“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.
I groaned like some drugged animal giving birth in a public zoo, but I was loving every minute of it. The Crisco made it easy on my hole. I opened right up and accepted every round fat rubbery inch of the fake dick that Giselle pounded so mercilessly into me.
And my eyes were glued to the photo in front of me, I was transfixed by that gaping hole. I was suddenly in love with the mystery girl in the Polaroid. I knew now what had stretched her open, I knew now how she must have felt – spread wide and securely battened down. A gag probably shoved into her mouth, too, so she could grunt over and over in it as her rectum was filled to capacity, her ears filled with the sounds of Giselle’s own grunting, from all the strenuous effort . . .
When Giselle had worn herself out she disappeared briefly into the half-bath then re-emerged with a soaking towel. The towel was hot and felt great against my tired hole. And when Giselle had wiped away most of the grease, there was the familiar bright flash again behind me and the sound of the grinding inner workings of the camera. By the time she’d untied my gag, the new photo was ready.
“What do you think?” she asked softly, as she laid the Polaroid of my seriously opened hole on the floor in front of me. “You think you can handle that berry now?”
I’d forgotten about the strawberry. “I suppose so,” I panted, although I wasn’t entirely sure.
“I’ll wedge it in with a little honey and then I’ll eat it out of you. But I want to get a picture of it first. My husband loves these pictures,” Giselle explained, “the ones with the food in the girls’ asses. He carries them in his overnight case and takes them all over the world.”
I wasn’t sure I was particularly pleased with that idea, but I couldn’t keep Giselle from wedging that sticky strawberry into my gaping hole. It took it easily this time, the berry perched right there in my puckered anus. Then the camera flashed away. I wondered what her husband looked like; would I ever recognize him on the street? Would it haunt me that somewhere in the world a man was flying from place to place with a picture in his overnight bag of me with a strawberry in my ass? And what about the mystery girl in the other Polaroid? What kind of food had ended up in her stretched hole?
But my worries melted away when Giselle’s mouth found the berry. True to her word, she nibbled it out. She plucked the stem clean and then sucked the berry and gnawed it and licked it until it was gone.
“Come on,” she said, as she undid all the hardware, the buckles and the restraints, “let’s go to bed. Let’s make a little love.”
She refilled my wine glass but I didn’t want it any more. I just wanted to be flat on my back underneath her on her big bed. The sun was just coming up in all those enormous penthouse windows, so when she straddled my face for some sixty-nine I could see her bung hole clearly. It was stretched like mine, but hers was permanent. She lowered it right onto my tongue while she shoved my thighs apart wide and buried her face between my legs. Her hot tongue licked at my tender aching worn-out hole, while her fingertips deftly massaged my clit. I tried to rub her clitoris, too, but she didn’t seem to want that. She seemed content to just ride my tongue with her open hole.
I licked her asshole with all the earnest attention I could give her, but after a while, I must confess I couldn’t help it; the way her mouth was making me feel between my legs absorbed more and more of my concentration. I couldn’t give Giselle the amount of attention I should have. While her fingertips slipped all over my swollen clit, and while her tongue licked eagerly at my played-out asshole, I couldn’t help myself, I came. I dug my fingers into Giselle’s gorgeous ass and clamped my thighs tight around her head and came.
And since it was 1980 I didn’t sleep with her. I stumbled into my clothes and left. I kissed her goodbye and all, but then I went out alone for breakfast.
A couple nights later she called me. “My husband’s in Thailand,” she said. “What do you say we go at it again? Are you up for it? You’re not still sore, are you?”
My bung hole quivered. “No, I’m not sore,” I said into the receiver.
“I have some new things that we could try putting up there. Are you game?”
And I realized I was. It was the beginning of my inevitable descent into hell with a completely insane person. “I’m game,” I confessed.
“Good,” she exclaimed quietly. “Be a doll and pick up some film. Now how do you feel about root vegetables?”
2. Swingers
Friday night I went home with some married people. I wish I could tell you they were those vibrantly tan, Hollywood fast-lane types but they weren’t. They were just married people. Intellectuals. Two married couples clearly pushing something like their mid-fifties. I have to say they weren’t even very attractive. They certainly weren’t fans of cosmetic surgery or fad diets.
You’re probably wondering why I went home with them, then. I’ll tell you. They asked me to.
I was hanging out in one of those book bars. You know the one, the really well-lit place. Small and stuffy with the built-in bookcases lining the walls, a teeny-weeny fire in the equally microscopic hearth. I was there being stood-up. Nothing serious, though, no tragedie l’amour. It was just my intensely hyper garment-industry-worker girlfriend who had stood me up. She’d obviously got snagged into working more overtime.
So I was alone in a surprisingly comfy chair, nursing a glass of red wine tentatively since I wasn’t sure if I was just going to turn around and go home. That’s when they walked in. Two unattractive married couples in their mid-fifties. They made an instant commotion, dragging a tiny table around and scooti
ng a bunch of comfy chairs together so they could all sit down in high spirits, practically on top of me, and proceeded to order an incredibly expensive bottle of wine. I loved watching that; the waiter trying to find a spot to stand in that was anywhere near them while they ordered, and then having to set up an elaborate pedestal wine bucket somewhere in reach of them, too. Thank God they smoked. They really needed some more stuff on that tiny table.
They couldn’t help but notice me right away since they were practically sitting in my lap, and they kept trying to engage me in their small talk. I resisted their stabs at friendliness until they offered to share their wine, which necessitated their ordering another bottle. The waiter was really glad to see a fifth party, me, push into the already unmanoeuvrable fray. So physically we got close in a hurry. We couldn’t help it. Still, one of the women, Fran, seemed to impinge on more of my personal space than I thought was really necessary. Right away I figured she was hitting on me. It took a couple glasses of that expensive wine before I realized they were all hitting on me.
I went home with them mostly because I couldn’t believe they’d had the balls to ask me. They were so matter of fact about it, too, like they always came on to younger, much more attractive single women and got affirmative results. I was swept off my feet by their sheer blind optimism. Well, no. Actually I was swept off my feet by them, literally. I think they wanted to rush me into the nearest cab before I could change my mind.
We wound up in the home of the couple who lived closest to the bar. It was a really nice apartment. That couple, Cy and Ruthie, had never had any kids. Every extra penny had been available for them to spend on themselves. They favoured upholstery, too. Everything was upholstered, in every conceivable pattern. I could tell an interior decorator had been paid handsomely to have his or her way with Cy and Ruthie. But I ceased noticing the decor when Fran started to undress me.
At first I felt alarmingly uncomfortable because no one else was undressing. I shy away from being the only one naked in a crowd of strangers and I was wondering what I’d got myself into. But after she’d stripped me naked, Fran pushed me gently down on the sofa and began to massage my feet. I began to relax. I sank deep into the upholstered sofa while Fran sat on the coffee table in front of me with both my feet in her considerable lap. Her hands were unexpectedly soft and steady. She worked each and every one of my toes and the balls of my feet with just the right amount of pressure.
She smiled encouragingly at me while the others just watched. I wondered if I was being lured into some exhibitionistic pas de deux with Fran. As I sunk deeper into the couch in an increasing state of bliss, I wondered how a group of people arrived at that sort of arrangement. “Hey, I know,” I imagined them saying, “let’s all go out together, find a girl half our age and watch her get frisky with Fran.” There would be general agreement all around.
Then Fran broke my reverie. She lifted my foot to her mouth and sucked in my big toe. I was ready for it. Fran’s mouth was so warm and wet, I moaned. And slowly but surely things started to move around me.
Cy got out of his chair. He came over and stood by Fran, his crotch level with her face. He unzipped his fly, but when he took out his dick it was flaccid. Completely limp. Fran didn’t seem at all perturbed but I felt a little indignant. I was thinking, Hey, I’m naked here! The least you could do is worship me, have a raging hard-on! But, alas, Cy was no longer nineteen and Fran appeared to be used to it. She went right to work with her mouth, alternating between my big toe and Cy’s flaccid dick until remarkable things began to happen. It turned out Cy was hung.
Ruthie came over to join us then. She undid her husband’s trousers completely, letting them fall rather dramatically to his ankles. Then, while Cy went to work on Fran’s mouth with his stiff dick, getting her complete attention now as my feet lay limply in her lap, Ruthie kneeled behind Cy and seemed to be tonguing his ass. Her face was way in there and I figured if I was Cy, as I watched his huge erection pumping in and out of Fran’s mouth while his wife, fully dressed and on her knees, tongued his asshole . . . well, I figured I’d probably be liking that an awful lot. I got wet between my legs watching those three carry on like that.
Kenneth, Fran’s husband, was the last to take the plunge, but suddenly he was sitting on the couch next to me and he was naked. He had a lot of hair. A touch more than I would have preferred. He didn’t seem to notice that he didn’t appeal to me, though. He lifted my arms and held my wrists together behind my head, then proceeded to lick my armpits. It was an unusual move but it made my nipples shiver and get erect. As Kenneth licked his way down to my breasts and when his mouth closed around my erect nipple, I moaned again. Hairy or not, he was good with his mouth. My nipple swelled from the perfect pressure of Kenneth’s sucking and I decided, at that moment, that I ought to have sex with older people more often, they understood pressure.
The coffee-table gang was starting to get rambunctious. Fran was flat on her back now as Cy straddled her on the low table, completely humping her face. She was making these eager but smothered little sounds that made it seem like she was liking it a whole lot. And Ruthie had removed Fran’s panties. She’d pushed apart Fran’s legs and buried her face between Fran’s fleshy thighs.
Kenneth’s mouth was still working expertly on my nipples, moving from one to the other, tugging tugging tugging, but now one of his hands was between my legs, rubbing my slippery clit.
I didn’t think I’d be able to take much more of it; the free show on the coffee table and the prefect pressure on each of my three most responsive spots. I thought I was going to come.
That’s when Cy startled all of us. He stopped humping Fran’s face and went for her hole in a hurry. Ruthie had to get out of the way fast. She plopped down next to me on the sofa. She was the only one still dressed. She began to unbutton her blouse while Kenneth was rolling a rubber onto his erection. I felt a little overwhelmed. I didn’t know who to focus on. It was obvious Ruthie wanted me to suck her fat little tits, but I was kind of hoping Kenneth was wanting his dick in me because I was definitely ready for it. That’s when it occurred to me to quit sitting like a blob on the sofa and get a little assertive; get into the rhythm of being a swinger. Nothing was preventing me from having them both.
I turned over and raised my ass in Kenneth’s direction while I let Ruthie guide my mouth to one of her jiggly tits. “Would you look at that tight tush,” Kenneth declared as he slapped my ass hard. “Fran had a tush like that when I married her. Thirty years ago.”
Then he mounted me. He slid his substantial hard-on into my soaking hole without needing any help from me. He slammed into my hole hard, making me cry out right away. He had a firm grip on my tush and was going to town.
Ruthie lifted my face from her breasts and started kissing me. Deep. Her tongue was crammed into my mouth while I grunted from the force of Kenneth’s cock pounding into my pussy from behind.
I had never been with more than one person at a time before. It was kind of a scary feeling. I felt myself becoming insatiable. It wasn’t long before I was flat on my back on the carpeting. Ruthie had stripped completely and was straddling my face. She had a tight grasp on each of my ankles as she kept my legs spread wide, giving Kenneth’s hard cock free rein on my helpless hole, pound pound pound.
Ruthie’s snatch was completely shaved. Her mound was smooth from the tip of her clit to the cleft in her ass. It had to be a wax job, I thought, she was that smooth. And I wondered: who waxes a fiftyish woman’s pussy completely bald? I figured her husband, Cy, had something to do with it.
Cy was sitting in a chair now, sucking on a cigar, taking a breather, but his dick was still rock hard. It was poking straight up like the Chrysler Building. Not that I could see him too well with Ruthie’s ass in my face, but I could tell that Cy was watching me get nailed. I was curious what he was thinking.
“I have to pee!” I suddenly announced as the urge came unmistakably over me. Rather than cause a chorus of disappointment a
nd regret among my fellow swingers, the news didn’t cause them to miss a beat. They’d switched partners before I’d even stood up.
When I came back into the living room (and I hadn’t been gone long, mind you), Fran was down on all fours with Kenneth’s hard-on seriously down her throat and Cy was fucking her ass. The incessant pounding she was getting at both ends was making Fran’s boobs bounce around like crazy. The whole thing was mesmerizing; what the men were doing to her and the way Fran seemed to be wildly into it.
Ruthie came in from the kitchen with a tray of decaf espressos. She had that look on her face, like she’d had her orgasm and was feeling completely contented. She sat down next to me with her cup of espresso and we both watched Fran go the distance with Cy and Kenneth. And right when Fran started to jerk around and squeal, an indication that Fran was probably coming, Kenneth pulled his dick out of her mouth and shot his load in her face.
She seemed a little peeved by that, but she didn’t do much about it because Cy was still going hog wild on her ass. I wondered if Kenneth was going to hear about it later, though, when he and Fran were home alone: “How could you come in my face like that?” I could hear Fran saying. I knew she’d be capable of some serious chiding. “In front of everybody,” she’d probably continue. “You know I hate it when you do that.”
But for now everyone was amicable. Everyone was drinking decaf espresso except me. I hadn’t come yet. I felt fidgety and distracted. Since I’d never been a swinger before, I didn’t know the proper etiquette. Was it up to me to let everyone know I wasn’t through yet, that I hadn’t come?
I felt so ignorant, so ill equipped to swing. I toyed with the idea of slipping off to the bathroom again, to take care of myself alone. No one had to know what I’d be doing in there. I could come quick, I felt certain of that. Still I felt a little let down. I’d been having too much fun with everybody to suddenly resort to climaxing alone, in some stranger’s bathroom.
The Mammoth Book of Erotica presents The Best of Marilyn Jaye Lewis Page 2
