My next-door neighbour was hot. She was a thirty-something single woman and man she had the body of a goddess. If she was the one I could lose my virginity to, I’d die happy. I was a single, virgin 18-year-old boy and she was all woman with curves to kill for. That day, she saw me watching her, so she smiled and waved at me. I returned her acknowledgement and decided that now is the time. After 5 years, I am writing my experience of how I had lost virginity to a woman anyone can die for.
My name is Aryan and I was posted in Chickmanglur, an area with a lot of hills and coffee plantations. I was sent there for handling the production work. I was given a guesthouse to stay and a house-help, a man named Hari, who helped me with basic things I needed. His wife used to prepare food and do cleaning stuff for me. His wife, Rekha, was a very beautiful and desirable woman. I am going to share my story of how I came closer to her and had sex with the wife of caretaker of my guest house.
Jace and I had been dating for some time and had even indulged in sex. However, when it came to anal sex I was a virgin. As Jason likes to call it “this ass is mine”. Truly it probably is, as he is the only one who has been there.
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.
When I was 12, I went to shop for shoes with my mother. I would walk around the store, making my mother laugh out loud. The onlookers at the store, would often look at me in astonishment and wonder, “How is this little boy handling pencil heels so well”?. My mama knew it back then that I was born different and she fought the world to make me who I am today, a proud cross dressing gay male.
I had a maid working for me for a year now and often I had caught her masturbating. She didn’t know yet, but when she thought I was away, I would secretly watch her as she cleaned my bedroom. And one day when I caught her masturbating on my bed, I gave her a good pounding – in her pussy with my cock. Now she would sometimes shamelessly walk around only in an apron, showing me her cunt. So, one day I brought James, my friend, over to watch my juicy maid.
For a woman, it is often difficult to decide between someone who fulfilled my sexual desires and someone who makes a great father to my kids. I love my children but lately, my sex life wasn’t even remotely exciting. It was the same missionary after Sunday lunch when the kids were napping. And I was frustrated.
I met Lisa in college and then we also had some steamy webcam sex. But that’s not the end. It was because she wanted to relax sexually and didn’t want the hassle of dating a guy. I wanted her. Oh, I so wanted her. But she kept denying me. And now we are stuck together on a plane. Right next to each other, in economy. Why, you ask? Because we are on a freaking college trip or an educational trip if you prefer. That was it. I had some sexy moments up in the air itself.
I am recounting this tale as it happened when I was in college. I was still discovering my sexuality and wanted to try everything. So, I ordered some sex toys online, keeping it for future use. I had a girlfriend and I would fool around with her. We had had sex occasionally but I was a young horny guy, wanting to explore more – try toys and some kinky acts. And I was preparing for it – a sensual and sweaty night.
Daryl was supposed to be my one night stand, but instead he took pleasure in fucking me again on a secluded beach. It was the attraction that I blamed for this. We met on the night before but couldn’t get to fucking because he had a medical emergency…yeah, he couldn’t get his dick up. I laughed and laughed. But he found me the other day, when I was lounging on the beach. That’s my story of how he fucked me on an open beach!
I am 45 years old and my name is John. My wife is a socialite. She has so many friends that she is invited to various weddings and parties all the time. I am a person who likes to stay indoors after a long day of work. Although, this one time she forced me to attend a wedding with her. I had come home early from work and so, I agreed. Didn’t know this would turn into an affair with wife’s friend.
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.
The first time I had sex with a man when I was nineteen. I knew I was attracted to other men and boys but in my very traditional family homosexuality wasn’t even talked about. I didn’t realise what my feeling meant. But that night, my first gay sex experience with a man changed everything.
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’m not saying I was a bad lover to begin with, because who in their right mind willingly cops to something like that? What I will say is, that before I accidentally found my way down a porn channels rabbit hole, I was much less aware of all of the incredible things a single body can do and feel. That’s how it led to immense sexual satisfaction.
I had been lonely for a while and I missed having someone to talk to or even have sex with. I was bored and my work kept me busy 6 days of the week. Italy is a beautiful place to live but if you are single, nothing that a place can do for you. I wanted some company one night and decided that I would try a phone sex service. I was open to talking to a stranger on phone sex and get something to manage my boredom and loneliness.
I was at my farm house. I was just remembering the good old times I had spent with my husband at this place before getting divorced. However, ever since my divorce, I had a couple of dates with younger men. It was always fun to indulge with them as they had great energy and they could satisfy my needs. Although, my recent partner John had gone out of the town and I was missing his touch. You need to keep finding ways of satisfaction when you miss someone.
I was a student by day and a firefighter by night. I had joined the team two years ago and was trying to get a college degree by attending classes at night. I often used to silently masturbate when I would go to the library, as I was alone in the evenings, at the almost closing time and it would take the edge off a bit. During one of these times, I saw the local librarian and oh she was hot. Perky tits, tight ass and a low cut blouse. Wow. She would probably feature in my fantasies for a while.
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.
I was practicing as a general physician in a rural community and would often see cases that were out of my scope. However, as I was the nearest doctor, I would see a lot of local patients with various ailments. One day, a skinny and heavily pregnant woman came to my office and boy did that session last. She seemed young and was unmarried. And when she came in, I oblige to her request and I fucked my pregnant patient.
I was meeting a group of guy friends at a bar. It was a renowned gay bar where drag shows were held on Tuesdays. So I went there, a woman. I was bisexual and enjoyed dallying with both sexes. I was enjoying the show, singing along when I went to get a drink at the bar. Max was serving drinks and the first thing I noticed about her was that she had heavy eye jewellery. Piercings and heavy makeup made her eyes pop even more. I didn’t know I would end up sleeping with the Waitress I met there.
Carla, my girlfriend and me were looking at options to move in together. We had just started dating, but my family knew that I was a lesbian, a long while back. Carla was new in my life and it felt like I was dating for the first time. Yes, when she arrived, I felt butterflies in my stomach. I loved what she could make me feel and I knew there was a special connection that makes me horny with my Lesbian girlfriend.
I had an affinity towards women’s clothes and have a lot of crossdressing fantasies. The soft silks, shimmery fabrics and bold colours – I loved them all. But I was a boy and all my friends would laugh if ever a boy wore a pink shirt. And I loved hose colours. I wanted to raid my mom’s closet, wear her dresses, put on makeup and strut like the diva that I was. But I held this in me for many years, until one night I saw my parents. They had dressed up in costumes I believe. My mom was a policeman and dad played a nurse. It seemed they were role-playing, but mom was a man and dad was a woman?
I am a real estate agent and often visit houses or homeowners who want to make a listing for sale. That day was hot and I was sweating, so instead of my usual business attire I was wearing a tank top and a mini skirt. I had an appointment with the homeowner of a large ranch style house which had been recently renovated. I had been eyeing that house for a while as I knew I could get a good commission out of it. The story is not about making commission but how I got tied and ass fucked.
Hi, guys, this is Andrew. I have always been attracted to mature and older women. I used to stay with my family in Miami. But recently I had to shift to Orlando for my post-graduation. To start with I am a 23-year-old guy. I am an average looking guy but quite friendly with people. I started with my course, and I used to stay in a rented flat. I had a classmate named Ugaan who used to live just near my home. So we both used to spend time together playing or roaming. Once he invited me to his place for dinner. I also agreed and went there. He used to live with his Mom Roslin, though she was 45 years old, she was a pretty and attractive lady. One day I went to his place. As she gave me a glass of water, she bent to put it on the table. I saw her cleavage which got me hard. I knew it was wrong, but this made me think about her in another way, and destiny had something else defined for us that led me to have sex with my friends mother.