Caught, Stripped and fucked in the ass
by amazonboy

amazonboy@rediffmail.com for comments and ideas



As I was in bed I could not help thinking, about what had happened to me
earlier during that night. My memories over powered the fact that my eye was
beginning to swell and my nose was bleeding again. I guess I should start at
the beginning. My name is Mike Stephan and I am eighteen years old and I go to
a small catholic high school. Until this night I had been the classic bumbling
virgin. I always seemed to say the wrong thing at the wrong time. I live small
town and word tends to move pretty fast here. So if you screw up once, you
don't get too many chances to make up for it. Naturally all my chances to make
a good impression are used up.

Last week I was walking my dog, T.J. We were about a few blocks from my home.
I was being pulled along the sidewalk by T.J. I was grumbling about having to
walk the dog so late at night.

My dad said, "If the dog makes a mess you have to clean it up." Obviously I
agreed to the task and glad I did.

Finally T.J. found the spot to do his business. We were in front of
Johansson's house and I was trying to coax T.J. to hurry up. He would not
listen. I noticed a light go on. I looked up. I was relived it was a light on
the second floor. I saw someone cross the window and I have to admit it felt
wrong, but I wanted to get a closer look.

To the dismay of T.J., I tied his leash to the lamppost and made my way to the
widow to investigate. I could not see a thing looking up at the widow from the
ground. There was a tall oak tree behind me and the bottom branches were
pretty close to the ground. I grabbed the closest branch and climbed up. The
climb was hard, but I managed. I sat on a strong branch half way up the old
oak tree. I was at eye level with the window. There were enough branches and
leaves to cover me.

I almost fell down the tree when saw Alyssa, a girl in my senior class,
walking around her room in her bra and panties. The sight of her perfect "B"
cup breasts supported by a thin white bra and the skimpy little panties were
burned and fused into my mind. There was no way I could look away, but the
growing pressure in my shorts averted my gaze from that beautiful female
specimen, just a few feet away. My manhood tried everything in its power to
bust out of my pants.

I was blinded with desire; I had to release the strain. I unzipped my shorts
and my dick happily popped out to say Hi! I grasped my shaft with eager
enthusiasm and began pumping in classic masturbation sequence, slowly. I
wanted to make this little pleasure of mine last longer. But my eagerness took
over. Up and down I moved my hand, faster and faster. Mounting pressure was
great, and I shot my spunk into the cool night air.

Sense returned. I realized it was time to go. Stealthily, I hopped down from
the tree and made it back to the impatient T.J. waiting to go home. T.J. and I
walked back home. I had a grin on my face.

During the next week, I repeated this little ritual every night around the
same time. My parents got used to the idea of my taking late night strolls
through the neighborhood. I could not stay out too long lest my parents worry.
Because of the limited amount of time I had to watch Alyssa, all I was able
see was her in her bra and panties. That was good enough for me.

My parents told me they were going for a family reunion during weekend. I was
able to convince them to let me stay back at home. When they left I decided it
was time fulfill my dreams.

After dinner I walked over to Alyssa's house. I settled myself once again in
my usual spot on the oak tree. A few minutes later Alyssa came into her room
drying her long blond hair wet from her evening shower. I brought my old
friend; My dick; and began to stroking it. As usual Alyssa's perfect tit pair
supported by that little bra drove me crazy. My eyes widened when it appeared
as if Alyssa was about to open her bra. My heart sped up to incredible speed.

I froze when I heard, "Get down right now young man!" from below. Because of
the shock I fell out of the tree. I was physically ok. But emotionally... was
another story. I got on my feet and was face to face with Alyssa's mother. Her
name is Jessica. She is in her early forties but was an Amazon at 6'4,210
pounds and still very attractive. She was wearing a black nightgown. I could
see her body sheen straight through it. God, her "C" cup breasts were amazing.

Sadly, the mom's tits were the last thing on my mind at the moment. She was
pissed. "What the hell do you think you were doing perched up there?" demanded
Jessica.

"Uh...Uh..." was all I could say. I realized my dick was still hanging out of
my pants. My manhood shrank like my confidence.

She forcibly grabbed my hand. "You're coming with me boy. If you give me any
problems I will call the police. Do you understand?"

I shook my head in agreement and was led into the house. I was so scared and
ashamed I could not look at her. Alyssa's mom took led me up the stairs into
what appeared to be her bedroom. I was glad I did not see Alyssa along the
way. If I had seen her I would have died of embarrassment.

She closed the door behind me and told me to stand in front of the closet. I
complied with her command. Alyssa's mom sat at the end of her bed. I was no
longer worried about zipping up my pants because my prick had shrunk into my
pants.

"So tell me young man, what were you doing sitting on the tree?" asked
Alyssa's mom. "And I don't want to repeat the question. I want an answer now!"

I took a deep breath and all I could muster was, "I was watching your daughter
undress and I was masturbating."

"What did you say? I couldn't hear you."

"I said I was watching your daughter undress and I was masturbating."

Alyssa's mom then looked at my crotch. I tried to cover myself, but she shook
her head and I put my hands back at my side.

"What were you masturbating with? I don't see anything." She remarked.

"With my penis." I answered. My face flushed with embarrassment.

Alyssa's mom laughed at these words. "Okay, now I have to see this. Take off
your shirt, pants and underwear and give them to me." I wanted to refuse. I
had no choice. I did what she said and I reluctantly gave her my cloths
standing stark nude in front of her.

I tried to cover my pubes with my hands. She grinned, shook her head and
slowly I put my hands back at my sides. My scared prick and nuts did
everything in their power to hide from her fierce gaze.

"My goodness you are so small." She said with a smirk. "I'm guessing you are
still a virgin. Are you?"

"Yes, I am," I answered, but in my defense I feebly replied, "It gets bigger."

I could tell she was about to burst out laughing. She restrained herself.
"Okay, show me!" she answered with a devilish smile.

My face was red. I wanted to die right there. No such luck. I tried to grab my
shaft, but it was no use. I was too nervous. I massaged my limp dick, but no
amount of manipulation could get a hard on out of my deflated unfriendly
scared penis.

"Oh God! This is pathetic. Come here!" exclaimed Alyssa's mom.

With my head hung low I stepped forward. Alyssa's mom sat me on her lap facing
her and started to caress my family jewels and slowly she stroked my shrunk
shaft with her soft hand. Pleasure soon over powered my embarrassment and my
old friend rose to the occasion. "Oh... God! I am going to cum!" I murmured. I
placed my face on the mom's shoulder as I was embarrassed. She quickened her
strokes on my shaft. It was too much. "Ah...ahhhhh!" I said as my juice shot
out on her breasts.

She threw me off her lap. I fell down on my butt. I was breathing hard.
Looking up I saw Alyssa's mom rubbing my cream on her breast. She tasted the
last drop and smiled back at me. I could see a hungry look in her eyes.

"Now it's time to teach you a lesson," giggled the mom.

She went out of the room and came back in a few minutes. With her finger she
motioned me forward. I obediently crawled to her and looked up into her eyes.
She hiked up the skirt of her nightgown and spread her leg.

She was wearing a strap on dildo. I happily took the gift into my mouth... I
wildly sucked on her plastic cock like there was no tomorrow.

Alyssa's mom answered my efforts by a long sexy moan. She placed her hand on
my head and slowly pushed the plastic phallus deeper into my throat. My dick
throbbed with anticipation. She pulled my head free of her cock.

"That's enough. Time for the main course," she said with a grin.

Alyssa's mom sat back on the bed and I sat on her lap facing her. She grabbed
her strap on and placed the large bulbous mushroom head on the entrance of my
asshole. I had shat before the stroll. I didn't bother to wipe. I was lucky
some of the pulpy shit was still clinging to my anal entrance. It was the only
natural lube at the moment. The odor of my shit swirled around the room. I had
a problem taking her plastic cock in my vestibule. It was painful.

Alyssa's mom giggled and said, "Let me help you."

When she grabbed and squeezed my penis, I lost control and shot my load on her
stomach. She shook her head and smiled.

"This really is your first time, but at least you're still hard." She guided
her strap on into my virgin anus. I had to steady myself. I didn't want to cum
so quickly again when she fucked my ass. When she was confident I wouldn't cum
she forced it all the way inside.

God, it was wonderful. Gradually she increased her stroke, speed and length of
travel, and began pumping in and out. Alyssa's mom dug her nails into my ass
and kept on saying harder, faster. She slammed her cock inside me as fast and
as hard as I bounced up and down on her lap. The pressure to cum was
unbearable.

To my relief Alyssa's mom told me to cum on her body. At those words I emptied
my sperm on her thighs. I collapsed on her.

She smiled and patted my back and said, "Not too bad for a first timer."

I chuckled. All was right with the world. I heard a truck pulling up.

"Shit. my husband is back!" hissed Alyssa's mom between clenched teeth. She
pushed me off into the hallway.

"Don't worry I'll clean up. Get out of here before he sees you," she said
slamming the door shut.

I tried to ask her for my cloths, but then I heard the front door slam. I
bolted through the first door that opened. I closed the door behind me and
realized I was in Alyssa's room! Thankfully she was not in. I heard footsteps
coming up the stairs and I hid in the closet.

I could hear someone talking in the hall. It had to be Alyssa's father. After
awhile it was silent. When I felt safe enough to come out, the door of the
room creaked open. It was Alyssa. She wore a small t-shirt and a pair of white
cotton panties. She stretched and yawned. To my surprise she pulled of her
t-shirt and flung it to the floor. Her perky breasts presented themselves to
the room. Her small nipples hardened when they met the cool air.

I thought I was spent, but my penile member proved me wrong. It stood straight
out horizontal and wanted to say hello to Alyssa. To my horror she heard the
closet door creak. She walked over to the closet and flung the door open. She
was surprised to see a naked boy in her closet. The same grin her mom had,
appeared on Alyssa's face too.

"So you were the one with my mom," Alyssa said with a smirk.

"Wait. You are in my class. Mike?"

I nodded in agreement.

"Alright Mike. Lay down on my bed. I'm going to show you how it is really
done," giggled Alyssa.

I did as she said. My member stood straight up like a flagpole and it seemed
she was about to plant the flag, so to speak figuratively. Alyssa walked over
to her dresser and pulled out a strap on. She opened the package and wore it
on her pubic crotch.

"There we go. Nice and neat," she replied.

I was in total awe as Alyssa sat me on her lap facing her. She positioned my
ass exactly aligned to her plastic cock. She took a deep breath and lowered me
onto her plastic cock. Alyssa slowly slid me down her plastic strap on until
she entered me completely to the hilt. She let out a low purring sound from
her gut that I will never forget.

When I was confidant I began to move up and down on her cock. My ass was
tight. It felt like her strap on was going to tear my anus. I had to place my
hands on her shoulders for balance. I wanted to make this last as long as
possible. I was on the brink of Cumming. I held it at bay.

Alyssa's tits were bouncing on my face. I took a hard little nipple into my
mouth and started to suck and nibbling as a newborn. Her purring turned to
moaning. Remarkably she squeezed my member harder with her hand. It was
driving me crazy. Then I whispered in her ear, "I'm Cumming. I'm Cumming."
That was it; I arched back when I shot my load on her.

Breathing hard Alyssa kissed me on my cheek. With the strap on still buried in
my ass and said wearily, "That was great."

"Yeah it was."I said.

Alyssa pulled out the strap on from my ass and sat me on her thighs. She was
about to say something, but a knock at the door interrupted her. I jumped off
her lap. Alyssa started to freak and I didn't know what to do.

"Alyssa?" It was her dad.

There was just one way out now. I opened the window and jumped out reaching
for the nearest branch outside. I grabbed it and made my way down to the
ground. I did not hear any yelling. So everything seemed to be fine. I
realized I was still naked. I turned around and started running towards home.
I looked back hoping to get one more glimpse of Alyssa. When I turned to face
where I was going, I collided with a protruding branch. I was flung down on
the ground and dazed. I got up and hurried off home.

Back in my room I threw myself on my bed. I could feel my eyes begin swelling.
My nose trickled blood. Like I said, the memories of my encounters over
powered the pain showing on my face. I closed my eyes hoping the next day's
show would as good.