Continuation of the back story...Don't worry, I'll get to the good stuff.
Over the years me and John have gotten pretty close, I eventually told him I was Gay and he said he was pretty sure he was Bi, but only had thoughts but no gay experiences, I told him "that's the way I started out too" , we talked for 2 hours about some of my experiences, and told him about some wet stuff just to see his reaction, but not everything since I didn't want to spook him off from our occasional pool jumps and the rare chances to see him wet fully clothed...
Things got interesting about a year ago, he got into a big fight with his parents and he showed up at my door, I could tell he had been crying, and he asked if he could stay at my house for a few weeks until he could find an apartment, I have a dedicated guest bedroom, he's used it a dozen times himself, so it was absolutely no problem at all...We talked for about an hour about what happened, and it was mainly about him not doing chores around the house, and his parents telling him he needed to pay $40 a week rent. I told him that it seemed pretty reasonable to me considering how much apartments rent for in our area, eventually he grudgingly agreed with me but still wanted to look around.
We had a few more beers and then I reminded him he still had work early in the morning and stood up and told him "I'll get your room ready", he looked like he was in the verge of crying again, looked up at me said " I really don't want to be alone tonight, is it ok if I sleep with you?"...How could I refuse.
We stripped down to our boxer briefs and climbed into bed, and I guess his emotions were frayed, because all of a sudden he started crying, I never saw him cry before. I rolled over and we were face to face, and next thing I know we were holding each other, and I gave him a light kiss on his cheek telling him This will pass" and then his lips met mine, it wasn't a deep kiss, but it was our first real kiss...But it was enough to get me instantly hard. Then suddenly I felt something hard was pressing into my stomach, John laughed and said "Well, I think I can confirm that I'm officially Bi" and we both shared a laugh. I asked if I could feel him through in boxers and he said yes, I informed him that we are about the same length, but he was more thicker than me, the next thing I know I felt his hand around my cock and he said matter of factly "Your right, I never thought about it"...One thing led to another and we both started stroking each other through our boxer briefs, suddenly he shot a load so powerful that it went though his boxers and up my hand, not just once, but over and over, and then I also came. This time we kissed passionately for the 1st time, we continued until we were both spent. We both laughed and I said " I think you messed up my bed", and John replied "ya think?" I got out of bed and went to my dresser where I keep 2 packages of new underwear, and handed him a pair of black Calvin Klein boxer briefs and a washcloth. We both changed into clean underwear, I told him how hot he looked in CK's and he mentioned how comfortable the CK's were.
I turned on my light to set my alarm clock for him to get up for work, and asked what time he needed up, but no response, he was fast asleep, looking like a sleeping angel.
The next morning the alarm went off, he woke up, stretched out turned and looked at me and said "Thank you for last night" . I asked if he was ok with what happened last night, he smiled from ear to ear and said "fuck yeah!"
I got up, went into my master bathroom, and tout on the counter another new pair of CK's to go to work in, a fresh towel, and a new packaged toothbrush for him to take a shower. It was still dark so he walked outside to his car in his old slightly stained sleeping CK's (I wonder if any of my neighbors are up and walking their dogs) and he got his spare work uniform. When he came in I handed him a fresh brewed cup of coffee, he stood at the counter and couldn't help but stare, even with him messy hair, he could be a model for Calvin Klein underwear! He finished his coffee and jumped in the shower, I stripped the bed and started a load wash, including 4 slightly dirty boxer briefs, lol.
John called me later in the day and said his parents had worked it out, and thanked me again for last night.
I hung out with him and his co-workers from time to time, usually on Fridays after work, everyone he worked with were as nice and friendly as John. But unfortunately during this Pandemic, his hotel occupancy dropped by 60%, so a few of his co-workers got laid off, and the few that were lucky enough not to be laid off got some pretty severe pay cuts due to reduced hours. Money got tight for John, but I always picked up Johns tab, and he always left the tip. So when his boss invited me to her wedding, I gladly accepted...Now it's time for the wedding...