I’ve shared this here before and decided it’s probably better suited for this specific subforum. Here are some of those earlier posts: the community page reference Before diving into the details of my chastity journey, I should give a little context about who I am. I’m a 22-year-old guy, standing at 6’5” and weighing around 220 lbs. Exercise isn’t really my thing, so my physique is pretty average. My interest in women sparked when I saw Girls Gone Wild on TV at age 13; later, messing with a friend at 15 made me realize I liked men too. Even though I got plenty of blowjobs for about a year, I didn’t fully identify as bisexual until college. Despite having opportunities, I haven’t really entered into sexual relationships since high school and don’t feel much need to right now, preferring to wait until my career and income are more stable. My interest in kink traces back to two main points. My high school fuck buddy had a strong underwear fetish, which rubbed off on me. Once I realized kinks were real things, I experimented for a bit before stumbling upon photos of Taylor St. Claire’s ruined orgasm and T&D work one summer morning when I was fifteen. Something clicked, shifting my fantasies toward T&D. Since then, I’ve discovered the broader world of chastity and teasing/denial (TD) and enjoyed all the media it produced. For a long time, my interests stayed in fantasy land despite numerous ruined orgasms and occasional weeks of teasing. I thought about this idea for a while before finally buying some toys: a Fleshlight and a solid Chinese knockoff CB-6000S. Once I clicked that cage on, the fantasy became real. Now I understand why people love it. The constant sense of neediness, arousal, and submission is incredible; I’m hooked. The past week was intense. What started as just something to do for wank fodder turned very real by day three. I felt a type of horniness I didn’t know existed. I stumbled a little during a teasing session almost cumming but held out the rest of the week. During a hormone-fueled frenzy earlier on, I bought a Rude Boy vibrator. Being an anal virgin, this bold move made sense at the time. After trying it Friday and failing slightly, I mostly put it away, using it just to tease my locked cock. By Sunday night, though, the lockup was getting to me as prostate congestion symptoms started showing up. So, I bit the bullet and decided a milking was necessary. It took some effort, but I managed to position the vibe correctly. I played around until I found my prostate, increased the speed slightly, and used the toy like a dildo. When milked, you’re supposed to feel that urge to pee, which is what happened, so I worked it faster. A dribble of milky fluid leaked from my semi-hard cock, followed by three strong spurts of cum onto my shirt. Drained but feeling quite slutty:p, I cleaned up and went to bed, though part of me kept screaming that I hadn’t really cummed. Even though I stroked a bit yesterday, no actual release occurred. Back into chastity I went. Now that the wall of text is done, I’m at a crossroads. I’ve felt slutty and horny all day (did I mention buying a dildo today?;)), yet I remain locked up. Honestly, that feels correct. However, I’m struggling to decide my next move. I plan to hold out for the next three weeks but am unsure how that period will conclude. Regardless, here are my rules:
- No cumming until November 2nd, so no ruined orgasms allowed.
- Chastity release only for cleaning and teasing sessions.
- Three teasing sessions per week, each limited to ten minutes. I can prolong the fun but must stay locked; again, no cumming. During these times, I can do whatever pleases me—jerking off or using the Fleshlight—but I cannot penetrate it with my cock. The 30 total minutes of teasing time can be done all at once or split up.
- Two milking sessions per week with no strict time limit on duration. However, manual stimulation isn’t allowed while actually playing with the toy during a session. So yeah. Hope this was enjoyable to read. Looking forward to input on how and when I should conclude this teasing phase.