The Babysitter - The highschool babysitter takes his virginity.
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Crazyhorsesghost
Jul 27, 2008, 12:58:36 AM7/27/08
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The first time Jennifer came over, I thought nothing of it. I was
eighteen, moving quickly towards independence, and frankly, not the
least bit concerned that my parents didn't trust me enough to watch
over my seven year old brother. I don't blame them, because aside from
occasionally doing some homework, all I ever did was play video games,
listen to heavy metal, and read comics. It's not that they didn't
think I was a total hellian, it was just this issue of responsibility
that seemed to convince them to shell out the money to hire someone
"more capable of getting Randy to bed on time." At least when any
babysitter came over, they left the explicit instructions to leave me
alone unless I turned the music up to loud or if smoke was coming from
my room. So during Jennifer's first visit, a night my parents went to
the movies and then to dinner at the new Italian place downtown, I
never once emerged from behind my locked door. I just sat there and
played video games and watched TV. I didn't hear much from the rest of
the house, except for Jennifer yelling out to Randy that it was lights
out.
Her second visit was exactly two weeks later and this time I actually
had to meet her. I had accidentally left my door cracked and my mom
had pushed it open and announced that it was time I met Jennifer.
Although I disagreed, Jennifer appeared right behind her and smiled.
An average girl, I remember thinking. A senior in high school, she had
long brown hair and soft, brown eyes, but she wasn't a knock-out. Her
breasts were big, though, and I also remember her kind of catching me
staring at them as my mom formerly introduced us.
"Hi," I said bleakly, trying to play uninterested.
"Hi," she responded, "If you need anything tonight just ask."
And that was that.
It was the third visit I'll never forget. This was the time my parents
were going to dinner and theater and had actually set a bedtime for
me. They said it would be after one before the came back, and by then,
they proclaimed that I was to be in bed with the lights out.
I was playing one of my favorite games that night when I heard a
tremendous rumble echo through the house. So for once, I left my
bedroom to see what was going on. I walked into the living room to
find Jennifer on top of Randy pinning him to the ground, both
laughing.
"I told you I'd catch you!" she laughed, "Bedtime."
"Okay, okay," Randy gave in.
That's when she noticed me.
"Hi," she said, her expression a surprised one, "I didn't expect to
see you tonight."
____________________________________________
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____________________________________________
"I just heard all the noise," I shrugged.
"Oh," Jennifer answered, "I didn't mean to bother you, your baby
brother here is impossible to get to bed."
"I'm not a baby!" Randy objected.
"Fine," Jennifer smiled, "Then be a big boy and go to bed by
yourself."
Randy huffed, but agreed. And soon, I was back in my room again
playing video games. It was a little after eleven when there was a
soft knock on my door.
I opened it and there stood Jennifer, her breasts looking bigger than
ever behind her plain, blue tee shirt.
"Hey," she said, "Not to bug you, but please be in bed when your
parents come home, okay?"
I smirked but nodded. Fair enough.
"Don't make me wrestle you down, too," she said with a smile. I
laughed softly.
"Fat chance," I retorted as she turned to walk away.
"Fat chance of what?" she turned around and asked, "Of you being in
bed or me wrestling you down?"
"Either," I responded and right then she grabbed me. Shocked, I could
do nothing but watch as she pushed me to the ground and straddled me,
pinning my hands to the floor.
"Hey!" I objected, "That hurt!"
Jennifer smiled and tightened her grip.
"Let me up!" I demanded.
"What's the magic word?" she asked, and as she did, I realized
something awful. My dick was quickly growing hard. I frantically
struggled to save face, but as she shifted to keep her position, she
obviously noticed. Her smile turned to a complexed look.
I expected her to jump off me in anger, but instead, she just loosened
her grip on my hands. I quit struggling and felt my face grow beet
red.
"My, my," Jennifer said and sat up straight, the weight of her now
completely on my waist and crotch.
"I'm really sorry," I began.
"Don't be," she said and smiled, "That's a great compliment."
"Thanks," I responded, still embarrassed to all hell.
"Can I ask you something personal?" she asked, and as she did, she
shifted slightly, grinding herself briefly on my hard dick. The
sensation was unbelievable.
"Okay," I said, only slightly aware that I thrusted my waist up just a
tad, bringing on another sensation like the first.
"Are you a virgin?" she asked.
"Yes," I answered honestly, without hesitation or even consideration
of lying.
"Do you want me to get off you?" she asked next.
"No," I answered simply, but this also truthfully.
Then, without further conversation, she pulled off her shirt. And as
she did she grinded herself against my dick again and I remember
gasping lightly. Her breasts were beautiful. Fully developed and
stout, I just stared in amazement. Next, she reached back and removed
her bra and now I saw all. Nipples, breast, everything.
"What do you think?" she asked matter-of-factly.
"I like them," I answered and thrust my waist up again.
"Touch them," she said, and so I did, reaching up and carefully
massaging her breasts.
"Can I ask you something?" I asked as she purred to my careful
massaging.
"Anything," she answered in a sexy tone.
"Are you a virgin?"
"No," Jennifer answered bluntly, "I lost my virginity when I was
thirteen."
At this, she winked, and my dick grew harder than ever.
"How many times have you had sex?" I asked, feeling very brave at my
hard line of questioning.
She laughed and leaned down on me, letting her nipples touch my face
and then leaned back up.
"Not enough," she finally answered and put her hands on my chest.
I didn't know what to say, next, but fortunately, she kept the
conversation going.
"Can I ask you something else, something really personal?"
"Okay," I replied, noticing she was grinding herself up and down my
dick now.
"Would you tell your parents if you lost your virginity tonight?"
"No," I answered quickly, my heart for the first time beating in
nervousness.
"Would you tell your parents," she asked, then paused, then
continued," If I pulled your shorts down and screwed the ever living
hell out of you?"
My heart stutter stepped and I lamely shook my head.
"Am I scaring you?" she suddenly asked and quit grinding. Instead of
responding, I simply jerked my waist upwards. At this, she smiled and
continued grinding.
"Do you want to have sex?" she asked, "Don't feel pressured."
I just nodded.
"Is that yes you're being pressured or yes you want to fuck?" she
clarified.
"I want to have sex," I said and that was all that was needed.
Jennifer got on her knees and unbuttoned her cut-off jean shorts and
pulled them down to reveal black lace panties. She stood up, removing
the shorts and then the panties, and I remember watching in amazement
at her jiggling breasts. Her pussy was beautiful. I stared and almost
came as she sat back on me, now completely naked. My shorts had an
elastic waist, so removing them and my briefs seemed to be one natural
motion for her. My hard cock finally came free, and before I could say
anything, she grabbed it and lowered herself greedily onto it. The
feeling was at first strange, very hot and wet, but then I adjusted
and the sensation was all pleasurable. Jennifer gasped and leaned down
on me and rubbed her breasts in my face. Then, without warning, she
sat straight up and began bucking her body on top of me. There was
nothing soft about this lovemaking. She was frantically riding my
dick, sliding up and down, and then around, rubbing my chest with her
hands. She was fucking me hard, and soon she was leaning back and just
thrusting her hips back and forth. I could no longer take it, and as
she sat back up and began madly jerking back and forth, I came with a
mighty force. This she noticed and yelled out "Cum for me, baby, cum
for me!" "Oh God!" was my response. "Keep cumming! Oh keep cumming!"
she yelled back I did and when it was over the bucking stopped and she
slowly slid off.
"What did you think?" she asked a few minutes later as we lay side-by-
side.
"That was great," I said and I wasn't lying.
It was ten minutes later that I got my first blowjob. It as a week
later that we did it doggy-style on my bed, and then tried 69 on the
living room floor. The week after that, she introduced me to anal sex.
This followed, of course, by sex in the shower.
For a babysitter, Jennifer did a pretty damn good job, I thought. Even
better, when some months later, she brought her friend Allison over.
But that's a story for another day.
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eighteen, moving quickly towards independence, and frankly, not the
least bit concerned that my parents didn't trust me enough to watch
over my seven year old brother. I don't blame them, because aside from
occasionally doing some homework, all I ever did was play video games,
listen to heavy metal, and read comics. It's not that they didn't
think I was a total hellian, it was just this issue of responsibility
that seemed to convince them to shell out the money to hire someone
"more capable of getting Randy to bed on time." At least when any
babysitter came over, they left the explicit instructions to leave me
alone unless I turned the music up to loud or if smoke was coming from
my room. So during Jennifer's first visit, a night my parents went to
the movies and then to dinner at the new Italian place downtown, I
never once emerged from behind my locked door. I just sat there and
played video games and watched TV. I didn't hear much from the rest of
the house, except for Jennifer yelling out to Randy that it was lights
out.
Her second visit was exactly two weeks later and this time I actually
had to meet her. I had accidentally left my door cracked and my mom
had pushed it open and announced that it was time I met Jennifer.
Although I disagreed, Jennifer appeared right behind her and smiled.
An average girl, I remember thinking. A senior in high school, she had
long brown hair and soft, brown eyes, but she wasn't a knock-out. Her
breasts were big, though, and I also remember her kind of catching me
staring at them as my mom formerly introduced us.
"Hi," I said bleakly, trying to play uninterested.
"Hi," she responded, "If you need anything tonight just ask."
And that was that.
It was the third visit I'll never forget. This was the time my parents
were going to dinner and theater and had actually set a bedtime for
me. They said it would be after one before the came back, and by then,
they proclaimed that I was to be in bed with the lights out.
I was playing one of my favorite games that night when I heard a
tremendous rumble echo through the house. So for once, I left my
bedroom to see what was going on. I walked into the living room to
find Jennifer on top of Randy pinning him to the ground, both
laughing.
"I told you I'd catch you!" she laughed, "Bedtime."
"Okay, okay," Randy gave in.
That's when she noticed me.
"Hi," she said, her expression a surprised one, "I didn't expect to
see you tonight."
____________________________________________
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____________________________________________
"I just heard all the noise," I shrugged.
"Oh," Jennifer answered, "I didn't mean to bother you, your baby
brother here is impossible to get to bed."
"I'm not a baby!" Randy objected.
"Fine," Jennifer smiled, "Then be a big boy and go to bed by
yourself."
Randy huffed, but agreed. And soon, I was back in my room again
playing video games. It was a little after eleven when there was a
soft knock on my door.
I opened it and there stood Jennifer, her breasts looking bigger than
ever behind her plain, blue tee shirt.
"Hey," she said, "Not to bug you, but please be in bed when your
parents come home, okay?"
I smirked but nodded. Fair enough.
"Don't make me wrestle you down, too," she said with a smile. I
laughed softly.
"Fat chance," I retorted as she turned to walk away.
"Fat chance of what?" she turned around and asked, "Of you being in
bed or me wrestling you down?"
"Either," I responded and right then she grabbed me. Shocked, I could
do nothing but watch as she pushed me to the ground and straddled me,
pinning my hands to the floor.
"Hey!" I objected, "That hurt!"
Jennifer smiled and tightened her grip.
"Let me up!" I demanded.
"What's the magic word?" she asked, and as she did, I realized
something awful. My dick was quickly growing hard. I frantically
struggled to save face, but as she shifted to keep her position, she
obviously noticed. Her smile turned to a complexed look.
I expected her to jump off me in anger, but instead, she just loosened
her grip on my hands. I quit struggling and felt my face grow beet
red.
"My, my," Jennifer said and sat up straight, the weight of her now
completely on my waist and crotch.
"I'm really sorry," I began.
"Don't be," she said and smiled, "That's a great compliment."
"Thanks," I responded, still embarrassed to all hell.
"Can I ask you something personal?" she asked, and as she did, she
shifted slightly, grinding herself briefly on my hard dick. The
sensation was unbelievable.
"Okay," I said, only slightly aware that I thrusted my waist up just a
tad, bringing on another sensation like the first.
"Are you a virgin?" she asked.
"Yes," I answered honestly, without hesitation or even consideration
of lying.
"Do you want me to get off you?" she asked next.
"No," I answered simply, but this also truthfully.
Then, without further conversation, she pulled off her shirt. And as
she did she grinded herself against my dick again and I remember
gasping lightly. Her breasts were beautiful. Fully developed and
stout, I just stared in amazement. Next, she reached back and removed
her bra and now I saw all. Nipples, breast, everything.
"What do you think?" she asked matter-of-factly.
"I like them," I answered and thrust my waist up again.
"Touch them," she said, and so I did, reaching up and carefully
massaging her breasts.
"Can I ask you something?" I asked as she purred to my careful
massaging.
"Anything," she answered in a sexy tone.
"Are you a virgin?"
"No," Jennifer answered bluntly, "I lost my virginity when I was
thirteen."
At this, she winked, and my dick grew harder than ever.
"How many times have you had sex?" I asked, feeling very brave at my
hard line of questioning.
She laughed and leaned down on me, letting her nipples touch my face
and then leaned back up.
"Not enough," she finally answered and put her hands on my chest.
I didn't know what to say, next, but fortunately, she kept the
conversation going.
"Can I ask you something else, something really personal?"
"Okay," I replied, noticing she was grinding herself up and down my
dick now.
"Would you tell your parents if you lost your virginity tonight?"
"No," I answered quickly, my heart for the first time beating in
nervousness.
"Would you tell your parents," she asked, then paused, then
continued," If I pulled your shorts down and screwed the ever living
hell out of you?"
My heart stutter stepped and I lamely shook my head.
"Am I scaring you?" she suddenly asked and quit grinding. Instead of
responding, I simply jerked my waist upwards. At this, she smiled and
continued grinding.
"Do you want to have sex?" she asked, "Don't feel pressured."
I just nodded.
"Is that yes you're being pressured or yes you want to fuck?" she
clarified.
"I want to have sex," I said and that was all that was needed.
Jennifer got on her knees and unbuttoned her cut-off jean shorts and
pulled them down to reveal black lace panties. She stood up, removing
the shorts and then the panties, and I remember watching in amazement
at her jiggling breasts. Her pussy was beautiful. I stared and almost
came as she sat back on me, now completely naked. My shorts had an
elastic waist, so removing them and my briefs seemed to be one natural
motion for her. My hard cock finally came free, and before I could say
anything, she grabbed it and lowered herself greedily onto it. The
feeling was at first strange, very hot and wet, but then I adjusted
and the sensation was all pleasurable. Jennifer gasped and leaned down
on me and rubbed her breasts in my face. Then, without warning, she
sat straight up and began bucking her body on top of me. There was
nothing soft about this lovemaking. She was frantically riding my
dick, sliding up and down, and then around, rubbing my chest with her
hands. She was fucking me hard, and soon she was leaning back and just
thrusting her hips back and forth. I could no longer take it, and as
she sat back up and began madly jerking back and forth, I came with a
mighty force. This she noticed and yelled out "Cum for me, baby, cum
for me!" "Oh God!" was my response. "Keep cumming! Oh keep cumming!"
she yelled back I did and when it was over the bucking stopped and she
slowly slid off.
"What did you think?" she asked a few minutes later as we lay side-by-
side.
"That was great," I said and I wasn't lying.
It was ten minutes later that I got my first blowjob. It as a week
later that we did it doggy-style on my bed, and then tried 69 on the
living room floor. The week after that, she introduced me to anal sex.
This followed, of course, by sex in the shower.
For a babysitter, Jennifer did a pretty damn good job, I thought. Even
better, when some months later, she brought her friend Allison over.
But that's a story for another day.
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