A fellow NN member suggested I post my memories from my blog here. I've had some adventures and I felt like sharing them with everyone.
Here goes nothing! I hope you like it!

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. So every once in awhile I'd show up, wait for the kid to come home, make sure he had some food and that he did his homework. A couple hours later his mom, Gina, would come home and I was done.

One day when Gina came home she said her friend needed a sitter and asked if I'd be interested. I thought why not.
Before I knew it Paula had called me to sit for her son. Gina was there when I showed up, they only lived a couple blocks from each other. As I played a game with her son, I could hear them chatting in the kitchen. Paula's husband hadn't "touched" her in a couple months. The last thing I remember hearing was "I'm going to lay spread eagle on the bed and yell take me!" Gina sushed her. It's so long ago I don't really remember more about that night, other then being surprised to hear a mom being interested in sex.

I sat for Paula a few more times. She was always on the phone when I got to the house and usually she would complain about her husband. Her husband seemed to be absent. Thinking now, he probably was having an affair and Paula wasn't admitting it to herself.
One day while on the phone she said "Something's gotta change. I almost jumped the pizza delivery boy!" She laughed and shook her head.

Something clicked. Hearing Paula say pizza boy, more specifically, "boy" flushed me with excitement.

I was a late bloomer. Let's face it. I was a boy babysitter in the burbs. I had a girlfriend once, but we were so young we didn't really know what we were doing. Porn wasn't available like it was today. I had a couple Playboy magazines my neighbor threw out and those magazines saw more action in those years then I've had since then.

Point is I realized Paula wasn't just a mom, she was a woman. I look back now and I'd say she was a fit, 40 something woman.

The next few days all I could think about was Paula and those words, "jump the pizza boy." I was happy to have those Playboy mags.

That next week I found myself standing by her front door. I knew her son was at school, I had a really bad plan, but I couldn't work up the nerve to knock. My hand was stuck in midair, my heart was beating so hard I could hear it.
And then I knocked.

My 16 year old fantasy has something to do with Paula coming to the door in lingerie and jumping my bones immediately.

When Paula opened the door she looked like she was in the middle of something and annoyed to have someone at the door. When she saw it was me, she was confused and asked what I was doing there.
I could feel the blood rushing through my body. I was so nervous and I choked. "I wanted to see if you needed my help?"
Paula was even more confused and said no. I'm sure she could see I was struggling. "Is there something else you want to talk about?"
"yeah... I deliver pizza now."
She was very confused at this point and I could sense her patience was disappearing. "I don't understand."
"Pizza. I deliver pizza. I'm a pizza boy."
She looked at me like I was insane, and then it hit her. She turned beet red and took a deep breath. "Maybe you should go home."
I said ok and turned around and knew when I heard the door close that I was out of a job.
I pulled my bike off the ground and began to leave when Paula called out to me. I turned.
"Why don't you put your bike around the back."

Paula opened the sliding door on their back deck and let me in. She told me to sit and I did. She left and I could hear her finishing a laundry cycle. I wanted to leave. I knew I was in trouble. She took a long time and when she came in she had a glass in her hand. She sat and looked at me.
"Have you been with a girl before?"
"Yeah, or course, yes!" Way too eager and she could tell I was over stating.
She took a drink and walked over to me and asked me to stand. I did. She got close to me and put my hands on her hips. Her breath was sweet with alcohol as she nipped at my lips.

I was a 16 year old virgin. I was raging and so ready to go. I ran my hand against her crotch over her pants and rubbed like I was buffing a car. She stopped me. "Hold on" she undid her pants and took my hand. She gently put my finger on that wonderful spot I had yet to understand.
"You feel that?" I rubbed and she reacted "gently. gently...." she guided my hand with hers. "Always start there, ok?" I nodded. She lead my hand back just a little and guided my one finger to coax her lips to separate. As they did I could feel her wetness. "Feel that?"
"Uh huh!" I was concentrating on not cumming.
"remember, always start here." She moved my fingers back to that spot I came to learn so well.
She rubbed me through my pants but I think she knew I was not going to last long. I think the only reason I was still standing is because I had rubbed myself raw with those magazines, thinking about her.

My 16 year old fantasy involved throwing her on her bed and having sex with her as she screamed my name.

In reality she laid me down right there in the living room. She took off her pants and sat on top of me. I could feel her warmth through my pants. I reached down to take off my pants and she climbed up me until her panties were right at my chin. I looked up at her as she looked down at me. I think she was contemplating if she was really going to do this.

She stood and took off her panties and I stripped my pants off. She snuck a look at my cock and lowered herself onto my face.
Eyes locked as I took a deep breath of her savory sent and began to lick. "remember the spot" I hit it and her eyes closed and she started to moan.
Her breasts were begging to be touched, so I reached up under her blouse and grabbed them.
"Gentle" She took off her shirt and her breast bounced free. What a fucking view. I still love to have a woman sit on my face.

How I didn't cum is a mystery to me. I was wriggling around hoping she'd touch me. I wasn't about to touch myself because I'd explode. So I slid my hand down her ass until I felt the fur between her legs. I reached further and found her lips and pushed a finger deep into her. Her eyes shot open and she moaned. She put her hand on my head and pushed me against her. "Use two fingers."
I slipped another finger and she almost jumped up she was so heated. "Oh god.Oh god!"
That was the moment I learned about gentle and slow versus hard and fast. She ground her hips against my face as I lapped her up and twisted my fingers inside her. Her breasts shuttered as she worked my face.
She screamed so loud when she came I thought the neighbors would come to see if she was ok.
Looking back, I realize now that she was as eager as I was to get some relief. She hadn't had someone touch her in months.

I was so ready to cum I reached down and started to stroke. She stopped me and pulled my hand away. I was literally in pain I wanted to cum so badly. She put my lips against her wet, wet pussy and ground my face into her.

As she started to get really excited she stopped and stood up. I was so confused. I started to get up and she pushed me down. She turned and straddled my face cowboy style. As she bent down I lifted my head and licked like I never licked before. I snuck my fingers in there and was playing with her pussy anyway I could imagine.

She moaned and rocked and I could feel her breath on my cock. She gently touched me and my hips went a foot off the ground. She teased me with a lick here and a stroke there to ratchet up the excitement.

As I got closer so did she. It was so hot. Then, she grabbed my cock at it's base and stood it upright. I looked down to see her lips slide down my shaft.
"I'm gonna cum... I'm gonna cum... Mrs. Jones I'm gonna cum"

If I knew anything from my only girlfriend it was that girls didn't like cum at all and to warn them when it's coming. I tried to pull away, but she put her arms over my legs, trapping me.
"I'm gonna cum" Her mouth slid up and down and I watched as she took my load. I'd say like a pro, but she was a housewife from the burbs, and fucking hot as hell.
She sat up to grind onto my tongue and stroked me so I'd buck. ( Yeah, she gave me the name. ) She came again and collapsed onto me.

Eventually we fucked in almost every corner of that house. She was most excited to have me fuck her in her husband's baseball room. Basically a man cave. Before we fucked(She had me bend her over his pool table), she took extreme pleasure in sitting me in his chair and sucking my bone dry. I was excited to just be there, but my favorite was always when she sat on my face.

Later when I was babysitting for Gina, she came home the one day and after she paid me she asked how things were working for Paula. I said they were good. 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." Her husband was not listening or didn't care.

My 16 year old fantasy would have been a threesome, but that was never going to happen. I found out later, on the rare pizza delivery to Gina, that she knew Paula and I were going to go for it. She had me pegged as a "naughty one". She could tell because I'd stay around longer when she wore her tighter nurses dress and got dinner ready while we talked. "Dinner always means a lot of bending over for pots." She was right.

When I got older and a real girlfriend it all stopped. It was hard to pretend I was babysitting anymore and I didn't want to do that to my girlfriend. I think I became the assertive person I am because of what I learned from the two of them. They gave me confidence in myself for the first time. For that, I think of both of them fondly.