Indolent Ivan

Story Info
He really shouldn't have introduced Josie to Wren!
9.6k words
2.9
7.7k
1
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

February 24

From JosephineMiller

To: Wrenjohnson

Wren, this is great. I couldn't believe it. Ivan proposed last night. He presented me with a diamond engagement ring. I was kind of like "I hope this isn't a bribe, you're still not getting to orgasm till the end of next month." Although for a ring like that, I might have given up the whole Mistress/Slave thing and given Ivan a blowjob.

What I really loved was, Ivan gave me such a nice Valentine's gift, too, an emerald necklace from Camphor's Jewelry, and some guys would have combined the engagement jewelry with the Valentine's thing. I will have to get him to watch his money better when we're married, but now I'm lovin' it!

By the way, he was able to take the two foot wide Mangler strap-on finally. It took some serious lube, and he did some crying, poor baby, but Ivan's rear is really seriously loosening up!

February 25

FromWrenjohnson

To: JosephineMiller23

Josie, I am so happy for you! It was so awesome getting together with you guys again. I really think Ivan's behavior as a submissive could use significant improvement. It's nice that you guys are engaged, the Instagram shot of the ring was impressive, but I just don't think you are genuine in the whole domme thing. Or he's not really a submissive. Weekend "warrior"? That's cool I guess. Loved the ring though.

And by the way, when you marry him, you really should take over the finances. We'll get more into that later.

About the dildo-Duncan found that sitting on it for an hour a day really spread his cheeks, and he was much more ready when I had him receive Urbitron's cock, the guy I told you about in the ex-convict poetry group I've been hosting.

February 30

From: JosephineMiller

To: Wrenjohnson

What do you mean, Wren? Ivan and I aren't genuinely a sadomasochist couple? I'm certainly his dominant Mistress. I spank him, I've given him enemas, humiliated him in public, and I don't let him cum much. Ivan is a total submissive. He's learning now how to drink my pee and concentrating on licking me all over.

Sure, he was into the scene before I was, and he had to teach me a few things on how to tease and discipline him, but this is what he wants, and mostly it's what I want too. You don't think I rule this guy's life? I have him in a freaking chastity belt!

April 11

From: Wrenjohnson

To: JosephineMiller

Josie, I don't mean to hurt your feelings. I liked meeting you. After all, it was Ivan who got in touch with me after he found my profile on Bondagematch, and found out we were only eight miles away. I thought Ivan was cute, and when he invited me to get together with you guys for that first weekend, I had a great time.

But some red flags went up when Ivan told me how he had a motorcycle, and about his hang gliding and his Jetski. There seemed to be so many guy-type activities, Josie.

The men I date, the submissive ones, don't really raise too much hell, there isn't much recreation for them outside of serving me. It's either going to work, or being on their knees, thinking of ways to make Wren happy...looking after my house and my car.

It's helped a lot that I have enslaved so many different types-Duncan does my taxes, and Whitey's a mechanic, that kind of thing. And they are usually on the spot for me. Sometimes they take me to dinner or a show, but more often my boys procure tickets for me to go to an event with someone more, uh, manly.

I was really kind of put off, Josie, when you guys took me to that bar and I met Ivan's "pals". They were all making dirty jokes, and farting and that kind of thing. Ivan got kind of loud, and really, as a sub, that's not the direction I'd take him in.

Duncan, a guy I'm dating now, I don't see him all that often, we go on one date a week, or every ten days, but I made him give up his friends, especially the annoying female ones.

I don't mind him having an interest in opera or culture, but the first night we were out playing pool, I watched him joking with his male friends and flirting with waitresses, and I told him coldly that I wanted to go home early.

His friends were kind of put off. I looked very cute in a tight white top, and my hair was all curled, and so some guys were thinking, lucky Duncan, he can take Wren home and fuck her, and others were going 'Hey, don't let that girl tell you what to do.'

This had happened before, and Duncan had learned that when we'd gotten home, it didn't mean hanky-panky, I just wanted my way, so this time he'd said "Honey, we're in a billiards competition, can we go in half an hour?"

And Josie, I slapped Duncan as hard as I could across the face, and he almost fell.

And for a moment, I thought Duncan would tell me to go to hell, I wondered if our spanking games were just that, a game, but He drove me home and then when we got inside, I didn't take anything off, but I had Duncan strip and I tied his hands and ankles together and put him in my closet, and then I went back to the pool hall and hung out with his friends till three a.m.

And, the next day, Duncan heard about this and whined to me "If you wanted to be there, why did you have me take you back and lock me in the closet?"

And I answered him by whipping his bare ass and telling him that shooting pool isn't for faggots and ladyboys. I also told Duncan that if he wanted to keep seeing me, he would have to give up billiards, and playing in that ridiculous rock band, and that he'd have to donate his sports racer to the Salvation Army.

And Duncan could have told me no, and broken up with me. He's a good looking guy, and some of the women he's dated were as attractive as I was, some even younger and cuter, but I scratch his itch, and he knows that he's a pantywaist deep down, and so he did what I told him to.

Now, even though I only see Duncan now and then, sometimes only once a month or so, I still have him on a strict schedule. Every night when he comes back to his place after work, Duncan has to punch in with one of those factory things.

After he's punched in, Duncan has a TV dinner and then strips and kneels in front of his door with a cold Martini in front of him. He has to kneel there between seven-thirty and midnight...he can't answer his phone or anything else.

On weekends, he comes and cleans my place and then goes back to his and straightens up there, and then is on his knees from four in the afternoon to one in the morning.

Duncan never knows whether I'm going to drop in on him, and w hen I do drop in, he'd better damn well be kneeling. Sometimes I send a male friend of mine, to check on him, a surprise visit, and Duncan must reward them with a little oral. If he's not kneeling, or the punch card shows he got in late, my friend will whip Duncan's ass with a bullwhip I have hanging on the door.

And, of course, Duncan is in chastity. I have no real interest in a face to face long-term relationship or marriage with Duncan, but seeing him every couple of weeks is enough for me, and it just thrills him. He's lost touch with his other friends and family, but really, it's all about me.

Oh, in reference to your question over the phone about the whole chastity deal? It's interesting...I have to say, I think piercing is your only option.

I'm sorry Ivan is so freaked out by getting his dick pierced but the problem is, almost any non-piercing chastity device can be escaped from.

Actually, I have my ex-husband Chandler in a belt, he's living in Dubai, and when he reported that he'd been unable to get out of his belt, but could use a vibrating wand to create the stimulation to cum in it, I had to order him to go see a male hustler for a whipping...I can't get there to do it personally!

Duncan was in a spiral cage circling his penis, and the hinges caused some chafing. I don't care that much, but I hate hearing him whine about it...The problem with the cage, of course was that Dunc couldn't get a complete hard-on.

His dick would bulge out through the bars but when I teased him in it, he became very uncomfortable, and of course at night, when nocturnal erections happen, it makes his crotch feeling trapped.

The best part of course is giving him teasing hand jobs while his cock is caged. He sometimes shrieks when I rub his dick, poor Duncan, and quite frankly, I don't generally carry his keys around. So why not give him jerking sessions without bothering to unlock it?

This way, I can, after Duncan has brought me to many orgasms, play with his caged dick all I like, without having to tie him up or all that nonsense. Since I've not brought the keys with me most of the time, there's really no purpose in him whining about how he wants me to let him out.

I drop over to his house to fool around, and when Duncan comes to mine, quite often I will mail his keys away so he can't ask about them-and then recently when we went to the Caribbean, I just left the keys at home.

I didn't tell Dunc this, of course, not at first. I implied that if he serviced various men, as well as me and took his punishments gratefully, that I'd unlock him every three days, and it was a month long holiday.

After about twelve days I told him, laughing, that there was no hope, and of course by that time he'd sucked off the ship's purser and then the hotel bellhop when we reached Bermuda.

I cannot tell you how funny it was, watching poor Duncan kneeling on the white sand, crying his eyes out...but I did let him jerk off when we got home. He had been so generous!

But although Duncan has handled his cage without piercing, he's not terribly coordinated, and so I don't have to worry about it-he'd never get his dick back in, if he did pull the cage off! Ralph, like your Ivan, is far craftier with his hands, and so I had to put him in a piercing.

And even then-I caught him once with the entire device half hanging off his dick. He couldn't get out of the piercings, and so he was just a-jerkin' away. I did not give him a pleasant half hour after that little mess!

I finally had to put Ralph into what they call a "Tetherspout" this is when one puts a metal hollow spout, which resembles a sounding needle, into the urethra Then you lock on a little retainer which keeps the spout locked... to keep it in, I put a tiny lock on the end, so it bounces about. but the spout is so small that it's not uncomfortable for Ralph when he's flaccid. On the other hand, I have a long, hard spout I can insert when I feel like caning Ralph's penis and don't want it to get small. I may try a knitting needle!

And yes, he can pee, but not standing up. Ralph must squat like a girl and try not to let the spattering of the urine go on his pants, because, of course, his pee is circulating around the little lock. It's a problem for him, not me. I tell him to be careful, because of course he doesn't want to ruin his Brooks Brothers suit!

Here's a funny story-Ralph purchased this gorgeous suit from a tailor in Hong Kong, it had Ralph's name in gold script on the inside of his jacket. One afternoon, I was trying to teach Ralph how to swallow all my urine when I peed in his mouth, instead of letting it splash all over the place.

To illustrate how important it was not to let urine get all over the place, I squatted my 110 pound body just over Ralph's big head, but I made him lie his head on his folded Hong Kong tailored suit.

"Now you're going to be very careful, or this suit will be ruined, honey. Silk is not improved with pee on it." Ralph got it all down without a problem, and then he ate me to several orgasms while I was squatting there.

So I removed his chastity device and told Ralph he could beat his meat. It had been 37 days, not that long, but still frustrating, and this was last spring, when all the secretaries had been twitching their little asses walking back and forth in front of Ralph's office building.

So Ralph, all backed up from a month of unrewarded desire, began jerking off, and every time he came to a point of near orgasm, I would order him to stop and put his hands behind his head until he calmed down. I did this six or eight times, and when he got too excited and I let him shoot his load, I pulled his Hong Kong pants in front of his dick, and he made the most beautiful stain.

I made him wear it the next day to work, and it was big and white and looked like...something gross. Hilarious, right?

But yes, you're going to have to put your fiancée into a piercing if you want him not to "Cheat" on you. it's the way things are!

April 19

From: JosephineMiller

To: Wrenjohnson

I loved what you said, Wren about the chastity thing. That's hilarious, and I ended up getting Ivan pierced. He cried during the whole thing, and the piercing dude laughed at him, but it's done, no more masturbation.

But about what you said earlier, about how I'm not controlling Ivan's whole life, which implies I'm not his total dominant. Really?

That's a little dramatic isn't it? I mean, sometimes when I tell Ivan I'm dropping by and he'd better damn well be naked on his knees, he certainly cooperates. But shit, if he wants to hang out at home and play with his Xbox, I don't want him to be miserable.

Sometimes if he's pissed me off, I sentence him to write five pages of the dictionary within 24 hours, and that's kind of an imposition. Ivan loves his buddies, and they aren't that annoying.

George Casemont, Ivan's best friend is a bit of a loudmouth, but I can put up with Casey, and Rod and Flynn and "The Squirrel", they're okay. Men need time to blow off steam and tell dirty jokes, that sort of thing

And yes, the other night Squirrel pinched my ass at the bar, but Ivan's so generous with me, he takes me on trips and he's amazing, that tongue between my legs. I mean, BDSM shouldn't be our whole life, should it?

I do hear Ivan telling me now and then that he wishes I was more into taking him beyond his limits, and I guess I wonder what that means.

April 23

FromWrenjohnson

To: JosephineMiller

Josie, babe, the scene shouldn't be YOUR whole life. I date normal men, I fuck 'em and blow them, and make no unreasonable requests. But for a man who you're involve with who aspires to be a slave? You should be able to order them to leave work when you request. I did that with Duncan just the other day. I told him to leave an important board meeting he was having and come to my place and clean my bathroom and parlor for a cocktail party I was having that night-that he wasn't invited to!

I texted him while I was out of town, and he went and did the important janitorial work I needed. And Dunc's devotion gets better every day. He sends flowers and surprise candy and jewelry now and then, and he's just a sweetheart.

I have no interest in a part timer. I did have a lovely time with you and Ivan when we got together, but I was amazed that he was dressed for most of the time we were hanging out at your place, and that you had to help with the cooking.

You two were joking about his crappy culinary skills, but he should be taking a class. I had Duncan and another sub of mine, Ralphie, take cooking and beautician classes and now Dunc is working on light carpentry.

Sure, you should be hang-gliding and water-skiing, and using Ivan's equipment, but do it with nice, studly, regular men. Ivan is gorgeous and very masculine (that will be reduced if you have him sucking your friends' dicks now and then) but his role is to serve.

The idea of giving up the fun things he loves to do will arouse him further. Ralph has a fifty foot Sunseeker Predator, a gorgeous boat.

Ralph took me and Carlos out on it, and did most of the work, and when it came time for lunch, Ralph stripped and served us cold chicken and white wine, and then went below to kneel naked in the hold while Carlos and I enjoyed the sunshine.

Ralph caddies for us at his club and waits while I play tennis, that kind of thing.

Don't you see? Ralph is thrilled to find me theater and opera tickets, and then to be tied up in my basement while I'm enjoying them with another. He understands who is Number One...

Next week I'll have you over to Ralphie's house. He'll serve us dinner and then wait on his knees while we eat, except when we need our wine glasses re-filled.

And then I'll show you my recent implement purchases, we can take turns using them on Ralph's tender bottom

Ivan needs this too, whether he knows it or not.

You'll love the "fighting whip" I got. It's made of Latigo, and is only about three feet long. Of course I don't fight with it, Ralph takes down his pants and I love the kick the whip has as it cracks across his skinny little ass.

I used to use these glorious Australian kangaroo whips, but latigo has a rare power to it. Ralph screams like a little bitch, but the upper arm exercise I get is so worth it, you know?

This Latigo thing is single-tail and when I'm not hammering Ralph with it, I can use it to grab shit on the dining room table, though it also destroys things.

Don't worry-Ralph bought it for me, and our goal is that he can take twenty across the ass cheeks. With no screaming. One thing that will help is, I am not letting Ralphie out of his chastity belt again for anything-even teasing-until he can keep his mouth shut for a little flogging, Goals, right?

May 8

From: JosephineMiller

To: Wrenjohnson

Wow. What I love about you, Wren is, you're younger than I am, and such a sweet little honey blonde, and yet you are such a terror with those implements! I really enjoyed this time we had, I wish I could have brought Ivan. And the best part was, Ralph knelt and THANKED us, and kissed our feet and he brought me to about eight orgasms when you "lent" him to me while you and Carlos went to Dave and Buster's.

If I'd had the key to Ralph's chastity, I would have sneaked him an orgasm, I'm afraid to say, he probably could have talked me into it, what with being a celebrity defense lawyer...

Ralphie told me how much he loves you and he's learned to love Carlos. He is hoping that he will be able to keep his mouth shut more in coming "corrections"...you didn't tell him that Carlos is going to be giving him the whip next, have you, you bad girl?

**************

July 10

Ivan smiled, and rubbed Josie's back. He kissed her ear, as she lay against him, smelling her pretty shampoo. God she looked good in the tie-dyed shirt, it grabs her boobs like a catcher's mitt...so hot, so tight.

And her snug jeans were great too. Having her butt casually pushing Ivan's crotch as they watched "Law and Order" was making him wild.

Josie shifted a little , and Ivan looked down her marvelous bosom. She always wore these push-up bras, and though the tits were gorgeous naked, in this tie-dye, they were insane.

It was kind of a extra thrill, because Josie hadn't let Ivan see her in the birthday suit too much lately. He'd told her about his clothed-female-naked-male fantasies and all, but this was a little too often. Sometimes she would only take off her pants and panties to let him eat her out, but wouldn't remove her shirt at all.

Ivan hadn't cum now in over a month, and the chastity cage was digging into his sensitive organ. She'd gotten a cage for him, so his dick was visible, but it was attached to a piercing all along the underside of his dick, and then his dick was curved, so he couldn't really get completely hard, although man, did he still get excited. Too excited, and it hurt.

The chastity fantasy was tougher than the reality.

The other night (while she was dressed primly in a sweater and skirt) Josie had ordered Ivan to strip and she'd given him a long hand job stroking, after she'd locked his wrists behind his back in handcuffs.

It had been quite a massage. Josie had rubbed his dick, his inner thighs, his stomach, his nipples...and then she'd shoved a long cucumber shaped dildo up his rear, which had been exhilarating and made Ivan wonder if he was bi.