Three Sisters: A Crazy Lesbian Orgy

Summary: Jasmine and her two sisters cross every taboo line.

Note 1: This is a Valentine's Day 2014 Contest entry...so please vote.

Note 2: This story came about one night when trying to console my sister after a rough break-up. A lot of good food, and exotic wine and the conversation got very, very personal. The dialogue at the restaurant in this story is mostly authentic as best as I could recall it a few days later...the rest of the story as well as the flirtation with the waitress is, of course, fiction.

Note 3: Thanks to Robert, goamz86, Wayne, SimonBrisco and MAB7991 for editing this special story (well special to me).

3 Sisters: A Crazy Lesbian Orgy

Like most great things in life, it happened rather unexpectedly.

Jill, my oldest sister, had caught her boyfriend of over ten years getting head from another guy. Things had not been going well for the past year between Jill and her long time boyfriend, Adam, but this was not something any of us would have ever expected. Adam was a man's man, and apparently that meant having sex with men.

To make matters worse, Jill had caught him just a few days before Valentine's Day. Thus we decided to have a special sister's night out on Valentine's Day. Caroline, the middle child, agreed as her husband was out of town working and, not surprisingly, my husband, Howard, had no problem not going out to an overpriced dinner and instead staying home to watch hockey.

Before I continue this crazy story, I should highlight that although Jill is the oldest and I the youngest, only four years separate all three of us. Mom was a baby making machine, producing Jill, and then, sixteen months later, Caroline and, lastly adorable ol' me just fifteen months after that.

Although we were sisters, I should also note that we all looked very, very different. Jill got the breasts both Caroline and I had wished we had throughout high school and college, but less so now, as we don't have to carry them around all day at work. Jill was also the only blonde, taking after dad, with blue eyes that drew men at will and yet she was the shortest of us at 4'11. And although she wasn't fat, she was big-boned, again like father, and that had always been her insecurity issue. In fact, she is in great shape for 43. That said, usually she was the glue that kept our family together...the one who always had it going right. She was structured, a psychologist not surprisingly, and the one out of us three who dressed for comfort rather than fashion.

Caroline, on the other hand, was Jill's polar opposite. The rebel of the family since high school, she willingly admits that from sixteen to thirty were her 'slut years' (she won't give an official number, but she does admit whatever number we guesstimate...we should probably double that). She loves tattoos, is a brunette with hazel eyes, annoyingly slim, married to a rich banker (we call her 'trophy' to ruffle her feathers, even though she has a job as a nurse and makes very good money) and always wears the latest and hippest fashions. Her insecurity issue is that she never got breasts. I mean, she has them in the most remote sense of the word, but even though she has long legs, a perfect body and tight ass (she works out every day...it would be nice to have a pool in my backyard too), she fixates on her tiny almost non-existent breasts. She has contemplated getting breast implants for years, but so far we have managed to convince her not to.

Then there is me. I am the plain Jane of the group. The shy one; the boring one; the one with kids. Jill didn't have any because Adam didn't want any, and Caroline didn't have any because she learned, after spending a lot of money, that she was physically unable to. I, on the other hand, had three and they fucked up my body good. Besides having thyroid issues, which makes reaching orgasm twice as much work, I have never lost the baby weight, especially in my ass. I have green eyes, brown hair (with tinges of grey if I don't dye it) and an adorable smile. My breasts are an average 34b cup, enough to showcase in the right outfit, but not enough to get much attention. My husband is a leg man and thus doesn't focus much on my breasts. He's more interested in my very toned legs...especially in nylons, which he expects me to wear every day.

My job is very stressful. I am a high school teacher and have to be mentally strong all day, and therefore I like to just let go at home...thus I am very submissive to my husband. Oh, and my biggest secret is that I write erotica on a website called Literotica and not a single one of my friends or family know. My writing over the past three years has covered a variety of genres and themes, with the most common being lesbian and incest. That said, I write fantasy and, truthfully, never considered seriously crossing the line.

Now that you know a little about us, let me get on with my tale. This story is actually about how the three of us crossed a line that we never even considered crossing until that fateful night that I am about to describe.

Caroline had insisted we all get dolled up for our 'Valentine's No Men' evening as she booked us a table at the most expensive restaurant in town. Again, it must be nice to have connections and money. Caroline, being Caroline, insisted we meet her Thursday evening to go clothes shopping...her treat. By the end of the evening, each of us had a dress that you would wear purely to draw attention, with matching heels and new lace undies. It cost over two thousand dollars but Caroline shrugged it off by insisting money is made to be spent. Jill joked it wasn't her money, to which Caroline countered, "All the more reason to spend it."

On Friday, Caroline again insisted we meet right after work, this time at her favourite hair salon where we got our hair, nails and make-up done. By the time we arrived at the restaurant, we had already polished off a bottle of wine and looked like three elegant cougars on the prowl. I was in a red dress, with a black belt that showcased every curve I had (the good and bad), with matching four inch heels and beige pantyhose that really did accentuate by best asset, my legs.

Jill was in a multi-coloured dress that was longer than mine but tighter on the top, making her breasts the obvious attention spot for our waiter or waitress.

Caroline, of course, was in a gold gown, with a side slit that showed off a ton of leg and the fact she was wearing thigh high stockings rather than pantyhose.

I asked, as we drank cocktails at the bar while waiting for our table to be seated, "Aren't thigh highs a little provocative for such an outfit?"

"Cameron insists I only wear thigh highs as it gives him quicker access to the goods." She shrugged, adding, "His words not mine."

I often wore thigh highs for Howard for the exact same reason, but I wasn't one to openly share my sex life. Instead I shrugged, "Whatever floats your boat."

Jill joined in, "I never wear pantyhose, I hate them."

Caroline said, "They are like make-up, or heels, just another way to enhance your look."

"They are uncomfortable," Jill said, before adding, "plus I always get runs in them."

"First, that is why I wear thigh highs, they are very comfortable. Second, if you buy quality hosiery, like Wellford's, they last forever and you feel like you are wearing silk...because you are."

"If you say so," Jill shrugged.

"I am so making you try some on when we get back to my place!" Caroline said.

Jill agreed, because it is always easier to agree with Caroline, "Whatever you say."

Caroline smiled, "Excellent, you are finally learning."

"Just trying to shut you up," Jill countered.

Caroline laughed, "I just aim to please."

Jill quipped, "That is why you were so popular in high school."

"And college," I added.

"Jealousy," Caroline said, all sing-song, knowing it was true and also letting us know she was fine with her slutty past.

A cute host led us to our table and it was obvious he was overwhelmed by the three of us. He stared at Jill's cleavage, my legs and Caroline's everything.

Once we were seated, Caroline asked Jill, "Are you ready to jump on the horse again?"

"God no!" Jill said dramatically, "Men are currently off the menu."

"Does that mean you are switching sides?" Caroline asked playfully.

Jill shrugged, finishing her drink. "It couldn't be any worse than being with a man."

"It's not worse, it's just different," Caroline revealed, surprising both of us.

"You have dyked out?" Jill asked, surprised.

Just before Caroline could reply, our waitress, a cute blonde in her early twenties, arrived at our table.

"Hi, my name is Emma and I will be your server for the evening," she greeted.

"Good evening, Emma," Caroline replied, obnoxiously like she always is.

"Good evening, ma'am," Emma replied politely.

"Ma'am," Caroline gasped as if she had been greatly offended. "I am no ma'am!"

The poor girl went red, obviously not used to such a response. She stammered, "S-s-sorry."

Caroline smiled, "I'm Caroline or Goddess of Beauty, you may choose."

Emma smiled, quickly playing along. "Can I get the Goddess of Beauty something to drink to start?"

"Yes, a bottle of your best wine," Caroline answered.

"Of course, will that be all?" Emma asked.

"For now," Caroline smiled warmly.

Emma left and Jill scolded, "That was a bit much."

Caroline smiled, "Just warming her up for you."

"She is half my age," Jill said, flabbergasted by the suggestion.

"The young ones are usually the most eager to please, or at least the easiest to train. Well, them and married women with husbands who neglect their sexual needs, of course," Caroline shrugged.

I asked, trying to be crude, "Have you eaten cunt since you got married?"

"Is the sky blue?" she answered.

I joked, today being a cloudy miserable day, "Not today."

"Fine, are Jill's tits huge?" Caroline rephrased.

Jill quipped, "Especially in this ludicrously tight dress you made me wear."

"You're getting laid tonight. If not by some college stud with a big cock who can get it up five times, by some sweet lesbian or bisexual," Caroline boldly predicted.

"How can you tell if a girl is a lesbian?" I asked.

"That is hard sometimes, but almost all girls, especially younger ones like our Emma there, are bisexual...it is the new 'in' thing," Caroline explained.

"It's 'in' to suck cock and eat cunt?" I asked.

Caroline laughed, "Where did that nasty mouth of yours come from?"

"I learned from the best," I shrugged.

"We will see if that is true," Caroline said, her tone ominous in a way I couldn't explain. "And trust me, it is 'in' to be bisexual."

"If you say so," I said, the conversation getting a bit uncomfortable. I had fantasized about women for the past three years: mostly younger girls who I fantasized would seduce me and make me their pet teacher. On occasion I would see a black woman and get wet wondering what it would be like to submit to a black woman or a black man for that matter. Yet, that was the reality of fantasy...it was just fantasy.

The thoughts of making my fantasy a reality really changed when a new teacher, Amber Addison, started at school. She was young, fun, beautiful, black, and seemed to flirt with me. She told me how good I looked most days, squeezed my shoulder and arm on many occasions and even put her hand on my leg at the bar during one of the Friday night happy hours. Although nothing had happened, she had definitely triggered my curiosity. My masturbation fantasies of late had not been of my husband, or a gangbang (another secret fantasy of mine) but of Amber seducing me and making me hers.

"Oh my God, Jasmine, you have a crush on someone," Caroline accused.

"I do not," I quickly refuted, even as I felt the heat in my cheeks rising.

"Have you already eaten pussy?" Caroline asked.

Thankfully, I was saved by the waitress who brought us some stupidly expensive wine which she poured for each of us. As she leaned forward, I noticed her breasts were quite voluptuous as well, although not as big as Jill's. After she poured the wine, she also took our appetizer orders.

Once she was gone, Caroline repeated her question, although with a little less frankness. "Is this just a crush or has it already become something more?"

"I would never cheat on Howard," I answered, avoiding the question thus putting automatic admittance in the mind of Caroline.

"Oh my God, Jasmine, you are such a Leave it to Beaver woman," Caroline accused.

"Why, because I am loyal and traditional?" I asked, getting annoyed by my sister's overbearing personality.

Jill chimed in, "Leave Jasmine alone."

"I am just saying it is not cheating if you are just eating cunt or getting your cunt munched by another female," Caroline said.

"Oh I can't wait to hear this logic," I sarcastically responded, even though part of me was curious, particularly with my crush on Amber.

"I would never cheat on Cameron with another guy," Caroline began.

"How 1950's of you," I said, unable to hold back my sarcasm.

Jill giggled as she finished another glass of wine.

"On the other hand, having a little lesbian rendezvous is completely kosher," Caroline said.

"Because?" I asked.

"Because my husband doesn't have a cunt. He can't provide the lesbian experience," Caroline answered.

"So eating pussy, not cheating," I clarified. "Sucking another man's cock, is cheating."

"Exactly," Caroline nodded, as if that cleared up everything.

"Does the lesbian fucking you with a strap-on count as cheating since your husband does have a cock?" I asked, trying to poke holes in her bizarre theory.

"That is a grey area," Caroline answered. "But I can't say I haven't been on both the giving and receiving end of a nice strap-on." Finishing her wine, she looked around to see if the waitress was coming, before she answered, "Can you keep a secret?"

"Of course," Jill and I simultaneously replied. Although we were both disturbed by our sister's slutty behaviour and obnoxious personality, we did seem to live vicariously through her wild nature. Plus, judging by her tone, this was going to be a doozy of a reveal.

"Do you know what pegging is?" Caroline asked.

"No," Jill and I simultaneously answered, both of us leaning forward to hear Caroline's suddenly more discreet voice; although truth be told I did know what 'pegging' was through my writing.

"Are you ready to order?" Emma asked, making all three of us jump.

"I think we are," Caroline answered, smiling. Each of us ordered while an older gentleman brought us our appetizers.

Once we were alone again, Caroline filled each of our wine glasses and said, "A toast."

"To what?" Jill asked.

"To sisters who don't do this enough," Caroline answered.

"Agreed," I said, raising my glass.

"Fair enough," Jill agreed, raising her glass too.

We clanked our glasses, giggled like school girls and each shot half our glass of wine.

"To a crazy night," Caroline added, finishing the glass she had just poured.

Not wanting to be outdone, I finished my glass of wine as well...I was now well on my way to being drunk. "More," I requested, handing my glass to Caroline.

"Is our baby sister getting a little wild tonight?" Caroline asked.

"Maybe," I shrugged coyly.

Caroline poured herself and me another glass as Jill inquired, "So what is pegging?"

"Are you sure you are ready for this?" Caroline asked.

"You can't start a story and not finish it," I said.

"Fair enough," Caroline said. "Pegging is when the girl, wearing a strap-on, fucks a man in the...."

"Ass?" Jill asked, her eyes going big.

"Do you peg Cameron?" I asked, the thought of her big burly husband taking a strap-on in the ass both disturbing and hot.

"I told him if he wanted my ass I got his," Caroline smiled, revealing yet another naughty aspect of her life.

"You take it up the ass?" Jill asked, clearly overwhelmed by all these sexual revelations.

"Oh fuck yes; it is the ultimate act of submission. Giving in to the ultimate taboo and giving complete trust to your lover," Caroline explained. "Plus, once you get used to having a cock in the ass it really feels fucking amazing."

"I would never," Jill said.

"Never say never," Caroline smiled.

"Oh, I'm pretty confident," Jill countered.

I recalled my ex-fiancé, Mike, taking my ass and although I didn't enjoy it the first time, I soon began to crave it and would beg for Mike to fill my ass with his cum. Of course, this was not something I planned to ever share with my sisters...nor was it something a gentleman like Howard would ever think to do to his wife...unfortunately.

I tried it once years ago," Jill admitted, "but it hurt too much."

"Oh, it takes patience and lube and a lot of wine the first time," Caroline smiled.

"When was the last time you took it up the butt?" Jill asked.

"Last weekend," Caroline answered freely with no shame at all.

Jill sighed. "I haven't been laid in six months and you get it in the butt."

"Really? Six months? I would die," Caroline said, as if she were told she had six months to live.

I joked, looking at Caroline, "Does anal sex count as sex?"

"Of course, so does oral," Caroline replied.

"Well, in that case he has had sex with me, but not vice versa," Jill said.

"You give him head, but he doesn't reciprocate?" I asked.

"He will just walk over to me and shove his cock in my mouth," Jill admitted, tears starting to roll.

"Oh, honey," I said, moving to her, even as I tried to figure out how someone so strong as Jill could be used so easily.

Caroline said, "What happens once he shoots his load?"

"Caroline, enough!" I sternly said, giving Jill a big hug.

Jill, between tears, admitted, "Either he comes in my mouth or shoots his cum all over my face or tits. He loves coming on me."

"Wow," Caroline said. Even she was surprised.

"But he thinks eating pussy is gross and he doesn't really like having sex," Jill continued.

"He thinks it's okay for you to give him head and not give it back?" I asked. "What an asshole."

"That is a fucking understatement," Caroline said, before adding, "plus, eating pussy is not gross but rather a sweet, sweet delicacy."

"Oh for Christ's sake, Caroline," I said, frustrated that Caroline never knew when she went too far.

"I am just saying, it is just a pathetic excuse by a pathetic man," Caroline said.

Just then, Emma arrived with our meals. Noticing it was an awkward situation, she handed us our meals and asked, looking at the almost empty bottle of wine, "More wine?"

"For sure," I said, thinking getting Jill shit-faced was definitely in the cards.

Emma left and for a few minutes we ate and drank in silence. As I ate, I tried to figure out how Jill, the strongest of us, could be submissive to a dick like Adam. The thought of Adam walking over to her all pretentious and shoving his cock in her mouth was so shocking and yet, truth be told, the thought of Howard doing that to me was quite a turn on. Howard was a gentleman though, and never caught on to the obvious reality that I was submissive no matter how much I hinted.

My ex-fiancé, Mike, was a dominant man who knew exactly what I needed sexually. I remembered the time he walked into my apartment, walked up to me, put his hands on my shoulders and guided me onto my knees. I sucked him, as expected, swallowing his load before he fucked both my pussy and ass. And then I remembered other times when I had submitted to him like when he made me blow him during Christmas at my parent's house, with both my sisters asleep in the same room; or when I had to suck his cock under the table at a restaurant, and again at a Broadway play; or the time I had to ride him in the back of a taxi.