Lana's Leap Pt. 02: The Lessons Begin

I want to thank all of you who sent me feedback and words of encouragement. I was truly humbled by the positive feedback I received—and all of those who pleaded for another installment of Lana's adventures.. To get a little "H" on my first submission was more than I could have hoped for

For those of you that gave me suggestions for Lana's adventures---sorry—I never know what Lana will do next—I just relay the story.

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Lana could not believe that she had actually come without having a single finger laid on her. Her breathing was shallow, she could feel the flush that always followed an orgasm. Her nipples were solidly erect, and quite visible through the silk blouse. Her cunt was soaked.

Drew stood, leaving Diane curled up on the rug leaning on the leather armchair. Diane told him that aside from Kiko's assistance, she had loaded all of the contact information into his Palm Pilot—along with the local time in Tokyo. Crossing to Lana, Drew motioned for her to stay seated. He gently stroked her head and said "I'm out of town for the next week, Diane will spend that time bringing you up to speed on our little family here. Listen to her, she knows everything about Enigma there is to know." With a small smile and a wave to Diane, he left for the airport.

The room was quiet for a few moments, then Diane stood up. Without any attempt at getting dressed , she looked at Lana. "Well you're still here" she laughed "and if that didn't scare you off nothing will I suppose!" Diane crossed to Drew's desk and picked up her purse. Standing naked in front of a full length mirror, she began to repair her makeup. Turning aside to Lana, she said' "Lets take a few minutes to get freshened up shall we, then I'll buy dinner??" Lana nodded, still taking the last hour in. Lana excused herself and went into the ensuite, where she used the time to clean up, including removing her panties, which were by now completely soaked through. As she stood looking at her reflection in the vanity mirror, it occurred to that not wearing panties didn't seem as unnatural as she once would have thought.

When Lana came out of the ensuite Diane was just slipping into her dress and Lana had a full frontal view of the delicate chain and charm dangling from Diane's bald cunt lips. As Diane finished dressing she took Lana by the hand and said "Lets eat...sex always makes me hungry"

In the restaurant Diane told Lana the story of how she met Drew.

"I come from quite an abusive family situation. My father was an alcoholic and my mother was diagnosed, too late in life, with clinical depression. At 18, I left home, and to support myself, worked as a stripper. The money was great, and I enjoyed the attention, but by the time I was 22 I was burned out and knew that I could not go on too much longer. So I started looking for a "straight' job. The problem was, I had no skills, no training and certainly couldn't tell anybody what I had been doing for the last 4 years.

I answered an ad for a "Personal Assistant", that's where I met Drew. I remember wearing the frumpiest, most boring suit I had for the interview" the blonde laughed "actually the only one I had"

"Anyway when I met Drew, I had the same reaction you did. I was mesmerized by him. We spoke for two hours. I told him what I wanted from life. Strangely, he did not ask me about what I had been doing, or what my qualifications were.

At the end of the two hours he looked at me and said "So you're planning on giving up dancing??"

He had known all along. The year before he had a group of Japanese investors visit the office, and of course, entertained them in the way they expected. So for several nights he sat in the club and remembered me from that time.

I told him my plan and he simply stood up and said "Fine, I'll see you Monday morning. I am not exactly sure what your job description will entail, we'll make it up as we go along."

Finally, he smiled and said "Diane, you look so incredibly uncomfortable in that suit. Please don't wear it again, I think you're more the short skirt and heels kind of girl."

"For the next six months he took the time to teach me all about the business, and gave me a lot more responsibility than perhaps I should have had. But I was determined not to let him down. He trusted me and never once made a pass. Six months almost to the day, things changed."

"We were working on a huge contract. Winning that job would take the company to a whole new level. Drew had been working night and day putting the deal together. The nature of the deal was such that I couldn't contribute much, other than eliminating any other distractions from his life."

Diane looked at Lana conspiratorially "Plus, I have to admit, the fact that he was ignoring me sexually, was beginning to get to me. After all, as an ex-stripper I was used to men falling all over me. Drew had all but ignored me. I made a point always to dress the way he liked, and made it obvious that I was receptive to his advances. Still nothing."

Diane dropped her voice to the honey dipped, sexual tone Lana had learned to expect. "So the next morning I dressed to kill; semi sheer silk blouse, no bra; tiny, pleated skirt that barely covered my pussy; spike heels, the works. That entire day I made quite the spectacle of myself, continually dropping files so I could bend over and pick them up in front of Drew. When I came into his office, which was tiny in those days, I would cross and uncross my legs giving him the complete show. Sharon Stone had nothing on me!

As the day came to a close I walked into his office. He was standing leaning against the front of his desk reading a file. Determined to get him to acknowledge me, and help him alleviate some stress I approached him. Without speaking, I started unbuttoning his shirt, worked my way down to his fly, released that beautiful thick cock and gave him the blowjob of the century!"

The two blondes giggled like schoolgirls. It was clear they were becoming fast friends.

"Since that day Drew has not only taught me about the business, but also about what his pleasures and preferences are. It has been a remarkable journey. One I hope you'll enjoy as much as I have. I'll teach you as much as I can."

Lana looked thoughtfully at Diane "If you had told me three days ago what was in store for me in the weeks and months ahead, I would have thought you were crazy. But right now, right here, this just feels right. If you'll take it slowly, I'll do the best I can. "

Diane replied "You have a deal. The boss is out of town for all of next week, so that gives us a bit of a head start. First things first. Monday morning we're going to hit the stores and get you a brand new wardrobe! I'll pick you up at 9 sharp."

By 8:45 Monday morning Lana was waiting downstairs in her apartment lobby. At 9 sharp a candy apple red Boxter convertible with the top down, came roaring up the driveway with Diane at the wheel. Diane was dressed in a tight leather mini skirt with a matching short leather jacket. The skirt was so short that Diane's lacy stocking tops were clearly visible as she sat in the bucket seat. The outfit was, as always complete with heels and jewellery

Minutes later they were on their way to some of the cities most exclusive boutiques. It became clear to Lana that Diane was well known in most of them. First stop was Ivy, an upscale lingerie store. There, they were welcomed by Irma, the proprietor, a stunning younger Sophia Loren lookalike. Diane and Irma kissed and hugged. Lana noticed that the kissing and hugging was not the usual air kissing one would expect, but rather had a sexual overtone to it. In fact, Irma's hand lingered on Diane's leather clad ass. Irma then approached Lana and began to look her over from head to toe.

"Well Diane she is a beauty, and what a luscious set of curves! I can see why you would choose her as your replacement. I'm sure Drew is delighted. I've taken the liberty of laying out a few basics. Come now Lana , off with those clothes! Lana looked at Diane and the blonde nodded. Lana self-consciously stripped down to her bra and panties. Irma laughed "Oh that will never do...off... with the lot!" Soon she was stark naked.

Irma then handed Diane a series of bras, garter belts, bustiers and other assorted pieces. Diane took her time helping Lana try the items on and Irma helped ensure a proper fit. Several times during the fitting process, Lana felt Irma's hands caress her in an obviously sexual manner. Diane would laughingly scold her. Among the items were a set, in various colours, of demi bra's which gave Lana pronounced cleavage but left her now erect nipples bare. Together with a matching garter belt and stockings, Lana felt herself become moist at the reflection in the full-length mirror

With a flash of an American Express card, Diane and Lana were off to find some outerwear. Over the next couple of hours the two women bought a collection of skirts, dresses, tops and blouses. All of their selections were provocative and revealing, and with each purchase Diane would describe to Lana what Drew would like about each particular purchase. Slowly, the young blonde started to understand her boss's preferences. After a light lunch, shoes were the order of the afternoon.

Lana noticed that sometimes, Diane would purchase two of a particular piece of clothing. When asked, Diane told Lana that she always kept some clothing at the lake house and at Drews city home. "In case you don't get home the night before." she winked. Lana blushed. "Which reminds me" Diane snapped her fingers. We need to pick you out a couple of bikini's" When Lana replied that she had a couple all ready Diane quickly explained "Not the kind the Boss likes"

Next stop was a store specializing in tropical wear. Lana knew the store, she had shopped there herself. Diane had Lana try on several thong bottoms, but unlike the earlier purchases did not spend so much time on the fit of the tops. For the first time Lana found herself picking out bikini's based on how revealing they were, rather than how modest. In fact she tried on several wearing a pair of high-heeled sandals Diane had selected. Diane noticed how quickly the young blonde was becoming aware of her body.

At the end of the day, the girls piled an overly large collection of purchases into the tiny trunk of the sports car and Diane dropped Lana off at the apartment, with instructions on the morning. That night Lana spent several hours trying on each piece of clothing. By late evening her cunt was soaked and she had fingered herself to several orgasms from her fantasies. Drew Rice was the central figure in all of them. In the last two she imagined Diane Crawley watching quietly from the sidelines.

Overnight a midsummer heat wave moved into the city. By 9 a.m. the next morning, the heat along with record breaking humidity, was oppressive. When Diane pulled up to Lana's building the young blonde was waiting. Lana looked stunning in one of her new outfits, a red and white patterned sundress, which ended 5 inches above her knees. The dress was low cut, displaying Lana's cleavage, which had been accentuated by a pushup bra. A pair of white strappy sandals showed off Lana's tanned, bare, legs.

Diane whistled a wolf whistle. "Now that's more like it, little one! You look good enough to eat" Lana felt a strange but pleasant twinge in the pit of her stomach at Diane's compliment. As Lana slid into the leather bucket seat she felt the cool leather on the backs of her thighs and her ass as the dress road up. "Today" announced Diane as she slid her hand over and patted Lana on the thigh " we're off to the spa, then we're going to spend the rest of the day by the pool at Drews house. I brought the extra bikinis from yesterday. We can go over some office procedures just as easily from there as anywhere, I have my laptop."

At the spa Lana had her hair trimmed, her makeup made over, a massage, a manicure and a pedicure. Lana looked with amazement at her new nails; long and red. "Just the way the Boss likes them" Diane confirmed. The most memorable part of the spa visit was when Diane and Lana had a Brazilian wax. For Diane it was second nature, for Lana having herself exposed that way for anybody other than her doctor was a little unnerving, especially given the casual conversation that took place during the process. Diane had the attendant leave a small tuft of hair just above Lana's now bald slit. Lana found out that the company had an account with the spa and could access it anytime she felt the need.

Drew Rice's house was nothing like Lana expected. The house and property were situated a 10 minute drive from the office on a cul de sac that ended on a ravine. The house was situated such that it had no adjoining neighbours. The property itself was surrounded by 10 foot tall, old thickly grown hedges, which added to the private nature of the house. The house itself was smaller than Lana expected. When she mentioned this Diane replied "Drew is personally a very private man. His style is luxurious but understated. The flash and glitz of the office is more to impress clients than Drews personal style."

As the car came to a stop Diane turned to Lana "Gosh, it is hot. Lets get into our bikini's first...then we can get a cold glass of wine and a snack. Lana smiled and readily agreed. Inside, the house was simply but luxuriously appointed. The large kitchen opened, through French doors, onto a patio surrounding a small pool. Diane directed Lana to "her" room "although"she said with some sadness "I guess after this week its now technically your room"

Lana hugged the older woman and said, "I'd like you to always consider this your room. Anytime." Diane brightened and suddenly kissed the young blond directly on the mouth. Letting the kiss linger she said, "I knew I had made the right choice. Now lets get changed."

Lana slipped into a bright fire engine red thong bikini that Diane had picked out the previous day. As she tied the brief top around her neck she saw Diane looking at her with a quizzical expression. Lana stopped and said, "Is there something wrong?" Diane laughingly replied "the Boss likes an all over tan, except for the bottom. It's a particular preference of his. He likes me tanned totally on top so that a low-cut dress doesn't show lines..but likes the look of the white thong tan lines on the bottom. So...I don't wear the top!".

"And so... "Lana laughingly replied and tossing the top at Diane "neither...will I!!"

The two women grabbed cold bottle of white wine, and after filling up generous portions, took their glasses on a tour of the house. Last stop was Drews room. Like the spare room, it was very tastefully decorated with a huge custom-made bed. Like the spare room it had its own small terrace and an absolutely palatial bathroom/jacuzzi/shower enclosure.

Diane said "It's much too hot to work, lets play a little hooky. I'll grab the wine and meet you by the pool" Lana walked out to the pool, and, while passing through the French doors she caught a reflection of herself. She stopped and studied the reflection. She saw a tall, curvy, beautiful...and sexy woman. Lana looked at her figure accentuated by the high-heeled sandals and the thong bottom. With her trimmed hair, new makeup and long red nails she was a striking young woman. Lana was reminded of the first afternoon she tried on T's present, and the immediate aftermath. In a repeat of that event Lana casually tugged on her nipples, but this time she kept her eyes open. Lana only stopped when she heard Diane's heels clicking across the tiled kitchen floor.

Diane saw Lana looking at her reflection. Walking up behind Lana, Diane tucked herself against Lana's bare back and placed her right hand on Lana's hip. Lana could feel Diane's perky breasts and hard nipples press against her. Diane looked at the young woman's reflection, and laying her chin on Lana's shoulder remarked quietly "You certainly are little one, you certainly are." The older blonde terminated the moment by placing a deep kiss at the base of Lana's neck. The two women moved out to the pool deck.

The pool deck, like everything else was tastefully appointed. Lana and Diane sat together on a double size chaise lounge. Over the next hour they finished off the wine while talking about Drew and the company.

Soon Diane turned to Lana and said "While Drew likes you tanned, I don't think he'd be very happy to see you sunburned. Turn over young lady and let me put some lotion on you.

Lana followed Diane instructions. Diane took a generous portion of lotion in her hands, and slowly applied it to Lana's bare back. Lana sighed "Mmmmm, that feels almost as good as the massage this morning" Diane continued her ministrations. As she coated Lana's back her hands moved lower to the high cut waist band of the tiny thong bottom. Continuing her applications the older woman's long fingers moved over the waistband and directly onto Lana firm young ass cheeks. The young blonde started and Diane said "Is that a problem??" "No...I was just surprised...it actually.. feels.. good. Diane applied more lotion and moved off Lana's ass and onto her thighs. As her hands slid towards the inside of the thighs , Diane detected an imperceptible shift of Lana's weight, spreading her legs slightly and putting more pressure on her mound.

Suddenly Diane stopped "Awwww" Lana sighed "finished already?"

"No" Diane replied in her honey dripped tone "Now you have to turn over so that I can do your front. You would like me to do that wouldn't you??" Diane continued as she ran a long red nail down Lana's lower back"

Well...I guess its important that I not burn..."Lana turned over

"Good, now close your eyes and enjoy. It was obvious that Lana's nipples were erect and Diane could glimpse a small patch of moisture dotting the crotch of her thong. Diane applied more lotion purposely avoiding Lana's full breasts. As she moved lower on Lana's stomach the young blonde started to squirm slightly. "Ohhhh that feels so good" moaned the young woman softly, her legs spreading..

Diane knew the time was right. Given the sexually infused last few days, combined with the fact that Lana had not had any sexual connection for well over a year, Diane knew her awakening was due.

Slowly Diane leaned over and ran her tongue over Lana's nipple. The young blonde moaned "Ohhh Diane I shouldn't...we...its not..." Diane lifted her tongue off Lana's nipple and cupped both breasts, gently tugging both nipples. "Shhhh... little one, just lie back"

Diane caressed Lana's nipples with her fingers and with her mouth. Slowly she moved lower down Lana's flat belly, leaving a trail of moist kisses. By now the young blonde was arching her back and lifting her hips off the chaise lounge. Finally Diane slid her long fingers under the waistband of the thong and began to peel it over Lana's hips. Diane smiled when she saw Lana adjust her hips so that the small piece of clothing could be removed easily. Now Lana was naked, her legs spread. When Diane ran her fingers over the young blonde's bald cunt, she was amazed at how wet Lana was. Like a cat, Diane gathered up some of the cream and lifted her fingers to her mouth.

Diane continued her trail of kisses until she was at the top of Lana's slit. Slowly parting Lana lips she allowed a surprisingly large clit to become exposed, and gently licked the small bud.

Lana's response was instantaneous "OHHHHHHHHHHHHH" she moaned as her hips spasmed around Diane's head. Diane let Lana's clit slip out of her lips and continued to lick and suck Lana's young cunt. While attending to Lana's cunt, Diane looked up the length of the now loudly moaning young woman and watched as Lana, eyes still closed, tugged and pinched both nipples.

Within minutes, Diane felt Lana's hip movements increase, lifting and thrusting toward Diane's mouth. Soon the movements became more violent and Diane felt Lana reach down and grab Diane's head , holding her mouth directly onto her clit. Lana let out one, long, rising, moan as her back arched clear off the chaise lounge. Lana held her body rigid like that for several moments finally collapsing back onto the cushion. Diane crawled up beside Lana and gently stroked her hair. Lana was sobbing "When Diane asked the problem, Lana replied smiling between sobs "No, no, no, nothings wrong. I just never, ever came like that. I never knew...it could be...so..." her voice trailed off .