Trials and Tribulations of ChasteDilf13

I've posted a few status updates on this subject in the past and decided I may as well begin a Journal instead. I'm not exactly sure where I'm ultimately going with this, but for now I wanted to write about my recent experiences with my loving Wife and now Keyholder.

Backstory

Except for the fact that she keeps me caged, our relationship is pretty normal. We've been together for about 14 years, married for the last 6, and have two kids. We both work from home so we get to see eachother most of the day. About two years ago I suggested we try chastity. We had a pretty good sex life and would fuck regularly, however I would also masturbate frequently and I found I didn't give my wife the attention she deserved.

At first she was timid and had difficulty adapting to the dominant role of a Keyholder. Over time she became more confident, and got a taste for what a chaste man could do for her. I think she's now at a point where she knows what she wants and isn't afraid to take it.

When we first started our journey she felt bad for me being caged, unable to achieve orgasm. She'd let me out to orgasm every few days, basically our regular sex schedule but without masturbating in between. She found that as this went on my stamina continued to decrease, almost to the point where I could barely enter her. We slowly began to experiment with new toys and she's found a few that she really likes, that could give her bigger and more frequent orgasms than I could with my cock. Over time she's also found that I don't *need* to orgasm to be happy and have a healthy sexual relationship with her. She can keep me denied and we're both better for it.

Today my wife enjoys nightly or bi-nightly sex, while I'm kept caged. She has me oil and massage her soft body, then bring her to climax repeatedly with manual stimulation and toys. She'll reach orgasm 5 or 6 times a night, until she's just spent. In return she'll give me frequent Tease and Denial sessions. My T&D sessions usually involve me being restrained and released from my cage, then edged repeatedly. Most of the time I'm left to cool and and returned to my cage. My KH will usually edge me 2-3 times per week.

More recently my Keyholder has begun to come up with more creative ways to make edging more challenging and fun. The other day (we both work from home remember), she made a point several times to remind me she was wearing my favourite thong and no bra. It's amazing I got any work done that day.

Which brings us to the reason I started this Journal. My Wife/KH decided to theme our most recent T&D sessions. She dubbed them the Sex Olympics. I posted a few status updates about this but decided that a more detailed story may be fun, so here we go.

The Sex Olympics

Near the start of the Rio Olympics, my wife mentioned to me that she wanted some attention that evening. It had been 2 days since she got off and it was time I fulfilled my duty. She said that in the evening she'd have a special challenge for me afterwards.

The evening started off pretty normal. She got naked and lied on the bed. I began to oil and massage her shoulders and back. She began to relax as I worked my way down her lower back to her legs and thighs. I tell her it's time for her happy ending as I begin to gently massage her lady parts with my fingers. I use the dildos, slow at first then more intense as her orgasms rack up. She'll usually finish with the biggest toy, an 8" dildo with a wide girth. After she's spent she tells me to lie on the bed.

She grabs the wrist straps and restrains me to the bed frame. She covers my eyes with a blindfold and tells me I've qualified for the Sex Olympics, and tonight was my first group stage round. If I ultimately make it through to the Gold Medal I'll get a special reward.

She removes my cage, oils my cock and says I need to withstand 100 strokes in 3 minutes. At this point I'm so horny I'm shaking. The clock rolls over and she begins stroking. She explains this is only the first group stage challenge, and if I pass I get into the quater finals. She starts stroking faster. She says the challenges will get harder at each level. I tell her to stop several times, but ultimately made it in under 3 minutes with a little time to spare. She was kind and mostly focused on the shaft instead of the head. She gives me a kiss and says it's time to clean up and put my cage back on. Group stage complete!

A few days later she requests her normal attention; a full body massage with happy endings. After a massage and as many orgasms and she can handle, she says it's time for the Quarter Finals. It's been 10 days and 4 T&D sessions since my last orgasm. I was wound right up. She has me lie on the bed, cuffs my wrists together and removes my cage. She covers my eyes with a blindfold and tells me to keep my hands above my head. She generously oils up my cock, then climbs on top so her pussy lips are massaging the length of my shaft. She reaches down and firmly grabs my cock with her had and presses it against her pussy lips, then starts grinding forwards and back. She says welcome to the Quarter Finals while she's playing with the head of my cock. "These will only get harder". I could barely hold it together, but I finished the 100 strokes with only seconds left. She congratulates me and gives me back my cage, she says I made it to the Semi Finals!

The Semi Finals were tonight, and she wasn't lying about it becoming more difficult. She has me come down to the living room where she's wearing her yoga top and a sports thong. She tells me to grab a beer while she puts on Dance Central (If you aren't familiar, it's a dancing game for Kinect). She does a few of her favourite songs until my eyes are just glazed over with desire. She turns off the game, rolls up the carpet and turns on a TV show. She kisses me gently, then tells me to sit on the floor next to the sofa. She sticks the suction dildo to the hardwood floor, bends over and starts fucking it while I'm told to watch. She rides herself to near climax then reaches for my key... my head is spinning!

She removes my cage and places the biggest suction dildo on the floor in front of me. She oils up the dildo and slowly slides down onto it. She then leans forward and says I've now started the Semi Finals, Good Luck! She takes the head of my cock in her mouth and grabs my shaft with her hand. She begins riding the dildo while simultaneously stroking me and giving me head. I watch as I struggle to maintain my cool. I close my eyes several times to focus on my breathing. I tell her to stop several times as I'm on the edge, she keeps riding the dildo in front of me.

It felt like we just started and she lifts her head up and says I made it to 100 strokes, she's proud of me. She really did her best to make it as difficult as possible. I thank her for the amazing experience then lift her onto the sofa. I return the favour by using my tongue to massage her clit while I fuck her with the big dildo. She's so worked up that she comes hard over and over. She's spent and tells me to go clean up, I made it to the Finals, I'm going for Gold!

That's all I've got for now! I finished the Semi Finals not 2 hours ago, so I expect it will be another day or two until the Gold Medal round. She says if I pass I get a special reward. I'll update this journal after our next experience in the Sex Olympics! And for anybody interested, there is a pic of my Wife/KH in her outfit from tonight in my gallery.

Thanks for reading!

 

Gold Medal Round

Yesterday my Keyholder decided it was time for the Gold Medal Round. She had been teasing me all day, asking if I was mentally prepared for the final test. She said I'd have a "special reward" if I passed, so I need to be ready. She had me so worked up I was legitimately nervous!

When we sat down to relax in the evening, my Keyholder wanted a back rub. She asked me to sit on the sofa and she sat on the floor in front of me. She took off her top and told me to massage her shoulders. After about 20 minutes she was starting to feel really relaxed and leaned her head back into my lap. She says her chest needed some attention. I put some more oil on her and begin to massage her beautiful breasts. She's moaning and says this just warm up for the final. After a few sensational minutes she instructs me to stay on the sofa while she goes upstairs.

I'm called up a few minutes later. I walk in the bedroom and she's wearing a short mini skirt, knee high socks, a sheer white blouse and crotchless panties (Pictured in my gallery BTW). She's pulled the dresser from the wall with her favorite suction dildo stuck to it. She takes the key, undoes my cage and tells me to sit on the floor in front of the dresser. She grabs restraints and ties my hand behind my back. She stares me down while she lubricates the dildo, then gets on all fours and begins to slide herself onto the toy. She flips up the top of her skirt so I can see the dildo entering her while her ass highlighted by the crotch-less panties. She leans forwards and takes me in her mouth and I instantly say stop, I'm near the edge and she hasn't touched me yet!

She continues to fuck the dildo while I try and gain some composure. I'm only semi-hard, yet I feel like I could cum with the slightest touch. I take a few deep breaths while I watch her continue to fuck the dildo. I manage to regain some composure and she again takes me in her mouth and starts getting me hard while she fucks her toy. It only takes a moment before I'm rock hard. She pushes me backwards, gets off her dildo and sits on me. She grabs my cock and touches it to her pussy, I instantly yell stop! I squeeze my PC muscle as hard as I can, but I can't bring myself back from the edge. She lets me ruin and watches as my cock drips cum. She laughs and says she didn't even start the challenge yet, all this was just warm up! She's feeling generous so she'll consider this a false start, but there will be a penalty...

She unties my hands and lies on her back on the bed. She instructs me to get her off. I kneel down and begin to lick her freshly shaven pussy. I massage her clit while fucking her with the suction dildo. She comes several times and is in the throws of yet another orgasm when I pull out the dildo and grab the bigger toy. I can feel her cumming hard as I slide the biggest toy into her. She comes twice more with the big dildo before she says she can't take anymore. I've lost track of how many times she came, it was at least 5 times.

She lays still to relax a moment and looks over to realize I'm still rock hard. I don't know if it was out of pity, or kindness or she just wanted more, but she tells me to lie on the bed. She again restrains my hands above my head, then climbs on top of me. She grabs my cock and begins to rub the head against her wet swollen pussy. She asks if I'm ready, I only get one false start. I'm as ready as I'll ever be.

She slides down my cock and begins to slowly rid me. She doesn't just gyrate in place, but brings herself up and down to ride the entire length of my cock. I don't know how many "strokes" she was going to require from me, but I had to say stop several times so I could bring myself back from the edge. As time went on I needed more frequent stops to stay composed. At one point she climbs off and I thought I had made it, Gold Medal! She says the final 25m is the hardest part of the sprint, then pulls off her crotchless thong and turns around to ride me reverse cow girl. She leans forward so I can see her travelling the length of my cock. I closed my eyes to focus on my breathing and was just about to say stop when she climbed off, she said I finally made it.

She gives me a kiss and says she was proud of me, but that I'd have to be penalized for the false start. Her intention was to give me my reward the next day but that instead I'd stay denied until Saturday. I was relieved and thankful to my Keyholder for the generous terms.

So I guess that's it for the Sex Olympics until my Awards Ceremony. I'm not quite sure what my Keyholder has planned, but I suppose I'll find out this weekend! Thanks for reading, I hope you enjoyed it. I'll be sure to write about any future challenges my Keyholder decides to put me through! Thanks!

 

I finally got around to writing the third and final part of our Sex Olympics; My Reward! You can read the final chapter on Tumblr:

https://chastedilf13.tumblr.com/post/150700672312/trials-and-tribulations-of-chastedilf13-part-3

 

Yeah, 10/10. Would play again

 

I'm currently in the middle of a month long lock-up. Yesterday, my wife finally began to feel better after being sick for weeks. She went to bed a little early and said she wasn’t yet feeling 100% and wanted to catch up on her sleep. I wished her good night and she went off to bed.

When I came upstairs an hour or so later, she was still awake. She told me to get the harness and dildo, and to bring some lube. I excitedly complied! I warned her that after 2 weeks in lock-up there’s a chance I would cum in my cage, but she didn’t care if I ruined.

She pulls off her covers and lies on her side, and pulls her top leg towards her chest. I start to rub her pussy with my hands and slide a few fingers in her. Not only is she dripping wet in anticipation, but after several weeks of being sick without sex she’s small and tight. I can just get a few fingers in her.

She begins to moan and says “fuck me”, so I lube up the dildo and slowly slide it into her. She moans as she gets used to its size while I slowly work up a rhythm and gently massage her clit.

After a while she pushes me off and turns around so she’s on all 4s. She leans onto her elbows and sticks her pussy up in the air. She says she wants to get “railed”. I grab her by the hips and slide the dildo into her, and start thrusting. I can feel myself getting more excited as her moans intensify.

As her excitement grows I can feel myself loosing control. Even with my cock caged and ignored I can’t maintain control and start dripping cum onto the bed. Luckily my cock is irrelevant and I continue to pound her tight pussy until she cums hard on the dildo and collapses on the bed.

She eventually notices the wet spot on the bed where my cock dribbled, and asks if that was me or her. I embarrassingly admit that I came in my cage before she did. She laughs and says “And that’s why you fuck me with a dildo”.

--

This post is mirrored on my Tumblr: https://chastedilf13.tumblr.com/

 

Its been a long time since I've posted and I've figured it's time for an update!

My lockups are usually 2-4 weeks long, but recently my lockups have been shorter than normal. Life's been a little crazy the last few months, and it's been interfering with our bedroom time.

One of the things keeping me busy is that I've been spending hours every evening after the kids are in bed to renovate our basement. I'm making it into a MomCave for my wife. I only have a few hours a night, and there was a significant amount of work to be done. I've spent about a month and am only now finishing the drywall. I still have to prime, paint, install trim, subfloor, laminate, resurface the staircase, and install the new pot lights.

So this week my wife says that she's now anxious to have her basement finished, and said that my lockup will end when her basement is done. After more frequent releases, my current predicament is a little daunting!!

Never failing to keep me on my toes, my wife also suggested that once the basement is done it would be a great canvas for a photoset, and she even has a new outfit for the occasion.

I'm so happy to be married to such an amazing woman, and to get to serve her. It looks like my basement Reno timeline went into overdrive!

Thanks for reading!