High School Sissy free porn video

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Even when growing up I always seem to be on the fem side, my shape
was more of a girls shape then a boys. As I was growing up my parents would
always dress me clothes that were stuff that a boy would wear, because if
they dressed me in something that was sex neutral I be mistaken as a little
girl. As I got a little older I liked being a boy since jerking off was
always fun. But when I was alone I find a way to get into my older sisters
room and try on here clothes. By the time I was 16 I have to say that there
were times I be able to get dressed in one of her outfits and almost pass
for a girl.

One weekend when I was 17 my parents were going to be way for the
weekend they had decided to go visit my older sister at her school. It was
a good day?s ride so they figured they make weekend out of it. They felt
that since I had my driver?s license and be able to get where I needed,
they also felt I could take care of myself. They also decided that they
take my other sister with them. When they left on Saturday morning, before
I even got out of bed. I woke up and was feeling horny so I was going to
jerk off but decide I would wait. Since no one be home for the next 2 days
I hit my older sister?s room to see what trouble I could get into. Since a
lot of her stuff was at her dorm room I found some boxes in the back of the
closet. I went thru them and found a few outfits that would fit me since
the truth was I was on the thin side and had a shape closer to a young girl
then a boy. The only give away was my cock and even that was smaller than
average. Just for your information I had played with another boy before.
The boy was one of my best friends. I had at times sucked his cock a lot
more then he sucked mine. Even a few times he fucked me I did like that
very much I liked feeling like a pussy boy.

But back to the box of clothes, I pulled them all out and was
surprised to find a dildo in the box. I figured I had time so I selected a
few items that I wanted to try on, I found some frilly under panties and of
all things there was a padded bra in the box. I put the outfit on and have
to admit I looked pretty good. I then used the dildo on my ass and was
fucking myself and the more I did the horny I get. I decided to get on line
and go to a gay site that had cam access so the guys could see me all
dressed up. I got mixed reactions some guys like the girlie guys and some
did not. I started chatting with a guy a few miles away from me and he
really liked the idea that I like dressing like a girl and asked if he
could get away. I said I could and he asked if I would drive over dressed
like I was. I figured it seemed like a good idea at the time so I did.

My hair was on the long side so I could be easily taken as a girl
driving in the car. So here I was in daylight I went out and drove over to
the guys house, I just felt like a girl and a slutty one at that. When
arrived there and went into his house we played and he did treat me like I
was a girl and he did fuck my boy pussy and my mouth for the few hours. It
started to get dark and the guy was tired from fucking me so it was time
for me to drive home.

Since I had not brought any other clothes I left still dressed
in my sister?s outfit. I drove a while then my car oil light came on, I got
out and checked oil and sure enough it was low. I knew there was a gas
station a few blocks away so I decided to walk. So here I was in a section
of town that was not the best and in a short skirt with half my ass
sticking out, I imagined I looked sexy but I was thinking this was not the
best idea I ever had. I needed to get a can of oil so off I went, I reached
the gas station walked in and picked up some oil and walked back as fast as
I could. The guy in the gas station did look at me a little strange I think
he suspected there was a cock in my panties, but he did not say anything
and I walked off back to my car. When I got back to the car I opened the
hood and was bending over pouring the oil in, I realized there were a group
of four guys walking over to me. I was finishing up when I felt a hand on
my ass. That in itself was not a problem but what was when the happening
was he reached down further to get a hand full of pussy, but then he felt
my cock. He grabs me and says to his friends we got us a faggot pussy
boy. He then grabs my cock and holds on and starts dragging me with him,
the other boys follow. I am pulled into an old building a few hundred feet
away from where my car was. Then this guy who's got my cock tells me to get
on my knees and he lets go of my cock and then drops his pants and out
falls a good size cock, the guy was around 19 years old. Then he grabs my
head and tells me to open and shoves his cock in my mouth. Being a cock
sucker that I am I was OK with this. I have to admit I liked being forced
to suck the guys cock. After the boy fucked my mouth he said let?s see if
he has a tight pussy, then I am bent over and my panties were ripped off me
and while bent over they fucked one after another. There were the 3 other
guys and then again by the guy who I had sucked off to start with. By now
my ass was sore but I did get to feel like what a girl would if she was
getting ****d. I had to stay long enough for 3 of the guys to fuck my ass
again, but by then they were getting bored with using there pussy boy.

They let me leave so I walked back to the car with cum
leaking out of my ass, no longer even had any panties on to catch some of
the cum. I drove home and if I was not such a pervert I would have felt bad
about what happened, but instead I went to my room took the dildo that I
used before and fucked myself even more and jerked off thinking of all
those cocks that used my boy pussy.

A few days went by and my ass was no longer sore but I had the
desire to have it filled again like it did last weekend, The friend I
played with was fun but the guys on the street were rough and they just
used my boy pussy like it was there for their enjoyment. The crazy part is
I felt my position in life was to make guys use me for their pleasure. When
I put on the girls clothes I just felt like I was a cock sucking slut that
had to be used. I did not care if they fucked my mouth or my ass just as
long as they filled me with cum. I was not sure what I was going to do
about it. I went out a few nights and traveled over to the area where the
guys who ****d me the other night hung out, I was not dressed like a girl
but would have liked have been but the house was not empty so that I could
have. I was able to find the same guys, they were outside an old house that
I think was vacant and they took it over as a club house. I did not stop
but I was sure that at least 3 of the guys that were there were the guys
that fucked me.

I waited for the weekend and my parents were going out and my sister had
a place to go. I told them I was going out, and was going to spend the
night at my friend?s house, they were OK with that because they knew
sometimes we get involved in video games and I wind up staying late. If
they knew the truth sometimes I stay late because my friend happens to also
be fucking me. But the fact that he fucks me sometimes is a different story
when he does I am not dressed like a girl I am just a normal teen age boy
cock sucker. So back to my plan after my parents and sister left, I pulled
down the box of items that transform me from being a boy into a teen girl
and a slutty one at that. I then got dressed and made sure I did a good job
making sure my boy pussy was loosened up with the dildo and that my pussy
was nice and clean.

Then as soon as turned a little dark outside I walked to my car and
made a trip straight to where I knew the boys that fucked me last would be
hanging out. I saw them standing around on a corner under a street light,
there were 5 guys this time. I rolled up and opened up the window I made
sure that they could see me dressed in my sexy clothes, the one guy came
over who had grabbed my ass last time and he recognized me. He just said
to the other guys look that cock sucking faggot is back guess she wants a
lot more cock. I just smiled and said you have that right and with that
they told me to park and come with them. I followed them to the house I saw
them using the other day as a hang out. When we walked in there were a few
more guys there and the one guy who brought me in said to the other guys
look what I found a faggot who thinks he is a girl. Then again he does suck
cock very nice and his ass did feel good when I fucked it last time. With
that a few of the guys knew what they wanted. I watched as a few of the
guys removed there pants and their cocks were exposed. They gestured for me
to come over and service their waiting hard cocks. As the good cock sucking
girl that I wanted to be I just got down on my knees and crawled over to
them, I knew it looked real slutty but that is what I just wanted to be a
slutty cock sucking pussy boy. I took the first guys cock in my mouth and
did so because even if it was not supper hard it was the biggest cock out
of all of them. I started sucking him taking him in my mouth as deep as I
could, sometimes choking on his big cock as he fucked my mouth. I did not
as of yet get to be rewarded by his cum since another guy stopped me and
made me suck him for a while. Then six guys formed a circle around me and I
would go from one cock to cock just sucking them a while then moving
on. Never getting my mouth filled with cum that I wanted and needed. This
went on for a long time then one of the guys grabbed my head as I was
sucking his cock and did not let me move on as he shoot his load deep in my
mouth. After that I moved to the next cock still tasting his cum but also
the taste of the new guys cock. A few guys while I was sucking this guy?s
cock were jerking off so I was now getting my face and head coated with
cum. I was still busy with a cock in my mouth or I would have told them do
not waste any cum, I wanted in at least one of my holes.

The cock that was in me shoot his load into my mouth he pulled out
and I felt some cum that was shot on my lips dripping down so I used my
fingers to move it to my mouth and swallow what I could. Then the guy who
fucked me first last time told me to get up and bend over the arm of the
chair and I did that and he ripped off my pantie and slid his wet hard cock
into my boy pussy. I moaned so the guys knew I was loving this, He just
fucked me hard. I could tell he was there to satisfy him but doing so made
me feel even more of a slut. I kept telling him to fuck me harder and he
did, but doing so made his ride a lot shorter and he was soon spurting his
cum into my ass. I just loved the feeling and was just the start for the
night. I stayed bent over the arm of the chair and guy after guy took my
ass. There were so many guys fucking my pussy I lost count as the guys took
turns fucking me hard. I stayed till late in the night and while I was
being fucked some of the guys left and some new cocks showed up. After so
many guys fucked me my ass was so filled with cum it was dripping out but I
was still wanting more. This went on for another 2 hours then it was time
for me to leave.

I left but not sure why I was feeling this way but I still wanted
more, and it was late so I could not go home now dressed like I was. Now my
outfit was half missing and if I bend over my boy pussy would show cum
dripping out of it. I decided that the guy I met on the internet was not
that far away and he lived alone so I called him. He was sleeping but when
he heard my voice he told me to come over. I arrived and when I walked in
his house he could see what shape I was in, He told me to bend over and he
took a look at my boy pussy and said how many times did you get fucked. I
smiled and said not sure lost count. I figured he was going to fuck me and
I was more than willing to let him. He wanted to wait after we both went
back to bed and he said he fuck me when we both woke up. I agreed to this
but trying to sleep naked next to this man was not easy and next thing I
realized is I am under the covers sucking his cock.

I think that woke up his cock at least and he fucked me one time
before we both crashed. I assume all the sex had the day before tired me
out because I slept later then I would normally sleep. When I woke up I
heard talking from the other room, I was wake enough to remember what took
place yesterday and that I stopped by this guy?s house last night.

I made some noise getting up and the man who house this was came
in, along with 2 other guys. The guy who fucked me last night told me to
bend over he wanted to show his friends what my well used boy pussy looked
like. I did as he asked and they could see my hole was still stretched and
dried cum all around it. I figured the fact that these 3 men all around 30
were looking at a boy pussy of a k** was 17 was a turn on because all of
their cocks started getting hard. I figured they just fuck me then but the
guy who owned the house told them if you thing that?s hot you need to see
how he came dressed yesterday.

The guy had me get up took me into the shower now we were both
naked and he helped was me up and cleaned all the dried cum off my pussy
and legs. He got me out dried me off and put some cream in my ass using his
fingers. The cream did fell soothing and also greased up my hole. He then
had me put on the outfit I had on yesterday minus the panties since in all
the sex I had I had lost them. When we came out of the bathroom he had me
spin around and his two friends looked at me and from there hard cock I saw
they approved.

I spent the rest of the day sucking their cocks and them taking
turns fucking me, over and over again filling my boy pussy with their
cum. While we were having fun I received a message on my phone that my
parents were going out again so that took care of figuring how I was going
to get back in my house wearing a mini skirt top and no panties.

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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

4 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

2 years ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

3 years ago
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I...

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