A gay story: MWM Bisexual Musings Ch. 01 We ran around the neighborhood together for years, the aggressive son of the only divorced couple we knew that went to St. Patrick’s Catholic Church in the late 70s/80s. Jack had knocked out my front teeth in kindergarten, was a back roads drinking buddy, was a better athlete than I spurring on my competitive side and became my freshman college roommate.
Jack was part of the my second male experience, though it was thinking only my sexuallity, like most people, considering everything…if given the opportunity. He would clean the room naked, after ROTC, his large cock semi-hard, shooting clothes into the hamper, my eyes mesmerized.
Why he didn’t he come on to me, or me on to him, our 80s disposition on homosexuality to big to overcome. I would alternate thinking of young women, or Jack’s cock, masturbating just below him in our bunk, especially during slow times meeting women at the college.
We attended the same college for a time, and then soon after I transferred, he needed a place to stay, he had two failed jobs after graduation, ending up in my basement. There he courted his future wife, having met that summer and two years later they were wed.
My first experience came when I was 18 and a senior in high school, wmy 19 year-old friend Thomas was back from college. He was a neighbor and we had learned golf, front yard football and built things in his garage together with his Dad’s tools. He introduced me to beer and had always dated the prettiest women in high school.
It was late after a football game when he asked me about my cock.
“How big is it, Donnie?” He said after some drinks, we kidding about my lack of dating prowess, though I had gotten my first blow job on my 18th birthday.
“My cock?” We had talked about taking a piss just prior, blushing I ignored the comment, his ire bristled. He had some middle eastern decent, dark and swarthy, and he approached me.
There was no warning, I looked down and he was holding his cock out, it was a lot longer and thicker than mine, a good two inches I thought. I had measured mine at 6″, it was skinnier, though Kerri, who got my BJ cherry, called it ‘handsome’.
“Ummm, mine’s 6 inches I think…”
“Figured,” he said, and put it back inside his pants. “Are you hard?”
“yeah…” I said softly, getting a smile out of him.
“Oh often do you jack it?”
“Too often…” I said, noticing my cock growing even firmer.
“Take your pants down,” he said, and lowered his jeans, it standing firm and large. I fumbled for my waistline and was soon naked from the waist down. He looked at it mine, and stroked his.
“Kerri said it was ‘handsome’…” I joked, trying to cut through the uncomfortable sexual tension.
“Mine’s a ‘hand’…and then ‘some’…come hold it Donnie…”
I moved to him, he reached down and he wrapped finger around me hard, I closed mine and felt his. It was soft and firm, the diameter felt amazing compared to what I had been stroking all my life. He began to slide his hand back and forth on mine, and I followed his lead.
I didn’t make eye contact, just staring at his, the precum funneling out of the tip, he leaned back on a pile of cement meant for their new patio and moaned.
“Mmmmm, faster Donnie,” he said, stroking me faster to his own command.
“Shit!” I exclaimed, my cock sending a flume of cum out, he pulling his hand away getting none on it, while it splashed on my jeans on the floor.
“Put mine in your mouth!” he commanded, my embarrassment for cumming leading me to my knees, the post orgasm let down began to kick in. “Feel it on your lips at least.”
“Ohhhh,” he moaned, his hand still at the base, my lips on the velvety shaft, the tip on my tongue, these feelings, smells and tastes of that moment still rise up now that I’m close to 60.
I pulled off him, the spell broken from my climax, the cum cooling on my groin evaporating in the fall night air of the garage.
“I’ll finish myself,” Thomas said, stroking faster, leaning over and finally cumming staring at my face and limp cock.
We never spoke of it again, the next day admitted only that he had some shots and ‘didn’t know what came over him’ and now is married, many grand children, very right wing and all about good Christian values. We had met over the years, but they lived south of us by five hours and after attending our wedding I didn’t see him much.
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Jack had just been divorced when he called to stay at our house, alone this time.
He was 60 and I was eight months away from turning the same. This was 41 years from him dancing naked, my thoughts of him and our college years. Jack and his wife Cassie had two kids later than my wife Mel and I, and they were both in college. He had suffered from PTSD from his time in IRAQ, though stifling it enough to make the rank of lieutenant colonel in the Illinois National Guard.
The trauma, years away from Cassie and the kids training and service, and the neighbor across the street, drove a wedge that they amicably ended their marriage just a couple months prior to his recent call.
“It is Todd?” Jack told me their daughter asked about the neighbor and Cassie, but Jack didn’t confirm or deny any of it, moving instead onto all the things he gave her in the divorce.
“It’s too bad,” Mel, my wife said. “We were getting to see them over the past year more often, them traveling through seeing their folks.”
Aging parents and funerals, the glue that binds you to your past. Jack and Cassie both visited a half-dozen times, though when we were in the man-cave, separate Cassie would tell Mel how bad it was, and Jack, well was just Jack.
He was a fit, 5’9″, natural muscle tone, though he added weight the past couple years, his hair short but intact, was into wearing those colored thick framed glasses. He was the product of an olympic athlete in his father and Minnesota high school basketball star in his mother. One recovering from a stroke in Michigan, the other bedridden in Nebraska. He had the body and shape of an athlete.
“It sucks because his mind is so right, but his body has failed,” Jack said of his 88 year old Dad. His mom was being cared for by his sister who built a wing on five years ago and now has services for her brought in to help with her recovery.
“Cassie isn’t coming and her parents, well let’s just say that bridge is burned,” he said, noting they used to stay just minutes away from us at his in-laws.
“We got plenty of space,” I said, then confirmed when. “This weekend?”
Mel looked at me and gave a signal, reminding me she was gone with a friend to her bachelorette party (a new marriage at 50).
“It’ll be a guys night, Mel’s out of town.”
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Jack and Thomas’s cocks were on my brain once the internet and chatting anonymously became a thing. I’ve shared my stories in chats, writing blogs under different usernames, anonymous emails. I would edge and must have helped men cum thousands of times online since the early days of AOL’s clumsy fax sounding bings and clicks before announcing triumphantly – “you’ve got mail.”
Mel caught me once, my cock in hand and we had to change her username after I shared some porn and was caught. I made an excuse about my tailgating friends sending me something I didn’t know what I was getting.
Then 10 years ago there was the email fling I had with a former girlfriend, writing long, descriptive emails about things I fantasized about doing to her now.
Our marriage survived my hyper sexual nature and online interludes and we currently sit a year away from 30 years together.
Mel left early that Saturday morning, it was a nice summer day, I was in shorts and got some yard work done, played with the dog and late afternoon got online to a cock 2 cock chat. I edged some, sent some emails to a couple interesting men I had been corresponding with, and before cleaning up, started on the bourbon.
I had questions about Jack being overseas for a year at time a couple stretches. He had talked about his officer buddies and their treks to the woods in Colorado. I had imagined his cock feeling like Thomas’s sliding into my throat and maybe he had already had male lovers in the service.
I began to approach the notion that maybe he’d want me the way I wanted to please him.
Erect, I got a glass of bourbon and water, our plans were to grill, hang out enjoying some good bourbon and conversation. There was one phrase that pushed the fantasy of his cock towards reality in my mind, drunk with Cassie there, he admitted he was “attracted to intelligence”.
He was a brilliant man, and I often struggled to keep up.
I didn’t eat lunch, let the alcohol do it’s job, my mind now practicing possible entries into going down on Jack. In the past jacked off thinking of his cock, but never walked the seduction, or possible entry to getting on my knees in a formulaic manner.
The narrative I used while chatting or roleplaying online is different. Looking at my living room I could picture us with a drink in the chairs, engaging in conversation. One possibility would be I could lead him back to the intelligence comment he made, and what that might mean, asking a clarifier like “is that specific to one gender?”
I imagined being so bold, letting whatever answer, comments or questions land, exploring them and at some point admitting I had always wondered about his cock, or what he was thinking nude, cleaning house in our dorm room.
It would be then I would be confessing I wanted to go down on him, maybe even throwing in the Thomas mutual jack job, cock in my mouth, experience.
I mixed another drink, got a text he was 30 minutes out and fired up the pellet grill. It was pushing 7 p.m. and I quick rinsed off in the shower while the grill heated up.
I changed into a t-shirt, happy with the drop in weight I had from working out, boxers and shorts with Sketchers on getting the steaks ready some “Chicago” seasoning.
I poured a drink in my garage, having the ice, bourbon and water available as Jack pulled in, convertible, bought ten years ago during his mid-life crisis.
“Dump that garbage, I’ve got a good bourbon for you,” Jack said, hugging me with a bottle in his hand.
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Up until now what you have read is a true depiction of events this past summer, my thoughts and events of my past. Of course the names and situations adjusted enough to allow for this to be published and to protect any direct matching of details.
The following is how I wish it could have progressed.
Our plates were filled with red steak blood, the New York Strips a perfect medium-rare, the bourbon Jack poured from his favorite distillery, smooth and we were several pours in, making our way to the fire pit just off my back patio.
“Love the place Donnie,” Jack said, patting me on the back. “The steaks were amazing and nothing like a good baked potato.”
I had the wood set up for the fire, had a pile to put on as it died down, the bourbon and a beautiful clear night’s sky made it relaxing.
My intentions for the evening made me nervous.
I updated him on the kids and talked about the house, we had moved in just over a year ago with my new job, which allowed he and Cassie to stop so much last year.
“You saw it coming, didn’t you?” Jack asked about their divorce, then pouring a little bourbon more into mine and his glasses. The fire was starting to die down, we were an hour out there and I tossed another log on top.
“Cassie confided in Mel a couple times, yes we saw it coming.” They had individually alluded to years without having sex, I used this as my onramp to more “interesting” topics.
“What have you done for sex since you’ve indicated it’s been years for you two.”
“‘Spanktravision’,” he said using an old time reference of cable tv sex programing late at night. “The modern version is pornhub.”
His quick response fell out of the air and and flat, my hope for something more revealing not so simple. I looked at him, my desire instantly fueled by alcohol, was to be between his legs going down on his cock.
“You’ve always had someone Jack, be it Char, Tammy or whomever,” I said. “No judgement here.”
“Have YOU been faithful?” He asked changing the subject, not the path I was heading down, though I adjusted quickly.
“Depends on what you mean by faithful,” I said, then talked about the online affair from 10 years ago.
“I can’t say I’ve done anything like that…” Jack said, I sensing him playing with me now, not a real answer because it didn’t rule out anything else.
“I find that hard to believe since you introduced Mel and I to your first chat online.” I said recalling his telling a story back in the early internet days about chatting with someone and they all of a sudden asking what he was wearing and saying they were nude.
He’s attracted to ‘intelligence’. a voice in my head said, and as typically happened I choked, blurting something random out that in my mind was a good idea.
“I’ve gotten off a lot online…a lot.” I stammered, trying to take it to another level, but failing.
I wasn’t sure if this landed smart admitting to such a basal, primary need. I had woven sexual questions and he asked about my fidelity. I showed my honesty for how I was getting satisfied.
He fiddled with the wood in the fire, thoughts must have been racing through his mind. His next comment was almost as random as my last.
“Ever fuck Mel up the ass Donnie,” Jack said aggressively, maybe sensing my direction or my futility in adding to the conversation, still catching me off guard, changing everything abruptly.
“Umm, no…”
“Oh…ever want to?”
In that statement I heard my friend from years ago, the devious boy who took things too far, not the distinguished gentleman bearing bourbon.
“Of course…”
“Why didn’t you…she didn’t want to did she?”
I slowed down, thought of a time early in our marriage.
I talked about our neighbors in the first town we lived, a little younger, hot and how the man was always talking about anal.
“We had the conversation around the conversation, so I knew Mel wasn’t interested,” I said, looking at him, who had sat up straight, eyes awake and wide, though I knew he was as buzzed as I was my mind searching for a bridge to other things. “I wouldn’t call it a bucket list item for me.”
I’m guessing the alcohol kicked in, Jack’s next comment took our conversation off the rails…where I wanted it to go.
“Shit it’s hot and tight, it grabs your cock and, woah…” He said, his mind somewhere distant. “What is a bucket list item for you Donnie, if fucking your wife in the ass isn’t.”
Bingo…
“I have to admit, since the day I saw your large cock dangling while you cleaned, I’ve wanted one in my mouth,” I said, sat back gave him a glance then looked away.
“Interesting…Did you know I was hard that afternoon?”
“Duh…yes.”
“I’m hard now…”
“Care to help an old man out on his bucket list?”
“Indeed I do…”
Jack looked left and right, though it was nearing Midnight we could be seen from the road and the neighbors on the right.
“Inside…” I said and we gathered everything and rushed up the patio steps standing in the kitchen. “Probably down in the basement out of sight the…”
“No…right in front the window,” he said, pointing to my swivel chairs where we could be seen with the lights on, turned away from the outside, me well on my knees, moving vehicles couldn’t possibly figure it out.
Jack walked to the chair and looking at me, reaching or the belt and buttons on his shorts, he lowered his shorts producing his cock, a good 7+ inches, thick head, about what I remembered, though his balls were shaven clean and he stepped out of his shorts and sat down.
“Just imagine your Mel, or Kerri and what they’d do with this…and just do that…”
“That’s a whole other bucket list…”
“Sign me up…”
“Could you see Mel and I doing this together?” I said clumsily moving towards him, on the floor, my arms over the arm rest, above his cock sticking straight up. Jack adjusted moving his cheeks to the edge so his balls dangled.
“I could actually, make you both my naughty cocksuckers…You like dirty talk Donnie??”
“I don’t hate it…”
“Suck my balls first then…”
“That’s just dirty,” I laughed, and placed my hands on his muscular thighs, leant in and first put my lips around his head. It was soft as I had imagined, the precum tasting like mine, my hand underneath to feel his balls first. I slid my tongue down the shaft and angled my head, a hand went to the floor and I pushed my mouth up to take in one of his balls.
“Mmmm, good little bitch Donnie, I like that…Mmmmmm”
I slid the other hands up his cock, it felt like Thomas’s back in the day, a little shorter and thinner. I stroked him gently nursing his balls and sack with my mouth. I licked under his sack, finding his taint and then worked back up and positioned myself between his legs.
“Mmmm…good start…”
I engulfed his head, sucking around it, then pushed it back over my tongue. I felt it reach the back of my throat, angled some and got another inch inside, maybe a little more than half in my mouth. I sucked on it and remembered how unsatisfying that was when done poorly, I would get bored, roll off and just end up fucking Mel.
I tilted more, pulled it out spitting on the tip, and pushed it back in, this time getting another full inch or more back.
“Your a good boi, Donnie, take it all…”
I repeated, pulling it out, spitting on the edge, rubbing it with my hand, doing it again, seeing the porn stars doing this, I got him maximum lubricated and then slid my face and throat balls deep on his cock.
“Hang on Baby, so good…”
He took my head, braced it and began thrusting with his hips, I was now stationary and he was moving, fucking my face and throat in an instant.
The wet, sexual penetration noise elevated, his breathing spiked and he was slapping my chin with his balls in a half-squat fucking my throat deep.
“Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght! Gahguhgght!” he thrust into me relentlessly until…
Abruptly he stopped and pulled out.
“I hate to tell you but I don’t cum usually like this…I tried…”
“I want you to finish…” I said and raised an eyebrow…
“Donnie are you…”
“Let’s go,” I stood, took his hand and pulled him off the chair and towards our bedroom which is just off the kitchen.
I stripped, his eyes on me while he walked in, watching me, clothes hitting the floor.
“It’s different, it’s too…”
“Let’s do this,” I said and tossed him some cream from the dressed that I used on my dry skin, I had also used fucking a cucumber feeling what this would be like, knowing it was what I wanted. I went to crawl on the bed, show him my ass, and let him start riding.
“Wait,” he said, grabbing my hand and pulling me away the bed. I feared he was backing down, my cock was so hard, I lunged at him as he lunged at me, our lips met, our hands were on each other’s face, his tongue in my mouth. His fingers pressed into my temples, cheeks, scalp, down my neck, our mouths fought for dominance, I felt his cock slide under mine and mine along his, we opened our eyes and looked at each other. “Fuck, you’re hot as shit.”
He turned me and moved my hands to the bed.
“I love standing…”
He took the cream, a hearty three fingers worth, touched my balls, rubbed up over my taint, sending shivers before pushing it over my hole, inside my hole and then covering his cock. He got just a little more and covering just my hole before rubbing more into his shaft.
“Ohhhh,” I moaned, his hands on my hips, the tip at my hole and he began to push. “Ohhhhh Jack…Yessss”
The pulsing flesh slid inside me, his head first. It filled me like nothing could ever, had ever…would become my obsession.
“OH GOD!” I exclaimed, it’s warmth, soft hardness, I nearly came right there, he pushed in slowly not backing up, probing, making the path perfect. His hands were on my hips pulling me to his hips. “JACKKKK!!! OH FUCK YES!”
He pulled back and began to thrust a few inches back and forth at a time, the lubrication not ideal, but it got things started and he got an inch longer back and forth after about five minutes. I was a little taller, his body draped on my back, his hips driving back and forth.
“Christ yes Donnie, Yes!” Jack exclaimed, now pumping faster. “Your hole is so fucking tight…YES!”
I fell forward onto my knees, his cock popping out for a moment, and then he saddled up behind me, I grabbed a pillow holding it, looking back and let him go fast in and out of my man pussy, his stamina both a blessing and a curse.
Jack rode me for a good 15 minutes, fucking me faster, before I began to egg him on.
“Come on Jack, fill me…I want that cum…that warm in my ass. Bucket list! FILL ME JACK!”
“AHHHGggghhh!” He exclaimed and I felt the rush, I felt the warmth, he sprayed inside my ass, I felt his cock inside of me, still there, he pumped slower, and kept moving.
“Finish Donnie,” he said reaching around and stroking my cock, sliding it in his fingers, curling gently, squeezing while rubbing. He was still inside me while his hand was pressing the tip, down to my balls pulling and jerking until I came.
He pulled out and I didn’t hesitate to whirl around and take his cock in my mouth, tasting him, sucking cum out of his shaft, his fingers going to my lips too, smearing my cum on his cock while I took him inside my mouth repeated, sucking, dropping, sucking, dropping.
I fell to the right, laughing, “Oh FUCK! That was good,” I said, looking over at him.
Epilog: All of my thoughts, and all of the discussion is true (may not have been discussed that night) and the intention is still there. Everything was set up when Mel called and her Mom wanted to see Jack and have dinner.