This week, a man who works in management considers the future with his girlfriend: 50, divorced, in a relationship, suburbs of D.C.
DAY ONE
4 a.m. Right after waking up — I’m a pretty early riser — I cruise Match. I’m not single and it’s not that I plan on acting on anything … I just like to see what’s out there. My girlfriend, K, and I have been together for over three years now. We met online; it’s the easiest way for middle-aged people to meet someone our age with similar interests.
5:16 a.m. I send K a quick text to let her know I’m thinking about her. We have plans tonight, since both our kids will be with our exes. Our sons are 12 and 16, close enough in age to get along and have some common interests. We both have dual custody, splitting time 50/50, but with work, travel, and social events, there never seems to be a standard week. Both our exes live close, so there is not a huge handoff issue. We both try to do what is right for our kids.
7:30 a.m. Once I’ve worked out and gotten ready for work, I watch YouPorn, then I cruise MFM bisexual stuff. My fantasy is to one day have a MFM or MMM threesome. While I’ve cruised Grindr many times in the past, I don’t think I’ll ever act on it. I am the guy who messages, sends a few pics, then ghosts. It’s the taboo that turns me on, I think. But if I ever found a couple I could trust and had enough of a buzz, it could happen. Maybe.
5:11 p.m. Getting ready to see K, which means it’s time to shave the pubes. I like to groom pubic hair and shave my balls and shaft before I have sex.
6 p.m. At K’s house. We’re grilling fish and vegetables, even though it’s winter. We light the grill and stand outside with some red wine.
7 p.m. I feel a little buzz. Our talks are lighthearted and enjoyable. We talk about work, our families, potential vacation spots for the summer. We both like the beach, which is where we go with the kids, but we both prefer the mountains when we are alone. We like to hike and then visit wineries or breweries.
We see each other alone one or two times a week, sometimes more and sometimes less, so we cherish the time. As our kids grow older, they’re becoming more independent, which leads to more time together. Sometimes, if we only have to do a one-kid drop off for an event, we’ll do a “carpool date,” where we go to a bar or restaurant and have a drink, just to be out together.
9 p.m. We’ve both been waiting for this. It is a slow seduction, undressing each other slowly, standing in the glow of candles. We’re both 50, and I’m proud we’re still very into each other.
Plus, I took a Viagra about 30 minutes prior and I’m rock hard. I don’t always take Viagra — I just notice that sometimes my cock has a little difficulty staying completely hard. I like to think of it as an insurance policy.
9:15 p.m. We go down on each other; I want her to have an orgasm before I penetrate, to make sure she’s taken care of. Then we flip around to various positions and finish with me behind her. I come deep inside her, and we are both exhausted. No round two.
DAY TWO
6:30 a.m We slept in. (Normally, I like to be up at 5 a.m. to work out.) No morning sex, though my cock gets hard easily — the Viagra I took last night is still in effect.
7:15 a.m. On way to work I get a call from A. I had an affair with A four years ago (she was married and I was single). It lasted a few months before fizzling out, and now we’re good friends. Her husband is kind of a dick, so I’d say what we’re doing now is maybe an emotional affair. I sense she wants to cross the line again, but I don’t want to misread her and make a mistake — or cheat on K. Plus, we work together, so it could be awkward.
6:30 p.m. Headed to dinner with K and our kids (P is hers and C is mine). They get along well. Eventually, we’ll need to talk about possibly combining our households; we have talked about how being married would be nice, but we have never really discussed how we would do it, or our parenting styles. K is more relaxed and caters to her son, while I’m stricter with mine.
10 p.m. I head home with C, then fall asleep watching TV.
DAY THREE
5:30 a.m. My running group meets at 8 a.m., so I have a little time to kill and I’m back on Match cruising through. I don’t know why I do this. Partly for the people-watching, I guess?
8 a.m. Meet up with the run group. Great nine-mile run followed by some coffee afterward. K and I train together as much as we can, and we’re planning a sprint triathlon in the summer this year.
5:30 p.m. Happy hour with K, and we both enjoy a few drinks. Then we go home and cook together — mini pizzas, not a huge or complicated meal, just fun to make the dough together and make separate pizzas that we share.
10 p.m. We head to bed, and enjoy a nice round of 69.
Occasionally, in cuddle times like this, K will ask me how many women I’ve slept with. I always deflect the question, but the truth is I know the answer: 63 total different partners. Sex is intercourse; I do not count blow jobs and hand jobs or multiple times with same person. I’m ashamed that I cheated on my wife when we were married — with nine different women. I vowed never to do it again, though I have to admit … I think about it sometimes.
My ex and I were married for ten years, and we got divorced over irreconcilable differences. She was suspicious about me cheating, but I never admitted to it and there was no hard proof. In the course of fighting to stay married, I realized I was unhappy: I did not love her, I was not attracted to her, and I wanted to reboot my life, typical mid-life crisis. I am glad I got divorced, if not I would be in a loveless unhappy relationship. I only wish I could have been happy for C, but C is happy for me and my ex. She’s remarried now, and I’m happy for her. We get along okay and are cordial at joint events, but still, she can turn on me quick.
DAY FOUR
7:30 a.m. Sunday means sleeping in past my usual wake-up time. And since my ex is dropping C off this morning around 9 a.m., I head home.
9:30 a.m. I drink coffee sitting on the couch with C, and get caught up on new events and high-school drama. We have a good relationship; I like to think I am a good dad.
5 p.m. K and I are off to the local brewery with friends. Our kids are off with their friends. K and I have the same taste in beer and food, we match on so many levels … it’s times like this that I really think we’ll eventually make the next step.
10 p.m. Back home. I check out a little porn and read some sex stories. I always gravitate to the bisexual or gay ones.
DAY FIVE
6 a.m. I get a call from A on my way to work. She’s still having troubles at home and definitely needs someone to talk to, I think. I always wonder in the back of my mind if we will hook up again. But logically, I know I don’t want to cheat on K.
1 p.m. On a work call with someone I met about a year ago at a conference. She’s cute — I stalked her on Facebook after we met and found out she had a boyfriend, but I just looked and he doesn’t seem to be on her page anymore. She’s 20 years my junior and an associate (I’m in management), so she’s probably not flirting, just being nice.
6:30 p.m. Home with my kid. We order in pizza and watch TV together.
10 p.m. I check out some Xtube, watch a little outdoor bear threesome that looks pretty real/amateur, without much kissing involved.
DAY SIX
5 a.m. Back on Match. I did not do this for the first two years of my relationship with K, unless we had a fight (I did it while I was married too). Our relationship may be at a crossroads right now. I keep thinking we should take the next step, and pretty much wanting to — I just need to make sure I know what I want and what I am doing. Social media makes everyone’s life look better than yours.
11 a.m. I head to the gym. I missed working out this morning.
6 p.m. Wine with K, no kids tonight. We make and enjoy a light salad with roasted pork; we’re trying to eat as healthy as we can. If we cut out wine and beer, we know we’d both lose weight.
8 p.m. We sit and talk — we’re not big TV people. We have a few shows we binge-watch, but we try not to be caught up in “must-see TV.”
9:15 p.m. We are in bed, no Viagra. No major issues, just need to make sure my cock stays stimulated. A nice slow session.
10 p.m. Spooning, we talk about nothing. I might not know for sure where we’re headed, but I do know I enjoy being with K on a mental and physical level.
DAY SEVEN
11:30 a.m. I head to the gym for a quick workout. There are some hot moms — nothing like some attractive women to motivate me.
6:30 p.m. K comes over for dinner. Her kid is with her ex so we try to squeeze in a quickie when we can. Our sons get along really well … their relationship reassures me that K and I may have a future together.
7:30 p.m. Steaks are on the grill and baked potatoes are almost done. K loves when I cook. She’s an “okay” cook and she knows it, so the cooking in our relationship is mostly on me.
10 p.m. K Leaves and I head to bed. We’ve had a really good week, and I’m pretty excited to see what’s next for us as a couple. I like to think we will get married; I think we’re good for each other. I know I have a wandering eye, but I am a good person and I like to think my days of infidelity have passed. If I want us to have a future together, I know it has to stop.
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