gay crossdressing sex stories

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.

I was living alone for a while now and didn’t have a permanent partner. I did enjoy casual sex once in a while and had a vibrator ready in my drawer. Lately I had been dreaming of my ex a lot and had dreamt about having an affair with my ex-boyfriend too. I don’t know why, it just happened. And then something unthinkable took place. He moved in next door!

I had always focused on having a good body and participation in athletics had kept me fit. But today I was out of a job, being freshly fired. I hadn’t thought about what I would do as I had a mountain of debt and I was also raising my 1-year-old nephew. I needed something asap to pay the bills and feed ourselves. It is at this time that my cousin introduced me to Jofre who produced porn films. And tomorrow I was going for a screen test. Getting kinky while watching porn is different and being watched is completely different.

This happened as a result of a challenge. A dare to be specific. It was a Hen Party and we were at a place with many other girls, some of whom I didn’t know. I am Jennifer, 26 years old. We were drinking and having fun. There were games and one of them was truth or dare. Feeling brave I took a dare and I had to kiss a girl. I didn’t knew this would lead ahead to a beautiful lesbian sex experience.

When I turned 18, I was moving out to California for college. As my stay wasn’t figured yet, my mom invited my dad to our home and proposed the idea of me living with him and his wife for a few months. My dad and his wife were very happy to hear that and came all the way to Toronto to pick me up. I was never close to my dad, but I always remembered my first experience of sex with my stepmother.

They always say, the first time is shocking, the second surprising and the third, well, there is no stopping. I have been a very adventurous and rebellious girl. I like to question things and people quite often, which earns me, quite a reputation. With this typical characteristic of mine, I was asked to leave my home and never show my face again, by my own father. They said that they have tolerated my gypsy spirit, but they can’t anymore as they were answerable to God. How did everything change and how unconventional anal sex brought back pleasure in my life is what I am going to share in this story.

I came out as gay to my parents when I was around 25 years old. I knew that I wasn’t attracted to girls, but I was finding it difficult to have a meaningful relationship. I wanted hugs and cuddles, quiet nights with my partner just watching a movie and hot sex of course! I did meet attractive men of my age, but most were just wanting to have fun or wanted to explore. I wanted more, something more long term. And I guess it was because of this, that I didn’t find many partners. My sex partners were also reducing as I would start checking if he could be the one. I badly needed a passionate night with a gay partner soon.

The newest trend in the dating industry is not a new app but a whole new experience of dating someone. It is called a girlfriend experience. As the name suggests, you can now hire a beautiful girl for a day to walk around the city hand in hand or just cosy up in bed all afternoon. These girls are highly trained escorts. Unlike the traditional understanding of an escort, these girls go beyond just sleeping with you to deliver utmost pleasure in their time. You are literally like friends with benefits, who do not shy away from lending an ear when you are in need. Toronto being one of the most craziest cities of Canada has also the need of some softcore romantic life instead of just sex and there comes the need of girlfriend experience escort in Toronto.

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 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.

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.

I was an active guy who liked sex quite a lot. In fact, before Janey came into my life, I was sleeping with a new girl every night. Then Janey came and we got into a relationship. One year into it, my urges seem to be coming back. Although Janey is enthusiastic about sex, I can’t shove my dick in her 24/7. I had sex cravings at times and didn’t know what to do about it. Then I found out about cam sex but also banged my girlfriend hard after doing cam sex with other girls.

When you are married for 10 years, your sex life tends to get a bit boring. It is the same old missionary followed by doggy or little suckity-suck here and there. Sometimes, even the thought of having fun with a new partner, runs through your mind. But, it’s all the same. You will spend the initial years of your relationship, discovering the body of your new partner and then it all goes back to where you left from. So, the question is, does that make it a wise investment? Well, in my head, its not worth it. So, I tried to put in a bit more effort of making our marriage interesting. I started off by re-observing everything Ronald did on everyday basis to keep sex life active.

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.

The day had arrived when I was going to shoot the movie. Jofre was on set and there were more people than last time. I told Jofre that I was uncomfortable with so many people on the set. He assured me that once they set up, the actual shoot would only have a handful of staff and they would be discreet. That gave me some courage and then I saw Joanne walk in. She was looking good but had too many clothes on I guess, so she went to the changing room and then re-emerged in a transparent shirt and shorts. Enough imaginations of banging the blonde, I wanted it quick, real!

I had been working for Perez for a year and had seen his roving eyes watch me. I knew what he thought of me and wanted me to sleep with him. But I hadn’t given him that opportunity yet. As a result I did get secret gifts and requests to give in to him. The truth was, I was attracted to him and was just about to give in. That mutual attraction with my master would lead to a blasting sex, I didn’t know.

My name is Ashley, I am 18 years old. Most people would describe me as outgoing and laid back. My parents are quite successful. My mother is a human rights lawyer and my father runs a large company. I guess that’s why they place such high expectations on me. They say laid-back means lazy and my only drive is to a party, but what do they know? I will get to my dad’s secretary part of the story little later.

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.

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.

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.

The days were monotonous since they were confined to work and a dying relationship. I have been in a relationship with this amazing guy for almost two years. Initially, the bond was thriving, so were our genitals. But with time, he grew more occupied with work and consequently, the time he devoted to me in bed reduced and I had to rely on the vibrator in the drawer. Touching myself, thinking about the men in the magazines and porn had a drastic effect on my sexual fetishes. I admit that I was tired from the lack of action and I cheated for sex.

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.

It was a normal Friday during the summer month of the year. Me and my friend had decided on visiting a strip club far away from the city which was famous for 5 strip dancers who used to run it. The strip club was very popular because of the variety of themes that the boys incorporated in their dance and strip shows. I had never seen their pictures but had heard a lot about these strippers. I was excited to visit this strip club as I had never been to a male strip club. I had never thought in my wildest dreams that I would end up having sex with a stripper during my first time at a strip club. Once we reached the club, we saw that the crowd was full of women and some gay men dressed in short and kinky clothes.

Shreeja and Neha looked at their husbands lovingly. They both have bonded together very well and they were glad since they themselves have been inseparable since childhood. Naman put an arm around his new buddy Raghav and looked back at his wife chatting happily with her friend. He announced they are going into his study for watching the game and having a few drinks.

Ed clicked on the ad that kept showing up in his browser. It was an invitation for free online sex. It led him to a portal that had a list of pretty girls.  It seemed they all wanted to chat with him..a sex chat. He scrolls through the list just for the heck of it and then his eyes fall on someone called Amber. He clicks on it and she makes an appearance on screen. That was the beginning of finding pleasure through webcam sex.