Visiting Sherie & Rick Ch. 10

"Now Harold, you be nice to Widow Johnson. Don't embarrass me. You do what Prudence asks, and you'll be ok. As a widow at her age, she's just very sex-starved, except for poor Ricky when I make him go to her. So she kind of unloads a month's-worth of her quirks on him all at once. She's really very nice once you get to know her. Just do as she asks, and don't upset her, ok?"

"But Sherie, what about you and me? I've been working hard all week, and you are supposed to be my reward, aren't you? This chastie has got me entirely horny for you. I have been dying to see you the way I've always imagined, you know, um, topless. And bottomless. Please? Pretty please, take your blouse off? C'mon, Sherie, gimme something, please?"

"No, Harold! And get those filthy thoughts out of your head! Why, I thought that device would help you maintain more civility than that. Or do you need another week in it to teach you better behavior around women? Actually, I think that's exactly what you need; another week of penis solitude. But now, though, it's some maturity discipline that you need, and I think Prudence can deliver perfectly. Especially when she realizes you aren't bringing the key along this weekend -- she's gonna hate that! Now get going. I told her you'd be there before dark, and you haven't much time. It's the old house up on the ridge. You should know it well. You pass it every time up the mountain. The one with the old hand-pump well, out front, and usually with washing hung out on the clothesline. Now get going. And remember, be nice. Don't embarrass me. And who knows, Harold, maybe you & me, we'll get our chance, MAYBE, if you make more progress next week. At least I'll talk about it with Rick this weekend while you're with Widow Johnson. Rick can be very negotiable after some solitude of his own. And he'll be elated to hear you're taking his place with Prudence this month. He might feel extra sorry for you. Maybe enough to give me his permission for you to get a (modest) little striptease, if you ask him nicely next Saturday night?" *wink*. Now get going, you."

And her cute little wave sent me jogging slowly up the hill. And yeah, I knew the old house, having passed it several times a day. I always felt a pair of eyes on me as I ran by it. Once I even caught a glimpse of the ol' gal as she was hanging out laundry, peeking at me over the large, white sheets. I couldn't get a good look, but she seemed trim enough. And tall enough to see over the clothesline. Hair down to here, you know, in the back, almost to down to her waist. Who knows, she might even have been good looking back in her day.

I can't believe I'm going there to service her, though. Or be disciplined by her. Dang. I can't even imagine.

But I dutifully jogged onward & upward. I cannot displease Sherie if I have any hopes of being with her next weekend. I just need to keep that hope in view, no matter what happens up here on the ridge.

Indeed it was dark by the time I arrived on the weathered old porch, knocking lightly, hoping no one would answer but knowing I couldn't be that lucky.

The door opened narrowly, cautiously. The old woman could be holding anything behind the door and I'd never know it til I was dying of a shotgun blast.

"Well well, who might you be?", she said, eyeing me through the narrowly opened door. "Did you come here to rape me, young man?"

"No Ma'am. My name's Harold. Sherie sent me here to help you -- not harm you."

"I don't believe you. You're not Richard. Where's Richard?"

"Sherie sent me in his place, Ma'am."

"I don't believe you. She wouldn't do that. She know's I need his little penis. A girl has needs, ya know. And I think he needs what I have to give him, too. We have a unique relationship, he and I. Sherie wouldn't deprive me of my needs."

"No Ma'am. That's why she sent me. To take care of your needs."

"I'd need you to prove it. Did she tell you like she tells Richard, um, to be sure to do what I ask?"

"Yes Ma'am."

"If that's really the truth, then you would take off all your clothes, right there on the porch if I asked."

Would I though? This is the moment of truth.

"Yes Ma'am."

"Well then, what are you waiting for? It's dark; nobody's going to see. Just you and me. Now, get em off."

I did as she asked, mostly though with my back to her though. I'm not at all anxious for her to see my shiny chastity device; that's for sure.

"Oh, I see you're the bashful type. Would you prefer Prudence not see your naked penis?"

"Yes Ma'am, that would help me a lot. I'm embarrassed. I'm not used to this sort of thing. I only came here to help you. So if you would do me that kindness, I would be ever so grateful. May I put my unders back on, please?"

"Well, I suppose I could allow that, now that you've proven you're on the up & up. But allow me to do that. I haven't dressed a young man in his tightey-whities for many a year."

I stayed turned away as she opened the door and came out on the porch to pick up my underwear. Instead, she gathered my other clothes and unceremoniously threw them over the rail, into the bushes.

"We might have visitors. We wouldn't want them to see a young man's clothes at the front door, would we?"

Before I could answer, she picked up my shorts and approached me. "Now stand still. Let's get these back on you. And don't worry. I won't look. Lift your foot."

As she dressed me, she took her own sweet time and a certain amount of liberties feeling my calf and thigh in return for what she deemed to be a kindness. Thankfully she stopped short of reaching through my legs to my balls and penis. She left me a shred of dignity; what a relief. I could have kissed her at that moment.

"Ok, young man, I mean Harold, come on in and we can get started. You know it's been a while since I've had a man up here, don't you? So what do you think I want (really badly)?"

"Someone to hug you, Ma'am?"

"You're rather slow, aren't you Harold? So maybe I need to be clearer. Let me sit down in this oversized leather chair. If I pull my dress up a bit will that help you find a better answer? There, how's that? Or do I need to pull it up a little higher? To my thighs, Harold? Ready to guess again?"

"Yes, Ma'am. I think you'd like me to caress & kiss your calves & thighs?"

"At least you're on the right track. So why don't you go ahead an get started. And just keep following my hemline, wherever it leads. And don't make me have to talk you through it. Do be a good boy and do what good boys are supposed to do for their female supervisors."

I began. Reluctantly. But what choice did I have? "Just do as Prudence asks and you'll be ok," Sherie had counseled me. And if I do that, I might get my chance with Sherie. So I kept that vision as I knee-walked my way in between Widow Johnson's legs, and leaned in to started kissing my way up to her hemline.

And it inched a bit higher yet.

"Don't be afraid, Harold. It won't bite. But if you don't follow orders, one of my implements might bite. You wouldn't want that, would you Harold?"

"Nm Mn'nm".

"Good boy. Don't lose contact with my hungry thighs when you answer me. Keep your tongue on me at all times, or I swear you'll wish you had."

"Yth Mn'nm"

And she raised the hemline again. "Be a good boy and I might let you under my dress."

OMG. Am I really doing this? Oh please don't make me go there. But Sherie is worth it. I will do whatever this lady asks, to get a chance to fuck my redheaded dream girl-next-door. Here goes...

"Yth Mn'nm. Pleeth ltt mm eet yuu, Mn'nm"

"Ok young man. Have it your way. You can dive under my dress. Get your head right in there and let me cover you up. Here, let me give you a little help staying right in there tight. Don't worry, you don't need all that much air anyway; you can breathe pussy air."

And with that she pushed my head down with her hands wrapping my head in her dress. I could scarcely breathe at all -- and I was licking her snatch like a mad man struggling for air.

"That's it, boy. Get in there. Deeper. Ahhh, yeah, there! Harder. Deeper. There. Oh shit. You mother fucker, fuck that pussy with your tongue, boy. That's it. Fuck it, boy! Eat that tastey mature pussy! Ooooo. ooooo. oooooooo aaahhhh."

She made me eat pussy like I had never known pussy-eating before. And I learned I loved it!

"Aaahhh. Perfect, you little boy-toy. Now give me a few minutes. Go get me a cigarette. And then stand in the corner until I'm ready for you again.

"What??? Why? I did what you wanted, Ma'am. Here's your cigarettes. Can I go now?"

"Did you just question my wishes, boy? Do not know what happened to Ricky when he tried that shit with me? Did Sherie not tell you to do what I asked? So how do you propose to apologize and make it up to me? Heh, boy? Now go stand in the corner while I answer that question for you. Go on. Go."

And I went.

She smoked, and blew it my direction. I could feel it drifting in on me. I hate smokers. And having an older lady smoking and making me stand in the corner like a child was just about my limit.

Til I thought about Sherie's slight breasts, and smallish girl's bra. I wanted that to happen so badly. So I stood there, not saying a word.

"Ok, boy. I've decided to be lenient this time. Just stand there. And if you beg to go down on me again, and I mean beg, I'll only give you one stroke, as a light reminder to always do what you're told in this house. My late husband got the hang of it during our honeymoon, and we went on to have 50 years of a wonderful female-led marriage. Now move your feet back, back some more, keep going til you are about to fall off of that wall. Good. Stay there and don't move."

"Your whities are going to come down for this."

I felt her thumbs tuck into my waistband. And she inched them down painfully. Down. Down, but oh so slowly. Is she trying to humiliate me, or trying to get me to flinch or move?

"Step out of them, boy. And prepare yourself."

I heard her walk out of the room and down the hall. And them return. And suddenly she was breathing her smoky breath right in my ear, and whispered to me:

"If you move... you'll get another. Do you understand?"

"Yes Ma'am."

"We shall see."

And with that, I braced for it.

Instead, she stopped breathing on me, turned and walked away.

And then came running back across the room at me, and laid a viscious stroke on my bare bottom with what could only have been a 4-pound solid mahogany paddle like that of a school marm back in the day.

I crumpled into the corner as I cried out in pain.

"Get up, you sissy. You apparently need another one."

"Please Ma'am, no more. I didn't mean to move, you surprised me and I lost my balance."

"So you're talking back, presumably asking for yet another one too?"

"No Ma'am.". And I returned to my position.

"Two more you shall have." And she closed in on me this time, holding me with one arm around my waist like she was going to dance with me; well, with my backside, that is.

And dance she did -- lighting my butt-cheeks on fire with two quick and harsh strikes. I went limp again, but she didn't let me fall.

"Oooooo eeeeeee!"

"Oopooo eeeeeee!"

"Oh you say that so nicely, boy! I loved that. Now beg to go down on Ms Prudence again. Only this time, in the kitchen."

"May I please pleasure you again, Widow Johnson?"

"Yes you may, boy. Right this way."

And I followed her, knee-walking dutifully to the kitchen, where she with a simgle motion cleared the table with her arm, and laid back on it.

"Get your head under that dress, boy. And get ready to breathe pussy-air again.".

And she pushed my head down tightly into her, squeezing my head between her bony thigjs like a vice. And soon bucking her hips up and down as I ate her vigorously. I think her taste was becoming sweeter to me the second time, almost like honey. I think I'm actually liking this mature pussy!

She soon came again with my head and tongue trying to keep pace with her bucking up and down, while shouting obscene instructions to me.

"You'll pay for that, boy! It was too good, and I cannot NOT punish such licentious behavior in my house. You were enjoying it too much. Admit it. You were really digging my pussy and you couldn't get enough, could you? And don't deny it or I'll take you out to the carriage house for a real whipping next time!"

"Yes Ma'am, you were delicious down there."

"Lean over the table then, son, and take what's coming to you for your unruly tongue, taking advantage of this poor widow's vagina.

I was afraid not to. So I did.

But this time, she released the catch on the dining table and pulled it apart, replacing the middle leaves with two custom-made pieces that, together, comprised two wrist-sized holes, into which she inserted my hands, closed the table and latched it tightly.

Then taking her time, she went out of the kitchen, returning with what appeared to be hand-sewn cloth stirrups for my ankles. Almost a quilt-like look & feel to them. Like your grandmother sewed them. And with them, she secured my ankles to the table legs.

"Ricky loves the dining table. Ha ha, not really. But maybe you will. Tell me what you think when we're done."

*********

I awoke from the recurrent nightmare I had fought off all night -- an older lady, first with her finger working its way into my anus. Then being jacked off by her with her free hand. I dreamed that I came buckets-ful... which she would pour carefully into a saucer and hold my face down in it, unable to breathe. Then I would awake, still bound to the table, and eventually would again fall asleep, with the dream starting all over again.

"Good morning little sleepy-head. Did you sleep well last night?"

"No Ma'am."

"Well, I'm sorry about not letting you sleep in on a Sunday morning, but after all it is Sunday, and you know what that means: Judgment Day. And you will need to be judged for hiding your little secret from me."

OMG. I suddenly notice the draft on my privates. No tighty-whities! She knows. Dang.

"Now where's the key?"

"Sherie has it"

"Are you telling me the truth, young man?"

"Yes, Ma'am."

"Then you won't mind a swift kick to your nuts, will you, boy? Or would you prefer to change your story?"

"No, Ma'am. Please? I'm telling you the truth!"

"Prepare yourself, then."

"No, please, I beg you!" (But I tensed up for what what coming, anyway.)

HER KICK LANDED SQUARELY ON MY NUTS! And the whole table shook, with me writhing in pain, from my gonads seemingly coming all the way up through my throat!

"Oooooooooooiwwwwwwwwwwww!"

"What a shame. Oh well, I guess you wouldn't enjoy any penetration sex right now anyway. So, sorry I had to do that, but it won't keep you from dutifully pleasuring a lady twice your age, now will it?".

And she climbed up on the dining table and laid back, positioning her bare legs on either side of outstretched arms, and her long, blue-print dress directly in front of my face.

"Shall we begin?"

Like I have a choice? "Yes, please, Widow Johnson."

And with that, she scooted ever closer, lifting her dress as she inched forward like a log on a sawmill, covering my head with the dress and forcing my head ever deeper into her womanhood.

The smell was overpowering. I swear she hadn't bathed since Rick had last serviced her with his dick. But I ate her hairy snatch just as she desired. All the while, pretending it was Sherie's, albeit wondering when Rick had last had that pleasure.

Prudence writhed and bucked, and forced my head down even harder, unable to breathe, until at last cumming with a shout.

"Son of a... BITCH, YOU MOTHER FFFUCCKKERRRRR!"

***

It seemed like forever as she napped there on the long dining table, still with her dress laying now comfortably over my head. I had not dared to wake her after she had fallen asleep there. But now her thighs were stirring, although possibly just dreaming of young men at her beck and call, pleasuring her, one after another, as if paying their weekly room rent in a boarding house.

She was coming to.

"Good boy. We shall have to do that again, sometime soon, Harold. But first, let's get you undone. That must be very uncomfortable by now."

And indeed it was.

"But you won't mind me taking a few pics for my album first, will you? Maybe a little video, even? Look down the table and talk to me; tell the camera what you liked most about eating my mature pussy, Harold. Go ahead, speak up. Make it good enough to warrant your release from the table."

Looking directly into the lens...

"Yes Ma'am. I loved it. Thank you for letting me dive into your treasured womanhood. I especially liked diving under your long home-sewn dress, kissing my way up your slim thighs, to your pubic forest. And licking each shred of your experienced bush along the way, into your delightful cave."

"Did it make your little caged dicklet hard, young man?"

"Fuckin' aye, Ma'am."

"Ok, and... Cut. Perfect. Good boy. Let me undo this little latch, and... there you go."

After loosing the middle leaves, my sore hands became free. I shook life back into them as Prudence freed my ankles.

"Ok, so I know you're probably anxious to leave and go home to Sherie, I understand. Go. And maybe if Sherie sends you up here next month, I'll let you in on my other fetishes. But for now, just give Prudence a passionate kiss and be on your way."

And she gave me the sweetest kiss on the lips, briefly dancing her experienced tongue into me, and back out again, making my dick throb in its cage, then breaking it off, shoving me toward the door.

"Don't forget to pick up your clothes out of the bushes. Lol. As if you would. Ha."

"What about my undies. Can I have tgem back please?"

"No, I think they're mine to keep. But I'll trade you these." And she pressed something into my hand.

A pair of panties, likely from her younger, sexier days. "Put them on underneath your jeans. No one will know. Just you & me."

"No thanks, Ma'am. If you don't mind, I'll just put em in my pocket to remember you by and our weekend together."

"Ohhhhhhh.". Her little smile turned upside-down, clearly disappointed. "Please? You'd make my day, if I knew you thought of me enough to do me that kindness. You know. As a reminder of you getting your head down under my blue print dress and diving in. Stealing my panties to wear home, would kind of make the storyline complete. After you leave I will probably get on my bed with a dildo just thinking about you in them."

How could I disappoint her like that? It now seems like such a small thing to ask. And I can imagine her getting off again, thinking about her young stud wearing her panties under my jeans.

Aw, what the fuck. So I walked out onto the porch and turned around to face her, and winked as I slipped into them. Running down the stairs, I grabbed my jeans and jerked them on quickly over my pantied cage, tied my shoes, and then, blowing her a kiss, I jogged out of sight down the ridge.

****

Rick & Sherie's porch light was on for me. Going inside, I couldn't tell exactly what had gone on today but I had a pretty good guess. Rick was nowhere to be seen, but his clothes were in a pile by the front door and Sherie was eating a steak dinner by herself. And most importantly, I saw the corner of a red-checkered tablecloth trying

to escape the picnic basket in the pantry.

"So, Harold, did you enjoy your weekend with Prudence? Rick was jealous."

***