Miles's Conundrums

Submitted by: Justin

Gretchen smiled as she moved her long nails across my purplish, throbbing shaft.

 She looked so cute... A pale beauty with short, slightly spiky hair.

Gretchen is a little on the chubby side, but in a sexy T&A kind of a way.

She was wearing a tight top and snug courdoroys as she leaned across the bed toying with my tortured Willy.

"What's wrong, Miles? Having a bad time?" Gretch asked me bemusedly, as she stroked my quivering shaft with a sharp thumbnail.

"I guess you're having a hard time with the 103 days so far?" Gretchen smiled at me evilly.

Two and a half years ago when we'd started playing dominance games, I'd confessed to Gretchen my desire to be put into chastity, and to "earn" my orgasms.

"How do you mean?" Gretchen had asked at the time.

 She'd already begun to enjoy the whole aspect of all the oral sex on her side, and my increased participation in the heavy housecleaning.

"Well, it's such a thrill making love to you." I had told her. "I really think that your sexual favors should be earned by me." Gretchen had laughed at the time.

"Well, I already cut you off when I'm on the rag, or when you stay out too late with those idiots watching MSNBC."

This was true, Gretchen would most certainly cut me off even before we were married, just tell me no sex, because she was mad, and make me do all sorts of chores and favors to get her in the mood.

This really had thrilled me, though her previous boyfriend, who had been a friend of mine, had told me many times that Gretchen was a "ballbreaker"

When Gary had broken up with Gretchen, he'd warned me. "No, I don't mind if you date her, man, but she's really high maintenance."

Why had that excited me? The idea of trying to please this imperious princess had been just possessing to me.

 I'd immediately begun to prove to her that I was no insensitive Gary type, that I was primarily focused on making Gretchen pleased.

We never switched the check or any of that nonsense, I always picked it up.

After we'd married, it had been so gradual how we'd moved into a state of Gretchen being my dominant.

 I was an investment banker and brought home most of the bacon, and Gretchen did a little film-making.

It was her career, but truly much more of a hobby.

 Theoretically, Gretch was supposed to look after the house, and make things comfortable and relaxing for me, and I was glad to subsidize her projects.  

But it had seemed from the start that whenever I got in at night, the house was a bit of a mess... Gretchen was quite often sitting in front of the TV.

"Oh hey babe." she'd say as I dragged in from a long day.

 "Didn't get too much done, but there's some kinda TV dinner thingie in the kitchen, you know I can't cook."

 And I could never get upset with her, and often I'd take off my jacket, put on an apron, and make us a good meal, as my mother had taught me to cook quite well. 

 Then I'd try to pick up her discarded deli wrappers and stray shoes, and sweep the carpet a bit.

 "Your ass looks so cute when you're sweeping, honey" Gretchen would say with a laugh.

I'd often make her a special dessert, and spend excessive time rubbing Gretchen's feet, hoping to get lucky at bedtime, and sometimes I did--

Gretchen was a great lover, and she had a tight vagina! But more often than not, she was tired from whatever she'd been doing.

 I'd warm her up with a little cunt-lapping, and then a little more.

"God you're so good, Miles!" Gretch would say, gasping. "Can I come up now, and stick it in?" I'd ask hopefully. "No, just a little more, please."

Gretchen would push my head further into her hot pussy, and I would lick her til  she was exhausted.

"I'm way too tired now for screwing, babe, I'm sorry." Gretchen would kiss me good night, and tickle my cock a little.

 "It's this damn project I'm on."

And there I'd be lying next to her beautiful body, my cock bouncing like a metronome.

Then I'd try not to bother her... though I wanted to touch her milky full buttocks, or if she was lying with her face to me, her full breasts.

But Gretchen got very annoyed with me if I disturbed her sleep. What a curse it would be, rolling around on the bed, my cock stiff and painful!

At first we still made love three times a week, with me eating her out about six times.

Once in a while I got a blowjob from Gretchen, which she was quite good at.

 But then it cut down to once or twice a week, and Gretchen was amused, and then irritated by my sulkiness when I'd ask her, pleadingly, why she only wanted cunnilinguis.

One afternoon, I'd been scrubbing the bathroom floor, and imploring Gretchen "C'mon dear, don't you think I want to make love, too?" Gretchen had laughed.

At the time she was wearing a halter and shorts, and I was working in only a long-underwear bottom.

"I get such a kick out of it when you roll around and moan on the bed, and then when you go to the bathroom and jerk yourself off."

 Gretchen had made an imitation of my light pants,and "a--ahhh", which was an exaggeration of my orgasm.

"It's just so funny, Miles. You're like a fourteen year old, still."

"And there's nothing, NOTHING funnier than a man who's pouting because he can't get any."

Gretchen laughed. "You just strut around looking miserable like you're going to have a tantrum, and I'm just fascinated by that.

I was telling some of the guys on the film site about it, they thought it was hilarious."

 My face had burned as I continued the scrubbing.

 All the guys Gretchen worked on her film projects with were tall athletic types, and I was a short little banker.

Several of them were ex-lovers of my beautiful wife, and then there were the "guys" who were beautiful girls who worked with Gretchen.

Some were actresses, some film strippers, and it was so humiliating that she'd tell them that!

"Can't you keep our private problems in the house?" I'd asked.

"What problems, Miles?" asked Gretchen implacably. "I'm not having any problems."

And neither was I after I began to come to terms with my desire for servitude.

 The problem was, I thought I just wanted it to be a weekend thing--and Gretchen was very good at that.

WHACK WHACK THWACK! "Ohhh!" I moaned after one of my early whippings.

 Gretch had tied me over the arm of the sofa with my pants and shorts  huddling about my ankles, and she'd exercised a bamboo cane she'd picked up at a flea market.

"What're you whining about, Miles?" Gretch had asked cheerily. "This is your dream!"

WHACK WHACK SWAT! "You wouldn't believe how your butt looks now, hon. You've got all these purple marks all over your right cheek."

I'd turned with tear filled eyes to look at Gretchen in a snug striped turtleneck, slapping the cane in her hand. WHACK WHACK! I'd burst into tears.

Gretchen had looked concerned and pulled me off the couch and began stroking my bottom.

Then she turned me around, pushing my scorched butt against the sofa, and she began to pull on my cock, which had lengthened.

 "You want this, right, Miles?" Gretchen had breathed in my ear. "God forbid I do the wrong thing by you."

I was biting my lip, trying not to sob further. "N-no Miss's what I need!" Gretchen had laughed.

"Miss Gretchen, huh?" She'd stuck a wet tongue in my ear and began toying with my cock all the more.

 My hands were tied, of course, to keep from jumping away when I'd gotten the caning, and now all I could do was writhe as she'd stroked my bulging cock.

  Gretchen had pulled and stroked my cock until I began feeling the familiar pulsating at the base of my tortured penis, the pull of the cum, which was now rising.

 It had been several weeks since I'd had sex with Gretchen, and I at that time was not a masturbator, having given that up after college.

Gretchen had at this point become quite used to my oral ministrations, and depended on these for her release.

And she had learned to make me go through all sorts of measures to "Get me in the mood" to actually  be allowed to stick my dick in her.

Gretchen's soft, beautiful fingers were now playing a lullabye on my long-denied cock.

And her other hand was squeezing and pinching my bare bottom, welted as it was from the bamboo cane.

I was rather worried that our housemate might come home and wonder about...

Why my fully dressed, sexy wife was standing, and stroking her hubby's cock while his pants and undies were down on his Hush Puppies.   God, Gretchen's fingers were incredibly skilled. "Having fun, baby?"

Gretch's voice tinkled, and now she was kissing my ear, her tongue exploring my sweating neck.

 I gasped and my stolid erection began drooling excessive precum.

 I was getting closer to release. Oh, to cum in her hand. I wanted it so badly!

  My cock quivered as Gretch's long, purple nails had tickled the vein crawling across the shaft.

"It's such a thick, burgundy vein, honey" Gretchen whispered.

"It almost matches the shade of my nails, but not quite....but I'll make the vein purple in time."

Oh, God, that voice. The way she could turn me into jelly! What kind of a monster was I creating?

As Gretchen's forefinger moved back and forth across the vein, her thumb tormented my frenum, and my balls felt leaden with backed up spooge of several weeks!

"Are you excited, hon?" Gretch had asked me. "Do you like this?" God, I was hotter than any sex experience previously...and I'd once been with a Playboy Bunny!

This was better than any blowjob, any time a girl had let me take her from behind...

I'd just had my ass blistered, and now I didn't know if I was going to be allowed to cum!  Unbelievable!

Gretchen stopped for a moment. "I think you need to service me a little, baby.

 You're having all the fun." Gretchen had then pushed me to my knees and pulled up her white miniskirt.

 No panties! I'd gotten between her legs.

"Gretch, undo my cuffs." I mumbled. " I need my hands to pleasure you."

Gretchen laughed. "No you don't, just lick away. If I don't like it, no more playing with Mr. Willy" she'd said.

On my bare knees, scraping the hardwood floor, I'd licked away until Gretchen had experienced two shuddering orgasms...

It had taken about forty-five minutes...

 Finally she'd dropped her skirt down and helped me up again, and resumed her operations on my sweating, painful organ. 

I began getting close to orgasm yet again - "Your legs are shaking, honey...I think you're ready to have a wet one, eh?"

 Gretchen laughed as she tongued my neck some more.

"I bet you believe you deserve it, because you've made me feel so good, eh?" I moaned, and my legs shook more and more.

"Well, I hope you liked your –oh-orgasms, Miss Gretchen." I had said tactfully.

 Gretchen had laughed deep in her throat...and all of a sudden I felt very close. It was coming fast.

Damn! Gretchen now was slowing her masturbation a bit, and the semen receded back to my balls.

I relaxed, biting my lip and my cock drooped a bit, and Gretch began stroking faster again, pulling the frenulum.

 Watching Gretchen's lovely nails as they played across my cock, I had begun getting more and more  excited.

Slam! The door to the kitchen opened and shut. My worst fears were realized.

It was Tom, our handsome housemate.

"Tell him you're busy in here, honey." I whispered to Gretchen as she toyed with my organ.

 "It's ...just weird.. keep him out of the room." I said again.

"Hey Tom!" Gretchen had shouted out, "What're you up to?" Tom had strutted right into the living room.

"Not much Gretchen, what about you?"

His eyebrows had risen as he viewed me with my pants and undies down, my ravaged ass jiggling.

 Gretchen let go of my cock and stepped away.

"What the hell's goin' on?" Tom had asked.

Gretchen had smiled and picked up the bamboo cane, waving it about. "I'm just having a little kinky session with Milesy here."

Tom laughed as Gretchen lashed my bare butt once or twice. He watched me twist and bounce, my hands still cuffed.

"This is so weird, Miles." Tom laughed. "Gee, do any of the fellows know about this?"

 Gretchen laughed, too, and whacked me a couple more times.

 "Jesus-please Gretchen." I begged, tears rolling down my cheeks.

"I'll stop if you let me tongue kiss Tommy here." Gretchen laughed.  I stood up indignantly. "Absolutely not."

WHACK WHACK WHACK! Gretchen lay the cane about me a few times, and I began crying heavily despite myself.

Tom was grinning from ear to ear.

"Whatever you want, honey....but we're married!" I had pleaded with her.

 Gretchen had laughed and gone over and given Tom a big, tonguy kiss...

Tom had ground his body against her as I stood, drawers down, humiliated.

"I gotta go out, but we should do this again sometime!" Tom laughed, kissed Gretch again. "Don't be a bad boy there, Milesy."

Gretchen grabbed my ear "Say yes sir, uncle Tom." She whispered in my ear....

I gritted my teeth. WHACK WHACK My ass was roaring. "Y-yes sir, Uncle Tom!" I sobbed, and his laugh was the last sound I heard.

Gretchen looked abashed. "Poor thing, you're not mad at Gretchie are you-ums?"

She kissed me deeply, and her soft fingers dropped to my sweltering cock again, and she began pulling it gently.

"N-no, I just didn't want anyone to know - discretion and all that." Gretchen rubbed faster.

"Oh, honey, discretion's not that're just a sissy-boy....Tommy knows that.  

Why do you think he has to do all the repairs around're not mechanically inclined, you say, but really, you're just a sissy-boy!"

  Gretchen's long nails moved faster and faster and my cock got longer and harder.

  My legs wobbled again, and Gretchen's fingers slowed down. "Please go faster, honey."

   I begged. Gretchen looked annoyed.

  "I'm not your honey..."she said. "I'm Tommy's honey, maybe..but you're just a wimpie boy, you know."

  I looked at the floor, sad and abashed.

  "Tell Mommy you want her to go faster." Gretchen whispered in my ear, and I begged. "Mommy, please go faster...please?"

  Gretchen had smiled craftily, and nodded a bit, and the fingers began wandering more rapidly across my cock.

   My legs began trembling as I approached orgasm...her fingers slowed again

"Poor baby can't cum?" Gretchen asked unsuspiciously.

  I shook my head and tears rolled down my cheeks. Gretchen giggled softly and rubbed a bit faster.

  I felt the impact of the backed up seed beginning once more to roll forth in my cock,.

  Closer and closer I was to release. "Close your eyes, Miles." Gretch whispered in my ear.

  "I'm going to give you a helluva surprise, baby, like you've never had." I closed my eyes, bit my tongue and waited. 

   WHACK! THWACK! Suddenly my cock felt incredible pain, as I felt a sliver of fire through it, and I opened my eyes in abject horror.

  Gretchen had taken up the cane again and was flailing at my cock! WHACK  WHACK THWACK!

   I tried to back off from her, but it was difficult maintaining my balance.

  My hands were secured behind my back and my pants were clinging around my ankles.

  I dropped to my knees, and finally the caning let up, Gretchen laughing, the stripes jiggling on the top.

  "Poor baby. Don't you think that's funny, Miles?" Gretch asked as she helped me up.

  At the end of that evening, Gretchen had removed the handcuffs, and allowed me to fuck her, though I hadn't been allowed to cum until she'd released three times.

  . And although my butt was horribly sore, and I was unable to look Tom the housemate in the eye for many months.

  But, I had had to admit to myself that it was one of the hottest experiences I'd ever had.

  As time went on, Gretchen gradually began to take over. She did less and less around the house, and I was expected to pick up the slack.

   My pants and underwear began being taken down regularly, if there were marks on the baseboard or streaks on the windows.

  Once, when I'd neglected to scrub out the garbage pail, Gretchen tied me naked to a ceiling loop on the back porch.

  I was shuddering, wondering if the teenage girls next door might happen to peer over the fence!

  Gretchen and I had traditional sex less and less. If I wanted to get into her pants, it became more and more of a reward.

   "I don't know, I'm just not that attracted to you...and you're too grabby"

   Gretchen had begun telling me. She spent less and less time in states of undress in the house.

  Gretchen still, of course wore tight clothes and cute little bustiers ("The guys at work dig it, you know, Milesy.")  

But didn't undress around me much, except that I was allowed to eat her out late at night.

  Still, she was teasing me beyond belief, twitching her full round buttocks across my crotch as she passed me while I was making dinner, or kissing my neck casually now and then.

  I began to beg her for sex. "I just am so horny, honey." I begged.

  "I mean, I work all day for you, and when I come home I want a little relief, you know?"

  Gretchen had laughed. "But you understand, Miles, that after people have been married a while, sex stops being the prime focus of the relationship." 

  We had been married for nine months.

   One night I was watching Gretchen paint her nails in the living room.

  Clad in a casual tube top and tight jeans, she was mesmerized by the  frosty pink she was pouring all over her long talons, and I was gaping at her.

   The more we didn't fuck, it seemed the more beautiful Gretchen was.

  She looked up at me. "What's wrong, honey?" Gretchen asked.

  "W-well, it's been such a long time since - since we had um, relations." I said.

  "I know." Gretchen had laughed. "I don't really feel that way about you right now, Milesy."

   She turned to her frosty pink nail polish. I bit my lip. Goddamnit.

  When I was in high school and college there were plenty of girls who'd told me they didn't feel that way about me..but I was married to this girl!

  What the hell was that?

  "Gretchen, please." I moved a little closer to her. "It's been nearly five weeks since we made love.

  I try to be a good hubby to you, and we have something special." I was babbling. I sounded like a Partridge Family album or something..

  Gretchen had looked up at me again, amusedly. "You're that horny, huh?" she asked, smiling.

  "Yes, please let me touch you, Gretchen." I pleaded. "Not even oral sex - I mean, you don't have to suck me but - "

  Gretchen's brow furrowed. "I know I don't have to suck you, or blow you, you fucking asshole. How dare you imply that I'd ever have to?"

   Gretchen had turned then to her nails and gritted her teeth. Oh shit, what was I going to do? I couldn't alienate her.

  "No, please, Gretchen, I didn't mean it that way" I begged.

  "I just want to make love to you, because I'm so horny....

  Don't you want to take your clothes off and make gentle love, like we used to?" I was babbling at this point.

  Gretchen had turned to me again. She toyed with her hair, and looked me in the eye in that sort of limpid way she used to - I grinned feebly at her.

  Gretch put down her nail polish brush and began toying casually with her nipple through the tube top.

  I stared as if hypnotized. "God all this attention is so flattering, Milesy." Gretch said, running a long pink tongue across her full lips.

  The door opened and Tom walked in, and headed for the stairs. "Hey, Gretch, Miles. How're you doing?"

  "I'm trying to decide if I'm going to give Miles any action." Gretchen laughed lightly. "He's begging me again...remember last  night, all the crying?"

  Tom laughed, and my face burned. His bedroom was right next to ours.

  It was true, I had been sobbing because Gretchen had not let me touch her that evening, and oh, how cute she'd looked in her Merry Widow! 

  Tom had  winked at Gretchen. "Good luck, Miles!"

  He went upstairs. "I wish you wouldn't tell him our business dear." I said feebly, but I knew it was no use.

  I really should've gotten Tom to leave some time ago.

  In the beginning I'd enjoyed having my old college roommate living with us.

  Tom had a minor construction job as opposed to my fabulously remunerative investment banking career, and it was great to give him a low rent.

   But now that Gretchen was here, it seemed that there was something weird going on between them, though I couldn't figure out what it was at the time.

  "Poor Miles" Gretchen said now to me. "You need a little attention, and I need a little entertainment.

  We each have to give a little." That sounded good, I thought, biting my lip.

  "Why don't you take your clothes off?" My eyebrows raised. "Here in the living room?"

  I smiled shakily. "Let's get upstairs, huh?"

  Gretchen laughed. "No, let's get wild here in the living room, take off your clothes, won't you?"

  I excitedly stripped off everything, and stood in front of her, grinning unsteadily, with my cock poking straight out in front of me.

   "Get me a drink, babe." I ran and got her a gin and tonic, and came back with my big grin.

  Gretchen burst into laughter. "God you look like a porno version of Howdy Doody."

  She took the drink from my hand and sipped it.  Gretchen casually put out a long leg and used her clog to poke my cock.

   The wood was cold against my rock hard cock and I gasped.

   Oh, I was so horny. "Gretchen honey, lets go upstairs and get it on, in the bedroom. I don't want people to---"

  As if to give reality to my fear, Tom came down the stairs. He saw me standing naked as Gretchen was playing with my dick with her shoe.

  Bursting into laughter, Tom shook his head, and went on his way through the kitchen.

  "Oh God." I bit my tongue. I got mad then.

  "You know, Gretchen, we should have the house to we can play around in the house naked. I'm going to tell Tom to move out next month."

  Gretchen moved her clog back and then lightly kicked me in the balls. I moaned.

  "Don't do that, Miles." Gretchen said sharply. "I like Tommy's good energy for me."

  What the hell did that mean? "But want to be more attractive to me, do you Miles?" 

   I nodded my head, suddenly totally aware of my nakedness and my potbelly.

  "Whatever you think, dear." Gretchen toyed again with my cock, now glistening with precum.

   Her clog pushed lightly against the scrotal sack that she'd just kicked so violently.

  "I want you to do something interesting for me...make me amused, honey." Gretchen said casually. "How about you paint your nails with my nail polish?"

Story continues in [ Part Two ]
[ Back to chastity fiction page ]

Page last updated 08-Aug-02 by: