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Tuition Assistance By Gingerfred Man Chapter One - Busted College life started out very well for me, Bobby Pipeuse. Mom and Dad sent me to a fine, expensive university where I could develop my skills in drama - my lifelong passion since I wowed 'em as Curly in my high- school production of "Oklahoma." I enjoyed living in the university's dorm, where I was even indulged by a private room. I didn't even mind the institutional food. My classes - both drama-related and non-drama - were great. Since Mom and Dad were paying full freight, as well as sending me $100 a week in spending money, I had plenty of time to study. And plenty of time to goof around with my friends. But that only lasted one semester. Then the roof and the walls caved in, as the floor collapsed and it was all sucked into a bottomless vortex. Dad lost his job. Mom had never worked. Neither had saved a nickel. And neither had paid my tuition, room or board for second semester. My parents told me all that over Christmas break and, unlike most teenagers, I felt bad for them. And didn't spend all my mental energy thinking about how their misfortune was destroying my plans. Though it did. Almost. Against their advice, I decided to go back to school for the second semester. I took out student loans and worked two jobs - waiting on tables and catering jobs. I tried to juggle it all, but it wasn't working. Two weeks before finals, I checked my distribution box in the dorm and found an official notification that said, "Dear Mr. Pipeuse, we are sorry to inform you that due to non-payment of fees, you will be removed from the dormitory and dis-enrolled from the university, effective [two weeks hence] unless you make a payment to the Registrar of $6,432.78." That was that. I could have paid the 78 cents, but not the rest. I was doomed. I would be crated up and shipped back to my hometown in a box marked "Deadbeat." Or perhaps sent in chains to debtors' prison. Not that I didn't expect it. The university had been dunning me for weeks. But this seemed final. It would have been perfectly normal of me to say, "Screw it," at that point. Leave the university town. Hop a freight car to nowhere. Maybe hitch to New York or L.A. and get an acting job there. But I was never normal. I had promised the folks at the Hungry Heifer that I would wait tables for them all weekend, so that was what I did. Gloomily. Though I did it. All would have been so different if I hadn't gone to the restaurant that night. Very different. I sleepwalked through my shift until about 8:30, when an extraordinary couple came in and was seated at one of my tables. Context is definitely called for here. The Hungry Heifer is a large restaurant for large people. The men who eat there haven't seen their bellybuttons in decades. The women are as bovine as the restaurant's name. Despite their girth, or perhaps because of it, the men were great tippers. That was why, four or five shifts each week, I dealt out slabs of beef with heart-stopping side dishes. The couple who came in that night were as incongruous in that setting as a boy in a beauty parlor. The man was a silver fox - middle aged and obviously wealthy. The woman was taser-blast stunning! She appeared to be college age, with gorgeous features, expertly cosmetized. Her long, silky blonde hair framed her face in a halo of femininity. Her red dress screamed "Fuck me!" so loudly that it even stirred the cholesterol junkies consuming singed animal parts all over the restaurant. Her legs screamed "Fuck me!" even more loudly. They began at the hem of her flouncy, achingly-short skirts. Curving south through scrumptious, dark-tan-stockinged thighs. Sliding down to shapely calves and knees that I ached to put her on as she sucked my cock. Ending in red pumps so high she could have dunked a basketball without jumping. Barely-there, pencil heels. The fox and the angel seemed very absorbed in each other (duh - any man on earth would have wanted to be absorbed in that one), so I waited a bit before presenting myself for their order. When I did so, it was surprise time. Big surprise. Angel looked away from fox and locked eyes with me. I almost creamed my pants. But that wasn't the surprise. This was. "Bobby? Bobby Pipeuse? How are you? I haven't seen you in years. [To silver fox: "Honey, Bobby and I went to high school together."] We did? No way. I had no recollection of anyone in our school being one-millionth as sexy as the lady in red. I would have remembered her until every neuron in my brain had stopped firing. She went on, "Oh, Bobby, you and I simply must catch up. Why don't we have our dinner, then, when your shift is over, you can come sit with us and tell us what you're doing. That's all right with you, isn't it, Skippy?" Skippy? The silver fox was "Skippy?" Apparently so. "Of course, my Darling," fox said to angel. Which was the same response any sane man on earth would have made to someone toting a pussy like the one she surely must have carried. I took their orders: half-slab of ribs for him and a girlie salad for her. Both were firsts for the Hungry Heifer. No one ordered half- anythings. And salads were fooda incognita as well. Goodness knows how the chef managed to whip up a salad for the babe. Or how she managed to eat it. They chatted amiably throughout the meal, polite to me, but clearly absorbed in each other. At one point, if I didn't know better, I would have sworn that angel's hand dropped below the tablecloth and gave fox a nice, slow handjob. I may have been imagining it. But he certainly looked very happy for about fifteen seconds at one point of the evening. At 11, my shift was over and angel and fox were the only patrons left in the restaurant. Fox looked familiar to me, but I couldn't place him. Angel looked just a tiny bit familiar too, but some context wasn't there. Angel invited me to sit with them and I did so. She spoke, "Bobby, I can tell that you don't remember who I am at all. But that's understandable. I was very different in high school." Weren't we all? Still, even in a potato sack, angel would have stiffened cocks all throughout the postal zone. She smiled gorgeously. "Bobby, my name is Gretchen. Gretchen Schtupmore. Does that ring a bell?" I shook my head dumbly. "I knew a Tommy Schtupmore. He was two years ahead of me. I think he played football. Was he your brother?" She smiled again. "Not exactly. It doesn't matter. I remember you. A nice guy. And a good actor. Are you studying acting at the university?" That question did me in. Mortifyingly, tears welled in my eyes and I began to weep. I told Gretchen and "Skippy" my sad story, about my parents' destitution, my expulsion and my complete lack of a future. Gretchen was fantastically sympathetic. She put her arms around me and told me not to worry. Easy for her to say. Then she did something that changed my life forever. "Skippy," she said. "It's not right that Bobby's life should be ruined because of some old money thing. Can you help Bobby out on this?" Skippy looked into Gretchen's beautiful eyes and gave a man's best answer, "Of course, Sweetheart. I'll see to it first thing in the morning." Huh? I stopped crying and looked at them both. Puzzled. Mildly hopeful. Then it dawned on me. The silver fox was Dr. Russell T. Academia, the university's dean. I still had no idea who Gretchen was, but she had apparently just saved my career. Through the all powerful weapon of pussy. She even pressed her luck. "Skippy, Sweetie. Why don't we go to your place now and you can put all that in writing before we 'get comfortable.' Then Bobby can call me tomorrow morning, we can meet somewhere and he can pick up the paperwork that lets him continue as a student here." Skippy smiled. "Of course, Honey," he said. If Gretchen had said, "Skippy, you can fuck me if you get into a crouch and bark like a chicken," Skippy would have figured out a way to do that. Gretchen wrote her phone number on a piece of paper, told me to call her the next day, Saturday, after 10, and left with a very happy Skippy. Could it all be true? I found out soon enough. Chapter Two - Payback I got to my dorm room filled with what I prayed wasn't false hope. Aside from a nagging feeling about recognizing Gretchen from somewhere, I was feeling great when I went to sleep and great when a ringing telephone awakened me. I picked it up and mumbled, "Hello." "Hi, Bobby," the telephone said. "It's Gretchen." I sat up alert in bed. "Good morning, Gretchen," I said. I rubbed my eyes and said, "Thank you so much for being so kind to me last night...you and Dean Academia." "It was our pleasure, Honey," she said. "I have good news for you. Skippy took care of everything for you. Your tuition is taken care of for the rest of the term. And your room and board. Though you may want to reconsider that part." Huh? Why wouldn't I want room and board? I had to eat and sleep, didn't I? But I was in no position to disagree. "Thank you so much, Gretchen," I said. "You're a lifesaver! How can I ever thank you?" "Not necessary, Honey," she said. "Anything for a high school mate. But I would like to talk to you about something. Are you free for lunch today?" I was puzzled about the "high school mate" part. But of course I agreed to meet Gretchen for lunch. After showering and shaving quickly, I got my bike and hustled over to the address Gretchen gave me. It was a very ritzy condo building about a mile from campus. Gretchen was definitely living large. I took the elevator to an upper floor, sought out the apartment number and knocked on Gretchen's door. She opened the door almost immediately and there she was. Spectacular as she had been the previous night, if not more so. She was wearing a lovely, yellow, sundress with spaghetti straps and a short hemline. Which showed a lot of fantastic leg! Encased in tan, seamed, fully- fashioned, reinforced-heel-and-toe stockings and accented by dark red toenail polish and strappy, yellow, four-inch-stiletto sandals. Totally fuckable. As if that did me any good. She was the kind of girl who was squired around by guys like "Skippy." Not broke, younger-than-her losers like me. Though she didn't treat me like a broke, younger-than-her loser. She was sweet and gracious. She kissed me on the cheek and I got a whiff of her "Poison" perfume. "Oh, Bobby," I'm so glad you could come. It was so wonderful to see someone from back home. And I'm so happy Skippy could help you. Come in. Come in." I came in. The place was beautiful. Modern, comfortable furniture. Expensive everything. I suspected a rich Daddy back home. She led me to the dining room and sat me down, then served me a very "healthy" lunch of various greens and lemon juice. The conversation was easy and comfortable. She wanted to know all about my drama classes and my drama with my family. She claimed to know my parents and gave details that showed she did. She knew tons of people back home that I knew. After about an hour of that I was consumed by curiosity. "I'm sorry, Gretchen. You've been my great benefactor and you're the most beautiful girl I've ever met. But I just know that the first time I had ever seen you in my life was last night. There's no way I or anyone could forget meeting you. Who are you?" Gretchen actually blushed at the praise. She leaned forward as if sharing a secret, even though we were alone. Reflexively, I leaned forward to listen. "I wasn't always Gretchen Schtupmore, Bobby." Huh? I couldn't grasp the concept, then maybe I did. "Did you marry a Schtupmore?" She smiled. "No, Bobby. I was once Tommy Schtupmore." What? How could.... Wait a minute. I asked dumbly, "What do you mean?" "I was a boy and now I'm a girl. By choice. And as you said, the results were pretty good, don't you think?" Stunned silence from me. A placid smile from Gretchen. Waiting for me to process. Processing. I had never heard of such a thing. Was I ever that na?ve? "How?" I asked eventually. "It was something I had to do, Bobby. I was never happy as a boy. Always knew I was a girl. Right after high school I left town and started dressing as a girl. Then I made a few 'augmentations' to make me a bit more girlish. I made a lot of new friends - especially men who were sexually attracted to me. Men who were looking for some real femininity from their companions, even if the companions were genetic males. I got a long way depending on the kindness of strangers. And so did you last night." I was having difficulty focusing my eyes. So much to think about. We took a couple minutes break, saying nothing as thoughts flared through my brain. Then Gretchen said, "You must be stunned. I'm sorry to hit you with that, but there's no good way to tell anyone is there? Can I answer any questions?" Only a million. I, of course, asked a dumb one. "Does Skippy know?" Gretchen sort of politely bit her lip so she wouldn't laugh at the concept. "All my gentlemen know, Sweetheart. I still have my boy parts between my legs and always will. And I'm very generous with my gentlemen." So, she's a boy masquerading as a girl, but she still has her cock and balls. She lets men undress her and do things to her. She probably sucks men's cocks too. Was she gay? Somehow that didn't seem like the right word. None of the usual definitions worked. I thought that all through and finally said, "OK. I'm glad you're happy being who you really are. Tommy was a nice person and I'm sure you are too. And I'll always be grateful to you for what you did so I could finish the semester. This summer, I'll go home to take a year off and earn some money. I'll tell everyone at home what a great person you are. When I come back to school 16 months from now, maybe you'll still be here." Apparently that was exactly the right thing to say. Gretchen got to her beautiful feet, walked over to me, asked me to stand and hugged me. I thought I would feel gay about being hugged by "Tommy" Schtupmore, but I didn't. I felt aroused. Please don't let her hug me too tightly, I thought. But then she did. And my hard cock rubbed against hers. Which should have disgusted me too. But it didn't. Gretchen was a girl. To me and the rest of the world. A knockout-beautiful girl. But I still broke the hug first. She invited me into the living room and seated me in an easy chair. She sat in a chair nearby and said, "Thank you for being a grown-up about my situation, Bobby. It's a great comfort to me that the folks back home accept the real me." I was feeling pretty good about myself at that point. Then Gretchen changed the subject to what was still my favorite subject - me. "Bobby, you don't really have to drop out of school, you know. There are options." Options? "Like what"" I asked. "Well, you're an actor, right?" "Yes, I am," I affirmed. "How would you like an acting job that would pay your tuition and living expenses through graduation? A difficult role, but one I know you can play well and will enjoy." I thought, who do I have to kill, but I said, "Tell me more." Gretchen stood up and walked to the couch, which was on my right. She sat and appeared not to notice that her dress had eased up beyond her stocking tops. I saw just a hint of her bare thigh, which was wildly exciting to my stiffening cock. "As I told you before," she said, "men today need some femininity from their companions. They're definitely willing to pay for it. Just the feminine companionship - I'm not talking sex. Someone who wears real stockings and big heels with her dresses. Someone who spends time on her make-up to please her man. That was the principle I used to succeed, when I came here, disowned by my parents, without a friend. Only enough money to buy a basic, feminine wardrobe. It worked for me. It can work for you." Gretchen stopped when she saw the look of horror evolving on my face. She jumped in and said, "I'm not asking you to become a girl like me. Oh no. You can stay Bobby Pipeuse. I just want you to assume the role of a girl now and then. I'll train you in the role. You can even move in with me if you want - I have a spare room. I'll set you up with dates who will expect nothing more than an afternoon or an evening of sweet feminine companionship. You'll be paid $250 a date and can stop any time you want. Are you up for the challenge of the role of a lifetime?" It all sounded great - the money - the living in this lovely condo - with Gretchen. Except for the "dating men" part. Gretchen understood. "Don't worry about the men, Bobby. You'll enjoy the gentlemen I pick. You'll like the attention they'll give you. You'll like the money. And you can stop any time you want." How could I refuse? I couldn't. So I didn't. Gretchen squealed and ran over to me. She flung herself onto my lap and hugged me. Then she kissed me. On the cheek. Then on the mouth. I was kissing a boy on the mouth. And loving it. Gretchen wasn't a boy. Or a girl. She was the best of both. Sadly, Gretchen broke the kiss abruptly and stood up. "Oh my goodness, Bobby," she said. "We're wasting time. I've got to get you ready for your new acting role and there's so little time. I'm pretty sure I can get you your first gig tomorrow afternoon. We'd better get moving though." Tomorrow? I was going to be a girl tomorrow? A non-sexual, yet intensely feminine man's companion by tomorrow? It was a huge challenge for an aspiring actor. Too bad I couldn't accept the challenge. "I can't, Gretchen," I protested. "I have my shift at the Hungry Heifer from four until eleven tonight. Then tomorrow I'm a food server at a catered party all day." "Pish-posh," Gretchen said. Pish-posh? "That was the old you," she said. "The new you is going to work with me and me alone. You'll make plenty of money and enjoy the work immensely. Now let's get on the phone and quit those jobs right now." It was a big leap. But Gretchen's logic was pretty sound. Plus she had very nice boobs. And great legs. It was very difficult to say no to her. I got on the phone and quit my jobs as Gretchen smiled approvingly. Chapter Three - Learning the Role Gretchen put me right to work learning my new "role." She took me by the hand and led me to her bedroom. "Off with those clothes, Mister. All of them." Naked! She wanted me naked? Did she want to have her way with me as a way of sealing our contract? No such luck. "Go right into my shower and wash yourself really well, especially your hair. When you come out, you can wear a towel, but that's all. Now snap to it, my new employee." She didn't say any of that in a mean, domme sort of way. It was all light-hearted. But firm. I complied. While I was washing up and trying to get my cock in a more placid state, Gretchen was assembling stuff from her things. Girlie stuff. I emerged from the shower wearing a towel, as directed. Gretchen came up to me, snatched the towel and giggled. I was naked. In front of my dream boy-girl. With my respectable, six-inch, uncircumcised cock at full attention. Gretchen said playfully, "I see you like what's happening so far. I don't think you'll like what happens next, but it's necessary. I'm going to show you how to shave your body hair, starting with your legs and armpits." Well, there went wearing shorts during the upcoming summer. But an actor must suffer for his art. I wasn't very hairy and apparently I was a quick learner, because I shaved my armpits, then my legs to a silky smooth. While simultaneously being mortified by my nakedness in front of a "mothering" Gretchen. Gretchen made my "situation" worse by showing me how to rub a soothing lotion on my legs and armpits after shaving. I only had a few chest and stomach hairs, but we shaved those as well. Then she asked me to turn around. "I know you won't like this, Sweetie, but it's necessary. Hold your bottom cheeks apart while I shave you there." That didn't sound pleasant. I almost rebelled at that. But I clearly owed Gretchen. And we had made a deal. It was considerably more pleasant than I had imagined, though. I held my bottom cheeks open as Gretchen wet the inner regions with a warm, soapy washcloth. Then I felt her warm, soft hands applying lather to my "secret place." [That was the good part.] She shaved my anal area quickly and expertly, dried me off, then rubbed the freshly shaved region with soothing cream. [That was the best part] My poor willie was in a sorry state when she asked me to sit on the side of her bed. "You're being wonderful, Bobby," she said. "I can tell you're a real acting professional." I glowed a bit at the praise. Though I had never actually been paid for my acting. "You're going to LOVE the next part, Bobby. Stockings feel so good on freshly shaved and lotioned legs. And look what I have for you. A beautiful pair of black, seamed, fully-fashioned, reinforced-heel-and-toe stockings." Omigosh. Stockings. The kind women wore in the 1950s. The kind Gretchen wore. The kind the girls in my masturbation fantasies wore. Gretchen showed me how to roll each stocking into a little doughnut and slide it up my leg. When I managed to get each one up my leg without running them, several things happened. First, and most embarrassingly, I lost a whole load of creamy sperm all over my stomach. It had been aching to come out since I had first seen Gretchen the night before. Though I never thought it would emerge because of the feelings I got from wearing stockings. Weird feelings. Girlish feelings. Gretchen took it all in stride. "That's OK, Honey," she said. "It's perfectly natural. You're having an exciting day and it's just begun. Here are some paper towels. Let's clean you up and get your garter belt on so your stockings won't droop." Mortified, but curious, I sopped up the lake of cum on my belly, tossed the soiled paper into a trash can, and watched Gretchen as she taught me how to put on a garter belt, then hook it to my stockings, check and adjust my seams. "Tomorrow morning, or maybe even later today, I give you a manicure and pedicure and show you how to paint your nails, but I wanted you to have a little high-heel practice first." High heels. But I never.... "Just slide these on. That's right. Do you like them? They're only two-inch stilettos. Training wheels, really. But they're a start. Try to stand." I did. And I wobbled. And thought of chucking the whole thing. But then I saw my reflection in the room's full-length mirror. I liked what I saw. My legs looked great! With the garter belt and heels, from the waist down, I was a very hot-looking babe. Except for the rapidly restiffening cock. But nobody's perfect. Gretchen helped me get the hang of high heels and in an hour or so, I was moving pretty well. At which point she switched me to three-inch heels and I wobbled for another half hour until I was OK again. Thankfully, no four-inch heels followed. Gretchen then said, "You're doing so well, I'm going to give you three rewards. First, I'm going to give you a bra and panties to wear so you won't feel so exposed. I accepted gratefully. Though the panties were quite tented in Gretchen's lovely presence. When bra and panties were in place, Gretchen announced the second reward. "I'm going to strip down to bra, panties, garters, stockings and heels too, so we'll be dressed alike." Wow. I unzipped her sundress and she pulled it over her head. Revealing a babe in the full flower of babehood. Gretchen had real boobs. At least I thought they were real. They looked real. And though I couldn't see the nipples, they occupied her lacy, white, strapless bra fully. I would guess maybe a 34B. Her waist was slim and girlish, with a delicious innie belly button. Her panties were white, brief, nylon and wispy. And severely tented. Apparently she liked our training session as much as I did. Her ass was plump and filled her panties sexily. Her legs were even more beautiful than mine - which was a high compliment - I have great legs. And I envied the ease with which she moved in her skyscraper heels. Somehow I managed to croak out the question, "And the third reward?" Gretchen smiled and said, "A tension reliever. Lower your panties to your knees and I'll show you." I complied with that very welcome order. Gretchen stood face to face with me and said, "You're so sweet and such a fast learner. I just know we're going to be great friends. We're going to learn how to do make-up next and kissing lipstick to lipstick is such fun. Would you like to kiss me as I get rid of all that nasty boy's cream for you?" I could smell her perfume. And felt the warm glow of her femininity. "Yes, please," I said. "But wouldn't it be nicer if I could relieve your tensions at the same time?" I couldn't believe I had just propositioned a guy. Well, sort of a guy. I was getting over all that very quickly, though. I loved Gretchen's response. "I thought you would never ask." She lowered her panties to mid thigh and, holding me in her beautiful arms, kissed me and rubbed her stiff, thick cock against my enflamed poker. I returned the kiss, the embrace and the rubs. All thoughts of gayness fled my brain. We kissed and hugged and rubbed. It felt wonderful. She felt wonderful in my arms. The stockings felt wonderful on my legs. And we were both leaking so much juice that the cock friction was delightful. I wanted it to go on forever, but Gretchen soon squealed softly and gave up her cream. All over my delighted tummy, prick and balls, which triggered my little blast. It was a wonder I was able to remain standing on those heels as I emptied my testicles. It was a very nice cum. We kissed a little during the cooling-off period, but then Gretchen was all business again. "We have to show you how to do your make-up, Bobby. I see great potential there for you and I think you'll really like the results." I kept telling myself, "It's just a role. An acting job. With good pay. And better benefits." We toweled the cum off each other while it was still wet. Though I could still smell its sweet aroma. Did I want to taste Gretchen's cream? Maybe a little. Then Gretchen and I sat at her vanity table on matching stools. We looked in the mirror. Gretchen looked beautiful. I looked boyish and frumpy. Still, she said she saw potential in me. So I was hopeful that I would look all right with some make-up on me. Otherwise, my acting job was going to end quickly. What man would want a feminine escort who looked masculine? Gretchen didn't seem worried, which eased my concerns. And so to work. Gretchen produced a color chart, which she held against my face. She took her time evaluating things, then disappeared into her huge closet. Five minutes later, she emerged with a large tray of cosmetics. "These should do, Bobby. Let's try this shade of foundation." She showed me how to apply it, then seemed pleased with the results. Then some blush, with equally good results. I saw myself changing and was enthralled with the process. The eyes were the real transformers. They presented the greatest technical challenge, what with the mascara, the eye liner and the eye shadow. I paid careful attention to the process. When the entire warpaint had been applied, I was prepared to go on a raiding party. I was pretty. Not beautiful, like Gretchen. But interesting. More like Katherine Hepburn or Barbara Stanwyck versus Gretchen's Lana Turner or Deborah Kerr. Interestingly pretty. Gretchen disappeared again and returned with a short, blonde wig, with lots of curls. She showed me how to put it on, then sat down beside me to consider her achievements. I looked very good. Feminine. Sexy, even. Just a role. Good job. Better benefits. Not gay. Still, my cock was quite stiff. Was I turned on by my image? Or by the idea of being a girl? Gretchen complimented me on my beauty. But then the drill sergeant in her re-emerged. "Wash your make-up off, Bobby. Then I want to see you do what we did by yourself. I complied. With good results. The third time I applied the make-up, I think I looked better than the first time. So did Gretchen. "I knew you would be a fast learner, Bobby. You're smart and pretty. Now let's work on your female mannerisms." Gretchen drilled me on feminine mannerisms for two-and-a-half hours. I must say, I applied my acting skills to the problem and solved it to Gretchen's satisfaction." "You're the best yet," Gretchen said at one point. I didn't think she meant to say that because she changed the subject immediately. Were there others whom Gretchen trained? Others for whom she arranged dates? Apparently so. Though I didn't think it politic to press the point. At six, we stopped and went to the kitchen. Gretchen popped two Lean Cuisines in the oven and began tossing a salad. She asked, "Did you bike over here?" I said yes. Then she asked the big question. "Would you like to stay with me for a while until you make enough money to rent your own place? I'd love to have you and it would get you out of that awful dorm." Would I? Wow. Gretchen was pleased that I accepted. She surprised me when I said I had to secure my bike, which I had parked outside and that I would gather my things at the dorm and move in with her the next day. "Don't be silly, Bobby. Just give me your keys. I'll have it done." Have it done? I retrieved my keys from my boy pants, and when I came back to the kitchen, Gretchen was just getting off the phone. She smiled at me as she wiggled to the bedroom and brought back two lacy peignoirs. "Put this on," she said. "We should be decent, not just in our panties, bras, garter belts, stockings and heels when Kevin knocks." Kevin? "One of the security people for the building. He'll be here in a minute or so, then he'll secure your bike and get your things at the dorm." Kevin would do that? That was a lot of work for someone he didn't know. Though he apparently knew Gretchen. Maybe quite well. Moments later, the doorbell rang and Gretchen answered it. "Come in, Kevin," she said. "I want you to meet my friend Nicole. She'll be staying with me for a while, so please extend her every courtesy. It's very kind of you to do this favor for Nicole. I'm sure she'll want to thank you properly before she leaves here." Nicole? I was Nicole? Well, Bobby didn't go with the way I looked. But did Gretchen just promise Kevin sex with me at some point? I hoped not. Because that was not me! Though Kevin was a very nice looking young man. Mid 20s. Tan and fit. Normal clothes. No prison tattoos. And he had a nice smile. With just a hint of leering lust in it. Which was entirely appropriate, considering how hot I looked. I shyly thanked Kevin, then Gretchen led him to the door and gave him a nice kiss on the mouth - no tongue as far as I could see. "Thanks, Gretchen," I said. "Don't mention it, Nicole." OK. I was in character as Nicole. I would stay in character. OK. We ate our 150 calorie meal and cleaned the dishes. Then Gretchen gave me that manicure and pedicure she promised me. Which made me feel extremely girlie. Soon it was bedtime. Gretchen helped me wash off my make-up, then apply cold cream. She gave me a pretty, white, satin nightie, which was the only garment I wore to bed. Gretchen wore a lovely, pink nightie. We pulled down the covers and slid into Gretchen's bed. It was king- sized, compared to the queen-sized bed in what would be my room. Unsure of what I was to do, I lay there waiting for Gretchen to act. "You were wonderful today, Nicole. Come here and put your head on my chest." Eagerly, I complied. She hugged me and I felt safe and warm. Already I was feeling feminine. Because it was the role I was playing. "Let's kiss and tickle each other's pickles until we cum," she said. "Then we'll go to sleep." It was a good plan that we executed to perfection. Chapter Four - Dating I slept wonderfully until I was awakened by Gretchen's call to breakfast. She had made us egg-white omelets and dry, wheat toast. They were good, though I began to wonder if I would ever eat fried fat again. We cleaned up and Gretchen told me about my day. "Kevin put all your dorm stuff, including your bike, in your new room while we were sleeping. You can sort it out later. I got an email from your date, Mr. Ryan, and he'll be here to take you on a picnic at 11:30. He's sweet and harmless and he won't do anything you don't want. Just like all our gentlemen. Let's get you nice and pretty for him." I had a deep fear in the pit of my stomach - right where that undercaloried omelet was sitting. I would be alone with a man. A man with animal urges and disgusting needs. What if he saw how beautiful I was, forgot I was a boy playing a girl, and molested me? Or what if he didn't like me? Thought I was ugly or too masculine? What of he had no interest in satisfying his disgusting needs with me? That would be bad too, right? Gretchen assured me that all would be well as she had me shower, powder and blowdry. She supervised my make-up and put me in a long, straight, brunette wig, which she tied in a ponytail. I put on my tan, seamed, fully-fashioned, reinforced-heel-and-toe stockings; strappy, red, sandals with a three-inch-stiletto heel, lacy, white garter belt; white bra, white bikini panties and white petticoats, because my dress was a retro masterpiece - white with red polka dots. To top it off, I accessorized with seductive perfume, a gold chain necklace and gold, clip-on earrings. I looked hot! Very hot. Don't-tear-yourself-away-from-the-mirror hot. It was a good thing I was wearing petticoats because my cock was ridiculous. I thought Gretchen would "handle my problem" for me, but she was in a rush to get herself dressed before Mr. Ryan's arrival. We were ready at 11:28. He was prompt. And very nice. I'm guessing he was in his late 40s. Good-looking. Fit. Tall. Wearing a seersucker suit, bow tie and a straw boater. A real traditionalist. Gretchen greeted him warmly with a cheek kiss. They obviously knew each other. He was very courteous to her and when they turned toward me so that Gretchen could introduce us, I could see that he was moved by the sight of me. No, I'm not exaggerating. And no, I don't mean he got an erection. His eyes actually teared up a bit. As if I were the fulfillment of some dream. He came forward and gallantly took my right hand in his, then brought my manicured, red-painted fingertips to his lips for a gentlemanly kiss. This was a man who could sweep a girl off her feet. Had I been a girl. "I'm so pleased to meet you, Nicole," he said. "It's so kind of you to accompany me on our picnic this afternoon. I brought a full basket, so I hope you're hungry. The way I had been eating at Gretchen's I was plenty hungry. Though it wouldn't be feminine to hog out. I was very shy around Mr. Ryan, which he seemed to like very much. We said goodbye to Nicole and headed for the elevator and just like that I was on a date with a man I just met. And I was dressed as a pretty girl. Which surely enflamed his hormones. Courage, I told myself. It turned out that I didn't really need it. Mr. Ryan was sweet and solicitous. He held all the doors for me, even as we walked past a leering Kevin in the lobby. He opened my car door and made sure my skirts were in before he closed it. Thankfully, I remembered to hold my legs together as I sat in the car. He chatted about the weather and himself and how pretty I was and himself. Which was fine with me, since I didn't have much to say about Nicole, someone who had literally been born yesterday. In about ten minutes we arrived at the town's best park. He found a parking space, then helped me out of the car. He retrieved a blanket from the trunk and a wicker picnic basket from the back seat. We walked from the parking lot to the picnic area and I held his arm. Which surprised me as much as it did him. It was a bit of a walk, which was no "picnic" in three-inch stilettos, but I enjoyed it very much. Men were staring at me. Lustily. I had never turned a head in my life. Until that moment. I loved the tug of my garters on my stockings as I walked and the feeling of the breeze up my skirts. And the men's stares. Mr. Ryan noticed the heads turning. And he also noticed that I gripped his arm more tightly when the craniums pivoted. He liked that. We arrived at a nice picnic spot and he spread the blanket. He helped me sit (legs femininely tucked under my skirts, high heels demurely removed) then he proceeded to set up the picnic and serve me. I could get used to that. The food was excellent and yes, I did eat some deviled eggs, potato salad and cold, fried chicken. I became less shy, telling him some non-gender things about my hometown, my family and my college life. It was an extremely pleasant experience. Then it got better. I helped Mr. Ryan clean up, pack the basket and fold the blanket. He helped me to my feet and I slid my heels back on. He was very interested in that particular operation. I held the blanket under my left arm and he held the basket with his right hand. Again, for an unknown reason, I put my right hand in his left hand as we walked back to the car. His hand was warm and I felt something I had never felt before - adored. He hardly knew me, but he was perfectly willing to adore me. This was a man who was truly starved for femininity in his life. And I was mainlining it right to him. About halfway back to the car, I had to stop, though. "My feet hurt, Mr. Ryan," I said. He didn't offer that I could call him Henry or Willie or Sam. He liked being Mr. Ryan to me. But he was, as always, very courteous. "Please, my dear Nicole. Sit on this bench and rest. I would bring the car to you but I would have to run over all these picnickers to do so." Bad option. The bench sounded great. He seated me at one end of the bench and asked, hopefully, "May I remove your shoes?" I think he might have expired if I had said no. I said yes, gratefully. He removed them reverently touching my stockinged feet a bit more, perhaps than was absolutely necessary. But it was very nice. He stood up, then placed the blanket at the other end of the bench. "Nicole, why don't you put your head on this blanket. I'll sit at the other end of the bench and give your feet a nice massage." The poor guy's lip was quivering with prayers that I would say yes. A massage of my tired feet sounded great to me, so I said, "Thank you, Mr. Ryan. That would be very nice." He moaned softly at my words, then we rearranged ourselves as he suggested. I lay with my head on the blanket, held my dress down so that few of my petticoats showed, and put my feet on Mr. Ryan's lap. He quivered with pleasure as he felt each stockinged square millimeter of my pretty feet. Then he gave me a darned good foot massage. Good enough to make my feet walkworthy and my cock stiff. The man knew his craft. And he worshipped my feet. He sighed as he peered at my pretty, painted toes through one reinforced portion of my stocking. His hands roamed lovingly along the seam that traversed my sole and landed at the other reinforced portion, the heel. I could have stayed there the rest of that beautiful day. As it turned out, I think he did massage my feet for about an hour without a word between us. He had to have a hardon, which I could have easily confirmed with an errant foot. But that would have spoiled something beautiful, so I didn't. Finally, I decided it was time to go. I suggested that we leave and rather than act disappointed, he thanked me profusely for the past hour of our lives, then he lightly kissed the toes of each of my stockinged feet. That was the closest I came to cumming that wonderful afternoon. Very close. But I'm glad I didn't. It wouldn't have fit with the rest of our date. I sat up, thanked him sincerely, then planted a soft kiss on his cheek. His cheek was hot. He looked at me with fierce adoration in his eyes, stood up, then knelt to put my shoes back on. We walked back to the car, arm and arm, that time and we drove to Gretchen's apartment. He parked in Gretchen's lot, helped me out of the car and said, "That was one of the best dates of my life, Nicole. If you could see your way to seeing me again, I would love to arrange another date with you through Gretchen." As an answer, I startled Mr. Ryan by leaning forward, putting my hands on his shoulders and kissing him full on his lips. I broke the kiss and said, "I had a wonderful time too, Mr. Ryan. You're a sweet, loving man and I would love to see you again. Thank you for everything." He beamed. Then he reached into his suit coat pocket, extracted a small envelope and pressed it into my palm. He doffed his straw boater to me, got in his car and was gone. Oh my. So much to think about. I had just kissed a man. Willingly. Role play or no role play. I had just agreed to another date with the same man. And since the date would be made through Gretchen, it would be another "paid date." We all know another name for "paid dates," don't we, girls? Even worse, if the envelope contained what I thought it did...it did - money. Two one-hundred-dollar bills. I was getting paid $450, in exchange for holding a man's arm and hand, kissing him and letting him mildly indulge his stockinged foot fantasy for an hour. That was when I first wondered what Gretchen charged over and above the $250, plus tips, that I earned that day. And, based on her slip of the tongue, I wondered how many other "girls" there were like me. Making Gretchen rich. On the other hand: I had enjoyed myself tremendously with Mr. Ryan. It was probably the best date I had ever had. I not only was good at playing the role of beautiful girl - I quite liked it. Two days ago I was broke, working two jobs and about to be kicked out of school. Today I was flush with cash, with paid tuition and a hot, feminine roommate. Who was clearly using me, but not without great mutual benefit. I stood outside for a while wondering if I should just tell Gretchen to forget everything. Go back to being an obscure, poor, pathetic boy. Reduce my sex life to being envious of monks. I wasn't crazy. I went back to Gretchen's apartment with a clearer understanding of what was happening, but no clue as to where it was going. Gretchen let me in and greeted me with a big hug. Which made my prick stiff because 1) Mr. Ryan's sweet kiss had steamed me up much more than I thought possible, 2) I hadn't cum since Gretchen and I "handled each other" before we went to sleep the previous night and 3) Gretchen was wearing black, seamed, fully-fashioned, reinforced-heel-and-toe stockings; a black, lacy garter belt; black thong panties with a sexy pouch for all her pink pretties; and (I'm not making this up) FIVE-inch- high, stiletto, fuck-me pumps. No bra. Beautiful boobies rubbing against me as she kissed me enthusiastically. Between smooches, she said, "Oh, Nicole (Bobby was not on her mind). Mr.Ryan called me and he was ecstatic. He said it was the best date he had ever had and he can't wait to see you again. And he will on Tuesday night, OK?" Mr. Ryan thought I was his best date ever? I was very pleased at that. He was my best date ever too. I was creeped out at that. Gretchen went on. "I knew you would be a great actress. I knew it. You are a great actress." Actors (and actresses) love praise. I was definitely no exception. And a second date with Mr. Ryan would be very nice. Bankroll-enhancing too. I was about to agree to the concept, thinking I would have 48 hours to process what it all meant to me before seeing that nice man again. But Gretchen had other ideas. "Another nice man, Mr. Pesto, called me and I told him all about you. He would love to have you over his place for pizza and a movie tonight, No funny stuff. Can you do it? For me? And for yourself, of course." Another date. That same day? I couldn't. Could I? I spoke. "I have school work. Things due on Tuesday." "That's fine," Gretchen said. "You'll have all day tomorrow to work on it. I'm out tomorrow and Kevin brought all your stuff here, including your laptop. Please say yes." I said yes. And quivered at the thought of playing my role with another man. And maybe getting a creamy reward from Gretchen. Perhaps oiling up Gretchen's titties and rubbing them together on my cock until I started a fire in my testicles. But no. "Mr. Pesto will be here in less than an hour, Sweetie," she said. "We have to freshen you up before he comes. That's a gorgeous outfit, but Mr. Pesto likes his girls in black clothing. And with blonde hair." And so it was. We rushed around until I was refitted for the next sortie as they say in the air force. My straight, lush, blonde wig looked fabulous against my basic black minidress; black, seamed, fully-fashioned, reinforced-heel- and-toe stockings; black four-inch-stiletto pumps (oh my!) and somewhat more dramatic, night-time make-up. Looking at myself gave me a hardon. Looking at the suddenly unattainable Gretchen gave me a hardon. Thinking about all the stuff I had been doing in the past two days gave me a hardon and I hadn't had relief in 20 hours. Was that Gretchen's intent? That I would be hard up to cum when I went for my date with Mr. Pesto? Could she be that manipulative? Maybe. Gretchen was pretty lavish with praise for my beauty - which was, I must say, well-deserved. Forget what I said about being almost beautiful, but not quite there. As a blonde, I got there. Gretchen covered herself with a black robe just before Mr. Pesto arrived. "I'll just introduce you to Mr. Pesto and then the two of you have to scoot. I have to get dressed for my date tonight. He'll be here in 20 minutes. When you get home, I'll be 'entertaining' in my room, so we may not be able to talk in the morning before you go to class. Have a great time tonight, Nicole. You'll like Mr. Pesto. Ooops. There's the doorbell." She opened the door and brought Mr. Pesto in. He was CUTE! I mean, a woman would think so. Late thirties. Broad shoulders and thin waist. Nice shirt and pants. Friendly looking. Intelligent face. Piercing, blue eyes. Cute. And very gentlemanly. He praised my beauty and his good fortune to meet me. A nice little scene cut short by Gretchen's insistence that we scoot before her paramour arrived. Like Mr. Ryan, Mr. Pesto held all the doors for me as we walked from the apartment to the car. Past a leering Kevin the doorman. Even though I hardly looked like the same "girl" who dated Mr. Ryan earlier that day. Like Mr. Ryan, Mr. Pesto talked mostly about himself, though he seemed interested in me too. So far so good. We arrived at his condo building and for the first time as a girl, I was alone with a man in his home. Alone with someone who lusted for my young, supple body. Was it hot in there? I told myself that if I got through the date, I could go back to Gretchen's, lie on my bed, pull down my panties and shoot out all my accumulating sexual tension. Couldn't do any such thing with Mr. Pesto actually around. Not around a man. No way. Though he was very nice. And apparently very rich. His apartment was super first class. Modern everything. More about that later. His first question after he watched me assess his living situation was, "So, Nicole, do you like pizza?" "Oh yes, Mr. Pesto," I answered honestly. Real food was way better than that healthy stuff Gretchen fed me. Notice that, like Mr. Ryan, Mr. Pesto let me call him Mr. Pesto, not Tony or Bruno or Rico. Odd. Anyway, Mr. Pesto said, "Great, because we're making it from scratch and you're helping." It turned out that Mr. Pesto made pizzas in his huge, fully equipped kitchen. He even had one of those big pizza ovens you see in pizza parlors. And a big, flat, wooden spatula to put the pizza in and pull it out. Mr. Pesto said "from scratch" and he meant it. We made the dough right from the flour and the sauce right from fresh tomatoes. I half expected him to send me to the backyard with a bucket to milk a goat for the cheese. It was great fun and he was wonderful company. And my cock kept getting harder and my balls bluer. We put the pizza in to bake and he asked me what movie I wanted to see. "Gee," I said. "I don't have the newspaper. What's playing around here?" He laughed. "No, Honey. I meant what movie of the last 70 years or so do you want to watch. I'll download it from the Internet and we can watch it in HD on my home theater system." See, he had every gadget. I thought a second and said, "No question, then - my all-time favorite - 'Animal House.'" His face lit up. "That's my favorite too. I have that on DVD, let me set it up." We even had similar taste in movies. Did I mention that he was cute? And that my balls ached from continued stimulation without release? His home theater system was in a nice room connected to the kitchen. The only furniture was a plush, two-seater couch and a coffee table. "Let's eat our pizza as we watch the show," he suggested. That would have driven my mother crazy, since meals were to be taken at a table, she always said. But she wasn't there that night. I agreed eagerly and carried sodas, napkins and plates to the coffee table. Mr. Pesto carried in the steaming, sliced, beautiful pizza and set it on a special rack. "Mange," he said. Which I think means "eat" in Italian or Lithuanian. Though I don't think the spelling is right. I ate. Unladylike to do so, I know, but I ate three-eighths of the pie as we watched the scene where the pledges join the Delta House. Mr. Pesto was delighted that I ate so much. Thank goodness I didn't burp. Finished eating, I sat back with Mr. Pesto and kind of leaned into him. My shoes were off and my skirt had ridden up a bit to show the beginnings of my stocking tops. He put his arm around me and we watched and chuckled. It was very comfortable to be in that man's apartment, eating his food and now sharing a relaxing cuddle with him. Looking back on it, I think the turning point was when we watched the scene where Bluto uses a ladder to peep on the sorority girls as they undressed. All those pretty, young girls in their retro bras, panties and fully-fashioned, reinforced-heel-and-toe stockings. That was the scene that stirred my soul as a boy and was stirring it as a girl. I looked up at Mr. Pesto during that scene. I saw that he felt the need for femininity when he saw that scene as well. I parted my mouth, looked into his eyes and tilted my head slightly back. It was a clear invitation for a kiss. And so he kissed me. I kissed back. One part of my conscience called me a gay little slut for kissing two men in one day. I told that part to shut the fuck up. Kissing Mr. Pesto was fun! Lots of fun. He was a great kisser and his tongue tasted great too! We kissed for a long time, which made the ache in my balls almost unbearable. So it wasn't my fault when I lifted my skirt to show him my stockings tops, bare thighs and black, bikini panties. The naughty man took that invitation too. He caressed my thighs, stockinged and bare, very nicely as he took my breath away with his ardent kisses. I was very steamy and ready for almost anything when he suggested that I remove my panties as he removed his trousers and boxers. It wasn't my fault. Did I mention that? And that he was cute? Next thing I knew, my panties were on the coffee table among the pizza remnants. My skirts were up around my belly button and Mr. Pesto was stroking my naked, skinned, nearly purple cockhead as he kissed my neck. Just to be fair and to let him know how much I appreciated the pizza lesson and dinner and everything, I was stroking his enflamed cock as he was stroking mine. Again, not my fault. Merely a courteous act. I must say though that it was probably the most exciting five minutes of my life. It was so wrong and dirty and gay and amoral that it had to be exciting and fun, He spurted first. I had made a man cum. With my hand. As I let him kiss me and stroke my own, stiff penis. Not your ordinary day. The full notion of what I had done made me spurt. Hard. Seven thick ropes of cum, all the way up to my neck, where a hot blast struck Mr. Pesto in his manly ear. I wondered idly whether I would be paying the dry cleaning bill for that dress or Gretchen. Or Mr. Pesto. No matter. It was way worth it. And a medical necessity. I couldn't have lived much longer with my testicles in that condition. When we had calmed down a bit, Mr. Pesto got up and went into the kitchen for some Wipe-Ups or whatever they're called. He seemed concerned about the cum stains and he wiped up most of the long, thick, cum strands that decorated my cute dress. All the while he was gently doing this, I sort of had my eye on his cock. Which was still "out there," since he hadn't repantsed. Of course, I hadn't either. So my popsy was sort of sitting there, breathing free air, as he futilely attempted to clean me up. When he was finished, he stepped back and sort of chuckled. "The dry cleaner will have a great story to tell his friends about this dress. You annihilated it!" I giggled. Actually giggled. Not chuckled or laughed. I giggled. Which seemed to delight him. And make his cock twitch upward. Which made my cock twitch upward. He said, "I know this sounds like closing the barn door after the horse has run away, but maybe we should remove that pretty dress for the rest of our date. Just as a precaution. Unless you want me to take you home right now. Or we could put my pants and your panties back on and just watch the movie." Not on your life, buster. I stood up, turned around so he could unzip me, then pulled my cum- stained, "Monica" dress (though hers was blue) over my head. I tossed it and my black slip behind the couch, then stood as Mr. Pesto admired me. I looked pretty good in my black bra, garter belt, stockings and heels. He thought so too. I know that because his cock leaped to a three- quarter stand. Mr. Pesto didn't expect me to have boobs, so he didn't miss them. Or did he? The naughty boy stepped forward, took me into his arms and kissed me deeply. His fingers fumbled with my bra catches, and he finally deciphered them. My bra fluttered to the floor and he held my naked top half against his clothed top half as we kissed. His bottom half was naked, but my bottom half was stockinged and heeled. Both of our penises were naked and fully stiff. We rubbed them against each other, swapping sweet goo, as we kissed. It was heavenly and after a few minutes, I squealed and spurted my cream again. All over his private parts. And his nice shirt. Mr. Pesto sat and pulled me onto his lap. He launched a major oral offensive on my right nipple, an area in which I thought he would have no interest. He was interested. I was very interested. And surprised. I had no idea having my nipple sucked by a rampant man moments after a debilitating orgasm would be so pleasurable. It was, girls. It was. He switched his kissing, sucking and licking to my left nipple. I began a sweet manual friction on his drooling, reinvigorated cock. Heavenly sweet sensations trumped the Dirty Duo of Emotions - shame and guilt. I would confer with them later. Though they shouldn't really apply, since I was playing a role. Professionally. It was work I was doing. Sometimes work can be fun. Then the bad man slid his finger into my anus as he kissed my nipple. That was very naughty, girls. Over the line. And, of course, it made me ejaculate helplessly. And squeal like a little sissy. I had let a man stick his finger into my bottom in order to make me cum. And enjoyed it immensely. Far beyond any role I was playing. I guess my cummy delight made Mr. Pesto cum, because I had long stopped stroking his big Johnson. I couldn't "Code Blue" and masturbate a man at the same time now, could I? But cum he did. All over my hand, arm, and tummy. It was a very messy night for us both. But a great one. That sort of emptied our balls for the evening, so we just kissed for a while, then cleaned up and got dressed. Just as we learned that Bluto was to become a U.S. Senator. I'll never watch "Animal House" the same way again. "I had a wonderful time, Mr. Pesto," I said, as my date escorted me to the front door of Gretchen's building." "It was one of the best dates of my life, Nicole," he answered. "I'll ask Gretchen if we can get together later this week." I liked that idea a lot, except for the part where Gretchen was running my dates. Of course, I definitely owed her. My life had gone from zero to ten since I met her. Mr. Pesto kissed me again and I'll be darned if I didn't lift one high- heeled foot backward - just like in the movies. He pressed a small envelope into my palm and I scooted into the lobby. Thank goodness that Kevin wasn't on duty. I was beginning to think he was an android. In the elevator, I opened the envelope. Three $100-dollar bills! I had $1,000, tax-free. All mine. One day's work. Oh, the possibilities! I let myself into Gretchen's apartment and, true to her prediction, she was in her room, "entertaining" some very lucky guy. I went to my room and sat on the bed. What a day! What a great day! I was not only convincing as a girl, I drove men sex-wild. The shocker was that I liked being with men when I was a girl. I liked it a lot. The cumming was wonderful. So was the money. I undressed and thought about the next day. School and schoolwork. Dressing as a boy. Ick. But necessary. Because I was in school and I was a boy. Really. Wasn't I? I undressed slowly, reluctant to shed my female persona. A lot of self-admiration in the full-length mirror. Hanging things up, I noticed that Gretchen had moved quite a few girlie things into the room for me. Lingerie. Stockings. Dresses. Heels. Wonderful things. And there, on the bed, was a lovely, pink nightie. With cream lace. Lovely. I undressed completely and put the nightie on. I admired myself in it for a bit, then got into bed and turned off the light. Before I drifted off to a well-deserved sleep, I heard Gretchen's moans and squeals of ecstasy. She was taking quite a pounding! Lucky guy. Lucky girl. Chapter Five - Other girls I awoke that Monday morning to the same sounds I had heard when I drifted off to sleep. Gretchen was being vigorously and thoroughly fucked. It was 6:30. Maybe her guy was parked in a zone where they ticketed you at 7. Or he just liked to fuck, early or otherwise. I arose and went to the bathroom that was en suite with my room. Brushed my teeth. Shaved my face. Then, for some reason, shaved my legs and armpits. I dressed in my boy clothes. Double-ick! But I couldn't just show up at my "Principles of Endophilology" class as Nicole after attending as Bobby all semester now could I? Or could I? No. Boy clothes it was. Though they were so - dull. And, I was beginning to think, not the real me. I was going to make myself some breakfast, but I didn't want to run into Gretchen's "entertainment." Gretchen only had disgusting, healthy stuff in her fridge anyway, so I grabbed my books and laptop, then slipped out of the apartment and past the newly on-duty Kevin. Who didn't give me a glance. Where was that leer? Oh. I was in boy clothes. Triple-Ick. The day was an unfulfilled ache. I went to class, then to the library to finish my paper and most of the stuff I needed to do for the rest of the week. I wanted my schedule clear for when I could "girlie" again. I wanted to talk to Gretchen about my dating schedule. Just to make sure that I was "working" the right amount of hours. So there weren't any unnecessary downtimes like that Monday. I tried to call her, but she wasn't answering her cell. So I went to Gretchen's around five and she was there! And she was not alone. There were two other young ladies with her. They were drinking tea and eating watercress sandwiches. The ladies were about my age. And they were beautiful. They wore cute summer dresses; seamed, fully-fashioned, reinforced-heel-and-toe stockings and big, sexy heels. I felt like a bag lady in my boy clothes. Gretchen stood up when I came in. "Oh, Nicole," she said, "I'm so glad you're here and can meet Ashley and Tiffany." Ashley and Tiffany stood and smiled sweetly. Not reacting to the incongruity of a dull-looking college boy called "Nicole." Were they? They were. "Ashley and Tiffany were once boys, Nicole. They've been 'dating' under my gentle suggestion for almost a year now. And, as you see, they're thriving." Yes they were. They were fucking gorgeous. Thrivingly gorgeous. Was this my future I was seeing? If so, it looked awfully good. "I was just telling Ashley and Tiffany about the grateful call I got from Mr. Pesto about your date last night. Tiffany said, 'A star is born,' and I think she's right." I was a star? At dressing up and driving men lustful? It appeared I was. Ashley said, "Why don't you get out of those awful boy clothes, Nicole. We want to see how pretty you are. Tiffany and I can help you." Can do. Before we retired to my room, Gretchen gave her regrets for the evening. "I'm off to dinner and a 'sleepover' at a friend's house, Nicole," she said. "Mr. Ryan will pick you up at six tomorrow night, if that's all right." Try and stop me, I thought. I wanted to see what Mr. Ryan had in his trousers. And the money wasn't bad either. I eagerly agreed to the date, then was hustled off to my room by a giggling Ashley and Tiffany. The girls were very girlie. Ashley undressed me as Tiffany picked out my lingerie and stockings. "Oh, Nicole," Tiffany said. "It's so wonderful that we'll all be working with Gretchen. After all, it's not really work, is it?" It certainly wasn't. I thought about that as I stood there naked in front of two delicious pantyboys. The thoughts of Mr. Ryan and Mr. Pesto brought my penis to full stand. Which, of course, made the girls giggle. "Is that for us, Nicole?" Ashley asked, "Or are you thinking about Mr. Pesto? He's very cute, isn't he?" Had Ashley dated Mr. Pesto too? Well, he had good taste. She was a knockout. Both girls were blonde (of course) and it was clearly their own hair. Both had perfectly made up their pretty faces. Both were delicately perfumed. Both had killer legs encased in sexy stockings. There was an important difference, but I didn't see it quite yet. I sat and applied my make-up, with some sweet advice from Ashley. Meanwhile, Tiffany had stripped to her white garter belt; white "granny panties;" tan, seamed, fully-fashioned, reinforced-heel-and-toe stockings; and blue, strappy, four-inch-stiletto sandals. No bra. Yum. When Tiffany appeared in my vanity mirror, I saw two of her very likable traits. She had a really big cock and some really big boobs. Not breast forms. They were hers. Bigger than