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Little Ditty 'bout Jill and Dianne

"One of these EAs learned more than the company paid for"

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Competition Entry: LGBT Sex Stories

(I hope John Mellencamp will excuse me)

They got off the elevator and headed down the hall toward their room. Two twenty-five year old recently promoted executive assistants sent to this conference by their employer.Their respective bosses had decided that it would be team building, not to mention expense saving, to have the women share a room while attending the three days of workshops and seminars covering various tasks they would be required to perform in their new roles.

Jill joined the multinational straight out of college four years ago only weeks before her seminar partner Dianne was hired hailing from a different Alma mater.Within the first year each demonstrated the intelligence, common sense as well as clerical skills to be put on the fast track. It definitely had not hurt their meteoric rise that they were both very good looking and well built. Jill was slightly taller at five foot six with a fairer complexion and golden hair. Diane had olive skin and auburn hair. Both had substantial busts and tiny waists. Though physically similar in many ways their personalities are night and day. Jill the fun loving outgoing party girl—Dianne quiet, reserved and introspective.

Jill swiped the key card through the slot in the door latch and pushed the door open. This was the second time the young women had been in the hotel room. The first had been just to drop their bags off before they rushed down to the meeting room for the opening session.

“I’m going to take a shower,” Jill announced as they entered the room. “Why don’t you take a look at the pamphlets and figure out where we’re gonna go for dinner.”

“Sure,” Dianne responded, placing her purse on the writing table and opening the drawer.

Flipping open the vinyl information folder the shower started running as she browsed the list. There was a good variety of cuisine listed. Dianne focused on a couple that offered Mexican fare and looked like they were only a couple of blocks away. Tossing the portfolio on the table, she picked up the TV remote and switched it on. Slipping off the jacket of her blue business suit she hung it on the back of one of the chairs and flopped across the foot of the double bed nearest the TV cabinet. Pulling her knees up and resting her head on her bent arm she aimlessly flipped through all the available channels. Returning to one of the talk shows she put the remote aside.

The show had just started. It appeared that the topic had something to do with lesbian relationships. The host was asking some woman about leaving her husband to live with another woman. Dianne watched with mild interest as Jill emerged from the steaming bathroom wrapped in a white hotel towel.

“How do you feel about Mexican tonight?” Dianne asked, taking in the blonde’s towel clad form.

“Sounds good to me,” Jill replied standing in the doorway rubbing her golden locks with another towel.

Dianne couldn’t help noticing how Jill’s breasts moved around under the towel in response to her arms being above her head drying her hair. She was ashamed of herself when she felt a little twinge between her legs. The towel was barely long enough to cover her blonde roommate’s butt. With her arms above her head like that Dianne thought she almost caught a glimpse of Jill’s pussy peeking out of the bottom. Giving herself a mental slap she turned back toward the television.

“What are you watching?” Jill asked as she plopped herself down carelessly near the pillows of the bed Dianne was reclining at the foot of. Out of reflex Dianne looked at the woman who was speaking to her and found she was looking directly at Jill’s neatly trimmed bush since the bottom of the towel had flipped slightly open and her co-worker was sitting with one leg bent at the knee and the other still hanging off the side of the bed. Dianne felt sure she must know she was exposing herself but she didn’t seem to care. Quickly turning her head back toward the TV Dianne replied, as casually as she could,

“It’s got something to do with lesbians.” Dianne shuddered a little as she said the word.

There was a pause as both women watched the small screen where two women were explaining to the host how they had become lovers after meeting in a grocery store.

“Have you ever made out with another woman?” Jill asked

“No!” Dianne replied too quickly, “have you?”

“Yeah, I did a few times in college.”

Dianne hoped Jill hadn’t heard her little gasp—after all who was she to judge.

“Have you ever thought about it? You know… fantasized?” Jill probed.

Dianne felt the heat rising up her neck and she knew she was blushing. She had looked at other women and thought about what it would be like to touch their soft smooth flesh, and have their gentle little hands touch her but she was far too shy to admit it. She focused on the TV trying to fashion a response. Out of the corner of her eye she noticed that her roommate’s hand was now resting on her crotch. Dianne turned her eyes enough to see that Jill’s middle finger was slowly stroking the soft folds of her labia. Completely flustered and unable to come up with anything reasonable she finally said,

“I don’t know.”

“What do you mean you don’t know? You must know what you fantasize about.”

Dianne kept her head turned toward the talk show but out of the corner of her eye she was watching Jill’s finger slide between her full lips up to the first knuckle and move up to the large looking hood that covered her pleasure center. Dianne was shocked as stirrings of arousal tickled between her legs. Still trying to figure out what to say, her eyes strained the limit of their orbit to watch Jill retract her clitoral hood exposing the hot pink pea sized organ. Jill’s finger extended downward again between those pliable lips and collected some of the juice that was beginning to emerge from within the dark recesses. Moving upward again her finger carried its load of lubricant and smeared it on the stiff love button.

Only a few seconds had passed since this conversation started but to Dianne it seemed like a long time. Everything seemed to be happening in slow motion. She felt her nipples stiffening inside her bra and the tickle between her legs was becoming a hum. She felt her pussy swelling and knew her own lubrication had begun to flow.

“Come on Di ’ admit it! You’ve wondered what it would be like to have another woman eat your cookie,” saying this Jill extended her leg so that it made contact with Dianne’s thigh just below the hem of her short skirt. The shy brunette flinched at the contact, but did not move away. Jill’s foot began a slow caressing motion on Dianne’s upper thigh.

“This one girl, Brenda was her name, got me started with women. I learned a lot from that dyke,” Jill said as her foot worked its way higher so it was now under the hem of her roommate’s skirt.

The soft painted toes made contact with the smooth warm bare flesh above the lacy top Dianne’s garter-less hose.

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Jill’s foot felt cool against her burning skin and again Dianne did nothing to dissuade the invasion. Jill rotated her ankle so her toes were now stroking the inside of the thigh.

“You’d be amazed at what an educated tongue can do! Brenda ate my pussy like no man ever could. When she sucked my clit the first time I came so hard I thought I was going to explode!”

The erotic statement coupled with the caressing toes forced a deep moan from Dianne’s core. Emboldened by the reaction Jill slid her foot even higher until it contacted the silkiness of her victim’s panties. Dianne kept her eyes on the TV not daring to look at the blonde’s face. She was sure her tense expression would betray her arousal. It didn’t matter. Jill’s toes made contact with the crotch of Dianne’s underwear and she sighed,

“My God Di, you’re so wet!”

With the toes now pressing very close to her pleasure center, Dianne surrendered to the awesome sensations. She allowed her head to turn fully toward her unlikely lover. Jill had loosened the fold holding the towel over her breasts and laid it completely open. She was now using three fingers of her right hand to make firm circular motions at the top of her vulva while her left hand was squeezing and pulling her right nipple—all while pressing on Dianne’s seeping mound with her left foot. Suddenly, in a very agile move, she rose to her knees and very lightly pushed on Dianne’s shoulder. The brunette offered no resistance in being knocked off her supporting arm and onto her back. Jill swung her right leg across the prone woman and sat completely naked straddling her hips. Dianne looked up at the smiling face of her blonde roommate as Jill said, “I’m gonna make you feel sooo good!” With that she began to work the buttons of the brunette’s blouse.

Looking down as the nimble fingers released one button after another, Dianne watched as the lacy white bra encasing her twin beauties came into view. Raising her eyes she watched the Jill’s boobs jiggle as the blonde concentrated on her task. Trying to block the nagging conscience that kept telling her that this was wrong, and that she should stop it right now, she concentrated on the details of the woman’s chest. She noted that there was no tan line, telling her that Jill sunbathed topless if not altogether nude. There were tiny freckles below her collar bone and above the round firm up turned breasts. The right nipple was very stiff and protruding compared to the left, a remnant of the squeezing Jill had just finished giving it. Dianne was getting an impulse to grab and squeeze the soft flesh dangling so close to her face.

Jill opened the blouse, and with a mischievous smile forced her hand under Dianne’s back, searching for the hooks holding the bra in place. This of course brought her tit within a tongue’s space of Dianne’s mouth. The brunette stuck her tongue out contacting the pliable right nipple which immediately began to stiffen. Jill emitted a sweet little groan and ground her pelvis down on top of Dianne’s, but continued to search out and unfasten the hooks of the prone woman’s bra.

After her initial tentative contact Dianne sucked the firm cap of Jill’s boob between her soft lips and gently applied her teeth. Jill squealed at the unexpected pleasure. Grasping the shoulder straps she pulled back up on to her knees taking the only thing between her and Dianne’s heaving breasts with her. The action pulled her nipple out of the prone woman’s mouth with a soft pop. Tossing the lingerie aside She looked down at the slightly pancaked boobs with their semi erect tips

“You have such beautiful breasts,” Jill sighed. Reaching down she pushed the firm full melons together creating over four inches of cleavage. Rotating her thumbs around she teased the dark nipples to full erection.

It was a good thing that Dianne’s skirt had flipped up above the waist band of her white bikini panties. Jill was grinding her pussy against the woman under her. If the skirt had been in between all the girl juice from both sides would have made an incredible mess of it.

“Now I’m gonna take your panties off and eat your pussy,” Jill whispered.

She slithered down Dianne’s body dragging her tits across the soft flesh of her abdomen—a little friction over the crumpled skirt then on to the soft wetness of the upper thighs. Letting her knees slip over the side of the bed Jill’s knees arrived on the floor between Dianne’s open legs. She gripped the waist band of the tiny panties and started pulling them down.

“You’re gonna have to help,” she said.

Obediently the brunette bent her legs putting her heels on the bed which allowed her to get her knees together and raise her hips off the bed spread. Jill tugged the soggy silk up the thighs, over the knees and down the calves of her cooperative conquest. When they slipped over the delicate painted toes she dropped them to the floor. Reaching under Dianne’s bent legs she wrapped her arms around the girls thighs bringing her shoulders almost up against Dianne’s butt. Her hands now coming down from the top she used her fingers to pull the woman’s slick labia apart exposing her ultimate treasure. Jill, who had some experience with these things, was amazed at the size of her roommate’s clitoris.

The size of a marble it protruded from under its protective hood and shone wetly. Jill inhaled deeply the girl’s muskysweet aroma. She plunged her tongue as deep as she could into the flooded love tunnel. Dianne let out a deep guttural groan and thrust her hips toward the invader. The action caused Jill’s upper lip to collide with the enormous clit. A rocket of pleasure launched from her pounding pussy that exploded in Dianne’s head. The sensation was too intense so her hips recoiled then thrust forward again. The convulsions repeated four or five times as Jill held on to the woman’s pumping hips. Jill adjusted the position of her mouth slightly so she was able to capture the pulsating pleasure bud and suck it greedily. Dianne’s hands seized her own breasts squeezing and pulling.

When Jill felt the first spurt of ejaculate hit her chin, she released the clit and opened her mouth wider to receive the precious fluid. The second and third spurts were not quite as powerful as the first, but Jill managed to reach out with her tongue and capture them. Dianne was, by this time, was reduced to quivering and moaning “Oh my God!” over and over. Jill diligently lapped up all of the dripping cum and lubricant. The continued stimulation of her vulva sent delirious little aftershocks to Dianne’s brain.

Finally raising her head Jill panted, “Wow, Dianne I don’t think I’ve ever seen anybody cum that hard!”

Dianne was too spent to respond, she just lay there still holding her breasts and trembling. Jill rose from her kneeling position between her roommate’s legs and deposited her overstimulated naked body beside her exhausted partner on the bed. Gently stroking the brunette’s slightly damp hair she whispered, “You see what I mean about an educated tongue?”

Published 
Written by Jackie1137
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