Memoirs of My Gay Life
I was a size queen.
But I guess that's no way to start a story; I'm James and I've been gay all my life.
My first time having sex was with a guy I only hung out with once in a while. He only lived in my area during the summers between college semesters. I can't get into the backstory but here are some highlights: we had been looking at a titty mag in the garage. John was thrilled to be seeing boobies. I was at a loss as to what made them so fascinating. He liked them big. To me, the bigger they were the floppier they were. After a bit we both had erections. His was no doubt due to the images. I think mine was the result of the illicit activity we shared. The magazine hinted at lusty sights below the waist. Whenever it almost showed a pussy John would get revved up. I, however, was curious about sights below John's waist. The mag also had a section called "Confessions". Mostly it was guys talking about the first time they saw a girl's boobs or their past sexual activities. Quite a few were from guys who had either jerked off together or tried oral.
After a bit John asked me if I beat off. I lied and told him I didn't. But the direction of the conversation had us both breathless. Then he asked me how big mine was. I honestly hadn't measured it yet. John didn't know how big his was either.
Jumping up he said he had a ruler around somewhere. Not finding one we decided to hold ours next to each other's to compare.
We both enjoyed the feeling of another dick embracing our own. They looked roughly the same.
With our dicks touching and our heads bent to look, John said, "Those two guys in the magazine took each other in their mouth. The one said it was incredible to feel warm lips and the other said it tasted great."
There wasn't even any talk about who would go first or did we really want to do it. I just bent at the waist, taking about half an inch of John's dick into my mouth, I tongued it eagerly. John asked, "It taste good. Doesn't it?" I agreed. Getting down to my knees I started sucking in earnest.
It was obvious that John loved every second of it. I did too. I just didn't moan the whole time. In a couple minutes he jetted a few spurts of cum in my mouth. I never thought to pretend that I wanted to spit it out. I just swallowed cause that's what we read that girls did. While I had been sucking his dick I was too turned on not to jerk off. If John was disappointed or relieved not to suck mine, he didn't say.
That day and later I kept thinking about comparing dicks with my other friends. Whose would be big? Whose would be bigger than mine? Would they want me to suck their dicks?
I never sucked John again. He must've freaked out because he was scarce after that.
That was the beginning of my obsession with big cocks. From then on whenever I hooked up with a guy it was always my quest to find a guy with a big one.
A few years later with a handful of experiences behind me I had yet to have a girlfriend. It's not that I never considered getting one, I just never met a girl that attracted me and most were distasteful.
So, with my obsession for large, I started frequenting gay bars and bookstores. A day didn't go by that I couldn't find a big bad cock to suck while jerking off.
A lot of the guys wanted to continue with other activities or even date. It was easier and safer to keep at it with the same big dicked man so there were times when I had a steady fuck buddy.
The first time I got fucked, my boyfriend, Bradly, had surprised me with a blowjob one night while watching TV. In the middle of a show he slipped down between my legs removing my pants. I had blown him maybe fifty times so far, but he had not blown me once. I was good with our arrangement and I thought he was too. I started to object but Bradly shushed me telling me that little bitches should be seen and not heard. His bossy talk always made me obey.
I did like having a friend to go to social events with and I learned to appreciate other aspects of a man. For example, I like a guy with a wry sense of humor and a protective nature.
My circle grew and I found long term friends in the gay community.
But I digress, Bradly sucked on my cockhead, made his way down the shaft, sucked my testis, then headed south to tongue-tickle my perineum and finally rim my ass.
It was my first non-BJ activity. Pushing my legs up and holding them there he spent some quality time lapping away. I enjoyed it but I could tell he liked it more.
I didn't know he planned to push his big cock into my ass. When he rose up my first thought was that he was going to kiss me - the scariest thing I could imagine. As soon as his large appendage touched my anus I knew what he intended.
I've mentioned that I have a thing for big cocks. Cocks that can never be swallowed in their entirety. When I sucked Bradly I could take in seven inches, eight inches on a good day, at most. It wasn't that I couldn't deep throat a big dick, it was that when one is thick enough it's harder to go deep.
So, Bradly was selected to be my regular cum provider because his cock was huge and here he was about to slam it into me. I was scared my first fuck would hurt yet relieved that her didn't want to kiss. He repositioned my ass on the couch saying, "Grab your buns and spread 'em like a little fuck toy". Any reservation I had melted with his dirty talk.
Bending forward I looked down, afraid to watch it rip into me. I could see that it was already greased up, and totally hard. Seeing it my fear grew, I closed my eyes then turned away like a boy getting a vaccination. As if that would help with the pain.
Holding my hips he didn't slam me but eased in gradually. It stretched but didn't ever hurt. My erection had faded when I first understood his intent and it never revived. My dick flopped back and forth wildly while Bradly fucked me with about four inches of that beast. It had never occurred to me that it wasn't necessary to plunge to the hilt. So never going in more than half way he built up to a crazily active slam-fest, depositing a load that would leak out for the next few hours reminding me that I had been royally reamed.
Bradly sometimes blindfolded me and sat on my cock, fucking himself. His ass was snug and always brought me off. But being blind to what was happening was the biggest thrill.
After that I would enjoy sucking and getting fucked by big cocks, occasionally keeping a guy around and sometimes hooking up with an average dicked man if he really made me feel especially abused. A throwback, I guess, to life with my father.
I met my friend Amanda at a queer dinner party. She was a charming fag-hag (not gay) and after I got to know her, her natural bawdyness gave me an emotional completeness random guys did not.
Over time we became inseparable friends with her being the light of my life.
The years ticked on and our friendship deepened as we weathered life together. She was there for me through the death of my mother, the AIDS test scare, and my cancer diagnosis and remission, while I buoyed her spirits through her brother's car accident and her auto-immune problems. Why did no one warn me life was so painfully difficult or how important a good friend would be?
**
When we were both in our forties we moved in together. We got along nicely, she was a great roommate. I had no regulars during that time, just some pretty fantastic encounters.
There was the time I re-picked up a guy I'd met before and brought him home. In the privacy of my bedroom he tied me up with a few belts and pounded my ass doggy style.
The next morning when he finished showering we all had breakfast. I hadn't cum the night before so when he hinted that he would like to use my mouth I was ready. Amanda asked if she could watch. I'd had plenty of guys in and out but never had sex in front of my lady friend before.
Terry turned to Amanda, "Would it be alright if I tied him up?" She didn't know I was into being abused and I wasn't real keen on my world's colliding.
Amanda put my worries to rest, speaking to Terry, "I love tying my lovers, and I'm pretty good at it. Can I tie him for you?"
The two of them were engrossed in talking about tying guys up and kind of ignored me. When they finished talking Amanda went and got a whole basket full of various ropes and stuff. Who knew?
Terry said he wanted to fuck my mouth against the couch. Together, they led me over and had me sit on the floor in front of the couch. They turned me around with a pillow on the couch behind my neck. I felt safe with Amanda there. In my usual hookups I don't always know the guys that well.
She had me sitting on some sort of cushioned pad with a dildo sticking straight up into my ass. My arms were stretched tightly, fastened to the front legs of the sofa. Both my legs were bound with multiple coils of rope.
In addition, my dick was encircled by a rubber cock ring which made it harder than ever while my balls were stretched with a ball stretcher thingy. .
When Terry approached me, I'd had sex with him three times in total, and I just realized I'd never seen his cock before. He said, "I just filled your ass five hours ago so I might not be super quick here." Amanda giggled her approval.
Soft, it was seven inches long; I'm really good at measuring a cock with my eyes. Though that'd be the same length my ass would have measured it to be. When he went to put it through the red silicone lip shaped ring Amanda had fitted in my mouth it wouldn't go through. Amanda called it a 'face trainer' - she was so disappointed when she had to remove it.
She looked at me, bound and spread there in front of the couch, with a wicked glint in her eye, commenting that without my mouth being held open, something was missing. Why couldn't she have been a guy? She was so right for me.
"Stand up!" She barked at me.
Of course, I couldn't stand. I couldn't move my legs. I couldn't bounce on the dildo. The only things I could do was move my head and speak, at least for the time being. I looked at her quizzically.
