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Maintenance 8 - Daria Werbowy

Maintenance 8 - Daria Werbowy

7 months ago
A Convenient Handle

A convenient handle

What's the longest relationship you've ever had with a boy *without* locking him up forever?

Not long enough! I think longest-lasting boy was three boyfriends ago. He lasted about three months before curiosity got the best of him. He was a pretty big talker and loved to make fun of the boys I keep locked. Motorcycle dude. You know the type. The more he learned about what I do to boys, the more hilarious he thought it all was. In fact he got in trouble several times in the court of Agni because he kept mocking the guys who came to see me for their unlocking.

We were messing around after dinner one evening; he was naked and trying to get me off the computer and into bed. While he waited, annoyed, he absentmindedly fiddled with the cage that I keep on display. He was pretty familiar with it because he loved to twirl it on one finger and grin like a wolf any time a locked boy was present.

Him: “I don’t think I’d even fit in one of these things.”

Me: “You would.” I was only half aware of him, busy with my work.

Him: “How do you know?”

Me: “I’ve personally put that thing on hundreds of dicks. I know exactly what size of dick it fits.”

Him: “Are you saying I have a small dick?”

Me: “I’m saying you’re a big dick and that you have an average sized penis.”

Him “No way…”

He put it next to his flaccid penis, sizing it up.

Him: “See. I’m too long.”

Me: “By a quarter inch. That’s just the right size.”

Him: “It’s not wide enough.”

Me: “It is.” I went back to my emails.

I didn’t notice what he did next. After several minutes he sort of huffed.

Him: “Huh. I guess it does fit.”

My attention was suddenly yanked from the computer.

Me: “You didn’t!”

Him: “What? I just wanted to see if it would fit. I didn’t lock it.”

Me: “Jeff! It doesn’t matter! You put that on your dick! It already changed you. Your brain is being rewired so fast right now and you’re just sitting there. Take it off! Now!”

Him: “Ha ha! Whatever! I’m not like one of your idiot circus freaks. I’m just messing around. Sheesh.”

Me: “Then why haven’t you taken it off?”

Him: “Because it bugs you that I’m wearing it. It doesn’t hurt and it’s not hurting anything.”

Me: “Of course it doesn’t hurt. It feels fantastic, doesn’t it? It feels like nice cool grip on your cock.” I slid from my computer chair to sit next to him on the love seat. I ran my hand up his leg toward the cage. “Jeff, if you don’t take this off now I can’t be held responsible for what it’s going to do to you.”

I remember his face in that moment very clearly. It was the face of pleasure drunkenness. He was trying to macho if off but the dumb little smile and dilated pupils told me what I was afraid of. It was too late for Jeff. He snorted at my assertion but still didn’t take the cage off.

Me: “And if you think that feels good, you have no idea. You haven’t really experienced it until you feel the cool metal ring slide behind your balls. There’s nothing like it. With the whole thing on it feels so snug and so perfect.”

He turned the ring over and over in his hands, considering my words.

Him: “No, I know what you’re doing. No thanks. I’m bored. Can we have sex now?”

Me: “Sure! Just take it off, Jeff.”

Him: “You take it off.”

Me: “Jeff, I know you want to feel the ring. You’re going to start getting hard any second and it’ll be too late. Now or never, Jeff.”

Him:  “Fine! But then we have sex.”

Me: “Sure.”

He slid it around the base of his cock and I helped him close it up without pinching him. I put the lock in the hasp but didn’t lock it.

Him: “It actually does feel pretty good.” He adjusted the cage and hefted it. He played with it a little, jiggling it and bouncing it to get a feel for it. “Kind of like a really deluxe cup or something…but better.” He stood up to walk around in it. He hopped a bit and jogged in place. I remember giggling at naked Jeff jogging in my living room. “It’s sort of heavy but it’s amazing how it hugs the body. I thought it would fall off but it’s just, bam! Just right there.”

Me: “Feels good, doesn’t it?”

Him: “Actually, yeah. Feels great.”

Me: “You don’t want to take if off, do you?”

Him:  “I could wear it for a while if I had to.”

Me: “Could you? I don’t know, Jeff. You aren’t exactly the patient type.”

Him: “I’m patient! I put up with you, don’t I? I could wear this for a long damn time.”

Me: “You couldn’t last two days in that thing. You’re not as strong as the weakest of my boys.”

Him: “Not strong?! Care to make a bet?”

Me: “Sure! Two days. No asking for release. If you make it I owe you twenty bucks and a blowjob. If not, then you wear if for a weak.”

Him: “You’re on!”

I motioned to the lock and he snapped it shut. I could see the little latch in his brain flip at the same instant, as if that was what made the “snap” sound. He got that drunk-looking vacant expression as he tugged at the cage, that face that I love so much, the expression of a man who is slowly coming to grips with the fact that he no longer has access to his favorite member, the realization of true loss of control.

Me: “Ok, now on to the sex that I promised. And since your cock is occupied with his new metal girlfriend I guess you’ll just be going down on me this time.”

You already know what happened to Jeff, don’t you good reader? He didn’t last two days. He lasted about 18 hours before he begged me to take it off so he could “nut”. I don’t think he even realized he was losing the bet when he did. It didn’t help that I wore yoga pants and a low-cut, tight-fitting top around the house the whole weekend and kept bending over in front of him with every opportunity. Woops!

Jeff and I stayed together for another month but his love affair with chastity grew out of control faster than he expected. By the time I finally let him down easy, he didn’t really even care that I was breaking up with him. All he seemed to care about what that I continued to be his keyholder to help him through, to support him in his transition to extended chastity. I was glad to do it and to add his key to my collection–just another locked boy.

PS: I’ve been seeing a new man lately. We’re taking it very slow. So far he’s lasted a couple months without succumbing to the lock. Root for him, guys!

PPS: Hey Jeffy! You say you don’t have a tumblr account but I know you perv me on here all the time. I hope your new metal girlfriend is treating you well! I do miss your cock on occasion but not nearly as much as you do.💋

eating a girl out for the first time? as someone with a couple of decades' experience (i started young, ok?), can i offer some advice?

take your time. your aim isn't to make her come as fast as possible, it's to make sure she enjoys every moment. slow down, revel in the process of finding out what she likes.

tell her how beautiful she is, how tempting her cunt looks, how intoxicating it smells, how sweet she tastes. she might be feeling vulnerable, especially if she's inexperienced too - it's your job to make her feel safe and adored.

enjoy the journey - i know you just want to feel your tongue on her clit NOW, but exploring her thighs, working your way slowly to her folds, trailing all the way up her cunt, drinking her juices, letting her feel your breath before she feels your touch...it'll be worth it. for both of you.

learn to read her body with all of your senses. she might be vocal but she might prefer to bite her lip or enjoy being gagged. you don't need to hear her words to know what to do. you'll feel her muscles twitch and relax - learn what it means when she lifts her hips, squirms or sinks into you. she might taste and smell differently when she is close to coming for you. pay close attention to her clit - if you're lucky and you've done a particularly good job, you might see it twitch as she recovers from the perfect orgasm. enjoy it.

you can be vocal though. moan into her. use every sensation you can. light flicks to determined, long, slow licks. blow gently on her wetness. how does she react to your lip piercing? your teeth?

build and add to the experience until she's completely overwhelmed. play with her nipples. run your nails over her skin. lift her legs and spank her.

chances are, she'll get to the point where she really needs you to fuck her. slip your tongue all the way down and inside her. if you can't breathe, you're doing it right. that means you probably won't be able to keep it up for hours, so save this move for when she's right on the edge and you're ready to let her tip over.

if you're especially lucky and she's a squirter, you will get absolutely soaked. enjoy it. show her you're enjoying it. moan into her cunt; she'll come even harder.

if she needs to be fucked harder, slip your fingers inside her cunt and curl them up towards your tongue as it circles her clit. all of her most sensitive nerves will be between your tongue and your fingers. you'll be able to feel every tiny twitch inside her; it's the most beautiful place in the world to be.

when she can truly take no more, stay close to her as you drift away from her cunt. kiss your way up her tummy and her chest, let her taste herself on your lips as you hold her and let her ride out the aftershocks. trail your fingertips over her back. whisper in her ear. tell her everything you loved about eating her out.

8 months ago
Done In Collab With @misswatsonssissyhandmaid
Done In Collab With @misswatsonssissyhandmaid
Done In Collab With @misswatsonssissyhandmaid

Done in collab with @misswatsonssissyhandmaid

I Know Mean Girls Turn You On! You Love Being Bullied By Mean Girls!

I know mean girls turn you on! You love being bullied by mean girls!

Girls make you weak and mean cyber bullies make you weaker!

8 months ago
The Power Is Addictive!

The power is addictive!

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