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I remember being stuck inside my apartment during those rainy nights. Boredom and frustration lead me to chat with strangers online and suddenly my rainy nights weren’t so depressing anymore. I saw Katya that night and just loved the way she responded to me. Even though we were physically apart she definitely lit my fire.

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.

Sheila and I had been seeing each other for two weeks now and she is my lesbian partner. I was waiting for her naked in the bathtub. I press my nipples thinking about her as I take my bath. Soon I am dressed for bed and its then that she comes in. She sees me in see-through nighty and a naughty grin overtakes her face.

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.

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 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.

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.

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!

Hi, my name is Sam and I am a 26-year-old, slim physic cross dresser. I am a fashion designer and have a thing for female clothing. Not only I love designing female clothes but I also enjoy dressing as a girl. Coming to my story, this incident took place some years back when I was around 20 years old and had cross dresser romance session with my real Aunt. With fair and curvy physic, I can look more girly than a girl with my cross dressed attire.

This is the second part of my previous story. I will write about how I had rough Cross dresser Sex with him.

I never believed in online dating. Although, I had been single form quite some time now. So, a friend nagged and tricked me in to registering on one of the sites. I did not use it for almost 8 days. However, it was the weekend and I had no plans. So, I thought of checking the dating site if there’s something interesting. I found out quite some good options and thought that connecting with them is not going to cause me any harm. Little did I know that I was going to experience something crazy and it ended up having the best sex but was dramatic at the end.

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 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.

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?

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 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 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.

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.

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.

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.

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.

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.

I was working as a janitor in a college and I had an unbelievable experience. I wanted sex and release for a long time, and one day I got. The series of events leading up to that are also interesting and it all started with a new professor who had just joined.

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.