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Middle-Aged Wifey's First Anal

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You’d be surprised how long we waited to go all the way.
3k words
4.42
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Part 2 of the 3 part series

Updated 05/10/2024
Created 01/27/2024
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If you know how my wife is you'd be surprised how long we were married before I finally took her ass. We'd been together six, almost seven years before we went all the way. It was definitely worth the wait. I find that everything we do for the first time together is worth the wait. Not only is she a first-class lay... I also love her very much.

It's not that she wouldn't give up the ass or that I didn't try. We tried. Rita was in a phase of sexual discovery when we married, a second marriage for both of us, and giving me her posterior cherry seemed appropriate. Still, despite her maturity she was relatively inexperienced and every time we went for it she tightened up and couldn't take it. I can hardly blame her.

The last time we tried she said I should just force her. Knowing now about her secret kink, I think she would have liked it better if I had. But forcing that seemed like a good way to injure a person. I told her there was no need to rush, that I would be patient as long as she promised to let me be her first. If you know how my wife is you'd know that wasn't a sure thing.

I didn't feel deprived without it. We had a few hundred positions and variations to explore in the meantime. Rita had a lot of catching up to do, sexually, and her appetites were as wicked as her imagination. And to be honest, if I really needed to do that there were women willing to accommodate me. Our marriage wasn't open but it was certainly flexible.

Also, despite her hangups she really enjoyed ass play. I thought at first she was being extra permissive about it to make up for disappointing me. But ultimately there was no mistaking the profound effect that being touched back there had on her. It turned her arousal up to eleven and her satisfaction off the charts. Somehow I was first to learn this about her.

If you're lucky, you find a woman who will let you stick things up her butt. If you're very lucky, she enjoys it too. Even better if she has a nice shapely ass and a cute little pucker with low mileage. I only had to ask and if she was the least bit inclined she would roll over or bend over or put her feet behind her head for me. More often than not, she was so inclined.

In fact, I rarely even had to ask. Over time we grew to understand each other's urges and habits, to recognize each other's moods. I liked it best when she would ask me to go there, this otherwise dignified woman, lewdly assuming the position, spreading her cheeks and inviting me to do the most disgusting things to her. I never refused, even if I wasn't feeling it.

She liked to be fingered, of course, usually with just one or two fingers or a thumb while we did other things. We went shopping for bananas and cucumbers and a few things she would prefer I didn't mention. When we visited the adult store she would select an anal toy about every other time. I wondered if she ever used those toys when she was by herself.

She had plugs of every type and size, sometimes wearing them in public. She liked to surprise me with one, letting me discover it while I was copping a feel or stealing a glance. Then I'd have to suffer in lustful longing until I got her alone for the big reveal. Then I might pull it out of her nice and slow or leave it in her while we screw.

She had probes of varying thicknesses and textures. These were for me to use on her. She'd let me help get her ass ready for fun, a ritual I adored. Then she'd select a probe for me to squeeze up her tight ass and fuck it in and out of her. Some of her probes were smooth and slender. Some had ripples or veiny ridges. Some were fat; big as my cock... or bigger.

She had a big suction-cup dildo that was dedicated to her back door. It looked and felt realistic, big balls and all. It was narrow at the tip and widened out near the base, ideal for going deep and wide. She would stick it to a big wall mirror and back up to it. Then I'd get in front of her and enjoy her throat while she fucked herself in the ass. What a wonderful sight.

She had anal beads that we loved to use. Her favorite set was like a string of pearls that I pulled out of her in one smooth motion just as she was starting to climax. My favorite had big squishy beads the size of ping-pong balls. I'd take my time pushing all five of them up into her butthole. Then I tugged them out, one at a time, while eating her ginger pussy.

I remember the first time I licked her anus. I didn't just lick it, I ate it like it was a pussy. Never felt inclined to do that before. We saw it done in a video so of course we had to try it. I suggested putting something sweet on it. She said I either liked the way her ass tasted or I didn't and I might as well find out now. Turns out that yes, I do like the way her ass tastes.

She's gone down on my ass as well, not because I wanted it but so that I would know what it was like. It made me very self-conscious so I tried to be sensitive to her feelings when I did it to her. I wouldn't sample the goods without asking first. But again, I rarely had to ask. Sometimes when I was enjoying my favorite dish she'd just roll over and offer me dessert.

*****

You're probably thinking that after years of play Rita should have been ready for the real thing. It would cross my mind now and then but I didn't press the issue. I figured she was saving it up for a special occasion and it would be worth the wait. Like I said, I wasn't in a hurry. As long as I got to be the first I could be patient.

The special occasion came in the summer of Rita's oral obsession. You might be familiar with the story of how she allowed someone to photograph her with his penis in her mouth and the pictures wound up on the internet. This was the first time I was confronted with evidence of her dalliances. Also, she never let me take pictures like that. So I was a little hurt.

To make up for it she promised me as many blowjobs as I wanted. She ended up giving me much more than I wanted, at least three every day and more on the weekends. When I talked to her about it she said she didn't want to stop. Obviously, obsessively sucking dick was something she was doing for herself. I had to do something to keep her under control.

That's when I made the decision to bring in Kevin, my friend and business partner. Kevin was much younger than us, in his early thirties. He and Rita had some sexual tension between them and I knew it was only a matter of time before they got together. I was pretty sure they hadn't been intimate already. Rita was a slut but a well-behaved slut, usually.

I didn't like my wife to have long-term affairs. I didn't want to risk her falling in love with someone she was sleeping with. I also didn't want her messing around with someone who was close to us. Now I was voluntarily breaking both of those taboos. Better this than have her out there looking for other dicks to suck. She was happy with this compromise... a little too happy.

So for the rest of the summer Kevin got pretty much unlimited oral privileges, with certain conditions. I planned to let the two of them have greater liberties in the future if they could be trusted to follow the rules now and to stop when I said stop. As it turned out, though, they took it to the next level much sooner than expected, and with my approval.

*****

I thought Rita was playing a joke on me when she told me what she wanted. She said she had pretty much gotten over her oral fixation which was good news to me. But in her quest to become an expert cocksucker she had run across a certain sex act that she felt she had to experience to feel complete: she wanted to suck two dicks at once.

Neither Kevin nor I were too keen on the idea of our penises rubbing together even if they were in my wife's mouth at the time. But if you've read her version of events you know she persuaded us to go along. For inducement, she offered up her pussy to Kevin. Which, technically, meant that I was offering it to him. But that's fine; just ahead of schedule, is all.

To me she offered up her ass. Mind you, her ass had been promised to me since our honeymoon. I could probably have taken her any time or many times in the past few years. She was offering me what already belonged to me and offering to Kevin what also belonged to me. But I admired her style and resigned myself to a Labor Day weekend of corruption.

*****

I didn't watch them fuck. I'm not that kind of guy. I thought about it though. She is the sexiest woman I've ever known and it might have been interesting to watch her. Rita told me later that he took out a few years of frustration on her before pulling out and coming all over her stomach. Then he rolled her over and kept on fucking. It must be nice to be young.

He must have had a good view of her green jeweled butt plug while he did her doggy. I had her wear that mainly to prevent him from "accidentally" slipping into her butthole. He would eventually get her ass, but not now, not yet. But it was kind of a relief to let them finally fuck, just like I used to help his parents in the bedroom when I was the younger one.

The other reason I had her wear the plug was so she would be ready when I gave her my surprise. After they said their goodbyes, Kevin and I had a scotch and a smoke and I walked him out to his car. Then I suggested Rita hit the shower while I changed the bedding. But as soon as I heard her turn on the water I disrobed and joined her in the shower.

Her eyes got wide when she saw me. But she gained her composure quickly and switched the shower controls from rain to mist. As a cloud of steam built up in the stall she turned to face the corner and rested her head on her forearms. She looked so beautiful there, glistening wet skin, breasts quivering, her poor defenseless ass awaiting my touch.

*****

I stepped behind her and ran my hands over her shoulders and down the hourglass of her figure from ribs to hips. I put my arms around her and pressed my chest against her back and my stiff dick into the cleft of her soap-slick fat ass. I moved my hands up her belly and cupped her plump saggy breasts, fingering her slippery nipples.

"I'm gonna fuck your ass now," I murmured in her ear.

"Don't stop," she replied. "Whatever you do, don't stop."

The stainless steel buttplug lay on the bench beside her and I knew my course was clear. I took my stiff penis in hand and began lazily rubbing it up and down in her crack. I could feel it catch at the depression around her bum hole and my dick got even harder in anticipation of going all the way, of finally feeling her anus wrapped around every inch of my dick.

I leaned forward and tasted her shoulder and pressed the head of my dick against the soft skin of her anus. I cautiously pushed forward with my hips and felt an intoxicating sensation... a strange combination of resistance and of slippage. I could tell I was hitting the mark by the sharpness of the "ah... ah... ah..." sounds my wife was making.

I pressed and pushed with slight thrusts of my hips until the fist I had wrapped around my cock was digging into the soft flesh of her cheeks. I had the tip inside her and an inch more, not quite to the widest part of me. This was farther than we had ever gone and I stood there breathing on her shoulder while I savored this sweet victory.

Then I drew back that extra inch and pushed back in, started giving her that inch, in and out, in a miniature fuck of her slutty stretched-out anus. I let go of my cock and put both hands on her hips. It was an amazing sight, half my dick sticking into her ass. She was taking it passively up until then so I pulled back gently on her hips to make her participate.

She did not disappoint me, pushing her ass back on my dick, and I felt her tight sphincter muscles pinch me as inch after inch slid into her colon. When she was down to the base of my penis I let her take a moment to get used to it. Then I started to fuck her asshole. I moved my hands up to her tits and fucked her ass gently but relentlessly.

From then until I came she would be nothing but a whore for me to fuck. When I felt tempted to take it easy on her I reminded myself she just got pounded by my friend after sucking his dick every day all summer long. I reminded myself we were here in the first place because she screwed some guy at work and let him film her sucking his dick.

I admit I was working out some hard feelings while I picked up the pace, sliding my prick nearly all the way out of her anus before grinding it back in, eliciting groans from her that echoed from the shower walls. I mean, she had permission to play, and she didn't really play that often, but I still had some resentment about it. Petty, I know, considering how often I played.

Rita put one knee up on the bench and I moved my hands to her shoulders, not missing a stroke in her anus. The shower mist kept us wet and slick and I didn't feel any friction. The only sensation was the touch of her soft tissues on the head of my dick and the tightness of her muscles gripping my shaft like a fist, but not so tight now as when we started.

Her other knee went up on the bench and her arms and face were smashed against the wall. She sat on her haunches so that her ass stuck out toward me and I rested my own knees on the bench, rotating my hips against her bum. I wrapped my arms around her and my chest molded to her back. I rested my cheek on her neck and made sweet love to her butt.

"I'm going to come in you now," I told her. "You ready?"

"I'm ready, James. Put your love in my dirty ass."

I shut my eyes and focused solely on the sensation of my cock pistoning in and out of her anus for the first time, of the feeling of her skin against mine, of the softness of her breasts trapped under my forearms. I felt the eruption coming and heard a long low moan rising from my throat. Time seemed to stop for a few long seconds and I came so hard. Definitely worth the wait.

And then she was my dear sweet wife again. My smart, sophisticated wife and not just a slutty whore for me to butt-fuck. I ran my hands over her shoulders and slowly withdrew from her suddenly very tight ass. Her anus clung to me while I pulled out, stretching my dick until the head popped out and her poor battered rosebud irised shut.

*****

My wife had quite the weekend. She sucked two cocks at once. She got savagely railed by a guy twenty years her junior. Then she got fucked right in her asshole. I was pretty confident that would satisfy her for a while. I'd watch her, though, and Kevin too. If they behaved themselves I could find another reason to get them together. If not...? Well, I hoped they'd behave.

I switched the shower control to jets and washed my dick. I stepped out of the shower and dried off, brushed my teeth, went into the bedroom to put on my pajamas. Rita joined me in bed about an hour later. She was wearing a sheer shortie nightgown, no bra or panties. She had the bottle of lubricant and a towel and set them down on my night table.

"When you wake up in the morning just roll over and do me," she said, "Don't warn me. Don't even wake me up."

"Just do you?" I asked rhetorically.

"I want to wake up with you balls deep in my ass, first thing in the morning."

"Morning might come earlier than you expect."

"That's the spirit," she said with a serious look in her eyes.

She crawled under the covers and snuggled up to me. I turned out the light and tried not to think about the crack of dawn. We may have created a monster here. Well, she was my monster... for now, at least.

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OnlyHappyEndingsOnlyHappyEndingsabout 1 month agoAuthor

Thanks Yeah, I know a little about it.

erectus123erectus123about 1 month ago

Very sweet, sexy story. Yes, two cocks in one mouth can be very entertaining. Does anyone know more about anal than Happy? I doubt it. - 5

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