Maybe Something Different

She couldn't help herself today. We made it 8 days. I wasn't begging or asking, but she wanted to see me get off.

 

I'm kind of giving up on things ever changing. It's funny how many times I've expressed a desire to wait longer, and she agrees to do that and that it's better with me waiting. But, after a while she can't help herself. Inevitably she will start making me cum every day; often more than once. It's fine, but I see how silly my ideas are that this will ever turn into something more.

 

The last time I posted I was basically accepting that chastity and longer term denial will not happen with us. In the period before that post and a bit after, I kind of lost sexual interest due to being frustrated. After the third time messing around and me being nearly unresponsive, she really was bothered and wanted me to be honest with her about what was going on. I don't like telling her that she didn't do something right, but she really wanted to know what was up. So I told her how she always says we will be doing longer terms of denial and how much better it is that way, and then she gets really horny and into me and just wants to make me cum day after day in a row.

As of now, I haven't had an orgasm or a ruined orgasm since last Thursday. I think it's too soon to say anything changed permanently, but this is something that has never happened with us before. She seems to be really taking it seriously. Originally she was going to make me cum tonight, but then she said she really wanted to go until Friday. Now, she's not sure what will happen Friday.

She's been getting plenty of attention, and, though there's been no full or ruined orgasm for me, she has milked my prostate. After 2-3 days I get very uncomfortable. She is helping get rid of built up fluid, but that's all. Our first one was Sunday, and we had the second one tonight. Tonight was thicker, and she is getting so much better at doing it. She edged me earlier in about 20 seconds. Then she changed into pajamas and told me to bring her the wand, take off my pants, and get on the floor. Soon she had the glass wand in my butt, and I was starting to drip. When the thicker stuff started falling out I was making moaning noises and told her it was really frustrating. She said, "Oh, I'm sorry, but not really." And she kept pushing it in, twisting it around, and pulling it out.

 

I don't have a hard time sharing my feelings with her, but I didn't want to tell her how she should go about doing this once we start. I think I was also always a little afraid I'd get what I wanted. That is great advice (IP-Chaste) to express my appreciation. I've been doing that in direct and indirect ways.

She's starting to embrace it. Yesterday I texted her that we just broke a record of one week without any kind of orgasm (ruined or otherwise). She responded, "Well I want to make it longer than a week." She said she wants it to be 10-14 days. When I heard that I was really surprised, and then I realized that this Friday was supposed to be a ruined one. So I asked, and yeah, she is kicking around the idea of giving my a ruined o after that long of time. She said the full one would be after another two weeks or so, but she's not sure if we'll wait that long.

We were intimate so frequently this week. Last night was really hard for me. I initiated sex, and she really got into it. I'd told her I like talking during sex, and she started saying things to me while we were in the middle of it. It was great feeling her cum a few times. However, because she had milked me on Wednesday, though I was extremely desirous, I wasn't having a hard time keeping away from the edge. So I could really push it like she wanted. But after a while, she really did motion me off. That's something very rare. She always wants me to ejaculate in or on her after sex. I laid down, and she started playing with me. I told her how good it felt and how hard this was to do right now. So she started getting me close, but nothing more.

I was talking to her about how this is starting to mess with my head having it become so real. She lovingly said, "I'm sorry it's hard right now, but this is continuing. You're going to love it."

 

I want to hold off on the milking, but the urge to pee and discomfort I get after 3 days of teasing is so bad. I’m so frustrated and ready for more once she finishes milking. She didn’t used to like doing it, but now she said she’s ok with it and likes parts of it.

 

Last night was an accidental ruined o. She didn't realize how close it was, and I couldn't get the nerve up to warn her. Funny thing was that once she took her hand off and it started shooting out, she got so worked up that she grabbed it again. It was a strange feeling. There was a lot of build up I could tell, but something went off in those brief seconds before she put her hand back on it. So, I lost the urge to keep ejaculating and didn't get the huge sensitivity. There was still a huge thick puddle on my stomach.

This morning I was not really feeling the desire to wait much at all. She came walking into our bedroom when I finally woke up wearing these new tight yoga pants and was saying how good they fit her. Obviously knowing what she was doing, she did a goofy little dance turning around so I could see all of it. I wanted her right then and there, but she wasn't having it.

I had asked her how she felt now about this going forward. She's full steam ahead with this new schedule, and initially wants to do twice a month regular orgasms working toward one a month. She did say that is just a rough estimate, and it's more fluid. But, if I was wondering, that was how she hoped it would develop going forward. I was really not into it, but I'm willing myself to comply. Then, because she had to go do things, she gently demanded I lock up. She said something like this before leaving, "Look, you wanted to do this longer and didn't like when we did it my way. Now you are getting what you want. Be good while I'm gone, not that you have a choice really. Loves you!!"

I'm excited and intimidated by this at the same time.

 

My post elsewhere about milking vs ruining led me to ask my wife what she felt about the two.

She does enjoy giving me a ruined orgasm. She likes being able to feel and see my erection during it, to see how much pleasure I'm getting, and watching the ejaculate come out. And, because it's not time for a full orgasm when she is doing this, she appreciates that my mood is not usually going to drop as much. However, it still drops for us and sometimes a lot. We'd had more success with it in the past, but lately the drop is worse.

For milking, she said it is a really great tool and that it got a lot easier the more she did it. She said she doesn't really find the act of doing it physically exciting though. She doesn't touch my penis except occasionally, I'm not erect, etc. It used to seem too medical to her, but she's not put off by it anymore. She does think it's exciting to see how much build up is coming out and the noises I make. As I'm so into the submissive feeling, I asked her about the sense of control. She likes it, but it's not as big of a deal for her. What she likes most is knowing that there is no relief to my sexual tension, and so I will be just as into her, if not more, right after the milking. The last time she milked me was insane. She'd finished, and we were lying in bed. I was completely hard and felt like I was on the edge of orgasm though she was doing nothing to me. I wanted sex with her so badly at that point and to feel her body all over. I'd never felt such an urge to have her.

I think if we could learn how to do ruined orgasms without a drop in sexual tension, she would prefer those. In the past she's even said, "I never thought I would like doing these as much as I do."

 

Yeah, you really have mastered it. I don't think we are giving up on it yet. Whenever the next time is that we attempt it, I'm going to try to get her to let go earlier. I'd like to see how she'd feel about being able to do it perfectly.

Btw, I'm still enjoying your journal entries, and it's good to hear from you on here again!

 

It’s something how much easier it is than it used to be dealing with the waiting. It’s been a hellishly busy fall with nearly 40 hours of work on weekends alone occasionally. The whole tease and denial makes it easier somehow. At any rate, I’m finally getting a relaxing weekend and getting back to some video games. It’s been too long since I last played Dark Souls 3.

 

This weekend she couldn't stand waiting for me to cum any longer. She was bent over our bed. We had been having sex for about 20 minutes, and I knew I was close. So I pulled out trying to cool down. She gasped "No!! Cum inside of me. Don't stop!" I wasn't going to argue. I started going again, enjoying every sensation. As I felt the first bits of climax starting she began to contract rapidly around me. In response it was like I had a mini orgasm and then a deeper one started that about made me swoon. It was quite powerful.

So, after this weekend, we began today with me getting locked up. It's starting to make me feel a little different at this point. She's never been so into keeping it up. When we were at our separate jobs, I was texting her about how this is starting to get challenging since it's moved past the elation of the first week. She responded, "I know this is hard but the spot we were in this weekend compared to last is soo much better. I feel soo much more connected to you when we do this"

Last night she was playing with me and said "It's going to be 7 more days until you get another ruined orgasm. At least 7!" I'm going to try to be as encouraging as I can be now.

 

Funny, the more we've done chastity consistently and the longer I'm waiting, the more bored with it I've become. It's also making me less into her. She came into the bedroom tonight, and I knew I'd not be able to respond to her. So I just sort of indicated I wasn't into it at all.

 

We stayed put this year for Christmas. It's been wonderful not driving across country in potentially hazardous conditions. With all the extra time, we've been trying to get into the bedroom a lot more often. A couple of days ago was one of those instances where both of our bodies seemed really in tune with one another. I wasn't about to let it all end in just a half hour or so. So I kept stopping whenever I was getting near orgasm, and then we'd just spend a minute together looking at each other and making out. After an hour of that stop and go love-making, we finally quit. She went to the bathroom, then came back in and made me erupt all over her hands.

The day after that, she told me I have to behave and not do things without her on break. That got me thinking about how intense things are when we start playing with orgasm control. So, yeah, it's another one of our on cycles for our version of chastity.

I'm pretty excited. I asked her if she would get into like a 69 position to show herself off to me while she played with herself. I think she's going to do it. In a spontaneous way, this has happened in the past, but this has the addition of her express intention to tease me with it. I wanted that tonight, but she said she is going to make sure it's looking its best before she does it.

 

Yesterday began with her grinning about how automatically hard I was for her in the morning when she pulled the covers off me. Wasting no time, she started fondling me. She was trying to be careful to prolong it a bit more. It wasn't much use. When she really gets into touching me, she starts to make little moaning noises. She was doing that when she'd stop or slow down and hold it at the base or by my balls. It maybe took five minutes; I thought she was going to ruin it. Instead, once she could tell the inevitable was about to start she recommenced stroking it and for quite a while after the first few jets. We stayed in bed, and I tried nuzzling into her. Funny thing, I'm overdue for a haircut, so she kept her hand on top of my head to keep the hair out of her face. I was laughing and so faced the other way while she spooned me.

That night, after we ate our dinner, I started reminding her about the exhibition she had hinted at doing. She did it! I watched her play with herself until I couldn't just watch. I pulled her to my face trying to get to the wetness I'd watched her build up and got her anus instead (she slightly moved last second). She pulled back and then used my erection to help play with herself. Eventually, she mounted me facing away while I rubbed her anus. I didn't end up having an orgasm; this was way more about her anyway. After she got off of me, she lied on her back and I rubbed the tip of my penis in between her buttocks while I massaged her clit with my thumb. I've never done anal sex with her, but she gets so excited about my penis being near her ass. I did put my finger in while giving her oral, but she's not usually into that. I did it for a while and then she motioned for me to pull my finger back out. She said she's definitely going to try showing herself off to me like that again and did enjoy the sensation of being touched back there.

She gave me the green light on our new strapon harness. Our old one has been broken for ages. I got a unisex one. I've wanted to try doing that to her. She picked a new dildo for it too. It's this curved one that's purple and not too long and not too thick (like 7" long and 1.5" diameter). I have a surprise coming though. I got something a bit bigger in addition to the purple one. We've never tried anything inside her that is larger than me. I don't know if she'll like it, but, if she doesn't, I'll try to convince her to use it on me.

 

To make the last post have something to do with chastity, she’s not mentioned me locking up but once, at the start of our break. She goes back to work much sooner than I do, so I wonder if she’ll start to use that while she’s gone during the day.

I don’t put it on anymore unless she asks me to do it.

 

We had some fun twice today, but it was only her touching me (no orgasms). She said she hadn't recovered quite yet from the riding she did. I had a big work load, and she promised to give me some fun at certain key points of progress. I love how much she likes to touch me.

I dropped her a few hints about the surprise dildo that was on its way. I let her know I took the time to measure myself so she'd be getting something bigger. She didn't seem thrilled by that. She said it was already a stretch to have sex. It almost always takes a while for her to get relaxed no matter how wet she is. I am afraid she's going to say no when she sees that thing. It's not that huge, but I think its not being me will make her reluctant to accommodate the size.

Later, when she went to bed ahead of me, she texted me asking, "Why does it excite you so much to get that for me?" My response, which I think is part of the truth, is that I want to see her get sensations she's never had before from penetration and that I think it will be hot for me to have to use it while not getting anything myself.

At the end of the day, I will be fine being the one who ends up getting fucked by it.

 

I've had no orgasm for the last 3 days, but we have been intimate with each other at least twice a day. Today the new harness and the smaller dildo arrived. She said that one would be perfectly fine for me to use. I had to try on the harness. It seemed to fit fine; I've never tried it in action though. I may get practice tomorrow. She said MAYBE I would get to use that on her tomorrow, but I wouldn't be allowed in. She also said MAYBE she'll use it on me.

The thing is just between six and seven inches and not all that thick. It might still be a pleasurable change for her given the new shape (it is very curved). The one that is bigger than me is coming tomorrow. I'm hoping to use that one on her. No idea why, but the thought of seeing her filled a bit more than I can manage is really hot to me.

 

The anticipation for me is building. We had afternoon cuddles for like 5 minutes. Now she’s showering. She asked if I needed to put on the toy. I didn’t really respond. She’s going out for some errands after her shower. I’ll see if she tells me to lock up.

It has been years since she’s pegged me. Unless she’s going to be especially teasing, I’m going to be cumming so hard tonight.

 

She just said, “stop lollygagging and put it on. It’s day four and it’d be irresponsible for me to leave you home alone and unlocked.” She was grinning at me when I handed her the key. I asked her if she ever thinks about it still as something crazy that I’ll lock something around me and give her the key. “Oh it’s crazy. From the first time you brought it up I thought it was. But if you want to give me that control, hey that’s on you.”

 

I got pegged last night with the new thinner but very curved dildo. Finding the right position took us a while. It ended up that her lying on me between my legs was the best. It was such an odd sensation. It has a smaller tip then what we used in the past, but the curve made a difference. She touched me lightly initially before we settled into missionary. I touched myself for a while, but once she found the spot and rhythm I just hugged her close to me.

It was feeling great, though it took a while for me to enjoy it, and I was expecting a prostate orgasm. The new dong had other plans. For me, when I'm getting closer from anal, it builds and drops several times before orgasm. It was building up to what I thought was the orgasm when it suddenly just left me with very little pleasure as I felt my semen spurt and dribble. It went all over us. Though the closeness to her while it happened was very lovely, the let down at the end was so frustrating. I was putting her hand back on me soon afterwards wanting her to finish me again with her hand. She touched it lightly and then left it be. This was like the most ruined orgasm I've ever had. Taking a prostate milking is much easier because there isn't the ecstatic build up to let down. She seemed to be hiding how amused she was that it was frustrating.

It makes me wonder if I just have to adapt to the way this one works in order to experience it in a more pleasurable way, or if instead it will just give me that ruined orgasm experience every time. If we keep playing the waiting game for a full orgasm, I think she might make use of it in between the full ones. She said tonight that it wasn't an uncomfortable feeling to her like it had been before and that she did want to do it more often to me. I heard her even moaning lightly when she was grinding it into me at some points.

Before the pegging, I got to try out the bigger new dildo on her. She was shocked when she saw it and didn't think it would go in to her. I asked her if we could try, but she wouldn't say yes or no. She played with me for a while to get in the mood. Then she pulled me up onto her and used me to rub herself, finally pulling me into her. We had sex for a while, and she said I could try the new one out if I wanted. I worked it slowly in and was gentle with it. I tried licking her while I did that as she has gotten off that way from more modest sized things in the past. She stopped me after like two minutes. She's not a huge fan, but she's curious enough to say we can try it again some time in the future. It did feel good, but also painful I guess. Afterwards she said she felt slightly embarrassed that it went in.

To say something a bit more chastity related, she wants me only to orgasm fully four times in January. I'm guessing once a week. Right now it sounds really hot, but who knows how long this high will keep up. Oh well, I'm having a ton of fun with her so far on our break.

 

Last night was really good. After the prior day’s foray into new sex toys, oral and intercourse were wonderful. She had two orgasms and then she slowed herself down while holding my erection to ask if I could wait longer. I said yes. She smiled and then gave me such an intense orgasm. I’m fortunate not to feel a drop as some describe.

She’s thinking up resolutions. I said, “I’m only thinking up resolutions that sound hot and are arousing to tell you about.” She shook her head smiling because she knows that’s true.

 

New territory for us tonight, she asked me to help coach her to ruining my orgasm. It was quite frustrating but hot. She did two in a row. She played with me normally to edge me several times. Then I told her to start squeezing and releasing the head quickly. There was the hang time and then the slow trickle. I want to know what she thought of it. We had to exit bedroom time quickly after that and haven’t talked much about it. I’m still coming down off the frustration.