How It All Started...
It was the summer between high school and freshman year at college, and my parents were throwing one of their famous parties for their friends. Basically it was all 'old' people (so I thought at the time) who basically just drank for hours, ate a ridiculous amount of food, and often didn't see the last people leave until the next day. They only had a few a year, but it was all their social circle would talk about for months after.
This night started off no different than the many other parties I had been through. I made quick appearances, said 'hi' here, hugs where appropriate there, suffered the normal litany of comments about how big I'd gotten, and a slew of the same questions about college plans.
As soon as I could I would duck out to play video games, or just hide in general. I was fairly successful for most of the night, braving the crowds only when I needed more snacks or drinks.
The party was still going fairly strong when 1am rolled around, and I decided to call it a night. I made a quick round, told my dad goodnight, and a few others, couldn't find mom at all, then headed to my room.
With the door shut behind me, the party noise muted at last, I got undressed, grabbed a hand towel, pumped a squirt of lotion in my palm, hit the lights, and laid back on the bed to enjoy a leisurely stroke before going to sleep.
When I jerk off I try to make it last as long as possible, without rubbing myself raw of course. I use long, slow strokes, alternate pressure, and spend time enjoying whatever the object of my fantasy might be at that time. Due to this I was pretty deep in my self pleasure when the door opened, and my mom flicked the light on.
Someone had forgotten to lock the door.
The sudden change from light to dark, combined with coming out of my fantasy to what was going on in my room caused me to hesitate for a fraction of a second, before grabbing the only thing near me, my hand towel, shoving it over my throbbing cock, trying to cover myself.
"Mom! Knock!" I squeaked out, sitting up, trying to make the towel cover as much of my nakedness as I could.
Mom, for her part, seemed fairly oblivious. She shut the door behind her, obviously unsteady on her feet even in my panicked eyes.
Her maroon tank top had a small stain above her right breast, it looked like she had halfheartedly tried to dab it away with something, and only manage to make a larger wet spot on her tight shirt.
She made her way over to the bed, barefoot, her heels lost some time ago whether for comfort or because she truly lost them I'd never found out. Without her heels on she came to my shoulder height when standing, something she always seemed immensely proud of for some reason,
"Sorry.. Sorry honey. I just wanted to come say, say goodnight."
She reached out and ruffled my hair, smiling a drunken smile, then sat heavily next to me on my left, shoulder to shoulder on the bed. I could smell the alcohol sweating out of her. She was absolutely wasted.
Regardless I still tried my best to cover myself, and my maddeningly hard cock still bouncing to my heartbeat covered only by a small hand towel.
"What.. what's wrong, honey?" It literally did not sink in to her that something was amiss until that moment.
"It's just that, you need to knock mom. You know that." I said, calmer.
"I know, I just wanted to say good night. I.. what.. what are you covering?" Without pausing, she reached across with her left hand and plucked the hand towel away.
"Ooooh." She said sitting up a bit straighter. "Oh I see."
I tried to grab for the towel, covering myself with my other hand, but she managed to keep it away fairly easily by simply dropping it on the floor as far away form me as she could reach.
"Oh honey, don't, don't worry about that. It's perfectly normal." She leaned her shoulder against my shoulder playfully, which caused her breast to push against me as well.
"MOM!" I covered myself with both hands.
"Oh stop it. You think I don't know about what you do? Here, let me see what we're dealing with." Removing my hands was not a hard task as they were doing a poor job of covering my erection anyway. 'Tsk'ing she slapped my hands away, then pushed my bare torso back with a, forcing me to choose between falling over completely, or to brace myself with my hands. Instinct forced me to choose the latter. The result of course left me very exposed.
"Wow. You are a man now, aren't you?" She said softly, and before I knew it my cock was in her soft, cool hand.
"You're gorgeous honey, I'm so happy for you." Her petite hand dwarfed by my thick cock, deftly began taking experimental strokes as she talked.
"Do you use lotion? Oh my god your skin feels so silky and smooth."
Still sitting next to me, mom's right hand working my cock, her left crept on it's own accord to her ample tits, absently caressing her left breast while she stroked.
I had no idea what to do. So I took the path of least resistance and did nothing, leaning back on my elbows, looking down the length of my lean, naked body, as my drunk mom pumped my cock and fondled herself. It was a bit much to comprehend at the time, so I locked up effectively.
"Like I said honey. This is natural, you need this." Her own breath was coming a bit faster I noticed, and color had risen to her cheeks. A hunger lit her eye that I'd never seen before. For all that she still carried on as if we were having a normal conversation.
"I know all these years that you've had to work off this energy, that's why I never said anything or stopped you. My god your cock is beautiful.." she licked her lips at the last, breaking her 'this is normal' façade for a moment.
Catching herself she continued.
"and.. umm.. where was I? Oh yes, you gotta get. That. Cum. Out." She started to pump faster, feeling my cock thicken in her hand.
I felt my balls tighten in warning, and my orgasm building. I'd already been stroking for awhile before she came in, so I wasn't going to last long.
I found my voice at last.
"Mom.. I." I gasped out
"I know honey." Her voice, now raspy and low. " I can feel it. Let go, let it out honey. I wanna see my boy shoot for mommy."
Her words were sending me quickly over the edge. My hips started to push up involuntarily as my ass and thighs tightened in response to my building climax.
"It's ohmygod mom.."
"I know honey. Cum for me. Get the cum out." Still only using her right hand on me her left had snuck into her tank top and was pinching her right nipple while she watched my cock with laser focus. Her posture was perfect, like she was sitting at a job interview, or a principal's office.
"That's it honey, let it go.. you can do it for mommy.."
With a low, crunch inducing, groan I came. Hard.
Mom laughed when I came, in both surprise and delight, her smile widening with each thick, ropey jet of semen that jetted out of my balls onto the floor, and her hand.
"Theeeer you go honey. Oh my.. wow.. " she kept stroking, though more lightly, as I jet after jet of cum. "That's perfect honey, you are such a good boy."
At some point I gave up watching and laid back full on the bed, eyes closed as mom gradually slowed her stroking, seemingly enjoying the jolts of pleasure that she was sending through my body with each stroke.
"There. You feel better now honey?" She said, standing.
She cast about for something to clean her hand off with, my cum still covering much of it. As she looked for the half remembered hand towel she absently started to lick her fingers clean as well.
"Mmmm.. that was mmm.. You needed that honey. You can't let that build up in your system too much. It's bad for guys." As she lectured me she finally found the towel, bent at the knees demurely to pick it up off the floor.
Wiping her hands she faced me again, a big smile on her lips.
"I.. uh.." she looked down realizing how hard and prominent her nipples were now poking against the thin fabric of her tank top. "uh.. oh. Well I guess I need to go change my shirt."
She moved towards the door, mostly in a direct line, and hit the light before opening it. She stood outlined against the light from the hallway, still breathing a bit hard, her breasts moving with her breath.
"Good night honey, I love you."
The door shut leaving me in darkness.
I got back up to my elbows in the dark, still not sure what type of truck it was that had hit me. I had never come even close to how intense of an orgasm I had just had. But... mom...
'But mom' indeed. Mom, had done more to me in a few short minutes with one hand than all the girls I'd been with up to that point.
That was the night, the eye opening event, that made me realize that there were far more options available to me in life than I had thought there were even an hour before."