It was Samuel Johnson who said, "Depend upon it, sir, when a man knows he is to be hanged in a fortnight, it concentrates his mind wonderfully."
And that, sort of, is how I ended up where I am today - heading out to the suburbs to meet a couple I connected with on a gay dating site.
First, some context. I'm 61, and divorced for more than a decade now. I tried a couple of dating sites and met a few women, but none who clicked. I'm not a tall guy - 5' 5" and carrying a few extra pounds - and not very athletic. I've always been self-conscious about my height. So, not exactly an alpha male and not exactly a magnet for the opposite sex.
But there was something more at play.
For years, I had wondered what it was like to suck a cock or get fucked. But I was too scared to actually act on it. I made do with online gay porn, jerking off to stories and videos on various sites. Just fantasizing.
I tended to gravitate towards amateur videos, not professional ones; they just seemed more authentic, and earthy. And I found I got more aroused the more aggressive the tops were, especially if bears or daddies were involved. I then started seeking out videos with threesomes, specifically those with one serving the other two. I'd watch the same videos over and over, fantasizing about being in the middle of a spit roast.
I realized by then, of course, that I had submissive tendencies. Hell, I'd probably always had submissive tendencies, but they'd been latent.
Around the same time, I started using toys. A butt plug "starter pack" was first, and once I had conquered those (with a lot of lube), I tried a couple of lifelike, flexible dildoes. I practised sucking on them and using them where they belonged. It got to the point that when I inserted them, it felt fucking great when the head passed the ring and touched my prostate.
But still, it wasn't the real thing. I wondered what the heat of a real cock felt like, or the taste of someone else's cum, or what the thrusting of anal sex felt like. But there was that fear of the unknown, getting into a situation I couldn't handle, or getting found out.
And then the pandemic hit. Even if I was going to take the next step for real M2M sex - and I wasn't sure I was brave enough - any thoughts of that were kiboshed.
Until now. Vaccines have arrived and the end of this hellish pandemic is within sight. And if I learned anything while cooped up in my apartment, it's that life really is short. I made it through unscathed, and was vaccinated. But one thing the pandemic had done was to focus my mind and overcome whatever fears I had, and see if reality could match fantasy.
I searched for gay dating sites, found one that looked promising and posted a profile. My profile photo was a shot of me in my underwear, from the neck down. I took some other more revealing photos and placed them in "private" mode, so I could share them at my discretion. My profile said I was new to this, and looking to explore my sexuality. Safe sex was a must, and my preference was for guys my age or older, with cut cocks.
I got a lot of hits at first - I think all new profiles do - exchanged chats with few guys, but nothing was panning out. And then I saw a profile that piqued my interest: 2Bears4u. A couple, both in their mid-sixties, looking for a sub. Interestingly, they liked shorter guys. There were no photos, but the poster said he was 6' 1" and 230 lbs, and his partner was 5' 11" and 215 lbs. Both were cut. They liked oral, ass play, fucking, bondage, kink and, well, just about everything you could imagine.
I sent them a message: "New guy here. I'd be interested in hooking up if you're willing to take a chance with a guy who has no experience." I provided access to my private photos and waited.
Twenty minutes later, a reply came: "We don't normally entertain straight or bi men, and we've found that most chicken out and don't show up. Why should we take a chance with you when there's plenty of experienced subs out there to do our bidding?"
"I can only promise that I won't chicken out," I replied. "And I'm eager to give it a try."
Another 15 minutes passed. Then a reply: "You read our profile carefully, I take it. So, you know what you're getting into. This afternoon at 4 p.m. or forget it."
"Yes," I replied. "I can do that."
He sent me the address.
I closed my laptop. My heart was racing with nervous anticipation. It was just after noon, and I had a few hours to think about what I'd just put in motion. Not a video and toys - the real thing.
At 3 p.m., I had a shower, put on shorts and a t-shirt, and headed out, plugging the address into my GPS.
Forty minutes later, I arrived. The house was a two-storey Cape Cod, with a solarium on one end. It had a huge front lawn and a couple of huge fir trees that provided a bit of privacy. In the driveway was an expensive import SUV, and an old restored pickup truck from what looked like the early '50s.
There was a lawncare company truck parked in front, so I drove past and parked down the street, sticking my wallet and smartphone in the glove compartment and locking it.
My heart was racing again as I walked up the driveway to the front door and rang the bell.
The door opened. Looking down at me was a silver-bearded beast of a man, with closely cropped hair to match. He was barefoot, wearing a baggy black hoodie and gray gym shorts.
He smirked and said, "Come in, newbie. We're going to have a delightful time with you."
He had a slight British accent.
I walked past him, and entered the foyer. "Strip," he said, sternly.
The door was still open, and he was leaning against the wall watching me. I kicked off my sandals, and took off my clothes and handed them to him. He looked me over. I had never felt smaller in my life. I was nervous as hell; my legs were literally shaking.
I glanced outside and saw a young woman walking by with a dog. Her dog was sniffing the ground, and as she stood there waiting, she looked up towards us. I quickly averted my eyes. When I looked again, she was gone. After what seemed like a minute, he finally closed the door.
"You won't be needing any clothes for a while," he said with a sigh, tossing them on the floor atop a couple of pairs of muddy boots, laying askew. "Follow me."
We walked down a long hallway past a number of rooms to the back of the house, through the kitchen and into a sunlit family room. It had a huge dark green sectional couch along one wall, facing windows that looked overlooked the back yard. The windows, with open shutters, flanked a stone fireplace in the centre with a big screen TV above it. In front of the couch was an antique coffee table with art books placed carefully. At the far end sat two two leather armchairs, in front of glassed-in bookshelves with books and small sculptures lining them. Atop a small table between the chairs was a nearly fully brandy decanter and two glasses. On the hardwood floor lay an expensive looking carpet, like something imported from Morocco.
My host turned around and faced me, standing over me, inches away - an intimidating figure.
"My name is Ray," he said. "And you are?"
