Unexpected First Anal M2M
- 4 years ago
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When I was 28 and after my divorce, I had a bit of a sex drought and was feeling pretty horny and felt that I would go try my first M2M action since college. I had a couple of drinks at happy hour with my work counterparts and when they left to go home I decided to check out an anything goes bar down the street. I was quite nervous as I paid the cover charge and entered the bar. I entered and noticed it was obvious that it was mostly gay and guys there. I walked in and being a bit shy I...
I woke up hard and wet this morning. In my slumber, I began to rub my hard, precum covered cock with the vivid images of my recent dream. When I was in university I had a very close friend, he was straight, the boyfriend of one of my girlfriend’s. We shared many intimate moments and we lived in a constant bromance, we got d***k together, slept in the same bed together, we would hug and kiss, share secrets, he was the first person I ever came out to, in fact he asked me out right if i was gay...
Doctor Dan hmmm he was a sexy older gentleman with whom I had my first panty wearing episode, we had met on a website for casual encounters, I was expanding my sexuality and had come to some sort of terms that I was bi sexual. I am very intrigued by the male body and it’s appendages yet I still lust over women and their sexy bodies so I guess that makes me bisexual. Sorry got side tracked. The first time I ever met with Dan was at is place it was a tall tower overlooking a bay a beautiful condo...
A few years back, when I was in Chicago, my libido led me to a adult video arcade with Gloryholes. I paid the admission fee and got my tokens, for an extended night. I went upstairs to this little place that was well reviewed and hung out a bit and watched the action. About half the of the 12 booths were occupied, and there were another 5-6 guys that would cruise around and then go back out to the main area of the store. I could hear the video’s playing and some “other” noises, both of which...
Meeting someone online was exciting! Here’s my story of when I met “Jeff” We first started chatting on a website for bisexuals I believe I had posted an ad and he responded, I was just getting comfortable with finding my sexuality and we talked a lot about that, he had some experience and I was full of questions, I told him all about myself growing up from being a dirty hamper raider to eventually enjoying wearing women’s clothing on occasion, we talked about everything we were like a couple of...
I had recently graduated high-school and was working some residential construction to get some extra money for college. One day a co-worker, Jase and I were assigned to replace a toilet at nice ritzy home on the mainline outside of Philadelphia. Jase was a middle aged man with clean cut brown hair and brown eyes. He was 6’4” tall and quite muscular from working in the trades his whole life. We got there arrived at our clients home early to have the owner let us in. The owner met us in...
I was at a porn theater and had just gone a blown a guy eating a huge load of cum. My cock was out as I sat and slowly stroked it. The hot encounter that I just had made me incredibly horny and I was hoping for a little help with my cock. After about 15-20 minutes, I decided pull up my pants and try a local porn shop with gloryholes to see if my luck would be better. The movie on the screen was getting close to the money shot, so as I walked up the isle I looked over my shoulder. I got...
When i was a Junior in college, i was rooming with a friend named Joel. Joel was 5-9, blonde, blue-eyed guy that had a reputation with the girls as being a player. Besides his good looks, he was rumored to be hung like a horse, which I heard from more than one reliable source. For some reason, i had a curiosity to see his dick, not only soft, but hard as a rock. However, he seemed shy around guys and I never saw him without baggy shorts in our dorm room. To this day, i still do not...
A few years back, when I was in Chicago, my libido led me to a adult video arcade with Gloryholes. I paid the admission fee and got my tokens, for an extended night. I went upstairs to this little place that was well reviewed and hung out a bit and watched the action. About half the of the 12 booths were occupied, and there were another 5-6 guys that would cruise around and then go back out to the main area of the store. I could hear the video’s playing and some “other” noises, both of...
Doctor Dan hmmm he was a sexy older gentleman with whom I had my first panty wearing episode, we had met on a website for casual encounters, I was expanding my sexuality and had come to some sort of terms that I was bi sexual. I am very intrigued by the male body and it’s appendages yet I still lust over women and their sexy bodies so I guess that makes me bisexual. Sorry got side tracked. The first time I ever met with Dan was at is place it was a tall tower overlooking a bay a beautiful...
Meeting someone online was exciting! Here’s my story of when I met “Jeff” We first started chatting on a website for bisexuals I believe I had posted an ad and he responded, I was just getting comfortable with finding my sexuality and we talked a lot about that, he had some experience and I was full of questions, I told him all about myself growing up from being a dirty hamper raider to eventually enjoying wearing women’s clothing on occasion, we talked about everything we were like a couple...
I woke up hard and wet this morning. In my slumber, I began to rub my hard, precum covered cock with the vivid images of my recent dream. When I was in university I had a very close friend, he was straight, the boyfriend of one of my girlfriend's. We shared many intimate moments and we lived in a constant bromance, we got drunk together, slept in the same bed together, we would hug and kiss, share secrets, he was the first person I ever came out to, in fact he asked me out right if i was gay...
I had been chatting with this local guy for quite some time. With wife, c***dren, and work we never have hooked up. He said he was a high-level executive at a national hotel business overseeing a new hotel being built in Atlanta. His profile had him at 190lbs, and 6-4 and a married white male. Through all our chats he never sent me a body or face pic, but that was ok. His cock pic was enough for me. He had an awesome cock. It was a nice uncut, thick, and the head of his cock was like...
Between my junior and senior year, I worked residential construction with a neighbor. He had a small team, and I was hired on to do handy type work. One day he and I went to measure/estimate a master bathroom remodel. While we were there the owners left, telling us to lock up when we finished. Part of the remodel involved redoing the closet to create an entrance into the bathroom. In the closet we came across a huge stash of porn magazines. My boss said lets check out how kinky these...
I dont know what came over one but I agreed to it. As the door open I laid blind folded and naked face down on my bed with three pillows under my waist. The door shut and the next thing I heard were foot steps coming into my bedroom. All kinds of things raced though my head as my stranger got closer. Hmmm he groaned as he saw my naked male body in front of him. I heard the belt being undone and him stepping out of his pants. Then I two firm hands spread my cheeks. I could feel his...
I sat in my favourite bar sipping at my glass of Chardonnay; I had been coming to ‘The R Lounge’ for a couple of years. I watched the guy talking to his friends across the room. They were all dressed with a bit if style but he had caught my attention. He was wearing trousers with a casual blue and black stripped shirt. He was probably five feet nine inches tall. He had an average build; not to slim but trim enough to know that he tried to stay fit. I guessed he was around forty years old. But...
CrossdressingHey all this is Raj, 23 from Bangalore. This is story of mine having sex with an unexpected person and how it turned out to be one of the best ever had. The story begins when I completed my boards exam and waiting for the results. During that time my family decided to go on a vacation to Andaman and Nicobar islands but I stayed back with a lot of stubbornness as was not interested to roam around so being the only son my parents weren’t so confident on letting me stay home alone so they asked my...
IncestHi , this is Suraj here going to narrate an Incident. I was working in a MNC Software company at Bangalore. I got assigned to a New Project and when I entered the Offshore centre of that Project I saw lots of known faces , many friends and few unknown ones. Among the unknown faces was a late twenties lady . She was like steal a glance on me. Anyways I thought maybe as I came new to this Project , might be she is just seeing how we see a Newcomer. Time passed , I was getting Knowledge transfer...
When Jake first realised he was attracted to his mother, he had no idea that his lust would take such an unexpected turn, leading him down roads he never would have imagined in his wildest dreams. Jake was eighteen, and had just finished high school when he started planning to seduce his beautiful, 42 year old mother. Just the thought of sucking on Lucy's big, delicious breasts was enough to make Jake's uncut 7-inch cock stand up straight and start oozing with pre-cum. Following the advice of...
A Sudden Turn Of Events It sounded so simple. All I had to do was spend a degree of time with him as his companion - his 'female' companion at least that was the plan. A facade maybe, but one that would project a convincing enough image of being his attractively dressed, feminine partner and a woman on his arm. He wanted the vision of an ideal housewife, a homemaker and as an added bonus, if at all possible, someone who could maybe even fill in as his secretary! This role wasn't...
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...
Author's Name: Lee Anne Montgomery ([email protected]) Story Title: Woman Partner (Chapter 27, An Unexpected Turn of Events) ******************************************************************** This work is copyrighted to the author (c) 2003. Please do not remove the author information or make any changes to this story. You may post freely to non-commercial "free" sites, or in the "free" area of commercial sites. Thank you for your consideration. I look forward to, and hope...
She was locked in her room doing god knows what and I was chilling in my room in nothing but a pair of sweatpants watching a UFC card on some random streaming site like I always do. (Fuck paying for PPV) When all of a sudden, my sister walked in, wearing a pair of short sweat shorts and a t-shirt. "Hii, what are you doing," she said, glancing over at my computer screen. "Eh, just watching the fights as usual. What about you, What you up to?" I replied with my eyes still fixated on the...
Hello again everyone.I hope u remember from my last story “blissful pleasure beyond imagination” Just to refresh your memory,I am Rajat ,25 years from Bangalore working as a part time gigolo.I would like to take this opportunity for the overwhelming response I got from you guys and ladies So without taking much time,lets come to the story in hand After my first encounter..I was wondering how to get more clients when one of my friends suggested me a site called locanto.So I put up an ad there...
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...
This story is a bit long, but I hope you all enjoy it. Feel free to leaving any comments, good or bad. ------------------- I stood outside the window of Room 5B of the Lucky Aces Motel, patiently regarding my fingernails. Could probably use a manicure at some point, I thought. Inside, I can hear the muffled voices of Ted Ryan and Meg Landy. Ryan is a 38 year old married father of three boys, and Landy is a 24 year old sales woman at the car dealership at which they both...
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 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 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...
Hi this is Rohi, I am gonna share with you a story of me and my School friend I use to live in a rented house in Mumbai alone. My daily chores include of morning office evening making dinner and sleep.one day I was bored of going office so decided to skip by giving reason of not well. It was raining heavily outside suddenly I called my school friend Priyanka who was working in nearby area and told her to visit at my place as I was alone and bored . She came within an hour fully drenched in...
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...
Unexpected Mommy - Part 1 By Trish5160 My name is Alex. I'm 14 and out of three boys born in my family, I was the youngest and like the runt in a litter of kitties. I am either blessed or cursed with gynecomastia, depending on your perspective. Gynecomastia is unexplained breast development in guys. No one really knows why this condition exists or what triggers it. There are a lot of theories, one being an imbalance of hormones at birth. A boy like me who's body has produced...
I have always loved reading. I read all sorts of books, both fact and fiction. I like travel books, history books, biographies, mysteries, murders, in fact all sorts of reading material. My very favourite are short stories with a twist in the tale: Those clever stories that have an unexpected ending. A favourite author is Jack Finney whose tales are often about shifts in time. The titles of his various books on Amazon give the clue to his obsession with time - “Time and Time Again,” “About...
I was going home after a long day’s work and didn’t feel like driving in the crappy weather. It was raining cats and dogs, anything was hardly visible and roads were flooded. In that weather, I found a girl looking for lift. I had to stop and I watched her as she slowly walked towards my car. She stood at the window hesitating. I assured her I am not some kind of psycho. She smiled and slowly got in. I turned on the blower, she was dripping wet. I started the car and slowly drove around. I...
ShemaleDennis had the whole thing planned out, start to finish. That's what he told Tyler, the day before, when the two of them had met at Dennis' dingy, makeshift office in Miami. "The rocket leaves tomorrow morning," Dennis said. He leaned forward on his formica desk and pointed vaguely at Tyler. "And you're going to be on it. You blow this part, it's your fault. Not mine." "I'll be there," Tyler said, nodding furiously. Tyler would agree to anything at this point. Anything to get him out...
An Erotic Turn of Events: Chapter 1We own a modest home that has a large apartment on the lower floor. We currently have rented to a very nice woman I'll call her Cathy. She was an attractive woman with bedroom eyes and a body well proportioned. I found her very sexy and she dressed that way. She was friendly and almost always said hello when I saw her, often with a certain look in her eyes that made me feel a little weak in the knees. She often spent long periods away from home and could be...
Turn Of EventsBy: Londebaaz ChohanAlly Inc. a freight shipping, moving and packing company was still a family owned business but of course growing fast. Somehow the nearby school authorities were able to convince the elderly chairman of the company to provide some jobs to the suitable candidates after they graduated from the school and to build a better rapport, school also agreed to provide young volunteers for the company; eager to learn the job with a hope that after their graduation, they...
I would like to again thank Ms. Sharon Johnson who had the courage to edit my poor spelling and grammar. W/O her help this story would be less than half of what it is now. Thanks to her, this story is much more romantic and loving. Her hard work is sincerely appreciated. Thanks Sharon! From the man’s viewpoint: ‘Good night my love’, I said as I let go of her hand and watched as she closed the door. Standing there in the hallway, I wasn’t sure how she really felt about tonight. If only that...
After a long day at work, I'm sitting wearily in front of my computer. I need relaxation, the thought of spanking relaxes and excites me. I start to click through various websites. At some point, I discover a German event site called Arsch Events, doesn’t sound original, rather cheap and vulgar. Nevertheless, I look at what there are for events, after all, I don't want to attend an event, just browse a bit. The following events are listed:Spanking School Spanking Court Spanking...
SpankingUnexpected Consequences A cross-dressing husband is caught, understood and surprised! My gorgeous wife had taken the weekend away to look after a sick friend of ours and would be away from Friday night to late Sunday. I had mixed feelings, being sad at her absence over the weekend but.............well my hidden 'special' needs were screaming out for fulfilment and here was a rare but opportune time to indulge them! Saturday mid-morning saw the sudden re-appearance of Claire. I heard...
Paul went out into the hallway wearing a red nightgown and housecoat, checking to make sure the coast was clear. Once confident that nobody else was upstairs, he signaled to Tyler, who made a quick, butt-naked dash from Paul's room to his own. Yes, there was nothing wrong about what they had just done; and yes, they were both immensely glad that they'd done it... but that was the kind of thing that stayed a secret between the two satisfied participants, whether they were men, women, or a...
I stood naked in front of my full length mirror. I absently stroked my shaven pussy as I thought about my evening with Gerald. It had been two weeks since we had our unexpected encounter. I constantly thought about seeing him again. He hadn’t come back the following day and I was beginning to think he was regretting what he had done. I didn’t completely blame him, I mean he did have a wife and kids. I’d better get dressed, I thought. I was meeting the girls downtown at our favorite bar. I...
Two totally true stories from when I was much younger. Two different strangers (both of them hot by the way) try to hit on me. And they both succeed...Story 1: I was 22. Me and a friend walk into a jazz bar for one last drink to cap off a long night of bar hopping. A live jazz band was playing and they were very very good. The place wasn't crowded but it wasn't empty either. It had a great vibe going that night.I notice a very pretty woman with a hot body sitting on some much older guy's lap a...
Unexpected MorningWhen looked upon her eyes shined as if to radiate the passion for life which lay within. Eva stood in the cool morning air, her flesh tingling after the cold water of the lake. Every morning she took delight in the peace this sheltered lake gave her before the day really began. It made her feel centered and had the effect of purifying her of any worries she might have of what the day held in store. But as she stood there naked letting the suns spring rays dance on her body she...
It was a warm spring evening and the smell of the rains from that afternoon was still in the air. With the windows of my truck rolled down as I drove, I could smell the sweet smell of the spring plants mixed in with the wet stone smell coming up from the streets. I enjoyed the refreshing air. I had been home alone, bored, and decided to seek some excitement. I had no idea what awesome experiences were in store for me this night. In my head I had been going back and forth about where to go. A...
I had been house sitting for the last week while friends were away. A beautiful home that had a gorgeous pool and hot tub that I had been dying to use. Unfortunately terrible weather had prevented it until today. Today was perfect for a lazy day lounging by the pool and I intended to make the most of it. I slipped into my bikini, grabbed all the essentials for the day and made my way to a banana lounge where I could read, doze and work on my tan for as long as I wished. By mid-morning I'd...
Straight Sex“Just a minute,” I yelled. Rolling out of bed I picked up some random clothes that where laying around, not bothering to check exactly what I was putting on and not caring at this time in the morning. Whoever was knocking had better have a good reason for waking me up early on the weekend. There's no way I'd be able to fall back asleep either. My German Shepherd was barking, it's tail wagging, no doubt happy I was starting the day early. I walked to my front door, running my hand through my...
Unexpected MorningWhen looked upon her eyes shined as if to radiate the passion for life which lay within. Eva stood in the cool morning air, her flesh tingling after the cold water of the lake. Every morning she took delight in the peace this sheltered lake gave her before the day really began. It made her feel centered and had the effect of purifying her of any worries she might have of what the day held in store. But as she stood there naked letting the suns spring rays dance on her body...
Hi guys, I’m Varun(name changed) from Bangalore. I’m a bisexual strongly attracted to men who are older than me. Possibilities do exist. So if you wanna know more about me and my experiences, get in touch with me. So this story is about an unexpected encounter that happened to me last year. I was 19 years old then. I was always fascinated to see new dicks and gave a fetish for underwears. Also, I like exploring sex in public places. This story outsets when I wanted to inquisitively experience...
Gay MaleUnexpected MorningWhen looked upon her eyes shined as if to radiate the passion for life which lay within. Eva stood in the cool morning air, her flesh tingling after the cold water of the lake. Every morning she took delight in the peace this sheltered lake gave her before the day really began. It made her feel centered and had the effect of purifying her of any worries she might have of what the day held in store. But as she stood there naked letting the suns spring rays dance on her body...
This story is the continuation of the previous story. As I told before having sex with one girl led to a snowball effect. It’s really surprising to see that there have been so many women around me; whom I thought didn’t even care about boys or made people feel that they were confined to themselves; were not like that. It was the case of Janani Priya that taught me a lesson. We are all deluded about people. We just can’t find who is what. Ok enough philosophy for today. Ill introduce myself...
Hi guys this is a story when I was I had a huge crush on a girl called Neha. We were good friends but she always used me in her studies to get her work done. I helped her thinking that she respected me and we were good friends but that was not to be… After knowing each other for two years we were supposed to go for a college trip to Manali for a couple of weeks. My friends always told me that she was a bad girl and stay away from her but I never listened. I wanted to propose her but I never...
This happened a four months ago. We have one manufacturing at Nagpur. As I am the head for India and as part of employee engagement we used to have our family day function at each location. I had requested my assistant Asha to go to Nagpur and help the team a week before so that we have 100% participation from employees and their family. While discussing this I got a call from Nagpur factory that employee involvement is not at all there and that he is confused. Local HR is busy with day to day...
Hi! All friends, I am back with another interesting episode of my unexpected. but exciting and real encounter. Your valuable comments are welcome. After that exciting evening in his house, we became very intimate and one day, he planned for a long night-session of sexecitement, as his mother would return only after one more week, but I discarded it as impracticable and left it at that. The following Sunday, Sanjay anna(uncle) lunched with us and with my parents’ permission, both of us went to...
Gay MaleHello friends, hope you liked my earlier story with my master. Here is another one for you to read and offer your valuable comments and encouragement With the summer camp and the feverish activities associated with it coming to a close, and sir’s absence for nearly three weeks( on domestic reasons), I felt miserable, like a fish out of water. The fantastic taste of that unbelievable and unexpected sweet forbidden pleasure with sir (My master love-locked me -3) was haunting and making me...
Gay MaleUnexpected Outcome At the ripe young age of 25, I had everything going for me. I could get all the dates I wanted and with almost any of the town's hottest- looking ladies, too. I had college degree and a good, well-paying job, a nice car and a decent apartment. Then, one day, my world came crashing down around me and everyone else too, for that matter. No one knew it at the time for the only news available at this point was that the Earth was going to have a near-miss experience...