Fiction: Secretary's Diary

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.

Fiction: Genie

One day, as I walked along the beach at sunset, melancholy, depressed about my lack of luck in love,  a strange looking bottle caught my eye as it glistened in the fading sunlight.  I picked it up, cleaned it with my sweater, and nearly shit myself as a massive djinn billowed out of the bottle.

"You have released me from my prison of a thousand years.  I grant you anything you wish for," said the djinn.
Unable to pass up such a wicked deal, I instantly wished for infinite wishes.  The djinn was reluctant, but he had to accept.  Oh, well.  That's his problem.

Amazed with the possibilities, the infinite possibilities, I sat there dumbstruck.  Then I wished myself a few trillion dollars, and a harem of beautiful women.  That's when my good fortune began.

My women were all ugly.  So I wished for new women.  I had to give specific details, and I found myself completely unable to sufficiently describe a woman adequately enough so that she would appear to me as perfectly as she had in my imagination.  So I began to pick and choose from the real women in the world.  I started with the [girl I met at a live music show who models skin care products].  And I added the blonde from music class and the hippie girl from school.  I had them all at once.  I didn't give a damn what any present girlfriend thought, although I made sure to wish for her eternal happiness with men, out of a sense of combined guilt and respect.


But this grew tiresome.  Mostly, the girls just didn't connect as well as I could have hoped.  I wished for them to, but it wasn't the same.

Then I got the idea.

"Djinn," I asked, "I wish for my ultimate sexual fantasy to be fulfilled immediately, whatever that may be; and to make sure that there is no mistake, I wish that you might have a perfectly clear idea of exactly what my fantasy is."

Then the djinn replied, "These wishes test the limits of my power.  You must choose now whether you want to keep this fantasy as reality or return to an entirely mundane way of life of before.  They are your only two choices."

"So, let me get this straight," I said.  "I have a choice of either living my ultimate sexual fantasy forever, or returning to my normal life forever.  Tough choice."

"Do not choose too quickly.  No one fully understands the extent of their fantasies until they truly live them out. . ."

"I choose to live my fantasy forever," I immediately answered, perhaps too rashly.  But I think it must have been the best decision I ever made, even though I had my necessary doubts for a long time afterwards.


The djinn laughed and said, "as you wish," and snapped his fingers.  He disappeared in a puff of smoke, and I looked forward to being swept away by beautiful maidens who would fuck my ever-potent immortal dick forever until the end of time.

But it didn't happen.  I stood on the sidewalk where the thought had struck me to wish for this and waited for things to happen instantly.  But nothing came.  I began to wonder if the djinn had somehow tricked me.
Just then, an explosion rocked me off my feet.  I was knocked out cold.  When I woke up, it was in a dark room, all alone.

I felt fine.  I was uninjured.  But I had to wait for hours for anything to happen.

It was then that I noticed that I was naked, and in a small cell.  A huge beast of a man came to my door, unlocked it, and dragged me out.  I was powerless, and surrounded by big burly guards.  They threw me into a room, where a beautiful woman sat upon a sort of throne, attended by plenty of other beautiful girls, scantily clad.  I was made to kneel in front of her.  So much for my fantasy, I thought.

"You have been chosen," she announced to me, "to further the causes of women.  You will soon be indoctrinated in our ways."  She waved a hand, and the room cleared, and we were alone together.

She came off her throne, and sashayed over to me.  She was wearing fishnet stockings, a tight little skirt, and a tight little blouse, accentuating her tits, her ass, and her legs.  She was blonde.  It was the Noxzema girl, the hippie girl, the music girl, all the beautiful girls wrapped up in one.  My eyes virtually popped out of my head.  "Do you like girls?" she asked.  I could only stare in amazement.  My dick was flaccid with embarrassment.

"Well, you don't seem to be very excited.  But I know that you are.  You have to do me a favour.  You see, I need some people to help me in my little cause.  And you're a prime candidate.  I know you like girls.  I know you want to fuck me.  But I have to change all that.  You don't have to understand why.  There's nothing you can do about it.  You've been chosen.  You will do everything I tell you to, not because I tell you to, but because you will desperately need to to fulfill your own petty desires.  Any questions?"

I stammered.  This was pretty much what I had told all the girls in my harem when I wished for them and got them.  Except for having to change anything.  I started to get a huge boner.

"Since, you're speechless, let's get started."  She shoved her genitals in my face, and let me undress her, bit by bit.  I worshipped her every curve, every little feature.  We fucked like animals for a long, long time.  It was the best sex I had ever had.  It is still the best sex I have ever had.  I will never forget it.  I thought that my existence would hereafter be slavery to this beautiful woman forever.  And I could never get out of it.  And I feared that my decision had been too hasty.  As much as I enjoyed fucking this goddess, I didn't want to be her slave forever.  But it was only just beginning.

We did it all.  She blew me.  I ate her out.  We had 69.  I tit fucked her.  I fucked her up the ass.  She fucked me up the ass with a dildo.  I dressed up in her clothes.  We added one of her girls into the mix.  We tossed her and added another man in.  I was shocked to discover how far I would go to please us both.  For the first time ever, I had a sexual encounter with a man, albeit she was the focus of my attention.  I actually sucked him off for her.  Throughout the entire time, I must have come a hundred times, and instantly reloaded.  It was fantastic.

I was quite surprised when, after she had finished with me, she turfed me, naked as I was, and exhausted from so much incredible gratification, onto the street.  I was alone and helpless.  I hated her for treating me like that, and vowed to either forget about her, or if I ever saw her again, to kill her.  I was completely disillusioned about my djinn.

I went home to my palace, and fucked the girls in my harem as I had before.  But they were so very bland compared to the goddess.  I thought of her in her little panties and bra as I had my way with my harem girls.  The picture jsut wouldn't go away.

I hoped to forget.  But I just couldn't get that picture out of my mind.  I found myself thinking about those panties.  How I had worn them myself, how much fun I had with her.  I tried to recreate the experience I had with her with my harem girls.

I had routinely had several at a time, so that was nothing new.  And I had sucked every part of their bodies, and had every part of mine sucked in turn by each of them.  So I experimented with their panties, too, and restored some of the drama, some of the chemistry.  Only the harem girls laughed irreverently, secretly, at my little experiment.  They didn't appreciate true femininity.  They didn't know how to please me like that goddess did.  I continued to do it, and continued to titillate myself, in spite of their derision.  I'm sure they like it anyway.  I sure as Hell did.

But I couldn't get away from it.  The panties were my only link to the goddess.  Sure, they weren't hers, but still, the fact that I wore any at all made me think of her.  I needed to relive that moment.  I desperately needed to wear women's underwear to satisfy myself.  It slowly became a necessary staple in my sexual encounters with my harem girls.  Soon I couldn't do without them.  I would buy new lingerie for them with the view in mind of slipping into it myself after stripping it off of them.  

It got to be so bad that I couldn't come without girls' clothes on me.  I needed to wear panties to come.  It sure was ironic: here I was asserting my manhood with the harem girls by wearing their underwear.  Eventually, I stopped touching them, because I could get more satisfacton from just prancing around in their panties and brassieres and teddies and garter belts than by fucking them.  I was completely transformed: I thought of the goddess, and of my pleasure in recreating the experience of that fantastic encounter.  I stopped having the girls come to me, strip, and give me their clothes; I asked them to bring it to me first.  I asked to try things on with them.  Of course, this was still always in our private sexual encounters.  Nothing was ever said about this outside of the proverbial bedroom.  I never ventured out of the bedroom to get women's clothes on.  Up to that point, anyway.  I just felt the need to wear girls' stuff so strongly that I eventually started stealing into the girls' wardrobes to steal a peek at their panties.  And then to touch them.  And then to wear them, while they weren't around. 

I started wearing girls' panties under my clothes.  It made me feel so sexy, so connected to that mysterious goddess.  My girls would never miss their panties, considering how much underwear they had to choose from.  Still, I was careful never to be caught by them wearing it before they gave it to me.  For a while at least.  Then I started meeting them, and stripping down to my panties and bra.  We were virtually mirror images of each other.

Even that wasn't enough.  I still felt too distant from the goddess.  I started thinking about how great it felt to be feminine.  I realized that the goddess wasn't the center of my sexual thoughts anymore.  I was just using her as an excuse to justify my wearing women's underwear.  I began to realize that this must be leading up to my ultimate sexual fantasy.  It was just too incredibly tantalizing to give up.  On a whim, I shaved my legs.
Pretty soon, I was completely femininely attired under my clothes: under my shirt and pants, I had some kind of lingerie covering a hairless body.  My hair was long.  Being feminine made me feel incredible.  I saw less and less of the harem girls.  I relished taking off my suit at the end of the day, and finding my femininely attired body underneath.  I wore girls' panties all the time.  

Now I was thinking that this is the height of my eternal fantasy.  But little did I know how much more there was to come.  

I didn't expect one day as I went on my daily walk to spot the woman who had introduced me to such unearthly delights.  I ran after her, and I accosted her.  How I wished I still had the power of wishes, so that I could subjugate her and keep her forever in my harem!  But that would not be the case.  Instead, I had to go the old fashioned way.  I had to talk to her.

She recognized me instantly.  She gave me a wink, and we flirted over a cup of coffee.  She invited me back to her place, and I accepted.

Once inside, she said, "so, by now, you must have found yourself making choices you never thought possible."  I asked her what she meant, knowing full well what she meant, but too guilty to admit it.  She stepped towards me, and tore off my shirt, revealing my flowery, lacy bra.

"Ha!  I knew it!  Well done.  Go home.  I'm glad to see you're doing what I want."

I was hurt.  Again.  I couldn't believe that she was turfing me again.  I pleaded with her to keep me along, to have another fling just for old times' sake.  She laughed, and pushed me to the door.

"But wait," I pleaded.  "Can I at least have something to remember you by?"

"I suppose," she answered, and she disappeared into her bedroom.  She came back and handed me a bikini.  I was enthralled, and looked forward to slipping into it later.  Satisfied (amazingly) I left.  And did I ever wear that bikini!

But it wasn't enough.  I had to have more.  I needed to be more feminine.  On a whim, I started looking into taking female hormones, to give me tits and a waist, and remove my hair, and change my voice.  After a long time of deliberating, I took the plunge.  I started turning myself into a girl.  After only a few years of constant masturbating in women's clothes, I began to notice significant improvements to my figure.  I was looking good.  I started wearing skirts and blouses.  My harem women were both appalled and amused.  My guards and servants were shocked.  I was beginning to flaunt my femininity.  I wore makeup, pantihose, heels, the whole works.  I had made myself into a complete transsexual.  All I needed was a cunt, and I would be female.  I often wondered at this point if this was my ultimate sexual fantasy.  But it wasn't over yet.

To try to feel more feminine, that is, to continue in the way that I thought I had to go to fulfill my fantasy, I started to pick up men.  I started having sex with men.  They fucked me up my girlish ass, and I sucked their dicks.  Those who found out that I was actually still a boy either didn't care, or ran away.  I didn't care who knew.  But I found that I didn't quite enjoy it.  I still longed for femininity.  I still wanted to caress tits (not my own) and eat pussy.  Pussy was still tops on my mind, and it wouldn't go away.  I was stuck.

Then it all came to fruition.  As I strutted my girly butt down the street, she made herself visible to me again.  She took me back, and told me, "yes, now I can see that you're almost ready."  I followed her home again, and she led me into a large chamber.  In it were the beautiful servant maidens I had seen before, when I was brought to her naked.  Each and every one of them had a dick.  They welcomed me to the fold, and I stripped down with them.  These were men, too.  

Now my fantasy came to its conclusion.  I found myself cuddling up to one of the "girls," and admiring her beautiful, lithe girl's body, and rubbing my silken-covered cock against hers.  I was rubbing up against the most beautiful women on earth, and they were all men.  The feeling of silk on silk, of lace on silk, of satin on lace, etc. etc. etc. gave me the most pleasurable experience since the one with my goddess.  Then I understood that I was to attend on her always, just like the rest of the girls.  

So my ultimate fantasy had come true: I got to fuck my goddess, and her servant girls, some of whom were actually transsexuals.  

Then djinn reappeared to me, and asked me if I ws still happy with my choice.  And although I was reduced to a sex object, always fucking, always ready to come, always hard, and immortal, I had to say, YES, I want to be like this forever.  So here I am, wearing girls' clothing only, and rubbing up against another girl's dick, while eating out the goddess.  Forever.