Wannabe Sissy Part One The initiation
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Panty Sissy Initiation free porn video
My name’s David. Like sissy boys, I learned the joys
of masturbation at an early age. I couldn’t help what
comes natural. But what came after that, well, I’ll let
you decide.
After about six months of jacking off in my room, I
became more brazen. I was almost eighteen when my parents
went out on the town and left my sister
Kelly and I alone for the first time . I was supposed to watch over her, and not let
her stay up too late, but she ended up watching over me.
I told her she could stay up until 9, but she had to get
her pajamas on now. Then I went into my bedroom and took
off all my clothes and just put on a bathrobe. The rest
of the evening I watched TV and played games with Kelly,
secretly excited with being naked underneath my bathrobe.
Sometimes the folds of the bathrobe would part when we
were sitting on the floor, and I would be slow to close
them back up, but I was never really naked, and Kelly
never said anything, so I thought my secret game was
safe. My erection was getting harder (and harder to
hide), so I finally sent Kelly to bed at 9:30.
I then rushed to my room, stripped off my bathrobe, and
began touching myself, stroking my cock and remembering
all the excitement I felt earlier that night. Then Kelly
surprised me by opening my bedroom door, and seeing me
naked, asked me what I was doing. I half-heartedly tried
to cover up, but my mind was going a thousand places at
once. I couldn’t decide what I should do, or wanted to
do.
I said, “I was doing something private”, and that she
should go back to bed and not tell Mom and Dad what she
had seen. “You will understand when you’re a little
older.”
“I’m thirteen, just like you”, she replied. “Besides, I
wanna watch. If you don’t let me, I’m gonna tell.”
“OK,” I said, “but you got to take your underwear off
first. It’s only fair. You’ve already seen me naked, and
you didn’t knock first, so I should see you the same
way.”
“Just for a second,” she said. “Tell me what you were
doing.”
So, at the tender age of fourteen (almost), I got to tell
my sister all about sex; jacking-off all the while and
staring at her open pussy as she sat cross-legged three
feet away from me. She may have heard what little I
knew, but that night is when I learned about
exhibitionism. I was confused by all the thrills, but I
didn’t want it to end. I must have played with myself for
an hour while she watched. And I loved watching her
watching me. I don’t know what else would have happened
if we hadn’t heard the car in the driveway.
Kelly rushed to her room, and I jumped up, getting ready
to turn off the light when I saw her underwear still on
the floor. I grabbed them, snapped off the light, and
dived into bed. My heart was pounding, partly in fear of
getting caught, partly from the excitement of being
caught by my sister, partly in the thrill I got of doing
something so “naughty” while Kelly had watched, and
finally in the uncertainty of what would happen next.
For the next hour I kept my eyes closed. I couldn’t
sleep. I was just listening, wondering what would happen.
Would Kelly say anything? I didn’t know. Finally the
house grew quiet. Then I realized Kelly’s underwear was
somewhere in my bed. I had to get rid of them before
morning, or at least hide them somewhere.
But in the meantime.
Oh, what a night that was. Exhibitionism, panty sniffing,
(almost) endless masturbation, and more mixed emotions
than I could handle.
Which made the next days all the more confusing. Kelly
didn’t say ANYTHING about what had happened. Just like it
never happened.
Here I am, a budding exhibitionist, and nobody’s
watching.
Chapter Two
***********
Kelly never told.
She never said anything to me, but sometimes she would
give me a secret smile when I came out of my bedroom
after beating off for a while.
At first, I thought she was afraid of getting caught, but
now I’m not so sure.
For a while, she would sneak to my door and stand in the
hallway while I was jacking off, not knowing she was
there. Then she would open the door just a little, and
watch. Just enough to let me know she was watching.
I liked this. For the most part, anyway. There where a
few close calls when Mom came down the hall and Kelly ran
to her room, leaving my door open and me buck-naked on
the floor with a hard dick in my hand and my mind
elsewhere. It was still exciting to do it while she
watched, but it wasn’t the same as that first night. And
Kelly doesn’t open the door that often, so the thrill was
more in the past memories.
We’re older now; we both just got driver’s licenses.
Kelly’s developing a fine figure, with oh so soft
breasts. I wish I could touch them, stick them in my
mouth. Or eat her pussy, I’d love to do that. But I
haven’t been able to tell her.
Kelly’s been on a few dates, and I hear she’s a tease. I
can believe it. She still opens my door once in a while,
but not very often. Last time she did it, she had just
come out of the shower. She opened my door, then opened
her robe. What a glorious sight. I stroked harder than
ever. She never said a word, just smiled. I rubbed myself
raw that night, and then had to give myself a rest for
the rest of the week.
I go out once in a while, even had a girl friend or
three. I’ve had sex with them, eaten their pussies, and
shared many intimate moments with them, but I couldn’t
bring myself to tell them of my really hidden fantasies.
I’m becoming obsessed with pussy. I’m afraid I’ll do just
about anything to get it, and I’m not sure where that
will lead, so I hesitate. No one knows, except for Kelly.
And I haven’t told her all my fantasies, yet. But I think
she has a few of her own.
Seventeen is a wonderful age. I have a car, so I can get
around, and I’ve discovered the X-rated Drive-in movie. I
go there every Friday night, sometimes alone, sometimes
with a date, but I go EVERY Friday.
At first, I was somewhat shy about being at such a place.
I wanted to masturbate to the movies, but I didn’t want
to get caught by someone going to the refreshment stand.
So that first night I just enjoyed the movies and
pleasured my self at home the rest of the night with
memories of what I had seen earlier.
But the thrill was too great. The next time I went to the
drive-in I wore shorts and a tee shirt. Within half an
hour I was naked from the waist down, and stroking in
time to the movies. The driver’s window was down ’cause I
was so sweaty, and the windows were steamed up. I still
kept an eye in the mirror for people walking by, but now
I was hoping a couple of girls would wander by. Boy,
would I give them an eyeful. Sometimes they’d scoot on
by, and sometimes they would linger.
“Poor boy, all alone?” one pair asked me. “We’re going to
get sodas to wash down all the come we sucked out of out
boy friends cocks. Shoot off for us, please.”
How could I refuse? One of the girls stood right next to
my car door, and raised her skirt just enough to show me
that she wasn’t wearing any panties. I stuck my nose
right in her crotch and sniffed. And kept on stroking.
She grabbed me by the back of the neck and rubbed my face
with her cunt lips. Oh ecstasy! She even let me take a
couple of licks, but then said, “Gotta go now. Lover.
Maybe we’ll meet again. You lick real good. Bye.”
My heart was pounding, and my cock was throbbing. What
could top this?
I was soon to find out!
There’s a certain unwritten etiquette about drive-in
masturbation. Usually there’s an empty space between each
car. Sometimes a guy will park on my passenger side, but
I’m not interested, so eventually he’ll go away.
That night was different. I was still recovering from the
soda pop girls when a couple pulled up right next to my
driver’s side. A high school couple! I was stroking
again. The girl slid over to my side to get the speaker,
and then slid back. After a minute, she was back by my
window.
“Excuse me,” she said. “Our speaker is broken, and I was
wondering if you could turn yours up a little bit.
Otherwise we’ll have to move somewhere else, and I kind
of like it here. I’m here with my fiance, and I’m afraid
he’s the jealous type, but I think we can still have fun
together.”
“I’ll be glad to share”, I said. “My name’s David.”
“I’m Dawn”, she replied. “You come here often?”
“Every weekend.”
‘How about tonight?’ she smiled.
I hesitated. “My dick’s sore, and my shirt’s wet, but I’m
not through yet.” I answered.
“Maybe you need something softer,” and with that she rose
up off the seat and pulled her panties off from under her
sundress. And threw them in my window. “We’ll talk later,
I’m going to fuck my date first.”
She slid back over and unzipped his pants. I could see
her play with his dick as he rubbed her breasts.
I wrapped her panties around my dick and keep in time.
Dawn was watching me, so I held them up to my face, and
sniffed her womanhood-scented panties. She lifted up her
skirt, climbed on top of that cock, and began to fuck.
All the while she rested her head on his shoulders, and
watched me. I was so delirious, I couldn’t keep my eyes
open; but every time I looked, I knew she was watching
me.
“I thought that was you,” I heard over my shoulder.
“Oh no”, I thought. “I forgot to check the mirrors.”
There stood Kelly, watching me again. I wasn’t about to
stop, but she reached in and grabbed the panties out of
my hand.
“These yours?” she asked. “I know they’re not mine.”
“They’re mine,” Dawn said, “but he can keep them if he
wants to,” the entire time still fucking her fianc�.
“I’m Kelly,” she replied. “And this is my pussy whipped
brother, but I guess you’ve already met.” With that she
held Dawn’s panties in my face and said, “Don’t stop yet,
David.”
Then she slipped Dawn’s panties over my head, arranging
them so I could see out of the leg holes, and reached in
to grab my cock. Leaning in the car, she began to jack me
off.
“Like this?” “Go ahead, tell your friend what you think
of her panties.”
The aroma was just too much. ” I love pussy,” I replied.
“I’m going to keep these, and never wash them; and I’ll
sniff them every day as I jack off.”
Kelly kept pumping on my dick. Sometimes rough, sometimes
gentle, somehow I wasn’t surprised she knew what she was
doing.
When I was about to come, Kelly whispered in my ear,
“Raise up, so your friend can see you come.”
I was in her control. Anyone watching would have seen my
cock in the window. I wasn’t about to stop now. I shot a
big load of cum in Kelly’s hand.
“That’s a good boy,” Kelly cooed. “Rest a minute, I’ll be
back.”
My heart was pounding, I was breathing hard, and every
breath reminded me again of Dawn’s panties still on my
face.
Dawn had moved back to my side, and was watching
everything with interest.
Kelly talked with her for about 15 minutes, but I
couldn’t make out what they were saying.
Then Kelly turned to me and said, “David, I did come here
with a date, so I got to go. Make sure you thank Dawn for
her panties. Now go buy them both some drinks.” And with
that she was gone.
I struggled back into my clothes and went to the
refreshment stand. When I came out, I had a hard time
finding my car. It was where I left it, but Dawn’s was
gone. When I climbed in, I saw a note on the windshield.
“We’ll meet again” is all it said.
Chapter Three
*************
Kelly is so coy at home. She acts like nothing ever
happened. She still peeks once in a while, but now she
mostly throws her panties in my room when I’m not around.
I have to rush home to get them before Mom finds them,
but I also rush home to play with them. Sometimes I even
put them on. The feel of silk and lace is a new high for
me. I wonder what Kelly has in mind next.
I was soon to find out.
Kelly told me not to make any plans for Friday night. I
spent the week in frenzied anticipation. When Friday
came, I found out that our parents were going to the
movies! After they left, Kelly peeked into my room. I was
jacking off, wearing her silkiest panties. The feel of
the silk against my balls, and lace on my legs gave me an
incredible hardon.
“I thought you might like those,” she said. “I’m going to
take a shower. I want you to go to my room and find the
lingerie you like best. If you’re wearing it and
masturbating when I come back, I’ll let you keep it.”
I rushed to her room. I knew where she kept her nighties,
and I knew just the one I wanted. She had the flimsiest
lace-covered babydoll outfit. I’d seen her wear it
several times. It was thin enough for me to know she
shaved her pussy, and was very feminine. I shuddered as I
pulled it over my head. I climbed on to her bed, and
pulled my panties down to my ankles. The feel of the
silky material excited me so. I laid back in
anticipation, and was soon rubbing the material all over
my body.
Kelly was taking her time. It had to be the longest
shower she ever took. I was timing my strokes to her
arrival, having to stop several times, ’cause I didn’t
want to come prematurely. Finally the doorknob turned.
There stood Kelly, and her best friend Leanne.
“See, what did I tell you,” said Kelly. “David can’t help
it. He’d make a perfect pussy slave.”
I was shocked. And excited. I couldn’t stop. I looked
both girls in the eyes, and stroked faster. The girls
came into the room, and sat down on the bed with me.
“Would you like to be MY pussy slave?” asked Leanne.
“Yes,” I groaned. The thought of being a slave to this
red-haired beauty was just too much. “Command me!”
“That babydoll looks nice on you,” Leanne replied, “and
you may keep it; but if you’re going to be MY slave, you
have to dress like I tell you. I brought something else
for you to wear. Slow down, I don’t want you to come
yet.”
She grabbed the panties from my ankles and gave me a
garter belt and nylons. The belt had little red roses on
the front.
“Put these on.” She commanded.
With both girls watching, I fastened the belt around my
waist and rolled the nylons up my legs. I hooked the
nylons to the belt, and made the garter straps as tight
as I could. The nylons felt great against my legs.
“You’ve done this before, haven’t you?” asked Leanne. “If
you’re going to be my slave, you must answer me
truthfully.”
“Yes, Mistress, ” I said shamefaced and excited. “I can’t
help it. It makes me feel so aroused.”
“That’s alright, ” Leanne cooed. “You’re doing well, and
deserve to be rewarded. Now scoot down to the edge of the
bed, and hang your head over the side, face up.”
My cock ached, it was so swollen. The babydoll brushed
against it and I shuddered. So far I liked this game. It
took every ounce of will power not to come all over
Kelly’s pink sheets. I moved to the side of the bed in a
trance, my eyes blurred from the excitement. I had obeyed
my new Mistress’s first command, and now I was to be
rewarded.
Leanne hopped off the bed, and unfastened her skirt.
Underneath, all she was wearing was crotchless panties.
Her red pussy hairs glistened. The hair was so fine, I
could easily see her pouting pussy lips. She turned
around and backed up to the bed, sitting down on my face.
“Now I’m going to teach you how to please me,” she said.
“Lick me, eat me, until I come in your face.”
I grabbed her hips, and pulled her down further onto my
face. The taste, the aroma, the feel of Leanne dancing on
my face was making me insane. I licked, as if my tongue
had a mind of it’s own. Leanne squirmed and pressed down
harder. “Yes, mistress, this is what I need,” I thought
to myself.
Then Leanne came. It was a taste of heaven. I spewed come
all over my frillies, and Kelly’s bed. Leanne’s pussy was
slick with come. I let go of her hips, so she could get
up, but she just slid on my face more.
“I’m not through with you yet,” she cried. “Now lick me
clean.”
More pussy licking? Oh yes! I didn’t want it to stop. My
tongue was very tired, but I wasn’t going to stop; not
yet. Leanne’s pussy slid all over my face, covering me in
her sticky nectar. I licked for about ten more minutes,
sticking my tongue deep inside her. I wanted every last
drop. Finally, Leanne slid to the floor, panting. She
reached up and tweaked my stiff and sore nipples under
the gauzy material.
“I think this will work,” she murmured.
I was giddy with excitement. BOY, did I like this! I
didn’t want it to stop, ever! What had I gotten myself
into? After a few moments, I got up, and started to
remove my sticky nylons. I knew my parents would be
coming home soon.
“Wait,” said Leanne. “The night is far from over. I’ve
got one more lesson for you tonight. I want you to go put
sweat clothes and sneakers over your girlie clothes.
We’re going to go visit Dawn.”
Chapter Four
************
Strange sensations flooded my brain. I sat between Kelly
and Leanne in the car. I was wearing a sweat suit, but
the sensations on my skin were of lace, silk, and nylon.
“David,” said Leanne, “you pleased me well. I asked if
you wanted to be my slave and you said “Yes”. I want to
know if you were serious, or just caught up in the
moment; so I will ask you once again: “Would you like to
be my pussy slave?” Before you answer, remember this: if
you so “No”, we will have fond memories, but this will go
no further; if you say “Yes”, I expect you to obey me
completely, and always answer me truthfully. If you ever
change your mind, all you have to do is say the secret
word, “Pinocchio”, and this will all end, forever.
What is your answer?”
“Yes, ” I whispered.
Kelly drove us to a section of town I’d never been to
before. We went to a subdivision of new small houses
crammed together on narrow streets. There were few
driveways, and everyone else parked on the street. It
must have been a mess getting out of there in the
morning.
The girls led me to a little yellow house halfway down
the block. So this is where Dawn lived! Kelly knocked on
the door, and some girl I’d never met before open the
door. There was a party going on. There were food and
drinks out, and presents stacked on the table by the
wall. There were ONLY girls there; about eleven of them,
including Dawn.
“Hi David,” yelled Dawn, “come in; we were waiting for
you.”
“David,” said Leanne, “this is Dawn’s batchlorette party.
I told her that you would help serve the food and drinks,
so that we girls can enjoy the party. Now say hello to
Dawn, then go help out in the kitchen.”
I made my way over to where Dawn sat; a little self-
conscience about being the only guy at an all-girl party,
and greatly self-conscience of my frillies caressing my
skin.
“Hello Dawn,” I said. ” I’m glad to meet you again.
Kelly didn’t say anything about your party when she
brought me over here, or I would have brought a present.
I hope I’m not intruding.”
“Don’t worry about it,” grinned Dawn. “I asked Kelly to
bring you. I was just telling the girls how we met, and
they all wanted to meet you.”
My face was turning red. I wanted to run away, but
strangely enough, I wanted to stay, too.
“Girls,” Dawn continued, “we WANT David to join our
party, don’t we?”
“Yes!” they all chorused; “We want you to join us.”
“See,” said Dawn. “You can be just one of us girls. Now
please go help Lisa in the kitchen, so you both can get
back out here sooner.”
Confused, dazed, and secretly thrilled, I scampered out
of the room.
I found the kitchen, manned by a short cute blonde
cutting up green peppers. Tomato sauce was simmering on
the stove; five bowls were sitting by the sink, each
covered with a small hand towel, and a large array of
liquor bottles sat on a table by the door.
“Hi,” said the girl. “I’m Lisa. You must be David. Dawn
said you’d be here to help. I’m in the middle of making
pizzas, and I could sure use a hand. I’ll tend bar and
cut up the veggies if you’ll roll out the dough. Pizza
pans are under the sink. Let me get you a drink first,
though. You look like you could use one.”
A drink; I probably could use one indeed. I took a deep
breath; my head was still
reeling from all that had happened so far. I nodded my
head and took the amber-filled glass from her hand.
“Thank you. I’ll get right on those pizzas.”
We chatted about several things as we worked; where we
went to school, (Lisa and her friend Amy had both
graduated the year before), future plans, Dawn’s wedding,
and favorite places in town. (I didn’t mention the drive-
in.) I found out that this wasn’t Dawn’s house, Lisa and
Amy shared it. Lisa was busy with drinks, filling snack
bowls, and chatting with her friends as they came by, and
I stuck the pizzas in the oven, washed dishes and
glasses, and wiped the counters. Working in the kitchen
had given me a few moments to regain my composure and
reflect on what had happened so far; and I liked it.
Soon the pizzas were done. Lisa and I took them into the
living room and set them down wherever we could find
room.
There weren’t enough chairs, so I leaned against the
wall.
Dawn was opening gifts, and the girls were making risque
comments about lingerie and wedding night sex.
“David,” said Leanne, “we want you to enjoy the party.
Come sit on the floor and take your shoes and socks off.
You’ve been standing for at least the last hour.”
My shoes AND socks? I hesitated. If I did that, they
would see my nylon-covered toes! Then I thought of all my
previous exhibitionist fantasies. Here I was the only
guy, with eleven or twelve girls who had already heard
about Dawn and me at the drive-in. They already knew!
Leanne was challenging me to live out a fantasy I had
never considered. Masturbating for a room full of girls
who WANTED to watch me!
I shivered with excitement, and slowed did as Leanne
asked. The girls giggled, as the shiny nylon became
apparent.
“What did you think of Dawn’s wedding lingerie?” asked
Leanne. “Do you like it?”
“Yes.” I replied. “It’s very sexy. I’m sure it would look
good on her.”
“David,” continued Leanne, “why don’t you show Dawn the
type of lingerie YOU like.”
I couldn’t stop. I shivered with excitement as shyly I
took off my sweatshirt. The babydoll had bunched up
around my shoulders, and when I smoothed it out, my
nipples ached. The girls smiled and gave me all the
encouragement I needed to slip off my sweat pants. In
addition to the nylons and garters, Leanne had given me
her crotchless panties. I was flush with excitement. My
dick was stiff and standing proud. All the girls were
clapping and whistling. I was naked and dressed at the
same time; and I was enjoying it.
“Now,” said Leanne, “it’s time for me to give Dawn my
present. David, masturbate for the girls, and don’t stop
until you cum.”
Leanne handed me a jar of Vaseline. I slowly smeared it
all over my throbbing cock, letting each girl see me
revel in the silky softness.
I stroked. Watching all the girls watching me. I stroked
to each girl, slowly at first, then adding a few quick
strokes; giving each one eye contact, and a smile. They
were all watching me. I wanted them all to see me
masturbate. I wanted to watch them watching me. Watch me
jack off until I came. I wanted to watch them watch me
cum. I was in paradise. I played with my nuts, stopping
to regain my breath. The girls were cheering me on. Some
of them were flashing their panty-covered pussies at me.
I didn’t want to stop, but I didn’t want to cum, either.
I just wanted it to last as long as possible. I slid my
fingers to the base of my cock, pressing the skin into my
groin, making my cock stand out farther. The girl sitting
on the couch in front of me, Amy, grinned. I smiled back.
Then I started stroking again, faster. I still remember
that smile. I came. I shivered. I caught my cum in my
open hand and smeared it back on my still throbbing
shaft. My cum was a lot silkier than Vaseline, so I
stroked for a few minutes more. My cock was super-
sensitive. My cum, silky at first, felt like the lingerie
caressing my body. The more I stroked, the stickier my
cum became. Then I stopped, exhausted, spent.
Dawn walked up to me and raised her dress, to show a
shaved pussy underneath. Then she placed her leg on my
shoulder, grabbed my head, and ground it into her pussy.
I lapped and sucked on those sweet lips. She pushed me
down to the floor and sat on my face. My head was covered
by her dress, so I just closed my eyes, and enjoyed the
sensations. Soon my face was just as wet and sticky as my
groin.
Dawn crawled off, to be replaced by another shaved pussy,
Kelly’s. Tired as I was, I licked her as best I could,
but mostly I just let her smother me and slide all over
my face.
Other hands were caressing my body, stroking my cock. I
got semi-hard again. Lisa brought out a bowl of soapy
water, and several girls proceeded to give me a sponge
bath and helped dry me off. I just lay there, totally
exhausted, and totally exposed, with no desire to cover
up.
Finally, Lisa and Amy helped me to the couch, and made me
sit between them. Lisa handed me a drink. Then Lisa and
Amy each took one of my nylon-covered legs and hooked it
over one of theirs, leaving me still fully exposed, my
nylons rubbing against theirs. They asked if I wanted to
stay for the night, but I guess I’ll have to ask Leanne
first.
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