JoeBob waited with great nervousness at the table at Solozzo's Pizzeria. He wondered whether his date would show up. Would she be a beast? A lot of the women who were involved in the BDSM scene were just uggoes or fatties who were desperate for a man, why not a kinky one?
That had been the problem with Elaine. She actually had had a pretty face, and nice big boobs, but she had been a chunker. JoeBob had met her at Weight Watchers, not even a kinky place, and he'd taken her out a few times, and then confessed that he has fantasies of her tying him up and whipping him.
Elaine had really been a sport. She'd twirled her dark hair around her shoulder, and invited him back to her place. "Now do I keep my clothes on?" She'd been quite a good student, actually.
Once she figured the whole deal out, she'd gone into her closet, and then changed in the bathroom and come out in a tight black tube top (big women look good in those, if the boobs are large enough) and heavy light blue eye-shadow.
Elaine had ordered JoeBob to strip and lie on the bed, and she'd used his belt until her arm was tired—lots of anger there! But after a few months of this, Elaine had complained that they didn't make love—sure, she enjoyed him performing between her legs, but it creeped her out when he'd jerk off on her shoes. It just wasn't her thing.
Then there had been Cassiopia. Cassiopia was also a husky gal, with a pretty face but an unfortunate complexion. JoeBob had met her through the same ad he was using now, and she was a local girl. Cassiopia was experienced in the scene, and had her own tight PVC leather corset outfit, and didn't look bad in it.
When JoeBob had gone over to Cassiopia's house, he'd found she already had a submissive, a hippopotamus shaped chick called Lilith. Despite her girth, Lilith did kind of turn JoeBob on, she'd stripped immediately out of her registered nurse's uniform and crouched at Cassiopia's knees, and JoeBob had watched, entertained as Cassiopia had put out her Virginia Slim on Lilith's already rather scarred buttocks.
But then Lilith had sat and watched as Cassiopia had ordered JoeBob to strip, and then she'd tied his hands and begun masturbating his cock, calling it "miniscule". After JoeBob became hard, Cassiopia had become enraged. "Did I give you permission to have an erection?"
Cassiopia had gotten this little black stick out, which apparently was a taser of some sort. She touched it to the tip of JoeBob's penis, there had been a ZZZAPP, and JoeBob had fallen to the floor, clutching his penis and screaming.
"Get up. You are going to learn to keep your penis at a respectable size, and not get all bulgy just because a lady has a polite interest!" Cassiopia had pulled poor JoeBob up by his hair, and instructed him to stand again with his hands behind his back.
Cassiopia had begun stroking JoeBob's cock once more, and eventually it began swelling again. This time Cassiopia took a long wooden pointer and whacked the tip of JoeBob's erection, and it wilted.
Then Cassiopia stroked JoeBob's cock again, this time super fast, pulling her hand away and punching him in the testicles when he began moaning in desire. She did flash her boobs at him, but that didn't make up for the pain in his balls!
"You must learn to stay limp until I instruct you to do otherwise." Lilith was laughing, relaxing in a bean bag and watching JoeBob's discomfiture. Finally, Cassiopia had allowed JoeBob to masturbate into a glass and drink it, and he'd thought he was in love.
This seemed to be the ultimate relationship to the masochistic JoeBob. But on the other hand, Cassiopia really didn't want JoeBob—she wanted his wallet! She was really a lesbian, and although she let him kiss her inner thighs, she only allowed Lilith's head between her legs to do the serious carpet munching.
Cassiopia had locked JoeBob in a chastity belt, which turned him on, but then she'd told him that he would have to pay fifty bucks every time he wanted to masturbate!
JoeBob had thought he could live with beating off once a week, but he'd discovered that he was constantly going to the ATM and then dropping in at Cassiopia's.
She would take the money, and then order him to strip, and stroke JoeBob's cock and balls for quite a while before finally doing something horrific like making Lilith rub her feet on JoeBob's dick until he came, or having him jerk off with his left hand, licking his fingers afterwards...within four months, JoeBob had spent $900 just for the right to orgasm...
Cassiopia had taken JoeBob to a big time lesbian orgy, but she'd ordered him to strip naked (before anyone else did) and then kneel in the corner for the entire event!
In a way this was the kind of hard-core submission that JoeBob had fantasized about, but it got really boring just staring into the corner for four fucking hours. The one time he sneakily looked around him, Cassiopia had run up and whipped him HARD with a bullwhip until he had his nose firmly pressed back in the corner, and his butt was nearly bleeding!
Another time, Cassiopia had called JoeBob out of the corner so that one of the few young guys there could give him a hard over the knee spanking with a paddle. JoeBob had tried to explain that he was not gay, but it was to no avail, and he had been sobbing like a baby by the time he'd hobbled back into the corner!
After it was over, Cassiopia had ordered JoeBob to lick the scum off the two or three guys who had been there...licking their penises, and when he'd asked for relief, she'd ordered him to fork over a C-note and then had him jerk off before the entire, laughing party!
But then Cassiopia had begun pressuring JoeBob to move in with her, and turn his finances over. JoeBob was a submissive, but not THAT submissive. He learned that Cassiopia had another slave out of town, Jerome, and that not only did Jerome give her almost all his income, but she locked him into a rubber suit, with a feeding tube and kept him in complete bondage every weekend!
Then, while JoeBob was still "dating" Cassiopia, another guy had moved in, a sheriff's deputy, and she'd taken HIS salary and given him a closet to sleep in. Cassiopia kept this dude on a leash, literally, and actually had him walking around on all fours naked in the front yard, and this had garnered complaints from the other tenants in Cassiopia's building...she'd called them "Fundamentalist Tea Party types"
Lilith also gave her entire nurse's salary to Cassiopia, and allowed herself to be rented out as a submissive for hire, turning that cash over to Cassiopia as well. JoeBob had too much common sense to get involved with a situation like this.
JoeBob had expanded his father's tree surgery business, and had most of the municipal contracts in Buttermilk County for pruning, and most certainly wasn't going to give all that cash to Cassiopia. He had a life outside of the BDSM world—he ran marathons, went skiing and played in Dungeons and Dragons tournaments...
Cassiopia had responded to JoeBob's pulling back by telling him he would now have to pay $200 a shot to masturbate, and he'd ended up having to break open the chastity device and change his phone number. Cassiopia was a sickie!
The next experience JoeBob had was with a couple. Kinsey and Duquan. "Some men are a little put off by a couple" Kinsey said to JoeBob after they came to his house "But truly; if you're going to submit why not make it to both of us?"
JoeBob was a little nervous, but Kinsey was quite attractive, she was curvy and not too fat, and had curly strawberry blonde locks, and Duquan was a quiet type, a coal black man with a thick handlebar moustache.
After a couple of dinners, and going out once for drinks, JoeBob said okay, why not? But again, the couple was out for money. "You have to understand, JoeBob, that Duquan and I are professional BDSM people." Kinsey had told him.
Unfortunately for JoeBob, she didn't tell him this until Duquan had stripped and bound him, and Kinsey was playing with his cock, rubbing ice on it, and then rubbing it with her talented long nails.
"You can't tell me you've not been aroused by the whole fantasy of being dominated by your wife and her lover, right? This is just that." Kinsey said, smiling. JoeBob was about to tell Kinsey that this would be interesting if she was his wife, but wasn't she DUQUAN'S wife?
And, that first evening, as Kinsey continued to stroke JoeBob's swelling cock, Duquan unzipped his pants and stuffed his own cock in JoeBob's mouth. JoeBob actually tried to keep his mouth shut, but Kinsey grabbed his nipple and twisted it till JoeBob screamed.
After she'd teased JoeBob a bit more, and he'd sucked Duquan to a messy "completion", Duquan pulled his dick out of JoeBob's mouth, and Kinsey bent JoeBob over the hassock and whipped his bare ass until he cried.
Then, she untied JoeBob and had him watch on his knees while she and Duquan made hot, passionate love. After this was over, she ordered JoeBob to lick the juices off both of them, and give Duquan a nice, post-fuck blowjob.
But he was quite aroused when it was over, and obligingly gave the couple a check for five hundred bucks. This, Kinsey said, was his "tribute".
On the next date, only Duquan had shown up, which had not been so cool for JoeBob. But, as Duquan said, it really wasn't up to him. The two men had eaten and then Duquan had brought JoeBob to a gay dungeon house downtown.
"I brought you here, because I noticed on our first outing that your fellatio skills are severely lacking" Duquan said, as he tied the naked JoeBob to a sawhorse in the middle of the dungeon. "You are possibly the worst cocksucker in Buttermilk Falls."
JoeBob had had to try his mouth out on several men, and Duquan had given instruction, not too patiently "Lick the bottom of the cock...that's right, the underside. Now suck with pressure...more pressure!"
When JoeBob fell back in the penis slurping , Duquan rewarded JoeBob's reluctance with a flogging, and JoeBob got a little better at it. But his heart was never in it, sadly.
On the next outing, Kinsey had brought up the chastity belt thing. "You know, I believe in supervising my slave's orgasms when he's not around, JoeBob. We have to have you fitted for a chastity belt."
JoeBob was a little leery of this, because of the experience of having to pay for his orgasms, but Kinsey and Duquan assured him this wouldn't happen. They wanted occasional "tributes" but as Kinsey said, paying for an orgasm would give him too much control over when he had it!
Kinsey did give wonderful teasing hand jobs. That evening, she'd tied JoeBob down and begun stroking his dick until he began trembling, and then she squeezed the tip of his cock until he flagged. "See, you need to understand, JoeBob...the main deal here is pleasuring Mistress Kinsey and Master Duquan, not whether you get to make a mess."
It had been hellish though, as JoeBob stared at Kinsey's cleavage in the tight mauve body stocking. Duquan was in the corner, playing with a Game-Boy, and JoeBob wondered idly when Game-boys had replaced playing Solitaire...but then his attention returned to Kinsey as she ran her soft fingers up and down his full testicles.
