Had Amazing Sex With My Crush Who Turned Out To Be A Shemale free porn video

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My name is Nick. I am Software Engineer residing in Las Vegas- the perfect place to be working by the day and partying by the night. I absolutely loved the night life of Las Vegas. Occasionally on weekends, I went out partying at a nearby nightclub and casino. That is where I met Cassandra. She was a regular visitor too just like me. I often noticed her and sometimes even stared. It did not go unnoticed by her and she made the first move to get introduced. Soon after, we were making plans together to hang out. Cassandra had the prettiest face and eyes I had ever come across. Her body was gorgeous too but it was hard to take off your eyes from her face and I wanted to have sex with my crush. Little did I know much of it was plastic back then.

We had been hanging out for quite some time and I finally gathered courage to tell her about a date at my place. She looked at me intensely and quietly for some time. I almost started thinking how to keep a brave face if she refused. That’s when she nodded slightly. I was overjoyed. She smiled shyly at me but something told me she was a bit hesitant too.

The plan was on the next weekend. Through the week, I cleaned up my condo and made sure it was perfectly presentable to a lady. I made arrangement for our dinner date at home. I was hoping it would be more than just a dinner and hence kept condoms and lubes at hand. On Friday night, I patiently waited for the most anticipated knock on my door. At eight in the evening, it happened. I literally jumped off my couch to get the door. There she stood- a vision is a tight bottle green bandage dress. She smiled and walked in to my house.

We chatted for a while and dined together. We opened a bottle of champagne, and in the next few hours, we both were rather drunk. I hinted that she should stay over and much to my happiness, she complied. We started with a good old classic movie. But soon we got bored when she suggested watching porn. I let her select from my collection. She rummaged through and then pulled out a tranny porn much to my surprise. She was surely kinky and so was I to have sex with my crush.

As we watched, it was turning us on immensely. I looked at her to find she was staring at me. I moved forward to kiss her and she kissed me back. As I casually slid my hand down to her breast though, she stopped me. She whispered, “wait- there is something I want you to know first.”

I looked in her eyes and asked what. Instead of saying anything, she started undressing slowly and in a teasing way. She revealed a perfect pair of globes and the most tight-abed torso. She removed the dress entirely to reveal only her panties.

I was already hard and wanted to hold her when she started pulling down the panties. Then I was in shock to discover she was actually a shemale. I didn’t know how to react and was feeling turned on and shocked at the same time. Her angelic face was hesitant and she looked at me questioningly. I didn’t know what came over me as I started removing my shirt and walked towards her to kiss and hug her again. I nipped at her neck and hugged her tightly.

I was excited and I lifted her off her feet and she wrapped her legs around my waist. I carried her to the bedroom and when I laid her down on the bed, she sat up and started pulling down my pants. She kissed my chest and slowly went down. She pulled out my dick and then kissed its tip. Slowly she took it all in her mouth and started sucking on it. As she sucked and choked on my length, I almost forgot she was a shemale and I wanted to have sex with my crush irrespective of who she is.

I looked down to find her dick was hard too. It made me curious and she caught me looking at it. She smiled and asked me to go down on her if I want. I did want and I kneeled between her legs. It was the first time ever I was going to suck a dick. I hesitantly put my mouth on it. It smelled pleasant enough. I slowly put the entire length in my mouth. As I sucked on it, she moaned out loud. I was probably doing it right as I slowly started to increase the speed. She pulled me up and, on her body, and started kissing my lips again. I sucked her tits hard and bit on them. It looked pretty. I flipped her over and positioned my dick at her ass. I took some lubes from the side table and massaged it on my dick and her ass hole. I slowly put one finger in at a time and started massaging the lube deep inside her.

Then I position the dick and pushed it hard inside. She gave out a gasp and moaned loudly. I started banging her hard. I grabbed her boobs and felt them jiggle in my fingers. She was moaning very loudly and I felt her balls slapping on mine. It kept sending a jolt through my body. I did not realize I would enjoy this sensation so much. After almost half an hour of relentless fucking, I was orgasming finally. I came hard inside her ass and slumped on top of her.

I slowly took out my dick and went down on her again. As I started sucking on her dick, it felt so good. I could feel she was close to orgasming. She orgasmed hard in my mouth and her juices dribbled down my chin. Once we both had our fill, we laid down beside each other giggling and hold hands. I enjoyed having sex with my crush which turned out differently, but I don’t regret it.

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For already several weeks I surf through a website that advertises women, men and also shemales. Since my great experience with the other shemale during my holiday (see one of my other posts) the craving grew bigger and bigger to meet up with one again.So last night I decided it was that far. I drove to the address I got from her on WhatsApp and rang at the door. After paying her the agreed amount (love the humiliation factor of this, need to pay someone to fuck my ass) she showed me the...

4 years ago
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first time with a shemale

Anyone who has read my other stories will know that they are based on real events, this one is also based on an actual event. It happened on a recent trip to Thailand.We arrived in Thailand on a Friday morning, looking forward to a well-earned break. Jaq and I worked long hours, and we lived for our holidays. We had decided to visit Thailand as we were both curious about the availability of good looking shemales.It had long been a fantasy of ours to try a threesome with a shemale and hoped this...

Trans
3 years ago
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My first time with a shemale

OK, I was wasting my time on shamble videos and pictures on the web for about 8 years! When I first entered a porn site I almost got sick, but soon I got really curious about it but didn't dare to click that button; couldn't explain why I wanted it so much though. Eventually I pressed it. I started with shambles alone, then shambles fucking girls, then shambles fucking shemales and end up with shemales fucking guys... I started loving it, watching it on a daily basis. My fetish for thong...

3 years ago
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My first encounter with a shemale

I am a straight guy who had never strayed before.. however i had been having urges over shemales and started wanking to shemale porn every now an again online. i have always been interested with my ass being explored but i never found men attractive. with shemales it was different. they are beautiful, slender but also filthy at the same time. it seemed perfecti had planned a europe tour some years ago and my first stop was amsterdam. after a few hours of roaming the red light district i was...

2 years ago
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me my daughter and a shemale

my last story was with my daughter for the first time now we both have shemale girlfreind very beautiful ones they would come over me and my daughter would put on our sexy heels she picks my shoes now lol and they would fuck us both on the same bed theses shemales are in good shape they would fuck me and my daughters tight lil asses and shoot globs of cum then they would watch us creampie it out one of them came over one night when i got off work my daughter wanted me to tougue out her shemales...

3 years ago
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The Studio and the Shemale

When the company I worked decided to relocate to the north of England, it was made clear to me that there would not be a job for me there and so the decision whether to move woth or leave was decided for me. The redundancypayment was extremely generous, as it should be, I had been with them since I left school. So now I had to find a new job and the decision was whether to stay in the line I was in or change careers, but With the redundancy payment as it was there was no rush.Quite by chance I...

3 years ago
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shemale on shemale

Hi dear it just a story may be its real cany sure some 1 told me & i write this 1 for u Hi mai ap ki friend ap ka leya aik or story la kar aee hoain, mujha 1st three stories ka jo respons mila vo to mai ko bata nahi saktee, par ap ka tnx zaroor kartee haoin dil sa. Isee ka sath maree 4th story ap ka leya. Ya mara sath hona wala aik ajeeb or anokha waqia tha. I mean really very different, mujha movie dakhna ka mood huva to mai cenma chalee gae wahan khelade 420 film aksha ki lagi thee new film...

Lesbian
3 years ago
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Passionate Sex with a Beautiful Shemale

a man and his shemale lover get down to businessWill led Sarah by the hand into his bedroom. He closed the door as they entered and pulled her towards him. He placed his hands around her, caressing her toned stomach as he slightly nibbled on her earlobe. He could feel her trembling in his arms. Sarah lightly ground her ass into his crotch, rubbing herself against his hardening cock.“Mmm,” she moaned, feeling Will’s lips kiss the nape of her neck, causing her to break out in goosebumps. She...

3 years ago
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1st time with a shemale

I have always enjoyed playing with my ass hole, about two years ago I was in Chicago and went online to Eros and chose a shemale named with held. I called her up and she came to my hotel room. I was very nervous when I opened the door. She was about 6' tall and was a very good looking Latino. She bent down and gave me a kiss right on the lips and man where her lips where soft. She went into the bathroom and asked me to relax and she will be right out. I was lying on the bed and she came...

4 years ago
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My First Time With A Shemale

Hello Indian Sex Stories readers, thank you for your continuous support. Your support helped me to experiment more and more with different kinds of people. This time it was an unexpected encounter with a shemale. I hope you like this one. Email me at & tell how hard I made you cum ;). And also if anyone from Mumbai or Thane want to have a session with me than you can email me without hesitating. I don’t judge people don’t worry. So let’s come to the story. This is a recent story that happened...

Gay Male
2 years ago
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First Time with a Shemale

This is a true story about my first time being with a shemale. I happened just over a year ago on the tail end of a business trip to Amsterdam. I had a couple of free days at the end of my trip to enjoy and explore the city. So naturally, I decided to check out the night life and that meant a visit to the Red Light District.I spent a lot of time just walking around and taking in the sights and sounds of the area. There were so many people walking around and it was alive with all their energy. I...

4 years ago
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Threesome In Thailand With Hooker And Shemale

Hi friends. It’s your favorite writer Abhay from Jaipur. Thank you all for the huge response for my last sex stories. Now I am back with my recent real encounter. You all know my vitals and so I am skipping that part. Suggestions and comments are always welcome. I respond to every email I get. So, let’s start with my real life incident. It all happened in May 2018 during my vacation trip to Thailand with my wife and another couple of friends. Our vacations were nearing the end and I wanted...

3 years ago
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First time with a Shemale

First off this is a true story. I lost my virginity at a young age so sex is always been something usual for me. As far as how I lost my virginity... thats another story. I have always dated women that were openminded, bi-sexual and down right sluts. I have been in strange conversations and situations because of being soooooo "openminded", heres my story... Bella and I were getting dressed for a night on the town. We had plans to meet a couple from a a website we were members of. So we were...

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