WELCOME TO MY GALLERY


Let's Have Pizza Tonight

My wife called from work and said she'd be home soon.
"I expect you to be pretty for me Sissy."
Yes my love" I answered. I had already had my bath, shaved and started my makeup.
I think I feel like pizza tonight  so order one now and it should be delivered around the time I get home."
Yes my love I'll order it as soon as we hang up."
"Oh and one more thing Kaaren, remember to tip the delivery man", she said giggling, "you know how much he enjoys delivering for you."
She couldn't see but I was blushing beet red..
"Yes dear, I'll take care of the tip dear."
I heard her laugh and say "I'm sure. See you in a little while my sweet Sissy."
She hung up before I could even say goodbye.
I dialed the local Pizza Parlor and ordered our regular pie, olives and anchovies. When I gave the man the address he told me they would deliver it right away.
The pizza arrived before my wife got home and after I paid for the pie I gave my standard tip.
The only thing that confuses me is why it took two men to deliver one pizza pie?



My wife called from work and said she'd be home soon.
"I expect you to be pretty for me Sissy."
Yes my love" I answered. I had already had my bath, shaved and started my makeup.
I think I feel like pizza tonight  so order one now and it should be delivered around the time I get home."
Yes my love I'll order it as soon as we hang up."
"Oh and one more thing Kaaren, remember to tip the delivery man", she said giggling, "you know how much he enjoys delivering for you."
She couldn't see but I was blushing beet red..
"Yes dear, I'll take care of the tip dear."
I heard her laugh and say "I'm sure. See you in a little while my sweet Sissy."
She hung up before I could even say goodbye.
I dialed the local Pizza Parlor and ordered our regular pie, olives and anchovies. When I gave the man the address he told me they would deliver it right away.
The pizza arrived before my wife got home and after I paid for the pie I gave my standard tip.
The only thing that confuses me is why it took two men to deliver one pizza pie?



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Wedding Night

It was our wedding night and my wife-to-be had planned it all right down to which panties I wore under my tuxedo. We danced and drank and enjoyed our special night until we finally retired to our room where her night became more special.
She looked at me and sighed, "Oh Kaaren, I love you so and just as soon as I'm done here we can cuddle and you can use your amazing tongue for me".
Looking at our wedding album you might wonder where I am in this picture...well...who do you think had the camera!





It was our wedding night and my wife-to-be had planned it all right down to which panties I wore under my tuxedo. We danced and drank and enjoyed our special night until we finally retired to our room where her night became more special.
She looked at me and sighed, "Oh Kaaren, I love you so and just as soon as I'm done here we can cuddle and you can use your amazing tongue for me".
Looking at our wedding album you might wonder where I am in this picture...well...who do you think had the camera!





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Date Night

I love date night, I get to see my beautiful wife at her finest and I get to help make her as alluring as possible for her man. I do this because I know she'll come back to me happy and eager for me to give her my total devotion and a few orgasms too!!!




I love date night, I get to see my beautiful wife at her finest and I get to help make her as alluring as possible for her man. I do this because I know she'll come back to me happy and eager for me to give her my total devotion and a few orgasms too!!!




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You've Been A Very Good Sissy This Week

You've been a very good Sissy this week and I think you've earned a reward so I asked my boyfriend to do me a favor. He has had his eye on you, don't try to deny you've been flirting with him. But I'm in a generous mood Kaaren and I think I'd like to see your eyes when he takes you just like you always look into my eyes when he takes me.




You've been a very good Sissy this week and I think you've earned a reward so I asked my boyfriend to do me a favor. He has had his eye on you, don't try to deny you've been flirting with him. But I'm in a generous mood Kaaren and I think I'd like to see your eyes when he takes you just like you always look into my eyes when he takes me.




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What would you do Sissy?

What would you do sissy? What would you think...my goodness...what would you say if you knew? As much as I love to torture your mind by keeping the identities from you I wonder what you would do?
If I was to pull the blindfold off now and you could see your best childhood friend indulging in his lifelong fantasy.
I invited him and told him he could do what he wanted as long as he didn't give his identity away. I expected him to do something else but after seeing you he confessed to me in whispers that he had always had a crush on you and that you had never known.
I gave his hard cock a squeeze and told him I would love to watch.
Oh Kaaren I am so tempted to pull that blindfold off but my hands are busy inside my panties right now...maybe next time...




What would you do sissy? What would you think...my goodness...what would you say if you knew? As much as I love to torture your mind by keeping the identities from you I wonder what you would do?
If I was to pull the blindfold off now and you could see your best childhood friend indulging in his lifelong fantasy.
I invited him and told him he could do what he wanted as long as he didn't give his identity away. I expected him to do something else but after seeing you he confessed to me in whispers that he had always had a crush on you and that you had never known.
I gave his hard cock a squeeze and told him I would love to watch.
Oh Kaaren I am so tempted to pull that blindfold off but my hands are busy inside my panties right now...maybe next time...




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Always Be Prepared

When I was a Boy Scout the motto was always be prepared and even though they threw me out for that whole girl scout uniform incident I have always remembered to always be prepared.
So thank heavens I was properly groomed and tucked the other day when those nasty boys sneaked up on me.




When I was a Boy Scout the motto was always be prepared and even though they threw me out for that whole girl scout uniform incident I have always remembered to always be prepared.
So thank heavens I was properly groomed and tucked the other day when those nasty boys sneaked up on me.




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I Can't Speak For All You Sissies

I Can't Speak For All You Sissies out there but I first tried this when I was 14 and I nearly broke my neck. I could get tantalizingly close but I was too small and I just couldn't reach. I had to settle for shooting at my mouth from a distance!







I Can't Speak For All You Sissies out there but I first tried this when I was 14 and I nearly broke my neck. I could get tantalizingly close but I was too small and I just couldn't reach. I had to settle for shooting at my mouth from a distance!







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Our Wives Decided

Since we seemed to get along so well online our wives decided that we should spend some quality time together in real life. As they made the final adjustments and discussed their plans for the evening all we could do was look into each others eyes and helplessly feel our bodies reacting to each other.
Laughing as they left they made sure to leave the light on so we could see each other.
"You sissies have a good time, we're going to the club and maybe we'll bring a couple of real men home wouldn't that be fun for all of us!" my wife called out as she pulled the door shut behind her.







Since we seemed to get along so well online our wives decided that we should spend some quality time together in real life. As they made the final adjustments and discussed their plans for the evening all we could do was look into each others eyes and helplessly feel our bodies reacting to each other.
Laughing as they left they made sure to leave the light on so we could see each other.
"You sissies have a good time, we're going to the club and maybe we'll bring a couple of real men home wouldn't that be fun for all of us!" my wife called out as she pulled the door shut behind her.







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I think he might be ready for you dear

I really don't think your boyfriend needs any help from me. He seems ready.
Maybe if I behave really well you would let me watch?
Please? Pretty please?








I really don't think your boyfriend needs any help from me. He seems ready.
Maybe if I behave really well you would let me watch?
Please? Pretty please?








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I said I'd Unlock Your Cage And I Did

I don't think you should blame me if you had your little cummies before you even got close to my pussy. It's up to you to learn to control yourself. So after you've licked up this mess it's back into the cage. I think we'll try 3 months and see if you'll have learned anything by then.



I am a bit disappointed though I''m not surprised. I wonder if my boyfriend is free later?


I don't think you should blame me if you had your little cummies before you even got close to my pussy. It's up to you to learn to control yourself. So after you've licked up this mess it's back into the cage. I think we'll try 3 months and see if you'll have learned anything by then.



I am a bit disappointed though I''m not surprised. I wonder if my boyfriend is free later?


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Kaaren It's Time For Bed

No, not for me silly Sissy, I'll be entertaining my boss for the next few hours. I think I'll put you down for the night and you can clean me up in the morning.
You can suck on this paci all night and maybe, if you're a very good sissy, maybe my boss will let you suck his fantastically manly cock  before he leaves in the morning.
Feel free to listen to us but you are forbidden to watch and the cage will certainly keep you from misbehaving otherwise.
Good night Sissy, Here's your little cuddle bear. Sweet dreams.


No, not for me silly Sissy, I'll be entertaining my boss for the next few hours. I think I'll put you down for the night and you can clean me up in the morning.
You can suck on this paci all night and maybe, if you're a very good sissy, maybe my boss will let you suck his fantastically manly cock  before he leaves in the morning.
Feel free to listen to us but you are forbidden to watch and the cage will certainly keep you from misbehaving otherwise.
Good night Sissy, Here's your little cuddle bear. Sweet dreams.


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Maybe It Doesn't Mean Anything But...

Here we have two teen-aged boys, living in a small town . Based on the clothes I'd say it was during the 50's or early 60's, before the internet, before vcrs, before dvds, before readily available porn mags, before movie nudity, before the entire sexual revolution.
Anyway here we have two teen-aged boys with surging hormones and x-ray vision walking with a hot redhead and what are they doing? Looking under each others clothes!!!
I bet if they looked a little deeper they'd find that they were both wearing prettier panties than their girl friend.



Here we have two teen-aged boys, living in a small town . Based on the clothes I'd say it was during the 50's or early 60's, before the internet, before vcrs, before dvds, before readily available porn mags, before movie nudity, before the entire sexual revolution.
Anyway here we have two teen-aged boys with surging hormones and x-ray vision walking with a hot redhead and what are they doing? Looking under each others clothes!!!
I bet if they looked a little deeper they'd find that they were both wearing prettier panties than their girl friend.



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Memorial Day 2013

People sleep peaceably in their beds at night only because rough men stand ready to do violence on their behalf.- George Orwell

Remember the fallen, the men and women who didn't come back. Remember their families.

So many stories that were never told.


On a lighter note....



People sleep peaceably in their beds at night only because rough men stand ready to do violence on their behalf.- George Orwell

Remember the fallen, the men and women who didn't come back. Remember their families.

So many stories that were never told.


On a lighter note....



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Blindfold

"Do you know why I love to blindfold you Sissy? It's because it forces you to imagine the unimaginable. You don't know if I'm alone or if my friends are here. Or maybe if your friends are here! You don't know if the next hand that touches you will be mine or someone else's. You can't tell if there's a hard cock inches from your mouth or if there's a sweet pussy almost close enough for you to lick, In the dark your mind imagines all of this and more. I know you do because I watch your little clitty twitching as I move around the room. As you strain with all your senses to figure out what's next."

"And you will find out Sissy," she laughed, "when I decide...all in good time!"








"Do you know why I love to blindfold you Sissy? It's because it forces you to imagine the unimaginable. You don't know if I'm alone or if my friends are here. Or maybe if your friends are here! You don't know if the next hand that touches you will be mine or someone else's. You can't tell if there's a hard cock inches from your mouth or if there's a sweet pussy almost close enough for you to lick, In the dark your mind imagines all of this and more. I know you do because I watch your little clitty twitching as I move around the room. As you strain with all your senses to figure out what's next."

"And you will find out Sissy," she laughed, "when I decide...all in good time!"








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Sure We Can Still Have Sex Sissy

After she put me in chastity I became very depressed. I missed the closeness of having sex with my sweet wife although I was so small and fast that she rarely got any enjoyment from it.
"Cheer up Sissy", she said to me, "It'll only be for a couple of weeks till we see if you can learn better control. Besides you know it's your tongue I love best and well...to be honest your little clit can't compare to my lovers glorious hard cock."
"But I miss being with you so much, I know I don't make you cum that way but I love feeling so close to you."

Several days went by when my wife met me at the door with a smile and told me that tonight we could have sex all night long if I wanted. I was ecstatic! She told me to get naked and wait for her in the bedroom she had to get something for me. I know she had hidden the key to my chastity so I left the room to allow her to get it without revealing the hiding spot.
I quickly undressed and waited but when she came into the room it wasn't the key she had at all. She helped me slip it on and then she rode my "big hard dick" all night long!!!





After she put me in chastity I became very depressed. I missed the closeness of having sex with my sweet wife although I was so small and fast that she rarely got any enjoyment from it.
"Cheer up Sissy", she said to me, "It'll only be for a couple of weeks till we see if you can learn better control. Besides you know it's your tongue I love best and well...to be honest your little clit can't compare to my lovers glorious hard cock."
"But I miss being with you so much, I know I don't make you cum that way but I love feeling so close to you."

Several days went by when my wife met me at the door with a smile and told me that tonight we could have sex all night long if I wanted. I was ecstatic! She told me to get naked and wait for her in the bedroom she had to get something for me. I know she had hidden the key to my chastity so I left the room to allow her to get it without revealing the hiding spot.
I quickly undressed and waited but when she came into the room it wasn't the key she had at all. She helped me slip it on and then she rode my "big hard dick" all night long!!!





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Kaaren I'm Going To Be Late

"Kaaren my appointment at the salon is taking a little longer than I expected so I'm going to be a little late. My new Boss is stopping by to discuss my position so keep him entertained until I get there."
"Yes my love," I answered "Is there anything in particular he would like to have?"
"I don't know him very well so be friendly and receptive, I won't be long. Have to go, Bye"
Before I had a chance to change there was a knock at the door. As I let her Boss in I thought of a good way to keep him occupied, and maybe help my wife's career.
"Come in," I said, "let me help you get comfortable".






"Kaaren my appointment at the salon is taking a little longer than I expected so I'm going to be a little late. My new Boss is stopping by to discuss my position so keep him entertained until I get there."
"Yes my love," I answered "Is there anything in particular he would like to have?"
"I don't know him very well so be friendly and receptive, I won't be long. Have to go, Bye"
Before I had a chance to change there was a knock at the door. As I let her Boss in I thought of a good way to keep him occupied, and maybe help my wife's career.
"Come in," I said, "let me help you get comfortable".






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You're in Trouble Now Kaaren

"Kaaren", my wife yelled, "get in here and explain yourself".
With great trepidation I entered  my wife's home office, a room that was off limits to me unless I was cleaning or she summoned me.
As I entered I saw the stack of bills and the banking software on her computer.
She glared at me and motioned for me to kneel which I quickly did.
"Do you have any idea in that sissy head of yours how much money you spent on lingerie and clothes last month?" she snapped at me.
"I'm not really sure my love,"  I nervously answered, "perhaps I got carried away?"
"Perhaps?!?!" she shouted, "With what you spent on lingerie alone I could have paid this months rent. And to make it worse not one piece was for me!"
"I'm sorry my love...I lost track...everything was so pretty..."
"Well you'd better work out a deal with the landlord because we can't pay the rent this month!"
"What do you mean...a deal?"
"Well, I think you can figure out something,"
There was a knock at the door.
"Get going sissy, you make the landlord happy and maybe he'll forget the rent this month."
I went to the door, smiled at him and dropped to my knees.
I did know what to do.



"Kaaren", my wife yelled, "get in here and explain yourself".
With great trepidation I entered  my wife's home office, a room that was off limits to me unless I was cleaning or she summoned me.
As I entered I saw the stack of bills and the banking software on her computer.
She glared at me and motioned for me to kneel which I quickly did.
"Do you have any idea in that sissy head of yours how much money you spent on lingerie and clothes last month?" she snapped at me.
"I'm not really sure my love,"  I nervously answered, "perhaps I got carried away?"
"Perhaps?!?!" she shouted, "With what you spent on lingerie alone I could have paid this months rent. And to make it worse not one piece was for me!"
"I'm sorry my love...I lost track...everything was so pretty..."
"Well you'd better work out a deal with the landlord because we can't pay the rent this month!"
"What do you mean...a deal?"
"Well, I think you can figure out something,"
There was a knock at the door.
"Get going sissy, you make the landlord happy and maybe he'll forget the rent this month."
I went to the door, smiled at him and dropped to my knees.
I did know what to do.



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I Love Redheads With Something Extra

This sweet red-haired beauty stopped me in my tracks.She has a beautiful smile and legs that go on forever. If she has any flaws it would be that she hasn't learned to tuck her clitty back leaving that little telltale bulge that makes my mouth water.





This sweet red-haired beauty stopped me in my tracks.She has a beautiful smile and legs that go on forever. If she has any flaws it would be that she hasn't learned to tuck her clitty back leaving that little telltale bulge that makes my mouth water.





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Hurry Up Kaaren

I've been dripping my boss's cum into these panties all the way home, take them and don't waste a drop. Then I'll need that tongue to freshen me up so get your sissy ass moving!







I've been dripping my boss's cum into these panties all the way home, take them and don't waste a drop. Then I'll need that tongue to freshen me up so get your sissy ass moving!







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You'll Never Really Know

When you return to work on Monday you'll never know which one of the men there was the one I invited to use your sissy mouth, Think about that whenever you're in a group, one of them has used you like the sissy you are!




When you return to work on Monday you'll never know which one of the men there was the one I invited to use your sissy mouth, Think about that whenever you're in a group, one of them has used you like the sissy you are!




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Part of a Sissy's Duties

It is every Sissy's duty to make sure your Mistress' lover is properly aroused and ready to give her what the Sissy can't!


It is every Sissy's duty to make sure your Mistress' lover is properly aroused and ready to give her what the Sissy can't!


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Now Lick It Up Sissy

Lick It Up Sissy, Every...Single...Drop!!!!


Lick It Up Sissy, Every...Single...Drop!!!!


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My First High School Dance And More

About a week or so after Gail made me wear her bra she called and told me that she was taking me to her High Schools dance on Saturday night. She was just under a year older than me and attended a private school whereas I went to the local public school. She was a sophomore and I was a freshman.
I was excited about the idea of going out on a real date with her despite all she had done to me. I have already explained that I was in love with her as only a 14 year old boy could be in love.
She was giving me the details of when and where we would meet, I would come to her house and her Mom would drop us off. It wasn't a formal dance, just a local band playing the hits of the day so I should dress casual but neat. The tickets were three dollars and I would buy our tickets at the door.
I eagerly agreed to all of this then just before she hung up she dropped the bomb on me.
"Make sure you're wearing that pretty bra and panty set you stole from me under your clothes", I heard her laugh, "I'll be checking when you get to my house."
"Aw c'mon Gail please", I pleaded, "don't make me wear that stuff. I told you I was sorry, you already um...you know...punished me".
"Just do it, sissy", she said crisply, "or Mom and Dad get the picture of you wearing my bra with your little bitty peepee sticking out."
I wsa trapped and felt tears welling up, "Please...OK...I'll do it....just don't show that picture to anyone."
"I bet you're crying again", she laughed, "god what a sissy you are! Be here at 6:45 on Saturday. Don't be late. Goodbye"
Before I could even say goodbye I heard her hanging up.
Instead of excitement about the dance I now dreaded what she might do, but I dreaded it all the way to the bathroom where I locked myself in and stroked my little dick until the first spurt hit the opposite wall, it took all of about 15 seconds to cum.
On Saturday I carefully picked out heavier clothes that I thought would conceal what I was wearing. I got instantly hard as I slipped on the panties and then clipped the bra around my belly before pulling it up and slipping my arms through the straps. Using a handful of toilet paper I jerked off for the second or third time that day, I was 14, remember, I could do that then.





I put on a pair of loose jeans and a dark colored collared shirt, I added a sweater over the top of that, feeling confident all was concealed.
I arrived at Gail's house at 6:40 making sure to give myself some extra time so as not to annoy her. She met me at the door with a beautiful smile and a short kiss on the lips.She slipped her arms around me and I felt her trace the bra straps with her fingers.
"Good boy",she said, taking my hand and pulling me into the house.
Her outfit was typical for her, a short gray skirt with a pretty print blouse. She looked incredible.




Her Mom was always nice to me and told us we made a nice couple, I thanked her as behind her back Gail was rolling her eyes. She bundled us into the car, Gail sat in front as I sat alone in the back, for the short drive to her school.
When we arrived Gail assured her mother that we would be fine walking home later and we would be home no later than 11 o'clock. Her mother reluctantly agreed and wishing us a good time drove off down the road.
I had passed by Gail's school a few times but I really didn't know anyone who went there other than her.
We walked to the entrance and I bought our tickets while Gail stepped away to see some of her school friends.
When I turned to look for her I saw her talking to a couple of girls who were looking my way and laughing. I hesitantly made my way toward them.
Slipping her arm around my back and laying her hand directly on the bra band she said, " Oh here he is, I'd like you to meet my friends Lee and Laura".
The girls said "Nice to meet you." before dissolving into giggles.





Gail just smiled, took my hand and led me to another group of girls.
"Hi ladies," she said, "this is the boy I told you about." turning to me she said "This is Christine, Ronnie and Kerri."
They all laughed as they said how nice it was to finally meet me.





Gail took my hand and lead me away after telling the girls we'd see them later. I said something unintelligible provoking further giggles from the girls.
"Why are they all laughing at me Gail? You didn't tell them about my wearing...you know..this stuff did you?"
"You mean that you're a sissy wearing a bra and panty set that you stole from me? Why would I do something like that?" she leaned over and kissed me hard on the lips and slipped her tongue into my mouth as her hand rubbed over the bra outlines through my sweater.
"C'mon," she said, "let's go on in. I want something to drink and I feel like dancing"
We entered the dance as the band started playing some rock song I don't remember. Gail started swinging her hips in time to the music and asked if I would dance with her. I told her I really didn't know how and she shrugged and pulled me onto the dance floor anyway.
I tried to follow her moves as she danced nut I was so nervous that I just made a fool of myself and embarrassed her.
"Fine," she said, "you go stand over there and wait for me and I'll dance with my girlfriends"
I stood near the refreshments as I watched her and her friends dance. I was painfully aware of how tight the panties were as they were holding my little hard-on tight against me thankfully not exposing my arousal to all around me.
As I stood alone I observed that most of the girls were dancing but most of the boys were not. The boys were clustered in groups laughing and yelling and making lewd comments about some of the girls, you know, being teenaged boys.
I didn't know any of them and none looked interested in meeting me so I stood apart and alone watching the girls move so smoothly on the dance floor.
After about a half hour Gail waved to me to come to her. She told me she and her friends were thirsty and would I be a sweetie and bring the three of them some drinks.
Blushing furiously I rushed away to the refreshment table and poured several glasses of punch and carefully carried them back. The other two girls took theirs but Gail told me to take hers back and put more ice in it and I of course hurried to do that.
When I returned with her glass she smiled at the, now laughing, girls and simply said "See, just like I told you".
Turning back to me she said "OK, that's all, I'll call you if I need you"
I heard the laughter as I walked back to where I had been.




After about 10 minutes the girl she had introduced to me as Kerri walked up to me.
Having a good time?" she asked "It looks like Gail's been ignoring you."
"No I'm fine....um it's just that I ....um...don't dance very well"
Before I knew what she was doing she had slipped her arm around me and said, "That's OK, I'm sure you excel in other areas"
I felt her hand slip over the bra and hoped she hadn't felt it. I almost jumped out of my skin as her hand slipped back up and stopped, her finger tracing the bra strap.
"Oh my,"she said with a big grin on her face, "what have we here?"
I tried to stammer something while trying to walk away but she wouldn't let me go.
"You know that Gail has told just about every girl here that she was bringing a sissy boy with her tonight, don't you?"
I couldn't answer as my face was pure red with embarrassment.
"Haven't you noticed all the girls pointing and laughing at you?"
"I um thought it was...something...um I wasn't sure...."
" I'll tell you what you seem nice and I don't think what Gail's doing to you is fair, come with me and we'll find a quiet place and talk, OK?
Not waiting for my answer she took my hand and pulled me behind her toward one of the exit doors.   I turned and saw Gail watching us leave before turning back to her friends, dancing and laughing.
Instead of going outside Kerri led me upstairs into the school. It was a little eerie being in the empty hallways of a school. The band playing downstairs was reduced to a muffled echo.
She led me to a door marked teachers lounge and pushed me inside.
I was confused and didn't know what was going on.
"You know" Kerri said, "all the girls are laughing at the idea that you're wearing girl's undies. I know I felt a bra under that sweater are you wearing panties too? Gail said you would but I can't tell through those jeans".
I was panicked, oh my god I thought, she'd told them all!!! I was the reason they were all laughing....they all knew my shameful secret. I burst into tears and fell to my knees sobbing, I had been completely betrayed by the girl I loved. How could I even show my face to get through the crowd to the door.
Kerri knelt beside me, she was stroking my hair and pulling me toward her. She held my head against her chest as I cried and cried. She made some soothing noise telling me I'd be alright and that I'd done nothing wrong. She kissed my hair a few times slowly moving from my head to my forehead.
"It's alright baby" she cooed at me, "Its alright".
Slowly she slipped down and kissed me lightly on the lips. I was still crying lightly as she kissed me again, this time with a little more pressure and her tongue touched my lips.
Breaking the kiss she looked at me as she wiped the tears away. I was so confused that I didn't know which way was up.
"Better?" she said smiling.
"A little, I guess" I answered through sniffles.
She pulled me tight against her and kissed me with all she had, her body pressing against me as her tongue explored my mouth. Her hands slipped under my sweater and felt my chest through the bra before slipping down quickly under my pants and feeling the soft panties I was wearing.
"The others may laugh", she said looking at me with lust filled eyes "but I think this is just sexy as hell, Can I see what you look like in your undies, please, please."
She got up and moved to the door, realizing it had no lock she pulled me into the bathroom and locked the door.
"Now," she said, "we're alone and no one can see. Please can I see?"
My head was spinning and when I didn't answer she started pulling my sweater over my head.
What the hell I thought, might as well. She seems like the only nice girl here.
So I nodded my head as my face blushed crimson and started to unbutton my shirt slowly revealing the yellow lacy bra.She licked her lips as she reached out and ran her hand over the empty cup. She asked me to turn around so she could see and I slowly turned until I faced her again.
She looked into my eyes and said quietly, "Can I see the rest too? Please? Pretty please?".
Nervously with shaking hands I unbuttoned my jeans and pulled down the zipper, they fell halfway down my legs on their own as they were a little big on me. She took a deep breath and slipped her arms around my waist as she leaned forward and kissed me. I was rock-had in my panties as her hands roamed over my body.
She stepped back and looked me up and down before settling her gaze on the small bulge in the front of the panties,
"You look so pretty and sweet in those undies, I just have to get a closer look"
She dropped to her knees and pulled my panties down so that my little dick was sticking straight out at her. If I hadn't jerked off so many times today I'm sure I would have cum right there.
Reaching out she took my dick between her fingers sending electric shocks through my entire body, then she shocked me by taking my entire dick into her mouth,
It was bliss, hot, wet, her velvet soft tongue licking the underside of my dick and it took about 5 seconds before i moaned and warned her I was going to cum. She kept me in her mouth as I shot my load into her and she swallowed it all, sucking on me for another minute as I shuddered with the aftershock of what had just happened





As she leaned back she took my tiny soft cock between two fingers.
Smiling at me she said, "It's so cute and small, the last guy I did that with almost choked me to death but yours is so nice"
 She got up and kissed me again and then I realized that I could taste myself on her lips. I didn't care. I had gotten a blowjob! An actual blowjob from a pretty girl! I was in heaven.
"We better get back to the dance", she said "Gail will probably be looking for you, why don't you give me your number and maybe we can get together sometime."
We stepped back out into the teachers lounge and she found a pen and paper and wrote down my number.
She helped me straighten my clothes and, taking me by the hand,  we walked back to the dance. I saw Gail was still with her friends and I saw some girls notice me and whisper and laugh but I was above it all.
Kerri squeezed my hand and stepped away. She smiled and mouthed the words "I'll call you" before turning and joining the crowd.
I resumed my waiting position and before long Gail joined me and said she was tired and wanted to go home. She guided me through the crowd to the door with her hand on my back holding the bra band.
I heard the laughter fade as we walked outside.
She slipped her hand down the back of my pants and rubbed my ass through the panties as we walked home in silence. When we got to her door she kissed me and gave me a strange look, I just smiled back at her.
"Go home sissy, I'll call you soon".
As I was walking away she called out to me, "Make sure you hand wash your panties sissy, a girl should always have clean underwear."
Thankfully no one was out but I'm pretty sure she hadn't checked before she had said that, I don't think she would have cared.
When I got home I went straight to the bathroom to slip out of the bra and panties and to take care of another stiff little dick, by now I was bearly shooting anything at all.
I slept well that night.


.
















About a week or so after Gail made me wear her bra she called and told me that she was taking me to her High Schools dance on Saturday night. She was just under a year older than me and attended a private school whereas I went to the local public school. She was a sophomore and I was a freshman.
I was excited about the idea of going out on a real date with her despite all she had done to me. I have already explained that I was in love with her as only a 14 year old boy could be in love.
She was giving me the details of when and where we would meet, I would come to her house and her Mom would drop us off. It wasn't a formal dance, just a local band playing the hits of the day so I should dress casual but neat. The tickets were three dollars and I would buy our tickets at the door.
I eagerly agreed to all of this then just before she hung up she dropped the bomb on me.
"Make sure you're wearing that pretty bra and panty set you stole from me under your clothes", I heard her laugh, "I'll be checking when you get to my house."
"Aw c'mon Gail please", I pleaded, "don't make me wear that stuff. I told you I was sorry, you already um...you know...punished me".
"Just do it, sissy", she said crisply, "or Mom and Dad get the picture of you wearing my bra with your little bitty peepee sticking out."
I wsa trapped and felt tears welling up, "Please...OK...I'll do it....just don't show that picture to anyone."
"I bet you're crying again", she laughed, "god what a sissy you are! Be here at 6:45 on Saturday. Don't be late. Goodbye"
Before I could even say goodbye I heard her hanging up.
Instead of excitement about the dance I now dreaded what she might do, but I dreaded it all the way to the bathroom where I locked myself in and stroked my little dick until the first spurt hit the opposite wall, it took all of about 15 seconds to cum.
On Saturday I carefully picked out heavier clothes that I thought would conceal what I was wearing. I got instantly hard as I slipped on the panties and then clipped the bra around my belly before pulling it up and slipping my arms through the straps. Using a handful of toilet paper I jerked off for the second or third time that day, I was 14, remember, I could do that then.





I put on a pair of loose jeans and a dark colored collared shirt, I added a sweater over the top of that, feeling confident all was concealed.
I arrived at Gail's house at 6:40 making sure to give myself some extra time so as not to annoy her. She met me at the door with a beautiful smile and a short kiss on the lips.She slipped her arms around me and I felt her trace the bra straps with her fingers.
"Good boy",she said, taking my hand and pulling me into the house.
Her outfit was typical for her, a short gray skirt with a pretty print blouse. She looked incredible.




Her Mom was always nice to me and told us we made a nice couple, I thanked her as behind her back Gail was rolling her eyes. She bundled us into the car, Gail sat in front as I sat alone in the back, for the short drive to her school.
When we arrived Gail assured her mother that we would be fine walking home later and we would be home no later than 11 o'clock. Her mother reluctantly agreed and wishing us a good time drove off down the road.
I had passed by Gail's school a few times but I really didn't know anyone who went there other than her.
We walked to the entrance and I bought our tickets while Gail stepped away to see some of her school friends.
When I turned to look for her I saw her talking to a couple of girls who were looking my way and laughing. I hesitantly made my way toward them.
Slipping her arm around my back and laying her hand directly on the bra band she said, " Oh here he is, I'd like you to meet my friends Lee and Laura".
The girls said "Nice to meet you." before dissolving into giggles.





Gail just smiled, took my hand and led me to another group of girls.
"Hi ladies," she said, "this is the boy I told you about." turning to me she said "This is Christine, Ronnie and Kerri."
They all laughed as they said how nice it was to finally meet me.





Gail took my hand and lead me away after telling the girls we'd see them later. I said something unintelligible provoking further giggles from the girls.
"Why are they all laughing at me Gail? You didn't tell them about my wearing...you know..this stuff did you?"
"You mean that you're a sissy wearing a bra and panty set that you stole from me? Why would I do something like that?" she leaned over and kissed me hard on the lips and slipped her tongue into my mouth as her hand rubbed over the bra outlines through my sweater.
"C'mon," she said, "let's go on in. I want something to drink and I feel like dancing"
We entered the dance as the band started playing some rock song I don't remember. Gail started swinging her hips in time to the music and asked if I would dance with her. I told her I really didn't know how and she shrugged and pulled me onto the dance floor anyway.
I tried to follow her moves as she danced nut I was so nervous that I just made a fool of myself and embarrassed her.
"Fine," she said, "you go stand over there and wait for me and I'll dance with my girlfriends"
I stood near the refreshments as I watched her and her friends dance. I was painfully aware of how tight the panties were as they were holding my little hard-on tight against me thankfully not exposing my arousal to all around me.
As I stood alone I observed that most of the girls were dancing but most of the boys were not. The boys were clustered in groups laughing and yelling and making lewd comments about some of the girls, you know, being teenaged boys.
I didn't know any of them and none looked interested in meeting me so I stood apart and alone watching the girls move so smoothly on the dance floor.
After about a half hour Gail waved to me to come to her. She told me she and her friends were thirsty and would I be a sweetie and bring the three of them some drinks.
Blushing furiously I rushed away to the refreshment table and poured several glasses of punch and carefully carried them back. The other two girls took theirs but Gail told me to take hers back and put more ice in it and I of course hurried to do that.
When I returned with her glass she smiled at the, now laughing, girls and simply said "See, just like I told you".
Turning back to me she said "OK, that's all, I'll call you if I need you"
I heard the laughter as I walked back to where I had been.




After about 10 minutes the girl she had introduced to me as Kerri walked up to me.
Having a good time?" she asked "It looks like Gail's been ignoring you."
"No I'm fine....um it's just that I ....um...don't dance very well"
Before I knew what she was doing she had slipped her arm around me and said, "That's OK, I'm sure you excel in other areas"
I felt her hand slip over the bra and hoped she hadn't felt it. I almost jumped out of my skin as her hand slipped back up and stopped, her finger tracing the bra strap.
"Oh my,"she said with a big grin on her face, "what have we here?"
I tried to stammer something while trying to walk away but she wouldn't let me go.
"You know that Gail has told just about every girl here that she was bringing a sissy boy with her tonight, don't you?"
I couldn't answer as my face was pure red with embarrassment.
"Haven't you noticed all the girls pointing and laughing at you?"
"I um thought it was...something...um I wasn't sure...."
" I'll tell you what you seem nice and I don't think what Gail's doing to you is fair, come with me and we'll find a quiet place and talk, OK?
Not waiting for my answer she took my hand and pulled me behind her toward one of the exit doors.   I turned and saw Gail watching us leave before turning back to her friends, dancing and laughing.
Instead of going outside Kerri led me upstairs into the school. It was a little eerie being in the empty hallways of a school. The band playing downstairs was reduced to a muffled echo.
She led me to a door marked teachers lounge and pushed me inside.
I was confused and didn't know what was going on.
"You know" Kerri said, "all the girls are laughing at the idea that you're wearing girl's undies. I know I felt a bra under that sweater are you wearing panties too? Gail said you would but I can't tell through those jeans".
I was panicked, oh my god I thought, she'd told them all!!! I was the reason they were all laughing....they all knew my shameful secret. I burst into tears and fell to my knees sobbing, I had been completely betrayed by the girl I loved. How could I even show my face to get through the crowd to the door.
Kerri knelt beside me, she was stroking my hair and pulling me toward her. She held my head against her chest as I cried and cried. She made some soothing noise telling me I'd be alright and that I'd done nothing wrong. She kissed my hair a few times slowly moving from my head to my forehead.
"It's alright baby" she cooed at me, "Its alright".
Slowly she slipped down and kissed me lightly on the lips. I was still crying lightly as she kissed me again, this time with a little more pressure and her tongue touched my lips.
Breaking the kiss she looked at me as she wiped the tears away. I was so confused that I didn't know which way was up.
"Better?" she said smiling.
"A little, I guess" I answered through sniffles.
She pulled me tight against her and kissed me with all she had, her body pressing against me as her tongue explored my mouth. Her hands slipped under my sweater and felt my chest through the bra before slipping down quickly under my pants and feeling the soft panties I was wearing.
"The others may laugh", she said looking at me with lust filled eyes "but I think this is just sexy as hell, Can I see what you look like in your undies, please, please."
She got up and moved to the door, realizing it had no lock she pulled me into the bathroom and locked the door.
"Now," she said, "we're alone and no one can see. Please can I see?"
My head was spinning and when I didn't answer she started pulling my sweater over my head.
What the hell I thought, might as well. She seems like the only nice girl here.
So I nodded my head as my face blushed crimson and started to unbutton my shirt slowly revealing the yellow lacy bra.She licked her lips as she reached out and ran her hand over the empty cup. She asked me to turn around so she could see and I slowly turned until I faced her again.
She looked into my eyes and said quietly, "Can I see the rest too? Please? Pretty please?".
Nervously with shaking hands I unbuttoned my jeans and pulled down the zipper, they fell halfway down my legs on their own as they were a little big on me. She took a deep breath and slipped her arms around my waist as she leaned forward and kissed me. I was rock-had in my panties as her hands roamed over my body.
She stepped back and looked me up and down before settling her gaze on the small bulge in the front of the panties,
"You look so pretty and sweet in those undies, I just have to get a closer look"
She dropped to her knees and pulled my panties down so that my little dick was sticking straight out at her. If I hadn't jerked off so many times today I'm sure I would have cum right there.
Reaching out she took my dick between her fingers sending electric shocks through my entire body, then she shocked me by taking my entire dick into her mouth,
It was bliss, hot, wet, her velvet soft tongue licking the underside of my dick and it took about 5 seconds before i moaned and warned her I was going to cum. She kept me in her mouth as I shot my load into her and she swallowed it all, sucking on me for another minute as I shuddered with the aftershock of what had just happened





As she leaned back she took my tiny soft cock between two fingers.
Smiling at me she said, "It's so cute and small, the last guy I did that with almost choked me to death but yours is so nice"
 She got up and kissed me again and then I realized that I could taste myself on her lips. I didn't care. I had gotten a blowjob! An actual blowjob from a pretty girl! I was in heaven.
"We better get back to the dance", she said "Gail will probably be looking for you, why don't you give me your number and maybe we can get together sometime."
We stepped back out into the teachers lounge and she found a pen and paper and wrote down my number.
She helped me straighten my clothes and, taking me by the hand,  we walked back to the dance. I saw Gail was still with her friends and I saw some girls notice me and whisper and laugh but I was above it all.
Kerri squeezed my hand and stepped away. She smiled and mouthed the words "I'll call you" before turning and joining the crowd.
I resumed my waiting position and before long Gail joined me and said she was tired and wanted to go home. She guided me through the crowd to the door with her hand on my back holding the bra band.
I heard the laughter fade as we walked outside.
She slipped her hand down the back of my pants and rubbed my ass through the panties as we walked home in silence. When we got to her door she kissed me and gave me a strange look, I just smiled back at her.
"Go home sissy, I'll call you soon".
As I was walking away she called out to me, "Make sure you hand wash your panties sissy, a girl should always have clean underwear."
Thankfully no one was out but I'm pretty sure she hadn't checked before she had said that, I don't think she would have cared.
When I got home I went straight to the bathroom to slip out of the bra and panties and to take care of another stiff little dick, by now I was bearly shooting anything at all.
I slept well that night.


.
















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Fill The Cup Drink It Up - A Sissy CockTail

Recipe for a Sissy CockTail

1 sissy peepee released from 2 months in chastity 
1 old fashioned CockTail glass
1 sissy's hand
1 word of encouragement from Sissy's Mistress
1 stroke maybe 2 at most

Serve to Sissy warm and fresh



Remember to put back into chastity.
Enjoy



Recipe for a Sissy CockTail

1 sissy peepee released from 2 months in chastity 
1 old fashioned CockTail glass
1 sissy's hand
1 word of encouragement from Sissy's Mistress
1 stroke maybe 2 at most

Serve to Sissy warm and fresh



Remember to put back into chastity.
Enjoy



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The Moment Before Her Disappointment

This was her face just before she saw me remove my pants for the first time.
The only time I see this look now is when one of her lovers comes to call.


This was her face just before she saw me remove my pants for the first time.
The only time I see this look now is when one of her lovers comes to call.


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It's about time you got home

Go slip into something pretty you sissy bitch, then set the table for our dinner. After we've eaten you can get on your knees and make sure my lover is nice and hard for me. Go now while I have a taste of a real man's cock before dinner



Go slip into something pretty you sissy bitch, then set the table for our dinner. After we've eaten you can get on your knees and make sure my lover is nice and hard for me. Go now while I have a taste of a real man's cock before dinner



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Look Like An Angel

So sweet and so short, this dress is at once innocent and daringly sexy. Imagine the soft feeling as it swirls around your thighs!
A quick twirl on the dance floor and the whole place would see what's underneath. I guess I'd better wear panties with this!!!
It's another sweet dress I'd love to have in my closet


 Nice heels too!!!! I love open toe shoes.
So sweet and so short, this dress is at once innocent and daringly sexy. Imagine the soft feeling as it swirls around your thighs!
A quick twirl on the dance floor and the whole place would see what's underneath. I guess I'd better wear panties with this!!!
It's another sweet dress I'd love to have in my closet


 Nice heels too!!!! I love open toe shoes.
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I don't know What This Sissy Has Planned

I don't know What This Sissy Has Planned...


But Big Bird seems very worried!!!
I don't know What This Sissy Has Planned...


But Big Bird seems very worried!!!
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My Wife's Face During Sexual Ecstasy

My wife's face showing the pleasure that only being thoroughly fucked by a strong virile man can give her.


I usually see it from across the room if her current boyfriend let's me stay to watch!!!







This is my wife's face later after he leaves and I am cleaning her and soothing her sweet pussy. 


I usually don't see this as my face is buried between her legs.
My wife's face showing the pleasure that only being thoroughly fucked by a strong virile man can give her.


I usually see it from across the room if her current boyfriend let's me stay to watch!!!







This is my wife's face later after he leaves and I am cleaning her and soothing her sweet pussy. 


I usually don't see this as my face is buried between her legs.
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Beautiful Eyes

This sissy has beautiful eyes...and some other talents too!!!



This sissy has beautiful eyes...and some other talents too!!!



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Kaaren, the boss wants to see you right away!!!

"Kaaren" the boss yelled, "Get your sissy ass in here right now. I have something hard I need you to take care of!!!"



"Kaaren" the boss yelled, "Get your sissy ass in here right now. I have something hard I need you to take care of!!!"



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Just stay there and listen close

Remember this the next time you come home late after a stop at the pub with the boys. One of your friends is coming over and I'm going to fuck his brains out while you kneel there in your sissy maids dress. Maybe you won't be so eager to hang around with them after this.
I'm not going to tell you who it is but I will let you eat his cum from my pussy afterwards. So I guess if you suck off all your boyfriends you might figure out who it is from the taste.



Remember this the next time you come home late after a stop at the pub with the boys. One of your friends is coming over and I'm going to fuck his brains out while you kneel there in your sissy maids dress. Maybe you won't be so eager to hang around with them after this.
I'm not going to tell you who it is but I will let you eat his cum from my pussy afterwards. So I guess if you suck off all your boyfriends you might figure out who it is from the taste.



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I Love This Dress

I want this hanging in my closet!!!!


The heels are fantastic too!!!!
I want this hanging in my closet!!!!


The heels are fantastic too!!!!
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It's All In The Eyes

This sissy's eyes tell the whole story, she wants it so badly....


This sissy's eyes tell the whole story, she wants it so badly....


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You don't mind if Krissy Watches Do You?

My boyfriend left quite the load for you Sissy, he took me from behind and it felt like he poured a gallon of cum into my pussy. I've been holding it in until you got here so strip to your panties and get down there and start cleaning it up. My friend Krissy didn't believe me when I told her about you so she's going to stay and watch.
You don't mind do you?


My boyfriend left quite the load for you Sissy, he took me from behind and it felt like he poured a gallon of cum into my pussy. I've been holding it in until you got here so strip to your panties and get down there and start cleaning it up. My friend Krissy didn't believe me when I told her about you so she's going to stay and watch.
You don't mind do you?


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Okay stop your whining

OK quick, get out of those clothes and I'll let you try my slip on Sissy!



OK quick, get out of those clothes and I'll let you try my slip on Sissy!



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I Love Redheads

I Love Redheads, blondes are nice and brunettes are great but I absolutely LOVE redheads.

And a redhead, outside in pretty white panties.....oh my.....

This girl could get me to do anything for her,




I Love Redheads, blondes are nice and brunettes are great but I absolutely LOVE redheads.

And a redhead, outside in pretty white panties.....oh my.....

This girl could get me to do anything for her,




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Panty Obsession

I admit I have an obsession with women's panties, From that first pair I snatched from the laundromat to the dozens and dozens I've had over the years. It's not the fabric or the design that does it for me. I had a girlfriend who bought me men's nylon string bikinis when she suspected my interest, but they did nothing for me and were tucked away behind my boring cotton briefs and forgotten.
So if it's not the fabric or the style then what is it?



I think, for me, it's that they represent the ultimate in femininity. They are the doorway one must pass to reach that which we desire the most and so they also become my desire.To worship them is to bow to the superior woman, to wear them is to put aside my male ego and embrace the feminine side of me.

It was through my love of panties that Sissy Kaaren was born. If you've read my previous posts about my relationship with Gail you'd realize that none of that would have happened if Sissy Kaaren wasn't inside me She was inside me all my life and when I let her loose she showed me a new way of life. A softer, sweeter, prettier way.

Gee that sounded kind of schizo there, but I'm sure you other sissies know what I mean.

From that panty obsession I began to wear other feminine clothes and each time I tried something new it felt right. I wondered for a while if I was a Transexual but I have no desire to change sex. I found I liked being a sissy, I enjoyed being submissive to women and I liked the humiliation of being a man dressed in pretty women's clothes.

My eyes opened and with my panties on, I saw things in a new way. I wanted to try things I dared not share with anyone. I had desires I hadn't let myself feel let alone act on.

As my teen years progressed I understood more and more about who and what I was, I was a Sissy and I still am.

More of the stories of my life to come. I hope you will all stay with me for the ride.







I admit I have an obsession with women's panties, From that first pair I snatched from the laundromat to the dozens and dozens I've had over the years. It's not the fabric or the design that does it for me. I had a girlfriend who bought me men's nylon string bikinis when she suspected my interest, but they did nothing for me and were tucked away behind my boring cotton briefs and forgotten.
So if it's not the fabric or the style then what is it?



I think, for me, it's that they represent the ultimate in femininity. They are the doorway one must pass to reach that which we desire the most and so they also become my desire.To worship them is to bow to the superior woman, to wear them is to put aside my male ego and embrace the feminine side of me.

It was through my love of panties that Sissy Kaaren was born. If you've read my previous posts about my relationship with Gail you'd realize that none of that would have happened if Sissy Kaaren wasn't inside me She was inside me all my life and when I let her loose she showed me a new way of life. A softer, sweeter, prettier way.

Gee that sounded kind of schizo there, but I'm sure you other sissies know what I mean.

From that panty obsession I began to wear other feminine clothes and each time I tried something new it felt right. I wondered for a while if I was a Transexual but I have no desire to change sex. I found I liked being a sissy, I enjoyed being submissive to women and I liked the humiliation of being a man dressed in pretty women's clothes.

My eyes opened and with my panties on, I saw things in a new way. I wanted to try things I dared not share with anyone. I had desires I hadn't let myself feel let alone act on.

As my teen years progressed I understood more and more about who and what I was, I was a Sissy and I still am.

More of the stories of my life to come. I hope you will all stay with me for the ride.







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Caught - My First Bra

Several days went by after my unbelievable encounter with my friend Gail. I was jerking my little dick so often locked in the bathroom that my mother started talking about taking me to the doctor thinking I was having stomach problem. It was the only door in the house I could lock.
Every rime the phone rang I hoped it would be her inviting me back for more games. Although I always left there with a hard little dick I loved the attention she gave me and I was, I guess even then, a natural submissive.
In the meantime I was wearing her yellow panties for at least a few minutes every day and although I tried not to stain them during my jerk-off marathons I did get some pre-cum spots on them.
Finally on Saturday morning she called and told me to come over at 11, her family was out and she really wanted to see me.
I was beside myself with excitement, I had 45 minutes till I had to be there and she was just a few minutes away so I was back in the bathroom with her panties furiously sliding my finger and thumb up and down my little dick until I spurted so hard it hit the wall 6 feet away from me. Hey, I was 14, I could do that then.
I tucked her panties back into my hiding spot and dressed, told my mother I was going out and set off to Gail's house.
When she answered the door there was a different feeling from the other day. She seemed annoyed as she took my hand and led me through the house to her bedroom. She told me to wait there while she attended to something in the kitchen.
I sat on her bed, thinking of lying here with her rubbing her pantied pussy on my face and was instantly hard again. Like I said before, I was 14 I could do that then. I looked at her dresser and noticed some underwear sitting on top. I so wanted to reach over and feel the soft fabric but I had no idea how long she would be.



After a minute or two she came back into the room and started fussing with the bras and panties, her back to me as she put them in her drawer.
"Do you like looking at my underwear?" she asked while holding up a pretty pair of black panties, still not looking at me.
"Um I guess so," I kind of stammered.
Trying to recover and sound cool I added "Especially if you're wearing them."
"Anything else about my underwear interest you?" she still wasn't looking at me.
"Uh, no I don't think so..." my voice was actually cracking as I was starting to fear where this was going.
She whipped around at me with a scowl on her face.
Really?" she hissed at me, "Because the other day just before you got here I had folded my favorite bra and panties and put them in this drawer. After you left and I got out of the shower I opened the drawer to put on my favorite set of underwear and, you know what, the panties were gone. So you're some kind of pervert panty thief now? You would steal from me after we were so close? After all we did? Well...you took them admit it to me right now!"
I tried to deny but I felt my face flushing, giving me away.
"No Gail, I didn't take..."
I never got to finish the sentence. She smacked my face. Hard.
"Don't lie to me you sick little pervert" she yelled, "maybe I'll just call your mother and father and let them deal with you."
She knew me so well, she knew about the beating I had gotten years ago and she knew why.
"Please Gail," I had tears starting to form as I rubbed my stinging cheek.
"I'm sorry. Yes I took your underwear. I'm sorry," I said starting to cry, "I don't know why I did it I'll give them back. Please don't tell anyone. They'll kill me, I'm sorry I'm sorry." I was sobbing now.
She waited until I had calmed a bit then asked, "So what did you do with my underwear, pervert, tell me the truth or I make that call right now. Do you jerk your tiny little peepee into them?
"No" I said "no Gail I don't do that" It was technically the truth.
"Well then the only other answer is that you must like to wear them. Is that it pervert? You like to wear girls underwear? You like to put on soft pretty panties?"
When I didn't answer she smirked at me.
"So that's it" she laughed, I bet you look so pretty in your pretty panties...MY pretty panties"
Again I said nothing, blushing furiously yet my dick was rock hard.
"Get up you sissy" she ordered, "strip, I want you naked in 1 minute or I call your Mom"
I didn't know what to do but something deep inside me compelled me to do exactly as she said and I tore my clothes off and stood before her naked covering my little hard-on with my hands.
""Hands on your head" she ordered and I complied instantly.
She stepped forward and grabbed me, laughing she said, "There's really not that much here, you're probably closer to being a girl than you are to being a man"
She directed me to lie down on my stomach on the bed and I felt her sit next to me. She rubbed a hand over my ass as she said" You really do need to be punished for stealing you know"
She began spanking me, lightly at first and then harder and harder till I was crying and pleading with her to stop.


Tellingly I made no attempt to get up or physically stop her, it didn't even occur to me.
"Now your ass is a nice girly pink" she laughed.
She made me get up and as I rubbed my poor stinging butt she opened her panty drawer once again. This time she pulled out a very pretty yellow bra and held it up for me to see.


"This matches the panties you stole from me so you might as well have the entire set. Hold your arms out right now."
Wide-eyed I looked at the bra and pleaded, "Please Gail don't make me wear a bra, please."
"Arms out," she said "or I make the call".
Reluctantly I put my arms out and she pushed the bra up onto my shoulders. Stepping behind me she fastened the hooks. As she adjusted the straps I realized that this was just as good as wearing panties, the soft material touching my chest, the unfamiliar tightness and feel of the straps. I instantly knew there would be more bras in my future.
"Now just stand there a moment", in one move she pulled a camera from a shelf and told me to smile. There were no digital cameras then but there were Polaroids and in a flash she had a photo of my shame.
As the photo developed she told me to turn around so she could see how my pink ass went with my yellow bra. I turned away but could see her reflection in a small mirror on the dresser. 
She put the picture on the shelf next to the camera and slipped her pants down, she slid her hand into her panties and was rubbing herself quickly. 



Between the spanking, bra, domination, fear and now this I was dripping pre-cum and my little dick was actually close to bursting, it would probably only take a touch at this point. I watched her as she arched her back and obviously had an orgasm. What she did next nearly made me faint from lust as she took her juice covered fingers and sucked them clean of her own juices.
Finally she said, "Alright sissy I'm sick of looking at you. Put on your clothes and get out of here."
When she saw me reaching back to try and unhook the bra she stopped me. "That stays on until you get home sissy don't you dare try to take it off before you get there."
Again, I didn't even think of disobeying her and when I dressed the bra was pretty obvious under my light shirt.
She took my hand and walked me to the door, pushing me out she laughed.
"I suggest you don't stop to see any of your boyfriends sissy, your bra is showing through your shirt.. I'll call you soon.
I could still hear her laughing as I hunched over and ran for home praying I didn't meet anyone on the way.




















Several days went by after my unbelievable encounter with my friend Gail. I was jerking my little dick so often locked in the bathroom that my mother started talking about taking me to the doctor thinking I was having stomach problem. It was the only door in the house I could lock.
Every rime the phone rang I hoped it would be her inviting me back for more games. Although I always left there with a hard little dick I loved the attention she gave me and I was, I guess even then, a natural submissive.
In the meantime I was wearing her yellow panties for at least a few minutes every day and although I tried not to stain them during my jerk-off marathons I did get some pre-cum spots on them.
Finally on Saturday morning she called and told me to come over at 11, her family was out and she really wanted to see me.
I was beside myself with excitement, I had 45 minutes till I had to be there and she was just a few minutes away so I was back in the bathroom with her panties furiously sliding my finger and thumb up and down my little dick until I spurted so hard it hit the wall 6 feet away from me. Hey, I was 14, I could do that then.
I tucked her panties back into my hiding spot and dressed, told my mother I was going out and set off to Gail's house.
When she answered the door there was a different feeling from the other day. She seemed annoyed as she took my hand and led me through the house to her bedroom. She told me to wait there while she attended to something in the kitchen.
I sat on her bed, thinking of lying here with her rubbing her pantied pussy on my face and was instantly hard again. Like I said before, I was 14 I could do that then. I looked at her dresser and noticed some underwear sitting on top. I so wanted to reach over and feel the soft fabric but I had no idea how long she would be.



After a minute or two she came back into the room and started fussing with the bras and panties, her back to me as she put them in her drawer.
"Do you like looking at my underwear?" she asked while holding up a pretty pair of black panties, still not looking at me.
"Um I guess so," I kind of stammered.
Trying to recover and sound cool I added "Especially if you're wearing them."
"Anything else about my underwear interest you?" she still wasn't looking at me.
"Uh, no I don't think so..." my voice was actually cracking as I was starting to fear where this was going.
She whipped around at me with a scowl on her face.
Really?" she hissed at me, "Because the other day just before you got here I had folded my favorite bra and panties and put them in this drawer. After you left and I got out of the shower I opened the drawer to put on my favorite set of underwear and, you know what, the panties were gone. So you're some kind of pervert panty thief now? You would steal from me after we were so close? After all we did? Well...you took them admit it to me right now!"
I tried to deny but I felt my face flushing, giving me away.
"No Gail, I didn't take..."
I never got to finish the sentence. She smacked my face. Hard.
"Don't lie to me you sick little pervert" she yelled, "maybe I'll just call your mother and father and let them deal with you."
She knew me so well, she knew about the beating I had gotten years ago and she knew why.
"Please Gail," I had tears starting to form as I rubbed my stinging cheek.
"I'm sorry. Yes I took your underwear. I'm sorry," I said starting to cry, "I don't know why I did it I'll give them back. Please don't tell anyone. They'll kill me, I'm sorry I'm sorry." I was sobbing now.
She waited until I had calmed a bit then asked, "So what did you do with my underwear, pervert, tell me the truth or I make that call right now. Do you jerk your tiny little peepee into them?
"No" I said "no Gail I don't do that" It was technically the truth.
"Well then the only other answer is that you must like to wear them. Is that it pervert? You like to wear girls underwear? You like to put on soft pretty panties?"
When I didn't answer she smirked at me.
"So that's it" she laughed, I bet you look so pretty in your pretty panties...MY pretty panties"
Again I said nothing, blushing furiously yet my dick was rock hard.
"Get up you sissy" she ordered, "strip, I want you naked in 1 minute or I call your Mom"
I didn't know what to do but something deep inside me compelled me to do exactly as she said and I tore my clothes off and stood before her naked covering my little hard-on with my hands.
""Hands on your head" she ordered and I complied instantly.
She stepped forward and grabbed me, laughing she said, "There's really not that much here, you're probably closer to being a girl than you are to being a man"
She directed me to lie down on my stomach on the bed and I felt her sit next to me. She rubbed a hand over my ass as she said" You really do need to be punished for stealing you know"
She began spanking me, lightly at first and then harder and harder till I was crying and pleading with her to stop.


Tellingly I made no attempt to get up or physically stop her, it didn't even occur to me.
"Now your ass is a nice girly pink" she laughed.
She made me get up and as I rubbed my poor stinging butt she opened her panty drawer once again. This time she pulled out a very pretty yellow bra and held it up for me to see.


"This matches the panties you stole from me so you might as well have the entire set. Hold your arms out right now."
Wide-eyed I looked at the bra and pleaded, "Please Gail don't make me wear a bra, please."
"Arms out," she said "or I make the call".
Reluctantly I put my arms out and she pushed the bra up onto my shoulders. Stepping behind me she fastened the hooks. As she adjusted the straps I realized that this was just as good as wearing panties, the soft material touching my chest, the unfamiliar tightness and feel of the straps. I instantly knew there would be more bras in my future.
"Now just stand there a moment", in one move she pulled a camera from a shelf and told me to smile. There were no digital cameras then but there were Polaroids and in a flash she had a photo of my shame.
As the photo developed she told me to turn around so she could see how my pink ass went with my yellow bra. I turned away but could see her reflection in a small mirror on the dresser. 
She put the picture on the shelf next to the camera and slipped her pants down, she slid her hand into her panties and was rubbing herself quickly. 



Between the spanking, bra, domination, fear and now this I was dripping pre-cum and my little dick was actually close to bursting, it would probably only take a touch at this point. I watched her as she arched her back and obviously had an orgasm. What she did next nearly made me faint from lust as she took her juice covered fingers and sucked them clean of her own juices.
Finally she said, "Alright sissy I'm sick of looking at you. Put on your clothes and get out of here."
When she saw me reaching back to try and unhook the bra she stopped me. "That stays on until you get home sissy don't you dare try to take it off before you get there."
Again, I didn't even think of disobeying her and when I dressed the bra was pretty obvious under my light shirt.
She took my hand and walked me to the door, pushing me out she laughed.
"I suggest you don't stop to see any of your boyfriends sissy, your bra is showing through your shirt.. I'll call you soon.
I could still hear her laughing as I hunched over and ran for home praying I didn't meet anyone on the way.




















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Mutiny aboard The Raging Impaler!!!



It was a soft moonlit night and a steady breeze filled the sails of the infamous pirate ship "The Raging Impaler". All was quiet as the third mate crept quietly across the deck, keeping to the shadows as best he could. He was moving slowly aft toward the Captains cabin when a voice from the crows nest challenged him.
"Who be that hiding in the shadows down there, come out and name yourself".
The mate stepped into the moonlight and harshly whispered, "It's me Third Mate Dover, keep your voice down or you'll wake the Cap'n and you know what that would mean?"
The chastened crewman lowering his voice to a whisper answered back, "Aye sir, it's just I been a little uneasy tonight, a feelin' that things are awry".
"Never mind your feelings, just keep to your lookout."
Aye aye sir"
The mate, checking over his shoulder to see if anyone from the crew quarters had been roused by this exchange resumed making his quiet and  stealthy way to the Captains door. Normally waking the captain was unheard of but tonight he had to get to him and time was running out.
Without knocking he opened the door and crept into the cabin of the infamous pirate Captain Woodrow Bonner, Old Hardwood his crew called him. Lighting a lamp the mate turned to the bed and found the captain fully awake and pointing a pistol straight at him, His eyes grew large as he saw the pistol first and then noted that the Captain slept nude. His eyes flicked between the pistol and the captains' manhood which gave new meaning to his crew given name.
"What are you after boy", growled the captain rising to his feet, "what do you want to tell me before I have you keelhauled for daring to interrupt my sleep?"
Trying desperately to keep his eyes on the enraged Captains face The mate gasped out, "It's a mutiny Cap'n, the crew is turned against you! Most, if not all the officers too!! They'll be coming soon."
"Arrrgh, a mutiny is it?" the captain raged, "and who is the leader of this mutiny?"
"It was that sissy we took aboard Cap'n, she's turned the crew against you. I knew we should have had her walk the plank when we found she warn't a real woman. Hurry Cap'n let me help you dress so that we can flee in one of the boats!"
I can't believe it's possible", the captain said as he stepped into the pants the mate held open for him, "are there any others still loyal Dover?"
"Just me Cap'n." he said as he adjusted the captains belt around his hips.
"And why just you young Ben, when all the rest have turned?"
"I'll always be loyal to you my captain." said the mate as he buttoned the captains shirt.
Suddenly with a crash the door flew open and the sissy stood there looking no longer like a frightened prisoner. Over her shoulder stood the rest of the Impaler crew.





"Captain" said the sissy, "your ship and crew are mine. Surrender and I'll let you live, give you and your toady here some food and water and one of the small boats. Fight me and we'll take you, tie you over the railing and make you the receptacle of the entire crews filthy seed before you walk the plank What's it to be then?"

"Aye lass,I have no wish to die or to be used in such a manner. I accept your terms."

The crew let loose a rousing cheer as they lowered the boat with Old Hardwood and third mate Ben Dover over the side. "Three cheers for Cap'n Kaaren, Three cheers for Cap'n Kaaren!!!"

As they rowed away from the ship and the sound of the cheering men the Captain looked at his mate
"How did she do it" he wondered, "how did she turn my crew against me?"

"Well Cap'n", said the mate, "I believe she offered them something that you didn't"





There might be further episodes of the adventures of Sissy Cap'n Kaaren aboard The Raging Impaler as this has always been a favorite fantasy of mine. Feedback is always welcome.













It was a soft moonlit night and a steady breeze filled the sails of the infamous pirate ship "The Raging Impaler". All was quiet as the third mate crept quietly across the deck, keeping to the shadows as best he could. He was moving slowly aft toward the Captains cabin when a voice from the crows nest challenged him.
"Who be that hiding in the shadows down there, come out and name yourself".
The mate stepped into the moonlight and harshly whispered, "It's me Third Mate Dover, keep your voice down or you'll wake the Cap'n and you know what that would mean?"
The chastened crewman lowering his voice to a whisper answered back, "Aye sir, it's just I been a little uneasy tonight, a feelin' that things are awry".
"Never mind your feelings, just keep to your lookout."
Aye aye sir"
The mate, checking over his shoulder to see if anyone from the crew quarters had been roused by this exchange resumed making his quiet and  stealthy way to the Captains door. Normally waking the captain was unheard of but tonight he had to get to him and time was running out.
Without knocking he opened the door and crept into the cabin of the infamous pirate Captain Woodrow Bonner, Old Hardwood his crew called him. Lighting a lamp the mate turned to the bed and found the captain fully awake and pointing a pistol straight at him, His eyes grew large as he saw the pistol first and then noted that the Captain slept nude. His eyes flicked between the pistol and the captains' manhood which gave new meaning to his crew given name.
"What are you after boy", growled the captain rising to his feet, "what do you want to tell me before I have you keelhauled for daring to interrupt my sleep?"
Trying desperately to keep his eyes on the enraged Captains face The mate gasped out, "It's a mutiny Cap'n, the crew is turned against you! Most, if not all the officers too!! They'll be coming soon."
"Arrrgh, a mutiny is it?" the captain raged, "and who is the leader of this mutiny?"
"It was that sissy we took aboard Cap'n, she's turned the crew against you. I knew we should have had her walk the plank when we found she warn't a real woman. Hurry Cap'n let me help you dress so that we can flee in one of the boats!"
I can't believe it's possible", the captain said as he stepped into the pants the mate held open for him, "are there any others still loyal Dover?"
"Just me Cap'n." he said as he adjusted the captains belt around his hips.
"And why just you young Ben, when all the rest have turned?"
"I'll always be loyal to you my captain." said the mate as he buttoned the captains shirt.
Suddenly with a crash the door flew open and the sissy stood there looking no longer like a frightened prisoner. Over her shoulder stood the rest of the Impaler crew.





"Captain" said the sissy, "your ship and crew are mine. Surrender and I'll let you live, give you and your toady here some food and water and one of the small boats. Fight me and we'll take you, tie you over the railing and make you the receptacle of the entire crews filthy seed before you walk the plank What's it to be then?"

"Aye lass,I have no wish to die or to be used in such a manner. I accept your terms."

The crew let loose a rousing cheer as they lowered the boat with Old Hardwood and third mate Ben Dover over the side. "Three cheers for Cap'n Kaaren, Three cheers for Cap'n Kaaren!!!"

As they rowed away from the ship and the sound of the cheering men the Captain looked at his mate
"How did she do it" he wondered, "how did she turn my crew against me?"

"Well Cap'n", said the mate, "I believe she offered them something that you didn't"





There might be further episodes of the adventures of Sissy Cap'n Kaaren aboard The Raging Impaler as this has always been a favorite fantasy of mine. Feedback is always welcome.











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