It started with a simple strawberry. A bright red one with a long stem. Giselle had straddled my back again and lowered the long stem down in front of my face. She twirled it gently, holding the stem between her thumb and forefinger. “What do you think?” she asked. “Can you take it? It’s not too big but it’s awfully fragile.”
In an instant the bright red berry was gone and Giselle slid her slippery pussy slowly down my back, until I imagined she must have been on her knees between my spread thighs. The tip of the berry was icy cold when she pressed it against my tight hole, but I could feel my asshole clench even tighter. It was an involuntary reaction to the icy intrusion.
“I can see I have my work cut out for me,” Giselle announced solemnly. “We could be at this a long time.”
I felt something sticky dribble down the crease in my ass. It oozed slow, like honey. And I think that’s just what it was. When the slowly dribbling drop inched towards my clenching asshole, Giselle’s tongue was there to meet it. She pushed the sticky substance around and around, all over my anus. The stickiness felt strange. It was lightly pulling at my hole. But the warmth of her tongue, pushing into the tight opening now and then, felt good. My hole definitely liked that. When Giselle had licked the surface of my asshole clean, she dripped another trail of honey down the crack of my ass. Again, it oozed so slowly down I felt that this alone, this waiting on the honey business, could in itself take hours. My ass wriggled and squirmed impatiently, perhaps trying to assist the honey in its journey down, but when the honey finally reached its destination, and when Giselle’s warm tongue was once again there to greet it, the honey felt even more appealing than it had the first time. I felt my sphincter muscle relax a little. I felt it eagerly anticipate her poking tongue. I moaned into my gag. And I arched my ass open for her.
“This is definitely progress,” Giselle announced quietly. “But let’s not rush it. You’re not really ready for the berry yet.”
Giselle came around in front of me and I watched her polish off my glass of wine. She sat naked where I could see her and she lit a cigarette.
“I know how to remedy this, though, so don’t lose heart,” she said. “It takes patience and then you’ll be able to get anything you want in there. Even something like a strawberry.”
I watched her as she thoughtfully smoked and even though I didn’t have some long list of things I’d been trying to get in there, I suddenly felt like I desperately wanted to please Giselle. I wanted anything in my ass that she wanted to put in there. My hips were rotating restlessly against the ottoman while I watched her smoke. I could feel the wetness in my vagina beginning to drool down into a puddle on the carpeting. I didn’t know what she had in mind for me, but I had a pretty good inkling that my ass was going to get fucked good by this gorgeous skinny woman who, let’s face it, was technically old enough to be my mother.
When she finally stubbed out her cigarette, I watched her snap on a latex glove. I’d never been with anybody who’d worn gloves like that before, except the doctor in the examining room and it made my stomach a little queasy watching her snap it on. I wanted to ask her where she got gloves like that, but I had that gag stuck in my mouth and couldn’t say a word. But when she disappeared again behind me and, without much fuss, slid a lubed finger up my ass, I wasn’t thinking about buying gloves. I just gasped. Well, I moaned a little bit, too. She worked that latexed finger into me deep. And it was so slick with lube my tiny hole couldn’t put up any kind of resistance. It tried to push against the intrusion, but Giselle was insistent. She worked against the pushing hole. She slid two fingers in, in fact, and pumped them vigorously in and out while I grunted a little and tried to figure out whether or not I liked it.
But I didn’t have a lot of options. I was spread open for her either way. She paused for a moment and squirted the lube directly into my hole. It was an icy and unpleasant feeling, but the sensation didn’t last long. It was replaced by the less subtle intrusion of three greasy fingers this time. Three greasy fingers shoved into my lubed hole. Giselle was exerting herself, I could tell; she was grunting from the effort of pumping her three fingers against the muscle that was trying to expel her.
“Jesus,” I gasped into my gag. And my eyes were riveted to the picture on the floor in front of me. That gaping hole. It was going to be mine before morning came and I was sickly curious about how we were going to achieve this.
“Are you ready to pick up the pace?” she panted. “Are you ready for some action?”
Of course I couldn’t answer her and I guess she didn’t really expect me to, but Giselle came around the front of me then and let me watch her strap on the dildo.
“What do you think?” she asked urgently. “Can you handle this guy?”
She was referring to the dildo, to its overall size. But I was too caught up in looking at her. I’d been with girls before, and girls with dildos, too, but I’d never been with a woman yet who had actually strapped one on. Giselle looked hot. I was eager again.
“What do you think?” she persisted, as if she’d forgotten about the gag. “You think you can take him?”
I grunted my urgent approval as I watched her lube it up. Uh-huh, I grunted several times, and I even nodded my head.
And when she climbed onto me, mounted me, pressing the greased-up head against my asshole, easing the dildo into my rectum, it was like I was fourteen again and I was with that boy. We’d skipped school and we were hiding in his father’s den. It was dark and very quiet in there. Their maid was home, but she didn’t know we’d skipped school and snuck back into the house. She didn’t know we were hiding in the den. But we had decided we were going to do this thing, we were going to try it out. We were determined. And I’d brought my torn-out article from my mother’s old Cosmo and my plastic jar of Vaseline in my shoulder bag. We didn’t get undressed because we were afraid of needing to leave in a hurry. So we just unzipped his fly and took his hard dick out. We smeared Vaseline all over that thing. And then I leaned into one of his father’s big leather club chairs, I laid with my face pressed against the cool leather, while the boy shoved up my skirt and pulled my panties down to my knees. Vaseline makes everything a greasy mess, especially nice leather club chairs, but it sure helped that boy’s hard-on slide right into me, right into my asshole. It was like we’d talked about over the phone, he was actually fucking my ass. I wasn’t sure I really liked it, but I wasn’t sure I didn’t like it either. The pressure felt exciting, I liked the feeling of being filled up. But what I liked most was his fully clothed weight on top of me while my panties were around my knees, and the way he smelled while he grunted and pumped away at my virgin asshole, the way all boys smelled back then; like mown grass and sweat and tobacco and spearmint gum.
That was how it felt with Giselle, like I wasn’t really sure I liked it, but I wasn’t sure I didn’t like it either. The dildo felt huge in my ass and I was grunting into my gag. But her naked weight was on top of me. Her breasts were pressed flat against my back and she was sweating from the effort of pounding my hole. I loved all that sweat. And I didn’t mind it when she pulled the dildo out and reminded me I wasn’t fourteen any more and that it was 1980. She shoved a glob of Crisco up my ass and proceeded to pump me with a dildo too huge, too heavy to even attempt to fit into the harness. Giselle didn’t strap it on, she held it with two hands and shoved it clear down to its base, stretching me completely open.