The Wine Tour

The Wine Tour

Jake wasn't crazy about doing wine tours. During the week, he used his Sprinter van mostly to transport businessmen from downtown DC to Reagan National or Dulles International Airport. It paid reasonably well, but he always liked to supplement his income by doing gigs on the weekend, and when the weather was nice, that often-meant driving groups out to the Virginia countryside to tour the wineries. It wasn't his favorite kind of gig. The groups booking him for wine tours were often young, noisy, demanding and invariably after 3 or more stops, drunk as well. He was always happy to drop the last one off at the end of the day.

Sunday was a crisp fall day; the kind of day that brought people out in droves to see the fall foliage and visit the numerous wineries in the Virginia countryside. Jake was booked to pick up a group of women at an upscale home in McLean, Virginia and drive them to a series of wineries along the Route 29 corridor to Charlottesville. He pulled into the long tree-lined driveway at noon, and parked under the portico over-arching the entryway of the ornate Victorian home. The five women gathered there were engaged in animated conversation when he pulled up and took little notice of him. He jumped out and opened the sliding door of the van, the interior of which had been modified to allow for a more comfortable seating arrangement.

Unlike most vans, this one was not set up with bench-type rows of uncomfortable seats. Rather, he had configured it to hold no more than 6 people, with a comfortable semi-circular bench seat. It was complemented by a plush carpet on the floor, deeply tinted windows for privacy, soft lighting and a Bose sound system; none of which was likely noticed or appreciated by the women, who, still chattering, climbed in. This group consisted of more mature women, likely in their 40's or even 50's. They were well dressed and well turned out for a Sunday outing and Jake hoped that their behavior after a few stops would match their appearance. Of course, that wasn't his typical experience, but perhaps today would be different.

He managed to gain their attention long enough to announce the itinerary for the day before closing the door and climbing back into his seat, but he didn't expect that it really registered with any of them. The drive to the first winery took about 40 minutes. It was a small winery nestled against one of the many hillsides that lined the Shenandoah mountains that cut across central Virginia. Jake jumped out of the van, opened the door and took the hand of each woman as they stepped out. It was his really first good look at each of them. They were all quite attractive.

Jan was a blond; taller than the others with long legs and sculpted features. She might have been a model at some point in her life. Liz was a big, blousy brunet with large breasts, wide hips and large ass, but somehow, it all worked to her advantage. She had a bright smile and come-hither look in her eye and winked at him as he helped her out of the van. Grace was the smallest of the group; very petite, with pleasant features. She was clearly the shyest of the group and averted her eyes when Jake spoke to her. Patricia was also blond. While the others were dressed more demurely; mostly in slacks and modest tops, she wore a short mini-skirt over black tights with a tank top that barely contained her ample breasts. As she leaned forward to exit the van, she gave Jake a nice view of her bra-less breasts and prominent nipple rings. She smiled widely at Jake, fully aware of where and how he had looked at her. He smiled back and held her hand a bit longer than necessary as he helped her step off. The last to emerge was Emily, the only redhead. She looked a bit out of place in the group. She was much younger, indeed, girlish in her appearance; likely in her early twenties, although she looked much younger. Her manner of dress was quite modest - more "The Gap" than Neiman Marcus. She had a friendly smile however, and was the only one of the group to actually thank Jake for his assistance.

Jake watched them file into the winery as he parked the van and then waited for them to emerge. The understanding was that they would spend no more than 45 minutes at each winery in order to stay on schedule, but that seldom held. When they didn't appear as scheduled, he pulled the van up to the entrance and texted Liz, his group contact, to alert her. After about 10 minutes, they emerged, each feeling the soft buzz of their first glass of wine of the day. Patricia was the last to board, and as she did so, she leaned forward to give Jake a nice view of the "flip side." Her tights were actually thigh-highs that terminated just below her ass-cheeks, bare except for the narrow thong that lined her crack and disappeared into the nether region between her legs. Jake smiled to himself and thought that perhaps this particular tour would be more interesting than most.

The ladies were quite animated as they made their way to the next winery some 20 minutes away. Liz was the loudest of the group; also the most vulgar, as she recounted how she had spent the previous evening with her daughter's tutor. Jake couldn't make it all out over the loud laughter and occasional shrieks, but it apparently involved a stick of butter and Liz being bent over the tutor's lap. At the next stop, four of the ladies piled out, but Emily remained behind. "Not going in?" queried Jake. "No, it's not really my thing," she responded. He invited her to sit with him in the front seat while they waited as it was awkward talking over his shoulder. They chatted for a while and he learned that Emily was Liz's live-in nanny. She was only invited because it was her birthday and this was Liz's idea of a good time.

"So, do you have a boyfriend" Jake asked. "No," said Emily. I used to, but he wanted to do things that I wasn't comfortable doing, so we broke up." "Like what" ventured Jake. She blushed and said "you know, he wanted to get into my pants, and I told him I was saving myself." "Oh, so you've never....?" his voice trailed off. "No" she said, blushing again. Jake wanted to learn more but before he could the group came streaming back to the van. He loaded them up again. Both Liz and Patricia were a little unsteady on their feet this time. As he helped Patricia into the van, she brushed against him and he felt her erect nipple trace a line on his bare arm. She turned to smile at him and glanczed down at his crotch, which betrayed his growing erection. He smiled back and hopped back in the driver's seat.

The third winery was nearby and as the four ladies disappeared into the entrance, Jake turned his attention once again to Emily, who had remained in the front passenger seat. "So, you're waiting for Mr. Right?" "No, it's not that, she responded. I just want my first time to be with someone who cares about something more than just getting himself off." "I want someone who will take his time with me." Jake nodded knowingly and thought about the possibilities. "Of course,' he said. "You want your first time to be special, and it should be." He looked at her with renewed interest. Her light freckles complemented her red hair, and he wondered if she was freckled all over. She was wearing a thin white knit sweater. Her breasts were on the smaller side, but her sweater accentuated her curves and he could see the outline of her nipples pushing against the fabric. She also wore a plaid mid-length school-girl skirt with black tights. Her well-formed calves attested to someone who took care of herself. She wore no makeup but for some pale pink lipstick. Her hazel eyes sparkled.

When the ladies came out of the third winery, it was clear that they had made the most of their latest visit. All four were unsteady on their feet and Jan looked close to passing out. Jake helped them all back into the van. This time, Patricia was more forward than ever. She whispered a vulgar suggestion in Jake's ear as he helped her into the van and also placed her hand on his crotch and gave it a squeeze. Things were spiraling out of control. He had planned for five stops, but now it was clear that the fourth would have to be the last today. At least he had Emily to chat with while they waited. At the next and last stop, only three of the ladies got off. Jan was fast asleep now on the floor of the van and feeling no pain.

He turned his attention back to Emily, who remained seated in the front of the van. "So, what do you do in your spare time" asked Jake. "I read a lot," she quickly responded; "and I write a bit as well." "Oh, said Jake, what do you write about." There was that blush again. She hesitated before answering but then looked directly at him and said "I write erotica for women." She watched for his reaction but he seemed unfazed by her answer. "Where do you get your inspiration," he asked. As they both seemed comfortable talking about it, she opened up a bit and responded "mostly, they come from my own fantasies; I have a very active imagination." "Are you writing one now" Jake asked. "Yes, its about a young girl losing her virginity to an older married man." Jake leaned closer to her and put his hand on her arm. She did not withdraw. "Can you tell me a little bit about it?"

She smiled at Jake and began to spin her tale. As she got deeper into the story, she seemed to lose herself in the telling. When she got to her recounting of that "magic moment" when a girl becomes a woman in every meaning of the word, she was flushed and a bit breathless. Her story-telling had a clear physical effect on Jake as well, as he felt his erection pressing against his trousers, forming an all-too-obvious tent in his lap. He continued to stroke her arm as she spoke and moved his other hand to her knee. Again, she did not withdraw. Jake leaned in a bit closer. He looked at her rosy lips and imagined what it would be like to kiss her; indeed, to have her for the first time. "I love your story, he told her and I love the way you tell it. I see you as the girl in the story. Is that the way you imagine it as well?" "Yes," she responded. Jake moved his hand up from her knee to her mid-thigh. It was soft and warm under her silky tights. Again, she did not withdraw. Instead, she parted her legs ever so slightly inviting him to venture further.

Much to Jake's chagrin, they were suddenly interrupted by the sound of the van door sliding open and the three revelers clamoring their way back into their seats. They were thoroughly soused by now and Jake knew that there was no point in going on to the last winery on the tour. He looked at Emily and said, "I guess we better get these ladies home." They both exited the van to assist. Jake and Emily helped each of the ladies into the van with Liz being the last. Liz took Emily's hand and didn't release it, entreating "Come sit with me M." Reluctantly, M climbed in beside Liz and Jake slid the van door shut. The ride back to Vienna was relatively quiet as the wine and warmth of the day conspired to overtake. Three of the women had blissfully nodded off. Liz was still awake however. Her head was nestled against Emily's neck and her arm was around Emily's waist. She was speaking softly into Emily's neck and Jake strained to hear what she was saying.

Jake's eyes kept glancing into the rearview mirror and noticed that Patricia had now roused herself and had moved to sit on the opposite side of Emily. She leaned in, placed her hand on Emily's leg and said "how's our little girl doing?" Emily sat submissively between the two, a resigned expression on her face. Jake surmised that this was not the first time that she had been the center of attention for the two. Liz and Patricia smiled at each other and both glanced at the rearview mirror to check to see if Jake was watching as well. They saw that he had adjusted the mirror to give himself a better view. They seemed pleased.

Patricia turned her attention back to Emily. "Hey baby, it's been a while since we've played. Did you miss your Aunt Patricia and Aunt Liz?" Emily didn't respond, but she let out a little gasp as Patricia's hand found its way up her thigh to her panties. In the meantime, Liz continued to nuzzle Emily's neck and whisper into her ear. Her hand had now found its way to Emily's breast, which Liz was caressing through her sweater and bra. The clear outline of Emily's nipple pressed against the tight fabric. Jake felt his groin stir as he started to harden again. It was difficult to keep an eye on the road and still follow what was going on just behind him, but he did his best. Patricia pulled the loose straps of her tank top off her shoulders and exposed her left breast. She pulled Emily's head toward it and said "suck mommy's tit, M. Mommy wants to feel your warm mouth pulling on her nipple." Emily complied. Her rosy lips opened to take in Patricia's erect nipple and she began to suckle her, and to Patricia's delight, periodically pulled on the nipple ring with her teeth. "That's my girl, cooed Patricia. Make mommy feel good." In the meantime, Patricia's fingers had pushed the cotton fabric to one side of Emily's downy-covered pussy and she was now running her finger up and down Emily's slit, which began to wetten. Emily let out a low moan.

Liz smiled at Patricia and opened her blouse to the waist, exposing her black bra, her large breasts overflowing its cups. Liz looked up at the mirror and locked eyes with Jake as she undid the front clasp and let her breasts fall free. Her nipples were large and engorged, and white droplets of milk readily formed on their tips. Patricia looked at them in appreciation, pulled Emily away from her nipple and redirected her to Liz's.

Liz sighed as Emily began to suckle in earnest. "That's so lovely, my pet. Your warm mouth feels so good. Do you like the taste of Momma's milk M?" Emily nodded slightly and continued her suckling. Patricia dropped to the floor of the van, pushed Emily's skirt up to her waist, and tugged at her panties. Emily raised her hips up from the seat ever so slightly to allow Patricia to pull them down.

Jake readjusted the mirror to get a better view as Patricia pushed Emily's knees apart and buried her face in Emily's pussy. Emily began to moan into Liz's breast as she sucked noisily. Excess milk began to dribble down her chin. Jake was finding it increasingly difficult to concentrate on his driving, but somehow managed to keep the van on the road.

When they were 10 minutes out from Liz's house, Liz pulled her breast away from Emily's lips, righted herself, reattached her bra and buttoned up her blouse. She leaned in to give Emily a deep kiss just as Emily was beginning to cum from Patricia's expert ministrations. Patricia, her face wet and shiny from Emily's juices, looked up at Liz and smiled. Then she too gave Emily a deep kiss. "You taste of sweet nectar, M. I could spend all day between your lovely thighs."

Liz reached over and tapped Jake on the shoulder. "We're dropping Jan and Grace at Jan's House. I'll direct you. And then we're going to my house. Would you like to join us" she asked, knowing his answer well before he gave it. At Jan's house, Jake assisted Jan and Grace to the front door and then returned to the van. Patricia had hopped into the front passenger seat and smiled at him broadly as he climbed in behind the wheel. She had positioned herself with her back to the door; her knees drawn up to her chest. Once Jake was seated, she parted her knees to give him a clear view of her hairy pussy. "Do you prefer your women bare or natural, she asked, as casually, Jake thought, as one might inquire whether you prefer paper or plastic. Jake hesitated for a moment before responding 'paper', er I mean natural." She laughed and said and you would have said natural if I was shaved, right? Caught, he nodded yes, his eyes still fixed on her bush. "Drive, Jake. Let's continue this party at Liz's." Jake glanced over his shoulder. Liz had her arm around Emily and was stroking her hair.

It was a short drive to Liz's. When they arrived, Jake hopped out and went around to the passenger side to open both doors. Patricia swung around in her seat and gave him another bird's eye view of her pussy as she gazed with appreciation at the prominent erection clearly evident in his pants. Jake extended his hand to Emily. She took it, but averted her eyes as she exited. Liz stepped out behind her, took Emily's hand from Jake's and led her to the large ornate double doors of the entrance. Patricia smiled at Jake and said "looks like your lucky day sport. Wanna have some fun?"

Once inside, Liz led the way up the large circular staircase to the master bedroom. The room was decorated in a manner that would please the set director of Gone with the Wind, but Jake didn't much care how it looked, as he was laser-focused on what was unfolding before his eyes. Liz sat on the padded bench at the end of the king-sized canopied bed. Emily stood before her. Liz unfastened Emily's skirt and let it fall to the floor. Next, she unbuttoned her white sweater and draped it over the end of the bed. Emily stood there in her white cotton panties, white bra and bobby socks, looking like a little girl. She quivered a bit as Liz reached up and unfastened her bra, but did not resist. Jake and Patricia watched from across the room. As they did so, Patricia reached down and massaged the bulge in Jake's pants. Finally, Liz placed her hands on Emily's slim hips and slowly pulled her panties down. Liz then pulled Emily close and kissed each of her nipples, taking time to gently nibble each to an erasure-like hardness.

Liz directed Emily to lie on the bed, which she did, spread eagled. Leather straps extending from each of the beds four posts were then used to tie her in place, and a black silk blindfold was placed over her eyes. Liz stepped back to admire her prize, unfastened her floor length skirt and stepped out of it, revealing her long black stockinged legs, garter belt and black thong. Liz turned to look at Jake and Patricia. She pointed to an arm chair and motioned for Jake to sit. Then, she summoned Patricia to the bed with a crook of her finger. She directed Patricia to the head of the bed. "Emily wants to taste you Patty, don't you M? You want to taste some of that sweet pussy, don't you?" Emily was silent. Liz pulled a riding crop out from under a pillow at the end of the bed and snapped it against Emily's left nipple. Emily cried out as Liz repeated her question. "You want to taste that pussy, don't you M?" This time, Emily responded with a weak "yes, mistress". "I can't hear you dear," Liz responded as she snapped the crop against Emily's other nipple. Emily whimpered and said "yes, yes, I want to taste her pussy." "That's better" said Liz as she motioned to Patricia.

Patricia climbed onto the bed, hiked up her miniskirt and slowly lowered her pussy onto Emily's face. "Lick her pussy M. Taste that sweet pussy." Emily did what she was told. She took in Patricia's musky aroma and licked her juices as they began to flow from deep within. Patricia moved her hips rhythmically and began to moan. "That is so good baby. Lick your Aunt Patricia's pussy, lick it good."

Liz mounted the bed now and positioned herself between Emily's spread legs. She produced a small silver bullet-shaped vibrator, poured some lube over it, slowly inserted it in Emily's ass and turned it on. Emily's muted gasp was barely audible under Patricia's undulations. Liz was on all fours now, her face inches from Emily's downy covered lips. Liz placed her hands on Emily's lower abdomen and then let her thumbs travel down to the top of her vagina, where she gently parted the lips to expose the pink, erect nub of Emily's clit. She blew on it gently: then used the tip of her tongue to wet it. Emily's hips jerked up in response. Liz turned the vibrator to its highest setting and then proceeded to flick Emily's clit with the tips of her thumbs. Emily hips bucked again and her moans grew louder.