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Sue walked one block over and then another half a block up the next street to get to Robert’s house. Like the week before, she wore a skirt and blouse but skipped the bra and panties, knowing she would only be taking them off soon. She felt the cool afternoon air on her snatch as she took the short walk. When she arrived, she rang the bell and he answered quickly and let her in.
“I’m so glad you could make it today, Sue,” he said as he kissed her. She kissed him back lovingly.
“Wouldn’t miss it, Robert. And I’ve been looking forward to something new again this week. Will that happen?” she asked.
“Oh, I think it’s safe to say it will be different,” he replied. “I just hope you can take it, because you never know what the headmaster will come up with” he added with a chuckle, and she laughed.
“I do enjoy the role-playing, and I admit you’re pretty good at coming up with new things, like the spring-weighted nipple clamps; they were good. But don’t worry about me being able to take it, just bring it on,” she answered, in what sounded to him like a dare.
“Okay, I will. I’ve noticed over our first few get-togethers that you enjoy being submissive, Sue, as you are in our headmaster-student role-playing. You like that, don’t you? And I think you crave the unknowns, the thrill of not knowing what I’m going to do next?”
“Yes, I do like that. I admit that I enjoy being taken advantage of and the unknown makes it more exciting.”
“That’s perfect then. You’re perfect!” Robert said as he pulled Sue close to him and kissed her passionately.
She returned the kiss and they began to explore one another’s lips, their tongues meeting, probing, dueling each other. Both were getting turned on by the kissing and thoughts of sexual delights to come. As he held her close, Sue could feel Robert’s hard-on against her crotch as her pussy was getting wet with anticipation. After a moment more, Robert gave her a final kiss and stepped back. Changing to the academy headmaster’s voice that he used for their role-playing, he spoke.
“So, have you been a good girl this week, young lady?”
“Yes, sir,” she replied, playing her part as a student at the academy, “except for imagining all the naughty things you might do to me this week.”
“So, naughty thoughts again. Well, that will get you disciplined.”
“Yes, headmaster, if you must.”
“Oh yes, I must. Do follow me, young lady.”
He led her down the hall of his home to the bedroom, where he pulled an armless chair to the center of the room and grabbed a couple of towels, nipple clamps, and a paddle from the dresser.
“Let’s have you take your clothes off, please.”
Ever the obedient student, Sue pulled her shoes off, then her blouse, and finally her skirt and set them aside, revealing her lack of bra and panties, while Headmaster Robert laid a towel on the floor.
“I see you forgot your panties again,” he said.
“And my bra,” she replied.
“Very naughty. I may have to give you an extra spank or two today. But first, some nipple clamps.”
Robert took a good look at Sue’s perfect breasts, then tweaked her already erect nipples before attaching the nipple clamps that tightened when pulled. Then he sat down and placed a towel over his lap.
Do come and lay across my lap.”
Sue got on and lay across the towel covering his legs. Once she was settled in, with her perfect ass in the perfect position for her spanking, he attached the weighted spring to the chain connecting the nipple clamps and gave the weight a little pull to give Sue a little twinge. She knew that these were the same butterfly clamps he used last week, which tightened on her nipples more then less as the spring undulated, adding an effect to the spanking that she liked. With the setup ready, he took the paddle and began. Thwack! Thwack! One smack on each cheek to get things started. She remained quiet as he continued. Thwack! Thwack! Student Sue noticed the increased pain but said nothing. Thwack! Thwack! She was still quiet as he administered a final few strokes, though she did fidget on his lap, activating the nipple clamps. Thwack! Thwack! Thwack! Thwack! Sue squirmed with the pain at her rear and her nipples, but then, as quickly as he had started, Headmaster Robert stopped.
“That will be all the spanking for today. You did very well, young lady, so I will be treating you to something special, something different. Follow me.”
When she got up, he took the weighted spring off but left the nipple clamps on her and walked toward the bed, where he lay a towel in the middle.
Student Sue, noting her reddish cheeks in the dresser mirror, followed Headmaster Robert.
“If you’ll kindly lay down on your back in the center of the towel,” he ordered.
Sue continued in character as she crawled naked onto the bed and lay down on her back as instructed.
“Perfect!” he complimented her on following his requests.
“Now I’m going to prepare you for something new. First, I’ll blindfold you, and then I’ll restrain you. Do you understand?”
“Yes, sir,” she replied obediently. Sue was wondering what he was up to, but this sounded like fun.
Robert went to the dresser and got a blindfold. When he returned to her on the bed, he put the blindfold over her eyes and the elastic straps around her head. Now that Sue’s vision was gone, her sense of hearing was immediately more acute, and not being able to see what he was doing added a certain thrill of the unknown, which she liked. Sue could hear when Robert went back to the dresser and returned to lift her legs and place a bar of some sort under her knees. Then he attached something soft around her wrists, some sort of lashes she guessed, before lifting the bar and pulling her knees up with it. Then he spread her knees a few feet apart and attached her wrists to the bar, just inside of her knees. Sue was now restrained with her legs up in the air, bent at the knees, and held open by her secured wrists such that her legs formed a “Vee” with her crotch at the middle.
Blind, helpless, completely exposed, and more than a little turned on, Sue heard more sounds as Headmaster Robert continued, and she felt what was surely the spring being re-attached to the chain connecting the nipple clamps. She felt him attach the other end of the spring to the bar holding her knees and wrists apart. Moving her wrists a little to test it, she realized the spring again added nipple pain, as she expected.
Sue was blindfolded, wrists restrained by a bar that held her knees up in a “Vee” with her crotch at center stage, open and exposed, her hips tilted up, and her tits again connected to the butterfly clamps to add some nipple pain when she moved. She figured she must be ready. It was ingenious, and should be fun, she thought, whatever Robert was planning to do!
Now Robert went to the foot of the bed and climbed on. He used his hands to caress the insides of her legs, starting at her knees and ending at her pussy. Up and down he traced, first softly to tickle, then harder to soothe any itch he caused. Next, he touched her labia and ran his finger up and down her wet slit, opening it as he went. Robert continued to trace a finger over her tender tufts and folds before stopping at her clit. He caressed it lightly, rubbing across it very gently, but with her more acute senses, it felt very arousing. Sue wiggled a bit at the excitement it was causing her, which triggered the nipple clamps to tighten and hurt. She was enjoying how the blind and helpless position she was in added a thrill to his teasing at her clit.
Next, she felt Robert’s finger slide into her vagina, which was now very wet from the delight of his clit play. He quickly added a second finger and began to move in and out, finger-fucking her, which felt good, and even better when he positioned his thumb over her clit, so every in and out move caused his thumb to caress her nub. He continued his motions to Sue’s great pleasure, and she began to squirm. She was able to move her hips fairly well, but any movement of her wrists or knees caused the clamps to bite her nipples, which only added to the thrills she was feeling.
Sue was fully aroused despite the odd position he had her in, as he was gently tweaking her clit with his thumb in a regular rhythm now. And every time he drove her to squirm, she got a shot of pain at her nipples. She loved Robert’s creativity in coming up with this setup, and what he was doing at her clit was exciting her, especially with the added bit of nipple pain which always had an aphrodisiac-like effect. Sue knew she was close to an orgasm, but then Robert suddenly stopped, to her frustration.
She could tell he moved slightly on the bed, and then felt a cool liquid on her anus as he rubbed her “rosebud” with what had to be lube. It felt good, especially since it seemed that maybe Robert was going to fuck her in the ass, which would be great. The way he positioned her also made sense if that was his intention, since it tipped her rear to the perfect angle. She waited in anticipation as she sensed him undressing and was soon rewarded as he resumed his position, kneeling at the “Vee” of her legs and pressed his penis against her anal opening. Little by little he pushed the head of his hard cock against her tight hole, forcing himself into her just a bit, then pausing before pressing in again. She loved the feel of his penis as he worked his way in. She was able to relax and loosen her tight hole for him, and after several pushes, she could feel that he was soon deep inside her. Robert pressed further and was able to put his full length into her, and she loved the way it felt!
Thinking he would start fucking her ass, she was surprised that he paused with his cock entirely enveloped in her. But then she felt something else, this time at the entrance to her vagina. It was not fingers, but something larger… a dildo! Robert pressed it quite easily into her wet cunt, stretching her a bit as she felt its large size pushing into her. After a few in and out moves, it was fully inserted, and Sue felt the same pressures and fullness in her vagina and rear that she always felt during a double penetration. He began to move the dildo with his hand in sync with his resumed action at her rear, giving Sue a fine DP, though it was different in that there was only one guy, Robert. Still, it held about the same pleasures for her, and she appreciated his coming up with this idea. Meanwhile, Robert could feel the dildo pressing against his cock through the thin separation inside her as they slid in and out together.
As Robert had found a good rhythm, he slipped his free hand to her pussy and resumed caressing her clit with his fingers. Sue reacted almost immediately, moaning in pleasure and rocking her hips to his dual thrusts, as all the actions on her body combined to drive her wild, hitting all her sexual buttons at once. She pressed her hips into Robert’s thrusts, staying in sync with him, and squirmed relentlessly with the resumed sensations at her clit, while being driven over the top by the nipple pain she was causing herself with her squirming. Sue was beside herself in pleasure and couldn’t hold back any longer, exploding with a huge orgasm, the first followed almost immediately by more, spasming over and over, and squirting her juices over Robert’s hand, dildo, and cock. He continued to fuck her ass, pulse the dildo, and toy with her clit as she lubricated everything with her flowing juices.
They continued their two-person DP, driving each other to a delirious high as she squirted relentlessly for many minutes, until he reached his climax and unloaded into her anal canal. She felt the warmth of his load in her and emptied what liquid she had left onto him. They both collapsed, exhausted. Robert recovered enough to pull himself and the dildo out of her, and undid her wrists, allowing her legs to return to the bed. They relaxed, his cum dripping from her anus to join her juices on the towel, as he moved close to hold and kiss her.
When they were rested, he got up and brought her tissues and she cleaned up, while he took the wet towel away. He looked at her resting on the bed, so attractive, so beguiling to him. He was thankful to have found her getting propane that day a few weeks ago, and for all the wonderful sex they’d had since then. For her part, Sue loved his attentiveness and the role-playing fun they were having, with his unique brand of domination as the headmaster always surprising her with something new.
Sue got up and dressed, and they walked to the front door.
“So, same time next week, and how about here again?” he asked.
“Sounds great!” she said enthusiastically.
He kissed her goodbye, and she left. Walking home, Sue was happy about the good sex, the imaginative DP, and despite some soreness, she was already looking forward to returning next week for more.
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