Teaching Assistants

[Chapter one is located in the Transsexual/Crossdressers category.]

ANNA

The following afternoon as was custom Xander and Anna met for coffee before their Latin America class. Both were punctual to a virtue but this time she was early, giving her the pleasure to find him walking through the door. Well, walking was not the proper word for it, more like hobbling. He seemed to clench his butt cheeks and use a rolling gait as if he wore stiff prosthetic leg. He drew a few stares from his fellow regulars who, in a superficially familiar way, considered taking their eyes from their cyber-novel and ask him what kind of accident he got himself into but Anna, with whom he was near infinitely more familiar, knew where his clenched steps came from. Her reaction began as a chuckle she tried to contain with her hands but soon eyes from the same patrons shifted from him to her and a loud almost maniacal follow up drew the rest. They did not understand why she would laugh at her boyfriend's obvious discomfort or let alone why she would point and ridicule him while jumping in her seat.

He sarcastically smiled and chortled back as he waited for his coffee. She was still laughing when he hobbled to the table and, very delicately, set himself down. Still not settled, she continued to point with her whole arm and laugh.

"Yeah, yeah, but at least I won..." he tried to say over her cackle.

"I'm sorry..." she managed to say between breaths, "I couldn't quite hear you sissy boy!" He nervously scanned the audience hoping they did not hear this last part. Anna noticed and began controlling her laughing spasms. He angrily glared at her but in a playful fashion one reserves for pets when they do something irritatingly cute.

"Are you done yet?" he asked humorlessly.

"No!" she continued to laugh. It took a whole two minutes before she could calm herself down. Satisfied, he continued.

"I'm sorry I'm late, but..."

"BUTT is right!" she shouted as she shot forward and laughed again. Shortly her breathing returned to normal as if she recovered from a splendrous orgasm.

"You know, I may hurt, but I still won..." he defended smugly.

"Won what? We didn't bet anything."

"Pride. That's what we bet. The one who can raise his head in the air....."

"More like raise YOUR butt up high!" she resumed laughing yet again. He decided to add nothing for fear of baiting the hook further.

"So how're things with your TA?" he changed the subject from his accomplishment to her shortcomings.

"Huh?"

"Your end of the wager."

"What end? There is no 'my end' anymore because your end ended it. You won, sort of." He stopped to think about that. He was pretty sure their bet had an assumption of intercourse, at least on his part, associated with sex so in this regard he did not have it. However, he and his assertive TA certainly fucked.

"A technicality."

"And since when does that not count? If that's the case there are a hell of a lot of virginal gay men out there," she argued to the affirmative. "And why are you pressing me to..." she showed concern for the first time as she stopped abruptly and scrutinized the patrons. "Why are you pressing me to do someone behind your back? I thought we'd be done with that now?" she said as she reached and held his hands tenderly. It was strange—Anna was doing everything she could to argue Xander had unambiguously won and thus ended the bet.

Xander wanted to tell her exactly why; if she started fucking her TA on a regular basis, he would have license to see Stephanie and get the dominance he needed. Stephanie did things to him that a fellow submissive like Anna would never perform herself and he needed any way to let this happen and keep the deep emotional bond and loving relationship that he could never get nor desired from Stephanie.

Anna after all held the key to his heart. Besides, the thought of another man fucking her and, after he left, she rubbing his cuckoldom on his face, was naughtily arousing; his cock responded appropriately but was blocked by the chastity device he still wore per Stephanie's orders. This was the other reason he needed to continue seeing Stephanie—she held the key to his other love muscle.

"It was your idea and I want to give you latitude," he lied. "Remember what we agreed on from the beginning? For this to work we need total communication. I'm not forcing you," he wanted, "and it's not my decision," he wanted it to be, "and you've said your concerns like we agreed." Anna withdrew her hands and stared to her left. Though she did at times wish to wrap her smell fingers around Eric's hot prick and shove it inside her mouth or cunt, actually pursuing it was another matter altogether. Xander, it seemed, got past any initial fears and dove in head first...between his TA's legs. She had actually given up on the bet weeks ago when Eric casually mentioned that his girlfriend in Japan was visiting soon. Her mother, whom she had not gotten around to telling she was dating Xander, told her to go with it anyway since "those things never last." She nearly did try again but when a fellow student interrupted their meeting, it gave her an out. "C'mon, I'm not only giving you my blessing, I'm encouraging it. At least think about it?"

She stared at him. "OK," was all she offered before they changed the subject and eventually went to class. With the afternoon sky came Xander to her rooming house and they cuddled in darkness atop her sheets. Unlike usual, Anna felt naked despite his warm embrace. She stripped of all but her underwear and went under the sheets, Xander's arm firmly squeezing above her waist. Still she felt uncovered but she was unsure how else to remedy the problem. As a temporary solution she tucked the sheets around under her body and squeezed her legs together, feeling momentary relief but soon she became accustomed to this and was wanting again.

"Xander, squeeze me please..." she asked softly. He complied but it was far more delicate than she wished. Thinking it merely her mistake for not specifying how hard, she asked again. She grunted slightly as his forearm pressed her stomach against his body but she moaned as well. Unfortunately she felt his muscles quiver as they exerted themselves and she knew he could not maintain it for long; but after all that, she was still becoming acclimated anyway. Xander, who was slightly overweight was, though not enough for her needs, strong. He was always good at opening jars and soda bottles; with the latter he would habitually screw on the cap so tightly that anyone who wanted a sip had to have him open it.

She made her decision.

"I think I'll talk to Eric tomorrow."

"Good, I love you babe," he replied as he gently squeezed her small frame.

"I love you too..." and so they stayed like this until she had to leave for a shift at her job.

"Anna," a veteran waitress nearly a decade her senior called, "bus 5 and 15 already!" Holding a half wrapped flatware bundle, Anna scowled in her general direction and angrily slammed it upon the empty booth. It was the customary booth to use when wrapping silverware but really any one of the dozens of free ones in this slow Tuesday evening would have done fine. Though Anna was by no means afraid of hard work, even beyond creating a good impression for her new job, she thought it asinine to push herself like she would when the place was full. When they were busy, tables needed to be done quickly regardless of what else needed doing. And when they were not busy, tedious but interruptible work like wrapping flatware was done.

Anna bussed the dishes and wiped the tables with a warm wet rag in the sight of their few patrons.

"What are you doing?" A male voice called. It was her manager Tom, a man as non-descript as his name who, despite lacking exceptional skills in any category including management, ran a whole restaurant with a free hand. The owner, a charmingly beautiful woman named Constance, was also his wife and, like the restaurant, he deserved neither. Though not cruel or incompetent, his mere presence inspired contempt from his employees whenever they first realized he deserved everything less than he had. Turn over, either from firing or quitting, was measured in the months.

"Bussing," she replied curtly, sticking her tongue out slightly as she wiped a particular stain extra hard.

"But I told you to wrap! We're almost out," he ran his thumb and index fingers down his mustache out of habit, just one of many peccadilloes that made an otherwise decent man so detestable. Anna closed her eyes and sighed. She snapped up and bit her lip slightly. Carrying her rag, she passed her boss. It was pointless to offer her excuse since he would reiterate the chain of command, only making her argue that central decision making would be bad policy since delegated authority, while occasionally hitting a speed bump like just then, was as a whole more efficient. He would disagree, reminding her that he had managed this restaurant longer than she had been born, and, depending on how arbitrary he or she felt that day, Anna would be gone.

"You can never please 'em all," a new voice called to her as she walked past.

"Oh, hi Eric!" she beamed.

Xander sat typing the beginning of a class paper when Anna's distinct ring alerted him.

"'Ello babe, what's up?" he asked with a playfully fake Cockney accent.

"Get to my place quick. I'm out with Eric but he's in the bathroom," she said with a loud and urgent hush. "Get in my closet and stay there!"

"You're gonna fuck him? Wow, that was quick!" he said with great joy and surprise. Anna was passive just like him so the only way she could bed him so swiftly was if he made a move. "Wait...your closet? Why?"

"Hurry though—my phone doesn't have a speaker so you can't listen like I did and this'll be hotter. Stay there to watch until the end but text saying you'll be stopping by soon so he runs..." but she did not finish her statement as she cut their call short. He figured Eric must have come back from the bathroom—wherever that was. Leaving his report at mid-sentence, he immediately shot out the door and caught the bus for the one mile journey. With each stop and seemingly unnecessarily long pause or hesitation in traffic, he tapped his fingers against his thigh and secreted a cold sweat. His stop was immediately in front of the indistinct rooming house and, using a spare key Anna gave him some months back, he entered her room, turned his phone to vibrate, and walked into her spacious closet, shutting the doors behind him.

The plan as far as he saw it was to text message his imminent arrival right after they finished just so they could laugh at his frantic departure. Goosebumps crawled up his arms. This plan was even better than his speaker phone trick.

There he waited for twenty minutes, every time his spirits raised at the thought of the firm Eric kissing Anna's soft lips and impaling her to raucous orgasm, his penis battled its prison but inevitably lost. To make matters worse, he fantasized about the fun he would continue to have Stephanie. She mentioned something about clothes shopping, much to his delight. He was eager to get his female persona better dressed to satisfy Stephanie more than he had been able to with just his bottom. He wanted to be a whole woman for her bottom and top.

Two pairs of footsteps sounded outside her door before the clanking of a key unlatched it. Through a small crack, he saw Anna enter first. She threw her keys onto her night stand and kicked off her shoes while he dropped his bag onto the floor. Glancing over the closet he superficially examined his new surroundings before kneeling to untie his shoes, his back remaining straight the entire time. When he removed his socks, Xander marveled at not only the feet's size but how they were matching bottoms to the top that was his head; they were lanky with defined bones that gave them a square—nearly goofy—look.

"This is a nice place you've got here," he made small talk as Anna yawned, raising her hands ceilingward.

"Not really. It's a dump but it's cheap, clean, and all mine." She collapsed backwards onto the bed and laid there, arms outstretched like Jesus awaiting the pierce of the Roman lance. It was Christ's destiny to be impaled by the pointed shaft and he accepted the inevitable death with selfless obligation. Unlike Jesus however, Anna did not feel obliged at all. Her TA looked virile and had a brain to match his wiry but strong frame and she preemptively decided exactly what to do.

Like Xander when he left his phone on his night stand, Anne readily forgot he was even in the room as Eric walked slowly towards the bed and tugged at her clothing. Hovering over, he tucked his finger under her front pant waist and ran it underneath, catching a few hairs on her higher mons. It tickled her slightly but she resisted the turn-off of laughing and instead quietly inhaled as his fingers became his whole hand and a few hairs on her mons nearly became her clitoris. Armed with the patience and experience of an older man, he knew that bundle of nerves was far from ready to cum.

"So whose that guy I see you in lecture with?" he asked distantly as he caressed her flesh.

"That's Xander..." she supplied but awaited further prodding. She figured only answering direct questions would be a preventative measure in case blurting her arrangement with Xander was too tempting.

"Is he your boyfriend? Are you serious?"

"Yes he is," she answered his first question, pausing to consider the second. Yes, she supposed she was serious with him. But did this mean she was entirely loyal? Up until their wager she never seriously considered fucking another man—she had not even fucked her boyfriend yet. "Serious" contained gray areas further complicated by their arrangement and for once made her reconsider what exactly she had with him. She loved him deeply, she was certain of that even now after his incentive based cheating, but was it a lasting love? They were fundamentally different personalities, held different politics, and disagreed entirely on the metaphysical world yet they never fought. Xander insisted it was not because he quashed such feelings by bottling or humoring her whenever he took issue.

Always emphatic and filled with 'wisdom,' he told her repeatedly that "Suppression of emotions," he started with his tongue rubbing the crease inside his cheek, "is one of the surest ways to bitterly end a relationship." And though he had not initiated sex yet, at least with her, just the thought he possessed the self control not to act was refreshing compared to her other boyfriends. But still she needed an answer for Eric so she chose a simplified lie.

"No, not really."

"Good," he answered happily. He removed his hand and gently pulled at her shirt, bunching it up above her naval. Anna understood what he wanted and sat up gently enough to pull the shirt off, leaving her in her plain black bra. Looking at her soft young tits, he went for her pants yet again but this time unbuttoned and unzipped them. Anna hooked her thumbs inside to remove them herself but Eric's large hands gently slapped them. Instead he gestured for her to raise her ass. After she complied, he grabbed firmly onto her jeans and tugged ruthlessly until they were off, revealing her matching black panties. God's chisel did not leave any marks when he created this Venus whose curves were proportional yet voluptuous, with thin legs and arms but a bit of flesh in her stomach and a fair bit more in her bosoms which slowly raised and lowered in an anticipation as his eyes sought in vain for imperfection.

"Your body is that of the perfect woman," he stated simply while he caressed her soft stomach, tickling her moderately. Xander repeatedly told her that as well but despite his genuineness, it somehow meant more coming from Eric. His hands ventured to the lacy bra that centered her bosom as she lay on her back. He delicately cupped them, his fingers dimpling the tender flesh.

"Take it off," he gently commanded. She raised her back and expertly reached behind, removing to her the barrier not a second later. She lowered herself down, putting her hands behind her head to let his eyes bear her entire bosom. Her breasts were so ductile that, as they spread down the side of her body, his eyes made out fine columned wrinkles running about the length of her copious tits like a fine piece of paper crumpled and re-crumpled. Being still a young lady, her millions of footsteps had already abused them with innumerable bounces and jiggles. He reached with both hands and gently grasped the melons again. Without the bra they felt delicate and he feared that, by pressing his eager fingers too hard, they would bruise.

"Do you like them?" she asked, aching for a compliment from her silent partner. He shushed her delicately.

"No talking please..." he drifted as he leaned his head to the side and rubbed the moist skin between her grand tetons. He bent down to his backpack and pulled a ball gag out.

"Do you know what this is?" he dangled it in front of her.

"Yeah, I think," she replied unsure of her answer.

"Sit up." She rose into the light shining through her blinds, streaking her body with the street lamp's yellow sheen. Her head still shrouded in darkness, he found her mouth and securely fastened the gag behind. She groaned in protest when he pulled too tightly.

"Don't worry, you'll get used to the pressure," he smiled softly as the back of his hand graced her blushing cheeks. "Turn around, get positioned." Despite not knowing what position he wanted, she figured any enthusiasm was better than indecisiveness so she lied on her stomach. Careful not to press her breasts too hard as her chest stabilized her front, she raised her hips with her knees until her ass displayed itself proudly and her panties rode into her cheeks. "You're such a loud self-righteous person in section Anna," he continued to caress her naked perfection, "Yet you're so compliant. Why do you suppose that is?" Her replying words were of course muffled by the large red ball strapped to her face. He listened attentively and softly grunted. "Yes of course," he answered, pretending he cared.

He tugged at her panties, sliding them along her delicate curves until they stretched beneath her bush and exposed the vulnerable folds of her sex. "You are a woman of many opinions but you know so very little. You've yet to see what life has for you my dear," he whispered to her complacent form. "You want more out but you plague yourself with crisis. Just two months ago you talked with me about dropping out of school because you had a bad week. I'm sure to you this was just another week in a string of bad events that you've felt yourself a victim of," he awkwardly phrased, temporarily confusing her. "You are a victim" He brought his face closer to her ears and whispered softly. "You let yourself be the victim because you need the attention. That boyfriend of yours. You think you love him because he's attentive and listens, right? He indulges your spats thinking he's being supportive, right?" he answered his own questions. Though she would not admit it even to herself, he was absolutely right. As Xander looked on from the closet, he realized he knew it, too.

Eric softly kissed her on the cheek, forcefully grasped her wrists, and tied them behind her back so tightly that she could not break free if she tried. A funny word "if". It implies all manner of choice and freedom—none of which she had nor wanted. Her naked body broke out in goosebumps while as ran his fingers down her trembling spine until they came to the dent of her ass. Suddenly he open palmed slapped her right cheek leaving a red mark from the bursting capillaries saturating the area. She turned her head to look back and cried weakly through the gag. Her rapid heartbeat engorged her labia and vagina already oozing from the sweet waiting anticipation for whatever he would give her. His fingers continued down her crack, stopping at her nervously clenching asshole.