Sissy dreamlife
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My Sissy Life Part 10 free porn video
Part 10
After a while I heard the doors open, shut and the van started to move.
I heard my brother saying to my father that he was happy that Uncle John
was coming over tonight.
"I haven't seen him in along time, it will be cool to talk to him some
more," Jim said.
I could hear my family talking to each other as we rode home but I
couldn't really make out what anyone was saying exactly.
After a while I felt a bump as we pulled into our driveway. The van
stopped and everyone got out. I expected the door to open and my brother
or someone would let me out, but no one came. For, what I think was
about fifteen minutes, I laid there. It was completely silent as I
waited., all of a sudden the doors flew open and I saw my brother.
"Okay Bobbie," he said as he untied me "Uncle John will be here in a
little while. Go fix yourself up, dad wants you to serve drinks out on
the back patio."
He stood me up and took out the ball gag. He left the collar and leash
on.
I said, "Yes sir. I will be ready when needed." I grabbed my purse and
went inside.
I went to the first floor bathroom fix my makeup, make sure my hair and
uniform looked presentable. I wanted to stay close, incase my father
called me, so I didn't goto my room. I had all I needed in my purse.
It wasn't long before my father called for me. I went to the patio where
my family was there with my uncle.
I curtseyed and said to my father, "How may I be of service, sir?"
"Take everyone's order and be quick about it," he told me.
I took my uncle's drink order first. He said, "Oh, umm, well. I'm not
sure. Don't worry about it Bobbie, I can get my own."
My father said, "John, she will get it for you. That is why she is
here."
"That's really not necessary Jerry," he said. "I don't mind really."
I gave my uncle a look that was pleading. Trying to convince him to let
me get his drink for him.
"Sir," I said, "please let me get your drink. I would be happy to serve
you."
"Yeah Uncle John," Jim said with a laugh, "she loves serving. That's one
of the things she was trained to do. She can't think very well on her
own, so she has to be told what to do."
"Well, okay, I guess, umm, I guess I'll have a beer," he said.
I was very glad my uncle let me get his drink, I wasn't sure if I'd get
punished or not if I didn't.
Everyone else gave me their order I went to the kitchen to get the
drinks.
By the time I got back they were all in conversation. I served everyone
their drink.
I went to give my brother is drink he said, "Just put it down on the
floor in front of me sissy."
My sister giggled when she heard my orders.
I said, "Yes sir."
I was never to bend at the knees only at the waist. My brother was
sitting directly across from my uncle. So when I went to put my
brother's drink down, my uncle had full view up my dress.
It was very embarrassing, I'm sure my brother could tell. I was just
glad I did have me cleaning uniform on, that was much stiffer and would
have gone up more.
I curtseyed to everyone and asked if they needed anything. They all said
no and I turned to leave, knowing that I wasn't to stay in the room if I
wasn't needed.
Just before I was out of the room my brother said, "Hey Bobbie, come
over here and get my drink for me."
"Yes sir," I said.
I went over to him and gave my uncle the same show as before. I picked
up the drink and handed it to Jim.
He said, "Now get outta here and wait to be called."
"Yes sir," I said as I curtseyed and left the room.
About twenty minutes later I heard my father call for me. I rushed back
as fast as I could. My mother, sister, brother and uncle were kind of
huddled close to each other at the table.
"Yes sir, what can I do for you?" I asked my father.
"Refills for everyone," he said.
I said, "Yes sir."
As I curtseyed and turned to leave, I saw what the rest of the family
was looking at as my sister moved out of the way. There were 3 big books
stacked off to the side of the table they all had covers in different
shades of pink. A fourth book was open in front of them. They were
looking at photo albums. Photo albums of me to be exact. Four years of
pictures of me while I grew up as a sissy.
I went to get the drinks and came back. I went to the table where
everyone including my father was and served them.
My mother said, "There is Bobbie on her first day of fifth grade, she
was 13 years old. Look how cute she looked with her pigtails. Dressed in
her short flared cotton skirt and her My Little Pony t-shirt. With her
Hello Kitty book bag and cute little pink and white purse."
I gave out the drinks curtseyed and turned to leave. I really didn't
want to relive all those memories. I know I'm a sissy now, but those
pictures were from when I didn't understand what I was.
I was almost out of the room and my mother said, "Bobbie you may stay
here, you don't need to leave."
I knew that meant that I had to stay there.
"Is that when she 'came out' to the school?" my uncle asked.
"Oh, no," my mother said, "Bobbie was going to school with light make-up
on and her ears were pierced for a year by then."
"Yeah," my sister said, "everyone at school knew she was a sissy way
before she started dressing like one."
My mother looked at me and said, "Oh Bobbie, you looked so cute on that
first day. Look at that cute smile, those braces shining in the sun."
"She sure looks happy," my uncle said.
"She was happy," my sister said, "she could finally show the world that
she was a sissy."
They kept looking at the photo albums, my mother, sister or brother
would make a comment about them to my uncle.
"There's Bobbie at age 14, in her new serving uniform," my mother said.
"She was going to be serving at her cousin Scott's 15th birthday party."
"Yeah," my brother said, "all the guys really teased her about being a
sissy. It was so funny."
"The girls loved her dress," my sister said sarcastically as she
giggled.
"You can barely see the pink band-aid on her knee," my mother said as
she looked at my uncle, "she cut herself shaving her legs that morning.
You should have seen how much she would cut herself when she first
started shaving her legs."
My brother said, "Hey dad, that reminds me. Uncle John said when you
were in school you made some kid shave his legs, wear girls clothes and
stuff like Bobbie does."
My father smiled a little and said, "Yeah, Gail Wisner. That was a crazy
year."
"How did you get him to do it? Did ya beat him up?" Jim asked.
"No, I didn't need to," he said. "During the first week of 11th grade I
got into a fight with my girlfriend Katie in the hallway at school. Gail
heard all of it, he had a huge crush on Katie. He thought that she broke
up with me and so he asked her out. We didn't break up but just to get
back at me Katie said yes. Well, when I found out I went to his house to
beat the crap out of him. When I got there his mom opened the door and
she was hot. Her name was Mary. Now being 16 at the time I thought a lot
of girls were hot, but this was the first time I thought a mom was hot.
The term MLIF hadn't been though of yet. I thought that maybe I'd let
Gail off the hook, I mean if I beat him up I'd never be able to see his
hot mom anymore."
While my father was talking I was making sure everyone had a full drink.
"So, I asked to see his dad," my father continued. "His mom said that
she wasn't married anymore and that her husband left her for younger
woman. As soon as she said that, a plan instantly formed in my head, I
was going to have her. So, for the next few weeks I was Gail's best
friend, or so he thought. One day I came over when I knew Gail wasn't
there, when I got there his mom offered me some lemonade. We sat and
talked for awhile when I was going to leave she walked me to the door.
As I was walking I stopped, turned around and kissed her."
"Go dad!" Jim said.
"She didn't pull away," my father said, "she didn't try to stop me in
anyway. From then on we were all over each other every chance we got.
Only I wanted more, so one day I skipped school and went to her house.
Let's just say we were both very happy after that."
My sister asked "How old was she daddy?"
"She was 32," my father said. "She had Gail when she was 16. We were
good for the most part, but again, I wanted more. I didn't want to hide
the fact that I was having sex with Mary from Gail and since he was home
a lot I wasn't getting much. So one day I told him I was going to come
over after his piano lesson so we could hang out. He didn't really have
any friends so he was very happy that I was coming over. I got there
early and was banging the hell out of Mary, I had set her alarm clock
that was next to the bed off by a half hour. So she thought Gail
wouldn't be home for a half hour. When Gail got home he heard his mom
screaming and moaning, he thought she was hurt. When he opened the
bedroom door he saw his mom bent over the bed towards the door with her
head down, I was behind her with a big smile. He didn't know what to do
he just stood there and looked at us. His mom didn't hear the door open
and I kept slamming into her while looking at Gail with tears in his
eyes. He sniffed kind of loudly and his mom looked up just as I unloaded
into her. She let out an 'Oh god yeah.' before she stood up. She put a
short robe on and went over to give Gail a hug. Now most men would have
gotten mad and maybe tried to stop me, but Gail just stood there and
cried. His mom walked over to get him a tissue, as she walked up to him
she said 'Calm down sweety, we'll talk about this.' As soon as she
finished talking there was a small wet plop sound on the hardwood floor.
She said 'Oh my!' Gail looked down and saw that my cum dripped out of
his mom and landed on the floor."
"Holy shit!" Jim said.
"What did he do?" my sister asked.
"He burst out crying and ran to his room," my father said. "I kind of
thought that it was over between Mary and me. I told her that I
understood if she didn't want to see me anymore. She said that she was
glad Gail found out, now we didn't have to hide it. That blew me away, I
didn't realize that she wanted that too."
"My dad the stud," Jim said.
"Well, Gail cried and begged his mom to stop seeing me but she wouldn't.
He would cry every time he knew that his mom and I were having sex. He
cried all the time. Mary was getting tired of his constant crying, so
she really didn't try to make it easier on him. She would say things
like 'Gail, why don't you go up to your room. Jerry and I need some
alone time.' A week or two after he walked in on us. I was in school
and I heard someone say that Gail was crying in the mens room they said,
'Maybe he should use the woman's room, he is such a sissy.' All of a
sudden I had the idea of making him a true sissy. I knew I could get his
mom to believe that he was a sissy. And so, over the next month I
convinced Mary that Gail was a sissy. Less than a month later she had
him shaving his legs and dressing in only girls clothes at home. I told
Mary that things might be better for her if she had a maid, she wouldn't
have to cook and clean anymore. That's when Gail the sissy maid was
born. Things were much better after that, Gail served us food and
drinks, she took my coat when I came over, she cleaned the house, all
while I was plowing her mom in the next room. As soon as school was out
for summer Mary had Gail start full time corset training. Just before
12th grade started I was getting tired of just being with Mary, so I
told her that I didn't want to be with just her. She told me that she
was glad, because her and Gail were going to sell their house and move
in with her sister and two teenage nieces . There was a school there
that would let Gail dress in her sissy clothes. Mary thought Gail would
be happier if she didn't have to wear male clothes again."
"What happened to Gail daddy?" Kim asked.
"Well," my father said, "since her new school wouldn't accept the
credits from her old school she went back to 9th grade again. Shortly
after that, her mother put her on hormones. For her 18th birthday her
mother got her breast implants, 34D, she entered 10th grade with large
breasts. I can tell you that Gail was not like Bobbie. Bobbie loves
being a sissy, Gail hated being a sissy more than anything. But after
she got her implants she didn't seem to mind being a sissy as much."
"So, you kept in touch with Mary after she moved away?" Jim said.
"Yep," my father said, "Mary would send me pictures of Gail over the
years. In fact Gail was one of the servers at the reception after I
married your mom."
"Do you still talk to her mom?" Kim asked.
"No, her mom died about a year ago from cancer," my father said. "Just
before she died she called me up and asked if I could kind of look after
Gail. She never did very good in school and no one would hire a large
chested sissy. So I told Mary that I would try to do something. I
thought about it for a while and after her mom died I brought her to
work for me."
"What! She works for you?" both my brother and sister said at the same
time.
My uncle said, "Wow Jerry, I didn't know that."
"She doesn't really work for me much anymore and I never paid her when
she did," my father said. "Marcus form my shop, he likes girls like her,
now she lives with him. She cleans my office once a week now but I still
don't pay her."
"Marcus? The one that everyone calls Big Marcus?" Jim said. "That huge
black guy that can almost lift the back of your truck off the ground?"
"That's the guy," my father said.
"Wow, I'm glad I'm not Gail," Kim said.
My father laughed.
My uncle said, "Well, I'm getting a little tired. I think I'm going to
get going back to the hotel."
Everyone said their goodbyes and my father walked my uncle to the door.
My brother grabbed my leash and said, "Come on, I've got something to
show you."
Jim led me upstairs and into my room.
He said, "See that piece of wood over there on the floor sissy?"
"Yes sir," I said.
There was a piece of wood on the floor and against the wall it was about
three inches high, about 4 inches wide, 10 inches long and it was
painted pink to match my room.
"See those two hooks on the wall?" he said.
"Yes sir," I said.
"That is a new punishment, it's also to keep you out of the way and
still know where you are and what you are doing," he said.
"I don't understand sir," I said.
"Ok, let me show you," he said.
"First, go get on whatever you wear to bed," he told me. "I'll be back
in a second."
I put on my pink satin nightie. Jim came back with a pair of handcuffs
in his hand.
He said, "Ok, now go stand on that piece of wood and face the wall."
"Yes sir," I said and as I did as I was told the wood sank into the
carpet about an inch or so.
The hooks in the wall were small and shiny. They were circles with the
top cut off and were mounted in the wall at about the same level as my
nipples.
Jim said, "Lift your dress over your nipples."
I knew what was next. He came up behind me and grabbed my nipples, then
he hooked my nipple rings on the hooks.
He said, "Now put one foot on each side of the wood."
I did and there was a slight pull on my nipples. Then he took the wood
away.
"Now put your legs together," he said.
I did and there was no pull on my nipples anymore.
He had me put my hands behind me and he cuffed my wrists. Then he went
to my clothes hamper and took out the pair of panties that I had been
wearing all day and stuffed them in my mouth.
"I'll leave you there for awhile so you know what it will be like," he
said and he went down stairs.
I could have pushed the panties out of my mouth with my tongue but I
knew that I'd be punished for sure. I tried to stand on my tiptoes and
lift my nipples off the hooks but I couldn't get high enough. So I just
stood there and waited.
The end of part 10.
Elle
- 10.10.2022
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