An Itsy Bitsy Favor
- 2 years ago
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The Single Life: It's Complicated free porn video
The Single Life: It's Complicated
By RogerGirl
Well, it's been about a month since my double date with Ryan and we've
been hanging out a lot since then. Now before you jump to any
conclusions, we aren't hanging out in that way. We've been watching
sports and hanging out as friends. I know people say men and women can't
be friends, but I think we have proved them wrong. I've made it very
clear with Ryan that we are just friends and nothing more and so far he's
gone along with it.
Of course the media and tabloids paint a much different picture. If
anyone were to search his name online, they would be led to believe that
we are a couple. If we were a couple, we'd be the least romantic couple
ever. In the entire month we've been hanging out, we've never even
kissed. In fact the most physical contact we've had is a hug or a fist
bump after one of our teams scores or wins a game.
Now that I've set you straight on my relationship with Ryan, I suppose I
should admit that there is someone I've been thinking about a lot lately.
I know it's wrong, but I'm falling hard for Courtney. Despite knowing
that she is completely straight, has a boyfriend, and has only kissed a
girl for an acting role, I can't stop imagining her as my girlfriend.
You don't know how much self-restraint it takes not to kiss her every
time we are alone together.
For now though, I have been focusing on other things to keep my mind off
her. Recently, Teacher's Pets announced their feature girls for their
annual calendar and I was the top vote getter from the Los Angeles
restaurant. This weekend I am going to the beach for my calendar shoot
where a photographer will take dozens of photos of me wearing a skimpy
two-piece bikini. It's hard to imagine that not that long ago I was
dating girls in calendars like this and soon my bikini clad image is
going to be used as boner fuel by guys all over the country. It's really
very disturbing to think about.
For today, however, my priority is finding a babysitter for Emily until
she starts preschool in a few months. My mom recently found out her
father is ill and so she and my father are going to Florida to help take
care of him. While they are gone, I need to find someone to watch Emily
while I am at work. Teacher's Pets is no place for an almost three-year-
old girl to be spending her time.
So far I've seen quite a few applicants, but none of them have been just
right. I'm not too choosy in age or gender of the babysitter; I'm more
interested in their qualifications and their ability to handle Emily when
she is more difficult. I thought I had found one who was perfect, but
her rate was far too high for what I could afford. This is going to be
tougher than I thought. Oh, excuse me for a moment my next applicant is
here.
"Hi, Miss Thompson," a familiar face says as I open the door. "I saw
your ad and was wondering if I could apply."
"Of course, Jake," I say with a smile. "Come right in."
Now I know you're wondering and the answer is no. This isn't Chelsea's
ex-boyfriend Jake. Jake is a college student who recently moved into the
building. This is his first year not living in the dorms and he is about
to begin his 3rd year of college in the fall. Like most college
students, Jake is pretty desperate for a job and could really use the
work.
"Hi Jake!" Emily says excitedly as Jake comes in.
"Hi Emily," he responds cheerfully. "You're getting so big."
Jake is pretty good with Emily based on the times we've run into each
other in the building. From what I've learned about him, he has a
younger brother and sister and is the child of a single mom, although she
has since gotten married to a man with a son Jake's age. I've met his
family when they helped him move in and they are all very nice and I
admit I felt sort of a connection to his mom since I am a single parent
and she was also a single mom for many years.
"Well, Jake," I begin as he takes a seat on the couch, "can I get you
anything to drink before we begin?"
"Just water, thank you," he replies.
I must admit he is a lot more polite than I ever was at his age. I don't
even remember the last time I said thank you before becoming Caitlyn. As
I watch him playing with Emily, I can't help but notice a certain
nurturing quality in him that I assumed he acquired from years of looking
after his younger siblings while his mother was at work.
"Here you are," I say as I hand him a glass of ice water, "Now from what
I can see you are very good with her. I'm guessing you've spend a lot of
time looking after your brother and sister over the years."
"Yes, my mom was very busy and worked two jobs for a while," he began.
"At first she would hire babysitters to watch us, but when I got older
she left me in charge."
"Well you certainly seem qualified," I continue. "I would like to try a
monitored session though just to see how you handle yourself. I know she
seems cute now, but she can be quite a handful at times."
"Of course," he replies, "Also, I have no set rate. I'll take whatever
you can pay me."
"We'll worry about that later," I say.
I sit by as I watch him go to the kitchen to fix Emily her lunch. While
he makes her food, Emily plays in her princess castle in the living room,
in sight of Jake. Lately she has been really into princesses and I
bought her a princess costume that she likes to wear when she plays. I
watch them as Emily gets up and takes Jake's hand and leads him to the
tea set next to her princess castle. Jake is about to sit down at the
table with her, but she stops him as always. You see, Emily only allows
princesses to sit with her.
"No!" she shouts. "Only princesses."
"But, I'm a prince," he says. "Can't a handsome prince join you at the
table."
"Only princesses!" Emily shouts.
"I don't have a princess costume," he replies calmly.
"You can wear mommy's," Emily responds picking up the costume I wear when
I play princesses with her.
I look at Jake to see how he will handle the situation. As far as I know
Jake is not a crossdresser. I've been to his apartment a couple times
and nothing stands out as looking feminine. I also know him to be
straight since I've seen him with his girlfriend on several occasions.
In case you're wondering, he is around my size and if he chooses to wear
the dress it should fit him. Don't worry; it isn't a sexy dress or
anything, although there is some sexy princess dresses in my closet. The
dress is actually one that Fiona wears in the first Shrek movie.
Now there is a certain way I am looking for Jake to handle the situation.
On the one hand I don't want him to be a pushover and do everything Emily
asks. If he gives in too willingly to wearing the princess dress, it can
only be assumed that he'll give in just as easily when it comes to her
wanting Cocoa Puffs every morning for breakfast. That being said, I hope
Jake isn't the type of guy who thinks of himself as being too manly to
play a princess game with a little girl.
"Well, I can't wear the princess dress without the magic to turn me into
a princess," Jake says leading Emily to the kitchen where her lunch is
waiting for her.
"Magic?" Emily asks in wonder as she looks at her food.
"Yes, the magic is in your food," he says.
"I want cookies," Emily says looking at the half a sandwich, pieces of
fruit, and glass of milk before her.
"Cookies don't have magic," Jake says, "Only these food do."
Emily sits for a moment before tasting a piece of fruit. A look of
surprise comes over her face as she discovers she likes the taste. She
eats another piece of fruit and giggles as the juice drips down her face.
Jakes wipes her face with a napkin. Emily takes a bite of her sandwich
and drinks a sip of her milk. While Emily eats her lunch, I watch as
Jake takes the princess dress and quickly goes into the bathroom. When
he comes out a moment later, his long hair is loose and he has removed
his shirt to put the dress on. As expected he still has his pants on
underneath and hasn't stuffed the chest area or put on any makeup.
"Well, it looks like the magic worked," Jake says as an excited Emily
watches him in surprise.
"Yay!" Emily exclaims as she gets out of her chair and sits with Jake at
the tea set table.
They play princess party for a while before Emily begins to get tired and
he puts her down for a nap. After she falls asleep, he changes out of
the princess dress in the bathroom and washes Emily's cup and dish.
"You were very good back there," I say as he joins me in the living room,
"I hope it wasn't too awkward playing princesses."
"It's fine," Jake says. "It wasn't as bad as the time I dressed as a
girl for a project in high school."
"Really?" I ask in curiosity.
He goes on to tell me about how he dressed as his mom for a personal hero
project. The part that made him uncomfortable, however, was when he
agreed to become a girl named Kayla for a day and go on a date with a
boy. From experience I can tell how he must have felt, but for me it has
been a lot longer than a day.
"I have some pictures if you'd like to see," he says.
"Alright," I reply trying not to sound to anxious.
He goes back to his apartment and returns with his laptop. As I look at
the pictures, I admit I would have had a hard time believing the girl I
was looking at was really a boy. In one picture he is posed with his
mom, girlfriend, and a couple other girls at a mall and in another he is
seated at a restaurant with his mom, step-dad, and stepbrother. My
favorite picture, however, is the one where he is reading a bedtime story
to his little sister.
"You make a very pretty girl," I say. "Have you dressed up as a girl
since then?"
"No," he replies. "It was an interesting experience, but I don't think I
would do it again. Being a woman is a lot of work."
If only he knew. I tell him he has the job and we set up his pay and
schedule. By the time his classes start, Emily will already be in
preschool and my parents may be back before then. I also set a few
rules. For now, only I will be in charge of her baths and will give
Emily her bath before and after work. I also have set nanny cams around
the apartment for added security.
After giving Jake the rundown, I leave him in charge of Emily while I go
to the market to pick up groceries. As I walk through the store, I
happen upon Chelsea with her new girlfriend. Oh I should probably
mention that Chelsea is trying women now because of her terrible luck
with men. I don't know if she is bisexual, lesbian, or just going
through a phase. Unfortunately, I am not Chelsea's type, as she only
seems interested in very butch lesbians.
"Hi, Caitlyn," Chelsea says as she spots me. "This is Danni."
"It's nice to meet you," I say as Danni gives me a firm handshake.
We chat for a while and they invite Ryan and I over to dinner. As I
watch the two of them together, I can't help but notice how much happier
Chelsea seems with Danni. They make a very nice couple and I hope things
work for them.
After paying for my groceries, I return home to find Jake and Emily
drawing and coloring. I join them for a while before starting dinner.
Emily is drawing a picture of a butterfly and Jake is helping her pick
out the colors. Eventually, the dinner is ready and I invite Jake to
join us. Like before, Jake is very good at getting Emily to eat her
dinner.
Soon it is getting late, and Jake says his goodbyes. Tomorrow he will be
babysitting Emily while I am at work and at night while I have dinner
with Chelsea and Danni. Once he is gone, I tuck Emily in to bed and sit
on the couch watching a little TV before going to bed. I notice Jake
forgot his laptop and I open it to shut it off so that the battery
doesn't run out. On the screen is a photo of Jake as Kayla wearing a
bikini. I quickly shut off the laptop and go to my bedroom to go to bed.
I suppose I should admit that I have always been a fan of lesbian porn
and one of my favorites is when a hot mom seduces a hot babysitter. As I
lie alone under the covers, I begin to have a very erotic dream. Unlike
most of my sex dreams, Courtney is not present in this one. In my dream,
I find myself dressed as a sexy businesswoman when there is a knock on
the door.
"Hello Miss Thompson," Kayla says as I open the door. "I'm here to
babysit Emily."
"Oh, I'm sorry," I say. "I forgot to tell you that my parents have Emily
this weekend. Please come in though."
I watch as Kayla enters barefoot wearing a pair of short shorts that show
off her incredible legs and ass and a tiny tank top that shows off her
flat stomach and fantastic cleavage. It is clear she is not wearing a
bra. She crosses her legs as she sits down on the couch and I sit down
next to her.
"So how are you, Kayla?" I ask as I cross my stocking encased legs.
"I'm fine," she replies. "Ian is taking me out tonight for my birthday."
"Oh, it's your birthday?" I ask.
"Yes, I'm 21," she replies.
"Well, happy birthday," I say. "I wish I had gotten you a gift. I think
I may have something you might like."
I move closer to her and begin to gently stroke her bare thigh. She
becomes slightly uncomfortable and moves away.
"I have a boyfriend," she says.
"It's OK," I reply, "so do I. We're just having a little fun."
She smiles shyly as I begin to stroke her arm. She begins to relax and I
lean in to kiss her on the lips. We make out for several moments before
breaking the kiss. She looks more comfortable now and smiles at me again
as she raises her arms and I remove her tank top to reveal her
magnificent breasts. She lets out a soft moan as I begin to suck on her
nipples before removing her shorts. Just as I am about to go to work on
her shaven pussy, the alarm clock goes off and I awake to sunlight
peering in through a crack in the blinds.
I admit I am disappointed the dream is over, but the alarm came at just
the right time. I don't want things to become awkward when I see Jake
and imagining him as Kayla is the very definition of awkward. Jake is
probably the best babysitter I am going to find and I have to find
someplace else to focus my sexual frustrations. This has been the
longest I have gone without sex and I have to say it has started to take
its toll. I must find some new distraction if I am going to get through
the rest of this year.
Becky
- 23.01.2022
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