Kaaren You Look So Sexy

When I wear my maid uniform my wife always says I look sexy enough to make a dead man hard....

Looks like she might have been right about that!

You Have To Love August - The Pond

There's a pond in the woods where almost no one ever goes. I love this place, I can come here and just listen to the sounds of nature around me. Sometimes when I'm here I feel like I'm the only person in the world and I can be the girl I've always dreamed of being....

Couldn't be Clearer

My wife was doing some reading and I was doing some long ignored chores in the house.
"Kaaren,"" she called, "be a sweetie and bring me an iced tea."
I dropped what I was doing and rushed to get her the tea.
Placing it next to her I asked if there was anything else she needed.
"Well there is one more thing I'd like right now..."
She couldn't have made it any clearer...my other chores would just have to wait!

I Love This Dress

So short but not scandalous! So sexy but not slutty! A perfect dress to wear for an afternoon date with a hot guy, or a late night romp with your best girl.
I love the shoes too!!!

You Have To Love August - Coffee

Getting up early, slipping on some pretty panties I go to make the coffee. My wife still sleeping, snoring so softly, so beautiful. Opening the door I'm greeted by the warm sunshine and the dawn chorus of the birds, singing so sweetly. It doesn't get any better than this!

You'll Never Guess

You'll never guess what I got for you today Sissy....

That's right Sissy, I wanted to get you a present and I thought "What would Kaaren really enjoy?"


I'm glad you like it Sissy, thanks for sharing it with me you're such a generous Sissy

Getting Better But....

My my you have been practicing haven't you Sissy? You are doing so much better in taking him all the way, in fact I think you've just about mastered it. But what are you forgetting Sissy? You're concentrating so hard on your own ability you're forgetting to keep eye contact with your man. A man loves to look into a Sissy's eyes while she take him into her mouth. I guess you'll need more practice!

No Kaaren It's My Turn

The doorbell rang at a most inopportune time! But instead of how I usually handled this my wife told me to relax, she would tip the delivery boy this time!

You Have To Love August - Bright Sunny Mornngs

You wake up and it's a bright sunny day so you slip into something that makes you feel pretty. Poor men with their drab suits and ties and things, they may feel handsome but they'll never feel pretty!!

Which One Is The Sissy?

As the adorable Leeanne always asks, which one is the sissy? Hey wait a minute that guy is cheating!!!!

Not What You Were Expecting?!?!?

Not what you were expecting Kaaren?
I would think that by now this would be far, far more than you were expecting.
I guess another week or two is in order till you understand the way of things around here!!!

You Have To Love August - Me Time

I love taking some Me-Time, my chores are done and the sun is shining. Getting a little sun in my classic lingerie....wonderful!!!

Pull Over Kaaren

"Pull the car over Kaaren, right now." my wife practically shouted.
I swerved hard onto the shoulder and braked while looking at my wife, Her face was flushed and she was breathing heavily, oh my god I thought, what could this be?
"What's the matter sweetheart, do I need to call 911?"
She pulled her shirt open as she pulled my hand to her soaking wet panties.
"I need to cum right now Sissy....now ...now ...NOW...."
I felt her pussy spasm on my fingers and I knew she'd be OK. The sudden pain in my cage was something I'd become accustomed to!

What's Going On?

"What's going on?"
"Shhh Mama and Daddy will hear you."
"What are they doing?"
"Mama's giving Daddy a spanking!"
"Wow really?"
"Shhh I told you they'll hear."
"Why does Daddy keep saying Harder?"
"He must have been really bad and he doesn't think Mama's punishing him enough."
"Shhh you two, they'll hear."
"They won't hear, not with Daddy carrying on like that..."
"Why does he keep asking for more?"
"Why is Mama laughing?"
"Why is Daddy wearing Mama's Sunday dress?"
"Shhh they'll hear, be quiet I want to see what happens next!"

Hoping For Reward

I guess this is how the prospectors felt during the gold rush. You find the trail and follow it hoping to find the thing you desire most in the world!!!

Why Ballet?

When my wife enrolled me in Ballet class I was so embarrassed, not only was I the oldest student I was also treated as just another young girl by the Madame Instructor. I was not trained to portray any of the male roles nor was I allowed to dress any differently from the other young ballerinas

My wife told me it was good for me, I'd learn to be graceful in my movements, and it was good exercise. She said I would become stronger, healthier and more flexible. Well she was definitely right about the flexibility!


Endings and Beginnings

You really must read  How It Began,  Not Always Fun ,  Nothing To See Here,  My First Panties,  A Couple of Firsts,  Caught My First Bra,   My First High School Dance,  Kerri's House, for this post to make sense. This is the tale of my very first sissy experience and for good or ill it was the beginning of my sissy life. Obviously the dialogue is not verbatim but it's as close as I can remember it. The experiences were real as were the young ladies involved. I began this blog intending to tell how I came to be the Sissy girl I am today and this is the final chapter of the beginning, I intend to continue to tell more of my experiences, both good and bad and I hope you, my sweet readers, will come along on the ride.

A week or two went by since my delightful day with Kerri. I was reliving my experiences with her on an almost hourly basis. My tiny little dick was actually kind of sore from all my frantic tugging at it but, oh how I wished she would call and we could play those sexy games together again.
I could still picture her naked body; her tits and pussy were burned into my mind. The taste of her was unforgettable and I yearned to get down on my knees and use my tongue on her to make her cum again.
I was a little confused about wearing her clothes and how it made me feel, I mean I was a boy and I shouldn’t be wearing panties and bras. But I loved it. I loved the feel of the bra wrapped around my chest, the gentle tug of the straps on my shoulders. I loved the soft and sexy panties, cut so much smaller than my briefs and in soft cotton or nylon that gently cupped my little dick making me hard almost constantly.
When she had me wear the skirt and blouse I felt so different, as though I was a different person. I was me, but I was a feminine me, and to tell the truth, a happier me.
So it was with great anticipation that I ran for the phone when my mother called to tell me it was for me.
It wasn’t Kerri, it was Gail.
“Hello Sissy, have you missed me?”
I tried to hide the disappointment in my voice.
“Oh, hi….um yeah sure I’ve missed you. What’s up?”
“What’s up Sissy? Well my friend Kerri says that you and her had a nice talk at the dance while she gave you a tour of the school and so I offered to let her come over and we could have some fun. Be at my house at 11 on Saturday morning, don’t be late Sissy or you might get a spanking.”
My mind was racing; obviously Kerri hadn’t told Gail what had happened between us at the dance or at her house. But what could she be thinking? What was going on?
“Yeah I can do that,” I said, “11 on Saturday…sure no problem…”
“And remember to wear my bra and panties Sissy.”
“C’mon Gail please, I don’t want to do any of that stuff.” I don’t think I sounded convincing, I wasn’t that good an actor.”
“You just be here and be dressed or I could always give your Mom and Dad the lovely photo of you, you look so pretty in it. I’m looking at it right now.”
“OK Gail you know I’ll be there.”
“Great so we’ll see you then Sissy. Bye bye.”
It was hard to reconcile this girl I had grown up with as being my tormenter. I had always thought that we were friends. I had once thought we were more than friends, she had always been the boss in our relationship but now she was turning mean.
I was idly thinking about what might happen at Gail’s house and of course considering another trip to the bathroom to relieve my hard little dick when my mother shouted that there was another phone call for me.
I was very relieved when I heard Kerri say “Hello….Kaaren. How you doing honey?”
“OK I guess,” I answered a little shakily, “I got a call from Gail and….”
“Oh good, you didn’t let on about us hanging out together did you?
“No, I can’t afford to piss her off remember I told you she has that picture of me…”
“I know and that’s what we’re going to take care of on Saturday. When you get there she will probably try to embarrass you in front of me or make you do things to her, or me for that matter. I want you to just go along with it. Try to have fun like we did the other day at my house. At some point I’m going to get her to show me that picture and you can bet when we leave there that that picture will be in my pocket.”
“Wow that would be great, but there’s nothing stopping her from just telling my folks about the…um…underwear and stuff and then I’m just as dead either way.”
“I thought about that and I think you should just deny everything. You could call me and I would back you up, you know, tell your Mom and Dad that we’re together and Gail’s just being jealous and trying to hurt you.”
“I guess that might work, but how are we going to get the picture?”
“It’ll be like Mission Impossible on TV, we’ll play along and when she doesn’t expect it. pow, we got her.” She laughed, it was a wonderful sound.
I was beginning to like the idea, if I could get rid of the picture I figured I could walk away from Gail and into Kerri’s arms.
“Okay, I’m willing to try it, but she already told me to wear her underwear so I guess we’re not going to just talk.”
“Oh sexy Kaaren, what could she do that you haven’t already done with me? If you pretend it’s just us you might actually enjoy it.”
“I doubt it but I’ll try, thanks for trying to help me Kerri, you’re really great.”
“Okay Kaaren, I look forward to seeing you on Saturday. Bye.”
As we hung up a shiver of anticipation went through me and it was off to the bathroom again. Pulling on my little dick I was remembering Kerri’s naked body and thanking my lucky stars that she seemed to really like me.
The days passed and on Saturday morning I slipped into the bathroom and put on the bra and panties under my clothes, I wore looser clothes and hoped they concealed my secret from other eyes. I ran past my Mom and said I would be out with a friend from school and would be home later. I didn’t stop because if my Mom gave me a hug the secret would be out.
“OK,” she called after me, “supper’s at six so be home by then.”
“OK” I replied as the door was swinging shut behind me.
As I rode my bike toward Gail’s house my mind was racing, full of dread and full of excitement. I wondered what was going to happen and what new torments she had in mind. I was looking forward to seeing Kerri again and my little dick was rock hard in the soft yellow panties as I pedaled the few blocks.
When I arrived I put my bike in the driveway and saw a girls bike there that I figured must belong to Kerri. I turned and climbed the steps rang the doorbell, my hand shaking as I did.
Gail opened the door and I could see Kerri standing in the hall behind her. Gail had a big grin on her face.
“Hello Sissy,” she practically shouted the word. “Are you dressed like I told you to?”
So this was the way it was going to be, no build up just going for it right at the start.
“Yes Gail, you know I am.”
She grinned at me and I saw Kerri roll her eyes behind her.
“Show me,” she said, “take that shirt off and let me see the Sissy in his pretty bra. In my pretty bra I should say.”
I turned to close the door behind me but she stopped me.
“I didn’t say anything about closing the door; give me your shirt right now.”
Again you have to remember that I’m naturally submissive by nature and I had already experienced enough to know that she wouldn’t change her mind. She enjoyed humiliating me and in my deepest heart I enjoyed it too!
“Please Gail, someone might see me. Please let me close the door…”
Kerri started to say something but Gail told her to wait.
I slowly unbuttoned the shirt and slipped it off feeling exposed to the world as the soft breeze blew against my skin. The yellow bra seemed even brighter in the sunlight and I was terrified that anyone passing could see me.
“Very good Sissy now give me your pants.”
“Please just let me close the door, I’ll do anything you want…”
“Oh I know you’ll do anything I want already. You’re a wimpy little sissy who let’s girls push him around. Now do as I say or I’ll put you out on the front steps and make you do it out there!”
Over her shoulder I saw Kerri licking her lips and her hand was slowly moving over her breast. I almost came on the spot and I realized it wasn’t going to take very much more to make me cum in my panties.
I knew Gail didn’t bluff so I quickly kicked off my sneakers and taking a deep breath pulled down my pants revealing my pantied bottom to the outside world while the two girls got to see my little dick making the panties stick out and a little wet spot where I had dripped a bit of pre-cum.

Gail pointed at the spot and laughed, “Look Kerri, the poor little sissy is dripping in his pretty panties!”
Kerri stepped up behind Gail and although she was giving me a hungry look she said, “C’mon Gail, let’s take him inside. Close the door. What if one of your Mom’s friends goes by and sees him there like that?”
“Oh all right, I guess you’re right. One of those old neighbors might see him and have a heart attack.”
She pushed the door shut and turned to the stairs, as she had her back to us for a moment Kerri blew a kiss at me as I silently mouthed a “Thank you” to her. We followed Gail up the stairs, me behind her and Kerri behind me. I was painfully aware that she was at eye level with my pantied ass and I found that incredibly embarrassing even though she had seen just about every inch of me the last time we were together.
We entered Gail’s room and she and Kerri sat together on the bed leaving me standing, red-faced, facing them.
Kerri turned to Gail and asked, “Didn’t you two kind of grow up together, why are you being like this with him?”
“Yeah my Mom wanted me to marry him since we were babies. Ha, if she could see him now! Who would want a pathetic Sissy like that?”
Kerri looked at me, “So why do you do this for her? Do you like wearing girls stuff? Do you like when she picks on you? From the look of your panties you seem to be enjoying yourself.”
She was very good at pretending that she didn’t know all about me.
“She makes me do it,” I replied, “It doesn’t matter what I like. If I don’t do what she says she’ll show something to my parents and I’m afraid they’ll throw me out or beat me.”
She turned back to Gail, “You’re forcing him to do this, that’s kind of mean don’t you think. What do you have to show his parents?”
Gail was getting annoyed. This was not going the way she wanted. She walked over to me and slapped me, hard, the sound making Kerri jump and gasp. Tears immediately came to my eyes as my hands came up to protect my face.
“Tell her the story Sissyboy. Tell her how this started. Tell her what you did. Tell her what you stole.”
She slipped behind me and began slapping my ass, softly at first.
“I stole these panties from her drawer,” I explained, “ I don’t know why I did it but she knew I did it and to punish me she made me wear this bra and she took my picture in it and that’s what she has to show my parents. That’s why I have to do what she says.”
She slapped my ass hard enough to make me jump.
Kerri looked at Gail as she spanked my ass. She came over and traced a finger around the bra cups.

“What about the other stuff you told us Gail, you know about, you know, making him, um, you know how you used his face to cum. Can we do that?”
With a final resounding slap she stopped hitting me thank god; my ass felt like it was on fire. She smiled at Kerri and told me to lie on the floor. Gail was wearing a skirt and she stepped up and lowered herself onto my face, settling her soaking wet panties against my mouth and nose. She slowly began to grind against me as her breathing started to get heavier.

“Where’s this picture Gail,” asked Kerri, “I’d like to see it while I wait for my turn to ride.”
Gail laughed and pointed to the bookshelf. “I keep it in my copy of Alice in Wonderland.”
She was breathing really heavy now as her juices began to seep out of her panties onto my chin and lips.
I couldn’t see her but I heard Kerri moving around me. Oh my God, this was going to work! Kerri would get the picture and I can tell Gail to fuck off the next time she calls. She was groaning a little now and her body was starting to shudder and I figured she must be cumming soon. My little dick had pre-cum pretty much streaming now. One touch and I would explode. She was really grinding on my face now and it was actually a little scary because she was hurting me and she was cutting off my air for a little time. Finally as she moaned “Oh God,” she flooded my face with her juices as she came. She rubbed herself for a little while against my chin and I think she had another orgasm before she finally stopped.
As she caught her breath she looked at Kerri who was standing, staring slack-jawed at what she had just seen.
“That’s about all a sissy like him is good for, you want to try Kerri. You should have worn a skirt, I guess you can ride him with your pants on but that won’t be as much fun.”
Kerri looked at her and laughed, “I have a better idea than that.” She said as she opened her pants and began pulling them off.
Gail seemed actually surprised, “Kerri, you’re going to let him see you with no pants on! That’s so crazy. Are you sure? He’ll see almost everything.”
Kerri sat on the edge of the bed in her pretty white panties and told me to come to her on my hands and knees. She grabbed my hair and pushed my head between her legs. Gail was shocked when Kerri pulled her panties aside and pushed my face into her soaking wet pussy!
“Kerri! You’re letting him see you. Oh my god aren’t you embarrassed.”

Kerri was too busy to reply, she was pushing my head into her delicious crotch and I slipped my tongue out to taste her. I loved the taste of her and I knew she was going to cum very quickly. Then I felt the strangest thing. Her foot was near my hard little dripping dick and she started rubbing it with her toes. I began to spurt almost instantly and as I was cumming into my panties she came on my tongue. She pushed me away and lay back on the bed breathing hard. Gail seemed mesmerized by Kerri’s beautiful little pussy, bare and glistening with her juices and my saliva. Kerri was lying back with her eyes closed as I watched Gail lean close and reach a very tentative finger to touch her. Kerri purred as Gail’s finger made contact with her and slid between her glistening lips.

“Mmmm, enough sissy,” she groaned, she thought it was me!
Her eyes opened and she jumped back, “Hey HEY, what the fuck are you doing. Gail you lezzy what the fuck do you think you’re doing???”
Kerri scrambled around her reaching for her pants as I knelt there amazed at what had just happened.
Gail was babbling at her as Kerri pulled her pants on, “I’m sorry, I didn’t mean anything I don’t know why…”
Kerri looked at me and told me to get dressed, and then she looked at Gail and practically spat out her words, “You know a lot of us thought you might be some kind of lezzy but now I know for sure. Once I tell, your life in school is over.”
This was back then, things are different now, but back then what Kerri said was true. We all knew it. Gail was starting to cry. The power in the room had all shifted and now it was Kerri in control, I was pulling my shirt on as I watched them.
“Please Kerri, please don’t tell, please don’t do that to me…I didn’t mean to do it…I don’t know why I did it…please…please…” she was sobbing now.
Kerri looked down at her where she sat on the bed crying, “You’re saying the same thing he did when you caught him with your underwear but you put him through hell. You publicly embarrassed him and you used and abused him…well the shoes on the other foot now. I’m leaving and he’s coming with me. From now on you leave this boy alone, you want me to keep quiet, that’s the price. Oh and I’m taking that damn photo with me too.”
Gail had her head in her hands, crying and nodding, “Okay okay, if you want to take it then take it. Just please don’t tell.”

Kerri grabbed my arm and we walked to the door, as we left I could still hear Gail crying and despite all she had done to me I felt bad for her. We didn’t speak as we got on our bikes. We rode a block or two before we came to the road where we had to split up to go to our homes. Kerri smiled at me.
“I guess that all worked out OK then, we got the picture and we got Gail to agree to leave you alone too.”
“I know I shouldn’t but I feel kinda bad for her, she’s really upset and scared.”
“She’s tough she’ll be fine and just between us,” Kerri leaned in to whisper, “her finger felt fantastic!”
She laughed at the look on my face. Reaching in to her back pocket she handed me the wrinkled photograph and leaned over and kissed my cheek.
“If I was you I’d get some new underwear Kaaren. I’ll call you soon.”
She turned and pedaled away. I watched her go for a while before turning toward home. A chapter in my life had just ended, with a surprise ending, and hopefully a new chapter was beginning with a girl who actually liked me for whom and what I was.

I saw Gail now and again through the years since that afternoon, she had been very unhappy as a teenager and part of that seems to have come from her refusal to admit to herself or anyone else that she was gay. Being gay was tough years ago and it made her life harder than it should have been. We bumped into each other on the street not that long ago and we went for coffee. She told me how sorry she was for the way she had treated me back then and I told her she could make it up to me by paying for the coffee. We had a lovely chat and reminisced about old times and old friends and when it was time to part she hugged me and ran her hand over the bra strap she could feel under my coat. She laughed and smiled and I believe we parted as friends.

You Have To Love August - Making New Friends

As people leave home to go on their August holiday everyone just seems so much friendlier. My wife and I were out for a walk when we met the nicest father and son who were driving their RV around the countryside for a few weeks. My wife and Ray Junior seemed to really hit it off so I tried my best to entertain Ray Senior. I think we all had a lovely afternoon....

I Couldn't Believe It

I went with my girlfriend Sarah, you know Sarah right, yeah anyway she had this friend who was having a party and Sarah said I had to go because her parties were wild. So you know I'm always up for a party and when we got there it was just all women...yeah not a man in sight...I told Sarah that this wasm't really my idea of a party but she told me to have a drink and wait and see,,,
When I got my drink I swear the chick in the maid outfit who served me was a guy!

Yeah I know it was so weird but it was a little hot too, I mean some of the women there were pretty openly grabbing her, I mean him, under his dress! Yeah I know, it was kind of hot.
Then things quiet down and This woman, Sarah says her name is Beverly, introduces us to her husband. He's the maid! Yeah really! Then she has him kneel down and a guy comes in and she makes her husband suck his cock!

I know it's so weird but watching him suck that cock was so hot, I mean I was wet. Anyway in a few minutes here comes another guy. Yeah she made him suck them both. I mean he was like this...

I mean, it was like QMG, I was ready to cum just from watching. I don't know...it was just so hot thinking that guy was wearing a dress and sucking two cocks in front of a roomful of women because his wife wanted him to!

I really liked it and after I had a talk with Beverly about it she told me I should go for it, yeah with Mark, yeah I got the uniform today and if I'm right he'll be serving me as my maid by tomorrow.

Call me tomorrow and maybe if you like it we can order a uniform for your boyfriend too!

Sissy School - Back to Campus

The four Sissies had been inseparable in their first year. They  had bonded as roommates and friends during their introduction to sissy education. They had even enjoyed the summer holiday together.

They were already planning the mischief they would get into when they were summoned to the headmasters office where they all received a sound spanking. The headmaster wanted the four to know he was keeping an eye on them and that this pre-emptive punishment was just the beginning if they got up to anymore of the shenannigans they did last year!

It looked like another interesting year was beginning!

Bridal Shower

As all the girls gathered to wish her well the bride-to-be thought about her future, Obviously her husband's tiny dicklette would never satisfy her so she figured it would be chastity and panties for him. Her tastes ran to something a little more wild and manly so she laughed when they brought out the cake, she knew it would have been far more realistic if it had been chocolate!!!!!

Friday Is Date Night

Sometimes it reminds me of runners, racing for the prize!

Runners take your mark...

Get Ready...


Get Set....

Go!!! And they're off....

 And the winner is.....a three way tie!!!! Three very happy winners!!!

Cooling off afterward with a gentle massage

You Have To Love August - 1933

Sissies frolicking outdoors.....times change, sissies don't!

You Have To Love August - Tan Lines

I might have to hide them sometime soon but for now I think they are like flying my Sissy flag!

You Have To Love August - Summer Showers

A break from the August heat, I love to take a walk in the cool rain.

No Wonder

No wonder you're having such trouble with heels! You're taking such long strides, you have to learn that we girls take shorter steps. I know just the thing to help you with this, remember I only want what's best for you!

Go Read This Right Now!

Sweet Leeanne has posted the next installment of her journey to become the sissy we all know and love.
Go there right now, I mean it, right now! You can't see me but I'm stamping my high heeled sandal when I say that.
Oh I forgot to do the linky thing.....click here,

What are you still doing here? Go read it right now! I'll be here when you get back...

You Have To Love August - Decisions

She had packed a lovely picnic basket and as I sat with her she asked me what was my favorite thing to eat. The easiest decision I've ever had to make!

Kaaren!!!! What The Hell Is This!!!

My wife came into the room and stopped dead in her tracks. Her jaw hung open and she rubbed her eyes as if she couldn't believe what she was seeing.
"Kaaren!!!! What the hell is this? What the hell is going on???"
"Hi honey," I stammered as I started to explain, "You see I was doing my chores like you told me to when the doorbell rang. When I answered it Sister Mary here told me she was collecting for the needy. Well I invited her in and we got to talking and I told her that since you put me in that cage I've been feeling pretty needy too....and ....well one thing lead to another and here you are now,"

OMG Kaaren

OMG Kaaren without the cage I can barely find it!

Sissy In The Kitchen - Fresh Cream

Every Sissy knows what it's like to get a sudden blast of delicious cream in her mouth.