This is a work of fiction. None of these characters ever existed. If you are offended by lesbian sexual relationships between older and younger women, please read no further. (FF, Lesbian Beginnings)
18-year old Tiffany Madison was excited to be attending UCLA in the fall. Tiffany was an excellent student, and planned to major in pre-law.
Blessed with a good brain, but few financial means, Tiffany was understandably hesitant to incur deep financial debt from student loans. Her single-mother had passed away from cancer at a young age, and Tiffany had been living with her grandmother since the age of 10.
A loving woman, her grandmother was living on a fixed income in an unincorporated part of Clark County, Nevada, and was simply in no position to help Tiffany with her college expenses.
Some Pell Grant money would certainly be available to Tiffany, but she knew that the average cost for an out of state student, with housing, food, books, tuition, etc. would be in excess of $60,000 per year. The Pell Grant money would certainly be helpful, but even with that and a part-time job, it wouldn't cover the "nut."
Worse for Tiffany, she was cursed with extravagant tastes. Her 23-year old construction worker boyfriend had taken her to expensive dinners at the casinos, and had been generous with her in purchasing clothes, but Tiffany had no plans to return to that dusty part of Nevada, and was determined to leave that lifestyle and that boyfriend behind her.
A beautiful girl, Tiffany had gorgeous shoulder-length blonde hair, and was a perfectly proportioned 5'6". With the bubble-butt of a cheerleader or gymnast, Tiffany never had the time or money for extra-curricular activities. All of the boys in high school were keen to date her, Translation: Have sex with her, but she had no time for high school boys, or anyone else in her school. They couldn't provide her with the things she wanted... or felt that she needed, so she remained a mysterious loner among her peers.
Tiffany had read online about "Sugar Daddies," but was grossed out by the thought of being a fuck-toy for some sweaty, hairy old man who would always be pawing away, or laying on top of her grunting. And no matter how careful she was, there was always the possibility of pregnancy. And that would spoil all of her plans for her future.
So, what to do? Tiffany began searching the internet for upscale waitress positions at some fashionable West side restaurants in L.A. Perhaps being as pretty as she was could mean a lot of money in tips?
She was later told by a friend who was a cocktail waitress at one of the casinos that while Tiffany was indeed beautiful, she had to remember that every would-be model and actress in Los Angeles had the same plan. She would have to hustle for her tips, and put in long hours.
"You need a 'Sugar Mama,'" her friend said. "A what?" asked Tiffany.
Tiffany's friend explained that there were sites on the internet where young, pretty girls could meet older, successful women who would take care of them. It was the same concept as a "Sugar Daddy," but the women tended to be kinder and gentler.
Tiffany had never been with a woman before, but could think of few other immediate options. Payments would need to be made soon. Tiffany's friend sent her a link to a website in Los Angeles. It was sort of a lesbian older and younger dating site. It was known that long-term relationships had been struck up by clients to the site.
Tiffany downloaded an appropriate picture, and filled out the online questionnaire. Only the older women were required to pay to use the service, and the fee was by no means inexpensive. The service was meant to be exclusive, and not a site for suburban housewives to troll for some young trim.
The application for Tiffany to join the site was unsurprisingly accepted within 24 hours. Throughout the week Tiffany received several inquiries for dates for when she finally moved to Los Angeles. This was not a prostitution site. Tiffany was free to date or not date anyone she wished who inquired.
Some of the ladies who replied were just too old, and others were simply unattractive. Tiffany eventually whittled it down to three women that she would like to meet. All appeared to be in their 40's, and by their pictures were seemingly well off, and well put together.
Tiffany would be moving into her UCLA dorm in mid-August, and made arrangements to meet with each woman soon after.
Date number one didn't go so well. The woman was the CEO of a large fashion-based organization, had no desire for small talk, and was very handsy. She was only interested in fucking the pretty, 18-year old.
Date number two was a nicer person who owned a very successful CPA firm. Like many accountants, her conversation was awkward. Her online photo appeared to be a few years old, and she had clearly dolled herself up for the photograph. Knowing what some of her duties as a "Sugar Baby" would entail, Tiffany just couldn't imagine herself having sex with the frumpy accountant, regardless of how much money she might have.
Tiffany had always been more interested in date number three: Ms. Mary Ellis was the only female partner in a top-tier Beverly Hills law firm. As Tiffany was interested in pursuing the law herself, she was interested in meeting Ms. Ellis, and at least gleaning some information about her career.
The two agreed to meet on a Friday night at "The Palm," which is one of the finest restaurants in Beverly Hills. Mary was already sitting at the bar enjoying a cocktail when Tiffany showed up promptly at the designated meeting time of 7:30 p.m. "Punctual. A good sign," Mary thought.
Knowing that Tiffany was under 21, Mary nodded to the bartender, who nodded to the hostess, and the pair were seated immediately. It was clear that Mary was a well-known customer. The bartender brought Mary's drink to the table himself.
As has been explained, Tiffany didn't have a lot of possessions, but she did own a couple of very nice dresses. She was wearing a form-fitting little black dress that showed her best features in a way that other girls would envy, without looking the least bit trampy. The bottom on the dress was short... but not too short.
Tiffany had been meticulous with her makeup. She had applied just enough to look more grown up... but not too much. She looked beautiful, and not the least bit slutty.
Mary had come straight from the office, and wore a grey designer business suit. Her pretty brown hair was pulled up in a business bun, and she wore a pair of very expensive black Jimmy Choo heels.
Mary could tell by their conversation that Tiffany was intelligent and well-spoken. Mary knew how hard it was to get into UCLA these days, and Tiffany didn't hesitate in answering questions about her GPA and SAT scores. It also didn't hurt that Tiffany was interested in the law.
Over two hours had flown by when the check was presented to Mary. Tiffany had proven to be not only gorgeous, but intelligent and interesting.
Tiffany made it a point to not appear to be overly eager when Mary invited her over to her house to talk some more. Mary's eyes were transfixed on Tiffany's gorgeous ass as they exited from the dark restaurant.
The drive from the restaurant was a short one. Mary drove her silver 5-Series BMW into the gated driveway of her beautiful two-story Beverly Hills home.
The house was beautifully furnished, but looked more like a model home, not like a home that someone actually lived in. In truth, Mary did little more than sleep there, and almost never entertained.
Mary made two cups of coffee, and then sat next to the teen on the couch. Putting an arm around Tiffany's shoulder, she began to ask her about her lesbian experience. Tiffany admitted that there was not much, and tried to pass that off as being due to her youth and rural background.
Trying to think of an older woman that she was attracted to, she said that she thought Jennifer Anniston had great breasts. Mary chuckled. She explained that she was an entertainment lawyer, and was on a first name basis with virtually every celebrity in Hollywood, and Jennifer Anniston did indeed have nice breasts.
Looking deeply into Tiffany's eyes to see if she was a "star-fucker," the discussion of Hollywood celebrities didn't seem to spark any particular interest in the pretty teen. Tiffany impressed Mary with her scholastic seriousness, and that she wasn't just another aspiring actress, fresh off the bus from Kansas.
Knowing that she might blow it, but not having the time to invest in twenty dates to woo and win Tiffany, Mary brought Tiffany close for a kiss. Tiffany reciprocated nicely, so Mary upped the ante by feeling one of Tiffany's breasts over the fabric of her dress.
Tiffany knew that if she was going to go through with her "Sugar Baby" plan, it was now or never. She thought Mary was genuinely attractive, and very nice. She could imagine having a relationship with Mary, assuming that their were fringe benefits as part of the deal.
But could Tiffany eat pussy? She would soon find out.
Tiffany got up from the couch, and Mary thought to herself that she had perhaps gone too far, too fast. But rather than heading for the door, Tiffany dropped her little black dress to the floor, and stared down at Mary with a little smile.
The 18-year old's body was flawless. Her boobs were pink and perky 34-B's, although Tiffany rarely wore bras. Her blonde hair radiated from her tan skin. Wearing only a small black thong, Tiffany kept her heels on knowing that they would make her legs appear longer and leaner.
"This is a smart cookie," Mary thought to herself, and opened her arms to welcome Tiffany back to the couch.
As Tiffany sat, Mary had her mouth all over Tiffany's young tits. Tiffany closed her eyes, hoping to just get through this first lesbian experience. Mary gently kissed and licked the teen's breasts and nipples. It felt warm and nice, Tiffany was surprised to learn.
For the time being, Mary confined her hands above Tiffany's waist. Kissing the girl, Mary lovingly ran her hands over Tiffany's arms and fingered between her breasts.
Still fully dressed, Mary invited Tiffany to continue in her bedroom. Mary stood up and extended her hand to the teen. The pair walked hand-in-hand to the second floor bedroom.
Mary couldn't see it, but Tiffany's bubble-butt, held in the back by only the tiny strip of her black thong, jiggled sexily up the stairs.
Mary's bedroom appeared to be a palace to Tiffany. Mainly done in shades of white, expensive paintings hung on her walls. A large, canopied bed dominated the room.
Tiffany sat on the edge of the bed surveying the room in wonder. Mary began to meticulously undress. She believed in orderliness, and hung up her suit carefully in the closet.
Mary was a full-figured woman, but not the least bit fat. She was known to go to the gym as early as 5:00 in the morning. She had a firm, athletic ass, sturdy legs, and breasts that were 40-D's. Now stripped down to elegant flesh-colored silk bra and panties, Tiffany was surprised by how Mary had somehow been able to hide her big tits in that business suit.
Sensing Tiffany's nervousness and inexperience, Mary sat next to the teen and stroked her hair, while whispering reassuring words.
Mary reached for Tiffany's hand, and moved it onto her bra and exposed cleavage. Mary chuckled and pointed it out when Tiffany began to smile.
Tiffany was invited to unfasten and remove Mary's bra. Tiffany audibly gasped as Mary's large breasts were revealed. Her areolas were a light chocolate brown, and were the size of 50-cent pieces. Her nipples were already erect.
Mary helped position the teen on the bed, and began to kiss her and stroke her breasts. Mary then lowered one of her large breasts over the teen's mouth, and Tiffany began to suck. Her intensity deepened with the new experience.
Tiffany was relieved that the experience was not nearly as bad as she had feared. In fact, most of it was quite enjoyable.
Just as Tiffany thought that, she noticed that the now-nude Mary was hovering between her legs, and kissing her tiny black panties.
A lesbian virgin, Tiffany knew that she was about to be eaten out by the powerful lawyer. She had had sex with her construction worker boyfriend, but it was all so quick and slam bam! She really hadn't enjoyed it much it all. But she did enjoy the presents that he gave her.
Tiffany tensed up, closed her eyes, and gritted her teeth as she felt Mary removing her panties. Mary tenderly kissed and licked around Tiffany's inner thighs, and patted Tiffany's bald pussy.
Tiffany had trimmed and shaved her pubic area for the first time the night before. She felt that a shaved pussy would make her look more sophisticated, like the runway models she had seen.
Mary was taking her time. She patted and played with Tiffany's pussy with her hand. Tiffany reacted to the touches, but Mary wasn't quite sure if it was fear or pleasure.
Ever so carefully, Mary's tongue entered Tiffany's pussy. Tiffany's old boyfriend back in Nevada had never bothered to go down on her even once, so this would be Tiffany's first "taste" of oral sex.
Still tense, Tiffany could feel sense release melting from her body as Mary opened up a new world that Tiffany had never experienced before. Initially trying to fight the pleasure, Tiffany's body spasmed as she exploded in orgasm. Her legs were trembling involuntarily.
Trying to catch her breath, Tiffany asked, "What the heck was that?" Mary explained that Tiffany had just experienced her very first orgasm. Tiffany sat up to see what Mary was doing between her legs.
As Mary continued to lick her pussy, Tiffany involuntarily arched her back and tilted her head back in ecstasy. Tiffany imagined her eyeballs rolling to the back of her head in pleasure.
Flipping the teen over, Mary began to kiss Tiffany's butt cheeks, which caused Tiffany to giggle. Undeterred, Mary climbed on top of the teen and began humping her. Mary's big breasts slapped across Tiffany's back, and she reached under the teen to latch on to her breasts and she pounded the Tiffany with her crotch.
As the lovemaking continued, Mary straddled her pussy over Tiffany's face. If Tiffany was unsure if she could eat pussy, she was now faced with it... literally. As she wrapped her hands around Mary's waist and ass, she slowly, tentatively began to lick, as if checking to see if it was spoiled or radioactive.
Tiffany continued to lick, and came to the stunning revelation of why her relationships with boys, going back to junior high, seemed so empty and unfulfilling: Tiffany was a lesbian, and didn't know it until that night.
With that discovery, Tiffany let her lesbian inhibitions go.
The naked pair woke up the next morning in Mary's bed. Tiffany's hand was over Mary's body, cupping one of Mary's large breasts. Mary leaned over to kiss the teen, and it was happily reciprocated. Tiffany felt reborn.
Mary reached into a nearby drawer, and pulled out a small light blue box and presented it to Tiffany. Like her name, it was a beautiful Tiffany watch.
Mary looked deep into Tiffany's eyes. "I had a good feeling about you when we exchanged messages online. We have similar interests, and I admire how sincere you are about your education.
"I would like you to move in just as soon as you can. You will have free access to the house, and I will provide you with a car so that you can get to and from UCLA.
"I want you to know that you're not a prisoner here. You can leave whenever you want. By the same token, I can ask you to leave if I feel that things aren't going well.
"Any presents that I give, like the watch, will be yours. However, I would need to take the car back. Trust me, I think this is going to be great for both of us.
"Are you in?" Mary asked. Tiffany smiled and nodded.
Mary pushed the bedclothes to one side, and began to devour Tiffany's pussy. Tiffany tenderly stroked Mary's brown hair.
Next Part... Moving In
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