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 was a part of our college football team and had practice that afternoon. I arrived at the locker room to change and saw this skinny older guy. He was wearing spectacles and talking to coach. That was the first time I saw Laurent. Later I found out that he was a visiting Maths professor. He taught at the university. We slowly became friends, even though we were from opposite spectrum. I was a jock and he was more interested in theorems. Everything seems so good so far right? It went way too far from just studies and I ended up having sex with my maths professor.
I have always heard or read about the extra-marital status bit had never been across any real incidents in my life until a few years ago. I am Nikita and I am 23 years old now. This incident happened when I was 19. I accidentally witnessed my uncle, father’s brother, having an affair with our maid. I have no idea when it had started and why. My aunt was pretty and sexy and every man’s wet dream. And still, my uncle was sexually attracted to our maid. Ours was a huge house, three floors, one for each brother.
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 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.
My boyfriend was meeting me tonight for Valentine’s Day. I knew there would be flowers for me and anal for him. He loved it. Loved the way my tight ass took him, the way I moaned in pain and pleasure. So I waited for him that night, in my sheer blue bra and wanted to get licked in the ass. Then he entered the room.
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.
BJ was my first boyfriend and I had met him at a party with common friends. It was strange how I, a virgin at 26 met another virgin who was 24. He was nice and while friends at first, we moved into the dating territory soon enough. The first kiss was weird and sloppy, wet almost. I wasn’t sure if I had wanted to kiss him and he wanted to very much. Soon our relationship progressed and we experienced first sex soon.
My marriage was a peaceful one, devoid of stressors and shouting matches. But sexually, I wasn’t too satisfied. I was looking for something, wanting something more and this actually showed in my acts. Once, I was fucking my wife and although her pussy was squeezing me in the right ways, I wasn’t feeling excited enough. So much so that in the middle, my cock suddenly went limp. It was then that I thought that maybe I needed a second partner in my life to make more excited.
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’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.
This is the final part of my story Gay Experience with a stranger. I will write in continuation of the cross dresser sex and how he fucked my Asshole.
I was waiting for William to come online. I was pregnant and the pregnancy hormones were making me crazy horny. When he was at home he would fuck me senseless all hours of the day. But he had to go out on a short business trip and I was horny as usual. We had had virtual sex in the morning and now I was waiting for him to help me find release. We were going to try webcam sex.
It was a lazy morning, I was sipping cola when my phone vibrated, someone had pinged me on Instagram. The notification flashed on my screen. Alex had sent me a ‘hey’, I jumped on my seat, my heartbeat pace increased. Numerous questions were popping in my head all at once, ‘why would he text me?’, ‘he might want something from me!’. ‘But what can he want?’, I push back all my thoughts and try to think of what to do next. I don’t want to text him instantly, that would show him my eagerness. Alex was my classmate in 11th grade. As far as I know, he had a pretty girlfriend, I remember stalking her on Instagram. Back in school we never spoke, not that I never noticed him. I did, but our friend circles were quite aloof from each other. I also knew he was having friends with benefits relationship with quite a few back then.
I have been into cross dressing for a while now and have kept it a secret from my wife. She likes to play and is a dominatrix. Usually, we go into dom and sub mode where I worship her cunt with my tongue as she flogs my ass. I like getting dominated by my wife. But tonight, she saw me, in my female form. I was at a local club, which she doesn’t frequent, with my gang and we were all dressed up as pretty women. I was wearing her glitziest dress and had a full face of makeup with a wig. Yet she recognized me. Now I am going home and I am not sure what awaits me.
Hi, I am Shail and I am 21 now. The incident I am going to narrate happened in high school when I was 16 and became slut of my friend. My parents wanted a daughter but I was their only kid so, my mother often used to dress me up like a girl when I was a child. That stayed with me as I grew up. I used to dress up as a girl in the solace of my room as my parents strictly ordered me not to dress like a girl ever. I had no idea this will change my entire life. One day I was dressed up as a girl when a friend from my high school came banging in my room. It was then that I realised my room wasn’t properly locked.
Alyssa is my sexy servant. Not literally but I like to dominate her sexually. It isn’t BDSM – our relationship, but just that we like role play where she is at my mercy and I can do all kinds of things with her during playtime. But that time I invited a common friend Walter to enjoy playtime with us.
Sheila was going to see Dr. Dray. He was a supposed gynaecologist who specialised in herbal medicine. “What was that?”, Sheila had thought, but she went anyway. When she arrived at the clinic she was met by the nurse and told to lie down with her legs open and panties down. As she lay, she saw that the nurse was watching her and her eyes were glued to her cunt. She was going to meet the horny doctor there.
Shana was my aunt – my dad’s stepsister. She was a little different from my stiff collared family. She was visiting this week and I was going to see her after five years. I was eighteen now, ready to join college. It was my last week at home and Shana who was 30, was visiting. Destiny had different plans and I had sex with my aunty.
I have been exploring my sexuality for a while now and while I cannot confirm that I am a straight man, I am still not sure which category I fall into. But a trans person is living right next to my apartment – Benny and I feel like doing dirty things with him. I mean like he dresses so well and rocks a full face of makeup with a slight beard. He does have generous boobs and I have thoughts of my trans neighbor, every time.