A few years ago during the Summer of 2009 I was sixteen years old and a sophomore in High School. I lived with my father in a pretty nice house at the end of a Cul-de-sac in an upper middle class neighborhood in Santa Rosa, California.
That was the summer I met Ashley and her son Cameron. They moved into the house next to my own. Ashley was in her mid 30s and single. I thought she was attractive, even though she was a little on the heavy side. She was short (about 5'2'') and had a really pretty face with big dark eyes and long dark hair. She had a swarthy Mediterranean complexion, a nice pair of tits and an ass that looked just about perfect packed into a pair of blue jeans. I'd stare at her through the curtains in my bedroom when she was in her sideyard planting flowers and usually get really hard staring at her big round ass.
One day I decided to introduce myself. It was about her third week in the new house and she came home with a big load of groceries. I walked over to her car and smiled.
"Need a hand??"
She looked up and returned my smile. "Oh hey, your my neighbor right??"
"Ryan," I held out my hand. We shook briefly.
"Hi Ryan, I'm Ashley," she said. "And yeah thank you. Just grab a bag and follow me into the house."
I did as she instructed. Once inside I noticed she didn't have very much of anything. The living room was pretty much empty. Only one small room off to the side was furnished and I assumed the bedrooms.
"Big old empty house," she sighed. "I'm starting over."
She set down her load on the kitchen counter and showed me her ring finger. I could see where a ring used to be, but it was gone now. "Recently divorced from my son's father."
"Oh, sorry to hear that," I set my bags down next to her own.
"Don't be," she headed back to the car. I followed her. "I and Cameron are a lot better off. Cameron is my son by the way, have you seen him yet??"
I had. He was about seven or eight years old and very obviously retarded. I saw him playing in the yard from time to time.
"He's the little red headed kid right??," I asked. "The one that plays in the backyard."
"That's my boy," she grinned and lifted out a particularly heavy bag. I took it from her. She thanked me.
"He's my heart and soul," she said. "Just like I'm sure you are for your mom."
"I wouldn't know," I said. "My mom died when I was about Cameron's age. Cancer."
"Oh my gosh," she put a hand up to her mouth. "I'm so sorry, I shouldn't have...."
"It's fine," I smiled. "It's been a long time. Just me and my dad now. I mean he has a girlfriend but he doesn't bring her around much."
"I see," she watched me set the bag down. "Well Ryan, it was certainly nice meeting you and I appreciate the help."
I grinned. "Anytime. I'm nearly always home. Home schooled. So if you ever need a hand, don't hesitate."
"I'll remember that," she smiled back.
It was about a week later that Cameron came home crying. I saw Ashley comforting him on their front porch and looking furious. I walked over.
"Is Cameron ok??"
"Damn little bullies," she kissed his forehead and rocked him in her arms. "Some kids from school follow him home everyday and tease him. Call him names."
"Jeez," I frowned. "Well, if you'd like I can walk him to school and then back home again everyday. I'm an early riser and I don't really have much else to do anyway."
She looked at me gratitude in her chocolate eyes. "Really?? It wouldn't be an imposition??"
"Not at all," I said. "Nobody will bother him anymore. I'll see to that."
"Oh thank you so much!," she smiled brightly. "Your just the sweetest thing."
And so I started walking her son to school everyday and back home again. I saw his pack of bullies and I made sure to put a good scare into the leader, a buck toothed fifth grader that looked like his family gene pool needed a little chlorine in the worst way. With their leader cowed, the rest scattered.
After that I saw Ashley on a pretty regular basis. I even began fixing things around her house, when I noticed her trying to repair the garbage disposal in her kitchen. I'd always been pretty handy with home repair. It was sort of a hobby of mine. I even barbecued with them.
"I haven't had really good cue in forever," Ashley said, turning up the volume on her stereo. It was tuned into a classic rock station. I stood over the barrel barbecue in my backyard. Dad was pulling another long shift at work and I'd been home alone when I noticed Ashley trying to get the charcoals in one of those cheap single use disposable grills lit. I called her and Cameron over.
"Dad and I barbecue a lot," I said. "Well, we used to anyway. I've been using this grill since I was Cameron's age."
The kebabs smelled mouth watering and Ashley looked even more edible in her jean cutoffs and SF Giants tee. I was pretty sure she'd caught me staring a couple of times, but how could she expect me not to stare?? She looked amazing.
And that's pretty much how things went for a few months. I was always around helping out in one way or another, spending time with Cameron while Ashley worked in her office, teaching him to play catch, shoot a basket and play croquet (he loved croquet - even Ashley would join in, forgetting her stacks of paper work). One night I even scared off a would be burglar with my Louisville slugger.
And so a day came in mid August when I'd brought Cameron home from school and Ashley and I stood in the kitchen, while he played in his room.
"You've been such an enormous help to me," she told me. "I really want to repay you and since I finally have my head a little above water, I want you to have this."
I stared at the small roll of money in her outstretched hand.
"I don't want your money," I said, shaking my head.
"But you deserve it," she stepped closer. "Its the least I can do."
I shook my head again. "I haven't been helping you because I expected anything in return. I did it because well, because I like you."
"There you go being a sweetheart again," she smiled. "But I don't feel right not rewarding you in some way."
"Well," I said, then stared at the ground. "If you wanted to reward me, you could. I just don't want money."
"I don't understand," she withdrew her hand and the cash.
"Well," I sighed. "Nothing. Forget it."
"No tell me," she said.
"It's just that, it seems to me that I'm doing all the things that a man of the house would do if there was a man of the house," I said. "I guess I'd just like to be rewarded like the man of the house. If that's the job I've been doing."
She stared at me a long moment and I'd just decided I'd allowed my little head to royally fuck things up between us when comprehension dawned in her eyes and she nodded. "I see. And how exactly does a man of the house get rewarded??"
I shrugged. "You know?? Your the woman of the house. I've been acting like the man of the house. Doing repairs, protecting Cameron and spending time with him. Spending time with you both. Chasing off that creep the other night. I guess I'd just like to spend some time together with you. Just us."
"You want to have sex with me," she asked.
I could feel a warm flush of heat rise up the back of my neck. "Well yeah."
She thought it over a moment.
"If we do this, nobody ever hears about it. If you speak one word of it, I deny every bit of it and I never have anything to do with you again. And it doesn't mean your my boyfriend or I'm your girlfriend. As it happens I have a date with a guy I work with this weekend and I'm kind of hoping it leads to something. If so, I don't want you getting jealous and acting out."
"I'm fine with that," I promised.
"You positive??" She asked.
I nodded.
"Ok then," she smiled prettily. "Since you've been my knight in shining armor, I'll give you what you want. Can you come by later tonight around 11 o'clock?? Cameron will be asleep by then and I'll be finished with my take home work."
"Sure," I nodded. "Should I bring condoms??"
"Not if you trust me when I say I'm clean, because I am," she told me. "I'm on the pill. You can come inside of me if you want to."
Hearing her say "come" caused an instant erection in my pants. I wanted her so bad. I wanted her now, not later.
"Can I touch your tits before I leave??"
She laughed and nodded. "Go ahead. Just a quick feel, then home. I have work to get on in my office."
I stepped closer to her and reached out and cupped her left breast. It was warm and heavy. My thumb ran over the slight bulge of her nipple.
"I have a question," she asked. "Are you a virgin??"
"No," I said. "But I've never been with a real woman before. Just girls my own age."
"I see," she said. "And how big is your cock??"
"I don't know," I said, still fondling her breast. "Pretty big I guess."
"Nice and thick??," she asked.
I nodded.
"Ok then," she smiled at me, her dark eyes twinkling. "You've felt some boob. Go home and jerk off. I can see your hardon through your jeans. You look pretty big to me. I hope so anyway. I'll see you later tonight my man of the house."
After masturbating furiously in my bathroom I spent over an hour naked in front of the mirror staring at myself. I had a pretty nice physique for a sixteen year old, but would it impress a woman?? I wasn't sure. I grabbed a ruler and measured my cock. It was no world record winner but it was larger than average, according to the information I found on the net. That at least made me feel a little less insecure. I just hoped I wouldn't come too fast. And I held out hope she'd let me come at least a couple of times before sending me back home.
I showered twice and then shaved my non-existent facial hair before applying some of my dad's after shave and cologne. I hoped she liked Brut. But then, I started thinking what if she didn't like it?? I showered again. Clean without a scent was better than clean with a scent she might hate, I decided. All there was left to do was wait. Time crawled.
The phone ringed around ten o'clock. I felt my guts twist. Was she backing out?? "Hello??"
"Hey champ," it was my dad. "I'm going to be stuck here at the hospital for a while. There was a pretty bad wreck on the Interstate and we have some very sick people on the way in. I'll be needed in surgery."
"Ok dad," I breathed out in relief. "I'll be fine."
Great I thought, I wouldn't have to sneak out then. Not that my dad would mind. He knew I had a crush on Ashley and he'd even jokingly asked me once if I was "hitting that" yet. "Just be careful champ," he'd said. "Wear protection. Its all fun and games until you wind up with a baby or an STD."
I considered raiding his underwear drawer for the box of condoms he kept there. Remembered what Ashley said and thought about how great it would feel sliding inside of her skin on skin. I forgot about the condoms. I trusted her.
Finally at a quarter til eleven I slipped out the back door and made my way to the back of Ashley's house. I knocked and she opened it for me.
"Hey there," she smiled. I smiled back.
"You look great," I said, despite the fact she was still wearing the same thing as earlier. She giggled and locked the door behind me.
"My bedroom is the big one on the left, just off the hall from the kitchen," she explained. "Go in an undress. Get into bed. I'll be there shortly baby."
Her calling me baby worked its magic. Instant hardon. A voice in my head mockingly said "We're too easy" I agreed. But I didn't care. I found her room and kicked out of my clothes in record time. I sat back on the bed with the blanket covering my stuff member.
The bed was enormous and covered in fine silky sheets and a heavy blanket. Tons of pillows lined the headboard. The room smelled like cinnamon. I loved it.
About ten minutes after I'd sat down she appeared in the doorway wearing a black lace trim teddy. I gulped.
Her tits looked even bigger than usual and she'd let her long dark brown hair fall down to the small of her back. She closed and locked the door and walked sexily toward the bed.
"I like toys," she purred and took a box from beneath the foot of the bed. It contained furry handcuffs, a huge flesh tone dildo and other items I couldn't begin to describe. "And I like it rough and dirty. I want you to treat me like a slut. Can you do that baby??"
I nodded. "Ye...yeah."
"Good," she crawled up onto the bed and leaned across me, we kissed. Her tongue probed every inch of my mouth. "Now use me as if I was your personal whore Ryan. You can do anything. Tie me up. Cuff me. Fuck me in the ass. Fuck my mouth. Come on me anywhere. Call me a dirty bitch... you own me for the next two hours."
What followed was the most amazing night of my teen years. Guided by Ashley's directions I had sex in a way I'd never had it before and it forever made any other kind of sex too boring for me. It became all I ever wanted.
We moaned and groaned and made each other come until I felt exhausted. When we were finished, she kissed me and smiled. "Not bad. I'll shape you up yet."
Ashley would go on to begin a relationship with her friend from work and once he became a more permanent fixture around her place, I found myself alone at home again most of the time. But Ashley still called me over a couple of times a month for some late night fun.
I moved away from home this year to go to college and I don't see her anymore. But I'll always have the memories and who knows?? If I ever find myself back in Santa Rosa, things could pick right back up again.