My desire for chastity alongside her requirement for penetrative sex

Hi all, I’ve been experimenting with chastity alongside my wife for some time now. I’m usually locked up around the clock, and she desires penetrative sex roughly once a week. Typically, I am permitted to ejaculate frequently, and often she allows me an extra 1-2 masturbation sessions each week as well. This means I achieve about 2-3 orgasms weekly while she gets one. Previously, we experienced two separate months where I was denied orgasm, which I really liked, and I believe she did too. I’d like to move further in that direction and plan to tell her soon that I want fewer orgasms than hers and not always ejaculate during intercourse. To be honest, my ideal scenario is being locked up for long stretches while licking her until she cums daily. However, the issue is that she CANNOT cum from oral sex alone. I’m unsure why since she clearly enjoys it, but she invariably asks me to “come inside” so she can reach climax. I suspect this might be because she rarely masturbates (she insists she has never done it, even back in her teens…). So, I don’t want to top from the bottom; if she prefers PIV sex, that works for us. The main challenge is that if I go longer without ejaculating, I may struggle to maintain stamina! Even after just a few days, holding back my orgasm until after hers becomes quite difficult. This is especially true when she wants rough or fast intercourse, or in positions that feel particularly good for me. My self-control is decent, but it’s still tough not to lose control. Since we use withdrawal as our birth control method, I really can’t afford to ejaculate prematurely lol. So, I’ve been weighing a few potential solutions:

1. Wearing a condom to last longer, specifically one with lidocaine. The drawback is that she absolutely HATES the sensation of condoms. It feels different to her, and she simply refuses for me to wear them.
2. Using a penis sleeve instead of a standard condom. I purchased a penile sleeve before but unfortunately (being quite horny at the time) I got one that adds 2 inches in length, which was too long/big for her. It might be possible to try one that doesn’t add much size and acts more like a thick condom, though it would still likely not feel exactly like natural skin, presenting a similar issue to condoms.
3. Using a strap-on while remaining locked up. Yes, this is largely fantasy territory. I doubt she’d enjoy it at all. If the sleeve has a 1% chance of her liking it, this option stands at 0.1%. She has never bought or used a dildo in her entire life.
4. Ejaculating quickly to get that out of the way, then performing oral sex as foreplay until I become erect again, followed by PIV where I can last longer. This could work well, though obviously, I would be ejaculating (ending orgasm denial), and honestly, I don’t think I’d be very keen on continuing afterward once I’ve come! (Also, not entirely sure about the pregnancy safety of this approach…)
5. Pressuring her into giving up PIV sex forever, so it’s just me licking her until she learns how to cum from oral alone, after which she can finally toss away the key and I become her devoted slave as seen in those chastity captions! (just kidding) tl;dr: I’m at my wit’s end. I’m 99% certain she wouldn’t mind long periods of orgasm denial for me, but it would mean I struggle to last during sex, while she requires hard, prolonged PIV with her actual penis in order to cum. PS: Just wanted to mention that she actually enjoys it when I manage to ejaculate in under a minute during a handjob and sometimes likes doing a 30-second countdown. I think we would both really enjoy “PE (premature ejaculation) training” together, but I can’t sacrifice my stamina for those once-a-week sessions when she needs them!

My wife easily cums from me fingering her, so that's not really a problem for me. In fact, it's rare for me to actually make her cum with my penis alone because it just takes longer doing it that way. However, I do love the idea of making her climax through penetration. We've very (VERY) tentatively mentioned getting a strap-on (yes, they are made for men too) specifically for this purpose. At least in my mind, it seems like quite a bit of fun. Have you discussed it with her?

She isn't interested in toys unfortunately. I've given her vibrators and the aforementioned sleeve before but she didn't care for them. Sadly, she also can't cum from oral or fingering either. Maybe it's my technique, but she always ends up asking for my penis anyway.

She sounds very much like a younger Mrs. Groove regarding masturbation habits and the lack thereof. To this day, she dislikes condoms or any artificial appendages. So here are some ideas to consider. There is a book available titled “she comes first”. It’s not bad, but perhaps you can find something there to improve her responses to oral and fingering stimulation. Consider numbing cream for you. There have been several discussions on this forum about how to use it effectively. Try a ruined orgasm for yourself by giving her PIV immediately after; you will stay hard with little chance of coming again. Regarding her masturbation habits, it took Mrs. G several years of well-timed conversations before she was willing to let me watch her in the act. She has learned over time that this is a major turn-on for me and a great option for t&d (tease and denial). I have consistently reassured her that watching her body move is one of the most beautiful experiences I’ve ever witnessed. It doesn’t happen often, but when it does, I embrace every moment. She only uses her fingers; no extra tools are necessary. We cuddle a lot afterward, and I brush her hair. Good luck and be patient; it sounds like you have plenty of opportunity to discover new ways of being together.

> Tongue+groove wrote: ↑Fri Jan 10, 2025 11:01 am > As for her masturbation habits. It took several years of appropriately timed conversations for Mrs. G to be willing to let me watch her in the act. I mentioned this to her as well, but I don't think she's fully convinced yet:D How did you manage?

Be patient, gentle, reassuring, admiring, complimentary, and above all loving. There isn’t really one right answer here, but a few ideas come to mind. Many women can be quite physically self-conscious. Sometimes while she is changing, ask her if you can watch her. Let her know how beautiful her nakedness is and how much you love looking at her. I have even told Mrs. G that I still lust for her. A significant step forward was when she understood that I masturbated over her. She eventually allowed me to look while I wanked to her image. It took a bit of time, but she began appreciating that my self-pleasure came from her. Another positive development is moving toward mutual masturbation once she gets used to your wanking in her presence. If you haven’t done it before, start simply. Lie side by side without even looking at each other; maybe interlock legs. Then both of you have a private moment. At one time, this was a nice getaway from normal sex for us. We’ve even performed on each other like this, and timing is quite fun with this challenge. I’m not saying we did all this solely so I could watch her, but it was enjoyable getting there. It took many years. Find your own path, and I am sure others here can tell you more. FWIW the last time I got to watch, it was a brass ring event. She led me by the hand to the chair in our room, sat me down, and said if you touch yourself anywhere at all then the show is over. She then dropped her towel, crawled onto the bed, stared into my eyes while she did it. Her eye contact only broke when they rolled back during her orgasm. Afterward she said, "Hopefully you enjoyed that, now you can come to bed." She fell asleep in my arms while I strained in my cage, basking as I replayed the memory. Best of luck and patience; patience, patience.