A Gift in Disguise Ch. 19

Tom, during my after-dinner introduction I will introduce you first. I'll explain that you were a collegiate competition swimmer and that you're not a professional model or actor. I will also tell the audience that you're the principal male model but not the only one in most of the photos that Risa and Mikki selected for the display they will be viewing. I'm not going to explain why they selected you, though. I want the audience's imaginations and maybe fantasies to begin taking shape at that point.

You should expect to be ogled by the women and some of the men when I introduce you, Tom. Always keep in mind that Boys Will Be Girls Night at The Club is when the men are encouraged to be very sexy women and the women are encouraged to be as masculine as they want.

To very subtly enhance the chosen sexual role for the night of every one of our audience members, Tom, I'd like you to be dressed in a well-fit dark business suit with a color-coordinated shirt and tie. If you don't already have an outfit that will work, I'll rent one for you. You are a very handsome, virile, athletic young man. I promise you are going to be very surprised at how much a power outfit that projects and emphasizes your decidedly male sexuality will promote and intensify the sexual fantasies of everyone there.

Additionally, Tom, I'm going to ask you to be at The Club at least an hour before the guests start arriving. I'm going to have The Club's makeup artist there to highlight some of your facial features so that The Club's lighting makes you look even more desirable than you already do to the audience.

Misako already knows how to dress and make herself up without being gaudy or too obvious to send an unmistakably enticing look regardless of room lighting color or intensity, but you may not. You'll just have to trust me on this, Tom. Once you get used to it I think you'll like the look my makeup artist gives you, and I guarantee the audience will, too. You the superstud male and Misako the epitome of transexual femininity are going to drive our members and guests deliciously and lustfully wild."

Mikki had been watching me carefully and read my look of hesitation and spoke to me before I could respond to Bethany.

"Tom, I know the prospect of wearing makeup will seem awkward for you at first. Believe me, it felt a little funny even for me the first few times I experimented with makeup as an early teenager. But you have an advantage that I didn't have. Your first time wearing makeup is going to be applied by a woman who knows how to accentuate every male model's masculine features so that someone looking at him is really turned on by what they see. You're probably concerned she'll have you looking like a drag queen, but that's not how you'll look at all.

Marlene -- that's Bethany's makeup artist -- Marlene has a keen sense of what The Club's audience wants to see when they look at a woman or a man, especially a straight guy like you. I know how seeing a man or woman Marlene has made up turns me on. I only hope I can restrain myself until we're together after the guests have gone to their rooms and we've gone to ours. I can almost promise you that when the night is over, you're going to ask Marlene to teach you how to do your own makeup. You're straight, but a slight skillful application of makeup not only accentuates your manhood to the cis women there, it also cleverly and subtly hints at a sexual femininity to trans people like me and to bi or lesbian women. I have a feeling I'm going to be just a bit jealous at the sexual attention you'll get at The Club."

Mikki's words of reassurance had a sexual tug-of-war effect on me. One side of me had been silently screaming, "I'm a straight man, dammit!". But the other side was uncharacteristically intrigued with the idea that I could somehow arouse both men and women to really want to have sex with me. Recalling my responses to Stephanie in college and then my unbridled pleasure while actually having sex with trans woman Kerri Kavenaugh at my friend Emily's home definitely helped me make my decision. And the look Mikki had given me just now when she explained how my being made up would affect her nearly made me cum right then and there.

Then Bethany stepped in to close the deal.

"Look, maybe this will help," she continued. "Remembering that the night's theme is crossdressing and transgender sex and also remembering that The Club has hosted a night with this same theme in each of the past two years, you will see some members and guests that night in various states of cross-dressing. In fact, The Club's promotions for that evening strongly encourages the boys to come as girls and the girls to come as boys, even if they've never crossdressed before. This is the night we encourage experimentation with sexual role reversals and role playing to intensify members' and guests' sexual drives and pleasure even if they're there intending to just be admirers and not participants. Even I was surprised the first two years at how easily members and guests adjusted to their sexually-reversed roles. They have all enjoyed it far more than they expected to, I think.

My point is, if members or guests were uncomfortable with transsexuality or transgenderism, they wouldn't even be there that night, let alone participating by cross-dressing themselves. Based on our first two years of 'Boys Will Be Girls,' I can promise you that you will be surprised at just how much care and preparation the members and guests put into their respective role reversals. They really get into it. You won't see outrageously attired and made-up television drag queens there; you'll see just how sexy and elegant cross-dressers can be in both attire and behavior.

I'd suggest that you approach your conversations with the thought in mind that everyone there has a very healthy curiosity about sexuality, including cross-dressing or trans life. Hopefully you'll be as comfortable answering their questions as they will be asking them: honestly and maturely. If you're a little uncomfortable, tell the audience about it and explain why. Believe me, they'll understand and be sympathetic. You honesty will be appreciated and respected. Tom, they know and can see that you're straight, so your being not just willing but eager to appear live and onstage with Mikki, a gorgeous trans woman, will almost certainly prove to be a turn-on for some of the folks.

If you're so inclined, you're completely free to express your own comments about any members' or guests' costumes, accessories, and makeup. Don't hold back from being a little flirtatious if it seems to feel right. And Tom, don't be the slightest bit surprised if some of the costumed members and guests see trans potential in you and genuinely encourage you with helpful hints about how you could start cross-dressing yourself. Privately at first, of course, but who knows? Maybe next year..."

Mikki's and Risa's nods of agreement with Bethany's remark caught me a little off guard, but before I could say anything, Bethany continued.

"As you know, The Club's rules forbid members and guests -- that will include you -- from having sex with others except their dates while you're at The Club, but if you and one or more of them want to arrange for any contact off the property, exchanging names and phone numbers here is perfectly appropriate.

To that end, I've developed an informal practice to discreetly facilitate outside meetings. To protect everyone's privacy and avoid misunderstandings, I've discouraged anyone's exchanging their real-world business cards. Instead, don't be surprised when and if someone hands you a plain white business card with only a name and phone number, nothing else. That is the informal but completely appropriate signal that they would like to talk with you on the phone. Where you go and what you do with it after the evening ends is up to you -- completely up to you. No one will feel the least bit offended if they've given you a card but never receive the call they hoped for."

Possibly recognizing that she had reassured me as much as possible, Bethany moved on to Mikki.

"Mikki, your deepest feelings about being a transgender woman are going to be of great interest to the audience. That you are also the talented professional photographer who took the photos they will be seeing is going to add an extra dimension to your obvious physical beauty and radiant sexuality.

I'm pretty sure that each man in the audience will have wondered at one time or another what it feels like for you, a really beautiful and desirable trans woman, to experience sexual pleasure. The men will probably want to know how and when you physically and emotionally fully committed to openly live your life, including having sex, as a woman. They are going to want to know what led you to make that final decision to fully transition. And, they'll probably ask you if you have any lingering regrets about that decision.

You might get one or two questions about the medical side of your transition, questions about the choices you made for any hormone replacement and reconstructive surgeries, but I kind of doubt it. Nevertheless I'd suggest you and Tom talk about that after dinner privately tonight so neither of you are surprised if the question comes up.

Mikki, you know as well as I do that each biological female there is going to be mentally comparing your comments and answers to her own feelings as a woman. I guarantee that some of those biological women are also going to wonder what it would feel like if they as a woman actually had a fully-developed and functioning cock like yours.

Some of the women are going to be excited at the thought of 'lesbian' sex with a trans woman. Do you come on to them like you're a man or will they feel something entirely different than when they're with a man? How much different will your cock feel from how it feels to them to be fucked with a strap-on? Who knows, one of them may even come right out and ask you if any woman's experience with you has caused her to feel more excited with a trans woman than another biological woman.

Tom, because you're a cisgender male, I'm sure this will feel more awkward for you. About all I can tell you is to expect to be asked if you have ever had the urge to cross-dress and then to explain those feelings one way or the other. Someone may also ask if you ever wanted to be a woman even briefly to experience what she experiences sexually. And because most men are aroused watching two women having sex, you might get asked if you've ever imagined being a woman yourself and then having sex with another woman. I have never met a man who hasn't experienced these feelings in some form or another even if they won't admit it, so that night I really want you to feel completely free to acknowledge and describe yours.

You can certainly expect to be asked how your sexual feelings as a cis male toward Mikki are different from your sexual feelings toward a biological woman. What attracts you to her? How does your sexual attraction to Mikki feel differently than your attraction to a biological woman like Risa or me, for example.

The point is that some of our members and guests may be struggling a bit to explain or maybe rationalize their own sexual excitement by being with cross-dressers or being cross-dressers themselves, so don't be too surprised to see some head-nods in agreement to your comments. The more comfortably and honestly you respond, the more relaxed and even reassured members and guests will be.

You might as well know that before our first 'Boys Will Be Girls' night, I wondered many of these things myself, so if someone in the audience doesn't ask you to elaborate on that, I'm going to. My only suggestion for you is, don't tailor your answers to what you think either the men or women in the audience want to hear. Please be forthright with them. You're not going to offend them.

After dinner tonight, I hope the two of you will talk openly and honestly in the privacy of your suite so when you start getting the questions at 'Boys Will Be Girls' night, you won't be caught off guard by what you may be asked and with what you hear each other answering."

Bethany paused to see if either of us had questions. We didn't, so she proceeded.

"One thing that should make it easier for you at 'Boys Will Be Girls' night: Some of our members and guests have actually been evening headliners themselves for other monthly themed nights including our 'Keeping It in the Family' night. They have engaged in live, onstage sex because they were practitioners of the sexual behavior that was the theme for that particular evening. They've experienced the pressures that both of you will be feeling, so I can promise you that none of them will ask any inappropriately gross questions.

You will be very surprised when you talk to couples who have been an evening's featured performers onstage. Many were initially reluctant, but afterwards, they have all told me pretty much the same thing: Once they overcame their initial performance anxiety -- no pun intended -- they actually started getting into exhibitionism. Exhibitionism in front of an accepting and encouraging crowd can actually become a surprisingly powerful aphrodisiac. That's proven to be consistently true regardless of the evening's theme.

They also found that their conversations in subsequent evenings with members and guests who had watched them were far easier, far more enjoyable, than they imagined they would be. Their courage, if you want to call it that, to have sex onstage for all to see was genuinely admired and respected by the members and guests who watched either live from the VIP room windows overlooking the stage or on the audio-video feeds into their guest rooms.

Of course in your case, I'm not expecting you two to have sex as part of your presentation. Nevertheless, if something happens to cause you both to want to change that, please feel completely free to go comfortably with it. If it's truly spontaneous for both of you, it is more likely to arouse and entertain the audience and maybe even encourage reluctant ones to join in with their evening's partner. It will make the evening a lot more fun for the two of you, too.

To make it easier for the two of you to get comfortable communicating with each other, I've invited Risa to stay with me in my apartment tonight while the two of you share one of the two-bedroom, separate bathroom VIP suites we use to accommodate foursomes and couples swapping spouses and partners.

I've queued up your suite's A/V access with a few of The Club's video recordings of previous theme night onstage sexual presentations by members and guests. The idea is for the two of you to watch one or two of the videos on your suite's hi-def video system if you want in order to get an idea of how quickly and comfortably our members and guests get over their stage fright as the night's headline entertainment. And as I said, we've done two 'Boys Will Be Girls' nights before the one you two will be headlining, so I've included the videos of both onstage performances from those nights.

I should be completely honest and let you know that to ensure success, the headliners for the first two 'Boys Will Be Girls' nights we held were hired professional entertainers from the local underground x-rated live stage groups. Technically, you two will be the first amateurs. But again, I want to stress that you two aren't expected to even have sex when you headline "Boys Will Be Girls' night. Your presentation is going to be just what it's billed to be: An exhibit of Mikki's photographs that almost always have a still-mysterious and unexpectedly exciting effect on people who see them. The four of us are already prepared for the likelihood that some and maybe even all members of the audience will experience intense spontaneous arousal. Some will even have sex and even orgasms right there in the exhibit room. I just wanted to prepare you so you could be comfortable with however they and you respond."

Bethany's explanation had reassured me as much as it could, but I could tell that both Risa and Mikki were still far more comfortable than I.

"So let me give you both a few questions so you have some idea what to expect during your presentation.

Tom, why did you agree to be the model for Misako's photos including some of them on display here tonight?"

I explained very briefly about how Sharon and I knew each other as neighbors and how I had been in school with Sharon's trans daughter. I explained that Sharon's daughter knew Mikki as a professional photographer with a unique gift for photo composition and that as a favor to Sharon, I had told Sharon's daughter she could show some of my competition swimming photos to Mikki. After seeing my photos taken by other photographers at swim meets, Mikki had sensed I had the qualities be a good subject for some of her very unique and special photos, so she asked Sharon and her daughter to introduce me to Mikki.

"And did you know that Misako was a transgender woman before agreeing to model for her?"

"Yeah, Sharon had told me, but she really didn't make a big deal out of it. It was like, 'By the way Tom, Misako Sato is a trans woman. Is that going to matter?' I said 'No' and that was it."

"And what about when you saw Misako in the water in her one-piece swimsuit for the first time? Weren't weren't even the slightest bit turned on?" Bethany asked with both vocal and visual signals of disbelief.

"You know how much a woman in a revealing one-piece swimsuit turns me on! Well, Mikki is unquestionably a drop-dead knockout in the swimsuit, but strange as it may seem, I was more surprised and actually very impressed with her athletic ability at the pool than anything else. I had been expecting her to take all the photos from poolside rather than actually being in the water with me. I assumed she'd be dressed poolside casual -- you know, maybe comfortable shorts and tank top or something like that. But the way she handled her photo gear in and out of the water so smoothly and skillfully... really impressive for a woman. And she's really a good, strong swimmer even when she's handling camera gear in the water. That can't be an easy thing for anyone to do, especially not a woman.

As for my not being instantly turned on seeing her in a swimsuit, that may be because at collegiate competition swim meets it's very common for men and women to see each other in tight, revealing competition suits. And too, most women who swim competitively have more prominent muscular development, so their swimsuits are chosen for functionality and conformity to the athletic association rules rather than advertising the woman's figure. Regardless, competitive swim meets are just not inherently sexual situations in spite of how much skin is showing. We're focused on the other team's skills and our own performance, not on their bodies or on anyone taking photos.

In talking with me before she changed into her swimsuit and began photographing me, Mikki had been pleasant but comfortably businesslike. There had been nothing even remotely sexual in our conversation at all. She is really an amazing and talented woman. Truthfully, I was really fascinated with how she was able to see and then photographically capture the otherwise hidden sexuality in her subjects to the point that seemingly innocent photos could generate explosive spontaneous orgasms.

She had explained that she felt or saw the intensity of my concentration on swimming in the photos. What she saw had been a remarkably powerful attractor to her photographer's creative intuition. She told me that when Sharon's daughter showed her my photos, she had one of the strongest reactions she'd ever had about her ability to photographically capture a model's latent sexuality.