Sylvia was flat on her back with her wrists roped firmly behind her and her ankles pulled far apart and into the air by more ropes tied to the bedposts above her head. The position wasn't particularly uncomfortable, at least not if she didn't have to stay like that for any length of time. What was more uncomfortable was Jason's cock pressed against her anus as he knelt between her spread legs, and the unrelenting pressure that was slowly forcing her reluctant sphincter open.
She remembered sitting in the bar on her first date with Jason, saying "I don't much care for being fucked in the ass. I've tried it a few times, and it doesn't hurt nearly as much as I expected it to, but it doesn't do a lot for me." Now here she was, doing exactly that. What a difference a few weeks makes.
Just a few hours before, they were at Clancy's bar having their usual date night drinks and talking about all manner of random stuff. As it usually did, the conversation eventually slid around to sex, particularly kinky sex and what sorts of kinks they might like to try when they got back to Jason's. Jason had texted earlier in the day to ask her to wear clothes and underwear that she wasn't particularly fond of. She didn't know exactly why, but she had a pretty good idea. Accordingly, she dressed in a skirt and sleeveless top that she had bought without realizing that she was going to hate the colour - an excessively vibrant pink that looked a lot more excessively vibrant when if was no longer washed out by the fluorescent lights of the store. The outer clothes were paired with a pair of panties and a bra that she had been planning to throw out because their elastic was getting overly relaxed.
As she wondered exactly what was going to become of her not-fond-of ensemble, Jason leaned in and broached the subject of anal sex, a topic that had not come up between them since her brief dismissal of it on their first date.
"I remember you saying that, although you have no objections to it, you really don't get much out of anal sex. Do you remember that?"
"I do remember that. Stan, the man I tried it with a few times, did all the right things to avoid hurting me. He used a ton of lube, he went super slow, he always stopped and let me get out in front of any spasm of pain that happened as he was going in. It didn't hurt once he was in, but I never seemed to get even close to an orgasm from it. I've read that some women get a whole lot of pleasure from anal, sometimes even more than old-fashioned PIV, and I have a few friends who say that as well, but not me. I guess my nerve endings aren't in the right place or something. I'd much rather have a cock in my pussy, or even down my throat."
"When Stan tried fucking you in the ass, did he tie you up first?"
"No, actually. He wasn't much into bondage, although he sometimes did it to please me. When we tried anal, he said he wanted to experience one kink at a time."
Jason got a thoughtful look as he digested this piece of information. "Hmmm. Bondage seems to be a really important part of the experience for you, isn't it?"
"Well, it wasn't quite as big a deal for me then as it seems to have become lately. But yes, I always seem to cum way harder when I'm tied up, and especially when I'm gagged as well."
"And when Stan was doing your back door, was he doing anything to your front door at the same time? Tongue, fingers, toys, that sort of thing."
Sylvia suddenly thought that Jason was beginning to sound more like a sex therapist than a date. But at the same time, she was interested in where this was going. She had never stopped to analyze why her brief forays into anal with Stan had been so disappointing.
"As a matter of fact, he didn't. He just focussed on driving his cock into my asshole. He held out for a long time trying to make me cum, but eventually he gave up and just shot his wad up my ass. He seemed to enjoy it, but it really wasn't a very exciting night for me."
Jason put his elbows on the table, rested his chin on both fists, and gazed at her thoughtfully for a few seconds. "Tell you what. Would you give it one more try? If you'll let me up your ass tonight, I'll use everything I know about you and your body to see if I can coax out a good one."
It was Sylvia's turn to be thoughtful for a few seconds. "Why not? The worst that can happen is nothing, and then you'll have to get me off some other way. You've been very, very good at that so far."
So it was settled. In spite of herself, Sylvia found herself squirming with anticipation. She had really wanted to like anal, if only because it was one more kink that she could add to her list of good experiences. The slightly taboo aspects of anal intrigued her, and if Jason could figure out how to make it work for her, it would be a triumph.
She had managed to work herself into quite a state of excitement by the time they reached Jason's apartment. They barely had time to sit down on the couch before Sylvia had Jason's face in her hands and was pulling him in for a long, hard, hungry kiss. Jason, equally worked up, reached behind her head with both hands and locked her mouth on his. They explored each other's lips and tongues for several long minutes, then broke off for air.
Once she'd caught her breath, Sylvia squirmed off the couch and knelt between Jason's knees. She fumbled with his belt and zipper, got his pants open, and reached in to rescue the excruciatingly hard cock that was jammed into them. Jason lifted his bum enough to allow her to slip his pants and underwear down and then dropped back down again, keeping his knees well apart as she gazed up into his eyes and wrapped her warm, wet mouth around the head of his cock. Her agile tongue stroked the tiny valley of his cockhole for half a minute, then circled around the base of his glans where it met his shaft. She had learned on previous dates that he especially liked those moves as a way of getting his cock thoroughly warmed up.
Sylvia started rocking forward slightly on her knees, taking a little more cock in her mouth with each rock. Jason desperately wanted to thrust into her for a good, forceful session of face-fucking, but he knew that going too fast and taking away too much control was an excellent way to trigger a choking fit and end an excellent head session prematurely. He restrained himself and let her set the pace, just resting his hand on the back of her head without putting any pressure on it and forcing himself to relax his hips and let her take as much of him in her mouth as she felt ready for.
After a few bobs that brought his penis right to the back of her mouth and the entrance to her throat, she pulled back, took a deep breath through her nose, and lunged forward to take his cock all the way down in one smooth motion, his balls bouncing lightly off her chin. She held him there for several seconds, making swallowing motions to massage his shaft, then pulled back, took a couple of deep breaths, and then lunged forward again.
Jason was in heaven. He so loved the feeling of a tight, wet throat around his cock, and the things her tongue was doing on the underside of his shaft as she slid it in and out were massaging him toward a slowly growing orgasm. Sylvia, too, was enjoying the sensation of her mouth and throat around a magnificently hard penis. She also loved watching the expression on his face gradually changing and the way his breathing got more and more ragged as his orgasm rose, finally starting to come in deep gasps with each lunge on his cock.
She knew that if she didn't stop soon, she was going to get a load of salty cum down her throat that would put the evening on pause before it had properly begun. With an effort, she pulled back and let his cock drop out of her mouth. Jason leaned back on the couch to recover, and she stayed on her knees between his legs, a trickle of saliva running down her chin, to wait for what he would want to do next.
"Shit, Sylvia. I've never met a woman who could deepthroat a cock as well as you do." He reluctantly stuffed his still-hard cock back in his pants and stood up. She took that as her cue to stand up too.
Jason took her by the elbow and wordlessly walked her to the bedroom. She wasn't surprised to see a coil of rope on the edge of the bed, and two more pieces of rope already tied to the top bedposts. He pushed her onto the bed face down, and she let her hands lie loosely at her sides so he could tie them how he wanted them. She found it odd that they were both still fully clothed, but she figured that she'd find out soon enough what his intentions were in the wardrobe department.
He brought her hands together behind her back, palm to palm, and wrapped several turns of rope loosely around her wrists, then wrapped rope between her wrists to cinch the rope into rope-handcuffs: impossible to slip out of, but not dangerously right. She felt him tie off the rope, then he said, "On your back."
Sylvia obediently rolled over and lay on her hands. She noted that Jason had left a long piece of rope hanging out of the wrist-tie, and she wasn't surprised when he tied it to the bar at the bottom of the bed, pulling it tight so there was no way her body could slide up the bed. Then he took first one ankle, then the other, and bent her legs up and back. He used only moderate pressure, and stopped bending when he could feel that her joints really didn't want to go any farther. Then he tied the ropes from the bedposts around her ankles.
