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.
