What A Crossdresser Wants - Part 1

PART 2 | ALL STORY LIST

The white, 10 business envelope had no printing; my name is handwritten on the front. I found it sitting in my chair Monday morning when I arrived at work and came to my cubicle. I wondered who it was from; if it were official company communication, it would have been in one of our letterhead envelopes. I sat down, opened it, and found a folded letter-size sheet of paper. On it was a printed photo, obviously taken by a smartphone's camera, and my eyes widened in shock.

Someone had snapped a photo of me in my "other life" and left it here waiting for me in this envelope. It was a photo of Andrea, no question. The dress, the face, the wig, the décor of the club…they were unmistakable. I had thought nobody in the office knew I was a crossdresser, but here in my hands was proof that I was wrong. My heart was in my mouth, and I started shaking with sheer terror.

Under the photo was printed from Microsoft Word or some other word-processing software, in that annoyingly overused Comic Sans font. It read:

"Dear Andrew: Is this you?

"I took this picture at a club last Saturday night, and after looking closely, I am positive it was really you. If I am wrong, please forgive me and destroy this note. I swear to God, I am NOT trying to blackmail you or get you fired; I am really just curious. You looked really sexy - if I hadn't known your face from work, I would almost never have guessed you weren't a real woman. I would really like to get to know this other side of you. Please let me know if you are interested; I promise never, EVER to tell anyone no matter what you decide.

"Your friend always, Wendy."

I gaped at the signature. Was this the gorgeous young lady I had spent two years or more working alongside, who sat just down the row of cubicles from me? Young, pale-skinned and freckled, busty and red-haired, blue-eyed and very cute, Wendy Parsons had always seemed a bit friendlier to me than most of the people there…but I had put it down to the rapport I often had with women, with whom I had always gotten along much better than those of my own gender. She strongly resembled a younger version of the actress who plays Joan on Mad Men -- Christina Hendricks, I think her name is -- right down to the epic prow. I had always loved the way her wavy crimson mane cascaded down from her head back over her shoulders and the way her ample breasts filled out the front of her businesslike blouses and dresses. Sometimes I liked to imagine she wore something cut a bit lower than usual or left one extra button unbuttoned just for me to enjoy…but of course, that was mere fantasy.

I sat there for what must have been close to an hour, not even getting any work done, just trying to cope with the news that at least one of my co-workers was on to me and deciding what to do. Was it really from Wendy or one of my other co-workers who'd spotted me and was trying to trap me?

Finally, Wendy herself answered that question. She came walking down to my cube and saw me with what must have been a shell-shocked expression on my face. "Andrew? Are you okay?" Her tone was genuinely concerned, as was her face.

I managed to look up and say, "Uh…um…yeah, I think so."

"I am so sorry," she said, entering the cube and lowering her voice. "Should I have given you that after work? I didn't mean to upset or frighten you, truly I didn't." She got down on one knee so that she was looking up at me and laid a gentle hand on my arm. "Can we talk about it? Say, around lunchtime?"

All I could do was nod numbly and mumble, "Okay."

Wendy leaned close enough for me to both smell her perfume and catch a glimpse down her blouse's neckline and whispered, "Andy, please don't be afraid. If you really don't want to talk about it, you don't have to. You can just shred the damn letter, and we'll forget this ever happened if that's what you need to do."

I looked into her hypnotic blue eyes gazing up at me, absently admired the glossy red lipstick she had on, and let out a long breath. "No, I…we can talk about it if you can find someplace private."

"Okay, how about my car? We can pick up something at a drive-through window and sit in my car and talk over lunch. Would that be okay?" I nodded.

"I'll come for you around 12:30, okay? We can go then. Anywhere you want to eat, I'll take you -- my treat." She smiled at me and walked away.

"So tell me about it," Wendy said eagerly about four hours later, as I munched my burger and we sat in her blue Ford Focus four-door in the parking lot outside the restaurant. It was one of the chains that bore her name, and we had joked about it and how much she resembled the pigtailed girl depicted in its logo. "How long have you been doing this?" Her tone was relaxed, conversational, and not at all challenging or contemptuous. We could have been discussing the last company party or a pro baseball game played the day before. I searched her face for any hint of mockery or disgust and found none -- just what looked like kindness, sincere curiosity, and perhaps a touch of excitement.

I took the time spent swallowing a bite of burger to collect my thoughts. Finally, I said, "Um…since I was in my early teens, I think. But I've only started going out in public recently."

"How did it start? Curiosity? Trying on your mom's pantyhose or undies one day when you were home alone?"

"Something like that," I said, nodding.

Wendy then looked at me with an embarrassed expression. "I…have a confession to make," she said, smiling a bit sheepishly. "I actually have been interested in guys like you--I mean, 'girls' like you--for quite some time. I've visited a couple of websites where crossdressers hang out and found out about the club some of you go to.

"I got a couple of girlfriends to go there with me one night, just for kicks, and spotted this woman with the exact same color, length, and style of hair I have, in a dress that looked an awful lot like one I've worn to go out on occasion. I sneaked a closer look and was amazed to see a face I recognized, even under all the makeup and the wig. I wasn't entirely sure, though; I thought I might be mistaken. So I came back a week later, and sure enough, there she was…or rather, there you were again. I snapped a picture with my iPhone, but I didn't have the nerve to talk to you there and then, for fear you'd run away or make a scene or something. So I went home and looked at that photo…and got myself off looking at it again and again and again, the whole rest of that weekend. But it took me another couple of weeks to work up the courage to leave you that note." She looked fearful now. "Are you mad at me? I wouldn't blame you, honestly. And I swear the photo isn't online or anywhere else but my phone. I'll even delete it if you want. That's why I printed it out rather than just emailing or texting it to you; I wanted to avoid any chance it might get intercepted in transit."

"Um, no, I guess not. I thought about it. To be honest, I actually feel a bit flattered. I did sort of pattern my look after you."

"Well, then, now I feel flattered," she said, sighing with relief as she smiled back. "You really wanted to look like me?"

Now it was my turn to look embarrassed. "Uh, kind of, yeah," I said. "Is that bad or creepy?"

"Oh, no, not at all!" Wendy replied, laying a hand on mine. "Maybe some other women might think so, but not me. I've wanted a 'special' girlfriend like you for a long time, but I never thought in a million years I'd find her where I work!" She was eyeing me with a coy smirk. "Shame on you for hiding it from me so long!" she said, playfully wagging her finger at me.

My heart was pounding. Was this for real? Was I dreaming? Here was one of the sexiest real women I knew, actually saying she was interested in me as Andrea…or maybe both Andrea and Andrew.

"Does that mean you think I'm…attractive?" Wendy said shyly. "Are you into women? Or are you gay?"

"Yes and no, in that order," I said. "I absolutely am turned on by women--being with them and being like them…especially you."

"Really?" she said as she blushed clear down to her cleavage. "Does this…doppelganger of mine have a name?"

"I usually go by Andrea when I'm en femme," I said.

"Andrea," she said thoughtfully, trying out the name on her tongue. "What a lovely name…for a lovely young lady." She smiled again. "Well, now that I know something about you and 'Andrea'…and you know that I know…and assuming neither of us is upset…what do you think we should do about it? Or rather, what would you like us to do about it?" Her hand was still holding mine, and she squeezed it firmly yet gently.

"Um…I dunno," I said. "What did you have in mind?"

"Well, I would love to see how you go from being this normal-looking guy to a bombshell fellow redhead. Would you be willing to let me watch you transform yourself? Maybe even help you out a little bit? And then we could see where things go from there." She gave me a sly grin.

I could feel myself becoming aroused. "Okay," I said.

She smiled warmly again. "Then why don't you come over to my place tonight? Around 7:00, I'llemaill you directions. Bring whatever you need with you. I'll fix us some dinner, and we can talk some more…and then I want to meet Andrea!"

I rang the doorbell at her apartment that evening around seven. I was carrying what I called my "Andrea bag": a large, soft-sided overnight bag with a floral print on the outside. It had been made by Chic and still had the tag on it reading "For the natural woman." I had found that a hilarious private joke, given what was inside it: all the clothing, accessories, and paraphernalia that went into turning myself into a very unnatural "woman."

Wendy opened the door, looking incredible. She had done up her hair and makeup as though going clubbing and wore the same dress I had bought a copy of for Andrea: sparkly purple silk with sheer sleeves and a shirred front. Sheer, dusky hose and high-heeled sandals, and a gold bracelet on one arm completed her look. She was taller than most women; without the run-come-fuck-me heels, we might even be about the same height. The dress was tight and cut high up the thighs and low down the neckline, revealing Wendy's impressive curves and cleavage that I had so often admired, lusted after…and envied. She smiled with delight seeing me look her up and down, drinking in the sight of her.

"Andy! You like?" she asked, twirling around and posing to let me see the whole ensemble.

"I love it," I said. "You look incredible."

"Why, thank you, sir! Come on in dinner's almost ready." She kissed me on the cheek and practically hauled me inside. "You're trembling! Are you all right?" She sounded concerned again.

"A little nervous, I guess," I said weakly. "I've never done this with a real woman before." The truth was that my heart was in my mouth. What if she turned out to be some sort of psycho? But there was also nervous excitement.

Wendy closed the door, took my face in her hands, and said gently, "Hey," taking me in her arms and holding me close, and speaking softly in my ear. "You don't have to be afraid. First off, nothing is going to happen tonight that we don't both want to happen -- I give you my solemn word. Second, there is nothing bad or wrong or sick about you at all. You have nothing whatsoever to be ashamed or embarrassed about…and third, your secret is absolutely, positively, completely safe with me. It'll be our secret now -- just you and me. I would never, ever tell anyone without your permission. I know it can't be easy for you to open up about something this private with someone for the first time...and I feel honored and touched and grateful that you're willing to share it with me...not to mention really turned on." There was that devilish grin of hers again.

Then she leaned in to kiss me much more passionately, the way I had long fantasized about her doing but never dared hope she would ever actually do. I tasted her creamy red lipstick on my lips and felt her tongue sliding between them. Her voluptuous body pressed against me from ample bosom to rounded, broad hips. She kissed me hungrily for close to thirty seconds, a kiss full of sensuality and promise. Finally, she broke the kiss and breathed heavily, our faces no more than an inch or two apart. "Oh, my," she said huskily, her face flushed and grinning. "If that's how you kiss as Andrew, I can't wait to see how Andrea kisses!"

"Wow," I replied. "I wish I'd known this was all it took to get you to notice me; I'd have come out to you ages ago!"

"Oh, believe me, I did notice you…but I didn't want to be accused of sexual harassment. But if you had come out to me sooner, we could have had so much more fun together." Wendy grinned conspiratorially. "But don't you worry—we're definitely going to make up for a lost time! Let me fix you a drink, and we can get dinner on the table. Will you let me take your bag? I'm just going to put it in the bedroom for later." She looked at me questioningly and held out a hand for the bag. When I nodded, she took it from me and sashayed off, giving me a lovely rear view as she swung her hips seductively, clicking her way down the hall on the tall heels.

Dinner was chicken fettuccine, Alfredo, with broccoli; how had she known it was a favorite dish of mine? She must have seen me eating some in a frozen dinner during lunch break at work. A bottle of red wine stood on a side table, and she poured some into crystal goblets for each of us. We ate, drank, and chatted about everything and nothing, and she asked more questions about my cross-dressing that showed she had indeed done her homework.

"I've heard that some crossdressers like to be dominated," she said at one point. "There are even websites and services that offer what they call 'forced feminization.' Are you into that sort of thing?"

"Oh, God, no," I replied. "I've never been able to understand why someone would want to be humiliated or punished or hurt for doing this."

"Maybe they have some part of them deep down that feels guilty about what they're doing," she observed. "It might be their way of coping with that guilt and still being able to have the fun part."

"I suppose so…but I already feel embarrassed enough about this part of myself. If I'm going to share it with someone, I want it to be someone who treats me with kindness and gentleness…as an equal with her."

"Then we're absolutely on the same page," she said, smiling. "And what did I say about not being embarrassed or ashamed?" She pointed the finger at me. "No shaming allowed…including shaming yourself. Okay?" I nodded.

"Are you transgendered? Planning to transition? Or is this just an occasional bit of role-play for you?"

"Well, I wondered about that for a long time," I replied. "If I did have gender dysphoria, I mean. But after a lot of therapy and research and thought, I decided I probably wasn't a woman trapped in a man's body. I do like being a guy some of the time…but this is mainly a sexual thrill for me."

"Oho! A fetish, huh?" said Wendy with another devilish smile.

"I guess so. I know I don't really have more than a little better insight into what being a woman really is than most men. I can step in and back out of it at will, but you real gals aren't so lucky. I'm probably deluding myself about what it's really like to live as a woman."

"Oh, I don't know," said Wendy. "I believe we all have elements of both genders within us; the balance is different in some of us, that's all. And I sure wouldn't wish sexual assault, discrimination, or menstruation on you…but I don't think there's anything wrong with exploring how the other half lives now and then. In fact, I admire you for it; you have more courage than a lot of macho guys. You know, I once dated a guy who couldn't stand to hold my purse for me in public—not even for a minute or two! Like it had girl cooties on it or something." She laughed and smiled. "I can tell you would never have that problem. Don't you think we'd all be living in a much better world if more men would put themselves in our shoes—so to speak?" I couldn't help but smile at that.

Dessert was Black Forest cake with ice cream, another longtime favorite of mine. Finally, the meal was finished, the dishes put away in the dishwasher, and Wendy sat down on her very modern-looking sofa in the living room, patting a spot on the cushion beside her by way of encouraging me to join her. We were each on our second glass of wine, and she raised her glass as I sat down. "To new friends…and lovers," she said, her smile suddenly turning slightly lascivious. I clinked my glass against hers, and we both drank.

"Feeling better now?" she asked.

"Yeah, I think so."

"Good. I want you to feel completely at home and relaxed here, always. From now on, my home is yours too…and Andrea's. Come over anytime you want to, and we can do whatever you like, whether it involves cross-dressing or not." She fished out a key from inside her cleavage and handed it to me, grinning. "In fact, I even had a spare key made today, just for you."

"I don't mean to seem ungrateful, but…are you sure you really want to do that so soon?" I said, taken aback by her generosity. "I mean, we barely know each other."

"Now, you know that's not true, Andy," she chided gently. "We've been working together for nearly two years now. I wouldn't make this kind of offer to just anyone…and I've seen enough of you by now to be fairly sure you're not secretly a murderer, thief, or rapist. And I hope you don't suspect me of being any of those things." She smirked, then leaned close with an earnest expression. "Please, take it. I want you to have it." She put down her wine glass on the coffee table, placed the key in my open hand, then closed my fingers over it and took my hand in both of hers. Hardly daring to believe my good fortune, I slipped it into a pants pocket.

Leaning back on the sofa, she extended an arm to me. "Come on, relax!" she said. I leaned back next to her, and she slipped the arm around my waist and nestled in under my own arm. She picked up her glass again and looked at me over the rim, her blue eyes lidded in purple eye shadow and accented by long dark lashes. "Speaking of Andrea…are you feeling ready to introduce me to her?" she asked coyly.

I gulped, swallowed another sip of wine, and nodded. "I...I think so," I mumbled.

She smiled again. "Then why don't we go into the bedroom so you can get started? You can even borrow some of my things if you like; you look like you're not all that far from my size."

"Thank you," I said. I took a deep breath, pocketed the key, and thought, Okay, let's do this. come to play with us…but we'll do it one of these days.