OK, let's face it: that's not a very compelling story. It's just not quite as interesting when I haven't been. . . converted yet. The conversion is the best part. There's little that's psychologically interesting about having already experienced it all, and just chronicling how I'm doing it again. It's just that it gets so boring to tell the same old story over and over again. I can pretty well reduce it to this: I am forced, duped, or otherwise compelled to wear women's underwear; I discover that I like it; I continue to wear it and get a sexual kick out of it, and long to become a girl. The story ends when I decide at last that I want to be a girl. The fun is all in the discovery and the forsaking of manhood. So really the best thing I can do is come up with new fantasies telling that same story again and again.
By the way, I had Anca petting on top of me, and I was feeling like our roles were inverted. I felt like I was the girl, getting fucked by the strong body on top of me. She was having her period, so we couldn't fuck; but I was in the right mental state to feel like a girl.
Anyway, another tedious fantasy:
Life is tough these days after graduating. It's so hard to find a decent job. So I ended up as an office temp.
My boss was female. She was a very aggressive woman. She loved authority. But she was also quite an attractive woman.
OK, let's try this again, as a diary:
Monday
My interview at the Butterfly Corp. went quite well. Must say that the woman who interviewed me, who will be my boss if I get the job (knock wood) was quite a sexy woman. She wasn't necessarily beautiful, but something about her was sexy. The way she carries herself, the way she moves, I don't know what. But I look forward to seeing her every day. Imagine having her to look at every day! Yow!
Monday
So I started my new job at the butterfly corp today. The boss, Ms. A., is quite the knockout, alright. My job sucks. I have to be her gopher, in effect. I do all the dirty grunge work around the office, but mostly menial tasks for her. I get her coffee and take her clothes to the cleaners. I type up letters for her. I'm almost her secretary. I wouldn't bother with this job if the money weren't so good, and if the boss wasn't so attractive.
Monday
Still adjusting to new job. Boss gives me lots of funny looks, I think. I always wonder when things like this start if they're all in my imagination, or what. But I can't help ogling her as she moves around the office. She always wears skirts, to show off her wonderfully lithe legs. I don't think I could ever love her or anything, but damn it, she's sexy. I just can't get over it. I might even say that I think I'm developing a crush for her. Yikes! What kind of weird position does that put me in? I do look forward to coming in to work every day, though, and what can I say? It's good for a start, I suppose. Who knows? There might be some room for advancement in there.
The following Wednesday
Argh! I don't know what to do anymore! The boss propositioned me. She asked me if I would like to meet her after work for some dinner. I didn't know what to reply. First of all, I have a horrible crush on her, which makes working for her almost intolerable. Second, I don't know whether I should feel threatened if I don't do it. She'll probably fire me. What will I do then? I desperately need the income. But hell, she's attractive enough, and I do have a thing for her, so what do I care if I whore myself to her? Who knows, I might get a raise or a promotion. . . The trouble is, how do I explain all this to L [my girlfriend]? She sure as hell doesn't have to know.
Thursday
Dinner was tasty. So was Ms. A. She brought me home with her tonight for a nightcap. I couldn't refuse her advances. Even if my morals or my code of ethics had tried to stop me, I don't think I could have resisted her. She has me in the palm of her hand, and she knows it. She barked out commands in bed, which I gladly followed. It wasn't about me, it was all about pleasing her. We both want nothing more than to please her. She sure has a nice body for a woman her age. Christ, she must be only 30. Anyway, she kicked me out when she was done with me. I wonder how I'll face her tomorrow. And she warned me not to tell anyone about it, or else I'd lose my job. She'd fire me for sexually harassing her by spreading rumours about things that went on between us. And who would believe me over her, anyway? Well, that's fine with me. Who would I tell, anyway? It would be pretty embarrassing, I think.
Friday
Ms. A brought me into her office for a closed-door meeting today. She had me fuck her right there against a wall. It was a real quickie. Then she told me to get out and the day went on as if nothing had happened. I'm never leaving this job.
Monday
I thought about Ms. A all weekend. She obviously hasn't. She tells me now when we small talk before I bring her her coffee about what she does on the weekend. She went out with some other man, she tells me. Had a great time. A wonderful man, possible husband, she says. Is she saying that just to needle me? She knows that I wouldn't dare mention what went on between us. That would be taboo. So I worked all jealous and pissed off all day long. She must be playing mind games with me.
Tuesday
Ms. A didn't call me into her office today again. I'm wondering if I'll ever have that privilege again. Life sucks.
Monday
Finally, after a whole week without tasting of my boss's flesh, she called me into her office again. "Rob," she told me, "You're doing such a wonderful job around here, but I'm feeling the pressure from upstairs. I'm afraid that I'll have to reconsider your position with this company if I want to keep you." I was scared stiff. Was she letting me go? "The department doesn't have it in its budget to keep a gopher around for me. But there is a possibility of me getting a secretary." "Secretary?!?" I ejaculated. I don't want to be a secretary. No way. I'm a writer, not a damned typist. "Yes, a secretary. Now, since you're so good," she said, getting up from behind the desk, and sitting on the corner right in front of me, showing me plenty of leg, and fondling my shoulder, "I don't want to let you go. You'd be doing pretty well the same work, but it would be more formal."
I can't repeat exactly what she said. But she expects me, in short, to be her secretary, but not in the modern, gender-inclusive sense: she wants me to fill the role of a female secretary. All the other execs have one, she whined, and she wants one, too. But it wouldn't look right if her secretary were male. For one thing, people would think she was doing it for sexist reasons. For another, they wouldn't appreciate putting someone of my talents in such a tedious position. I asked her what she meant by having me become her female secretary. She told me that she would fill me in later as she gathered more information on the subject. So she left me out in the cold on that one. But then she made me give her head after, and then I resumed my workday. I expect a more detailed answer by the end of the week.
Wednesday
This is getting pretty weird. I don't know who I am anymore. I did things today that I don't think I'll ever admit to doing to anyone. I can't believe what that woman made me do!
I don't know quite how to say this. Suffice it to say that I did something very perverse, and very nasty. Something that no man would ever admit to. But what's a diary for? I have to intellectualize this, I have to look back and figure out what the Hell I was thinking.
Today, Ms. A surprised me in her office. She had given me some lingerie outfit to take to the cleaners. Or so I assumed. She had me close the door when she called me in to get her laundry. But that's when she started kissing me passionately, trying to seduce me. Of course, it worked quite well. This time, however, she had me take my pants off entirely. I was wearing nothing below the waste. We sometimes do this to enjoy some exotic positions on her desk. But she took away my boxers, and handed me her lingerie. "I'm afraid," she said "that you're going to have to change a couple of things in your lifestyle." She commanded me to put on her panties. I stood there dumb with her underwear in my hand, incredulous. "Put them on," she growled, "or get out of my office and go home." Intimidated by her threat, I stepped into her panties. Yes, I wore her underwear. But that's not even the worst part.
We hadn't had sex yet. She was still horny. I had been, but I felt a little silly and very embarrassed to be wearing her underwear. Nonetheless, she threw me on her desk and rubbed her crotch on mine. "Get used to it," she said, "or else you're fired." This time she made me come, and she made me clean it up myself. She made me lick up my semen.
I came out of that office frightened out of my wits. Underneath my dress pants I wore frilly panties. I had no choice but to wear them all day long. But it's worse. Much worse.
I think that that was by far the most intense sexual experience I've ever had.
She made me take home another lingerie outfit in a cleaner's bag. She told me that I'd better be wearing it tomorrow, or else she would fire me.
This would normally be the place to ask: what should I do? But I think my choice is pretty clear. I don't even have trouble making it. I'm going to wear that lingerie under my clothes tomorrow. I need the job, for one thing. For another, who has to know except for her and me? And besides, it's really not so bad to wear. I barely notice it.
Thursday
What an embarrassing mistake!
I had it all planned: I would keep the lingerie hidden in the trunk of my car so that L wouldn't see it. Of course, it would be disastrous if she ever found another woman's underwear on my person. So I would drive to work, and change into the lingerie in the washroom. Simple.
So that's what I did. My heart pounded all the way. I could barely eat this morning. But I got to the washroom safe and sound, with the lingerie concealed in my tote bag. I didn't realize how difficult it would be.
I forgot how busy that washroom can be. And, like every other washroom, there's a good foot-high opening between the floor and the bottom of the door. How was I going to manage this without being seen? I took my pants down, as if I were taking a shit. I put the panties where my boxers were. I quickly lifted my leg and put it back in, deftly removing my loafers as I did so. I don't think anyone noticed me doing it. It could have been quite noticeable: I had to put on these silky burgundy panties, very frilly and high-cut, and make sure that no one would see my legs. But that was the easy part. That and the bra.
There were also some stockings in the package. I hadn't anticipated that. But somehow I managed. It was very hard: I had to take off my sock somehow, and put it back on, without anyone noticing. Then I had to do it again. I must have spent 10 minutes in there trying to figure out what to do with the garter belt. Fortunately, I gave myself plenty of time. So off I went to the office with sexy women's lingerie under my clothes. I was mindful to take a dark solid coloured shirt to make sure that the bra wouldn't be noticeable underneath. Still, I feared that the strap would show under the material.
With all this rigamarole, however, she didn't even call me into her office. I prayed all day that my ordeal would have some kind of benefit, but she never asked to see me. Only at the very end of the day did she come to my desk and tell me, "don't worry, I didn't forget what I told you yesterday. Consider yourself lucky that I didn't have time to check. You'd better wear it tomorrow, though, or else, you know the consequences.
So, just like that, I was duped. She made me wear her lingerie all day, and she didn't even bother to make sure. So now I have to worry: will she check tomorrow? And if so, I'd better be wearing it. I cannot risk that she calls me into the office, and I'm not wearing it.
Tuesday
Finally, she checked me out today. She was quite pleased. She was glad to see that I had heeded her warning. It was a test. She had been playing with me all along. She complimented me on it, too. I was red-faced. The things I do to keep a job! It all paid off, though, because she mounted me like she did last time. I'm not ashamed to say that it surpassed even that moment as the greatest sexual thrill ever. And I did it all in women's underwear! She told me to take it to the cleaners to get rid of my come stains, and she handed me back my boxers, which she had kept in her desk. She told me that I could wear those again if I wanted to, that my job wouldn't hang in the balance. That's when I asked her about my job. "Oh, I still haven't found out yet. I'll let you know as soon as I can."
So what do I make of this? I wore her lingerie for five days, and what for? More importantly, she made me feel things that I'm not sure I can admit to myself. What was it about that experience that made it so good? I'll tell you: it was the lingerie. She made me totally aware of what I was wearing when she humped me in her office. She snapped my garter belt, my panty elastic, my bra. She fondled my nipples. I swear that I felt like what I imagine a woman feels when she's getting laid. I don't know what this means, I don't know what this makes me. But I wore women's lingerie, and I liked it. Even so, I hope that I never have to do it again. I can't handle it.
Thursday
She has me like putty in her hand. She has me begging to wear her underwear in her office. She told me that she won't let me, unless I shave my body hair, and get my own. So that's what I've done. L is baffled. She doesn't understand. She caught me wearing her bathing suit today. I wanted to see if it was anything like lingerie. It was almost as good, I must say. She is packing her things up and leaving me. She hates me now. But I couldn't care less. Ms. A will certainly keep me satisfied.
As by her suggestion, I bought some lingerie after work. It's going to take me a while to build up a wardrobe. But I'll go to work from now on all sleek and sexy under my business clothes. All feminine. As long as L doesn't tell anybody about this. . .
Friday
Finally, Ms. A has told me what I have to do to keep working for her. She explained what she means by becoming her female secretary. I have to become a woman, at least on the surface. She's going to pretend to fire me, and I will come in for an interview as a woman, applying for the secretary's job. So I'll be coming in to work from now on in skirts and blouses and dresses. And I'll still be Ms. A's gopher. Only, I'll be a girl now.
This could be more interesting if I have my narrator decide to wear women's underwear only after finding out what the new job entails. But that could be tedious, too.
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