In spite of a hot summer, or perhaps because of it, the bar seemed empty to Karla on this particular Wednesday evening. Of course, she had no true point of reference for she had just recently turned twenty-one, and tonight was but a third or fourth time entering such a venue. A few eyes centered on her as she walked through the door, to which she nodded timidly and tightened the grip on her shoulder bag before sitting down on a stool completely at random.
The bartender, a man in his early thirties, had a shaved head and a large gauge ring in his left ear. A black T-shirt bore the bar’s emblem, and Karla could make out a few tattoos edging out from beneath the sleeves. He looked tough, perhaps stereotypically so, and it seemed to quell some of the woman’s anxieties in a rather roundabout way. The man approached her, carrying a beer glass which he cleaned dutifully – again, in a quite stereotypical manner.
“What are you having tonight?”
“I’ll take… the house porter?” Her novice answer appeared to satisfy him, and he returned with a glass full of black liquid. She thanked him, handed over the money, and walked with it deeper into the venue. Pressing it to her mouth, she marveled at how dry it felt going down, though it was not exactly unpleasant to her. It was a nice change of pace; her prior experiences with alcohol were always tainted by wines and hard liquor, the college benders her friends forced upon her often ending with her passed out on some couch. Yet it gave her the privilege of no longer being a mere lightweight, something she took a bit of pride in.
“Karla? Over here!” The source of the shout was a woman standing near a pool table, cue in hand. Only when Karla got close did she realize the woman was on old teacher from her high school days.
“It’s been a while, Mrs. Langley.”
“We’re both adults, silly! Just call me Diane!” Diane Langley was an English teacher, and in her first year on the job, Karla had been one of her most challenging pupils. There had been some serious animosity back then; but the teacher, now twenty-nine, was willing to let that be water under the bridge. “Did you ever decide on college, or are you working now?”
“I’m just doing training courses at the community college. It looks like I’ll end up a radio dispatcher or something like that.”
“I’ve heard it’s stressful, but certainly not bad! You’re making a name for yourself, at any rate.”
Karla couldn’t help but blush. “Thank you so much. With things the way they were, I’m surprised that you have any faith in me at all.”
“You were going through some heavy stuff for your age. The fact that you managed to push through it is what’s important. Also, you look good! I only heard this secondhand, but you started transition shortly after graduation, right?”
“Something like that,” replied the girl. Originally born male, she had gone by the name Kase until she turned eighteen. With the freedom of adulthood, she could dress female full time and focus on perfecting her feminine mannerisms. Hormone therapy, meanwhile, had been a tedious process to obtain. Only in the last few months had she been able to get things organized on that front, and how far she would go was still a mystery to her.
“Well as I said, you look good. Anyway, what say we play a round?”
“No pun intended, but I’m sure you would school me pretty badly if I tried.”
“I’ll be gentle!” teased Diane as she waved to one of the bar’s servers. “We’ll play for fun though with a twist. Hey mister, bring us three more of what she’s having!” The man nodded, returning moments later with three more glasses of porter.
Karla watched this exchange with a raised eyebrow. “I take it you’ve done things like this before?”
“Something like that!” She set one of the glasses next to the one Karla had already started on. Of the two remaining, she drank a bit of the first so that its volume would match. “This will be the starting point for our game. Each time a shot is made, the other person takes a drink. When the eight ball is pocketed, the loser downs the last of her share. Sound good?”
With a nod, Karla grabbed a cue and took the break shot. The balls rolled across the table, though not a single score was made. This was made all the worse when Diane, expertly handling her stick, sank not one but two solids in short order. “Ha! Looks like I’ve still got it. Drink up, missy!”
Wanting to give Karla a chance, she decided to hold back her true skill for now. It took three more turns for the young transgirl to sink her first ball; things were clearly not going well. Taking a drink, the teacher grinned mischievously before lining up her next shot.
“So I heard my sister may be in your class this year,” Karla began. “Hopefully she won’t cause as much trouble.”
“That again, huh? Like I said, you were fine; but I will admit, your sister is quite the gifted girl.” Diane sank another solid and handed over control. “She’s running an upper B in terms of GPA, plus she’s athletically inclined.”
“I like to think if I had done the activities she’s doing, life in high school may have been very different.”
“You probably felt you couldn’t do those things.”
“Yeah, but let’s not go into that.” Karla pocketed a stripe, making the score 2-3. “In any case, she has her delinquent moments; she’s just good at hiding them. She needs to be careful because, as it’s said, certain mistakes can ruin your life.”
“I’ll have to keep an eye on her then,” replied the teacher as she pocketed two more stripes. “In the meantime, your first glass is looking quite empty! Better be mindful of your own behavior!” She was right, as the alcohol’s effect was becoming more and more intense for Karla. Each missed shot brought her former teacher – now her mentor, essentially – that much closer to a swift victory. It was awful but at the same time rather awe-inspiring.
Soon enough, Diane had sunk her seventh shot. “I have a question. Now that you’re in transition, what’s your stance on sexuality?”
“T-That’s a personal question!”
“Aw, come on! We’re friends now, aren’t we?”
Face and chest a deep scarlet, Karla answered in a rather hushed voice, “I’ve been with both but prefer women…”
“Very, very interesting. Eight ball, middle pocket.” There was an audible clink and then a ka-thunk as the ball feel into its destination. In one fell swoop, Karla had been completely and utterly dominated. All she could do was finish the second glass, her head starting to spin even before she had swallowed the last drop.
“I… may be at my limit already…”
“Oh? I didn’t expect that to happen so soon. You’re in no shape to get yourself home, so why not stay at my place? In fact, I insist!” Wrapping an arm around Karla’s shoulders, Diane led her out of the bar and into the setting sun. The teacher lived in a studio apartment a few blocks away, though by the time they made it to the front door, the college student was already half asleep. Diane quickly set Karla on a couch with a thin blanket to make her comfortable. Satisfied, she went on to prepare some things for later.
Later came in the span of a few hours, Karla wiping the drool from her mouth as she awakened. Confusion turned to embarrassment as she recalled the events of the bar. She felt that her pride had gotten the better of her, and in reality she was still too young and inexperienced to be considered an equal. She was still just a student and Diane her teacher. Karla suddenly wished that she could disappear, or at least redo the night.
“So you’re awake, finally.” Diane’s voice brought Karla to reality. She looked in the direction the words had come from, and what she saw caused her jaw to drop. Diane had changed into a cheerleader uniform not unlike the ones worn by students at the school where she worked. “I see I have your attention. Get up, because I have a set for you as well.”
Karla was quick to leap off the couch, rubbing her eyes to make sure she wasn’t dreaming, and then taking the garment from her teacher’s hands. Yet as she was about to look for a washroom, she was stopped by Diane. “No need for that. Here is perfectly fine, and make sure you remove everything.”
“M-Ma’am, are you sure? I mean, I still have a… you know…” A firm nod tells Karla that it’s better to simply go through with it without any regret. She removes her blouse and shorts, tights and camisole, then finally her panties. Fully naked, her body’s androgyny is much more evident, but her soft and supple skin emphasizes her feminine self.
It was having a definite effect on Diane. The older woman watched intently as her pupil donned the knee-length skirt and long-sleeved top, black with orange accents and bearing the high school’s logo. Karla’s smooth cock poked out cutely against the fabric, and Diane caught a faint glimpse of tender balls each time Karla bent backward to put on the orange knee socks.
“I remember when you were in school,” began Diane, “you would always do contortion stretches and a part of me often wondered if you kept that up once you graduated. Could you show me your talents, my dear Karla?”
“I… I don’t know, ma’am… It’s just… so…”
At this point, Diane knew she had the transgirl right where she wanted her. With her own special brand of dexterity, the teacher sat down on one end of the couch, bringing one ankle behind her neck and then the other. Her skirt flipped up, revealing that she too was devoid of panties, tender pink womanhood already slick with arousal.
The sheer provocativeness of it all caused Karla to freeze up, cock stiffening beyond any of her attempts to suppress it. Impure thoughts raced across her mind, and she couldn’t help but voice the loudest of them. “Mrs. Langley… can you…?”
“I can. The real question is, can you?” The teacher’s words were almost like a challenge, thus Karla could no longer deny herself this course of action. Sitting on the opposite side of the couch, Karla placed both of her ankles behind her, leaning forward to take the head of her cock into her own mouth.
Diane moaned deeply. “Oh fuck, girl… suck that cock of yours!” She traced her fingers up and down her rear before leaning forward and placing her tongue in her pussy, licking ravenously. The two of them continued to moan louder and louder at the sight of each other, this form of mutual masturbatory oral sex driving them absolutely wild.
Karla bobbed up and down on her length as if it were candy. She could see every circular motion of Diane’s tongue, the scent of the woman’s arousal wafting into her nose, mixing with the sweat she could smell on her own cock. It was all so good that she had to force herself to stave off climax as long as possible. Eventually though her orgasm would bring forth streams of sticky white which flowed down her throat and caused her whole body to shake with burning pleasure. Diane matched this with a release of her own, squirting juices all over her chin, lips and the inside of her own mouth.
As the two unfolded, Karla had a million questions. “How did you… When did you… Why did you…?”
Diane wiped away the excess fluids with a grin. “I’ve always had a penchant for flexibility myself. My ex-husband could do the things you just did, and we had many a passionate night together.”
“Ex-husband? You’re no longer married?”
“It happened about a year and a half ago. I didn’t bring it up because, well, it’s more fun that way! As it stands, you seem like you’ll be way more fun than he ever was!”
“What are you i-implying, Mrs. Langley? Y-You can’t be saying you like me t-that much…!” Karla’s heart was racing. She had always considered Diane an attractive woman, and she knew deep down that she could in no way resist anything this woman asked of her.
“I can read what’s in your eyes, Karla. You and I have shared in experiences that few will get to see or emulate, yet so much for you remains unexplored. Allow me once more to become your teacher, and I shall instill upon you the true wonders of the human mind, body and soul.”
Karla was at a loss for words, so she merely nodded and pulled herself into Diane’s lap. The two shared a passionate kiss in which the fluids of their bodies swapped over, a symbol of their freshly forged sexual communion. After their lips had parted, Diane moved out from under Karla, disappearing to her bedroom for just a moment.
When she returned, she had a long silicon double dildo in her left hand and two rolls of medical wrap in her right. “Tonight I shall make you a proper woman. If you could please remove your stockings for me?”
“Y-Yes, ma’am!” Karla did so in haste, watching with curiosity as her teacher slid the coffee table against the wall. She was instructed to sit on the floor and bring her legs up in a wide V shape, which she obediently did. Her teacher then removed her own stockings and placed her legs in the same position against Karla’s own.
The transgirl was no stranger to anal, yet something of this length was genuinely a first for her. The section pushed inside her had to be at least twelve inches, curving and twisting into places never touched. Diane smirked at Karla’s reactions before taking the other half in her own rear end – a little too effortlessly or so Karla thought.
Next came the wraps. Diane used them to pin her right leg to Karla’s left and vice versa. “If you’re confused, allow me to explain. This is a form of reverse tug-of-war. If I press forward, your legs move back, and that cute little ass of yours takes another few inches of dick. The game ends when one of us cries for mercy or when the dildo is completely inside one of us. Did you get all of that, darling?”
Was it even possible to be filled like that? Karla was curious to know, but she had no intention of losing, either. “I’m ready when you are.”
“Wonderful! Oh, and one more thing.”
“Y-Yes, Mrs. Langley?”
Instead of an answer, Karla received a spasm deep inside her when Diane squeezed the shaft’s midpoint. This toy was a vibrator! Though it shook only from the ends, it fired off precision pulses that made Karla’s knees weak and her mind hazy. Diane was quick to exploit this, pushing forward so Karla would gape and the inches of silicon could gently glide in.
Each moment brought Karla closer and closer to failing this challenge. She knew Diane expected as much to occur, that this was more a placement than an actual proficiency test. Regardless, she wanted more than anything to surpass the poor impression which had persisted through the night. Giving her legs a light bend which Diane was forced to match, she pushed forward with all her might and arched her back.
Unfortunately, she had miscalculated. Bending her legs in this way served only to open her insides as wide as possible, the lengthy shaft now flooding in faster with no way to stop it. Yet by forcing the shaft to bend even hard in Diane’s body, Karla had managed to trigger a powerful orgasm within her teacher. Against all odds, the young transgirl had won.
Diane’s entire body was flushed pink in orgasmic bliss. Once she calmed down, she instructed Karla to lay still as she undid the wraps. “This may sting,” she remarked with a giggle before grabbing the exposed end and pulling the entire length from Karla’s rear in a single, fluid motion.
The sensation was so powerful that Karla screamed, body shaking violently and cum dribbling from her cock as the orgasm was truly milked out of her. When her legs fell either side of Diane’s, she found herself too tired to straighten them, let alone stand. Having her legs splayed out like that felt so immodest but at the same so erotic. She felt as if she were turned into a living love doll, molded by her caring owner.
What had the two of them become, anyway? Were they mistress and pet, or did this make them girlfriends now? She quickly rationalized that titles were unimportant, pushing the thoughts away with a relaxed sigh.
“Are you feeling okay?” asked Diane.
“I can’t stand up… I think I’m spent for the night…”
“You performed admirably, Karla. We’ll be able to do more when your body is ready.”
With that, Diane helped her new pupil to the shower and cleaned her thoroughly. The two of them dried off and climbed into bed together, naked bodies twisting and rubbing throughout the night. As Karla slept peacefully between the arms and legs of her partner, she could still feel the love echoing inside her, the happiness of having found someone she could connect with in every conceivable way.