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Introduction:

Good things cum to those who wait. In this case, 20 years.
Author’s note on what to expect: This includes a now adult male connecting with one of his mother’s counterparts, plus a little playful baby-talk as a small dimension of the story

“Jack darling, I need a favor. Mrs. Isaacs had a fire in her kitchen, and is going to need somewhere to stay for a couple weeks while the repairs are going on. Be a dear, call her and offer her one of your extra rooms?” My mother’s ‘request’ may be phrased like a request, but really, what she means, is, “Call Mrs. Isaacs. Let her stay in one of your extra room for as long as she needs. Do it now!”

Normally, I roll my eyes and begrudgingly comply with most of my mother’s ‘requests’. This one however, was very different. Because in this case, I was excited in a multitude of ways.

I had known Mrs. Isaacs my entire life. She was a neighborhood mom, my mother’s longtime friend, rival, and occasional sworn-enemy. She was about 5 years younger than my mother, and most egregiously (at least from my mother’s perspective,) she was prettier, taller, thinner, and blonder than my mother as well.

Under such close quarters, the lives of our two families had been inexorably intertwined every step of the way. Both my sisters (but not me) had counterparts in Mrs. Isaacs’s family, and there were carpools, sporting events, Fourth of July events, and suburban life in general to keep us always on top of one another (but not in the fun way). The relationship between Mrs. Isaacs and my Mother was reasonably friendly, but in certain ways, also involved obligatory “good little Mom” duties too. They belonged to the same clubs, the same PTA, the same social circles, so they had to be civil and sugary-sweet to one another.

Now as an adult, I was in my thirties, and Mrs. Isaacs was in her early fifties. She was still as beautiful and sexy as ever, always elegantly dressed, but never overly dressed for any occasion. And yes, she had always been a fitness buff, and nowadays did Yoga. And she wore Yoga pants quite often too, especially on Saturdays after her class. Would you believe, by sheer coincidence, that I had adjusted my ritual of visiting my mother, to happen on Saturdays? Imagine that!

The reason for my Mother’s request is that several years ago, I had gotten very lucky in real estate. I took a gamble and with every penny I had, bought a huge old house in a very questionable neighborhood near downtown. Given the neighborhood, it wasn’t expensive, but luckily for me, the neighborhood got hip, then trendy, then upscale. After several years of the neighborhood evolving, I was now the proud owner of a huge house in a historic neighborhood. And I had more than enough room for visitors. Lots of visitors. Mrs. Isaacs would be the first one representing someone I had lusted after for years though.

So, I followed my orders. I called Mrs. Isaacs, and invited her to stay with me during her kitchen repairs. I was a little hard just talking to her, because on top of how she looked and how pleasant a person she was, she also had always possessed one particularly sexy mannerism. She tended to sigh. And apparently, she sighed even more during phone calls, directly into the mouthpiece, so while I’m on the phone persuading her to come, and that I don’t mind at all, and that I wouldn’t even hear of accepting even a penny from her, I got hard.

The emotional upheaval of the fire, even though it was small, with things like having to arrange repairs and deal with insurance had poor Mrs. Isaacs emotionally drained. With all the upheaval, she clearly was enjoying having someone who would just listen, and not be full of advice. She was being downright chatty, and I was thoroughly enjoying the conversation. We talked about the kitchen fire of course, about the pending repairs, but also about where her daughters were now, a little about how the woman Mr. Isaacs had ran off with was younger than his daughters, about her job, my job, things like that. Even after half an hour, the conversation was still going strong, and I was getting to know Mrs. Isaacs in an entirely new light, this time with me in the role of an adult.

An adult, except for the part that during the conversation, I had gotten harder, because I gathered from a number of cues, that she was talking to me while in bed. What was she wearing? A nightgown? A nightgown with no underwear? Nothing at all? My imagination was running wild, but we agreed, she’d come over once the contractor arrived to work on the kitchen, likely in about 3 days. And the agreement we came up with, was that I absolutely was not accepting any payment from her whatsoever, but she’d cook for me. “As long as you don’t burn MY kitchen down.” I thought to myself, and chuckled to myself.

“As long as I don’t burn your kitchen down, right?” she said at the very same time, and we both laughed. Her laugh also involved a sexy breathy sound into the phone receiver. It was too much, and I reached into my boxers, and started lightly masturbating while talking to my Mrs. Isaacs.

“I was gonna say!” I joked back. Mrs. Isaacs chuckled, and I followed with “It’s so nice talking to you, Mrs. Isaacs. I’m looking forward to you spending time here; I just wish it was for something more pleasant, like expanding the kitchen or something else more fun.” To me, it was a double entendre, because in my own mind, the fun would include her in Yoga pants, but I felt as if it was too subtle for her to interpret it that way.

“Call me Debra. Actually, just Debbie. I always wondered why you called me Mrs. Isaacs.”

“What?!” I said in mock indignance. “You mean, all these years, I could have been calling you Debbie like Janis and Samantha did? Janis and Samantha were my older sisters, and I always felt like they were closer to Mrs. Isaacs than I was. “My mom always told me to call you Mrs. Isaacs, so that’s what I did. I’m a good boy!” I joked. “I felt as if I had to call you that, and that somehow my sisters were part of some special club who were part of your inner circle.”

“Oh no, I’m so sorry! You could have and should have been calling me Debbie all this time!”

“Well, thank you, that’s great to hear. All those years, I was so jealous. They got to call you Debbie, but they also got to spend so much time with pretty Mrs. Isaac, and I didn’t.”

“Awww, that’s sweet. But it was just because they were older, and on the swim team with my girls.” Then she paused, and jokingly said “So what are you trying to say? That I’m not pretty any more?”

“Oh my gosh, no. You are pretty, gorgeous, cute, and beautiful, all in one. Consider my earlier comment poor word choice!” I laughed, scrambling to correct myself. I knew it seemed a bit weird to be saying this, but I also needed to make sure it sounded sincere, and that I wasn’t just saying it to be polite. She really was stunningly pretty.

“You’re sweet.” she said, with just enough of a pause to make it clear she appreciated the compliment. “But seriously, it’s official. It’s Debbie from now on. And blame your Mom for telling you to call me Mrs. Isaacs. I always thought you were adorable, always running about in your little track team shorts.”

“Well, there were all the other ‘old people’ grownups, and then you. I always thought YOU were adorable” I said with emphasis. Right after I said that, I wondered if I should have said it out loud.

She giggled and sighed at the same time. “Well, Debbie it is from now on. It’s settled.”

“It’s a deal.” I said, somewhat glad that my flagrant flattery went over without sounding awkward. And she did giggle. That made me smile on the inside. And get harder yet again.

Another long, deep sigh from Debbie. “I suppose I’m keeping you up, forcing you to talk to an old lady. I should let you go to bed.” She had phrased it in a way that could be interpreted as a statement, but just as easily as a question, and sighed. I was completely enjoying the conversation, and that last sigh caused a little involuntary expulsion of pre-cum into my boxers.

“Oh, I’m absolutely fine, don’t worry about a thing!” I said. Then the little voice in my head joined the conversation again. Oh god, don’t make me say that, you damn little voice. Stop, don’t make me say it! “And actually, I’m already in bed, so it’s all O.K.; you’re not keeping me up. Well, not much.” God damn voice. I dropped in a cryptic erection reference, less subtle than the first, but I hoped, still at least somewhat subtle where I could pretend it was innocent.

“Actually, I am too! Oh my gosh, we’ve been talking for 45 minutes! I really shouldn’t be keeping you up like this.” If this beautiful woman formerly known as Mrs. Isaacs knew exactly how “keeping me up” had more than one meaning, I might be in big trouble!

“Nope, I’m not going to sleep. You can’t make me!” I joked, just as a healthy bit of pre-cum glided out of my cock and into my waiting fingers. I used the precum to lubricate my penis, sliding my hands up and down it’s now slippery length.

“Well, once I’m there, I’ll see to it that you don’t stay up too late, young man!” she jokingly scolded. “Actually, can you hang on for just a minute?”

“Sure, I’ll be right here.” This was so strange. Here I was, having an almost flirtatious conversation with beautiful Mrs. Isaacs, who would be moving in with me temporarily for two weeks.

“Ok, be right back!”, and I heard a little rustling, which I assumed was her getting out of her bed, then footsteps and a swish swishing sound, which I surmised was her clothing, possibly a robe.. It sounded like she had the phone in her hand, then I heard a light thud, I assumed the sound of her resting the phone down. A couple other noises off in the background, then the sound of water trickling. She was peeing off in the relative proximity of the phone! Now, it’s not that I’m turned on by listening to someone pee, but I am turned on by the implications: It means they are comfortable enough with me to pee in the background, and it also means they wanted to keep talking enough that they didn’t end the call. So yes, the implications of it were definitely a turn on.

A few moments later, some ruffling, then the sound of a faucet running, clearly her washing her hands, but the smart woman, she also flushed the toilet right then too, thinking the sound of the faucet would drown out the sound. She came close to succeeding, but I did hear. Then, the sound of the phone being picked up, although she didn’t start talking quite yet, then footsteps again, this time no swishing sound, then the same sound as earlier, in reverse of my Mrs. Isaacs getting back into bed. “Back!” she exclaimed.

“Yayyy!” I joked. Keep in mind, whether it’s real or not, in my mind the swish swishing sound that had now stopped, meant that maybe, just maybe, she was now naked. Or perhaps just in a pair of panties? And she was in bed, talking to me, also in bed, and we both knew that the other person was in bed. “Actually, can you hold on a second for me now?” I asked.

“Oh, geez!” she quipped. “Of course. But hurry!”

“You know I will!” I replied. I got out of bed, and had to make a split second decision. And of course, that little voice I mentioned earlier again had to get involved.

“Take your phone with you to the bathroom too!” the voice said. “Then make sure she hears the elastic of your boxers coming off of you. But tell ya what, don’t make the peeing noise too loud, you don’t want to gross her out.” This time, I had to concede, that little voice was being helpful.

So, I did it. I kept the phone in my hand as I walked to my bathroom. In my case, with the old house and wood floors, my footsteps were quite loud. When I got to the bathroom, I planned ahead, and rested the phone near the edge of the counter, but about five or six feet from the toilet. I intentionally stood close to the phone and slid my thumbs into the elastic of my boxers, pulled at them then let them go so the snapping sound would be clearly audible over my phone. I did the same thing as I stepped out of them, making sure I was standing near the phone, and making sure the sound of it would be unmistakable. I repeated with my shirt, making sure the sound of each button being undone was loud enough to be heard. Then I went pee also, being careful to try and make the sound vaguely audible, but not so loud to be obnoxious. Then just like Debbie, I turned on the faucet, and flushed while the faucet was running to drown out the sound. I washed my hands, dried off, and picked up the phone. I decided to talk as I walked back to bed, now completely naked.

“I’m back!”

“Everything come out OK?” she said laughingly.

I chuckled. “Umm.” was about all I could come up with for a response. By now, I was climbing back into bed, and I decided to make sure I fluffed the pillows and ruffled the blankets so she would hear. It took a moment or two to get comfy and situated in bed.

“All tucked in now?” she asked, sounding just a bit mischievous.

“Yes’m.” I said, trying to sound like a kid talking to his elder. Which I was. Except I was naked and hard, and I had every reason to believe she was talking to me in the nude also.

“Hmmmmm.” she sighed loudly and so very sexily. “I’m glad, everybody needs to be nice and tucked in, I always say.”

“I agree completely!” Then of course, out comes that little voice of mine, telling me to say things I probably should not. “Dammit! I should have made THAT part of the rental agreement!” As she laughed. I continued “I assume you’re all tucked in too?”

“Well.” she said, somewhat hesitantly.

“What? You’re not?” I asked, sounding surprised.

“Actually, no. I’m just lying on top of everything, not tucked in at all. With the fire and everything, I have to keep the windows open because of the smoke smell, and it’s a bit warm. So, no, I’m not tucked in at all, I’m having to use every trick in the book to stay cool. I have ice, I have the ceiling fan and a second fan both turned on high, and I’m lying here stark...” she stopped abruptly. This of course perked me up. She had to have been about to say ‘stark naked’, right? I decided there were not other words that would have fit the context. In my mind, I convinced myself she was naked. Was she rubbing ice cubes on her neck too? Her breasts?

“Mrs. Isaacs!” I said in a sympathetic voice, forgetting that I was allowed to call her Debbie now. I wanted to also say “Let me come over and tuck you in.”, but that particular battle with my little voice, I happened to win.

“Ok, listen. You have GOT to stop calling me ‘Mrs. Isaacs, do you understand me? It’s Debbie. Debbie, Debbie, Debbie. Pronounce it ‘Deb’ ‘Bee’” she joked.

“O.K., I can do that, Mrs…. Ummm… Deb-Bee!” I joked back. Then I continued, “I’m really excited. I’ve never actually called you anything but Mrs. Isaacs before this evening. I’m so honored by the promotion! It’s like I’m all big now, I’m a grownup!” This time around, I knew the double entendre wasn’t as subtle as before. In fact, it probably wasn’t subtle at all.

“Well, you are a grownup. And the fact is, if I’m going to be having long conversations late at night with you while I’m lying naked on my bed, you can NOT be calling me ‘Mrs. Isaacs’. It just isn’t right.” she said in a firm voice. Oh my God, did she just tell me she was naked? She did!

I was so caught up pumping my cock, I didn’t respond quite quickly enough. And when I did start talking, I realized I was breathing heavily too. “Well, I suppose I should confess, I’m naked too.” I said, not quite a blurt, but not as suave and debonair as I would have liked to sound. At the same time, it was a relief. She probably knew, but it felt good to say it out loud.

“Are you now?” she cooed.

“I am.”

“And what are you doing?” she asked.

“Ummmmm.” I hesitated. “I’m not sure I should say?” I said playfully.

“Spill!” This was a reference to earlier days, where she would say ‘Spill’ as her way of letting you know you know when she had caught you at whatever it was that you had been doing. And we knew, when Mrs. Isaacs said ‘spill’, you confessed!

My turn to breathe deeply into the phone and sigh. “Well, O.K. What I’m doing, is I’m thinking about your naked body, Mrs. Isaacs.”

“So little Jack likes thinking about old Mrs. Isaacs all naked?” Wow, this was a turn of events. An hour ago, she was Mrs. Isaacs, stately and majestic. Now, she was Mrs. Isaacs, sexy baby-talk role player.

“Yes, Mrs. Isaacs. I’ve always imagined what you’re like naked, Mrs. Isaacs.”

“And what do you imagine?”

“Mrs. Isaacs, sometimes, I imagine that you’re naked, and your legs are apart, and I’m getting to kiss you.”

“Kiss me where, Jack?”

“Ummm.”

“Spill!”

“Well, all over. But specially, I imagine that I’m getting to kiss you right between your legs.”

“Just kisses?” she asked.

“God, no. I’d kiss, and lick, and suck Mrs. Isaacs.”

“You want to kiss and lick and suck old Mrs. Isaacs’s pussy, Jack?”

“God yes. I’ve always had the biggest crush on you, Mrs. Isaacs. I want to kiss you and smell you and lick your all over.”

“My pussy gets very juicy. Do you think you’d like licking my pussy if it’s all juicy?”

I was pumping my cock so hard. “Oh yes Mrs. Isaacs. I’d lick it and stick my tongue right inside your pussy. Oh god, Mrs. Isaacs, I’m so hard. I’m pumping my hard cock thinking about you.”

“You know, Mrs. Isaacs would take your cock and put it right into her mouth?”

“Will you stick your fingers into your pussy while you suck my cock, Mrs. Isaacs?”

“I’ve had my finger in my pussy for the past hour, Jack.” The switch back to grownup talk was abrupt, and even sexier.

“Listen carefully.” I said in a calm, but serious voice. “I’m putting on shorts and a shirt, I’m getting in my car and I’ll be there in 13 minutes and I’m going to fuck you, Mrs. Isaacs. I’m going to fuck you, lick you, roll you over, and fuck you again. Unlock the side door and stay naked. We’ll talk the whole time I’m driving.” I said, as I got up and hurriedly put some shorts and a T-shirt on.

“O.K.” she said, sounding almost meek, taken aback by the sudden shift. “I’ll be here for you, naked with my legs wide open and my finger in my pussy. Is that good?”

“Very good. What do you think I’m going to do to you?”

“You’re going to put your cock in my mouth, and then in my pussy, then in my mouth again, and then in my ass. And anything you want.”

“That’s exactly right.” I said.

“What else do you want to do to your old Mrs. Isaacs?” Baby talk again. The switching back and forth was intoxicating.

“Can I suck your boobies, Mrs. Isaacs? You know I’ve wanted to for so many years?”

“Of course you can suck my boobies, my sweet Jack. You can suck my boobies while you fuck me. You can take that big hard cock of yours and hold your Mrs. Isaacs down and fuck her really hard.”

By now, I was in the car, driving to Debbie’s house to fuck her. “Tell me about your pussy.”

“It’s completely bald and smooth. Laser smooth as a matter of fact. I’ve got three fingers in it right now too, but I’m ready to trade them for some hard cock.” Deb panted.

“I’ve wanted you for so long; I can’t believe this is happening.”

A soft smacking noise comes over the phone. “God, I taste good.” Debbie bragged. Then she did it again. “I’m so wet.” And then more smacking noises.

“Almost there. Is the door open?” I changed the subject. I really was almost there.

“Opening it now.”

“Get on all fours on the ottoman in the living room. Point your naked ass and pussy at the door, and get on all fours on that ottoman. I want your naked pussy and ass to be the first thing I see when I come through the door.”

“O.K.” Over the phone, I hear the door being unlocked. I hear the scraping sound of a piece of furniture being dragged. “How far away?”

I barge through the door. “I’m here.” I practically jump out of my boxers and go right up to Debbie, who had been very cooperative, and was on all fours with her glorious ass and pussy facing the door. I pause to get a look, and she is as lovely as I had ever imagined, limber, buff, and yes, naked. I hold her each hip in my hands, and easily glide right into her, the benefit of both of us having been so hot and excited for such a long time. My cock is inside my amazing Mrs. Isaacs. There will be lots of time for lots of things, but right now, I just want to fuck this woman. I’m holding her tight from behind, my four fingertips holding her by the hipbones, my thumb grasping her cheeks, and pounding into her pussy. From my vantage point, standing behind the ottoman, I see an adorable puckered little asshole just above my cock sliding in and out of her pussy. In due course, I say to myself, I’m getting all over that little asshole too.

“Rub your pussy while I fuck you.” I order. She actually already was, but she did it with a new vigor. I’m thrusting deep, and I feel her body trembling from the hours of anticipation, from my cock in her pussy, from her rubbing herself. I love watching my cock sliding in and out of her, glistening with her nectar. She is as delightful to thrust into as to look at. We find a rhythm, and I feel her body trembling more and more, and suddenly she rests her head down on the cushion of the chair and almost freezes. Except for the quivering and grasping and pulsating of her pussy. She is having a shuddering orgasm, with my cock happily still inside her. I learned a long time ago, there’s a time to thrust, and a time to be still and let the moment happen. I stayed inside her until she came back to her senses.

I started lightly thrusting in her again, but she pulled away. “Oh, God no, I can’t right now.” and she rolled over and into a sitting position, her face just inches away from my cock. “But I can do this, give me that cock.” and she gently took the base of my cock, pointed it upward, and eagerly licked her juice off of my balls and the underside of my cock, looking up at me seductively the whole time. Then a second round of long broad strokes with her tongue. Then a third time, starting way down at the bottom of my balls and all the way up, gazing into my eyes the whole time. As she paused briefly before taking me into her mouth she said, “God, I DO taste good.”

“Give me some.” She understood exactly what I meant, and while still sucking, she dipped her fingers into her pussy, then reached up with them so I could suck her fingers. “Oh my god, you really do taste heavenly.”

“Mmm-hmm!” she hummed, now taking me deep into her throat, bobbing her head up and down my cock.

“I want more.” and she complied, except this time with a double dip, first into her pussy then her mouth, then back into her pussy and into mine. The whole time, also sucking me very deeply and hard, except for the momentary finger sucking. “But I’m going to cum if you keep doing that.” I cried out.

She pulled away, and got back on all fours. “Cum in me. Fill my pussy with your cum. I want your cum dripping out of my pussy all night.”

I plunged back into her, but I was over the edge. It all came to an amazing climax at the same time. Her pussy quivering as her next orgasm began as soon as I entered her put me over the edge, and I start exploding deep in her. Burst after burst, deep into her pussy, the heat inside overwhelming us, the hot cum dripping out of her, making my cock so slippery inside her, and her hips bucking. Eventually, I thrust deep into her, and freeze, letting her pussy grasp at my cock until the orgasm passes. Both out of breath, I softly pull myself out of her pussy, and collapse onto my knees behind her.

She rolls over, and naughtily opens her legs wide to show me her completely smooth pussy. She dips her fingers into her pussy, and collects my cum onto two of her fingers, and takes them up to her mouth and sucks them.

“Suck your cum out of my pussy and come up here and kiss it into my mouth.”

Mrs. Isaacs isn’t just beautiful and sexy. She’s a little freaky too! It’s going to be an incredible two weeks.
12 comments

neddamzReport 

2016-01-05 12:29:24
Very nice story.
I wrote a true story about a lady on my paper route. It is titled "Exploring" and posted in the "Boy" section.
If you read it, please leave a comment at the end.
Thank you.
Neddamz

Anonymous readerReport 

2015-12-01 05:48:49
Very bad story

Anonymous readerReport 

2015-11-26 18:14:36
Any bd???

Anonymous readerReport 

2015-11-23 16:34:11
Came during the phone sex ;)

Anonymous readerReport 

2015-11-23 07:27:43
Those MILFs man...

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