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 they 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 key, just in case I was at work when she found inspiration. I didn't
think much of it.

   I only worked a few hours in the morning, cleaning up a local movie
theater from the night before. The rest of the day, I had to myself. I tried
to watch TV for a while, but quickly got bored. I tried to find some of the
local boys, who liked to play football in my yard, but didn't like me. I
was considered a wimp, especially since my sister was bigger than I was,
even though she was two years younger. Mary was also a bully to
everyone, including me. With no one to play with or no good TV shows
to watch I went back into the house. For some reason I decided to explore
my sister's room, so I went in to her room and start looking around. Her
room was very frilly. She was also messy. Pants, skirts, panties, and her
training bras were all over the place. I saw a pink, nylon, ruffled pair of
her panties on the floor. I picked them up and examined them. They were
very soft. I placed them up to my cheek to feel the smoothness of them. I
wondered what they felt like on my cock, so I pulled down the front of
my pants and underwear and rubbed them up against myself. I got an
instant hard on. In fact, I had never been so stiff.

   I thought, I have all weekend; I wonder what it would be like to dress as
a girl. I figured to get the full effect, I would have to shave
what little hair I had on my body. I ran the bath water and put bath soap
and baby oil in the water as I had seen my mom do on several occasions. I
stripped naked and got in. I found my sisters shaver, lathered up my legs
with soap, and started shaving my legs. I took my time, because I had
heard my sister complain about nicking herself. When I finished my legs,
I was amazed at how smooth they felt. I decided to trim my pubic area and
shave under my arms as well. I had left a small patch of pubic hair around
my still swollen cock. My underarm hair was gone with four quick wisp
of the razor. The baby oil had made my skin very smooth. I just soaked
for a while to feel the softness of my skin.

   I finally broke out of my fantasy and got out of the tub. I dried off and
put my male clothes in the hamper, besides, no one was home and I could
walk around naked, and no one would know. I decided I would stay in
my sister's room for the weekend. I found the pink panties I had played
with before. I pulled them up my legs. My cock became hard again as I
adjusted them around my waist. I just stood there feeling my cock through
the nylon material. I thought, "Stop, I have to put on a bra, and a?" I
picked up one of her training bras. I put it over my shoulders and tried to
snap it in place, but couldn't. I thought, "How does sis put this on?" I
decided I could hook the bra and twist the bra around front, then pull up
the shoulder straps. I tried it, and it worked. I decided I didn't want to
dress all the way up, so I pulled out one of my sister's camisoles and put
it on. I was really hard now. I closed her dresser drawers and walked out
in to the living room. I twirled around feeling my body through the
lingerie.

   All the sudden I heard a voice say, "What do we have here?" I froze
with fear. It was Gina and she walked in front of me with a smirk. "I see
with have a girlie wannabe here." I tried to say something, but just started
crying. "Now, now you little sissy, what am I going to do with you?" I
just stood there.  I had never been so embarrassed. I tried to leave, but
Gina grabbed my arm, "Stand right there, you little sissy bitch, I tell you
when and where you will be, or I'll tell your family how the son is a sissy
and likes to wear his sister's panties." I just stood there and tried to stop
crying. While I stood in the living room I, Gina picked up the phone to
call some of her friends. "Yeah, come over, I have something for you to
see." I started to cry, "No, don't let me be seen by anybody, I'll be
good." Gina held my face and said, "Shut up you sissy, my friends and I
will have fun with you, and you will do as we say, or else." "Got it, you
baby? I just shook my head in acknowledgement.

   Soon, Gina friends showed up. There was Karen, Misty, and Carol.
The surrounded me and laughed and pulled at the panties I was wearing.
Carol said, "Look at the sissy, he likes wearing his sister's panties."
Misty pulled my bra strap and said, "He wears his sister's bra too." Gina
told them, "Have your way with this sissy, he needs to be taught how to
obey and serve." Karen, who seemed shy at first, pointed her finger in my
face and yelled, "Kneel you sissy slut," and pushed down on my
shoulder. I kneeled in front of her. She slapped my face so hard that my
cheeks became red. I started to cry again. Karen then unbuttoned her tight
jeans and pulled down the back exposing her tight round ass. "Lick my
crack you stupid bitch!" I stuck out my tongue and just laid it at the top of
her crack. She bent over and pushed he ass into my face. "I said, lick it
fucking sissy!" I started licking her crack. She moved up, so my tongue
would move down her crack. Soon I was at her hole. "Lick my ass hole
you cry baby slut!" I hesitated, so Misty slapped the back of my head and
screamed, "She said lick her ass hole you fucking cunt." I stuck my
tongue out farther and stuck it into her ass hole. Karen reached her hands
behind and grabbed my head and held it in place as I licked harder and
harder. Then she moved away and Carol pushed me to the floor. She had
her school uniform skirt on. She pulled it up. She was a wearing thong
pantie. She sat on my face front ways grinding her mound into my face.
"Open your mouth!" I opened my mouth a little, but she yelled, "Open
wider slut!" I open really wide and she forced her panty-covered pussy
into my mouth. She began to rub back and forth. Moaning louder and
louder. Then she pulled her panties to the side and spun around so her ass
was in my mouth. "Eat my ass you puke!" I stuck my tongue out and
rimmed her hole, because I feared what was coming next. Misty started
rubbing my cock through my panties. I became hard instantly. I heard her
say as I was licking Carol's ass say, "I see this sissy really likes his
panties and what is happening to him." The she slapped my dick, hard. I
yelped, but was muffled by Carol pressing her butt hole on my mouth.
Carol suddenly got up and yelled, "Get up bitch!" I started to stand, but
she pulled me up quickly. "Stand there like a good sissy bitch!" I stood
there with Carol's juice glistening on my face.

   I heard the voices of boys coming in the front door. I froze in shock as I
saw Drew and Harry standing there laughing at me. "What is he doing,"
he questioned Gina. Gina replied, "We have ourselves a little sissy here."
Carol looked at Drew and said, "I need you to payback a favor." Drew
said, "Yeah, anything for you Carol." Carol smiled and said, "Go to the
sofa and take off all your clothes." "In fact, both you and Harry take off
all your clothes." Drew and Harry looked at each other and said, "No
way, I'm not taking all my clothes off unless I get to see some tits and ass
with a lot of cunt thrown in." Carol looked at them with the look of the
devil in her face, "You will or I tell everyone about your little secret!"
Drew started to take off his clothes. Harry thought for a moment of what
could have scared Drew so much that he would start taking off his clothes.
Drew looked at him and said, "Just do it, I'll tell you later." Harry
thought, "What the hell," and started taking off his clothes. Soon both off
them were completely naked and sat on the couch. Gina said to them,
"Just lean back boys and enjoy it." Thinking they were going to get
pussy, they leaned back. Their dicks were getting hard with anticipation.
The Gina looked at me and said, "Get to it bitch, suck them dry." Harry
and Drew started to protest, but Carol quieted them with a look. Misty
slapped my ass and said get to it bitch!" I walked over and knelt in front of
Drew. I stuck out my hand and touched his cock. He leaned back to grant
me better access. I started stroking his cock. I felt it get warmer and harder
as I stroked it. Just then, Gina yelled, "Don't feel him up, suck his cock
you fucking slut!" "Start with his balls, sissy!" I held his cock as I looked
at his balls. I decided I'd better get started, so I lower my face and mouth
down to his balls. I stuck my tongue out and gave them a small lick. The
taste was not like I thought, so I started licking them more and more. I
then took one of his balls all the way into my mouth. His started to moan.
I felt his cock get hard in my hand. I left the one ball and went to the
other. I was getting into it.

I wanted to have the taste of his cock in my mouth. I stared at the head of
his cock and licked it with anticipation. I licked all the way down to the
base. Then I took his cock into my mouth. Working the head in, then
sucking all the way down. I started sucking up and down in a bobbing
rhythm. I reached over to Harry with my hand and started to stroke him
off as I was sucking Drew. Drew was started to force his cock into my
mouth at the same pace I was sucking him. I started to feel his balls. He
grabbed my head to keep his cock in my mouth. I felt his dick swell in my
mouth. Then he shot his load to the back of my throat. Since he was
holding my head in place, I had to swallow his whole load. He let go and
slumped back into the couch. Misty yelled, "Next!" I knew what that
meant. I started the same routine. I started with Harry's balls. Licking and
sucking them, as I did Drew's balls. I started stroking him at the same
time. Karen pointed out, "Our little sissy is still a virgin and needs her
little hole fucked." Gina pulled me up and said, "Sit on his hard pole and
get fucked as a sissy should be!" Gina then pulled my panties down and
off. I straddled Harry facing him. Carol held his cock as Gina pushed me
down on top of his rock hard cock. I felt a little pressure at first, but soon
his cock, which was lubricated with my saliva, slid into my virgin ass.
Karen said, "Pump up and down on his got you sissy!" I did as she said,
feeling everyone of his thrust into my sissy hole. I pumped and pumped
as hard as I could. I liked they way it felt as his manhood pushed in and
out of my ass. My cock was getting really hard as well. I didn't know
who was going to explode first, Harry or me. I found out I couldn't hold
my load and shot all over Harry's chest. He kept thrusting into my ass
harder and harder. The her grabbed my waist really hard and thrust me
down on his cock as he filled my ass with his hot cum. I pulled off and
put my panties back on. Gina said, "Your not done sissy, you need to lick
up you mess." "So get to licking, bitch!" I leaned over to Harry and
started to lick cum off his chest. When I was finished, Harry surprised me
by grabbing face and started kissing my cum soaked lips. Carol, said, "I
guess you all figured out Drew and Harry's secret, they love fucking and
sucking each other." "I guess they have a sissy slut to include in their gay
games." Gina said, "Don't forget, we own the sissy, and his parents and
sister won't be home for a few days."

  I was ordered to clean up and put on fresh lingerie. The girls made me sit
in a straight chair in the middle of the room while the planned what to do
with me for the rest of the weekend. Gina has ordered me to stop writing
for now, but she told me I would have to tell of all my humiliation later
on.

(the end)