Teaching Assistants

[[This story carries strong elements of mature and femdom in addition cross-dressing.]]

*

"Look at the girl at the counter behind me to your right," Anna said casually. Xander discreetly looked at the counter of the coffeeshop and saw a fairly thin woman in tight light blue jeans, arm in arm with a slightly taller man. Even in a pony tail her hair was long and, at least from the side, she seemed attractive inasmuch that she lacked any defining negative traits in addition to lacking great positive ones. She was a B average beauty.

He looked back to Anna, asking for a hint of what to look for but her eyes darted to her left without looking at him or the woman. He knew he was supposed to observe the woman discreetly because Anna asked he do it in such a way that would draw no notice in the crowded coffeeshop. If she were to purse her lips and mutter what she wanted him to notice, it could draw interest from the couple next to them or worse the woman (or worse still her boyfriend) he was supposed to examine; he looked again but this time noticed what Anna wanted him to see. Nodding his head backward as his fixed his gaze to Anna's brown eyes, he mimicked her casually secret tone for one discreet word.

"Thighs..." he said confidently. Anna smiled and returned his nod. Her eyes widened briefly in a quiet mock surprise.

"They don't touch, like, at all," she started to show cracks in her stealth voice as a laugh tried to force itself out. Though not a victim of excessive gaiety, she found physical traits, most usually clothing however, worthy of a good laugh. Xander wondered whether this was merely a critique of a sickly thin woman or a catty joke to make herself feel better; either way it was extremely feminine. Xander noticed that the women who had nothing to worry about, at least weight wise, were most often the ones who obsessed with it. Anna, though not obsessive or overweight, occasionally talked about her size with mild complaint but without fishing for a compliment. That was one of the reasons he loved her.

Anna recovered her composure and continued to hide her voice in "plain hear" (so to speak). It was a delicate method requiring careful sequencing and word choice. That meant that not only were curse words nixed but also normal words that sounded similar. And phrases composed of innocuous words like "go down on" also needed to be avoided or altered.

"So would she work?" She resurrected a conversation they had not five minutes ago. Their conversation was about a possible third partner but somehow, he didn't bother to remember why, they got diverted. He looked at the woman again.

"No, too skinny," he rejected. Xander was a proud chubby chaser but, as Anna was a shining example, he found thinner women attractive as well as long as they had an ass of some kind. Anna was his first girlfriend who weighed less than his soft frame. Noting his objection, Anna began searching for another candidate. Dwelling at one person behind him for a few moments, her eyes continued briefly but came right back to that spot.

"What about him?" she continued in plain hear. Xander turned his head and roughly located where her eyes fell. A possible grad student with hair swept to the side like Robert Kennedy sat sipping a chai latte and reading the city's free newspaper.

"He looks like the blond guy from Scooby Doo," he said contemptuously as he turned to face Anna. Squinting slightly, he turned again for a second look. "And I don't get that half shaven look. That would really scratch my thighs when he be-lows me," he continued, carefully choosing his words.

"Yeah, I can understand that concern," she nodded understandingly. Xander always prided himself on handling taboo or hilarious subjects in a deadpan fashion at will. It was a trait he rarely found outside his generally cynical yet funny family and Anna was the wriest person with whom he had no blood relation. It was another reason he loved her. "But he kind of looks like my TA from Latin America..." By that she meant her teaching assistant Eric from History 260, Intro to Latin America, a class they shared. Xander had only seen him in lecture since their large class had nearly ten discussion sections and three TAs. He looked again. Yes, she was right. Aside from the hairdo he looked like him.

"So you want to bring your TA into this?" Anna shook her head in reply and Xander, convinced she was no longer deadpan-humorless but serious, was quietly shocked by what she said next.

"No, I'd want him on my own. I'm not going to share him with you," she said in plain hear and avoided the f-bomb which drew eyes at any volume. He was not quite sure where to go from there. Was she serious or had she called his bluff? Should he play along if she was joking or would he really be entrenching himself and encouraging her to cheat? "He's just so brilliant and hard working..." she said almost dreamily as her index finger circled the lip of her coffee mug and her eyes stared expressionless into Xander's. She was serious. Anna, more than any girlfriend he had had in his comparatively limited experience, talked often of her ex-boyfriends and occasionally their sexual escapades. This sort of talk did not make him jealous and he tended to merely laugh them off but this sounded different; she was talking about fucking a man while they were currently dating each other.

Only when Xander came to university did he realize how fortunate he was to graduate High School without his virginity. When he discovered just how long it took what he termed "power couples" to first have sex, he was dumbstruck. Some who had been dating for two years had never even given oral whereas Xander, with the one High School girlfriend he had for the summer after he turned seventeen, went down on her after two weeks, and fucked after a month which included a one week vacation with his family.

Anna had had many boyfriends and, until it came up in conversation, he had just assumed she slept with many of them. He even told Anna how surprised he was to learn that, in terms of how many months after their seventeenth birthdays, she lost her virginity to her third (and first long term) boyfriend later in her life than he did to his first (and three month) girlfriend. But her 21st birthday was just four months ago and his was coming shortly so, if one were to go chronologically, she lost hers first. But what made him feel doubly worse however was that she was talking about fucking the TA when they had not even slept together after five whole months which, after casual conversations about her sex life, was not unusual and the reason she escaped sleeping with all her boyfriends. Nervously Xander decided to play along.

"Eric? But he's so goofy looking..." he squirmed uncomfortably and waved his hand away. Anna looked quizzically at him and he thought he noticed a bit of anger behind those brown eyes.

"He's not goofy looking," she defended, this time with a glare and a tone she reserved for sarcastic reprimands. He sighed quietly in relief that she was merely joking about the man.

"And he's kind'a short." Anna could not defend her TA there. For a man, he was indeed short but still quite handsome with a defined jaw and short but wavy black hair very unlike Xander's soft and almost feminine face and hands. He never felt self conscious about his femininity but it routinely embarrassed him whenever he wore his hair down and got mistaken for a woman.

"So how about your TA?" she asked in a normal voice.

"Merilen? She's OK."

"No, I mean look-wise. Would you bring her to bed?" She brought TA fucking back up again after he thought it was settled. What was going on here?

"Well, yeah, she's pretty." Indeed she was. Though she was a thin woman, even thinner than Anna, she made up for that short-coming with sexy tan skin and perfect but slightly accented English. He recalled her recitation of Spanish poetry in section once and, perhaps because he did not know Spanish, he became swept into the rhythms of words. He recognized many words from he had picked up among the Latin American community but, coming from the mouth of the sultry Cuban brunette, they and she seemed exotic—nothing like the poor Indian descended Mexicans who worked two or three jobs in the States to support their families stuck in the old country. "I wouldn't want to do her though. She's pretty and all..." he drifted.

"Would you to any other TAs?" She continued. Xander thought briefly and arrived to his History 398 TA Stephanie. She was a grown woman in her late thirties or early forties but aside from her gray hair, she did not look a day past 25. And even with the hair, he determined it was genetic since it came in one large patch. Two thirds of her right eyebrow and a portion of her temple on that side were a silvery gray. Though still thinner than he went for, that is to say normal weight, she drew his interest for her frankness and love of history. He told Anna about her.

"So do you want her?"

"Anna, I'm a man. I want every woman."

"But of all the women you know right now, no matter how shallow of a relationship you have with them, would you put her at the top of the 'if I could do her' list?" He thought about it for a moment.

"The top five I suppose."

"Great. Do you want to see who can do their TA first?"

"Huh?" he quickly ejaculated in the non-sexual way.

"You know, a competition. See who can get their TA in bed first..." she shrugged slightly. Was she serious? Xander waved her question away and tried to change the subject but she proved resolute.

"Why not?" she pleaded but still retained the conversational upper hand.

"Well for starters, you and I haven't even had sex." Anna said nothing but looked unsatisfied by his explanation. "And besides, I think my TA is a lesbian." Anna broke into a punctuated laugh.

"What makes you say that?" she nearly shouted amidst the close ears of the crowded coffeehouse.

"Well, her doctoral work is on lesbian pulp fiction and she teaches a history of homosexuality course in another college," he answered honestly. Those were two of the first things she told about herself in his section. The third was an explanation for her accent. She was from coastal Georgia and, like many left minded people who move up north, she was mildly ashamed and bashed her homeland every chance she got.

"Studying homosexuality doesn't make, or mean I should say, you're gay," Anna began defensively.

"No it doesn't. But it doesn't hurt. Think of Afro-American studies majors—how many white people do you suppose are in that field?" Anna pursed her lips.

"Granted. Well, my TA has a girlfriend in Japan. I think we've evenly matched handicaps."

"Oh bullshit! No way is yours comparable!" he abandoned the "plain hear." That was it. He had gone too deep. Now he was not sure if he was merely going along with the joke or encouraging his cuckoldom. Recovering, he successfully changed the subject and they talked pleasantly for another hour before she left for a class. She paused by his chair on her way out, nearly saying something but thinking better of silence and leaving him in favor of the mid-afternoon light.

Xander tried to do the homework he brought with him but he was too distracted by what could very well just be one elaborate joke. It was not until five pages into his book that he realized his eyes were merely glancing at the words and his mind, dwelling over the previous conversation, absorbed none of them. He noisily slapped his hardcover textbook shut and placed it in his backpack. After gulping his now cold coffee, he exited and walked across the street to the local coöperative book store, hoping for a novel to take his mind away from history and his girlfriend's inappropriate proposal. Perusing the stress induced bent and dusty shelves, he came to the latest Margaret Atwood and brought it to the counter.

"Are you a member?" a larger woman with a few piercings and tattoos asked from her stool.

"No." The woman looked at the book and smiled a bit. This was the kind of author to attract just the right kind of woman who would enjoy Xander's wit and intelligence and this clerk, who was a bit above his preferred body type, seemed to be taking the bait even though he wasn't trying. Ever since he started dating Anna, he found quiet relief in not examining every interaction with women for a sign, a hope they may have sex with him.

"Is that all for today then?" she asked in a lazy wo/man's suggestive sell. He absent mindedly turned his head to the shelves by the exit as he reached for his wallet. Just as he was about to say "no" once again and further rebuff the clerk, he noticed bold capital yellow letters against a red spine of a thick paperback amidst a sea of gray and black hardcovers. He nearly shrieked with delight. "LESBIAN PULP FICTION"

"Yes, one more thing," he said as he walked over and plucked the book from its home and slammed it upon the counter. The clerk looked at the cover which bore a color illustration of two women. The one in the foreground had a volumous fifties hairstyle, a naturally cinched waist and wide hips, and was striking a pose with her hands behind her head while stripped of all but her low rise underwear, which barely hid her pussy, and a bra that struggled to contain her massive pointy breasts. The other woman, wearing an elegant purple dress, was behind a sketchpad and stared lecherously in the background. The clerk gave him a queer look.

"Homework?" she joked, ready to become offended at a moments notice if he was buying it for titillation.

"You know, it kind of is. It's a TA of mine's doctoral subject." Believing him, the clerk's smile returned as she rang up the two books. He paid, thanked her, and exited. As he walked back to his apartment, he reached for his cell phone. Rather than use his limited daytime minutes, he sent Anna a text message. Also if she forgot to turn her phone off, the text's ring would be more brief than a call.

After her lecture, Anna switched her cell from silent to vibrate and quickly noticed Xander sent a text. She pressed VIEW and smiled playfully but with a bit of menace. Her right thumb typed the same text as her own reply; "Game on..."

Several days of discussion passed before Xander realized their bet, treated as a harmless novelty when proposed, could have lasting effects on their relationship. Anna concurred and they agreed that total communication was a must. That way either could back off without fear of ridicule and, if feelings for their TA conflicted with their feelings for each other, it would be discussed openly and honestly. Inexperienced with life let alone sex, neither considered the existence of similar agreements between loving couples nor the consequences of failure.

Over the coming weeks Xander read the compilation of 1950s lesbian paperbacks and was struck by how diverse they could be. Expecting merely sex at first, he was surprised to find tenderness, hate, love, lust, reluctance, hollow endings, hanging endings, and the same cynicism he encountered in other books. Furthermore this was all accomplished with mere excerpts from selected novels. The editor, who admitted to lesbianism in the introduction, explained quite well how such books could exist on the shelves of drug stores in Levittowns across America.

Slowly but surely, his archetypical understanding of the decade his parents were conscious for and the Cleavers seemed to exemplify was being deconstructed. Before he could execute his plan however (which was fortunate since he did not have one yet), he employed strategies to get in his TA Stephanie's radar. In section, he took longer than his peers to assemble his effects and thus be alone with her to talk for a few moments. He also contributed to the discussion as he normally would but with more conviction and insight.

Once, after a semi-private, softly spoken, and brief in-class argument with Stephanie about the Soviet Union's economic influence in the world economy, she offered departing considerations for the rest of the students; those words resembled his position instead of the one she believed not ten minutes previous. He thought it unlikely she had merely played Devil's advocate earlier.

Anna was doing far better. She routinely stopped by Eric's office hours and even sent a not-so-subtle e-mail asking him to coffee. He politely rebuffed with a banal message reminding her of his office hours. Sure she was shot down at first, but at least she had even asked. Xander's problem was merely finding an in. Anna, in another trait that made him love her, spoke the same way she dressed. When among friends and a careless comment came from her lips, one heard almost simultaneously a single reply.

"Inappropriate!" and they would all laugh.

She was an attractive young woman unashamedly throwing herself at a handsome (Xander did not think he actually was goofy looking) grad student whose girlfriend was probably the mistress of some Japanese salary man long since disinterested by his wife. Men were only as faithful as their options and, with enough persistence, Anna would become one. But Xander's in came just two weeks after they started their competition.

Study carrels in the library Xander worked were in high demand. Though they were in theory checked once a year to clean out unused but still registered ones, the practice seldom matched and he had to empty one five years unused. Among its assorted pictures of a probably long since gone girlfriend and office supplies was a book on San Francisco Queer culture. At first Xander thought it a good book to understand a family member who was recently divorced from a long marriage and, quite by accident, was revealed to be a closeted gay or at the very least bisexual. As he turned its pages, he remembered something Stephanie said one day in section.

"One of the great things about being a pop-culture historian is that I can make references to TV shows instead of, you know, books..." she humored. He tucked the book away. Though he still needed to figure out the delivery of his approach to Stephanie, he knew it would involve that San Francisco book, the pulp fiction, and his family member.

Also in the meantime Xander and Anna continued to socialize with their respective groups of friends and end their nights with a pleasant cuddle, spooning, and heavy petting. When they were not lying in one or the others bed, he rarely thought of sex. Her short blonde hair reflected the moonlight, shining upon her temptingly soft thin lips in the darkness. Whenever he vaguely saw her features in the darkness, he wished to work up the courage to ask for sex. Anna, despite her modern day interpretation of chasteness, had been quite clear a few months previous that she merely awaited his word for the go-ahead. Though she seemed very dominant and independent in how she carried herself, dressed, spoke, and resisted his attempts to buy her extravagant gifts, and pay for meals, she was sexually submissive. He called her, he made dates, and when lying in bed he assumed the dominant position by either wrapping his leg or arm around her while his nose nestled in the back of her baby soft dark blonde hair.

Sometimes she would take the initiative and remove her bra to let him play with her fairly large and soft breasts. He loved to reach his hand through the middle and gently rub her chest just below the neck. Also from behind he liked to encircle her aureola with his index finger until her puffy nipples stiffened to large points. Or when they did not lay down together he was quite content to massage her small feet for hours and, if he felt friskier, he would massage her inner thigh to give him an excuse to get his nose closer to her aromatic musk emanating from her wetting vagina. It was the best they could hope for as two submissive lovers unable or unwilling to initiate sex.