It was roughly December of 2009 when I first found out about male chastity - a discovery that left my blood pumping, and quite a lot of that blood went due south. The initial discussions on the subject with my then-girlfriend and now-wife went rather unsatisfactorily, from my point of view, as she seemed quite disgusted by the idea. From early on in our relationship, which started in 2007, she had known some of my kinkiness - wanting to wear her panties to feel dominated and, eventually but still early in the relationship, my previous sexual encounters with another man - but few or none of my kinks were things that got her motor running, and chastity seemed to be one thing that made that motor stall. I had (and in some ways may still have) issues and concerns about my sexual preferences and gender identity. In February of 2010, I chose to spend a week without masturbating or having sex and wrote a journal describing my sexual thoughts. By the end of the seventh day, I had written 50 pages, covering chastity, use of strap-ons, having an open or cuckolding relationship, dressing as or becoming a women, having my wife lead our relationship, and probably a whole lot more. I don't remember it all, and have since destroyed the pages. At first, my wife didn't want to read my book - I could be remembering that wrong, but at the very least, she chose not to read it at that time. I started going to a gender identity counselor once every two weeks. It turned out the counselor was a rather attractive Latina woman close to my same age (25 at that time), which made sharing my oh-so-private thoughts simultaneously difficult and arousing. I did not share my arousal with her, and tried very hard to keep it from my mind. After probably 6 or 7 sessions discussing my wants and needs, I came to the conclusion that I do not want to be a woman and, I would say, successfully ended my treatment. We traveled to our childhood home that Easter weekend to visit with my wife's family, and I brought my journal with me in case my wife might read it. On the ride back after that weekend, she read it. I felt exceptionally tense, aroused, nervous, and generally on edge for the hour or two it took her to read my thoughts. We spoke little, if at all, while she read and I worried that the depth and description of my dirty, kinky desires might be the end of our relationship. Instead, once she finished reading, she seemed open to the idea of having an open relationship. We'd discussed it before at my suggestion, but this time we were both agreeable to the option. We had a long talk about safe-sex practices, how we would share our experiences with each other, and probably other associated rules to the scenario that I don't remember. I don't know that it occurred to me then, but having my girlfriend become open to fucking other people after reading my innermost desires should have been a red flag. Able to look back at the whole situation now, it had no need to be a red-flag - we're happily married - but I'm surprised I didn't consider the possibility. A few weeks later, she took a school trip (she was in college) over a weekend as part of a leadership group, and made out with one of her classmates. She seemed hot and excited when she shared it with me, and it definitely got me wound up, too. Shortly after that, I had to take an overnight trip to do some training for my job, and used Craigslist to seek out a partner for the evening. That perhaps wasn't the smartest move, and I won't do it again, but it ended up working out fine. I posted that I was a bi male looking for more or less whatever - a woman, a man, a couple, a pair - for me to fuck, to fuck me - I was horny horny horny during that first day of training thinking about the possibilities; running back to my room during every break to check my email and see if anyone responded. This lead to some ups and downs. Unfortunately, I didn't get any responses except for fake ones. Fortunately, through someone else's ad I found another man who wanted someone to fuck his wife. Unfortunately, he'd already found someone to do so that day and she was pretty tired out. Fortunately... after some inquiry... he was willing to fuck me, and for me to fuck him. I'm going to leave you hanging with that, and will plan to share more later today.
Based on the guy's pictures, he appeared to be an Asian man somewhere in his twenties, with a reasonably-sized cock. It turned out he was probably closer to forty, and his cock was even bigger than my 7+ inches. I don't remember his name, so I'll call him Mark. Mark showed up at the hotel, and I took him back down to my room. We quickly disrobed, and I remember the excitement and tension of standing naked, hard as a rock, with another naked man. It had been about 8 years since my last male encounter, and he was the first new partner I'd had since my wife and I had started dating about two years before. We hopped in shower and, since Mark was taller than my six feet, I remember laying my head against his shoulder and chest while we washed each other. His skin was the softest I'd ever felt.. I'd been with an Asian girl before, and her skin was nowhere as soft as his. Mark kept grabbing my ass and stroking my cock and it made me feel a little dizzy and giddy.. like the little sissy I am inside. We finished up the shower and went to the bedroom. About an hour before, I'd turned the heater up as far as it would go because I wanted hot, sweaty, slippery sex outside the covers. We had some particularly unmemorable foreplay, and besides, I was anxious to get his big dick inside me. I got a condom onto him and lubed us both up, and straddled him. I had to be really gentle because the head of Mark's cock must have been close to a third of it's overall length - remember, his cock was longer than my 7+! - and was quite thick to boot. It hurt at first, the way it always does when it's been a while, but I quickly got into a rhythm. I had my hands on his chest and was smoothly riding that cock, letting the waves of pleasure wash over me as it slid in and out, knocking my prostate with every stroke. It was wonderful, and after a few minutes - I realized the curtains to my first-floor hotel room, which faced the parking lot, were open. Sure, the sheer curtains were closed, but it was night-time and we had the lights on. I don't know if anyone got a free show, but if so, I hoped they enjoyed it! I hopped off and closed the curtains. I tried to get back on Mark, but my ass seemed to protest. We decided it was time for him to take me instead....