Chastity in vanilla life discussion

Let me share a bit of my history with the Mr. first. Back in 2009, I wasn’t completely certain about my sexuality; let’s say I was roughly 60% gay and 40% straight, so properly bisexual. That year, I began dating a fairly masculine girl (let’s call her Mary) who I’d met through the car club, and we connected quickly. Even today, cars remain central to our lives as we organize track days and run our own car club.

After about a year of being together, I realized the sexual attraction wasn’t quite there, even though everything else in our relationship was wonderful. Also, I had numerous secrets hidden away that weren’t obvious. I have many kinks: I love men’s thongs (I wear them every day) and jockstraps, which meant hiding them whenever date night arrived so I could switch to boxer briefs. Bondage play and domination were things I wanted, yet my bisexuality was still largely unknown! Yes, I was suppressing these deep desires while not feeling fully aroused by the relationship; I definitely craved more cock (bluntly speaking, that’s what I thought). Eventually, I decided to end it with Mary because I needed more than what we offered each other. It felt harsh, but I didn’t want to live a lie or claim I was gay. Ironically, Mary’s first boyfriend had done exactly that: he met someone through the car club, realized he was gay, and left, which devastated her.

I moved to the opposite end of the country for my career, though Mary never left my thoughts. A year later (by then I felt at least 80% gay), we were definitely on talking terms again, if not quite best friends through the car club yet. Several girls showed interest in me during this time; I had to ignore or reject them while still closeted, sadly crushing their hopes without explaining why (life can be brutal). One night at a party, a petite Japanese girl asked directly why I wasn’t reciprocating her advances (I’m too socially awkward to notice these things often—I am such an idiot!). I told her there was another woman on my mind whom I couldn’t let go of. A couple of months later, while visiting my parents up north, I took the chance to reunite with Mary. She was thrilled because she hadn’t given up hope either.

On our first night back together, I planned to lay everything out when we went to bed. I had worn my favorite clever thong all day and into the evening barely containing a boner, so very excited to finally share my kinks. I stayed quiet until we were in the bedroom stripping off. As Mary undressed me and unzipped my jeans, she had a little “wtf” moment seeing what was underneath her curiously exclaiming, “What is this!?” Then came the floodgates: there I stood in nothing but my thong before her for the first time since we got back together. I explained that my initial breakup happened because I am gay and had been keeping too many secrets; I hadn’t wanted to say it sooner due to Mary’s ex-boyfriend doing the same thing. I also mentioned loving bondage, wanting to be cuffed up, adoring thongs a bit too much, etc.

From here on out, let’s refer to my partner as He—let’s call him “Barry.” Barry is about to undergo top surgery in a few months and has been on testosterone for two or three years now. It can be offensive to those who don’t know if you refer to a trans man like Barry using she/her pronouns, so keep that in mind! I only used them leading up to this point because back in 2009 and 2010, we didn’t yet know.

That night, we hooked up again. I thought I was the one with all the secrets, but Barry had nothing on him… He opened his floodgates too, revealing he was secretly a somewhat gay man, teaching me about gender dysphoria and what comes with it. Since that day forward, after coming out to each other, we’ve essentially vowed not to keep secrets, laying everything bare for acceptance (and we do accept one another). It’s uplifting to share our kinks—for example, walking around the house in a thong while cleaning—and funny enough, despite having underwear kinks within the chastity community, I don’t wear women’s underwear. These are strictly men’s thongs and men-only pieces, with occasional jockstraps and men’s bikini bottoms mixed in. We’ve explored bondage; my bedside holds bags full of ropes, chains, cuffs, and dildos… But things aren’t entirely perfect in the bedroom.

Barry is quite vanilla—which is why I’m posting here—as this story evolves into a man with chastity (and other kinks) trying to convince his more traditional half. From day one when we reunited, I told Barry, “My dick is yours,” which amusingly has two meanings in this context. What I mean is that I want him to have control over it. This dynamic was established even before I knew I liked chastity. I am very much the submissive partner; every time we have sex, I get pegged, but he never quite grasped what I meant by that or cared deeply for it. I want him to initiate sex and decide which kink we’ll explore tonight, yet this rarely happens. When kinks do appear in the bedroom, I usually end up controlling the situation and introducing them, though thankfully he plays along. If I chain myself up, our sex is great with passion present.

Unfortunately, dysphoria is a powerful force. It affects your mind, emotions, and desires. Barry frequently suffers from depression because of it. Sadly, in the trans community, this aspect is ever-present, leading many to take their own lives. Fortunately, Barry remains level-headed and admits he’s too stubborn to do something like that himself; we’ve established this truth between us. He has strong career ambitions and plans for new modifications and restorations on our many cars. We are emotionally stable in those regards, thank God… where the depression and dysphoria surface is primarily in the bedroom. Half of my reasons for initiating weren’t due to Barry’s disinterest in role-playing or sex itself, but because his dysphoria was interfering with him. Every time we were having sex, he would be reminded that he doesn’t have a dick and wasn’t deriving much pleasure from it.

It’s been nearly two years since we last had intercourse. In the last two years, I’ve maintained myself through a vigorous masturbation routine. I don’t mind too much because Barry and I are deeply in love and see ourselves together for many more years to come. We have so much in common; we never fight and thoroughly enjoy each other’s company regardless of physical appendages. However, I rarely masturbate in front of Barry—I suppose I’m a bit shy about it. Usually, I wait until he goes to bed to watch some porn (which over the last two years has featured an increasing amount of chastity content), or do it in the shower, or when we are home and he is out. A bag full of dildos keeps me happy enough.

Earlier this week, I got my first chastity device… initially keeping it a secret from Barry. It’s an HTv2, and right away I managed to wear it for two consecutive days, quickly figuring out how to relieve the ball burn and other issues. I’m not entirely sure why I proceeded with getting one, aside from wanting to try wearing something on my genitals during the day (appealing to my bondage kinks) and playing with the idea of being controlled regarding my orgasms through alternative means. Being controlled wasn’t actually a primary desire driving me… But I connected the dots pretty quickly with chastity and my earlier comments when we reunited about wanting my dick to belong to Barry.

I realized that this is truly what I wanted: FULL control. Here’s the funny part. A few nights ago, after just dominating my backside with a dildo and trying to force an ‘hands off’ orgasm (something I’ve managed many times outside of chastity before, but couldn’t do while wearing it), keeping in mind this fits right into my recent masturbation routine, so this sort of thing feels normal now. I was still in the shower with a semi and the cage on, that big red dildo sitting on the shelf beside me as I cleaned up… Barry walked into the bathroom for a pee. The toilet is right next to the glass door, but he didn’t even notice either the cage or the dildo! hah. The following morning was day 3 (this Saturday) in the holy trainer (for the very first time ever while in chastity). I decided to do the big reveal, keeping our theme of total honesty alive between us. He said “oh cute” right when he saw it (I felt instantly a bit demeaned, but then I realized I actually liked that feeling, hahaha) and we started talking about it. He asked about medical dangers with wearing one etc., but I assured him it’s safe and many thousands wear these for weeks or months on end. Then he flipped me over again, this time whipping out a new dildo he had bought (remember, we haven’t had sex in two years!). I was pleasantly stunned by this development; this particular model has a bulb that can be inserted so he can peg me like that. He’d actually kept it secret for a month since things got cold in the bedroom… Suffice it to say, it’s nice to clear those secrets out of each other’s closets again and return to a state of equal and total honesty. But still, Barry is vanilla (I can’t even get him to wear a jockstrap to keep his prosthetic in place; he’d rather just not wear the prosthetic at all than put on a jockstrap), and hasn’t really said a word about the chastity since Saturday morning. I think I want him to be the key holder, but for now I’m worried about wearing the holy trainer. That afternoon, I had to take it off as my balls finally started to ache… It’s the scrotum; mine isn’t very large, and the device stretched the heck out of it. After three days of being stretched, it finally said enough… and I am still recovering. I’ll jump straight back into the cage and start over again the moment the scrotum stops tendering up, while waiting for that to heal—getting plenty of moisturiser! That night, I made sure my rear end was nice and clean for anal intercourse, hoping for, wishing that Barry would initiate sex with his new dildo, but we only cuddled and fell asleep spooning (it’s the first time in about two years we’ve fallen asleep like this too, so things are already on the mend there!!!). It feels good to have that love return to the bedroom. So let us see where this goes. I’d like to keep this thread updated. It’s Sunday night now and I’m about to go to bed. Hopefully over the next couple of weeks we’ll finally break the dry spell between us, and maybe I can convince my vanilla better half to become a key holder. Thanks for getting this far… I thought I’d just write a few paragraphs, but instead it took 3 hours! It means a lot to me that anyone is reading this at all; thanks for coming on this journey with me. Much love <3.