Chapter 1408
"Not enough stimulation, huh? What should we do then?" Jillie mumbled, her mind racing for a solution. As a homeroom teacher, she was accustomed to quickly solving the myriad issues she faced at school. However, this situation was clearly beyond her area of expertise; after all, she specialized in teaching English, not human biology. She had never encountered such a dilemma before. Finally, she decided to seek advice from the person most affected. "Kevin, how can we increase the stimulation?"
To an outsider, it might have seemed bewildering to hear Jillie's question. A composed and mature high school teacher consulting a student on such a bizarre matter was certainly unconventional. However, understanding the context would reveal Jillie's profound compassion. She was willing to set aside her dignity and the decorum befitting an educator to ensure her student's well-being and future.
"I'm not sure, Ms. Mitchell," Kevin replied, though he knew exactly what could expedite his ejaculation. Whether it was a blow job, titjob, or intercourse, all were more stimulating than a hand job. Yet, guilt and shame weighed heavily on him, making it impossible to voice such requests. He could only muster, "Ms. Mitchell, you don't need to worry. It'll go down on its own after a while."
"That won't do. Look, it's still so erect. Besides, even if it goes soft, you'll have trouble sleeping if you hold it in without ejaculating." Jillie used her fingers to flick the still hard penis and said firmly, "Tell me, as long as I can do it, I will help you."
"Uh..." Kevin hesitated for a moment before tentatively saying, "If it's like that night with Ms. Nguyen..."
"No, absolutely not." Jillie quickly refused. That night, Maddy had used her mouth to help Toby with blowjob. As a woman of traditional values, Maddy was very conservative in her intimate life with her husband, always sticking to the same three positions. She had never given her husband a blow job, so the idea of taking another man's dick into her mouth was utterly unthinkable for her; it crossed all her boundaries.
"You could use these to squeeze it," Kevin suggested, pointing to Jillie's ample breasts. He figured he might as well make the request and see if she agreed; if she did, he would get to feel good.
"That's not possible, either," Jillie replied, this time with less of the earlier urgency. She hesitated briefly. After all, breasts didn't carry the same symbolic weight as the mouth. A woman might agree to be intimate but still refuse a blow job. However, she ultimately rejected Kevin's suggestion. Breasts were still too close to the mouth, and the mental image of a man's dick moving between her breasts would be too psychologically overwhelming. Besides, opting for breast sex would mean she had to remove both her dress and bra, which was neither convenient nor safe.
"Let's just forget about it," Kevin remarked, feeling quite dejected. If this wasn't possible and that wasn't either, he felt as though she was just giving him the brush-off. "Ms. Mitchell, I'll just masturbate myself."
"Try again, I promise I'll do it." Jillie claimed as she felt a bit embarrassed. She had promised Kevin out of sympathy, but in that situation, she couldn't think much. If she hesitated any longer, Kevin might lose control and assault her, and then everything would be irreparable.
"How about using your anus?" Kevin mentioned nervously. Blow job, titjob and intercourse were out, so the only thing left was the butt. "I'll just rub it on the outside, I promise I won't go in."
"All right then," Jillie reluctantly agreed. She truly wanted to refuse this request, as it was far too close to her vagina. If Kevin accidentally or intentionally did something inappropriate, she wouldn't have time to resist. She couldn't bear the thought of another man's dick entering her vagina; she wouldn't be able to face her husband afterward. Yet, seeing the hopeful look in Kevin’s eyes, she couldn’t bring herself to refuse once more. She feared that doing so would completely disillusion him, and as a teacher, she inherently wanted to gain and keep her students' trust.
Kevin, instantly elated, watched as Jillie turned around and once again positioned her plump, voluptuous buttocks towards him. Slowly, she lifted the hem of her skirt, revealing her enticing, snowy-white buttocks that had captivated him so deeply.
As a woman in her forties, Jillie was slightly overweight, but not to the extreme of someone like Alissa, who had an overly voluptuous figure. Jillie’s form was more subtly plump, with beautifully shaped, firm buttocks. There were even a few red spots on her skin.
At this moment, her round, fleshy mounds gave off a strong, mature scent, but what truly shocked Kevin was that the normally serious Jillie was wearing a pair of sexy black lace thong panties. The thin straps were deeply embedded into the cleft of her buttocks, and the small piece of fabric covered her plump mons pubis, outlining the contours of her labia. Through the panties, Kevin could sense just how full and inviting Jillie's vagina was. If he were to insert his cock inside, it would undoubtedly be an incredibly pleasurable experience.
Looking at the round, moon-like buttocks in front of him, Kevin couldn't help but swallow. Although Jillie's butt wasn't as plump and soft as Alissa's, as full and firm as Audrey's, as perky and sexy as Vanessa's, or as large as Grace's, it felt especially intimate and real.
"Kevin, go ahead." Jillie grabbed the edge of the nearby bench with both hands and slowly pushed her butt back, nervously saying, "Warning, no thrust. Got it?"
"Don't worry, Ms. Mitchell, I'll be careful." Kevin felt touched. Jillie clearly trusted him deeply to do this. He couldn't betray that heavy trust, or he would be too shameless.
He moved his swollen cock closer to Jillie's backside, and soon the glans touched her plump buttocks. Both of their bodies shivered as if an electric current had passed through them.
Kevin felt a tingling sensation in the glans, almost as if he was about to ejaculate. He didn't expect Jillie's butt to be so wonderful. His cock had just touched her butt, and he was already about to cum. This wouldn't do. He quickly took a deep breath, letting the glans separate from Jillie's butt. He had worked hard to get the chance for Intergluteal Sex with Jillie. If he ejaculated so quickly, it would be too regrettable.
"Kevin, what's wrong? Did you already cum?" Jillie held onto the bench, feeling both nervous and expectant. Although it was just Intergluteal Sex, it was still with a man other than her husband, and in the courtyard of a hotel. Maybe some students were standing by the window watching. They probably couldn't imagine their tutor teacher with her bare buttocks being played with by a male student.
But after waiting for a while with no movement from Kevin, she couldn't help but look back. In the darkness, she couldn't see his expression clearly. She wondered if he had really cum. Indeed, this was more stimulating than a hand job. She hadn't even felt anything, and he was already done. She felt a sense of relief. She didn't have to feel guilty towards her husband. After all, Kevin's dick hadn't even entered her butt crack, just touched her butt, which didn't count as real intergluteal sex.
But she also felt a bit disappointed. Was it really over so quickly? Jillie couldn't help but think it would be nice if Kevin could last a bit longer. She quickly dismissed the thought, reminding herself that she was helping Kevin release, not for her own enjoyment. She was a teacher and a wife and shouldn't have such thoughts about another man.
"Ms. Mitchell, I haven't even started yet." Kevin suddenly spoke in the darkness. Soon, Jillie felt his hot, hard dick touch her butt again. Before she could react, his dick was slowly inserted into her butt crack, pushing deeper.
"Oh my gosh!" Jillie's body trembled, instinctively twisting her plump butt, adjusting her position to make it easier for Kevin's dick to go in. Her previously disappointed mood suddenly became excited, as if she had moved from a dark valley to a bright prairie, basking in the sunlight, feeling incredibly comfortable and refreshed.
Jillie felt the waves of heat emanating from the cleft of her buttocks, immersing her in a heady, exciting state. The heat and firmness of his penis were beyond what her husband could ever offer. Although she knew such thoughts were improper, she couldn't help but fantasize about what it would feel like to have this dick inside her vagina. No, she couldn't allow that—not even for a moment. Intergluteal Sex was her absolute limit; she wouldn't compromise any further.
Kevin took in a deep breath, continuing to thrust his penis through the firm, tight groove of Jillie’s buttocks. The glans rubbed against the surrounding flesh, creating a multitude of electrifying sensations. However, without lubrication, even Jillie's smooth buttocks had friction. Soon, the glans became stuck, making it difficult to move forward. Additionally, Jillie's body was tense, and her buttocks clenched tightly, squeezing the glans and causing some discomfort. Instead of arousing the urge to ejaculate, it even started to soften.
Kevin felt a pang of regret; he'd had a similar issue while engaging in anal sex with Audrey that afternoon. He had thought, at the time, that lubricant would have been helpful and had intended to buy some but didn't after all. Who could have predicted he'd soon be leaving Skyview City and have another chance for Intergluteal Sex with Jillie? He couldn't just stop now, leave Jillie in that position, and run out to buy lube. Besides, the stores might be closed at this hour.
It seemed like he would have to do what he had with Audrey that afternoon. Kevin used his hands to spread Jillie's buttocks apart, slowly withdrawing his cock. It felt like his glans was almost raw from the friction, and his penis was softening. Jillie's buttocks were far more firm than Alissa's. If this continued, there would be no ejaculation—perhaps not even without causing injury. He guided his penis along the lower edge of her buttocks, aiming to maneuver it forward, intending to press the glans directly against her mons pubis, which was only possible due to his considerable length. For most men, such a maneuver in this position would be impossible.
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