Babysitting Bliss - Jenn gets done right, the first time!

[Crazyhorsesghost]

Scott had completely forgotten about an office function he was obliged
to attend on Saturday night and desperately needed a babysitter for
his niece & nephew that he was caring for that weekend.

Lucky for him, I lived downstairs and my mother was always offering my
services around the building as a babysitter.

I hadn’t babysat for many people in the building, usually working for
friends of my mom who lived elsewhere, but it seemed like easy work.
Put the kids to bed early, watch some movies, raid a fridge... and
just generally relax.

Scott was a couple of years older than me, ok… more than a couple. I
was only 19 and he was 27, but it didn’t seem like much of a
difference. On more than one occasion I caught him stealing a glance
at me, but never once did I think things would progress as quickly as
they did between us.

Whenever he saw me in the hallways, he was always very sweet and
talkative. Scott was always interested in how college was going, and
had even offered to help me on a few occasions.

Anyways, back to tonight.

My plan for a relaxing evening was cut short when I realized the kids
were hell on wheels. It took all my energy to finally manage to get
these kids into bed and asleep.

When it finally happened at about 10:30pm, I was so tired, that I just
didn’t think of what I was doing. Scott’s couch isn’t comfortable at
all; in fact, he could really use a new one, so I crawled into his
room and curled up on his bed to sleep for a bit.

I kept the door open, so that I could hear the kids if they woke up. I
pulled my jeans off and threw my socks into a pile. I didn’t even
think of Scott as I did this. I was wearing a long t-shirt and pulled
it down over my thighs as I leaned back onto the bed, subconsciously
grabbing his pillow, wrapping my arms around it and falling into a
deep sleep.

When I awoke almost 2 hours later, Scott was sitting on the edge of
the bed. I had no idea how long he had been watching me, but I could
see that he hadn’t just sat down.

“I’m sorry to have woken you up, I just got home” he lied, as I
suddenly realized that I was half-dressed and pulled his blankets
close over my legs.

“Oh, no” I stammered, “I should be the one apologizing, I shouldn’t
have gotten so comfortable in your bed, Scott.” I thought about
getting up out of his bed, but found myself in a very awkward
situation, as I didn’t want to be half naked in front of him, but
couldn’t stay in his bed.

“If your tired, feel free to stay here in my bed…” he stumbled through
the sentence and I could tell he was getting nervous. “I can call your
mom and say you fell asleep, and you can leave in the morning.”

It sounded like a great offer. I was already in bed, and staying the
night would get rid of the awkwardness of having to get up and get
dressed. I could do it in the privacy of his room in the morning
before leaving. I nodded in agreement and he left the room to call my
mom.

“Well, I think I woke her up, but she was fine with everything,” said
Scott as he strolled back into the room and began to undress. “I hope
you don’t mind if I take off my shirt and gather a few things before I
head into the living room to sleep, do you Jenn?” I didn’t know what
to say at first, but then he slowly revealed his tight stomach muscles
and I felt a strange feeling within me.

“No, not at all. Here would you like your pillow back?” I offered as I
stretched my arm and presented it back to him.

“No thanks, I have a spare in my linen closet” he stated as he slowly
undid his pants, slipping them off onto the floor to reveal his boxer
shorts. “So, are you dating anyone at school?” he questioned.

I sat up straight in bed and nodded my head back and forth. He seemed
surprised by my answer and his questioning started to excite me. Scott
started asking questions about the guys at school and suggested that
maybe they were intimidated by such a beautiful girl, which was why I
hadn’t been dating. He made me blush and he knew it.He asked if I had
been kissed and if I enjoyed it.

“I have been kissed a lot…” I said. “Most guys my age all want a lot
more than just kissing.” I pulled his blanket closer to my body, as I
noticed I was gradually getting more excited.

“And you don’t want more?” he questioned.

“Well, I do. Just not from them. I want someone with experience.” I
said. “Someone like you.”

At first I regretted what I had just said. Then I realized how much I
wanted him, so my regrets just disappeared, and instead I hoped he
wanted me too!

He sat on the edge of the bed, close to me and slowly leaned in. My
eyes instinctively closed and I felt his warm lips press against mine.
My body seemed to go limp at first as both our mouths impulsively
opened to find probing tongues waiting to explore each other.

I sighed gently as I felt Scott’s hand reach around to cup my head and
pull me closer to him. He leaned into me, pressing his lips against
the side of my neck and taking in my scent. With each move he made, I
was getting more aroused. I could easily see the excitement within his
shorts and this thrilled me more.

“I shouldn’t be doing this... we shouldn’t be doing this” he exclaimed
as he leaned back. “You’re the babysitter… and I’m well… I’m a lot
older than you.” He seemed nervous all of a sudden and it made me feel
guilty.

“Don’t apologize,” I answered. “I want you”

He reached around my waist and pulled me tightly to him. Scott leaned
me back onto the bed and had me spread my legs apart slowly. He ran
his hands lightly over my inner thighs and I felt a slight twinge in
my body.

“Have you ever had sex before?” Scott asked quizzically as he
continued to massage my legs tenderly. I nodded my head in
disagreement as I felt his hands move higher up my inner thighs.
“Would you like to?” he finished.

I was caught off guard, but the feeling within me was so overpowering
that I yelped a small “yes” as he leaned forward and kissed me. His
hand then cupped my covered pussy and rubbed oh so gently. I could
feel his hand tugging at my panties gently as he slowly moved them to
one side of my tender pussy lips. All of a sudden, I felt a finger
slowly run up the inside of my lips and I gasped.

Scott pulled me over to the edge of the bed, so that my legs were
resting on his shoulder as he was on his knees on the floor. My wet
hole was right in front of his face and I didn’t feel awkward any
more. I felt at home with him and it excited me. His fingers began at
first, slowly tracing their way around my lips, but never entering me.
Then I felt the strangeness of his tongue licking my hard clit. I
panted in exhilaration as he stuck his tongue into my tight, wet hole.

With every move he made, I got more excited. I had never felt the way
I was feeling with Scott at that moment. He peeled my panties off my
body and slipped one hand up between my tender pussy lips, rubbing
gingerly, as his lips closed over my hard clit. He began sucking it
hard between his lips then Scott put one finger against my slit,
spreading my lips open before pushing his finger into my soaking wet
entrance. My pussy grabbed his finger, taking it deeper into my tight
cunt until it was buried inside me tightly, like a vacuum.

I slowly pulled my t-shirt off and pulled my bra down to reveal my
overflowing breasts with hard nipples. Scott didn’t even pay
attention; he was too focused at the job at hand. He proceeded to bend
his finger slightly as he continued to suck on my clit. He could hear
my panting and as he opened his eyes, he saw my breasts rising and
falling as my anticipation grew.

He knew he was taking a chance, but he wanted to taste more of that
sweet cum on his tongue; he wanted to be the one to drive me over the
edge for the first time, the second time and the third time. Scott
felt my pussy gripping his finger and slid it a little deeper into my
tight hole. I was in heaven and I’m pretty sure he was too. He wanted
me just as much as I wanted him.

__________________________________________


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I couldn’t believe that this was happening to me. I had seen Jenn many
times in the hallway in the building and often masturbated while
thinking of fucking her body, but I never thought it would ever
happen.

My finger was soaking wet from drilling her slit for the past few
minutes. I knew she would come any moment and I wanted to make sure
she came once without penetration and had her exactly where I wanted
her; begging for more. She arched her back slowly and I reach my free
hand under her ass and began to circle her tight puckered asshole with
one finger. If I had my way, I’d be penetrating every one of her holes
tonight.

Jenn moaned loudly and I whispered to her to try and contain herself.
I had just remembered that the kids were still fast asleep down the
hall and I wanted to keep it that way. I pulled my finger out of her
tight pussy and lifted it to her lips. This would definitely quiet
her, I thought, as I plunged my wet fingers into her mouth for her to
suck on. She sucked feverishly as though this was her last meal and
would never be satisfied again. While she sucked, I leaned my face
down and proceeded to lick her gently from her tight asshole to her
sopping wet pussy.

As my tongue darted in and out of her hot wet hole, I placed one of my
fingers on her clit and began to rub it slowly. I could tell by her
low moaning that she was going to explode soon, so I would alternate
my motions by placing my fingers in her pussy and licking her clit
feverishly. When I thought she couldn’t take any more, I bit down on
her clit gently and plunged my finger deep inside her. Her tight pussy
clamped down on my finger and she came harder than anyone else I have
ever fucked.

I pushed her body onto the bed and lied down on top of her, kissing
her lips gently and running my hands all over her body. My hips were
equal with hers at this point, and she could feel my hard cock between
her legs. I sat up on my knees and took her legs and spread them as
wide as they would go, bending them at the knees, so I had a great
view of her sweet, wet pussy.

I grabbed her hips and pulled her body closer to mine, making sure my
cock was right in line with her open hole. My cock was extremely hard
and eager for her pussy to envelope it, so I leaned forward into her
and placed my head right at the entrance to her sopping wet pussy.
Jenn’s mouth opened and I could tell she was about to say something,
but before she knew it, I had thrust my hard cock deep inside her
virgin pussy and she was yelling loudly.

At first it sounded like yells of pain, and then slowly, they became
moans of sheer pleasure as I continued to ram my hard cock inside her.
My hands reached up and grabbed a hold of her breasts, pinching her
nipples as I kept fucking her. She was so eager to be fucked, and I
was in heaven with my cock buried up to the hilt in her wet box.

Keeping her tightly around my cock, I grabbed her waist and rolled her
over onto her front. At first, I pushed her chest down to the bed so
her ass was high in the air, and I had a nice view of her tight
asshole while I fucked her, and then slowly, I got her up onto all
fours. My hands reached down under her body and pinched her nipples
more, while her moans became more frequent. I was not in any hurry to
make her cum again, so I pulled out of her pussy and put my finger
deep inside her, getting it covered in her sweet juices.

I was tempted to lick them off, just so I could taste her sweet nectar
again, but instead I pushed her chest back onto the bed, and placed my
wet finger right at the entrance to her tight ass. I could tell she
was hesitant at this idea, but I knew she would go along with it once
she knew how fabulous it felt.

I continued to rim her ass with my wet finger, and then brought my
tongue down and began licking all over, and plunging it gently into
her tight ass. Jenn was doing a pretty good job of loosing up her ass,
so I decided to bring her back to the brink of ecstasy before I
plunged my cock into her tight ass and gave her the fucking of a
lifetime.

With her face down on the bed, I stuck my hard cock back into her wet
hole and finger her ass with one hand, and fingered her clit with
another. She was writhing pretty fast after only a moment of
pleasuring her; I pulled my hard cock out, and placed it right at the
entrance of her tight ass. I could tell by the look on her face that
she was worried it would hurt, but at this point I didn’t care.

As my cock began to work it’s way into her tight ass, she was
reluctant and her ass tightened up. I needed her to relax so that I
could fill up her tight ass, so I placed 1 finger on her hard clit and
began to rub it. She relaxed very quickly at this point and slowly I
was able to slide my entire cock into her tight virgin ass.

I worked my cock in and out of her ass very slowly at first, then
finally picking up the pace as I realized what I was doing. I was
finally realizing my fantasy, and if I had my way, she was going to
turn into my personal slut. I grabbed her auburn hair and pulled her
back towards me as I plunged deeper into her ass. Jenn pleaded with me
to fuck her, and I wasn’t about to stop, but then I realized that I
was on the verge of cumming.

I pulled out of Jenn’s ass and rolled her over onto her back. I placed
my cock just above her mouth and instructed her to suck it, offering
advice on how best to do this, as she was obviously inexperienced.
After 2 minutes, she had my cock deep in her throat and I was moaning
in pleasure, as I knew my explosion was imminent.

I pulled my hard cock out of her mouth and stroked it once until I
came all over her luscious breasts and face. I think this surprised
her, but she seemed to enjoy as she began to rub all my juice into her
skin. We lay down on my bed together and curled up in the blankets,
our arms wrapped around one another. I knew this was not going to be
our last time, but certainly was a memorable first time.







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