Memoirs of My Gay Life

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.

When I didn't stand she berated me, "You really do need a lot of training, Slave. Because right now you are worthless."

I objected, "You can't expect me to stand tied up like this."

Amanda whipped me with Terry's flaccid cock, "Your's is not to reason why. If I say stand then the least you can do is to try. You must try absofuckinlutely everything I ask of you. Now stand!"

I pushed against the restraints. Nothing moved more than a centimeter.

"That's better. You might make a useful cum bucket yet. Keep it up and I think no one is going to piss down your throat this morning. Well...if you continue to show promise."

She reached over to get Terry's belt from his pants where he had left them. Folding it over she draped it behind my head and gave the ends to Terry. "There! That looks better. Briefly she looked at me, "When it's hard can you take it all?" I nodded. Now, to Terry, she said, "You heard him. Fuck his skull." Which is exactly what Terry did.

He did a great job of it too. He used the belt to yank my mouth down over his expanding cock as he towered over me.

It was his cock thrusting into me but it was Amanda who was being so strong in our threesome. She wasn't even having sex with me, yet she was making this my best experience ever.

Replacing the pillow she climbed behind me. I felt the warmth from her naked furry pussy on the back of my neck as she grabbed hold of my head commanding Terry to fuck me deeply and finish off.

In a second he did just that. Terry bottomed out So that my nose and lips were pressed firmly against his hairy crotch. I felt the Anaconda pulse when he spit his seed, but that was it. More exciting to me was the wet trickle and feeling of Amanda's fingers rubbing her twat. I'd never before been turned on by anything female. Maybe I still hadn't - maybe I was just turned on by my friend rather than her sex. Or more likely by the long fat cock shooting off down my throat.

**

Another year went by. Amanda was not a part of my sexual encounters again. She dated who she dated and I dated who I dated. I worried she would settle down with some guy and I would lose my roomy.

Amanda and I got a puppy which rapidly grew into a full sized dog. But it turns out that's not what she wanted. She wanted a child. I went with her to adoption agencies then clinics to explore insemination.

She never could commit to either. Then one night we were watching telly when she turned to me all serious, "It would be so easy you know. For you to jerk off and give me your semen."

We talked about it for a couple of weeks then tried it out. I would jerk off into my hand, then we would meet in the hall and she would scoop it up and go back to her bedroom. Months went by to no avail.

We both reached the inescapable conclusion that the insemination needed to be more direct.

The following week, with doubt and a very soft dick I knocked on her bedroom door. She called sweetly for me to enter. There were candles and scents and it all seemed so foreign.

Entering slowly I spied her outline on the bed. She was covered from head to toe by a sheet. Not just any sheet but one with a life-sized image of a naked man - except that instead of a penis there was a hole in the sheet. I instantly deduced her plan and concurred with her idea.

When I climbed on top of her my forearms were on either side of her shoulders, my ankles inside hers, and our hips pressed together. The sheet hid her body from my sight but I could still feel quite a lot of what it felt like to be next to a woman.

I had trouble finding the entrance until under the sheet I felt invisible fingers grasp my cock directing me in.

The fit wasn't snug. There was no assring to grab the base of my cock tightly. Instead it hugged me subtly from tip to root. The feeling was so unlike packing fudge.

I thought back to a bossy hunk who forced me to fuck his ass once. He too had laid flat on a bed, except face down. His boi-pussy was tight and gooey with vaseline. He held my arms tight around him, holding my wrists close to his chest. I plunged hard and deep until I filled his ass with my cream.

In the present, my naked cock was intimately touching the walls of an actual slippery pussy. Her juices were mixing with mine in that little hole on the end of my dick, and my juices were seeping out, mingling with hers. The thought almost turned me off but so many times we had shared a glass or silverware, I just had to convince myself that our sexual liquids were no different than any other - except for the whole baby thing.

We didn't get pregnant that night, not for the next or the next...

Work kept me busier than when I was younger with less responsibility, so I wasn't hooking up nightly anymore. More like, on weekends only.

I started to look forward to insemination nights. I mean, a wet pussy feels pretty good no matter who you are. And I didn't need to go prowling. Amanda was enjoying it too. At first she hid it from me, but I could tell she was having orgasms from our love making. I only call it that because I loved my friend dearly and it was sex. However, that evil lust was absent.

Time flew and Amanda convinced me that it was silly to wait until ovulation. I didn't object to fucking every other night, or even every night.

One night I entered as scheduled to discover a sheet was thrown over Amanda's body as she waited for me in the doggy position instead of missionary.

It reminded me of the first time I was taken doggy. I was at the house of a straight guy I knew named Steve. Two of his buddies were there too. Steve had a huge cock but his friends did not. They took turns plowing my upturned ass starting from smallest to largest. I loved how they each had a different technique.

The first was nervous. Gingerly he rested his fingers on my hips working his way in, then finishing with a steady rhythm. The second talked a lot, going on and on about the joys of sloppy seconds. Steve followed up, digging his fingers into my flesh, pulling me forcefully back onto his violently thrusting cock.

I thought the gentle approach would be best with my female friend. But she had other ideas. Amanda pounded her ass back against me grunting with each full penetration. Her hips felt round and soft under my grip which needed to be firm to keep me from being thrown like a cowboy from a Broncos back. I came in seconds depriving Amanda of her orgasm.

I usually left right after depositing my sperm but with all the energy needed on this wild ride I fell onto the bed to catch my breath.

Concerned for Amanda I asked, "Did you, you know? Cum? I'm sorry I was so quick, it's just that I really liked that. It's surprising to me but you're really good."

Amanda answered and I could hear the dissatisfaction, "No, it's alright, it's all about a baby you know." Her arm reached out from under the covers and punched me playfully.

This devolved into play fighting and the next thing I knew I was wrestling naked with my best friend.

It ended with her sitting astride my chest. I could see her fully nude body, the first live nude woman ever. I had to admit, Amanda was an attractive woman; she just failed to have a big cock. She commented in an offhand way, "They say an orgasm helps a girl get pregnant, and being full of cum it probably tastes just like cock."

Bradly used to sit on my chest all the time. It was his favorite way to fuck my mouth. He would push me down then when he had me helpless he would rock forward to insert his cockhead into my parted lips. More and more of his big arched dick would go down my gullet into my well fucked pussy-throat. He liked to cum all the way in me. I liked to please him with my mouth and would beat off furiously.

I could have pushed Amanda off easily. But grabbing the sheet she tied my hands symbolically. That was all she needed to do. I nodded my head and replied, "Well, If it tastes like cum..."

Amanda inched forward on my chest. I encountered an unfamiliar smell as the first pussy to come near to my mouth was within striking distance. It wasn't bad, definitely not at all like a cock, either clean or unclean. I once had delighted in a monster cock right after the man pulled it from his wife's cunt. It didn't smell like that either.

Amanda warned me, "Ready or not, here it comes." Having said that she tilted her pelvis which caused the full experience of her sex to confront me.

It was indeed filled with my old friend. I like cum! Even my own. I licked it out savoring the bitter cummy flavor. After I got most of it, Amanda reminded me that I owed her an orgasm and that this was about her.

Diligently I devoted myself to the task, focusing on her needs. Now, no one had less of an idea how to eat pussy than I. I've never even read a single word about it. But, I didn't need to be concerned, Amanda ground her gash onto my face giving me commands the whole time.

I just listened and obeyed and I could tell it was working. It worked so well that as she approached her climax I got rock hard. She was yelling, "Suck the clit! Suck the clit!" and I was wanking fast, quickly approaching my own.

When we came Amanda fell off me, it being her turn to be out of breath. After a minute she got up to go to the bathroom, on the way she said, "I felt that hit my back. So you can't say you didn't like that too." I didn't have the heart to tell her that it was her dominant tone that pushed my buttons.

A couple days later I got a text on an unscheduled night, it was simple and straight to the point, "I need a screw." Was it a mistake to do it when we wanted to rather than just to get pregnant?

I popped my head through the doorway to her room only to find her naked and laying face down on her bed. No clothes. No sheet. I can appreciate an attractive form, like the fine lines of a champion dog. And she had fine lines - that's all it was. Nothing sexual here. I could take it or leave it. My dick decided for me and I took her. I took her from behind, laying on top of her.