the key is on my nipple ring

The Other Man October 28, 2010

I have mentioned a couple of times that the concept of cuckolding doesn’t really turn me on, either in reality or as a fantasy. But having read a number of blogs with cuckolding couples sharing their lives, I’ve been thinking about it more, which caused me to consider an experience I had about a dozen years ago in a different light.

It all started when an old high school friend, Zack, tracked me down on the Internet. This was pre-Facebook so finding old friends wasn’t quite as common as it is today. Anyway, he sent me an email and I was delighted to hear from him. It had been at least 25 years since we’d last seen each other. He lives in a state several thousand miles from me but in a wonderful coincidence, I was going to be presenting at a conference in a city about 100 miles from his home. I shared this info and he immediately jumped on the chance to get together for a reunion.

We emailed back and forth. I added an extra two days to my trip so we’d be able to visit without the interference of work. I was excited about seeing him again.

Our relationship in high school was not as boyfriend and girlfriend; rather, I had a steady boyfriend, Jeff. Jeff and Zack were best friends. Zack had a string of short-term girlfriends (a date or two or three). Since Jeff had a car (a precious commodity for a high school student) we often double-dated: Dev, Jeff, Zack and Zack’s girlfriend-du-jour. Looking back I realize that all those dates probably always felt pretty left out since the three of us were the good buddies. If I knew then what I know now, the three of us probably could have lots of fun, but alas, high school kids weren’t into kinky threesomes back in those days. Our loss.

Anyway, back to the trip. The night before I left, Ab and I had a conversation in which he said to me that he wanted me to “have fun.” I wasn’t exactly sure what he meant and he clarified that it was okay for me to have fun, whatever “having fun” turned into. In other words, sex with Zack was okay if things came to that. I was a little surprised since that was not what I was anticipating but it turned out that Ab was more prescient than me.

On the appointed day, Zack drove to the hotel where I was staying to pick me up. I was waiting in the lobby and the first thing he said to me was, “You’re still beautiful.” I wasn’t expecting that! As for Zack, he was looking pretty damn good, himself. He was one of those guys who had a slightly dorky look in high school—skinny as a rail (as he said, he had to hop around in the shower to get wet)—fine hair that didn’t look like much and the bane of all high school kids: a bad complexion. But now, 25 years later he had matured into a very handsome and buff man (he worked out) with piercing blue eyes, beautiful skin and not a touch of grey. I was smitten.

We drove back to his city, went out to dinner at a swanky restaurant with a lovely view, talked and talked while we ate and drank a lot. It was great. After dinner we went back to his house, still talking and drinking. There, of course, things got more personal.

My favorite memory of the night was when he confessed to me that he had always wanted to have sex with me in high school but would never make a move because of Jeff. Even so, he drove to a pharmacy three towns over to buy a condom! This was back in the quaint old days when you could only buy condoms at the drug store and the pharmacist, who knew everyone in town, would give the boys “a look”; thus anyone in need of a prophylactic had to go elsewhere to find an anonymous pharmacy and pharmacist. Zack told me he carried that condom around for years—it even made a ridge in his wallet. And it never got used.

Naturally, with a seduction like that, we ended up in bed. It was all very romantic with lit candles on every horizontal surface in the bedroom. I was swooning and because I had an implicit okay from Ab, I wasn’t even feeling a little bit guilty.

Then the grand irony of the evening: because he’d had so much to drink, he couldn’t get an erection! I wasn’t particularly put off by this. I was at the stage of my life where I had figured out I wasn’t going to have an orgasm through intercourse anyway, so it was fine with me if he did all the other stuff—fingered me, licked my clit. Unfortunately, I didn’t have a vibrator with me, otherwise I would’ve whipped that out. But he was very, very embarrassed and that pretty much put the kibosh on the rest of our night together. No orgasms for either of us.

He had to work for a few hours the next morning which was probably good to give us a little break. After that, we went out to lunch and then he drove me back to the hotel in the other city. We still had fun but there was a little undercurrent of unhappiness and sadness. It wasn’t the same wonderful feeling as it had been the day before.

When I got home I told Ab everything, of course. He wasn’t jealous nor was he upset since everything happened exactly as he had anticipated (well, not the non-erection part, but everything else). I got to experience a wonderful feeling of love and trust, knowing that he believed in me enough that I could go do this with an old friend but would not be tempted to run away with him forever. I sometimes wonder, however, if Ab’s reaction would have been different if Zack hadn’t had his performance problems. If I had come home and said, “He fucked me like a wild man and I had orgasm after orgasm until he was peeling me off the ceiling…” Would that have changed the dynamic? Would I have even been completely honest?

We’ll never know. It’s all water under the bridge now.

So, thinking of this in the context of cuckolding, this is probably the closest we’ll ever come. My husband sending me off into the arms of another man, with his knowledge and permission. I suspect he got off on this somewhat although we never really delved too much into that aspect of the conversation. Maybe I’ll ask him now, after he reads this post.

As for Zack, we stayed in touch for a few more months but eventually stopped emailing. We realized that beyond our shared memories of high school we didn’t have a whole lot in common and we certainly weren’t in a position to maintain any sort of a relationship. So that was that.

I just tried to look him up on Facebook and he’s not there. Google tells me that he is living in the same city and owns the same small business. I suppose I could email but I think at this stage, it’s best not to open that door again. Wise people know when memories are best as memories and I think this is one of those cases. Oh well. I did have a lot of fun for 24 hours and I’ll hold that close in my heart.