Diane's Open Relationship: Juan

My relationship of over eight years to my boyfriend Max was hanging on by a thread. It was bad. We were both miserable and headed towards an inevitable split. And if that wasn't bad enough, my work life was somehow even more miserable. I was suddenly doing three people's jobs and working sixty plus hours a week. At 52, I was in a job that I hated and a relationship that wasn't working. And then the pandemic hit.

I couldn't take it anymore. As awful as the pandemic was, it gave me time to stop and re-assess my life. Life can be taken away in an instant and I didn't want to spend another minute of it being miserable. I spent my life conforming to other people's standards and I didn't ever want to do that ever again. Life is too short to be miserable.

I broke up with Max.

I quit my job.

I cut my hair radically short and dyed it purple. I got a few new tattoos.

I eventually found a new job - it is much less corporate, much less bullshit (although definitely a sizeable amount of bullshit) and far more diverse. I can wear whatever I want and be myself. Nobody gives me shit about my hair or my tattoos - in fact, I'm often complimented on both.

I was starting to feel much better about myself and my life. I was even thinking of dating again. I had been with Max for so long, and before that was married for many years, so I was very much out of practice. And I imagine the prospects are limited for a 50-something divorcee.

But I feel like I have something to offer. I'm smart and accomplished and kind of cute. I have some style. I'm no beauty queen, but I've managed to stay relatively fit and healthy. I'm tall at nearly 5'10" and while my body isn't as pert as it used to be, men still check out my ass on the beach.

I made a few attempts at making an online dating profile, but couldn't get into it. I had met Max online, so I know online dating can work, but didn't seem to have the bandwidth to go through all the hassle of weeding through all the creepy guys and crazy messages and the unending parade of dick pics.

And I missed Max. We were good for each other in so many ways, but I couldn't take his constant absence. Max is always out of town for work, often half the year, and even when he is in town, he works nights and I work days. It was like being in a relationship with a ghost. And sadly, our sex life had become non existent the last few years. But I still missed him so.

I called him. We made a coffee date. We talked. And talked. And talked.

In so many ways we are not right for each other, but in so many ways we are. I love this man so much and didn't know what to do about it.

Max had brought up an idea years ago that I dismissed out of hand, but he was bringing it up again - an open relationship. I initially cringed at the idea. And while I consider myself progressive and inclusive and open minded, I still couldn't wrap my head around it.

I'm a romantic at heart I suppose - I love the idea of growing old with a special someone and taking care of each other. But I did have friends who were in open marriages and seemed to be doing well. After that coffee date with Max, I had a long talk with my longtime friend Aidan - a lovely gay man who was in an open marriage with his husband. They stopped being sexual with each other several years into their marriage but were still with each other romantically. They still planned on growing old together.

My anxiety ridden head and heart foresaw all the potential issues with jealousy and resentment and STIs, but for Aidan and his husband it seemed to work. Aidan reminded me that many monogamous couples cheat, and that its much healthier to be open about it. But I never wanted to cheat on Max - I just wanted more of his time.

I still had my doubts. I'm not a gay man - my sexuality is different and I'm not sure the scenario would play out the same for me. But I didn't want to continue to settle. Again, life is too short to be unhappy.

We decided to give it a shot. Max moved back in and after weeks of discussion, we agreed on the following ground rules if one of us wanted to date others: no one in either of our professional or personal circles, don't bring anyone back to our apartment, always practice safe sex, regular STI testing, absolutely no secrets, each other is always the first priority.

We did start having sex again. It was lovely - familiar and kind and gentle like an old soft t-shirt. But it was also a reminder that we simply did not have the sexual spark and energy that we used to - perhaps it was a sign that we were embarking on something necessary and needed.

A few months had passed and neither of us had partaken in the open part of our marriage. But our day-to-day life was better, more peaceful. Max's schedule became busier and busier, and in the past this would have led to arguments and tension, but that wasn't happening this time. Somehow the knowledge that I was free to find other romantic company helped ease my anxiety.

But how to find that romantic company? I was in kind of the same place when I broke up with Max - and I just didn't want to online date again.

Is there someone I knew that I might be interested in? There was someone I had to admit - but I had no idea if he would be interested or what he would think about my situation. I wasn't sure I had the courage to put myself out there with him.

Juan lives in my building. He's a very kind, jovial Puerto Rican man who always has a big smile on his face. Every time I see him, I can't help but smile as his positive energy is so infectious. He's around my age, a smidge taller than me, slim, with a thick curly head of hair. He has an adorable dog.

He lived alone, so I assumed he was single, but I had no idea. And I didn't really know him. It's not like I wanted to jump in bed with him. But he seemed kind and cute and someone I might like to spend time with.

So one Saturday evening, when Max was working late, I mustered up the courage and knocked on his apartment door and asked if he happened to be free for dinner. I was so very nervous, but Juan is so jovial and so relaxed, I had nothing to be nervous about. He enthusiastically joined me for dinner.

We had a great time. I don't know that Juan thought of it as a date, but if it was a date, it was a great one. We must have chatted for over four hours, and by the end of the night we agreed to do it again sometime. I didn't reveal that my relationship was open, but I did learn that Juan was single.

A few days later, we went for a walk, and a few days after that a movie, and then a day at a museum. They felt like dates to me and I imagine Juan must have been wondering what this was.

I was so nervous about how I would tell him about my relationship status -- but the words came out of my mouth and only after had I realized what I'd said. We were standing in a park walking our dogs and I just blurted it out. He gave me his signature big warm smile and held my hand. It seemed like we were now dating.

A few days later, on a rainy Saturday morning in which Max was working all day, I found myself in Juan's apartment - making out like teenagers. I hadn't kissed anyone besides Max in over nine years, and it was glorious. His smell, his taste, his presence were all new and different and wonderful. He kissed passionately, purposefully - I had not been kissed like that in a very long time. The last time I was this aroused, this wet, was when I first started dating Max.

It felt so good to be so turned on - to feel desired and to desire. I reached my hand over Juan's crotch - feeling his hardness over his jeans. I started undoing his zipper while he gently groped my breasts. My t-shirt and bra found their way to the floor as he pulled his pants down.

His cock was glorious - a big thick uncut erect penis. I had a few well-hung lovers in my past, but it had been many years since I'd seen or held a penis so large. I stroked him while kissing him and the combination of sensations had me in heat.

He removed his shirt as I kissed my way down his chest and stomach to his cock. I was mesmerized by his manhood and I wanted nothing more than to give my new lover a great blowjob. I licked, sucked, stroked and slurped as he moaned and groaned - it was all so gloriously slutty.

I worked my way out of my jeans and straddled his lap...his hard cock against my very wet pussy. I grabbed his head and kissed him passionately as I ran my hands through his curly hair. With one hand I grabbed his cock and reveled in its feel and size. I had not had a cock this big inside of me in a very long time and needed to be in control.

Juan put on a condom (a Magnum!) and I lowered myself onto him slowly. His thickness was stretching me. It was uncomfortable at first, but I proceeded slowly and deliberately. I breathed deeper with every inch I was taking, until he was entirely inside of me. I kissed him again deeply and began gyrating slowly, feeling his cock hit parts of me that hadn't been touched in years.

My movements became faster and stronger, and as I grabbed onto Juan's head, I had my first orgasm of the day. I let out a guttural, loud moan that no doubt was heard in the hallway. My pussy was fully relaxed and stretched, and in this position, I grinded myself to another screaming orgasm.

Juan kissed me passionately after the 2^nd orgasm, and still inside of me, turned me around on the couch so that he was now on top of me. He was in control now and began sliding himself in and out of me strongly and firmly.

I was in heaven as my legs were wrapped around Juan, feeling his manhood fill every inch of me. His rhythm became stronger and faster - it was he who was now making noise, sounding almost animalistic as he neared orgasm. He came in spurts, convulsing slightly as he collapsed on top of me.

My God I needed that. Juan slowly slipped out of me and carefully took off the condom. Judging by how full that condom looked, he needed it too. Seeing how much cum he produced made me a bit giddy.

That night I had dinner with Max, and as per our agreement not to have any secrets, I told him. I just blurted it out.

"I slept with someone," I said with a veneer of calm masking my anxiety.

Max looked up and after a brief pause replied.

"Was it a good experience?" he asked earnestly.

I waited a moment before answering - I could still feel Juan inside of me and couldn't help but smile.

"Yes...yes it was."