Straight Andrew Takes the Plunge

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?"

"Kevin," I lied, starting to feel nervous about being here.

"Strike one," he said, with a menacing tone in his voice. He laid a hand on my shoulder and tapped it a couple of times. He then lowered it and quickly grabbed my balls and cock, and squeezed hard.

I cried out, he let go and I crumpled to the floor. He crossed the room and sat down in one of the chairs.

"Crawl to me," he ordered.

I did as he said, the pain finally subsiding, and knelt in front of him.

"Now, your real name," he said.

"Andrew," I answered, my voice shaking. Fuck, what had I gotten myself into?

"Well, Andy, boy, here are the rules," he said. "You're not a child. Do as we tell you, don't fucking lie to us and everything will go smoothly and we'll all have a grand old time."

I simply nodded.

"Stevie, our guest is here," he called out.

Footsteps approached from down the hall. I turned around and there stood a stocky, bare-chested guy with nipple rings and tattoos covering his arms. He had a bit of a paunch. He was also bearded, with touches of gray, but bald.

Stevie walked in and patted my head, before sitting down in the other chair.

"Stand up," he said, without a trace of an accent. "Turn around slowly and bend over and show us your old cherry ass."

I slowly turned, and as I did, saw two gardeners in the back yard, glancing up at me. I turned beet red, as I bent over and exposed myself to Ray and Stevie, furtively glancing to my left out the window to see if the hired help were looking in. They had stopped working and were now staring, with big grins on their faces.

"Pull your cheeks apart," Ray commanded.

I complied.

"Nice," he said. "Turn around and face us."

I turned and faced them. I could feel my face burning as they looked me up and down. Both were smirking, enjoying my nervousness and the show they were providing the gardeners.

"You're a chubby little guy and not very manly," said Ray finally, as he stood up and walked by me towards the hall. "You'll do. Come, Andy. We're going get you into the shower and cleaned up for playtime. Maybe even let our crew outside have their way with you in the garage when we're done."

"I showered before I came," I said.

He stopped suddenly and turned around slowly.

"Strike fucking two," he said. He slapped my face, turned around and continued walking, with me following quickly, my facing stinging. We went up the stairs, through the main bedroom and into an en suite.

He turned on the shower and motioned me to get in, and left the room wordlessly. I entered and washed myself from head to toe.

Once I finished, I towelled off and walked into the bedroom. There was a huge antique armoire and dressers against the far wall, and night stands beside the king-sized bed. The blinds were open, and light flooded in. A sheet had been draped across the bed.

Stevie was laying on it, leaning against the headboard, naked with his legs splayed wide. He motioned me towards him and pointed to his cock.

"Playtime," he said, with a smile that was slightly unnerving.

This was it, there was no turning back. I walked towards him, climbed up on the bed and crawled towards him. I knelt down and reached out for his limp cock - thankfully it didn't look massive - and started stroking it. He placed one of his hands on my head and guided it downwards.

I kissed it first, then opened my mouth and put it in. It felt wonderful, soft and spongy. I swirled my tongue around the shaft and across the piss hole. I could feel it starting to get hard. I kept sucking and swirling my tongue around until Stevie was fully hard - I guessed he was about six inches, but not too thick. I felt proud that I had gotten him hard so quickly. I cupped his balls, and gently massaged them, alternating between licking his shaft from top to bottom and sucking him.

"Lick my taint," he commanded.

I bent lower, lifted his balls and started licking. It smelled a bit musky, but not unpleasant. I could feel my own cock stirring, getting hard. I kept at it for a few minutes, when he grabbed my hair, lifted my head and guided me back onto his cock. I continued sucking, tasting some pre-cum, and working his cock. Occasionally he would take it out and slap my face with it.

"You're not bad for a rookie, an old rookie at that," he said with a mirthless chuckle. "And lucky for you, both Ray and I have been known to blow a couple of loads each in the right circumstances. Maybe today will be one of those circumstances."

As if on cue, I felt Ray climb onto the bed behind me. He pulled my legs so I was now lying on my stomach, arms holding on to Stevie's legs, sucking his cock.

Ray slowly stroked my legs, running his hands up towards my ass. He gently slapped my cheeks a couple of times, before grabbing one in his hands, rubbing it. Stevie grabbed my head again and lifted it off his cock. I looked up, and there was that smirk again.

Suddenly, Ray started spanking my ass. I cried out, but he kept at it. He must have spanked me five or six times. Fuck, it stung. He then kissed my tender ass, spread my cheeks and started tonguing my ass. My cock, which had quickly gone soft during the spanking, started to stir again.

Stevie told me to work on his balls. I alternated between kissing, licking them and taking them into my mouth, as Ray continued working my ass with his tongue. It was amazing, and I was raging hard.

By now I had lost track of time.

Eventually, Ray stopped, and I felt lube being poured on my crack, and his hands rubbing it in. He inserted one finger and then two. He took them out, and replaced them with a dildo. It entered smoothly, thankfully, and he twisted it around, pulling it in and out.

I moved back onto Stevie's cock, working it from base to tip while Ray continued playing with my ass. I could feel Stevie's breathing get a little faster, and knew he was about to cum. I was about to get my first mouthful.

Suddenly frightened, I started lifting my head off his cock. He grabbed my head with both hands and held it there, grunting, "Swallow it all, bitch."

Ray stopped playing with my ass. Suddenly, Stevie grunted and I felt warm, salty cum filling my mouth. I swallowed as much as I could, but it was like a fountain of cum. Some of it leaked out of my mouth, and dripped down is cock. Finally, he was drained. He lifted my head and ordered me to clean his cock. I licked up the remaining cum, and could feel his cock slowly going limp. It tasted good.

Ray now moved up and was laying on top of me. I could feel his hard cock rubbing along the length of my crack. He bent down his head, and whispered into my ear, "Time to take your cherry and paint your insides with my cum."

"You need to use a condom, please, please," I cried. "My profile said only safe sex! Please, don't fuck me without a condom! Please!"

I tried to struggle, but he outweighed me by some 60 pounds. Stevie grabbed my arms and pulled them forward. I was trapped.

Ray laughed, and said, "Bitch, you are going to take it bare. We're both clean and tested regularly. I am going to breed that cherry ass of yours and you are going to thank me when I'm done. Now, you can continue to struggle and make it hard on yourself, or we can do it the easy way. You knew what you were getting into when you read our profile, when you reached out to us and when you came here. Nobody forced you. Hell, you just swallowed his seed and let me play with your ass."

I knew there was nothing I could do. I was trapped and had nobody to blame but myself. Fantasy is one thing, reality can be quite another.

He moved, and I felt his cock begin to slowly enter me. It was bigger than Stevie's in girth and longer. It hurt a bit and I held my breath until he was fully in me. He started fucking me, slowly at first, then harder and faster, before slowing down again.

"Don't want to blast too soon," he said. "I want your first time to last. And I want to savor every minute of taking your sorry old ass."

I'm not gonna lie. It started to feel good. Then it felt fucking great. I had a real cock in my ass, not a rubber dildo, stroking in and out. I started moaning, betraying my feelings.

"Oh, the little bitch likes it," Ray said. "They all like it when I fuck them, and you're no exception."

Stevie let go of my arms and slid down, and once again his cock was in my face. He grabbed it and pointed it towards my mouth. I opened, and he slid it in. My spit roast fantasy was now reality.

I sucked his cock, again swirling my tongue around while he held onto my head. He hardened quickly and started thrusting. I gagged. Thankfully, he pulled back and let me go at my own pace. Ray continued fucking me, alternating between fast and slow, propped up by his arms now. I have no idea how long this continued, but was amazed at Ray's stamina and ability not to cum.

Meanwhile, Stevie began breathing quickly again and I knew he was about to erupt in my mouth. I grabbed his legs, and suddenly he pulled out and sprayed my face and hair with his cum while laughing. I felt it dripping down my face, and I licked what was around my mouth. I don't know how he managed two big loads in such a short time-span.

Ray now ordered me up on my hands and knees and began fucking me doggie style. He reached around and grabbed my cock, which was still rock hard.

"Looks like he really likes it, Stevie," he said, he said as he began jerking my cock.

"I'm going to cum," I said, less than 30 seconds after he started masterbating me. Pathetic.

Ray pulled me up so I was on my knees, still fucking me, and Stevie slid down in front of me again. I came. It was like never before, strings of cum splashing onto Stevie's cock and stomach.

Ray began to breathe heavier and his thrusts became quicker. He grunt-yelled, and I felt hot cum shooting up my ass. Spurt after spurt after spurt, until finally, he stopped, and I felt him relax. I could feel his hot breath in my left ear.

"That's a good, bitch," he said, as he pulled out. "Now lick your cum off Stevie."

He got off the bed and went into the bathroom. I heard the shower, as I leaned forward and licked my own cum of Stevie, savoring every drop. He then crawled off the bed and went into the bathroom.

What now, I thought. I just laid there, with cum dripping off my face and out of my ass. I could hear their voices and laughter.

The shower stopped, and Ray came out, towelling himself off. This was the first time I had a good look at him without clothes. He was hairy and more barrel-chested, and harder than Stevie. He definitely worked out.

He put on some shorts, and left the room, returning about a minute later with my clothes. He threw them on the floor by the bed.

"Get dressed, you're done," he said.

Stevie was standing in the bathroom door, naked and just staring at me. I got off the bed, grabbed my clothes, and dressed in silence, feeling their eyes on me the whole time. I was a mess, dripping with cum, about to leave the house and walk down the street to my car. I worried someone would see me in my own version of the walk of shame. As I walked out of the room, I felt the abuse my ass had taken. I gingerly walked downstairs.

Ray followed me to the front door.

As I walked out, he said, "Do come again, bitch. We may even have some friends who'd like a piece now that you're broken in. A little gang-fucking-bang, as it were."

I walked to my car quickly, got in, started it and began the drive home, the smell of cum hanging in the air. I opened the window.

I smiled. I felt great.