The Grand Strategy

When I was a teen-ager, I was in a gang.

Ha! No, it wasn't a gang like you might be imagining, painting tags everywhere and selling drugs. I was in a gang of five teen-agers, eating marshmallow fluff and peanut butter sandwiches while playing video games, but it was a gang, nonetheless. We were tight.

There was Jim, with his Mother, Carol. Sorry, but I can't think about any of my friends without thinking of his Mother at the same time. As you'll see, the Mothers were as integral to our gang as any of us. Jim was the tall, gangly one and Carol...well, Carol was the sexy one. She was kind of short, plump, with big breasts and curly dark hair and seemed to always have a laugh on her lips.

Robbie was the smart one, but even more shy than me, if that was possible. He looked like Harry Potter, with his glasses and his forever unkempt hair. Robbie's brain always seemed three steps ahead of the rest of us. Robbie's parents were killed in a car crash when he was very young, and he was raised by his Aunt Ellie. Aunt Ellie was Robbie's Mom's older sister, so she always seemed older to us. We always called each other's Mother by her first name, but she was just Aunt Ellie, to everyone.

Roger was the athlete. He was always strong and well-built, and won every wrestling match. He played football and wrestled in high school and, while he wasn't the star in either, he was a solid member of both teams. His Mom, Mary, was tall, thin, and elegant. She was always dressed well, her red hair always perfect, and was the strictest one, apart from my Mom.

Lars was a Norse god. He was blonde, handsome to a fault, and smart. Before he became one of us, we hated Lars. Who wouldn't hate someone who all the girls went ga-ga over? His Mother, Bridget, was just as bad. She was a natural blonde with flawless skin, and could have been a model. Her face could have been on any magazine cover, and that issue would have sold a million.

Then there was me, Bill. Somehow I became the de facto leader of our group, even though I was the shy one. My Mom, Tammy, was beautiful in my eyes, but in truth she may not have been as pretty as some of the other Moms. She was tall, had the smallest breasts of any of our Moms, but a beautiful face and a killer butt. She was the most strict of any of our Moms, and as a result the guys didn't like hanging out at our house as much as the others. When we were hungry, though, my house was the one we went to. Well, either my house or Robbie's, but we always got better food at mine, I thought. When we ranked our Moms according to which one we wanted most, my Mom was always at the bottom, just above Aunt Ellie.

I asked the gang once, "Hey. What about my Mom? She's beautiful."

The consensus was that yes, she was beautiful, but they had to consider availability, and they figured she was cold as ice. "Man," they said, "You try anything with her and you'll get your jaw busted." So, that was it. I couldn't disagree with them. When we were war-gaming seducing our Mothers, someone would say, "Yeah, Carol would go for it. She acts like she would love giving it to me." But not Mom. Nobody ever said that.

Yep, we were a gang. Video games were our primary pastime, but when we got together you could always count on the conversation turning to sex eventually. We were teen-aged boys, after all. And after the ice was broken, when the conversation turned to sex you could count on our Mothers being a topic of the conversation at some point. But not at first.

I don't know if all teen-agers talked about sex that way, but we sure did. We were seniors, had all turned 18 and were, in our minds, men, but we were kind of sheltered. I'll admit it. We were nerds, even Roger The Jock. The first time we heard the term "MILF," and I think it was Jim who told us what it was, we had days of giggle sessions. We worked it into every conversation. When one of us wanted the game controller, we wouldn't say, "Give me the controller." We'd say, "Gimme that MILF." That would always get a laugh.

And once the word was used, you could count on someone saying, "Jim, your Mom's a MILF for sure," or "Lars, what's your MILF Mom doing today?" Once we started using that term for our Mothers, talking about them specifically in that way was not far behind. I remember, or I think I remember, the first time we really got serious about it. We were at Jim's house, and were joking around. One of the guys referred to Carol as a MILF, and everyone laughed. Then I said, "You know, she is."

"She is what?" someone asked.

I knew this might get me an ass whipping from Jim, but I said, "She is a MILF. She's a Mom I'd Love To Fuck."

You could have heard a pin drop. OK, making general jokes among us might have been one thing, but my saying that so directly was quite another. Everybody kind of looked down, then when nobody said anything, they all looked at Jim. I did, too, because I wanted to be able to run if he came after me. But he didn't. He said, in a low voice, "I know. Me, too."

"Whatta ya mean, 'Me, too?'" we all said, like a Greek chorus.

"She's a MILF to me, too. She's my Mom I'd Love To Fuck."

I looked around, and everyone was staring at Jim, each with his mouth open in either shock, or excitement. I know I wanted my Mom, she was my MILF, but until then I had no idea that anyone else in the universe thought the same way about his own Mother.

Jim continued. "Look, you guys are my best friends, so you might as well know. I can't think of anything but her. You should see how she looks in the morning when she wears nothing but a tee shirt and her panties. I can't help it. I'd give anything to get her in bed."

That broke the ice. Everybody started talking, and every one was admitting the same thing. Each of us wanted to fuck our own Moms. Oh, Robbie didn't chime in as eagerly as the rest of us. His Aunt Ellie was older, and she really wasn't his Mom. He said he wanted her, too, but he didn't say it with the eagerness of the rest of us and I wondered if he really did, or if he was just saying that to be part of the crew.

That became our bond. We were bonded together by a common desire to bed each of our own Mothers and, I have to admit, from that time even video games seemed to take a back seat. We were dating, with varying degrees of success, and had real girls to talk about, but our conversations would always include our Moms. They were our special desire. I know that the first time I got my hands on Becky's tits - Becky, who was a sex goddess in our class - I was thinking what it would be like for Mom's tits to be in my hands like that. When I lost my cherry, it was Mom I was fucking in my mind, not Becky. I suspect it was the same for the rest of the guys. Hell. I know it was the same for them.

We were obsessed. We'd begin talking about one of our Moms, and the question would always be, "Do you think she'd do it?" Of course, our fantasies were one thing, but I think in our hearts we knew the real answer. No. I mean, sex obsessions or not, they were our Moms. They didn't really even have sex, did they? That didn't stop us from coming up with new and varied strategies for fucking them, most of the plans fueled by things we had read on the web.

"Let her catch you jacking off."

"Grab her tits and start sucking. You know she wants it."

"Load up the car to go somewhere, get your Dad to drive, and get her to sit on your lap in the back seat because there's no room."

"Find something to blackmail her with."

Yeah, we had strategies, but I think we knew they were all fiction on the web and none of the stories we read were really true. We'd watch videos of supposed Mother-Son sex, and the porn star-looking Mother would be screaming, "Give me your huge cock! Fuck your Mother!" Since none of us could imagine our Mothers ever saying anything like that, in our hearts we knew it was all bullshit.

But that didn't keep us from plotting in earnest. I mean, maybe we couldn't get our own Mothers, but what if we tried our buddy's Mom? We were clever and sophisticated, so our plots generally involved rubbing against her ass. Except for my Mom, who was too strict and dangerously untouchable, and Aunt Ellie, who was too sweet and was ancient - she had to be 50, for God's sake - we'd develop elaborate strategies to touch one of our Moms' asses. OK, Roger's Mom, Mary, was pretty intimidating, too, like my Mom, but we weren't as afraid of her.

"OK, Bill. Go for it. Just go in the kitchen to get a drink of water, and rub against her when you walk by." They always seemed to pick on me, because I was the shy one. So, I'd go in the kitchen, walk by Carol, or Mary, or Bridget, and casually touch her butt when I went to the sink for a drink of water. We did it so many times, we must have been the best-hydrated guys in the world, but there was never a reaction.

"Don't they feel it? Maybe you're not doing it hard enough."

But, in the end, we were afraid. Half of us, I'm sure, lied about touching her ass and the other half did it so tentatively that she probably didn't feel it. Reach down and really grab a handful? Hell, no. Not me. That's a good way to get your head knocked off and a telephone call made to your own Mom.

And that's how we spent our last year in high school. There might have been a grand strategy to get your Mom in bed, but we didn't find it.

We each went to different colleges. All of us went away, except for Robbie, who stayed home and went to the local university. We wanted to be away, but he wanted to be home, and his school had a great engineering program, anyway. We'd get together when we came home for holidays, and it was always the old gang, together again. We'd always, over beers by now, get around to our Mothers, but it was more in a nostalgic way than that we were serious about it.

"Lars, you got that Mother of yours in bed yet?"

"Not yet, but I'm close. I know I am. I touched her ass."

We'd all laugh. "Yeah, right."

When we graduated from college, we kind of spread to the four winds and our time together was more limited. It was kind of sad, but we each made an effort to keep our gang. We'd talk on the phone sometimes, have group chats, and play on-line video games.

I was accepted into the local university's law school, and moved back home. I got my own apartment just off-campus, and it worked out great. I could go home when I wanted to see the folks, mostly my beautiful Mom, get a good meal, or do laundry.

My world opened on one fateful day.

I wanted a good meal on a Wednesday night, and went to the local Italian chain to get one. You know, the chain with the bottomless salad bowl and all the bread you can eat. That one. I was waiting to be seated and who should walk in, but Carol. It was like homecoming weekend. When she saw me she squealed, "Billy!" and gave me a big hug. She said Jim's dad was out of town for a week at a conference, and she didn't feel like cooking for herself. I explained that I was there for the bread, and we laughed. It seemed natural for us to eat together, so we got a table.

Carol was, as always, bubbly. She chattered away and I loved being with her, but I couldn't help but think she seemed a little nervous to be with me. I'm not the worldliest man around, but I can tell when a woman seems a little nervous when we're on a date. Now, this wasn't a date, but all the same. Sometimes the nervousness means she's really into you and expects something to happen, sometimes it means her car has a low tire, and sometimes it means she's just nervous. I didn't know what Carol's apparent nervousness meant, but I couldn't help my mind turning to what I wished it meant.

The conversation turned to the gang when we were at home, of course. We laughed about some of the things we had done, like the time Jim got a scratch on his dad's car and we were scared to death he'd find out. Carol covered for him, saying she must have scratched it. We had a good laugh at that.

After we had shared a couple of glasses of wine, I finally got up the nerve to ask her. "Say, Carol. Did you ever realize how we were all trying to get our hands on your butt?"

She laughed uproariously. She laughed so hard she practically choked. "Of course I knew. All the Mothers knew. We'd talk about the latest strategy you boys had worked up, and compare notes on how each of you did. You were always the shy one, so half the time I knew you couldn't work up the nerve to do it. Robby was the bold one. Sometimes he'd give me a good feel."

"Robby? Are you kidding me? Robbie?"

"Oh, yeah. Robbie was the quiet, silent killer. Robbie would just go for it, while the rest of you tip-toed around it."

"Wow. Robbie. Well, you were our number one MILF," I said, and she laughed. It was not a mean laugh, so I asked her, "So, our little secret was not such a secret after all?"

"Oh, no, Billy. You can't have a secret from your Mother. Of course we knew."

After that she seemed even more nervous, and talked non-stop about any and everything. I hoped I hadn't offended her. Christ. I hoped she wouldn't tell Mom I was a perv.

When we left the restaurant, it was natural for me to walk Carol to her car. She was on my right side, and she slipped her left arm under mine, hugging my arm as women do sometimes, as we walked through the parking lot. She had parked pretty far out, for which I was glad, because the effect of the way she was hugging my arm was that her breasts were squeezed against my upper arm. I couldn't help but wonder, especially after our conversation, if she had any clue what she was doing and what its effect was on me.

When we got to her car, she unlocked the door and then turned to tell me goodbye. I hugged her, she hugged me back, and then I figured, "Goddammit. Nothing ventured, nothing gained," and I moved my left hand around to cup her right breast. She kind of pulled back, not much, but enough so she could look me right in the eyes, and I thought, "Well here it comes. All hell is going to break loose."

But she said nothing, and she didn't remove my hand from her breast.

We didn't speak. Neither of us. We just looked in each other's eyes. After what seemed like about three years, I said, "Carol? Can I follow you home?"

She nodded, took my hand off her breast, and reached up to give me a peck of a kiss on the lips. "Sure, Bill. We can have another glass of wine and you can tell me some of the other things you rascals got up to."

I knew how to get to her house, but I stayed on the tail of her car like I was a detective on a hot pursuit. I didn't want her to get away, or try to lose me and drive somewhere else to avoid me. When we got there, she pulled into the garage and I parked in the driveway. She came out the garage door and said, "Bill, we may have snow so why don't you pull your car in the other side of the garage. That way, you won't have to clean your windshield later." She opened the garage door, and I pulled in.

She unlocked the door from the garage into the house and hurried in, leaving me behind. I was afraid I had scared her, so I was a little timid when I walked in. I found her in the kitchen, standing at the sink, opening a bottle of wine. I went to stand behind her as she filled two glasses.

"I'm into it now," I thought, "so let's get this show going, or go down in flames." She was still facing away from me, holding the two glasses, and I put my arms around her with my hands on her stomach. I pulled her back into me, pulled with my hands so her ass was against my rock hard dick, and said, "Carol, I don't think I want wine right now. I want you."

She put the wineglasses down on the counter, and turned in my arms to face me. I thought, "Oh, hell. Here it comes, 'Billy, you're just a boy, so go home.'"

But that didn't come. She looked me in the eyes and said, "You can never tell a soul about his. Promise." Sweeter words I had never heard. I crushed her to me, and we kissed deeply. Her tongue was like an animal. We stood there kissing, and I moved my hands down to that beautiful ass, hunching her against my dick.

"Come on, big boy. Let's go upstairs."

I picked her up in my arms, and she squealed. I went charging up the stairs with her in my arms, but I have to admit I was flagging by the time we got halfway up. I guess I'm destined to be a desk lawyer. I was never a jock, and was in no better shape now than when I was younger. I stopped to catch my breath, and she said, "Oh, put me down, you oaf. I don't want to give you a heart attack." I put her down, and we went into her bedroom.

The bedroom. Her bedroom. Her husband's bedroom. Jimmy's parents' bedroom. I had been in there before, but never like this.

She walked in ahead of me, stopped at the bed, and turned around to face me. I thought she might be having second thoughts, since she seemed suddenly a little shy, so I took her in my arms and again kissed her deeply. This time I didn't put my hands on her ass, but cupped her face in my hands and put as much love into my kiss as I could. I did love her. I had always loved her in a way, and I wanted her to know it.

She pushed me away, gently, and started undressing, then I started undressing her, and she started undressing me. Hell, I don't know who was undressing who, but we were pretty quickly standing there naked in front of each other. I stepped back, and devoured her with my eyes. She was, as we always thought, beautiful. Her full breasts, with a little sag now, had dark areola, and the little nipples were standing hard. She was a little plump, which I like, and her belly had a little pooch to it. Her pussy was the hairiest pussy I've ever seen.

I stepped to her, kissed her again, and then pushed her back onto the bed. This time the kiss was quick, because I couldn't wait to get down to those tits. God, they were so soft. I kneaded them like a good baker should, and bent my head to take her in my mouth. I sucked those things like a champion, taking as much of the breast in my mouth as I could and working her nipple with my tongue. She held my head to her breasts as I did it, running her fingers through my hair.

I kissed down her belly and stopped at her pubic hair. My God, it was glorious. Thick, curly, and almost blue black, it was so dark. I ran my fingers through it and she shivered. "Don't tickle, Silly." I eased off the bed so I was on my knees by the side of it, and pulled her to me. Bending my face into her, I used my fingers to spread her apart, and gently traced her female anatomy with my fingers - her labia, her tight little clitoris, and down. She whispered in a flirting little voice, "Picking on me," and with that, I dived in.

I traced her parts with my tongue, just as I had done with my fingers. She had her hands in my hair, holding my head, and after a bit she pulled me into her. I took that as my clue, and started sucking and licking with abandon. She was so into it that I thought she might smother me and I couldn't help it, I thought, "I wonder what she'll do with the body?," and laughed out loud. I looked up at her, and she looked right into my eyes.

"Come up here, Billy. Come here, Billy Boy."

I slowly crept up her body, and kissed her again, letting her taste her juice in my mouth. She licked my lips, and smiled.

She rolled me over onto my back, and straddled me. My dick was ready, and I started hunching, poking it at her pussy. "Not yet, Son. Mama's not ready yet," she whispered in her teasing little voice.

She looked in my eyes, and then slowly started down my body. I put my hand on her head, pushing a little bit, and she went right for my dick. She didn't fool around. She took practically the whole thing in her mouth, gave a big suck, and then pulled off. She looked at me and asked, "Are you ready for this?"

"Oh, yeah, Carol. I think we're ready."

She gave me the blow job of the century. She slurped, she sucked, and she licked. This was a woman who liked giving blow jobs, and knew how to do it. I knew I wouldn't last long, so I reached to her shoulders and pulled her up to me. She again straddled me, reached down for my dick with her left hand, and slowly lowered herself on it. The feeling was exquisite. She was warm, tight, and had the smoothest pussy I have ever felt. She started humping slowly, gave a groan, and then went at it while I hunched from below. We were going at it so hard that I slipped out, she hunched down, and I thought we might have broken the damned thing. She reached down, grabbed my dick, slimy with her juice, and put me right back in.