Unexpected Outing Part 4
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Janet Ballion knew she was blessed and lucky. She was born upper-middle class, was surrounded by a great support system filled with friends and family who loved her. The college girl was also a highly intelligent extrovert. Her looks were alluring and the people who were drawn to her stayed because of her charisma. The list of why she was as lucky as someone who had a horseshoe and found a penny right before hanging upside down to kiss a stone in Ireland just kept going. Even with...
It all started five years ago, when Maddie was thirteen. Being an only child, she needed a babysitter still when her parents were out of town or at an event together that Maddie couldn’t attend. Usually, Maddie’s grandparents would come by to watch her, or she would go to their house. However, during the winter, her grandparents would go to their home in Florida. Maddie could not remember where her parents went that night five years ago, but she remembered everything else. Her parents had asked...
First TimeSporty Spice's First Outing by Shauna H. I wasn't sure how far I could push things with Terri. I always thought that he would look really cute, if only I could find a way to get him 'dressed up'. Little did I think that my plan would backfire, and end up with both of us getting our first taste of cum! Terry was my young brother-in-law, nearly 14 years old. He was very close to Sandra, (my wife), particularly since his older brother had moved abroad for work. He didn't seem to...
Gary's Golf "Outing" Chapter 6 Suck-cessful Coming Out Party "Christie and I decided that tonight was the ideal time for my ?cumming out party.' The question now is: where do we have the party?" "I think I have the answer to that question, honey," Christie said. "Bob has to get up early for work, we may have to walk back to our condo if the cart doesn't start, so what better place to have a party than right here?" "Here? With all these people? No way," I protested. "Way,"...
by pete, June, 2006. Chapter 1. My name is Paige Wilson, I am an English Lit. and Geography teacher at a well known private school for girls in Toronto, I am just twenty-six years old, and I have a knack for getting on with my students. All of them are around fifteen, pushing sixteen, a difficult age bracket to teach, I have been told by my peers, myself, I didn’t feel that way. Of course my fellow teachers were right in a way, young female hormones were rampant, and my two...
This story will describe the events that occurred at a golf outing that I attended when I was 40 years old. I was a mid-level production manager at a small manufacturing company in the Atlanta area, and three of my co-workers and I arranged for a week-long golf outing in Hilton Head. I had worked with these guys for four years, and although we had a good working relationship, we had not socialized very much. But, we all loved the game, and took advantage of our one week production...
Thanks everyone for feedback through email and comments for my previous stories. Ppl can send me feedback at This incident happened between me and my office colleague in Bangalore. We were in same team and used to like each other company but nth serious as she was married. We used to do leg pulling to each other. But we were knowing our limit too. Our manager was planning for Wonder La(Amusement Resort) team outing and whole team was very exited. But in last moment plan got canceled because of...
Copyright by the author. All rights reserved. This story may not be reproduced without the express permission of the author. Bikini Beach: The Family Outing By Elrod W "This one doesn't look good, either." Mike Harwin slid his key into the ignition as he slammed the car door. He glanced over the seat. "Sorry kids, but this doesn't look like a very nice beach." There was an immediate cry of protest from little Jimmy and his older sister Nichole, seated in the back of the sedan....
Hi guys this is a fictional story about my mom and her lover. Hope it will make you horny. And it was as Sunday again and as usual my mom had a plan outside. I always wonder where she is going so early, that too on Sunday. That day I decided to follow her as I was so curious to know. I wanted to know where she is going. My dad was as resting, which he always does on Sunday, that is what a working man is supposed to do on weekend, but not my mom. Even though she is a working lady, she does not...
IncestDVD Night, or My Second Public Outing This is an autobiographical work of non-fiction. Everything described here, in all detail, is true, as it was in my first accounting "Buying Water as a Girl." I hope you enjoy, even though it's far more pedestrian that the adventures many of you had. It may interest only me. But my hands still shook from the adrenaline when back in the car. ---- Didn't Blockbuster used to be open to midnight at all locations? Didn't it? Now they close at...
Gary's Golf Outing Chapter 17 -- Four Maids A-milking I woke bright and early on Saturday morning, did my daily routine in the bathroom, plus I gave myself an enema. I shaved twice, shaved my balls and the stubble under my arms, some stray hairs on my legs and some peach fuzz on my chest. I had to glue my new falsies on my chest and I didn't want any hairs hanging onto them when I tried to take them off. I pulled the red panties up my legs, followed by my tan slacks and a dark golf...
Gary's Golf Outing Chapter 22 - It's Off to Work We Go Gabrielle's ass was sore when she woke up on Saturday morning. The all- night fucking by her wife, Kay felt good while it was happening but the strap-on penis had taken its toll. She gingerly walked to the bathroom and stepped into the shower. The warm sudsy water felt good so she was reluctant to finish. She tenderly patted herself dry and was very careful with her anal area. She found some ointment in the medicine chest...
This is a review I wrote of a session I did with a Mistress in London. My session with Mistress Morticia --------------------------------- I did it!!! I served a Mistress as a maid and we went out in public as Mistress and maid. When I first arrived I was led into a bedroom where I could change. Mistress watched as I did so and helped me zip my dress up. It is really quite erotic having a women watch you undress from your male clothes (well male exterior clothes, I spoilt the...
This story will describe the events that occurred at a golf outing that I attended when I was forty years old. I was a mid-level production manager at a small manufacturing company in the Atlanta area, and three of my co-workers and I arranged for a week-long golf outing in Hilton Head. I had worked with te guys for four years, and although we had a good working relationship, we had not socialized very much. But, we all loved the game, and took advantage of our one-week production...
Oral SexLast year, I wrote a story entitled Foul Language, wherein a bitter, angry Geoff Matheson had been through an ugly, unjustified divorce from his wife of 30 years. The most dispiriting part of the whole episode was the vile treatment he received at the hands of his wife’s divorce lawyer, one Claire LaPointe. Geoff survived the divorce, and moved to the West Coast to start a new life. He was not a happy man, and only the single good fortune of having a large corporation purchase an obscure...
“You wanna play a few with us? I mean we’re all waiting anyways.” One of the girls extended an olive branch. “Sure, I’m Scott.” “I’m Caitlyn, this is Casey and Hannah. I shook all their hands and smiled. “Nice hat,” Hannah remarked. “Thanks, I was born there, kind of have to be a fan,” I remarked of my Bills hat. She laughed and told me how a few of the players used to come into the Wegmans where she worked. We chatted for a bit while the group in front of us finished up the...
Following is a true account of one of my experiences of shopping for lingerie. (nosex). This happened a couple of months ago, and as far as I remember, the conversation went like I have described below. If you have not read my earlier story ‘Wonderful crossdressing shopping experience’, I’d suggest reading it first. ———————————————— Following my wonderful shopping experience on the Christmas eve, I was feeling elated. I had just bought a couple of very sexy women’s clothes, I had crossdressed,...
My wife had a yearly golf outing with her co workers. There was going to be 12 guys and her and three other women. I know that there would be a lot of drinking going on and the course was 45 minutes from our home. I told her that I would take her and pick her up because I did not want her getting in a car with someone that was drinking. She said she could get a ride there from one of her friends. She got picked up around 8:30 in the morning I never saw who was driving the van that picked her...
Kimmy and I have been together for a few years now. When we met she was sexually inexperienced, having not been any men before me. But after a couple years of having a steady boyfriend, she was finding her adventurous side. It started out just trying different positions in the bedroom, but then it extended to discrete touching in movie theaters and restaurants, and then blowjobs in the car on the drive home. I always tried to encourage these steps forward, hinting at fantasies of making a sex...
Fag Hags' Outingbypenisleeve©She was a friend, a good friend and wife of a mate. She had wanted to go out for the night and do ‘something wild’ for absolutely ages and had driven us all mad with her constant whinging about it. Mick her husband wasn’t interested and as my wife was working the 4 to 12 shift, I agreed to take her to a couple of night spots where she’d see some ‘wild’ things. They were gay locals where my wife and I frequently went and where we both enjoyed meeting casual partners...
189 AVIS AND JOE an outing[LATE ENTRY]Avis and I were out of town for a few days and we stopped off to spend the night and get a bite to eat. After dinner, we both were still a bit tense, so we decided to go to a bar that we had passed on our way to the hotel. Having never been in that particular bar before, we were not sure of what to expect. We entered the front door and looking around, the place seemed okay with some tables about and a long bar along one side of the room. I noticed a...
Usual Health WarningThe largest parts of this story are pure fantasy; the Mummy and Daddy episode in the hospital car park has a lot of truth. The author has no wish to promote u******e sex; but if that does appeal, then restricting your urges to your own ch1ldren has merit for the wider society.This story does contain (hopefully) fairly graphic scenes of fami1y intercourse, so please do not read if easily offended. Fami1y OutingTwo weeks after Ellie lost her anal virginity to her Dad during...
Dear friends, I am Srini, working as a software engineer in Bangalore. This story is on how I had sex with my office manager Lakshmi when we went on an overnight company get-together. So about myself, I am 26 years old and have been working for last 5 years in this company. My manager is a 30-year-old lady by the name Lakshmi. Ms. Lakshmi is a tall medium built lady, oval face, fair complexion and always well dressed. She always wears chunni with chudidar or salwar kameez. Her kameez or kurta...
First Outing By Pat The Bunny I thought about adding a disclaimer here about not reading this piece if you don't like its nature, but I don't need one. Because not only is this relatively mild story true, but I just returned from the events forthwith I shall now describe. I, like many here, have a fascination with the delicacy of the female form, their easy grace of mannerisms, and the constraining yet paradoxically free-form shape of women's clothes. Through the years I've...
Ed and I met through a site like this one. We talked back and forth through emails about our different sexual preferences. He let me know he was experienced with both men and women in threesomes and that he was a bisexual. He was older and his wife wasn't interested in sex anymore but he still had a strong drive.He told me enjoyed bothe sexes equally and had a man and a woman he saw on a regular basis.It tokk a while to get together. For a long time he would send me pics of him and another guy...
Buying Water as a Girl, or my first public outing This is an autobiographical work of non-fiction. Everything described here, in its detail, is true. Maybe one of the three people involved is reading this and recognizing themselves. If so, I'm sorry I lied to you. Drop me a line. To everyone else, enjoy. It's not the adventures some who are braver have had, but it was a thrill for me. ---- I sat in the car, breathing a little heavily, staring out the windshield at the Dunkin'...
Gary's Golf "Outing" Chapter One -- Seven Hole Washout My wife's mother called to tell her she wasn't feeling well and she wanted my wife, Kay, to come up to Chicago to be with her. She is a hypochondriac and it's not unusual for her to interrupt our vacation, or whatever we're doing, with her demands. I was hoping to play golf this day but it was getting cloudy as I drove my wife to the Fort Lauderdale Airport. As I kissed her goodbye, I told her to give my love to her mother....
Gary's Golf "Outing" Chapter Two -- Three Surprise Indoor Holes "Let's get out of these wet clothes and we'll take pictures later," Kimberly said. "Gary, you're our guest, so you can use the shower first. Leave your clothes outside the bathroom door and I'll throw them in the dryer and get you something dry to wear." Christie had gotten a bottle of wine and three glasses from the kitchen and we drank a toast to a new and long-lasting friendship. I got into the shower and looked...
Gary's Golf "Outing" Chapter 4 - (Fore Play in the Ball Room) Luckily for me, the room wasn't too well lit -- just the emergency lights, a candle on each table, and an occasional flash of lightning. It was also a good thing I was walking arm in arm with Christie and Kimberly when I walked into the ball room or I probably would have fallen flat on my face. My legs were shaking I was so nervous. But after a few introductions and explanations about my lost voice and a few comments like...
Gary's Golf "Outing" Chapter 5 -- Ladies Only I was so embarrassed I had to get out of there. "If you ladies and gentleman will excuse me, I have to go powder my nose. Which way is the ladies room, Christie?" "Wait a minute, Gabrielle, I'll go with you." She picked up her purse and mine, took my arm and led me down the dimly lit hall to the ladies' room. "You almost blew it, Baby." "Blew what?" "Haven't you ever noticed? Ladies never go to the ladies room by themselves nor...
Gary's Golf "Outing" Chapter Nine -- Hair of the Dog Back in the bed room Christie and Kimberly laid out my outfit for my first round of golf in drag. I put on a pair of pink silk bikini panties and a matching pink silk bra. Kimberly put breast forms in the bra that looked like real breasts; they even had nipples. I put on a short-sleeved pink golf shirt, but balked at the short black skirt that lay on the bed. "I can't wear that; I never saw a skirt that short. Everybody will see...
Gary's Golf "Outing" Chapter 10 - Ladies' Golf I kissed Bob Goodbye and went out in broad (forgive the pun) daylight for the first time as a broad; it will probably be my last time if this old broad reads me. As I approached the green I recognized my partner. She was the woman who peeped over the stall door last night as I was blowing Christie. She was in her early '50s and built like a fire plug -- about 5'2 and very solid. She greeted me with a strong handshake and a peck on the...
Gary's Golf "Outing" Chapter 11 -- Gary Joins "The Club" I called Kay when I got home and she told me she was definitely going to spend another week with Heather, or until she was sure her mother was going to be okay. Imagining what they were going to do relieved any guilt I felt about my weekend with Kimberly and Christie. I told her to take all the time she wanted, that she deserved a vacation, even though I would miss her. She said, "I'll make it up to you when I come home."...
Hi, I am already familiar with you all; I believe. Even then for new readers, it’s my pleasure to introduce myself. I am Rajesh, an engineer in profession, 43 years old. I am happily married with beautiful Priya for last 14 years and we are blessed with two children. We stay in company accommodation; our neighbours are mainly from the same organisation, all family persons. By staying for a long time in same locality, we have developed good family friendship with few families of same status. My...
Gary's Golf "Outing" Chapter 12 - A Night at the Casbah I went down to my apartment to get my shaving gear and called Kay. "Hi, Sweety; what's up?" "I should ask you that," she said. "Not much. How's your mom?" "She's okay. What's new there? Any storm damage?" "No, everything's pretty normal here. Brad was asking for you... Brad ... The guy from the penthouse who hangs around and gawks at you... Maybe you're right... Maybe he is gawking at me... I met his friend today...
Gary's Golf "Outing" Chapter 13 What's Good for the Goose is Good for the Gander I woke up with an incessant ringing in my ears. What is that? Is it ever going to stop? I opened one eye and saw that the sun was high in the sky. I raised my head and realized the phone was ringing. It was my wife calling from Chicago to see how my evening at the CD club went and to tell me about her night on the town. "Oh, hi Kay. What time is it? I just woke up. We didn't get in till late." "We...
Gary's Golf "Outing" Chapter 14 - Ladies' Favorite Activity I finished all of my work assignments and my home chores by Thursday. I had chatted with Kay a few times and was surprised when the phone rang on Thursday evening. "Hi Gabrielle, this is Kimberly. Are you all set for Saturday?" "Hi Kimberly, what's happening Saturday?" "Don't bull-shit me, you bastard. You know what's happening as well as I do and I'll bet you've been thinking about it all week." "I have...
Gary's Golf Outing -- Chapter 16 The Morning After I woke up the next morning in a cold sweat, a hot, cramped hand, a warm sticky substance in my mouth and a pole gagging me. I was afraid to open my eyes, but an expert cock sucker was sucking my cock and I had to see what was happening. The cold sweat turned out to be a pool of warm semen that had drooled from my mouth during the night and turned cold. The warm sticky substance was fresh cum from the pole that was trying to enter...
Gary's Golf "Outing" Chapter 18- Home Cumming "Shhhh," Kay said to Penny as she unlocked the door to her condo. "We don't want to wake Gary. He'll want to join us in bed. I want you all to myself tonight. Gary can wait until tomorrow night." She locked the door behind them and lit a night light in the living room. They tip-toed past the guest bedroom to the master bedroom. "Shhh," Kay whispered again and carefully peeked in. The room was empty. "He's not here," she whispered again....
Gary's Golf Outing Chapter 19 Kay Cums Home, Shopping Shenanigans Kay's home-cumming was a great start to a great week. Every evening was a variation on the theme that began early Saturday morning, and ended Saturday evening, with Kay sandwiched between me and Penny with me in front with my prick in Kay's pussy and Penny behind with her six inch clitoris in Kay's rosebud. Sunday's bedtime arrangement had Penny sandwiched between Kay, with Penny's clit in Kay's pussy and my 6...
Gary's Golf Outing Chapter 20 - House Guest "Are you ready for your ass-fucking, my love?" Kay asked when I opened my eyes. "Just as soon as I use the facilities," I responded. "Let me join you," she said. "I want to give myself an enema and I'll give you one, too." I wasn't keen on enemas but, at this point, I was ready to do anything Kay wanted me to do. I never thought I'd say it, but the enema was extremely erotic. Maybe it was because it preceded my first morning...
Gary's Golf Outing Chapter 21 - A Good Time Was Had By All I poked Kay's pretty pussy with my prick to wake her up. "What." She said groggily. I said, "I'm ready for my morning fuck." "What time is it?" she asked. "It's 7:15. What difference does it make?" "You have to be at the golf course by 8:30. We won't have time for your morning fuck." "Oh shit. I forgot all about golf. With my prick in your ass all night I couldn't think of anything else except getting your big...
Gary's Golf Outing - Chapter 23 - Party Preparations Somehow, Kay and Gabrielle left Betty's Boutique unobserved, Gabrielle in her red French maid uniform, red stockings and strappy red high heeled sandals, and Kay in the sexy black bra with her bright red lipstick painted nipples protruding through holes, a black garter belt and panties and black four inch high patent leather pumps. When Kay and Gabrielle got into the car, Kay said, "Can you drive with those shoes on or do you...
Gary's Golf Outing Chapter 24 - Brad's Big Birthday Bash Gabrielle woke up early Saturday morning with morning wood, even though she had spilled a copious amount of cum the night before when Kay fucked her with her squirting dildo. I guess sleeping between two gorgeous girls all night could contribute to that condition. Kay had fucked Heather the night before, too, but, of course, Heather had no visible signs of arousal. "Would you like me to take care of that for you, Honey?" Kay...
Hi All, this will be my first post however not the last depending on the responses I receive from you the readers of our favorite site :). Call me Sandy, physical look wise not a six pack carved body but having a little bulge in the middle with a frame of 5 feet 9.5 inches. Typical Mumbaite with easy going nature working in a MNC as a manager. The incident am gonna narrate took place when I was in Chennai. I was posted there to help set up the new location and new process. Was sent there for...
A DIFFICULT OUTING By, Salty Lady I was walking down the road in a black, flower print dress. My heals clicked on the pavement. The street lights showing my destroyed makeup. To myself I say. "But I do know what I need to do." THREE DAYS BEFORE Not a good sign when you are talking to yourself, but I was as I walked back to my dorm. "Twenty-four years old and I'm living in a fucking dorm full of eighteen-year-olds. I'm an average guy. I'm average height and average build, with...
Barbara stood staring at the outfit she had purchased for today's shopping trip with Cheryl. The black leather mini-skirt looked like it belonged on a 12 year-old, not a woman her age who was the mother of two. When she tried it on at the store, she had to buy a smaller size just to get the effect of 'barely covering your ass' that Cheryl had directed her to buy. It did barely cover her ass. If she were to bend over or reach for anything, the skirt rode up and exposed everything worth...
Hi this is Arjun again for ISS. This is my second story for ISS. To get to know a little about myself and to know what happened before this story PLS check out the previous story “Unexpected Restroom lust”. The previous story had a few spelling mistakes and I think this will too :P. Pls bear with me. This story is a continuation of my first sexperience with my college mate JananiPriya, that too in our college restroom. Weird place to have sex isn’t it. So, with no time to waste; ill start the...
Hi, this is my first story at ISS. I have been a regular reader of sex stories over here and at last thought to pen down my real experiences. This is my first experience which I am writing here. I am not a descriptive writer so Please forgive me for my mistakes. Fair comments will encourage me to further share my other experiences in a better way. You can send your feedback on my mail address at I m raj at present 32 years of age, highly educated,well mannered, suave and articulate . I stand...
Hello dear readers… Hope you are ready to be aroused by my new unexpected yet wonderful experience. Not delaying any more… here I start my experience :) I am a male bdw ;) and I am staying with my friends in a house. As many guys have that anxiety about woman and their hidden treasures, I was also curious about them and always wanted to have some fun with woman but never got a chance. So… why am I writing this post? It’s because every one is given a fair chance, I also got mine and that too in...
I get a call from Lisa“What have you got planned this Saturday”“Nothing really, was going to my mums, but apart from that nothing special…Why?” I asked“I have an idea, I think you will like….are you up for it then”Thinking about our previous encounters I was getting slightly damp in the crotch as she spoke“Yes…Alright then…what time” Lisa paused while she sounded like she was looking through something“About 8am…Is that good”I thought about what she might have planned“Yes…that’s great…are you...
"I am Me!" "A Night Out" By Anna Feie What can I say, I am Me! That's right, I am an older gal of indeterminate age. I have always felt that I am special - not better than someone else, but special in self. I had a normal childhood, grew up running wild. I spent the school years being a invisible student and the summers working outdoors for my parents or playing in the hundreds of acres of forest, waters, hills and dales surrounding my home. Events took a hand in my rearing. ...
Chapter 1 It was after ten o'clock on a gloomy January night. There was a cold rain falling, and it was being driven by a stiff wind. It was a good night to stay in. I was sitting in front of my computer about to finish my data entry assignments for the night. I thought I would read a porn story or two after that. The only light I had on in the house was the one on my desk. Suddenly, I was startled by a knock on my door. Being naturally suspicious of such unexpected visitors at...
Hello readers. Handshake to boys and boobs shake to girls. The story is a half-fiction and half-real, written for kinky and hardcore sex lovers. Relax and hands inside underwear now! I’m a 25 year old Software professional leading a healthy (I mean boring) life. I never had a girlfriend and led a lonely life nearly entire life. Although family life was nice, that desire to have a girlfriend was always there. Many might disagree but I feel a guy needs a girlfriend or at least a close friend who...
Reddit Unexpected Titty, aka r/UnexpectedTitty! Sometimes, we are lucky enough to be present during something unexpectedly hot, and that is basically what r/unexpectedtitty/ is all about. I think the name of the subreddit pretty much says it all, and you can expect a lot of unexpected titties or so to speak. With just a bit browsing, I am sure that you will get the gist of what r/unexpectedtitty/ is all about.Now, keep in mind that Reddit.com is a free website, and there are loads of NSFW...
Reddit NSFW ListTo understand how totally unexpected the event of several months ago was, knowing my history, well my sexual history, is helpful. I am a twenty-four year old lesbian. Well, at least I was a lesbian, but now I'm probably bi. The change in sexual orientation is what this story is about. I learned I was attracted to girls when I first turned sixteen and began exploring the secret world of sex in high school. Earlier, I didn't think much about the subject, and it wasn't a topic at home. Some of...
LesbianHey this is Dhruv. This is my first sex experience which I want to share with u guys. This experience and situation was completely unexpected. Its with my best friend Tina. Tina and me are best friends from childhood.. but one unexpected night got us together physically too.. Coming to info about me I am a boy age 21, and I am studying.. and good looking. My best friend Tina is my childhood friend. Both of us played together, shared everything..but never had such feelings of getting physical....
Hi friends… Gary from Calcutta. Thanks to ISS for publishing all my previous stories and the wonderful responses from the readers. I have been blessed amazingly in matters of love and sex, especially in last 3 years after coming to Calcutta. For those who are reading my escapade for the first time, I am a 34 year old guy with lots of sex drive. I love to keep myself fit by regularly gymming, and various sports. And being a part of a high end residential society, get many chances to interact...