The Lessons Ch. 22

He could lie about it. He could tell her that he couldn't see anything. But, he wasn't about to lie to her, just to get into her butt. "You're right," he said glumly.

Melissa though had the solution. "I know," she gleefully suggested. "Here, you lie down and I will sit on it." That was in fact a great solution, in many respects. "That way too I can pull back if it hurts, or something."

"Sure, great," Jim agreed. He fell back onto the bed, brought his legs close together to give her room, and grasped his cock to aim it straight up in the air to provide a good target for her landing.

Melissa giggled as she got into position: sitting on her knees, one on each side of him, her bottom directly over Jim's stiff, taught weapon. Her skirt was safely draped over her thighs, hanging almost to her knees. Her modesty was duly protected.

Melissa furrowed her brow in concentration as she slowly lowered herself down onto Jim's spear. As she did so she reached underneath her skirt with her right hand to help mark and steady the position of Jim's cock. Jim let go as soon as she grasped hold. She used her left hand to steady herself. Jim lightly held her by the thighs to help as well.

When the cheeks of her little bottom first touched the soft head of Jim's cock she hesitated. She said in a nervous, squeamish voice, "Oh my gosh, here goes." She then dropped further, letting the head slip in between the soft cheeks.

That felt considerably erotic, to the both of them. She put off the insertion a bit to enjoy the feel of the head of his cock sliding around and up and down the cheeks of her fanny as she slowly wiggled and maneuvered her butt. That felt even better, especially to Jim.

Melissa though could feel that she was essentially wiping off the lotion on his cock. She held still, let go with her hand, and sat firmly down on the top of his cock, like it was a place to rest her butt. This was also helpful in keeping it held in place, sticking up straight. She reached for the lotion. Jim though picked it up first and squeezed out more of the thick, slippery fluid into the palm of her right hand. She reached again under her skirt to grasp his cock and worked the lotion into his skin, focusing in particular on the soft, round head.

Jim closed his eyes and sighed with deep pleasure. He wonder if he should tell her that she really needed to hurry up or he would not last too much longer. However, he didn't want to rush her.

Seeing his eyes closed made it easier for Melissa to also work some of the lotion right onto her anus. She felt really silly and weird doing that, but it would have been much worse if he was watching her do it. She realized though that this would really help.

She again grasped the shaft of his cock and lowered her anus directly onto the tip.

Jim opened his eyes and smiled at her. She smiled back and said quietly, "Okay, here we go."

She sat down onto the head of his cock. Her instinctive reaction was to clench her sphincter to block its entry. But, she concentrated on just relaxing, like she wanted something to go out.

She could feel the tip of his cock pressing into and slowly expanding the ring of her butt hole. It felt quite strange, like she was being penetrated in a very personal, intimate manner. And, that was precisely the feeling that she wanted to have. She let her legs relax further, letting the weight of her body sink his cock up into her butt.

It wasn't easy. It was in fact rather hard. Fortunately, his cock was also quite hard because her little bottom did not want to take the bulbous head of his dick inside. It was true that she had, many times before, bowel movements that were plenty big, but they were going out, going out in the natural direction. This was a big headed club trying to force its way back in. It wasn't natural and it wasn't comfortable.

But, with a deep breath and concerted effort at simply relaxing her sphincter, her body suddenly dropped down and the head of his cock popped through the tight sphincter, which, just as quickly, shut tight again around the shaft an inch or so below the head. She stopped there.

It was really quite a sensation, like being plugged up her butt. But, it was a really nice feeling, like Jimmy was stuffing his hard cock deep inside her, which is precisely what he was in fact doing and what she wanted him to eventually do the real way. This was turning into a real good way of pretending to have sex. She closed her eyes, steadied herself, and sat still for awhile, letting herself enjoy the feeling of being so thoroughly penetrated.

Jim had his eyes open, enjoying the sight of Melissa sitting on him, sitting on his cock, now firmly embedded in her ass. He could see that his dick was difficult for her to take, but he could also see how aroused, how excited she was, and that made him all the more agitated. He could feel his cock swell within her butt, her anus tightly gripping his shaft, the head of his cock pressed up against the softly curved insides of her rectum.

Melissa knew that the first time a boy's penis entered her it would be particularly difficult, and having it up the rear was probably even harder to do. But, she hadn't expected that it would be this hard, that she would feel this loaded, this crammed. She carefully, slowly moved up and down the shaft. She never pulled up so much that the sphincter moved past his sulcus, not wanting to actually let him escape, and, with each lowering of her butt, she moved further down the shaft, bringing his cock deeper and deeper into her rectum. Melissa could not help but think that she was now in fact truly riding Jim's Pogo stick, although doing so in a rather difficult way. "Oh Jimmy," she whispered breathlessly, "You feel so big, so very big inside me."

Jim was having difficulty holding on. He felt like he was actually fucking her, actually sliding his cock in and out of her tight, virginal hole. In a sense he was. At least as far as his cock was concerned, he was. It was such a very powerfully charged feeling. Her hand always felt so good, particularly when she used her palm, fingers, and thumb to stimulate every inch of his cock in so many different ways. And, her mouth was often even better, with the intimacy of her tongue licking and lapping away at the sensitive nerves of the head of his cock as she absorbed his prick into her face.

But, this was also a uniquely special experience and sensation, his cock firmly lodged inside her butt, grasped so tightly by her sphincter and rectum, deeply embedded inside of her body as she worked her hips to slide in and out of her fanny, like she was actually doing it with him.

When she got all of the shaft embedded deep within her, she bent her knees further and leaned down onto Jim, letting herself relax to enjoy the feeling of her butt engorged by the deeply sunk bulb of his cock.

He reached up to her, and placed his arms around her. This was now so very close to truly making love. They wrapped each other in a warm, tender embrace, and kissed each other deeply, as Melissa resumed the slow thrusting of her hips, drawing his cock in and out of her butt.

She whispered in his ear. "I never imagined Pogo would feel so large, so huge, inside of me. You fill me up so much, so deeply."

With these words Jim could not help himself and he matched the thrusting of her hips with his own, being careful not to push so hard as to scare or hurt her, but he did have to join in on the grinding and pushing of their hips against each other.

This was definitely something that Melissa would not tell her friends, at least not for some time or at least until they shared something comparable with her. She felt so naughty, so dirty, but so very sexy doing this with Jimmy, to be taking him into her sweet derriere. She felt his hands even grasp the upper part of her cheeks of her bottom through her skirt. She did not object. It was only natural that he do so. The man would do this if they really were having sex, and the feel of his masculine hands on her fanny was so nice, so hot.

She squeezed her own hand in between their tightly crushed bodies and slid it down under her skirt to her pussy, to the lips of her very wet, flushed cunt and engorged, stiff clit. She pressed and wiggled her fingers against her clit as she began to repeatedly thrust her anus and rectum even harder down onto his cock.

Jim gripped hard on the cheeks of her butt as he responded to the quickening pace of her hips. "Oh gosh, Missy, I can't hold out longer," he warned.

Melissa opened her eyes, looked deeply into the passion in his eyes, and gasped in return, "Do it, Jimmy, do it inside of me. Squirt your penis inside me."

"Missy, please," he gasped, trying to hold on.

She gave him very short, quick thrusts as she pressed harder on her own clit and said, "Fill me up, Jimmy, I want you to fill me up with your juice, let me feel it gushing and spraying inside of me."

And so he did. He couldn't hold out any longer and the dam just burst into her ass. "Missy," he whispered, as his cock twitched and jerked inside her rectum, spewing out loads and globs of warm, wet, sticky cum.

As soon as she felt the first twitch of his dick, her own orgasm overwhelmed her. "Oh Jimmy," she gasped as she collapsed onto his body, pinching her clit with her fingers as tidal waves of pleasure swept through her, her whole body shivering and shuddering as she felt his cock continue to jump and kick in her butt, gushing streams of gism into her rectum.

When he was done he did not pull out. He did not in fact pull out for some time. They wanted to just lay there, slowly letting their breathing return to normal, and, more importantly, enjoying this blissful feeling of tenderly holding each other: for him feeling himself still embedded within in her, and for her feeling him still deep inside.

Thank goodness it wasn't real sex.

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I do hope that you enjoyed it. This one I enjoyed writing a great deal. If you have any suggestions for follow-up or variations, I would be most happy to hear them. In any case, please do take the time to vote! The encouragement is really supportive, particularly in the context of some discouragement. Best wishes.