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I grew up in a mid-size city, a middle class family and mostly sheltered from the big city life of Chicago just a few hours away. We didn't have rave parties and orgies, but we knew about them of course. I was the oldest by three years and always very protective of my baby sister. My family and I tried to keep the realities of inner city life away from her the best we could.

The world really opened up for me when I went away to college at Northwestern University. I found the "big city" temptations of drugs, orgies, and parties all in the microcosm of the campus. When my sister Diane turned 18 and graduated High School she joined me at Northwestern. I insisted we share a two-bedroom apartment and naturally my parents agreed. It made sense to save money this way and besides I would be able to watch over my virginal baby sister and keep the wolves at bay.

Boy was I ever mistaken.

The arrangement would cramp my style a bit. I was currently dating the wildest woman I ever met, Lila. She was an art major who rocked my world. She was a little shorter than I at 5'9 and volunteered to be a nude model at the art department. She worked at the local Hooters wearing those orange short shorts and skimpy white tank tops that really accentuated her 38C chest. We had dated for a couple of weeks when we started having sex regularly she was nearly insatiable. She would want us to role-play. I would pretend to be an art student and she would model and I would change her poses resulting in sex. Or she would pretend to be my French professor and seduce me.

We acted out our fantasies and it opened a new world for me. Then one night after sex we cuddled together and she told is she was bi-sexual. She also stated she would love to have a threesome with me and another girl. I was intrigued. Okay... I am a guy... so I was very excited. Since then wherever we went and saw a beautiful girl I'd whisper to her "how about her?" She would play along in a teasing way, but it never really materialized and after a week or so I just dropped it as one of her fantasies.

When Diane moved in, Lila and I had to curb some of our role-playing activities to the confines of our bedroom. I also felt embarrassed about having sex while my sister was awake in the living room or the bedroom next door, so we either waited till she was asleep or was gone. Most of the time on the weekends, I spent the night at Lila's place.

Diane and I got a long. She made fun of how protective I was of her. I would say stupid things like "Lila and I are just sleeping over because it's late and I don't want her to drive back to her place so late". My sister would recognize these apparent attempts to mentioning sex to her and she played along or teased me with "oh just sleeping eh... sure"

Now Diane is beautiful. At 5'5 she was prom queen, head cheerleader in high school and all that stuff. She is majoring in Drama and probably is destined to be one of those beautiful movie actresses. Most people think she looks a lot like Jessica Alba, but with a larger chest. Perhaps that is why I was always so protective, making sure the guys she went out with were "good guys" not slime or perverts. We both new and even Lila told me she assumed that my sister was having sex when she went out on dates, however, I didn't want to hear it or know about. My ignorance in her sex life was my bliss.

Let me defend myself here. I was protective but I wasn't fatherly. Diane had her own social life. She would drive out to parties or her girlfriends and go out on dates. The fact being that the more she was away from the apartment, the more fun Lila and I could have.

All that was the setup... now comes my story and perhaps you can help me with my problem.

Diane went out to a party and it was going to be one of those all nighters. I finished up at the library and raced home because Lila was going to be waiting for me to do some special role-playing she had planned. It was about 10:30 PM and I saw that Diane's car was gone from her assigned parking spot. I saw Lila in the guest parking and raced up to the apartment.

When I opened the door I saw the lights were off except for a couple of candles. There were two empty bottles of wine on the coffee table and some soft music coming from my bedroom. I grinned, wondering what Lila had in store for us tonight. I silently opened my bedroom door and saw in the dim candle light Lila nude on my bed facing down, her ass facing the door. I smiled and started taking off my clothes but then I her moaning and as my eyes adjusted it dawned on me that there were two people in the bed. In fact there was another girl under Lila and they were in a 69 position.

"She did it" I thought. She went and got us another girl. This was what she was planning and she picked the perfect night when my sister was gone.

I quickly undressed and moved to end of the bed. I couldn't really see much of the new girl since she was much smaller frame and her face was buried in Lila's pussy. The girls head was at the foot of the bed and Lila's legs hung over. Not to startle them I gently placed my hands and rubbed Lila's ass and hips. She moaned with approval as I began to lick and nipple at her ass, all the while trying to get a glimpse of the girl underneath without luck.

My cock was so hard watching this action I rubbed it along the crack of her ass while holding her hips. She stopped snacking on the snatch long enough to whisper a horny "yes" as she buckled her ass upward a little to allow me access. My cock found it's way easily into her very wet pussy. The girl underneath her didn't seem to mind, in fact I could feel her tongue running along my cock as it drew in and out of Lila's pussy. As I started pumping her faster the girl underneath licked my balls and when she took them both in her mouth I came in force. My own knees buckled and I climbed onto the bed leaning up against the pillows and backboard in a halfway sitting position.

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SnowBoard Trip

I had been planning this day since late December. I was sure I could pull this one off. I work most weekends when I don’t have plans with my man. This leaves me free on weekdays to play my own games. I have been snowboarding for over 20 years and I'm not that good, but it’s a rewarding activity for me. I was seeking lodging at a ski resort in exchange for a nice date with the right guy. I began by searching some of the websites that I belong to, but wasn't getting responses from people...

Cheating
2 years ago
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Snowboarder turns StraightMarried man into his co

My company's annual convention was in Vail, Colorado this year. My family had been planning a winter ski trip and I thought I'd take the chance to scope out Vail as a possible site. The convention was scheduled so that we attended meetings through lunch and had the afternoons to explore the town, ski, or network with fellow employees. As it turns out, I did some serious networking, but I doubt the new contacts I made will help my business and I definitely won't be adding them to my client list....

3 years ago
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Snowblind

I screamed desperately into the white veil, thrashing at the blank landscape with the least convincing punches I’d thrown in my life. The cold numbed and bit into my skin, forbidding me from forming feasible fists while my stiff, unwilling arms couldn’t wait to hug me once more. My club-like mittens uselessly tucked under my armpits, seeking any modicum of warmth. Turning back towards our makeshift camp, I could barely see the flicker of diminishing flames even from only a few feet away. The...

Love Stories
3 years ago
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Snowbound with a fun cougar the Finale

After I rested up from filling Sheila's mouth with cum, she asked me very meekly "May I show you something, Sir?"I nodded and she got off of the bed and went to her dresser. She took out an array or dildos, vibrators, cuffs, ropes, clamps, and more. She placed them all on the bed. I grabbed the leather cuffs, both wrist and ankle and the leather studded collar and told her to put them on. While she was putting them on, I gathered up some ropes, nipple clamps a leather whip, a butt plug and a...

2 years ago
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Snowbound with a fun cougar Part 2

I followed her up the stairs, admiring her shapely ass in her silk PJ bottoms. Enjoying how we had quickly settled into our roles as Dom and sub. When we approached her bedroom she gestured for me to go in first, "After you, sir." she said as she looked at the ground. I entered her bedroom and pointed to the king size bed, telling her "You're a bad girl and you need to be punished! Get on all fours so I can give you a proper spanking!"Sheila slowly walked to the bed, got up and all fours and...

3 years ago
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Snowbound with a fun cougar

This is a true story that happened many years ago. I was working as a software technician and was often making service calls around the state to different offices. There was a customer that I usually serviced in Princeton, about an hour south of where I lived. The company did medical billing, there were eight employees, all women. Sheila, the woman who owned the company was in her mid to late 50's, she always wore loose clothing, but was a bigger woman. She definitely had a BBW type of body and...

1 year ago
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Snowbunnies Directors Cut

“Oh my god, you pathetic little bitch! Princess, I was only joking when I said you had to color something before Daddy came in me again. I just didn’t want you staring at us like a sick little perv and touching yourself! It’s not like you can even jerk that pathetic little cock while it’s locked up in your chastity cage. But even if it wasn’t locked up, do you REALLY think that you could get hard? Seeing how we dated for 3 months and your prissy faggot ass never once got a hard on until the...

1 year ago
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snowboard weekends

I was finally going to try jay peaks with a bunch of friends from collegeit was organized and all, i got in the bus after the day at school, and they must have left that place for me after seeing i registered alonethey were 2 , been organizing this for the last 3 years of them degree , this year i was the choosen ''lucky one''they had booze and i spent the bus ride to the usa vermont with em drinking and chilling in the back of the buswe arrived at the hotel and i learned about the ''mistakes''...

3 years ago
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Snowbunny turned

African Anthropology, African Studies, and Black Philosophy had become some of the most common degrees for white females by 2018. The wave of multiculturalism led to many of them instinctively allying themselves with the progressive politics of the time favoring disenfranchised minorities. White guilt swept over them getting them in the door as they opened their minds and ideas to increasingly more extreme philosophies. White people brought slavery.White people brought colonialism.White people...

4 years ago
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SheCameFromNowhere

"Listen to me. No, no, listen", I paused, sighing as the man across the desk opened his mouth to speak. "Larry, for fuck's sake listen to me. You know me, alright? The studio knows me. The people know me. Have I ever let you down? In the ten years I've been with you, in the...nine movies I've been in? No, I haven't, have I? And you know my speciality, my talent, my...mimicry, right? So come on, just tell me what you think" "I don't know, Bob, it's a hell of a risk. What if you get...

4 years ago
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SNOWBOUND

SNOWBOUND CHAPTER 1I could not believe Danny Boy, my DB, was planning a trip to West Michigan in mid-winter. Is he crazy? People do not travel from Southeastern Tennessee up to Michigan in the winter. It's not done. I'm glad he likes my lighthouse pictures with all the ice and snow, but wanting to travel all this distance in winter weather to see them. Without a doubt, DB is crazy. But on the other hand, being able to once again see my best friend in the world at this time of year would...

1 year ago
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SnowWhite

I think of my early life as average for a woman of my time; went to college where I met Dan, married him, dropped out of college and worked mediocre jobs to help Dan get his degree. The plan was that after he got settled in his career, I'd go back to college and finish, but I got pregnant...then we had two more c***dren in quick succession. I became a housewife, Chair of our PTA, volunteer swing instructor at the local YWCA and the cool mom that always takes the k**s out for ice cream after the...

2 years ago
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NaNoWriMo 2020 Chyoa Edition

November is fast approaching which means NaNoWriMo season will soon be upon us. For those that don't know about it NaNoWriMo (National Novel Writing Month) is a creative writing challenge whereby a writer tries to write a 50,000+ word novel in the month of November. Our challenge here will be a different one but in the same spirit of encouraging writing and creativity. The first major difference will be that this will be a community challenge. I invite all writers, particularly first time...

3 years ago
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Snowbound With A Fun Cougar

I was working as a software technician and was often making service calls around the state to different offices. There was a customer that I usually serviced in Princeton, about an hour south of where I lived. The company did medical billing; there were eight employees, all women. Sheila, the woman who owned the company, was in her mid to late fifties, and she always wore loose clothing, as she was a bigger woman. She definitely had a BBW type of body and it was obvious that she had big tits....

BDSM

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