Chapter 1
Jack
I was quite taken with the girl named Gail who was our neighbor in the duplex behind ours. Gail was the daughter of our landlord. She was a year older than me and most times acted as if I didn’t exist even though I went to pains to get her attention.
It was a dark summer’s night and I just happened to see the light come on from one of the bedroom windows. Thinking it might be Gail’s room, I snuck out through my bedroom window and carefully made my way to the lighted bedroom.
I was stunned when I raised my head up enough to see into the room through the lifted blinds. This was not Gail’s bedroom. This was her single mother Jane’s bedroom.
Jane was just coming out of her bathroom, she was completely naked. My dick instantly jumped to complete erection as I gawked at her nakedness.
“Oh Fuuuuuuuck,” I moaned when Jane began smearing lotion all over her naked body. My dick jumped and seeped precum into my boxer shorts as she rubbed and groped on her own breasts.
“Fuuuuuuuck me,” I gasped when she laid back on the bed and began masturbating. I pulled my cock out of my gym shorts and began jerking off like a crazy man while I watched her finger fuck her pussy under her thick bush of black hair.
I don’t think I lasted 30 seconds before my cock exploded into climax. My knees jerked over and over while my dick sprayed cum all over the bushes against the house.
I could swear that Jane turned her head and gazed at me before I could back away from the window. Quickly, I ran back to my duplex and climbed back into my room through my window.
I was eating breakfast that Saturday morning when there was a call on the landline. Mrs. Gemhart wants to speak to you,” Mom announced. My hand was shaking as I took the phone. Did she see me watching her last night?
“Hello sweetheart, I was wondering if I could hire you to mow the lawns around the complex. I could give you twenty dollars each weekend,” she offered.
Twenty bucks for maybe two hours of work sounded like a gift to me considering I made less per hour at the local grocery store where I was a stock boy and box boy.
I readily agreed. Jane cheerily told me that she would have a little bonus for me each weekend.
I knocked on her door at a few minutes after noon that Saturday. I needed the key to the garage to get her mower out and other tools I would need. Jane answered the door wearing a very short robe. It was transparent and she was naked underneath.
My dick was so hard that I beat off in the garage before I came out to mow the four large yards. The entire two hours that I worked, my mind was racing. Wondering why Jane answered the door and exposed herself to me like she had.
When I finished, Jane insisted that I come into her house even though she was still wearing the see thru white robe. “Do you think I’m pretty Jack? Do I look better close up instead of from the window last night?” she asked.
“I-I-I…didn’t…I wouldn’t…” I was stammering trying to figure to get out of having been seen peeping on her.
“It’s okay baby, I enjoyed you watching me. It made me get off really good knowing that you were jerking off for me,” Jane told me. “Yes, I think you’re beautiful,” I blurted out the answer to what she’d asked me.
“How would you like to climb in bed with me and find out what it’s like to be with a woman?” she asked softly. “But I’m all sweaty,” I gasped. “That’s okay baby, it will just make our bodies slippery and a lot sexier,” she told me.
Without a word, Jane led me to her bedroom. I noticed that the blinds were closed today. After Jane undressed me, she pulled me to the bed. Once she had me on my back, she got between my legs and sucked my cock into her hot watery mouth.
“Oh gawd, Oh gawd, Oh gawd,” I panted. My hands came down on her head as she bounced her mouth up and down my drooling cock. I doubt that I last ten seconds before I blasted my load of cum down her throat.
“That’s okay baby,” she announced when I was apologizing profusely. “Now I will teach you how to eat pussy and get me off until your dick gets hard again,” she purred.
As promised, Jane did teach me how to eat pussy. How to lick her pussy lips. How to tongue fuck her. She taught me where her g-spot was and how to suck just right on her engorged clit. She taught me how to get her off with my fingers and mouth. Twice.
My dick was as hard as a crowbar when she rolled me onto my back. Effortlessly, she straddled my cock and shoved down till my entire cock was engulfed by her buttery hot and slick pussy. The very first pussy I had ever been inside.
The sensation of her slippery pussy riding up and down on my cock was electrifying for me. I was incredulous that I was inside of Mrs. Gemhart’s pussy. I had always dreamed that her daughter might be my first.
“Mama’s pussy is so much better than a younger girl would be,” Jane purred as if she’s read my mind. “You stay with me and I will teach you everything you will ever need to know about pleasing a woman,” she declared. I had no reason to not believe her.
I spent the entire summer fucking Jane every Saturday afternoon. There is no doubt that she taught me everything I would ever need to know about sex. At least that’s what I thought by the end of the summer.