random hookup stories

It was a Sunday afternoon and I had taken a long weekend off from work as I was too bored with my life. I had recently been through a very rough patch in my life. I had broken up my 10-year-old relationship with my boyfriend after which I was into severe depression. I wanted to stay alone for this weekend but somehow staying alone made me remember all the bad memories. So, I decided that Sunday night I would just let myself free and go out. I dressed up a black cocktail dress and applied bold makeup to feel different. I just wanted to feel someone else and not myself that day. Once I reached the nearby bar, I saw a few familiar faces as I used to visit this place often with my friends but tonight, I was all alone. I had never thought that soon I was going to meet a stranger who not only ignited my sexuality but also made me forget about everything around me.

Alessia was always a wild child and that what attracted me to her at first. There was this need to subdue her and fuck some sense into her, may be a wild sex session with my maid. I had made her my submissive and I could fuck some sense into her on a regular basis. I loved doing that – fucking her, especially if she resisted me. I smile at that thought and enter my apartment.

His eyes were following her every move. Katya was serving the drink in the billionaire’s party, moving graciously, heads down, shying away from anyone who made a pass at her. His gaze had so much intensity that even I could feel them from a distance, the strength of kinky sex and roughness. I had no idea what he has in mind but I was about to find it out soon. I, Anaita, am 24 years old, just the same as Katya. We have been friends for quite some time now and we even work for the same catering company. Katya is a shy woman of 23 years of age who thinks she is not beautiful enough. She would have a fit if she knew she was the centre of attention of a billionaire prince himself.

My name is Justin and I am a 22-year-old guy with a good height and an average physic. This incident is about an encounter about how I got fucked by a neighbour. I was alone at the home once. I took advantage of the opportunity of being alone and had a couple of glasses of whisky. After that, I sneaked in my sister’s room, took one of her dress, wore it, applied some makeup and started roaming in the house. Then, I pulled my dress up a bit and swayed my ass like a sexy woman. However, I forgot the window of my apartment was open. When I went to close it, I saw that the 63 year old neighbour of mine was staring at me and was clicking my pictures. I closed the door, undressed and slept.

I was dating Julianna for a while now. She was all of 21 and I knew she was it for me. I also knew that she hadn’t had a boyfriend before me. I had proposed her that Christmas and we were engaged to marry. It was a beautiful summer day and I had asked to take her on a picnic just to spend some time together – unsupervised. I hadn’t intended it, but we ended up making love under the open skies that day and devouring my virgin fiance.

The stock market today had given me a lot of profit, I was on the way to my apartment. I will have to wait for 10 full stations. I took a seat and started scrolling my phone, I had a lousy weekend ahead of me, many people had sent messages asking about my weekend plans. Two stations had passed and I was starting to feel sleepy, I gazed around me and found a cute guy staring at me. He had a huge book in his hand and a bag-pack, most likely a college student I thought. As soon as he noticed me looking at him, he turned away. The next station arrived and he stood up, it was a bummer, I thought he was leaving but instead he offered his seat to an old lady. How humble of him, didn’t know generations like these still existed. I noticed his broad shoulders and sleek back, when the seat next to me got empty I gently tapped on his shoulders and asked him to sit next to me. He got all shy but took the seat, “hey” I said, “hii”, he replied he had brown eyes and matching brown his frizzy hair which fell on his eyes. Until then, I had no idea that things are going to get hot and he will become my subway gay partner.

I am Sagar, a 24-year aged man, or woman you might say. I started loving the clothes of the woman since my teenage and I like turning into a woman. I always use to wear women’s nightwear while sleeping and even during the day I used to wear a bra and panty under my men’s wear. It used to give me immense pleasure. One day, I went to watch a late night movie. Beside me, a handsome man was sitting. After half an hour or so, I felt his hands caressing my thighs. I was a little confused but I was enjoying his touch. So, I let it be. His caress deepened and my erection was getting stronger with each stroke. Slowly his hands touched my hard cock and I sucked in my breath.

I was in my second year at law school, when a new teacher joined the faculty. She was in charge of teaching us Criminal Law. Five-foot-six, slender figure, dark brown hair with a few loose curls, our teacher Serena, was mesmerizing to say the least. She had a perfect cleavage and her ass was tight. As she stood in front of the class, doing her job, all I could do was stare at her. I imagined all the things that I wanted to do to her. I wanted to hold her and lick her into oblivion. So in order to get close to her, I approached her after class with the request to help me with the subjects personally since I was having difficulty in understanding the theories. I was just taking my chance but didn’t know I was going to experience bliss- my first lesbian experience with my teacher!

I had a high-flying career and was married for the last 10 years. But my husband was mostly away on business most of the year, saying that right now was the time to earn. I agreed with it. We could earn now and relax later. But lately, I had been feeling lonely and quite horny. I was angry and frustrated as I missed sex with a person. But because we had mutually decided to live like this, I couldn’t say much on it. I couldn’t say I changed my mind. So, I waited for things to change. I wanted get banged hard because I’ve been missing sex.

If you haven’t read the previous parts of this story read part-1 and part-2 to get the glimpse of this virgin sex story. BJ and I had been seeing each other a lot now. Ever since having sex on that day, it was difficult to be apart from him for more than a few days. We would talk on phone and I would wait for his call every day. I was loving this part of our courtship. We would still steal kisses whenever we got a chance, but I hadn’t had sex with boyfriend again. I was dying to try new things with him and soon the opportunity arose.

I was quite a skinny man at 18 and hadn’t quite filled out yet. I was not too attracted to girls, but Mom said that I would eventually. Because I didn’t care if girls looked at me or not, I never tried to get a hot body. I had a best friend, Shane with whom high school was not that hard. But one day things changed. That’s my story of how my best friend became my lover.

I remember the time I went to Mr and Mrs Lewis’ parties. Every year they threw an annual bash, complete with over the top decor and food. That year, I was sixteen and a hot Latina was serving cocktails. I was instantly attracted and got a hard on. She was wearing this short black dress, showing off her toned legs in heels. I was going to fuck her in those, I knew it. My kinky imaginations led to outdoor sex with the maid.

I am a horny lady and as my husband is out of town most of the time, I am usually left alone and find means to have sex with someone else. It was raining heavily last night and I was drinking a glass of wine while watching “Fifty Shades of Grey” on Netflix. I wondered how a man can be so good in bed. That’s my real story of how I ended up fucking a delivery boy as I was aroused badly.

My friends and I were planning a weekend getaway to my lake house where I experienced orgy with a shemale. I didn’t know that they were planning my birthday party too. I packed up and all of us headed to the house. Soon it was evening and I hear the doorbell. “Surprise delivery!” my friend Sean shouts. I go to the door and see a tall blonde walk in. She is dressed well, some cleavage too and heels. She has a large paper bag in hand and she sets it down on the coffee table.

I was working for Ash for a few weeks now and I knew the way he looked at me. He stared at my ass way longer than an “employer” should. And I was attracted to him, horny at times, masturbating to his thoughts, to an image of his naked body. I will tell how the attraction moved ahead and he spit cum in my panties.

It was 12 am at night and I just couldn’t get my eyes to close. I was thinking about Shari, how hot she looked tonight while setting up for dinner. She was employed with me and I was attracted to my maid. I couldn’t explain it, but it was there. She had come to me a year ago seeking employment. She studied during the night and worked for me during the day.

I was late! I was running for an internal meeting and when I burst into the conference room, I saw it was empty? Only Sean was sitting there looking amused. “The meeting is cancelled,” he said in an understanding voice. I take a breath of relief and sit on the nearest chair. I had a lot to do, so I thank him and start working there. It was a Friday so most of the staff leave at around 3 and it’s only me and him working. We didn’t disturb each other at all while working but now I feel something change and it became a fantastic night.

Shana was sitting on the bed with a sultry look in her eyes. I was going to fuck her, fuck a shemale. “ I am going to suck your cock and fuck your ass,” I tell her. “Yeah, I will do the same to you. Now come here. I want to suck your lollipop,” she says and licks her lips. The tone itself makes me go wild. I go closer and let my naked and hard dick hang in from of her. She takes it in her hands and rubs it between her palms.

This was the third time I was meeting Xena. I was having an affair with her and I had kept it a secret from my wife. What do I say? I was addicted to her or rather my cock was addicted to her pussy. And she was naughty as hell so I enjoyed doing things with her of sexual nature. I don’t feel bad having an affair with a hot escort like Xena.

I am Neila. I will share my story of how I my boss had BDSM Sex with Domestic Servant who worked with her. I was 19 years old when I signed up a job for a domestic servant. When I reached the place, it was an empty room. All it had mirrored walls and in the middle was a metallic table. I had no idea what to expect. I signed up because the pay offered was good and they were offering food and lodging. I had to pay for my student’s debt. While I was deep in my thought, I jumped up from my place when I heard someone walking in. It was a middle-aged woman. She looked sexy in her leather cat suit. She was carrying a cardboard box and a riding crop. Her long thick hair was neatly tied in a high ponytail and her heels made a clicking sound when she walked.

Hello friends, my name is Ricky and this is the story of how I became a paid cross dresser two years back. It was during the Christmas holidays when I was in need of some money. I called my friend Kris and asked for his help. Though he agreed, he asked a favour in return. When I met him, he told me that his job was in danger and that the only way to save is by pleasing my boss. He told that his boss was a bisexual who had a thing for cross dresser. I used to dress like a girl at times but never showed it to anyone. Kris came to know about it when he once caught me in a floral maxi dress, masturbating myself. That small incident changed my life and I became centre of attraction for rich gay men.

I had the will to live happy, that’s what my Nana had said. Today at 28 with a body on the heavier style, I still am sassy and outspoken. Sometimes I do feel let down by my body but I feel I make it up with my will to stand proud and strong. One day, I chose to visit some adult dating websites portal and signed up to see what it is about. What did I know that I would meet someone special from a dating website.

I was a forty something married woman, but I didn’t enjoy my sex life. My husband was always too busy and often away on business trips. I needed sex and for the first few years I used vibrators and other toys to manage. But I had always dreamt about fucking a boy toy, a young one and riding him till I was satisfied. And one day an opportunity knocked at my door.

I had never thought about BDSM as a sexual act that would appeal to me. So, I never even thought about trying it. But the first step into BDSM sex, for me was with someone so sensuous and beautiful, that I enjoyed it thoroughly.

I am a bachelor and working all day along with living along takes a toll. I lived alone in a PG and there is a maid that cooks and cleans for me. Slowly I got addicted to watching porn. I usually used to watch it alone and masturbate. But slowly I started becoming more addicted to it and started watching whenever I could. The story is mine where I had sex with my PG maid, so read on more.