My college best friend is a straight alpha
Hi Sam! I'm a fag in my late 30s living in the northeast US, and the straight alpha I'm longing to serve lives in the Midwest. I had a crush on the guy in college, but I moved on from wanting a romantic connection with him by the time we were done with school (almost 20 years ago). I found out after college that he'd been fucking guys all through college, but he was keeping it on the DL because he was concerned about hurting my feelings. I'm pretty sure he and another one of our close friends were also banging on the regular, and in retrospect, there were a few opportunities for the three of us to play that I was too chicken to pursue.
A few years ago, I brought it up, and he said, "Yeah, everyone needs a big cock up their ass sometimes." It wasn't what I was expecting, but I was glad that bringing it up didn't mess with our friendship. In 2022, I visited him for a week, and he flirted with me the whole time! In front of his girlfriend (now wife), he suggested that I might want to suck a load out of his cock—she looked mildly scandalized, but I got the impression he found a woman who lets him fly his freak flag. At another point in the visit, we were in the back patio of a bar and he was telling me a story about going to a strip club with friends, and he grabbed my crotch playfully at one point to make a point. My partner (male) and I went to his wedding last year, and though we didn't make out (like we did at a mutual friend's wedding a few years prior), we danced together and I felt the charge still there. I also met a friend of his during that visit, who he does a naked bike ride with every year; I also felt a charge with that guy.
It's obvious he was testing and provoking me when I visited, but at the time, I was too scared to jump on the opportunities he presented. We catch up on the phone occasionally, and the guy is still my best friend, but we don't see each other in person very often.
I fantasize constantly about serving him and his friend, giving them my holes and my hands and my mouth, letting them dominate me and in all ways treat me like the fag I am. He and his wife might be heading my way at some point this year—do you have any suggestions about how I can find and engineer opportunities, both now and when he's here, to communicate my eagerness to please without going overboard? I feel confident that our friendship can withstand some stretching of the boundaries that have been there for close to two decades, but I get the feeling the onus is on me to make the next move. What do you think?
