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Girl Friday By Gingerfred Man Chapter One - Casual day Lemon or baby blue? Perhaps pink? We all know what they say about girls who wear black panties, don't we? [Giggle] Fridays can be such a challenge. I mean, I had been wearing panties every day since my boss, Mr. Everhard's, "Girl Fridays" decree six weeks ago. But on Fridays, besides panties, I wore the miniskirt, stockings, garter belt and big heels to work too. On Monday through Thursday, when I'm wearing icky boys' clothes over my panties, stockings and garters, the color of my panties doesn't matter as much. But on Fridays, when I could "accidentally" expose my panties by lifting my skirt or the wind could raise my skirt or a lust-crazed man could flip my skirt up, bend me over, pull my panties down and FORCE me into satisfaction of his disgusting needs [which I did NOT want!], panty color could be crucial. OK, so already you can see how I'm not in a "normal" work situation and I'm not what most people would consider a "normal" guy. Well, my friend Paige would say that I'm "way better" than a normal guy. And she's "way right." I met Paige the day Mr. Everhard made "the announcement" at our company. We're a small advertising agency - twelve people, including the boss/owner/supreme leader, Rod Everhard. Three men, including the boss, me, the sometimes Ben Lickman, and my friend Billy Boffwell. Nine women. Good looking women - in their twenties and thirties. I was 25 - Billy was 24. Mr. Everhard was about 40. A good company to work for. Though "different" for sure. On "that day," a Thursday, Mr. Everhard called a staff meeting for all of us. Which was unusual in itself. If he wanted us to know things, he emailed us or blast voicemailed us. Face-to-face was so 20th Century. So we knew it was big. Mr. Everhard brought the meeting to order. "This is a great company and I'm really glad to have you all as a part of it," he began. Oh no. He was praising us. That meant he had either sold the company to port operators from Dubai or he was closing us down so he could seek enlightenment in Abbadabbastan. Wrong and wrong. He continued. "I know it's important for all you creative advertising people to dress like derelicts. No one can really think and produce in nice clothes, the current wisdom goes. But I'm sick of it. I know it's unreasonable to ask that you dress up five days a week, but I've decided that we're going to have a reverse casual Friday. Skirts, stockings and heels for everyone. Big heels too. At least three inches. And nice make-up. I want to see femininity on Friday and lots of it." Wow. My first thought was, "This is great! We have an office full of hot babes and they're finally going to start dressing nicely. Something to look at, every Friday." I looked over at Billy, my lone male colleague, to see his reaction. It wasn't happy, really. It was more...expectant. As if he were waiting for...more. He got it. Mr. Everhard turned to Billy and me and said, "And that includes you two as well. Skirts. Stockings. Big heels. Makeup. I want to see femininity wherever I look. If I don't, I'll find someone else to fill those stiletto pumps." Horror!!! Was the boss crazy? That was inhuman. Cruel! Asking, no demanding that his male workers wear female clothing to work every Friday. It was probably illegal and surely immoral. Billy and I would fight it. I knew that. I looked over at Billy for support, but I saw something else. I saw acceptance. Even cheerful acceptance. Billy was going to go along with that man's despicable delusion and I was going to be all alone. Or fired. What to do? When Mr. Everhard left, the girls set to teasing us in earnest. "Oh, I can't wait to see Ben and Billy's legs in stockings tomorrow," said Amber, the office manager. "I just know all the delivery men will be making a special trip back to their cubicles just to flirt with them." Loud giggles from all the office girls. Hot cheeks and deep shame from me. A happy smile from Billy. The thought of rough delivery men humiliating me every Friday, beginning the very next day, was terrifying to me. But Billy seemed OK with it. Hmmm. Well, sad as the prospect was, I didn't have many options. I could quit, but I loved my job, I needed my job and the job market was very tight. Maybe I could wear a kilt and tell everyone on my commuter train that I was converting to Scottishness. No, that wouldn't work. Scotsmen didn't wear stockings, heels and make- up, did they? Or so I imagined. All the office girls teased me every opportunity they got that awful day. Me. Not Billy. He seemed at peace with the prospect and teasing is no fun if the victim doesn't react. What was up with him, anyway? At around 4:45, Billy came into my cubicle and said, "Ben, look. Don't be worried. I can help you get through this, OK? Come home with me after work and we'll figure something out. You'll be fine. OK?" Reassuring words that meant little to me. Though it was kind of him to offer help. No one else seemed to be offering anything but ridicule. So I took Billy up on his offer. We left the office together at 5:30. In my hazy scenario of what would happen, Billy and I would go to some department store, suffer the humiliation of asking a saleswoman to outfit us en femme for work the next day, then ask a female relative to help us with our make-up. Billy had a different plan. He began by asking a strange question. "Are you a friend of Barbara?" Huh? Barbara who? My blank stare was his answer. "I didn't think so," he said. "Sometimes people who wear women's clothes to 'relax,' identify each other by saying that they're Friends of Barbara. I really didn't think you were, but I had to ask." Was Billy saying that he dressed in women's clothes? "To relax?" Was he gay?!?! "You really shouldn't play poker, Ben," he said. "Your face says everything you're thinking. I'm not gay. I just like wearing 'panties and things' sometimes. It's very...sensual. You'll probably enjoy it too. Most men who try it do." Me?!?!! Enjoy women's clothes? Horrors!!! No way! I was doing this temporarily. To save my job. Until I could find another job. Or the federal authorities dragged Mr. Everhard off to gender-offender prison. We reached Billy's apartment building. "Look," he said. "Just let me help you with your immediate problem, which is tomorrow, OK? Then you can start dealing with bigger issues." That sounded reasonable. I calmed down a smidge. His apartment was very nice. Almost too nice for a young man. Neat. Clean. No old pizza boxes. Lots of family pictures and knick-knacks. Kind of "girlish." Did he live with a woman? I stood there looking around a bit while Billy bustled around in the kitchen. He emerged soon, carrying a tray of cheese and crackers and a beer. In a glass! "Have a seat on the couch," he said. "Here's something to snack on while I consider your problem. And here's the remote." Beer, food and TV. Three of a man's four basic needs. That calmed me down a bit. I sipped beer, ate cheese and watched two sports guys arguing about whether some current ballplayer was better than some old ballplayer. Like any guy in that familiar situation, I calmed down. For about 40 minutes. Until Billy's bedroom door opened and someone I hadn't met emerged. Paige. Lovely Paige. Feminine Paige. Who looked like Billy, but didn't. Nice make-up on a pretty face. Long-legs in sheer, black stockings. Big, shiny, black pumps with five-inch pencil heels. A cute skirt and top. I was so dumb at that point that I looked toward the bedroom, expecting Billy to come out and introduce me to his roommate. Then she spoke. "My name is Paige. Do you think I'm pretty, Ben?" she asked. Oh no. It was Billy's voice, but softer and way more feminine. Paige was Billy! Billy didn't just put on a pair of panties to "relax." He transformed. Beautifully. Which was why he had no problem with "Girl Fridays." Which didn't help me at all. I still had problems. Beginning with, who the heck was this guy I thought was my friend and fellow male co-worker? Whoever "she" was, she was certainly pretty. And darned sexy. So sexy that, despite myself, I got a very large and throbbing erection in her presence. Which, of course, made things worse. Paige noticed my obvious arousal and blushed shyly when she saw that her appearance had pleased me. The whole thing just upset me more. Was my erection at someone who I knew was really a guy mean I was gay? Or did it just mean that I appreciated femininity? "Ben," she said, I know you're sorting through your feelings right now, but you'll be fine about all this. Trust me. Let's see how we can help you. Come into my bedroom and we'll see what we can do about tomorrow." Her bedroom? With her? What if something gay happened in there? Which seemed likely, considering the state of my swollen privates at that moment. But again, there didn't seem to be any better choices. I followed her. Into a bedroom of feminine splendor. Ruffles and pinkness everywhere. A large vanity table filled with cosmetics and girlie stuff. An open door to a closet brimming with feminine garments. Oh my. Paige snapped me out of my shocked state. "Let's get those boys clothes off and get you into a pair of panties. Thank goodness we're the same size." Clothes off? In front of this...this person who used to be Billy? There didn't seem to be any way around it. Especially since, if I didn't disrobe myself, she seemed intent on stripping me nude. I was blushing like a virgin bride when I stood naked before Paige's full-length, three-way mirror. Paige had to make things worse by commenting. "Very nice. You have a lovely body. Slim, with creamy skin and a nice, plump bottom. You'll look delicious tomorrow." I didn't want to look "delicious," tomorrow or any day. So why did my cock twitch when she said that? Paige didn't let that go uncommented upon either. "Well. Even if you don't like the idea, Little Missy seems excited by it." Little Missy? Oh. "Little Missy's a big girl," she teased. "Bigger than mine by a head. With a nice, pink mushroom and a lovely pink purse hanging down to hold your 'treasures.' You must have lots of fun with the girls." Another twitch. I hadn't really been much of a cocksman at that point in my life. A few quick fucks now and then. But I was too nice a guy for most women. The bad guys seem to get all the serious pussy. All that talk wasn't helping my condition. Why was I so excited? Paige stood behind me, watching my reaction as I looked into the mirror. "Let's try these panties on and then we'll see what we can do with cosmetics." She dangled the panties over my right shoulder. My first panties were pink and silky. I felt them against the skin of my shoulder and, involuntarily, I gasped. Paige smiled. That was apparently all she needed to know about me. She trailed the panties slowly down my front, "accidentally" brushing the pink teasers against my right nipple. Another gasp. Had I been able to call Scotty to beam me out of there and back to the Enterprise, I probably would have. And I would have regretted that beaming for the rest of my life. When the panties reached my pubic region, Paige reached around both of my hips, holding my new panties from hip to hip. The sensations were delicious. And humiliating. "Let's see how panties look on you," my tormentress said. "Oh, they look lovely! You'll be very pretty tomorrow. And look how excited you are." She was absolutely right. My upper lip was sweating. I was blinking furiously. And making strange little grunts. It was terrifyingly exciting. And deeply mortifying. I tried to fight it. I almost said, "Forget this, Billy. I'm leaving now and quitting my job tomorrow." Almost. But just as I was opening my mouth to say those words, Paige began to rub the panties over my cock and balls. Which made me completely inarticulate. And placed me completely in Paige's evil power. She wrapped the silky, pink treasures around my stiff, twitching cock and began to pump her pretty fist up and down. Up and down. Then all around the head. "You need to relax, Ben. Let me relax you, then we can get you ready for tomorrow." There was that "relax" word again. I didn't feel all that relaxed. Maybe I would if I just let myself go and.... Unnhh. Oh. It was so gay. And so wrong. But I surrendered to Paige's panty-penis pumping. Surrendered for the first time to my feminine feelings. And blew my guts out. I spurted so much semen into those poor pink panties that they were sopping wet. I drained my poor aching balls. Completely. I moaned with pleasure. That was the good news. The assault by a sledgehammer of shameful guilt was the bad news. That mixture of pleasure, humiliation and guilt was the headiest combination I had ever experienced. Another opportunity for me to chuck all the unexpected girliness presented itself. I could have dragged my semi-alive carcass into my man clothes and out the door. But having just experienced the most slam-bang orgasm of my life, it didn't make much sense to leave the scene of the slamming and banging. "I think you liked that, Honey," Paige said. "Let's get you spiffed up a bit and we can figure out a plan for tomorrow." Surrendering to Paige's superior will (and desiring further monster orgasms), I followed her into the bathroom. Like the rest of the apartment, it was pink and girly. How could I have worked with Billy so long and missed this side of him? "Let's get you shaved," Billy's feminine secret identity said. "You won't be able to wear stockings in the office tomorrow with those hairy legs." My poor cock twitched at the thought of walking around the office in a short skirt, heels and stockings! All the women would be looking at me! I would be so humiliated! And Mr. Everhard would be looking at me too! Massive humiliation! Oh my. I was stiff again. Why? I felt as if I were leaving my Home Planet and landing on a new world. Which was both terrifying and spectacularly arousing. Can you see why I had a major restiffie? It wasn't my fault, right? Meekly, I followed Paige to the bathroom, where she set about shaving all my hair below my neck. Below my neck! And I didn't resist! Even when she held my bumcheeks apart, quite professionally with her thumb and forefinger, and shaved the few hairs around my wrinkled bumhole. I groaned again and helplessly ejaculated! It was mortifying. And ferociously thrilling. Paige's eyes glowed as she watched me pour out my second tribute to femininity. And I had the oddest thoughts. I saw myself touching Paige all over. Just like the way she was touching me as she mercilessly dried me off and slipped pink stockings up each of my smooth legs. Oh! It wasn't possible, was it? I had a third hardon as Paige stood me up and hooked a garter belt around my waist and onto my stockings. Was she putting a pink bra on me? Hooking it in place despite my flat, chest. It was rubbing my nipples in the most arousing way. Then she had me put on pink panties! Panties! I was a man, darn it! No way I was... Oh! The panties felt so good as they rubbed against my circumcised cockhead. What was Paige doing to me? Then she did four horrible things in a row! 1) She sat me down and put makeup on me! 2) She slid two-inch-heeled pink shoes onto my feet. 3) She had me stand and put a pink, sheer, shortie nightie on me. 4) She undressed until she stood before me in only her bra, panties, garter belt and stockings. OK. So one look in the mirror affirmed that I looked hot as blazes. And my face looked better and femmier in makeup than I could have ever imagined. But I had never been so humiliated. And the thought of going to work the next day en femme was almost debilitating. So I did the only thing a red-blooded, cock-stiffened American boy could do. I moved in, took Paige into my arms, and kissed her. Rubbing pantied cocks as best I could. Now remember, I had already spunked twice. Paige had not spunked. So she should have spunked first. And she did. But I followed her by maybe ten seconds. Where was all that sperm coming from? Why was I so furiously aroused? And the big question - was I gay now? Hadn't I just kissed a man? And rubbed my stiffie against his? Kind of. But not really. Paige had a penis all right, but she was NOT a man. Snapping back to the issue at hand, my issue had drenched my panties. See how easily I called them MY panties? I was already losing my grip on what I had always accepted as reality. And loving it. "That was so nice, Honey," Paige breathed sexily. Let's take our panties off and get into bed. Maybe you'd better take that nightie off too. Going by the Handbook for Guys, "Humor anyone giving you multiple orgasms," I did as Paige said. So there we were. Lying side by side on Paige's bed. Wearing only our bras, stockings and garters. Oops. Paige unhooked my bra. And for some reason I felt more exposed than I had been when I took my panties off. Then I discovered the reason. Paige was rubbing and tweaking, just tweaking my right nipple! I screamed like a little girl punched by the schoolyard bully. And, I'm not making this up, I orgasmed again. It was practically dry. But mega-ballistic. I was quivering with the aftershocks as Paige kissed the inside of my mouth with her delicious tongue. It was so heady and absolutely fucking great that I did what any red- blooded American male who had just experienced his fourth orgasm would do. I fell asleep. I know. It was selfish to do so when I had had four love spasms and pretty Paige had only had one. But hey. I was sexually spent. Thank goodness my sexual stamina improved since then. But I was in a sleep deeper than the Marianas Trench. Nothing could wake me up. Then two things did. The first wisps of sunlight hit my face at 5:23 a.m. that morning. And the first lips of fellatio hit my penis at the same time. I was lying on my back and Paige was on her knees by my hip. Licking and sucking my cock!!! And doing it WAY better than any non-penis-equipped girl had ever done! It was so exquisite that tears formed in my eyes moments before I blasted Paige's tonsils with my first-of-the-day spermies. I was in heaven. Until I wasn't. There was no avoiding it after that. I was going to have to perform an act at least as homosexually homosexual as Paige had just performed for me. Which would pretty much make me homosexually homosexual, wouldn't it? Maybe not. Paige was still in her stockings and garters. So I could still rationalize that that stiff meat looking at me wasn't really relevant. Plus, Hannibal Lector said it best: "Quid pro quo, Clarisse. Quid pro quo." How dishonorable would I be if I didn't suck Paige's cock at that moment? And even swallow her spunk (ick!), as she had done for me? I was NOT to be dishonored! I swept aside thoughts that I desperately wanted to suck Paige's cock at that moment. And lick her balls too. Those impure thoughts were only sins if one lingered on them (Catholic Doctrine until fairly recently). I was doing the honorable thing. My duty. I wasn't going to enjoy it. But, of course, I did. A lot. I laid Paige on her back and touched her penis with my hand for the first time. My first, non-me penis-touching. I didn't die. Paige smiled at me. Goodness she was beautiful. I wanted to please her. And make her happy. She could see that. And she expected me to suck her cock, I think. I examined Little Miss Paige very carefully. Its fiery red head was saying things to me: "Kiss me, you pretty boy! Kiss me and let me show you how much I appreciate what you do for me." That was what I heard anyway. My only fears at that moment were: 1) I would do a poor job and she wouldn't cum 2) She would cum and I wouldn't have the chutzpah to take it all in my mouth and swallow Both fears were unwarranted. I wasn't actually a fellatrix natural or prodigy. But I seemed to be good enough for Paige. She squeaked and moaned and grunted and whimpered and even half-screamed when she shot her stuff into my mouth. I LOVED all that. For the first time in my life, I was certain that I had sexually pleased another person. And I had no problem completing the follow-through by swallowing Paige's surprisingly tasty issue. We did some sweet, deep kissing after that. Paige knew that she had dragged me across the Rubicon and I was happy being dragged in drag. The sexy stuff had to end because it was time to get up and get ready for my first en femme day at Mr. Everhard's House of Enforced Femininity. Chapter Two - Cathy Goes to Work I thought that Paige was being silly about stopping sex time when she did. But I was unaware of the prep I would need to look convincing for my first Girl Friday. Thank goodness we had already shaved my body. I had to shave my face, of course. And so did Paige. But the showering and hair washing took longer than usual, since Paige made sure that my bottomhole was sparkling clean. Makeup took an hour, since Paige fixed me, washed me, then had me rebuild my look. Corrections took a while. Paige had wigs for us both. Blonde, of course. Then we got dressed. Paige INSISTED that we wear real, black, seamed, fully-fashioned, reinforced-heel-and-toe stockings! And I was hopeless about getting my seams straight. But Paige pushed me into success. Garter belts, bras, blouses and miniskirts came next. And then the heels! Oh! My legs looked so effing hot in stockings and three-inch heels. Until I tried to walk. There went another half hour. Finally, Paige pronounced me ready for work time. We breakfasted on yogurt and dry wheat toast (ick!). And we were off in Paige's car. As we drove, Paige asked, "What name will you use when you're dressed, Honey? We can't call you Ben, can we?" I hadn't thought of that. How could I have, what with all the homosexual homesex and the crossdressing? So I just said the most generic girl name I could conjure: "Cathy, I think." Paige smiled. "Good name, Cathy. A pretty name for a pretty girl. I like it." I blushed. When we arrived at the office, Paige offered me the opportunity to appear we had arrived separately. "Unless you want everyone to think we're an item." I winced at that. Were we an item? Did I want Paige and me to be an item? I believed I did. But she was right. We, or at least I, would be eating enough crap from our co-workers that day anyway. Why make it worse? On a typical day, I rode commuter rail to work and walked five blocks. I would have been hospitalized had I done that my first day in heels. So I accepted Paige's kind offer to drop me off in front of our building, once she was sure that no Nosy Parkers were watching, I alit from the car with knees together as Paige taught me. Took a deep breath and headed for the elevator. Got off on the sixth floor. Heart pounding. Walked up to Linda, the receptionist. Wow. She was dressed like an actual woman and she looked great. I nodded at her and walked through the door toward my desk. "I'm sorry, Miss," Linda said. "That's for office personnel only. May I help you?" Oh my. I had fooled Linda into a) not recognizing me as Ben Lickman and b) not recognizing me as a man! A stunning achievement by my reckoning. "It's OK. Linda," I said. "it's just Ben. I'm complying with Mr. Everhard's decree about the Friday dress code." Linda stared. Processed. And didn't laugh. She hugged me and said, "You look amazing, Ben. How..?" "Determination to keep my job, Linda. But I had better get to work, so we'll talk later. OK?" She still looked semi-bewildered, but she let me go. To face the other eight potential critics. And Mr. Everhard. I sauntered in as casually as I could in my new heels. And was dazzled by the array of unfamiliar femininity. All nine female employees had, what was the expression, dolled up. Big time. And they looked great! Though I must say that Paige and I looked just as good. Where was Paige anyway? Wait. There she was. In all her feminine splendor. Eight sets of pretty, confused eyes swung in our direction. Amber figured things out first. "Ladies, say hello to Ben and Billy 2.0" They screamed and squealed and practically assaulted us with good will and admiration. Which was exactly the opposite of what I expected. Of course, who could have predicted that I would have been sucking Paige's cock that morning either. Just then, Mr. Everhard emerged from his lair to see what all the girlish fuss was about. And it was big surprise time again. "Well, Ben and Billy, I'm happy that you followed orders so well. Now all eleven of you ladies need to get to work." We hustled to do so. Though I did cast a gaze at Mr. Everhard. I know I didn't imagine what I saw. Mr. Everhard was looking at me, just me, "that way." Which was a punch in the gut to me. I didn't want my male, very bossy boss lusting after me. Right? Mr. Everhard went back into his office and I pondered what had just happened. Though work pressure distracted me enough to forget my unusual circumstances. At 10:34 a.m., one of the predictions a co-worker made the day before came true. A deliveryman who I knew as Brandon flirted with me. With me! And he knew I was really Ben. "Brandon," I said, "It's me, Ben. Our boss makes us wear girl clothes on Friday." "I know," Brandon said. "But you're amazingly beautiful." "Brandon, I'm a man." "Nobody's perfect," he said. Just like the closing scene of "Some Like it Hot," when Joe E. Brown meets all of Jack Lemmon's responses to his objections with similar responses. An unintended consequence. And an unsettling one. I did feel pretty good that Paige hadn't been propositioned by a man. And that Mr. Everhard hadn't given her the "filthy urges" staredown. We men are competitive after all. By 11 a.m. my poor penis needed attention. Both urinary and orgasmically. Should I go to the men's or the ladies? I asked Amber. "Follow me, Honey," she said. As far as I knew, Amber had never called me or anyone else at the office "Honey." Had I developed some new super power? Anyway, we got to the ladies. Amber opened the door, let me in, followed me and locked the door behind her. Uh oh. "Lift your skirt, Cathy, and get those panties down. You're going to urinate and then you and I are going to figure out why my ears have been on fire all morning every time I look at you." Huh! Amber WANTED me?!?!?! I lifted my skirts and dropped my panties. Exposing my shaved, red and very angry penis. Amber was in her late 30s and, dressed as she was, was very much a babe. I loved the fact that she was attracted to Cathy. Though she had given no such attention to Ben. But I had "difficulties." Peeing was an imperative, taking preference over even sex. And peeing with a raging Woodrow was a messy business. But Amber was wise. I had never been in the office ladies room and was unfamiliar with its amenities. My co-workers Carol and Kimberly were big lunchtime runners and had convinced Mr. Everhard to install a shower in the ladies. Amber made great use of it that day. She steered me to a spot just outside the shower, made sure my skirts were up and panties down, aimed my penis with her soft hand and said, "Go ahead and pee, Honey. Then we can have our fun." I wished she hadn't said that. It increased my sexual arousal and made peeing more difficult. But not impossible. I sprayed the shower and was greatly relieved. Amber released my cock, then ran the shower until all was clean. She then sat on a toilet and beckoned me over. My panties were still at mid-thigh. I was still holding my skirts up. I was very hopeful. And was not disappointed. Amber slid my cock into her sweet mouth and tongued the glans most succulently. But briefly. Before I could cum, she stood up and relocated so that she was facing the sink. She reached under her skirts and pulled her panties down to her knees. Her panties were sopping wet! She then gripped the sink, bent over and said, "I don't know why, but I want your cock in my pussy more than I've ever wanted anything in my life. I'm drenched already. Just shove it in and fuck me." And there she was. A delightfully pretty, mature woman. On her high heels. Bent over. Bare bum and bare, soaked vagina winking at me. A strap across each bumcheek, linking her garter belt to her stockings. Begging for my cock. Huh? I was living every male's fantasy by dressing as a woman. She didn't have to ask me twice. Oh! Her pussy was velvet. Even better since she didn't require me to use protection. She was moaning and gasping. Whimpering. And cumming. Then cumming again. She was leaking female cum fluid. And showed no sign of slowing down. It was perfect. I was already aroused by wearing femmies. I was fucking a beautiful woman whom I apparently could not disappoint. Who was neither nagging, manipulating nor emasculating me. My only fear was that Mr. Everhard and a SWOT team would break down the door and arrest me for excessive sexiness or malingering on the job something. No such fears were apparent in Amber. She was grunting and squealing through what I believed was her sixth stupefying orgasm when I shuddered and spunked. Hard. As our 45th president described his encounter with Marla Maples while he was still married to Ivana, "Best sex in my life." The setting was tawdry. We didn't even kiss or do foreplay. But my testicles didn't mind. Amber let out a muffled scream when I shot my sperm into her. Though she was so wet, I didn't see how she was aware of when I spunked. Phew! I was a little embarrassed when I reassembled myself, but Amber wasn't. She got a few tampons from the bathroom dispenser and plugged things up as well as she could. She fixed her hair. Looked at me and said, "Same time next Friday?" I nodded dumbly. What just happened? Amber was married, wasn't she? Yeah. I met her husband at the Christmas party. Amber left the bathroom. My co-workers gave me odd looks the rest of that day. At least I thought so. Paige confirmed my suspicions when we stopped work for a quick, late lunch at 1 p.m. "You and Amber reeked of sex, Honey," Paige said. "But that's a good thing. The ladies in our office admire your looks and your femininity. And so do I. I hope you'll stay over at my place tonight." I smiled broadly and accepted instantly. Though it did flash through my mind that had Amber made such an offer earlier, I would have eagerly accepted. Not that I would have accepted such an offer from that Brandon person. Or Mr. Everhard. Because I was NOT gay. Chapter Three - The Second through Fifth Fridays Paige and I had a delicious night of girlish delights. After work, we stripped to our stockings and garters, got into our tiny nighties, and kissed and licked balls and sucked cocks until the next morning. Paige fed me bacon and eggs, then politely, but insistently took me home wearing my boy clothes from Thursday. I was disappointed! Shouldn't we be spilling sperm all weekend? "I have a commitment, Cathy," she said. "I'll see you at work on Monday. Unfortunately we'll be Ben and Billy again. But on Thursday, we can stay at my place and get girlie." That sounded great to me. But it was noon on Saturday and getting into Paige's panties was 125 hours off. Sigh. I kicked around my apartment for a while. Brooding. Missing my girl clothes. Missing sex while girlied. Then I remembered some TV commercials about a place called "Timmy's Girlish Secret." A full-service, sissy supply store. Not that I was a sissy. But maybe I could just pop in and get some panties. You know. To wear. And a nightie. Or two. So I could sleep better. Just pop in. I drove the 3.6 miles to my local Timmy's Girlish Secret and popped in. For three hours and 28 minutes. And $2,124.18 worth of panties, stockings, garter belts, bras, night wear, day wear and high-heeled shoes. Oh yeah. And cosmetics. I guess I stayed longer than intended because my salesperson, Heather, was very friendly and helpful. And very sexy. I seemed to be the only customer that day who was alone and dressed as a man. But she was very sweet and understanding. And, since I had spent more than $2,000, Heather offered me a complimentary blowjob. Which I eagerly accepted. I was home by seven. Put my new things away. And got into my brand-new, lilac-colored, filmy babydoll. Omitting the matching panties. I admired myself in the mirror for far too long, got into bed, and barely brushed my cock with my nightie before it was spurting. Things had definitely changed in my life. I slept late that Sunday. Got up. Took a piddle, sitting down. With my babydoll still on, I made my self coffee and cereal. The phone rang. It was Maria from my office. That was odd. Maria was probably the hottest babe on our staff. Of course I was only able to discern that on that first Girl Friday, because before that, she had dressed like a ditch digger on her day off. I said, "Hello." She said, "Hi, Ben. Is Cathy there?" Huh? She wanted to talk to "Cathy?" Oh! Wow! I gulped. But rallied. "Just a minute, Maria," I said. "I'll get her." [Pause] "Hi, Maria. Ben says you want to talk to me." "Hi, Cathy. Say, I was thinking about what we were working on with the Shickelgruber account. Can I come over today and run those ideas by you?" We had never discussed a Shickelgruber account. Our firm had no Shickelgruber account But I wasn't stupid. "Sure, Maria. It's 10:30. Could you come by at 12:30?" "See you then." Oh my! Maria WANTED me! Me being Cathy, But I wasn't Cathy yet that day. And I had only two hours to become her. I went into action. Shaving. Showering. Dressing. By 12:28, I was wearing all pink - seamed, fully-fashioned, reinforced- heel-and-toe stockings; garter belt; bra; three-inch pumps. And the topper - a lovely, diaphanous, floor-length pink peignoir. No panties. Lots of cosmetics. Big, drippy stiffie. Maria knocked. I opened the door. Maria gasped. "Please come in, Maria." I said. "I'm afraid I haven't finished dressing yet. Please excuse me for a few..." Oh! Maria had me in her arms. Kissing me with tonguish passion. I swooned. Didn't know I could swoon. But I swooned. Maria was soon down to her bra, garters and heels. So was I. We were on the floor. Kissing and groping like high-schoolers in the back of a '57 Chevy. It was amazingly awesome! Maria was ridiculously randy. I touched her pussy and, like Amber's on Friday. It was drenched with arousal. I found her little love button as we kissed, rubbed it and she screamed out a showstopper of an orgasm. What happened next I can't describe fully because so much blood that would normally feed my brain had rushed to my cock. Maria practically RAPED herself. Shoving my fire-red cock into her wet, pulsing pussy. It was stunning! Here was a woman who never gave me a glance as Ben, but was ravaged with lust by Cathy. I LIKED it! And not just because it appeared I would be getting more ass than a toilet seat. I liked being Cathy. Wearing Cathy's clothes. Being pretty. Being desirable. Cathy was who I wanted to be. And not just on Fridays. At that time, such a notion was still fantasy to me. When we orgasmed, Maria and I screamed like little girl scouts who found out they won the cookie-sale competition. When our heart rates got below 150, Maria sucked off all the cum and girl juices from my cock and get me nice and stiff again. She got up took my hand and said, "Bedroom. Now!" So much for being manly and in charge. No problem. I led her to my bed, where she knelt on all fours, bum pointed toward me and said, "Lick my bumhole, Cathy. Please. I cleaned it before I came over. Get it nice and wet before you fuck me there." More loss of control, but in the best way, right? I licked and ate and tongued Maria's delectable anus. Listening with pleasure to her simpering grunts and squeals. And delighting that I could bring her to a big orgasm just from eating her ass out. After she squealed out the last of her cum, she begged me to bugger her. I first for me, And the best fuck of my life this far. My seven-incher slid into her bum with only minimal resistance. If it hurt her a little, I think she enjoyed that. Soon enough, my sword was in to the hilt. And my balls were slapping against her bum as I pounded her. Feeling very manly, despite wearing pink lingerie and half a pound of makeup on my pretty face. Anal sex was magnificent. Whole different "grip." Drier. No chance of procreation, Yum. Just to be sure that Maria was having a good time and would want to come back for more over the next 30 years or so, I kissed her neck as we fucked. Told her how beautiful she was. And rubbed her clitoris with a naughty thumb and forefinger. That did it. For both of us. Maria's orgasm triggered mine and we were shuddering and squealing. Most unmanfully. I didn't care. I saw a very bright future for Cathy. Rather than bore you with the details, let me summarize the next four weeks leading up to the flashback at the beginning of this true-life account. I got lots of pussy. Not as Ben. Always as Cathy. Six different ladies from the office "visited" Cathy at "her" apartment. Amber bent over for me in the ladies room every Friday morning and yes, we did one vaginal round, followed by a lovely anal. Paige (Billy) was incredibly proud of me! And we shared an all-night love session at her house every Friday after work. But she had "appointments" on Saturday and Sunday. Well, I had appointments too! Or at least Cathy did. It's funny. At the office on Monday through Thursday, the ladies, even the ones Cathy was banging, paid very little attention to Ben. As if the male me wasn't the same person as the female me. There were three exceptions to seeing Ben and Cathy as different persons. Billy (or Paige) of course. He was the one who really created Cathy. Along with the second exception - Mr. Everhard. The bossman seemed to be a lot more "interested" in me as both Ben and Cathy. Calling me in for client-related discussions all week long. Showing interest in me. I was a little uncomfortable about that. Didn't he know that I wasn't gay? I mean, except for sucking Paige's cock whenever I could. But I had long ago rationalized all that. Then there was the third exception - Brandon the deliveryman. He stopped by and chatted me (Ben and Cathy) up five days a week. Didn't he know about my non-gayness either? I didn't encourage him. Though perhaps I hadn't turned him down instantly on the fifth Friday when he asked me out for a drink after work. I was actually considering it. Out. On a man's arm. Taking in all the hot stares Cathy got from men instead of deflecting the stares. Maybe just once. But no. Brandon would probably be EXPECTING something for buying me a drink. Like a kiss. Or a few kisses. Followed by him unzipping his pants and FORCING me to suck his fat cock. Yuck! Right? Chapter Four - Date Night As we resume the scene of me getting off my commuter train on my way to my sixth Girl Friday, I couldn't miss all the hotness in the way men looked at my pretty legs in tan stockings, my yellow, four-inch pumps and my yellow sun dress. My goodness! Was I becoming a prickteaser? [Giggle] I hoped not. I arrived at the office and watched with semi-muted lust the way my co- workers eyed me down. Like a sex object. Not for who I was. It was deliciously degrading! Oh my. Brandon was already there. Delivering something or other. He gave me a mega-smile and the strangest thing happened. I got an erection. A real dress-splitter of an erection. Brandon said good morning to me and I smiled back. A la 1,000 watts. What was happening? He asked me again if I would have a drink with him after work and I though about the incredible sex I was going to have that Friday night with Paige. I thought about my heterosexuality and how Brandon would want to sully it. It was all wrong. I was no homo. So I did the only reasonable thing I could do. I giggled, looked down shyly and said, "OK. I'll meet you in front of the building at 5:15." Why did I do that? My brain said to me, "The fool is smiling at you. Catch him before he gets away and tell him you're not going out with him." But my cock was giving me another message. "Brandon is a nice guy. Cathy needs to see what it's like being with a man. Cathy is ready to be with a man. Brandon is that man." Oh! I was scared. And fiercely excited. Paige was VERY understanding when I told her that I would be breaking our regular Friday thing. She hugged me and said, "I'm so happy for you, Honey. I'll get another date for tonight easily. Lots of men like Paige." Men? Paige dated men? Every Saturday and Sunday? And other days too? How could I have missed that? Paige was letting MEN kiss her? She was sucking men's cocks? And maybe even doing other things? Oh the horror! Wait. Wasn't I in danger of having that happen to me that very evening? What if, despite my very sincere declaration that I was NOT gay, Brandon still tried to satisfy his filthy urges USING my body? What if Brandon thought I was so beautiful and desirable and sexy that he FORCED me to perform disgusting acts with him? Three minutes later, I was in the ladies room. Panties down. Left hand steadying myself on a sink. Right hand frantically rubbing my cockhead until I was crying out and squirting out six creamy globs of spunk into the sink. Why did the notion of being with a man excite me so? Was I a homo? Despite my ultra-femmy, "date" look with my female co-workers, I was always the man. I fucked them! They didn't put on some old strap-on and "peg" my pretty bottomhole. I'll admit to licking their pussies. And loving it. And I'll admit to licking three of my female co-workers' bumholes too. As a prelude to amazing anal sex. I loved anal sex. As long as I was the one penetrating the anus. I certainly didn't want Brandon penetrating my anus. With his filthy "business." OK. Cathy looked like every guy's wettest dream. But too bad for them. Cathy was in charge when sex was on the agenda. OK. I had sucked Paige's cock. Many times. And swallowed her girlish cream. But that was different. Paige was a girl with a penis. Which, I guess, was why she thought it was OK to date men. Ick! So why did I say yes to Brandon? Quickly. Which probably made Brandon think I was easy. And I was anything but easy. I would let the poor, obsessed guy down easy. Have one drink with him. As promised. Explain how he and I would never work. Pay for my own drink. Shake his hand. Wish him a good life. Catch a cab home. A good plan. So why, at 5:52 p.m. that day, was I in my apartment, in bed, with Brandon? I was wearing only my garters and stockings! Brandon was naked! And he was licking my nipples!! No one had ever licked my nipples. It was debilitating! It wasn't my fault, you know. His hygiene was excellent. He wore a suit. He told me how beautiful I was. And how lucky he felt to be even breathing the same air as me. And then her kissed me. It was exquisite. I was such a little tramp for a man. I stuck my tongue into his mouth before he did so in mine. Oh no! I creamed my panties. But Brandon was too much of a gentleman to mention it. He just asked if we could go to my place. And hailed a cab. We never did get that drink. In bed, Brandon was slow and thorough. The way a real man fucks his lover. He had me in a high dither with all that nipple licking. Which he simultaneously augmented with another move that startled me. Neither Paige nor my female co-workers had ever put their fingers into my bum. Nor had anyone else in my life. Thank goodness that changed. Brandon had my asshole on fire! He slid in one finger and I yelped. It was just so DIRTY! He slid the second finger in and I groaned. Sexily, I hoped. Brandon took my groaning as encouragement and the rogue eased in the third finger. Stretching me. which felt intimate and arousing. But that was only a prelude to the delights of the anus. I knew I had a prostate. Had never thought about it. Didn't really know what it was for. I learned of its best function at that moment. Brandon aimed his fingers at my prostate. Rubbing it. As he kissed, licked and sucked my right nipple. I'm only human. I screamed and creamed. Big, gooey, tasty strings of sperm and semen. All over my chest. And the back of Brandon's neck as he was nursing on my puffy. Oh dear, I shuddered and whimpered throughout the cataclysm. Then I did something that surprised us both. I cried. Brandon's heart appeared to melt. The way a good man's does when he sees a woman cry. But I wasn't a woman. I was just pretending to be one. And I had let a man do super-homo things to me. And [sob] I enjoyed it. Adored it. And wanted more. "What's the matter, Baby?" my co-conspirator in the destruction of my heterosexuality asked. He called me "Baby!" Which made things worse! I sobbed miserably. He held me in his manly arms. Which I liked. And that made things worse. Finally, I managed to calm my crying spasms enough to articulate, "I'm gay! I let a man do awful, gay things to me. Which makes me gay too." Brandon smiled. Which made me want to exercise my Second Amendment rights with him. This was a serious matter. But then he entered the path to redemption by saying, "Is Cathy a man or a woman?" I thought about that longer than I should have, then said, in a little- girl voice, "She's a woman." Then he said, "I agree. Cathy is a delightfully feminine, exciting woman. And I'm very lucky to be the man she has in bed with her. For heterosexual, consensual, ball-busting sex." My tears stopped. He was right. Cathy WAS a woman. And she had needs. One of which appeared to be doing sex things with a man. This particular man. Perhaps others later on. In fact, Cathy was looking at how stiff Brandon was as he held her in his arms. And how much Cathy wanted to touch Brandon's penis. So, as Cathy, a hetero, part-time woman, I reached down and took Brandon's cock in my hand. Brandon gasped. And I felt powerful. And womanly. I rose to my stockinged knees to perform a closer inspection of his excellent cockage. Mmmm. Just short of seven inches. Which is far from short. Uncut. Big, heavy balls in a hairy bag, Mmmm. I pulled back the foreskin and saw his glans. It was almost purple with excitement. Excitement that I engendered. Power! Brandon stirred. The poor guy was going to lose his load soon. I recognized the symptoms from my time as Ben. No sense wasting it. So, still kneeling [in apparent obeisance to my man] I took his knob into my mouth. And licked the underside most ferociously. The poor man did his best to hold back. And did so for a heroic three minutes. But he was vanquished. And I got my first mouthful of manjuice. Paige didn't count. It was delicious. And I swallowed it all. And kept licking until Brandon was half-hard again. At which point he drew me to his side for some kissing and pillow talk. Brandon, it seemed, was more than a delivery man. He was 26 years old and in his last year of part-time law school. He was very much a "pull myself up by my bootstraps" kind of guy. Another reason to like him. I told him about how I had been a college student at a small Midwestern school. Wait. Maybe that was from Penthouse Forum. Anyway, the talking stopped when Brandon was fully, achingly erect again - a condition I shared. I did ask him one relevant question: "Are you going to fuck me now?" A question I never thought I would ask. And I got an answer I never thought I would get. "Yes, Honey. Yes I am. Because I know you want that." Not a question. It required no answer. Other than me straddling Brandon's shoulders, facing his feet, and lowering my bum onto his face for a sweet session of analingual fuck- preparation. For the first time that lovely night, I surprised Brandon. But he loved the surprise. And dug his tongue into a place that had never known such an invasion. The randy lad ate me out for a good 20 minutes. Making me cum twice. And making me desperate to be fucked. Brandon was very accommodating. "On your back. Like a woman gives herself to her man." He barked. Oooh. I trembled as Brandon completed his pre-fuck preparations. He slid three pillows under my hips. Then he produced a bottle of Spermbutt Anal Lubricant. Which he applied with two fingers to my already sopping bumhole. Then slathered it all over his magnificent Cathy-pleaser. I mumbled, "Fuck me, Brandon. I can't wait." Which enflamed him even more. He shoved his cock halfway in, wriggled a bit, then completed the insertion. Ow. Not OWWWWWWWWWWWW!!!! But Ow. It pinched. Only pinched. A testament to Brandon's diligent ass-licking. Past the pinch, I adored being fucked. Even though it was the last, fallen defense of my expired male heterosexuality. I squealed and squirted a few, weak dribbles of my sissy cream. I grunted and gasped. I moaned and sobbed. I cried out, "Oh, Brandon! Make me pregnant! I want your baby!" I have no idea where that came from. But it was a very precise bullseye hitter for the male ego. Brandon's face turned red. His thighs shook. And he DUMPED a pint of cum into my sissy pussy. It was the best moment of both our lives. So far. Chapter Five - The Night after Date Night Brandon spent the night. But not the weekend. I wasn't ready for my bum to be fucked a fifth time. Well, maybe I was. But I sent him home after our fourth fuck in the 16 hours we were together. With the promise of another "date" on Sunday afternoon and night. I needed to rest. And collect my thoughts. Plus, Cathy needed a shave. And some maintenance. But there would be no rest for this sissy (which is what I had decided I was). When Brandon reluctantly went home at 9 a.m. on Saturday, I had no intention of dressing as Ben until Monday. Even then, I was wondering if I should start showing up at work as Cathy five days a week. I needed Paige's input on that. So I picked up my phone to call her. It surprised me by ringing just as I picked it up. Hmm. A number I didn't recognize. Probably someone selling aluminum siding. But I was curious. "Hello," I said. "Good morning, Cathy. This is Rod Everhard. Can you talk for a moment?" It was my boss! Mr. Everhard!! Asking for Cathy. So he wasn't firing me. Or asking for help on a project. Was he asking for something else? He was calling himself "Rod," so it was something else. And I knew what it was. "Yes sir. I can talk." Mr. Everhard cleared his throat. Was he nervous? I had never seen him nervous. "Um," he said. I had never heard him say "Um." "Cathy, I was wondering if you would like to have dinner with me. Um, tonight if you're not busy. Some other time if you are busy. If you would like." Oh! My boss was asking me out? Did he want to fuck me too? Apparently so. Did I want him to fuck me? My hardened cock told me the answer. "I would love that, Mr. Everhard," I said. "Shall we meet somewhere or will you pick me up at my apartment?" We agreed that he would pick me up. With any luck, we wouldn't actually be going to any dinner. We had luck. I was in full battle array when my smitten boss showed up at 6:30 p.m. Little black dress, stockings and lingerie to match. Black, four-inch, stiletto sandals. Lots of well-applied makeup. I looked way sexier than I ever had at the office. When Mr. Everhard saw me, I was glad that he was on our company health plan. I feared for his coronary coronariness. "You are amazingly beautiful. And sexy," he gushed. "The most beautiful and sexy woman I ever met." I shyly looked down and thanked him. And made no move to leave my apartment. He took my hand and gazed into my blue eyes. He kissed my hand. I gasped. He kissed my lips. I stripped. I was so easy. Which must be a big part of my charm. Four minutes later, Mr. Everhard and I were writhing in bed, kissing and groping each other all over. He was naked. I was wearing my bra, garters, stockings and heels. I think he liked me. I liked him too. He was manly and powerful. And yeah, it seemed he adored me. What's not to like? The man seemed to be particularly smitten by my stockings and heels. He began his by removing each heel, admiring it, then setting it aside. He then kissed each toe on my right, stockinged foot. Then the left. He returned to the right foot and licked it all over. Then sucked each toe most deliciously. By the time he got to my little toe on my left foot, I was in a sexual dither. Which he relieved by abandoning his foot adoration and placing his mouth on my thumping throbber. Five long sucks. Five hot licks of the underside of the knob. And I was paying my first tribute to Eros that fine evening. I payed him back in a manner that I knew he would love. I lay on my back, captured his stiff cock between the soles of my stockinged feet and rubbed them together all along his stiffness. Rubbing. For eleven grunting, ecstatic moments. His head almost exploded before his cock did. Oh dear! It was messy. Manly sploogee all over my pretty toesies. No problem. My boss licked all his sperm off my stockinged feet. And swallowed it. Something I could probably not envisioned six weeks ago. Or yesterday. He lay next to me after that. Kissing me. Telling me secrets. Big secrets. "I started this whole Girl Friday thing because of you, Cathy." Oh really? "Every time I looked at Ben, I imagined him in stockings and heels. I love stockings and heels. And only a pantyboy would be feminine enough to dress femininely every minute of every day. Ben had great potential. Your friend Billy had potential too, But he had a lot of mileage on him with men as Paige. I wanted someone who was discovering her femininity. You." Wow. Should I be flattered? I was. Should I feel sexually harassed? Stalked. A victim of a sexually hostile work environment? I didn't I loved my sexually charged work environment. The only thing it was hostile to was celibacy. I felt special. And rather than say so after Mr. Everhard's confession, I took his fat cockhead into my wet mouth and set out to restiffen his sissypleaser. He was 40. It wasn't instantaneous. But so what? I would gladly have sucked him all night. When he was at about three-quarters staff, he asked me to stop because he wanted to fuck me. If that was OK with me. To demonstrate, rather than verbally agree. I got out of bed. Put my heels back on, stood at the side of the bed and bent over. Front torso flat on the bed. Asshole winking at Mr. Everhard. He gasped. And went to work. In a different fashion than Brandon. But awfully good. Mr. Everhard pulled up a chair behind me, sat in it and began to kiss all around the welts of my stockings. Slowly. Sexily. He then kissed every pore of my shaved, plump bum. Avoiding the inner folds until he had driven me half mad with anticipation. When he finally dug in with his nose and mouth and tongue, I was half- frantic with lust. Oh my. Brandon was a very good ass-eater. Mr. Everhard was a world-class anal gourmet. Just a couple of minutes into his 25 minute feast, I succumbed to an agony of delight. And again moments before he stopped. My poor bumhole was soaked as he slid his Spermbutt Anal Lubricant- greased cock into my still-quivering pussy. So there I was. The impetus for a remarkably innovative work cultural change. A sex object for a half-dozen of my female co-workers. A full-participant in a transgender-transgender love affair. And the perfect paramour for two men. Why would I ever want to be anyone but Cathy? Please let me know what you think at [email protected].