Job Hunting
t was a really tough job market out there - I had recently graduated college, and going on as many interviews as I could schedule, without success. My girlfriend hadn't had nearly as much trouble, and had landed a well-paying job at an advertising firm. And since we were living together at least I had a roof over my head. I had paid my way through school with a combination of scholarships, loans and part-time jobs, but I just couldn't find anything now. It was already well into August, and the only contribution I was making toward our expenses was the little I made at three part-time jobs.
"Dammit, Jennie," I said to her one evening, "today had to be the most frustrating day of all. I had three interviews, but they were all the same `Sorry, but we don't think so. We'll keep your resume on file if something should turn up later.' Right, like they didn't trash them as soon as I left." "Don't worry, hon," she said, "I'm sure something will turn up soon." "I don't know," I said, I think I'm a victim of discrimination or something." "What makes you say that?" she asked, "you're not a member of a minority group - I think you're overreacting." "I don't think so, from something I overheard today. I had just walked out of the last interview and I heard one guy I was talking to say to the other, `Too bad - but I didn't expect it from his name.' I think if I had been a woman, I would have gotten the job. They were ready to interview a girl named Robin, not a guy." "I still think you're overreacting; you probably misunderstood what he said."
Well, it was three weeks after that night, and still no job. But now I finally had some evidence to support my suspicion. I had just come back from a long interview, and I had really hit it off with the interviewer. I was telling Jennie about it: "Then he said to me, `Robin, I think you'd be perfect for the job, and what I'm going to say is off the record, OK? I'll deny I ever said it, but ... well, my boss set down strict guidelines for hiring. We can hire guys who are in the top 5% of their class, but because we need to hire more women, we can hire them if they're in the top third.' See, Jennie, I told you so - I'm being discriminated against!" She sympathized with me, but just encouraged me to keep on trying. Another three weeks of no success had me pretty depressed, and we decided to watch some TV to cheer up. I hit the ON button on the remote, and what was playing but "Tootsie". Dustin Hoffman trying to make it as a guy, but achieving success only after he dressed up as a woman. "Boy, that's the right idea," I remarked, bitterly, "if you can't beat 'em, join 'em." Jennie looked at me strangely for a minute, then said, "You know, Robin, you'd make a better-looking girl than he does." "That's ridiculous," I said, "I could never get away with that - people would spot me in a minute." She didn't say anything, and I switched channels, ending the conversation right there. .
A few days later, we were lying in bed together, having just made love, when she brought it up again. "Remember what we talked about when we saw "Tootsie" the other night?" she asked. "Yes, I do - your silly idea that I could get away with dressing like a woman." "Well, I still think I'm right, that you'd be cuter than Dustin Hoffman." I really didn't feel like talking anymore about it, but she continued, "I'd be willing to bet I'm right." "Sure," I said, "bet what? You know I'm broke, and besides, its really a dumb idea. There's no way I'm going to dress up and go out as a woman." "Well," she replied, "we could bet washing the dishes for the next month." Both of us hated to wash dishes, and we rotated the chore every night. "As much as I'd like to not do dishes for a month," I said, "because I know I'm right, there's no way I'm going to make a fool out of myself." "What if there were a way, you could try it without any risk? she asked, "would you still be willing to bet?" I was tired by then and I said, "Sure, no risk, whatever you say." "So do we have a bet?" she persisted. "Yes, yes, OK, we have a bet," I said, and we fell asleep without any more conversation on the subject.
I didn't think about the conversation the next day, and I made us a cold dinner, waiting for Jennie to get home. She had called and said that she was stopping off at her sister's house and would be a little late. It was almost eight o'clock when she finally got home, and I told her, "I was starting to get worried about you," and I gave her a big hug and kiss, relieved that she was alright. "It took me longer than I thought it would," she said, "but we finally got done." "Done?" I asked, "what were you doing?" "Getting ready for our bet," she said. I noticed that she had two shopping bags with her. "What's in the bags?" I asked her. And she proceeded to lay out her plan: "There's an office Halloween party coming up, and that's where I'm going to win our bet. There'll be a million people there, clients, agency people, friends, vendors, and hardly anyone will know anybody. I spent the evening at Patty's getting your costume." I hadn't taken her bet seriously last night, but obviously she had! "What do you mean, my costume?" I said, suspecting the worst, and her answer confirmed it: "You can dress up as a woman for a Halloween party without any risk - lots of guys do. And since no one from the office knows you - no risk, just like you agreed to." I tried to argue her out of it, but there was no way she was going to cancel the bet. I resigned myself to the fact that she had the costume I was going to wear in the shopping bags. We sat down and ate, and we avoided the topic until she said, "C'mon, be a sport, you did agree to the bet, and its only for one night for the party. I don't want to make you feel bad, though, so I'm willing to cancel the bet, if you insist." "No, we made the bet," I told her, "and guys just don't cancel bets. I'll go along with it, though I'll feel silly as hell, and everyone will know I'm a guy. Besides, when I win the bet, I'll enjoy watching you wash dishes every night for a month. Who knows, maybe you get to like it, and you'll want to wash them all the time!" "Fat chance, buddy," she retorted, "and I still think that you'll be the one with dishpan hands! Speaking of which, its your turn tonight."
Sighing to myself, I got up and washed everything while she went inside. When I had finished, I joined her, and she turned off the TV she had been watching. "You know," she said, "you really have to try your best not to be discovered, if this is going to be a fair bet." I said that if I did anything that would deliberately made me win, I would lose. "Is that fair enough for you?" "Well, almost," she said, "but not quite." "What do you mean, not quite?" "Girls learn how to be girls as they grow up, years and years of becoming ladies," she said. "You can't just learn it overnight. To be really fair, you should practice." "C'mon," I said, "fair is fair, I agreed to one night, not `years and years of practice'. Besides, there's only two weeks until the party." "OK, I'll settle for two weeks of practice," - although I hadn't agree to any practice at all! - "let's get started, there's no time to waste." She took the shopping bags in one hand, and my hand in the other and led me upstairs.
In short order, I found myself standing naked in the middle of the bedroom, watching Jennie pulling clothes out of one of the bags. "I wasn't exactly sure about sizes, so I got a whole bunch of Patty's things - she's more your size than I am." It was true - I'm quite a bit bigger than Jennie, while her sister Patty is nearly as tall as my 5' 9" and has a larger frame than her petite sister. I have a very slender build, though, for a guy, and I guessed that we were probably about the same size. As often as Jennie and I had made love, it still felt strange to be standing naked in front of her while she was doing something else, and I found that I was getting an erection. When she saw it, she laughed, and began to stroke it, teasing me, "don't tell me that thinking about dressing as a woman is turning you on?" "N ...no, don't be silly, its just be naked while you're still dressed," I said. "Well, we have to do something about this," she said, continuing to stroke me, "or else you'll have a bulge in your panties." She knelt down in front of me, and took me into her mouth, quickly bringing me to a climax, while thoughts of how I would soon be dressed disturbingly ran through my mind.
"OK, now that THAT's out of the way, slip into these," she said, handing me a pair of white panties. They felt strange going on over my legs, and nestling around my groin, but I told myself that was to be expected - these weren't exactly my usual jockey shorts! Jennie helped me put on a matching white bra, stuffing the cups with a couple of pairs of her panties, after she fastened the hooks in back. She sat me down on the bed, and, as I followed her instructions for putting on pantyhose without causing runs, the bra felt really weird on my chest. The pantyhose felt even more strange, covering my entire legs with the feeling of the sheer material. "These are just regular daytime things," Jennie said, "I hoped that I'd be able to convince you to practice." She was really serious about winning this bet, I could see, and had planned the whole thing out. I stood up, feeling the tickling sensation of the nylon against my leg hairs, and pulled the slip she handed me over my head. She settled it around me properly, making the smooth nylon rub over my whole torso. She then lifted a pink and white striped dress over me, and I raised my arms so it would slip down into position. I began to button up the front of the shirtwaist dress, fumbling because the buttons were on the "wrong" side. "Well, you don't have much of a figure, dear, but at least everything fits pretty well. Except for the waist, of course." My waist did stretch out the waistband of the dress, and I said, "see, I told you this wasn't going to work."
"Don't worry, we'll take care of that when the time comes," she said, "after all, not every woman has a perfect figure." I didn't have a chance to ask what she meant, because she was handing me a pair of medium high heels to put on. The swishing, swirling feelings of the feminine materials against each other and my body felt extremely strange as I walked over to the bed and sat down to put on the shoes. "You're lucky my sister has big feet," she commented when I had put them on, and tried to stand up. I almost fell over because of the tilt they gave my body, but Jennie steadied me. "OK, practice walking around a little," she said. I did, feeling more silly than ever when she began to coach me on how to walk in a ladylike manner. "A little more hip sway, but not too much," she said when I exaggerated to my hip motion.. "You're not going to be a hooker, just a real lady."
She made me wear the clothes until it was bed time, and I had almost gotten used to the heels, but not to the feeling of the soft, silky clothes against me. I had an erection again, unusual for me, since I was strictly a "once-a-day" guy, and the oral sex Jennie had given me would have ordinarily finished me off for the night. Were these unusual clothes, and the way they felt on me the cause of it, I wondered. Jennie helped me get undressed, and I managed to hide my cock inside my robe as I went in for a shower. I came out, and Jennie went in for hers, and I found myself touching the things I had been wearing. I heard the door open, and feeling my face flush at almost being caught touching the feminine finery, I shut off the light. She hopped into bed next to me, and asked me, "that really wasn't so bad, was it?" "N ... no, I guess not, just strange is all." "Well, remember your promise, you have to practice every night until the party," she said, curling up against me. "You really did look pretty cute in the dress, not to mention in your bra and panties," she teased. "Oh, cut it out, I looked exactly like what I was, a guy in drag. You know, I'm more convinced than ever that I'm going to win this bet." "We'll see," she said, kissing me goodnight and turning over, "we'll see." I lay awake for a while waiting for my erection to go down, thinking about how the clothes had felt on me. The sensations of the smooth, silky clothing persisted in my mind, and a random thought came to me, about how lucky girls were to have all those nice-feeling things to wear, while guys had all the masculine, rough fabrics. My hardon never did go down as I lay there, but I eventually fell asleep anyway.
Jennie got up early to go to work, and I slept until about eight- thirty, when I had to get up to go to one of my part-time jobs. I saw the clothes I had worn still lying on top of the covers, and I picked them up to put them away. The silky panties seemed to have a life of their own as the smooth material caressed my hand, and I sat there, just experiencing it, until I realized that I would have to hurry to get to work on time. I put in my four hours of filing and got back home at about two o'clock. The work I had been doing was mindless, and the only reason they had me as a part-timer was because the secretaries hated doing it. I did a few chores around the house, as I always did; since Jennie was earning the money it was only fair that I do most of the housework - except for the splitting of the dishwashing, that is. I finished most of it up, and had gotten to the bedroom, where I was going to make up the bed. I saw the clothes still laying there, and with the best of intentions, I started putting them away. I hung up the dress in the closet, but then I was faced with the dilemma of where to put the undies. If I put them in Jennie's drawer, they'd mix in with her things and could cause a problem when she rushed to get dressed one morning. I didn't want to leave them laying around, so I made room in my underwear drawer, neatly folded them up and put them in there. Again, the smooth material sent strange sensations through me, and as I walked out of the room, I found myself with another erection. "This is ridiculous," I said to myself, "women's undies are only exciting with women inside them." But a nagging voice in my head raised a disturbing doubt about that: "Are you sure?"
I dismissed the voice, and began to prepare dinner for us. When Jennie got home, she asked me how my day had been, and I told her pretty much the usual, commenting on how the secretaries at work had been giggling to each other about something for most of the time I was there. "Probably just girl-talk," Jennie said, "somebody fooling around with somebody, or someone having problems with a boy-friend." We had dinner, and then Jennie said, "Time to practice, sweetie, you promised." I groaned, but followed her into the bedroom. Jennie looked around for the clothes, and I explained where I had put them, and why. She didn't say much, just, "how thoughtful." I stripped again, and feeling the beginnings of an erection, I quickly pulled on the panties. She hooked up the bra, and in just a couple of minutes, I was dressed in the same outfit as last night. But this time, my cock was rock hard inside my panties. Fortunately, the tight fitting panties kept it pressed up against my stomach unseen. Jennie taught me how to walk around more gracefully, and told me how to sit like a lady. "No, no, keep your knees together, and cross your legs at the ankles. You're not ready to learn how to cross your legs yet," she scolded. I tried to concentrate on everything she said, reminding myself that I had promised that I would do my best. Later that night, after we had showered, we made passionate love, and the aching I had been feeling from walking around in panties all night, with the silky material rubbing on my cock, finally subsided.
The rest of the week passed pretty much the same way, although we made love every night, instead of the more usual, every other night or so. When we got up on Saturday morning, Jennie said, "You know, Robin, I'm beginning to think you might win that bet, after all." "What make you say that," I asked. "Well, you've been practicing every evening, but, I don't think you are going to fool everyone like I thought you were. There's just not enough time to teach you everything you'll need to know. I'm ready to concede right now." "No, that wouldn't be fair," I said, "I really am trying, you know." In the back of my head, I was beginning to understand something else, but I guess I was just trying to convince her that I was being a good sport. "Well, we can keep trying, but we'll have to step up the pace a little." I said I was, and she said, "then, you'll have to spend all weekend at it - are you still game?" Again I agreed, and she said, "you can't wear the same things all weekend, but I don't want you to wear your costume, either. I'll run over to Patty's and get some fresh things, I'm sure she won't mind." So while I was having a couple of cups of coffee, she went out, returning with another shopping bag of stuff. "I got some sexier things this time," she said. "Maybe you'll get into it more with more feminine frillies. Here, why don't you go put these on while I have a cup of coffee." This was the first time I had dressed by myself, and when I saw what she had brought back, I immediately got turned on. I went into the bathroom and shaved as she had said I should.
The undies were all black, and very frilly indeed. I slipped on the panties, and I felt myself almost ready to come from the satin feel on my cock. Without even thinking, I sat on the edge of the bed, and jerked my cock into a gushing orgasm. There was no denying what had just happened now - wearing panties was a definite turnon for me. I was wracked with guilt and doubts, but I knew I had to keep this hidden from Jennie. I slipped my arms through the straps of a longline black bra, which fortunately fastened in front. I zipped up the bra, feeling the tightness of it as it molded my upper body. The next thing I picked up was a black girdle, that had four garters hanging from the bottom. It looked as though it were half as wide as I needed for it to be able to fit over me, and I struggled to pull its tightness up over my legs and waist. It reached up to the bottom of the bra when I finally got it all the way up, but I felt like I could barely breathe with it on. There was a pair of very sheer nylon stockings which I carefully rolled up over my legs and managed to fasten to the garters, once I figured out how they worked. Just then, Jennie came into the room, and looked at me. "God, this girdle it tight," I said, "how do you women ever stand it?" "We have to suffer for fashion, dear," she laughed, "and I think you're going to have to suffer a little bit more." "What do you mean?" I asked. "Your leg hair shows through the stockings, and I'm afraid you'll have to shave your legs." "Now, wait just a minute," I protested, "I never agreed to anything like that!" "But if you're going to do your best, you can't have hairy legs, and besides its not like you go to a gym where anyone else could see you." She proceeded to take off my stockings and marched me into the bathroom. I half-wanted to protest some more, but also wanted to feel how the stockings would feel against my hairless skin.
Oh, how wonderful they felt - my sleek legs being encased in the sheer nylons. "Are you starting to feel sexy," Jennie teased, but not waiting for a reply, she led me back into the bedroom. "I borrowed a cocktail dress from Patty," she said, fastening a flared crinoline petticoat around me waist, then putting a black satin dress over my arms and head. "Great," she said as I stood there in the short, sexy dress. "The girdle and bra shaped you into the perfect size for the dress." She placed a pair of very high-heeled black patent leather pumps in front of me, and I stepped up into them. She walked me over to her dressing table, helping me adjust to the 4" heels and said, "We're going to go all the way today, a real makeover." She stood in front of me, and first attached false nails onto my fingers. Then she began applying all kinds of cosmetics to my face, gluing on false eyelashes as the final step. Then she pulled a curly brunette wig out of a bag, placed it on my head, and brushed it out a little. "My God," she said, "I said you'd be better looking than Dustin Hoffman, but I never expected this!" She stepped away from in front of the mirror, and what I saw reflected back nearly knocked me off my seat - there was a gorgeous woman looking back at me. I couldn't believe my eyes - I couldn't recognize myself at all. I sat there, stunned. "I ... y ... you made me ..." I was at a loss for words. "Stunning, that's the only word for you, stunning," Jennie supplied. She helped me stand up on the heels, and walked me over to the full-length mirror. The image there was even better and more powerful than what I had seen in the face-only dressing mirror. From the curly hair to the spike-heeled feet, there would have been no doubt in anyone's mind that this gorgeous creature was anything but a woman.
Jennie stood next to me, and we were mostly a study in contrasts, the petite blonde and the tall brunette, one dressed for day, the other for evening. But there were similarities as well, the womanly figures, the sleek, stockinged legs, the definitely female faces. She turned to me and put her arms around me, then, hesitating for a split second, kissed me hard on the lips. "I've never kissed a woman before, and even though I know its you, my mind tells me that's what I just did." I looked deeply into her eyes, and said, "But I'm still the man who loves you, underneath all this, you know." Her hand moved down and brushed the front of my skirt, feeling the erection beneath the feminine coverings. "D ... does dressing like this turn you on, Robin?" she asked in a quiet, low voice. I didn't know what to say, and I hesitated before answering. I had finally admitted to myself that it did, but I wondered what effect it would have on our relationship if I admitted it to her. We had always been honest with each other before, but I knew this was a potential crisis situation, and there was no way for me to predict the outcome. Believing that honesty was the only way to go, however, I said, "I can't explain it, and this is something I've never even thought of before, but it is exciting, Jennie, very exciting." She weighed this in her mind for a moment, and then she said, "Robin, I ... I can't explain it either, but kissing you dressed like that was, is, exciting to me, too. I've never wanted to kiss a woman before, but seeing you like that, knowing that you're a man underneath the clothes, its gotten me all hot also. I don't know if its a one-time thing or something more but, ..." She stopped talking when I kissed her, and with our arms around each other, we hurried over to the bed. Without stopping to take off any clothes, we began to make love to each other. The sensations I was feeling from the clothes I was wearing were heightened as I touched her, and in just a minute, she had maneuvered my cock out from under my things, and had impaled herself on top of me. It couldn't have been more than thirty seconds later when I felt myself starting to come, and I felt Jennie's body shudder with the force of her own orgasm.
Later on, as we lay next to each other, Jennie said that she felt like she had a new girlfriend, and I gave her a hug. "But, you know," I said, "we can't stay in bed all day, I still have so much to learn if I'm going to be able to carry this off for a whole night at the party." So we got up, and for the rest of the day, Jennie tutored me on the fine points of femininity, walking, sitting, eating, everything I would need to know in order to pass undetected as a woman. That night, when it was time for bed, she helped me out of the things I had been wearing all day, and though they had been tight and restraining, and it really felt good to get my girdle off, I missed them when they were gone. I started to walk into the bathroom carrying my robe, but Jennie stopped me, and handed me a babydoll nightie set. "Maybe you should keep practicing," she teased, and taking it from her, I smiled and gave her a kiss. After my shower, I dried myself off and pulled the frilly panties on, again feeling the wonderful sensations flooding over my cock. The feelings spread to my entire body as I slipped the short nightie on. I looked in the mirror, and even without the curly wig and the makeup, I felt feminine and wonderful. Jennie said, "you look cute in that, and I'm glad that `one-size-fits-all' is good for you." "Me, too," I responded, "and speaking of `one-size- fits-all' ", I took her hand and placed it on my erection, nestled inside my panties. We hopped into bed, and again made love.
When I woke up the next day, I lay there thinking for a while about what had happened, and what might be in store for the future. I decided not to worry about anything, but rather to just let things work out themselves. I got up, feeling the soft nylon surrounding my body, and went downstairs to make some coffee. As I sat there drinking it, I found myself automatically sitting in a very lady-like way, crossing my legs as a woman would. I looked down at my shaved legs, which, of course seemed strange, and remembered how the nylons had felt yesterday. Jennie walked into the kitchen about twenty minutes later, and I had a brief feeling of anxiety, wondering how she might react this morning to seeing me without makeup and my masculine haircut. But she cut my worrying short when she came over and kissed me, and said, "I love you, I really, really do!" After she had her coffee, she announced that it was time for today's training to start, and we went into the bedroom to dress.
She decided that I should wear regular daytime things today, and she gave me a set of pink undies, which I immediately put on, savoring the feeling of nylon against my groin and chest. She looked at me and giggled, and when I asked her what was so funny, she told me that my chest hair didn't really go too well with the pink bra. I felt myself blush, and she hurried over and hugged me so I would understand she wasn't making fun of me. I took off the bra, and we went into the bathroom where I shaved my chest, which truthfully had never been all that hairy. Putting the bra back on felt better than before, though, and she gave me pantyhose and a skirt and blouse to put on. Next, she applied a cosmetics for a more natural daytime look, and placed the curly wig on my head. When she moved aside to let me look, I could recognize myself, but the face I saw was clearly feminine. "I think you should wear heels again," she said, "because that will be the most difficult thing to get used to." I didn't mind a bit, though, because I loved how they made my legs look in the sheer pantyhose, and how they helped me walk with a feminine sway. We didn't spend the whole day in training as such, though we did spend some time looking through some of her magazines, but concentrated on doing some things around the house so that Dressing would become a more natural thing for me. She also taught me a little about makeup so that if I had to fix myself up at the party I'd be able to do it. The hardest thing, I think, was remembering to try to keep the pitch of my voice higher than normal, so I would sound, as well as look, like a woman.
The rest of the week went by pretty quickly, with me dressing up each night for more practice. Actually, I wore panties all week, and a nightgown she had bought for me every night. I practiced putting on basic makeup a few times, and actually got to be fairly good at it. Then it was finally Saturday, and in the early afternoon, Jennie said that it was time to start getting ready. "But its so early, it won't take us that long." "Don't be silly, dear," she said, "we're barely going to be on time, even starting right now." She drew me a bubble bath, and I relaxed in the scented water for a while, until she came in and said that I should shave my legs and chest. I did that while I was still in the tub. I got out, and was ready to start shaving my face, when she suggested that, since we were going to be out for hours, and I didn't want five o'clock shadow to appear, I should use a hair remover lotion. She put the liquid on me, and I felt a strong tingling as it did its work. I waited about fifteen minutes, sitting there while Jennie took her own bath and shaved her legs and underarms. I hadn't done the latter, and when she looked quizzically at me, I just nodded, as if to say sure. She lathered my underarms, and carefully shaved me. I don't have much hair on my arms, but she decided that what I did had to go as well. I washed off the hair remover from my face, and we went into the bedroom. I felt more naked than I ever had before, with all my hair gone, but I realized how feminine my smooth, hairless body made me feel.
"Just out of curiosity," I asked, "what exactly is my costume going to be?" Jennie had made me promise not to look in her closet or the shopping bags, and I hadn't, as much as I had wanted to. "Well, I guess I can tell you now, since you'll be finding out anyway," she said, "you're going to wear the costume Patty had for last year - Scarlett O'Hara from `Gone with the Wind' !" The memory of the beautiful gowns in the movie immediately flooded my brain. And then I remembered the difficulty Scarlett had with getting herself down to a figure that would fit into the gowns! Oh, God, I thought, what did I get myself into with this silly bet?
Well, the first thing I found myself getting into was a pair of long satin bloomers, with lots of ru- es of lace, around the whole garment. When I put them on, the silky feel almost drove me crazy, and Jennie just smiled when she saw the reaction I had. Next came the corset, and this was unbelievable if you've never worn one. Jennie laid it down on the bed, and I slipped my arms through the top straps and lay on top of it. Then she began to lace up the back. It extended down from the top of my hips, and the first few eyelets weren't too bad. But then as she moved up toward my waist, the boned corset began to pull me in tighter and tighter. Jennie sat on top of me, and pulled with all her strength to close the corset back together. "Stop," I said, "I just can't get that small," but Jennie just kissed me on the back of my neck and whispered, "but you have to, or the gown won't fit." She continued lacing me unmercifully, and I tried to get accustomed to breathing without being able to really draw in air. The confining corset, I could feel, was molding me into the shape it wanted, irregardless of the body it was enclosing. Even when my waist had been pulled all the way in, the tight laces compressed the flesh of my chest, pushing the excess up toward the bra's half-cups. I didn't realize how much there really was there, until after she had finished the lacing and I stood up. "I think that with just a little more," Jennie mused, and she went over to her underwear drawer and removed the padding from one of her bras. She worked one into the bottom of each cup, pulling up on my gathered flesh so that it then rested on top. When she had finished, I walked over to the mirror, still trying to get enough air to breathe, and saw the result. There was the sweep of female hips, and my waist must have been drawn in at least six inches. But, best of all, there was the swelling of breasts as my own flesh rose out of the half cups of the corset top looking like real breasts. The cups pushed me together creating cleavage, and Jennie said, "fantastic, I was a little worried because the gown is kind of low-cut."
There were six long garters hanging down from the bottom of the corset, and Jennie sat me down while she rolled stockings up over my smooth legs and fastened them snugly, snaking the elastic straps through the bloomers. I looked down and saw the mounds of my breasts, the tent created in the front of my bloomers by the huge erection I had, and Jennie kneeling at my feet. She looked up at me lovingly, and caressed my cock, then told me to stand up. I did, but she stayed where she was, reaching into my bloomers to free my cock from its satin prison, and she proceeded to suck me to climax. I held here head tightly against me after I came, and the feeling of love passed strongly between us. She stayed there for a moment or two, then said in a husky voice, "we'd better get moving." She got my petticoat out of the closet, a voluminous bulk of crinoline and lace. "There's no easy way to get into this, but just step inside, and try to move your feet until they're on the floor. I stepped inside the waistband, and sort of walked my feet forward until they had cleared the crinoline tent. Jennie buttoned up the back of the waistband, which fit perfectly around my corseted waist. From the waist down, all I could see was the bulky petticoat, spreading around me like a pyramid of snow, extending down to the floor. I twirled back and forth, delighting in the feeling of the rougher petticoat material swishing against my silken stockings and panties. The only things left were the shoes and gown, and after she had helped me into emerald green highheels, the petticoat was raised off the floor an inch or so. That had worried me, whether I was going to keep tripping on it, having forgotten that my heels would lift me into the air. I stood there looking in the mirror, when I heard a soft rustling sound behind me. Jennie had gotten the gown out of the closet, and I bent down a little, raising my hands so that she could lift it over me. It was a beautiful emerald green velvet, lined with satin, and it slid down around me with a silky woosh-sound. I closed my eyes, not wanting to look until Jennie had fastened the back buttons. When she said she was finished, I opened my eyes, and saw the lovely gown around me, my breast tops rising above the neckline, and the long sleeves fitting around my arms, ending in green lacy cuffs. The gown fit perfectly, and Jennie had to practically drag me away to put on my makeup. She worked quickly, and with the final touches of thick black lashes and a long wavy wig, I was ready. She put a costume jewelry necklace around my neck, and clipped matching earrings to my lobes. Again, the sight of myself had me speechless, and Jenny sprayed a little perfume on me, completing my journey to femininity.
When I was able to speak, I asked Jennie what costume she was wearing, and she told me that she was going to be a flapper from the '20's. She got herself into her things pretty quickly, and stood next to me in front of the mirror. Again, we were a study in contrasts, her short, slinky dress against my elaborate gown, her unfettered body versus my shaped and restrained one. But there was no doubt about it, when you looked at us, all you saw was two beautiful females. I must admit, my face was not a soft example of feminine perfection in the classic sense, but rather a striking, handsome one in the female sense of handsome. We got together the things we needed, and were almost ready to go when I said to her, "Jennie, I have a problem. I know no one will be able to see it under my petticoat and gown, but I am as hard as a rock underneath. I'm worried I won't be able to control myself with my bloomers rubbing against me all night." She didn't even hesitate, and she crawled under my gown, and took me into her mouth. She was really turned on by seeing me, and I felt her rub herself against my ankle as she brought me to a climax with frenzied sucking and licking. She had disappeared beneath my clothes, and the sensation of coming was almost like a surreal dream. She came as well, and she rested her face against the bare tops of my thighs for a minute or two. When she finally reemerged, we hugged each other, then she suggested that I needed something to prevent accidents for the rest of the night. She went into the bathroom for a minute, then into her undie drawer, and came back with a sanitary napkin and a belt to hold it on. "This should do the trick," she said, and she disappeared under my gown again. I felt her pulling down my bloomers and fastening the belt around me, then pulling back my now-limp cock between my thighs. She held it in position with the napkin, then pulled my bloomers back up to hold the entire thing in place. We were now ready to go, and she placed another napkin in the purse I was going to carry, "in case you have an accident later, dear. We girls always have to be prepared for that."
She drove us to the catering hall where the party was going to be held, and on the way, I admitted how apprehensive I was. "You know, I'm still worried that I'll be found out." "So what," she said, "don't forget its Halloween and everyone is in one costume or another. Yours is just more elaborate than most." Her words comforted me a little, but I still had mixed feelings - some guilt at dressing as a woman, some fear that I would be discovered and ridiculed, and, of course, some wonderful feelings about the touch of these clothes on me. When we got there, and walked into the party, there were at least a hundred people already there, and I asked her, "how many people do they expect?" Her answer, "at least a couple of hundred" made me shudder a little - here I was dressed as a woman in front of that many people, but on the other hand, with that large a crowd, I thought I could manage to stay in the background. We went inside, and over to one of the bars to get a drink. Before I could ask for a beer, Jennie ordered two strawberry daiquiris for us. I sipped the sweet-sourness of the drink, and said, "this is awful! I'd rather have a beer." She laughed, and said, "Sure, and slug it out of the bottle like you usually do? Try to remember, you're a lady, and you have to act like one." I smiled sheepishly at her, acknowledging that she was right, and we began to circulate. It seemed that our exotic costumes were attracting a lot of attention, and we were almost immediately surrounded by a group of men. The contrast of my elaborately gowned body with Jennie's obviously near-naked one had the guys in a state of heat. They were performing the mating-dance ritual, competing with one another for our attention. "That gown certainly shows off your figure," one of the would-be Lotharios said to me. "Thank you, so much, kind sir," I simpered, laughing to myself at the one part of my "figure" that would knock him for a loop if he saw it. Music was playing in the background, and he asked me if I would like to dance. He was a pretty good-looking guy, dressed in a vampire costume, but I begged off with a "not right now, thank you". I really wasn't all so sure of myself in heels that I was ready to try to dance in them! Jennie decided that we should break up this little group, and asked me if I wanted to "powder my nose". I took the hint, and we walked over toward the ladies room. Suddenly, it hit me - the ladies room. That was definitely unexplored territory as far as I was concerned, and I said that to her. "Don't be silly, no one will know - those guys certainly had no clue about you."
There were only a few women in the room, and I immediately headed for a large stall designed for handicapped people. It was large enough to accomodate a wheelchair, and I needed to room for my gown. It still felt strange sitting down to pee, not to mention just trying to maneuver around my gown and petticoat so I could sit. I noticed that the whirlwind activity and conversation had taken my mind off how I was dressed, and my cock was still laying back limply; it seemed that I might be getting used to this a little bit. I fixed myself up, and joined Jennie in front of the makeup mirrors. She whispered that I could use a light dusting of powder and a reap- plication of my lipstick. I managed the powder OK, and was very carefully applying the lipstick, when another woman walked over and stood next to me. "My goodness," she said to me, "isn't that cos- tume killing you?" "Oh, its a little tight," I said, "but it really makes me feel so feminine!" I caught Jennie's eye in the mirror, and saw her holding in a giggle. "No doubt about that, dear," the woman said, "I saw all the Romeos around you two before. Say, wasn't that guy gorgeous, the one who's the vampire?" Jennie took me off the hook and joined the conversation, "Yeah, he was really cute." "I wonder how big he is," the woman responded, nearly knocking me over with her words. I had no idea that women's conversations about men were as graphic as men's were about women. "Oh, I never worry about that," Jennie quipped, "its not how big it is, its what they can do with it, after all!" They dissolved in giggles, and I tried to recover and join in. The woman left, still laughing, and Jennie and I were alone for a moment. "I had no idea that you girls were that gross," I commented. "Well, don't you think its fair?" she asked. "You guys talk about tits all the time, don't you?" I had to admit that she was right, and we went back out to the party.
The next couple of hours passed in a blur as the party swirled around us, and then the crowd started to thin out a little. Then Jennie said, "Oh, oh, here's my boss, Mr. Harrison," as a tall distin- guished looking guy walked over. "Seems like we should have come to the party together," he said to me, after Jennie introduced us. "I hardly think so, suh," I said in my sweetest southern belle voice, "after all, you are a Yankee!" He had on a blue Civil War officers uni- form. "Well, I personally think that we should end the `War between the States' ," he said, and before I could answer, he took my hand, kissed it, and led me over to the dance floor. I didn't have much choice about it, and I almost gave it away by raising my left hand to lead. I covered up by patting my hair, and soon found myself twirling around the floor, following his lead. He asked me about myself as we danced, through the first song and into the second, and we chatted for a while. Finally, the song ended, and again kissing my hand, he led me back over to where Jennie was standing. "I think your friend is absolutely charming, Jennie, I'm so glad she came with you tonight.And I'm holding you personally responsible for making sure she keeps our appointment." He said goodnight and walked away. "You seemed deep in conversation, Robin, what was he saying? And what did he mean, appointment?" "Jennie, you're not going to be- lieve this, but we have a big problem. He was asking all about me, where I worked, where I'd gone to school, and when I told him I hadn't found a job yet, he insisted on making an appointment for an interview for next Friday. I couldn't refuse him, since he's your boss. What a mess!" "Well, don't worry, we'll think of something, some excuse or something by then." We decided to leave since the party was breaking up, and Jennie drove us home.
"I guess you realize that I won the bet," were the first words out of Jennie's mouth when we walked into the apartment, "nobody had a clue all night." "I know, you're right," I said. "I didn't believe for a minute when I agreed to the bet that I'd ever be able to pull it off," I admitted, pulling her close to me in a hug, and kissing her, "but I did have a wonderful teacher." She closed her eyes and kissed me back passionately, then murmured, "I love the taste of your lipstick." We stood there kissing for a while, and then we moved toward the bedroom, arms around each other's waists. "You're a beautiful Scarlett O'Hara," she said as we fell onto the bed together, "and I want you right now!" She lay me down on the pillows, and raised my skirt and petticoat, laying on top of me with the velvet and crinoline crushed between us. We rubbed our bodies together for a while, and the sensations from the clothing and her body surged through me. She lifted herself away, and removed my bloomers and the sanitary napkin that was restraining me. My cock sprang to attention and she pulled off her dress and panties, leaving her wearing only thigh-high stockings and heels. She moved back on top of me, and I spread my legs so that she could fit between them. My breath was coming in short gasps, from her weight on top of me, and from the tightly laced corset, and I stopped breathing entirely when her wet pussy devoured my erect cock. I wrapped my stockinged legs tightly around her, and I could feel my high heels digging into her back. I had the sensation that the cock that joined us was hers, and I felt so very, very feminine as she pumped away on my womanly body. A bolt of electricity surged through my body, starting at the groin, and exploding in my head as I had a magnificent orgasm, and her whispered, "yes, yes, y-e-e-e-e-s-s-s," told me that she, too, had come. We lay there for a while, just like that, as I didn't want to let her get out from between my tightly wrapped legs. Then she helped me up, and, with great reluctance, she began to get me undressed. She helped remove my makeup, and we crawled into bed together, naked, and made love again, this time less furiously, but rather with a deliberate slow sweetness. As we lay there, drifting off to sleep, I almost started to mention the problem with Mr. Harrison, but decided that I didn't want anything to spoil what had been a perfect night.
The next morning we talked about how wonderful the party had been for a while, then when I thought the moment was right, I brought it up. We were sitting there in our own robes when I said, "Jennie, I really think that we've got a big problem here. Mr. Har- rison all but told me that he wanted to hire me, but he'll be really pissed off when he finds out that he was fooled and was dancing with a guy. I mean, he was being so gallant, kissing my hand and all, he'll go right through the roof. Maybe I can cancel the appointment and say that I found something else." "I don't know, Robin, that would sound fishy I think, since you told him that you've had no luck at all. He might get mad at me, since he said I was personally responsible for delivering you. That's all we'd need, for me to get fired." I agreed, since it was Jennie's earnings that were keeping us from being starving homeless people. We talked back and forth for a while, trying to figure some way out of the dilemma, when Jennie said, "this is hopeless. I can't figure out any way to solve this, un- less ..." "Unless what, Jennie?" "Unless you keep your appointment, silly." "But I can't do that - I just know he'll be pissed off when I walk into his office in a suit," I said. "Not if its a woman's suit," she replied. "Now wait just a second," I said, "I agreed to go to the party, that was one thing, but this is something else entirely. I'll never get away with it." "Sure you will, he'll be expecting to see a woman, and that's what he'll see. You can go in for the interview, and that will be the end of it. Simple, one hour and it'll get us off the hook." We had our first argument about it, because I felt that it was much too risky - if Mr. Harrison would be pissed off to find out I was a guy, how pissed off would he be if he caught me trying to pass myself off as a woman when he was interviewing me? Jennie believed that I could get away with it, but my confidence level wasn't anyplace close to that high. Finally, she used the ultimate female argument - she burst into tears, and what could I do but agree to try her plan?
"Listen," she said a while later, "we've got a few things going for us. First, your appointment is for first thing in the morning, so I'll be able to get you ready and go in with you. Second, he's not a real morning person, so he won't be as sharp as usual. Third, we have another week to work on you. That's a big help. We'll have to get you an outfit to wear, but I can always give it to Patty as a Christmas present, so it won't really cost us much." What she said seemed to make sense, so I told her that I guessed it would be OK, and that she should pick up the outfit for me. "We can't do that," she said, "you'll have to try it on, to make sure it fits right and looks good. I can't be running back and forth to stores all week, there's too much else to do. We'll have to go shopping today, so you can try things on before we buy one." Again I balked, arguing that I couldn't go shopping and try things on in stores. "Well, if you're going to pull this off," she countered, "you'd better be able to pass yourself off as a woman! And remember, there's no Plan "B"." So, about two hours later, I was nervously getting out of the car at a shopping mall, dressed in the pink and white shirtwaist dress I had worn the first time I'd dressed. Luckily it was a warm day, late Indian summer weather, and I didn't have to wear a coat, which I didn't have anyway. I was wearing the white undies and pantyhose, and when we got into the mall, I heard the clicking of our heels on the marble floor. This time, dressing hadn't excited me, because of the risk I was taking. Halloween was over, and if I were found out, I envisioned myself in jail or something for being in drag in a women's dressing room. We went into a department store, and hurried past the cosmetics section, with the sales people offering everything from samples of perfume to full demonstrations of cosmetics, into the women's department. "First, you'll need your own undies," Jennie said, "because I'll have to return Patty's stuff within a couple of days." She went through racks and racks of bras, panties, and other "unmentionables", selecting a few things for me to try on. "One good thing," she said, "is that we girls share dressing rooms all the time. No one will think it unusual for the two of us to go inside one together. She picked out a few things in her size, and we went over to the dress department. "I think that a suit might be better than a dress," Jennie suggested, "because everything will go together, and you won't have to worry about about something not fitting quite right, because they'll be separates." She picked out a couple of suits and blouses, and we headed off to the dressing room. My biggest fear, that the attendant would spot me, was allayed when I saw that she was only concerned with counting how many articles we were taking inside. We went into the cubicle, passing women in various stages of undress, and closed the door. "I'll bet this is every guy's fantasy, seeing lots of women in their undies," Jennie whispered to me. "Well, its certainly better than a sharp stick in the eye," I teased back, as I was undressing. She poked me in the ribs and said in a mock serious tone, "just remember who brung you to the dance, buster!" I quickly stepped into the panties that she handed me, and tucked myself back. She slipped the matching bra around me and fastened it, stuffing the extra panties that I was using into the cups. She handed me a white half slip, and then a silky white blouse with a lacy ru- e around the neckline. I tried on the skirt from the first suit, then the one from the second. "No, these won't fit your waist properly," she said. We'll have to get something to pull it in. Wait here a second." With that she went out, and I never felt so alone in my life. I was like a spy in enemy territory. She came back in just a minute or two with two things, a padded panty girdle and a waist cincher. She fastened the cincher around me, and the hook-and-eyes pulled my waist in. Then I put the panty girdle on, compressing my waist even more, but adding a little padding to my buns. The skirts fit now, and I put on the jacket. "Well, I think either of these will do," she said, "which one do you like better?" One of the suits was a navy blue, the other a nice green. "I think the green one," remembering how much I had loved the green velvet gown. "I agree, and besides, Patty already has a blue suit, so when we pass it along, she'd like the green one more."
I changed back into my own things, and we headed to the shoe department. I was again a little worried about being so close to someone, but Jennie reassured me, "don't worry, if its a guy, he'll be too busy concentrating on trying to look up your skirt." It was a guy who helped me, and Jennie was right. I was almost tempted to let the loser look ALL the way under my skirt, but I restrained myself. I picked out a pair of green suede pumps with a 2" heel that went perfectly with the suit, and after we paid for everything, we hurried home.
The next week was another blur, and before I knew it, it was Thursday night. "We'd better get a few things done tonight, so we'll be OK in the morning. She glued on extension tips to my own nails, saying that it was better not to have to worry about a stick-on nail coming off. When she had all ten fingers done, I was amazed at how much more natural they felt. She manicured my nails then, shaping the extensions and applying a subdued medium red polish. I was surprised when she started putting polish on my toenails, and I said, "why bother, he's not going to see them?" "Trust me, you'll feel more feminine with them polished," and when she finished, I found that even this hidden sign of femininity did make me feel more girlish. I took a nice long bubble bath, and shaved my legs and underarms. My face I would take care of in the morning.
When we went to bed, Jennie surprised me with a slinky black nightgown that I hadn't even seen her buy, and we slid into bed together, our silken covered bodies sliding against each other as we made love. I tried to be careful, but as I was getting ready to come, my long nails dug into her back. This seemed to excite her even more, and we lay there, out of breath, for a while until we fell asleep. The next morning was a panic, in retrospect, as two girls tried to get ready at the same time, but by the time we were ready to leave, I felt pretty confident that I was going to be able to pull my masquerade off. I wished, though, that I could have been wearing a heavier makeup, feeling somewhat naked and exposed with a natural daytime look, but Jennie patted my padded fanny and reassured me that I looked great.
The moment of truth arrived all too quickly, and Jennie brought me into Mr. Harrison's office, whispered, "Good luck," and left, closing the door behind her. "Good to see you again, Robin, glad you could make it," he started. "Why don't you sit here on the couch, where you'll be comfortable?" He proceeded to interview me, sitting next to me on the couch, and I noticed that he couldn't keep his eyes off me, focusing most often on my breasts and legs. I answered all his questions easily, having been on so many interviews already. "You know, Robin, I have to admit something. I thought you looked wonderful at the party, and you look just as nice today." "Well, thank you, Mr. Harrison, its very nice of you to say that," I replied. But the sleaze wasn't finished yet - he put his hand on my nylon-covered knee, and said, "I find you VERY attractive, and I'm sure we can find a job for you here." His hand moved slowly up onto my thigh, under my skirt. The son-of-a-bitch was making a blatant pass at me, and was about eight inches away from discovering my secret. My first impulse was to haul off and belt him, but I controlled myself and stopped the upward movement of his hand. "Mr. Harrison, I'm surprised at you, what kind of a girl do you think I am? I know you're married, Jennie told me so, and I wonder what your personnel people will think when I slap you with a sexual harrassment lawsuit?" He sat back in shock, realizing the position he was in. He stammered, trying to make excuses for what he had done, but I clearly wasn't buying it. "I just couldn't help myself, you were so beautiful in that gown, and your green suit reminded me of it ..." "Mr. Harrison, you are in a world of trouble, now, because my next stop is my attorney's office!" He seemed to shrink inside himself, and he began to beg me to forgive him and to forget what had happened. Finally he said, "Robin, please, I'll be ruined, isn't there anything I can do?" I loved the position of power I was in, and I realized that women were not the weaker sex after all. But I knew that with no witnesses to what he had done, I needed more leverage to take advantage of the situation. "You said that you definitely had a job for me here?" "Ah, yes, of course," he answered. "And what might the salary for this job be?" I inquired, adding, "remember you did say anything, right?" "Would er-ah $35, 000 be adequate, Robin? I'm sure we could go that high." This weasel was offering me $7,000 more than he was paying Robin, to save his ass.
"Oh, that sounds very fair, Mr. Harrison," I said, beginning to bait the trap. "You know," I continued, "I may have overreacted before, I'm sure you didn't mean anything nasty, did you?" "Oh, no, of course not," falling deeper into it. "As a matter of fact," I said, tracing a line on his cheek with one of my long red-tipped nails, "I found you quite attractive as well. Maybe we can reenact the Civil War someday," I teased. Thump! He fell all the way in. I moved my hand down from his face to his belt, and started to unbuckle it, saying, "perhaps we should seal our agreement, don't you think?" I almost felt sorry for him, but quickly got over it, as I unbuckled and unzipped his pants. He stood up, took off his shoes and stepped out of his pants. "Can we sit in your desk chair," I asked, innocently, "I love positions of power." He couldn't get there quickly enough, and I nestled on his lap, gazing up into his eyes. I felt his hardon pressing against my buns, and I wriggled around on it, driving him further to distraction. While he was lost in his fantasies, I reached over and picked up his phone. "Jennie, dear, could you come right into Mr. Harrison's office, I need your help." "W ... what did you do that for," he cried, and he tried to get me off his lap. "No, Mr. Harrison, you're not going anywhere," I said. And at that moment, Jennie came into the office, expecting the worst - that I had been found out. She burst out laughing when she saw the two of us, and quickly shut the door. "Mr. Harrison has made me a job offer, Jennie," I said, rising off his lap. "Stand up, you creep," I said to him. His hardon stuck out through the opening in his boxer shorts, but I could see it wilting away. "he offered me $35,000, isn't that wonderful? I was going to accept, but then I thought, you know how we girls gossip, and I just knew that you"d find out how much more I was making than you. That wouldn't be fair, would it?" "No, I guess not, especially under these circumstances, sexual advances and all."
The poor bastard just stood there, realizing that we had him by the short and curlies. "What are you going to do?" he asked, very meekly, his cheeks burning with embarassment. "Well, first of all, I think it would be only fair to give Jennie a raise, don't you?" "Ah, yes, of course, immediately." I handed him his phone, "OK, do what you have to do, right now." He dialed personnel, and said into the phone, "This is Jim Harrison. I need an immediate raise put through for Jennie Burns, to $35,000. Yes, I said immediately. Another company is trying to recruit her, and we can't afford to lose her. And prepare a contract for my signature, three years for her - I want to lock her in now." He listened for a minute and said, "of course I want raises specified in the contract, ah, five thousand a year," glancing at Jennie, who nodded her agreement. "Yes, five thousand a year. And I want that contract here on my desk within the hour." Some big shot Vice President, ordering people around, while trying to retain his dignity in polka dotted boxer shorts. "How about you, Robin," Jennie asked, "do you want to accept Mr. Harrison's generous offer?" This was the question I had been dreading. We could obviously get most anything we wanted, and I really wanted a job, but it was out of the question now for me to take it as a male. We would lose all the leverage we had if my secret were exposed. But if I accepted it, I would have to dress as a woman all the time. My cock stirred inside my panties, and I knew in my heart of hearts that I would not stop dressing when I got home today anyway. I loved being in frilly panties more than anything. "What do you think, Jennie, I think you have a great deal to say about this, since we'll be working together." That's what I said, but the hidden meaning to my question was clear - did she want, approve of, my continuing to dress as a woman? "Why, Robin, dear, I think it would be wonderful, and exciting, to have you working here with us." I could not have hoped for a more supportive, understanding answer.
I handed the phone back to Mr. Harrison, and he instructed personnel to draw up a second contract for me, on the same terms. Jennie slipped out of the office, but quickly returned, carrying her large purse. "I think we've treated Mr. Harrison so badly, Robin, don't you?" "Yes," I said, playing along with her, but not knowing where this was going. Mr. Harrison has a reputation for being a real hard-nosed businessman who always manages to come out on top. She pulled a Polaroid camera out of her bag, saying "we use this to take a quick look at ad layouts and things, but we have a better use for it now - insurance. Take off your clothes, you worm," addressing Harrison. He started to protest, but Jennie cut him off, "if you don't do what I tell you to, I'll call your secretary in to see you in your funky boxer shorts. And you know what a gossip she is - it'll not only be all over the company in twenty minutes, your wife will know in ten!" He had no choice, so he silently stripped everything off, and beagn to follow our instructions. "First of all," Jennie said, "you have to look like you're enjoying yourself. Rub that little cock of yours until it stands straight up." Mortified, he began to stroke himself into an erection. We then began to pose him with each of us, first with his arm around our waists, then in progressively more humiliating poses. We made him kneel down, and we took turns using his back as a footrest. Then we shot pictures of him licking our high heels, his erect cock in hand, showing how much he loved it. Finally, we bent him over his desk and whacked his ass with a ruler, until red welts showed up clearly all over. "Play with yourself as I'm doing this, creep," Jennie ordered, "make yourself cum in your hand!" He did, blushing the deepest red I've ever seen anyone blush. "That's what you wanted, isn't it?" I asked, and when he came in his hand, I continued, "you were probably hoping for a blowjob, to have me taste your filthy cum - rub it around on your lips for the final shot!" He groaned, but complied, and Jennie snapped two pictures, one with the cum pooled in his hand, clearly having just shot his load, and the second as his hand moved to his mouth and rubbed. "You might as well lick it off and swallow it, you pig," Jennie laughingly ordered.
After his final humiliation, we told him to get dressed, while we waited for the contracts to be delivered. I spent the time planning the wardrobe I was going to buy, and all the wonderful things I would be able to wear. He signed the contracts, and as I was ready to leave with our copies, I said to him, see you bright and early Monday morning, Mr. H!" "I think I'm feeling a little poorly, Mr. Harrison, would you mind if I took the rest of the day off?" Jennie said. He nodded his agreement weakly, and we walked out, arm in arm.
Well, this all happened three years ago, and to bring you up to date, we've both done wonderfully, both personally and at work. Mr. Harrison, poor dear, left the company about six months later, and both Jennie and I have been promoted by our new boss. We also got bonuses each year, and have been told that "old Harrison really knew what he was doing when he hired you two." I dress as a woman all the time now, and at Jennie's suggestion, I went on hormones for a while, and had a breast implant operation done. But I have no plans to go any further, as Jennie still loves her girlfriend's hidden secret.
FIN