Matt Chessen
Oct 11, 2015 · 14 min read

Getting to the President was just too easy. It was the middle of his re-election, so all I had to do was call the local campaign office and find out when his next fund-raising dinner would take place. Cleveland…that’s great. Campaigns are required to publish the names of all the people who donate over two hundred dollars a year, and I just scrolled to the top of the list. A bit of googling told me who the top five were. I needed to go to Cleveland and find one of them.

I checked the arrivals and departures at Washington Dulles and found a Southwest flight heading to Cleveland in two hours. I had shifted from Miss Lily, the portly asian entrepreneur, to Lu Wei, a Chinese national journalist, but I wanted a Ride with a U.S. passport and no complications. So I bought Lu Wei a ticket to Chicago on his iPhone, passed through security and then lingered around the Cleveland gate. I saw an older white guy approach the gate, look around and then retreat to the bathroom. I followed him in.

We were alone, so it was perfect. We did our business, washed our hands, and on his way out of the bathroom, I gave him a double-take and smiled in recognition. Of course I’d never met the guy, but I’ve learned that this always makes people think they should know you, or maybe they knew you and forgot. When I put out my hand and said “Cleveland right?” he instinctively took it, and I was in.

I used the handshake to steady my old ride as he wobbled on his feet and fell backwards. I’d only been riding him a few minutes, so he’d come back fast. I pulled him Lu Wei close with two hands as he regained his balance. My ride was just past sixty, but he was in solid shape. I dipped into his experiences — he liked to work out and row, which explained his barrel chest.

“What happened?” Lu Wei asked, baffled as to why he was in the bathroom.

“You look like you had a little spell,” I said. “You look fine now.” I patted him on the shoulder. “Have a nice day.” I turned and left the befuddled man to his confusion. My new vessel had a bulging leather wallet with seventy-six dollars, two credit cards, a drivers license, some old business cards, a couple of grocery store courtesy cards and a few wrinkled pictures of his family. In his other pocket, he had a boarding pass and a cell phone.

I still had plenty of time before the flight, so I found the most crowded seating area, wedged myself in between an obese heavy metal fan and a young attractive couple, and relaxed so I could enjoy one of my favorite hobbies. I snuck my arm across the top of the row of seats and started tasting my neighbors.

Behind me to my right, my mind explored the short, attractive mid-western girl with her look-at-me four inch heels and silicon enhanced cleavage spilling out of her top. More sexy than beautiful, you’d still think she’d be happy, but she sat in the waiting area with spikes coming from her eyes. She both loved and hated people starting at her pretty face and bulging tits. Something was there. She was neglected or abused, maybe by her father and now probably by some older guy — a stand in for dad. Now her whole image was about getting male attention she craved, but was also terrified of.

My mind slid away and I tasted the young couple sitting next to me. They were both in their early twenties, probably grad students returning to university. He felt gangly, and awkward, with a bit of hipster coolness but without much confidence to go with it. She was comfortable and attentive, but also slightly peeved. He kept trying to engage her in conversation as she studied her iPhone. She responded politely but shortly. He felt like the son of working class parents, in college on scholarship, reaching for something better. Her parents were affluent and professional, and she and her husband would probably be the same. It felt like she enjoyed the relationship they had and cared for him, but she knew she was out of his league and their time was finished. They would break up when they returned to school. She stood up and my consciousness returned to my ride.

She squatted to retrieve something from her bag. I admired the way the smooth denim of her jeans caressed her buttocks. She turned back to her seat. Her sweatshirt was loose and fell open slightly, revealing the barest curves of her upper breast. She must have felt me probing her with my eyes, because she flipped her had up and fixed me with a look that could have cut iron. I smiled and winked. Women hate it when you pretend not to look when they know you are. Better to just go with it and try to flirt. But my ride was just too old. She gave me the creepy old man look, switched seats to the far side of her boyfriend, who she cuddled for security. Perhaps I bought him one more week with her, lest she risk the free market and have to fend of men my age in bars.

It was time to board. My ticket was coach. I hate coach and needed to upgrade. But more importantly, something was stirring in me. Riding Chodak was an exercise in Buddhist restraint. At first it had been miserable, but after about six months, I didn’t even think about it anymore. It was all a part of washing away the tanha, the desire. But now, the tanha had retuned and I needed to let the poison out.

I really wanted to get laid.

As we were queuing, I looked around the boarding area but didn’t see anyone who matched the profile. So I bumped around in the priority line and shifted into a bland business executive.

“Whoa,” I said from inside my new ride, “you ok there sir?” I said, steadying the elderly man I departed. He wobbled a bit, but didn’t fall. I hate it when they fall. I feel so guilty.

“Uh, yes I uh.” The poor guy was baffled, wondering how he got here from the bathroom.

“You’re going to Cleveland sir?”

“Uh, yes, yes I am.”

“Well, you’re in the right place.” I turned and handed the gate attendant my first class ticket. He’d be fine.


On the way to Cleveland I sipped complementary Prosecco and scanned my ride’s memory. He was in town for a few meetings with an auto parts supplier that his company provided IT services for. Aside from a few drunken adventures in Vegas, and a homely, slightly overweight girlfriend, he didn’t have much going on in the mating department. I needed a more eligible ride if I was going to find the kind of woman I needed right now. My thoughts trailed back to the silicone enhanced chick at the airport. She would probably be good for a turn or two. There’s nothing more exciting than sex with an emotionally volatile woman. But I wanted a couple. A hot, young couple.

In Cleveland, I checked into my hotel, had dinner, then went out to Tremont to find my dates for the evening. I strolled up and down the street and examined the menu. The lesbian pair with the tattoos and dyed hair looked interesting, but I wasn’t up for anything offbeat. I just wanted some straight, deeply loving, hot sloppy sex. I found my playthings coming out of a sushi bar on Professor Ave. She was just my type — dark curly hair, hazel eyes, petite yet shapely. Her husband was a shade under six feet, well dressed and had a big smile. They walked arm in arm out of the restaurant, and I could tell they were in love. Perfect.

I walked briskly by them and brushed him on the hand. And I was in.

I turned to catch my old ride, and while he stumbled a bit, he caught himself and just kept walking like nothing happened. People are strange like that. Have you ever been driving and you don’t remember the last ten miles because you were caught up in thought? I think it’s like that for some people. They blink out of consciousness in one place, wake up in another, and they just assume they weren’t really paying attention.

“Are you ok Peter?” She was talking to me.

“Yeah, I thought that guy was tripping so I tried to catch him,” I said. “I think he’s fine.” I search my ride’s memory. He and his wife Shayla are supposed to go to a movie. Good thing they live in the neighborhood.

“Honey,” I said in my ride’s most seductive voice, “I know we’re supposed to go to the movie and all, but how about we pop back to the condo for a little dessert first?”

“Dessert?” Shayla asked.

I bend over and kiss her neck below her ear. Her hair smelled like lavender and the feeling of my lips brushing her earlobe sent a shiver up my nethers.

“Oh, dessert!” She said excitedly. “What are you cooking?”

“I was thinking about warming you up for about twenty minutes, then simmering both of us for an hour.”

“And then?” she said, sliding her hand from my hip to cup my buttock.

“And once you’re hot enough I’m just going to lick you all over.”

“Mmmm, that’s sounds delectable.”

I picked a good one. Game on.


Ten minutes later we were in Peter and Shayla’s bedroom, pulling each other’s clothes off. I really got lucky with this one. Shayla and Peter were trying to have a baby, so there wouldn’t be any condoms in our way. And whatever I was doing, she loved it. Whether people like it or not, they get into habits in the bedroom, routines. I think this is one reason sex with a new person can be so arousing — you don’t know what they’re going to do, and it adds an element of excitement to the mix. I could tell my style was different than Peter’s and Shayla was responding accordingly. And she was gorgeous. My first time, I orgasmed quickly. It had been over two years and it felt unbelievable. Shayla looked at me on top of her with those big brown eyes, affectionately but with a hint of disappointment.

“That was more like a quick sear,” she teased.

“It’s ok honey, I’m not done yet.” I rolled to her side and pleasured her with my hands. She closed her eyes and soft moans turned into pants and squeals. She was close.

I placed her hand on top of mine, and shifted into Shayla.

Peter was disoriented so I slid his hand away and finished with Shayla’s. My whole body arched and my pelvis shook for what seemed like an entire minute. I gasped for air and looked down at my breasts and erect nipples as the contractions lessened. Men have no idea how much more powerful the female orgasm is, and how good the rush of oxytocin can feel. It was like heroin for the soul.

I fell back into the bed, flushed and euphoric and looked over at Peter. He was understandably confused. A minute ago he had been walking down the street with his wife. Now he was in bed with her watching her orgasm. I slid my hand across his cheek and gave him a quick peck on lips.

“Thank you dear, you were amazing” I said and got to my feet. I walked to open the bathroom door, but opened the closet instead.

“You ok honey,” Peter asked.

I laughed. “Well I guess we’ve both had too much to drink.” I checked Shayla’s memory and pointed to the bathroom door. “I’m taking a shower.”

“You want some company?” Peter asked.”

“Not this time dear,” I said, tossing him a washcloth for cleanup. I’ll be right out.

I closed the bathroom door and ran the shower until it was steaming. The orgasm plus the hot shower was immensely relaxing, but as I ran my hands across Shaylas body, I became aroused again. With one hand between my legs, and another on my breasts, I brought myself to orgasm again leaning against the shower wall. I usually prefer riding men, but sometimes it is very, very nice to be a woman.

When I got out of the shower, Peter was asleep. The campaign fundraiser wasn’t until the following night, so I had some time to relax. I climbed into bed with him, curled up in his arms, closed my eyes and shifted back to Peter.

I could feel Shayla tense up when I shifted out, so I pulled her head onto my chest, my left arm circling her back to gently caress her bottom.

“You ok babe?”

“I just had the strangest sensation,” she said, at first tense, but relaxing as I pulled her close. “the last thing I remember I was about to come, then I was right here…like I lost a few minutes.”

“You did seem pretty relaxed.”

“Do you think I might have had a stroke?” Shayla said, concerned.

“Nah,” I said, yawning. “I’ve had that happen before. I read somewhere that orgasms can cause temporary memory loss. I’d just relax and forget about it.” She seemed to accept this and snuggled deeper into my arms. In a few minutes her breathing slowed and she drifted off to sleep.

I never knew what to say to people about the gaps in their experience but I knew obsessing about a stroke probably wasn’t a good way to go. So I tried to assuage their anxieties. But my experience of life was nothing but moral dilemmas.

I tried to only ride single people as much as possible, preferably reclusive introverted ones. Married couples were tough because married couples talk a lot and they tend to discover the gaps. When I’ve been riding them, they don’t remember anything. This disrupts marriages and families, which I don’t want to do. If Shayla talks to Peter about this conversation tomorrow after I’ve left, he’ll have no recollection of it, and then he’ll start wondering if something is wrong with him. So I try to limit the potential damage as much as possible by riding couples for a very short amount of time, or by riding one solitary person for a long time. In betweens tend to not go well.

But with Shayla asleep, I could relax until morning.


I awoke early, brushed my teeth and returned to bed. A few minutes of gentle stroking of her butt and breasts woke her up gently, and we made love again. This time I delayed my orgasm, and shifted into her just as she came. I’m not attracted to men, but I’ve learned that a dick inside my ride’s vagina during orgasm feels pretty much perfect, so I usually just close my eyes and go with it. Peter was obviously discombobulated since he stopped moving, so I gyrated against him until Shayla’s climax ended, then shifted back into him. I finished with my face pressed into her warm neck and collapsed into her, panting. There is nothing better than two orgasms from a man and a woman a few seconds apart. Two very different orgasms — one open, full body series of contractions — and one sharp, spasming release.

You might think it’s gross to swap all those bodily fluids, especially with me as a straight guy. In the beginning, it was. But after you’ve ridden South Asian prostitutes with scorching STDs and indigent alcoholics with DTs so bad they can’t keep food down, you don’t find some yuppie guy’s come so bad. I’ve ridden hundreds — maybe thousands of people. One thing I’ve realized is sexuality is pretty malleable. We’re all born with tendencies, and society and culture shapes those tendencies one way or another. Some are strictly homosexual, as their bodies will tell you. Some are very, very straight, and they’re bodies let you know that too. But sexuality is a bell curve and most of us fall somewhere in-between.

When I was younger my friends and I used to play a funny game with girls to get them to relax and open up. Guys would join in too. We’d ask them, ‘if I took your brain out of your body and put it in an attractive guy, would you have sex with men or women?’ Most guys said they’d have sex with women if they were in a woman’s body. Interestingly, most women said they’d have sex with women if they were in a man’s body. They said it seemed more natural and the parts all fit correctly, and that made sense. But at the time, I wondered why guys wouldn’t go for guys if they were in a woman’s body. Now I think it’s the balls. The cock is easy. Cocks are like titties — everyone loves a good pair of titties. But it takes a particular type of person to really love a pair of hairy balls in your face. I’m not a fan of balls.

I felt Shayla fretting, so I rolled off of her.

“Peter it happened again.”

“What did honey?”

“I blacked out again, when I came. I think I need to see a doctor.”

“You’re fine honey, I bet your blood sugar is just low.”

“Peter I’m serious.” Shayla pushed me off her and sat up in bed. She grabbed my hand and put it to her forehead. “Do I feel hot to you?”

I moved my hand to her breast. “You feel damn sexy to me.”

“Peter, be serious,” she said, moving my hand away. “I’m going to take my temperature.” Shayla went into the bathroom and I could hear her rummaging for a thermometer.

It was time for me to depart. I was interrupting the marital bliss and possibly giving Shayla a complex. And I was having post-orgasmic remorse. I just had sex with two people who didn’t know they were having sex with me. Was this rape?

On a meta-level, I wondered why I was having these thoughts. I never worried about it before. Shit, maybe all that time riding Chodak had given me a guilty conscience.

I thought back to my previous sexual escapades with couples. It was always consensual. I never put together a couple for the first time, or had sex with anyone who wasn’t already doing it regularly. Well, not usually.

Well, after I thought about it, I realized that actually wasn’t true at all.

How many surprise pregnancies did I create? Or how many women woke up in the morning with a strange man next to them? Those were the single people. Yeah, that was pretty wrong. But I was young and didn’t know any better.

With Peter and Shayla, it was different. With couples, for all they knew, they were making love with their partner. Their partner might be doing new things in a way they’d never experienced, but they thought it was all part of the relationship. Was this wrong?

My whole existence was wrong on some level. There was no way to live without inauthenticity. My body was gone, and I only lived on through others. So if I could only make love through others, so be it. I didn’t intentionally hurt anyone and I liked to think that I was adding a splash of variety into relationships.

I wondered if Shayla became pregnant and had a baby whether it would be mine. But I doubted that shifting into someone would change the DNA of their sperm. The kid would be Peter’s. I hoped. If not, there would be many many women with difficult questions to answer after childbirth. I made a mental note to check in on some of my old relationships and make sure their kids looked like their biological fathers.

Shayla had assuaged her fears about a rogue fever but had moved her naked body to the desk, where she was surfing the Internet for possible causes to her memory loss. I sent myself on an errand for coffee and muffins, and headed out to the corner bakery. I shifted into a passerby on the way. Peter and Shayla would just have to find their own answers to the mystery of the last twelve hours. I had bigger fish to ride.

USED: the game of life

Pre-publication exclusive for Medium readers. Comments and feedback encouraged.

Matt Chessen

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AI focused DiploTechy writer of fiction & non-fiction about the future of tech & humanity. Author of Broad Horizons Opinions mine not USG

USED: the game of life

Pre-publication exclusive for Medium readers. Comments and feedback encouraged.

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