Granddad's Diaper Sissy by Stephanie

[archives]

This from our 2000 archives.

Part 1

The following is a true account of what happened to
me when I was 21 years old and began one of the most
exciting and yet frightening periods of my life.
I had moved out on my own shortly after finding a
management job out of college. As a child I had been
diapered for bed wetting up until I was 12 years old
and it had set the tone for my interest in wearing
diapers. I was an only child to well-to-do parents
who spent more time socializing and traveling and
had little time for a child. In fact, I rarely saw
my father as he was always away on business. As a
teenager I fantasized about wearing diapers again
but the fantasy always was something involving just
me and not another person who participated.

All that was about to change, one day I purchased a
local Adult Oriented Newspaper that catered to
fetishes and other adult pleasures. Most of the ads
went right over my young, inexperienced head but one
caught my eye......."Older, professional.
father-figure in his 60's seeks a young, sweet,
sissy male in their early 20's who would enjoy being
Grandpa's 'little baby girl'. Must be slim, single,
submissive and available on weekends."

The phrase "baby girl" caught my eye as I knew it
meant wearing diapers. I had never thought of
dressing like a little girl but the idea seemed
appealing. I didn't answer the ad for a couple weeks
because the idea of being dressed up by someone the
age of my grandfather seemed odd. Yet at the same
time something in the back of my mind made it
exciting, I think it may have been that I grew up
lacking the attention of a father and my grandfather
and now was my chance to receive that attention from
a man I needed growing up.

I sat down and wrote a lengthy letter explaining
about how I had been diapered as a child for
bedwetting and loved the feeling of wet diapers. I
spent a long time explaining about how my father
neglected me when I was growing up and how I craved
the chance to be under the guidance of an older male
and finally have a father-figure in my life.

A couple weeks passed without a response, I had
given up hope when I finally received a letter in my
mailbox. I eagerly ripped it open and began to read
it while waiting for the elevator. His name was Bob,
he was in his early 60's, had grown children and was
widowed. He was a semi-retired physician and as I
suspected from his ad, he was looking for a young
man who he could diaper and dress up like a little
girl.

As soon as I got into my apartment I dialed his
number, the moment the telephone rang I lost my
nerve and hung up. It took a few hours before I got
up the nerve again to call, the telephone at the
other end was picked up before it could even ring. I
stammered out my first words and must have sounded
like a compete idiot. We talked for hours that night
and immediately hit it off, he had an authoritative
yet soothing way about himself that put me at ease.

I told him about my childhood and about how my
father was rarely around and I was eager to have a
father-figure in my life. He told me about what he
expected from me and how I would be treated, he
believed in strict, old-fashioned discipline and
made it clear that any misbehavior would be severely
dealt with. We agreed to spend that weekend
together, he gave me instructions to take the bus to
West Vancouver and where he would pick me up.

Saturday morning arrived and I was both excited and
terrified as my bus neared the stop. As I exited the
bus I saw who I assumed was Bob waiting for me
beside his car. He looked like your typical
grandfather, well dressed, gray hair, nice smile, he
waved and I walked over to him. I could see that he
was looking me over as I approached and I suspect he
approved. I was fairly small for my age, thin and
had longish hair. We talked for a moment and he
reassured me that everything would be all right as
he could see that I was very nervous. He chatted as
we drove up the long hill towards the nicest
neighborhood in the city. I didn't say a word during
the 15 minute drive, at one point he took my hand
and reassured me that I would have lots of fun and
he would make my fantasy of being diapered come
true.

We stopped at the end of a long driveway with a
large gate by the roadway. All I could was a long
curving drive through the trees but no house. As the
gate slowly opened he reminded me that once inside I
was to act like a young child of 10 years not as an
adult. For the fantasy to work it was important that
I not revert back to an adult male personality, and
in return I would be treated like a child in all
ways. I nodded my head and we entered his private,
secluded property. At the top of the driveway was a
huge old Tudor style home that looked more like a
mansion than a house for one person.

He gave me a quick tour of the house and lead me
upstairs to the washroom, I was told to shower and
then some down to the first door on the right. When
I was finished with my shower I noticed that all my
clothing was gone even though I had locked the
bathroom door. I wrapped the towel around m waist
and slowly walked towards the open door. Bob was
waiting for me inside a room that looked exactly
like a little girl's room, Everything was frilly and
lacy complete with dolls, teddy bears, ballerina
wallpaper and ruffled curtains. I must have looked
surprised, yet it turned to shock when I saw a large
crib in the far corner, beside it was a dresser and
on the other side a super large "changing table"
that could easily accommodate an adult.

Bob took me by the arm and lead me over to the
table, at the time I was about 5' 8" and weighed
less than 150 lb. while he was at least 6' tall and
easily weighed 200 lb., he lifted me up on to the
table and gently guided me on to my back. I recall
shaking with fear as he turned away to gather some
diapers and plastic pants from the nearby dresser.

He talked to me as if I were a child and explained
that even though I was 10 years old I still needed
to be diapered and liked to be dressed like a little
girl. He pulled away my towel and I could see that
he was displeased, I had forgotten to shave off my
pubic hair as he had instructed me to.

He gave me a stern lecture about not following his
instructions and that I would need to learn a lesson
on the consequences of not following his
instructions. He ordered me to get up off the table,
he took me firmly by the wrist and guided me over to
a chair situated in the corner. Before I knew it he
sat down and pulled me across his lap. Without
saying a word he proceeded to deliver a bare bottom
spanking like I had never had before. It was at
least 5 minutes before he stopped, by which time my
bum was right red and stung as if it were on fire.

He pointed towards the table and once I was on he
diapered me without saying a word. I was put into a
short little yellow party dress complete with white
crinoline and matching yellow rhumba pants to cover
my plastic pants. As he zipped up the dress I felt
the mix of excitement and humiliation yet also fear
at the same time. He told be to stay in my room and
think about my punishment while he prepared lunch.

[archives]

Grandpa's Diaper Sissy Part 2 by Stephanie



For the next hour or so Bob left me in the room, I wanted to escape and go home but that was hardly possible in my present state of dress. I began to look around the room to see what he had in store for me. The crib was just large enough for me and the mattress was covered in girlish sheets and a wind-up mobile was even attached to the railing. The changing table was obviously custom built as it could easily handle an adult, the sight of restraining straps at the top end scared me though, the drawers were stocked with baby pins, lotion, baby powder and some strange looking pills that I later learned were suppositories. On the dresser were stacked a pile of cloth diapers and plastic pants while the drawers were full of more along with ruffled pants, tights, ruffled anklet socks and other girlish underwear.



As I rummaged through everything I could fee my coc-k grow hard inside the tightly pinned diapers. I walked over to the closet and after opening the doors was shocked to find it full of the frilliest little girl dresses, nighties, rompers, crinolines, playsuits, shorts and tops that you could imagine. It looked like a little princess' closest except in adult sizes. Where did he get all of this stuff I wondered? Was this all intended for me and I wondered if he had other young guys that he dressed up like this? Looking at all these frilly things got me even more aroused, it was strange because I had never been aroused by frilly clothing before. I slid my hand inside my diapers and feverishly pumped my coc-k, it took only a few seconds and I squirted into the soft clean diaper.



It wasn't a moment to soon as I heard a key being inserted into the door lock and Bob walked in. He smiled when he saw that I had discovered the closet full of clothing. He sat down and told me that he wanted to explain things to me and answer any questions I had. He must have read my mind because his explanation answered all my questions before I could even ask them.



He explained that he had always wanted to find a young man who would agree to be a little girl for him, in the past others who responded to the ads were either too old and/or married, or just not the right person for him. He wanted someone who would be submissive, and also looked young and slightly effeminate while also available to spend weekends with him. I seemed to fit his needs as I had no girlfriend, looked slightly girlish with my longer than normal hair and was submissive. An accurate description was I was a the wimpy type of guy that the guys picked on in high school. The clothing was all custom made by a seamstress he knew and the babyish furniture was made in his workshop. He went on to stress that he expected me to act like a girl and over time it would be easier, I was to address him as "Grandpa" or "Granddad". I would also be expected to behave properly and any misbehavior would be dealt with rather severely as he believed in strict discipline or children. This lead him to the fact that I had not shaved completely like he asked and he would correct that during my next changing.



Lastly I should be prepared to be taken out in public while diapered and the diapers would be used for everything.



I looked at him with a shocked expression and he smiled, "Yes, you know exactly what I mean, you will be expected to make poo-poo in them like a baby."



I started to object but his stern look stopped me from uttering a word.

"For that you'll be spending some extra time in a dirty diaper to teach you a lesson."



He took me by the hand and lead me downstairs into the kitchen for lunch. I couldn't believe what I saw, he had converted a kitchen chair into a makeshift "high chair" except that it was normal height instead of high up. He sat me down, slid tray tightly into place and fastened my arms to a pair of restraints on the side of the chair so that I wouldn't be able to feed myself or resist him. Once a bib was tied in place he fed me about 4 jars of terrible tasting babyfood which I tried to spit out and at one point I almost vomited from the foul taste. All I succeeded in doing was making a big mess.



He seemed to enjoy my plight as he purposely would miss my mouth or over stuff my mouth so the food either escaped my lips or was smeared on my face. He chatted to me as if I were a child and laughed at all the faces I made. After lunch he let me watch Disney movies while he cleaned up, as I watched be gave me 4 baby bottles full of juice which I had to drink. It wasn't long before I could feel the urge to pee, I started to squirm on the floor until it was no use. My bladder exploded and the diaper absorbed the warm pee with no difficulties. No sooner did I pee than I could feel my coc-k harden in the warm, wet diaper. Grandpa came into the room and told me to follow him. Thank god the fluffy dress hid my bulging diaper.

[archives]

Grandpa's Diaper Sissy Parts 3 & 4 by Stephanie

No sooner did Grandpa get me outside did he realize that I had no shoes, he returned a few minutes later with a couple pairs of "Mary-Jane" style shoe. Most were too small but one pair were perfect. His yard was huge and high trees prevented any of the neighbors from seeing into it, plus the houses were so far apart in this neighborhood. There was a pool off the patio and down on the grass was a sandbox and swing-set. He told me he had them for visits from his grandchildren and grandnephews and grandnieces.

It was a sunny but windy day and the wind was really blowing up my dress, a couple of times lit lifted the dress right up to fully expose my rhumba pants. Granddad just laughed and took my hand as he showed me his garden which he obviously was proud of and I really couldn't have cared less about. It felt very weird have to have my hand held by a man but the fact that he looked so much like a grandfather made it easier. The wet diaper and frilly dress started to make me feel more girlish and I eventually began to feel a little less uncomfortable.
I was shocked when he stopped, turned to me and said, "I think it's time to have that diaper checked, lets see if all that juice has had it's effect yet."

Before I could react he reached up under my dress and pressed against my heavy, soaked diaper. He smiled and as I tried to pull away he pulled down the rhumba pants to expose my plastic baby pants.

"Oh my, it looks like someone had a big pee-pee already and you seem to be a heavy wetter too."

I didn't know how to respond so I just stared down at the grass in embarrassment. The rhumba pants were pulled back up, he patted me on the bum and continued the tour. In the basement of the house he had a workshop where he made furniture. In addition to normal furniture he also made baby style things like those upstairs, I was surprised to see a more realistic high chair being made and what looked like an old-style wooden playpen. He told me that in a few weeks they would be ready for my use.

For the next hour or so he had me play on the swing and even in the sandbox while he relaxed on the lounge chair watching me.

Periodically I could see him rubbing his crotch as he must have been enjoying the sight of me playing like a little girl. He called me up to the patio when he saw that my dress was dirty from the sandbox and he wasn't' too pleased.

"Let's get you changed into something more appropriate for playing in."

Once upstairs he got me out of the dress and wet diapers. As I lay on the changing table he proceeded to carefully shave my pubic area and finally around my bum so that I was now completely hairless.

It felt and looked so weird to be hairless and I was shocked that when he started to rub lotion on my bum and crotch my coc-k started to harden. He didn't say a thing but just smiled.

He double diapered me again and told me that my next changing would be at bedtime and he put me into a large pair of baby pants that had very tight leg openings to prevent leaks.

The shock of the weekend came when he said, "Now lets find you something you can wear to the zoo tomorrow."

I cried out, "There is no way I'm going out in public like this!"

Without wanting I received a sharp slap across the face from his hand and a moment later he pushed a pacifier in my mouth and tied the string tightly around my head to prevent me from spitting it out.

"We'll be going to the Vancouver Game farm in the morning and you definitely will be diapered and wearing something girlish yet passable in public. I have something planned for you because of your little outburst combined with not shaving properly and I know you'll never make that mistake again," he laughed as turned around and gathered some clothing.

I recall tears starting to form in my eyes as he showed me the outfit he intended me to wear. It was a pale yellow T-shirt, and light blue bib-style shorts with yellow trim. On the bib portion was a yellow appliqué lion, the straps crossed at the back and attached to the rear of the waist band. The worst part was that the shorts portion was kind of bubbled like a little girl's to accommodate the diapers and there were snaps visible between the legs to facilitate diaper changes.

I shook my head in protest and Grandpa smiled, "Don't worry, if anyone says something I'll tell them you're mentally handicapped as well as incontinent".

I actually started to cry, Grandpa told me that it might be better if I had a short nap before dinner and then I' d feel better. He put me into the crib naked except for the diapers and then pull on these large mittens to make it impossible for me to use my hands except for grasping large things.

I lay there still crying when he returned with some warm milk which he said contained a sedative to help me sleep. I don't even recall finishing the bottle before drifting off to sleep.

part 4

Grandpa's Diaper Sissy Girl - Part 4
 
I must have slept for a few hours because when I woke up it was beginning to get dark outside. The first thing I was when I opened my eyes was Granddad Bob looking down at me from over the crib railing.

I felt very weird and spaced out especially when I tried to sit up In the crib. It took me a few moments to get my bearings and then it hit me. My diapers were soaked and I hadn't even woken up when I did it.

Granddad helped me out of the crib and as I stood leaning against the changing table for support he helped me into a big, soft, fuzzy footed sleeper, "Here my little one, it's chilly now".

He put his arm around me as we went downstairs, my plastic pants making that unmistakable squishing sound of being soaked. He sat me In the "highchair", slid the tray into place and left my hands bound in the mittens while he prepared dinner. He was making one of my favorites, Kraft Dinner, with wieners, and I was starving. I ate as fast as he could spoon it into my mouth and by the time I finished the entire box I was ready to burst. He handed me a bottle full of apple juice, which I was barely able to grasp with the mitts and drank it up while he cleaned up the dishes.

After dinner Grandpa settled on the sofa and motioned for me to join him, I still felt groggy from the sedative and laying down seemed like a good idea. I wasn't quite ready for what happened next, as I sat down he gently guided me over so that I was cradled in his arms with my head against his chest and partially laying across his lap.

I was rarely hugged by my real dad and never knew my grandfather, initially I felt very uncomfortable but as he stroked my hair and talked softly to me I relaxed and closed my eyes. He gave me 2 more bottle of warm milk as I lay there for a few hours while he watched TV, when the bottles were empty he replaced them with a baby pacifier.

It wasn't long before I began to feel the urge to pee again and began to squirm,. Sensing my state he unzipped my sleeper and placed his hand against my diapered crotch as he coaxed me to pee for him. He kissed me on the forehead when he felt the warm rush of pee fill the diaper even more.

I must have dozed off again because I woke up laying by myself on the sofa while Granddad was in the kitchen preparing yet another bottle,

He told me it was bedtime as tomorrow was going to be an exciting day for me and he didn't want me to be all cranky at the zoo.

Once upstairs he changed me out of the soaked diapers, as I lay there naked he gathered a new sleeper and fresh diapers. Before rediapering me he spread lots of Vaseline across my bum to prevent getting diaper rash. I jumped with a start when he gently presses his Vaseline coated finger against my anus and pushed it inside me. It was the first time something like that had ever happened to me and I surprisingly didn't fight it, in fact I even spread my legs slightly to accommodate his probing finger.

"I wonder if my little one needs a suppository tonight since she hasn't had a poo-poo yet? Well, maybe not, lets see what happens because I don't want you making a mess while we're out."
He withdrew his finger tightly diapered me and warned me not to get out of the crib until he comes in the next morning. He handed me the remaining bottle and sat down to read me a story. I fell asleep in moments due to the sedative and tomorrow would bring a new stage in my life with a Granddad...............

[archives]

Grandpa's Diaper Sissy Part 5 by Stephanie



I slept straight through the night and only woke up after Granddad gently shook me on the shoulder. He helped me up and after checking that my diapers weren't too soaked took me downstairs for a big breakfast of Cream of Wheat and babyfood. I could see that the weather had changed and it was raining lightly, I figured the trip to the zoo was canceled because who would want to go in this weather.



Once breakfast was over he took me back upstairs for my bath, he washed me completely and once dry brought me back into my room where my outfit for the day was laid out. "We aren't still going to the zoo are we"?, I asked half hoping to hear the answer I wanted.



"Of course silly, a little rain won't hurt us and it will be less crowded won't it".



I was thickly diapered again and put into the T-shirt and shorts. The shape of the shorts did nothing to hid my diapered condition, in fact it made it pretty obvious that I was wearing diapers. You could hear the distinctive rustle of plastic pants with every step and I looked over to him with pleading eyes hoping he'd change his mind. It only got worse, from the closet he removed a large babyish looking diaper bag and filled it with spare diapers, plastic pants, wipes and another pair of shorts.



A short distance from the house we stopped at a 7-11 where Granddad went inside and purchased a coffee for himself and a large "Big Gulp" full of Coke for me. With that much pop I was certainly going to be wetting before we even arrived at the zoo. It was at least a 2 hour drive out of the city to the zoo, I hadn't been there since I was a kid but I recalled it was lots of fun. We drove in silence for the longest time as I slowly sipped my Coke through the straw. Bob broke the silence by asking me to tell him more about my childhood in particular my experiences with my father and diapering. He listened and asked questions but did not offer any comments as I told him about my experiences.



I was often diapered at bedtime up until I was 12 or so due to bedwetting. My mother was not the greatest at dealing with children and found it all a big inconvenience to her social life. After wetting the bed I was often scolded and that evening Mom would lay out some cloth diapers and plastic pants to be worn under my pajamas.



I'd always put up a fuss but in the end I'd lose the argument and be diapered anyway. At age 10 we moved to a new house and I had to change schools. Right from he first day I was picked on my the class bully, at the time I was tiny for my age and an easy target. My bedwetting increased to the point where it was occurring every night. Dad was getting annoyed with this babyish behavior, often would call me a "Sissy Baby" and would suggest that maybe I should be dressed like a baby girl instead of a boy. This made things worse and I'd dread it when he was home from business. One weekend he had had enough, I'd wet the bed again and Mom was scolding me when he walked into my room. He told my Mom that her method of dealing with this wasn't working and it was time for a change. He pulled me over his knee and spanked me until my bum was good and red, once done he announced that I'd be in those diapers the entire weekend. By the time I reached 13 the diapering stopped but my love of diapers and the humiliation I felt when wearing them had been formed for good.



By the time we reached the zoo I was already wet and it had stopped raining. Thankfully it was still cool so I wore a jacket which hid my sissyish looking outfit and my diapered condition. We spent the first couple of hours going through the indoor exhibits which it seemed like every other person was doing too. The crinkling sound of my plastic pants seemed to echo in the crowded area making me very self-conscious.



I whispered to Granddad that I wanted to go see the outside animals now, he replied in a louder voice than was necessary, "I think you should be changed first."



A couple of people turned to look in our direction as he took me by the hand and lead me out of the "Jungle Exhibit". We were walking back towards the entrance gate so I assumed he was going to change me in the car. Instead we went the Information Desk in the main building, I just about died with embarrassment when he asked the teenage girl at the desk if there was any facilities where he could change my diapers. The girl had a shocked look on her face but when he told her that I was mentally handicapped and suffered from incontinence she understood. The only place available was the "Mother's Room" but she thought it would be all right if he used it.



My face must have been beet red with embarrassment as he took my hand and lead me away from her desk, my soaked and sagging diaper must have been in full view for her to see. He whispered, "She was cute, I bet she'll be telling all her friends about this tonight."



There were a few moms in the room when we arrived so Bob asked politely if they minded if he changed me here. A couple looked at me strangely but said that he was more than welcome to change me. The changing table obviously were to small for me so he took me to a corner, removed a large changing pad from the diaper bag and laid it on the floor. He talked to me as if I were a child and told me to lay down. It was so humiliating as I spread my legs so that he could undo the crotch snaps of my shorts. I could see all the women were discreetly sneaking peaks as my plastic pants were exposed and finally my diapers. He put the soaked diapers in a plastic bag and then into the diaper bag.



As he pinned on a dry diaper one of the ladies asked, "Don't you find disposable better than cloth diapers?"



I couldn't believe this was happening, I wanted to get up and run out of the room. As he pulled the plastic pants back up he responded, "They definitely are more convenient but I find cloth much more absorbent."



He refastened the snaps and pulled me to my feet, I stared at the ground as he lead me out of the room. I recall having tears in my eyes from the shame and I begged that we go home now., he just ignored me back out into the zoo. By now the sun was out and it was getting warm, he told me to take off my jacket now but I refused. He gave me a stern warning that if I didn't I'd get s swat on the bum right infront of these people. I dared not risk that so I did. I felt as if every person in the zoo was staring at my outfit as we walked around the zoo looking at all the animals.



It was mid afternoon when we decided to leave, we stopped to get a couple of hot-dogs and pop which I promptly ended up spilling across my lap along with getting mustard on my shirt. Granddad made some comment about having me wear a bib and using a baby bottle next time. I was exhausted and slept most of the drive home, once there I changed back into my "normal" clothes as I had preparations to do for my meeting on Monday morning. As Granddad then drove me home he asked if I wanted to get together again next weekend too. He asked very hesitantly as he probably expected that I would say no. I told him that I could hardly wait and was hoping we could do this every weekend.



We made arrangements to talk during the week and plan out next weekends activities.

[archives]

Grandpa's Diaper Sissy Part 6 by Stephanie

For the next few days I had a hard time thinking about anything except my weekend with Bob. I was torn between the excitement and humiliation of being diapered and dressed up like a little girl, while on the other hand I wondered if I was crazy to get involved in something like as "perverted" as this with a man I barely knew. I also began to wonder if he would expect to have sex with me? The thought scared me yet at the same time as I lay in bed fantasizing the thought excited me as I stroked my p_nis.

By Wednesday I decided that I definitely wanted to continue the relationship with him, I had nothing to lose and everything to gain. I hadn't had a date in months, I had very few friends that I associated with on a regular basis and I spent most weekends at home watching TV so this would be quite an improvement.

When I got home from work that night Bob had left a message on my machine. We talked for a couple of hours, I felt more comfortable talking about things over the telephone instead of in person and was much more open with him. At first we talked about general things like my job and his family but eventually things turned to our weekend together. I had no preconceived perceptions and no idea what to expect so I was happy with how things went. I was scared about being out in public and preferred that I wasn't taken out but Grandpa was adamant that being out in public was important to him as well as being subjected to his friends. This shocked me as he appeared so conservative but in reality he was very active in the "fetish community" and his friends were very open-minded.

He asked me if I would be interested in also dressing and acting like a slightly older girl of around 13 or 14 instead of always being a "diapered sissy". I was honest with him and told him that it was the diapering that interested me the most as well as being treated like a little baby. He agreed that it was what he enjoyed too but he also liked the "school girl" look of a young teenage girl too. With my slim build, slightly long hair and some makeup I would be quite convincing as a girl. I was hesitant but when we agreed to compromise and incorporate diapering as a form of punishment should I act up while being a girl I thought it would be fun.

It was decided that I would spend the coming weekend with him from Friday evening to Sunday afternoon. On Friday I would be dressed like a "school girl" and then the rest of the weekend would be in diapers again. He made arrangements for a taxi to pick me up on Friday evening as he wouldn't have time to pick me up.

We hadn't talked about making our arrangement long-term and I thought it better if we saw how things went this weekend. I had no idea if I'd like the idea of dressing up as a girl, frilly outfits excited me but dressing like a teen had never entered my mind.

I arrived home on Friday later than normal and saw a taxi waiting infront of my building as I pulled into the underground garage. I dashed upstairs, threw my briefcase on the table and ran downstairs without even changing out of my suit. The driver knew where to go and within 40 minutes he was pulling into the long drive up to the house. Parked infront was a car I'd never seen before, as I got out of the taxi Bob opened the front door and came outside. He looked annoyed as he paid the driver and as soon as he gave the driver the money he gave me a solid smack on my bum.

"Now get inside and go straight upstairs to your room, I'll be right up!"

I could hear a man and woman chatting in the kitchen as I went up the stairs. A few minutes later I could here Bob coming up the stairs with someone, the sound of the heels on the wood floor gave it away that it was a woman. I stood nervously by the window as the door opened, the woman appeared to be in her 40's was tall, had too much makeup on and was dressed in a tight black skirt, white blouse, and heels. Bob introduced me to Barbara, she was a dear friend and a transvestite. Being a young, naive guy I'd never seen a TV before, at first glance she looked like a real woman but then I could start to see the differences.

"Barbara and Hans will be having dinner with us this evening. I was just telling them how excited I was to have a new "girl" to dress up and play with. Barbara is going to help you get ready while I go finish dinner."

"Okay doll, let's get you looking all sweet and adorable for your new daddy. Now get those clothes off", she teased as she went over to the closet.

First she helped me put on a white bra and matching panties followed my white cable-knit tights. A plain long-sleeved white blouse came next, which she buttoned for me and then she held up a short, blue pleated skirt with a bib front that had straps which went over my shoulders, crossed over and then attached to the back of the skirt.

The final touch was a pair of plain black "Mary-Jane" style shoes.
She stood back and looked me over, "I have an idea what will get 'Old Bob' nice and excited", she said as she went over to the dresser and returned with a pair of white, ruffled, rhumba panties. She helped me step into them and then took me into the bathroom to apply some makeup, the final step was to curl my hair slightly with a curling iron.

To my surprise I looked fairly girlish. My slim features and long hair definitely helped along with the lipstick and rouge. The skirt was awfully short and it didn't take much for the ruffled panties to become visible.

[archives]

Grandpa's Diaper Sissy Part 7 by Stephanie



I nervously walked downstairs into the dining room where Bob was setting the table for dinner. When he saw me he smiled and came over, he stroked my hair and gave me a playful pat on the bum.



"Stephanie, I'd like you to help me set the table. Please get the dinner plates from the china cabinet while I get the last of the cutlery out."



The plates were high on the shelf and I had to stretch to reach them. I took them down one my one and what I didn't realize was that he had spotted my ruffled panties and was standing right behind me. As I reached for the last plate he slid his hand up my skirt and rubbed my bum. The shock made me drop the plate, it landed on the stack of others and ended up breaking them.



Bob was furious, "How could you be so clumsy? Do you know how valuable those plates are?



He grabbed me by the arm and pulled me into the kitchen, with one hand he yanked down my panties and tights exposing my bum and with the other he leaned me across the kitchen counter. He pushed my chest against the cold marble counter with his left hand as he flipped up my skirt with the right. He began to spank me with his bare hand, they were full force smacks and it immediately began to burn. By the 5th smack I was squirming and by the 10th I was pleading for him to stop. He stopped momentarily and I thought he had finished but I was wrong. I could hear the drawer open, I looked over my shoulder and he held a "wooden spoon".



"No, no please stop!", I pleaded.



I yelped in pain when the first smack with the spoon landed on my burning bum. He smacked me about 10 more times, by which time tears were flowing down my cheeks and I was softly crying. When I stood up Hans and Barbara were standing in the kitchen doorway watching. Bob made me stand in the corner until dinner was ready, all through dinner I sat quietly in my chair, my bum still searing with pain.



After dinner Bob called me back into the kitchen, he had me sit at the table and gave me a pad of paper with a pen. "To teach you a lesson I want you to write the following 300 times 'In the future I will be more careful with Granddad's possessions'." You will sit here until you're done and not move unless you get permission first. He returned to his guests while I sat there for the next 4 hours writing my lines.



It was about 11:00pm when I heard Barbara and Hans leave, a short while later Grandpa came into the kitchen and looked at my completed sheets. Without he word he took my hand and lead me upstairs to his bedroom and locked the door behind us. He sat me down on the edge of the bed while he gathered something's from the ensuite. He returned wearing a robe and began to speak softly to me.



"You see my little sweetie, if you are going to dress all cute and adorable in your uniform you can expect to excite old men like me. Most men dream of having a school girl and now it's my turn, I'm going to show you how girl's must please a man and if you do a good job you'll be rewarded".



I started to get up but he put his hand on my thigh. "You don't have a choice now, if you resist it will only make it worse".



I was now terrified, I couldn't believe it, I was going to be forced to have sex with him. He removed his robe leaving him naked beside me, what happened next all started very slowly and I'll never forget the details.



He began to massage the inside of my thigh very softly and as he inched upward my thighs parted slightly. He gently pushed me back so that I was lying down, my skirt was pushed up and he teased my pen-is through the ruffled panties. Before I knew it my tights and panties were pulled down around my ankles as he now massaged my pen-is and teased my ass with his finger tips. I closed my eyes and let out a soft moan when he slid his hand inside my blouse and began to gently squeeze my soft, sensitive nipples through the satin bra.



He shifted his position on the bed and I felt something brush my lips, I opened my eyes to discover his semi-hard pen-is directly infront of my face. I pulled my head away but he grabbed it in his hands and pressed his pen-is more firmly against my lips.



"Open up," were his only words.



I did and he slowly pushed his thin pen-is into my warm, wet mouth.



I had no idea what to do and at first his presence made me gag. He slowly began to pump his pen-is in and out of my mouth but it only made it worse, he finally pulled it out and whispered, "suc-k and lick it a if it were an ice cream cone."



I noticed a slightly musky and salty taste as I did what I was told, within a few minutes it grew longer and harder, Thankfully, he did not have a large pen-is, it was quite slender and the head was shaped almost like a tulip. His breathing became deeper and then he abruptly pulled away.



"Roll over on your stomach."



I did as I was told, he took my hips and gently pulled them up motioning me to raise my bum and get up onto my knees. He left me there in that position with my chest against the mattress and my bum up in the air as he reached over to the bedside table. He pulled out a tube and began smearing it's contents onto his pen-is. Next I felt him smear thick globs of it between my butt cheeks. I struggled but he reached around my waist and firmly held me in place as he pushed the tube against my anal opening and squeezed some inside me. I flinched and struggled more when he pushed his finger deep inside me to lubricate my ass.



"Relax your muscles or it will hurt", were his only words as he pulled out his finger. I started to whimper and cry into the mattress as I felt the weight of his body press against my backside.



"Please don't, I do anything you want but please don't......".



Before I could finish the sentence he pushed his pen-is inside me. I let out a soft scream as he filled me making it feel like I was going to be ripped open. At first the didn't move and let me become accustomed to the feeling of his pen-is inside me. When I relaxed the discomfort subsided it was only then did be begin to gently pump his pen-is in a slow rhythmic motion. It went on for about 5 minutes before I could hear is breathing quicken and then very suddenly I felt a warm gush as his "love juice" filled my bum.



I lay on my back whimpering softly as he left the room for a moment, returning with a cloth diaper and plastic pants. Quickly he pinned the diaper on and slid the plastic pants up over them. I could feel the mixture of his "love juice" and the lubricant begin to ooze out of my bum as I lay there and fell asleep exhausted.

[archives]

Grandpa's Diaper Sissy Part 8 by Stephanie

I woke up the next morning with my bum still searing with pain. I couldn't tell what was worse, the pain from the spanking or from having my virgin bum penetrated from the first time. I desperately had to pee and when I did it only made the burning pain on my bum worse as the urine touched my swollen bum.

After breakfast Grandpa told me to quick shower and meet him in my room because we had a visitor arriving at 10:00am. The warm water stung as it hit my red bum, looking in the mirror I could see the evidence of how severe my spanking had been. My entire bottom was a faint pink except for 5 or 6 large red marks in the exact shape of the wooden spoon.

There was no way my poor bottom could handle another beating and I would have to be on my best behavior because Grandpa was still not too pleased with me. As I lay on the changing table Grandpa smeared soothing cream on my sore bottom before he pinned the diaper on he produced a butt plug, once lubricated he slowly pushed it inside me. Immediately my poor bum felt as if it were being torn open by the firm rubber plug. I was surprised how tightly my butt muscles gripped it in place. A cloth diaper and pink plastic pants came next and finally I was put into light pink tights and matching leotard which did nothing to hid my diapered condition.

Promptly at 10:00 the door bell rang and he lead me down to the door to greet our guest. Her name was Ava and she was the seamstress who made all the outfits for him, she was about his age and they seemed to be good friends. She wasn't shocked by my attire and merely smiled as Grandpa suggested we go upstairs.

For the next hour or so Ava had me try on each and every outfit over my leotard while Grandpa relaxed in the Wing-backed chair and watched as I came out in the outfits. Most of the outfits fit reasonably well and only required minor alterations if any.

He was pleased that not much work would have to be done and suggested to Ava that they go through her catalogues and pick out some additional outfits to make including some more appropriate ones that I could wear out in public. I let out a moan and he shot me a stern stare followed my a firm smack on my padded bum.

"We have guests coming in a couple hours so I want you to get changed into the outfit I've laid out in your room and then come downstairs".

He and Ava went downstairs to review the catalogues while I pondered who would be coming now. On the changing table he'd laid out the outfit, it was a white, girl's communion dress complete with white tights, rhumba pants and matching shoes. The dress was white taffeta, with thick ruffles around the hem, sleeves and high neck. The built in crinoline puffed it out and thankfully this dress was long enough to cover my diapers. Once dressed I decide to look around his room and adjacent study while he was occupied with Ava and I had the chance to be alone.

His night table drawers had the usual reading material, plus condoms and lubricants but nothing terribly exciting. His study proved to be much more interesting, there were numerous books on sexuality and folders of material dealing with various fetishes including tons of material on crossdressing and adult babies. On the desk was a file titled "Vancouver Daddy/Little Boy and Girl Society",

I was about to open it when I heard his heavy steps come up the stairs. I dashed out of the study, the rustling of the taffeta gave me away as I scurried into his bedroom just as he was opening the door.

"What are you doing up here?" he asked suspiciously.

"Oh nothing, I just wanted to make sure my outfit looked all right."

He gave me a suspicious look when he noticed the door to his study was left open. I got very nervous as he walked past me and disappeared into the study. He reappeared and seemed satisfied that nothing was disturbed. Ava thought I looked adorable in the outfit and commented that I was the cutest boy he'd had so far. I sat quietly beside Grandpa Bob on the sofa as they discussed some outfits feeling about as bored as I must have looked.

My interest peeked up when he said, "When Eckhardt arrives with his little Jamie we can see what he wants to order and finalize our choices."

What was that all about? It sounded like someone would be coming over with another person who was a "Sissy".

It was a little after noon when a car came down the drive and parked infront of the front door. Bob took me by the hand and lead me to greet his guests, when he opened the door a very tall, distinguished looking man in his 50's greeted him. He had a deep, booming voice, and spoke with a thick German accent. He must have been at least 6'5" and 250 lbs. and looked like someone you would not want to upset. Beside him stood a young guy probably in his mid 20's, he had longish blond hair, had a very slim build and was maybe 5' 6" at the most. He was dressed like a little boy in a sailor suit consisting of a white hat, white top with blue trim, white shorts, white knee socks and white saddle shoes with matching blue trim. The shorts were very short and puffed out by what I assumed were thick diapers and plastic pants. Around his neck was a baby blue ribbon with a baby's pacifier attached to the end.

The two adults returned to the family room while Jamie and I walked behind, I could now see through the thin white shorts the outline of his diapers and plastic pants and that distinct waddle that toddlers have due to their bulky diapers. Ava obviously knew Eckhardt to and they immediately discussed some clothing ideas for Jamie. Grandpa Bob suggested that Jamie and I go outside while they were busy. Anything beat sitting around the house so I started to get up but Jamie just looked over to Eckhardt and only got up after he was told it was okay.

Once outside it was my chance to find out more about Jamie and what was going on with us both. Jamie was 25 years old and had been with Eckhardt for almost 2 years, like me he was treated like a little boy every weekend and during his vacation from his full-time job. Like myself he answered an ad and he too had a diaper fetish since he was a child. He told me that both Bob and Eckhardt were very strict and expected to be listened to, it was important that I learn to act and think like a child as it would make the much more enjoyable and rewarding. If I acted up or ever made the mistake of embarrassing either of them infront of someone else I would regret it.

I told him about what had happened the night before and was shocked to hear that that was very mild punishment. I asked him about this "Vancouver Daddy and Little/Girl Society" that I'd seen in the den and he told me that it was a group of older business men that enjoyed treating younger men like little boys and girls. At the moment there were four men who each had a "child" and that the other two had girls like me. All the men were very successful and spent a good deal of money on making the experience as realistic as possible which explained all the clothing and furniture.

Since I was still new to this whole experience he told me that I could expect to be treated more severely at the beginning and once Bob was satisfied that I would always behave properly the treatment would become more relaxed. At the beginning the worst part is being taken out in public but once you get use to it it is not that bad.

"But how can he take me out in public dressed like a little girl, it's pretty obvious that I'm in fact a guy".

"Well, that's why he probably has had Ava make up some little boy clothing for you too."

The question I dreaded asking him was if he was expected to mess in his diapers too. He laughed when I did and told me that of course he did and if I hadn't done so yet I could expect it to happen soon. He told me about how for the first 3 weekends he avoided it too and it angered Eckhardt so he taught him a lesson he hasn't forgotten since.

Before I could ask what it was Grandpa Bob called us inside for lunch. The three adults and Jamie had sandwiches while I was put into the highchair and given a big bowl of oatmeal and a bottle filled with prune juice.

Jamie laughed when he saw it, "Looks like you'll be dealing with something else pretty soon."

It was pretty obvious this stuff was going to make me go to the bathroom. I rarely had bowel movements more than every 2-3 days but Grandpa Bob expected it to be a daily occurrence and preferably more. The oatmeal tasted fine but the prune juice was foul. I barely touched it by the end of lunch but I was made to sit there and finish it before I could get up and leave the table.

For the rest of the afternoon Jamie and I watched TV and at about 5:00pm he and Eckhardt left and my day ended uneventfully.