I was loath to confess to this gorgeous, glittering beauty that I didn’t know anything about the female body. I’d spent a lot of years being bitter about this fact, but then mostly I just accepted that girls didn’t want a broken man, and moved on to different aspects of life.
I had won the middle school spelling bee. Take that, guys who had had sex.
“Hey,” she said, when I was halfway into telling her my whole life’s story. “Hey. Don’t. Don’t worry about it, okay? Just tell me I’m pretty.”
“You are fluffing gorgeous,” I breathed. “Like a thousand miles out of my league.” She was hardly supermodel beautiful, but she was fit, smiling, and she was glowing with literal magic.
She grinned and kissed me on the nose. “Charm a girl’s panties off, why dontcha?”
She wasn’t wearing any. I didn’t mention it. Instead I breathed, “I feel like I won the lottery.”
The big leaf ball was soft, squishy, and full of water, and felt like memory foam. She had no problem reclining back into it and sinking in a couple of inches.
I reached out a hand toward Regina, who immediately grasped it and led me toward her thigh.
Gob, man, she was soft, smooth and cool to the touch. Just that initial contact, her hands on mine and then mine on this expanse of skin was enough to get me throbbing, painfully hard in my pants.
“Touch anywhere you want,” she murmured. Her voice was already heavy with arousal and need, and she did the touching by herself, while I got acquainted with all the different pces on her. Although my instinct was to just sit there gaping at her, I knew this might be my first and st chance to be with a woman. So I ran both hands up and down her thighs, loving the contrast between her soft skin and the silky material of her stockings.
Then I started massaging her calf muscles and up over her thighs. Just running my hands over her taut muscles as hard as I thought I could get away with, then squeezing.
“Mmm,” she groaned.
“Is that… that’s good?”
“Mmm yeah. Do my feet.”
She put her stocking-covered foot on my chest and I proceeded to run my fingers up and down over every bit. The whole time, I couldn’t take my eyes off the junction of her thighs. She was running two fingers down her slit, sometimes working in small, fast circles, other times just massaging like I was doing. Up and down, up and down. Peekaboo.
I’d only seen foot massages in movies and porn, but I tried to make it as nice as I could. Regina’s eyes slowly closed and she threw her head back, moaning appreciatively. Whether it was from my massage or her own hand I couldn’t tell.
Eventually she put her other foot up on my chest, then stopped and rolled the stocking down her leg, removed it, and gave me the foot back. I got right to work, loving the warmth and softness of her body.
I then noticed her other foot was sliding up my thigh and tickling against my cock.
Her eyes were closed and she was hard at work on herself, so maybe she didn’t notice. It was possible I was just being used as a toy for her pleasure, but this was the most experience I’d had in my twenty years of life on this earth. It was definitely my first public encounter. Very arousing by itself.
So while I watched her fingers sliding over her, and her foot sliding over me, I worked on her foot with both thumbs, learning every bit of what was what, and which parts made her go ‘mmm’ with regurity. Turns out I didn’t need to worry about that.
“Right there,” she murmured. “Right there, yeah, yeeeeaaaahhhh.”
I kept doing that, both thumbs into the arch in slow, rotating circles. Her lips parted and she mumbled that she was about to cum.
“I want to lick it,” I blurted.
It was through clenched teeth that she said, “Get down here, stud.”
I got down, caressing one leg still in a stocking, the other bare, and scooted up to get my tongue on her open slit. She humped her butt up and down, so all I had to do was stick out my tongue. Feet rested onto my back now, and I inhaled the intoxicating scent. I could’ve cum right then and there, but I was too focused on the sight and smell and taste in front of me.
She was delicious. This, I would learn, was the magic. She was buttery and tasty, and I pped at her. She smelled buttery, too, like a croissant. She still continued to fondle herself, work her clit, fingers bumping my nose. I didn’t care. I just licked and licked at everything I could.
“Oh, guh… fuh…”
She arched her back and shoved her midsection down into me. I got a flood of that buttery fvor, so I pushed my tongue into her as far as I could go. She rewarded me with a shrill squeal of pleasure, and her thighs convulsing against my ears. One hand was also clutching at my hair.
“Wait wait wait wait,” she panted, “St-stop.”
I didn’t want to, but it was necessary to follow instructions. After all, she was the guide and I was the newbie in this world. In reality I told myself that this was her show and she could run it how she wanted. I was just a sex toy if she wanted to use me like one.
Although I had no real idea what she was thinking in wanting to do this, with me, I wasn’t going to stop her and be like ‘aren’t you capable of finding a guy who can fuck you senseless?’ Whatever this was, I wanted it again, though I had a feeling it was a one-time thing.
She tapped the space beside her, so I settled down and id there. After a few more moments of shaky breath and composure, she sighed contentedly, slipped off the other stocking, and rolled over to put her head in the crook of my shoulder, draping one arm and leg over my body. My very stiff body.
Her leg slowly moved up, and then down. Sliding over my crotch.
She was the picture of contentment: eyes closed, tiny smile teasing her lips, total rexation… all except her leg sliding back up and her calf muscle sliding back up over my dick.
“Mmm that was really nice,” she purred in my ear.
“Yeah. It was.”
“I liked it when you got assertive.”
I mulled this over. I wanted… a lot of things. But they all boiled down to the same thing. The question was whether or not I could force myself to say the words. Indecision and terror gripped me. It was ughable; here was a girl who’d just showed me her everything, gave me her feet and legs to massage, and let me stick my tongue up in her. She would have sex with me.
But another part of me still screamed that it was a trap, that she was going to turn me down and ugh at how insulted they were at the prospect. Just like Jaime Riley had done, just like Jessica Kynowski had done, just like Stephanie Kildare had done. And none of those girls had been anywhere near as hot as Regina.
After some more indecision time, she just let out a soft and sleepy cooing noise. “It’s all right.”
“I want…”
“Mmm?”
“I want… you.”
“What do you want exactly?” she teased. Her breath was on my neck.
Deep breath, Chris, I told myself. You can do this.
“I want… to have sex… with you.”
She sat straight up, eyes full of mischief, grinning oddly. Was this the other shoe dropping? I held my breath in case the cruel ughter came out now. She swung one leg over and my boner actually came into contact with her bare pussy.
“What a coincidence! I also want to have sex… with you. Actually first I’m going to give you the best blowjob of your life, and then, pff, you’re what, twenty-two?”
“Twenty.”
She grinned. “Never correct a girl who gives you a couple extra years, until you’re at least forty.”
“Right.”
“Anyway I’m sure you can get it up again. Then, then we’ll have sex. Maybe twice.”
I sted, somehow, five whole minutes. Now, I don’t know what your stamina was like when you were a virgin, or when you were twenty for that matter, but I only sted five minutes because Regina was really good at her job.
She freed up my erection and followed this by grinning greedily up at me. I could just about see sparkles in her eyes.
“Ohhh Christopher, I can’t believe we’ve been friends for almost a full day and I haven’t had this inside me.”
She quickly took me into her mouth, and expertly massaged me while removing my clothing, staring up at me the whole time. I would have just bsted off right there if she hadn’t pulled off and grabbed on.
“Girthy,” she muttered. “And pretty long. I am gonna get some mileage out of this bad boy.”
She licked at it, causing me to groan. I resolved, right then and there, to keep hold of every moment of this encounter mentally, so I could repy it whenever I was feeling lonely. Regina popped the head into her mouth once again and pumped several more times, then smiled at the sounds she was forcing out of me. It was like she had a direct line to my orgasm, and she was stopping just before the finish line.
This went on for some time, with her caressing my balls, slowly jacking my cock, and sucking on it. She kept up the soft stream of compliments the whole time, telling me she liked the head, this baby was going to rearrange her insides, and she couldn’t wait to feel it all the way up to her diaphragm. After tickling my sack with her fingernails, she gave it a long suck, then whipped her shirt and bra off.
Now she only had on the pleated skirt, and she soon stood with her back to me, shimmied out of it, and tossed it out of the tree like no big deal.
“Do you want…” she asked, and lowered her midsection down onto mine with this seductive tone that nearly made me bst off in her hand. “…do you want to put it in me?”
“Y-yeah… I do,” I managed.
“First you gotta cum for me,” she said, and lowered her body down mine, pressing it against the bottom of my cock and sliding downward. Up her midsection, past her belly button and ribs. She stopped with it nestled between her breasts and pushed them together. “Maybe you can try this next…” With that, she pushed them together around my cock. She wasn’t massively endowed, but they were enough to form a channel of pillowy softness.
“Go on,” she whispered. “Funk my tits, Chris.”
I did, moaning and groaning like she was killing me. It felt like she was.
Again, I gazed down and got every detail. I didn’t know if this would be the only time with Regina, the beginning of a long dry spell, but I was going to use this encounter for years to come. I memorized the way my cock appeared and disappeared down into her cleavage, her pointed little tongue reaching down to get at the bead of precum she found, and the gleam of her perfect teeth when she gnced up at me and grinned.
Finally, on the downstroke, she let go of her tits. Taking my whole cock into her mouth, she sucked, hard. That was the end of resistance from me; I erupted with a shout. It was enough that I triggered her gag reflex, and she ended up coughing. My seed went dripping out of her mouth, but she swallowed before dipping back down and licking the rest up.
“Holy shift,” I mumbled over and over again. “Holy shift.”
“You came a lot,” she said, wiping her mouth with a thumb and sucking the rest off her lips. Her tone grew hungry again. “…and you’re still hard.”
A moment ter she’d straddled me again, and I could pinly see her glistening pussy ready to swallow me whole.
“Oh wow,” I said.
“Pay… attentio-uh!” She went so slowly, I saw literally every detail. Every bit of her enveloping me, even as the overwhelming sensations and the incredible tightness swallowed me up, I catalogued every microscopic event.
Finally, she was sitting on my thighs, hands on my chest, unmoving.
“You… okay?”
“I have a… confession,” she said through clenched teeth. More a hiss actually. “I uh… I’ve never done this either. And you’re… big. I’m just gonna sit here and let my pussy… get used to the size. Okay?”
“Okay.” When you’ve just been handed the best gift in the world, you don’t ask for a gift receipt. Or, hell, you don’t go talking back to the gift giver.
When she moved, there was a new wave of pleasure, and I looked down to see my dick reappearing, coated with a thin sheen of blood.
“Yeeeahhh,” she said, and sank back down. Her eyes fluttered closed and both of us let out mirror groans of bliss. This was the best day of my life. I hadn’t died, and now… I guess I could?
“Does it hurt?” I asked.
“A little.”
Another few strokes and it was clear it didn’t hurt any longer. She was shaking and shuddering, telling me how great it felt. It was so deep inside her, she said. It was really… fluffing… big.
She came just as I was about to tell her I was feeling that familiar rise.
“Uh…” I told her. “I’m gonna, I’m…”
She’d gotten one hand on her clit, massaged it all of three times, and colpsed down onto me, shaking like she had the first time with her thighs on my head.
With no idea what to do instead, I grabbed two big handfuls of Regina’s plump ass, pulling her up so I could fuck upwards from below. All the while I kept telling her that I was gonna, I was gonna…
In one lightning movement she got up off me and sank down to her knees again, this time taking the whole load on her face. I was ft out astonished at the amount, for one, and the fact that she would do this kind of thing. I painted her face and she moved around, eyes closed, so she could get as much of her face covered as possible.
She didn’t seem to know what to do with all of it. Her eyes darted to my face, then around at all the nothing we had avaible, then back at me. Finally, with nowhere else to put it, she scooped it onto her fingers and into her mouth.
Finally, after colpsing down onto the pillowy soft green bulb next to me, she snuggled up into my shoulder again. I put an arm around her and marveled at the softness of her skin and body. It just wasn’t possible to stop stroking her or squeezing this or that part.
“You must think I’m such a slu...” She got caught up on the word ‘slut’ and, not wanting to swear, turned it into, “…sludge.”
I ughed. “I don’t think you’re a sludge.”
“I just… this is the first time I got to escort a single new hire. And you were so cute. And then you nearly… anyway I don’t, this isn’t… I’m not normally like this.”
“That’s all right,” I told her, and continued hefting up both her breasts, one after another, then tracing the outlines of her nipples with my fingers.
She sighed contentedly and got a handful of my junk. “That was pretty fussing great.”
“I’m so gd you liked it,” I told her. “You were… amazing.”
Regina smiled indulgently at me, down at my already-stirring cock, and back up at me once more. She then proceeded to teach me all about a woman’s body. And use me for her own pleasure.
I spent more time touching and exploring in that single afternoon than in the entire rest of my earth life. We didn’t just do it once more after that.
This is Christopher making a core memory.