Jesss Babysitting Job Takes A Turn

Jess was in university and about to turn 21, and to make a little extra money she often baby sat for Rachel, a single mom with a young daughter named Sarah. A few months earlier, Jess began to think that Rachel was being flirtatious toward her. It began one night when Rachel invited Jess to stay for a glass of wine and then changed into a sleeping tee that barely covered Rachel's bum and showed off her fulsome breasts. A few times, Rachel bent over or sat with her legs in a position that gave Jess a peek at her body. After that evening, Rachel regularly poured some wine for them. and when they chatted Rachel would put her hand on Jess's arm or knee, and even once on her thigh.

Jess was certainly curious about, even attracted to women, and, after being seduced by her best friend's older sister, Jess had petted and a little more with two other girls, as well as having experiences with a few boys. She found Rachel sexy in an "older woman" kind of way; but Jess was afraid she was imagining things, so she forced the thoughts out of her mind. Jess liked Rachel and her young daughter and did not want to do anything to jeopardize her babysitting job.

Jess was left wondering until a recent Saturday. That day, Rachel said she would be an hour later coming from work and asked if Jess could stay until 1:00 am. Jess agreed, but Rachel got home at about 12:15. She insisted on paying Jess until 1:00 and poured two generous glasses of wine. After remarking how stressful her week had been, Rachel headed to her bedroom to change. When she came out, she was wearing a deep v-neck tee that barely reached the bottom of her butt and obviously had taken off her bra. When Rachel went to the kitchen and reached into her cabinets, the tee lifted, exposing her rear and pink t-back panties. After puttering around a bit, Rachel sat back down on the sofa near Jess, and Jess could see Rachel's nipples poking hard against her tee.

Rachel soon turned the conversation to more personal things by saying how hard it was to date as a working single mom, and she confided that she felt more awkward now "playing around" than she did when she was a teenager. Rachel refilled her wine glass, topped off Jess's glass, and kept chattering away, saying a single mom at her age had no chance to keep men interested beyond two dates without "a blow job and then some." The comment flustered Jess a little, and then Rachel put her hand on Jess's knee and said with a chuckle, "I'm thinking of trying the lesbian thing, do you know any hot girls looking for a mom willing to put out?"

It was an unseasonably warm spring night, so Jess had worn a peasant top and shorts. So, she was even more flummoxed feeling Rachel's warm hand on her bare leg. Jess blushed and mumbled something about Rachel being "pretty" and that she definitely would find someone special soon. Rachel kept her hand on Jess's knee and thanked her.

I hope you're right, Jess," she said quietly. "Is there anyone special in your life?"

"Not really," Jess said. After a pause, she added, "Well, maybe one or two people that I'd like to get to know better."

"Oh, you have to tell me more," Rachel teased, and her hand moved just above Jess's knee.

"Well one is a boy in my Literature class. We've chatted a few times, maybe even flirted I guess, and I can tell he's interested. So, who knows?" Jess said, finding it easy to confide in Rachel.

"And who's the other Prince Charming," Rachel said playfully. Jess paused for a second, suddenly a little less confident. But the wine, and maybe Rachel's hand on Jess's thigh, had an effect.

"Well, actually it's a girl," Jess said quietly but without reservation. "She works at the coffee shop with me, and she is amazing."

"Oh, I'm sorry, that was silly of me to assume it was a boy," Rachel said sincerely. "That sounds exciting."

"It's OK, I guess I'm still figuring things out," Jess explained. "It's not like I've had a lot of experience with either," she added and blushed a little.

"Well, good for you, Jess," Rachel said supportively. "You are so lovely that I'm sure you'll have boys and girls fighting over you all the time. A few seconds later, Rachel added, "I guess my remark about a lesbian looking for a hot mom was . . . a little awkward. I'm sorry." She shrugged and her hand stayed on Jess's thigh.

"No, it was fine. It made me smile thinking what you would have done if I would have said 'Yes, I do. Me,'" Jess said as she glanced quickly at Rachel's hand and then back into her eyes. Jess's heart was beating beat quickly as Rachel obviously was taking in the comments, and Jess was relieved to see Rachel's face soften into a warm smile.

Rachel then looked more intently at Jess. "I guess I would have said that I'm new to this . . . but I would love for you to be the first girl I ever kissed," Rachel said softly.

"Really?" Jess asked.

"Well, I mean that I ever kissed like this," Rachel said as she leaned in to kiss Jess, and her free hand moved to Jess's shoulder. Their kiss was deep and electric, both loving and passionate. Their mouths opened and their tongues danced. Jess tasted the wine on Rachel's tongue and the taste and smell of her mouth was familiar and inviting. Jess felt Rachel slide a little closer on the couch, and she wrapped her arms tenderly around Rachel.

As they kissed, Rachel kept her right hand on Jess's thigh and her left hand caressed along Jess's right arm until they eventually interlocked hands and fingers on one hand. Rachel's tongue explored Jess's mouth and she sighed softly. Rachel then guided Jess's hand to her bosom and pressed it onto Rachel's ample breast. Jess squeezed gently and let out a soft moan as she felt Rachel's boobs. Although Jess did not have many experiences to compare, Rachel certainly had the biggest breasts she had ever felt. Jess shuddered as Rachel's hand tracked higher up her inner thigh, and her nails gently scraped Jess's soft skin.

They broke their kiss and Rachel nuzzled and kissed Jess's neck. "You can squeeze harder if you like," Rachel coached with a whisper. Jess did as Rachel directed, squeezing Rachel's breast and even twisting a little as Rachel moaned her approval. Jess then felt Rachel's free hand on her breast through her top. Jess had smallish, perky boobs and often went without a bra. Rachel obviously enjoyed feeling Jess's youthful tits through just the thin top, and she squeezed heartily. Jess was surprised that she found the rough handling of her boobs erotic.

Rachel pulled back from kissing Jess's neck and ear, and she slid toward the corner of the sofa creating a little space between them. That caused Rachel to let go of Jess's breast, but Jess kept her hand on Rachel's luscious tit. Rachel looked lovingly at Jess, who could feel her heart beating hard and quickly. Rachel reached toward Jess's shoulder. "Come here, you beautiful girl," Rachel said quietly and she pulled Jess's head against her chest. Jess just went with flow as her face pressed against Rachel's big and inviting breasts. Jess felt both of Rachel's arms around her, holding her against Rachel's bosom.

Jess began kissing Rachel through her tee, which made the older woman moan with pleasure. The reaction emboldened Jess and she began licking and sucking her way until she was sucking Rachel's nipple through her increasingly wet tee. Rachel grabbed the back of Jess's head and cooed approvingly. Jess's hand moved to Rachel's other breast and felt her nipple poking through the tee. "That's it, sweetie, suck them just like that," Rachel said hoarsely. "You can do it harder."

Rachel's words sent a jolt of electricity through Jess's body. She sucked more passionately and her hand clawed at Rachel's other tit. "Wait babe, hold on," Rachel gasped. Jess paused for a second and Rachel quickly pulled up her tee to uncover her luscious boobs with two erect nipples. Jess was mesmerized for a moment before she looked at Rachel whose face was pleading for Jess to touch her. Jess reached for one boob, guided it into her mouth, and began squeezing and sucking greedily. Rachel groaned and again grabbed the back of Jess's head.

Jess was light-headed, sucking one nipple into her mouth and then the other, sensing how much Rachel enjoyed the attention and rough touching. She buried her face between Rachel's tits and enjoyed feeling smothered by the fleshy boobs. Jess began pinching and twisting the nipple she wasn't sucking, which had Rachel whimpering. "You can bite if you want," Rachel said breathlessly. Jess took that hint and bit gently on one nipple and then the other. "Mmmmmm," was all Rachel could muster until she said, "Harder."

Jess was so turned on, but she was afraid to hurt Rachel. Still, she bit harder, and then moved off the nipple and bit Rachel's meaty tit hard. Rachel moaned with pleasure. Jess then sucked hard on Rachel's boobs, which left two "love marks." Rachel then guided Jess on the sofa so that she was laying on her side with her head in Rachel's lap, much like a mother would hold a nursing infant. Jess looked up to see Rachel looking at her with glazed eyes and flushed cheeks. "You are so adorable sweetheart," Rachel said lovingly. "Are you hungry?," she added with a smile.

In the moment Jess surprised herself by playing along perfectly. "I'm very hungry mommy" she said innocently. Rachel eyes lit up, and she cradled Jess's head as if she were an infant, lifted and at the same time leaned in put her nipple into the younger woman's mouth. Jess "latched" and suckled Rachel's big tit as Rachel looked at her both adoringly and lustfully. After a few minutes of nursing play, Rachel began to rub Jess's boobs as Jess sucked. A few minutes later, Rachel moved Jess to the other breast and her hand reached down to caress Jess's tummy and then move lower. Rachel soon was petting Jess through her shorts, feeling the warmth and dampness of the younger girl's aroused pussy. Jess sucked harder and bit Rachel a few times when Rachel's fingers found Jess's clit through her shorts.

A moment later, Rachel deftly unbuttoned and unzipped Jess' shorts and slid her hand inside to cup Jess's pussy over her panties. Jess was so enamored of Rachel's tits she imagined swallowing them. The feeling of Rachel's hand inside her shorts was overpowering, and Jess wanted more. She reached down, lifted her hips and pulled her shorts down past her knees and kicked them off. Rachel looked at Jess and said, "We should go into the bedroom . . . just in case we wake you know who."

"Oh my goodness, you're right, I'm sorry," Jess responded, genuinely embarrassed that she forgot Sarah was sleeping not too far away.

"Don't be sorry love, I think I started this," Rachel said quietly. "Shall we?"

Jess stood up and picked up her shorts. Rachel stood up next to her and without pulling down her tee embraced Jess and kissed her deeply. Jess sighed and enjoyed the feeling of being in Rachel's arms and against her body. As they kissed, Rachel's hands caressed Jess back and then her panty-covered ass. Jess shuddered at the feeling of Rachel's naked breasts against her body. "Right this way," Rachel whispered and they walked hand-in-hand into Rachel's bedroom.

In the dimly-lit room, Rachel faced Jess again and lifted her top up over her head and off, uncovering her luscious breasts. Rachel paused for a second until Jess reached to lift her own tee up and off, leaving both of them in only their panties: Jess in a white bikini and Rachel in a yellow t-back. Rachel again embraced Jess and they kissed deeply. This time Jess felt Rachel's welcoming breasts against Jess's naked body as their breasts press together. Rachel's hands roamed over Jess's back and bum alternately rubbing and lightly scratching. Rachel guided Jess toward the bed and gently pushed her down across the bed sideways. Rachel then grabbed the waist of Jess's panties and pulled them down. Jess lifted her hips and Rachel slid Jess's panty down and off, leaving her naked on Rachel's bed.

Rachel was visibly moved by the sight of Jess in her bed naked. She lifted Jess's legs onto the bed and turned her 90 degrees so Jess laid longways on the bed. Rachel couldn't resist leaning over to kiss Jess again. When she did her breasts fell onto Jess's body until Jess grabbed them with her two hands. Hanging that way, Rachel's tits felt huge in Jess's hands. Rachel broke their kiss and moved up just enough so her big boobs dangled in Jess's face. Jess excitedly buried her face in Rachel's bosom, enjoying again the feeling of being smothered by Rachel's milky breasts.

Rachel maneuvered on to the bed and, on all fours, straddled Jess. Again, her boobs hung in Jess's face and Jess all but worshipped them, licking, sucking, biting, and pinching hard to Rachel's obvious delight. Rachel then slid down until they kissed again, and Rachel lovingly kissed, licked and sucked on Jess's face, before moving to her neck and chest. Eventually Rachel reached Jess's boobs, and she tenderly kissed and sucked them both. Jess's hands ran through Rachel's hair as the older woman tended to her small, perky tits. Jess moaned as she felt Rachel returning the favor by leaving a love mark on Jess's breast.

Then, Rachel continued her journey. She kissed and licked Jess's ribs and her tummy, using her tongue to tease Jess's navel. Jess felt Rachel's hot breath move lower. The younger woman stayed trimmed but not shaved, so when Rachel reached the soft fur, she was inches away from her ultimate goal. Jess reflexively opened her legs, anticipating the glorious feeling of Rachel's mouth and tongue on her pussy. The excitement of being in bed with an older woman and a mom was more than she dared imagine.

Rachel's heart was racing too. She could scarcely believe that she was finally about to taste her first woman, and the fact that it was Jess was breathtaking. Rachel hadn't thought about sex with a girl since she was a teen, and once she was married the idea really never crossed her mind. But the drama of her unexpected divorce and the challenges of dating as a single mother had Rachel re-evaluating lots of things, and Jess certainly awoke some strong and repressed desires. If anything, Rachel had some mild sub tendencies and she still enjoyed having her boobs handled roughly. So, she had been unsure whether to try to seduce Jess, but their flirtations over the past few months had made Rachel feel attractive and sexy, and fueled her attraction to her young babysitter. The thought of being an older and more experienced woman also executed Rachel.

Both Jess and Rachel felt electric jolts when Rachel's tongue finally found Jess's clit. The younger woman moaned loudly, her hands gently cradled Rachel's head, and Rachel's senses were on high alert. She bathed in her first taste of another woman's pussy, taking in the smell of Jess's sex and the combination of her soft fleshy folds and stiff clit. Rachel felt both aroused and a little pervy knowing that she was tonguing her daughter's favorite babysitter, and she liked both feelings. Rachel pushed Jess's legs further apart as her mouth moved down to lick and suck Jess's labia, and her tongue pressed inside Jess. Rachel was trembling with excitement and she wanted desperately to bring Jess to an orgasm.

Jess closed her eyes and focused on Rachel's tongue-lashing. It felt wonderful being with an older woman, especially one she considered a friend and a mentor. It also was exciting to know that this was Rachel's first girl-girl experience. Jess thought back to her first time and wondered if Rachel was as turned on as Jess was when she was seduced by her friend's older sister. It seemed so, based on how eagerly Rachel licked, sucked, and tongued Jess's pussy. Jess trembled as she felt a finger slide between her lips and press inside her. Rachel sucked directly on Jess's clit as her finger slid inside her young lover.

The attention and digital stimulation had the desired effect on Jess, and the sexual tension built in her midsection. Her soft moans encouraged Rachel, whose finger curled inside Jess and her free hand reached up to feel Jess's breasts. Jess ground her hips into Rachel's face, encouraging her to suck and lick more vigorously. Jess now fixated on the wave building in her body, savoring the moment and Rachel's oral ministrations. "Oh god, Rachel...," Jess gasped. "Oh yes. . . . .yes." The orgasm shook Jess's body and continued as she writhed on the bed holding Rachel's head between her legs. Jess came twice as intensely as she ever had before, and her body trembled long after the waves subsided.

Rachel was aroused beyond her wildest imagination. Bringing Jess to orgasm was the most exciting sexual experience of Rachel's life. She continued to tenderly kiss and lick Jess, resisting the urge to be more assertive because she knew from experience that Jess's nerve endings were on fire. Rachel closed her eyes and took in the wetness, taste, and aroma of their lovemaking. She stayed there a few minutes to allow Jess's body to recover. Rachel then slid up next to Jess, embraced her, and kissed her deeply. Jess savored the feeling of being enveloped in Rachel's arms and smothered by her open-mouthed kiss. Rachel's tongue, which had just given Jess so much pleasure, now explored Jess's mouth, and Jess felt Rachel's big breasts press against her body. They lay kissing for several minutes.

Jess wanted very much to please Rachel, and she began to kiss Rachel's neck before sliding further to kiss and lick Rachel's tits. Jess would have been content to spend the entire night nuzzling Rachel's big boobs, but she had another task to accomplish. So, Jess kissed her way down Rachel's belly until she reached Rachel's panty. Jess hurriedly pulled the waist of the panty down and slid it past Rachel's hips and then off. Looking into Rachel's eyes in the dim light, Jess brought the panty to her face and mouth and teased Rachel, who looked on adoringly. Jess then tossed the yellow panty aside and looked down to her prize, and Jess's body tingled when she saw that Rachel's pussy was smooth. Jess leaned in and both women moaned when Jess's tongue first pressed between Rachel's lips and slid up to her clit.

Rachel was not sure how she would respond to her first time being licked by a woman, and the intensity of her arousal surprised her. She was astonished too by how talented her young, often quiet and shy, lover was at cunnilingus. Perhaps it was the novelty of being pleased by a woman's tongue, but in the moment Rachel thought that she had never before felt such exquisite pleasure from oral sex. Rachel's hand moved to the back of Jess's head to gently hold her there, although Jess was not inclined to go anywhere else. "Oh damn it Jess, that is perfect," Rachel sputtered. Her words excited Jess and the young woman began sucking on Rachel's swollen clit.

It had been a long time since Rachel had reached an orgasm from oral sex. Her ex-husband would go down on her, but for several years it had been foreplay to intercourse. More recently, if any dates got that far, oral sex was a more one-sided proposition, with Rachel going down on several men, with only one returning the favor and not a lot of gusto. But this was different; Rachel felt a knot in her stomach that she usually felt only as she masturbated with a favorite toy. Somehow, Jess was doing everything her battery-powered friends did and then some.

"Oh god Jess, I'm going to cum," Rachel predicted. Her words spurred on Jess, who now pressed her face into Rachel's increasingly wet pussy. Jess was licking and sucking more urgently than she ever had before. "Touch my bum Jess, Rachel begged. "Please."

The second girl Jess was with had surprised Jess by putting a finger against Jess's bum and even pushing in a little. Jess was shocked at how good it felt, so she knew just what Rachel wanted. Jess moved a hand down under her chin and she pressed a finger against Rachel's puckered rear. Rachel's juices had run down so that her bum hole was drenched and Jess's finger slid in Rachel's ass just a bit. Rachel's body immediately tensed, and she let out a guttural moan. "Oh, fuck baby, yes, oh Jess," Rachel babbled. Jess shoved her finger in more and Rachel shrieked, causing her to cover her own mouth to avoid waking her daughter. Rachel's hand now grabbed Jess's hair on the back of her head and pressed Jess's face between Rachel's legs.