It was late Friday afternoon at the office. As head of technical services for an IT consulting firm, I'd had a busy week, and was really looking forward to a relaxing weekend. "Excuse me Carl," the intercom squawked. It was my assistant Brenda. "Mr. Wilcox wants to see you in his office right away."
Oh jeez, what now, I thought to myself. George Wilcox was the president of the company, and a very likable guy, but I didn't want to get dragged into some last minute assignment this late in the day. "Okay Brenda, thanks." I replied.
Resigned to my fate, I walked down the hall to George's office. After a light tap on the door, I opened it and poked my head around the corner. "You wanted to see me George?" I asked.
"Yes Carl, come on in," George said with a smile. If he was anything, George was certainly friendly, even to the lowest employee. About fifty, slightly graying at the temples, and in excellent shape, George presented a refined and sophisticated image, combined with a charming down home friendliness. A combination that guaranteed success in whatever he chose to pursue. Frankly, I liked him a lot.
"Have a seat Carl," George said, gesturing to the couch in front of his desk. "I'll get right to the point. You've been here for four years, and you've been doing a remarkable job. The problem is, we haven't spent any time together outside of this building, and as a result I know almost nothing about you. How you spend your free time, what you like to do, and so on." I squirmed uneasily, hoping this wasn't headed where I thought it might be.
"Hmmm, Carl, that worried look on your face isn't necessary." George said with a smile. "I'm thinking about promoting you, and I'd just like to know you better, that's all."
"Well George," I said, relieved at his reassurance, "I don't think there's much to tell. I'm just an ordinary 27 year old guy." That was an outright lie, but I wasn't about to reveal anything just now.
"I'd like you to come over to my place tomorrow evening Carl, around 8 pm, for a drink. We can talk about the future." I studied him for any sign that he knew my secret, but his warm friendly face didn't reveal anything. "Okay, 8 pm at my place. You remember where it is, right?" he said.
"Yep George, on the waterfront. I love the view from your deck. I'll see you then." We had several company parties there, so I knew right where it was. I got up to leave, turning to give George a smile as I left. Rats, I thought, as I walked down the hall. I like spending all my free weekend time dressed as a woman, and now George is asking for a chunk of that precious time. Darn.
I've been dressing as a woman on my own time for years, and have gotten so good at it that many people only know me as Carly. The grocery store, drug store, several local bars and restaurants have never seen me dressed as a man. Being 5'6" and 130 lbs, with a slender face and delicate features, I pass easily. With years of practice my makeup and feminine voice skills allow me to go anywhere I want as a woman. And not as a slut either, but as a refined and well- groomed young woman, and as a result I'm constantly being hit on by men. I prefer older men, as they appreciate my special charms more, men such as George, I thought. Hmmm, I mused to myself. An idea was beginning to form in my mind.
After work I hurried home, showered and shaved, and got dressed for the evening. After doing my makeup, I put on some nice lingerie, stockings and garter, 3" black patent pumps, and a teal knit dress, followed by a necklace and matching earrings. My strawberry blond wig completed the look, so I grabbed my purse and was out the door. The entire transformation took less than 45 minutes. I drove to a nearby hotel to have dinner and drinks, and to see what the evening might bring. As almost always happens I was in a gentleman's room soon enough, on my knees with his throbbing cock in my mouth, as I worked passionately to bring him to a climax. I loved weekends.
Saturday, I awoke with excitement. I had made a decision the night before about the visit with George, and I tingled at the thought of it. I was going to George's house en femme. He wanted to know what I liked to do in my free time, after all. Well, I enjoy being a woman, so I'm going to reveal it to him. I'll let him determine if I reveal my sexual desires or not. George lived alone, and as far as I know he'd never married. Hmmm, we'll see where this leads.
I spent Saturday shopping, first the grocery store in the morning, then the mall in the afternoon. Dressed in a nice skirt and blouse, I easily passed amid the usual weekend throng of people. At the mall I purchased new barely black stockings, and a new black half-slip with lots of lace. Stopping at the drug store I bought a new tube of KY lubricant and a bottle of Estee Lauder perfume.
After a light dinner alone it was time to get ready for my date with George. After bathing and shaving I slipped on a lacy black bra with my realistic latex breast forms. Realizing the outfit I would be wearing was somewhat low cut I took the time to create some cleavage, using surgical tape under my breasts. Next, I put on a lacy black garter, followed by the new barely black stockings. I pulled on my new half-slip, and slipped on a pair of 3" black patent pumps.
Sitting at my vanity I applied my makeup, starting with a light coat of foundation. Using an eyebrow pencil I lightly filled in my feminine eyebrows and underlined my eyes. I added black eyeliner above my eyes, followed by mascara. I tried not to overdo my eyes, going for a sultry but fresh, classy look. It worked. Finally, I applied my lipstick, "Currant" by Mabelline. A squirt or two of Estee Lauder finished the job.
I chose a matching skirt and blouse combination from Bob Mackie Designs, that he calls "Wearable Art". It was a periwinkle color, with black and pink geometric designs in a polyester and spandex fabric that draped beautifully. Tucking the blouse into the skirt, which fell just below the knees in a flare cut, and adding a black patent belt, made it looked like a sexy, alluring dress. Perfect for the occasion, I thought. I added a gold necklace and earrings. The necklace settled into my cleavage, which looked really sexy.
I put on my strawberry blond wig, brushed it a bit, and I was finished. I dropped my lipstick and perfume into my purse, along with the tube of KY lubricant (one never knows), and I was ready to go. I put on my black slinky knit cardigan, as there was a slight chill in the air.
I arrived at George's condo building right on time, pushing the button for his unit. The security door buzzed, and in I went. As I walked down the hall, my heels clicking on the hardwood floor, I realized I had crossed a threshold, mingling work with play. A dangerous game, I thought, as I nervously rang George's bell. The door opened, and George stared, dumbfounded, not recognizing me at all. "Yes?" he stammered, confused a bit. "May I help you?"
"Hi George" I said, smiling. "Aren't you going to invite me in?" Still unsure, George mumbled something, and stepped back, inviting me into his home. I walked in, looking around at the elegant waterfront condo. The large picture windows in the living room looked out over Lake Washington, with the lights of Seattle in the distance.
I stood in the middle of the room, looking at George, and said, "You wanted to know what I did in my free time George. Well, this is it. And please call me Carly this evening, okay?"
George just stood there, a bit red-faced, and asked if I wanted a drink, which of course I did, badly. I think I was just as nervous as George at that moment. As George poured each of us a drink he looked over his shoulder at me and said, "Let's sit out on the deck for a bit, while it's still warm enough, okay, ah, Carly." With that he handed me my drink, and lead me through a sliding glass door to the deck overlooking the lake. We sat in chairs around a small table. George just stared in amazement at me.
As I took a sip from my drink, my legs crossed in a feminine manner, George cleared his throat and said, "Forgive me, but I can't take my eyes off you. How long has this been going on?" I set my glass down, and smiled at him for a bit, wondering how much I should tell him.
"Almost all my life George. I've been good enough to go out in public since I was about 16 or 17 I think. I spend all my weekend time as a woman. It's the most enjoyable thing I know. I do all my shopping as a woman, I have a female driver's license, checking account, several credit cards. Really, an alternate life, if you will. Do you like it?"
"Like it!" he exclaimed. "I love it! I can't get over what a beautiful woman you are. The whole package is there, makeup, hair, clothes, voice, mannerisms. You've really mastered it, and I'm impressed." George looked at me for a bit, smiling. "I think you're the most beautiful woman I've ever seen. And, I might add, I'm really attracted to you as well." I smiled back at him, and slowly sipped from my drink. His words caused a stir of arousal in my loins, and I really didn't want an erection just then. I crossed my legs the opposite way, hoping I'd calm down.
We talked for about an hour out on the deck, mostly about the company, about my position, and about the possibility of a promotion to V.P. I was excited about that. I was worried, though, that my newly revealed lifestyle might spoil that possibility. George flirted with me quite a bit, which made me feel better, but also kept my arousal level pretty high. He told me how much he liked my dress, saying it made me look sexy. Finally, he suggested we retire to the living room, as it was getting chilly on the deck. I was getting my hopes up at this point that maybe this would take a turn for the better. I was getting so hot I could hardly stand it
As we entered the living room I took off my cardigan and draped it over a chair. George invited me to join him on the couch, so I slid down next to him, but not too close. He asked if I'd like another drink, which I did, so he left to make each of us another. When he returned he sat back down, but closer to me. Hmmm, I thought, is he going to seduce me? I was hoping he would, and just then he placed his arm around my shoulder, pulling me closer still. I melted in his arms, laying my head lightly on his shoulder, purring contentedly. I knew then exactly what was coming next, and I couldn't wait.
"Carly," he said softly, "I said earlier that I was attracted to you, and I meant it. You are so beautiful." I responded by sliding a bit closer, then placed my hand on the inside of his leg, a little below his cock. "Ummm," he moaned, "just what I had in mind." A growing mound now showed in his pants. I licked my lips, eager to taste his erection. I slid my hand further up his leg, and lightly brushed his cock. His pants were made of a light knit fabric, and I could feel everything. His breathing quickened as we kissed passionately, eager to be in each other's arms, and even more eager for what was about to happen.
"You know George," I purred softly, "I find you very attractive as well." He was breathing hard now, with anticipation of what was ahead. "As a woman, I know just how to satisfy a man." I knew he was mine, as my hand settled around his now rigid cock. "I think it would be wonderful if this found its way into my mouth." As I began stroking his cock he moaned with pleasure. I wrapped my fingers around his huge erection, feeling the throbbing head through the thin fabric.
"George," I said, breathless with excitement as I kissed him softly, "I want to take off your pants and get that big cock in my mouth baby. I can't wait any longer." With that I began to unbuckle his belt, and unzip his pants. With George's help I had his pants and shorts down around his ankles in no time. I slid down and kissed his raging erection, moistening it with my tongue, and finally took it into my mouth. He gasped and exhaled deeply as he moaned with delight. First the head, then a bit deeper, and finally I took it all the way into my throat, as George lightly placed a hand on the back of my neck. Moaning with sheer pleasure, I slid my mouth slowly up and down the shaft, caressing it with my tongue, driving George wild with desire. I really love sucking a man's cock and driving him wild. George was pushing my head down, and raising his hips up, trying to get his cock deeper into my throat. I was only too eager to help.
Sliding down to my knees, I began sucking in earnest, wanting him to come in my mouth. George had both hands around the back of my head pushing me down on his cock when, suddenly, he pulled me up, saying, "I don't want to come just yet Carly." Sitting me back on the couch, he slid his hand under my dress, feeling my erection through my panties. "Nice," he said, "just what I want." He slid my panties off, pulled up my dress, and began sucking my cock hungrily, like it had been years since he had done it. "Very nice," he said as he took a breath, "I've been wanting to do this for years." He resumed sucking, sliding his mouth up and down my raging erection. I was getting close to climaxing.
Suddenly, he rose up and said "Let's 69 on the floor." With that he slid down to the carpet, lying on his back, beckoning me to come down on top of him. I straddle him on all fours, pulling my dress up around my waist. As he took my cock into his mouth and began sucking, I slid my mouth down around his erection, bobbing up and down, hoping he'd come. We both moaned with pleasure as we sucked each other passionately. As I took him deep in my throat he stiffened a bit, then came with a tremendous climax, sending waves of sweet, delicious come into my throat. As I swallowed it I also came with a wave of passion, sending my seed deep in his throat. I savored his sweet taste as I licked and sucked his still swollen cock clean. I loved his manly taste and smell, and hoped I'd be doing this with him often.
Finally, we fell into each other's arms, completely spent after our passionate sex. It was the best 69 I'd ever had, and, I came to find out, the first time George had taken a cock into his mouth. "Carly," he said, " I must confess I hadn't done that before. I've been fantasizing about it for several years, but was afraid to try it. Thank you so much for being a woman tonight, for allowing me to have the kind of sex I've dreamed about. It allowed me to indulge my fantasy along with yours. It was great, and I love the taste of you in my mouth." Then, he kissed me passionately, over and over.
I finally excused myself, retrieved my panties and purse, and went into the bathroom, where I freshened my lipstick and straightened my hair and clothes. Satisfied, I returned to the living room, where George, now dressed, offered me a fresh drink. We talked for a bit, with George asking if we could date again. "Of course we can George." I said. "All you have to do is ask. I had a wonderful time tonight, and sex with you is terrific. We can do this as often as you like. Being a woman with a handsome, sexy man like you is nothing but pleasure for me."
George smiled, gave me a kiss, and indicated it was getting late, so I got up to leave. At the door, he kissed me again, passionately. I really like a man who kisses passionately, and I rubbed his cock as he kissed me to let him know. Finally, I turned to leave, my heels once again clicking on the hardwood floor of the hallway. I found myself thinking, with a smile, just who conquered who tonight?
Monday, I was scheduled to go to a client's facility for a week long trouble shooting job, thus I was out of the office nearly the entire week. I was able to check my e-mail, using the client's computer, and found an e-mail from George on Wednesday. He was asking if I'd like to meet for dinner and drinks Saturday evening at the Four Seasons Hotel. I promptly responded that I'd love to, and would meet him at 8 pm.
Saturday, I went shopping for a new dress to wear that evening, and found a lovely slinky knit black sheath, that fell just a bit below the knees. It fit perfectly, with long sleeves and a low-cut neckline. Wow!! Would I be a knockout in that.
At precisely 8 pm I strode into the Four Seasons dining area, dressed to the nines in the black sheath, with about 3 inches of cleavage showing, and 4 inch black patent heels. I turned more than a few heads as I looked for George, and finally found him sitting at a table in the corner. As I walked toward him, hips swaying and diamond necklace and earrings glistening, I could feel every eye in the restaurant following me. I loved it!
We had a lovely dinner, then a couple of drinks in the bar, before George invited me to his home. I followed him in my car, excited about the possibilities ahead. When we got to his parking garage, he waited for me to catch up, then we walked up to his condo together, arm in arm.
George made us each a drink, and we made small talk on the couch for quite awhile, kissing passionately from time to time. Suddenly, he turned to me and said, "I think you should come to work dressed as Carly from now on."
I was caught completely off guard with this idea, and stammered a bit. "George, I couldn't do that. What about Brenda and my other co-workers, and all our clients? I mean, they all know me as Carl." I gave him a light kiss on the cheek for the idea, but was sure it wouldn't work.
Finally, George invited me to his bedroom, saying he had something special in mind. I followed, anxious in anticipation. He kissed me several times, then reached around and unzipped my dress, letting it fall to the floor. Kneeling down, he slid my half slip and panties off as well, before pulling me onto the bed. I worked feverishly to get him undressed too, finally getting him naked on the bed. I was surprised at how well conditioned he was.
Lying beside him, I stroked his cock as it became more and more erect, and finally I rolled over and took it into my mouth. Licking and sucking, I wanted to get him completely aroused, when, much to my surprise, he wanted to 69 again. We sucked each other passionately for what seemed like hours, when suddenly he rolled me off, saying he had something else in mind. He wanted in the worst way to fuck me.
"Oh George," I moaned passionately, "I was hoping you would." I was beaming with delight at the thought of getting fucked by this wonderful man. I flashed briefly on the fact that I had been fucked perhaps a thousand times before, but I never looked forward to them as much as I did to this one. I said, "There's a fresh tube of KY lubricant in my purse dear."
George chuckled a bit at that, and said, "Ha, I bought a tube myself today." He retrieved his tube from the nightstand, and applied it generously to my pussy and his thick, hard shaft. "Lay on your back," he said quietly, "I want to fuck you from the front."
"George, I'd love to do that way. Please, hurry," I said breathlessly. He pushed my stocking covered legs up over his shoulders, and lowered himself down on me. I gasped breathlessly as he slid his swollen member effortlessly into me. I moaned in passionate delight as he slowly began thrusting deep into my pussy, then withdrawing, only to thrust in again, burying his member all the way in. I put my arms around his head, holding him tightly and kissing him as he fucked me harder and harder, our love making more passionate than the previous week. "Fuck me harder George," I cried, "faster baby, faster and deeper. Oh god I love it so." My breathing was becoming rapid and shallow, as my excitement and passion grew beyond belief. I was more excited and aroused than I had ever been before.
I absolutely loved this, and I tried to show it by responding to his thrusts. Moaning and gasping in joy, I pulled my legs tightly around his back, pulling him further into me. Finally, in a shudder of passionate climax, he came in a cascade of come, deep in my pussy. As he let out a gasp of pleasure I cried out in passionate lust. I kissed him over and over, telling him how good it was, how good he was. "Carly," he said, "I think I'm falling in love with you." I smiled, delighted to hear those words, and kissed him passionately. I was falling for him too.
Finally, as his cock slipped from my pussy, he rolled off and promptly went down on my erection, sucking voraciously, taking it deep into his throat. I shook and trembled, and finally came in a torrent of come, as he struggled to swallow it all. Finally, he kissed my still throbbing cock and cleaned it with his tongue. We were completely spent after that.
After getting dressed we shared a final drink, and talked a bit. "Carly, he said, "I'm serious about you being a woman at work, as well as in my bed. I think having a female executive would be good for our company profile, and you're the one for the job." I thanked him and said I'd think it over.
I spent Sunday washing my wig, lingerie, and clothes, and thinking about George's proposal to go to work as Carly. I had dreamed for years, actually, about doing just that, and the thought of it gave me goosebumps. I had always wanted to live full time as a woman, but I was worried about my career. I surveyed my wardrobe, and concluded that I could go a couple of weeks with the daytime outfits I had, and I could always buy more if needed. But, nah, I thought, as much fun as it sounds, it'll never work. Still, it might be fun to go in Monday dressed. I knew Brenda, with her wicked sense of humor, would get a huge kick out seeing me dressed as a woman. So, perhaps just for one day, I rationalized.
I picked out the outfit I would wear, a mauve and pink silk charmeuse blouse, black knit, knee length skirt, black leather 2" pumps and belt, and basic jewelry. A black blazer would complete the look.
The next morning I bathed and shaved, ate a light breakfast, then got dressed for the office. I put on an ivory bra and garter, nude stocking, ivory tap panties and matching half slip. Sitting at my vanity I applied light makeup, jewelry, and finally added a bit of perfume. After putting on my blouse and skirt, shoes and belt, and finally my blazer, I was ready to go.
As I entered the office building the security guard said "Good morning Miss Edwards." as he waved me through the door. I nearly froze in my tracks at that, puzzled about how he could possibly know who I was. Hmmm. Oh well, I smiled at the guard, and walked in, hips swaying in a very feminine way.
Walking down the hall to the tech support section, I spotted Brenda sitting at her desk. She looked up, surprised, and said, "Hello, may I help you?" She didn't recognize me, which was amusing, I thought. I smiled, and was about to speak when, just then, George approached from the rear.
"Good morning Carly, so nice to see you. You look great. Come with me and I'll show you to your office." He turned to leave, and I followed. Behind us, Brenda stood with her jaw open, not sure just what she had witnessed.
"Carly, Carly?" Brenda uttered softly. "What is this all about?" Hearing this as I left with George, I just smiled and kept walking.
As George and I walked down the hall in the direction of his office he turned and said, " Dinner tonight at my place? Please say yes."
I took his hand and gave him a light kiss on the cheek and said, "Of course darling. I'll see you at 8." Out of the corner of my eye I could see Brenda at the far end of the hall, watching intently. Well, I thought, our secret is out now. I don't know why, but that actually pleased me.
Arriving at the end of the hall, George motioned to an open doorway opposite his office. "This is your new home Carly." He gestured for me to enter the large corner office, which was furnished with very expensive furniture. As I entered I saw an engraved plaque on the door. I took off my blazer and sat in the plush executive chair behind a large gleaming mahogany desk. Crossing my legs like a lady, my eyes wandered back to that plaque on the door. I was beaming with a radiant smile, knowing a dream had come true. The large engraved brass plaque on the door read: "CARLY EDWARDS - VICE PRESIDENT"
Paula
If you like the above story, let me know at paulabthomas@yahoo.com.au