Jessicas Birthday Party
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Jessica's Live-In Babysitter - Part 3 free porn video
Jessica's Live-In Babysitter - Part 3
by CutePatti
The next day was Saturday, so all three of them were home. Sam was up
first since he was an early riser, but Jessie took advantage of a no
school day by sleeping in and, of course, Becky kept her routine of
getting up late due to her work schedule. He went into the bathroom to
shower and shave as usual. He noticed there was a half-empty blister pack
of small tan-colored pills laying on the vanity. He hadn't seen them
before but figured they must be Jessie's since only he and she used that
bathroom. He picked up the packet and saw on the back that the pills were
called Diane-35. He wasn't sure about the ingredients that were listed,
but judging from the size of the pills and the number of spaces in the
packet it seemed they were possibly birth control pills. Strange, he
thought. Why would Jessie have these? Or maybe they were Becky's and just
somehow ended up in here. He figured Becky still took the pill since she
did when they were dating. He just let it go and jumped in the shower,
relishing the feel of the refreshing water splashing on him.
He then dressed and went down to the kitchen to have his coffee and
breakfast and was surprised when Becky came down soon after. "Wow...you
sure are up early," he said. She let out a big yawn, "Yeah, there's some
things I need to get done today and I figured I might as well get up.
After all, I don't have to work tonight." She had been trying to adjust
to her new work schedule but it was hard after working only daytime hours
for many years. She poured herself some coffee and sat next to Sam as she
tried to clear her head.
He wasn't sure if he should, but decided to ask her about the pills he
had seen. "Uh, I hope I'm not intruding or getting too personal....but
when I was in the bathroom awhile ago I noticed there were some pills
sitting on the vanity. Just curious why they were there since I hadn't
seen them before." Becky still wasn't completely awake and thought for a
moment and then replied, "Oh...those must be Jessica's. She must have
forgotten to put them away." Sam was still curious since he again assumed
they were possibly birth control pills. "Well, I know it's really none of
my business but I am curious because those pills look a lot like, you
know, THE pill." He was a little embarrassed as he said it.
Becky laughed and told him to relax. "Yes, they are THE pill but those
kind of birth control pills are also used for other things. So don't
worry...Jessica is not promiscuous or sexually active and is not using
them for THAT purpose. At least I hope not. haha"
"Well, I didn't mean to imply that she is," he said but still looked
confused so she went on. "It's OK, I know you didn't mean anything by it.
So here's the reason she's taking them. Maybe you've noticed that
although she has really grown up a lot...at least in size, she has
not...well...she's not filled-out as much as she should have for her age.
She's sort of....er.....flat and not very rounded-out." Sam was getting a
little uneasy with this and thought maybe Becky really didn't want to
have to get into it. "I shouldn't have asked in the first place," he
said. "Let's just leave it at that and I sort of get the picture."
"No, it's OK," Becky quickly added. "You are living here and we are like
family so you should know what is going on around here. Anyway, I was
getting a little worried that she wasn't progressing, shall we say, as
much as other girls her age, like her friend Amy. You've seen Amy and how
she looks, right?"
"Yeah, I've seen her," he responded. "Jessica wasn't all that concerned
and when I talked to her about it she was like, it's no big deal and I
don't care that much. She didn't want to talk about it. But I decided to
take her to the doctor just to make sure all was well. Dr. Allen did some
blood tests and found that she has a lower estrogen level than she should
have and an elevated androgen level is causing it. So she prescribed
those pills for her. They are a strong combination of anti-androgen and
estrogen hormones that should help her out. The doctor said it happens to
some girls and described it as a way to hopefully induce her into a more
normal puberty. Nothing to worry about, she told us. Jessica is very
healthy and normal otherwise. So, any questions?" she sort of laughed,
"Or was that too much information?"
"No, it's OK," Sam said still a little uneasy. "But Jessie probably
wouldn't like me knowing this much about her and, uh, her problem."
"Don't worry," Becky said. "I won't say anything to her about us talking.
I'm just surprised you found those pills laying out in the open. Jessica
had told me awhile back that she didn't like the way the pills made her
feel and that she didn't want to take them as often as she should. But
maybe she has changed her mind. I hope so anyway. But so far, they
haven't seemed to be working. Or else she isn't taking as many as she is
supposed to. But that's up to her...I'm not going to force her because
she seems happy and she is totally healthy regardless of this. And Dr.
Allen reminded me that there are lots of slender females running around
perfectly happy."
All of a sudden Jessie bounded down the stairs and asked, "So, you guys
are talking about me, huh? I heard you explaining about my pills."
"Oh...uh, Jessie, I wasn't trying to pry in your private business, it's
just I saw those pills in the bathroom this morning and was surprised,"
Sam told her. "And I straightened him out on why you have them. So that's
all there was to it," Becky added. "By the way, have you been taking
them? I thought you didn't like them?" Jessie quickly responded, "Well, I
don't like them, but decided I am going to start using them again. So I
am. But I doubt they will help me like they're supposed to. So don't
expect to see any big changes in me. No big deal, OK?"
"Speaking of pills, like what is that great big pill that you always have
on the sink every morning?," Jessie asked Sam. "Oh, that's not really a
pill...it's a capsule, a vitamin capsule. I take one first thing every
morning and want to remember to take it so I put one out every night so I
won't forget." He explained to her. "Oh, OK. but it is so big. Is that
what a capsule means? I've never heard of those before." she said. Sam
laughed and said, "Well I guess it is like a pill and some pills are big
too. But a capsule comes apart in the middle so you can put whatever
ingredients in it you want to. I have these specially made for me with
the exact mix of vitamins that I want to take every day, so that's why
they're in a capsule. The company I order them from mixes it up and puts
it in each capsule." Oh, I see," she responded. "So that great big pill,
I mean capsule gives you a lot of stuff you need to make you strong, huh?
You never know, they may put stuff in it that you don't know about.
haha," She giggled as she said that and added, "Well, I'm sure the stuff
they put in it will be good for you. Probably better for you than my
little pills are for me," she said grinning.
"Well, special day's almost here," Becky said changing the subject
quickly. She smiled at Jessie
who smiled back and nodded. "What day is that?" Sam asked. "She didn't
tell you?" Becky replied. "I'm surprised. I thought for sure she'd tell
you she has a birthday coming up!"
"Really?" he said. "When is it?"
"Next Sunday," she said. "I mean Sunday next week, not tomorrow. I'm
gonna be fifteen!"
"That's great, you're really getting to be a big girl, aren't you?" He
said teasing her as he reached over and gave her head a little pat. She
smirked and stuck her tongue out at him. "And I suppose you'll be
expecting presents." A big grin spread over her face, and she said,
"Well of course! Lots of them."
"Oh, Jessica, don't be so greedy!" her mother interjected. "I don't want
you taking advantage of Sam's generosity. He's already been very nice to
you. Did you thank him for that ride he gave you and Amy yesterday? He
didn't have to do that, you know."
"Yeah, I thanked him," she said. "I gave him a really, really big thank
you, didn't I, Sam?" She looked over at him with a raised eyebrow and
winked. "Uh...yes, she did," he told Becky. "Both she and Amy thanked me
very politely."
"See?" she said triumphantly to her mother. "That's just the way I am.
If someone does something nice for me, then I do something nice for them.
But I still owe him, big time!" She looked at Sam and nibbled on her
toast.
"Oh, brother!" Becky said, rolling her eyes. "Laying it on a bit thick,
aren't we?" She shook her head and laughed. "Well, anyway, we'll have
to plan something nice for your birthday, maybe go out to eat or
something. Would you like that?"
"Sure," said Jessie. "And presents," she added under her breath,
grinning impishly. They all laughed. "We'll see," her mom said. "But
it's not your birthday yet, so you better be on your best behavior for
the next week."
Becky got up and took the dishes to the sink. "Today's my day for
dishes," she said, "but it's your turn to do the laundry. You didn't
forget, did you?" Jessie made a face. "No, Mother, I didn't forget.
I'll be your slave maid today, don't worry." She brought her own dishes
to the sink, then went into the living room and turned on the TV.
"I told you she'd try to take advantage of you, Sam," Becky said. "You
better be on your guard." He laughed. "Don't worry," he said. "I can
take care of myself."
"Hope so," she replied. "But I do worry -- you're such a softie! You be
careful around her."
"Oh, I will," he said. "Believe me, I will."
Later that afternoon Becky popped her head into the living room where he
was sitting on the couch reading. "I'm going shopping," she said. "Make
sure Jessica does her chores. I mean it. I'll be back in a few hours.
Bye."
"OK admiral...aye aye!", he said teasing her about her attitude. She just
rolled her eyes. As she went out the front door he returned to reading
his magazine.
Some time after she left, Jessie came down the stairs carrying a photo
album. She went into the living room and sat down on the couch next to
him. "What'cha got there, some old pictures of my used-to-be little
girl?" he teased. "Well, yeah...but that's not what I wanted to show you.
I was looking for a pic but then saw these and I thought you'd like to
see them," she said. "Since you liked my cheers so much yesterday, ya
know?" And she sorta leaned into him so he could see. She also crossed
her left leg over her right so her bare foot was touching his leg. He
took notice but tried not to stare at her pretty toes that were wiggling
a little. Man, he thought, she sure is a tease.
There was a page with several photos of what was obviously a young boy
wearing a cheerleader uniform similar to hers. Sam cleared his throat but
managed to say, "Ah...uh...well that is...uh...really something," was all
he could think of. She laughed and said, "OK, yeah I know you weren't
expecting to see this. haha. But I thought, ya know, after yesterday
being so much fun and all and then I ran across these. I figured I'd let
you see them."
Sam just sat there almost frozen and not knowing what to say or ask.
"Don't you think he looks good in my uniform? At least as good as a guy
can look in it? haha"
"Uh, well yeah I suppose he does, but who is he and why is he wearing it?
Was it some kind of prank or joke or what?" he asked. She responded, "No,
not a prank, not a joke, and that cutie-pie in a skirt is my boyfriend
Brian."
"Huh, I didn't know you had a boyfriend." He said still very nervous
about what to say. "Yep, I've got one, well at least sorta since mom
won't let me call him that. She says I'm too young for a boyfriend. Duh!"
she quickly said. She then just sat there looking at Sam obviously
waiting for him to react. She kept her foot pressed right up against his
leg. The silence was too much for him so he finally asked, "Well, so why
is Brian wearing your uniform if it wasn't a joke? Did you make him do it
just for fun or as a bet or something?"
"Nope...he told me he wanted to wear it so I let him.
And.....well.....remember what I showed you yesterday? You know, like
what I had on under my uniform? Well...he wanted to wear that stuff too."
Sam was getting really uneasy as well as a tad bit excited as she was
casually talking about Brian wearing her clothes as if it was a normal
everyday occurrance. He looked at the photos and it was obvious Brian
wasn't trying to look like a girl because he didn't have on make-up or a
wig. Just the uniform. Sam thought about all the boys he had seen on the
web, some dressed like this, and many of them providing him with some
really great jerk-off material. He loved the photos but had to be careful
with his reaction since Jessie was sitting right next to him.
It got quiet again and she just chuckled and then said, "OK, I'll tell
you why. Since you seem interested but don't know what to ask. haha." She
sort of elbowed his ribs as she said that. "It was for halloween last
year. OK?"
"Oh, I see. So you made him wear it for a halloween party, did you? That
must have been hard to get him to do that." he said. "No, duh.....aren't
you listening....I just told you it was HIS idea...I didn't make him do
it....he wanted to wear it and it wasn't to a party. It was just him and
me."
"But you seem OK with it. Like it didn't bother you. Almost like it's an
everyday happening," he said. "Haha...well, no, it doesn't happen every
day. But he...." Just then her cellphone rang and interruped her so she
answered it.
"Amy just called, and she wants me to come over right now. So I'm going
to ride my bike to her house, okay?" He frowned at her. "Aren't you
forgetting something young lady?" he asked. "What? Oh, you mean about
Brian?" she asked. "Well....er...yeah...that too. But also there is a
small matter of the laundry, remember?" he replied. "Oh, that," she said,
making a face.
She stood up and started to walk out of the room. Then she stopped and
turned around. "Hey, Sam?" she said. He looked up. "Yes? What is it
your majesty?" She laughed and then said, "Could you take my turn with
the laundry just this once," she pleaded. "I'll take your turn the next
two times, I promise. So please...pleeeeease will you?" He sighed.
"Really now, you can't always expect that someone will..."
"Pleeeeeeease," Jessie interrupted, "She says she really really has to
talk to me about something, and I haven't been to her house in ages,
and..."
"All right, all right!" he protested, "I'll do it, but just this once."
He sighed and put his magazine back down. "You know, you really are
going to have to..."
"Thank you, thank you!" she said, running up the stairs. "I'm gonna call
her now and tell her I'm coming. I'll make it up to you, I promise. Oh,
and please don't tell mom. OK? She'll kill both of us."
Sam shook his head and started for the laundry room. "No time like the
present," he sighed. "Better get this done before Becky gets home." He
had the washing machine running with the first load when he looked up and
saw Jessie come into the laundry room carrying an armload of clothes.
"Are you serious?" he said to her. "You mean you have more than this huge
pile that's already here? Good grief." She laughed and said, "Well, since
you are my maid you have to do it. So just go on and don't give me any
lip, miss!" He barely noticed she had called him her maid or even miss.
But they were both enjoying this teasing. This is so easy, she thought to
herself.
"Could you wash these too, please?" she said. "I forgot that my cheer
uniform needs washing. So here it is. Just make sure you wash it on
delicate and lay it out flat to dry. Don't use the dryer for it. OK?" He
was speechless as she handed him the gorgeous outfit that he had seen her
wear just yesterday. He stood there transfixed as she handed him first
the little half-tee shirt top and then the cute pleated short skirt. "Oh,
and also these things that I wore under it. I hope you don't mind." As
she watched his reaction, she handed him a little white bra, the cute
socks with the 'Tiger' embroidery on the cuffs, and finally the blue
panties she had flaunted and teased him with. As she handed him the
panties she said, "I'm not sure you noticed the other things...but you DO
remember THESE don't you?" As she put them in his hands he managed a
weak, "Yes, Jessie...I do remember." She formed a devilish grin and said,
"Yeah, I bet you do."
"Thanks a lot Sam!" she said, and turned to go out. Then she stopped and
turned around to face him again. "Uh, and remember...don't tell mom about
you doing my chore for me." She stood with her hands held behind her
back, looking shyly at the floor and biting her lower lip. "After all,
she doesn't have to know about everything we do, does she?" she said,
looking up at him with innocent eyes. He coundn't answer. "Oh yeah...and
have fun! You know...uh, with the laundry, I mean. Oh..and I'll tell you
more about Brian later. And don't worry about it. It's really no big
deal. I'm totally OK with it. And, like don't you think he looks awesome
in my uniform? Well not as good as me...but not bad for a fourteen year
old guy! haha Later! Bye!" With that she winked at him and skipped out.
He stood there, almost in a trance. Oh lord, what is she trying to? Or
is she doing anything? Does she really know what she's doing? But he
realized, when adding everything up that had happened since yesterday,
she was at least teasing him. Especially since she showed him photos of
her boyfriend dressed up in her cheerleader uniform. Oh god, those
photos. He looked so good in that uniform. Did he do it just for fun or
might he be more into it? Sam remembered when he was fourteen and spent
as much time alone as possible, masturbating while he wore his sisters
panties, bras and other stuff. Might Brian be doing that? Whew. Still, he
figured she couldn't know about his secrets. Otherwise she would have
most likely said something. But, he couldn't be sure.
He came out of his trance and saw that he was holding Jessie's blue
panties in his hands, the same ones she had been wearing yesterday when
she had flipped her skirt up so he could see them. And he was also
holding her cute and sexy uniform and all that went with it. And it
needed to be washed....so there would be no harm...no evidence if he.....
Oh, man. He groaned as the excitement of this moment flooded through him,
and he was aware of his erection growing as he thought of her standing
there with her skirt up, and of her standing in front of him, teasing him
with the uniform....flaunting him with these very same panties. And he
thought of Brian and the photos.
He suddenly came out of his trance and realized he had to do something.
Oh Jeez, I need it, I need this right now, he moaned to himself. He ran
out to check and make sure Jessie had left and as he was heading back he
noticed the photo album was still on the coffee table in the living room.
Oh, man. He figured he had plenty of time, Becky wasn't due back for a
couple of hours and he knew Jessie would be tied up with Amy for a long
time. So he grabbed the album and went back to the laundry room. He
quickly unzipped his pants and pushed them down and off along with his
underwear. Then he pulled off his t-shirt, socks and shoes. Oh my gosh,
shoes, he thought. Her cute sneaks. He had to have the whole outfit. He
ran upstairs to her room and the cheer sneakers were on the floor right
by her bed. He checked the size tag inside the tongue of the shoe and it
said 9. Wow, they just might fit. His cock was rock-hard and starting to
drip pre-cum so he got a tissue from her nightstand and wrapped it around
it so he wouldn't leak on the carpet.
When he got back to the laundry room he started putting on her things. It
had been a long time since he had actually worn any female clothing, and
yet here he was about to live out a fantasy that he could have never
dreamed possible. Possibly the ultimate fantasy. First the little bra. He
picked it up, checked the tag that was sewn-in and it said 'Teenform
Trainer. Size:34AA'. He slipped his arms through the straps and somehow
managed to easily snap the single hook at the back. It fit him perfectly
and his now hardening nipples poked through the thin fabric. He grinned
as he realized that both he and Jessie were a perfect AA cup and that
this was not only her training bra, but his training bra as well. Then he
remembered the little pills she was taking. Maybe 'our' next bra will
need to have a bigger cup size one of these days. He trembled as he
thought about that. Then he quickly brought the 'Tiger' socks to his nose
and was rewarded with just a hint of Jessie's sweet, delicate foot aroma.
Oh God! He then slipped her socks on his feet and could see the outline
of where her toes had been in the socks....the same socks his toes were
now occupying.
The panties would have to wait. He was far too hard and erect to even get
them on. So he next put on the little half-tee and it felt so good over
the bra. Then the sexy cute pleated skirt. No way could he fit in it, he
figured since it was a heavy non-stretch polyester fabric. But once he
had it up and in place, it easily zipped up on the side. Wow, he and
Jessie were the exact same size. He knew she was big for her age, but had
no idea she had grown to his size exactly. Unreal. And maybe Brian too?
Whew! He then kneeled down and took one of the sneakers and slid his
feet with the cute socks into it. Another perfect fit. His penis was
drooling a steady stream of clear liquid now and the soaked kleenex fell
to the floor. He got the other shoe on and just stood there for a
moment...relishing the feel of Jessie's clothes on his body. Clothes she
had worn just yesterday....now on his body. Fitting as if they were
custom made for him.
He wanted to put on the panties too, but he was too far along in his
excitement and needed to get off soon. His cock was pushing out the short
skirt and the head was visible. He was turned-on beyond anything he'd
ever known before. He lifted the skirt up and his full 8 inches sprang
out, fully erect and in need, and he wrapped the blue panties around it.
He picked up the photo album and found the page with Brian's photos.
Sinking down onto the floor with his back against the washing machine, he
placed the album on his legs and began to masturbate with Jessie's
panties, slowly rubbing the soft cotton fabric up and down his rigid
shaft, moaning in pleasure and frustration, thinking of her shamelessly
teasing him yesterday as she lifted up her cheerleader skirt. He looked
at Brian dressed in the same outfit he was now wearing. He wondered if he
was turned on when he wore it or if he just did it for fun. Then he saw
one photo where Brian had his legs spread wide enough to clearly see the
blue panties...the panties he was now jerking off with. And he saw the
outline of Brian's penis and what appeared to be a dark little wet spot.
Thinking of Jessie while looking at the photos at the same time, it took
just a few seconds for him to reach the point of no return. He felt her
bra tightly encasing his chest....looked at his feet in her cute socks
and shoes, and felt her panties urging him on to orgasm. Suddenly he
screamed out as the first long rope of thick white semen shot through the
panties, launched over the skirt and landed and puddled on the cute
embroidered Tiger enblem on the half-tee shirt. Five more shorter blasts
shot out, all landing on the skirt which was soon coated with long
strings of his hot white cum. Oh God, Oh God, oh yessssss! He came in
achingly sweet spasms, and wrapped his cock completely with the panties
as it bucked and spurted once more and soaked the blue cotton fabric with
more of his seed. He lay there, panting.....Jessie's uniform coated with
his cum, until he finally was able to catch his breath. The reality of
what he had just done hit him and he knew he had to act quickly before
either Jessie or her mom got home. But he took one more moment to savor
what was most certainly the best orgasm he had ever had.
Finally he stood up and stripped out of Jessie's cheerleader uniform,
bra, socks, shoes and panties. He then quickly put his own underwear,
pants, shirt, socks and shoes back on. He returned the photo album to the
coffee table and took the cheer sneaks back to her room. Shaking his
head and trying to regain his composure, he thought about how great it
worked out that Jessie needed him to do her laundry chore today. A set-
up, perhaps? Especially since she had brought her cute uniform to him in
person and handed it to him? Maybe. Or, maybe she did it just because it
needed washing, as she had said. Yeah, it really did need washing now!
And he smiled as he thought of Jessie's last remark as she left. 'Have
fun with the laundry.' Well, he sure did.
End of Part 3
Sherry
- 05.09.2021
- 36
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