"Yes, dear, a classic beauty. Now, the hard part, name me a man who is pretty"
"Um...," I stalled.
"Exactly my point. Men are not pretty, they are sexy. Women are pretty. But how did you describe yourself, dear, as sexy or pretty?"
"Pretty," I said.
"And how did you describe yourself," she smiled.
"Pretty."
"Yes, sweetie, pretty. You described yourself as pretty because you think of yourself as..."
"A woman," I answered, blushing.
"Yes. Yes. A woman. You want to be and act like a woman, don't you? Doesn't it feel natural to you?"
"Yes, I suppose it does."
"But, do you want to become one, like I asked before, you know," she made a snipping motion with her fingers.
I recoiled back from her, "No!"
"Oh baby, you are so perfect," she smiled, "because you feel just how I feel, about you, and I love you so much," she hugged me, our breasts touching for the first time, the feeling sending a shudder up my spine.
"Sara, I...," I moaned, moving in to kiss her.
"Sweetie, you're going to mess up your makeup," she laughed, gently pushing me away, "come on, let's go downstairs and get a bite to eat. I want you to walk around, get some practice with your heels, you know." It was not the first time that she would rebuke my sexual advances, and as I later learned, a small part of her greater plan.
We spent the say, two girlfriends, the experienced teaching the less experienced. Walking in heels was a chore, but apparently learnable. What was much more difficult was dealing with fingernails. That was no small chore. It was like I lost my fingers, and had to learn to use them all over again.
At the end of the day, after a day in femininity, we finally retired upstairs to our bedroom. I have to admit, my feet were killing me. Maybe heels were not so easy after all. In fact, my hands hurt a little, from using my fingers in new ways, my shoulders were sore, from the weight of my breasts. My goodness, it was not easy being a woman! Hell, it was not easy pretending to be one.
Sara was amused at that, of course, saying, "Baby, it's about time you learned what we go through for our men, and you have not even done any of the hard stuff men demand yet. Just wait." Her cryptic references scared me sometimes. The "yet" and the "just wait" made me a bit nervous. If I only knew.
I sat in a chair in our room, careful to cross my legs like Sara showed me. That was something I learned in our "deportment lesson" from the afternoon when we had tea. See, ladies drink tea, she said, not coffee. The lesson was humorous and serious. "What's the most guarded part of a woman's body," she asked me?
Naturally, I didn't know. "Her pussy," she answered for me.
"You see, since a pussy is what all those men want to get into, it's our most vulnerable part. It's the part we hide and protect, of course. We may show off our breasts, or legs, even our ass, but we always hide and protect our pussy," she smiled.
"Okay," I had answered her.
"That means you have to learn to protect your pussy and panties from view at all times, dear," she instructed me, frowning at the way I was sitting, legs apart, like a man. "A woman is most vulnerable when seated, so she keeps her knees together at all times. You will have noticed this, I assume sweetie? You will want to copy the actions of a real woman, dear."
"So, the simple lesson is this, from now on, you will keep your knees together like a girl. If you don't cross your legs, keep your thighs gently pressed together. It will help if you spread your feet and turn your toes inwards. This looks very sexy on a woman - maybe less so on a man. But then, you're not a man are you," she laughed quietly, as I crossed my legs.
"Hmm, did you hear that?"
"What?"
"That soft rasp of nylon as you crossed your legs, your stockings rubbing together. That was good, dear, you are almost a natural at that. Do that around a man with a fetish for pretty legs in stockings like yours and he will hit on you faster than you know."
"Are you going to get changed," Sara asked me, snapping be back to the present from our tea this afternoon.
"Change," I asked?
"For bed, silly. Get out of those clothes and into your pj's," she said, pointing to my drawer with my boxers and tee shirts, my normal 'ready for bed' wear.
I frowned, I suppose after a day dressed like this, I could hardly bear to shed my feminine clothes. Oh, things Sara was doing to me.
"What is it," she asked, seeing and sensing my frown. Heck, I hardly knew, or did I?
"Nothing Sara, I just, I suppose I liked dressing like this," I answered, hand on my drawer.
"Well of course you did sweetie," she smiled at me, an expectant smile.
I opened my drawer to get out a tee shirt and boxers. Should what I found have surprised me? I'm sure it does not surprise my dear readers in the least. Of course, it made sense to me later, and even then. No boxers or tee shirts. No. All gone. In their place? I laugh now typing this. Lingerie, of course.
I dug through the drawer, one part of me looking for my male underwear, even saying it, "Sara, where is all my underwear?" but another part of me taking stock of what was left in place. Bras. Panties. Slips. Garter belts. Teddies, and camisoles and tap panties, and nighties and packages of stockings. From different stores, different tags. Sara had been shopping.
Questions flooded my mind, but first to come out, "Sara when did you get all this stuff?"
She grinned at me. Of course. She had been planning for some time. This was not a spur of the moment purchase. What had she been up to? Shit, it almost scared me, what did she have in store?
"Don't you like your pretty things," she asked, a fake pout on her face.
"Yes, I...I love them," I said, my hands resting on them, unable to pull away, "but...where is my stuff?"
"You mean all the underwear for a man you had in your drawer?''
"Yes, yes," I said impatiently.
"Gone," she grinned, "off to the Salvation Army."
"Sara, seriously," I said, anger flashing in my eyes.
"Seriously, dear, gone."
"Dammit, Sara, I need men's...
She cut me off. "Need what? Boxer shorts? Are you going to dress butch on me? Are you going to wear boxers and a tee shirt to cover your breasts? Men's underwear? Are you going to try again to 'be the man' of the house," she mocked me. Her words stung me again, and she knew it. She planned it.
"Sara..."
"Still think you can be that to me."
My next question conceded the point, because I thought not of how I was a man, but rather a practical consideration. A 'real man' would have said, 'fuck you bitch, where is my stuff.' I thought of the nuts and bolts, not what she was doing to me.
"But, what am I going to wear to work?"
She laughed, catching the implication of my question, and said so, "Oh, not 'I'm a man, I need man's clothes' but instead, a practical question, how do I function as a woman? Are you conceding the point, dear? Admitting you are not a man?"
It felt like she slapped me, rhetorically. She was right.
"Don't worry, dear, go look in your closet, all your suits are still there. You obviously have to try look like a man at work, the lingerie is only for under. Don't forget, the breasts come off, the make up comes off, we can do some things to help you fool people at the office."
I was relieved, I know. I did want to play and impersonate a woman, I did not want to be one. Silly me.
Sara directed me to get undressed, shedding all my pretty clothes from the day, and helping me pick out a nightgown for bed. She said that my breasts flowing around at night would feel funny at first. Normally, I suppose, a woman likes to feel that relief at night, but until I became more accustomed to them, I should wear something supportive to bed. A nightie with a built in bra would do the trick. Pink satin to mid thigh, matching pink panties.
She showed me how to take off my makeup, I guess going to sleep with it on was not only a big no no, bad for a woman's face, but slight
ly trampy too. Still in the wig, slipping on the satin of the negligee, hairless, boobs sticking out, I still felt as feminine as I did all day. Shocked, still, at what she did.
Sara also undressed, putting on her own bed clothes, a red satin slip and panties. Finishing out night time routine, we slipped into bed, and carefully, Sara moved over to me, whispered in my ear, "I love you so much."
Her words pushed away any unease I was feeling, and I accepted her kiss, feeling her breasts again push into mine. Turning, kissing her neck, with no thought, my crotch came into contact with hers, and my hard cock, little as it was pushed against her through our panties, I felt the heat of her pussy, and I shuddered and sighed.
"John...John...what are you doing?"
"What. Um...I," I was still pushing at her, pathetic, I know, my cock through both our panties.
She sat up and reached over to turn on the light. "I thought this may be a problem."
"What do you mean," I asked, defensively.
"It's the whole transvestite versus transgender thing. You play a woman, act a woman, but, genetically, there is a part of you, the testosterone, that kicks in when you get excited."
"So," I asked, sexual energy still running through my body, even some confidence.
She knew to slap that down. "You honestly think you can be my man, sissy, with that little thing?"
I immediately lost my libido, shuddered, and shrank, lowered my eyes, afraid to meet her gaze.
Her eyes softened, "Oh, sweetie, it's okay, don't worry, I was afraid this might happen, that with a little sexual energy, your hard wired instincts would come out. Wait there," she jumped out of bed, and left the room.
She came back, carrying a bowl full of ice water, and something small in her hand. "You see, you need to learn to channel your sexual energy into pleasing your partner, not worrying about yourself. We are going to have to work on shifting your focus. Stand up."
I did, and Sara pulled down my panties, exposing my cock, still hard. "Awww, the little cocky is so cute," she said squeezing it and lifting the bowl up to me, pushing my cock and balls down into the cold water.
"Shit, Sara, that's fucking cold," I squealed.
"Hold still," she ordered, squeezing hard on my shaft. Within seconds, I started to shrink again, to hardly nothing, I suppose.
Sara took the plastic thing she had in her other hand, and took my cock in hand. She quickly slipped the plastic around me, as I looked on, puzzled.
"What is that," I asked.
"Shhh." She took a small lock from the package and connected it to the plastic.
"Sara, what the fuck?"
"Hmmm, perfect. This my dear, is a chastity cage."
"What the fuck," I shook my head.
She laughed. "A chastity cage, my love, specifically, the CB3000. This little piece of plastic, locked in place, makes it impossible for this little cock to get hard. You see, I suppose the worst thing would be for you to get confusing messages. I'm trying to bring out your feminine side, but your body may revolt sometimes, and try to assert the little bit of masculinity you have. It does this by sending hormones to your cock, making it hard, and trying to make your mind focus of fucking a woman. It's really a primal reaction. Of course, look at you, what woman would even want that."
"So, what we do is trick your own mind and body. When you are feminized, we make it so your little thing here can't get hard. This will focus your mind on the majority of your mind that is feminine, and teach it to ignore that small masculine part. Without the key, the key I have hidden, you cannot take this off."
"But, Sara, how can I, I mean, how can we, you know, how can I make love to you?"
"Sweetie, like a woman, tender, of course, using your mind, your hands, your mouth. The only way I want you, my love, focusing on your womanhood."
"But..."
"Shhh, sweetie, no butts. You have to focus, dear, focus. If you think like a man, you'll start to grow, and since there is no room to grow, it will hurt. You have to learn to forget about this," she touched the cage, "and focus on your mental love making."
"But, how...how can I, I mean, you know, have an..."
"Trust me, dear, there are other ways women orgasm, I'll teach you how my love," she said, pushing me back onto the bed, rubbing my breasts, forcing her tongue into my mouth.
Of course, I immediately started to grow, and even small, I quickly expanded to fill the space in the cage. Oh, it hurt. It was sore. Oh she was right, I had to focus on something else, something soft and feminine, or I was in for a long long night...
Part 03
"John, John...wake up," Sara's voice called to me across the dance floor. I think I was dancing, but I'm not sure.
"What, Sara, I can't hear you," I yelled across the dance floor, trying to keep eye contact with her as I moved around. "Wait, can we stop for a minute, Sara's calling me," I said to my dance partner. My male dance partner. Looking down, my doppelganger self was wearing a satin gown, the tops of my breasts showing. My partner had no face, but was clearly a man, his arms around my waist, pulling me closer to him, his groin to mine.
I winced in pain, not sure how or why he was hurting me.
"John," Sara called again from across the dance floor, laughing, "wake up before you get hurt."
I opened my eyes and Sara was there, standing over our bed. Confused, I shook my head. "Sara?"
"Having a pleasant dream," she pointed to my groin, where my chemise had ridden up, exposing the chastity cage she put on me last night. My dream, dancing with a man, had caused me to swell, and I was confined by the small chamber. There was no way I could tell her what caused this. The thoughts of the dream floated to and from in my mind, blurry. I know he kissed me. I think that's what did this to me in my cage. No way could I confess that to Sara.
She continued to smile at me. I began to seriously worry that she could read minds.
"Listen honey, you don't want to be late for work, do you? We can't call in sick today, so let's get going."
Reluctantly, I got out of bed, my soft sleeping clothes shimmering on my skin, my groin still tight in the cage she put me in. "John, you are going to have to try to avoid having any nasty dreams unless you want to wake up in pain every morning," she pointed at my crotch.
Every morning? How long did she intend to keep at this? "Sara? Every morning? I thought this was just for last night."
"Oh, sweetie, no, no. That chastity cage is a very important part of your training. You see, one thing we are going to work on is teaching you to orgasm like a woman, and forget about that little thing. There may be times I let you out, but trust me, you will be spending some time in there to start. Of course, you may miss playing with yourself, but I'm certainly not going to miss it," she laughed, a teasing, harsh laugh.
I started shaking. This was too much for me to handle. "Sara, I," I could not finish, and burst into tears, shaking uncontrollably.
"Honey...honey," Sara said, genuine concern evident in her voice, the harshness from moments ago entirely gone.
"Sara, I can't do this," I said, violently pulling the satin chemise over my head, breathing heavily. My hands tore at the fake breasts Sara had glued to my chest.
"Oh dear," she whispered, "Oh, John, please, stop...stop, John, they won't come off without the solvent. Oh, John, I'm sorry, I..."
"Sorry? How can you be sorry," I yelled, "this is your doing! This is what you want! Why are you sorry," I shouted, the anger pouring from me.
She just looked at me, not in defiance, not pity, but tenderly, a concerned wife.
"John, I'm sorry because I love you. I'm sorry because I don't want anything that will hurt you. I'm sorry, because I pushed you too fast."
"Sara, I just...this thing," I said touching the chastity cage, "it..."
"No, John, I understand. I just forgot."
"Forgot? Forgot what," I demanded.
"I forgot the connection, the hardwired connection."
I curled my brow, "the connection?"<
br />
"Of course, love. In my rush to...well...see you as, feminine, to help you, I forgot that as soft and feminine as you may be inside, as far away from a typical man you may be, and as hard as I push that boundary, you are not actually a woman. You may feel it, obviously, and I may try to see you as it, and mold you into that, but you still have testosterone, albeit not as much as a stud, but still, it flows through you."
"Sara, you are not making any sense to me," I answered, tears dried up, but as confused as I could be.
"John, I almost hate to explain it. I'd almost rather just do it, just work on this with you in the dark, but I suppose, I do owe you some explanations, don't I? See, what I forgot was that a man's sexual desire, his erotic pleasures, always start with the cock. Even for a man, like you, barely a man really, everything starts with the cock."
"What?"
Sara went to her dresser and took out a small key, walked over to me while speaking. "John, I'm going to feminize you completely. I'm going to turn you into a much a woman as I can," she said, unlocking the cage, tossing it aside, taking my soft cock into her hands, massaging it, playing with it.
"I'm going to keep you in satin and silk, bras, panties, stockings," she whispered, stroking my growing cock, "I don't want you as a man, I never did, I want you as a woman, my lover, my soft, tender, lesbian, so gentle."
I shuddered again, not from fear and hurt and anger, but from pure pleasure.
"Oh, Sara," I moaned.
"Is that what you want too, lover? Do you want that? Do you want to wear pretty things for me, to submit to me, to be my wife?"
"Yes, Sara, yes," I moaned, thrusting my hips to match the movement of her hands. With every question, she slowed the strokes of my cock.
"You want to wear my lingerie, my pretty bras and panties?"
"Yesssss."
"Hmmm," she smiled, stroking me faster again.
"You want your own things too, your own pretty lingerie."
"Yes....yes."
"Do you want me to date other men," she asked. I wanted to yell no...but I could not. Her hand...her touch...they were pushing me, overriding my brain.
"Do you," she asked, slowing her strokes.
"Yes, yes," I gasped, as she quickly masturbated me again.
A Change in Our Marriage - The Sissy Cuckold Page 7