“Oh… thank you,” Jessica said hoarsely. “But,” confusion set into her voice, “how does that help my head? You need to release my — mmphh!” As she felt something being stuffed into her mouth, she couldn’t believe that twice now she hadn’t seen this coming. She looked at Matt, trying to plead with him with her eyes, but he was hardly looking at her, as he started pulling straps around. As she explored the gag with her tongue, she realized it must be a ball stuffed into her mouth. Well, she thought, she certainly wasn’t going to be giving any more blowjobs with this in her mouth. But, from what she could feel of what Matt was doing, this new gag seemed to have an absurd number of straps. “mmhm?” she heard herself ask, realizing as she did that there was almost no chance of Matt being able to understand her.
“Hang on, I’ve … wow, this is really a lot of straps to adjust,” he said. She wondered briefly at this, then felt a strap going under her chin. Then out of the corners of her eyes she saw Matt pull two straps up on either side of her nose, that felt like they came together between her eyes, then another strap running over her forehead and over the top of her head. “Boys and their complicated toys,” she thought. Finally, he finished, and stepped away, and Jessica felt her head slumping down again.
“hnmm nnmph phhnph hmmp?” she demands, glaring at him.
Matt jumped. “Oh, right, sorry,” he says. She feels tugging at the top of her head, then he asks, “Would you mind just lifting your head for a second?” As she raised her head again to look forward, he says reassuringly, “There, that’s perfect. Just hold it a second more … there! Now you can relax.”
Confusion showing in her eyes, Jessica slowly relaxed her neck muscles. Her head fell just a bit then stopped, but she felt the straps surrounding her head pull tighter. “That’s the great thing about the harness gag, see. All those attachments, so I could just attach a rope to hold your head up!” Matt said cheerfully.
Jessica thought that if she were only free, she might throttle Matt for his cheeriness in the face of her debasement.
Matt started to undo his jeans. “Look,” he started, “I have to leave soon for the next visitor, but, well, I hope you don’t mind…” He blushed as he pulled out his straining cock. Her eyes got wide as she took in the girth of his penis as he started to walk around behind her.
The next thing she heard was the sound of scissors, slicing through her panties. Jessica waited, wondering if she was Matt’s first. Poor kid was going to be ruined, she thought, expecting women to come this wet already, not realizing that the foreplay had already happened before he got here. She wished the couple had stayed longer. They at least, she thought, seemed to know how to sex.
She felt him probing around with his penis, as though trying to figure out where the entrance was. She could help him if she had hands free, she thought. He hit her anus at one point in his fumbling, causing her to squeal in pain through her gag. “Sorry, sorry,” he stammered, withdrawing. Eventually he got it lined up and slid his cock all the way inside her vagina, causing her to shudder from the fullness she felt, stretching around him.
He started easing out, then back in, slowly building up a rhythm. It didn’t take long for her to start moaning from the stimulation. He might be young and dumb, she thought, but he did have a nice cock. He started slamming it into her, each time causing her body to shift forward, pulling the clamps tight.
Jessica could feel her eyes rolling back into her head as she started making more and more frantic noises. The mix of the pain in her breasts from having them stretched out with every thrust and the pleasure from being railed was overwhelming. Then to add to it all, he started spanking her ass as he thrust into her. It didn’t take long before, with a muffled scream, she finally came, her pussy spasming around Matt’s cock.
That was enough to finish him off, and she felt him shudder and ejaculate as he cried out in ecstasy, shooting his cum deep inside her. He leaned forward, his hands holding onto her hips, and finally he withdrew, giving her one last gentle slap on the ass as he did.
“Wow,” Matt finally managed to say, his voice shaky from exertion. He walked around back in front of her, struggling to pull up his jeans as he did. “Boy, I’m really glad I snagged one of my dad’s pills or I would never have lasted that long. Holy shit you felt incredible. Man, I wish I could stay for another round, but … rules are rules.” He bent down and gave her a kiss on her lips over her gag, reaching as he did to squeeze her tits one last time, then stood and walked out.
The wait this time was longer than before. Jessica waited in silence, feeling the cum leaking out of her pussy, the drool escaping the corners of her mouth, the tenderness of her nipples that had just been repeatedly stretched way more than ever before, and the rapid beating of her heart as she started to come down from her orgasmic high.
Finally, after what felt like an eternity, the door opened to reveal a man dressed in jeans, and some nondescript hoodie that looked like the kind that tech companies loved to give out to employees. He closed the door quietly behind him, then turned to silently appraise her, a smug smile playing across his face.
After a minute, he broke the silence at last, saying, “Hey there. My name’s Sam, and I believe I’m your final ride of this evening, so my job is to make it memorable for you.”
Jessica grunted through the gag, not bothering to try to form words this time, and wondered to herself whether memorable relative to everything else that had gone on would be good or bad.
“Now, let’s see here,” Sam said with a drawl, opening cabinets. “Nope, nope, too thick, too thin… that’ll do for the first part, but … oh here we go.” With that, he tossed a couple of coils of rope down on the floor next to her.
Her eyes grew wide as she tried to imagine where they could go. Each of them looked like they went on forever. What was there possibly left to tie, she wondered?
Sam grabbed the thicker of the two ropes and started uncoiling it with practiced ease. Then he grabbed the ends together and started pulling the two strands of rope rapidly through his hand. “Gotta find the middle,” he said, noticing her gaze. Once he had, he put the middle in the center of her back, underneath her arms that were still pinned behind her by the handcuffs, then dropped the strands down one side of her chest, then pulled them back up the other, laying them just beneath her breasts. He repeated this for a few loops, then she felt all the loops tighten, then he started wrapping around her chest again, but he had reversed direction, and now the ropes were laying over the top of her breasts.
Jessica felt him tying the ropes off, and as he stepped back in front of her to grab the other, thinner, rope, he looked satisfied, but she didn’t understand at all. He had even run the ropes each time under her arms, so other than squeezing her around the chest somewhat, this didn’t seem to actually add any restraint at all.
“Now, normally,” Sam said conversationally, as he started repeating the process of uncoiling the rope and then feeding the two strands through his hand, “this next part can be a little tricky to get just right. Sometimes have to start all over a few times. But, here you’ve got two things going for you. One,” he started, reaching up for a moment to give one of her breasts a gentle squeeze, “you’ve got the right size for it. And two, you are in the absolute perfect position.”
With the rope holding her head up by her gag harness, she couldn’t even bend down to see what he was doing, but Jessica certainly felt him feeding the new rope between her breasts, against her skin, underneath the coils he’d just wrapped around her chest. Then he seemed to pull the whole thing tight, pulling the two parallel sets of strands together in the center of her chest, squeezing her boobs from the top and the bottom. OK, she thought, squeezed boobs, but that sure looked like a long rope for that.
“Now this here is my favorite part of this,” Sam continued. “I’m not sure if you’ve ever had this done — have you?” he peeked out at her face from where he was squatting on the floor next to her.”
“nnnm mmhnph,” Jessica mumbled, hoping the confusion she felt would be evident on her face.
“I’m guessing that means no,” Sam said, ducking back under her chest. “Well, this’ll be memorable indeed then. Your first time! I’ll find a mirror or something so you can see after. You wouldn’t want to miss this.”
The next thing Jessica felt was Sam’s hand squeezing her left breast and then what felt like the cord being wrapped around the base of her left tit. He seemed to wrap it around a few times, slowly, then let go of her breast with his other hand, and then wrapped it several more times, tighter and tighter. Jessica started making pained noises through her gag. Her breast had never felt like this before — like it was being squeezed from all sides. Once he let go of the rope, though, the pain started to recede somewhat, but it still felt like it was throbbing. Then without a word, he repeated the whole process on her right side.
Sam finished, then said, “That might be one of my finest attempts at this ever. I wish I could take a picture of this, but rules say no. But, now, I did promise you a mirror,” he added, standing up. Jessica watched him, trying to get used to the new sensations from her breasts, while he started opening cabinets. “Now, where’d they move the damn thing to this year?” he muttered under his breath.
A couple of cabinets later, he found what he was looking for, and brought a decently sized hand mirror over and held it near the floor, under Jessica’s head and angled back a bit.
She had definitely never seen her boobs like this before. She thought they looked funny before, elongated from dangling down and being pulled even more by the clamps, but they certainly were elongated no more. She wasn’t sure she’d ever seen them look so round. Round and swollen, looking like two large orbs attached to her chest, the skin starting to darken slightly.
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