How I Became a Princess

By Pamela

(pamelapamela@hotmail.com)

I have a beautiful wife, Naomi. Our marriage is great. She’s in her early thirties and already a senior editor at a top women’s fashion magazine. We met at the counter of a small pizzeria on 49th Street near Lexington Avenue. She had made a sound of pleasure from how delicious her slice was and I laughed. One thing led to another, and we got to talking and then we dated and fell in love. From the beginning I believed that Naomi had way more talent than she credited herself with. I ended up being right about that since she used her skill and wits to rapidly shoot up through the ranks of the fashion magazine where she works. No small accomplishment. After her next promotion she’ll be editor-in-chief, I bet.

If you’re wondering what I do, I’m a medical researcher in a lab. I guess I’m handsome enough and exciting enough to satisfy Naomi – anyway we have lots of chemistry which helps our marriage roll along just nicely. The main points I want to emphasize here is that Naomi is beautiful and a major force in her industry. She’s a power woman if ever there was one – sophisticated and poised. She knows how to be in control at all times – supremely confident in her abilities. Fortunately, she’s also an empathetic woman who leads compassionately. That means she’s very much respected, admired, and loved by the people she works with.

Okay, so now let’s get down to brass tacks. I’ve been a secret crossdresser since I was thirteen. Naomi knows nothing about it – I only cross-dress when she’s away on business. I have my own small collection of women’s clothing – I never touch hers if for no other reason than we’re not the same size. She’s 36D and I’m a 38 bandwidth. The two bras I’ve managed to buy have DD cups. Her panties are size 6 and mine are size 7. Her dresses are size 8 or 10, mine are 12 or 14.

Beginning at thirteen I was drawn to cross-dressing to compensate for my lack of a girlfriend. The next best thing to having a real live girlfriend with whom I could hold hands and maybe even kiss was playing with my mom’s clothes. Helping to fuel my desire to cross-dress were movies like Cinderella and Sleeping Beauty where I developed an infatuation for the princesses. I developed princess envy and fantasized about becoming a princess myself. I prayed that a pumpkin coach would show up one day and my fairy godmother would magically outfit me with a beautiful gown. Unlike Cinderella I wasn’t interested in a Prince Charming. Rather, I wanted to offer my love and devotion to a woman – a very special woman. She would be an authority figure in my life, such as a teacher or a doctor, a confident, mature woman who would appreciate having a pretty, feminine princess to lavish love upon her. I had intricate daydreams in which I planned every detail of the pretty outfit I wore as a princess.

Despite the fact that in college and beyond I did have girlfriends – including girlfriends I slept with – the need to cross-dress never went away. The desire to be a princess retreated to the background though it could be resuscitated from time to time. Curiosity as to why I wanted to cross-dress became a preoccupation of mine off and on. I’ve had various theories about it – mainly concerning the relative influences of my mom and dad – but mostly it remains mysterious. I guess it’s like why do we like chocolate or avocadoes. We just do.

Over the last few years, as I entered my thirties and am now thirty-five years old, my desire to cross-dress has coalesced around my childhood desire to be a princess who would be devoted to the happiness of a powerful woman. Naomi could certainly fit that bill. She is gifted and self-assured and a woman I look up to with love and respect. Gosh, it would be fun to act out the role of princess with her!

Recently my desire to be a princess has escalated to the point that it could be called an obsession. I frequently daydream about picking out my underwear and the oh-so-wonderful dress. I’ll have beautiful long hair with a tiara of diamonds sitting on my head. I’ll wear beautiful feminine shoes with spike heels. The whole nine yards, in other words. Your classic fairy tale princess. I admit these are very strange longings for a happily married thirty-five-year-old man. But that doesn’t make them go away.

You can imagine how hard a sell this would be to Naomi: “Hey, Naomi, do you mind if I flit around our apartment dressed as a princess?” No, I can’t expect that laying out this fantasy for her approval makes any sense. A much more reasonable goal, however, is to get her blessing for me to cross-dress. Once the door is opened a bit I can try to push it open further. Who knows, Naomi might like me doting on her as a princess.

Putting aside my princess fantasy, having more time to cross-dress would be nice, and that requires having Naomi’s blessing. A major obstacle to confessing my desires to Naomi is that I abhor the idea of subjecting her to disappointment or, even worse, the idea that she married me under false pretenses. I knew I was a cross-dresser when I married her but never mentioned it to her. Of course, my excuse for keeping my mouth shut was the belief that I could successfully control my desire to cross-dress. Now I know that isn’t true. I either confess to Naomi and see if that leads to an opportunity to cross-dress or else struggle along without fulfilling my deepest desires.

After much thought I decided that I have no choice except to explore Naomi’s feelings on the subject of marriage to a cross-dresser. Why should I assume the worse when it could be – and this is wishful thinking – that she either doesn’t mind or actually prefers me in a dress. How to bring up the subject of cross-dressing is a puzzle that I’ve thought about for some time. Finally I’ve realized that one can’t plan such a conversation. It will have to happen spontaneously and I awaited an opportunity to begin my confession. When I do I will start out subtle and adapt to the circumstances revealing more or less of my desires.

One evening after Naomi and I returned from a fashion industry gala, she took off her beautiful dress and I found myself staring at her wondrous feminine body wearing a matching white bra, panty and garter belt set and stockings. I envied her and I wondered how much she appreciated that she could wear such pretty underwear. I know these are crazy thoughts but I couldn’t stop myself from thinking them. I then heard myself say impulsively, “Do you like wearing bras?”

Naomi looked at me amused and said, “Are you asking if I want to go braless?”

“No, not exactly. I mean, assuming you need to wear a bra, do you like wearing them?”

“You mean, do I mind the fact that I need to wear one?”

“Yeah, I guess that’s what I’m asking.”

“I don’t mind wearing bras. Going braless means my boobs sway around and it’s kind of uncomfortable. With a bra on they don’t move and I like that. It’s nice to have support. But of course I’m a D cup. Women with smaller breasts might not care so much about their boobs flopping around. There, are you satisfied?”

“Yeah, thank you. That’s interesting. So if your breasts were smaller you might not wear a bra?”

“No, I’m not saying that. I probably would still wear a bra.”

“Why would you? What’s the reason?”

“Greg, what’s going on here? Why a sudden interest in bras?”

I laughed and said, “It’s not a sudden interest. You’re so sexy in a bra it makes me get curious.”

“If you say so. Why else do women wear bras besides holding up large boobs? One reason is modesty so men won’t see our nipples or our breasts through the fabric. It could also be because it’s what women do. We wear bras. We could feel undressed going out in public without a bra regardless of the size of our breasts. Bras also give us a chance to enjoy being female – if that’s what we want to do.”

“What does it mean to enjoy being a female?”

“What does it mean to enjoy being a male? Take bodybuilders, for example. They preen in front of mirrors looking at their muscles. How is that not enjoying being a male?”

“Merely wearing a bra enables a woman to enjoy being a female?”

“In the sense that a pretty bra on a woman makes her feel pretty. Feeling pretty is certainly one aspect of enjoying the fact that one's a girl.”

“Do you like enjoying being a female?” I asked.

“Sure I do. Take the lacy bra, panty, and garter belt set I’m wearing now. They always make me feel pretty. I enjoy feeling pretty and that’s tied in closely with my enjoying the fact that I’m a woman.”

“Wow, I never knew any of this.”

“Really? There have been times when you’ve been so proud of your boner and the way you use it. That’s another way of enjoying the fact that you’re a man.”

I thought for a moment and said, “I bet a bride in her gown is thinking that she’s happy she’s a woman.”

“True. Wearing a pretty dress is definitely something that enables women to enjoy being women.”

“That’s so interesting.” Naomi’s apparent good mood, her openness to talk about such a strange subject, caused me to summon up my courage and say, “The whole question of wearing a pretty dress and also being happy to be a woman or, rather, feeling like a woman, is an emotion that I’ve felt.”

“What in the world do you mean, Greg?”

I felt my face flush and said, “When I was young and watching movies with princesses – like Cinderella or Sleeping Beauty – I knew that I would love to be a princess – especially wear a dress like they wear.”

“And the prince in shining armor?”

“No, that never tempted me. It was their clothing and being beautiful and feminine like a princess.”

“What are you telling me? You now want to be a princess? It’s a little late for that. I suppose most countries that have princesses can’t just create new ones whenever they want.”

I laughed and said, “What I’m confessing mainly is a desire to cross-dress. It’s tied in with a part of me that has always wanted to be a girl.”

Naomi stared at me for a long time. I was scared to say anything more. “I feel like you’ve ambushed me, Greg. What is it you want? A dress to wear?”

“I was hoping that you might not mind if I wore a dress – only at home, of course.”

“A princess dress?”

“Well, any old dress would do.” I lied.

“Am I in a similar position to one of those wives whose husband declares he’s gay and runs off with a boyfriend?”

“Oh, no, sorry! I’m not seeking a Prince Charming. If anything my fantasies include a powerful woman – she could be someone like you – that would appreciate my femininity. I don’t want to ever leave you. I love you madly and I’ve revealed all this because - to be truthful - if you didn’t mind then I’d be missing out for no reason.”

“But if I do mind?”

“Then I guess you’ll know me a bit better than you knew me before? I would never leave you because of this – you mean more to me than wearing a dress or being a princess.”

“How long have you been feeling this way?”

“Since I was thirteen. As I’ve gotten older I’ve accepted it as just being a part of my makeup – one of those personality traits that together make a person.”

“You’ve been secretly cross-dressing?”

“Yeah, when you’re away.”

“Wow, Greg. Behind my back. I don’t know what to think. What else do you do in secret?”

“Nothing, I swear. This is my one big secret. The thought of losing you was more than enough reason for me to keep my cross-dressing from you.”

“But now I do know about it.”

“Only because I’ve changed in ways that I never knew I was going to change.”

“Anyway, you present your need to cross-dress as a fait accompli. You’ve arrived at a point in your life where you have to cross-dress when in my presence.”

“What I’m saying is that I feel pressure to find out if there’s a way to not have to hide who I am but still be happily married to you. Or have I already revealed enough about myself that you’ll want to leave me.”

“I love and care about you as a person, Greg, you know that. But just like you have a need to express your femininity, I have a right to not want to be with a man of your ilk if I don’t want to be.”

“I agree completely. If you feel we have to separate then I’m sure we’ll both be very sad, but I’ll have the additional burden of feeling guilty that I caused this. So you can see just how traumatic this confession is to me.”

“I honestly don’t know how to answer you. Can I live with a husband who cross-dresses? Will his being feminine take away from my physical desire for him? I have doubts that I’m the sort of woman who wishes to be in a dominant position in her marriage. I like equality.”

“I’m only talking about one aspect of our relationship.”

“Be that as it may, I can’t answer these questions off the top of my head. So now I’m taking off my bra and other clothing and putting on my nightie and going to bed.”

I watched as Naomi got dressed for bed, abluted in the bathroom, and lay down on her side of the bed. I quietly undressed and slid in beside her. Usually we kissed each other good night but that wasn’t going to happen that night.

Before going to sleep I cringed at the thought that I’ve caused Naomi to think less of me. I was clearly no longer the man she thought I was. I would now forever be a man who wants to wear women’s clothing. I wondered how much I had damaged our relationship. Fatally? I’d find out soon enough.

***

The next morning, over breakfast Naomi said, “I woke up this morning thinking that I shouldn’t make hasty judgements and I shouldn’t promise you anything. We have to see how this goes, baby step by baby step. If it turns out to be unpleasant for me then I’m going to ask you to not cross-dress in my presence. If it turns out okay for me then we’ll settle into lives that are more or less like they have been - which I mean is happy and satisfying.”

“Thank you, Naomi. That’s all I can hope for.”

“It’s too soon to thank me. One of the ground rules here is I don’t want to be considered a co-conspirator in setting you up in women’s clothing. I will criticize when I have to. Other than that you’ll have to figure it out for yourself.”

“That’s fair, of course.”

“Not being a co-conspirator means not holding secrets when I don’t want to. I’ll determine for myself who I tell or not tell about your cross-dressing. In other words, you’re not in the driver’s seat and I won’t be under obligation to modify my behavior. You’ll just have to deal with me.”

“That’s all fine with me. I want you to be happy. I pray you can find a way to live with this that doesn’t cause you any misgivings.”

With that, Naomi had given me license to do what I wanted to do.

***

For a few days I contemplated what I needed for my debut dressed as a woman. First and foremost I had to get myself some boobs and shoes. Then I’d reveal myself to Naomi and see what reaction she might have. To get shoes I found a small shop on a side street in Soho and bought some low heels that fit me pretty well. To get boobs I went out to a medical supply store in Queens. I paid cash and was anonymous. It was good practice fortifying myself for Naomi’s response.

When all was ready, I decided that the next day, a Wednesday, I’d get home sometime ahead of Naomi and put on my woman’s outfit. Wednesday was always our Thai food day – a midweek respite from cooking dinner. Naomi would stop off at our favorite place and pick up the dinner. I put on my bra, panties, and pantyhose. For the first time I had breast forms instead of the balled-up socks I’d used before. I put on my light blue sheath dress – it’s more toned down than my other dress which is my favorite. That’s pink and white checks with a tight bodice and full skirt. Last was the low heels I had bought. My hair is fairly long and I combed it to either side in what I hope could be called my cute girl look. When my hair is a few inches longer and reaches my shoulders, it’ll be perfect.

I had bought a bit of makeup; mainly red lipstick, powder, and rouge. I put it on to the best of my ability. I wish I knew how to do my eyes. I’ve watched Naomi put on her eye makeup countless times but unless I physically imitated what she was doing it would be impossible to do it justice. With my lips bright red and rouge on my cheeks I looked in a full-length mirror to finally get a complete view of myself fully decked out.

Yes, the person looking back at me in the mirror wasn’t an obvious woman, but she also wasn’t an obvious man. With better makeup, a different hair style, I could see myself as being more woman than man. In the meantime, my large chest did wonders for announcing that I was female and with that I had pleasant spasms of femininity coursing through my body. All these feelings were helped by the unique feel of my underwear. There’s nothing in the boy wardrobe that feels like a bra or pantyhose! The main result of seeing myself in the mirror was to reinforce my belief that I was doing the right thing. The degree to which I felt a profound sense of contentment had to be an important guidepost that I was moving in the right direction.

I set the table and waited with trepidation for Naomi. This would be her first time seeing me in a dress. I hoped the shock wouldn’t be too great. I sat in the living room watching the clock. As soon as I heard her enter I’d get up and nonchalantly greet her as if everything were normal. By carefully looking at her face I’d get clues as to what to expect in her reaction to me.

Some minutes later I heard the door open and I got up to greet Naomi. As she approached the living room I heard talking and realized she wasn’t alone. I made a mad dash to the bedroom but Naomi saw me in the hallway and yelled out, “What in the world, Greg?”

I stopped and turned around. Naomi was joined by two other women. I recognized her boss, the editor-in-chief Glenda, and another woman I had never met before. I stared at them in astonishment as Naomi said matter of factly, “You know Glenda. Alicia is president of the corporation. Glenda and Alicia, meet my husband Greg.”

"Hi,” I said staring at the three imposing women with my eyes wide open and jaw hanging down. They were dressed as power women wearing finely tailored skirts and feminine blouses in different pastel shades. From their perfectly groomed hair, makeup, and polished fingernails down through their curvaceous bodies to their expensive stiletto heels the women exuded that sophistication and worldliness one would see, for example, in a James Bond movie. In my simple sheath dress and childish makeup I felt overwhelmed.

Glenda and Alicia smiled at me without saying anything and then looked at Naomi as if waiting for an explanation. Between the two of them, Alicia was closer to my height. She had an air about her that was both stern but also amused. She was definitely the kind of woman who was used to being in charge.

“Where were you running off to?” Naomi said.

“I didn’t know you were bringing friends home …”

“As you can see, my husband has some issues he’s working on,” Naomi said.

“Makeup?” Glenda said and she and Naomi laughed.

“That’s funny,” Alicia said. “I can’t recall ever being introduced to a transvestite husband.”

“Cross-dresser,” Glenda said.

“Pardon me, cross-dresser,” Alicia said.

“You owe the ladies an explanation, Greg,” Naomi said.

“I, I, um … I, um, ...” I said.

“Last week Greg confessed that he’s been a secret cross-dresser. Now he wants my permission to cross-dress without keeping it hidden.”

“Incredible,” Glenda said. “Imagine that. Hiding it. I wonder how many men do that?”

“Not too many, I would assume,” Alicia said. “I’m wondering why Greg no longer wants to keep it secret.”

“The older he gets the more he wants to do it. He needs more time to cross-dress than he can get when I’m away on business,” Naomi said.

“That’s easy to explain,” Alicia said. “Pleasure feeds upon itself. It’s Darwinian. Since cross-dressing gives him pleasure the more he does it the more pleasure he gets. In essence it’s an addiction.”

“That sounds ominous,” Naomi said. “Will Greg eventually have to cross-dress all the time? What about it, Greg?”

“I can see wanting to cross-dress whenever I’m home. But I’m not going to want to cross-dress outside.”

“Why not?”

“I’m shy. I think it’s a private thing for me.”

“It all boils down to an issue of trust,” Naomi said. “You say you don’t want to cross-dress in public but why should I trust you? I had trusted you until this confession of yours. How do I know that you don’t harbor other secret thoughts?”

“You’re right to wonder, Naomi. In my defense, I honestly didn’t understand that my need to cross-dress would grow past my current opportunities to do it in secret.”

“At this point I guess you’re waiting for my judgement on how you look in your blue sheath dress,” Naomi said.

“I know I’m not beautiful.”

“How could you be? But I’m not worried about beauty. Most important for me is if I feel comfortable with the way you look.”

“I also have another dress. It’s pink and white. Actually, it’s my favorite. I wore this one because I thought you might find it more refined.”

“Well, Glenda and Alicia, what do you think?”

“I’m fascinated by Greg’s bust,” Glenda said. “It really does shout out his femininity. Clearly a sheath dress is a good choice for him since it does just enough to accent his small curves. “

“I agree.” Alicia said. “I’ve never seen Greg in boy clothes, but in the sheath dress he’s more woman than man. No doubt, however, by being married to him you’ll have a much different reaction to his cross-dressing.”

“That’s true,” Naomi said. “Greg, fetch your pink and white dress.”

I got the dress and brought it to Naomi. She held it up and she and her friends examined it.

“It’s pretty,” Glenda said.

“Feminine,” Alicia said.

"Put the pink dress on, Greg,” Naomi said.

As I reached behind my neck to undo my zipper, Glenda said, “Let me help you.”

“Thanks.”

Glenda pulled the zipper down my back and I stepped out of the sheath dress. The women were curious about my pink and white bra and panty set. “Look at that,” Naomi said. “That’s the Prima Donna Novaro bra and panty. Exquisite taste, Greg, I must admit. I’m surprised that you have such a sharp eye for pretty bras and panties.”

“Thank you, Naomi. I took one look at the bra and I was in love with it.”

Alicia and Glenda laughed. “How cute, Greg,” Alicia said. “I would have reacted like that when I was a young girl. Gosh, if my mom were feeling good and wanted to make me super happy she’d allow me to buy a pretty, lacy bra. I’d be in seventh heaven!”

I looked at Naomi to see how she was reacting. I wondered if her comments so far meant that she’d be tolerant of my cross-dressing.

“Put on the pink dress,” Naomi said.

I did as she said, and Glenda zipped up the back. Now I truly felt girlish. The dress accentuated my bosom and the skirt fit in with my princess fantasy. The only thing that could be better than this dress was a real princess gown including all the underthings like several crinolines that would keep if poofy.

“Oh, what a dear!” Glenda said.

“I’m afraid, Naomi,” Alicia said, “that there’s an awful lot of girl in Greg. This dress really brings it out of him.”

“This is the problem I foresaw,” Naomi said.

“What’s that?” Glenda asked.

“Greg confided in me that he has a princess fantasy. He’d love to be a princess wearing a pretty gown. This dress is a step in that direction. I can see why he loves it so much.”

“You have a princess fantasy?” Alicia asked.

“I’m afraid so. I’m embarrassed to say that if I had the opportunity I would dress like a princess.”

Alicia laughed. “Like Aurora from Sleeping Beauty, or Rapunzel or Ariel?”

“I know it’s ridiculous. I first had the fantasy when I was a preteen and it keeps coming back to me every so often.”

“When I was ten I wanted to be a princess also, so I can relate to the feeling,” Glenda said.

“Me too,” Alicia said. “Almost all little girls want to be princesses at some point in their lives.”

Naomi laughed, “I shouldn’t be laughing but it is comical that Greg has the same temperament as preteen girls.”

“Were you hoping for a Prince Charming to awaken you with a kiss?” Glenda asked.

“No, …” I started to say.

“Greg’s fantasy has him doting on a powerful, older woman who appreciates his femininity and subservience,” Naomi said.

“How interesting,” Alicia said.

“I imagine that Greg has twenty-five years of suppressing his desires. By being frozen in time the pressure to act out his fantasy surged within him,” Glenda said.

“Be that as it may,” Naomi said, “looking at Greg in that pretty dress I have to unfortunately conclude that I really can’t go along with his cross-dressing in my presence. The truth is that he’s too pretty, too feminine, which takes away from my sexual attraction to him. As I already told him I’m not attracted to him fawning over me as if he were a girl. I’m one of those women that needs to feel like I’m making love to a man. I’m sorry Greg.”

I felt my eyes uncontrollably filling up with tears. Both of the paths ahead of me now were onerous. Either cross-dressing no more than I was currently doing or ending up losing Naomi and my marriage. Naomi saw my tears and said, “I’m sorry Greg, I can see how I’ve dashed your hopes. But I have to be true to myself. I don’t object if you cross-dress when I’m not around to see it. That’s not a problem for me.”

“I’m sorry, Naomi. I don’t know what’s gotten over me. Why I’m so emotional. I do appreciate your letting me cross-dress when you’re away.”

Glenda and Alicia looked as if they were touched by this tender domestic scene between Naomi and me. “Can I have a word with you,” Alicia said to Naomi.

The three women left to talk privately among themselves. They were out of earshot but I heard Naomi exclaim, “Really? Well then, that’s amazing!” followed by laughter. The women were gone for what seemed like ages until they finally returned. Naomi said, “Greg, you won’t believe it but, courtesy of Alicia, you’re looking at the new editor-in-chief of the magazine!”

“Unbelievable!” I said. “That’s great news. What happened?”

“Glenda is resigning to head up a magazine based in Paris. That long has been her goal.”

“Editor-in-chief, that’s … wow,” I said and wondered what if anything they had decided about me.

“Now, about your cross-dressing,” Naomi said. “I think we may have found a compromise that can make everyone happy.”

“Really?” I asked. That seemed too good to be true.

“Alicia thinks it would be amusing and fun to see you in the role of a princess.”

“What? She would?” I exclaimed. This was about the last thing I expected Naomi to say. Of the three women, Alicia – just slightly older than Naomi – had the directness and self-confidence of someone used to running a large organization. She was a woman who knew how to be a woman. I felt more than a little intimidated by her mental acuity and sexuality – exactly the qualities that I wanted in my princess fantasies. This seemed too good to be true.

“Yes, she would. So her idea is that you’ll spend a day at her house in Westchester where you could be a princess to your heart’s content. The both of you could see how it goes and decide from there about the future.”

I stared at Naomi not knowing what to say. My mind raced to try and figure out what Alicia’s motivation might be. Was she really just being kind to me? Would me being a princess fulfill a desire of hers? Was there a quid pro quo with Naomi? What was I not being told? How would I ever survive being alone in a house with Alicia? I’d feel so inadequate, but wasn’t that the way I was hoping to feel as a princess? Though I had these thoughts I knew that I was like a fish hooked on a line. As long as there was an opportunity for me to be a princess I was going to take it.

“I’m speechless,” I said. “It’s so unbelievably kind of you, Alicia, and, of course, my dear wife for allowing me to spend time with another woman!”

“There’s nothing to worry about in that department,” Naomi said laughing and Alicia joined in with her. For a brief second I wondered if they were laughing for different reasons than I imagined they were.

“It won’t be anything like that,” Alicia said. “Greg will be dressed to the nines in a beautiful princess gown and he’ll have the freedom to spend the day flitting around like a princess.”

***

After Glenda and Alicia left I asked Naomi, “What made you and Alicia agree on letting me be a princess at her house?”

Naomi smiled and said, “It’s kind of a coincidence, but Alicia has been considering ways in which our magazine can be of practical use to cross-dressers. By that I mean not just a place where cross-dressers can look with envy upon our articles on women’s fashion. Rather, we could have some articles devoted to useful ways that cross-dressers could up their game. Improve their femininizing skills.”

“You never mentioned this before.”

“It’s been mainly an action item that has yet to be explored. It occurred to us that Alicia can gain valuable information about cross-dressers and how they think by spending some days with you. Letting you express your feminine side will allow us to see – in an unbiased and objective way – exactly what makes people like you tick. We can then use that to formulate some content in the magazine as time goes by.”

“So I’m like a Guinea Pig?”

Naomi laughed, “Yes, if you’d like to see it like that. On the other hand …”

“I’m not complaining. I was worried that I was forcing you to make a concession against your better judgement.”

“As you see, far from it. I’m actually quite pleased you’ll be visiting Alicia. What she reports to us about your behavior will be helpful to the magazine.”

***

A couple of weeks later I took the train up to visit with Alicia. She picked me up at the train station. I was nervous to actually be one on one with her. That I would become a princess in her presence was both exhilarating and frightening. It’s one thing to fantasize about something and another to live one’s fantasies.

Alicia drove to a wedding shop owned by a friend of hers. “Hi Sylvia,” she said when we entered. “I’m not going to mince words. I want to make over Greg here into a princess. An absolutely adorable princess – as feminine as you know how to do.”

I got weak-kneed with excitement thinking how my lifetime of fantasy might reach fruition on this very day. Alicia’s attitude was: ‘Damn the torpedoes! Full speed ahead!” She had no concern for what Sylvia might feel dressing me as a princess, nor did she care what the few other women in the shop might think. After my emotionally trying interactions with Naomi I had reached a point where I was going to let myself blow in the wind to wherever it took me. A hundred times I begged Naomi for forgiveness if I had hurt her in any way and she denied that I had. She also had no complaint at all about having Alicia take care of me – in effect be my babysitter – as I acted out my princess fantasy. “Have fun. Don’t feel guilty.”

With Sylvia’s help we found the perfect princess dress. It leapt out at me the moment I saw it and Alicia agreed that I couldn’t do better. “When I was ten I would have died for this dress!”

It was a pale pink, strapless, tulle, tea-length ball gown, featuring a straight-across, strapless neckline that elegantly framed the décolletage. The dress was crafted with seemingly endless layers of tulle, the hand-draped bodice sculpted the upper body before erupting into a dramatic full skirt adorned with a bright pink bow along the back. Cinderella would have screamed with excitement if her fairy godmother had dressed her in this gown.

To top it off Sylvia produced seductively pretty heels for me to wear as well as stockings and a pink garter belt. A strapless bra with matching panty completed my outfit. “I’m getting you an A cup bra, Greg, because you’re a young princess. When you’re an adult your bosom may grow to a DD cup size, but you’ll have to wait patiently for that to happen.”

Alicia helped me with the stockings and bra and she and Sylvia helped me into the dress. I put on the shoes and walked out from the dressing room to step up onto a small platform in a room surrounded by mirrors. A group of women came over to watch as Sylvias scrutinized me from every angle. The ladies applauded when I twirled in front of the mirror happier than I could ever remember being – well, apart from the day I married Naomi!

“I’m so in love with this outfit, this dress, with everything!” I said to Alicia. “I feel just like a princess!”

“Would you like to go back to the house as a princess?” Alicia asked.

“Oh God, yes! I don’t ever want …” I stopped what I was about to say - which was that I didn’t want to ever stop being a princess. Naomi would be none too pleased if that were what I felt!

Sylvia instructed me on how to hold my voluminous skirts so they didn’t get caught on anything as I was getting into Alicia’s car. Once I was seated I had tulle piled up practically to my face. Alicia looked over at me and laughed.

“You’re just a big pink cloud, Greg.”

“I know. It’s so much fun. This is what I always wanted. I wished and wished and wished for it when I was thirteen. In all my dreams and daydreams. I wanted to be a princess.”

“A dream come true,” Alicia said. “When we get to my place we need to put polish on your nails and I have some ideas for your hair and makeup. By the time I’m done with you there’s no doubt that you’ll be a beautiful princess.”

***

At Alicia’s expansive house, she had me take off the dress while she did my nails, hair, and makeup. When she was done, I put the dress back on and Alicia led me to a mirror where I stared at myself in amazement. Maybe not as beautiful as Cinderella or Aurora but I could pass for a princess.

In a dream like state overflowing with feelings of femininity, Alicia led me to her living room where we sat down together on the sofa.

“You are a beautiful princess, Greg,” Alicia said and I giggled with happiness.

“I’ll never be able to thank you enough! How can I ever thank you?”

Alicia put her arm over my shoulders and held me. “You are a sweet princess. I like my princesses to be sweet. You know, kind, empathetic, concerned about her people.”

“I am, I am!”

“Good. Besides that you’re pretty.”

“I so love being a girl! Thanks for making this happen!”

“It’s my pleasure, I assure you. It’s fun to be a girl – and you should be a girl for as long as possible – but I would be remiss if I didn’t teach you about womanhood. Princesses do eventually grow up and I want to make sure you’re fully prepared for that life.”

“I would love for you to teach me about being a woman!”

“Great. Then I will.”

“What will you teach me?”

“I’ll teach you the secrets of womanhood. Every girl needs to learn these secrets if she’s going to become a woman.”

“Wow!”

Alicia laughed. “Yes, wow! Today I’ll let you explore all those special treasures that women have that make them who they are.”

“What treasures are those?”

“You will see. First, lay down and put your head in my lap.”

I got up and held my skirts so I could lie on my back on the sofa with my head in Alicia’s lap. She helped me smooth and straighten the many layers of tulle that had bunched up over me. I looked up into Alicia’s face as she smiled at me, her long stylish hair cascading around her face to just dance on my forehead and cheeks depending on how much she lowered her head. I didn’t know what was coming but I was excited and deliriously happy. I wondered if Naomi really didn’t mind me feeling this good or minded me having my head in the lap of another woman. Even more, I was aware of Alicia’s exceptional bosom that projected outwards just inches from my face. She was wearing a delicate white blouse that was just opaque enough to disguise the outline of her bra. She was wearing stockings and she hadn’t taken off her heels so that her knees were slightly raised creating a warm cradle for my head in the folds of her black skirt.

“Are you comfortable, my princess?” Alicia asked me.

“Oh yes, I am,” I said.

“Do you see my blouse?”

“Yes.”

“Tell me what you see as I unbutton it.”

Alicia started with the top button. By the third button I could see the swell of her breasts at the top of her bra. “I can see your bra and I can see your breasts.”

As Alicia undid the next button I had a remarkable view of the round protuberance of her twin breasts held by a deliciously pretty lilac bra. “Oh, Alicia, I love your bra.”

I watched in fascination as Alicia rested her pointer finger with its long pink fingernail on her bra. “Yes, this is one of my prettiest bras. I wore it special today because I know that my princess loves pretty bras. Doesn’t she?”

“Yes, I do,” I said.

“This particular bra has pretty pink flowers as you see.” Alicia’s finger traced the outline of several of the flowers on her bra cups. “The lace edging is so pretty, don’t you agree?” Her finger moved to the lace on the top of the cups. As I watched her finger I sometimes looked up at Alicia’s beautiful red lips as she spoke. “This part is very special,” Alicia said and her finger moved to the center gore. “Do you know why?”

“Why, Alicia?” I asked plaintively.

“Because it’s the space between my large breasts.”

I stared fixedly at the region between her breasts. The full shape of her breasts held by the bra cups was as beautiful as the Grand Canyon. “I love your breasts. I love your bra,” I said, overloaded with passion for Alicia and her chest.

Alicia finished unbuttoning her blouse so now I had a full view of her bra and breasts. “As women we have breasts and we wear bras. This is your first lesson. Take in every aspect of your view of my chest.”

“I’m also wearing a bra, Alicia,” I said.

Alicia laughed. “Yes, it’s good for young girls like you to practice wearing them. One day you’ll be confronted with having real breasts like you see in front of you.”

“I can’t wait!”

“Would you like to rest your face between my breasts?”

“Yes,” I said weakly. My strength was ebbing as I was in a near faint from sexual and emotional excitement.

Alicia unhooked her bra and took it off. I watched in awe as her breasts escaped from her bra cups and landed on her chest. “Hold my bra for me,” Alicia said.

As I took the bra into my hand, Alicia leaned forward as she gathered up my head in her arms and pushed my face deep into her breasts. I reveled in the perfumy warmth of her breasts smothering my face. This was a moment I would always treasure.

“Isn’t it nice being a pretty princess?” Alicia said. “You get to be appreciated for the beautiful girl you are.”

“It is so nice,” I mumbled. I wasn’t exactly sure why Alicia had handed me her bra, but I found that holding it in my hand made me feel strangely connected to Alicia. Actually, I felt that holding the bra made me a part of her. This was getting clearer by the minute. Whomever I was, my mind and personality were being subsumed within Alicia’s overwhelming presence. This was how she was making me into a princess.

After some time, Alicia leaned back giving me a view of her breasts. “Look at their size and shape. Feel them if you like. These are the breasts of a woman. They hold tremendous power over any prince you might one day meet!”

I gingerly felt the sides of Alicia’s breasts. They were smooth and soft and warm. Alicia used a finger from each of her hands to point at the hard bumps of her nipples. “These are my nipples. Each breast has a nipple. Each of your breasts has a nipple. Babies like to suck on them. You might have a baby one day that’ll suck on your nipples.”

I had a feeling that Alicia was going to offer me one of her nipples to suck on. My desire rose to a crescendo and I was preparing to beg her to let me nurse on her breasts when she said, “Would you like to suckle on my titties?” and laughed.

I nodded and she raised my head aiming a nipple into my mouth. I sucked on it gently, tugging at it with my mouth according to a genetically preprogrammed muscle response. It was innate, a reflex that required no thought. Alicia had a child now off at college. Having once been pregnant, under the prompting of my suckling small amounts of sweet fluid leaked out into my mouth. I hungrily swallowed her maternal offerings.

“Oooh, that feels good,” Alicia said. “You’re a good sucker, princess. Not too hard, not too soft, just right. Someday when you meet a prince and you marry him and have babies you’ll nurse them just like this.”

“Mmmmmm,” I said dreamily. Was it possible for a human being to be as happy as I was? I thought of my pretty dress and my sexy underwear. I thought of Alicia holding me, her wonderful breasts pressed into my face. Deep inside my dress, inside my panties my own sexual organ burned with lust and without my having to explore it I was sure that there was a prodigious leak of my own seminal fluid wetting my underwear.

After a while Alicia switched my mouth to her other nipple and I resumed feeding there. Alicia looked down on me and said, “What a lovely sight. My little princess lapping up her mommy’s milk. You will grow up to be the most beautiful princess in all the land.”

I smiled looking up at Alicia and made a cooing sound.

“I believe you’ve now got a pretty good idea of what a woman’s breasts are all about. Now I want to teach you about what to expect within a woman’s skirt.” Alicia gently removed her breast from my mouth and kissed me on the forehead as if I were her baby girl. She shifted her position raising one leg up to put her foot on the sofa and thereby giving access to whatever might be in her skirt. She had me turn on my side resting my cheek on her stockinged thigh so I could have a look up inside. “What do you see?”

“I can see garters that hold up your stockings.”

“What are they attached to?”

“A girdle? Are you wearing a girdle?”

“Yes, very good princess.”

“Your girdle is so fancy. Wow. It’s got so much lace and it must be an open bottom girdle! I can see your panties. They’re lacy like your girdle. I think they’re pink.”

Alicia pulled her skirt higher up her thighs. “Can you see better now?”

“Oh, your girdle and panties are lilac and match your bra! Isn’t that true?”

“Yes, very good princess.”

I continued to stare at Alicia’s womanly underclothes and how they held her flesh. She said, “Give me a second to take off my panties so you can get a good view of my vagina.”

I lifted my head off of her thigh and she stood up. I watched as she unhooked her stockings, raised up her girdle, and pulled down her panties and handed them to me. She laughed slightly and said, “I thought you might want to hold them together with my bra.”

“Sure, Alicia.” I did want to hold them. Holding her panties together with her bra accentuated my feeling that I was attached to Alicia. I was an extension of her femininity. I was dependent and sustained by her. Holding her underwear for her showed that I was committed to her. It was an act of obeisance and love. It gave me a purpose as her princess.

Alicia sat back on the sofa again and I returned to my position with my cheek on her thigh. I watched her point her index finger at her vagina. “As you know, panties rest up against our vaginas. What do you think of my vagina?”

“It’s pretty,” I said. Alicia had a shaved vagina and it’s vertical lip looked adorable with slightly puffy skin to each side.

“Do you have a vagina?”

Without needing to think I said, “Of course I do.”

“Why?”

“Because I’m a princess and princesses have vaginas.”

“Very good. You’re too young to know about a woman’s vagina so I'll teach you.”

“Thank you, Alicia. I’m eager to learn!”

“This is an opportunity for you to familiarize yourself with some of the most important aspects of vaginas,” Alicia said. “For example, when a vagina calls out for attention you have to make sure you do what it wants.”

“They rule?”

“Yes, they do. Especially for a princess like you. My vagina needs to always be a priority for you when it calls for attention.”

“What kind of attention?”

“This is perhaps the most important lesson I can share with you. You need to learn how a woman takes pleasure from her vagina. It’s one of the most profound secrets in the universe. Most men have no clue how to excite a vagina. Even many women don’t fully understand how or where they get pleasure from their vaginas. But you, my dear princess, you’re going to become an expert at knowing the pleasures of a vagina.”

“Wow.”

Alicia laughed. “It’s how you’ll choose your Prince Charming. He’ll be the prince that knows how to give your vagina pleasure!”

I had a sense that Alicia was being a bit dramatic but I could see there were many elements of truth in what she was saying. Naomi’s vagina has always been a great mystery to me. I think she did sometimes get orgasms from our intercourse but that was as much through her own effort as mine.

“I would love to devote myself to giving your vagina pleasure,” I said.

“I thought you would. So first of all hold out your index finger.” I did as she said. “Wet it with saliva.” I did that and she said, “Keep your hand loose and I’ll guide your finger into my vagina.” I felt Alicia move my hand until my finger touched the lip of her vagina. Then she expertly put it in the environs of her clitoris and began gently moving my finger up and back and sideways. “Ahhh,” she said, obviously enjoying my controlled touching. “Do you feel my girl boner forming?” she asked.

“Girl boner?”

“There’s a region that swells with blood until it’s hard and elongated.”

“Yes, I do feel that.” Alicia gave me a detailed description of how I was to gently rub my finger along her boner, on its sides, especially in circular motions at its top. I really appreciated the help and wondered if the same motions would work on Naomi.

“You’re doing perfectly. Not too firm, not too gentle. You have the touch of a princess!”

After fifteen minutes or so, I felt Alicia tensing up and she let out a quiet moan and sigh. “Oh, so nice, princess. That was my first climax. Now’s a good time for you to switch to your lips and tongue.”

“Great,” I said. The close proximity of her vagina to my mouth had been fueling my desire to suck on it. I moved my lips until they were kissing her sweet, warm, vagina, and I firmly slipped my tongue inside of her.

“You see how my vagina has captured you? You will be forever a slave to my vagina.”

I didn’t know if Alicia meant that literally or figuratively, but I was in no position to argue with her. I’m sure there was nothing more in the world I wanted to be doing than sucking on Alicia’s vagina. The more I sucked the more my mind fixated on pleasuring her. The more I heard her moaning and felt her tensing up the more I wanted to press my face into her vagina. This was a part of the role of princess that I hadn’t fantasized about, but I could see now that it was just another one of those glorious things that came with being a girl. Pleasuring a woman as her darling and delicate princess was now among my most desirable activities. Somewhere in the back of my mind I worried if Naomi would be upset but I knew that I was fully in Alicia’s control and it was pointless for me to worry about consequences or the future. At the end of the day there would be a reckoning. I’d wait until then to figure out what if anything I should tell Naomi about this day.

I think we all know where this was heading. After way too many climaxes for me to count, Alicia was in a state of unstoppable sexual hedonism. “Get on your back my princess,” she said commandingly, “and raise your legs up and apart.” I did as she said. She lifted up the skirt of my princess gown and its many layers of tulle to expose my panties. Somehow she knew what she’d find in my panties and she pulled it out to stand upright under its own power. She madly and half crazily impaled herself on me and humped me. “Oh my cute, adorable princess,” she whispered in my ear as she pounded away on me.

“You’re so strong and powerful,” I whispered in Alicia’s ear.

This prompted her to bear down even harder on me. Suddenly she called out, “This is so good, so good. Yes definitely! I’m going to keep you! Yes, that’s what I’ve decided! No question no question at all! I see it clearly! Oh, happy day!”

I didn’t know what in the world Alicia was referring to. I supposed it was nice that she wanted to keep me. In fact, considering how much I felt like she was in control of my mind and body I would be devastated if she didn’t want to keep me. But then what of Naomi? I was utterly mixed up inside between my increasing subservience to Alicia and my guilt about Naomi. Alicia’s personality was so overwhelming that I doubted that I had the ability to resist her dominance over me. I had no defense against her controlling my future – but hurting Naomi was never part of my plans.

I can’t tell you how long our rutting went on. The long preliminaries with my leaking had paved the way for a slow ascent to orgasm. The pleasure was indescribable – the kind you never want to give up. I let it percolate and percolate through my body. I was the maiden being taken by my mistress. Throughout our lovemaking I clung to the image of myself in my princess gown overflowing with femininity and beauty. Let my mistress ravish me – she can’t control herself. I am in a sexual black hole from which there is no escape.

When finally I burst into orgasm I nearly deafened Alicia and she collapsed next to me laughing. We were both rapturously thankful for the fun time we had had. As the pleasure ebbed from my body my mind remembered every nuance of our sexual bonding. There was no doubt in my mind that being a princess had everything to do with the success of my lovemaking with Alicia.

There was also no way to ignore the fact that I had cheated on Naomi. This couldn’t be what Naomi expected. No amount of words would undo that basic fact. For my part I had been carried away by Alicia’s powerful seduction. I wondered if I should say something about Naomi to her.

“I hope we can do this again soon,” I said, “though I don’t know if what we’ve done fits in with Naomi’s expectations. I’m not sure she was planning on our love making. I hope I haven’t hurt her.”

Alicia laughed for reasons I couldn’t imagine.

“What’s so funny?” I asked.

“It appears Naomi left out a few of the important details of our conversation two weeks ago in your apartment. I suppose she was a little hesitant about telling you. Obviously, she wants me to be the one to inform you.”

“What are you talking about?” I said, alarmed.

“Let me just rip off the band aid. She gave you to me as payment for my appointing her the new editor-in-chief.”

“Gave me to you?”

“Yes, that is, if I wanted you. The deal would be finalized after I spent a day with you. I had to see what kind of princess you were before I could commit myself. As you heard me say earlier I’ve decided to keep you. So you’re now mine. You’re my princess.”

“Like how often?”

“Greg, you’re not understanding. You’re now my princess. You’re no longer Naomi’s husband. You’ll be living here as my princess.

“Naomi gave me away?” I was still having a hard time comprehending what Alicia was telling me. It seemed otherworldly and bizarre. My life ahead of me was as Alicia’s princess - and I had no choice in the matter.

“Yes, for editor-in-chief. I’ve taken ownership of you.”

“You own me now?”

“Yes., as I’ve been saying. You’re mine. My princess.”

“And if I wanted to stay with Naomi?”

“You’re not hearing me. That ship has already sailed. It’s not one of your choices. Naomi will not take you back. You’re free to leave here, in which case I may or may not keep Naomi as editor-in-chief. I hope that’s not what you choose to do, though I’m sure you’re incapable of leaving.”

“How can you own me? Can’t I do what I want?”

Alicia laughed. “Greg, you’re still holding my bra and panty in your hand. There’s no way in the world that you’ll ever be able to sever yourself from my domination of you. I own you. Mind, body, and soul. You’ll be my princess from now on. At night you’ll be a pretty princess sleeping in my bed. During the day you’ll wear your gown and take care of the house.”

I looked at Alicia’s panty and bra and put them down. I looked at her naked body and my own pretty gown. My eyes met those of Alicia and I felt overwhelmed and enraptured. She was right about everything. I had no cause to walk away from the life she laid out for me. She was going to take care of me as her pretty princess. The dream I’d wished for a thousand times.

“Naomi was conflicted about denying you the opportunity to cross-dress and act out your princess fantasy. At the same time – as you can see today – I love having a man like you as my princess. I knew that Glenda had accepted an offer from a Parisian magazine that she had been negotiating with. Inspired, I told Naomi that I’d take you as the price for me appointing her the new editor-in-chief. She thought about it for a minute or two and decided that it was a win-win-win-win situation. She’d become editor, she’d not have to deal with your cross-dressing, I’d get a princess that I could play with, and you’d be a princess."

Alicia continued, "There were two conditions for the deal to go through. First of all you’d have to agree to be a princess – which obviously you are, and, secondly, I had the right to send you back to Naomi after the first day if I didn’t like the experience. I can assure you, Greg, that you are every bit the princess I was hoping you’d be. In other words, I’m quite pleased with you and am taking complete possession of you.”

Alicia's message finally registered in me and I wondered, “So what is my life as a princess going to be like?”

“You’ll live here. I’ll dress you as a princess – I’ll groom you as my princess. I’ll get all the advantages I desire from you being my princess. Like what we did today, for instance. You can expect that I’ll be coming back to ravish you whenever I feel like it. Moreover, you’ll be in charge of the house. You’ll cook, clean, and do the laundry while I’m at work. How does that sound?”

“So I’ll be wearing my princess gown every day?”

“Yes, of course you will. I’ll be getting you some other gowns to wear so you’ll have a choice every day. Everything you need to be a princess I’ll get for you.”

My imagination fixated on what the other gowns might look like. I wondered how many pretty gowns would Alicia buy for me. It would be so nice to have a closet with princess gowns hanging in it so I could pick whichever one I wanted to wear. “I would like to have some more gowns even though I love the one I’m wearing.”

“Good. So you do want to stay here as my princess, right?” Alicia said.

“More than anything, though I will miss Naomi, miss her a lot.”

“As editor-in-chief there will be many occasions when she’ll be visiting here. Parties and also some business meetings. You’ll get to see her and I’m sure she’ll get a kick out of seeing what a pretty princess you’ve become.”

“I will like that,” I said.

“Today you’ve become an extension of me,” Alicia said. “You’ve been hoping for many years to find a woman who would take full control of you, and that time has arrived.”

I looked at the dress I was wearing and picked up Alicia’s panty and bra again. This felt right. This was where I belonged. This was what I needed. Alicia was right about me.

“Naomi is waiting to find out if you’ll be returning to her or not. I’ll call her and tell her the good news.” Alicia called Naomi and put her on speaker.

“Hello, Naomi,” Alicia said. “Greg is on speaker with me.”

“Hi Alicia, hi Greg.”

"Hi Naomi," I said.

“I’m calling to say that Greg was the loveliest princess today. I am thrilled by his sweet, delicate, feminine nature and I’m going to keep him.”

“That’s great!” Naomi said with way too much enthusiasm. I would have thought that she’d be a bit sad to give up her marriage to me. “Congratulations, Greg. You’re getting everything that you dreamed of."

"Thanks,” I said. “I’ll miss you, Naomi, but I know that Alicia is going to take really good care of me as her princess.”

“She will,” Naomi said. “I never would have agreed to our deal if I thought for one moment that you wouldn’t be happy.”

I thought that Naomi might say that she’d miss me but she didn't. I did think it was a bit surprising how easily she gave me up. There was no doubt that becoming editor-in-chief was a higher priority to her than being with me. On the other hand, she no doubt thinks that I care more about being a princess than being with her.

“I’m going to have your things sent to Alicia’s,” Naomi said.

“Thanks.”

After some more pleasantries Alicia hung up the phone and turned to me. “You’re going to love the pretty nightgowns I have for you.”

“Nightgowns fit for a princess?”

“For sure!” Alicia said.

The End