Sissy Boarding School

Today's post is courtesy of Kevin (aka Karen) whose wife just recently officially made him/her a sissy cuckold.  Karen wrote the very first post for this blog at my request.  We had corresponded a few times and when I told her I was thinking of starting a blog and described what themes I wanted to feature, she volunteered to write a short story for me.  I hadn't heard much from her after that until two days ago when she sent me this little vignette, complete with pictures!   I hope you enjoy and I hope Karen continues to contribute when she can.

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    "First year students get the most basic of our rooms.  They're comfortable but simple.  If you get through your freshman year, next year's room will have more amenities" the dean of students said to Karen.  Her name was Ms. Smith.  She had a very pleasant smile but with an authoritative way about her.  "As you would expect gurls in their junior and senior years have the nicest rooms."

    Kevin's mother had decided upon this particular boarding school when she grew tired of catching Kevin rummaging through her things as well as his older sisters too many times.  As a single parent with a full time job, Kevin was becoming a little too much to handle. 

    "Get yourself settled.  Ms. Johnson will be stopping by later to issue you your uniform for class tomorrow and something for you to wear for dinner tonight" Ms. Smith said.  "Any questions?"

    "No ma'am" Karen said.  Ms. Smith just smiled, turned away and walked out of the room.

    The room was certainly not what Karen was used to.  Very tidy, feminine and totally void of any "maleness" like his room back home.  Though Karen had an affinity for girly things his room had all the markings of fourteen year old boy, with pictures of his favorite sports heroes on the wall and other boy things scattered about.  

    Everything in this room seemed so feminine with shades of pink everywhere and all types of little dainty things.  The twin bed in the middle of the room looked comfortable but Karen had a hard time imagining living here for four years.

    Despite its simplicity the room had a lovely view of the school's beautiful grounds.  Karen's room overlooked a lovely flower garden with brick pathways, grassy areas, bird baths and nice looking garden furniture.  It all seemed very peaceful and serene.  In the distance were lots of trees, fields and rolling hills.  "Kevin" was going to miss baseball and other sports.  There didn't seem to be any athletic fields in sight at all.

    Karen walked around the room.  At least there was a private bathroom even though it was pretty small.  She noticed it didn't have a shower and sitting on top of the toilet was a little tent card with the reminder: "Remember to take your seat!"   "There will be no standing to pee.  Ever." she remembered Ms. Smith saying downstairs in the large common living room of the dorm just after Karen kissed her mom goodbye earlier that afternoon.  It was all starting to be a bit overwhelming.

    Karen would make the best of it she thought as she put her small bag of personal belongings on the bed.  New students had received specific instructions of what to bring with them.  Other than the clothes on they wore when they arrived, the only other clothing items they were to bring were three pairs of simple white cotton panties.  Everything else was to be provided by the school.

    As she sat on the bed Karen looked around and decided to take a look inside the closet in the corner of the room.  It was wider that the one she had at home, with two doors that opened away from each other.  She opened the doors to discover the most beautiful collection of feminine finery in pretty pastels that she had ever seen.

    She couldn't believe what she saw.  How in the world was a school like this going to help her break what her mom called "this nasty habit of yours"????  As she ran her hands across the collection of pretty dresses, gowns and petticoats she couldn't help but feel the stirring in her loins...

To be continued.

Karen

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Loving a Sissy

The following was submitted by a reader of mine.  Lots to reflect in so few words.

How many of us can relate? 

 

A Love Story

She loved him. More than he knew, more than he ever imagined, so much that she tried to understand his dreams.

From the beginning, from her first discovery that he had been secretly wearing her panties, it wasn’t easy for Monica to accept that the man she married liked to dress up in women’s clothes. He’d tried to hide it from her, but when she found her panty drawer out of order, some panties stretched and one pair torn, she asked.

 

Tom turned away, embarrassed, but answered honestly, eventually admitting that what he’d done was much like what he did as a boy with his mother’s intimate things. There were tears, from him, not her. She wasn’t angry, she was curious. She listened, tried to understand as her six feet two, former college linebacker husband described how he grew up secretly wishing he was a girl.

Eventually he told her everything, told her how  he believed his wishes would go away if he grew strong muscles, learned how to be tough, and married a beautiful woman like her. But it didn’t work. As it turned out, the more he tried to be a man, the more he wanted to wear women’s clothes. It took several discussions over weeks for everything to unfold, but eventually he told her that he kept it all secret because he worried that she’d stop loving him if she knew the truth.

Monica connected the dots. The life they’d been living suddenly made much more sense. Her husband Tom could be wonderfully caring and sensitive, but he could be unpredictably moody, shift into a dark place, and withdraw from her, bury himself in his work. With this new information, she realized that Tom used work to hide from himself, to bury his desires, to turn away from the femininity he was trying to suppress.     

Monica began to give Tom what she understood he needed. Starting small, she replaced all his male underwear with panties. Just like hers, only in his size. He wept when he saw them. After that, he began coming home earlier from the office. Each birthday, anniversary, and Valentine’s Day, she bought him another item of women’s clothing. First it was babydoll pajamas, then a bra, then nylon stockings. Eventually she allowed him to have a conservative skirt and blouse. Whenever he started becoming moody, she laid out some “girl clothes” for him on their bed and he understood that represented her consent for him to be feminine for an evening or a day. They choose a name for Monica to call him during those times: Nancy.

 

It was their secret. Over the years, their friends commented about what a cute couple they were, how in love they seemed to be, how Tom looked at Monica with such devotion in his eyes, how much he did around the house, how much he did for her. They were constant companions, married for over forty years by the time they both retired.

It was never easy for her. She still saw him as the rugged football player she married, but she came to ignore what underwear he wore, and she knew it made him happy. On the Nancy days, her background in theater helped her see it as harmless play-acting. She understood the power of make-believe, and the power of desire. Most of all she understood the meaning of love.

Tom was incredibly happy and loved Monica very, very much. She was the center of his universe and he did whatever he could to make her happy.

 

My special thanks to the reader who submitted this cute little story.

Love,

sissy terrie 💔

Serving in Anonymity

Today's post comes courtesy of a contributor who insists on remaining anonymous.  So I'll just call her "Tinkebelle" like the maid in her cute and erotic story.  She promised me a follow up so keep your fingers crossed.  The story does leave us kind of wondering.....I hope you enjoy.

                         

"It's going to be a very small party.  Just women from my book club." Florence told Tinkerbelle who was mincing about the home in heels in a french maids uniform doing housework.  "I just thought it would be something you'd enjoy.  It's a good fit for some of the fantasies you've shared with me."

Tinkerbelle was filled with angst and even horror at the thought.  The 21 year old college junior had been secretly visiting Florence for nearly two years now, availing himself of the mature woman's service to crossdressers.  Florence liked the handsome, polite and even cute young man and began affectionately calling him "Tinkerbelle."  Eventually, she invited Tinkebelle to her home so that she could dress in her favorite maids uniform and actully do housework for Florence.

"I'm just scared of being outed.  Absolutely no one knows abut this side of me.  I just can't risk it" she told Florence.  "I hope you understand."

"Of course I do.  The likelihood of you knowing any of them is very small.  You're not even from around here and you've already told me you're going to grad school thousands of miles away from here" Florence countered. 

Florence was right Tinkerbelle thought to herself as she went about dusting the den.  But the risk was too high.  Nevertheless, in spite of the horror of being discovered, Tinkerbelle felt the physical arousal in the white ruffle panties under her short skirt.  Before she could say anything Florence broke the uncomfortable silence.

"I'm also a bit disappointed that you don't seem to think my makeovers would be a sufficient disguise for you.  Are they not good enough?" Florence asked Tinkerbelle.

"Of course they are.  They're beautiful" Tinkerbelle answered in shame.  She never wanted to upset Florence.  Though there was no sex exchanged between the two, there did an exist an intimacy that was difficult to describe.  Not exactly like a mother and son (or daughter) but something close.  Tinkerbelle did have a crush on Florence but tried her best to keep that a secret as well.  

"Well then think about it.  We have some time.  The party isn't for another two weeks" Florence stated rather coldly.  "I have some lingerie in the hamper that needs handwashing.  I don't want you to forget this time."

"Yes Ma'am" Tinkerbelle answered as she finished dusting and made her way to Florence's bedroom closet where she kept a hamper for the lingerie that needed washing.  

To be continued.

A Different Kind of Chastity

The sorority of sissies who are in some form of chastity continues to grow.  Each of our stories are different in some way.  Some of us had a yearning to be locked up by our wives or girlfriends, others not so much.

Today's post comes courtesy of Nancy, a sissy friend of mine who's willing to share her own chastity story.  It's the first in a mini-series of posts I'm sure you'll enjoy.

Welcome Nancy!

xox

sissy terrie 

Kelly & Me

After the kids left home, I thought there would be more time and freedom for sex, but my wife Kelly showed little interest. One evening after a few glasses of wine, I told her how much I loved her, how attracted I was to her, and asked if there was anything I could do to increase her interest in our sex life. She asked if she could be completely honest even if she had things to say that might be hard for me to hear. I was worried but agreed. 

 

This is how the conversation went:

Kelly: “If I am honest with you, will you be honest with me?”

Me: “Yes, of course.”

Kelly: “The last time we had sex, do you think I had an orgasm?”

Me: “Um, no, I don’t think so.”

Kelly: “And the time before that?”

Me: “I don’t remember…”

Kelly: “Well, I do…I did not…nor the time before that, and on and on. It actually has been some time.”

I was having trouble looking at her. I knew things hadn’t gone all that well, but didn’t realize.

Kelly: “Do you remember how long you lasted those last few times?”

Me: “Five, six minutes?”

Kelly: (laughing) “Oh my goodness! That would be wonderful. I checked the clock on the bedside stand. More like one or two minutes.” She sighed, leaned back in here chair. “Go to the garage, get  a tape measure.

I did as she asked. When I returned, she’d removed her top, exposing her black lace bra holding her ample breasts.

Kelly: “Come here. Drop you pants and make it hard.” She put out her hand and I handed her the tape measure. When I was erect, she learned forward and extended the tape measure. “Just over four inches. As difficult as it may be for you to hear this, after three children, your penis is too small for me. I have barely been able to feel it for years.”

I wanted to cry. But I had asked for the truth. My penis shrank in embarrassment.

Kelly: “I’ve been thinking, and I believe I have a solution. The last time I had an orgasm you provided it with your tongue. I am done with your tiny dick. You want to fuck me, from now on, you will provide me with an orgasm every time we make love – with your mouth.”

Me: “But, but, …

Kelly: “But nothing. You have been selfish for a long time. Do you want access to my pussy?

Me: Yes.

Kelly: “Then it will be with your mouth only. Let me ask you this? Have you been masturbating? The truth! Because I believe you have.

Me: (red-faced) Yes.

Kelly: “Well. That stops now.” She hiked up her skirt, spread her legs, pulled aside her panties, and pointed to her crotch. “Get over here and start sucking and I will tell you how we’re going to stop your nasty masturbation.”

 To be continued...

Nancy