Alyssa still is beautiful but there was just something
about her on Who’s The Boss? Aside from writing the
Samantha Micelli story, I never intended to do a story
about Alyssa Milano ever. But after I came up with the
idea for the “Making Babies: Sarah Michelle Geller”
story I felt a strong need to do a story about Alyssa,
during my favorite period of her life. Damn, she was
cute on Who’s The Boss? … Drools- G
[Sometime in 1986]
I hate going to the mall. With a passion! But I was out
of video tapes and one of the stores was running a big
sale on multipacks of video tapes.
I think the VCR is one of the best inventions ever. I
can record my favorite shows and watch them whenever I
Secretly, I record shows for the actresses that I lust
after. Specifically the young actresses.
I love to record shows like Who’s The Boss and Family
Ties because I have the hots for Samantha Micelli played
by Alyssa Milano and Jennifer Keaton played by Tina
Yothers. I could never fuck sweet, hot babes like that
but I can always fantasize about it, right?
Anyhow, so I had to go to the mall and decided to go at
the least busiest time. I went straight to the store,
bought several packs of my video tapes, and was ready to
get the Hell out of there.
Suddenly I smelled the aroma traveling all the way from
the Food Court… What the Hell, I can spare a few more
minutes to see what they’ve got.
Making my way in the direction of the delicious smells,
I wasn’t paying attention and I bumped into a girl
wearing sunglasses and a floppy hat. They both fell off
as she sprawled to the ground, and somehow my own
sunglasses came off as well.
“Damn, I’m so sorry!” I said. I bent down to retrieve
our sunglasses and her hat as she easily sprang right
back up. “I should have watched we’re I was going.”
“No, it’s my fault,” The girl said. “I was in a rush to
get out of here.”
When I turned around to hand the girl her sunglasses and
hat, we both gasped, wide-eyed.
“You’re Samantha Micelli!” I blurted out. “I mean Alyssa
At the same time the thirteen year old blurted out my
own name. “I’ve seen all your action movies! I LOVE all
of your action movies! You’re my favorite actor!”
Alyssa blushed a little when she realized what she just
We looked around. Fortunately, no one was close enough
to have heard our exchange or notice us at all.
Alyssa quickly threw her hat back over her long brown
her and put her sunglasses back on. I put on mine as
“I’m a big fan of you as well,” I admitted. I held up my
bag of video tapes. “I record your show, just to see you
over and over again.”
Alyssa blushed, but smiled. “Thanks!”
“I was getting ready to leave, but I can’t resist the
smells coming from the Food Court. Care to join me?”
“Would I?!? You bet!” Alyssa gushed.
We made our way to the Food Court without further
“How about Chinese?” I asked, spotting the kiosk on the
far side of the large room.
“I LOVE Chinese food! Good idea, I don’t think any of
the people working their will recognize us.”
We laughed. I’d been thinking the same thing.
We ordered and received our food, and sat down in the
nearly deserted food court.
At first we made small talk. The weather. Sports.
Fashion. But then I brought up Samantha Micelli.
“I love how you play the character,” I praised. “You
make her so believable.”
Alyssa blushed darker.
“I’m WAY different from Samantha! She insisted
defensively. “She can be very…wild…compared to me.
Can you keep a secret?”
“I’m still a virgin!” She leaned across the small table
Surprising myself, I whispered back “Want me to fix
Alyssa’s jaw dropped as her eyes went wide.
She quickly recovered, smiled and blushed again. The
girl blushed a lot.
“But I’m only thirteen…”
“And I’m over thirty,” I nodded.
“It’s…not that…” Alyssa said, biting her lip
“It was just an offer,” I said. “It would be an honor to
be your first, Alyssa Milano. IF that’s what you want.
Besides, it’s something I’ve always fantasized about.”
Alyssa smiled again, but mischievously.
“To bed a thirteen year old?” She asked teasingly.
“Ha ha. No, to bed you,” I replied. “Or Tina Yothers. If
you want I’ll make the offer to her too.”
Alyssa gasped. Then she giggled.
“I’ve never met Tina. But I love her as Jennifer on
Family Ties. She IS kind of hot,” Alyssa admitted. “If I
was a guy I’d want to do her too,” She grinned.
“So? What do you think about my offer?”
“To tell Tina Yothers you want to do her?” She grinned
“The other offer.”
“I’ll have to think about it,” Alyssa said. “I mean, how
often does a girl like me get propositioned by her
favorite actor? Not that I’d be able to tell anybody
about it if we did. I wouldn’t want you to go to jail. I
definitely don’t want you to go to jail…” She said,
putting her hand on mine.
“I agree, it’s a good idea to think about it first.”
We quickly changed the subject, Alyssa talking about her
homeschooling which I actually found fascinating.
We finished eating and returned our food trays. When we
reached the parking lot I asked her how she got to the
“Bus,” She said, without disdain.
“So you’re not waiting for anybody in particular?” I
asked. I wanted to offer her a ride but I wasn’t sure
“Actually,” Alyssa began looking up at me [she was just
around 5′ tall to my 6’5″], “I’m hoping for a ride from
my favorite actor. I’m hoping he’ll take me home with
him and make me a woman.”
I suddenly felt as giddy as a school boy. “Really?!?” I
asked. “I mean, are you sure?”
Alyssa nodded. “It’d mean a lot if you were my first.”
I wanted to kiss her, but here in public like this, that
wouldn’t be a good idea.
“Let’s go!” I said.
Alyssa giggled and followed me to my Mercedes. Soon we
were driving off and heading to my bachelor pad.
I was feeling really nervous. Like a teenager on his
first date. This was silly, I thought. There’s no reason
to be! This wasn’t “my first time at the rodeo”. I’d
fucked lots of women, starlets and girl next door types.
This wasn’t any different.
Except it was. It really was. I never fantasized about
any of the other women I’d fucked. And a fantasy of mine
was about to come true.
“I’m a little nervous,” Alyssa admitted softly, putting
her hand on me forearm.
“Good,” I said, putting my hand on hers briefly and
giving it a small squeeze. “Because I am too.”
Alyssa leaned her head on my shoulder as I drove the
rest of the way home.
I was soon parking my car in my garage and leading the
girl into my apartment.
Suddenly Alyssa turned to me, grabbed my neck and pulled
my face down to hers, kissing me.
“Let’s do this before I lose my nerve!” She said
Alyssa immediately started tearing off her clothes. Her
body was so beautiful…
She was slim without an ounce of body fat. She didn’t
really have any curves yet – well, actually her
small/medium-sized butt was very shapely – and her thigh
were slim and coltish.
Her breasts were perfect. They looked to be a C-cup,
large on her small body. And her pussy was unshaven,
obscured by a sea of dark brown curls.
I grabbed and swept her up in my arms. Alyssa shrieked
then laughed, wrapping her arms around my neck.
I carried the light weight girl up to my bedroom and
dropped her on my bed. She giggled.
I took her delicate hand and placed it between her legs.
I pushed her fingers against her pussy and slid them up
“Ohhh! That feels good!” Alyssa gasped.
I moved my hand and she opened her legs a little,
continuing to rub herself and moan.
She watched as I quickly undressed. If she’d seen all of
my movies then Alyssa already had an idea of the shape
I’m in, since I end up taking my shirt off a lot.
I’m well-muscled and don’t shave my chest, abs or arms.
The women love that.
When I slipped off my jeans and briefs, the girl gasped
“Will that fit in me?!?”
“Don’t worry, your pussy will accommodate me,” I assured
her. “It’ll probably be a tight fit at first but as you
relax and have orgasms your pussy will open more.”
Alyssa nodded as I mounted the bed and her. I gently
spread her legs and leaned down to kiss her finally. Her
lips tasted sweet. Like wild cherries.
I can feel her hand against my stomach as Alyssa rubbed
her pussy more vigorously.
She broke our kiss, head lolling back.
“Gah, what’s happened?!?” She groaned.
“I’m betting your about to have an orgasm, Alyssa
She thrust up her body against me and cried out. It
wasn’t a particularly powerful orgasm, but for a girl
like her I bet she thinks it is…
Her body went limp and Alyssa was breathing heavy. Her
hand slipped away from her pussy.
Opening her eyes, she smiled.
“That was wild.”
“I thought you said you didn’t do wild things,” I
teased. “Samantha did.”
“Well… I guess I’m learning to be a little more like
I slid up until my cock was against Alyssa’s slit.
Placing my hands on either side of her, I started to
slide my cock along her wet pussy. It slowly hardened
“It’s getting bigger,” Alyssa moaned. “And hard…”
“It has to be hard,” I said. “For me to get it into
Fully erect, I started to dry hump her faster. Alyssa
started thrashing under me, gasping and hissing. Her
pussy was getting wetter, coating my cock with its
Her convulsions grew stronger.
Alyssa was now moaning loudly. Her head thrashed from
side to side. As her second orgasm approached, I reached
between us and placed my hand against my cock, waiting.
Then she came. And I pressed hard on my cock, forcing it
to slide into her opening. I shoved it all the way in,
breaking Alyssa’s hymen as she was still orgasming.
I pumped in and out of her fast, her pussy getting used
to my size and shape somewhat, though I couldn’t go in
all that deep yet.
As I kept fucking her she orgasmed again, screaming
loudly now, her pussy gushing juices around my thrusting
cock and opening more.
As her body calmed, I found her pussy starting to relax
and allowing me in a little deeper. I slammed my cock in
and out of the girl hard, inducing orgasm after orgasm,
with Alyssa begging for more.
I lost track of how many times she came. I lasted about
twenty-five minutes before I grunted and jizzed inside
the girl deeply. I must have shot off in her eleven or
I can feel my jizz pushing out of her past my invading
Finally spent, I hardly lost my erection as I stayed
inside of her.
We were both sweaty, Alyssa had this glow about her now
as I looked down at her. I pushed a few sweaty locks of
her out of her eyes.
“How do you feel, Alyssa?” I asked.
“Good,” She smiled. “But sore.”
“No! It’s all right,” She insisted. “Not too sore. Not
so sore I don’t want to do it second time,” She
I felt my cock regain its full hardness.
“Oh, really?” I teased.
Alyssa nodded sheepishly, blushing.
“Does that make me some kind of slut?” She asked.
“No way! You only want my cock, not every guy’s cock
Alyssa nodded vigorously.
“You’re not a slut, sweetie.”
“Thanks,” She smiled. “Now fuck me again!”
“Fine,” I said. I flipped us over, making her squeal and
cling to me tight. “But YOU’RE on top this time…”