The Business idea pt 2 (R)
The second sessionw ith Jennifer
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I Added Chapter three to the BOTTOM of this page . . . let me know what you think . . . it gets a bit sexy this time :)

sissy ashleigh


The email I received from Jennifer the next morning made my heart jump a bit into my throat:

Hi hon . . .

I'm really excited for our second session this afternoon. Don't forget to bring your list of things you want to explore. I really want to be able to explore each of your kinks as deeply as possible and that may require we set up some time outside of our regular sessions :)

Also, i am hoping we can do something today. I will explain it when you get here. see you at 4 :)


Focusing on work was perhaps impossible to say the least. All day long I could only think about Jenns understanding face as she snugly taped my diaper on the night before. an, of course, how cute she looked in her own diaper and t-shirt.

I arrived at 4 on the dot, not wanting to be early and seem to eager and knocked. What came to the door was stunning.

Jenn stood before me wearing a full catholic school girl uniform. Black shiny mary janes with white knee socks. A short plaid skirt and a white blouse. A green necktie tucked under a breen wool sweater vest. her hair, again in two braided pigtails and those seductive glasses perched on her nose. I could notice from the poof of her skirt that she was, again, thickly diapered in a disposable diaper.

Hi sweetie she said and gently held out her hand to usher me inside. come in and sit down, we need to talk about todays session. I smiled and followed her in, listening to the soft crinkle of her diaper.

We sats and she crossed her legs . . . .she told me that she had an idea for today but wanted to make sure it was ok with me before forcing it on me. she explained that she thought some of my desires were connected to my childhood . . . friends i wanted but couldn't have, things i wanted from my folks but never got . . . and she believed we could work through that together . . . but first she needed me to be completely relaxed and honest with her . . . and the way to do that, was take on sub dom roles . . . and, going along my fetishes, she wanted to be my babysitter and me be her baby for the afternoon.

I stared dumbfounded at her . . . hadn;t I told her I didn't WANt to be a baby? Before I oculd protest she continued . . . explaining that she didn't want me to crawl around talking baby talk or mess my diapers if that didn't make me comofrtable. Instead, she wanted me to simply play the role of the baby and allow her to take care of me . . .

Trusting her i agreed and she then lead me to the bedroom. The closet was wide open with her full costume collection on display . . . but I was a bit more drawn to the bed. A giant baby pink blanket was spread out with a stack of diapers, lotion, powder, wipes a paci and a bottle. Jennifer slowly helped me take off my shirt off and then unbuckled my pants.

Sit on the bed hunny . . . she said with a coy smile. I listened and she slid my pants off followed by my boxers. sitting in front of her naked i blushed quite a bit. she smiled in an understanding way and held up a bright pink pacifier to my lips urging me to take it.

its ok hon . . . we're doing this for you . . . . i know it may feel a bit weird but please trust me . . . i relented and let the paci slide past my lips. it actually did feel a bit comofrting as jenn laid me back on the bed.her hands began rubbing a cool baby wipe all over my tush and diaper area . . . she giggled a bit as i squirmed when her fingers ran lightly over the crak of my botom . . .

oh my . . . does my little guy like it when i touch there? she asked coyly. i blushed but nodded ever so slightly. good to know, she said with a smile . . . she then rubbed lotion gently all over my groin, smearing it across my bottom, working it into the cracks between my thighs and rubing it gently over my ever growing member.

properly lotioned, she then proceeded to sprinkle powder across my backside and front, rubbing it in gently with her hand before pulling the thick, bulky attends number 10 brief up between my legs and taping it in place.

feel better sweetie? she asked . . . i nodded aorund my pacifier. she then walked over to the closet and told me she would be picking out my clothes today. she selected a sweet pink tshirt and jumper with the word "princess" across the front in sparkly letters. she asked me to twirl once for her which i did dutifully, loving the feel of the skirt brushing against my legs.

now, are you hungry, honey? she asked as a babysitter would really ask a four-year old. i nodded again, not sure yt how to talk around the pacifier whcih she had now clipped to a ribbon on my jumper. jenn lead me back to the kitchen and asked me to sit on a barstool . . . .when i did, she produced a tray which she set across the arm rests and hooked to some makeshift clasps, locking it in palce like a high chair.

jenn stood in ront of me and spoon fed me choclate pudding and some macaorni and cheese while we talked. i felt so secure and safe and loved i had no problem spilling my guts . . . telling her that most of my kinks weren't so much separate fetishes, jsut different variations of the same. being diapered and dressed up as a girl . . . . as a ballerina . . . as shirley temple . . . my desire to have my dressing filmed . . . . to be allowed to attend an all-girl slumber party and do girly things . . . to have a woman make love to me instead of the other way aorund . . .

with that last one she paused . . . do you mean, to be the woman sexually? she asked puzzled. no, i explained . . . . i don't want to be swith a guy or even be the girl . . . i want a girl to be dominant and controling . . . to do things to me . . . i flushed a bit (it's hard to say outloud that you like to have your bottom played with).

she nodded, seeming to understand and we went back to my snack. when we were done, she cleaned my face and lead me to the living room where we sat on the couch, talking more . . . i told her about how i had grown up as a sensitive boy, and i seemed to get along better with girls . . . but i could never really be included . . . i couldn't take the same dance classes or go to their slumber parties. i didn't want to BE a girl . . i just wanted to be PART of the gorup.

jenn just nodded the whole time, keeping her hand on my leg in a reassuring way. before we'd realized it, it was well past 8 pm and we were both getting sleepy. jenn leaned over and checked my diaper which i had wet a little while earlier. again she asked if i wanted a chaning and of course i nodded enthusiastically. she led me back to her room and had me lay down, lifting my skirt so that i was out of the way. she eased open the tapes and opened my diaper . . . sliding it out from under my bottom . . . then wiping me clean ever so gently . . .reapplying lotion and powder with a caressing touch. as she slid a fresh disposable diaper under my bottom jenn asked me what my plans for the next day were (it was a saturday) i told her i hadn't thought of anything and hse asked if i would like to try another session that was a bit more adventurous.

i nodded again as she eased the diaper closed and taped it snugly. she got up from the bed telling me to stay put and left the room. she came back with a slip of paper bearing an address.

now sweetheart, it's dark outside and oyu parked on the side of my place so no one will see you going to your car. i want you to wear your pretty outfit home and then wear it to that address tomorrow at 10 am sharp. i will be there with a friend of mine. i promise we are going to have a lot of fun . . . but before you go, we need you to have a proper girls name . . . .do you have any ideas?

i blushed because of course i had thought this through . . . i whipsered "ashleigh" in an embarassed voice. she smiled and told me it was such a pretty name and suited me well. she walked me to the door again but instead of kissing my cheek tonight, she gave me a gentle peck on the lips. goodnight ashleihg. i will see you at 10 am . . .

i floated to my car, savoring the crinkle of the fresh diaper, still sucking my pacifier and my head swimming about where this address was and what we might be doing . . .


My hands were trembling a bit when i pulled up to the address jennifer had written down on a piece of paper. It was one of those office complexes with a bunch of single story buildings that had to be navigated by a big directory. I couldn't see through the smoked glass . . . just a door with the address number and the mord "Brittany"s written in bold pink cursive . . .

I sat in the car a few moments before I saw jenn burst out the front door with an excited expression on her face. She ran to my window and kind of squatted down, resting her head on her arm on the fram of my door . . .

Ready to go have some fun? she asked sweetly . . . .I nodded and she pulled open my door and half dragged me into the building. what greeted me insdie was both breath taking and a bit terrifying.

Brittany's is a dance studio. We walked in to see full length wood floors, ballet bars, floor to ceiling mirrors . . . and the sweetest looking woman (well next to jenn) standing center floor. Jenn explained that her friend brittany is a dance teacher and wanted to help in my therapy . . . we were going to work through my dance class desires right here . . . I was speechless.

The first thing needed (explained jenn) was a proper wardobe. itturns out that Brittany (who is about 5'5" and has a perfect dancers body) also runs a ballet and dance costume shop adjacent to her business and jenn had picked out some clothes for me. She took me into the girls dressing room with her and there, laid out, were two PERFECT ballerina costumes . . .matching of course.

She explained that we would take a class together, but before we could I had to get dressed . . . she explained that the tights and leotard and tutu were kind of complicated and to prevent accidents, she wanted me to wear a diaper underneath. she quickly stripped off my jeans and tshirt (shes getting quite good at that) and had me lay down on a towel on the floor. She expertly slid a diaper under my bottom, applied powder and a gentle blow on my tummy before pulling it up snugly between my legs and taping it in place. when she pulled down her own pair of sweat pants i saw her own diaper already in place.

she helped me ease into a pair of pink tights, black leotard and puffy pink tutu (not classic class attire but this was about the experience) . . . she helped me slip on a pair of light pink slippers before bobby pinning a tiara to my head (like a good ballerina). Once i was dressed, she quickly put on her own matching outfit before taking my hand and leading me out to the floor.

Brittany was so kind and gentle, calling me ashleigh from the start and helping me through some basic barre work. She addressed jenn and i as "young ladies" and jenn would gigle with me whenever one of us made a mistake. before long an entire hour had gone by and our ballet class had ended. i floated back to the dressing room with jenn who had a smile on her face . . .

did you have fun my love? she asked sweetly. i nodded yes do you want to leave? she asked again with a sweetness to her tone i cant quite describe. i shook my head no. good she said . . . because i have a surprise . . .

but before you get your surprise, i want you to do something for me she said gently. i need to know that you trust me completely . . . . i want you to wet your diaper . . . right here in the dressing room . . . i want to know that you trust my instruction.

I hesitated only an instant before i let go and let the warm sensation flood my diaper. i sighed and she gigled as she placed her hand under my tutu to feel the warmth spread.

good girl she said as i was done and savoring the warm liquid surrounding my legs. She eased my tutu down and then helped me out of my leo and tights. she laid me down and untaped my diaper. . . . but left it hanging open with m arousal evident by a stiff member. she knelt next to me . . .

sweetheart, i have to ask you something . . . would you rather have me as your therapitst . . . or your girlfriend? I was stunned by the question but5 answered honestly tha ti felt closer to her than anyone ever and would love to develop a personal relationship.

good honey . . . because i do care for you too . . . i dont believe you need therapy, i believe you need a loving hand to simply accept and love you for what you are and what you need . . . she leaned down and kissed me . . . i swam in the warmth of her lips for what felt like an eternity . . . . i knew i was in love . . . this wonderful woman had seen me at my most vulnerable and could still find me attractive and worth her love.

now . . . what does my little sweety need most of all right now? she asked with a sexy gleam in her eye . . . i giggled and half-joked that an orgasm would be nice. she smiled and grabbed the baby lotion . . . squirting a bit on my member before she began to gently stroke it . . .

i simply closed my eyes and reveled inher touch. after a moment her soft voice asked if i only wanted her to touch me like a boy . . . or if i wanted her to touch me like a girl too . . . .i told her i didn't know what she meant. . . . i felt her finger gently slide from the base of my member back towards my bottom and i shivered with delight . . . she gently spread some lotion on my backside and eased her finger inside . . gently exploring my bottom for the first time while stroking my member. After a moment i exploded in a delicious orgasm . . . she used baby wipes to clean upand then eased a fresh diaper under my bottom and added powder before taping it in place. i reached for my jeans but she shook her head . . .

you have one more class my love . . . and with that she reached into a closet and pulled out a bouncy shirley-temple styled dress with patent leather tap shoes. come on honey she said, we dont want to leave miss brittany waiting . . .
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These lovely people support all the features in Sissy Kiss to contribute to our community! So it would help so much if you could check them out, and say your from Sissy Kiss. Some even give discounts, or free gifts by mentioning it!
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I just wanted to say that this is a really great story; your description of how "Ashleigh" feels is so real that I can use some of it to help me explain to my wife how I feel! Thank you so much *kisses* As for ideas for pt3, I think Ashleigh and Jennifer are going to meet another sissy girl and that they can do lots of girly dressing up games and maybe more....or it could be another Mommy who is happy to play the dominant role with Ashleigh in bed, just like he (and I !) wants *BLUSHES*

Hope that helps in some small way, but given how good the story is so far, I think you're well ahead of me!

Big hugs and kisses,  

babymarcie xxxxx
Marcie xxxxx
Sister to lisa123
sissy ashleigh
thanks for the sweet comments marcie . . . .would you mind e-mailing me ([EMAIL=""][/EMAIL]) i wanted to bounce some ideas off of you for future chapters :)

sissy ashleigh
It is wonderful to finally find someone who actually writes genuinely loving relationships; after reading so many where cruelty and betrayal are the central themes it is reassuring to find one that is based on kindness and love. You have done an excellent job delving into the psyche of your protagonist and in doing so have shown a better than average understanding of the human mind and how desires for compassion and acceptance often become reflected in one's sexual fantasies; it is commendable and surprising to find another who has taken the time to try and understand the subconscious. Have you taken any psychology classes? Also as someone who has similar desires as the protagonist of your story the fact that, as of this point in the story, he has managed to find someone who cares for him and is understanding and accepting has the effect of granting me, and likely others, the ability to hope to find someone just like Jennifer. I look forward to more and hope that her love and apparent devotion does not fade, nor mutate into something despicable.
Llllloooooovvvvveeeee Iiiiiittt!!!!
very well done love to read more
likes my fanny in warm hands and to be foundle by anyone you would like to play .
Mina Silverwind
I love your touching story, I love the new direction took your srory. and I eagerly await what will happen in the next chapter.
success is not how many times you win but is instead our ability to learn that we win by never giving up when times are tough.
it was gr8
 Princess are kind, brave, beautiful and determined they can do or be anything 
even change the world.  

 All girls are princess what you see in the Mirrors doesn't define you.
It doesn’t meter if you weren't born a girl. As long as your one at heart you too
are a princess 

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