I Had Sex With A Shemale And This Is What Happened

I Had Sex With A Shemale And This Is What Happened: Story Time

The filthiest and most erotic experience I’ve ever had… and it just so happens it was my first time with a shemale.

I’ve read several stories of first-time sex with shemales and none relate to my personal experience. So, for those who are interested in how to go about it and what it’s like this is my story.

How Does Sex With A Shemale Feel? MY STORY.

I’ve always been a straight guy as far as I remember. Married for over ten years and never strayed once.

However, sometime during my married life, I began to wonder what it would be like to suck another man’s penis and be penetrated. Don’t get me wrong, men don’t turn me on! Once, I tried fantasising about them but the reality of hairy bums just left me cold and emotionless.

A year ago, just around this time I began looking at tranny and ladyboy porn videos and realised that I was attracted to the male genitals when surrounded by the female form.

Something about chicks with dicks seemed so beautiful and exotic to me that I couldn’t stop thinking about them…

It was at that point that a seed of an idea formed.

Sex With A Shemale: The Brazilian Affair

Two months ago, I packed my suitcase and went on a solo trip to South America, Brazil to be exact. After walking around the quirky streets of Rio; binge drinking and being horny, I found a bar called Balcony Bar in Copacabana beach area.

I was instantly aroused as I noticed a wide selection of Brazilian shemales more than willing and eager to please me. One of them, Antonia, was giving me the eye so I came back later for another look…

Whilst I was away, I was constantly battling myself and thinking if I really wanted to do IT. I knew it would have to be special because it was going to be a one-off secret. After hours of soul terror and torture I finally decided to go for it. I just couldn’t fight this fantasy any longer.

Sex With A Shemale: The Shemale I Chose

The shemale I chose was from the outskirts of Rio de Janeiro and called Antonia. She was absolutely stunning, had incredible eyes and a jaw-dropping, curvaceous body. She told me she had a 7 inches long junk and I quietly opened the door to her bedroom…

Sex With A Shemale: A Mature Lover 

I told Antonia it was my first time having sex with a shemale and that I wanted it to be perfect. I explained to her that I wanted to be treated like a bitch, made to suck her big Brazilian cock and fucked in my boy pussy.

To my surprise, Antonia immediately pushed my head down to her cum cucumber and made me suck it. I tried to suck the best I could as I was really enjoying being treated like her little bitch.

Later on, she bent me over and lubed up my arse, while talking dirty to me about how she was going to push her hard shaft inside me. Then, she loosened me up surprisingly quick with two then three fingers, telling me not to worry and that she knew what she was doing.

Sex With A Shemale: She Knew What She Was Doing…

I enjoyed being the one to bend over with my man cunt in the air and no control. Antonia was so hot… as hot as the fire itself… The ways she moved. The way she made eye contact. The way she desired me. I felt completely at her mercy.

She gripped my buttocks and forced her junk in as I groaned. She got into a rhythm and pushed her dick deeper and deeper inside me, spanking my arse and telling me I was her little bitch in her soft, Portuguese accent.

Later, after about ten minutes of this incredible sensation, I pushed her back and asked her if I could ride her. She smiled and laid back. I jerked off a little as we kissed and then I also sucked on her soft, fake breasts. I licked her brown, tanned skin and then slowly lowered myself onto her.

Sex With A Shemale: It Was Incredible 

The experience was incredible. I found myself riding her cock harder and harder, groping her tits and moaning like I’ve never moaned before. I kept riding her hard until she told me to slow down. My tight, virgin arse was making her come. I leaned and remembered her that she was the first person to ever enter me. And she kissed me.

We fucked like this for another hour, I was aware my time was almost up but she was enjoying it and so was I.

The whole time I was with her, I felt like such as slut. A filthy whore. And… I was finally free.

At last, my arse got sore and I asked if I could return the favour. Antonia pulled her legs up by her head and allowed me to enter her. We fucked and then I pounded her arse doggy-style until I came.

After our time ended, I walked out feeling amazing, my arse was sore but I couldn’t believe I had done IT with a shemale. And I enjoyed it!

Now, I think about her and our secret more and more. Sometimes, I find myself sneaking off to wank to shemale phone sex and I’m considering another solo trip back to Brazil. Just to indulge in the ultimate shemale fantasy again!

I hope you enjoyed my story. I just felt like I had to tell someone.

Have you ever been with a shemale?

Once you have sex with a shemale you will be addicted. Try our chatlines, CUM find out…

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