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Member Since: 9-Jan-07
Location: US
Posts: 112
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Just getting started
Adventures in babysitting

When I was in high school a friend roped me into babysitting. She said it was super easy and Id only need to do it when she couldn't. I had no idea that it would lead to the defining sexual experiences of my life.

I mostly baby sat for this one kid who barely looked at me before he stomped upstairs. A little later he'd show me his homework while running out to play with his friends. His mom, Gina, would show up a couple hours later give me a few bucks and I'd be on my way.

Gina suggested me as a sitter to her friend Paula. Paula introduced me to sex and every way she knew to please a woman. She taught me how to make a woman cum, and more importantly, make sure she cums. I spent more time licking between her legs than between the pages of Playboy that

(If you haven't read my story about Paula, It's the first part of this story and Paula was my first. She launched me into the sexual life I've had. It's also super hot. smile)

It was a month or so before Gina hired me again. I was doing my homework when she arrived. Gina was a dentist’s nurse and she actually dressed like a nurse. White button down blouse, white polyester pants, white sneakers. (LOL!) I'm sure it was not meant to be sexy, but suddenly her unifrom was insanely sexy to my raging teen libido.
I swear to this day that her pants and blouse were tighter...
She unpacked some groceries while she asked about her son. I could barely focus as she bent and reached.

Gina was tiny, easily a foot shorter than me, but in that tiny package there was a lot of fire. She had soft, womanly curves on her small frame. that filled her pants with the stuff wet dreams are made of.
She ask me to put something up high. "Uh yeah..." I took my backpack with me to hide the fact that I was super hard.
She stayed close, as I reached up. Her perfume filled my nose as I tried to not be the teen boy I was. I said over and over in my head. "don't look at her boobs, don't look at her boobs."

I couldn’t help it, I looked. Her demure cleavage barely showed, but it was enough to make me blush with excitement. I said goodbye and ran out of there as soon as I could.

Our chats became a thing. She'd ask about stuff and probably thought I was an idiot because I'd lose my train of thought watching her beautiful body as she'd put dishes away, or reach deep into the fridge... There were times when I had to stay and sit longer because I was so visibly excited. This went on for a few months.

Gina hired me for a weekend night. When I got there she and her husband were ready to go. She asked quickly as they left if I could help with the laundry. "I'd really appreciate it." I reluctantly said sure and they were off.
After her son went to sleep I went to the laundry room, annoyed. I opened the dryer, reached in and grabbed the dry clothes. When I stood I realized I was elbow deep in her panties. There were other things, but my eyes were glued to a red set of panties on the top. I leaned in and took a deep breath of fabric softener, cotton and teen fantasy.
I rubbed myself through my jeans, imagining Gina's lips on the other side of the cotton pressed against my nose.
Then I noticed a dark curled hair. I could barely control myself.

And by barely control myself, I mean not at all.

Now you have to remember, I was a teen boy. Looking too long at a Georgia O'Keefe painting could make me cum. The thought of Gina 's wet lips and my tongue separated just by thin, red cotton.... I'm surprised I made it to the bathroom.
I imagined Gina in those panties as I rubbed myself with them. It didn't take long before I felt the building excitement. Her panties turned a deep crimson as I came into them. When I was done I hid her panties deep in a laundry basket and hoped she wouldn't notice.

When they got home Gina was clearly tipsy. As we talked. Gina took off her coat. She was wearing a short black dress that clung to her body. It had pulled up, showing more of her legs than she expected. She grabbed the hem and wiggled her body trying to pull it down. She barely covered her thighs and her cleavage bloomed forward. It was mesmerizing, and I think she knew it.
My release from before only made me more excited to see her. I was ravenous... The sight of her filled me with desire.
She asked how things were working out with Paula. I said they were good.
And I will never forget the next moment.
"I heard you're delivering pizza now. If you're ever delivering on our block let me know. I'd be interested."
Pizza delivery was my code with Paula. Paula not only told Gina we were fucking, she was sharing me.
I was so worked up I felt myself turn red with lust. The look on her face made it clear she noticed.
Her husband was clueless.
"Yeah.. anytime."
"Great." She put money in my hand, her skin touched mine for the first time and I wanted to scream with pleasure.

It was a couple weeks before Gina hired me again. I could barely think all day I was so anxious to see what was going to happen. Gina was early. She gave her son some money and said he should go out with his friends and have fun. "Be home for dinner."
She was shy, maybe embarrassed. She talked with me briefly about school and stuff. She caught my eyes on her legs. I was sweating from the tension-
"Could I have some water, Mrs. Matthews?" Gina poured me some water. She saw how wound-up I was.
"You ok?" she asked. She put her hand on mine. I looked at her and realized she was more nervous than me. This was totally new for both of us. "Yeah.. I'm just..." I looked at her lips...
She nodded. "Yeah."
She asked me to help her put dishes away. As I put one up high, I felt her hand touch my exposed stomach. I turned to her and she ran her hand up my chest. Her eyes locked on mine and there were a few moments of "are we doing this?" My hands found her hips and I caressed her gently.
Her hand found the bare skin at the top of my jeans. She lingered there as we took in the lustful anticipation.
She lowered her hand and let out a breath as the girth of my shaft filled her hand. "Oh god..." She stood on her toes. As we kissed she firmly rubbed me. I untucked her shirt. I needed to feel her skin.
She was giving my cock long hard rubs. She looked down at my hips as I pushed against her hand. "Oh my god..."
with her lips brushing against mine she whispered "I want you in my mouth."
before I could say "uh huh..." her was pulling my pants down.
She opened wide and wrapped her lips around me.
I clutched the counter for balance as Gina's hands glided the length my shaft, slick with her saliva.
She pulled me out of her mouth and look at my now pulsing penis, her hand firmly sliding from top to bottom.
top to bottom.
top to bottom.
"Oh my god..."
I would say I'm average size, but the way she looked at me was like I was huge.
Paula told me later that Gina's husband was "unusually small." Gina told her a few times that besides not feeling appreciated , she wanted... more...

I watched her beautiful hips and shoulders wriggle as she tried to fit more into her mouth.
I swear I love fully clothed blowjobs because of Gina.
The crown of my penis popped out of her mouth and she rose off her knees. Her dark lustful eyes locked with mine. Her lips and chin glistened as her hand rubbed the length of my cock, her fingers would cup my balls, then up again.
"I want this inside me."

I dreamt of this for so long & the teasing was so brutally hot, I'm surprised I was able to perform.

I didn't cum watching her curvy, petite body climb the stairs in front of me.
I didn't cum when she wriggled out of those pants.
I didn't cum when her nipple was in my mouth, or as my tongue ran down her happy trail.
Or as I took in her musky scent through her panties.
Or as I tasted her for the first time.
Or as she moaned and guided my fingers to how she liked to be touched.
Or as I watched those breasts heave as I licked her closer to an orgasm.
Or when she pulled at me, we slobbered a kiss and she said "I want you inside me."
I didn't even cum when my fully engorged tip pushed against her, and the ridge of my crown splayed her lips wide,
But when my head slipped into her petite body. and she gasped like I was completely in her. I almost came.

I closed my eyes and froze.
"Don't stop there...go deeper..." she was breathless and on the precipice of an epic orgasm.
I was frozen. We sat for a moment. She played with herself as I gained some control. Gina lost patience.
She wrapped her legs around my ass and pulled, thrusting my cock deep into her...
It felt like I was going further into her than she'd ever had. she let out a guttural "Huuuuuahhhhuhh!" as a sank deep into her.
I learned what the word tight meant that day. It felt like her hand was wrapped around me squeezing.
"Go hard."
I understood what that meant. I quickly pulled my hips into the air and thrusted. Her breasts bounced "Moohha... Mmmm harder....."
Our skin slapped together as I pushed into her.
It's probably takes longer to read this then it took me to feel my orgasm rise again. I'm sure she could tell because she pulled me to her. Her warm breasts felt amazing against me. Her legs bound me to her. My last few thrusts I pulled her off the bed, then dropped her while I went deep into her.
Her pleas of "harder" were punctuated with my thrusts making them gasps of lust as much as demands for deep, hard pleasure.
"Huhhaarder. Huhaarder.. Huhaarder..
I felt my cock engorge and I squeezed to hold back the cum...."uhhhhghdh!"
I tried to pull out but she was wrapped so tightly around me I couldn't.
I had never cum inside a woman before and it was magical.
She swirled her hips as I ground deep into her, I pumped releasing my pressure. I could feel my cum making our tight bond slippery and silky. It made me want more and I thrusted harder.
When I finished I opened my eyes to find her staring at me. she whirled her hips and I did the same. she nodded.
"Uh huh... uh huhhh.. uh huuhhh....mmmmmmm.... She arched her head back and stiffened up like a board "MMMMMhhuhaaaa. She writhed her hips, grinding her orgasm longer.....
It was beautiful, lush, hot, sexy and I wanted more.
But we only had so much time so we dressed and I ran home eager for our next visit.
Gina and I didn't have as many times together as Paula and I, but they were insanely hot. I fell in love with petite bodies because of her.

She told me that Paula had told her about me almost immediately. She asked Paula if I was big. Paula said "see for yourself."
She admitted she was teasing me for a few months and loved it when she knew I was excited. She loved knowing I was undressing her in my mind. When I was reaching high to put stuff away, she was measuring me with her eyes. She also told me she had masturbated to me, which made me blush, but was extremely hot.

Eventually I was able to have my eyes open and watch her orgasm while I filled her with cum.

She had only ever been with her husband, who wasn't cutting it and probably never did. She wanted to try different positions to feel a thicker, bigger cock inside her.
Eventually her favorite was to ride me. I think because she loved my hands on her body because I fucking loved feeling her. As she got closer to cumming I'd run my hands along her thighs, cupping her plump ass, and I'd help her up and down. Eventually I'd be lifting her off my throbbing shaft and thrusting her onto it. She'd moan almost continually. It would always make me cum hearing her pleasure grow as she pounded against me. "mmmMMmmmmMMmmmMMmmmmMMmmmmMMmmm"
After we'd both cum, she'd pulse her hips feeling my still throbbing cock in her and giggle ijn a way that said "That was goooood!" Gina truly knew how to enjoy and I love her for that to this day.

I hope you liked the story. comment if you do and PM if you want. I love pmssmile

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Member Since: 15-Jun-05
Location: US
Posts: 149
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GREAT story, in line with your usually HIGH standards.

THANK YOU! So love hearing about your adventures!

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Member Since: 9-Jan-07
Location: US
Posts: 112
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Tasties said:

GREAT story, in line with your usually HIGH standards.

THANK YOU! So love hearing about your adventures!

Thank you, I'm happy you like it!


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Member Since: 18-Aug-05
Location: US
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Love the story
Great job sharing such a fun time for you. Hope to read even more.

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Member Since: 9-Jan-07
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Candy52958 said: Great job sharing such a fun time for you. Hope to read even more.

Thank you! I'm glad you liked it! Gina & Paula (Not their real names) were life changing for me. Gina was especially good for me because she just had a joy for sex. She'd beam with happiness after our sessions.

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Fantastic post, we both loved reading it xx

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Member Since: 9-Jan-07
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cissyboy1uk said: Fantastic post, we both loved reading it xx

TY! I'm happy you both liked it! I hope it made your evening a little hottersmile

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