Mrs. Sinclair Pt. 01

She wasn't old but she was older. A very mature woman. Wrinkles had started to appear on her face but only up close did I notice them. She was a redhead with greenish eyes. She didn't have a model's body. She wasn't skinny with perfect firm breasts and lifted-up butt. She actually had a belly you know like a real person does. She must have been in her fifties. She was older than my mom and all I knew about her was through my mom. She had been my neighbor almost all my life. She had divorced a long time ago. She was my lonely redhead neighbor.

My mom thought she was a nice and a bit naïve lady. Ordinarily I'd see her she would wear very conservative clothing. Regularly I saw her at the church my family attended where she would help organize events. She also worked for an insurance company though I don't know what her job title was. Mostly though she was at her home doing who knows what. The only times I saw her wearing something different was at her backyard doing her routinely garden work. For this she wore different clothing. Now it was nothing crazy but my favorite were the denim shorts because they were pretty tight. She would get on her knees and lean over the flower beds giving me a perfect view of her shorts stretching to the shape of her ass. She had nice mature woman breasts and a nice plump ass. That was my view of this woman.

I wasn't obsessed with her and I would have forgotten about that but things changed. The day after my eighteenth birthday something happened. My parents made me a small dinner for me. It was a small party, just my immediate family and a couple of my friends as the very next day my last semester in High School would start. After we had dinner and my friends left, Mom prepared a plate, wrapped it up in foil and sent me to the neighbor's house with it. I've done this before since the woman lived by herself and my Mom was good friends with her.

She opened the door already wearing pajamas. As I said before she was quite conservative. Her pajamas were normal. Lose white pajama pants with vertical red and pink lines. Her top was this-long sleeve button up nightshirt.

"Hello, I'm sorry to bother you Mrs. Sinclair but yesterday was my birthday and today we had a small dinner to celebrate. Very small thing, and so my Mom prepared some food for you."

"Oh, thank you! Congratulations how old are you now? I hadn't even noticed how big you are now!?"

"I turned eighteen yesterday. I have school tomorrow though so we just had a small celebration nothing fancy."

"Wow, 18 already. Time sure flies. Hey, I didn't know it was your birthday but I'll tell you what. I'll improvise a gift. Come inside and I'll find you something."

"Oh that's not necessary. I don't want to bother you."

"It's no bother at all, it pleases me, come on in." She turned around and I turned my head towards my house in the dark, everyone about to go to sleep. Then back towards the doorway where I saw Mrs. Sinclair's ass walk away from me. Even with pajamas the shape of her cheeks were clear.

I'd never been inside her home. I was expecting religious objects and a cluttered place but it wasn't that. It was spacious and on her wall a few paintings hung. None were religious it was all abstract art. She led me to her living room and asked me to sit.

"Can I get you something to drink? I was making tea. Would you like some?"

"Um, yea, sure."

She walked to her kitchen and while she got me a cup I admired her home. I didn't notice while she walked towards me but it was impossible to ignore when she sat the cup in front of me. Was I imagining things now? The top buttons of her long-sleeve blouse were open so that when she bent to place the cup more cleavage than I had ever seen from her was at display. She wasn't wearing anything underneath but I couldn't see any nipple. She had large breasts. Now what really turned me on was my brain playing games with me. I wanted to believe that those buttons were not open like that when I walked in. As she stood the buttons were obviously open and I was almost certain this wasn't the case when I talked to her at the door.

"Okay, I'll go get something for you don't go anywhere."

"I'll be here." Finding myself in this situation, as she walked upstairs moving those hips graciously, my mind started playing fantasies I had perfected. I half believed this woman would be walking down with no clothes or I would hear her tiny sexy voice asking me to go upstairs and to my delight I would find her in bed.

She made her way downstairs after a few minutes.

"I have a book for you and I just remembered it's actually down here in the living room".

I didn't say anything just smiled and observed. She moved toward a shelf next to where the TV was. Strange that she went upstairs to look for a book instead of on her bookshelf. Her back was towards me as I got to see something different once again. Then my jaw almost falls off my face. I couldn't believe what I was seeing. She had changed her pants. She was now wearing black leggings. They clung to her lower body so tightly. These were not see-through material but her legs were meaty and her ass was hypnotizing well shaped. Not something I imagined this church lady would ever wear.

After looking over the top shelf she gave me the real gift. Slowly she bent over, ass directly at me. She stood at a 90 degree angle and slightly would move her ass left, then right, as she looked over the book spines. Was she wearing anything underneath? I shifted my sitting position to a more comfortable one sliding a bit downward and opening my legs a bit. I was wearing black dress pants for the party and the bulge in my pants was going to be noticeable if this continued.

What a spectacle.

"I can't believe I can't find it." She fell to her knees and awkwardly and unnecessarily lifted her butt a bit. "I can't read these titles I need to get really close". Yes, what a spectacle.

But finally she found it. Stood up and handed it to me.

"Now that you're all grown up this book hopefully motivates you." I looked at the title How to Win in Life! By Marlene Lewis. Mm. Looks like a corny self-help book. But it wasn't hard to receive the book and smile. I already had my gift. I had never spent this much time talking to the woman let alone the image of her ass in those leggings now forever burned inside my head.

"Thank you I really appreciate it," I said "I will be leaving for college in a couple of months but, um, I know we barely know each other but I've grown fond of you over the years as neighbors. I do mean it thank you..." where that come from? Then I somewhat awkwardly opened my arms and she leaned in for a hug. Then she moved her feet right up to mine. I was taller than her, her head leaning against my upper chest. Then the hug lasted longer than a usual hug. "You're so sweet!" I could feel her breath on my neck and her breasts against me. Carelessly her hands fell down to my ass and though she didn't put pressure I could feel them resting there ever so slightly inviting me to move closer. Then I felt my boner against her. We were way too close so the bulge in my pants was pressed against her. I don't know what part of her body it was but it turned me on more than anything that had happened that night.

She didn't say anything but she must have felt that. And that was something I would jerk off to that night because sadly we ended the hug then she thanked me for the food and all I could do was say goodnight and leave.

I saw her again the next day. As I walked home from school she was outside her home watering her plants.

"Hey John, how was school?"

"It was fine ma'am, the usual stuff."

"Are they keeping you busy these last few months? Aren't you a little early today?"

"Actually not, I'm done with the class requirements so this new semester I just found out I will have two free periods. I could take a class but I rather be off school two hours early. That's why I'm so early."

"Oh wow, you will have a lot free time then."

"Yeah, I'll find something to do I suppose."

"Mm, well you know what maybe I could use some help. Would you like to make some money?"

"Well, sure. I'm not sure I could be of much help for you but I can try."

"It's not a favor, I'll be paying you. Think about it and let me know."

"I'll do it!" I exclaimed a little too eager there. I was really looking forward to doing nothing with my free time and even though making some money was good what I didn't have to think about much was that getting to ogle Mrs. Sinclair again was too good to pass on.

"Do you want to get home and then come back?"

"It'll be fine I can get home later no one is expecting me this early anyways."

She led me inside and proceeded to remove her thin coat. It doesn't get too cold here in Southern California.

"I think I'm going to have you help me with moving some boxes upstairs and organizing." She had some boxes in the living room and I didn't ask what was inside them. I followed her upstairs with one of the boxes as she led me to a room. She walked in front of me and then told me to put the boxes on a table.

I still think this is where the games officially began.

I walked into the room behind her and stopped to hear her instructions. The room was being used as a storage place by the looks of it since there were other boxes around and some old furniture and stuff like that which made the place difficult to walk through. When she finished...

"Okay thank you Jack." Then she walked towards me. "Oops let me squeeze through here dear." She didn't give me time to think, I simply turned left and moved back as much as I could to let her through. The box was in her way though so I started lifting it but she didn't wait. She walked through, with difficulty. She faced the wall that I was facing so that her ass inevitably would be brushed by my crotch the way you might have to on the subway. Thankfully for me the position of the box in my hands forced her to bend her knees a bit. So the 'brush' became total contact. She moved fast towards me but slowed down enough once we touched for my dick to have a reaction.

It felt good but having not expected it diminished my reaction. This was not the case again because this started a series of games Mrs. Sinclair and I started to play. The respected lady I saw at church liked to play games. She came back upstairs after a few minutes with a water bottle for me.

"Should I leave it on top of the table?" She could have handed to me but instead started walking and slightly pushed her butt towards my private area. I knew she had to walk out again. I could have moved but I didn't, I just waited feeling a growing erection. Again she walked through, this time I faked a 'problem' balancing and held her in front of me without caring that my erection would be felt by her.

"Ah, you okay?"

"'Yes, I just lost my balance there for a second." I said as I still held her against me.

She then walked downstairs like nothing. It took me an hour to organize the room and my thoughts, then I walked downstairs looking for Mrs. Sinclair. She was cooking.

"Hey Mrs. Sinclair I finished organizing everything upstairs. Maybe you'd like to come take a look?"

"I'll check in a little bit. Aren't you hungry? I'm almost done cooking."

"Now that you mention it, I am a bit hungry."

"Good, and you're a grown up now you can call me Andi."

"Okay, Andi. Actually I just realized I didn't know your name."

"Why would you right?" She smiled at me. "It makes me feel old though when you call me Mrs. Sinclair. Besides, I got divorced a long time ago and never took his name."

"So technically it's Ms. Sinclair right?"

"Hah 'yea I suppose. Somehow that's so much better than Mrs."

"Then can I call you Ms. Sinclair? I feel like it sounds," It kind of turns me on. "Mm. I don't know, sounds better to me."

"That's sweet. Yeah you can call me that as well but there's no need for formalities. Help me set the table won't you? Reach those bowls from there won't you?"

"Sure." That long skirt she was wearing would kiss her ass and look so tempting. Obviously, the cupboard was above the stove and right now she stood in front of the stove. I decided that this time I would make the move. I was nervous though, what if I have been imagining things. What if she gets mad and I get myself in trouble. So I slowly came up behind her staring at that big ass, in the process provoking my penis to become erect. I took my time but ever so slowly I started to feel her butt against me. Reaching up looking for the right bowls I moved a bit against her skirt. To my delight they were a bit far and I had to push closer. Why not enjoy myself some? So I grabbed one bowl and took it to the table, then came back for another one. She kept cooking like normal while my hard on pushed against her cheeks.

I found the rest of the stuff and set the table. Afterwards we went upstairs to look at the room and the teasing continued. "It looks great!" Blah blah blah. Every time she'd bent over to check what was inside a box I had to struggle not to jump on her. I wanted to fuck her while she still wore that skirt. I preferred the leggings though. We talked and I moved some other stuff around.

"Okay, it's been a while. I'll let you go now and if you'll come back tomorrow I can have more stuff to do and I'll even pay you." She smiled at me.

"Sounds great Mrs... Andi. I'll come back tomorrow at the same time."

And so I did. That night I masturbated thinking about her but soon I found that abstaining myself some nights in a row made my erection brushing against her so much more intense. It was difficult because I started to fantasize about Ms. Sinclair all the time. This continued for the next day. On Wednesday she wore leggings again.

"Those look good on you Andi." I complimented her in an offhand way at some point. She wore them again from that day on. On that Friday she wasn't even wearing them but she went and put them on at some point while I worked. I ogled her every day and she gave me so many chances to push my erection against her. I was timid at first but as the days went by I started to worry less and less. We didn't talk about it but we both knew what was happening and the lack of acknowledgement honestly turned me on. I ate with her every day and I discreetly would peek her cleavage. But as I was saying the discreteness went away.

"Should I clean the table now?" She would ask me. Which was code for me to get ready. I'd say yes and she would walk over to my side of the table to lean and put her breasts right in front of me. I wouldn't hide my stare at all. It was glorious and different every day. Some days she didn't seem to wear a bra and her breasts would stretch her blouse. Other days she wore a bra but her blouses would be a lot more open. She enjoyed herself too. She would touch me a lot. My ass, my chest, my arms and so. Once I was sitting on the floor putting together a desk she had bought from IKEA when she came behind me and said "thanks for helping so much!" as she hugged me. Her breasts against the back of my head and her arms curiously around my chest and arms. I'm not a bodybuilder but I'm fit. This also turned me on very much.

This went on for two weeks. I hadn't told anyone I was doing this. On the second Friday I worked for her I decided to wear basketball shorts. I never wore basketball shorts to school but that day I did. It was risky, you know because those don't hide an erection at all. By the end of the day I knew it had been the right choice.

Ms. Sinclair prepared normal jobs for me which were getting pretty obvious she didn't need. I watered plants outside. Did her front lawn, again. It hadn't grown in the last two days. Then I followed her upstairs where she went down on her knees to look through some drawers. She pulled out papers, read them, and then passed them up to me. I was to put them in order. As usual with something like this I would stare at her butt just getting hornier and hornier. Finally a tent was visible on my shorts. Bravely I decided just to ignore it and enjoy it.

The lady had a harder time ignoring it. It was a big tent. It must have looked funny too. As she turned around to pass me some papers I caught her eyes staring at it. Lustful eyes. I pretended to be distracted reading one of the papers as she passed me another one which gave her the opportunity to bump her hand against my erection. This was such good teasing that kept me hard. So now every time she passed me something her head would bump against my head. When we finished I moved before she stood up. I had a question you see.

"What is this about Andi? I'm not sure which pile it belongs to." I moved forward and put my tent next to her head over her shoulder. I was over her as I handed her the papers. She took the papers and scanned them. As she read them I moved my cock against her head until I was well pressed against the side of her head. How could we keep acting? She read the paper and told me what to do with it. Then she started to stand I moved backwards but then she lightly got hold of my shaft as she stood. It looked like she needed it to stand and her hand felt so fragile and small against my cock. She let go of it after a few seconds but it was so fucking hot.

We ate as usual. Afterward she wanted to watch a show which was unusual but I agreed. Sat on the couch and invited me next to her.

"Isn't it cold Jack? Aren't you cold?" It wasn't. She didn't wait for my answer though and stood and grabbed a small blanket sitting at the other couch. She then sat down again now much closer to me and laid the blanket over both of us. Her hands quickly got curious again. We watched a half hour show as she moved her hands up and down my left thigh. Then surprise! She found my shaft again. She didn't grab it, instead she decided to pet it. Down my leg and then up and up all the way over my cock. This quickly got me hard again. But the show was done too soon.

It was time to go. Actually it was later than usual. We hugged goodbye and I put my hands on her ass for the very first time. I didn't squeeze but I made the hug last longer and left my hands there.

"Okay young man. I really appreciate you coming. You've been working only on weekdays but I actually had another job in the garage for you if you wanted to come in tomorrow. It's going to take a few hours I think."

"Oh man. At noon tomorrow I have to meet some friends. Um, maybe I can get started today? It's only 3:30 after all."

"That'd be great if it okay with you. Maybe you'll want to call home and let them know you'll be late?"

"Yes that's true," I pulled out my phone. "I'll call my mom don't worry, she's still at work though."

We walked back inside, me behind her staring at her cheeks, with my mom on the phone.

"Hey Mom...yea... hey I'm with friends right now, do you mind if I stay at Steve's house tonight?" I lied. I hadn't said anything about Ms. Sinclair's odd jobs. In fact, on Sundays at church when I saw her, my family and I would just say hi as usual so she hadn't said anything either.

As expected my Mom couldn't care less and said yes. Ms. Sinclair didn't say anything either. She heard me lying and she hadn't said anything about me staying at her place but I knew she knew that was the plan now.

The job wasn't big but it was dirty. In her garage she had her old car and it needed an oil change, the air filter replaced, and even the battery. She had all the parts ready so I worked. It was only 5:15 when I finished though and she read my mind.

"Thank you so much but wow I'm sorry I didn't think about how dirty you'd get!"

"It's okay, these aren't new clothes or anything Andi." And I live next door.

"Nonsense. I think you should clean up, maybe take a shower. I can't let you go home like that." I followed her upstairs where we entered her room then we kept going to a room I had never been in. It was a spacious bathroom. We entered then she stopped. "Okay, leave your clothes on this chair then I'll come back and take them so I can wash them. There's a bathrobe hanging on that wall you can use," I nodded "Okay sweetie I'll be right back."