Emily is going to stay with Derek for a week while I’m out of town and we have a bet over whether I will remain locked in [chastity] [tease and denial]

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So this one happened pretty recently. I had to drive out 5 hours for a work onsite, and I would be staying there for a whole week. Of course, Emily was sad to see me go and we talked about her coming up with me but working out of a hotel room is not really where you want to be if you have the option. A few days after, she said she’d been thinking, and that maybe she could stay at Derek’s while I was gone. Just floated it out there casually with this mischievous look on her face.

I told her I’d think about it but honestly I had thought about it too and I’d already made up my mind about it. The idea of her spending a full week at his place, sleeping in his bed every night and doing everything with him while I was five hours away in a hotel room made my cage feel super tight just thinking about it. But I played reluctant and told her I wasn’t sure. She told me to think about it and then brought it up again during an edging session when she already had me pretty desperate. I was tied up on our bed, her two fingers working me over slowly and gently, and she started talking about how hot it would be. She told me Derek was already excited about the idea too and told me to imagine her starting up every morning in lingerie with a footjob or a deepthroat. She edged me over and over while she made her case and eventually I stammered out fine, okay, yes, and she smiled and got all giddy like she’d broken me down, which I guess technically she had, even if I’d wanted to say yes from the start.

Then I brought up the cage.I told her I wanted to be unlocked for the week. She shook her head immediately and said she wanted me pent up and desperate when I got home, that it would be better for both of us. I pushed back and she thought about it for a second and then said “we could do a bet,” which of course I was open to. We went back and forth on the rules for a while, during which she continued playing with my penis.

The final rules were: She’d use our little disco ball motor and attach a feather to it so it would spin against me (we’ve done this before a few times. I’d have to last fifteen minutes without hitting the edge while she teased me however she wanted, as long as she wasn’t touching my penis directly. She could touch me anywhere else. She also got to edge me beforehand a few times, and I negotiated a five minute break between the last edge and the start of the timer. I wasn’t allowed to cum or ruin, and if I felt myself getting close I had to call it. I also wasn’t allowed to look away if she was showing me something.

Two days before I was leaving she went over to Derek’s like she does most evenings. She came back a little later than usual and I was already lounging around naked because I knew we were starting as soon as she walked in. She came through the door and immediately climbed into my lap and started making out with me, warm and a little flushed. She told me he was already looking forward to having her to himself and teased me a bit about how good she’d gotten fucked. Then she pulled back and looked at me and said “okay, let’s get you all tied up.”

She used one of our chairs and tied my arms behind the back of it, my legs to the bottom, and then ran ropes across my torso and upper thighs until I couldn’t really move at all. She loves the bondage part and takes her time with it, and by the time she was done I was already straining just from anticipation. And of course as soon as she undid the cage I was fully hard immediately. Oiling up her hands, Emily settled onto the arm of the chair beside me and started stroking me with two fingers, slow and light. Her other hand came up to hold the side of my face and she kissed me while she stroked, super intensely, and I kissed her back of course. I remember pace of the kissing was much higher than that of the stroking. I couldn’t thrust or anything, only sit there and take it while she worked me up. She edged me five times like that, kissing me through all of it, starting back up without warning each time after she’d let me come down, and by the time she was done I was leaking and throbbing and my whole body felt strung out. She set the five minute timer and stepped back.

She put a blindfold on me and I heard her setting up the motor between my legs. Then she left the room for a couple minutes. I could hear her moving around, opening something, and just doing some random stuff. I just sat there in the dark, imagining what she was doing and trying to get myself as far back from the edge as I could before the timer went off. It wasn’t really working. Then the alarm sounded and I heard her click the little motor on.

The feather hit the underside of my penis and I jumped about as much as the ropes would let me. It was set to the highest speed, one full rotation per second, and the sensation was this relentless light brushing had no pause to it, just the same maddening touch cycling over and over against the entire length of the underside of my penis. And then she took the blindfold off.

She was standing in front of me in a lingerie set I had never seen before. Black, with a choker at her neck that had two thin straps running down from it that crossed over her chest and covered her nipples, basically functioning as an X shaped bra but leaving almost nothing to the imagination. Her nipples we’re hard and poking into the material. Tiny matching black panties, lace along the top, completely sheer below it, with little fuzzy socks on her feet. She was smiling at me, this bright excited smile, probably because of whatever my face looked like in that moment, which I can only imagine.

“Derek got me this a while ago,” she said. “I wasn’t allowed to show you until now but he said I could use it to make you lose the bet.”

Then she turned around slowly and bent forward, spreading her cheeks open with her hands, and I noticed there was a hole torn open in the fabric right over her pussy. She looked back at me over her shoulder.

“He did that so he could fuck me while I was wearing it,” she said. “Which we’ve done a lot of times.”

She straightened up and turned back around and looked at me with this expression like she was little sorry for me, but not really, before she put her teasing face back on again.

“You’re never going to get to touch me in this,” she said. “But at least you finally get to see it.”

Her pussy was visibly wet already, which it always gets when she’s in full teasing mode, and I was already throbbing against the spinning feather just from the last thirty seconds. She did a slow little show for me, turning around, running her hands down her sides, and blowing me a kiss, before she settled into the chair across from me. She crossed one ankle over the knee of her other leg and reached down and slowly peeled off one fuzzy sock, then the other. Her feet were, of course, perfect. I immediately noticed she had gotten a pedicure that I didn’t know about, and her toes were painted black, which she usually doesn’t do, and she flexed them slowly and spread her toes and just let me look for a second.

“I got a pedicure earlier before I went to Derek’s,” she said, holding one foot up and tilting it side to side. “I know it’s your favorite color baby, but you’re gonna be out of town…,” she cooed to me with a mock sadness that made me throb hard against the feather.

She smiled.

“They’re going to be just his to enjoy all week.”

I was already trying to manage my breathing, trying to focus on something neutral and stay level headed. The feather was relentless. It just kept going, and the sensation was already proving to be bothering me. I was doing okay but I was starting to worry about lasting all 15 minutes.

Then she reached for the oil and poured it slowly over both feet and started rubbing it in, working it between her toes, across her arches, over her heels, taking her time with it, until they were shining and dripping. She held them up toward me so I could see them properly.

“Theyre gonna be soooo soft for him all week,” she teased. “He told me he’s gonna have me dressed up and tied facedown while he tickles them whenever he wants, and I told him okay.”

She said it so casually, like she was just sharing her plans for the week, and I felt my cock twitch hard against the feather and had to really focus to center myself. I was leaking profusely, had been since before the timer started honestly, and I could feel it. She could see it too.

She tilted her head and looked at me with this expression of exaggerated sympathy, complete with this adorable fake pout she does.

“Oh sweetie,” she said, stroking a finger down the side of my face. “You’re already struggling and we’re barely getting started. I don’t think you’re going to make it.” She paused. “Your little guy’s about to pop any minute.”

I didn’t think that was true but her teasing me about it was definitely making it harder to stay confident.

She let that sit for a second and then added, completely casually, “You know Derek could sit there all day and not have any issues holding it.”

I was concentrating as much as I could, but I knew that was true. She always teased me about our stamina difference to get me worked up and it never failed.

“I want you to really think about whether you even want to win this baby,” she said. “Because if you’re unlocked, you’re not getting any sexy snaps from me. You’ll get my face on FaceTime and that’s it.” She smiled. “But if your mean little cage is on, I’ll be sending you pics that will make you want to explode”

She said it in this warm gentle voice with a giddy grin and sparkling eyes, clearly having the time of her life. I was trying and failing not to think about everything she was telling me. I was trying not to think about anything except staying below the edge.

Then she lifted one oiled foot and spread her toes for me, and held it directly over the spinning feather. The feather was brushing the bottom of her sole, maybe three inches from my penis, and she just held it there. She completely lost her composure, giggling and slapping her hand against the armrest of her chair, her leg jerking. She held it there for a few seconds just laughing and then pulled it away.

I groaned. I couldn’t help it. It was this sound of pure frustration and maybe a little fear because I was already closer than I wanted to be and we couldn’t have been more than three minutes in.

She stretched out on her stomach on the ground then, feet up behind her, kicking them lazily, chin resting on her hands, and looked at me.

“I’m going to wake him up like this every morning,” she said, and mimed giving a blowjob, twisting her hands in the air in front of her and bobbing her head up and down. “Every single morning.”

Then she stood up and turned around and bent forward again, spreading so I could see the torn hole in the fabric, and told me she was going to be cooking for him every night in something sexy and an apron, and that after dinner he was going to take her to bed and do whatever he wanted with her. Then she turned back around and sat back down.

“We also have a planned edging session,” she said, like she was going over a calendar. “I’m going to take an Adderall and he’s going to edge me for thirty minutes straight, no safeword. Then a water break. Then another thirty minutes.” She laid back in her chair and spread her legs so I could see her pussy through the hole. “I’m gonna be tied up like this, probably gagged too. He always makes sure I can’t move at all and I’m completely exposed. And he works me over sooo good baby, starting at my feet with a little kissing and gentle tickling. You know how sensitive they are, and then my thighs, he sucks and licks all over them, and his strong hands are just gripping me. Even if I wasn’t tied up I wouldn’t be able to get away. And then he gets to my pussy and that’s when I really lose it. I never know if he’s gonna eat me out while using a dildo on me, or if he’s gonna tease my clit with feathers, just holding it still. My favorite is when he fucks me soo slowly I can’t cum from it. Before long, my legs are shaking and my wetness leaks all over me and the towel under me. I just moan and plead, trying to tell him I’ll do anything to cum, but there’s nothing I can do. He always says he loves how desperate my eyes look, and how my mascara starts to run. “

I had completely lost track of the timer at this point. I was just trying to hold on. The feather was doing this thing where it had gotten wet and would catch slightly on the frenulum at the same point in every rotation and every time it did I felt like I was fighting for my life. I was twitching against it trying to breathe slowly and evenly and focus on something else but there was nothing else I could focus on because she was right there in front of me in that lingerie with her oiled feet and her wet pussy, talking about Derek edging her for an hour with no safeword.

Then she got up and walked toward me and I felt the blindfold sliding back over my eyes. She kissed my cheek, then her voice dropped to a softer tone.

“Oh my sweet baby,” she said. “You’re wearing that cage this week for sure. I thought this was going to be way harder to win.”

And then her lips were right at my ear. She licked it and then whispered, “This was me earlier today.”

An audio started playing. It was her and Derek, clearly mid-fuck, and she was loud, really gone, and then I heard his voice say “are you gonna keep him caged all week?” and she moaned “mmf, oh god, yes” and then a few more seconds of them together before it cut off.

I my penis clenched and I felt the precum sliding out of me. I was trying to hold completely still, trying not to twitch into the feather, and to breathe steadily. I heard her sit back down in front of me and then felt something warm and soft brush against my lips. Her foot, the oiled sole moving slowly across my mouth. I kept my lips pressed together, telling myself I still had time, that I could hold on, that if I just didn’t move and didn’t think about the audio I could get through the rest of the fifteen minutes. Surely this was almost over, which is why she was pulling this strategy out

“Just open up babe,” she said. “It’s not going to make a difference anyway.”

I didn’t, studying my resolve.

Then another audio started. This one was her getting edged, it was hard to tell if she was also getting fucked, but she was begging him, her voice completely wrecked, saying she’d do whatever he wanted, and I heard him tell her he just wanted to keep playing with her, and she let out this ragged broken groan and there was creaking in the background that I knew from experience was the sound of her pulling at her restraints and failing to move, and then it cut off, and Emily said, “That’s gonna be me all week baby,” rubbing her toes against my lips.

I lasted about three seconds after that.

I felt it building fast, way faster than I could manage, this wave coming up from nowhere and tried to fight it down, but at the same time I involuntarily tried to thrust and the ropes stopped me. At this point I knew I had lost and was about to tell her, but before I could say anything the foot was gone from my mouth and Emily had snatched the feather away. Emily said giggly, “You lost baby”

She took the blindfold off and looked at me with the same fake pouty expression, and I just sat there still twitching. She teased me about it for a little while, asking how it felt knowing I’d be locked up all week while she was at Derek’s, telling me she was going to think about this moment when she was falling asleep in his bed. Then she enthusiastically leaned in toward me and asked if I wanted more.

I immediately told her yes

She laughed and said “I was hoping you’d say that.”

She kept me tied to that chair for another twenty minutes, working me up and letting me down over and over, more of the show, more dirty talk about the week, what she was going to do for him, what he was going to do to her, until I was so far gone I couldn’t put a sentence together. Then she locked me back up and untied me and made out intensely for a few minutes before we showered together and got ready for bed. She fell asleep curled against me pretty quickly and I lay there caged and leaking and thinking about the long and erotic week ahead of me.


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