A Submissive Sissy

Here you'll find my favorites Sissy & Femdom stories, the best one I've ever read over the net since many years and believe me, that's a lot ! I'm also a wool fetishist, so you may come accross this type of topic around here too... Hope you'll like it !

Sara Girl

Room & Board 6

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I fell asleep wrapped in Lisa's arms, content, yet uneasy. I feared losing Lisa because of Amanda, but something even more compelling than before was not present. The small part of Amanda I saw in Lisa. Not the dominating bitch, but certainly the confident woman who knew what she wanted, who "wore the pants" so to speak.

But...what would she really think about her boyfriend wearing the panties?

How far was the gap between Lisa and Amanda?

I fell asleep in love. And in danger.

I woke up the next morning actually thinking about what I should do to make Lisa happy. I knew I had to get back to Ms. Drake's soon, but I still had time to do something for Lisa, something Amanda had taught me. I quietly slipped out of Lisa's bed, leaving my beauty softly breathing her morning sleep, and padded naked into the kitchen.

I pranced around, my nakedness not quite as humiliating as a maid's uniform, but still, cooking for Lisa while she slept, I felt vulnerable.

When I was done, I quietly carried a tray with a carafe of coffee, a single coffee cup, a cup of juice, toast and jam, and fruit back to the bedroom. Somewhat embarrassed, approaching the bedroom, I thought of myself in a maid's uniform again.

Lisa was stirring. She looked up as I entered the bedroom carrying the tray, pushed herself up onto her elbows when I came over next to her on the bed. "Breakfast?" she said sleepily.

"Yea, I thought you'd like something before I took off."

"Take off where?"

"Back to Ms. Drake's. I have to work today."

She frowned. "I was hoping to keep you to myself today."

"I know, but...we had last night, today's work."

"Did you already eat?"

"No, why?"

"There's only enough for one," she said looking at the tray. To be honest, I'd not even considered bringing some for me too. I'd automatically thought of serving her.

"I...I just wanted to...to do something for you."

"You're sweet, James," she said with an innocent, self conscious smile. "Thank you. Wow, breakfast in bed after last night. You're too much!"

I set the tray down beside her, stood up, unsure what to do. There wasn't room left in the bed beside her and I didn't want to sit down in the chair across the room; that was too far away from her. Instead I just stood there at the foot of the bed, hands clasped lightly behind my back, head slightly bowed, eyes downcast.

"Hmmm, this is so nice." Lisa was carefully spreading the jam on her toast. I had a momentary sense of dej  vu. I was in the mental state of mind of a servant, like I was...

Serving Amanda and her guests, dressed feminine. Oh god, I was...I couldn't be...

"Will you?" Lisa showed me some jam on her finger and then pointed to the carafe of coffee, conveying an innocent request for me to pour her coffee.

"Yes Ma'am," I said, not quite thinking about what I was saying.

Lisa almost blushed. And so did I. I could feel myself stirring. Hardening. There was a strong submissive vibe flowing through the room, through me. I felt it. My nakedness, my serving. I wasn't fully erect, but I was swollen. No doubt about it.

Lisa just watched me pour, eating her food, quietly drinking her juice and coffee, checking my hardening cock out of the corner of her eye ever few moments. I felt so...so honored, as if I was privileged just to be standing here, serving this beautiful woman breakfast.

She took a sip of her coffee, looked at my erection again. "You know, I had fun last night Jamie."

"So did I, Lisa. You know, you looked beautiful last night at dinner."

"Thanks, Jamie. I liked looking pretty for my baby. Besides, I kind of like the effect it had on you," she giggled a girlish laugh. She was moved her foot from under the sheet, slowly, until her toes were just under my erection, lightly teasing my balls.

"Hey, I do have to get going you know."

She pouted a fake pout, kept tickling my balls. "Love em and leave em," she asked finally.

I backed up, looking for my suit and the rest of my clothes. "Yea, that's me" I responded, knowing neither of us meant it. I felt I had to get out of there. Now.

As I got my tie and other things from the middle of the room, Lisa sat up a little more and pointed to the corner. "Don't forget, your panties are over there, darling," she joked in a mocking tone.

I swear, if Lisa kept up any more panty talk even she, clueless, would soon pick up on the establishing correlation, or hell, even the fact that, they WERE PANTIES! I don't think that would have gone over well.

I grabbed them and slipped them on as quickly as I could.

Lisa looked at me. "Jamie, come here." Fuck she was going to look at them more closely in the light. She was going to find out. Joking aside, there was no explaining this to her, Amanda's role, anything.

"Yea," I croaked, walking slowly to her side. She was staring right at me...right at them, head slightly tilted...did she know?

"Um, nothing," she looked up from my underwear, "I just want a kiss."

Leaving, I decided she did not know, but certainly, this was not something that I could hide forever. Something had to give or I was going to snap.

Back home, I slipped quietly into my rooms without seeing Imelda. I wasn't sure what time Amanda was going to be back, but I didn't sense she was around yet. I decided to get out of my rumpled suit and shower.

I was in the bathroom drying off when I heard Imelda's voice sing out. "Miss Jamie." She walked into the bathroom, not even caring that I was standing there naked.

"Good, you shower. You need dress now."

"What for?"

"Ms. Drake home, she want to see you right away."


Imelda chuckled. "She talk to Mr. Stockwell."

My stomach sank. I knew this could not be good. Suddenly my incredible evening with Lisa was totally forgotten, replaced by a sense of impending doom.

Imelda seemed to take particular joy in directing me what to wear this morning, giving me a pink satin and lace bra and panty set to start with.

"I have to wear a bra again?"

"Yes, you wear bra all time here."

I noticed that this bra did not have the cups filled, maybe it wasn't too bad, for having to wear a bra. I could hide it with a sweatshirt, perhaps forget what was on around my chest.

Like that lasted? Imelda promptly filled the cups with a pair of silicone forms, giving me very life like breasts.

"You like breasts, no?" She knew I didn't. I didn't even justify her taunt with an answer. "No matter, you get used to them."

She watched me put on the panties. "I tell you before, Ms. Amanda right, you cute in pretty panties. Little bulge hardly in way."

Amanda. Imelda. Lisa. Panties. Even I had to admit I did look cute in them. Hell, I could not help thinking about panties all the time.

The "uniform" for the day, because it was the stupid uniform agreement that got me dressing like this in the first place, was a pair of nude pantyhose, a light blue pleated skirt, a white cotton short sleeved blouse, white lace ankle socks and black heeled mary jane shoes. Imelda said I'd be cleaning later, and this was what I was to wear for that, after talking to Amanda.

"We do makeup today?"

"Are you asking me, Imelda?" I'd of course say no, given any say in the matter.

"No, not really. Ms. Drake want make up, so we do make up." I was actually getting used to it. With each application, it became more and more routine. Panties were routine. Dressing completely as a woman was becoming routine. Make up was becoming routine.

After Imelda finished my transformation, again turning me from a fragile man to an uncomfortable woman, she led me downstairs to Amanda's office. The door was closed, but a straight backed wooden chair was outside the door. I could hear Amanda's muffled voice, presumably talking on the phone.

"You wait here, Jamie. Ms. Drake get you when she done."

I assumed it would just be a minute. But ten, then twenty minutes later, I was still sitting there, growing more nervous by the instant, the unknown more unsettling, my mind fixating on all the things she could do.

Finally, half an hour later, the door opened, and my employer, my incredibly attractive employer, walked out and told me to come into her office.

I followed Amanda in, fixated on her gorgeous legs, as I often did. She was impeccably dressed, as always, in a black skirt suit and blouse. My eyes were drawn to the black nylons covering her legs, imagining myself kneeling before her, just licking and worshipping, making love to her legs, if nothing else.

"Sit down, Jamie." I sat in a chair facing her desk. She went around, sat down, giving me a view of her legs under the desk.

"So, my dear, I had a conversation with Richard yesterday."

I think I gulped so loud that even Imelda, wherever she was, must have heard it.

"Care to guess what we discussed?"

"Nnnoo, Ma'am."

"I'm very disappointed in your behavior, Jamie. I sent you over there to help out, no strings attached, no pressure for you, and yet I get a very negative report from Richard. My friend. Do you know how embarrassed I am? Do you?"

"No, Ma'am."

"How poorly your behavior reflects on me? Honestly, Jamie, flirting with Richard like you were some...some common tramp? I didn't know you found men attractive, James."

Goodness no! That wasn't it at all. Ms. Drake, I'm sorry," I said, shifting nervously in my chair.

"I realize you are a bit confused about some things, but honestly, I never expected you to flirt with him. I understand your infatuation with me, I even think it's kind of cute, but Richard? Richard?"

"I'm sorry, Ms. Drake, really, I don't know what happened, but I promise it won't happen again." And that was the absolute truth, I never wanted to, and certainly didn't plan, to flirt with a man! I was living that experience again inside my stomach right now, remembering Richard, his strength, pressing against me, his body. I shook.

"I accept your apology, Jamie, but that's not quite good enough. Don't get me wrong, Richard handled the situation how he wanted, he's satisfied, but that still does not satisfy me."

"I'm not sure what you mean, Ms. Drake." I shifted uncomfortably in my chair, self consciously tugging down my skirt.

"You disappointed me, let me down, Jamie, that can't go unpunished."

"Punished?" Punished? Was I ten years old? "What, am I grounded?" I said sarcastically, regretting it as soon as I said it. She might do just that.

"No, James, you're not grounded, though I assume that time away from Lisa would be punishment for you. You are, however, going to get a spanking."

My eyes bugged. "You're not serious!"

"Oh, I'm quite serious. Sissies that misbehave like that get a spanking. I've found it's quite effective in training a confused creature like you." There it was again, references to the past. I was more and more convinced that I was not the first person to experience this, that I was a part of something bigger, something I did not understand.

"You...you're really going to spank me?" The way I asked it betrayed the hint of eroticism that a spanking from Amanda might entail.

She laughed. "Well, no, I'm not going to spank you. I think that's more a reward than a punishment."

Imelda! My eyes widened again.

"That's right, sissy, Imelda will be administering your punishment."

"Please Ms. Drake," I trembled. That wasn't at all erotic. Lying across Ms. Drake would be a fantasy. Imelda's hand on my ass would be horrid!

She grinned at me. "Oh, I suspected you'd be begging for it sooner or later."

"I'm not begging for it," I protested, sitting up straight.

Amanda stood up, walked to the front of her desk and leaned against it, contemplating me. I was almost panting, staring at her legs, so close to me.

"I know, sissy, I know. But that's not the point. The point is that sissies that misbehave must be punished. You misbehaved. Ergo, you'll be punished."

"But why Imelda?"

"Why Imelda? She has much more experience, that's why, sissy? Why, you'd rather I do it?"

"Yes," I blushed.

"I imagine you would, but that's just the point, dear. Punishment from me is hardly punishment now is it? Now, I'll call Imelda, but I want to see you back here when she's done."

She called for Imelda, who came back wearing a knowing grin. "Yes Ms. Drake?"

"You may take care of what we discussed."

Imelda almost seemed gleeful. "Are you sure, Ma'am?"

"Yes," Amanda sighed, "I'm afraid it must be done."

"Yes, Ms. Drake, it for the best." Imelda walked over to me. "Come, Jamie." She took me by the arm, led me roughly out of Amanda's office down a hall I rarely went down in my duties at the house, into a room I'd never been in.

It was decorated sparsely, wood floor, dark wood walls, a few chairs, and a table with corner. It looked like a study that was not used.

"Come, over here, on table." With her hands, Imelda indicated that I was to lie across the table, basically presenting my ass for the beating I now dreaded. Sure, I'd seen porn with spankings, erotic spankings. Somehow I did not picture this as something erotic. Maybe naked, with Amanda. Hell, even with Lisa, but not like this, not with Imelda, not here, or now.

"You lucky, Ms. Drake not say you pull down pantyhose and panties." I felt Imelda flip my skirt off my ass, onto my back, exposing me to her, protected now just by the panties and pantyhose I was wearing.

"What are you going to do Imelda," I asked, voice shaking.

"In old days, called hairbrush discipline." She showed me a large wooden brush. "Ladies use on bad boys and girls, help, sometimes husbands. Like this." Imelda walked to my side, swiftly raised and lowered the brush to my ass with a stinging blow.

"Ouch! Christ, Imelda, that hurts."

"Yes, it hurt Jamie. Punishment. Sissy not forget first punishment." She whacked my ass again.

"Ouch...ohhhh, Imelda!"

"Oh, Jamie, it hurt worse soon, you have thirteen more to go."

Imelda continued to use the brush on me, never hitting in the same place twice, expertly wielding the torturous implement.

With the tenth stroke, I realized it. Through pain, I realized I had an erection. The rubbing on the table top, through my soft panties and pantyhose, with the pain, caused me to get erect. Oh fuck, I was erect! Damn Imelda, that was more embarrassing than the spanking. The pain, not quite as bad as the hardness between me and the table.

I started to tear up by the thirteenth hit. I was breathing heavily with the fourteenth, almost sobbing, crying out in pain. The final one, the final blow was the worst, the pain shot through me, all over me!

"Ohhh, it hurt, no Jamie?"

"Oh fuck yes, Imelda," I half sobbed, letting her pull me up off the table, mortified at what had just happened to me.

Imelda shot her hand under my skirt, put the big paw right on the front of my nylons. "I see it not all bad, no? Sissy might like." Dammit, why did I have to get excited? Nothing was exciting about this.

She led me back down the hall, back to Amanda's study.

"Done, Imelda?"

"Yes, Ma'am."

"Thank you." Imelda turned to leave. "Oh, Imelda, did you check? Did he?"

I saw Imelda's eyes twinkle, and I knew what she meant. My face flushed at the thought of her hand on my erection. "Yes, Ms. Drake."

"Jamie, sit down," Amanda indicated to the same chair I'd sat in not too long ago. I did as ordered, visibly wincing in pain. Fuck, my ass was on fire.

"Hurts, does it? Imelda really does know what she's doing." Amanda, unconsciously it seemed, briefly touched her own ass. Wait...had she felt the same thing? From Imelda? Why would that have happened? Amanda looked at me. She raised her eyebrows at me, almost challenging me to ask,

"Did..." But I was not brave enough to finish the question.

"I trust we'll have no more bad reports from Richard?"

"More? You mean I'm going to have to go back over there?"

"Why yes my dear, you are, why?"

"I just..." I bit my lip, I wasn't sure what to say. "But he's a man, I don't like being around him like this, it's so intimidating, I feel...I don't know, it's hard to describe, he makes me feel..."

"Inadequate?" she asked helpfully.

I swallowed hard. "Yes, yes, inadequate. Like I'm...less than a man, and Lisa and...." I started to tear up. "Why, Amanda? Why are you doing this? What did I do? I don't understand, I'm so confused, I feel so foolish. Lisa?" The words just rushed out in a jumbled mess of feelings and tears.

"Come here, Jamie," she said softly, taking my hand, standing me up. She wrapped her arms around me, took my head into her shoulder and rubbed my hair while I cried. "Shhhh, it's okay, baby, it's okay." I could feel her breasts pushing against my chest, against my fake breasts as she pulled me tight to her,

"Go ahead, Jamie, let it out...shhhh....it's okay, honey, it's okay."

I shuddered, the tears slowly subsiding. "Why, Ms. Drake?" I asked again.

"Come here, James, sit down." Amanda led us over to her couch where we sat down, side by side. She took my hands in hers, turned, looked at me.

"James, do you know what a transsexual is?"

"A...a transsexual...isn't that a man, well, a woman that thinks she or he is trapped in a man's body? You know, someone that wants a sex change."

"Basically, yes. Are you a transsexual?"

"What?" I practically yelled.

"Do you want a sex change?"

"A sex change?" I sat up, shocked, yuck!. "No...my god, no, that's disgusting!"

She patted my hand. "Shhh, don't get worked up again. I know, Jamie, I know, don't worry. How about a transvestite? Do you know what that is?"

"Um, yea, that's...that's a man that wants to dress as a woman."

"Hmm, yes. Now, are you a transvestite? Do you want to dress as a woman?"

"No, Ms. Drake, no...no, no, no!" I was insistent. I didn't want any of this, not the panties, not the bra, the breasts, the makeup, any of it.

"It's okay, Jamie, I know, I know...just bear with me. What about a sissy? What's a sissy?"

"Um, a...a timid man, I don't know, a wimp?"


"Yea, I guess?"

"Not manly? Effeminate?"

"I suppose."

"Unassertive. Cowardly even. Easy to push around. I think a childhood taunt might be a pantywaist?"

I just blushed, she was hitting very close to home.

"Hmmm, let me ask you this, is Richard...Mr. Stockwell, is he any of those things? You've met him several times, right? Would you use a single one of those words to describe him?"

"No, god no. He's a...a..."

"A man's man?"

"Yes, yes."

"Would you call him a sissy? Or a pantywaist? Could you imagine him in panties," she half laughed.

"What? No, never?"

"Certainly not to his face, right? He'd probably spank your ass, wouldn't he?"

I thought of Richard, the power he projected. "Yes," I whispered.

"Can you picture him letting someone spank him?"

"Spank him?" Now I laughed. "No."

"Or order him around?"

I shook my head. Um, no, of course not.

"Think he'd wear panties if someone told him to?"

"Panties? No, I can't imagine him doing that," I laughed.

"Are you a sissy?"

She caught me off guard. "What?"

"Are you less masculine? Wimpy, even? Effeminate? Are you? Are you Jamie?"

"I...I...no...I mean, I don't..." I suddenly felt uncomfortable again. Panties? Spanked? Ordered around? Dominated? Wasn't I doing just that?

"What are you wearing, Jamie? Panties? Nylons? A skirt? You're not sure? And aren't you wearing them because you were ordered to by me? I'll ask you again. Jamie, are you a sissy?"

I blinked my eyes, looked away from her glaze? How did this happen? Was I? Was I a sissy? Really? "I...I don't know."

"Maybe it's hard to admit, but look at it like this, Jamie? You don't want to be a woman? You don't want a sex change, right?"


"And you don't want to dress like one, correct?" She emphasized 'want'. No I didn't want to do this, I never had until she ordered me to.

"No I don't."

"Yet, my dear, you do it anyway, why?"

"Because...because you make me."

"Hmmm, because I make you? That's an interesting answer, but that begs the question, why do you think someone lets a woman make him do these things?"

"I don't know."

"You do know. Because they are weak, effeminate, unassertive, cowardly..."

"Because...because they are sissies?" I finished her sentence. My god, was I all that?

"Oh yes, Jamie, you get it, don't you? Jamie, I understand you're discovering this side of yourself, or what it means, for the first time, but I suspect you've always felt a bit, um, uncomfortable around women, no?"

"Maybe a little."

"A little intimidated, especially by pretty women?"

"Yea, I guess."

"I know it's hard for a young man to understand, Jamie, what that means, but trust me, a knowing woman understands. I could tell from the moment I first met you."

"You...you knew? How did you know?"

"I can tell, Jamie, its obvious. Why do you think I hired you?" She frowned, it was so obvious.

That was like a slap to the face. She hired me...because...she knew? "You hired me because you thought I was a sissy? You...you...you planned this all along?" I stood up, the discovery had an exciting effect on me. "But why, Amanda? Why? I never asked for this? I didn't look for this? Why did you...are you...doing this?"

She smiled. "Because it's fun."

"Fun? Fun for who? You're ruining my life!"

"Fun for me, of course. I've told you quite a few times how much I like young men like you in panties, haven't I? It's really quite simple, dear, I like feminizing little sissies like you. I...well...get off on it."

"But I...I don't!"

She laughed. "You don't? Are you kidding me? You most certainly do. Oh, don't get me wrong, I know you don't get off on being feminized, not like a crossdresser, you get off on the power, Jamie. Don't like to yourself. You get off on a woman dominating you."

"But I...I don't."

She snorted. "Don't you? You even get off on your precious Lisa doing it. You can deny it all you want, Jamie, but that doesn't change it one bit."

I started breathing heavily. My god, she was right!

"Of course you do. The funny thing is, a sissy like you is disgusted by it just enough to make it all a bit unsettling. You're not a masochist, I know the submission tears at you, pulls you apart. You picture yourself as a normal man, but you also know you're not. That's the really fun part, Jamie. I know you're so torn about it, and that more than anything is what makes it so fun for me."

"But you're messing with my life." I really was angry, at her for doing this, and at myself for letting it happen. "That's not fair. School...Lisa."

"Well, to be fair, I did pick you before you met your Lisa. That, my dear, has turned out to be quite a little bonus."

"Bonus? Bonus? You talk like this is a game to you."

"Well, it is, in a way. To be honest, I didn't intend for Lisa to be involved, but it has been quite interesting. You know, I'd really like to meet her, she must be quite a woman."

"What?" Meet Lisa? When pigs fucking fly.

"What's Lisa phone number?"

"Are you kidding? You...you're going to call her? I'm not going to...you can't do that." It was one thing to do this to me, but it wasn't fair to bring her into this. This was bullshit.

"Well, I can, pet. The easy way or the hard way. I can just go through my phone records and get her number, and, oh, invite her over for lunch some afternoon. I'm sure she'd love to see her boyfriend at work in a skirt and blouse, or even a maid's uniform. Or you go write down her number and I'll simply go to lunch with her. I'm not kidding, Jamie, I am going to meet her for lunch." Her face was frozen. I knew she was deadly serious.

"The number, Jamie."

Shaking, I walked to her desk, wrote it down on a piece of paper. "Please, Ms. Drake," I begged.

"Come here." I walked over to her. She pointed, directing me to kneel beside her. "I think I'm going to like your little friend. I mean, if she can put up with you, why, I think I'll get along just fine with her."

I realized there was no way out of this. One way or another, Amanda was going to call Lisa. The easy way or the hard way. I had to do what I could to control it. "Yes Ma'am."

"It's all of you own doing, you know. You sissies are your own worst enemies, unable to control your desires, sometimes not even knowing you have them, but under such a spell when someone pushes you down the path. You just crumble to the power."

She moved one of her shoes up toward me. "Kiss this, slave."

I looked at her like she was crazy, but she just stood there, one foot out, challenging me. "You heard me."

Every part of my body told me to run away right then and there. Every part except the part that made me kneel down in front of her. I took her dainty foot into my hands, brought it up to my mouth, slowly planted a kiss on her foot.

"Do you love her? Lisa?

"Yyyes, Ma'am," I whispered, lips still touching the leather of her shoe, inhaling the sweet scent.

"And yet you submit to another woman. And yet you allow yourself to be feminized. And yet you kiss another woman's shoe. So fucking destructive, damn all sissies."

"Please Ms. Drake," I said, feeling her drift back again into an emotional pain from the past.

"You love a man and find out he's a sissy? Do you know what that does to a girl? To find that out about him? Do you?"

"Nnnooo Ma'am." I was on the verge of tears.

"She loves you?"

"Yes." I felt a single tear run down my face.

"I loved him," she sighed, closing her eyes.

"Who? Who Ms. Drake?"

"It doesn't matter, Jamie. Because she wasn't like me, though, she didn't consider my feelings at all. I grew up with her, I thought it would be different when I moved out and met someone. But no, it didn't matter. Not once I brought him home to meet her. She didn't care what we thought. Do you know how hard that was? I won't let Lisa go through that, Jamie. I never thought we'd turn out like this, but I promise it will be different."

I just continued to kiss her shoe, her foot, softly tasting the leather, scared by Ms. Drake, scared for myself.

"You're such a good foot worshipper, Jamie, really a natural, aren't you. Just like a sissy, my dear."

And so I spent the next ten minutes doing just that. Yearning to go higher, up her legs, up to her pussy, where I'd found such joy with Lisa, but afraid, too, afraid of Amanda, afraid of betraying Lisa, afraid of my own reaction.

Amanda's legs had spread apart while I was nose to her foot, so I didn't see right away that her skirt had ridden up to the tops of her milky thighs. Suddenly I realized I could see her garter straps, the welts of her stockings, her soft skin, her panties. Amanda reached down, pulled my head up by the chin so I was kneeling in front of her, staring directly at her panties, the folds of her womanhood pressing against the taut fabric.

"Can you smell it, Jamie? Can you smell me? I can." She was possessed. There was no other reason she'd be toying with me like this, playing with me. "I know you love my panties, don't you? Even more so when I'm in them, Jamie, so close to you, so available."

"Ms. Drake, please," I croaked, mouth suddenly dry. This wasn't fair.

"Go ahead, Jamie. I know you want to kiss them. Go head, gently."

I couldn't. Lisa! No! No! No! This was wrong. Very wrong. "Nnnno...no...no, I...I can't."


I was shaking.

The slap across my face was more painful if only because I didn't expect it, was totally shocked by it. "You love her, I know. But you serve me, sissy, don't you forget that. Ever."

"Please," I begged to no avail. She was testing me. To see if I'd compromise. NO!

I caught Imelda out of the corner of my eye and assumed she'd rescue me from this fucking crazy woman.

"Kiss my panties, Jamie. They are what got you into this mess anyway." Amanda saw Imelda but did nothing. There was no hope there.

Trying to push Lisa out of my mind, trying not to think of the betrayal, I started to lean forward.

Just before my lips touched her panties, Lisa at last out of mind, Amanda brought her image back, wouldn't let me forget just how dangerous this was.

"Think of Lisa," she spat at me just as my lips came into contact with the satin panties. The heat coming from them was intense. They were damp. I could smell her now, more pungent than Lisa, stronger, more intense.

"Don't move slut, don't move an inch." I froze, my mouth closed, but my lips resting on Amanda, on her panties. This was worse. I'd made love to Lisa like this, tenderly, licking her, loving her. This was unbearable.

Amanda...Amanda then fucked my face. She grabbed my head, pushed me into her crotch, rubbed my face, my closed mouth on her pussy through her panties. She used my face, took it, possessed it, owned it as she owned me. It wasn't pleasure for me, it was agony. It was betrayal. I was powerless.

It was rape. That's what it really was. She raped my face. Until she came. She fucked my face. Completing my shame. And I loved it. I was shaking, I loved it so much.

Finally she pushed me away. Her scent was all over me, juices bled through the satin of her panties, covering my nose, my mouth, my face, the scent. I knew I'd smell her all day, my mistress. Amanda Drake.

"Take her away, Imelda, I'm done with her," Amanda ordered me dismissed, her girl dismissed, sent away from her glorious presence to stew in my shame.

I could hardly talk to Lisa over the next several days.

Two days later I was sitting in the kitchen drinking a cup of coffee before going to class when Amanda walked in. I immediately got up to go pour Amanda a cup of coffee, but she waved me down. "No, no, sit Jamie, read your paper, I'll get it myself." Amanda was barefoot, and my eyes slowly traveled her long toned legs as she poured her coffee, up to the hem of her champagne satin robe that ended well above mid thigh.

"Are you working from home today," I asked. It was after nine, late for her if she was going to the office. She certainly wasn't soon, not dressed like this.

Amanda sat down across from me, and as she did, her robe, loosely tied, became more undone, so that her breasts -- covered only by a sheer cream bra -- were suddenly revealed. Ms. Drake may be approaching middle age, but her breasts, either on their own or with the help of a great doctor, were as beautiful as any young woman's -- even my Lisa's.

Amanda looked me in the eye, saw the direction of my gaze, looked down, and realized I was staring right at her breasts. And before my eyes, her nipples hardened! Oh, god. Despite the tingling in my jeans, in the pink panties I was wearing, I couldn't move. Amanda made no move to cover herself. In fact she shifted ever so slightly backwards so that I could just see her tight stomach, the top of the waistband of her panties, though I couldn't really move my eyes from her breasts.

"You know Jamie, I'd normally be flattered by the attention, but I can't help wonder. . . is it my breasts or my bra?"

"Ms. Drake?" What was she talking about? Probably nothing good, that's for sure.

"Well, you see, when you first started working for me, I'd assume you were staring at my breasts, like you did those times I sunbathed. But now, now that we've discovered what you really are, I wonder if it's not really the bra, not what's inside the bra?"

I gulped.

"I mean," she took a sip of her coffee, "are you fantasizing about playing with my breasts..."

I shuddered, my half erection folded so tightly I could not grow anymore without adjusting myself -- and it was painful.

"Or are you fantasizing about wearing my bra?"

I just wanted to melt into my cup of coffee and read my paper before class! Why did she have to torment me any time I saw her?

"Cause panties are one thing, but to really feminize a boy like you, I need to know you dream about my bras. You do, don't you Jamie? Dream about wearing my bras?"

I was now in full pain!

"Or Lisa's bras? Does she wear pretty lingerie, Jamie? Tell me, when you see her in her pretty bras and panties, do you ever think about wearing them? You must, I know you must."

"I..." But she wouldn't let me talk, and instead she stood up, her robe falling around her, then to the floor. She was turned slightly sideways, and my eyes fell to her ass. Bare -- she was wearing a cream sheer thong!

"You know Jamie, when one of my gentlemen friends sees me like this, I know all he is thinking about is getting into my bra -- and I don't mean wearing it. But I don't know with you, dear, which you dream about. Playing with my breasts or wearing my bra? Lisa's breasts or her bra? Being a man or being a girl?"

"Ms. Drake, I..."

"No, don't answer yet, dear. I was going to wear this bra today to my lunch date with Lisa..."

My eyes went wide! Lisa!

"Hmmm, but I think I have a better idea. Do you want to wear it today? Wouldn't it be sweet if you were wearing my bra when I had lunch with your girlfriend?"


"Breasts or bra, Jamie. Boy or girl? Touch these, or wear this? Man or woman?"

"Ms. Drake," I shifted, my erection finally popping unfolded, the blood rushing into it.

"Just say it Jamie, say 'bra' and this is yours to wear under you sweater today, or breasts, and maybe I'll let you touch them. Pick, Jamie. Be my girl, Jamie, be my girl. Just say it."


"Bra or breasts?"

I was about to explode. "Bra," I croaked.

"And the panties too?"

"Yes," I almost shouted.

"I'm a girl."

I looked at her.

"Say it, 'I'm a girl,' I want you to say it."

"I'm a girl." My face was frozen red.

"Good, good." She picked up her robe. "I'll have Imelda bring them to you dear, so you can be my girl today."

"Yyyes, Ma'am."

"You get comfortable with a bra, Jamie, and you'll really be my girl." She started to walk out of the room with her coffee. "You know, I would have let you have the breasts instead, if that's what you'd wanted." She left the room, leaving me -- her wreck of a servant -- in her mysterious wake, visions of her breasts and her bra dancing in my brain.

I was still wearing Amanda's bra and panty set that evening when Amanda came home. Imelda said she'd had lunch with my Lisa, then went to her office. I was upstairs studying, trying to concentrate, anyway, wracked with fear over what Amanda may have told Lisa. I'd tried to call Lisa several times but just gotten her voice mail and she'd not returned my calls.

I somehow had myself convinced that Amanda had told Lisa about me and that Lisa would never speak to me again.

I turned my head when I heard Imelda come into my room. "Ms. Drake ask for you," Imelda said. I stood up, legs shaking and started for the door, but Imelda had not moved. "She say you just in bra and panties of hers you wear today." Self conscious as always around Imelda, I undressed down to the bra and panty set Amanda had ordered me to wear earlier that day, my cheeks flushing when Imelda looked at me. "You pretty."

Only when down to the light bra and panty set did Imelda lead me out of the room down stairs and into a sitting room where Amanda was enjoying a glass of wine.

I was visibly shaking, certainly not from cold -- what had she done? "Ms. Drake, you..." I started to both ask and accuse, but she cut me off.

"Shh." Ignoring me, she looked over to Imelda. "You see it too, don't you?"

"Oh yes, Ms. Drake." What were they talking about?

"I thought as much. Certainly his legs are pretty enough shaved, and his chest, it helps being naturally hairless, no? She even kind of picked up on it on her own. Remarkable girl, Imelda."

"To see, yes."

"What?" I wanted to scream, but too scared to do so.

"Look though, you see what I was talking about Imelda? In sheer panties?"

Imelda moved closer to Amanda, looked right at my crotch. Normally the mild humiliation would have had the perverse effect of exciting me, but right now I was too preoccupied and terrified about what Amanda may have told Lisa.

"See, Imelda, it's not the bulge, it's too small to really ruin the effect, especially soft it's really just a mound anyway. But you see, right, the problem?"

"Yes, Ms. Drake, I do." Imelda pointed to my crotch, "the hair, no?"

Amanda clapped her hands together. "Exactly, see, I knew I wasn't imagining it. Maybe she'll pick up on it even more if we..."

"Pick up on it...?" I asked quietly, though they both ignored me.

"She know." Imelda asked. Oh my god, did she tell her?

"Well, Imelda, I certainly didn't want to scare the poor girl now, did I? I couldn't exactly ask her, but I got the sense that she felt something there in the fog, something she couldn't put her arms around, but could sense enough to know something was there."

"And?" Imelda asked, really for both of us.

Amanda didn't directly answer the question. "She's really quite an amazing young woman, Imelda. It would be a shame if our little Jamie lost her, wouldn't it? But honestly, I don't know how she'll handle it."

I was dying as I stood there -- maybe she didn't tell her? I don't know, dammit, what the fuck! This wasn't fair, Amanda was teasing with me, a cat toying with a mouse. It was killing me!

"So, you think it help?"

"Well Imelda, I think it will clarify some issues, if nothing else, let the poor girl make a better decision, one way or the other."

"When," Imelda asked.

"Oh, right away. Go set it up now." Imelda quickly left the room, almost rubbing her hands together she looked so excited.

"Ms. Drake, please, what did you tell her," I finally broke my silence.

"Well, I didn't tell her that while we were having lunch her boyfriend was wearing my bra and thong panties cause he'd rather dress in pretty lingerie than play with my breasts, sissy."

"Ms. Drake," I gasped, actually picturing Amanda saying just that!

"Stop. I'm not cruel, Jamie. We had a nice lunch. I wasn't kidding, she is an amazing woman. You know, she's prettier than I imagined. I bet she must really catch some looks from men, doesn't she?" I thought of the waiter, the valet at the restaurant, looked down, face red again.

"Hmmm, yes, she told me about the waiter. How did that make you feel? Seeing a man ogle your girlfriend like that? Just sitting there, feeling the cotton panties you were wearing while a real man hit on her?"


"Not being able to do anything. Not much a man, were you, even on your big date? Hmmm?"

Imelda walked back in the room. "Oh, ready, Imelda?"

"Yes Ma'am."

"Good, yes, this is going to make things look much better." Amanda stood and left the room, Imelda and I trailing her, following her to a guest bath. We walked in Imelda pointed.

"Everything ready." Imelda pointed to the ornate countertop where a white towel, a bowl of water, a pink ribbon, a straight razor and electric clippers were neatly laid out.

"Take off your panties, Jamie," Amanda ordered me.

"Ms. Drake, what...what are you doing," I asked in a panic.

"Imelda," she said, ignoring me. Imelda stepped forward and roughly pulled the panties down over my hips and off me.

"Ms. Drake," I said loudly.

"Do we need to use those to gag you, Jamie?" That both sickened me and shut me up. "Better. Imelda, on his hands please, behind his back." Imelda pulled my arms behind me, wrapped the panties around my wrists, binding them.

"Shall I," Imelda asked.

"By all means," Ms. Drake said, leaning against the wall. Imelda picked up the long pink ribbon, looped it, tied it around the tip of my shrunken penis.

"I'll take that end, Imelda," Amanda said taking the ribbon and pulling it tight, enough that it was uncomfortable, but not unbearable. I watched Imelda pick up the long straight razor. She...she wasn't going to

"What are you doing to do," I asked breathing quickly, fear in my eyes and my voice. I was trying to back up from Imelda, but that also meant backing away from Ms. Drake who was holding tightly to her end of the ribbon, just increasing the strain on my little cock.

Amanda looked up at me. "Jamie, calm down, she's not cutting it off, my goodness, I'm not a sadist. She is going to shave your pubes, you'll look much prettier and more feminine, more like my little girl."

While I never really thought they would actually hurt me, her words did comfort me. Maybe the comfort caused the small sexual twinge that ran through me, causing my soft penis to jerk the ribbon.

"Oh," Amanda said, feeling it. "you do want to be my girl, don't you? Soft, feminine. Be my girl."

I couldn't help it, my humiliation was the center of my excitement right now, even though my growing erection only made the ribbon tighter and more painful.

"That works, doesn't it Imelda." Imelda laughed, put down the straight razor, and picked up the clippers, turning them on and taking them to my groin, making quick work of much of my pubic hair.

"Better, much better. Go ahead, lather him up." Imelda got the bowl, filled it with hot water, then took a shaving brush and bowl from under the sink. She applied the shaving soap to my cock, my balls, the brush dancing all over me, making me grow a little more, painfully more.

"I'd stand very still, Jamie," Amanda warned me. Imelda took the razor to me again, like a surgeon wielding a scalpel, removing what was left of my hair. The combination of humiliation, excitement, and pain from the ribbon was overwhelming, so much so that I had to struggle to stand still.

Imelda stood, rinsed the razor, put it on the counter and looked back at our employer. "Yes, go ahead, she deserves it."

What? Oh, I realized as Imelda began stroking my lathered cock. Ohhhhhh.

"Feels good, doesn't it pretty girl. So smooth." Amanda tugged the leash that was pulling my cock. It actually hurt and felt good, pain and pleasure.

"You'll look so much prettier in panties now, Jamie, my smooth girl. That's what you wanted, isn't it? To be my girl? My sissy? Or is it Lisa's girl?"

I shook all over, not from the approaching orgasm, though that was coming, but at Amanda's use of Lisa's name.

She laughed. "Oh, I know you want to be my sissy, Jamie, even as you know it's a man like Richard that I want, not a little girl like you."

Imelda quickened the pace of her masturbation, just when Amanda pulled harder at the ribbon.

"I just wonder what your dear Lisa wants. A smooth, feminine little creature like you, your shaved clitty, all pretty in your bra and panties..."

She pulled harder still. "Or a man like the waiter, a man she can fuck over and over."

That was too much for me, to close to my insecurities, too painful.

And too erotic.

I exploded all over Imelda's hands just at that moment, a violent orgasm that released all the tension Amanda had built this afternoon.

As I shook, Amanda held the ribbon firm, keeping me in pain while I withered in pleasure, only releasing the slack when I was about to collapse, laughing at what she'd created. "Clean her up, Imelda, I'm going to dinner with Richard. He'll get a kick out of this, though I wonder what young Lisa is going to think."

Ohhhhh, I just moaned and moaned and moaned.

Two weekends later.

"Come on Jamie, let's go upstairs," Lisa bugged me, sitting in my car outside her apartment after we got back from seeing a movie.

"I really am tired," I faked a yawn, trying again to come up with an excuse to avoid just what she wanted. I was surprised she didn't get angry, for she had every right to, I had been avoiding alone time with her. But that wasn't Lisa. Disappointment, maybe, but not anger. Just as Amanda had really avoided talking about her lunch date with Lisa, Lisa did the same. Maybe they really did just talk about normal things. I'd worried about Amanda telling her everything and losing her, but now I was letting that fear keep me from spending time with her. Afraid how she'd react to my shaved pubes, I was pushing her away.

But Lisa was not one to take no, not from me, not from her beloved. She looked at me with a naughty look on her face. "I went shopping at Victoria's Secret today -- don't you want to see what I bought for you."

I jerked in the white high cut cotton panties I was wearing today. They passed as men's briefs, just barely, if that. But that was the best I was allowed to wear when I was with Lisa -- Ms. Drake's rules.

I swallowed hard, at first taking her meaning to be that she bought something for me to wear. Then I saw her hands unbuttoning a button on her silk blouse, revealing a hint of the silk bra covering her breasts. "Don't you want to see the rest of it, James."

No, she didn't buy lingerie for me to wear, but to see. Odd. I felt relieved, but strangely a little disappointed. "Come on, you're not that tired, are you?"

Fuck no I wasn't tired -- not after seeing the soft fabric covering her swelling breasts.

"You want to see the rest, don't you?"

Five minutes later we were in her bedroom, undressing one another. She got out of her blouse and pants in no time, modeling for me the pink silk bra and the matching panties. Pink doesn't work on every girl, but it was amazing on my Lisa. She took charge undressing me, ripping off my shirt and my pants, but leaving my cotton briefs on me. I was self conscious about both them and my smooth balls. I wanted to put off any discovery, and in the process give Lisa what she really loved about our love making.

I helped her into the bed, knowing she'd be sure to appreciate the oral attention at which I excelled. If I did well enough, she might even be content, and not even discover my smooth skin.

She did respond to my oral performance, but wanted more. She was going to find out. I was on my back when she reached for the waistband and pulled the panties off me, not quite looking at me as she pulled them over my feet. She dropped them to the bed, not the floor, as I silently wished. I tried to kick them away -- fuck!

The tag was sticking up, out, obvious. The Victoria's Secret tag! Fuck. Suddenly, the discovery of my smooth cock and balls was of less importance than those panties. I watched her eyes to see if they locked in on those vile panties, but she didn't. She was focused on my hairless pubes.

"Oh, Jamie, you're...I mean, you..."

I wanted to hide, tried to laugh it off. "I don't know what came over me Lisa, please don't stare, I know it looks foolish..."

She was now toying with me, running her fingers gently over me. I closed my eyes, her soft touch was driving me wild. "You're so smooth, James, so soft, like a...a..."

Girl? That's what my mind was yelling at me. I look like a girl! I waited for her to let go, to cry, to realize what kind of man she was dating -- in fact not a man at all, not after Ms. Drake was done with me. But she didn't say anything. She couldn't. It sounded like "girl" was on the tip of her tongue, then quickly, her mouth was, um, otherwise occupied. She gently took my soft erection into her mouth and started sucking me, moaning my name. I couldn't take much of this, not without...I wanted to let her know, to tell her to stop, but she didn't take or didn't care about my subtle hints.

"Jamie," she moaned, moving her mouth over my soft skin. I felt her climb on top of me, take me inside her, my soft skin on her wet folds.

I couldn't hold back and exploded inside her. Flushed with guilt, I only lasted fifteen seconds, my whole body shaking, overwhelmed, the room spinning, I was hyperventilating, until I think I blacked out.

Or close to it. I just lay there for five, ten minutes, Lisa gently licking me, cleaning me off with her tongue, running her hands over my smooth skin. With the shaving of my pubes, I was almost hairless now. Soft after my orgasm, smooth, I'd never felt more feminine, even when dressed with Amanda. Didn't Lisa see it? Why?

I had to get dressed, get the cotton panties, again, my thought going to that stupid Victoria's Secret tag.

"What are you doing?"

I had the panties in my hand, tag safely hidden. "Um, just...just getting dressed, I...I guess I'm hungry." As good an excuse as any to cover up.

"Hmmm, I'm not. Not anymore," she said playfully. I knew she hadn't orgasmed, and I was being incredibly selfish, but I just couldn't.


She was teasing me. "It's okay baby. It's still early, we can go grab something if you want." The traditional post sex munchies? Even when it was hardly post sex for her. The guilt I felt, the shame, like the first time we had sex, was eating me away.

Yes, anything, yes! I turned, wanting to get my briefs and pants on quickly.

"You don't want to. . ." She froze. She was staring at the panties half balled up in my hands.

"James...are...are those...are those really..." The quizzical look took over her face.

"Come on, don't you want to go eat," I asked, trying to redirect her.

"Give me those," she said, holding out her hand.

"Lisa, please."

Her eyes narrowed. She bit down on her lower lip, her face distorted, then clearing slightly. "Now." She raised an eyebrow, left her hand out, waiting. That was the first time she'd ever taken that tone with me. It was not a request I could easily ignore. I meekly handed the cotton panties to her.

Lisa took them, held them up, examined them, then went right to the damning evidence-the Victoria's Secret tag.

"James...these...these really are panties."

Deny? Fuck yea I was going to deny. "Lisa, no, they aren't."

"Victoria's Secret! They don't make men's briefs, James."


"You're wearing panties. Fuck, these...these are just like...you've..." It dawned on her. "You've been...every time we..."

"Lisa, please..."

"I...I don't get it...why did you..."

"Baby, don't look at me like that." I moved towards her, started to put my hand on her arm, but she jerked it back.

"Don't! Stop, I...I need to think."


"Please, James, just...I think you'd better go home."

Oh god! This is what I'd been dreading. No! No!

"Please Lisa," I begged, on the verge of tears.

"Go, just go," she almost sobbed.

I didn't know what to do. I took the panties back from her, put them on while she stared at me, hurt and humiliated. Not me, her. Crushed. I got dressed, tried to kiss her, tried to hug her, tried to tell her I loved her, but it wasn't right. She was angry and hurt and...

And I walked out of her apartment not knowing if I'd ever see her again. Amanda Drake did this to me!

No...fuck no...it was worse. I did this to myself! My infatuation with Amanda Drake had led directly to this destruction.