Good Neighbors Ch. 11

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May 16, 2023 // By:analsex // No Comment

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Lena Gets Behind the MILF Rules

Hi! Lena here. It’s been a busy summer! It is hard to believe I’ve come so far from grieving over the loss of my fifth husband in just these past two-and-a-half months. It’s also hard to believe our young men are preparing to leave for State College in only a few days. We have all learned so much about ourselves, about our young students and, most important of all, I believe we have all discovered just how important having meaningful, productive purposes for our lives can be.

Liz, Abbie and I have talked mornings over coffee and our workouts about all that has gone on and we have slowly, gradually begun to agree about so much of the important work we have undertaken this summer. Each of us has memories – adventures, really that have become truly defining moments for each of us in these past few weeks.

We have all come to hold some very strong convictions regarding our work with these five young men. Educating them, preparing them for the responsible roles we were certain they were to play in the world has become our calling. This may sound silly to you, but we were truly energized and united in our devotion to educating and enriching the lives of these young men. We felt we had become their guides for the next phase of their lives. That’s what MILFs are for.

Liz, Abbie and I were so taken by the gravity of all this that we have taken two important steps to help guide us. First, we defined ourselves and what makes us the unique women we are.

The definition of a MILF: A MILF is any mature, attractive woman who has been fucked by a grown man young enough to be her son.

Next, we developed seven rules to guide us in our work. It took some time to develop these rules, and each has come out of a great deal of sweat, dedication and heartfelt experience. What follows are our seven rules.

In the presence of impressionable young men, a MILF:

is always prepared
appreciates and responds warmly to compliments
expects thoughtful, gentlemanly behavior at all times
takes every opportunity to educate her students
dresses to be appreciated
never conceals the joy of her orgasms
strives to learn and improve for her students’ benefit

Now, make no mistakes about how strongly the three of us feel about our new rules because we each embrace them fully. I do, however, support and live by a few of them more reverently than others, as do Liz and Abbie. Young men still find me attractive, and I intend to use that fact for both their benefit as well as mine for as long as possible.

I personally contributed rule three. Young men ought to exercise a high degree of propriety and civility – particularly when it comes to this grandmother’s snug little exit door. My first experience with Jeff and Benjamin convinced me the two of them were in dire need of a lesson in etiquette. I took up the task of their first lesson the very next weekend.

“Good to see you both,” I told them as I welcomed them the following Saturday morning. I had managed to dig out that snug little pair of pink shorts Benjamin had swooned over so many years ago and I can honestly say with pride, my ass looked magnificent in them. They were snug at my waist and left just a hint of my cheeks exposed in back. My most recent husband, Norman had loved those shorts too. He would grab my ass every time I wore them, give my butt a squeeze and groan out, “Damn, woman you’ll give me a heart attack showin’ off your beautiful ass in those shorts!”

Sadly, I did give him a heart attack, but fortunately for Benjamin, I wasn’t wearing these shorts at the time, or I would have thrown them out ages ago. I didn’t expect to give Benjamin or Jeff a heart attack, but a hand on my ass and a playful squeeze from them would be ever so reassuring – if they asked me politely first.

“Who-o-o-ee!” Benjamin whistled when he caught a glimpse of me from the rear.

“Does that mean you like, young man?” I asked, thrusting my ass out for them both and looking over my shoulder at them.

Benjamin’s eyes grew huge, and he immediately leaned toward me, both hands poised to grasp my bottom as if his life’s work had suddenly become holding and fondling my cheeks.

“Ah! Ah! Ah!” I scolded them both, “How do you know I want you to put your hands on my bottom?”

“B-but-!” this dynamic duo whined out, almost in unison.

“But nothing. Did you ask? Politely?” I challenged.

The smiles began to drain from their faces. This time it was my turn to take advantage of their shock in this situation. I wasn’t about pass up an opportunity for two handsome young men to caress and admire my bottom but first they would need to learn a thing or two and they would of course have to work a bit harder before they could rest a hand on my backside.

“May we -uh examine those lovely shorts you’re wearing?” Jeff asked, a bit more contritely.

“You can check them out from right Avrupa yakası escort bayan where you are, gentlemen. Do you have some good reason for examining my shorts?” I asked.

Benjamin, the true lover of my ass in the room, spoke up, “Well . . . they fit you so perfectly . . . and you look so . . . comfortable in them. I just thought you might want to let us feel how comfortable you are in them.”

“So, you like the way I look?” I asked, pressing them for more.

“Oh, god yes!” Benjamin sighed, his eyes never straying from my outthrust posterior.

“Well, since you’ve asked me nicely and you’ve expressed an appreciation for my -um shorts, I suppose it wouldn’t hurt anything if each of you placed a hand here,” I said with an exaggerated gesture to my left cheek, “And here,” as I motioned to my right cheek, “Then you both could walk me to the living room.”

The two eased forward, more cautiously and reverently now. Their big, warm young hands each clasped my ass gently and we set off ever so slowly into the living room on our way to the couch. Their hands cupped my bottom more carefully and with far greater care this week. It was a lovely and remarkable turn of events to have my bottom being appreciated with such loving attention. It was so nice I stood for a long moment when we reached the couch and simply let them fondle me my ass. I was in heaven.

Finally, when I began to fear I wouldn’t be able to hold them off, even if I had wanted to, I said, “Why don’t you boys sit down, and I’ll get us something to drink.”

It took a moment, but they did finally and reluctantly withdraw their hands and sit. I noticed they left a narrow space between them. It was just enough space to accommodate me and leave me snugly hip-to-hip with them both.

“I’ll get us all something to drink,” I announced before sashaying off to the kitchen.

I returned two minutes later with a small tray containing two sodas for them and a glass of merlot for myself. Both young men appeared to be quite disappointed after taking the drinks I offered them when I sat in the armchair across from them.

“Wouldn’t you be more comfortable sitting here, between us,” Benjamin suggested with a glint in his eye.

“No, I wouldn’t,” I answered directly, then added, “Not until we’ve had a little talk.”

I crossed my legs, turned slightly in my chair to let them appreciate the full length of my smooth thigh and began, “You took advantage of me last week. You caught me at a very vulnerable time, what with my grieving over my last husband’s passing and all. You both were pushing your luck – and you probably need to know you can go to jail for what you did to my backside right there on that couch.” I pointed to the spot between them where Jeff had pulled me down on his big, throbbing cock and kissed me while Benjamin had climbed atop us both and planted himself deep in my asshole.

Their eyes grew wide at this last bit of information. I guess it never occurred to them that sodomy might be anything more than naughty.

“B-but we didn’t mean to do anything wrong!” Jeff sputtered.

“Yeah! We just thought the shock of it might help you. You know . . . maybe snap you out of the funk you’ve been in for the past year,” Benjamin added nervously.

The shock had indeed made a big difference, but I wasn’t about to tell them this just yet. I intended to lay down a few rules they needed to live by from now on. While the two of them worried about their possible legal problems, I took a long sip of my wine and let them stew.

Finally, after my second sip of wine, I spoke up. “Your little scheme went a long way toward snapping me out of my ‘funk’ as you call it. So did both your performances with each other’s mothers in the wee hours of the morning a few days ago. Seeing you with them is what really lit my fuse.”

“What performance?” Jeff asked defensively.

“What exactly did you see?” Benjamin asked with every bit as much surprise in his expression as Jeff was showing.

I’m sure these boys weren’t having half as much fun with me as they had hoped. After all, we all still had our clothes on and I was certain they were both a long, long way from growing any kind of stiffness in their pants.

“You two won’t get jealous or embarrassed now, will you? I mean, what I saw did involve your mothers and you – and not necessarily in the proper order,” I half-teased them.

Jeff glanced at Benjamin, then back to me and answered, “I guess we can handle whatever you can throw at us.”

I paused a second, smiled at them both and began, “Well, I was sitting on the front porch – another one of my sleepless nights – when Marty’s rickety car rolled into your driveway, Jeff. Marty and Preston got out and then, Benjamin your mother crawled out. She was naked as the day she was born and walking like she owned a good piece of the world. After she kissed Preston and Marty in a most Escort Ataköy unmotherly way, she got you, Benjamin, to walk up to the garage door with her, holding hands the whole time. The way she was walkin’ – well, let’s just say a streetwalker didn’t have anything on her.”

I paused to see if anything I’d said had struck a nerve in either of them. They were calm, so I went on, “When your mother got Benjamin in the garage, she pressed him against the car and pulled his pants down to his ankles and then she ran off into the house. The last I saw of you before the garage door closed, Benjamin, you were tearing your pants off like they were on fire and hopping real fast to get in the house after Jeff’s mother.”

After another pause, I added, “I don’t think either of you went in the house for milk and cookies.”

At this, Benjamin managed a grin and mumbled, “No cookies. We went straight to bed.”

I was surprised by his comment. I was also surprised that Jeff didn’t show any shock at Benjamin’s comment. I could only guess that the two of them had already spoken to one another about at least some of this.

I pushed on, turning my attention to Liz and her arrival a few minutes later, “After Marty and Preston pulled their pants on and left. – Did I mention that they didn’t have any clothes on either? Well, they didn’t! – A couple of minutes later a big ol’ pickup truck rumbled down the street and pulled into your driveway, Benjamin. There were two people in the back, and they were both gruntin’ and breathin’ real hard. I don’t think they were Indian wrestling, either. . . Anyway, the fellow in back turned out to be Edward. He popped up out of the bed of the truck so I could see him and then you, Jeff got out of the front of the truck. Pretty soon after that, Edward picked Benjamin’s mother up out of the bed of the truck. She was limp as a dishrag. She must have been worked over pretty good from the way she was hanging in Edward’s arms. Anyway, Edward handed your mother over the side of the truck to you, Jeff. You had her punch in the code on the garage door opener to get inside. It took her a long time. Then you carried Benjamin’s naked mother inside in your arms. I have no idea how or where her clothes went to. And I also don’t think you two went in and had milk and cookies before bedtime, either.”

I let the silence settle on them before continuing. “Now that you know a bit more about the things that helped to end my grieving, I hope you’ll understand if I don’t fall all over myself to thank you for all that rough treatment. Besides, I’m also going to try my darndest to get to know Marty, Preston and Edward much better too!”

“So, what do you plan to do about what we – what I did to you?” Benjamin asked cautiously.

“We-e-e-ll . . . I want you to know I’m not nearly as upset as you might think. It may shock you or it may just give you reason to be proud of yourself, but you were the first man who ever managed to shoe-horn yourself into my backside. And I’ve had several men try. You two were also the first to ever double-team me like that. I have never had two men cream me the way you two did,” I told them calmly before smiling. “And . . . I might just try it again – under certain conditions.”

Benjamin and Jeff sat up a little straighter there on the couch at my words. Benjamin almost let himself grin.

“What ‘conditions’?” Jeff asked cautiously.

“For starters, you’d have to ask permission. I mean, you can’t just shove a greasy dick up my ass without so much as a ‘howdy-do.’ And that’s just for starters.”

Benjamin frowned and asked, “Exactly how do we ask something like that?”

“I’ll get to that, but first there are some other ground rules. After asking, you have to be patient and you need to be willing to help me prepare for anal sex. I’ve thought a lot about this, and I have a few things I’d like to try if you really want to do this. Some of it you may not like doing. Some of it will take a good deal of time.”

“Like what?” Jeff asked.

“One of my childbirth classes taught me some relaxation techniques that might just help. I figure if they can help me through twelve hours of labor contractions and passing an eight-pound screaming baby out of my belly, they might just help ease several inches of hard throbbing dick up my rectum. Along with relaxation, I’m thinking an enema might just cut down on the mess as well. It might also make a little more room for the two of you inside me. Have either of you ever given an enema?” I asked matter-of-factly.

I got two radically different reactions from them at my question. Benjamin’s face lit up. You’d have thought I’d handed him the keys to a Ferrari and told him to find out how fast it would go. On the other side of things, Jeff’s face twisted up into something wrinkled and ugly. You’d have thought I had smeared my own shit on the tip of his nose.

I took note of the shock and glee I was seeing and Şirinevler escort told them, “This is an all-in or all-out proposition. You both have to agree.”

They looked at one another, exchanged an almost imperceptible nod, and I knew instantly that before these two were finished with this fifty-eight-year-old grandma, I would likely either be hospitalized or left with a smile on my face and a spring in my step that would last through Christmas.

“As long as I’m the one giving the enema!” Benjamin almost shouted.

This, I told myself, was going to be an opportunity for my young studs to learn some valuable lessons at my knee.

“Oh! One last thing – along with the enema kit, I want one of you to get a small – and I mean small butt plug. I think I’m going to need a little stretching to get ready for this. Also, we’re gonna need some kind scented oil for lube.”

“Okay. I can do that,” Jeff volunteered quietly.

We sat in silence for a moment, Benjamin grinning happily and Jeff sitting quietly, but clearly just as alert and interested as his partner in this lesson.

“Did you gentlemen want to do this today? If so, you’d best get to it!” I told them.

“Today? Now?” Jeff asked.

“Can you think of a better time?” I challenged them.

Sixty seconds later I was closing the door on two very eager young men on a mission. Twenty-five minutes later, Benjamin reappeared on my doorstep, enema kit in hand.

“We split up. I thought things would go faster that way,” Benjamin explained as he fidgeted with the package in his hands.

Jeff arrived five minutes later, a little out of breath and clearly excited. “I had to drive a little farther. Boy, that sex shop downtown by the hardware store has some . . . well – interesting stuff!”

He held out his hand to display a shiny, clear glass plug that was perhaps six inches in length. It looked awfully big in my opinion, but then, I was also imagining how it would feel lodged in my rectum. That made it much more personal. It had a small knob-like handle on one end and the other half was a pear-shaped pommel that tapered to a blunted little tip. I felt my rectum tense slightly, imagining all that smooth glass stretching me, my little sphincter at first straining to accept the broadest part, and then suddenly snapping down snugly about the narrow stem immediately above the handle. I was in for one of the great challenges of my life. I already knew the two of them would work in absolutely perfect unison together and I could only pray Jeff and Benjamin would be gentle and considerate with me throughout our lesson. Of course, as I reminded myself, that was the whole point of this lesson.

“Jeff, why don’t you put that in your pocket and keep it nice and warm for later. As a matter of fact, why don’t you put that oil in a nice warm place too,” I told him.

We were together in the living room again when I asked them, “Do you still want to do this?”

They nodded eagerly and so I prodded them, “Then you’ll have to ask me for it.”

“Silver Fox, we would very much like to fuck you in the ass. Would you mind?” Benjamin asked without a moment’s hesitation.

His question, direct as it was, struck me as, well – rude. Yes, Benjamin was certainly about to fuck me in the ass but the saying ‘fuck you in the ass’ was a little too crude for my tastes. There had to be a better way to discuss this all and I racked my brain for a more suitable way to frame our little adventure.

“Instead of ass-fucking or anything that crude, could we refer to it as a rear-end collision?” I asked them finally.

Jeff grinned and said, “Oh, you mean like a three-car pileup?”

“Then you don’t mind getting stuck in bumper-to-bumper traffic?” Benjamin chimed in.

I kind of liked the way this was going and added, “Well as long as we don’t have to call a tow truck and I don’t need any bodywork when we’re done. Let’s see if we can keep the damage to a minimum.”

We all got a laugh out of that and finally I said, “Sure, let’s go see if the three of us can create a controlled pileup together.”

“Better buckle up. This could be a bumpy ride,” Jeff joked.

Once upstairs in my bedroom, I sat them both on the bed and gave them the rest of my ground rules for this adventure as well as instructions concerning a proper and safe enema. As Benjamin prepared the apparatus, I spread a towel out on the bathroom floor to lie down on. While an enema is always unpleasant, the process went smoothly enough, and I emerged from the bathroom a few minutes later clean once again and now quite nude. I discovered Benjamin and Jeff sitting on the bed, both equally naked. Now, most men are quite skittish about spending their time in the nude with another male but that definitely wasn’t the case with Jeff and Benjamin. Perhaps Abbie and Liz bathed them together as children or possibly it was simply a part of the deep, almost spiritual connection the pair shared with one another, but they were most definitely primed and ready for me when I appeared.

They didn’t stand when I entered the bedroom, but their cocks certainly came to attention for me. It’s so reassuring for me to know that at fifty-eight years old I can still draw the attention of such handsome and virile young men!

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