My mother was a beautiful woman. Tall with shoulder length black hair and an hourglass figure. She had bright blue eyes and full lips that she always kept glossed in red lipstick, a large bust, flat stomach, curvy hips and a full bottom that had many men and women lusting after her. She conveyed an angry-dangerous sexuality. She and my father divorced when I was two. He died in an auto accident a year later so I never really knew him.
My mother is a lesbian now and is openly gay and has been in several relationships with other women. She is very dominant and is a powerful CEO of a large company. She is also very active in the LGBT community and openly supports that cause. She was very strict with me but I knew that she loved me and wanted me to be successful in whatever I did.
I sometimes wonder if she had wanted a girl though because she used to dress me up as a little girl. She would have me go around the house as if I were her daughter. This took place till I was about 6 before she really stopped. I never thought much of it other than our playing together.
Mother had an active sex life bringing home many attractive women who were younger and sometimes older than her. I think she got a kick out seducing married women and turning them towards being lesbian.
My senior year in high school, not long after I had turned 18, I discovered her sex toy stash in her bedroom. There was a large assortment of vibrators, dildos, plugs, and a long silicone snakelike thing called a Square Peg Slink. It was about two and a half feet long and starting at the tip was tapered to about 6 inches at its max circumference. For some reason the thing intrigued me and I knew I had to have it in my asshole. I had been visiting gay porn sites and masturbating for some time now. I only recently had begun to finger my own ass as I jacked off to those videos. I knew in my heart I was gay and was attracted to older father figure types. I guess this was because I did not have a father figure in my life. I had not done any dating in high school but no one suspected I was gay because I was pretty straight acting.
When mother was gone, I would go into her bedroom and masturbate on her bed because she had a large screen smart television and I could play gay videos on it from our WiFi. I would stretch out and stroke my cock wishing I was the guy in the videos being covered in cum and getting his asshole pounded by all those large cocks. I would experiment with her variety of dildos and vibrators.
I found that I loved the feel of the slink going in and out of my ass as I jacked off. Once I was able to get it all the way inside my asshole, my bowels start relaxing on it, it seemed to start to moving on its own! The slink started moving inside me like a snake, poking and sliding inside the depths of my inner being. It was a very intense sensation. I could not get it all the way in as my asshole would not open that far. But I loved the way it massaged my prostate.
One afternoon after school, while my mother was at work, I went to her bedroom to jack off. I had just finished cumming my brains out and was in the process of pulling the slink out of my ass when I heard my mother come home. Panicking, I quickly turned off the television and grabbed my towels and the slink and cleared out of her room. I figured I would clean the toy up and return it later.
The next day, after school I didn't jack off but did put the slink back in mother's bedroom hoping she had noticed it missing. I was wrong. That evening at dinner she asked me point blank if I was gay. I stammered I didn't know. Then I said "No. That is not true. I feel pretty sure I am."
Mother told me she was proud that I was coming out to her. She also told me she had suspected for a while but was pretty sure last night when she turned on her television and it was playing gay porn. She also noticed one of the toys was missing. She said she didn't me using them, but to just make sure I clean them properly before putting them up. I explained to her I had and that I had returned her slink.
She told me she would love to have a "Coming Out" party for me if I was willing and that is would be a nice way to meet other gay men my age. I told her I felt like I was more attracted to older mature men and she told me she had a friend I should meet. Mother said he was in his early forties, fit and very attractive. I said sure. Mother smiled a mischievous smile and said she would set it up.
Several days later mother me an address and told me she wanted me to go visit this man and discuss any concerns I had about my sexuality. She said he was carpenter and owned his own construction company. She also said he was gay. She said she had known him for many years and was a very nice man. She also said that if she was still straight she would hop into bed with him because he was very rugged looking and handsome. A regular Marlborough Man. She said his name was Richard Martin.
I drove over to Mr. Martin's house and it was a very large with an enormous brick wall going all around. I was very nervous and rang the door bell. I was greeted by the most handsome man I had ever met. He was wearing jeans and a white t-shirt. You could see his muscles rippling underneath his shirt and his chest and arms were very hairy. He has salt and pepper hair and a black beard of about 2 weeks growth.
I said "Hello Mr. Martin. I am Steve."
He said "Call me Richard."
He invited me into his home. He asked if I would like a beer and I said I would. We relaxed in his den and the afternoon went pretty fast.
After a couple of beers, Richard said "Well Steve, lets get on with your education." He pulled out a small brown bottle and handed it to me.
" Here, take this and sniff it."
I unscrewed the lid and the bottle made a soft hiss. I put it up to my nose and sniffed. I felt his hand reach around my head and his thumb pushed one of my nostrils closed, his fingers pulling the bottle closer to my other nostril.
"Breathe deep boy".
My heart started to race and my head started spinning, but I felt really good. I felt like I could do anything. My hands were shaking and my heart was pumping out of my chest. I slowly unscrewed the lid and gave the bottle a long, deep sniff. While I began to feel slutty and my head was exploding...everything went into slow motion.
I saw Richard unbuckle his jeans and removed his shirt. He slid his boxers off and I was entranced!
When Richard's big piece of male meat came into view, it was clearly over ten massively thick inches of rigid cock. I'd seen magazines before, some that had men along with women. But, none where the men had anything between their legs like the huge slab of flesh jutting out in front of me now.
The thick soft veiny skin that covered Richard's sturdy shaft continued over the flaring ridge of the doorknob-sized head that made up nearly four inches of the full length. Only a fourth of the tip lay revealed in front of me. The outline of the bulky brute underneath was thrown out in such high relief, it explained why the foreskin aspect hadn't shown through the outline of it swinging inside Richard's shorts on previous occasions. I'd only seen a couple of un-cut cocks at the gym in school, but always thought they looked odd. On Richard, it made his cock look especially mysterious, masculine, and hefty. One thick vein curved off center from the left up from the base to the edge of that huge slab of meat before it slimmed out just before then edge of his foreskin. It branched out in irregular directions that crisscrossed with those stemming from another large vein that angled up from just under the other side of the big cock's proud width. Like the heavy hood of foreskin, those veins only made Richard's cock look even more powerful and exciting.
It was darker than the rest of the tall burly and muscular man in front of me. Though all the hair over his body hid most of the skin underneath, it was clear that the hulking bulk of Richard's cock was a deeper brown than even his tanned arms and legs.Everything about the big man's big cock enthralled me...the slightly darker color, the over ten inch length, the tremendous girth, the slight upward curve, and the strong branching veins roadmapping mighty male meat. Richard did nothing to hurry me, and let me take my time simply staring in awe before moving my hand back up to explore the big straining meat by touch.
I squeezed it with my hand, marveling in the three inch distance between my thumb meeting my fingers. It jerked and bobbed inches from my face. I let go and curved my fingers to "pet" it along it's thick ten inch underside, a thick tube the size of my middle finger ran from base to tip.
Richard's wide meat jumped and bobbed again as a rumbling grunt came from above me and thick pearly white fluid pulsed from the tip and drooled down toward the floor. A hand reached for the back of my head and gently urged me forward. The broad drooling head reached my lips, wetness spread across them and dribbled down my chin. I panicked. I knew nothing about how to do this except for the jokes I'd heard about keeping teeth off it. Richard pressed forward and my mouth opened of its own accord.
The thick head pushed at the same time as the big cock lurched upward and something thick and salty with a slightly tangy flavor flowed inside. It wasn't really a good or bad taste. The fact that it came from Richard's cock, though, left me wanting more. My lips stretched as far as they could go around the big man's extreme girth. I had to strain my jaw uncomfortably, but the discomfort held no comparison to the excitement of having the big man's cock inside my mouth. I only had my tongue to use and, not knowing what else to do, I slid and lapped it against the prominent tube running along the underside until I was rewarded with another thick flow of salty fluid into my mouth.
Richard pressed farther and sank more of his muscular cock inside until it hit the back of my throat. He still pushed further and I had to reach up and around his wide hairy thighs for balance. A soft quiet groan met my ears and he eased that thick meat back out to the head before sliding back inside as far as it would go. His legs bent and then straightened as he pulled back out and then pushed back in again. My jaw still ached from keeping my teeth away while my tongue kept at its lapping and slurping of the thick hooded head inside.
I pulled at it with my mouth, suctioning against the huge width especially when Richard would draw it back from my throat. With my tongue snaking over its surface, it darted unintentionally underneath the thick cowl of foreskin. My tongue felt tightly hugged inside Richard's velvety foreskin and the spongy flesh of his burgeoning cockhead. He stopped all movement with a deep rasping sigh and I began sliding my tongue left and right to caress and explore the doorknob sized head cloaked in its thick soft sheath of skin.
Richard's free hand came down and grasped his thick hard veiny cock about midway down. Slowly, he pulled the skin over it farther and farther back as the hugging sensation on my tongue slid away and began to feel the full bulk of his meaty cockhead bared inside my mouth.
The hand on my head slid to the back and became an immovable wall when Richard suddenly thrust against the back of my throat and slid past. I fought against the hand holding me in place as that huge cock shoved its way down into my throat and toward my stomach. I swallowed hard against it, trying to force it back out while unable to breath. That only seemed to incite him more, and he hunched his hips to bury himself more deeply into my throat.
"AHHH AHHH AHHH AHHH AHHH AHHH!"
The ragged sounds came from above me in short gasping breaths. He pulled back out and left me with only a second to draw in a deep quick breath before cutting it off by thrusting back deep into my throat.
I became left completely absorbed in the huge fat cock thrusting down my throat and filling my body as well as the big strong older hairy man behind it. The humongous cock shoving down my throat. That incredibly long, incredibly fat cock being hauled back out. Shoving inside.
Pulling out.
Shoving in.
