Tommy's Torment

About two hours later, he heard the front door open and close and footsteps on the stairs. Tommy had been struggling in vain but could not get free. The edibles were working their magic and his untouched cock was throbbing as his imagination was running wild. Sheila came into the room carrying a duffel bag and brushing snow off her coat. Looking at his hard cock, she said, "it looks like someone missed me. Oh, I hope you don't mind that I changed clothes" She unbelted the trench coat she was wearing to reveal a black bustier that barely contained her large tits. She had on a garter belt and pantyhose and looked like she could have been comfortable in any of the movies on Tommy's laptop. She slowly unzipped the front of the bustier to reveal more and more of her great cleavage. Finally, she hit the bottom with the zipper and sexily peeled of the garment. "Now Tommy, you must keep your head flat on the bed, ok? Otherwise, I'll need to use the feather on your feet again, and you don't want that, do you Tommy? He vigorously shook his head no, he for sure did not want that again. He planted his head firmly on the bed and wondered what was coming next.

Sheila knelt over the top of Tommy and slowly caressed and pinched her hardening nipples. She had always had great nipples that were super responsive and sensitive and was sometimes embarrassed when they poked through shirts even with a thicker bra. They got especially hard when she was excited, and she was very much so right now. She put her nipple right above Tommy's eyes as she pulled and teased it. She still had her black leather gloves on from her trip outside because she noticed some of the teasers on the computer had worn leather gloves. Maybe Tommy had a bit of a glove or leather fetish? She slowly dragged the now rock-hard nipple across Tommy's nose and the ball gag, "do you want to suck my nipples, Tommy?"

Tommy, of course, could do no such thing with the ball gag buckled into his mouth. He stared, wide eyed at the big rock-hard nipple just inches from his eyes. He wanted so much to suck on it that his breath was coming in ragged gasps around the ball gag. He could see from the look in her eyes, that she was enjoying teasing him, perhaps too much. She looked like the women in the movie, who got off from tormenting their men, the more they teased them, the more excited they got. He had never expected to see this from his mom's best friend.

Sheila, after running both her nipples over Tommy's ball gag for several minutes stood up and went to her duffle bag. "I brought us some additional toys." She pulled a hitachi vibrator from the bag and set it on the bed, along with a few additional feathers - "I know you really like these." "Oh, here's a fun one, let's see how you like it, but only for a few minutes. The gal at the sex shop says it's one of her favorite toys." She pulled a cock ring with a small cylindrical attachment from the bag. "It's a vibrating cock ring and you can set the intensity, and the length of time it stays buzzing. Then it shuts off for a bit until it comes back on. The gal said her partner never could cum from setting #1, but he sure wanted to... Let's see." For the first time, Sheila touched his pulsing cock. She attached the vibrating ring just below the head of Tommy's cock and tightened it up. Already the cockhead was leaking precum, just from the anticipation of it all. Sheila turned the switch on, and the buzzing started.

Ohmigod, it felt so good! The vibrator was like nothing Tommy had ever felt, it was pushing him closer and closer to cumming. And then it shut off!! His eyes shot open, and he saw Sheila giggling at his situation, "oh, this will be fun." A minute later, the buzzing restarted, and Tommy again was being brought slowly to orgasm, but once again after thirty seconds or so, it shut off. "I should leave you here with this on you for an hour or so", Sheila chucked. Sheila let him go through a couple more cycles and then picked up one of her pointed feathers. "Maybe this will help you out" She gently took the very tip of the feather and ran it along and around his straining cockhead. Tommy bucked against the bed and frantically tried to escape from the bindings, but it was no use. The ring started buzzing again and Sheila moved the feather point to his balls and ticked them while the vibrator inched him closer to cumming. He was going to shoot this time! The addition of his balls being tickled by the feather was going to be enough to get him over the top. Here is comes...! And then the buzzing stopped, and the feathering stopped. "Oh, you poor thing! I was sure that the feather would be enough to get you off, but now you are even more frantic than before. Well enough with that toy for now, what else do we have?" She pulled various nipple clips, butt plugs, and other toys from the bag. She removed a small jar of something and said, "oh this is for later, in case you are naughty".

"Oh, I almost forgot to show you my surprise! I noticed something in almost all your videos and image files and luckily, I was able to find a salon that was open at this hour. I have a hunch you will really like this one. Tommy stared wide eyed as she slowly started removing her gloves while staring into his eyes. He gulped visibly. "Do you have a bit of a long nail fetish, Tommy? It seems you like long nails with square tips and French manicure the best?" She removed her left glove and Tommy was staring at some of the most beautiful and sexy nails he had ever seen. They were probably an inch past the fingertips, finished in a square end and were gleaming white and pink in the room light. His cock twitched at the sight and Sheila giggled. "It looks like I did it right." She slowly tickled the talons across his hardening nipples and down his stomach. She got so close to his cock but veered at the last moment and gently tickled his inner thighs. Over and over, she almost touched his now dripping cock. Finally, she gently tickled his balls with the long, beautiful nails and with just her index finger, scraped her nail very slowly from balls to cockhead. Her other hand had been teasing her own nipples. "Well, I think it's time one of us got off"

She knelt on the bed with her shaved pussy inches from his bulging eyes and gently teased her clit with a long-nailed finger. Her half-closed eyes stared into Tommy's pleading face as she rubbed some of her juices below his nose. It had been a long time since she had been this turned on. She continued to tease herself for several minutes and then climbed off him and went to her bag.

"You know, Tommy, that you were naughty. I asked you specifically about any more fantasies or fetishes you might have, and you didn't say anything. You didn't mention that you had a thing for long nails and you very much do. I'm going to enjoy teasing you slowly with my ten new toys, but first I think you need to be punished for being so naughty.

"I did this to my ex-husband on occasion when he misbehaved and stayed out too late with his buddies. He would awaken the next morning and find himself helplessly tied to the bed. I'd tease him slowly almost to the point of cumming while I got myself off. He'd accuse me of overreacting to his small indiscretions because I loved teasing him so much, which may have been at least partially true. But then I read of a new teasing technique and I began to use it on him when he was most naughty and really needed to be punished. I was only able to use it on him twice before he left me, because, "you are one psycho bitch and get off on watching me suffer." It was true, I'd found that I would get such a powerful orgasm by watching him thrash in agony as his orgasm was just out of reach."

She grabbed Tommy's shirt from the floor and wiped off his dripping cock. This is the one that I saved for when my hubby really needed to suffer. She reached into the bag and took out a makeup brush, one that probably would be used to apply blush powder. She grabbed the jar and opened its wide lid and swirled the brush inside. She brushed the powder liberally onto Tommy's hard shaft and long-suffering balls and then carefully closed the lid and put the brush back into it's bag. She pulled up a chair to the bedside and grabbed the longest pointiest feather and the hitachi.

An hour later, Tommy was going insane! The itching powder that had been applied to his raging cock was driving him crazy. The itching was the most intense feeling he had ever experienced, and his wrists were raw from pulling at the cuffs trying to reach his cock to rub it, to scratch it, to somehow get himself off. She had been very slowly, almost lazily, tickling the huge purple head of his cock with the pointed feather. She watched him thrashing, and the helplessness in his eyes while she held the vibrator to her clit with her other long nailed fingers. "Tommy, I told you that if you asked me to, I'd scratch your hard cock with my long sexy nails, but I'm not sure why you won't do it. Just beg me and I'll do it." Tommy's guttural pleas were incomprehensible around the ball gag as he tried to beg her to rub his cock with those long nails. "What is that Tommy? I can't understand a word you're saying. I wonder if the vibrating cock ring would help you out?" Tommy began weeping and Sheila smiled...