The Grand Strategy

I was on a roll. Three for three. As I said, I was not looking at this as an ego thing, but I couldn't help feeling pretty cocky. I had been to visit Carol and Aunt Ellie a couple of times each, and every time was better than the previous. These were women who loved a good loving. Carol was especially fun, and would usually say something during our lovemaking that would crack me up. She was a fun fuck. Aunt Ellie was loving, too, but I have to admit that we had gone about as far as I thought we would. She wasn't into experimentation. I suspected that my times with Aunt Ellie would dwindle, but we would always have our special bond.

I didn't think I was ready yet for Mary, Roger's Mom, because she was so much like my own Mother, Tammy. While I thought Bridget was unattainable because she was so beautiful (and I was pleased to learn differently), I almost knew Mary was unattainable because, like Mom, she was just so straight-laced. Mary was the consummate soccer Mom. She was usually our designated car pool driver. No matter the hour, she was always perfectly dressed, not a hair out of place, and perfectly made up. She brooked no deviations from her rules. Because she was so much like Mom, I joked with her more than the other guys did, and usually referred to her as "Drill Sergeant." I thought her strictness was kind of cute because I was used to it with Mom. When she'd lay the law down, "You boys quieten down back there!" I'd laugh, while Roger just rolled his eyes. Of course, it was the reverse with my Mom. Roger would joke with her, while I was the one rolling my eyes.

Mary. She was taller than average, willowy thin, and had the most beautiful red hair. I saw her occasionally around town since I had moved back and she seemed hardly changed. Her hair was still a beautiful red, which I suspected was chemically enhanced by now. While Mom had let her hair gray naturally, I guess Mary wasn't ready for that yet. Her hair had always been her crowning glory, so I could understand. I have to admit, there was a time in college when I seemed focused on redheads. I'll admit it. I love a red-haired bush. Would I ever get to see Mary's?

I was intimidated by Mary. The thought of her ever doing anything that was not right and proper was beyond imagination. If anyone was going to freak out on me and call Mom, it would be Mary. Man, that's a conversation I did not want to have, so I was afraid and could not come up with a good first step.

When I did see her in town, we would always hug. The last time, about a month ago, I had hugged her really tight. She acted kind of flustered, and I thought I had been a little over the top. Since I had gotten that reaction from her, I didn't know how to get her moving into a man/woman realm, rather than a quasi-Mom/son realm.

Since I was so hesitant, I thought I'd call her. Maybe I could say things over the telephone that would be more difficult face to face. So, I did. One Thursday afternoon, I worked up my nerve and called her at home. When she answered, I said, "Hi, Mary. I haven't seen you around town lately and thought I'd call to see if I could contribute to the ransom. Have you heard from Roger lately? When's he coming home?"

She sounded as if she was glad to hear from me. She laughed and said, "Who? Roger? Is he the boy who used to live here? I don't know when he'll ever show up again." I laughed with her, but her voice had a winsome quality to it that told me that Roger was not keeping the home fires burning.

"Oh, he's probably just busy, Mary. You know how it is."

"Yes, but you can find time to call me, Bill."

Here I took a tiny step. "Yeah, but that's because I've always had a weakness for hot red-haired soccer moms."

Her laugh was delicious. "Maybe you can transfer some of that to Roger, then. Is it contagious?"

"It's not contagious, Mary, but I'm afraid it's incurable. I've had it forever."

"Bill, you have always been such a kidder. I could keep the others under my thumb, but I could never intimidate you."

"Oh, yeah, Drill Sergeant. You've always had me pretty well intimidated."

At this point, I reached down, made sure I still had a pair of balls, and once I decided I did, I went for it. I had not planned this, but it seemed like it might be the right opportunity.

"Did you ever know, Mary, how much I always wanted you?" I said it in a light-hearted way, kind of bantering to fit our conversation, but the message was clear.

"Bill. Is that something you should say to a woman who cleaned up your puke from the mini-van after you got carsick and threw up?"

I laughed. She remembered that. "Probably not, but it's something I would say to the hottest soccer mom in the state."

She didn't respond to that directly, and I thought maybe I had pushed too far, too soon. She said, "So, when am I going to run into you again?"

"I dunno," I said. "When are you going to be out again? If I'm going to stalk you, you're going to have to help me out a little."

"Shy Bill, a stalker? I don't think so. As a matter of fact, though, I was just running out to the grocery to pick up a few things."

"You're not going to believe this, Mary, and I promise I'm not really stalking you, but I was going to get some frozen pizzas. Maybe I'll see you there."

I didn't need frozen pizzas. I had a freezer full of them, but I grabbed my jacket and ran to my car to get to the grocery store. I got a cart, went to the freezer section and grabbed some pizzas, and then cruised the aisles looking for her. After about 20 minutes with no sign of her, I was beginning to fear I might be looking suspicious, so I headed toward the check out, disappointed. From the store entrance I heard, "There you are! Fancy meeting you here."

And there she was. Beautiful. She had on black yoga pants and an over-sized sweater, and looked great. The sweater was emerald green, kind of hung off her shoulders, and her creamy freckled skin looked delicious. I stopped short, took a long exaggerated look at her from bottom to top, and said softly, "And you wonder why I've always wanted you?"

With that, she hugged me lightly, but seemed nervous. She stood there with her arms crossed over her breasts, in what I interpreted as a defensive posture, and I didn't know what to say or do next. Had I already blown it?

Just as softly as I had spoken, she said, in a joking way, "Maybe I'm the one stalking you, big boy. You ever think of that?"

I laughed, relieved. She didn't seem mad or scared, and as long as we could keep joking with each other, maybe I could get my foot in the door. "You would never have to stalk me, Mary. Say the word and I'll set up a pup tent on your front lawn."

This was now uncharted territory. I was openly flirting with her, which I had never done before. At least, I had never flirted so openly.

"Ha!," she said. "Settle down, big boy. You're squirting musk all over the store and you'll ruin the fresh vegetables."

Now that was funny, and we both laughed at it. She hugged my arm, pushing her breasts against it like Carol had done, and said, "Are you finished? You want to walk with me while I pick up a few things?"

Oh, yeah. Yeah, I did want to walk with her. I pulled my cart behind her in the narrow aisles, and appreciated that sweet ass in her yoga pants. Once she turned around to ask me something, and caught me looking at it. She laughed, took a sale leaflet from her cart and held it over her butt, and I didn't know if she was laughing at me or with me, but I didn't care. That was a sweet ass.

I had never seen Mary like this. She was practically being flirtatious with me, and that was out of character for her. She was the Drill Sergeant, and Drill Sergeants don't flirt.

She needed only bread and milk, after all, so we headed to the checkout together, me with my two pizzas and her with bread and milk. After we had checked out, I carried her bag out to her car and we stood there talking. She had her arms crossed over her breasts again.

"So, is that all you're eating these days? Isn't Tammy feeding you better than that?"

"I eat at home when they need the cupboards cleaned out, but most of the time I just chow down on pizza or Chinese at my apartment. I'm still a growing boy, you know."

She hesitated, and I saw her kind of chewing on her lower lip. "Roger's dad is going to visit his Mother this weekend. I miss Roger and all you boys. If you're not going to Tammy's for dinner tomorrow, why don't you come and I'll fix you a real meal." She kept her arms crossed over her breasts and looked down nervously. "But if you have other plans, that's okay."

"Are you kidding, Mary? Pass up one of your meals? What time? Can I bring wine? Anything else I can bring?"

"Just bring your hungry self. I think he's leaving after work, so why don't you come about six? And yes, some white wine would be good."

"It's a date!," I practically had to hold myself to keep from shouting. "I'll see you then."

Driving to my apartment, I was so deep in thought it's a wonder I didn't run off the road.

She only bought bread and milk. Did she really need it? Couldn't she have gotten that at the gas station service mart near her house?

Why make a point that Roger's dad was not going to be there?

Why was she dressed so sexily? Was that for me?

Why invite me at all? We had seen each other occasionally for months, and she had never asked me to come by. Why now?

The next day dragged on. I went early in the day to buy a couple of bottles of wine and then had nothing to do until I went to her house. I changed my clothes about three times, trying to decide what to wear, and finally decided on a pair of khakis and a short-sleeved oxford shirt. Real imaginative, right? I was as nervous as I had ever been for a date, and this wasn't even a real date. This was just me going to my bud's Mom's house for dinner, right?

Finally it was time to leave and I drove carefully to her house. Now was not the time to run into a ditch. I could just see that. "Hi, Mary. I'm stuck in a ditch and can't make it." Yeah, there would probably never be another chance like this, and I wasn't going to jeopardize it.

When I got there she met me at the door. She had on yoga pants again, in a light blue color and a white short-sleeved sweater. The sweater had a droopy collar, kind of low cut, but I couldn't really see it because she had her arms crossed again. Her hair was up in a pony tail, which was very attractive on her. I kissed her on the cheek and sniffed at her neck. "Wow. What is that? It smells delicious."

She said something about the brand. I didn't know it, so couldn't comment other than, "I really like it on you. Nice."

Mary took the wine, turned, and led me into the kitchen where she was finishing supper. I didn't waste any time checking out that ass in those blue yoga pants. She seemed to be putting an extra movement into her ass, and I hoped she was remembering when I was checking her out at the grocery store. If she had not liked it, why had she worn yoga pants again?

She flitted around the kitchen, checking this and checking that, and talking non-stop. She kept her arms crossed and seemed to be avoiding facing me directly. I think she was as nervous as I was. I hoped she was, because that meant she might be thinking the same thing I was thinking. While she was taking the pork chops (I love pork chops) out of the oven, I checked out those tits. Her nipples were standing tall, like proud little soldiers, and they must have been an inch long. Where in the hell did those come from? I had never seen such large nipples before, and I sure had never noticed them on Mary. She appeared to have a light bra on, but that didn't stop those nipples.

She caught me looking, I think. She said, "I've got a little chill. I think I'll go put a light sweater on." When she returned she had on a light cardigan, buttoned up, but it couldn't hide those nipples. Even if it did, I knew they were there and I knew she was excited. For the record, it wasn't chilly at all in the kitchen.

I opened the wine while she plated the food, and we moved to the dining room.

"Dining room? I'm honored. I thought I was a back door, kitchen table kind of guy."

Laughing, she said, "It never hurts to have a little elegance in your life, you know."

I poured the wine and raised my glass to her. "Mary, you are the most elegant thing I will ever have in my life." She blushed.

The meal was delicious, and so was Mary. She was still nervous, but the wine seemed to calm her after awhile and we talked and talked. We didn't just talk about when I was a kid with the gang, but we talked about politics, and the economy, and global warming. She was enchanting, and could talk in depth about any subject. I was entranced. How could I ever have thought this woman was cold and Puritan? She was vibrant and alive.

We finished one bottle during dinner and I insisted on cleaning up the dishes for her. She stood behind me while I was at the sink and we continued talking naturally. I don't know if she realized it, but we were talking like a man and a woman, and not as a friend of her son and his Mom. I was loving it. When I finished the dishes I dried my hands and she said, "That Mother of yours has trained you well."

I smiled and looked her dead in the eyes. "I've more training yet to get, Mary." It may have been lame, but it was the best double entendre I could think of. She blushed again, and said, "Let's sit down in the den. You want to bring the other bottle of wine?"

"I dunno, Mary. I don't want to fall asleep on your couch."

"Well, if you do, it's okay. Not like you haven't done it before."

She sat on the couch, and I sat beside her so we could put our wine glasses on the coffee table. I could have sat in the chair at the end of the coffee table, but she didn't seem to mind when I sat beside her.

We talked and talked. She told me how hurt she was that Roger was not closer to her. She said he seemed distant when they talked, and he never called her. She always had to call him. When he talked, he seemed to speak only in monosyllables. She said she was worried about him. She thought he sounded depressed.

I told her that I had been the same way, and finally realized I wanted a much closer relationship with my Mom. I purposely said, "much closer," because I wanted her to wonder what "much closer" really meant. She didn't ask, though, and I didn't tell. I told her not to worry about Roger. "You know he loves you, Mary. He always has, and he always will. What man wouldn't love you? You're perfect."

"That's the problem, I think, Bill. I've always tried to be perfect, and I think it's intimidating for him. I wish I had been less perfect, sometimes."

"Mary, he'll come around. I did. He's probably under a lot of pressure. Be patient."

By that time, the only thing left we had not discussed was quantum mechanics, and I knew I'd be out of my depth there. There was a silence between us. Mary was looking down at her lap, and glanced nervously at me. She crossed her arms again.

I thought I was reading the signals right. She was warm and open with me, except for the crossing of the arms and I didn't know how to interpret that. During our conversation, she had occasionally touched me on the leg as she made a point. If she were a date my own age, I knew how I would interpret those signals. But she was Mary. Perfect, proper Mary.

It was do, or die. It was maybe you win if you do take the chance, or certainly you go home and masturbate in frustration if you don't take the chance. "Here we go," I thought. "Time to charge the ramparts, my lads."

"Mary?," I broke the silence. She looked at me expectantly, wondering what I was going to say. "Would you be offended if I tried to kiss you?"

"No, Bill. I wouldn't be offended, but I'm not sure it's the right..."

I leaned in to her, took her face in my hands, and interrupted her words with a gentle kiss to her lips. She closed her eyes, and relaxed in my hands. I continued the kiss, making it a little deeper and a little more passionate, and tentatively probed her lips with my tongue. She slightly parted her own lips, and I put as much passion and love in that kiss as I could. I could taste the wine on her lips, could smell the scent of her perfume, and I almost passed out.

After a few minutes of gentle kissing, I pulled back.

"Wow, Bill. I was not expecting that."

I didn't say a word, but went in for another kiss, and she responded this time with what seemed like a hunger. I put my right hand behind her head, pulling her into me, and she put her arms around my neck. I was pushing it, I know, but I put pressure on her and she laid back onto the arm of the loveseat, with me laying on top of her. I was not about to stop kissing her, both because I loved kissing her and because I didn't want to give her a chance to say, "Stop it. Get out."

She pushed me back and giggled. "You've got to let me catch my breath, Bill."

"Mary, you take my breath." Lame, I know, but I was doing my best, OK? I ran my fingers over her hair, and she reached back and released her pony tail. She raised up, pushing me off her, bent over and shook her head to free her hair. She looked at me, and this time she came to me for more kissing. I ran my fingers through that glorious mane of red hair and returned my hand to the back of her head.

"Bill," she breathed. "Are you sure about this?"

"I have never been more sure of anything in my life, Mary. I was not lying when I said I have wanted you forever. I have to be honest, Mary. I didn't need pizzas yesterday. I have a freezer full of them."

"Bill. Oh, Bill. I didn't need milk," and she laughed. We both laughed, and then we kissed again and she laid back on the couch again and pulled me with her. I pulled my left hand back, and cupped her right breast. I could feel the nipple in the palm of my hand. She bushed her fingers in my hair, and pushed my head down to her breast. I gently used my teeth and nibbled at her nipple through her sweater. I raised my head and looked at her beautiful face. She had her eyes closed, and softly said, "Mmmm."

I raised her sweater up from the waist and lowered my head to kiss her belly. I raised the sweater the rest of the way, over her breasts, and paused to enjoy the sight. She had on a sports bra and the sight of those cute little breasts filling the cups was breath-taking. I pulled her left breast out of the bra. I looked at her face, and she had her eyes squeezed shut. I teased my lip across her nipple, flicked it with my tongue, and then took it in my mouth. I didn't take more of her breast in my mouth, just the nipple, and I sucked it to beat the band. She whimpered, and I took my mouth off it to look up at her.

"I've always been embarrassed by my big nipples. They're grotesque, aren't they?"

"Good God, Mary!, I exclaimed. "Are you out of your mind? Those are the most beautiful things I have ever seen. They're perfect. Why would you say something like that?"

"Oh, the girls in school always teased me about them. They nicknamed me 'Eraser,' because they looked like pencil erasers. I hated them."

"Well, I love them. I'll bet Roger wouldn't let you wean him until he left for college."

She took me in her arms. "I'm glad you like them, Bill." I pulled back and helped her take both sweaters off, then the bra. Her skin was so creamy, with a light covering of freckles. I have never seen anything so lovely, and I told her so. She pulled me into her breasts and said, "Enjoy them, Baby. Tonight they're yours." And I did.

Mary loved having her tits sucked. They were a size like Mom's, I would imagine, that were just right to suck almost the whole breast into my mouth. I sucked and used my tongue on those nipples, working them around in my mouth. She shivered with delight. "Big nipples, little breasts," she said.