Jimmy Becomes Jenny Ch 4 Jenny s New Toy
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Jimmy Becomes Jenny -- Ch. 2: Jenny Learns The Ropes free porn video
***STANDARD DISCLAIMER***
Do not read this if you are under the age of 18 or it is illegal where
you live. All characters in the story are at least 18. If you don't like
this sort of story, then don't read it. Also, this is fiction. Any
similarity to anyone living or dead or to actual situations is entirely
coincidental.
***END STANDARD DISCLAIMER***
Jimmy Becomes Jenny
By Cheerleader Tina
Chapter 2 -- Jenny Learns The Ropes
When I woke up, I was confused. I wasn't in my room, and while it looked
familiar, I didn't know exactly where I was. Then I noticed Miranda next
to me and I remembered the previous day and recognized my sister's
bedroom. I sat there for a minute, feeling Miranda's body pressed up
against me. My hand wasn't on her breast anymore; it was on her stomach,
so I slowly moved it down toward her pussy. I began gently rubbing her
clit, and I could feel her start to get wet.
She woke up and said, "Hmmmm, that feels good, but you better not start
something you can't finish."
I kissed her neck and rolled her over to face me, then I lifted up her
nightie and started kissing her breasts, working my way down her body.
By the time I got to her crotch she was moaning and working her pelvis
into my hand. I pulled my hand away and she grabbed my head and pulled
it tightly against her. I stuck out my tongue and licked her clit, then
I started eating her in earnest. She rolled over on top of me and
started grinding her pussy into my face. Then she turned herself around
and I felt her leaning over. When she took me in her mouth I paused my
licking, enjoying the sensation, but she squeezed my head and I got back
to work.
When we finished sixty-nining each other Miranda rolled off of me and
said, "Jenny, you are so good at that, I think I'll have to keep you."
I just nodded, unable to speak. She stood up and grabbed my hand,
pulling me to my feet. We stood there in my sister's room, wearing her
nighties, covered in each other's juices. She stripped off the nightie
she was wearing and left the room, saying she was going to take the
first shower.
"You want me to come help you, make sure you don't miss any spots?" I
asked her.
"Down boy," she told me, "there will be plenty of time for that later."
With that she left, closing the door behind her. I figured I'd better
put the room back the way it was so my family wouldn't notice. I put the
covers back in their original position and started stacking the drawers
more or less where they had been. I took off my nightie and hung it back
up in the closet next to the one Miranda had been wearing. When I was
finished, all that was left was the pile of Miranda's own clothing. I
picked up her panties and sniffed them deeply, only to have Miranda walk
through the door.
"If you like them that much," she joked, "you can keep them. In fact, I
insist on it. I have to go home now, my mom will be pissed if I stay out
all day. But I had a lot of fun, and I'd like to do it again tonight. My
mom works the late shift, so we'll have the whole house to ourselves
tonight. Can you come over around 8?"
I told her I could, and she giggled.
"Great, I'll see you then. One more thing though. I want you to keep
these panties handy, and every time you get hard today, I want you to
jack off into them."
"What for?" I asked.
"I don't want you to forget about me or about Jenny today. Just do it
for me, please?" She gave me a pouty look.
"Sure, I'll do it, I was just wondering why," I told her.
While we talked she had gotten dressed, but she hadn't put her bra on.
She handed it to me instead.
"Keep that too. You can wear it when you masturbate, to help you think
of me."
I told her that I didn't think I'd need any help thinking of her, but if
she wanted me to, that I would.
"Aww, you're sweet Jimmy. Bring them both with you when you come over
tonight," she told me. She kissed me again, and when we finished she
spanked me lightly and said, "I'll see you later. Have fun today!"
Miranda left and I went to my room to get dressed. I decided to go back
to my own clothes for the day, so I put on a pair of boxers and some
cargo pants. I grabbed a T-shirt but decided that I'd just wear the bra
all day, so I put it on first. When I was done hooking it, I had another
erection, so I dropped my pants, took Miranda's panties in my hand, and
masturbated. I came all over the front of them and then used them to
make sure I'd gotten it all off my hands. I took them with me and went
upstairs for breakfast after I finished dressing.
I spent the morning eating and watching television. By late afternoon I
had masturbated twice more and was beginning to get sore. Miranda's
panties were getting crusty and hard too. My parents called a little
before dinner time to make sure everything was going okAY. I told them
to tell Karen that Miranda had stopped by to pick up the uniform but I
left out all the details of the evening. By 7:00 I was getting antsy,
and thinking about the evening ahead had gotten me hard again. I
masturbated one more time before I left for Miranda's house.
About ten minutes later I knocked on Miranda's door. She opened the
door, but refused to let me in until I showed her the bra and panties. I
lifted my shirt up quickly to show her the bra and then pulled the
panties out of my pocket and handed them to her.
"Wow, you've been busy today," she commented as I walked in. "I didn't
think you had this much in you. I hope you aren't completely empty, I
have some plans for tonight."
"What kind of plans?" My curiosity got the better of me.
"Why don't you come up to my room and find out," she told me, pointing
to the stairs nearby.
I walked upstairs, Miranda close behind me. She reached up under my
shirt from behind and began playing with my bra.
"Did this do its job today?" she asked.
"Yeah, I wore it all day." I replied.
She unsnapped it and let it hang from my arms under my shirt. We got to
her room and she told me, "Lose the shirt."
I did so, tossing it into a corner. Miranda removed the bra and tossed
it into the hamper.
"I want you in something sexier than that one tonight," she explained,
opening her closet.
She walked in and grabbed a light pink bra with a cute bow for the front
strap. My attention, however, was drawn to a black and red corset with
garters at the bottom hanging in the center of the closet. When she came
back out to give me the bra, she noticed where I was looking.
"Sexy, isn't it. You want to try it on, don't you," she said.
I nodded.
"I don't think that's going to happen," she said, "Corsets are only for
real girls. You just like to dress up like one. I don't think you're
ready for that yet."
"What do you mean?" I asked.
"If you want to wear my corset," she said, "you're going to have to earn
it, and you're going to have to show me how much you want to be Jenny
for me. If you want to try, we can start over here."
She pointed at her bed, a large four-poster. She handed me the bra and
matching panties and told me to put them on. I put the bra on first
before I pulled my jeans and boxers off. I pulled the panties up,
tucking my penis into them before finally settling them on my waist. She
led me over to the bed and I lay down in the center.
"Give me your legs," she instructed.
I moved my foot over by her hand and she wrapped a leather strap around
it and buckled it tight. She moved to the other side and did the same to
my other leg. I saw ropes connecting each of the cuffs to a bedpost. She
moved up to the head of the bed and cuffed each of my wrists the same
way. I could still move all my limbs, but not very far. Once I was all
cuffed, Miranda tightened each of the ropes in turn until I couldn't
move at all.
"Now that I have your attention," she said, climbing into the bed and
straddling me, "let's see if we can't have some fun."
She reached over to the nightstand and picked up a long, fluffy feather.
She gently stroked up and down my sides and stomach, then moved up to my
bra. She slipped the end of the feather under the cups of the bra,
teasing my nipples. I was loving it, and my cock was straining in my
panties, trying to untuck itself. Miranda put the feather down my
panties and teased me even more.
"Oh God, that feels good," I told her.
"Shhhh, no talking," she said.
She went back to tickling my sides. I tried to squirm away, but I
couldn't go anywhere.
"Please, go back-" I stopped when she pulled the feather away entirely.
She said, "I said no talking. We'll have to take care of that."
She got off the bed and went over to a chest in the corner. I could just
barely see it from my position on the bed. I heard a lock click open,
and then saw her lift the lid of the chest. When Miranda came back she
was carrying a bunch of things with straps, I couldn't tell exactly what
was there.
"Well, now you have a choice. I'm going to gag you, and you get to pick
how. Your options are a ball gag, a ring gag, and a penis gag," she
said, holding up each one in turn.
"Umm, the ball gag," I said. I wasn't sure what a ring gag was, but I
didn't want to gamble on it being worse than a ball gag.
"I figured as much, I knew you didn't really want to be a girl and wear
my corset," she said, pulling the ball gag out of the pile she'd set on
the edge of the bed.
"Wait, yes I do," I replied. I really did want to wear the corset. "I
meant to pick the penis gag," I said, hoping that was the right choice.
She picked it up and made some rough adjustments to the strap. It was
about 6" long and bigger around than the dildo Miranda had used on me
the day before. She held it up in front of my face and I opened my mouth
so she could put it in. When it was in my mouth I waited for her to
cinch it up behind my head.
"Good choice, Jenny," Miranda said when she was finished, "I'm sure
you'll enjoy sucking on that cock for a while. The ring gag would have
been an okay choice too, I could have put my panties in your mouth for
you to suck on instead, but I can see you're getting into this and
willing to go all the way. You must really want that corset. I can
understand why, it certainly is sexy isn't it?"
I tried to speak around the gag, but all I got out was a mumble, so I
nodded my head. Miranda went back to teasing me with the feather as she
talked.
"I told you that all the cheerleaders do the same thing you did
yesterday to become a part of the team. The cheerleading team shares
everything, clothes, toys, and occasionally even boyfriends. That dildo
in Karen's underwear drawer was originally mine, but when I joined the
team it became all of ours. But today it's yours, to keep. You can fuck
yourself with it when you think about being one of us. I know you
enjoyed it yesterday, do you want it back in now?"
She went over to the chest again and pulled out the pink dildo that I
recognized. She grabbed a jar of Vaseline and brought them both over to
me. I thought about how much I had enjoyed Miranda playing with the
dildo in my ass and I moaned in anticipation.
"No, you don't want that one again?" she asked. "I'm surprised, I
thought you wanted to be more like a girl, and all girls love their
dildos. Oh well, I guess I'll just put it away and we can keep playing
like this."
I tried again to talk around the gag, but I still couldn't get anything
intelligible out.
"Oh I get it, you want something bigger. You want to see how much you
can take."
Miranda walked back over to the chest and pulled out a 10" black strap-
on. My eyes must have gotten wide because she said, "Don't worry, I'll
take it slow. I don't want to hurt you."
She came back over to the bed and added the strap-on to the growing pile
of toys. Then she came over to my head again and removed the penis gag.
She pulled it out of my mouth slowly, and it made a sucking sound.
"Did you enjoy sucking that cock Jenny?"
I knew what she wanted me to say, so I said it. "Yes, I loved sucking
it."
I was humiliated to be saying it, but I knew it would be more likely to
get me into the corset. Miranda told me to open my mouth as wide as I
could, and I did. She put the ring gag in and placed my teeth in the
notches in the rubber. Then she strapped it around my head. I expected
her to put her panties in my mouth like she had said she was going to,
but she didn't. Instead she went down to my feet and unhooked them from
the posts. Then she pulled my panties all the way down to my ankles,
then around the cuffs and off me entirely.
She brought the ropes attached to my ankle cuffs back up to the head of
the bed. She wrapped them once around the post and then started pulling
them tight, forcing my feet closer and closer to my hands, bending me in
half. I realized how exposed my ass was, and began expecting to feel the
strap-on in my ass. Instead I felt Miranda's hand grab my cock and guide
it toward my mouth. It didn't quite reach, so she pulled the ropes even
tighter. When the tip of my penis was in my mouth, she stopped.
"Now, you're probably going to cum while I'm fucking you. I want you to
swallow it all, okay? It tastes great, and every girl loves to eat her
boyfriend's cum. I'm almost jealous that I don't get to have it myself,
but like I said, we cheerleaders share everything, and I'm happy to
share my boyfriend's cum with you, Jenny," she said.
I saw her putting on the strap-on, and heard her open the jar of
Vaseline. I felt the cold slimy tip pressing up against my asshole and
tried to relax and take as much as I could.
The strap-on was ribbed, and every inch that she put in me sent shivers
up my spine. When it bottomed out and hit my prostate I felt waves of
pleasure running through me. Miranda started pumping in and out of my
ass and I noticed myself trying to pump with her to get it deeper. Every
time she pumped, my cock went further in my mouth, right through the
ring. I didn't really want to eat my own cum, so I tried to hold my
orgasm, hoping Miranda would finish before I did. It didn't work, and I
erupted, spraying cum all over the inside of my mouth. I did my best to
swallow it, trying to get it out of my mouth, but the gag prevented me
from getting it all down.
Miranda noticed my plight and came and sat on my chest after releasing
my legs from the bedposts, the dildo still attached to her waggling
gently as she scooted her way up.
She said, "Poor Jenny, can't get the cum out of her mouth? I think I
know how to help get rid of that taste."
She unhooked the straps on the dildo and tossed it on the floor before
sitting on my face. I started licking and noticed that it got some of
the taste off my tongue.
I started licking as fast as I could, and I heard Miranda say, "Oh wow,
Jenny, that cum must have really turned you on. I'll bet you can't wait
to have some more. You may not like the taste, but I can tell you love
to eat it."
I didn't even try to respond, I just kept licking until I felt Miranda
orgasm.
When Miranda's orgasms subsided, she climbed off of my face and sat on
my chest. She picked up the panties she had worn the day before, the
ones I had masturbated into several times, and wadded them up. I
couldn't close my mouth to keep her from putting them in my mouth
because of the ring gag. I could still taste a little bit of my own cum
from before, mixed with the taste of her pussy juices. Now I had a much
stronger taste of my cum from the dried residue on the panties. She
pushed them in slowly with her index finger, filling my mouth and
muffling any attempts to make noise.
Miranda got off the bed and returned to my legs. She reattached them to
the end of the bed, but she didn't tighten them. She went back over to
the toy chest, bent over to get something, then changed her mind and
began dragging the chest over to the bed.
When she got it there she grabbed something out of it and said, "Now
that I know you want something bigger than your new dildo, I've got just
the thing to keep you full until I'm ready to fuck you again."
She held up what looked like a small dildo, about the same size as my
pink one, but with a bulb hanging from the back by a rubber tube.
She lubed up the butt-plug and gently pushed it inside me. Once it was
in as far as it would go, she began squeezing the bulb. I felt the plug
begin to inflate inside me. I tried not to say anything, hoping that
would make her happy and she would stop on her own. She didn't, and
eventually I grunted from the pressure in my ass.
"Is that big enough, Jenny? I'd better make sure, we wouldn't want it to
fall out," she said.
She squeezed the bulb a couple more times and then I heard her taking
the tube off the back.
"There, that should keep you full until you're ready for another
fucking, don't you think?" she asked.
I nodded, hoping she would fuck my ass again soon.
"You're doing very well today, Jenny," she said, "I'm almost convinced
you want to be my girl and wear my corset."
She reached down and gently rubbed my breasts through my bra. She silk
sliding across my nipples made them stand up straight.
"Since the cheerleaders share everything, I've been thinking about
sharing you with them. I won't make you, I promised I wouldn't tell
anyone, but I think we could have a lot of fun. I was going to call
Cindy and have her come over and play with us. I'll leave it up to you.
Do you want me to call her?"
Miranda unlocked the ring gag and pulled it and the panties out of my
mouth so I could speak.
"I'd rather have you all to myself," I told her truthfully, "but if you
want to call Cindy, you can. She won't tell anyone else, will she?" I
asked.
"You really are a sweetheart, Jenny. No, this will be our secret, just
between us cheerleaders. Cindy won't tell anyone, and neither will the
others. We won't even tell all of them yet. I'll go call her then, and
while I'm gone, you can put on the corset." She untied my arms and legs.
"Go ahead and take that bra off first. Put it on, I'll tighten it when I
get back."
She kissed me deeply. "Mmmmm, I love that taste," she said.
She left, closing the door behind her. I took off the bra I was wearing
and walked into the closet. I carefully took the corset off its hanger.
Stepping into it, I pulled it up past my waist and around my chest and
stomach. I fumbled a bit with the clasps in the back before I finally
managed to close them all, feeling the garter straps bounce against my
legs as I worked.
When I was ready, I waited for Miranda to get back. She came in soon
afterward, and said, "Looks good, Jenny. You'll need some panties,
stockings and shoes to go with it though. Why don't you go see if you
can find any heels that will fit you, I'll pick out the others for you."
I said, "Okay," and went to the back of the closet where Miranda's shoes
were stacked neatly on their own small shelves.
I found the biggest looking pair I could find, a pair of shiny, red, 3"
heels. I picked them up and went back into Miranda's room. I held them
up for her approval.
"Those might fit, yeah," she said, "They look good too. Here, put these
on first," she instructed, handing me the stockings, "then put the
panties on over the top. Roll the stockings up before you put them on,
that will help."
I took the stockings from her, rolling them up like she had said. I slid
them up my still hairless legs, loving the feeling. It was an amazing
sensation. When they were pulled up as far as they would go, I hooked
the garter straps to them.
As I put the panties on I asked, "I thought you were supposed to put the
panties on before the garter straps?" I wasn't sure where I had read
that, but it sounded familiar.
"That's only if you're a proper young lady," was Miranda's reply. "Sluts
like us wear our panties over the garters so we can get them off quickly
if the opportunity arises. In fact, I don't usually wear panties with
that corset, but if you don't, you'll tent out your dress, and we
certainly don't want that."
"My dress?" I asked.
"Of course, silly," she replied, "the whole purpose of the corset is to
fit into a dress, and I have just the thing. My prom dress from last
year. It's got the sexiest tiny waist on it. I'll have to tighten that
corset first though."
She motioned me over to the bed and told me to grab one of the corner
posts.
She tightened the laces a little bit, then said, "Okay, hold on to that
post tightly, breathe all the way out, and don't breathe in until I tell
you to, okay?"
I grabbed the post and I felt Miranda put her foot in the small of my
back. I took a deep breath, then let it all the way out. Miranda yanked
on the laces and pushed me with her foot, squeezing my stomach and waist
until they hurt. I couldn't hold my breath any longer, so I inhaled as
deeply as the corset allowed.
"That was good, Jenny, can you do it again?"
I felt her wrap the laces around her hand, preparing to do it again. I
breathed all the way out again, pushing as hard as I could. Miranda
pulled the laces and pushed with her foot again, tightening the corset
some more.
She tied the laces off, telling me, "Take small breaths, and don't try
to move too fast. We don't want you to pass out and hurt yourself. I'll
go get your dress for you."
I nodded my thanks and Miranda went back to her closet. She pulled out
an off-the-shoulder, royal blue ball gown. She unzipped the back and
lifted it over my head, instructing me to put my hands up. I did so, and
she slid the gown over my arms and head, lowering it until it rested on
my arms just below my shoulders. She didn't zip the back up right away,
telling me to wait for a minute. She left the room and I heard her
running down to the kitchen. When she came back she was holding two
rather large balloons filled with something that looked like water.
"Pull the front of your dress and corset out as far as you can," she
told me.
I did so as she set one of the balloons on the floor. She took the other
one and put it in the cup of the bra in the corset. It was cold, not
frozen, like it had just come out of the refrigerator, and I gasped in
surprise.
"Sorry about that," she said, "I didn't use water because I wanted them
to move better, but I didn't want the pudding to go bad sitting out all
day. It'll warm up in a bit."
She put the other one in the other cup, then fiddled with them a bit
until they were situated the way she wanted them. The knots on the
balloons ended up pointing straight out and were visible even through
the ball gown, making it look like I had real breasts with hard nipples.
When my breasts had been arranged to Miranda's satisfaction, she stepped
around behind me and zipped the dress up. She went to her dresser and
pulled out a pair of long, white, gloves. She rolled them up like I had
done with the stockings and then held them up one at a time for me to
put my hands in. When I had done so, she rolled the gloves up my arms,
past my elbows, as far as they would go. She grabbed a makeup kit from
the top of her dresser and opened it, revealing several different shades
of lipstick. Grabbing one with a bright red label, she pulled off the
cap and twisted the bottom, revealing the end of the lipstick. She
showed me how to hold my lips, then applied the lipstick to me.
As she was putting it away, I heard the doorbell ring.
...To be continued in Chapter 3
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