Teaching Assistants

Her feet smelled about as good as feet can so he slouched closer to bring more pressure to bear until contented coos escaped grinning mouth. Her periodically looked to her face, gladdened every time he saw her smile and closed eyelids. "Ok, that's enough," she finally said after twenty minutes. But by that time Xander had forgotten her lesson on compliance and continued to massage her feet for good measure. He was swiftly reminded of his place when her foot kicked out of his massage and struck his open jaw. "I said stop!"

He cried painfully as his teeth dug into his tongue. He instinctively clenched his mouth with his hands as if the pressure would do him some good, but it only seemed to squeeze out tears. "Oh quit your sobbing!" she commanded as blood passed through his fingers and onto his sheets. She looked at the drops with disinterest. "Fine. Go to the bathroom and fix that." With her permission, he sprinted out and into the bathroom.

Xander's face was flushed red and his eyes watered but stopped crying He removed his hands from his face and was relieved to find just how little blood there was despite the pain. After rinsing his hands under cold water from the faucet, he cupped them to hold the liquid and brought it to his mouth where he slurped, swished it for several seconds, then spat out a red tinted cocktail. He repeated this several more times, each time the water becoming a lighter shade of pink, until it was perfectly clear again, and his dangling hair was wet at the tips.

Hunched over the sink, he looked into the mirror. He remembered he had the authority to boot her out and for a moment he wondered if he should continue with Stephanie; the moment passed however when he told himself she simply liked to be dominant and his bleeding tongue was merely an accident of overzealousness. There was nothing wrong with passion--he got carried away sometimes, too.

"Xander, I'm waiting!" she reminded him. He turned off the bathroom lights and walked back into his bedroom, shutting the door. "Turn the light on," she ordered as she sat up from the bed. He complied and saw her body in total clarity. It was slightly wrinkled, a bit more than he would expect for someone not even forty, and dotted with many small light freckles as if from over tanning. It was not an unbeautiful sight but merely one of the many possible imperfections for anyone. "Strip," she casually instructed as her hand flicked at him. When he hesitated, she kept her gaze but turned her head down expectantly. He quickly complied and started to hastily remove his clothes. "Slowly..." she stressed. He complied but hesitated again when he came to his boxers. His cock raged and pushed against them like a pup tent. She gestured impatiently for him to take his boxers off and he did so, his cock bobbing. Free from its restriction but with this nakedness revealed to a near stranger, the two circumstances worked against him and his cock remained in a semi-erect four inches firmly pointing downwards. She chuckled a bit to herself.

"It's not completely hard yet," he offered as a reasonable excuse.

"Oh I'm sure it's not," she laughed even more, diminishing his erection further. "I'm glad it's not hard." With that she came off the bed and reached into her backpack. She pulled out a small hollow device resembling a plantain but slightly larger and made of clear plastic. She came to him and knelt before his penis as she held the cylinder up to it. Though nervous, he dared not shuffle away from her.

"What's that?" he asked nervously.

"It's a chastity belt. It keeps you from masturbating. What I do is," she began as she inserted his dick into it. "...place this part around your dick and lock it together with another end past your balls so the only way you can take it off without my say so is to rip 'em off." With familiar ease it was on before he could protest. It was smooth and seamless not unlike an experience where his doctor, while informing him of the importance of checking for a hernia, had already pressed his fingers against the wall of his scrotum and finished the examination before he realized it had taken place.

"Why am I wearing one? I thought you wanted to have sex?"

"Oh no, you misunderstood. I want to fuck you." This answer did nothing for his question but he dared not ask again. Walking to her backpack, she bent down, exposing her puckered anus and hairy pussy. She removed a blue skirt with large pleats and a pair of fishnet stockings, turned around, and threw them them into his hands. "Put those on..." she simply said as she stood impatiently. He cautiously complied and tried to stretch the stockings up his leg but met resistance from over-stretching enough to let his his toes poke through. "Bunch them up like a sock and roll them," she instructed.

He complied and soon the stockings were wrapped tight but comfortably around his legs. He gently rubbed them together and took a few steps, feeling quite natural in them. The tightness convinced his body he was wearing pants yet his hairs felt naked with exposure as he moved his legs through the air. Stepping with his toe first, he walked like he would if he was in his mother's high heels, a childhood pleasure he has long since outgrown and forgotten about. It felt feminine and very sexy. Coming to the mirror, he saw his toned feminine legs and, if they were not so hairy, they would have matched how he felt.

Using the mirror for guidance, he cautiously stepped into the skirt, his long wetted hair dangling helplessly past his chin. When it proved resistant to his hips, he forced it to higher to his waist until it gently pinched, giving him a muffin top. Thrilled by the sight of himself, his cock grew against its newfound cage. Never before had he worn ladies clothing but he absolutely loved how his morphed lower half looked even with the useless but still masculine dick between his legs; it was as if from his waist on down he WAS a woman and, with his long blond hair, his top was halfway there. Stephanie saw the gleam in his eyes and walked into him until her soft breasts pressed into his back. Her hands fondled his bound cock and bare chest.

"I see you like your clothes," she cooed softly as her mouth grazed his neck and her hands continued to play with his flesh.

"Yes," he quaked, his voice throaty with guilty pleasure. He felt wonderful in this strong woman's arms. The pain on his scalp and his tongue vanished and was replaced with the warm satisfaction that his dressing up pleased her enough to keep her with him.

"You're a good looking slut, aren't you Alexi?" she continued in a soft drawl. He hesitated briefly but, remembering the potential reprisals, he played along.

"Yes..." he said pleasurably.

"You're a bad girl. You wanted to fuck me with your cock—you can't do that since sissy sluts don't have cocks, do they?"

"No, we don't..."

"'No' is right." Her hand migrated up to his throat and her fingers wrapped around it, gripping him before tossing him backward to the bed. "You're not a sissy slut," she strutted closer, "You're just a cross-dressing whore! Look at you!" fiery anger replaced her sensual demeanor as her eyes glowed red. "You look like a fuckin' queen!"

"No!" he pleaded with her. "I'm not a queen!"

"Yes you fuckin' are don't lie to me! I know when you lie!"

"No, no, it's true! I'm a sissy slut! Please believe me!" he continued pathetically, his eyes starting to water. Some of her fire seemed spent but she continued to glare at him suspiciously.

"Alright, if you're a slut, where's your cunt?" she argued. He looked hopelessly around his bedroom as if searching for a way to prove that he really was a slut and thus keep her inside his competition with Anna; but strangely another side of him wanted to for a different reason altogether. His eyes lit up when he realized the solution and he turned himself around so his ass faced her, raised his skirt, and showed his asshole to the woman he needed to please. He wiggled it enticingly, his kept package slapping against his thighs. Turning his head, he beamed at the answer and hoped it would satisfy her.

"You call that a cunt?" she asked derisively. He nodded. "I bet it hasn't even been fucked yet you sissy fucking slut." Again he nodded, unsure how he could be a slut with a virgin hole, but she liked the answer so that was all that mattered. "Good. Kneel in front'v your bed and stick your pussy up," she commanded. He enthusiastically complied though ignorant of her intentions.

Again she went to her backpack but this time pulled out a tube of lubricant and what he vaguely remembered was called a butt plug. She came to his ass and knelt down as she violently pulled the fishnets down his cheeks. He hoped she didn't rip them needlessly. She applied some of the cold gel to his anus and some to her fingers as they gently explored his rectum. Realizing she planned to place the uncomfortable looking plug inside, he struggled to convince his anus to stay open. His effort paid off and within moments she had both fingers pressed against the walls of his colon, shortly followed by the plug which, with some force, rested snugly in his cavity. She wiped her fingers on his carpet.

Much to his surprise the plug felt comfortable in his anus...almost as if it was a hole meant to be filled. He forgot to pull his stockings back up so she forcefully did it for him; again he wished she did not ruin his new article of clothing.

Stephanie walked to the sole remaining light and turned it off before coming back to bed, lying down, and spreading her legs wide. Her hands came to her pussy and rubbed it enticingly. More than ever, Xander's cock throbbed as he imagined seeing his dick slide in and out her snatch and her soft lips kissing his chest—but well trained already, he simply stood and watched until she told him to come.

"Eat me..." she commanded. He walked on all fours to the foot of the bed. And begin he did. Always a gentleman when it came to cunnilingus, he primed the pump and first began with her thighs. She grunted with frustration and again dug her fingers into his hair, dragging his tongue instead to her already dripping pussy. Her juices had already curled the fine dark hairs into locks and his tongue, spreading and mixing the delectable nectar with his saliva, spread it to the rest of underbrush. No shy fold or deep crevice escaped his injured tongue that pressed on despite the pain and, with each slurp and lip smack, he was rewarded with pleasant coos and soft moans. Completely embedded into her muff, he felt his plug slide out ever so slightly. Terrified, he worried it would escape and anger Stephanie enough to make him lose his bet—thankfully it never did.

"Yeah, that's it..." she began to speak as his arms wrapped around her thighs. "That's a good slut...suck...suck...suck...lick...lick...suck..." she droned monotonically but with pleasure. "That's a good slut..." Her breathing became quicker and he thought she was near orgasm but, after clenching his hair, arching her back, and nearly screaming at the top of her lungs, when all was said and done, she simply calmed down and rotated her hips clockwise, forcing him to continue and keep pace with her pleasured gyrations. After half an hour his jaw locked shut and his tongue resumed bleeding and dripped onto her pussy and his bed sheets.

"I can't go on," he apologized, his voice muffled by a limp tongue and his own hand's pain relieving grasp. Stephanie's breathing slowed but her eyes stayed closed. "My tongue is bleeding again..." he explained just in case she was angry.

"That's all right," he was shocked and relived to hear. She sat up, her body glowing in the faint light coming through the blinds. "I came a bunch of times already," she explained. "Besides, it's time I fucked you." His heart lit up and his eyes glowed. He was finally going to fuck the sexy older woman and his dick, still imprisoned and raging more than ever, would be freed! "Slide up the bed but keep your pussy in the air," she commanded and he obeyed without the slightest hesitation. Maybe it was easier to take the belt off from behind. His knowledge of what a butt plug was however did not mean he anticipated what came next. He had only a vague notion it would involve penetration but he assumed sex would come afterwards and he could cum; after all he did for her, he deserved it right?

Stephanie went into her backpack one last time and pulled out a thick eight inch strap on. She fastened it around her waist and applied generous amounts of lubricant. He did not see her as she came onto the bed but felt her impression shifting the mattress and especially when she forced his stockings down his ass again. He disliked having his skin exposed like that. It felt wrong somehow that he was less like a woman. She raised his skirt and found the plug struggling to escape its anal hold and his caged cock dangling uselessly between his legs. She delicately pulled the plug out but before his muscles could close his anus, she stuck the strap-on tip in its place and held it there. Xander felt an emptiness in his ass and an overwhelming need to fill it despite the short interval but he dared not demand that from Stephanie whom he greatly feared to displease. Slowly but surely that emptiness was filled beyond the former's coziness as she steadily pegged him with more of her artificial girth. The pain was sumptuous as he felt her dick go deeper and deeper, stuffing his bowels with what only came naturally for someone dressed as he.

"Oh you like having your pussy filled, don't you slut?" she asked belligerently as the massive cock came to the hilt inside his asshole. "You know, for a virgin you take it pretty good. You're not a whore lying to me now, are you?"

"No, this is my first time. I'm a slut! I love your cock please don't stop!" he shouted back to her as he wriggled his hips, begging for more.

"So now you want it?"

"I've always wanted it! Please don't stop, I need your cock inside my pussy! Fuck my fucking cunt forever please!" He had to keep her going. The pleasure was immeasurable as every nerve in his colon stretched around her cock, aching for stimulation.

"That's what I wanted to hear," she said. His eyes rolled to the back of his head as she pulled backwards, reverting his bowels to their former unnaturally unfilled size and awaited further penetration which it soon received in greater frequency. His hands clenched the sheets and her hips pushed against his ass as she pumped and pressed onto his prostate until pre-cum dripped upon the bed. At times it hurt but he knew that was the price to fill him up as he desperately wanted. She called him "sissy" and "slut" and other names. But those were merely because he was playing a part in a larger sexual game that won him a bet. Then something unexpected started to happen.

"I think I'm gonna cum!" he yelled back as his balls began to slowly quake.

"Great, the perfect sissy slut can cum just from intercourse—I didn't even have to touch your little clitty!" she exclaimed as she picked up her paces. "Tell me before you do..." she instructed. An hour of love and frustration had centered entirely at his balls; they endured massage, cunnilingus, abuse, and now ass fucking but finally, as his dick pulsated against its restraint, he was going to come on his bed without anyone or anything else touching it. Like always, it started in his balls and raced through but unlike other times, his fairly soft penis seemed to shudder with its arrival as the first powerful spurt came to the tingling tip.

"Now!" he exclaimed when it exited his semi-erect cock and dolloped hard onto his sheets. As three more equally large loads emptied his frustrated balls, he felt something gooey strike the walls of his bowels with each new sputter of her thrust.

"What's that?" his voice trembled.

"Cum you slut. I bought it in a sex shop." He quickly realized she meant fake cum when she squeezed the second load from a reservoir. He readily embraced the thought of being filled with clean cum without a man involved. After all, he wasn't gay.

"Oh yeah, fill me up, give me all your cum!" he played up the part. She squirted enough for five sex deprived men, smothering his bowels. He sighed contentedly and Stephanie, keeping her surrogate dick inside, guided him to his side so they lied together in a spooning position. He faced the night stand that held his phone and a possibly masturbating Anna on the other end.

"That was wonderful," he said dreamily.

"I'll make a good sissy out of you yet, slut. Soon that cum in your cunt won't be fake and you'll become a slave to it. I can tell," she said as she swayed her hips slightly to move the fake cock around inside him. He did not have an answer for her but he knew her to be wrong. He was not gay, he was merely dressed like a woman and getting fucked by one—still straight sex. While it was not normal per se, it certainly did not make him gay or wish to engage in dangerous sexual practices. But otherwise too pleased, he did not try to refute her and he simply reached for his phone and ended the call.

"What was that?" she asked curiously amidst the cell's shutting down music. He had planned for such a question.

"I'm setting it to vibrate for the night," he replied to her satisfaction and she snuggled her hips closer to his so he became even more filled with her cock. Her arms lovingly wrapped around his waist and her nose rested on his neck, inhaling his apple scented conditioner. They fell asleep together, a smile on both their faces. It was only natural.

*

[[The compilation "Lesbian Pulp Fiction" is an actual book by author Katherine V. Forrest. This story is based on true happenings. Only names, places, and some events have been changed.

Don't forget to vote and constructive criticism is welcome. Chapter two, Anna's portion in the bet, is next in the BDSM category.]]