Encounters With My Married Best Friend

I’ve only written one other story so this will be my second. I’ve had quite a few close male friends whom I’ve had sexual encounters with. The last post was about my best friend Chad. This one will be about my best friend Andy. 

I met Andy when we were in our Sophomore year of high school (we’re 32 currently). We locked eyes in our gym locker room. I identify as bisexual (only ones who know for sure are my mom and two sisters). Andy on the other hand is straight (I mean you can make your own assumptions after reading). Andy was always such a good looking man. He’s about 6’1 and has one of the best smiles you could ask for. Pearly whites and adorable. Since we’ve grown older he’s lost all of his hair and is bald and a bit insecure. He got married to a girl he had started talking to when we were in high school and now have two kids with her. When he and he first got together his now wife and I didn’t get along. We had issues because both of us talk “reckless” and don’t monitor our responses to one another. Andy would cheat on her all of the time the first few years of their relationship. His mother even had me lying to his current wife (gf then) about his whereabouts when he would be cheating on her. She and I became really cool because I got to a point where I broke bro code and told her he was with another girl. She then retaliated against me and put out rumors that I was gay (was confused at the time and didn’t want to admit I liked guys too). After a while of them being together we just accepted the fact that he was going to be with her and I was/am his best friend and just keep the peace. She’s a really sweet girl and has a lot of stuff going on in her life and we’ve helped each other and and have been there for each other like family. Just wanted to give a brief back story on our relationship. 

Now, back to Andy. From the time we met in high school we haven’t gone more than a week without seeing each other and no more than a couple of days (if even) without talking on the phone. This guy was fine and all the girls in school wanted him. I was so jealous and would tell girls if they asked about him “he was in a relationship” even if he wasn’t just so he wouldn’t get into a relationship and forget me. We joke about it until this day about how we pretty much dated in our late teens-early twenties because we would always stay the night at each other’s houses and pretty much talked on the phone constantly. When we’d stay the night at each other’s houses we’d always sleep in the same bed with each other and would have a lot of touching. With touching I mean (at least in the beginning) was us wrestling in the bed before we went to sleep. Like we’d have a full out brawl in bed with sweating and all pretty much every night. I guess it was a way to get out our sexual desires without taking it too far (as two “straight” guys). 

Ever since then we’ve had multiple encounters that just have me questioning his sexuality and how to proceed with our relationship. There was a time when he’d bend me over the kitchen counter or washing machine and would dry hump the hell out of me (which was super hot at the time). I did go too far one time when we were younger where I gave him a hickey. He slapped the hell out of me and we never talked about it again. I have a nice ass for a guy and he is an ass man and constantly grabs and caresses it pretty much any time (including in front of his mom & step dad). I worry that he’s embarrassed of me because he’s married now and has kids and I’m sure his family wonders why I’m still hanging around being single with no kids. He on the other hand makes me feel so comfortable. I’ve tried to distance myself so he can enjoy his life with his family but he constantly invites me to gatherings that include his family and he never seems to be embarrassed to be around me or grab my ass around them. 

Our most recent serious encounter was the early morning of my 30th birthday. I stayed the night at his house (his two kids were with their grandmother) so it was just him, wife and myself at the condo. We ended up having some drinks and food and his wife ended up getting drunk too fast and passed out in their kids room. Andy and I stayed up having some drinks and talking. I got tired and wanted to go to sleep as we were going to be heading out pretty early to go out of town for the weekend for my birthday (and yes, the wife was coming along). Andy got up to go to the bathroom and on the way back I asked him to get me a blanket out of the hallway closest. He responded “no.” So I got up and walked towards the closet and said “Can’t get men to do anything these days.” Jokingly by the way. He ended up walking behind me and started grabbing and caressing my ass as I was walking back to the couch. I acted unbothered and just laid on the couch on my back and had the cover over me. Andy ended up laying on top of me. Like in the most awkward way possible. I started rubbing his back and kissing his neck. He starts kissing my neck back and dry humping. I then reached down and grabbed his dick. He immediately got up and went to the bathroom without saying a word. I was like “oh well” in my head and put my head down on the pillow. He comes back out the bathroom and was walking around the side of the couch where I was laying and kind of fell over. I grabbed him and pulled him over the couch back on top of me. We started rubbing and kissing again (on the neck and cheek). He then gets up again and whispered his wife’s name. I was like what? He then just walked into his bedroom and shut the door (again the wife was in the kids room). I didn’t hear from him the rest of the night and we haven’t spoken about it since. 

I know he has grown to love his wife and would feel super guilty if something ever REALLY happened between us but I can’t help to wonder if he would ever really take it that far of if I even want it to go that far. I’m not gonna lie. When we’re in the moment I will willing take his dick either in my mouth of ass (just saying) but then what? This sucks. Thanks for reading and let me know if you want more detailed stories and can share any advice!