My Bisexual Bucket List

When the big metal door opened, my first thought was that he looked a bit like Alec Baldwin. No, not the hot young "30 Rock" version of Alec Baldwin. More like the current mature version with graying hair and a couple of extra pounds.

Still, he was definitely handsome enough for me to want to kiss when he opened the door as we first met in person. I smiled and leaned in for a smooch... but he physically recoiled. "I'm not looking for romance," he said with no humor whatsoever. He ushered me in and locked that heavy door behind me with a loud click.

I had connected with him via one of the hook-up apps after recently getting back in touch with my long-dormant bisexual side. I needed one final fling with guy sex while I was still relatively young and fit.

I had kind of a bucket list of gay shit I wanted to do one more time: suck a few really nice cocks, get a couple of world-class blowjobs, enjoy a hot threesome and, most importantly, find a guy to really fuck me properly. I'd had a couple of messy, drunken anal experiences when I was younger, and I wanted to try it one more time while I was sober and in the moment. Easy enough, right?

Well, as you likely know if you're reading this, being a married bisexual man on the downlow often sucks. And not in the good way.

Yes, there is the ever-present fear of getting caught or catching something. And you have to sort through a million flakes and wannabe "jerk buddies" on the various sites. There are also countless curious, cock-obsessed dudes trapped in sexless marriages but terrified of actually hooking up.

The short version is that attractive guys with working dicks who can host are the pink unicorns of the bi universe. Thus, you need to be patient with the bullshit, but you also have to be able to sense when the opportunity is right to take a leap of faith.

I took a few of those leaps the past couple of years -- including a couple of fun encounters with good, sexy men I met here on Literotica. I also had a gay friend who suffered from ED but happily introduced me to the joys of a mind-blowing prostate massage. And there was one steady guy with whom I crawled into bed a half-dozen times. He was kind and considerate and he unknowingly helped me check several things off my list, including a very hot threesome with another friend of his.

He also gently reintroduced me to anal sex and I soon found I loved being fucked. He was by no means a "dom," but he helped me realize how much being submissive turned me on. He called me his preppy little fucktoy and he was amazed at how a masculine, straight-acting guy like me could turf into such a cock whore. But, even that nice relationship eventually got weird and ended.

At that point, I thought about just declaring bucket list victory and calling it a day. But I still had a nagging itch for more. Specifically, I still wanted to find a real top with a big cock who would use my ass for his pleasure. I wanted to be a submissive little slut. And that's what brought me to that penthouse apartment in a nearby city that day.

When the door clanked shut behind me, I realized I was on the top floor of a largely unoccupied old office building. The building itself was a ghost town but the penthouse level my new friend occupied had been the headquarters for an insurance company or something back in the day. Now he had set it up as a crazy apartment with a dozen rooms, each decorated with sort of a different purpose or theme.

Yes, he had a bedroom, a kitchen, a bath, and an actual office for whatever the hell he does for a living. But there was also a little art gallery, a library, a weight room, a room with a golf hitting net and, of course, a fun room that was clearly set up for sex. It featured a giant video screen that constantly had porn playing along with a couple of couches and an impressive collection of sex toys.

My odd new friend had rolled a big joint and we each had a couple of nice hits. He almost never talked but finally he said, "Take your clothes off." I quickly complied.

I stood naked before him, my own cock semi-hard, as he walked around me and silently inspected my body. Then he too shed his clothes. When he turned back toward me, I got my first look at his cock. It was very big -- about 8" long, beer-can thick at the base and rock-hard.

I was, in a word, smitten.

He sat in an overstuffed chair in the sex room and beckoned me over. I dropped to my knees between his legs and proceeded to worship his amazing dick for the next half hour or so. I swirled my tongue around the head of his cock and tested how much of that big shiny dick I could get down my throat. All while looking up into his eyes and watching how he reacted to my efforts.

I stayed on the floor between his knees and followed his terse instructions to suck his big balls, lick his ass and play with his nipples. There was no chatting or making out. I was there to serve him... and I liked it.

I could tell he was getting close when he suddenly hopped up and pulled me over to a barstool in the middle of the room. He sort of nodded toward it and I got the message. I bent over the stool and spread my ass cheeks. He lubed me up and used his fingers and a dildo to stretch my hole and prepare me for his invasion.

As I wiggled my ass suggestively waiting for him to penetrate me, I was super horny to finally be fucked by a real top. This seemed like my bucket-list moment.

The head of his big, rocket-shaped cock entered me easily enough but the rest of it was much wider and girthier. He repeatedly pushed his monster all the way in and I tried, but I just couldn't take it. I pulled away and got on my knees and took his dirty dick in my mouth and cleaned with my tongue and sucked it until he shot his cum down my throat.

I left thinking, "That was weird, and I'm probably done with him."

Yet that was only the first of what turned into multiple visits. I would get a message on the app that said, "I'm open at 3. Come over. Wear some turquoise panties." And I would immediately reply, "Yes daddy."

He was the only guy I ever called "daddy." He tapped deeply into my submissive desires and I loved it. I have a busy, demanding life and a high-profile career. Everyone looks to me to lead and decide. But I occasionally crave giving all that up and being a panty-wearing, cock-sucking sissy for a stud like him.

Over the course of a couple of months, I would go to his crazy place, put on thigh-highs, garters and lingerie and wait for him to direct me. No chatting, no kissing, no hugging... just doing what he told me to do.

Sometimes he would pose me and take sexy pictures of my panty-covered ass or my hard cock. It was incredibly hot to be his toy.

I mostly stayed between his legs, nursing his cock, sucking his balls and eating his ass. With a little practice, I learned to enjoy deep-throating him. I practiced -- a lot -- and he seemed to enjoy the results more with every visit.

Sometimes he would decide to fuck me and I loved it but still struggled to take all of him. One day I had the urge to try to sit on his cock cowboy style. I pulled my pink thong to the side and lined my hole up with his cock. Eureka!

I was able to slowly work my way down bottom out on him. I finally could take all of his fat dick down to the base. It was heaven bouncing and grinding my ass on it. I looked down to see precum flowing from my slit as his cockhead banged against my prostate.

During one session I was wearing purple lacy panties and white thigh-high stockings and he decided to pose me for pictures in the big empty stairwell of the building. It totally turned me on when he would tell me what to do and then take those pictures of me. I was holding the stair rail and bending over for him when he said, "Don't move."

He left and came back holding a piece of cord and a black scarf. He tied my wrists to the banister and then covered my eyes with the scarf and secured it behind my head. I was bound, mostly naked, and blindfolded in the stairway of an empty building. And my cock was rock-hard. I was totally in his control.

I could hear him taking pics and then felt the tip of his cock tickling my hole before he shoved it fully into me. My howl of pain and pleasure echoed down 9 floors of the stairwell. He instantly snapped, "Be quiet!" before reaching down to pull off my panties and shove them into my mouth.

He proceeded to breed my ass while I was bound, gagged and blindfolded. When he finished, he left me there for a while and I could feel his cum trickling out of my hole down my white stockings and onto the concrete floor.

I was torn between with weirdness of the whole thing and the fact that it was the best sex I'd ever had. It was so kinky and dirty and hot all at once. I could certainly cross amazing anal sex off my bi bucket list if I wanted to, but I still felt unfulfilled in one way: I wanted him to fuck me missionary style.

To me, there's nothing more feminine or submissive than the idea of being on my back, legs in the air with a big cock inside me. It seems utterly vulnerable but also so connected because I'm face-to-face with the guy who's using my ass for his pleasure.

The next time he messaged to come over, I replied "Yes daddy... but I want you to put me on my back and fuck me like a girl today." Predictably, his only response was "Ok."

I stopped on the way and picked up a new lingerie set: all black lace panties and a bra with garters and stockings. (Just a note that I'm 6' 1" tall, 180 pounds and pretty fit. I look damned good in lingerie for a 63-year-old dude.)

I rode the elevator up to his penthouse knowing that this was likely going to be the last time and the finale of my bucket list adventure. As always, he was monosyllabic and weird until I came back from the bathroom dressed in the sexiest underwear ever and he said, "Fuck yeah." I secretly wished I had thought to buy some cheap high heels to complete the look but this was as close to bisexual hotness as I could get.

I wandered around the big crazy space, posing for pics and sucking his cock in several of the rooms. Finally, we got to the art gallery room, a small space with a dozen pieces of art on the wall and a padded bench in the middle.

I crawled up on the bench and got head down and ass up so he could take pics of me with the garters and stockings. I started talking dirty: "Do you like that ass, daddy? Bring your big dick over here and let me suck it before you fuck me. Do you show your friends those pictures and tell them I'm your fucktoy? I'm addicted to your cock and I'll do anything you want. Please just fuck my pussy like a woman."

I rolled over onto my back on the bench and my stocking-covered legs up in the air. He ran his hands up and down my legs and rubbed his cock on my silky black nylons. He lubed me up and stretched my hole with a finger, then two, then three. I was almost lightheaded with desire.

At last, he put my ankles up over his shoulders and leaned forward. He worked his big cock into me an inch at a time and then he started to fuck me steadily and forcefully. He reached down and pushed a couple of the same fingers he'd had in my ass into my mouth while his pace quickened. I continued the dirty talk: "Yes, fuck me hard. Use my pussy and fill me up with your cum. Please grind that fucking cock into me."

The weight of his body on top of me kept me helpless. He absolutely owned my ass... and the rest of me. I figured out later he fucked me silly for about 30 minutes. It was exactly the bucket-list fantasy I'd always had about being used hard by a big-dicked top.

I was shattered momentarily when he pulled out and left my pussy empty, but I quickly realized he was bringing his hard, slimy, dirty cock around to my mouth. I leaned my head back over the edge of the bench and he fucked my mouth almost as hard as he'd fucked my ass. He quickly came hard, and I savored, then swallowed, his salty load.

He left me laying there, stunned and extremely satisfied, as I replayed the best sexual experience ever in my head.

A few minutes later I was dressed back in my regular preppy clothes and hitting the down button in the elevator. My ass was happily sore, and I felt as sexually satisfied as I ever had.

Driving home, I replayed the experience in my head. I knew I was finally done with weird penthouse dude and I had, at long last, checked the final item of my bucket list.

Am I through with guy sex now? Well, I feel like I experienced what I wanted to experience and I deleted my account on that hook-up app. But I'm still here... and you never know who you might meet on Literotica.