Archive for July, 2009

It warms my heart to see my new sissy girl having so much fun with her femininity.

Tuesday, July 28th, 2009 by Mrs Loving

I’m going to teach you how to be playful and seductive with your skirt–teach you how to be a sexy sissy girl.

    “Skirts are very different from wearing pants,” I explain.  “You are more exposed and vulnerable in a skirt.  If you trip or fall down, your skirt could come up and show your panties. That would be very embarrassing.  Of someone could come up to you and pull up your skirt and feel your bottom.”  “Really?,” Monika asks, eyes wide with fear.   “Yes, someone could do that, but mostly I’m going to teach you how to be playful and seductive with your skirt–teach you how to be a sexy sissy girl. Doesn’t that sound like fun?”  “Yes!” she agrees, relieved at the idea of choosing to be sexy, rather than being abused by someone else.  
    Monika excitedly starts playing, swishing her skirts, twirling around, sticking her butt out and pulling up her skirt and petticoat, showing her ruffled panties.  I egg her on, fondling her ass, when she shows it to me, playfully pulling her panties down in back and spanking her ripe little sissy butt cheeks.  She giggles delightedly, her cheeks flushed . It warms my heart to see my new sissy girl having so much fun with her femininity.

Now that’s a very unacceptable pose for a sissy. Put your hands at your side in a more submissive pose

Tuesday, July 28th, 2009 by Mrs Loving

“Your sissy cock is so hard, I don’t know how I’m going to get it into these girly panties”

    I hold the panties at knee-level.  “Step through the leg holes, one at a time,” I instruct, and Monika obeys.  I pull the panties up to her knees,letting her get used to the idea of actually wearing the panties.  “Sissy girls and ladies have very sensitive inner thighs,” I explain, as I stroke her thighs sensually from knee to groin, gliding my hands between her legs, under her balls and softly caressing the underside of her sissy cock.  “That feels good, Mrs. Loving,” she says, watching me intently.  She throws her head back and puts her hands on her hips and moves her legs further apart, as she gets more aroused.
    “Now that’s a very unacceptable pose for a sissy,” I exclaim, slapping her hands down off her hips.  “You look like a cocky little boy!”  “I’m sorry, Mrs. Loving,” she says, waving her arms, at a loss as to what to do with them.  “Put your hands at your side in a more submissive pose,” I order, and she drops her arms immediately, keeping them tightly at her sides.  “That’s better,” I say, noticing her cock getting even harder.  “Your sissy cock is so hard, I don’t know how I’m going to get it into these girly panties,” I tease, as I slide the panties slowly up her thighs and over her ass, letting her cock and balls dangle outside for a moment.  
    “That’s a lot of flesh to get inside a pair of dainty girls panties,” I remark.  She giggles, her cock twitching.  “The proper position for a sissy cock in panties is either straight up, pointing to your belly button, or out one of the leg holes.  We’re going to start with the straight up position.  Now take your hand and grasp your balls and slowly glide your fingers up the underside of your cock, bringing it flat against your belly,” I coach.  Monika follows my directions.  When her cock is flat, I pull the panties up holding her cock in a vertical position. She is so hard that the head of her cock peeks over the top of the waistband. I look her in her eyes and tell her how naughty it looks while I tickle the tip of her sissy cock gently with my fingers, eliciting little gasps from Monika. I stroke my hand over her panty-covered cock, positioning it at a slight angle so that we can modestly cover the cock head while containing her erection. “There, that’s better,” I say, satisfied with the arrangement…

There’s no need to be embarrassed. Masturbation is a perfectly normal activity for girls, boys or sissy boys and girls. Everybody masturbates

Monday, July 27th, 2009 by Mrs Loving

 “I’m going to rub some slippery lotion on your sissy cock. I think you’ll like it.”

    It is time to return to a subject we just touched on earlier in the day–masturbation.  When I questioned her earlier, she  admitted to playing with herself, even hinting at her Momma teaching her how or using Momma’s “cream” to stroke herself.  
    “Your Momma wants to be sure that I teach you how to play with yourself correctly. Do you remember when we talked about that earlier today,” I ask.  Monika nods, eyes downcast.  “There’s no need to be embarrassed.  Masturbation is a perfectly normal activity for girls, boys or sissy boys and girls.  Everybody masturbates,”  I declare enthusiastically.  “They do?” she gulps.  “Yes, indeed, and I’m going to show you how to do it right.  Would you like to learn?,” I ask, slipping my hand under her skirt and feeling her very hard cock straining against her panties.  “How does it make you feel to talk about this,” I ask, already knowing what her response will be.  “Good,” she answers, suppressing a naughty smile.
    “Well, that’s the right attitude.  You should feel good, because it’s lots of fun. You’ll see!”  I sit down on the couch and motion for her to stand in front of me.  “Pull up your skirt.  I want to check your panties.”  She obliges, looking shy.  Her panties are bulging with her rigid cock that is not only peeking over the edge of the waistband of her panties, but it is pulling the panties away from her body.  
    “It looks like these panties are getting uncomfortable,” I say, trying not to laugh.  “I’m going to pull them down to give you some room.”  She giggles as I slip the panties down to her ankles.  “Now sit down here next to me and pull your skirt up.” I say, patting the seat next to me and smiling reassuringly.  
    Monika leans back and pulls up her skirt.  I leave the panties around her ankles, just because it looks so naughty and cute!  “Spread your legs apart to give yourself lots of access to your sissy cock and balls.”  She spreads them.  I lean toward her and put my left leg over her nearest thigh to add a subtle element of restraint.  She squirms.  
    “I’m going to rub some slippery lotion on your sissy cock. I think you’ll like it.”  I say, spreading some slick lube all over her cock and balls.  Her cock twitches and she gasps at the pleasure.  “That feels really good, Mrs. Loving,” she says, beginning to moan.  “I’m so glad it feels good, Monika.  I’m going to start touching you and showing you how to masturbate and then, in awhile, I’ll tell you to take over.”  She shuts her eyes and moans in response.  I begin to glide my hands up and down her cock and all over her balls, faster and slower. She moans and writhes under my touch.  
    “It’s time for you to take over,” I say, placing her right hand on her cock. “OK, she whispers, breathing rapidly.  “Try different strokes, harder, lighter, faster, slower. See what feels good to you.  When it starts to feel almost painfully good, then stroke faster and harder.”  She groans and speeds up her strokes.  I murmur sissy “sweet nothings” in her ear as she masturbates, telling her what a pretty sissy she is, how proud I am of her, what a pretty sissy cock she has, how sexy she looks with her panties around her ankles, how she is much too cute to be a boy, etc……
    “Oh, Mrs. Loving, it’s feeling so good, so so good,” she says, as she grips her cock and strokes faster and faster.  “Ah, ah, oh!” she groans as my sissy girl squirts lots of hot cum out of her cock and her strokes slow down and she squeezes the last drops out.  “What a good sissy girl you are, cumming for me like that,” I praise.  I lift her cum-splattered fingers to her lips.  “Taste your sweet cum for me, Monika. Lick it off your fingers while it’s still warm.”  She looks at me wide-eyed as she hungrily laps up her copious cum.     I look at her lovingly and tell her, “You’ve been a perfect little sissy girl! I’m so proud of you.” She smiles sleepily and nuzzles my neck. I hug her and kiss her gently on her forehead. Marie will be so pleased when I tell her what we accomplished today!

This is the dress your Momma picked out for you. Are you ready to wear it, my budding little sissy girl?

Friday, July 24th, 2009 by Mrs Loving

What a lovely specimen of sissyhood she is becoming! I am thrilled, and I know her mother will be as well

    Finally, I hold up the dress.  It is a little girl party-style dress, satiny peach-colored with a ruffled neckline, puffed sleeves, and a full skirt.  “This is the dress your Momma picked out for you. Are you ready to wear it, my budding little sissy girl?” I ask.  She smiles shyly and nods.  “OK, step into it,” I say, holding the dress out.  She steps into the dress and I arrange the skirt and the petticoat underneath.  “Hold your arms out now,” I say, and Monika slips her hands through the puffed sleeves. I twirl her around and zip up the back.  There is an apron that matches the outfit which I fasten behind her back in a big bow.  
    “And now for the sissy socks and shoes,” I say, motioning her to sit on a nearby chair. I sit on the sofa and tell Monika to rest her foot on my knee.  The socks are stretch lace with a little ruffle around the ankle.  “Have you ever seen such girly socks before?” I exclaim.  “No, Ma’am,” she answers, a little dazed by the relentless onslaught of sissy clothing.  I slip on the socks and the shoes, which are black patent-leather Mary Janes with a strap and buckle.  They fit perfectly.  
    I help her up and encourage her to play with the skirt and petticoat.  She obliges by swishing them around, wiggling her body, occasionally sticking her butt out and flashing her ruffled, peach-colored panties. What a lovely specimen of sissyhood she is becoming! I am thrilled, and I know her mother will be as well.

I pull her close and grab the waistband of her petticoat and panties, showing her engorged sissy cockhead

Thursday, July 23rd, 2009 by Mrs Loving

We’ll just keep that tucked in for now,

    I grab the petticoat from the sofa and tickle Monika with it, gliding it over her bare skin.  “Girl’s clothes are more sensual,” I say.  Monika laughs, clearly loving the feel of this very feminine garment on her skin.  I hold it open for her to step into and pull it up to her waist.  “Move around in it. Play with the petticoat,” I suggest, motioning her to twirl around, which she does with enthusiasm, tossing the petticoat around.  
    “Try some teasing poses,” I say, demonstrating by slowly pulling my skirt up, exposing my stocking tops.  “Look coyly over your shoulder as you swish your skirts around, threatening to expose your panty-covered ass, “ I coach, wiggling my own ass.  She responds playfully, wiggling her butt, looking over her shoulder and throwing her skirt up to show her ass.  
    “Now turn around and face me and toss your skirts around in front, showing the front of your panties,” I direct.  She zestfully obeys, flipping her skirt up and wiggling her hips, showing the crotch of her panties with her hard cock visibly bulging.  I pull her close and grab the waistband of her petticoat and panties, showing her engorged cockhead. “We’ll just keep that tucked in for now,” I grin, caressing her silky cockhead, as she wiggles with pleasure. My sissy girl is beginning to warm up. I am so pleased…..

Luckily, you have pretty budding little sissy breasts. Have you ever worn a bra before?

Wednesday, July 22nd, 2009 by Mrs Loving

The Bra

    “The bra is a uniquely feminine garment,” I say, holding up a slightly padded A-cup white bra.  “Luckily, you have pretty budding little sissy breasts. Have you ever worn a bra before,”  I ask.  “No, Mrs. Loving,” she admits.  I look her in the eyes, and start to unbutton my blouse.  “I’m going to demonstrate some techniques for you,” I say, smiling.  She looks anxious, eyeing my chest, as I unveil my lacy white bra, cupping my small breasts.  “Let me put the bra on you first and then I’ll show you how to adjust it to fit your sissy tits.”  She cooperates, letting me slip the bra over her breasts and hook it in the back. I adjusted the bra straps to fit just right. “Ladies, and sissies need to adjust their undergarments to fit just right, “ I add.  “Now I’ll show you how to give yourself some cleavage,” I say, further unbuttoning my blouse and leaning forward at the waist.  As I do so, I pull up gently on my breasts to give myself a little cleavage.  Monika watches attentively.  “Now let’s see if we can adjust your little titties,” I say, helping Monika to lean forward and pull up on her tiny breasts.  “Well, we’ve got a little cleavage there.  Your breasts may get bigger in time. You look pretty in your bra, how do you feel?” “I feel like I’m starting to look like a girl,” she admits. “That’s a good start,” I say, encouraging her.

Monika stands wearing only the white padded bra. Her cock is hard as she contemplates the panties I am dangling in front of her

Tuesday, July 21st, 2009 by Mrs Loving

“Would you like to wear these panties?” I ask her seductively.  Monika hangs her head down, avoiding my eyes as her cock gets harder, pointing straight at me.  I reach forward and pull her toward me gently by her cock.

    I walk over to the sofa where Monika’s sissy clothes are laid out and pick up the satiny, peach-colored, lacy panties and I hold them up, smiling.  “Panties are a very feminine garment.  These are even more girly than the naughty panties you wore here under your overalls, aren’t they?” I ask.   “Yes, Mrs. Loving, I’ve never worn panties like those before,” she admits.  
    Monika stands before me wearing only the white padded bra.  Her cock is getting hard as she contemplates the panties I am dangling in front of her.  “Would you like to wear these?” I ask seductively.  She hangs her head down, avoiding my eyes as her cock gets harder, pointing straight at me.  I reach forward and pull Monika toward me gently by her cock.  “Remember what I told you about sissy cocks never lying?”  “Yes, Mrs. Loving, but I don’t know what that means.”  “If your cock gets hard when you are being sissified, it means that you are sexually-excited by the idea of feminization, even if it’s ‘forced. Our cocks and pussies and clits don’t lie.  They tell the truth about what turns us on.” I explain. “Does that help you feel better about your sissy training?” I ask.  “I guess so. It makes me feel good, kind of tingly inside, Mrs. Loving,” she admits.  “Well, that’s a good start,” I say, continuing to stroke her cock and pulling her even closer, as I sit down on the sofa in front of her.

Preparing Monika for the Dressing

Tuesday, July 21st, 2009 by Mrs Loving

Let your body respond to the forbidden pleasures of sissy feminization

    Monika stands nude in front of me, casting her eyes down, trying to cover her sissy cock with her hands.  “Don’t cover yourself. You’ll be dressed soon enough, because I’m going to dress you in sissy clothes.  Are you ready?” I ask, as I stand up and put my arms around my nervous little sissy girl-in-training.  I reassure her. “Let me know if you are feeling scared at any point.  I’m here to help you and protect you. I made a promise to your Momma that this would be a strict, challenging and loving experience.”  She seems to relax her body, and I give her a sensual and sexy hug and stroke her cock lightly.  “If we keep this sexy, you will enjoy it more.  Let your body respond to the forbidden pleasures of sissy feminization.  Your sissy cock doesn’t lie, “I remind her as I stroke her hardening cock.  “Does this feel good, Monika?” “Yes, Mrs. Loving,” she admits reluctantly.

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Thursday, July 2nd, 2009 by Mrs Loving

My little sissies are in in a twitter.  Prancing around in their pretty sissy dresses waiting for my next tweet.

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