A gay story: My Dream Solution Ch. 01 [Note: This is a long introductory setup to a multi-part story. There is *no* explicit sex in this first chapter. If you are looking for quick, hot read, move on. This is not it. Things will heat up in later chapters, I promise. –Cyanlot]
Chapter 1: When I Hit the “Change of Life”
When Massachusetts became the first state to legalize gay marriage, Todd and I were ecstatic. We didn’t have to move to get married; we could do it in our home state. We didn’t rush to be among the first to take advantage of the new marriage equality. Better, we thought, to take our time, plan a terrific ceremony and party, and do it right.
And we did do it right. We’d come out to our families long ago and both of us had, at least after the initial shock, received the love and support of our families—Todd more than I, but even my basically conservative family dealt with it pretty well. So, on the day of the ceremony, all the people we were really close to, family and friends, were there.
You might think that, having lived together for five years already, marriage wouldn’t make any difference in our lives, but it did. It was a subtle difference, but we both noticed it. We were, now, even more of a couple: Todd and Ron, living in happily wedded bliss.
And then a wrench got thrown into the works. Todd’s company offered him a big promotion—great news—but only if he would move to Arkansas—not such great news. Arkansas not only doesn’t permit gay marriage, it refuses to recognize gay marriage. And it’s not just the legal implications that were concerning. The new position would be in a production facility in a small, mostly rural area that was definitely very red politically, Bible-thumping religiously, and straight-laced socially. A gay couple wouldn’t do well in that environment, and there would be special antipathy, we suspected, for a gay couple that thought of themselves as married. We would definitely be moving to “marriage is between one man and one woman” territory.
But Todd already makes the bulk of our income and would make a lot more if he could accept this position. I’m a freelance graphic artist; I can work from anywhere. There wasn’t really anything keeping us in Massachusetts, except the quite reasonable desire not to live where people would despise us and the law would discriminate against us. Still, it wouldn’t be forever. This was a stepping stone for Todd. A couple or three years successfully managing this facility would put him in a great position to move back to the modern, civilized world, maybe to a choice location overseas.
So it was decided. We both had misgivings—the very same ones. But we both saw that this was an opportunity not to be missed and decided Todd had to accept the position. We’d make it work somehow.
After the decision was made and Todd had officially accepted the new position, we planned a trip to scope out the housing situation. There was no urban area so the hope of finding a progressive enclave—a small community of like-minded, if not like-sexually-oriented people—was a vain one. The apartments that were available weren’t great—none of the benefits of city living, but the drawback that your neighbors know too much about what you’re doing.
All of this we could figure out from searching on the Internet. It wasn’t until we went down to Arkansas to house hunt that we appreciated the full implications of this move for our lives together.
We told Connie, the realtor we’d decided to work with, that we were old college roommates and because I didn’t make much money, I needed to share living expenses with Todd. I don’t think for a minute that she bought the “just friends” line, but it provided a good cover: she knew, we knew she knew, she probably knew that we knew that she knew, but no one had to explicitly acknowledge our relationship. (Of course, we’d taken our rings off and were careful not to give any indication, even to Connie, that we were married.)
I think Connie was cool with the situation. Good! At least not everyone in this area was a hopeless bigot. And Todd and I were certain that she knew that we were a couple when she gave us some oblique advice. Without ever suggesting that the information was directed at us for practical purposes, Connie managed to steer the conversation around several times to how conservative and straight-laced most of the people in the area were. She even described them as “intolerant” of people who are different from them. One of the first questions we would be asked, she said, is what church we go to. And eyebrows would be raised if the answer was “none,” which it would have been without her advance notice. She told us that it would be best if we tried to fit in, or at least appear to fit in.
Todd and I quickly confirmed our suspicion that a gay couple, married or not, wouldn’t be welcome here. It might even hamper Todd’s work at the new plant. He had to supervise a lot of local workers. He’d be their boss, of course, but it’s much easier to supervise people who don’t consider you an immoral degenerate.
Todd and I found a few houses that would work. And, man, were the prices terrific! We could afford five times the house we could buy in Boston. While we were still in town on the housing visit, we narrowed it down to two houses. Both were out in the country—not far, but enough to give us some privacy. We went back home, certain that we would buy one of those houses, but very uncertain about how we could live in the area at all.
All the way home on the plane and for days afterward, we talked about what our lives would be like there. We were committed now—it was way too late to turn down the position—we just had to figure out how to make it work.
One morning, I woke up with an idea. (Isn’t it funny how that happens? You ponder a problem for days and think you’ve considered every possible solution. Then, out of nowhere, another alternative comes to you in your sleep. The power of the unconscious mind, I guess.)
It was a wacky idea and I almost didn’t have the courage to suggest it to Todd. But, finally, after another long discussion where we’d come up with no good solution, I decided to float the idea.
“What if you don’t go to Arkansas with a husband?” I asked. “What is you go with a wife?”
“Sorry Ron, you don’t get rid of me that easily,” Todd joked. “This isn’t worth my switching teams for.”
“That’s not what I mean.” Todd was puzzled. “I mean, what if you and I were to go down there as a husband and wife.”
“What? … What are you talking about?”
“I’m serious. You’d tell everyone that you’re there with your wife, that would be the public story. Either of these houses is secluded enough that, when we’re alone, we can just live our lives normally.”
“But, come on …” he protested. “It would never work. There will be functions that we’d have to go to as a couple. It’s not as if I could always say, ‘My wife is under the weather.'”
“I thought of that.”
“Yeah … and what’s your solution?”
“Don’t laugh,” I cautioned. I felt silly now. When I’d first thought of this idea, it hadn’t seemed as ridiculous as it was starting to sound as I tried to put it into words out loud. “I figured I could get Alex to help me pass.”
Todd didn’t laugh, which was good, but he did look astonished. Alex was a friend—well, really more of an acquaintance, one of those people who you knew and ran into because he circulated with people who circulated with you. He was a transvestite, and a damn good one. He could fool just about anyone. Even those of us who knew him well, couldn’t help but see him as a woman when he was dressed.
“If anyone can help you do this, it’s Alex. But are you sure you want to do it.” I could see that Todd was beginning to consider my idea seriously. When you thought about it for a minute, it was easy to see that it solved a lot of problems.
“It’s worth a try,” I said. Todd didn’t raise any objections, which I took to be assent.
“How did you come up with this wacky idea, anyway?” When I confessed that it had come to me as I was waking up one morning, Todd dubbed this my “dream solution,” and that’s how we referred to it from then on.
I was serious about this, at least about seeing if it might be possible. So I called Alex and set up a time to meet with him. I didn’t want to tell him about my plan, my “dream solution,” over the phone but I wanted to get going on this so I arranged to meet with him the very next day.
That night, after dinner, Todd suggested that we go to bed early. This was only one, of many, ways that we had of signaling that we wouldn’t be going to sleep right away. I found that reassuring. Though I was committed to exploring my dream solution, I was anxious about it. I wasn’t at all sure that it would work of course; lots of things could go wrong. But, more importantly, I was worried about what it would do to my relation with Todd if it did work.
Todd and I had one of the best relationships I’ve seen. You never really know what goes on in other people’s relationships, unless they’re sharing way too much information. But I didn’t know of any relationship—gay or straight—that was closer, more respectful, more egalitarian, or more fun than Todd’s and mine.
One of the things I most valued about our relationship was that neither of us was the dominant one, sexually or in other ways. There was no “top” and “bottom”. We stood together side by side—close together—facing the world with openness and joy.
What if my dream solution led us to fall into a traditional husband/wife model of interaction? I know that this “traditional model” was never as ubiquitous as it’s currently fashionable to portray it. My father and mother certainly didn’t have a “traditional” husband-dominant/wife-submissive relationship. But it was still a model that some couples fall into. I valued the best-friends, egalitarian relationship that Todd and I had. I didn’t want to compromise that. What is my dream solution turned into a nightmare?
It was because of these sorts of anxieties that I was especially reassured by our lovemaking that night. Todd had initiated the evening’s early retreat to the bedroom, but in the bedroom I was completely reassured of the nature of our sexual relationship and, I trusted, the ways that we would continue to interact with each other outside the bedroom.
If anything, Todd was going out of his way to assure me that my willingness to take of the role of “wife,” as far as the outside world knew, wasn’t going to change anything at the core of our relationship. He was, I think, being especially careful not to be dominant that night.
I was reassured; and I was completely wrong. Things would change, more than I could have guessed, but not exactly in the ways that provoked my anxiety.
Alex and I met the next morning and I found it surprisingly easy to tell him about Todd’s and my plan—my dream solution—for dealing with the problem we faced. It’s not as if Alex was going to judge us badly. In fact, he was more than intrigued by the project. He looked at me very closely and in a way that I don’t think I’ve been looked at before. I guess he was sizing me up as a potential female impersonator. After a moment, he smiled and nodded. He’d help me … us … do this. He seemed to consider it a challenge and one that he was confident he could meet.
“So, when do we start,” he asked.
“I don’t know …” I began, but he interrupted me.
“Now!” he said, forcefully. “Let’s go.”
I couldn’t think of any reason to put it off so we were soon in the car and on our way to the shopping mall and some specialty stores that Alex knew well.
“Some things we can get at women’s shops and other regular stores,” Alex explained. “But to carry this off, you can’t just wear women’s clothes, jewelry, and make-up. We’ll need to go to stores that have specialty items to make men look more like women. And some things we’ll need to order online, where we can get a terrific selection.”
“Are you all in on this, Ron? Cause it’s going to cost you some money.”
I told him I was all in, I didn’t realize until we’d hit some of the stores how far in that meant. Sheeze! women’s clothes are expensive and I needed a lot of them.
We spend the whole day shopping. It would have taken much longer if I’d tried to do this alone. Alex knew the options—what would work on me and what wouldn’t—and he was very decisive. At Victoria’s Secret, he picked out two weeks’ worth of bras and panties and other undergarments that I didn’t even know the names of. I had no idea what the difference was between a chemise and a camisole. But Alex did and he picked out everything with only an occasional request for input from me.
I was hugely embarrassed when he told the clerk that the lingerie was for me and we wanted to try some of the things on. He gave me no warning he was going to do that and I was aghast when he did. The clerk was completely professional about it. If she found it humorous or embarrassing, she showed no sign of it. As if this happened every day, she walked us back to a special dressing room in the back of the store off of the storage area, saying that we would have more privacy there.
Once in the dressing room, Alex, with an armful of sheer and lacy lingerie, told me to undress. I was a little hesitant. This felt weird. Todd and I aren’t prudish, but we’re sure not swingers. We’d been exclusive since we’d been living together. It wasn’t some sort of sacrifice for either of us, I don’t think. Sure, we were attracted to other men, but we really just wanted to be with each other.
I hadn’t been undressed in front of any man other than Todd and my doctor for a long time and undressing in front of Alex felt strange.
“Come on … come on,” he said in a light tone that put me at ease. “I’ve seen lots of dicks before. I’m not trying to get a glimpse of your equipment—though I’m sure it’s fine equipment. We just need to make sure that things fit right.”
So, I undressed, stopping with just my underpants on until he told me that I could hardly try on panties over my underpants.
“Okay, nice,” Alex said. “Once we take care of your body hair, you’ll do fine. You have a pretty good figure.”
No one has ever said that to me before. Men talk about their build, not their figure. I’d just never thought about what sort of *figure* I had.
Alex had me try four or five pairs of the panties. I didn’t see why I needed to try on more than one to make sure what size fit me. But Alex explained that with the different cuts—bikinis, Brazilian, thongs, briefs, tangas, and a bunch more the names of which I couldn’t remember—I needed to try several on.
The putting on and removing of the silky panties had a predictable effect on my cock and I felt myself flush red as my cock rose under my panties.
“Oh, my,” said Alex. (I wished he had been enough of a gentleman to simply ignore this, but that wasn’t his style.) “I can see that Todd will be in for a special surprise when you dress for him.”
“I’m not dressing for him,” I replied defensively. “I’m dressing for when we’re out in public.”
“Well, you might need him to take care of that before you go out. You know, there’s only so much we can do to hide bulges down there.”
Alex was enjoying teasing me and I thought it best to just let this pass. I was happy, though, when we moved from trying on panties to trying on bras. For each of the bras I tried on, Alex carefully felt inside the cups and I could see him visualizing how they would look filled out with whatever prosthetic breasts he had in mind for me.
After Alex made judicious choices about the panties and bras and I got dressed, we left the dressing room. Alex put some things back, picked up replacement items that he was sure would work now that he’d seen some things on me, and some special stockings and pantyhose. (He said we’d get lots of regular ones somewhere where they were cheaper.)
We went up to the counter to pay and the same clerk waited on us. I wasn’t sure whether or not it would have been better to have a different one. This one knew who we were buying for, but I’m guessing a new one would have suspected as much. Maybe it was better to have only one person knowing what we were doing. And, at least she’d shown that she was cool with it.
I wasn’t up for doing the dressing room thing in every woman’s clothing store that we visited so I convinced Alex to let us buy lots of stuff—dresses, skirts, blouses, pants, and shorts—try them on at home and return what didn’t work.
When Alex would try to hold something up to me in the store, I pushed his hand away and told him to use his imagination. He looked disappointed, but went along with it.
After we’d shopped out the mall, we headed for one of the specialty stores that Alex knew. The two clerks greeted him warmly and by name when he came in. The name they greeted him by, though, wasn’t “Alex”; it was “Alexis”. It was strange to see the instantaneous transformation of Alex when he entered the store and began talking with the clerks. Alexis sounded so “fem”—not just his word choices, but the pitch and intonation of his voice changed.
Alex was dressed in men’s clothes, but if you closed your eyes and listened to the conversation, it sounded for all the world like girl talk.
“I’ve got a project here, girls,” Alex/Alexis said. He looked at me and so did the two salesclerks. “Do you think you can help me transform Ron into Ronda?” I hadn’t thought at all about what I would call myself as Todd’s wife, but I instantly realized how much sense this made. If Todd were to slip and call me “Ron”—or even “Ronny”, as he sometimes does—this would never be a problem. These would just be his cute nicknames for me.
“Well,” said one sizing me up, “I think we can do a pretty good job on the stuff we do. But you’re going to have to work with him on posture, body language, and all that stuff.” She looked at me again and said, “You’ve got a ways to go with him there, Alexis.”
I’m not normally slow but it was only then that I realized that the two store clerks must have been transvestites, too. They were big girls, but there was nothing in their looks, their voices, or the way they carried themselves that made that in obvious conclusion. Once I was thinking it, I could see that it was possible. But if I’d just met them in some other context, I never would have suspected. I was starting to have hope that, with Alex’s help, I might be able to pull this off.
There was no need to be anything but completely open about what we were there for, of course. We went back to a private dressing area of the store and, after I’d taken off all my clothes except for my briefs, both “girls” went to work trying various items on me.
One of the most important things, they assured me, even more important than breasts, they said (though I couldn’t believe that) was to give me a waist. They tried several corsets on me, insisting that I’d need more than one style for different styles of dresses and pants.
As Alex went out to get the clothes we’d bought from the mall, they admired their work in the mirror. It was remarkable what the corsets did to not only give me a waist, but to emphasize my hips. If I squinted, it really did look like I had a decent female figure.
Alex returned with what looked like everything we’d bought at the mall. I thought he was just going to bring in a few bras so that the girls could give me breast forms or whatever those fake breasts are called. But Alex said that if we tried on my dresses and other outer clothes, we could see better which breast forms were right. Besides, we could get the girls’ opinions of which clothes worked and which didn’t. They were, Alex reminded me, experts.
They insisted that I put on not only a bra, but that I take off my briefs and put on one of the panties, too. “It’s important to have the complete look,” they insisted. So I found myself for the second time today, and only the second time in many years, stripping completely naked in front of people other than Todd.
They had me put on pink lacy panties and a matching bra. Then Starla, I think her name was, brought out a tray of breast forms in different sizes. She carefully placed one set in my bra, had me turn and pose in different positions, tried several other sizes and shapes, and then settled back on the first pair she had selected.
Then we went through most of the outfits Alex and I had purchased, seeing how I looked in each of them. To me, my image in the mirror was a confused and confusing one. If I looked just at the span from my neckline to my hemline, I looked like a woman with good, in fact great, figure. But a glimpse of my face, or my hairy legs belied that image.
The girls and Alex appeared to be able to focus only the relevant parts of my body, ignoring the tell-tale traces of masculinity. On their suggestion, I sorted the clothes into those that would work and those I’d take back. When they were finished reviewing all of my clothing choices, they had me get back in the outfit they seemed to like best: a short, tight blue skirt and a lighter blue satin blouse.
Both the girls left for a moment leaving Alex and me alone. “You’re going to look great, Ron,” Alex said encouragingly. “Or I guess I should say, Ronda.” I smiled. “If you’re a good student—if you pay attention to what I teach you—you’re going to pull this off.”
Starla, and the other clerk, Becky, returned with a cart filled with shoe boxes and bigger boxes. I didn’t know what the bigger boxes contained until Becky opened one and pulled out a wig. They tried half a dozen wigs on me, maybe more.
“This is really crucial,” Becky said. “You can increase your femininity by going with bigger, more stylized hair, but if it’s too garish, you won’t be convincing. We need to find one that will soften your facial features but look natural. This isn’t the time to go for platinum blonde or wild redheaded curls.”
They settled on a wig that was light brown, with lighter highlights, and gentle curls that came down about three inches below my shoulders. I couldn’t really appraise it with my obviously masculine face centered between the feminine locks. Alex, Becky, and Starla, though, were very pleased with the look.
“You need to get your shoes here. You can find shoes large enough to fit you in a regular shoe store, but you won’t find stylish ones. Women with feet as large as yours, don’t wear stylish shoes. You need to.”
Then we went through about 20 pairs of shoes. I had to stand up and walk—well, try to walk—in each pair. Shit, I thought, this is hard. I started to have doubts about whether I’d be able to learn to walk with confidence, let alone in a feminine way, in these heels. Alex assured me that I’d get the hang of it. All they wanted to see now was whether the shoes looked good on me and how the heel height made my legs and ass look.
We finished with the shoes, selecting ten pair to purchase. I was trying to keep a rough tally of the costs. This wasn’t going to be a cheap trip but, I figured, whatever it took. The financial cost was a very small factor in this plan. Oh well, “in for a penny, in for a pound,” I thought to myself. Besides, Todd would be making enough more money in his new position that we could afford to have two wardrobes for me.
I gave Alex my credit card and he and the girls went out to tally up the damage while I changed back into my regular clothes. I got to the counter just as they were finishing up—just in time to sign the credit card charge slip—and I saw Alex putting some boxes I didn’t recognize into the bag.
“What’s that?” I asked innocently.
“Oh, nothing. I’ll show you later.”
I was curious and pressed once, but Alex put me off, telling me he really had to show me and I shouldn’t worry about it.
On the way home, we hit the drug store where Alex picked out, in very quick order, nail polish, false eye-lashes, and an array of make-up that was truly impressive. I guess I’d never realized how much stuff women used. Though, as Alex explained later, real girls could get away with less; I needed to use every trick in the book to feminize myself. So, we left the drug store with two large bags of every type of feminine beauty product known to man and a bunch of the everyday stockings and pantyhose that were much cheaper here than at Victoria’s Secret.
It was late afternoon by the time we got back to my place. I was ready to call it a day. I had some work to do on a project that was due tomorrow night and I felt that I’d had enough of the pursuit of my dream solution for one day.
But Alex hadn’t. He said he was busy tomorrow and wouldn’t be able to help me so we needed to get more done today. Todd was going to be working late today—he wouldn’t be home until about 8:00—so it seemed like a good opportunity to learn what I could from Alex. I decided to try to rally for more work on the plan.
Alex gave me my assignment: put away my new clothes and shower, washing completely with a strong soap, then report back to him with just my towel on.
It was weird putting away all of the women’s clothing—my women’s clothing. I made room in the closet and my drawers and carefully put away all of the clothes. The strangest part was folding and putting away the bras, panties, and other lingerie. At the moments where it really struck me that these were *my* bras and *my* panties I felt a wave of uncertainty and nervousness. I wasn’t at all certain that I could do this. But I’d come this far and it would have been really stupid to stop now. Besides, I couldn’t figure out how Todd and I would live comfortably in Arkansas any other way, so I had to make this work.
I took my shower, dried off and walked out to the kitchen with the towel wrapped around me. Alex was busy cooking something apparently. And the dining room table was covered, not with a table cloth, but with a sheet. I had no idea what Alex was up to, but I was soon to find out.
When he looked up, he said, “Wrong way to wear the towel.” I looked baffled for a second, I guess, and he went on. “Well, I guess it’s okay for now, but that’s another thing you’ll need to learn to go two ways on, depending on whether you’re Ron or Ronda.”
He touched the pan that was cooling on the stove and said, “Alright … a little warm, but it will be alright.”
“What’s that? What are you doing?”
“I told you we’d have to take care of that body hair. That’s what we’re doing.”
“I’ve got a razor in the bathroom. What’s all this for?”
“A razor! Oh, boy! You don’t know the first thing about being a girl, do you?” Alex stirred the pan gently and continued. “That’s okay, though. Ignorance is correctable. That’s why you have me. So, here’s your first lesson. You’ll have stubbles in a day if you just shave; you need to get the hairs out by the root if you want it to last for a while.”
“Okay, but what’s that stuff you’re cooking?”
“Sugar paste, Sugar.” I guess Alex was trying to be cute. But I’d never heard of sugar paste so I was more interested in what it was than his cute little play with words.
“It’s better than waxing—less pain and faster. Hard to find someone good at doing it, but this is your lucky day. I’m an expert.” Alex picked up the pan and nodded toward the table. “Get up on the table and lie down. Stomach or back, it doesn’t matter; we’re going to need to do both sides.”
So I got my first sugaring treatment, which was also my first depilatory treatment of any kind if you don’t count shaving my beard every morning. It didn’t hurt too much on my legs and arms, where Alex started. It hurt more when I did my underarms. When we started to slather the sugar paste on my groin area, I stopped him.
“Hey, I’m not planning to pose in a bikini. I just need to pass in ordinary clothes. You don’t need to do anything down there.” And I moved to get off the table.
“Oh, no you don’t,” Alex said with surprising authority. “This is part of your training.” I looked skeptical. “No, I’m serious, Ron. If you want to act like a woman, you’ve got to feel like a woman. Why do you think we picked out all those panties?”
He had me there. I hadn’t thought of that when we were shopping. Once it occurred to me, I was at a loss to explain why I hadn’t said that I didn’t need panties. It wasn’t as if I was going to pose in my lingerie, either.
“Here’s why. You’re not going to act like a woman—not in any way that will convince people—if, under your dress or skirt, you’re wearing your Jockey briefs or boxers. It just won’t work. And the same goes for your crotch hair. Sure, women have hairy crotches, but if you pull on your lacy pink panties over a hairy crotch, I can assure you, you won’t feel feminine.”
“I don’t know.”
“Trust me,” Alex said. “Or not … and I’ll just go home now.”
I relented and found out that there were places where tearing hair out by the roots hurts even more than in your underarms. If Alex had wanted to check out my equipment earlier, he was sure able to satisfy his desire now. He had his hands all over my cock and balls as he worked to denude my groin. When Alex was finished, except for the hair on my head, I was as naked as a newborn.
Alex ran his hands over me, inspecting his work, I guess. But then his touching changed to something different. He had pushed my cock over to the side and was massaging my balls.
“Stop it, Alex,” I said, hoping he was just teasing and not making a serious seduction attempt. If it was a seduction attempt, it was a weird one. He was just pressing his fingers against one of my balls and pressing it gently, but with increasing pressure, against my pelvis.
“Take it easy. You need to relax.”
“No. What are you doing?”
“I’m going to show you how to hide your equipment. And don’t give me this, ‘I’m not going to be a bikini model’ crap. This isn’t just about feeling like a girl. This is about looking like one. Some of your outfits will work without you tucking, but not all of them. Some of those dresses and skirts, and all of your pants and shorts, will show a definite bulge if you don’t tuck. So you have to learn how to tuck. And I’m going to teach you. It won’t hurt, though you may feel a little discomfort until you get used to the feeling.”
I relaxed a little, convinced at least that this was a legitimate part of my makeover and not some crude attempt to initiate sex—something that I was definitely not interested in right now. Alex continued to gently massage one of my balls, putting and more pressure on it as he pushed it up into my abdomen.
Now, I’d had my balls retract before. Sometimes when I was swimming in really cold water, I’d take off my swimsuit to find that I had no visible balls; they’d retreated for shelter and warmth. I hadn’t even felt them retract. But this was different. Alex was forcing the issue and, there was, indeed, “a little discomfort.” Sometimes when doctors and dentists use that phrase, it’s a gross euphemism. What they really mean is, “this is going to hurt like hell, but I’m not going to tell you that in advance.” But this wasn’t really painful, just a little uncomfortable at first.
When both balls were neatly tucked in my abdomen, Alex turned to get something. I saw him take something out of one of the boxes I hadn’t recognized at the shop. He unwrapped an item that looked like a very large, flesh-colored Band-Aid, shaped strangely.
“This is called a ‘gaff’,” Alex explained. “There are lots of kinds and you can just use tape—medical tape, not scotch tape, which won’t hold, or duct tape, which will hold all too well. But I like these because unlike undergarment-style gaffs, these are completely invisible under your panties, and they’re easier to use than tape.”
Alex exposed the adhesive on part of the gaff and wrapped it around my cock. He had me rock back and lift and spread my legs, exposing my ass to him. I could tell that the gaff had adhered well to my cock when I felt Alex draw it back tightly between my legs. He exposed the adhesive on the rest of the gaff and taped it to the insides of both my cheeks.
I realized that this gaff was designed so that it didn’t cover the end of my cock and, while it was stuck to both sides of the insides of my buttocks, it was split and didn’t cover my asshole either. This allowed, I realized, normal bodily functions. Then it occurred to me that eliminating bodily waste wasn’t the only normal bodily functions that this gaff was designed not to interfere with. That wasn’t going to matter in my case, though. I wasn’t going to be dressed like this when Todd and I were together alone. I could see, though, why some crossdressers and transvestites would want the gaff designed to allow for backdoor sex.
“There! Now get up and let’s see how this looks.” I started to get up and winced because I felt “some discomfort” in my groin. “Take it easy,” Alex cautioned. “It will take some getting used to, but soon you’ll be able to move without even noticing that you’re tucked.”
We walked to the bedroom with me completely naked and feeling rather odd in the crotch. When we got to the full-length mirror in the bedroom, I was stunned. If you looked just at my groin, ignoring the fact that I didn’t have much of a waist, had no breasts, and had a face that didn’t look very feminine, I looked like a woman. Pulling back my cock tightly the way Alex had between my retracted balls, even gave me a pronounced camel toe.
“Wow!” I said unselfconsciously. “That’s amazing!”
“Pretty good, huh?” Alex complimented himself on his work.
“I’ll say.”
“Now let’s see what we can do with clothes and make-up.” Alex sat on the bed. “I want you to pick out your clothes, everything, panties, bra, corset, … everything. You have to get used to doing this. And I want you to start thinking like a girl.”
“What do you mean?”
“All your life, when you were picking your clothes to wear, what sort of internal dialog was running in your head?”
“I don’t know. I didn’t think much about it.” I paused. “Sometimes I was thinking, ‘Can I wear this another day, or does it smell too bad already.'”
“Yeah, well, girls might think that sometimes,” Alex laughed. “But they also think things like, ‘This is pretty,’ This is soooo cute,’and ‘This is Wow, I’ll look really sexy in this.’ Guys are not only not inclined to think that way, they’re conditioned not to. You need to overcome that conditioning.”
Alex went on, unconsciously slipping into lecture mode. “Look, Ron, I know that you and Todd aren’t into being feminine. I get that. But if you’re going to pull this off, you need to do that. Think of it as method acting: you’ve got to *be* a woman to act like a woman. I want you to turn off your internal censor that tells you not to think things like, ‘This is soooo cute,’ and ‘I’ll look great in this.’ Embrace those thought. At first, you’ll probably have to force them. You know: fake it until you feel it.”
So I tried. I felt silly, though. Going through what I’d turned into my lingerie drawer, I picked the lavender panties with the matching bra. It seemed ridiculous to think to myself, “These are pretty; I’m going to love slipping these on my smooth, sexy body.” But I did it.
I guess you can get used to just about anything. The beige corset I picked out would make my waist so slender and sexy, I thought to myself. The tight black pencil skirt would show off my well-formed ass and my terrific thighs. The purple silk blouse could be unbuttoned enough to be suggestive but still modest—a very attractive look, kind of sexy librarian style. I picked out black thigh-high stockings, not pantyhose, thinking how sexy they would look over my slender calves and thighs.
When I walked to the closet again to pick my shoes—black three-inch pumps with an open toe—Alex clapped.
“What?” I said. “Did I pick well?”
“No … well, yes, you did. But that’s not what I was clapping about.”
“Then what?”
“Didn’t you notice?”
“Notice what?” I was genuinely baffled and didn’t appreciate Alex dragging this out.
“How you walked.”
“What about how I walked?”
“I can’t believe you didn’t notice it. When you walked back over to the closet, your hips were swaying. When you bent down to pick up the shoes, you bent down like a woman. You picked up your shoes like a woman would.” Alex was excited. “I’m not saying you don’t need lessons. There are a thousand things to learn about how women move, how they sit, how they talk, how they look at people—a thousand things you’ve never thought about that you’ll need to learn to do differently. But you’ve definitely got an inner girl. You’ll learn.”
I hadn’t noticed any difference in how I walked to the closet. But now, thinking back on it, I had a kind of bodily memory of how I’d moved and I thought that Alex might be right.
“Now let’s see you put on your bra and panties and stockings. I’ll help you with your corset and then we’ll see what we can do with make-up.” Alex turned toward the desk in the corner of the room—which he was obviously planning to highjack for a dressing table—and then stopped and turned to me. “And remember, everything you do, you do as a woman. Putting on your panties and things isn’t just a task to be completed. Be mindful of what you’re doing. You’re dressing to be a sexy, desirable woman.”
I tried to comply. I pulled my panties up over my smooth thighs and, I realized that this could be a very sensuous experience. Looking down at myself, and in the mirror, I was astonished at how perfectly the panties fit now. Not at all like in the dressing rooms where I’d worn them before. Turning to the side, I saw that I had no manly bulge. I wasn’t planning to be an underwear model, but I could be if I wanted to.
I knew to put my bra on backwards and then turn it around. The bra was very sexy, and I liked the way it looked, except for the emptiness of the cups—something I knew was soon to be rectified.
Pulling up my stockings was especially sensuous. It required effectively caressing my legs, which were incredibly sensitive in their hairless state. I felt my cock strain against its restraint.
“Nice!” Alex said. “Now come over here and sit down.” He’d arrayed the equipment for my facial makeover on the desk. First, though, he got the breast forms out and positioned them in my bra. When he was happy with the way they sat there, he took them out individually and slathered adhesive on the backs, carefully repositioned them, and pressed them to my chest.
The entire evening had been, by definition, transformative. But there were moments that were especially salient. Looking, for the first time, at my crotch with my cock and balls tucked was one of those moments. And feeling the weight of the breasts on my chest, looking down and seeing them fill my bra, this was another such moment. It was like a new threshold of femininity was crossed.
There was no mirror by the desk so I couldn’t see that Alex was doing. He set about his work, though, with enthusiasm and obvious expertise. He started with my fingernails. “We should have done your toe nails, but that can wait for another time.” False eye-lashes, eye-liner, mascara, various creams and powders, lip pencil, lipstick, the whole nine yards.
“Just one more bit of make-up,” Alex said, turning me toward him. He used one of the make-up brushes to create the illusion of cleavage on my chest, above my bra. Even from the perspective I had on it, this was rather amazing. I couldn’t wait to see myself in the mirror. I was sure that it would look as if the gentle swell of my breasts began above my bra.
Alex wouldn’t let me get up yet, though. We had a couple more things to do before I could see myself. Alex went over to the dresser to get my wig and some of the jewelry we got at the mall. On the way back, he picked up my shoes to bring them to me.
“We should have gotten your other ear pierced when we were at the mall today. I thought about that when we picked out your jewelry but it slipped my mind. We’ll make do with one earring for now.”
He positioned my wig, being careful not to mess up his work on my face. He used bobby pins to keep it firmly in place and a brush to do the final touch-up. Then he took out the gold stud in my right earlobe and put in one of the dangly earrings we’d purchased today. A necklace and bracelet followed and he instructed me to put on my pumps.
“Now, walk over to the mirror. And remember, you’re a woman. A beautiful, desirable, sexy, woman, who can have any man she wants. Walk over slowly. You’re not just putting on a show; you *are* the show.”
He needn’t have cautioned me to walk slowly. I had to do that to keep from falling in the heels. Other than trying these on at the store, I’d never worn high heels and I realized that walking in them wasn’t an innate skill—at least not for me.
I tried to walk in as feminine a way as possible. I’m afraid I wasn’t very good yet. But I made it over to the mirror and when I saw my reflection in the mirror, I was stunned—really stunned. It didn’t look like a reflection of me. It was a woman in the mirror. She moved her arms and legs, her whole body, in perfect sync with me, but she was a woman and I was a man. Every inch of her was woman. She had slender, well-shaped calves and thighs, smooth, hairless skin, a sweet little crotch with no unsightly bulge, a slim waist, nicely rounded B-cup breasts, and an inviting cleavage. She had full red lips, dark eyelashes, and a milky-smooth complexion. This couldn’t be me.
Then I remembered what Alex had been telling me throughout the day, sometimes explicitly but more often by implication. I’ve got to feel like a woman. So I looked at myself in the mirror—I admired myself. I silenced the voice in my head that was saying, “This isn’t me.” I generated another voice that said, “This *is* me; I’m a beautiful, sexy woman.”
I smiled, and the woman in the mirror smiled back at me, and I was her.
Alex gave me a few minutes to take this all in, to appreciate the amazing transformation. Then he told me to put on my blouse and skirt and pose again in front of the mirror. I picked up my blouse gently and slipped it on, slowly buttoning up. Looking in the mirror again, I saw what a terrific job Alex had done creating the illusion of cleavage. No one would think that this was a paint job. It looked for all the world like natural cleavage. Trompe l’oeil! Who knew Alex was an artist?
I bent over from my waist to pick up my skirt. I could feel how, in these heels, this made my butt stick out. I’d seen women do this and figured it was a uniquely feminine way of bending over. I pulled up my skirt, zipped and hooked it, and smoothed out my blouse.
The look was complete. It had been complete woman even before the blouse and skirt, of course, but now I looked like a woman who could walk down the street and be noticed, not as a crossdressing man, but as a very attractive woman. Well, that is, if I could walk in these shoes.
“You’ll get the hang of it quickly,” Alex said as he saw me take a few wobbly steps. “What time does Todd get home?”
“About 8:00 today.” Looking at the clock for the first time, I realized that this was in only about a half hour. “Oh, I’d better get out of this stuff.”
“Are you kidding?!” Alex was appalled. “You’re not taking a thing off until Todd sees you.”
“I don’t know. Dressing isn’t part of our lives.”
“Well, it’s going to be in Arkansas. You’d better get used to him seeing you in women’s clothing.”
Alex was right, of course. There was no reason to put off letting Todd see Ronda. If he couldn’t tolerate me as Ronda, then we’d need to have another plan for Arkansas. Best to find out now.
“Let’s go into the living room and I can start showing you some of those thousand things you need to learn. I want to be here when Todd gets home—I want to see the look on his face—I think I deserve that—but I’ll leave then. And you can get out of these yucky women’s clothes as quickly as you two want then.”
Alex said “yucky women’s clothes” with a feigned disdain that I suspected was intended to mock me. He knew that I’d never been into crossdressing and he knew the reason I was willing to try it now. I felt as if he might simply be teasing me about what he thought might be my revulsion at his fetish—though it never revolted me; it just didn’t excite me. But he also might have been suggesting, by exaggerating my rejection of women’s clothes, that I wasn’t so confident anymore about my dislike for them. I didn’t know what Alex was implying and I decided it didn’t really matter.
In the living room, I began to learn some of those thousand things that Alex kept referring to. I couldn’t believe how much there was to learn. Women do everything differently: sitting, standing, and walking—all had to be relearned with subtle and not-so-subtle shifts from how I did them normally. And talking like a woman wasn’t just about the pitch of your voice. Alex said I needed to learn new cadences, inflections, and even word choices and sentence structures. Men and women interrupt differently, too.
There was way more than I could learn tonight, even if we had all night to work on it. Alex reassured me that this was okay. It’s a process; perfection is out of reach, but it’s important to come as close as possible.
And he explained why even seemingly trivial aspects of female behavior are crucial to the female impersonator—the man who doesn’t just want to wear women’s clothes but wants to pass as a woman. What you have to avoid is anything, even something minor, that will be a yellow flag—anything that will make anyone think, “hmmm, that wasn’t quite right.” Because once you’re subject to heightened scrutiny, you’re in trouble.
We spent the half hour that we had mostly talking about the range of activities I needed to develop a “Ronda way” of engaging in. Alex demonstrated some things and I tried to imitate him. It was frustrating but, even in critiquing me, Alex was positive and supportive.
Time passed quickly and I was surprised when I heard the garage door open for Todd’s car.
“Just sit there like a proper lady, Ronda,” Alex said. “I’ll meet Alex at the door and introduce him to you.”
Alex left for the front door, and I waited anxiously. What would Todd think? Would he be disappointed by what he saw as a failed attempt to become a woman in order to give us cover in Arkansas? Would he think I was too successful and be turned off—or worse, disgusted—by seeing me as a woman? By the time I heard the front door open, my heart was pounding and my hands were trembling. “Dear me,” I thought to myself, trying to lighten my mood, “I fear I might need some smelling salts.” But the truth was that I was really scared.
[To be continued …]