The Bet

The past year has been a troubling time. The population of the planet has been caught in a state of prolonged chaos; sickness reigned and families have been destroyed. Society has seen an upheaval unlike anything that existed in the past hundred years. Those of us living through this pandemic have been forced to find comfort wherever we can and my comfort has been in my memories of past joy and pleasure.
Memory is fleeting and at times unreliable but it does have one positive aspect; it is flexible, allowing those people possessing the specific memory to see it for what it is, was or could be. If something is troubling or disappointing, an ingenious person’s subconscious can edit parts of it, rewrite the script or, in the direst situations, erase the story entirely. Many of us now get to rewrite our histories and tweak the stories that make up our lives, many without knowing it.
One story in my collection of memories that I have chosen to edit involves a high school friend named Richie. This boy was not from my neighborhood so the only real interaction that we had at first was in school but over time we might meet up on the weekend at the homes of mutual friends. We had a lot in common and had all sorts of goofy fun when we did get together so this was a very pleasant part of my life at the time. By the time that we reached senior year in high school we were 17 years old and already a bit wild but in a good way.
Together with our group of friends, we would pass the time on Saturday and Sunday playing pool, tinkering in the basement workshops, listening to music and talking about the girls that we knew. Richie usually had the craziest stories about girls and all the sex that he had with them but most knew that his stories were fabrications and told in a good-natured fun sort of way to elicit a laugh. We did laugh and we made fun of each other as kids did back then; nothing was serious. Richie even went so far as to bet a blowjob on one silly thing or another and if he won he insisted that someone owed him one and if he lost he would laugh it off saying that no one took him up on the bet in the allotted timeframe. We had plenty of laughs over the premise but nothing ever came of it.
One afternoon three of us were hanging out playing pool in the basement of Richie’s house and there was bet suggested on the sinking a certain ball. Richie said that one of us would have to give him a blowjob if he made the shot but knowing his skill at pool I quickly declined to participate. Our other friend was not fast enough to do the same and before he got the words out of his mouth Richie sank the ball in question. Richie started laughing hysterically since he finally won the bet he always wanted to win, putting someone on the spot. Naturally, our friend unceremoniously told Richie to fuck off and simply walked out. Richie and I had a good laugh and continued with a new game.
It was not long before circumstances arose that lent themselves to a new and different wager. I had to make a specific bank shot and Richie said that I would never do it; normally he would prove to be right. Nevertheless, as he made his predicted wager I casually took the bet and, without much preparation and time to choke on the shot, I sank the ball in the required pocket. I looked at Richie and said, “Okay big shot, now what are you going to do?”
Richie had a fallback for these type situations and he played his predicted next card. He said, “Whip it out.” Now usually no one would take him up on this because most of our friends were reluctant to exposing themselves in front of others, opening themselves up to Richie’s ridicule for the sake of a silly bet. Today the calculation was different. No one was here except Richie and me and he couldn’t make fun of me in an empty room. Richie walked over to a chair and sat down smiling broadly figuring, I believe, that he had won again. But not so fast.
I slowly walked over to face Richie as he sat in the chair and unzipped my jeans. His eyes became a bit wider as I reached into the fly and pulled out my semi-erect penis, pointing it at him. I wondered what he would try next to avoid paying up on his lost wager or would he really do it. To my surprise Richie leaned forward without hesitation and gently wrapped his lips around the head of my now erect cock. He looked up at me and then proceeded to move his head up and down allowing the shaft of my dick to slide in and out of his mouth. I was awestruck and excited by what was happening but not only because I had finally gotten Richie to fulfill his bet. I was happy and excited because I had developed a physical and emotional liking for him over time and wanted something more sexual in our relationship. Richie was doing to me what I ultimately wanted to do to him but could never bring myself to be bold enough to initiate contact or broach the subject with him.
Richie must have been reading my mind, or perhaps he picked up on the unconscious signals between us and felt as I did, because he leaned back without saying a word, unzipped his jeans and pulled out his stiff cock. “Now it’s your turn and don’t think of backing out. I know you want it as much as I do.” he said. I couldn’t utter a sound so, without comment or protest, I looked into his eyes as I went down on my knees and took his erect penis into my mouth. It tasted wonderful and the smooth skin of its head was a delight to my tongue. I moved my head up and down listening to Richie’s soft moans and words of encouragement. Fairly quickly I felt his muscles stiffen and his hot cum shot into my mouth, hitting the back of my throat.
I let his cum linger in my mouth for a while before swallowing it so that I could relish the taste of him. As I savored the experience, I soon realized that while Richie lost the bet he got the blowjob anyway; this was quite unfair in my opinion. Still on my knees, I looked up at him and told him that he truly owed me a blowjob and that I intended to collect it. His only comment was to wonder out loud what people would say when he told them that he got me to suck his dick on a bet and that he shot his load in my mouth. His bravado was legendary and most took it with a grain of salt but I warned him that if I hear any of this come back to me I would bite the tip of his cock off the next time I took it into my mouth. He laughed and said that he would never take that chance since having a steady blowjob was always better than spreading some silly story.
As I headed home on the bus, I wondered what really set things into motion between us and how it managed to culminate with sex. Richie and I were friends and we definitely liked each other but it did not seem like the type of romantic entanglement that would have existed with a girl. I did not feel embarrassed or ashamed about what transpired but, on the other hand, I did not seem to feel much of anything and this puzzled me. I could still taste his cum in my mouth and smell it on my breath, both pleasurable sensations, but what comes next? Was it just the sex that I wanted more than a romantic sexual relationship? We didn’t kiss that day and if I am truly honest with myself I would admit that that didn’t bother me. I wanted to suck Richie’s dick and feel him cum in my mouth and Richie wanted a blowjob; we both succeeded in getting what we wanted most but something was missing.
Richie and I hung out as we used to and even managed an occasional blowjob every once in a while, but we never went beyond that. After we graduated and started working, we drifted apart as it seemed too difficult to move forward and build upon what we once had. When I look back on those days, I imagine things taking a different turn but that might simply be wishful thinking based upon today’s more tolerant approach to gay relationships having seeped into my consciousness. Times were different then and it would be difficult to live an openly gay lifestyle or even one remotely non-traditional, or is this just an excuse for not pursuing a relationship with someone I cared about? Many gay people shied away from openly displaying it in public and most lived in a closeted world. Richie and I were good friends and that would be fine but it would be impossible to be too affectionate in public. Perhaps it was this fear that stifled my view of intimacy and ended what could have been a nice relationship. We never had those moments of making out in the car or in a darkened room, or holding hands as we walked on the street; it is a shame and something that I often regret.
When I remember the events of the day that we played pool in his basement, I like to add a bit more romance into the equation. We still have sex but this time I introduce kissing, passion and mutual orgasms. I see a tender goodbye that afternoon and a developing romantic story that goes on for a while. We might fall in love and go steady as was the norm in that period. Richie could give me a small ring or even an ankle bracelet that I would wear under my socks so as not to draw attention to our secret. It would be a beautiful memory to have now, a long-ago love story that would keep me warm on cold nights instead of remembering the truth and wondering about what could have been. A simple bet and two different stories of the circumstances surrounding it. Hopefully I will live long enough for my memory to decide which one to keep and which one to discard.