a problem for you. I also need to buy a panty and perhaps a girdle, one with garters.”

Cindy came up to us and she added, “Really it’s just his band size that we need. I suppose it’s a 36 but we ought to be sure.”

“Of course,” Gabriella said. She found a tape measure and had me take off my shirt. She put the tape around me at the location of my nipples and read off 35 ½, “So you are a 36. What cup?”

“What size breasts would you like, Greg?” Cindy asked me.

The two women were staring at me and I said, “I’m not so sure what’s best. Your size?”

Cindy smiled, “DD? That’s so sweet, Greg. I like that. I like that we share the same bust size. It’s so cute of you.”

“So 36DD,” I said to Gabriella.

“You’ll find quite a few 36DD bras where you’ve been looking. You’re probably a size 6 panty and for your foundation I suppose a medium would be about right. Let me know if you’re having a problem or need some advice.”

“Thank you,” I said.

Cindy and I resumed looking through the bras. “Greg, here’s a very pretty bralette.” She held up a bra to show me. “See, no underwire in this bra. Long line bras like this usually offer a very comfortable fit. I love the all-over slightly sheer lace and the wide lace panel under the cups. That’s the magic, how it can support you without underwire.”

I examined the bra and said, “It’s really nice. Does it come in my size?”

Cindy looked and said, “Only in black.”

“I don’t really want to get a black bra. I mean I think that my first bra ought to be a prettier color.”

“I agree. Let’s keep looking.”

We sidled along slowly and found several 36DD bras that I held up and thought about. Then I saw a bra that instantly knew had to be the one. “Oh, Cindy. Isn’t this the perfect bra for me?” I asked.

“Oh, wow, that is a nice one. See if they have it in your size.”

“Yes, this one is light pink and its 36DD.” I examined it closely. “It’s so perfect. I love the embroidered motifs on the tulle background, and it has lace flowers framing the décolleté. Yes. This is my bra.” I looked below where panties were hanging. “Oh my God, Cindy, they also have size 6 panties.” I took a panty off the rack, and held it up with the bra to show Cindy.

“By all means, Greg this is such a lovely choice of bra and panty set.”

Gabriella came over and said, “Found something you like?”

“Oh yes,” I said, enthusiastically. “This is the prettiest bra and panty I think.”

“You’ve got great taste.”

“Thank you,” I said. “Now I need to find a girdle to hold up my stockings.”

“You could also wear a garter belt.”

I looked at Cindy and she said, “Let’s have a look and see what’s best for Greg’s figure and taste.”

Cindy and I followed Gabriella over to the foundation area of the store. In front of me were girdles of exquisite beauty as well as girdles that seemed to be purely functional. “I love the pretty girdles,” I said to Cindy and Gabriella. “These without the lace I’m not so excited about.”

“I’m the same way,” Cindy said. “It’s nice that we both appreciate the prettier girdles and bras, isn’t it?”

“Yeah,” I said.

“I agree with both of you,” Gabriella said. “For me, lingerie should be pretty and feminine, but many women feel that they have more important things to do than worry about having girly underwear, and I have to respect that.”

“Just like some boys, like Greg for example,” Cindy said, “who, unlike most men, have no problem with wearing pretty girls underwear. It takes all kinds to make a world. I personally celebrate the wide range of preferences that people have.”

“I couldn’t agree with you more,” Gabriella said. “Since I’ve owned this shop, I’ve met many boys like Greg over the years who look up to women and wish to emulate them. Especially by forming a love of pretty bras, panties and girdles.”

“See Greg?” Cindy said, “See how much women appreciate boys like you. Boys that we can share our thoughts with as if we were two girls. It’s a delight.”

Listening to Cindy I felt like I was hitting homerun after homerun on this excursion. I was absolutely behaving in a way that she wanted me to.

“So which particular girdle would you like?” Gabriella said.

I had a craving to wear a particular open bottom girdle that was pink and had an elegant lace design. “That’s the one that I would prefer,” I said, pointing to it.

Gabriella took one off the rack and held it up. “This is a favorite of mine too. In fact, I’m wearing one now. If you don’t mind, let me show you.” Without waiting for an answer, Gabriella hiked up her skirt and slip to reveal herself wearing exactly the girdle I had picked out. I stared at the beautiful shape of her rear end in the girdle and the way the garters attached to her stockings. I felt a stab of jealousy since I doubted that my butt would fill out the girdle as nicely as hers did. But at least I could imagine that I looked pretty in the girdle. “It’s made of lightly controlling floral lace elastic nylon spandex. Power net inner panels help to smooth the tummy. I love the inch wide waist band providing stay-in-place comfort. The four garters are detachable.”

“It really is so attractive,” I said. “I’d love to try it on.”

“Very good,” Gabriella said. She lowered her dress and we walked to the fitting room. Gabriella said to Cindy, “Does he know about using the paper?”

“I’ll go in with him and make sure he understands.”

I didn’t know what they were talking about, but Cindy followed me into the single dressing room that was behind a curtain, and I figured there was something that she would have to tell me about women’s dressing rooms. Apart from the first time I met Cindy when she inspected my penis, she had not seen me naked. I wondered if she would consider it cheating if she saw my cock again. “Take off your shirt and let’s see how your bra fits.”

I took off my shirt and then I was confronted with having to put on the bra. I could see Cindy looking at my chest, shoulder and arms and she said, “You have pretty arms, Greg, and sweet shoulders. Do you need help with the bra?”

“I’m afraid so, Cindy, I’m sorry.”

“Don’t be sorry. For every girl there’s a first time. Usually our moms are around to show us how to put on our bras. I’ll be your pretend mom!”

It was clear to me that Cindy was enjoying this experience. Apparently I had stumbled upon a central facet of herself. A girl’s afternoon on the town shopping for pretty lingerie was right up her alley. Once the bra was on, Cindy said, “It’s even better than I imagined, Greg. The bra accentuates the feminine side of your arms and shoulders so you look just like a girl. How nice that is! Those large cups have to be filled. Let me ask Gabriella if she sells falsies.”

Cindy was about to leave when Gabriella came to the curtain and said, “How are we doing in here? I’ve brought you some falsies, DD falsies. I figured the gentlemen will need them.”

Cindy took the falsies from Gabriella and said, “Thank you. I was just about to ask you for some.” She handed the falsies to me and I inserted them in my bra. Suddenly it was as if I had entered a magical realm where I was a girl. Having breasts in front of me and contained in the pretty bra caused a wave of feminine feeling to cascade over me. I felt my face get flushed and I almost wanted to prance as if to show off that I was a girl.

“Are you okay?” Cindy asked me.

“Yeah. I’m sorry. Wearing a bra for the first time is kind of, I don’t know, exciting?”

Cindy laughed, “I felt the same way.”

“And having these breasts in front of me, it’s kind of powerful. I feel like I’ve become sort of a woman. I think I’m being too honest. Will this hurt me in the competition?”

“I love the way your mind never stops whirling away. My suggestion is to trust yourself and your instincts. If you’re wrong, you’re wrong, but at least you were yourself. I’m not trying to get a fake you to win the competition. I want the winner to be who they really are.”

“I see what you’re saying.”

“Good. Now for the panties. We need to make sure that size 6 fits you.”

“I’ll have to take off my pants and underpants,” I said.

“True, Greg. You’ve got an excellent understanding of clothing.”

I laughed and said, “You know what I mean. I don’t want to cheat in the contest.”

“Cheat?”

“If you saw me naked …”

Cindy laughed and said, “You mean if I saw your wonderful cock again I would have to pick you over Henry! While it’s tempting to base the competition on penis beauty, that isn’t the way I intend to choose. So let’s get you naked so we can see how cute you look in the panties. Now you need to put this tissue paper inside the panty so you keep it clean. Women tend to leak a little and we wouldn’t want that to happen to a panty we’re just trying on and might not buy. You also might leak something from your magnificent penis!” Cindy laughed at her joke.

I kept the tissue paper inside the panty and pulled it up my legs. It fit me quite well. “I think it fits, don’t you?”

“Yes. Turn around and let me see your cute butt.” I did as she said. “Yep. These are the right sized panties for you. Now you need to try on the girdle.”

The girdle had a side zipper which I unzipped and then undid a couple of hook and eyes that were underneath it. I slid the girdle up over the panty and clipped it and zipped it up. It was a bit snug at my waist. The garters dangled lightly against my thighs. I was delighted with the feel of the girdle. Women were so lucky that they could get this pleasure every day if they wanted it. I also enjoyed the feeling of the bra on my chest and the lovely shape it gave me. I wondered why one often heard that women are not crazy about wearing bras. I was having an epiphany staring at myself in the mirror with Cindy behind me. I couldn’t give this up for anything. Why had it taken me so long in my life to discover the extraordinary happiness that can come from fine lingerie? Women like Cindy seemed to be as smitten with it as I am. Perhaps part of Cindy’s thinking in having the contest was to find a boy who felt like she did about lingerie. In other words, not just that her boyfriend should admire women, but he would want to share the fun of lingerie with her. I’ve certainly proved my creds in that department. I wonder if Henry has done that. I felt like he probably hadn’t. By my analysis I must be far out in front of him.

“Come show Gabriella,” Cindy said.

She escorted me from the changing room and Gabriella came over to look at me. I saw a smile break out on her face and she said, “Lovely, just lovely. He’s a darling, isn’t he?”

“Yes,” Cindy said. “This is such a nice underpinning for Greg. Let’s pay for it and get your dress.”

***

To get next door, I put my shirt and pants on over the bra and girdle, not even taking out the falsies. When we entered the costume shop, the proprietor had the French Maid dress waiting for me. I went to the dressing room and stripped down to my underwear and Cindy helped me on with the dress. I put the black choker around my neck and slipped on the fishnet hose and secured them to my girdle. The shoes were interesting to wear. They completed the look and Cindy thought they were sexy. The high heels took some getting used to in order to walk to the center of the shop to show off my outfit.

The proprietor said, “What a transformation! I guess some boys just have girl curves in them, just enough to give one the appearance of a girl. If I didn’t know you were a boy, I would think that you’re truly a French Maid.”

“To be honest, Greg, you look smashing,” Cindy said. “Just the right amount of natural femininity together with your mincing walk and hand gestures has stripped away your masculinity.”

“I hope you’re happy,” I said.

“I’m very pleased, Greg,” Cindy said.

It could not be clearer to me that Cindy enjoyed having me wear a dress and act like a woman. How else to explain her excitement in my transformation from Greg to French Maid? What deeper implications this might have in winning the competition remained to be seen. After I paid for the dress, Cindy and I went home in a taxi. I didn’t change back into my boy clothes and if the taxi driver thought ill of me he didn’t say anything. When we got back to her apartment, I spent the rest of our time together waiting on her as her maid. I did a lot of curtseying and saying “Thank-you Ma’am” and otherwise playing the part. I’m pretty sure she loved it.

***

I spent the day Sunday dreaming of Cindy and how much fun I had had shopping with her. I wore my French Maid outfit around the house and thought about what I should do on Monday when I showed up. Ultimately it depended on what Henry did. He had from noon to midnight. I wondered if he could rally from far behind to take the lead. Maybe he would think of some incredible Hail Mary that ended up scoring a touchdown for himself.

***

I discovered the next morning that Henry had definitely thrown a Hail Mary but whether or not it was caught I couldn’t tell. I was incredulous to hear from Cindy that Henry brought the accouterments of a toddler to her apartment, including diapers, bottles, binkies, dresses, and everything a mother might need to take care of her child. He dressed himself in a diaper and plastic pants and put on a frilly pink dress. Then he brought Cindy a bottle with milk in it and had her feed him. They spent the day playing children’s games and having Cindy change his outfit from one cute dress to another. Henry seemed to be playing to Cindy’s maternal instinct. I guessed that he was convinced that she had a strong desire to have a baby and be a mother. He was both trying to tantalize her by the fun of being a mommy and signaling to her that he would love to have a family with her. If he was right, this could be a game changer. I tried to get clues from Cindy’s voice as to whether or not she had approved of his gambit, but they were ambiguous.

I now had a critical decision to make. Do I follow along with the new direction that Henry pioneered, or stick to the kinds of things that I’ve already seen work for me? What specifically should I do for my next visit to Cindy? I probably needed to find new ground. Scoring more points for the same things I had already done was treading water. Cindy had a firm understanding of our closeness in shopping and love of lingerie. She had also seen that I presented nicely as a woman in a dress. There was no need to do more of the same, or was there?

I thought back on what had transpired thus far in the contest as concerned me directly. The common theme that had garnered Cindy's most enthusiastic response was when I showed her that I had a feminine side. The things that made her feel close to me all had to do with me taking on the part of her de facto girlfriend. If I extrapolated further, it was evident that Cindy wanted me to actually be her girlfriend. In other words, her perfect boyfriend is a man who will fulfill the role of her girlfriend. The only masculine thing that she wants from her boyfriend is his penis because she obviously likes them. This must be the great truth about her. She limited her search for a boyfriend to men that she thought could toss aside their masculinity and become female. But still have a penis!

With this insight I knew what my final pitch had to be. I had to show Cindy that I wanted to and could abandon all of my male characteristics. I would be her girlfriend. However, her girlfriend with a penis. I would now show up at her door as the most convincing girl I could be. Not just acting out a part as a French Maid, but fully transforming my mind and body to acting and appearing like a girl. When Cindy opened up the door to her apartment she would take one look at me and know that I have given up all my masculinity for her.

First on my list would be getting a pretty dress to wear. After some research I decided that I’d get a tea length bouffant style dress. Probably pink with substantial pouf. It would be as feminine a dress as could be found. My hair was slowly growing out but not there yet. I’d have to get a wig and I’d need the help of a cosmetician to apply makeup to my face and to paint my finger and toenails. It would be a very busy afternoon.

I went to a local dress shop I had walked past many times. There, the salesgirl, who couldn’t have been even 21 fitted me in a poufy gown of rose-colored pink tulle, whose many skirts billowed out from my waist. It had a wonderful flowery display across the bosoms down to the waist in a lighter shade of pink. I bought matching heels and pantyhose that the girl recommended I wear. She also sold me a handbag to go along with the dress. For the first time I would learn how to hold makeup, my wallet, keys, and other essentials in a pocketbook. Next was a wig shop where I bought a wig of long brown hair that matched my own. A nail shop took care of painting my finger and toenails and I imposed upon the woman who had worked on me to show me how to apply some basic makeup to my face.

When I returned home I spent a couple of hours preparing myself to visit Cindy. When I was fully decked out in my dress, wig, stockings, heels, and makeup I gazed at myself in a large mirror. If I didn’t look closely at my face and softened my vision, I was looking at a woman. She was wearing a marvelously poufy dress that spoke of a sensual all enveloping femininity. Cindy would be immersed in this womanly presence and realize that this was it. This delicate and beautiful creature was the girlfriend Cindy was hoping to find at the end of her contest.

The last great frontier I'd have to cross is to make my thoughts those of a girl. I'll have to develop my mind so that it is indistinguishable from that of a female. Fortunately, I believe that I’m already halfway there. Once Cindy chooses me as her boyfriend, my daily life with her will bring me to become ever more feminine until all traces of my male mind are gone.

I steadied myself, put the strap of my purse over my shoulder and stepped out into the world as a woman. I took a taxi to Cindy’s apartment, ignoring whatever stares were sent my way. I was on a mission to conquer Henry once and for all time. If my theory was correct I would be delivering to Cindy exactly what she was hoping to get. She should declare a winner this very evening!

I rang the bell to Cindy’s apartment and waited. I heard her footsteps approaching the door and then it opened. She gazed at me in astonishment. Then she backed up so as to let me in. “Oh my God, Greg. You’ve transformed yourself into such a pretty girl. Makeup and a wig! I love it. And such pretty nails. Your dress just takes my breath away. How did you ever find such a darling dress. I absolutely love the pouf! You'll have to loan it to me! Your shoes are dreamy and you have a lovely purse. How did you know that you’re everything I ever wanted in a boyfriend?”

“You mean a boyfriend who is your girlfriend!”

“Yes! That’s exactly it! Are you going to be my girlfriend from now on?”

“Yes, Cindy.”

“No more boy for you?”

“None, whatsoever.”

“Except your penis?”

“Yes, of course. My penis is devoted to you. Any way you want to take advantage of it you are welcome.”

Cindy laughed. “That’s an offer I can’t refuse!”

We looked at each other for a few minutes without talking. Cindy kept examining me and she said, “We’ll get your ears pierced and I can’t wait until your hair grows out so we can get it styled. You’ll look enticing with some bracelets and a necklace.”

“I'll love to wear them. I promise to be the girl you want me to be.”

We sat side by side in a love seat in the living room. There was electricity in the air. I felt my heart beating a mile a minute. I could see rising passion in Cindy’s face. We had been spending so much time with each other, every other day, as we became closer and closer to each other and more familiar with who we were. Behind the scenes a sexual tension had been forming. The fact of the competition had pushed that out of our minds since nothing could be done about it. But now, this evening, wearing my pretty dress and newly acquired female persona the barriers that had separated me from Cindy were ready to tumble down.

Cindy started to put her arm across my shoulders when she stopped. “Okay, Greg. There’s something I’ve got to do. It’s only fair.” I watched as Cindy got up and retrieved her smart phone. She dialed a number and I heard her say “Hello, Henry.”

Then ensued a one-sided conversation.

“Oh, you guessed why I’m calling.”

“It’s not that you lost, it’s that Greg won.”

“I did love mothering you.”

“You were a cute baby, Henry.”

“To be honest, a toddler in diapers was a bit young. I think I would have preferred if you were at least ten years old.”

“I’m sorry Henry, but you hedged your bets with the French Maid costume. A good idea that didn’t quite come across as well as it might have.”

“I appreciate it Henry. You are a gentlemen and I will also miss you very much.”

“You too, Henry, have a good life.”

Cindy hung up the phone and sat down next to me again. I had a few tears in my eyes and I said, “I feel sad for Henry.”

“So do I. He was quite a lovely boy.”

“What’s he going to do now?”

“He’ll be fine, I’m not worried. People get over breakups. It happens every day. What would you have done if I had chosen him?”

“I can’t even begin to say. I’ve fallen so much in love with you. But you’re right. Eventually I would have returned to equilibrium, though I’m pretty sure I’d try and remain a girl.”

“That’s why you and I were meant for each other and not Henry. He isn’t a natural girl like you are. I love that you gave up your masculinity for me. Well, all except that penis that I intend to acquaint myself with. But even more importantly, your masculinity was really an illusion. I’m certain that you’ve always really been a girl, which is why you so effortlessly became the girlfriend I’ve always wanted.”

“I never knew that the happiness I'm feeling now was possible.”

“I want to hear all about the stunning dress that you’re wearing. I can’t believe how pretty it is and how pretty you look wearing it. You picked it out yourself?”

I was about to answer when Cindy said, “One second …” She put her arm across my shoulders and leaned in and began kissing me. She was hungry for my tongue and mouth and we had a long profoundly deep kiss. I felt my heart fluttering during the kiss and I even began to feel a bit faint. Cindy was a great and passionate kisser. I felt her beauty overwhelm me. The thought that we would soon be in bed together was almost too much to bear. I felt an enormous desire to give Cindy all the love I had within me. She broke off the kiss and said, “What were you saying about the dress?”

I gathered my thoughts. “It’s a pink tulle …”

She interrupted me saying, “You’re a fine kisser. Your lips are luscious. Go on …”

“It’s a pink …”

Cindy’s lips were back on mine. A moment later she broke off the kiss again and laughed. “I love you Greg.”

The End