OUTED IN THE OFFICE
Fiction by Cynthia V. Hart
The white #10 business envelope had no printing on it, just my name 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.
It was a photo of Andrea, no question. The dress, the face, the wig, the décor of the club…they were unmistakable. Someone had snapped a photo of me in my “other life” and left it here waiting for me in this envelope. 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 printing 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 lunch time?”
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 chain 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 e-mailing or texting it to you; I wanted to avoid any chance it might get intercepted in transit.”
I thought about it. “Um…no, I guess not. 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’ll e-mail 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: purple sparkly 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 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 cross-dressers 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 a 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. I stood up a bit unsteadily. “Lead on,” I said.
She got up, took my hand in hers and pulled me after her.
Within a minute I was in her bedroom. I wasn’t sure what I had expected it to look like, but it was beautiful; very tasteful without being exaggeratedly feminine. The décor was mainly green and purple -- to offset her own coloring, I suppose. Curtains were drawn over the windows, and a vanity table and dresser stood against one wall. A walk-in closet stood with its door open, revealing racks of dresses, blouses, skirts, pants and other items on hangers and a rack of shoes in various styles.
I hesitated, wanting to go ahead but somehow unable to. “Are you feeling self-conscious with me here?” Wendy asked solicitously. “I know this is probably moving pretty fast for you. For me, too, if it’s any comfort…but I really would like to meet Andrea and make her feel very welcome.”
“I’m sorry,” I said miserably, sitting on the bed and looking at the floor. “I don’t know what’s wrong with me. This is the sort of thing I’ve fantasized about for years…and now that it’s finally happening, I freeze up. I mean, what the hell?”
Wendy sat beside me and took my arm gently. “It’s okay, sweetie, really. You’re probably not used to doing this with an audience -- even a friendly one.” She looked deeply into my eyes. “Would it help if I undressed, too?”
“Maybe,” I mumbled, embarrassed at my hesitancy to accept a very clearly given invitation like hers.
She stood up and turned her back to me. “Unzip me, would you please, love?” I complied with trembling fingers. She let the dress slide down her shoulders, revealing a whalebone corset with black-ribbed purple satin panels and open cups displaying her magnificent huge breasts, their stiff nipples the size of berries and cookie-size areolas wrinkled with obvious arousal. Black frilly garters at the bottom of the corset held up her thigh-high stockings so much like mine, crossing a pelvic region utterly bereft of panties that held a thick, curly red bush of pubic hair. She stepped out of the pile of cloth on the floor that her dress had become, and walked over to the dresser, opened a drawer and drew out a pair of black velvet opera-length gloves, which she slid onto her arms and tugged into place -- the perfect final touch. She smiled and struck a classic pin-up pose: left leg cocked forward, poised atop her tall heels, arms up and hands behind her head. “I thought seeing me in this sort of outfit might help get you in the mood.” She moved in to kiss me again, on my lips and cheeks and neck, sliding hands over my body and unbuttoning, unbuckling and unzipping, and before I knew it I was starkers and my shoes and clothes were lying on the floor beside the bed.
“Is this better?” she murmured, still smiling. "Or do I look too domme for you?"
“Oh, no, not at all,” I said, awestruck. “You are incredibly lovely.”
“Well, aren’t you sweet? Now it’s your turn to get beautiful.” She looked at me seductively from under her purple eyelids and thick black lashes again, and gestured toward the vanity chair meaningfully.
My bag was sitting next to the small vanity, and I sat down in the chair and opened it. Wendy sat on the edge of her four-poster bed and watched in fascination as I lifted out items from the bag: first the purple-and-black bra and panty set, then the frilly waist cincher and black full-fashioned stockings with seams up the back, then my pair of size-12 purple pumps and my copy of Wendy’s dress. I drew out a wrapped condom, unwrapped it and slipped it over my penis before sliding on the panties and tucking it back between my legs to create a smooth, feminine front. “Good idea,” said Wendy, grinning again. “Wouldn’t want to stain those lovely, sexy panties, now would we?”
My arms, under-arms and legs were freshly shaved for the occasion, and I rolled each stocking over its leg carefully, working it up slowly to avoid runs or tears and tugging it smooth at the top. Then I hooked the waist cincher around my already narrow midsection, breathing in deeply and sucking my stomach in as far as I could, then tightening its laces and hooks to give me the “hourglass figure” I craved, and snapped the garters onto the stockings, front and back. I ran my hands over my newly sheathed legs and thrilled yet again at how silky and sexy they looked and felt.
“Wow,” said Wendy, “you have great legs, honey!” I could only smile bashfully; as she'd said, I wasn't used to doing this with an audience. I then took out my RealBreasts™ and some surgical glue, and glued each prosthetic to my smooth chest. The edges were so thin you could hardly see them once they were on. When I was sure the glue was set, I took the bra and hooked it around my waist backwards so that the clasp was in front, then turned it around so the cups were under my new boobs. I pulled the reinforced straps over my shoulders and settled each breast firmly into its cup.
“So that’s how you get that marvelous cleavage!” Wendy exclaimed. “You must be at least a D-cup!”
“38-DD -- just like you,” I said, grinning. I looked at the result in the vanity mirror and was as turned on as usual by what I saw. From the neck down, I looked like a hot, buxom woman in sexy lingerie.
Now it was time to put on Andrea’s face. I chose a purple eye shadow to match Wendy’s, rose blush powder and the fire-engine-red lipstick I loved so much. First I laid on a light coat of foundation and beard cover, just enough to hide blemishes and smooth out my features without looking caked-on. Then the blush, the eye shadow and black pencil eyeliner, then the mascara to bulk up my lashes like hers; and finally the creamy red lipstick, framed with a pencil lip-liner. A couple of dangly clip-on earrings from the bag went on my earlobes, and a jingly silver bracelet and female-styled watch on my wrist.
I noticed a bottle of perfume on the vanity. “Is this what you’re wearing?” I asked Wendy.
“Mm-hmm,” she said. “You want to try it?”
“Could I? I love the smell.”
Wendy smiled and gestured to it. “Be my guest.”
I spritzed a bit on my wrists and behind my ears, and another down my newly-acquired cleavage. Then I stood up and stepped into the dress, working the zipper up the back and closing the little clasp at the collar. Finally, I pulled out my pride and joy from the bag: a Styrofoam wig stand with my gorgeous red human-hair wig on it. I pulled a wig cap over my own medium-short hair and then lifted the wig off its stand, bending over to slip it over my head and tug it down into place in back. A couple of hairpins from the bag clipped it into place. Sitting down again, I combed the tangles out, then picked up the pumps and slid one hosiery-clad foot into each, and admired how they plumped up my calves as always. Finally I stood up, turned back to Wendy and said in my best, high-pitched soprano, “How do I look?” I smiled and posed for her.
Wendy gasped a little, then stood up and came to me, her face filled with astonishment and delight. “You look absolutely amazing, my dear,” she said. “Let me hear you say your name.”
“Hello, I’m Andrea,” I said, offering her a hand.
“I’m Wendy, and I am so thrilled to meet you at last, Andrea,” Wendy said, taking my hand in hers and clasping it firmly. “You really are quite beautiful… but you haven’t done your nails yet. Would you like me to help you with that?”
I nodded, thrilled beyond words myself. She pulled up the chair and sat me down on the bed, then asked, “Do you have your own nail color?”
“In the side pocket inside the bag,” I said. “There’s a cosmetics bag in there with three or four bottles. You pick the shade.”
She reached in and got the cosmetics bag out, examining it to find the bottles of nail color. She eyed me thoughtfully for a moment, then chose my favorite color. "'Ravishing Red,'" she read from the label on the bottle. "To match those delicious full lips of yours,” she said and uncapped the bottle as I sat down again and held out my hands. “Incidentally, I noticed you keep your nails just a little bit longer than most guys. That’s one of the things that first made me wonder if you might be a part-time woman.” Her eyes twinkled with merriment as she opened the little red bottle and started brushing it over my nails. In a few minutes all ten of my fingernails were glossy red and dry, and I pulled out my purple cloth purse from the bag to finish off my look. I had already stashed my wallet and keys in it before coming over.
“I can’t get over how much like me you look,” Wendy said, looking my new figure up and down. “Aside from some slight differences in facial contours, it’s almost like looking in a mirror. You even have blue eyes just like mine! Of course, you’re a hair taller in heels, but still…we could be sisters. It doesn’t hurt that you’re built the way you are.”
“Well, I never much cared for working out,” I said. “Since I was never that good at being a real man, I figured I might as well enjoy being a fake woman.”
She laughed out loud. “I love that! But I think you might be sexier with green eyes. We should look into getting you some colored contact lenses…and some green outfits, too.”
“I already have a cute green dress at home. I could wear it for you sometime, if you’d like,” I said.
“I’d like that a lot.” She sat on the bed next to me and crossed her legs next to mine. “Don’t our sexy legs look great together, girlfriend?” she said. “And I see we share the same taste in trashy lingerie, don’t we?” She grinned shamelessly at me as she rubbed her own nylon-clad legs against mine sensually and slipped an arm around my waist.
“I guess we do,” I said.
“I had a feeling we did,” she murmured, sliding her hand up my nyloned leg and caressing my thigh. “You’ve obviously had some practice at this. Who would ever expect to find a big, long, hard surprise under that tight dress?”
“Thank you. You don’t look bad at all yourself.”
“Let me see you walk, dear,” she said. I rose and did my best to totter over the carpeted floor from the vanity over to the window and back in my five-inch-heel stilettos. “Swing your hips a bit more,” Wendy said. “You’ve got it, honey, so flaunt it! And remember, you’re a woman now, so you have a lower center of gravity. Watch me closely.” She did the same walk-and-turn far more gracefully than I had. “Put your weight on your toes as you walk, not your heels. Now can you try again?”
I watched the play of her shapely muscles, limbs and ass and tried to mimic her movements. She clapped her hands in applause. “Much better!” Now it was my turn to blush.
“You look just like you did the night I snapped that picture of you. Is that intentional?" she asked.
I lowered my chin and looked at her through my lush new lashes. "Maybe," I said, smiling slightly.
"I thought so," Wendy said with satisfaction. "With a bit more training, I bet I could take you to the fanciest, straightest restaurant in town and nobody would bat an eye!” Then she grinned again. “Would you like that, Andrea honey? To have us go out somewhere as girls together? Two hot redheaded babes out on the town, seeing how much trouble they can get into—would that turn you on? I bet it would; I know it would turn me on.”
“Do you really think I could pass?” I asked.
“Are you kidding me?!? The way you look, and with me along to reinforce your illusion? Trust me, sweetie -- nobody would look at you and see anything but 100 percent real live, natural-born woman!”
“Oh, you’re just saying that to make me feel good.”
“No, Andrea, I’m really not.” She took my chin in her hand. “I wouldn’t lie to you about that…or anything else. You really do look beautiful and sexy as a woman. You almost look better than me! I’m honestly jealous. And I really am serious; I’d love to go out with you the way you look now, any time you want…or do anything else you’d like.” Then she kissed me again, deeply and passionately just like before, our glossy lipsticked lips sliding over one another, tongues dancing in each other’s mouths. I could feel our big, soft boobs pressing against each other as she slipped her arms around me and held me to her tightly.
“I want you to make sweet, soft lesbian love to me, my darling Andrea,” she whispered. “Would you like that, too?” She slid her hands up my bust and squeezed my ersatz melons gently.
“Mm-hmm,” I could only moan.
“I thought so,” she said with satisfaction. “And Friday night, when we don’t have to work the next day, why don’t you plan on coming back and staying the night? We can both get gorgeous…and go out to that club together.” She nuzzled my neck and played with my boobs, then slid a hand up my skirt and into the front of my silky panties. “You like that idea, don’t you, you hot little thing, you?” I nodded and whimpered with pleasure as she slid fingers up and down as if massaging the clitoris I wished I had. “You like having someone slide a hand down those pretty panties and play with your pussy, don’t you? I can feel you getting so wet.” She put hands on my head and guided my lips to her left nipple, where I sucked eagerly as she gasped in pleasure. She pulled me to her more tightly and cooed, “Oh, yeah, honey…suck my tits like I know you like yours sucked.” Her fingers played with my own silicone “nipples” through the fabric of my dress and bra. “You’re a goddess! I want you so much…” She pulled back a little and eyed me from head to toe. "You look so sexy in that, I almost hate to ask you to take it off...but would you?"
I nodded and turned so she could have the pleasure of unzipping me. She stepped back and watched as I coyly lowered one strap off a shoulder, then the other, while turning my head back over it and giving her my best come-hither look. Then I slid the dress back down over my hips and let it fall around my silky-hosed legs and high-heeled feet. Before I knew it, she was lying prone on her back in the bed, and I was lapping at her slippery labia and clit, tonguing her into ecstasy as she writhed and moaned and bucked and thrashed. “Oh, yeah! You know what another woman likes, don’t you, honey?” she gasped as I licked and teased with my tongue sliding out from between my glossy red lips. “Are you trying to drive me completely crazy?”
“Well, duh!” I giggled. “Am I succeeding?”
“Yes,” she whimpered. “Please, don’t stop…” She pulled my crimson-tressed head deeper into her crotch, and I slid a couple of fingers with glossy red nails on them in and out of her glistening opening as I licked. She finally came in a yelling, shuddering orgasm. “AAAGGGH! Ohhh…” I stopped and watched her lay there, cupping and squeezing my lace-encased breasts in my hands the way I’d seen women in porno photos do, pouting sexily and licking my lips. “I want you inside me,” she finally said when she had her breath back.
I mounted her, clad only in my lacy unmentionables, stockings and heels, matching her in all but the shoes, her own hosed-and-heeled legs wrapped around my satin-cinched waist. Any porn mag or website would pay top dollar for the kind of hot girl-on-girl images they could have snapped of us. I kissed her softly on the mouth as I reached down to free my now-stiff member, which had been getting more and more difficult to keep concealed as it got harder and harder watching Wendy. I pushed the tip of it gently as I could into her moist lower lips, and she reached for it to guide me in, gasping as I entered her. “Oh, my…that strap-on feels so real -- and big!” she giggled, grinning knowingly at me and winking.
“Only the best for you, my love,” I said as I plunged deep into her. Our boobs jiggled with each thrust as I kissed her and moved in and out of her lower wetness, deeper and faster and harder all the time, penetrating her with both tongue and cock, until I finally could hold back no longer and came like gangbusters, spraying what must have been a gallon of semen into the condom. When my own shivering and shuddering was done, we lay there in each other’s arms, basking in afterglow.
“Is my lady pleased?” I asked at last.
“Very,” said Wendy, smiling dreamily. “Is mine?” She laid a hand on my blusher-shadowed cheek and caressed it.
I looked down at her, my red tresses dangling around our faces. “Am I your lady?”
“Do you want to be? Forever and ever?”
“Oh, yes, Wendy.”
“Then you are my lady - my beautiful twin sister - and I am yours. And when I’ve managed to recover my strength, I’ll go get my own big, thick strap-on and return the favor. Have you ever been fucked as a woman?”
I shook my head in the negative. “Not unless you count doing it to myself.”
“Well, tonight, my sweet girl, you are going to get it good and hard like I know you love it…and then you’ll really be one of us -- a real woman just like me.” She smiled and slid her arm around my cincher-clad waist. “You really are the best of both worlds. I’m so glad I ran into you at that club…and that I took a chance and reached out to you.”
“Me, too,” I replied and kissed her softly.
And when she did get her second wind, she kept her promise and filled my “pussy” (anus) with big, hard rubber cock. I came again sooner than I had ever thought I could after the first time, on all fours with her entering me from behind, and then again on my back underneath her with my high heels and stockinged legs in the air, playing with her boobs as she played with mine. Moaning and crying out like she had, I felt sexier and more gloriously female than I ever had before. It was nothing short of paradise. I knew then that I was hers…and she was mine, forever. I had finally found the woman of my dreams…one who loved my feminine persona and wanted to share it.
We’ve been together ever since, going out not only to drag clubs but regular ones and even a lesbian bar, where we both enjoyed being chatted up (and occasionally hit on) by all the baby dykes and butches and femmes. We still haven’t worked up the nerve to invite a third person, male or female, home to play with us…but we’ll do it one of these days.
END
Comments
Interesting, and never under
Interesting, and never under estimate the power of a Red head. Janice Lynn
Great story
I enjoyed the story. I think many wish something along that line would play out in real life;-))
Hugs,
Janet
its only monday
and after reading this I need the tranquilizers already, gorgeous horny story!
Ohhhh! I have to read this again... and again...!
What a dream - have you been inside my head, or what!!!??? You're a star! Thank you Cynthia! xx Ginger
Wow, HOT!
Pretty nice if Andrea had her own breasts, then everyone could just about feel everything.
Somehow, I've been horny all day. Ya got me to rub one out, but I managed to keep my panties on.....
Thanks for that.
Hugs and Bright Blessings,
Renee
I Kept Waiting For the Other Boot to Drop
I really thought he might be betrayed. Thankfully that was not the case.
Portia
If Wendy's for real...
...I would enjoy her taking Andrea to being more of a woman in her own right. As I see Wendy more toward making him her lesbian lover.
Warm moist hugs, JessieC
Jessica E. Connors
Jessica Connors
I just came across
I just came across this gentle story of understanding and acceptance
and found it very enjoyable
Thanks
SamanthaAnn
A nice reread
Thanks to the solo tease. A nice story where the protagonist doesn't have to be TG just enjoy his femininity. Sweetly written with just that touch of fear that a crossdresser feels when he's found out, A favorite to read on occasion when I want a lift.
Commentator
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Interesting
Not sure about the fetish part, but I enjoyed the story.