Challenge Accepted

As of posting, I'm in the middle of being chaste till I meet with Old Guard. This would be the longest period of not jacking off; a week and a few days. This would be easier if there was a chastity device preventing me to even touch my cock (I leak a lot), but when you're not jacking off for someone it's a little easier. In addition, there are also tons of distractions from jacking off like work, projects, friends, and family. (Except the fucking dog whose licking all over the fucking place.)

After seeing Old Guard, I have at least a day and a half to jack off like a gym rat on a cheat day. One porn after another (I try to cum after the seven minute mark) in a quiet space where I can't be disturbed, licking my fingers of the evidence. When we schedule the next meeting, I tell him that I wont be jacking off until then. Fucking genius.

Reminding myself of this predicament, I remember jacking off in the school bus; I was the last kid to get out and all I need to do was to open the fly of my school uniform shorts (sexy amirite?), and later on slacks pants, and rub my cock through my white briefs until I explode. It was easy, all I need to do was look normal from the chest up and leave the cum on my briefs till I go home.

I can lie about being chaste and since I can do multiple orgasms alone (Seven within approx 24 hours) and with someone (Old Guard: four, two of which are dry, within approx 32 hours), I need to make sure not to jack off 5-6hours before I get to his place. But like any overachieving asshole, I'm into games and challenges. Also, I actually believe in the value and integrity of my word, and when I say, "I will not cum," I will not fucking cum. I don't know why I make it harder on myself.

Exhibit A: On one of our first tries for a missionary position, Ace's 7" would really hurt me. Sometimes, I make his job harder by not telling him and taking it like a trooper. He'd notice though and we'd go back to spooning.

"I was just seeing if I can go further," I reasoned as we cuddled.

"uhuh," he replied. His cock still inside me.

Exhibit B: I borrow a dozen library books all at once. I also try to read two at a time.

Exhibit C: I actually fainted during a workout. (2)

This adventurous spirit probably came from a past so restrained in all material and non-material ways (most where my fault), that one day I just said, "fuck it, let's let loose."

However, in some twisted paradox, I come to love the restraint Old Guard provides.

At one time, we started to drift off to sleep and it's the most comfy and horny state I've been in. My wrists and ankles are cuffed together with soft black leather, and he's spooning behind me, hands all over my body. My shallow breaths and mewls were interrupted by an occasional smack on my ass or stomach. He told me I was hard all night.

Maybe this "kink", as Old Guard would say, comes from my love of the bear necessities. The appreciation I have to the limits I learned to appreciate, respect and, at the same time, push against.

Or maybe I'm just a pig with untapped potential?