This is a work of fiction. Names, characters, business, events and incidents are the products of the author's imagination. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All persons portrayed in this work are above the age of 21.
Please note: This is my first attempt at dual perspectives. Let me know if it works for you. It did for me, numerous times!
Prologue
Growing up in the north country (upstate New York) had its ups and downs. Back then, there was no such thing as being gender fluid, perhaps the closest thing was being called effeminate but to a kid in High School it meant being called a fag and that's what happened to me in the spring of my junior year. Some guys on the football team thought I was getting too close to their girlfriends and thought it would be a good idea to put me in my place.
I admit, I was a little naive back then and when I went home afterwards all upset, my father had to explain it to me and pointed out my mannerisms. Growing up with 4 sisters had a bigger influence than I imagined. My father asked me whether or not I was gay and I told him I didn't know.
My father's words stuck in the back of my mind and I started noticing both men and women in a different light. I found both sexes turned me on and while I had an easy time attracting women, it was the 1980s and trying to be with a guy was a real challenge and I didn't want that kind of stress.
In my junior year at SUNY Plattsburgh I met this woman and we were the perfect match. Ironically, she was a little dominant and I fell into a submissive roll around her but I was happy. We even looked similar and were around the same size. We wore each other's clothes and she loved it when I was dressed up in all her lingerie and fucked her brains out. It turned me on to be dressed so.
Our families joked that we must have been twins separated at birth. We got married right after graduation and started a small software company doing early biometrics applications. We never had kids because we poured our lives into the company and each other.
In 2005, my wife, Heidi, the love of my life, had an allergic reaction to something she never knew she was allergic to and died. I was devastated by her loss. I wanted to keep her memory alive and vowed to never replace her and thought, as perverse as it may seem, that I should seek intimacy from a man. I fantasized about this constantly but always used the excuse that I was too busy with my company to act upon these desires.
Thirteen years later my software company got bought out. My team and I were rich and could retire but the acquiring company asked me to stay on and relocate to Boston. There was nothing holding me in Plattsburgh except the memories of my dead wife so I relocated.
However, being single, mid 50s and moving to a new city was quite an upheaval. I decided I would change a few things, one of which was to no longer be a recluse and try to meet new people, and try to pursue a relationship with a guy, however, I didn't know the first thing about dating a guy, or meeting new people in general so I took up some new activities to help me get out and socialize with others.
I joined a car club and spent weekends going to car shows and driving to fun places but always felt like the odd man out because I was single and everyone else was partnered up. The other pastime I enjoyed was skiing. Living in Plattsburgh I lived close enough to some big ski resorts in the Adirondacks that day trips were easy and I went as frequently as possible although I always skied alone.
There were some smaller mountains within an hour's drive of Boston but not as challenging and so I thought about joining a ski club. I found a few online but had no way of knowing if they were any good or not so I started asking around the office if there were any ski clubs in the area that they would recommend. One woman in accounting said she had a good friend that was a member of a group called Ride with Pride and she skied every weekend with them and that I should check them out. She cautioned me, though, that they were a gay group.
The Ride with Pride Ski Club was having a membership event the following Friday at a local brewery and I decided to go check them out. My work colleague was spot on because the first thing I noticed was that all the men were with men, and the women with women.
I was given a name tag and introduced myself to few people and then I realized, that most people there were grouped by their sex. I thought that this could be my opportunity to meet a man and fall in love.
The membership director introduced himself, "Hi, I am Theodore Bennington, but you can call me Ted." He said, holding his hand out for a shake.
I grasped his hand firmly and I felt something that I never felt before, a shiver shot through me and I felt my penis stirring.
"Marcel Morin but please, call me Marc." I noticed his raised eyebrow and added, "My family is from Quebec but I grew up on the US side of the border."
"Interesting. Do you have any questions?" Ted asked.
"Just one." I thought about how I wanted to say this and then I got closer to Ted, close enough that if I reached out I could grab his hips and pull him into a kiss. I was so nervous that I thought I might stammer and then I said, "I am not sure how to say this, I guess, technically, I am straight as I have never been intimate with a man before but don't get me wrong, I am not opposed to it."
I stopped talking and thought about what I should say next, then, "I am interested in seeking intimate company of a man, just that I am not sure how to go about meeting one." God that must sound so corny.
"But I didn't come here thinking this was a place I could," I thought for a second for the right word to say and the only word that came to mine was, "Hookup.
I really like skiing and perhaps being around others who are gay would give me some insight in how to meet someone." I said with a blush. Wow, I guess I just came out to a total stranger.
Ted smiled at my admission and said, "Very interesting. We have never had a straight member, let alone someone who is bicruious but I don't see a problem." Ted said with a smile on his face that imitated the Cheshire Cat.
Then he added, "Welcome to Ride with Pride. And don't worry, I will keep your secret safe." He winked at me.
Ted held out his hand again and I grasped it firmly.
"Oh, in that case I guess the only person I will have to worry about hitting on me is you." I said with a smile as I continued to hold his hand and I stared into his eyes. Then from out of nowhere I said, "Has anyone ever told you, you have great eyes?" I felt a blush rise as I thought about what I just said - I am flirting with this guy and I have no clue if he is with someone. How stupid of me. Then I let go of his hand.
Unfazed by my comment Ted got down to business by saying, "Well, here is our PayPal account." He handed me a card. I pulled out my phone and paid the full amount. He looked at his phone with it dinged and said, "Welcome to Ride with Pride Marc."
He held out his hand again and we shook on it. I felt a shiver go up my back.
"Let me introduce some of the other more prominent club members." Ted said.
Throughout the rest of the evening I met a bunch of people but didn't remember many names. They were really friendly but I couldn't get Ted off my mind and I kept stealing glances at him the whole evening. I have never felt an attraction to a guy before but for some reason I was drawn to Ted. He was taller than me, bearded, and looked really athletic. He didn't fit the gay stereotype that I was familiar with. I wondered what it would be like to be with him,
Ted
This new guy, Marc, was on my mind the whole night. The fact that he was bicurious told me the his door was open but I had to be careful. Then I thought, it's been five years since I was intimate with someone so this could be a learning experience for both of us.
Jane, the club President walked up to me and said, "Good work tonight Ted. 11 new members and I like that one guy, Marcell. He looks like a catch. You seem to be keen on him the rest of the night." Jane said, wiggling her eyebrows.
"He said he was straight." I said.
"Hah, the way he was looking at you all night tells me he thinks he is straight but he looked like he had the hots for you." She said with a big smile.
Then she added, "Well, I don't think we have ever had a straight male in the club." Jane said. "No worries, if he's OK with this then it doesn't bother me."
When I got home, I Googled him. He didn't have a Facebook or Instagram, at least nothing that I could find. There was one article mentioning his name saying he sold his company in Plattsburg, NY to a company here in Boston and that he was hired on to continue running the company as a division. Not much else.
I pulled out my cock and started stroking it thinking about him and what I might do with him if it got that point. It's funny, I have never been with an older man before but this guy had me hot and bothered really quickly.
In my mind's eye, I fantasized how I would introduce him to gay sex. We would start out by kissing and touching each other. I would make the first move and pull out his penis and stroke him nearly to his peak and then stop. Next I would start kissing and licking his body as I took off his clothes.
Taking him in my mouth I would suck him to completion, happily swallowing his cum and then kissing him afterwards to judge his acceptance. If he had no problem tasting himself then I would encourage him to give me head. Afterwards, we would cuddle and fall asleep in his arms.
I knew I should have taken off my clothes but it was too late. My orgasm was messy but it felt so good. It had been awhile and there was a lot of cum. I cleaned up what I could and then threw my clothes in the washer and took a shower.
Then my mother called, reminding me that I had to do some work for the Boston Symphony Fundraiser she was putting on next month.
Marc
Over the past month I picked up a few things that made my masturbation experiences a lot more pleasurable keeping in mind that I wanted to have sex with a man. I slipped on my cock ring and then my vibrating butt plug. Turning it on to the lowest setting sent a light vibration straight to my prostate and my penis got hard. Then pulled out the suction cup dildo and affixed it to a wall facing the mirror.
I loved sucking the toy while slowly stroking myself and watching myself in the mirror. I usually edge until I can't take it anymore and then I would lay on my back, turn the virbrator to max and watch my penis shoot loads of delicious sperm all over my chest and abs.
Tonight, however, was different. In my mind's eye, I pictured it was Ted's cock I was sucking. It didn't take me long to reach that plateau of bliss only this time I came in my hand. I coated the dildo in my cum and started savoring my cum as some of it was pushed into my throat by sucking on the dildo and the remaining I kept in my mouth.
Tasting my cum and having my mouth full of faux cock really excited me and I turned up my vibrating butt plug. The sperm from my previous orgasm that was in my hand made a nice lubricant as I sucked harder and pushed the dildo deeper into my throat. The taste of my sperm, combined with the delicious friction on my penis and vibrations at my core were pushing me towards another erotic nirvana that I have never experienced before. It was explosive. Cum went everywhere and I happily cleaned everything with my mouth. God, I want Ted.
Ted wasn't far from my mind the rest of the week. I Googled Ted and found that there was a lot on him. Lots of great pics that I masturbated to at night.
It appeared that the Bennington family was steeped in old money. Ted didn't come off that way, in fact he was very likable. Perhaps, because he was gay? I also found an interesting article in the Herald about Ted having a nasty breakup with what the paper called a Trust Fund Baby from another Boston dynastic family.
I also found an erotica website one night and read about all manner of gay interactions that added to my lust and fueled my masturbation sessions. I replaced the characters in the story with Ted and I. One thing was clear, I definitely wanted to be on the bottom of our relationship.
My favorite fantasy was where I was on my back and he was on top of me, inside me, kissing me passionately. His penis hitting my special spot. Our earlier foreplay was hot and we wouldn't give ourselves the release that we both desperately wanted. Instead, we would hold off until he entered me. He is a passionate and selfless lover, making sure I always came first and then he would take his pleasure.
Ted
A month prior to our first trip I sent out an email letting everyone know about our first trip, subsequent trips, asking for RSVPs so I can get an idea on how many buses I would need. I also announced the new members and as usual everyone just hits Reply All, saying they are coming and including funny anecdotes for everyone to read, or welcoming the new members.
Marc's reply was only to me. He said in his note that he was really excited to be skiing with this group and couldn't wait to see me again. I wanted to read between the lines and say that he really wanted to see just me again but I held off not wanting to set some non-existent expectation that he actually wanted to start something.
