Sylvia's Bondage Date Ch. 5

Sylvia rang the doorbell of Jason's condo and waited. This was going to be interesting. After a few dates at Clancy's, and then a date that was kicked up a major notch at Pacino's, Jason had offered to cook dinner for her himself. She had no idea what to expect, but she knew from experience that when a bachelor offers to cook a woman dinner, he generally prides himself on his cooking and knows how to provide something a cut above Kraft Dinner.

Jason answered the door with a big smile on his face. Sylvia trusted that Jason would warn her if he intended to tie her up and cut her clothes off again, so she had gone all-out on her wardrobe once more. He paused to run his eyes up and down her electric-blue dress with another of the plunging wouldn't-you-like-to-grab-these necklines that always made his penis twitch. This one was set off by a pair of dangly diamond earrings and a small diamond solitaire strategically positioned just above her breasts. Jason had an eye for jewelry, and although he couldn't be sure without a close inspection with a jeweler's loupe, he strongly suspected that they were real.

He would have been right. They were a gift from a former lover, who lavished expensive gifts on Sylvia in order to encourage the behaviour he wanted. It worked for him, too, until it didn't. He started pushing their kinky sex far past her boundaries, and after the night he tied and gagged her and then used a cane on her bare ass to make welts that took weeks to heal, there was no amount of expensive jewellery that would get him another date. He was lucky that he didn't have to go to emergency to get his gifts removed from his ass.

After Jason had admired her for a few long seconds, he backed away to make room and said, "Sylvia, you look absolutely wonderful. Come in!" He flicked the door closed, put his arms around her and pulled her in for a long, lingering, smoky-hot kiss. He could feel her nipples, hard as little diamonds themselves, pressing against his chest, and she felt the pressure of his growing erection against her thigh.

Eventually they broke the kiss and came up for air. Sylvia inhaled the delicious scent of frying bacon and asked, "Are we having bacon for dinner?"

"Not exactly. That's for me to crumble on the Caesar salad. I know you love pasta, so we're having veal-stuffed cannelloni. I have a fancy-ass pasta maker that makes cannelloni tubes, among other shapes, and I think they're way better than the ones you buy ready-made. And I know a butcher that still sells veal. It's almost impossible to get in grocery stores these days - I think people just aren't willing to pay what they have to charge for it now. But there's nothing better in terms of meat."

"Aren't they horrible to the calves to come up with super-tender veal?"

"That's European white veal. You're right, they pen the poor things up so they can't get any exercise and the meat stays white. This is Alberta red veal. The little guys get to move around until they're whacked for their meat. Yes, they're killed young, but until then they have as good an existence as any farm animal is likely to get. Frankly, I think it has more flavour than white veal, but it's still far more tender and delicate than beef."

"OK, I'm sold. It sounds and smells divine. But how do you get the veal inside those little tubes?"

"Trade secret. But you know me. I'm pretty good at squeezing things into tight places."

Sylvia winced at the crude inuendo, but she had to admit that he was right about what he could fit into tight places. And, just like her mouth, which was watering at the thought of veal cannelloni, another of her tight places was moistening at the thought of what they might be having for dessert.

***

Sylvia put down her fork and sighed a contented sigh. "Jason, that was absolutely divine."

"Did you have enough? I deliberately served modest portions so we won't be too full and bloated later."

"It was perfect. Most restaurants serve you way too much, especially pasta, and you're right, too much food makes it hard to enjoy any after-dinner activities."

"Speaking of which - all evening I've been dying to see what's inside that gorgeous dress. Not that I don't know, but I always love it when you show me again."

Sylvia's smile broadened. She pushed her chair back from the table, leaned forward slightly, reached behind her back, and pulled the zipper of her dress down. As the fabric relaxed, the V-neck that had precariously held her breasts in place gave up and let them slip out.

She usually wore a bra, but tonight, she couldn't figure out how to wear one without messing up the effect of the dress's neckline, and since they wouldn't be out in public, she had decided to try without. It turned out to be a good decision. Her breasts weren't exactly small - the small end of C-cup - but they weren't huge, and they were firm and sat high on her chest without sag. A bra would have prevented them from jiggling and kept her nipples from making little bumps through the fabric of her dress, but frankly, she wanted to tease Jason with both of those effects. Also, she had found that the feeling of fabric rubbing gently on her bare nipples whenever she moved was subtly erotic.

The effect certainly worked. Jason had had a hard time keeping his eyes off her tits the whole meal, and now she was happy to show him the full glory of what he had been craving. She shimmied her shoulders a bit to make her tits wiggle invitingly, then stood up to let the dress slide to the floor at her feet.

Once she had decided to forego the bra, she had decided to forego panties too. She usually liked the sensation of undressing, or being undressed, one piece of clothing at a time. But this time, she revelled in the sensation of revealing her entire body from head to toe in one seductive motion.

She held her pose across the table from Jason, standing with her feet slightly apart to emphasize the ample pussy that peeked from between her legs. The expression on Jason's face as she was suddenly revealed was priceless. She thought he might be about to cum in his pants as he gazed admiringly at her toned body wearing nothing but the diamond that sparkled on her chest just above the valley between her breasts.

"I take it you like what you see," she teased. She took her right hand and pressed it against her mons, sliding a finger between her labia and rubbing it slowly against her clit, already engorged with desire. Just in case Jason wasn't already melting with need, she put her left hand on her right breast, pinched her nipple gently, and rolled it between finger and thumb.

"Oh shit, Sylvia, you know I like what I see. But I'd like to feel what I see too. How about you get down here and help me out with this?" He pushed his own chair back from the table, unzipped his pants and undid his belt, and released an obviously aching hard-on.

Sylia dropped to her hands and knees and crawled under the table, leaving her electric blue dress behind. She arrived at Jason's chair, flipped the tablecloth up to cover his lap, and brought her lips down around the tip of his eager penis.

She wondered what it would be like to do this in a public restaurant. She had read about plenty of under-table blow jobs on Literotica and other smutty sites that she masturbated to between sex-filled weekends, but she really couldn't imagine it being as simple as it was as made out to be. Even though the tablecloth more or less hid what she was doing, she knew that her head was making a bulge that anyone could extrapolate into clandestine sex. And as she started to bob on Jason's cock, she knew that the tablecloth must be also bobbing suggestively, and that the gasps he was making would make it utterly clear what was going on under it. She decided to relegate the idea to the realm of fantasy - hugely erotic fantasy though it was - and avoid the arrest for public indecency.

Right now, though, she didn't have to worry. She could just enjoy the feel of the cock in her mouth as she took it a little further in with each bob. Soon it was all the way down her throat and his balls were gently banging against her chin with each bob. He was thrusting back to meet her, and she revelled in the way he filled her throat. His firm crown slid up and down and massaged her throat, and she dug her tongue into his cockhole every time she pulled back to snatch a breath. She felt her breasts rocking back and forth on her chest, a sensation that added to the incredibly erotic feelings that blowing Jason always aroused in her. It wasn't long before he pulled out of her throat, gave a few more thrusts against her agile tongue, and began to pump hot semen into her mouth.

As his spurts gradually subsided, she kept her lips sealed around his softening cock as he shuddered through blissful aftershocks. Then she swallowed and, once her mouth was empty, worked her tongue around his tip to clean off all the residual cum. She was glad that Jason wasn't one of those men - probably influenced by too much porn - who like to pump cum all over their partner's face, breasts, or other parts. That makes sense in porn, since viewers need a good view of the cum shot, but in reality, it's just messy and unsatisfying.

Sylvia was a little puzzled. Jason didn't usually let himself cum from a warm-up blow job, wanting to save his load for a later fuck when he had her securely tied up to feed his dom fantasies. But who cared? If he wanted to cum in her mouth right away, who was she to question? She figured that he had a plan - Jason always seemed to have a plan, and she loved him for it, since his plans always seemed to involve showing her another new way to have ecstatic pleasure.

Once Jason's breathing has slowed to a more or less normal rate, he hitched his bum up off the chair and said, "Help me get these fucking things off." She reached up and pulled his open pants and underwear down and off. He unbuttoned his shirt and shucked it off awkwardly, still seated in his chair, but then he stood up, and she popped her head from under the tablecloth to gaze at his naked, buff body with his penis dangling contentedly.

He held out his hand and helped her up from under the table. He led her by the hand into the spare bedroom and stopped in front of the closet-cum-sex dungeon.

"Ready for some more adventures?" Still savouring the salty-bitter taste of his cum on her tongue, Sylvia just nodded.

Jason opened the door to the closet, and Sylvia had to confess to herself that she was glad to see that Consuella was nowhere to be seen, nor was any other third party. She had to admit that it had been incredibly arousing to have a suspended, naked woman watch intently while Jason fucked her ass and then augmented the fuck with anal beads. Although it had played at the corners of her mind a bit, exhibitionism had never been high on her fantasy list, but Jason had known just how to pour gasoline on those half-buried erotic fires. Still, she was selfish enough to like having Jason to herself again.

Jason produced the spreader bar that he had introduced her to the last time. She was happy to see it - she had loved having her body helplessly folded up with her ass in the air. She got down on her hands and knees to let Jason fasten her ankles into the cuffs to force her legs wide apart. Then she reached down between her legs so he could fasten her wrists to the bar and keep her folded into her utterly exposed position.

As she usually did, she squirmed and pulled against her restraints, not trying to get free but just enjoying the fact that she couldn't. She focussed on the feeling of her pussy and asshole being pulled slightly open by the bar that kept her legs so widely separated, and she wondered what Jason was going to put in what part of her body next.

He presented her favourite gag in front of her face, and she tipped her head back and opened her mouth as wide as she could. As he pushed the stuffer ball behind her teeth and buckled the wide leather panel across her lips, she hoped he had washed it off after it had been in Connie's mouth the previous week. She knew he would have - Jason was always a stickler for sanitary sexual practices, and if his cock was ever up her ass, he never shoved it in her cunt afterward without washing it first. Mostly, she was just glad to have her old gag back, although she had to admit that having her panties shoved in her mouth and sealed in with tape had been an interesting throwback to their first date. Whatever she was gagged with, she always loved the feeling of something plugging her mouth and multiplying her helplessness.

Sylvia closed her eyes and fantasized about what Jason would do next. She wasn't surprised to feel him pull her bumcheeks apart to get better access to what lay between them. His warm, wet tongue slipped between her labia, twiddled with her clit for a minute or two, and then travelled between her lips the long, slow length of her vulva until the tip settled at the entrance to her vagina. She made a long, low moan of pleasure behind her gag, and would have squeezed her legs together to increase the sensation if she hadn't been prevented by the spreader.

Jason's tongue penetrated a short distance inside her. A tongue isn't really made for penetration and he couldn't reach her G-spot with it, but the sensation of having it even a little way inside her body was electrifying. She jerked in her bondage and let a shrill "eek" out through her nose.

Jason played in her cunt until it was gushing with juices, then continued up her perinium, licking and flicking all the way, until he reached her anus. As he worked his lips and tongue in and around her asshole, she could feel the sensations building until they erupted in the first orgasm of the evening. It wasn't a huge one, but it was a satisfying precursor of more to come once Jason's dick was finished its refractory period. Her whole body stiffened, her head tipped back, and a low, guttural "MMMPPPHHH" erupted from behind the gag.

Knowing that she would be hypersensitive for a minute or two after her orgasm, Jason paused his tongue and just held her pussy soothingly in his hand while she came down. Once her breathing was more or less back to normal, he crooked the first three fingers of the hand that was holding her pussy and slid them inside her. She was so wet and slippery that Jason had no trouble getting in right to the last knuckle, which gave her vagina a wonderful stretched-out feeling. From behind her, his fingers were crooked the wrong way to massage her G-spot, but it didn't matter. As he thrust his fingers gently in and out, the sensations radiated through all the parts of the buried clitoral tissue that made up her G-spot as well as all the sexually sensitive tissue around it. The beginnings of another orgasm began nudging at the edges of her nervous system, and she made another long "Mmmmppphhh" of satisfaction.

There was a bit of awkward fumbling behind her that she couldn't quite see, and then she felt a cold squirt of lube hit her asshole and run down her crack. Jason's hand moved a bit, and she felt what had to be his thumb gently but firmly push its way past her sphincter and into her rectum. Jason's fingers were still in her vagina, and he pinched the narrow barrier of tissue that separated her vagina and rectum between fingers and thumb. As he made gentle massaging motions with that hand, he brought his other hand around and rubbed firmly on her clitoris, which was now heavily engorged and standing out like the last joint of a little finger.

The stimulation from every part of her pelvic region at once was driving her irresistibly toward another orgasm, much bigger than the preliminary one. Her toes curled tightly and her hands, still cuffed snugly to the middle of the spreader bar, balled into tight fists. The wave broke over her with another heartfelt "MMMMPPPPHHHH!" pushed out through her nose by the gag that stuffed her mouth and sealed her lips.

Again Jason took his hands away and let her recover. He came around to the side of her folded body so he could watch her sweat-streaked face as she came down, more slowly this time owing to the greater power of her second orgasm. She couldn't help noticing that his dick was no longer dangling contentedly and was becoming semi-erect. She knew that before long it wouldn't be just his tongue, lips and fingers that would be pushing her nervous system into overdrive. Her pussy clenched with anticipation as she thought of Jason's fat, firm penis thrusting into it.

He went around behind her again where she couldn't see him clearly. Sure enough, she felt a firm cock push between her labia and begin a slow, careful penetration of her pussy.

Wait a minute. What the fuck? That wasn't Jason's dick. It wasn't warm, it was too hard, and it felt fatter than Jason's personal tool. And she could feel ridges on it where a real dick wouldn't have them. She twisted around awkwardly so she could see what was going on behind her, and wasn't surprised to see that what was thrusting its way up her vagina wasn't a penis but a big dildo that looked like it was made of some kind of metal. But what she was surprised by was that the dildo was attached to the end of an arm, and the arm was attached to the piston of a machine.

Her first reaction was, "Fuck!" She had never had a partner want to try out a fucking machine on her, and she wasn't sure she wanted to now. It seemed too weird and impersonal by half. She had expected a living body part, and she wasn't at all sure that her body would enjoy being fucked by something that looked like a miniature Dalek.

She made a loud interrogative "MMMPPHHH?" behind the gag, and the dildo paused its slow, relentless journey into her body. Jason came around to the side so they could talk - or he could talk, anyway - face to face. She noted that he had a remote control in his hand.

"Ever used a fucking machine before?" She made a negative "Mmmmm-mmmmm" noise.

"Want to try one?" She went "Mmmmmmm" in a way that suggested that she was thinking about it but not sure.

"Here are a few reasons you might like to try it. You don't usually take long to cum, but Steely Dan here can keep going for as long as it takes. I can set the depth and speed precisely so it can plough you really deeply without hurting you. And it can give you an extra fuck or two while I'm waiting for my cock to recover. Want to give it a try?"

Sylvia turned the offer over in her mind. Even though she hadn't been born when Naked Lunch was the darling of the beat crowd, she recognized the William Burroughs allusion in the name. Nonetheless, she still thought she'd really prefer a real cock filling her holes. Steely Dan just seemed too - well - steely for her taste. And she couldn't see what pleasure Jason would get out of watching a machine fuck her instead of doing the job himself.

But what the hell? Her dates with Jason were always an adventure full of new experiences, so why not give it a try? And besides, in the time Jason had been talking to her, the cold steel, parked part way in and part way out of her vagina, had already warmed up to body temperature.

"Mmmm-hmmm," she said with an affirmative cadence.

"Brave girl," said Jason. "Now, let's finish setting the depth." He clicked a button and the dildo resumed its slow, patient journey into the depths of her body.

"Now, this is important. The second you feel it touch your cervix, let me know." He watched her face closely as the intruder sank deeper and deeper. When she felt it start to bottom out, she said "Mmmppphhhh" quickly, and Jason stopped it.

"Now we pull back half a centimetre or so and set that as maximum penetration." He pressed another button. "Now the other way. Let me know as soon as you feel it's about to fall out." The dildo slowly withdrew until it was just about to come out of her vaginal canal. "Mmmmppphhh." Jason stopped it and pressed another button.

"Now let the fun begin."

The dildo began thrusting slowly, penetrating deep into her but stopping just short of a painful collision with her cervix, then pulling back almost, but not quite, to the point of coming out. Sylvia was beginning to see the point. A human being could never penetrate that deeply with no danger of hurting her, nor could he pull back that far without risking a pop-out that would spoil the rhythm. And the little ridges were doing a great job of adding extra stimulation, even better than a heavily veined cock.

Jason slowly increased the speed until the machine was really pounding. If a man had been going that fast into her, his pubic bone would have been punching uncomfortably against hers. But the machine had no pubic bone to get in the way, and it could slide in and out without making her body jerk forward with every thrust.

Then Jason started demonstrating another advantage. Whenever he had his dick in her cunt, it was too awkward for him to reach down and frig her clit. But with the machine doing the heavy lifting, he could get into any position he wanted to use his fingers on her other sensitive bits.

A third orgasm quickly started spreading through her body as Steely Dan relentlessly plunged in and out. She had never been fucked so deeply and hard without any of the usual discomfort that comes with an intense fuck. The shiny steel, slick with her gushing juices, produced almost no drag, and it didn't seem in any danger of making her sore. She bit down hard on the ball in her mouth as her orgasm quickly rose, broke, and flooded her body with intense sensation. Her scream would have been ear-splitting it it hadn't been blocked by the gag.

Even though her orgasm had burst over her and then subsided, the machine kept relentlessly pounding. She felt another orgasm rising, hard on the heels of the first one, but she wasn't ready yet. She had no objection to more orgasms, but she needed a minute or two for the first one to resolve and for her overstimulated body parts to stop being overstimulated.

Steely Dan didn't care. It just kept going until another orgasm was forced out of her overworked vulva. This wasn't fun anymore. As a third orgasm began to form before the second one had settled down, she decided she'd had enough.

"Mmmpphh, mmmpphh, mmmpphh."

Jason stopped the machine right away, again leaving it parked half in and half out. He peeled open the Velcro that was holding the gag in place and pulled the ball out from behind her teeth. "Do you need me to get you out of there?"

She took a few deep breaths, the first she'd been able to take through her mouth all evening. "No, don't untie me yet. And don't pull Dan out yet either. He's great. But for God's sake, turn him off for a couple of minutes when I cum so I can reset my cunt and my brain. You always do that for me, so your machine needs to as well."

"Fuck, I'm really sorry, Syl. The ads for these things always cite endless stamina as one of their advantages."

"That may be so, but a girl needs a quick break to resolve an orgasm before having another one. Otherwise it's just torture."

"OK, I get it." Jason sat back and watched her face again as she lay with her cheek against the carpet and waited for her heart to get back to normal speed.

"OK, I'm good. Shove that gag back in and let's get back to work here."

Jason pushed the ball back in and cinched the Velcro fastener behind her head. Then he started the machine again, somewhat slower this time. She focussed on the way her vagina was tightly stretched by deep penetration and then allowed to relax as the dildo pulled almost out, rhythmic waves of sensation radiating through her as another orgasm quickly rose. Jason used his fingers to help her along again, but this time when she made a loud "MMMMPPPPHHHH!" and stiffened every muscle, the dildo stopped, parked as far into her as its setting allowed.

After she had lain gasping for a minute or two, she turned her head and made her affirmative "Mmmmm-hmmmm," and gave him a thumbs-up sign with one of her retrained hands.

Jason gave her a few more minutes to relax. Then he came around behind her again, kneeling with one knee on each side of the dildo pole. Sylvia felt another squirt of lube on her asshole, followed by a finger pushing it far up inside her rectum. Then she felt a cock-head press against her brown pucker with gradually increasing force until her sphincter gave way and the tip slipped inside. This time she noted with satisfaction that it felt like a living cock: warm, firm but not hard, and instantly responsive to its owner. Jason's refractory period was obviously well and truly over.

Jason gradually worked his cock further and further up Sylvia's ass, listening carefully for any signs of pain and stopping immediately to let any spasms subside before pushing again. It took him longer than usual to get his cock balls-deep in her ass because the dildo was taking up a lot of room next door and compressing her rectal canal, but eventually she had something firmly seated in each hole.

Sylvia had never been DP'd by two men before, let alone by a man and a machine, and she wondered what it would feel like. She reflected that she had enjoyed her earlier fingers-and-thumb two-hole penetration, and that Jason had sometimes fucked her while she was wearing a butt plug in her ass, so this man/machine DP couldn't be all that much different.

Once Jason had gotten Sylvia's asshole used to being stretched around his dick, he began to thrust gently in and out. After a few thrusts, he turned on Steely Dan, and it began thrusting into her again as well, continuing to push to the very bottom of her vagina. Jason set up a reciprocal rhythm, thrusting in when Dan was pulling out, sending wave after wave of pleasure through Sylvia's body.

Having both holes deeply penetrated alternately was a totally new sensation, and one that Sylvia instantly knew she liked. Even though her overstimulated body and nervous system were getting tired of orgasm after orgasm, she felt one more rising in her body. Jason was obviously aware that she was beginning to wear out, and he kept both himself and his mechanical alter ego to a moderate pace so as not to push her too hard at the end of a long, powerful session of sex play.

Moderate or not, this mixed-species DP was having a powerful effect. Every nerve in Sylvia's body was on fire, and Jason was having similar feelings. Fucking Sylvia in the ass while Dan's shaft worked between his knees to fuck her cunt was the most erotic thing he could remember ever doing. The orgasmic sensations started gathering in his balls and pelvis, and despite his good intentions to go easy, he found himself driving harder. Sylvia didn't seem to mind, though. The muffled sounds she was making seemed to indicate nothing but intense, burning pleasure.

Not surprisingly, Sylvia's worked-over body was taking longer than usual to cum. Finally, Jason couldn't hold back, and he jammed his cock as far as he could up Sylvia's ass and let loose pump after pump of warm semen into the depths of her body. Normally, he would have been apologetic at finishing before she'd had time to cum, but this time he knew that Dan could finish the job.

He held his softening cock up her ass, keeping his load of cum plugged in her rectum as the machine thrust away for several more minutes until her orgasm broke over her. He pushed the stop button, and he and Dan stayed pushed into their respective holes until Sylvia had finished shuddering through the aftershocks of one last tremendous climax.

Jason pulled his cock out and grabbed a handful of tissues to wipe up the cum that oozed out. Then he backed the fucking machine out of Sylvia's vagina and unfastened her gag.

"Finished, Babe? If not, I can turn Dan back on."

"Don't you dare. That was one absolutely fantastic ride, but my nervous system is shot to hell and my cunt is starting to get sore. Tonight I need a long, slow turn in that soaker tub in your fancy bathroom."

Jason pulled open the Velcro on the spreader bar, and Sylvia unfolded herself and rolled over on her back, stretching like a cat in the sun. They lay side by side, playing gently with each other's bodies and relaxing after their heavy workout. Sylvia held Jason's limp cock in her hand, and Jason played with Sylvia's nipples.

Finally, Sylvia propped herself up on an elbow and said, "You were right about the light meal, but now I'm really hungry, and I need something before I go for that soak."

"I just happen to have some home-made cannoli in the kitchen."

"Fantastic. After the calories we just burned, something sweet is exactly what I need."

"Me too."

***

As they lay in bed later that night, they were both physically exhausted but strangely not sleepy. They chatted about the relative merits of fifties beat culture, fucking machines, voyeuristic threesomes, suspension bondage and the other kinks they had tried out, and Jason had apologized several times for overdriving Sylvia's body with Steely Dan. Now they lay side by side in silence, Jason resting a forefinger between Sylvia's pussy lips and Sylvia holding Jason's balls gently in her hand, not trying to start any overt sexual activity but just enjoying the quiet intimacy of touching each other's bodies.

"You know," said Jason finally, "You don't have to go home tomorrow."

"Mmmmm?" said Sylvia, slightly confused.

"You could go home and get some clothes and toiletries and stay a while. We haven't done much together except fuck. It would be interesting to see what would happen if we spent more time together."

"Are you saying what I think you're saying?"

"I'm not suggesting getting rid of your apartment and moving in long term. Not right away, anyway. But when I said 'I love you' the other day, I don't think it was just the oxytocin talking. I'd like to see if we can make this work on other levels than just eating and fucking. Not that either of those are bad things."

Sylvia let go of Jason's balls and put her hands behind her head in thought. "I think that's a lovely idea. I've wondered the same thing. But let's keep our wild kink sessions to Friday date nights. Even if we have regular sex whenever we feel like it, I'd like to keep those date nights special."

"Agreed. There's only so much wild kink the human body can take."

Sylvia rolled over half on top of Jason, slipped a hand behind his head, and gave him a deep, passionate kiss, which he returned with equal passion.

"See you in the morning."