Teaching Jessica
Lesbian Story - Teaching Jessica
The sun streamed through the tall, thick panes of glass to fall on half a dozen canvases in varying stages of completion. The angle of the late afternoon light set a diffuse golden tone in the high-ceilinged room that made the paint colors deeper and more intense. Haley glanced at her delicate watch, and then gave a final word of instruction to the young man standing before her.
“All right class, that will be it for the day. Good work everyone. Remember, the studio will be open for after-hours work on Mondays, Tuesdays, and Wednesdays beginning next week and running until the start of the exhibition.”
It was mid-fall in New Hampshire, a beautiful time of year when the trees were just starting to reach peak foliage color. Haley taught most of the advanced fine arts courses at the small, exclusive college nestled in the White Mountains. She was young for a professor, only 29, but had already achieved a measure of success in a few small galleries, and had recently been invited to join the faculty after receiving an advanced degree from a renowned school in Paris.
She glanced up at the row of offices lining the south wall of the room at the second story. Actually they were more like finely appointed cubicles, since there were no walls between them - nor even anything separating them from the painting studio. Of course, in the spirit of historic preservation, the buildings were not to be modified from their original configuration, so it was not really a surprise that some overflow administration functions had been squeezed in this way. Haley hadn’t had the opportunity yet in her six weeks with the school to make her way up and see exactly what the offices were used for.
Suddenly a head appeared over the chest high wall that did double duty as a pseudo-privacy barrier as well as a safety rail marking the edge of the loft. Haley felt her chest tighten with excitement. It was a small blonde woman she had noticed only twice before. The blonde had long, wavy hair and piercing green eyes that sat behind an unusual and interesting pair of glasses. About 5′4″, she had a petite frame that was always draped in fashionable clothing. Haley felt her thighs tingle when the blonde caught her gaze and waved her up.
“I’m Jessica,” she introduced herself simply once Haley found the stairway up. She held out a delicate hand with a perfect French manicure. Haley was surprised by the strength of her grasp as they shook hands.
“Haley,” she reciprocated. “I teach the upper-level fine arts courses here.”
“I know,” Jessica smiled with a row of beautifully white teeth. “I watch you a lot.”
Haley tried to mask her expression, but Jessica saw through the attempt and blushed, realizing that her wording sounded a bit strange.
“I mean I watch your class a lot, and look at the paintings. When the Dean decided to open this row of offices over here, I jumped at the chance to get one of them. I just love art,” she explained.
Haley was more used to being the leader in a conversation, but Jessica had definitely taken her by surprise. She flipped her own long, straight blonde hair back from her face and flashed Jessica a warm smile. “So what is it that you do here?” she asked. “I’ve been meaning to come take a look up here, but I’m always too busy.”
“I work in alumni relations,” Jessica said, then gave Haley a short description of what that entailed. “Mostly, my day is spent on the phone or talking with people,” she concluded.
“I’ve only seen you in passing a couple of times before today,” Haley noted.
Jessica nodded. “I host a number of events as part of the job, so I’m often out of the office or traveling.”
“That must be tough on your husband, if you’re married,” Haley ventured. She was digging for information, not having noticed a wedding band. Something about Jessica excited her very deeply, but she guessed it was too much to hope for that this stunning woman would be bisexual or a lesbian.
“No, I’m not married,” Jessica said wistfully.
“Boyfriend?”
A sour expression crossed Jessica’s face. “If you can call him that, I guess.” It was obvious that it was a sore subject, so Haley left it alone. Instead, she broached a new topic.
“Say, those are great glasses!”
Jessica smiled gratefully, both for the compliment and for being off the hook about the boyfriend subject. After a few more minutes of talking, she suggested that they get a bite to eat in town.
Later that night, after a few glasses of wine, platefuls of pasta, and copious amounts of giggling, Haley was lying in her bed. Or perhaps floating upon her sheets would have been more accurate. She was positively smitten. They had gotten along amazingly, soon talking like lifelong friends. The tingling in her cunt was still present, and growing more intense by the second as she reflected upon the evening. Soon Haley could feel a thin trickle of her honeyed juices slipping out of her gash to soak the hem of the nightgown she wore.
Haley was not the prototypical lesbian - not by a long shot. Slender and busty, with fashionable long hair and an affinity for makeup, she would never have been called a “dyke” by anyone. But she hadn’t been with a man since her first year of college, and didn’t have any desire to have one again in the future. Her interests and passions lay with the softer sex, and if there was one thing that she enjoyed more than anything else, it was parting the vaginal lips of another woman to kiss her in that most intimate of ways. Her already moist twat grew positively runny as she considered what Jessica’s pussy must taste and smell like.
Being gay in a small New England town did not leave much opportunity for romance, unfortunately, and Haley hadn’t been with a woman in several months - since before leaving France, in fact. Fortunately, she was not opposed to vaginal penetration as some lesbians are, and in fact loved her small collection of dildos and vibrators. One of the few benefits of living alone, she thought to herself, is that she didn’t have to hide away her toys from prying eyes. In fact, for convenience, she kept her favorites underneath the second set of pillows on the bed. She reached for them now.
Haley withdrew a slim, curved tip plastic vibrator and a thick cyberskin dong from her hiding spot. Turning the vibrator on to a low speed, she mashed it against her clit and let her mind wander. Inevitably, visions of a naked, writhing Jessica filled her mind. Haley felt her body heat up as she envisioned their bodies intertwined in lust. She slowly increased the speed of the vibrations to match her arousal, but did not use the dildo yet. She usually preferred to climax at least once before pressing the thick dong inside of herself.
That climax did not take long to achieve. Simply imagining kissing Jessica’s soft red lips and tasting her sweet tongue was enough to bring Haley to a nice orgasm. She continued to turn up the vibrations without stopping, and then started pressing the dildo against her oozing gash. She didn’t try to fuck herself right away; instead she applied consistent pressure on the base of the dildo, letting it slowly sink into her as her pussy stretched to accommodate its girth. After a few minutes and some rocking of her hips, the toy was completely buried to its thick latex balls in her hungry cunt.
That was the signal for her to let loose, and she did. With long, steady strokes, she began working the cyberskin cock inside of herself, alternately withdrawing it to the thick head and then plunging it back into her steamy depths. All the while, she kept the vibrator, now on its highest speed setting, firmly pressed against her clit. The powerful sensations drove her wild and she came twice more as she tried to envision her fingers buried in Jessica’s clenching pussy.
Over the course of the next couple weeks, Haley and Jessica saw each other occasionally. As she had described, Jessica was often out of the office, and as a professor Haley spent as much time out of the classroom as in it. However, when their schedules coincided, they found themselves drawn together. They rapidly became close friends and arranged to have lunch together whenever possible.
Haley learned gradually that Jessica’s boyfriend of the past year, Harry, left a lot to be desired. It wasn’t that he was abusive, or anything so dramatic, but over time she began to recognize a pattern of neglect and apathy that was shocking to her. It was hard for her to imagine that anyone, male or female, could look at her petite blonde friend without being consumed by her. It wasn’t that Jessica was abjectly sexual. She simply exuded an aura of femininity, well put together yet delicate, that mated to her beautiful face and slender body to create a sensual desirability. Their lunches inevitably left Haley heated and masturbating both in the women’s room during the day, and in her bedroom at night.
But as exciting as this time was, it was also immensely frustrating for Haley. As their friendship deepened, it became more difficult than ever to hold back the passion she felt. And there were no signs that the feelings were reciprocated. Haley found herself staring constantly at Jessica’s firm 32B breasts, especially on those days when Jessica wore a tight sweater or let some cleavage show via a loose blouse. There were at least a couple of times that she really felt like she had been “caught”, but Jessica never said anything about it.
One Friday evening they went to dinner at a neighborhood Spanish restaurant and rapidly put away a pitcher of sangria. Haley had noticed that Jessica was dressed a little sexier than normal, and wearing a touch more makeup. As they chatted and nibbled on appetizers, giggling frequently from the intoxicating effects of the fruity liquor, Haley couldn’t keep herself from making a comment.
“Jessica, you look great tonight,” she said lightly. “What’s the occasion?”
Jessica scrunched up her face in irritation and waved the waiter over for a fresh carafe of sangria. When her glass had been refilled, she finally responded.
“I was supposed to see my boyfriend tonight, the asshole. But right before I ran into you he called and cancelled - said there was a game on that he was going to watch with his buddies. He pulls this shit all the fucking time!”
Haley was shocked by the sudden outburst, which was followed almost instantly by giddy laughter as Jessica realized she had stunned her friend. She had not previously sworn once, much less three times in a single sentence, in front of Haley.
Haley struggled to find something to say. From what she had come to believe, this was vintage Harry, and she felt that the guy was a real jerk who didn’t deserve his fabulous girlfriend. But then she was also biased with a hidden agenda, so how much could she really attack the guy without looking like a jerk herself?
Luckily Jessica solved the problem for her by calling for the check. She flirted with the waiter for a few moments until she had convinced him to pour the rest of their pitcher of sangria into a couple large to-go cups. “Let’s get out of here,” Jessica said, taking Haley’s arm.
“Where do you want to go?” Haley asked. Not that it really mattered, since she would have gone just about anywhere in order to spend more time with the object of her desires.
“Isn’t your place just around the corner?” Jessica asked gaily. “We can play cards or something.”
That settled, the two blondes left the restaurant arm in arm and headed out along the moderately trafficked Main Street. Haley had rented a medium-sized apartment right in town when she had arrived at the college earlier that fall. It was convenient to shopping, dining, and the small four-screen cinema downtown. This evening she was very glad to have chosen such a convenient location. Jessica surprised her once again as they passed the corner store by her apartment though.
“Hang on for a second - I want to get some cigarettes,” she said and dashed inside.
She returned in a minute with a pack of Marlboro Lights 100’s and matches. Stripping the wrapping from the box, she pulled out an all-white cigarette and put it between her lips, then lit it with a match. Haley was amazed and it showed on her face.
“I didn’t know you smoked,” she said incredulously.
Jessica grinned and exhaled a stream of smoke. “I only do it when I’ve been drinking and in certain moods,” she admitted. She took another deep drag and pulled Haley along before any further questions could be asked.
Upon arriving in the apartment, Jessica cooed with delight at the canvases that covered the walls. Most were unframed and had a raw, powerful energy to them. She examined each closely, not realizing that Haley was standing right behind her until she backed up into her. Haley felt her cunt lurch when Jessica’s back pressed against her breasts. Jessica stepped only slightly forward and looked over her shoulder into Haley’s eyes. “Did you do all of these?” she asked breathlessly.
“Most of them,” Haley nodded. “You like?”
Jessica’s eyes were glowing. “They’re incredible. You’re a wonderful artist!” They talked about the paintings for a few minutes, and then Jessica asked where the bathroom was.
“Down that hallway, across from my bedroom,” Haley pointed. She headed into the kitchen to get real glasses for the sangria while Jessica went to the restroom. A couple of minutes later a surprised burst of laughter startled her. Jessica was standing in the doorway of the bathroom, looking through her open bedroom door.
“I see why you don’t need a boyfriend,” she teased nervously, reaching into her purse and taking out another cigarette.
Haley was aghast, and felt the blood drain from her face as her angelic friend mirthfully lit up. Dreading what she knew she would find, she walked to the doorway and looked in - and there it was, her biggest dildo sitting atop the second set of pillows. She hadn’t been expecting company and hadn’t bothered to hide it after an interlude the night before.
Suddenly Jessica realized how stricken and embarrassed her friend was. “Hey, don’t worry about it,” she said touching Haley’s shoulder. “Hell, I wish I were so lucky to have toys like that. Harry won’t let me.”
Something snapped in Haley at that moment. She no longer cared about the risks of rejection. She was so desperately attracted to Jessica that nothing was going to be able to stop her from acting.
“Well, that’s one reason I don’t have boyfriends,” Haley said softly. She sidled closer as Jessica took a long puff from her cigarette. “And to be blunt, your boyfriend sounds like he doesn’t deserve you. You should be treated better.”
A pink flush began traveling up Jessica’s neck and cheeks. She found herself looking intently at Haley’s ample 38D breasts advancing towards her.
“I have to tell you,” Haley warned in a husky voice, “Looking at my tits like that is going to cause an intense reaction.”
Jessica looked up, blowing out a stream of smoke. “Umm…you, well…you’ve looked at my chest…I think…maybe once or twice…”
That was as far as she got before Haley’s lips were upon hers, gentle but insistent, probing. A moan escaped unbidden as she opened her smoky mouth and let Haley’s tongue penetrate to flick against her own in a wet duel. Jessica felt Haley’s hand slide up to cup one of her breasts and found her body responding, pushing forward to increase the amount of contact.
“Oh God,” she whispered. “I’ve never done this before…been with a woman.”
“You wanted it, though,” Haley insisted.
Jessica nodded, kissing Haley again. “I did…I didn’t realize it, but that’s exactly right…I think I sensed that you…”
Haley hushed her, kissing her firmly and expKellyng her delicious mouth with an agile pink tongue. “I’m going to show you pleasure in ways your boyfriend couldn’t dream of,” she promised. She led Jessica into the bedroom and began unbuttoning her blouse.
Jessica wore a navy blouse and a cream colored skirt, with flesh colored lace bra and panties. It was a subtle but sexy ensemble that was soon revealed as Haley pulled away the blouse and skirt. She cupped one of Jessica’s pert tits in her hand and lifted it, kissing the smooth flesh to the accompanying moans of her inexperienced friend.
Jessica was like putty in her hands. She was in sensory overload as her mind tried to process all that was occurring. When Haley hooked two fingers in her panties, she obligingly rocked her hips and lifted her feet to enable the underwear to fall away, revealing a closely trimmed blonde bush. The sight was incredible, exactly as Haley had imagined it. She moved a finger down to tease a droplet of wetness from between the slightly dangling lips, then brought it to her mouth and enjoyed the flavor.
“Mmm,” she moaned huskily. “You taste just like I’ve been hoping you would.” Noticing Jessica starting to bounce a little on her feet, Haley realized that her new blonde lover was a bit impatient. She moved her hand back down between Jessica’s legs and found her to be quite wet. Casually, she rubbed a finger lightly up and down through the moist slit for several seconds as they kissed again. Then she pushed Jessica toward the bed.
Her voice a little shaky, Jessica motioned with her half-gone cigarette. “Do you have someplace I could put this out?” she inquired.
“Don’t worry about it - it’s kind of sexy. You can smoke while I eat,” Haley replied, pressing Jessica onto the sheets of the bed so that she was resting with her legs spread widely. Haley knelt before her nearly naked friend, still fully dressed herself. “Pull the cups off your tits,” she commanded softly. Jessica instantly complied, revealing disproportionately large areolas and nipples the color of pink grapefruit. Haley lowered her face into Jessica’s oozing sex.
This close up, the scent was intoxicating. She paused to simply breathe it in, enjoying the familiarity of aroused female musk, and the subtle differences that made this pussy foreign to all others she had known. She could smell different flavors of it as her face moved slowly closer to the source. Slowly it grew richer and more intense until her lips were resting in the slick crease and her nose was tickling the clit. Jessica arched, trying to increase the gradually building pressure against her mound.
“Come on Haley, lick me,” she begged. She took a drag from her cigarette and exhaled hard. “I want to know what it feels like to have a woman do it.”
As much as she wanted to wait, make Jessica beg for it until desperate, Haley couldn’t restrain herself. Not after those hard weeks of hiding her feelings. She simply pressed her tongue into the depths of the steaming slit and tasted the sweet honey within. Then in a single long stroke she licked from the base of Jessica’s gash up to her clit. From the head of the bed came a loud moan, muffled by the soft legs pressed against Haley’s ears.
For the next few minutes Haley settled into a straightforward routine. She would lick and kiss Jessica’s erect little clit until her body rocked from side to side in vast waves of pleasure. Then she would slip lower, until she felt the folds of the soft vaginal skin spread to engulf her tongue and let the warm cunt-syrup collect in her mouth before swallowing. Soon Jessica was in complete rapture.
When Haley pulled away for a moment, Jessica’s disappointment was instantly obvious. Haley simply smiled mysteriously and asked for the big dildo on the pillow.
“Oh God,” Jessica whispered as a fresh trickle of wetness escaped from within her. “I need something so badly…but it’s so big. It’s much bigger than Harry’s cock. In fact, it’s bigger than anything I’ve ever had inside me…” Nevertheless, she grasped the heavy dong in one hand that failed to close around it, and slowly handed it to Haley.
Haley smiled. “Close your eyes baby,” she whispered soothingly. “I can make you feel better than he can.” It was the opportunity that she had awaited since the moment she first saw Jessica - a chance to introduce her to the pleasures of the gentler sex, and to show her why someone like Harry who didn’t appreciate her properly did not deserve her.
She wiped the thick black dildo through Jessica’s dripping gash several times until it was well and completely lubricated. Then, once again affixing her mouth to that delicious rosebud clit, she began working it into Jessica’s depths with short, firm strokes. The head slipped in surprisingly easily, since it was actually the thickest part of the dildo. However, at about an inch in, Haley encountered some resistance.
From that point on, every stroke of the dildo was a struggle against the natural tightness of Jessica’s tunnel. With each thrust, a bit more of it disappeared into the blonde thatched pussy as the skin stretched to accommodate the immense girth. Within seconds of starting, Jessica began riding one gigantic wave of constant climax. She had never been so thoroughly and completely filled in her life, and the experience was incredibly intense for her. Her cries filled the room as she begged Haley not to stop, never to stop…
Finally Haley came up to lie next to the exhausted, lithe blonde whose darkest nether regions she had so skillfully probed. Most of Jessica’s makeup had sweated off from the pleasure she had received, but to Haley she looked incredible beautiful. They kissed gently for several minutes and Haley enjoyed the feeling of Jessica sucking her own essence from her tongue and lips.
“I want to do you now,” Jessica said. “I don’t know what to do, exactly, but I want to try.” So saying, she put her hands on Haley’s shoulders and pushed her flat onto her back. The position caused Haley’s large breasts to strain the buttons of her blouse, and Jessica used her teeth to sensually release each button from its tension. Soon the shirt fell away of its own accord to reveal a full-cupped black satin bra.
“It’s takes quite a bra to hold in boobs like yours, doesn’t it?” Jessica teased her. Fortunately, it was a front clasping bra, which made it quite easy to free the heavy tits from their confinement. Haley’s nipples were of average size, but quite dark, and very hard by this point. Jessica lowered her head to Haley’s chest and began gently suckling on one breast almost as if she were nursing. At first Haley found the sensation merely interesting, although erotic since it was her lover’s first contact with another woman. But after a few minutes of the steadily growing pressure she found her breath growing short. Meanwhile, Jessica was firmly pinching and rolling the other nipple with one hand, and squeezing the breast she was sucking with the other hand, as if she were milking it.
The sensation grew in intensity until Haley felt like there was a direct electrical connection running from her breast to her pussy. Jessica’s intense suction felt like she was trying to draw the essence of Haley’s sexuality out through just the nipple. Surprisingly it led to a small orgasm. When Jessica pulled away, the nipple was red, swollen, and throbbing with blood flowing near the skin.
“That was nice,” Jessica commented. She then turned her attention to the other nipple and repeated the process. It came faster this time, and also more powerfully, and within a few minutes another climax rippled through Haley’s body.
Jessica gave Haley a few seconds to recover, then slid downwards - rubbing her much smaller breasts down Haley’s legs as she drew off her pants. Gazing upon the shaved twat that glistened before her, Jessica felt an overwhelming desire course through her. Suddenly she understood instinctively what Haley must have felt between her low legs. She lowered her mouth to the bald cunt and took her first taste of another woman.
It rapidly became five, then twenty, then hundreds of tastes as she let her pink tongue explore the myriad crevices and folds of skin down there with leisurely abandon. For Haley, though, there was nothing leisurely about it. She was shuddering with pleasure at Jessica’s raw talent.
“The dildo…” she gasped, “Give it to me…hard - fast!”
Jessica felt around the bed without turning her face away. Soon enough she found the thick dong and grasped it. It was still sticky with her own juices. She put the head of it to Haley’s cunt and, heeding the frenzied demands, pushed it smoothly up her until the heavy cyberskin balls were bumping Haley’s puckered anus.
“Fuck…” Jessica whispered in shock, amazed at the ease with which the dong had slid home in her new lover. Haley reached down and took dual handfuls of Jessica’s wavy blonde hair, pulling her face tightly into her pussy and climaxing so hard that she squirted small amounts of cunt juices onto Jessica’s lips and cheeks. Her screams were loud enough to echo from the walls and Jessica was thankful that the windows were closed.
Some time later, as their bodies lay entwined and they snuggled in a romantic afterglow, Haley asked the question that was sitting heavily in her mind.
“So Jessica, was this a one-time thing? Or do you think you might be interested in being my girlfriend? And what about Harry?”
Jessica smiled. “I think Harry is history. You definitely made me feel better all right.” And she leaned in to kiss the new woman in her life.
THE END
Lesbian Story - Teaching Jessica
