Hey everyone, if you've been reading my stories, you know how Derek loves to get under my skin with his constant gloating about fucking Emily way more often than I do, and how he's always pushing for me to be denied longer. This story is actually very recent, and I was already pent up from 2 weeks of no orgasm. Derek snapped one afternoon with a gif of a guy in a chastity cage dripping precum everywhere, accompanied with a message like, "This is u. can’t even fuck your own wife properly.” Then he said “She likes my dates better too lmao" It pissed me off, especially since I know our dates are always good, so I responded that it was bullshit, she only likes them because of how he fucks her, not the dates themselves. He laughed it off in his texts and came up with a bet right there to see who could plan a better date, judged by Emily.
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The stakes he proposed were a pretty good deal in my favor to be honest. If I won, I got a full week with her all to myself, no Derek at all, no texts or visits from him, and as many unlocks and orgasms as I wanted, with full access to tease and play with her however I liked. If he won, he got her for a whole weekend, Friday night through Sunday, and as punishment for losing, I'd stay locked in my cage for an entire week after with no unlocks whatsoever, and her only teasing would be with her feet and lips on my balls, nothing else. I was a little hesitant, but the idea of winning and having her undivided attention for a week was too tempting, especially since she's been denying me more lately. We each talked to Emily about it separately, me first while we were cuddling one night, and she lit up at the idea, saying she loved us fighting over her like that. She of course agreed right away, saying how she loved being the prize and the judge.
I started planning my date immediately, already knowing she would love my idea: a fine dining sunset dinner cruise on a big boat, focused on intimate decor/vibes. Derek claimed he needed Saturday for his, so mine was set for Friday evening, which was perfect. A few nights before, Emily had me tied down for one of her edging sessions, her feet in my face while she slowly stroked my unlocked penis with oiled hands, twisting just under the head to keep me on the brink. That's when she casually mentioned she might have let a hint slip to Derek that could give him a leg up. She said it happened while he was fucking her the other day and asking her questions, and she blurted out that my date involved something scenic and romantic. My cock throbbed hard at the thought of her giving him an advantage like that, and she noticed, scrunching her toes right in my face and giggling. "Are you gonna convince me to go a whole week without him fucking me, baby," she whispered, rubbing her soles on my cheeks. I groaned and said that wasn't fair, but she just shrugged and said there weren't any rules against it.
Friday evening finally came, and I picked her up for the cruise. She looked stunning in a flowy sundress that hugged her curves, her hair down and a big smile on her face. On the way to the boat, she was scoffing at her phone, and I asked what was so funny. She said Derek had texted her something cocky, like how my date wouldn't be as good as his and she should look forward to an actually fun night tomorrow. Smiling, she put her phone away and said he was just being an asshole, then leaned over to kiss my cheek and tell me she was excited for our evening.
The date itself was amazing. We boarded this big ass boat that took us out on the water a bit before the sun was starting to set. We were seated on the top deck overlooking the water with a bunch of other couples, each at their own table (of course). There was live music playing softly in the background, a nice three-course dinner, and the sunset was really nice and lasted a long time since we were on the water and there was no land to obscure it. We talked about everything and it was super romantic but I wont bore yall with that part
During the sunset part of the dinner, while we were sipping wine and holding hands across the table, she slipped off one of her heels started teasing me discreetly. Her bare toes found their way to my crotch, rubbing slowly over the cage, enough to make me shift in my seat. "Feel that, baby?" she whispered, her foot sliding down to gently squeeze and roll my balls between her toes. She was grinning from ear to ear and had the most adorable sparkle in her eyes. I tried to stay composed since there were other people on the boat, but it was driving me crazy as she kept it up through dessert, occasionally using both feet and motioning them like she was giving me a footjob. She even leaned in at one point and murmured, "You're throbbing sooo hard baby… too bad it's locked up."
After the cruise, we walked along the dock hand in hand, then drove home still buzzing from the night. Once we were back, we cuddled on the couch, making out softly at first, her body pressed against mine as I held her close. It escalated a bit, with her grinding gently on my lap, but she kept it light, whispering how much she loved the date and how thoughtful it was. While we were tangled up in our bed, after we had done our nightly routine, she grabbed her phone and responded to Derek's earlier text, typing something like, "Don't be so cocky, tonight was amazing." She showed it to me with a wink after sending it, and we went back to cuddling and kissing until we fell asleep.
Saturday rolled around, and Emily headed over to Derek's place around 5pm, dressed in her pajamas. I didn't know what he had planned, and neither did she from what she told me. I didn't hear from her all night except for one text saying she'd be home late shortly after she got to his place, and then a short facetime about an hour after she left. It was a video of her in this super slutty outfit: a strappy top that didn't actually cover her boobs, just outlined them with thin black straps, paired with nipple-covering stickers, and a tiny black miniskirt that barely reached mid-thigh. Her makeup was heavy, with thick black eyeliner and mascara giving her a rave slut type of look. She said, "Do I look good? Derek picked it out for me, it was all laid out when I got here." She lifted the skirt slowly to show a minuscule thong that hardly covered her pussy, then did a twirl, the bottom of her ass cheeks peeking out before she blew me a kiss and ended it. I was instantly rock hard in my cage, leaking like crazy, and I texted her saying how insanely sexy she looked and asking a million questions about what was going on. Of course, she didn't reply, leaving me alone all night with my thoughts racing.
I spent hours pacing, playing with my cage through my pants, my heart pounding as I imagined what they were doing. I pictured her in that outfit, riding me reverse cowgirl with her ass bouncing and her panties pulled to the side, or on her knees sucking my dick, fingering herself as she worked me over. The hottest fantasies were of her tied up like that, helpless while I teased her, fucked her slowly, and tickled her feet while she went insane. But knowing it was Derek getting all that attention instead had me throbbing and frustrated, precum soaking my underwear as I tried to distract myself.
I actually watched her location on my phone for a lot of the beginning of the night, seeing that she stayed at his place for a while, before they finally left and went to a venue.
Finally, around 2 AM, she got home, already showered and changed into a different short dress that was still slutty but nothing compared to what she was wearing earlier in the night. She had that familiar post-fucking glow, her eyes a little dazed and satisfied. I started asking how it went, but she just jumped into my arms, wrapping her legs around my waist as I grabbed her ass with my hands to hold her up. We made out right there, her tongue dancing with mine as we moved toward the bedroom. I kept trying to ask questions between kisses, but she shushed me teasingly, saying, "Not yet, baby." Once we were on the bed, she pulled my pants off, giggling at the wet spot on my underwear from all the leaking. "Look at that mess… you must have been thinking about me all night." She restrained my arms and legs to the bedposts, then unlocked my cage. My penis sprang to its full four inches, twitching eagerly, and she leaned down to lay soft kisses all over it, dragging her lips along the shaft and using my precum as lube to make it slick.
"Are you sure you want to hear it, baby? Are you sure you can handle it?" she teased, her breath hot on my skin. I nodded frantically, saying yes please, and begging to know who won. She placed her soles right in my face, scrunching her toes playfully, then lubed up her hand and started with excruciatingly slow strokes along my length. " I was doing this to Derek earlier, except I needed both hands for his." My cock throbbed at that, and she began telling the story.
She said once she got to his place and changed into the outfit, they started drinking a little and did some stims. She climbed into his lap and sat right on his dick, making out like that without full sex, just his hard cock inside her as she rocked back and forth with shallow movements. Then he lay on his back, and she sat on his cock while giving him her feet to play with. He kissed and gently tickled her soles, making her squirm and giggle on top of him. I was groaning and thrusting into her hand the whole time, and she teased me that it was kind of like what she does to me, except he gets to tickle her feet and feel the inside of her pussy, which made me throb with jealousy.
Eventually, they were buzzed and took an Uber to the show. It turned out to be a concert with a less known group that Derek had introduced her to recently, and she'd gotten super into their music. They had VIP standing area right up by the stage, dancing together all night. She grinded on him a lot, her ass pressed against his crotch, and he even picked her up on his shoulders for a bit, both of them having a good time. After the set, they got to meet the group, who told Derek he was lucky and laid compliments on her, making her blush and feel amazing, like a reverse groupie where they wanted her instead. Then they left, grabbed a late bite at a steak house, and Ubered back to his place.
By now, I was begging her to tell me who won, if I got her to myself for the week. She didn't answer yet, teasing instead, "I don't think you even want me to yourself… you just want as many cummies as you can handle for a week." She kept stroking slowly, saying, "Imagine if you could just bend me over whenever you wanted and have your way with me," and I groaned, picturing it vividly. But she reminded me their date wasn't over and continued.
She kept those slow, torturous strokes going on my penis as she continued the story, her soles still in my face. "So we get back to his house, and I'm ready to fuck him right there in the entryway," she said, her voice low and playful. "This was over two hours before I got home, so there was plenty of time for him to have his way with me." She explained how Derek told her to freshen up downstairs while he got the upstairs ready, giving her a quick kiss and a smack on the ass before disappearing. She went to the bathroom, cleaned up a bit, refreshed her makeup and put on some perfume. Then waited down there for a bit until he finally called her up. When she walked into the bedroom, it was candlelit and smelled nice. Derek had cleaned himself up too for the impending fun.
They started going at it immediately. She told me she couldn't keep her hands off him, and made a grab for it right away, wrapping both hands around his shaft while dropping to her knees to take him in her mouth. She worked him up slowly feeling him grow until he filled her grip. Her hand mimicking the motion on my much smaller penis, giving it a few extra squeezes for emphasis, she said "I needed both hands just to handle him properly.." I groaned into her feet, my hips bucking as she threw in that size-based teasing, comparing how his cock stretched her lips while mine would fit right in.
They continued fooling around for a bit, shifting to 69ing on the bed, Then she focused on servicing his cock again, stroking and licking while he played with her feet. He kissed the arches and ran his fingers lightly over her soles to make her squirm and giggle. "I was so horny, baby, begging for him inside me, but he loved dragging out the foreplay, seeing how desperate I got. "
Finally, after what felt like an eternity of teasing, he told her to climb on top of him and keep her arms up on the headboard. She did, straddling him and gripping the wood tightly as she lowered herself onto his cock. She made sure to tell me she let out this delighted noise when he finally pushed inside.. Even though she was on top, he was the one in control, his strong hands on her hips lifting her body up and down effortlessly, setting the pace as she rode him. After a few minutes of that, they switched positions to her favorite. She got on all fours with her ass up while he stood at the edge of the bed and fucked her from behind. He held her hips and slid his cock in and out too slowly for her. She showed me exactly how slow it was by mimicking the speed with her hand on my penis, long, drawn-out strokes that had me whining and thrusting. During this, I hit a hard edge and she giggled, pulling her hand back completely, teasing me about how I wouldnt even be able to keep up with his slow pace.
She went on, describing how she was begging him to go faster, whimpering as she grasped at the sheets with her hands stretched over her head. Her legs were shaking uncontrollably, and she said it felt so good, like she was in a trance.
Her begging went on for a while longer, with him giving her ass some sharp smacks that left red handprints and teasing her soles lightly with his fingers. She was really losing her mind when he started to pick up the pace a little, driving his cock into her deeper with each thrust, and asked her if she wanted to cum. She groaned out an enthusiastic yes, and then he asked if he was going to be fucking her this week, and she groaned out another enthusiastic yes. I hit another edge right there, my penis twitching wildly as she described it, so she stopped stroking for a second, leaning down to give the head some soft kisses while it bobbed in the air. I groaned out, "Oh god baby… so he won?" More precum leaked from the tip, and she giggled, a bit of it dripping onto her thumb as she teased the underside lightly. "Yes baby, your date was amazing, but getting the band to drool over me was just soo perfect. It made me feel like an actual princess."
She kept going, saying he picked up the pace even more, fucking her faster now as he asked if she would be able to handle a week without his dick if he made her. She grunted out, "No please!" her words shaky and desperate. Hearing this was driving me insane with jealousy, my mind flashing to images of her submitting to him like that, and she was just teasing me with one finger the whole time at this point because I was so worked up and so close to the edge I couldn't even take her two fingers under my head. So she just stroked my frenulum with that single finger, keeping me hovering right there. And then he asked her what my penis was going to be doing, and she told me her response came one word at a time, separated by his thrusts: Locked… up… all… week. She said he kept fucking her hard like that, holding her hips and pulling her back onto him while she threw her ass up into him, meeting every stroke until he made her cum her brains out. The orgasm lasted like two minutes as she shook, her pussy clenching around him. He fucked her all the way through it, not stopping until she was completely done, just lying there spent and panting on the bed. After a moment to catch her breath, she got up and gave him a blowjob, sucking and stroking until he came all over her face.
The whole time she was telling me this, I was just thrusting up into the air, trying to get more stimulation, but only her one finger was there teasing me, barely enough to keep the edge alive. I was begging her, "Baby please let me cum, please I can't take it anymore." She said, "But you lost the bet, sweetie, so you get another week in the cage, this time with no unlocks." She grabbed the cage and placed it over the head of my penis, pressing it down and threatening to make me soften, and I whimpered, "No baby please, no oh god please just let me cum." Then, scrunching her soles in my face, she pulled the cage off really quickly (and in hindsight with a goofy theatrical flair) and started jacking me off with her full hand this time, full speed and firm grip. I lasted probably five strokes before I started cumming, a massive load dribbling out of my penis and down the shaft. I moaned super loud, my whole body tensing as she kept stroking me all the way through, overstimulating me for some post orgasm torture, until I went soft and was gasping for breath. She wiped my penis off gently with a wet wipe, put the cage back on, and untied me.
Then we just cuddled for a bit and made out and got ready for bed, where we fell asleep cuddling some more.