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 7

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"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 had done 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.

I moped for three days. Amanda knew what had happened. She even had the nerve to snicker when I told her. Snicker? It was her fucking fault, and she laughs at me? "You didn't really think you'd keep a woman like her did you, Jamie?" She taunted me on purpose. Why? She did this, and now she taunts me. Like it's my fault.

"So your little woman dumped you," Amanda said as I sat at the kitchen table crying my eyes out for the third time in a week. "Sweetie, not every woman is as understanding as I am. Not every woman wants her boys like I do, all soft and pretty and wearing panties."

"This is your fault," I lashed out. "You...you did this to me!"

"My fault? How many time have we had this discussion, Jamie? My fault. There is the door. Walk out it. Go. Go if you must. Take off your panties and go, I'm not stopping you."

I sat there, unable to move. Wanting to run away, to get as far away from this evil woman as possible, but frozen. I could not even look her in the eye. Was it my fault?

"But I'm...I'm a man," I whispered.

Amanda, shot back at me, her anger rising. She seemed half to be venting that anger at me, half toward some ghost in her own mind. "A man walks out that door, Jamie. A man doesn't let a woman do this to him, Jamie. A man stands up to his mother-in-law, Jamie. A man would not take it. A man would never have let her..."

Her face was flush, her breathing shallow and rapid.

"Let her what, Amanda, what?" What the hell was tormenting her? Mother-in law? What was she talking about? She's not my mother-in law. I just stared at her, bewildered.

"A real man never would have let...let her...mother..."

'My mother'? Had she gone out of her mind? What was she talking about? "I...I don't understand."

"Ms. Drake," Imelda's voice from behind me startled me. "Please."

Amanda quickly stood, looked at Imelda, opened her mouth to say something, thought better of it, then changed her mind again. "Why, Imelda, what's it matter? Why can't I?"

"Please, Ms. Drake." Amanda's mouth tightened. "You do what you want. You can. Just you should not. You know...you know it not time."

"Fine, Imelda, it doesn't matter anyway. Let him find out later, it won't change anything, will it. It's too late for that." She stalked out of the room. I had a feeling that this superb woman had just very nearly lost control of herself and was only now stiffly recovering it. I'd complained that I was a man once too often? What was this?

I just stared at Imelda, mouth open. "Imelda, what...what is going on? What was she talking about?" I think a piece of me was grasping at understanding, but just could not quite fathom it.

"She never should have hired you, I told her the resemblance was too close, that she'd get emotionally involved."

"Too close to who?"

"Please, it not matter, Jamie."

"Why? What am I missing? She almost told me, didn't she? Does it have to do with this, what she's doing to me? Why?"

"Jamie, I no can tell you. I work for her, she...she tell when she want, if she want."

"But this is not fair, dammit, I...I have a girlfriend...this is not fair...to me...I have Lisa."

I stormed out of the room, pissed again at both Imelda and Amanda. Who the fuck were they to mess with my life? I was not some toy to play with!

I spent the next week in a funk, depressed. I avoided Amanda and Imelda. I slept late, did no work around the house. Part of me wanted them to kick me out, to make a decision for me. I was too weak to leave, but I was not going to talk to them.

I went to classes, though that too pissed me off. I had to wear panties-they'd taken all my male underwear, and since I had no cash or credit cards, I couldn't buy anything. I tried going 'naked', but caught myself in my zipper on Tuesday and went back to panties. Maybe I secretly wanted them, I don't know. I slept in them when I didn't have to, maybe I wanted them.

To avoid Amanda and Imelda, I went to a bar every night till I thought they were alseep.

To avoid Lisa, I skipped the college bars, instead going to a lounge nearer Amanda's home.

Friday night, when I got home, slightly...okay...half...mostly crocked, I found Amanda waiting for me. Not in the kitchen, where she often was, or her office, where I'd sat at her feet often, but my bedroom. Not her first time here, but not her usual haunt, either. Rare enough that she startled me, then worried me.

She was standing, arms crossed, a vision of a dominant woman. She was wearing a little black dress, black nylons, heels. Her hair and makeup were done. She looked like she had a date.

"Oh, hi," I said, the first words I'd spoken to her in a week.

"What's the matter with you, James?" Oh, I was James now?

"Nothing," I mumbled.

"You haven't been doing your work for me. All week. Worse, you've been avoiding me, sissy," she said glaring at me, chilling the room with her voice.

I recoiled as if struck; how quickly she went from James to sissy, from the masculine to the submissive.

"Struck a nerve, did I?"

"I'm not a sissy, I've told you that," I shot back.

"Wearing panties?" she quickly retorted.

I looked down.

"You know only women and sissies wear panties, Jamie."

"Why are you doing this to me," I answered, tears in my eyes.

"Imelda didn't tell you then, didn't she? I...I don't really believe I owe you an explanation. I mean, you are free to leave any time you want. Why do you stay? Because I let you date Lisa. That doesn't change what you've become, now does, it, sissy."

My face reddened.

"Sissy," she said again, taunting me now.

"You...you ruined it with her!"

"Your precious Lisa? Ruined it? Don't forget whose home you live in. Here, you're under my control. I didn't ruin it with her, I just forced you to confront something you'd rather not confront. Believe me, you only became a sissy because you want it."

"You wanted it, not me. I don't understand you...what ever happened to you before...I didn't ask for you to do this to me!"

I didn't expect the slap. Her hand stung my face. "You didn't ask? Like you had to ask, Jamie? God, I knew there was a sissy inside you from the moment I first laid eyes on you. You may not have known, but I did. Of course you...you accepted all this," she said sweeping her arms about my feminine room. And if Lisa loves you, she'll accept it. Just like I...it doesn't matter. It's too late for anything else. Trust me, that I know, if nothing else. It's all or nothing now."

"That...that's not fair." God, how I loved Lisa and how it pained me to be away from her. But she'd...she'd asked me to leave. Because I'd...I'd....

"Do you love her?"

"Yes," I answered instantly.

"And if she loves you, she'll accept this part of you. James, I talked to her, remember, I understand her. This will work out if it's meant to work out. I think, like me, she'll accept it."

Like her? What the hell did she accept? What happened to her? I had my suspicions, but I wasn't sure? Who? Her brother, her lover, her father? Who...she had to have accepted someone. Richard, maybe? No, never, not him. And how could she know Lisa would accept this, accept me?


"That's so...so fatalistic."

"And so full of faith. And she doesn't even know the half of it yet, does she. She saw you in panties. Wait till she sees you in a garter belt. Wait until you wear a dress for her. Or a maid's uniform. If she's who I think she is, she'll want it, even if it scares her. She'll learn what she really wants."

"Just like this is what you want for me?"

"Sweetie, I wanted this for you the second I saw you."

"But I'd never worn panties before. Dammit, I should have rejected you? I thought..."

"Maybe you should have, Jamie. But you didn't, you couldn't. You won't."

Her face softened for the first time that night. "The point is, if she loves you, and if she's anything like well...she'll be back."

"I don't know..."

Amanda walked over to me, put her soft hand on my cheek. "It's out of your hands, sweetie, there's nothing you can do anyway."

I shuddered, lost in the smell of Amanda's perfume washing over me. Amanda leaned closer, her lips touched my ear, kissed it gently. "Trust me, sissy, trust me."

She let go, turned, started to walk away from me. I almost collapsed onto the floor, watching her walk towards the door.

"By the way, Jamie, the reason I came up here was because I have a job for you."

"A job?"

"Yes, you are under my employ, remember? You can try to avoid me, but you've work to do. Richard and I are in my bedroom, I want you to get dressed and bring us a bottle of wine. If you'd been around, maybe you could have done some cleaning too. But, well, here you are now, might as well put you to work. Get dressed."

She swept her hand towards my bed. "Just because your Lisa doesn't want a sissy doesn't mean I'm not going to use you when I need you."

I looked towards the bed and saw a neatly folded pile of clothing, and a few other things.

"The bottle is in the wine chiller. I want it served in half an hour."

I walked towards the bed, the things. A sheer bra with breastforms inside. A white satin shirt, black satin shorts, black hosiery, panties, heels. I was to be a woman, or close to it, serving my employer and her lover. No wig, no makeup...close to a woman...but not quite. No...a sissy. A wig and makeup would make a woman. I was to be a sissy.

Sighing, I undressed. I could not get Lisa out of my mind, looking at the clothing. Would she really accept me like this? A sissy lover? We were really meant for each other? Dammit, fuck Amanda Drake!

Pissed, I picked up the white bra-pocket bra, the tag said. I wrapped the bra around my chest, feeling the heavy tug of the silicone breasts imbedded in the bra. Underneath the bra was a pair of tight white panties. A gaff. Really, something to designed to hide my bulge. In just the bra and panties and already I felt feminine, girl like. I glanced in the mirror, my figure was trim, a little curved. How was Lisa ever going to accept this?

I picked up the pair of black pantyhose that completed the lingerie. Slipping them onto my shaved legs, I could not help but notice how sheer they really were. They made me look even more feminine. But without a wig and makeup, not completely. Sissy, really.

Could I ever be Lisa's girl?

A uniform. Of course, serving my boss, my mistress, and her lover. What else? I'd worn this one before, recalled hating it. At least in a skirt, I was giving up all pretense of being a man. This, the black satin shorts, the white short sleeved satin blouse, they'd leave me in between worlds. Not quite woman, certainly not a man. They screamed sissy. These were for a sissy.

I'd forgotten how tight the shorts were. I'd never be able to wear them without the gaff. Even with, I thought, they'd never fit if I was endowed even just like a normal man. Shit, as it was, the front of the shorts looked no different than if a woman was wearing them. Small penis tucked away...a feminine front.

The short sleeved blouse served to show off both my artificial chest and my thin arms. Dainty even. Feminine.

Not that the four inch heels didn't have the same effect on my legs, especially with the sheer nylon encasing them. Feminine.

Looking at myself in the mirror, I saw my face. Soft, maybe feminine, but not yet a girl.

Not man or woman. Damn Amanda!

After getting the wine and two glasses from downstairs, passing an Imelda with a satisfied smile on her face, I went upstairs and knocked on Amanda's door.

"Come in," I heard Amanda call.

I walked into the suite of rooms into the softly lit bedroom to find Amanda and Richard relaxing on the bed. Richard was shirtless, wearing only black dress trousers and his socks. Amanda was still in her little black dress, reclining against his bare chest, the fingers of one hand running across the muscles of Richard's hairless tan chest. I didn't know where to look -- Amanda's legs, exposed to the milky white thigh above her stocking tops, Richard's strong chest, the wall.

"Pour us a glass, will you sissy."

"Yes, Ma'am," I answered.

"You're so cruel, Mandy," Richard laughed.

"Am I now? Why, taunting you with such a pretty creature?"

"Oh, she's breathtaking, I'll give you that."

"Hmmm, want to borrow her again?"

Richard chuckled. "She's got a girlfriend."

"Not now she doesn't," Amanda corrected him. "She dumped him."

"Wanted a real man?" Richard asked Amanda, though it also taunted at me.

"I'm not sure, sweetie. I think she's not sure what she wants."

"Well, I know what I want," Richard said, taking Amanda's shoulders into his hands.

"Wait," she giggled, "let me hang my dress up." Amanda stood up. "Help me, Jamie."

I teetered to Amanda on my heels, reached to the back of her neck to undo the zipper of the dress, and helped her step out of the black fabric. "The hanger is in the closet," she ordered. I could hardly move, as my gaze did not want to break away from Amanda's body. She was wearing just a black garter belt and stockings. No bra. No panties. She was amazing.

"Go hang it up, sissy." How I just wanted to gaze at Amanda. How I longed to take the place of Richard, to find Amanda in my arms.

It did not help matters, walking back to the bedroom from the closet, teetering on my heels, my midsection, my crotch held tightly by the satin shorts. The physical reminder of Amanda's punishing feminization of me.

The harsh reminder of-of what? I never asked for this, never wanted this -- dammit, why couldn't I act like a man? Was I really this? A sissy?

Looking at Amanda on the bed with Richard-the now naked Richard, arms wrapped around Amanda, kissing her deeply, I almost cried. How could I ever have this with a woman? I...I never could, could I? Not as a man?

Richard grunted between kisses, nodded his head my way. Amanda looked back, saw me staring at them. At her beautiful body. At Richard's beautiful body. At his naked cock. "Is she staring at me or you," he asked.

"That's all for this evening, Jamie," she said dismissing me. I left, tears finally forming as I closed her door, forming in front of Imelda who was standing there watching me.

"Shhh, don't cry Jamie. You must know you can never have her."

I walked quickly to my room, Imelda right behind me, watching me as I sank into a chair, watching me cross my legs like a woman, the gaff and my small size making it easy for me to sit ladylike.

"Why does she do this? I...I can be..."

"Be what? Her lover?"

"Yes," I whispered, looking down at my nylon covered legs, which took any conviction from my voice.

Imelda laughed. "Jamie, you can never be that. Look at you...you not man like Richard."

"But I thought she...she likes boys in...in panties."

"She does. But...after her...after her husband passed away...she...she'll never take one as a lover again. For him...for his memory."

"Then why the hell is she doing this to me? Dammit, Imelda, she was practically fucking Richard with me standing there."

"She do that with her husband too."

"What? Why?"

"Remind him his place. That he sissy, not man."

"She...she...did that in front of her husband?"

Imelda nodded. "In front of sissy, yes."

I was confused. She once made love to other men in front of her husband? Her husband was a sissy? Like me? I couldn't deal with that! I couldn't deal with any of this!

"But I'm a man," I tried again. Imelda looked at me, smiling.

"Are you? Is that why Lisa no talk to you? You too much man for her?"

"Imelda, I love her," I cried again. "Don't you see, I just want...I just want to be her boyfriend, to be normal for her."

"That Ms. Drake's point. You can't be that. If Lisa love you, she must love sissy." Imelda shook her head, turned and left the room, leaving me crying on the couch.

I slept there on the couch, crying myself to sleep, too sad to even get up and go to my bedroom, only kicking off my heels and covering myself with a blanket to ward off the cold. Maybe I was punishing myself for being so weak.

Lisa had to love a sissy. She did, she had to! But I never wanted to be a sissy yet here I was all the same. Hoping Lisa could somehow love this, love me.

The following Saturday I was sitting at my now usual table at the bar near home, doing my usual, drinking to escape my problems. I was too weak, too cowardly to just leave Amanda's. I was a fucking sissy, wasn't I? A man would put up with this? Never!

Lisa. Oh, fuck, Lisa! I looked up, assumed I was having a vision. Lisa? It was Lisa. Sitting down half way across the room from me. With a guy. Was she...was she on a date? No way!

My love?

I started to get up, to get out of there. I couldn't face her like this. But realized I could not without passing right by them. I sat there, willing the floor to open up and swallow me.

Lisa's date, if that's what he was, got up and walked to the bar. He was tall, muscular. His light blue shirt was painted on over his muscles. I sighed. A man. I recognized a man when I saw one.

By now, I was stewing, watching them talk, flirt. Casual touches, arm against arm. She touched his chest when she laughed at something he said.

They kissed. I watched his tan arm move around her back as he kissed her. I thought of Richard and Amanda. I stirred.

I felt it in my panties. I stirred. The pink panties I was wearing under my pants. He kissed her and I was getting an erection. I closed my eyes, pictured her naked body. I thought of kissing it. I thought of Amanda. Richard's erect cock pressing against her leg. Hard, big. I felt my little cock stir again.

I swallowed hard. Richard. Amanda. Lisa. Her date. A mental image, Lisa on her back, this muscled man on top of her. Fucking her.

I was erect now. Sissy. You'll never be her man. Stop! Stop thinking like that.

Lisa stood up. Had my eyes been closed? Had she seen me? She was walking right towards me.

"James," she said by way of hello, her tender eyes almost apologizing for the awkward situation. "I'm sorry, I...I didn't know you were here."

"It...it's okay, LIsa," I said, trying to will myself to shrink. "I...I miss you."

"I know." She was sweet. "I...I just don't know if..."

We were watching each other, when suddenly some guy bumped into her, spilling his drink onto the side of her blouse and skirt. Without thinking I quickly grabbed the napkin from my lap and handed it to her. She just stared. She took the napkin in her hand but stared at me.

I looked down...What the....my crotch. She was staring at...at my erection. Lisa looked back to the table where the guy she was with was sitting. Back to me, then down to my pants.

"Lisa, I..."

Lisa looked back at her date, then down at my crotch, at my erection. "Um, Jamie, I...I have to get back to Mark."

And with that, Lisa and I looked at each other awkwardly, until she walked back to her date. They spoke, smiled, paid their bill and left. It took me ten minutes to be physically able to stand up and go.

That night I dreamed of Amanda and Lisa and Richard and Mark. Women, men, sissy.

I saw Lisa the following week in the library where I was doing some work. She wanted to talk. She said we needed to talk.

"We need to talk."

"Okay." Did we ever. Not that I knew how to talk. Not that butterflies were not dancing in my stomach over what I knew had to be the subject matter of our discussion. "Here?"

"No, no, not here," Lisa answered toying with a loose strand of hair. "Somewhere, more private. Can we drive over to my place? I'm done for the day anyway, and well, it's quieter."

Into the lion's den where she'd caught me wearing panties? Sure...let me just go hang myself first.

We drove over separately. I kept saying a few words in my head. "Lisa, I love you." "Lisa, I'm so sorry." "Lisa, I'll never do it again." Would one of those win her back?

I guessed I'd promise anything. I had to...I loved her.

The smell of Lisa's apartment hit my nose as soon as she opened the door and walked in. The feminine smell. Lisa's smell. I wanted her so badly.

We sat down across from one another, Lisa on a chair, me on the couch. I'd have almost rather sat next to her, as across from her I could not help but stare at the length of her legs exposed by her skirt when she sat.

"Lisa, I...I want to explain," I started.

"No, wait Jamie, please, hear me out first." I just wanted to cry.

"Jamie, I've been thinking a lot over the last few weeks...I'm not even sure where to start or what to think. I...I'm sorry, I'm kind of uncomfortable talking about this."

"Lisa, I should apologize...I..." She held up her hand again, stopping me.

"No...please...this is my fault, let me finish." Her fault? What was she talking about?

"Your fault...how is this your fault?"

"How? I'd been teasing you...I called your underwear panties, I'm not even sure what came over me...what I was thinking when I said those things. It's just that...our love making was so...so different....from any man I've ever been with, from...from anything I've ever experienced...I know felt it too...I guess I should have been flattered that you'd actually put on panties for me. That you'd do something like that to please me."

I tilted my head. She lost me. Please her? What was she saying? That I'd put on panties for...for her? "Put on panties for you?"

"Really, Jamie, you thought you'd pay attention to what your woman wants, and you actually went so far as to wear panties for me because you heard me say I wanted you to. And I rejected you....sweetie, I'm so sorry." A tear was forming in her eye.

"But you...you think..."

"Yes, you do something no man would ever do and I get mad...what kind of girlfriend am I? That's my fault."

I still wasn't quite getting it. "But you kicked me out?"

"I know love, and I'm sorry. Making love with you is so confusing...I mean, it's the best, sweetest, most tender sex I've ever had...and I admit, I...I actually did picture you as a girl a few times. I don't know...you must think I'm a freak."

Her the freak? Fuck...what the fuck...this was unreal.

"You pictured me as a girl when we were making love?" My head was starting to hurt from the spinning. Clearly the world was tilted.

"I don't know what it is, Jamie, I just never met someone like you...and when we...when we make love...it so different than anything I've ever done with a man...I admit I did fantasize about you in panties, and it did feel so...so feminine. But I guess it just sort of weirded me out a little to see it...I think I was afraid of my own feelings. Will...will you forgive me?"

"Of course, Lisa," I almost shouted. Then I thought of Mark. "You...you want to get back together?"

"If you'll have me," she said shyly.

"What about...about that guy?"

"Mark? I know...I'm sorry...he's like...this is funny, but, he's just like the men I dated before, strong, masculine, but...missing something. Missing what you have. He's nothing like you." By which she must mean soft, feminine, of course. Lisa stood up, walked to the couch, sat down next to me and looked into my eyes. "Will you forgive me?"

How could I argue with her?

"Why did you go out with him, then," I asked, thinking I should just forgive her, but unable to stop myself from asking the question.

Lisa moved her hand to my hair, toyed with it. "I guess seeing you in panties kind of scared me. At the same time it excited me, it scared me. I ran from that, afraid to admit how much it made me happy. I just kind of ran as far as I could."

To a man, she meant. As far away from a sissy, of course. Should I ask it? "As far away?"

"Yes, I...when I saw you as kind of feminine, so I guess I just kind of ran to...well, to a man."

"A man," I repeated softly, feeling a stir inside my pants.

"Not that you're not...a..." she could not say it.

"What, a man?" That came out harsher than I wanted. She was questioning my manhood? Of course.

"Sweetie, don't be mad, I told you, I love you how you are, I can't even picture you any other way. Believe me, that's what makes you special to me. Jamie, please, just...forget about him...forget about trying to be all macho...I love you how you are." She kissed my cheek. "Please, will you forgive me?"

"Yes," I whispered, not trusting my voice, feeling her soft hand where it rested on my bare arms.

"James, I swear, I am in love with you," she said, leaning to kiss me. God, that soft passionate kiss. Those wet lips, that tender mouth. That mouth that was kissing a man last week. That mouth, the woman I loved.

"Jamie," she said, finally breaking our kiss after several minutes and just before my hands got to the front of her shirt, her breasts, "will you...will you still do that for me. Can we...can we try again?"

"Try what?" Right now, as emasculated as I was, my upper brain was not quite functioning. Little Jamie was the one doing the "thinking" this second. Thinking just of Lisa's breasts.

"Will you..." she was embaressed, "you know...do what you did before?"

I looked at her puzzled, thought process stuck between my pants and my head.

Lisa looked down shyly. "Will...will you wear a pair of panties for me?"

I started to shake...both heads reeling! She fucking wanted me to wear panties. "You...you want me to wear panties...now...but...I thought we...you know...could kind of..." I was thinking of make up sex.

"I...I know...will you...wear panties...while we..." She looked towards the bedroom.

"You want me to," I gulped, "wear...wear panties while me make love." My god, that sounded so deviant out loud. Yet the word panties from her mouth sounded so erotic.

"Yes, please," she whispered a little more aggressively. "I..." She took a deep breath, gathering something inside her. "I want you to wear my panties while we make love."

I almost ejaculated. Fuck! How the hell could I say no to that? "Um, o...okay," I answered trying to sound reluctant, though it was apparent I was quite eager.

She quickly jumped up and tugged me to the bedroom, almost as if needing this before she lost some nerve.

"Why...why do you want me to...I thought you didn't like it," I asked her as she led me by the hand to her bedroom.

"I never said that," she said, sitting me down on the bed. "It was a shock, yes, but I told you...I don't know...it's hard to explain..." She sat down next to me.

"Lisa, I..."

She kissed my forehead, then my lips. "I told you before, making love to you is so different than having sex with a man..."

The corners of my mouth tightened.

"No, that sounded bad, I'm sorry. Not that you're not a man, or anything, you just are so tender, it...its almost like making love to a woman."

"You thought of me as...as a woman." Like this was surprising.

"Honestly, a little, yes," she actually blushed. "Maybe I'm just playing out some fantasy in my mind, I don't know. It was almost like I was experimenting, making love to a woman, but...but safe somehow, because it's you instead. And then you actually pick up on this and try to wear panties for me..." She kissed me again.

"You don't see me as a man?"

She bit her lip. "That sounds so...harsh, sweetie. It's not that, I mean...I know you're not a woman...but..." She didn't answer the question. That was answer enough.

"But I'm not a man like some of the men you've been with, right? So you can fantasize that you're making love to a woman."

"I don't know why I was mad. You're so special, Jamie. Please, you were willing to indulge me once, can we try again?"

I gulped. Could we try again? I would have worn a dancing bear costume to try again with Lisa. But she didn't want a dancing bear costume. She wanted panties. "Sissy," I thought, Amanda's voice suddenly running through my consciousness. She wanted me to be a woman. She wanted me to be a sissy. Both of them.

"Please," she asked again, kissing my neck, my face, "please try again."

"O...okay," I nervously answered. Then, "Yes."

Lisa kissed me deeply on the mouth. So much passion. Just because I said yes. Oh, god. Finally breaking away to walk to her dresser, to open her drawer of lingerie. She pulled out something, dropped something on her dresser, turned to me, holding a pair of white satin, lace trimmed panties in her hands. The look on her face was so innocent, so inviting, so seductive. She really wanted me to wear those panties, her panties, her pretty panties for her.

"Lisa, are you sure you want me to wear..." I was still having trouble saying it in front of her.

"Sweetie, please, yes. I want you to wear my panties. You...you did this once before and I rejected you. I promise you, I won't again. Yes, I...I really want you to. You don't have to be shy, I...I know a man would never even consider this...but...please." The way she said please...I could not resist even if I wanted to resist. The veiled reference to my lack of manhood was too much.

I tried not to shake when I nodded that I would. She smiled an incredible smile, walked towards me, handed me the satin panties. The tension was thick in the air between us, the panties electric in our hands. Touching the satin, it dawned on me that I had a problem. I was wearing panties right now! Not as pretty, but pink cotton. Women's panties. I...I couldn't let her see that, not yet...she...she'd wonder...maybe even reject me again. I looked around the room, tension rising in me.

Lisa saw the fear in my eyes, mistaking it for nerve. "Sweetie, I...I'm sorry, you...you must be a little uncomfortable, I know. Why...why don't you go into the bathroom and change, I know you probably want some privacy getting ready, don't you?"

"Yes," I said a bit too relieved. I was walking a dangerous line here.

"I thought so. Then I can make myself look pretty while you're in there doing the same."

"Pretty," I gulped.

"Yes, I want to look pretty for you too...fair's fair, right? If you're going to be pretty for me, I should be pretty for you, too." She picked up whatever she'd placed on the dresser, something for her to slip into, I presumed.

"Okay," I said, starting to walk to the bathroom, my back to her.

"Wait, Jamie, will you..." She had what had been folded up in her hands unfolded, held out to show me. I looked at the white satin, spaghetti strap garment. The lace around the bra cups and alongside the slit on the left side. I looked down at the panties in my hand. The lace. The lace matched what was in her hands. The panties matched the babydoll she was holding outwards towards me. They were a set. This wasn't for her to wear. Oh my God, she meant it for me.

"You...you want..." My throat tightened. That babydoll was not meant for her. Whatever she was going to do to look pretty, that babydoll was not a part of it.

"Will you wear this, too? Please? It will look so pretty with the panties."

That softly spoken word again. Panties. I melted.

"You...you don't have to," she said quickly, probably wondering if she'd pushed me too far, "but...it just...matches so nice...you'll...you'll look so...so...pretty." The last word passed her lips with a hint of hunger. A hint of desire. Something she wanted, needed.

There must have been a hunger in my eyes as well. She just walked forward and handed it to me, eyes down, almost embarrassed. "It will just take me a few minutes...I...I'll call you," she said.

I went to the bathroom, now holding both the babydoll and the matching panties that belonged to my girlfriend. Unlike almost any man, well, really, any man, I wasn't hoping to see them on her, I was already feeling a longing to try them on myself! But I wasn't a sissy, dammit. Right?

I kept telling Amanda. I was not a sissy. I did not want this. She made me, that's the only reason. I could not say no to Amanda. But I could say no to Lisa, and I didn't. In fact, I wanted it. I wanted to wear this, I felt it, the need, the desire.

I closed the bathroom door, leaned back against it, trying to catch my breath. Not for the first time, I thought this was a terrible mistake. I wanted to be her lover, but her masculine lover, right? I could be...I should be, a man for her, not this. I thought of Imelda's words, if Lisa was going to accept me, it would only be as a sissy. How could she know that? Was it true? Was this it, a sissy or nothing? She wanted this? Did she really? Would she reject me again?

I suppose I had to find out. I undressed, careful to hide my own panties by wrapping them up in my pants. I was surprised I wasn't hard, given the extreme sexual tension I felt. I knew I was excited, sexually, but I wasn't erect. I must be close to it, but not close enough yet. Or was it the feminine feelings? Was that stopping it?

I stepped into Lisa's panties, pulled the delicate satin up my legs, carefully over my hairless legs, tucking my...my what...my cock...my clitty...my little thing...into the crotch of the satin panties. I paused, shaking my head at the bizarre situation. Was it a cock? A man would have been hard as a hammer, thoughts of fucking Lisa rushing hormones, blood, excitement to his cock. A man would not be tucking his flaccid little organ into satin panties. How could I call it a cock? It was soft, small. Not very masculine...nothing masculine here. This is what she wanted.

I slipped the babydoll over my slim chest. Looking in the mirror, I realized that, except for the lack of a bust, my figure was quite feminine. Slim, lithe, soft. I realized just how easy it was for me to look like a woman. I looked more womanly in women's clothes than I did manly in men's clothes. Add make up, styled hair, breasts, I'd certainly pass. Is this what she saw? When I was naked, was it easier for her to picture me a woman than a man? How could it not be?

My god. My hair was already getting a bit longer, at Amanda's direction. If it was styled...even flat chested, even in just a babydoll and panties I was almost a woman. Almost? I looked feminine. Without makeup, breasts, hair, I still looked feminine. Soft. Tender.

Waiting for Lisa to call, I started to sit on the toilet seat -- too cold, so instead I just leaned on the counter, looking into the sink, biting my lip. I was as nervous as a bride must be on her wedding night, I thought not without irony. How many brides waited in the bathroom on that special night, nervous to go out?

Gazing at my reflection in the mirror, I thought, what the hell. I picked up a bottle of Calvin Kline Eternity perfume sitting by the sink, squirted myself like I'd seen other women...well, real women, do. I inhaled the sweet scent, breathing, letting the scent wash over me, the femininity wash over me.

Was I going too far? She had not called yet. Might as well...I...she wanted this, right? There was a bottle of mousse on the counter. A dab in my hand, into my hair, messing it up, trying to make it look feminine.

Fuck, looking at myself -- thin, satin covering my skin, the scent, the tossed hair...this went too far! I was going to shock her again. I really did look like a woman!

"Jamie," Lisa called from the bedroom. "Are you ready?"

I realized it was now or never. Too late to change anything back. If I did not walk out of the bathroom and into the bedroom like I was dressed now, I might as well throw my own clothes on and storm out. If I loved Lisa, I had to go out there now, dressed as I was. I don't know that I could ever be a "man", not now, not after what Amanda had done to me. I had to take this chance. She'd never see me as a man...not once I opened that door.

I slowly opened the door, walked into the bedroom. The lights were off, the shade drawn. The only light came from candles she'd lit and placed around the room. It was romance, pure romance. And I was the woman.

Lisa sat on the edge of the bed, one leg tucked beneath her, the other tanned leg hanging to the ground. She was waiting anxiously for me. She was beautiful.

Lisa was dressed in pink, a pink chiffon babydoll, slit right up the middle, cupping her breasts gently. I was suddenly jealous of her breasts. I could just see a glimpse of her pink panties, covering her womanhood, her temple.

I heard her gasp when she looked up at me. I'd over done it! I almost turned right back into the bathroom, but managed to hold for a second. "Jamie, you...you're so pretty," Lisa said, standing up gracefully, taking two steps towards me. She paused, sucked in a harsh breath, then practically jumped to me, taking me in her arms, mouth desperately seeking mine, kissing me. Her first kiss was almost violent, needy, but she slowed down, became gentler, and tugged me towards the bed. The kiss was acceptance.

"Lisa," I started, "I feel..."

"Pretty, please say pretty," she pulled me sitting down with her. "You look pretty, you smell pretty. Please, tell me you feel pretty." She looked a bit shy again.

"Is...is this what you want? Your boyfriend to be pretty?"


"I...I can't lie...I...I do feel...god, pretty."

"Shhh," she said, kissing me again. "Please, before I lose my own nerve, Jamie, just...just be a girl for me."

Her girl? Now -- today? Or always? What did she want from me? My brain was trying to think rationally, but her mouth on mine, her breasts pushing into my chest, satin, chiffon, feminine, woman...they...I was losing focus. Thinking of her...thinking of being her woman.

"Make love to me like a woman," she whispered as she licked my ear.

I was overcome. I...I was her girl. I surrendered to her, to the feminine hormones that seemed to pulsate through me.

We kissed and kissed. Touched. We were two...two women...we were one...one woman.

I was on my back, Lisa on top of me, kissing my neck. "You're so pretty," she said, licking me. She kneaded my chest through the satin babydoll. Her hand wandered down my stomach. I lay back, letting her make love to me, to lick and explore me, to make me feel truly like a girl.

I was lost in it, in her. I felt her hand move towards the waistband of my panties, and I suddenly realized I still was not really hard. Swollen, yes, but not erect at all. I tried to sit up, turn her over, the male part of my brain unwilling to admit that there was some feminine part of me at work here. The male part ashamed to have a soft lump for her to find.

"No, just lay back, sweetie," she said, her hand moving lower.

"Wait, I..." But her hand was on me, on my mound, over my flaccid penis.

"Oh," she gasped.

"Lisa, I'm sorry," I said, trying again to sit up, fearful she was going to realize I was a freak. I should have been erect, so excited, not so small.

"You...you're so soft," she said, smiling, hand rubbing my crotch through my panties.

"I'm sorry," I blurted out.

"Oh, sweetie, no, it's okay. You're small anyway, I mean, it's not like you're as big as...I mean...you're not like a...I don't want this to sound bad or offend you, but..." she giggled, "it's so cute."


"Cute, like...like a girl," she was rubbing me. "Come on, don't give me that look, Jamie, I mean that in a nice way. You are kind of small, you know. This...this is what a girl should find in another girl's panties, a soft mound, not a...um...not a cock."

As if on cue, I started to swell a little more. She felt it with her palm, through the panties, which caused her to laugh.

"See, you like being a girl, don't you." The tone of her voice was strange, both harsh, yet tender, dominating but seductive. So much that I thought of Amanda.

"This is just a little weird, Lisa."

Lisa pushed me back into the bed, climbing on top of me, her own soft mound on top of mine, massaging me. She licked my ear, kissed, it, tugged it. "Do you want to stop? Or do you want to keep being my girl?"

Her humping was driving me wild. Stop? I did not want to do anything that might make her stop.

"Oh, Jamie," she moaned again, continuing to hump my panties. "I...I don't even understand this myself, but...but this makes me so hot...I..." She shuddered, a miniature orgasm washing over her.

"Lisa..." I too moaned feeling the heat inside her.

"You like it, you like it. Being my girl."

"Yes," I answered, not thinking, still swelling.

"Hmmm," she rocked back and forth. "You're getting more excited. You like being my girl. I can feel your...I don't know what to call it, something small." she laughed.

I moaned again, shaking more.

She focused on my eyes, while her own orgasm washed away. She focused on turning me on. "Oh, that turns you on, does it? Hearing me talk like that? Telling you how small you are?"

Fuck, what was she doing to me? I just rolled my eyes back, moaned, "Liiisssaaaa."

She giggled. "You like hearing you're not a man? How you have such a small little...pussy?"

"Lisa!" I tried to sound angry, but my lustful thrusts were too intense.

"Hmmm, hit a nerve?" She was kissing me again, going faster, going towards her own edge. What was she doing...her self discovery was killing me.

"So much smaller than any man I've been with, little girl." Her voice sounded in my mind too much like Amanda's.

"Please, Lisa," I begged.

She sounded like she was orgasming again, her moaning, her humping.

"Stop?" she asked me, no longer moving, pleasure moving over her. Even teasing me she was concerned about me.

Stop? God no. "No, no, please, no...no...don't stop," I begged, suddenly conscious of the feeling of Lisa's breasts rubbing on my chest through our babydolls. Feeling conscious of the soft satin, the chiffon, her hair, our scent, the perfume.

"Ohhhh," Lisa moaned, shuddering again, a bit more violently, the waves of orgasm washing over her for a second time, twice for her, none for me. As she let the orgasm run through her, she slowed down her dry humping on my crotch. I was shaking myself, pleasured, erotic energy running through me, but not enough to orgasm. I could if she continued, but I could not get close enough, it was elusive, out of reach.

She was moving slower and slower, her own orgasm subsiding. Leaving me.

"Lisa, please...please don't stop," I begged, shaking, knowing just a few more minutes and I'd go over the edge too.

"Just...just a minute," she cooed, kissing my neck again, my chest, gently lifting her panties off mine, leaving me there...to just enjoy her mouth on my skin.

"Lisa...please...can I..."

"No," she giggled, "let me kiss you. Just relax, let me...let me make love to you like a woman. Just, trust me."

She kissed down my stomach, her tongue a hot flame licking downward, teasing me, taunting me, until she was kissing the front of my panties.

"Oh, Lisa," I moaned, pressing my hips towards her.

She laughed. "You...you really do look so pretty dressed up in my panties, Jamie, in my lingerie."

"Ohhhhhhhhhh," I moaned loudly.

Lisa's voice got a serious tone. "You...you like being my girl, don't you?"

"What...what do you mean?"

She sat up, looked at me. "I mean, you are doing this for me, I know I asked you, but, but you like it, god, you love it."

I just looked at her, afraid to acknowledge just how close to the truth she was.

Her hands...her hands were my undoing. They moved slowly to the front of my panties, slowly, gently, erotically, rubbing me.

"You like it don't you?"

I still did not answer. Lisa stopped touching me.


"Answer me," she said, quietly, but clearly a command. An order.


"Do you like it? Do you?" She wasn't moving her hands.

"Yes, yes," I sighed, "please, don't stop." I was immediately rewarded by her light massaging of my crotch and shook, pleasurably.

"Do you really like this," she asked, removing her hand from the panties I was wearing.

"Yes, god yes, Lisa." I was rewarded with her hand on them again, lightly massaging me.

"Jamie, I...I love you."

The hormones must have been flooding through me, clouding my brain. I felt desperate to cum, to orgasm. We'd started making love as two women, but Lisa had somehow stumbled onto something more.

"You're so cute, Jamie, it's...this is like a truth serum."

"You're teasing me," I protested while she played with me through my panties.

"A little." She moved down again, until her mouth was hovering over my swollen penis covered by the satin. "This is how women make love, though, isn't it?" She started kissing me through the panties. "So tender, using their mouths. I kind of like this, making love to my girlfriend."

I was shaking and moaning, my hands somewhat involuntarily running over the satin front of the babydoll I was wearing. I was her girlfriend.

Lisa looked up at me while licking. "Hmmm, that's it lover, play with your breasts."

"Please, Lisa, don't," I begged, her words almost too much.

"What, don't you want breasts?" Her mouth did not go back to my panties. She was waiting for an answer. Her teasing, no playing without an answer.

"I...I don't know," I answered as honestly as I could.

She giggled, licked the front of my panties. "I guess that will do. At least you're honest." She licked again, watching me shudder. "Of course, a man would have said no." She kissed me again before moving on the bed so that one leg was under mine, arranging ourselves so that our crotches were touching through our panties, facing one another.

She started humping me again. "Jamie," she whispered seductively, "rub your pussy on mine."

I was moaning and humping her now, almost unaware of anything in the room beyond her. What was she doing to me? Why...why was she enjoying this?

Before I could even begin to think, it ended for me. I erupted in one of the most powerful orgasms I've ever had in my life. I erupted rubbing against her, cumming on her like a bitch in heat....cumming on her as she orgasmed too, together with me.

We both shook, moaned, became one until she collapsed on top of me, a tangled mess of limbs and satin.

Ten minutes...fifteen...finally.

"Lisa...what...what happened," I asked, unable to wrap my mind around the passion I felt for her.

"I...I don't know...that...that was amazing," she stretched, still tangled up in me.

"I mean, I didn't want...are you...are you okay?"

"Okay? My god Jamie...that...that was amazing."

"Amazing...you're not mad at me?"

"Mad, why would I be mad at you?"

"I...I don't know...I guess...I mean...you said...I said I was a girl...how...how can you...how can you love me?"

"Jamie," she protested, "I'm the one that asked you to do this. How could I not. My god, I...I've never felt so close to someone."

"But you had sex with me like I was a woman...how can I...how can you...how can I be a man for you?"

"I don't know Jamie...honestly, this is kind of confusing for me too. I made love to you like you were a woman. Forget about you, you were just doing what I asked. Think of me. What the heck does that make me? A lesbian?"

She'd made me a girl! As if! "Do...do you like other girls, Lisa?"

"I've never been with a woman, Jamie."

That did not answer my question and I told her so.

"Do I like girls? I...I don't know...maybe. I know I loved making love to you."

"Like I was a girl?"

"Yes," she blushed. "But we've always...um...kind of done it like that, haven't we?"

"Not with me wearing panties!"

"No, maybe not, but I would be lying if I said I didn't think about it. A lot."

"About making love to me like I'm a woman?"

"Yes," she blushed.

"How often do you think about that?"

"Sweetie, I do love you."

"How often?"

"Well, um," she bit her lip, "almost every time since the first time."

"And you thought of making love to a woman before me?"

"Yes." She admitted it nervously.

"So what...so you're a lesbian," I asked. "Where does that leave me?"

"I don't know Jamie...I...I love you...besides I...I can't be a lesbian...I mean...I'm attracted to men...I like sex with men."

"Like Mark."

"Sure," she answered before getting quiet. "I...I'm sorry...I didn't mean to...I mean...we were...."

I stiffened a little, realizing what she meant. "You slept with him." It was a statement, not really an accusation.

"Yes, yes. I...I'm not going to lie to you. We...we were..."

"On a break," I asked.


Lisa's toned leg was mashed up against my crotch, against the softness in my panties.

"But he fucked you. Like...like a man."

"Jamie...please...I didn't do that to hurt you!"

"And...and you know...you know you are not a lesbian because you like sex with men, right?"

"Yea," she answered warily.

"A man like Mark fucking you."


"But...but you don't like sex with me, do you?"

"Sweetie, I just loved having sex with you."

"Not like that...not like...not like a man fucking you!"

Lisa did not move or answer for a good minute. "What do you want me to say, Jamie? That I like a man fucking me? Is that what you want to hear? Or do you want me to lie to you? I'm not going to lie, okay? Of course, I like a man fucking me."

"Lisa I didn't mean it."

"No, you did...well, let me finish. Okay, I admit it...I know I'm not a lesbian because I really do like sex with a man. Yes, I had sex with Mark, while we were not talking to each other. That's what you wanted to hear? How good he is in bed?" I could not tell if she was angry. Hurt, maybe?

He leg never moved from my crotch. So she felt it. She felt me swelling through the panties.

"Well, he...he's okay. But I don't love him, I love you. Don't try to compete with some man that meant nothing to me but a great fuck."

"But you don't like it with me...didn't you say that?"

"I said...I thought you understood...you are such a good lover as ...as...well...like this...as a woman. Please Jamie, I don't really understand this myself...how am I to explain it to you?"

"Am I really that bad a lover," I asked.


"Please, Lisa, I answered your questions..."

"You're the best girl lover I've ever had."

"Lisa, I'm serious."

"You mean as..."

"Yes, as a man. I'm not a good lover like a man, am I? Like Mark?"

"It's not like..."

"Lisa...I have to know."

"Sweetie, I like this better." By now there was no hiding my swollen cock. She giggled now. "But you like being my girl, don't you?" LIsa started rubbing her leg over my swelling crotch.

My voice cracked. "Yes." She had the tables turned, was asking the questions.

"Let someone else be the man, Jamie, just be my lesbian lover."

I shuddered more violently, and before I knew what happened I was shaking, squirting, suddenly orgasming again.

"That's my sissy," she said softly, "that's my girl."

And drifting off to sleep with Lisa's sweet mumblings playing in my head.

I woke up still tangled up with Lisa who herself was sleeping peacefully. Her arm was draped over me. I could not help looking at her. Gazing at her face, I wondered for the hundredth time, what I had done to deserve her, what was I doing, and how the hell was I going to make peace between my situation at Amanda's and my situation with Lisa. I loved her, but I was still infatuated with Amanda. Somehow I doubted this would turn out well.

I feared I'd lose both, trying to keep each happy. Looking at Lisa's beautiful face, conscious of the lingerie between us, I somehow knew I had to choose Lisa. But how?

I heard Lisa's breathing change, she started to stir; she must not have been sleeping that deeply. "Hmmmgggff," she said, stretching, trying to untangle her legs from mine. In a way I hoped she'd stay asleep, so I could avoid this unpleasant scene, given my post orgasm loss of libido, when suddenly being dressed in my girlfriend's lingerie was not so appealing.

"Shhh, you don't have to wake up," I whispered.

She twisted her head, stretched, her hand landing on my chest, on my nipple, which she started slowly rubbing through the satin babydoll. "I wasn't just saying that before," she flicked my nipple. "You really do look pretty in lingerie."

"Lisa...I...this feels weird." That's right, assert your manhood. Sure, that will work. "Pretty? I mean, that...that's a strange thing to say to a man." I kind of gulped when I said that, putting little conviction behind the words. Man? Now I was going to try to be a man? After everything Amanda had made me do for her? After earlier, now dressed like this.

Lisa had been looking me in the eyes, but looked down, as if embarrassed herself. "I'm sorry, Jamie. I...I thought you liked this...I didn't mean to...I don't know what came over me."

Good, fuck it up again. She rejects me, then accepts me back, and I'm following it up with rejection.

"Lisa...I...I did like it...it's just that...we...I mean, this is a little weird, that's all."

"I know." She still wouldn't look up at me.

I frowned. "Do you really think I look...pretty in this...this outfit," I swallowed.

Lisa tilted her head back up, doe eyes so innocently staring into mine. "Yes, I James, I do."

"Lingerie, though? Seriously, Lisa, I...I don't mind, but what man would..."

"What man would wear lingerie? I...I don't know," she quickly answered.

"You...you never did this with a man before?"

"No, of course not, Jamie. None of the men I dated would have let me do this to them. Say things to them... but they...they were not like that."

"Not like what?"

Lisa sensually toyed with my nipples. "Soft, sensual, loving, caring, sweet, tender..."

"You sound like you're describing a woman, Lisa."

She didn't respond, but continued to play with my nipples through the satin until they hardened. Finally, "I know. Jamie, I just thought...you know, you did this for me, so, well, if this isn't okay...I mean..."

"What, you want me to wear your panties home, too," I asked joking.

She looked up, a mischievous grin in her eyes. "If...if you want...I mean, if you're willing...I think it would be kind of cute...a little reminder of me?"

"Okay, okay, if...if you insist." Insist? Internally I was jumping up and down. But why? Amanda and panties. Lisa and panties. Imelda and panties. This should be disgusting to me...but I was thrilled.

I was thrilled.

I walked into through Amanda's rear door into the kitchen, practically floating. My afternoon with Lisa was in one respect disturbing, but I had her back. My joy was short-lived. Amanda saw to that.

"Where the hell have you been, Jamie," Amanda demanded, walking into the kitchen.

"Um...I...I was at school," I said, only lying by omission. Something made me hold back the little detail about spending time with Lisa.

"You, sissy, had a list of chores to do before five this afternoon."

I remembered that list. Nothing too heavy, but...she was right...there were things to do. Instead of spending the afternoon with Lisa, I was supposed to be here, working for Amanda.

"I...I forgot."

"Forgot? Did you somehow mistake me for a normal employer? Forgot? You are not asked to do much, thus I expect all to be done when told!"

"I'm sorry, Amanda," I said, whispering the rest under my breath, "for gods sake."

"My office now!" I guess I didn't say it as quietly as I thought.

Amanda grabbed me by the ear and dragged me out of the kitchen, down the hall to her office. She was clearly pissed. Wonderful. Just fucking wonderful!

"Amanda, that hurts." Her nails were digging into my ear.

"Amanda? It's Miss Drake to the help, and this is not going to hurt as much as your ass is when I'm done."

The click clack of her heels on the hardwood was ominous and foreboding.

"Miss Drake, please...I'm sorry, I really am."

"Hmmm," she said, pushing me into the office. "Over there, lean over, hands on the desk."

I assumed a submissive position on her desk while she went around and used the intercom. ''Imelda, he's back. We are in my office; please bring a crop down here."

"Yes, Ma'am," Imelda answered pleasantly, as if relishing the thought.

"Drop your pants, Jamie," she ordered me.

I stood up, unbuckled my belt, started to lower my pants. "Miss Drake, please," I said, turning to look at her.

"Eyes forward," she hissed. I sighed, lowered my pants, and resumed standing submissively, my ass out, an inviting target.

Waiting was intolerable. I wondered if the anticipation of a spanking was worse. No...no, the spanking would be worse, I'm sure.

"Here you are Miss Drake," I heard Imelda say.

"Thank you Imelda. He's getting twenty strokes. Ten for being late and ten for not addressing me properly. Perhaps you'd like to watch and count."

"Oh, yes Miss Drake."

I heard Amanda walk closer to me. I did not know when the first blow would come, so I was tense, gripping the edge of the desk tightly. Nothing. Nothing. I was starting to shake...one can only be tense for so long, but no blow came. I was holding my breath, finally released it, tension draining.


"Ouch," I yelled from the surprise blow. I'd started relaxing.

"One," Imelda called out.

Fuck that hurt!

WHAM! "Two."

"Hmmm," I groaned. She was not playing around. This really fucking hurt!

"Miss Drake, his panties," Imelda said just before the third blow landed making me grunt louder.

"I see that, Imelda." See that? My panties...my panties...what about my panties? Oh, shit, they were Lisa's panties. "Jamie, where did you get those panties?"

"My...my drawer," I lied.

Two rapid swipes immediately followed.

"Four, five," Imelda called out.

"No, only four, Imelda," Amanda said, "she's getting double while she lies."

Oh, fuck, my ass was burning already at four. How much of this could I take?

"Where did you get the panties," Amanda demanded, "I did not buy those for you."

"I...I don't know," I said.

Three more blows, all on the same spot, but me on the verge of tears.

"Five," Imelda said quietly. I sensed a shared pain in her voice.

"Ouch, shit, please...please, they...they are Lisa's, I gasped.

Whack! "Six." Only one blow, but oh how it burned.

"You stole Lisa's panties," Amanda asked incredulously. Two more blows. That made seven officially. I was ready to cry.

"Please," I begged.

"You fucking sissy panty thief." Her next blow was delivered upwards, directly onto my penis.

"Ohhhhhhh," I cried loudly, almost falling over. "Ms. Drake!"

"Eight," Imelda called out.

I could not take twelve of those! I'd pass out. "No, no, it's not like that...I...I didn't steal them...I...Lisa asked me to wear them."

Nothing. I expected another quick succession of blows. Nothing. I dared not turn around, so I gripped the desk tightly, trying not to tremble.

Finally, she spoke. "Lisa asked you to wear panties?"

"Yes, yes," I cried, tears starting to flow.

"When, pray tell, did she do this?"

"Today. Today. We went to her apartment and...and made love. She...she asked me to wear her panties and...and her nightie. She thought I was wearing panties when she caught me because I thought she wanted me to!"

"These are Lisa's panties?" Amanda asked. She was right behind me, stroking my ass with the crop. "These lovely satin panties have covered fair Lisa's ass and pussy?"

"Yes, please Ma'am, I'm telling the truth, I swear!"

The crop left my ass, only to return with another single stinging blow. "Nine," Imelda counted.

"You made love to her dressed in lingerie? She...she saw you as a sissy? I don't believe it, you're lying."

Two hard swats with the crop. "Ten."

"I told you, no lying!"

"No, please, Ms. Drake, I'm not...its true, it really is."

"And you actually made love to her wearing these panties and lingerie?"



"Yes, yes."

"You fucked her, sissy? Don't tell me you did that."

"What? No, no...we made love like..." I paused, tears still flowing, embarrassed to say it.


Two more blows. "Like what? Like what?" Her voice was sharp, harsh, loud.

"Like women," I sobbed.

"Well, well, well. Lisa really does have it in her, doesn't she?"

Bam, the crop stung my ass.


"And did you enlighten her? Did you tell her about your own fascination with panties? How they led to your downfall? Did you tell her about all the pretty things you've worn for me?"

"No, no, god no!"

Another blow, number fourteen.

"No, I suppose not, sissy. You'd probably terrify the poor girl. Better she learn properly, don't you think Imelda?"

The fifteenth blow.

"What...what do you mean, properly?"

I yelped...the sixteenth blow was the hardest yet.

She did not answer. Instead, she deliberately finished my punishment, the final blows resulting in more tears, almost constant.

"Ms. Drake," I cried.

Amanda walked to my side, reversed the crop so the striking portion was in her hand. She took that up to my face.

"Kiss it," she ordered, making me lovingly acknowledge the crop that had tormented my ass. She then moved the crop down my neck, over my outstretched arm, to my chest...lower, to the front of my panties, Lisa's panties, to the erection I had inside them.

"What I mean, sissy, is that Lisa will learn what you are when I properly present her with the sissy I've been training for her."


"Soon, now, don't you agree Imelda."

"Yes, Ms. Drake, I think he almost ready."