Tranny Girl's Craiglist Fun! free porn video

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My name is Jack, I’m an average enough 18yo guy. Perhaps in a physiological sense, I’m more feminine, I have shoulder length blonde hair, and tranquil blue eyes. Coming from my father’s side of the family. My mother seemed to give me her own felinity. I have little to no hair body, my voice was higher than average, and I suppose I was kind camp. Ohh, I also had a cute and tight little bubble butt.

However, by night I was far from average. Porn always had fascinated me. Initially the classic “lesbian porn” for me, but when I discovered the delight of the “shemale” category I changed completely. My masturbation sessions revolved around the allure of a gorgeous sexy women complete with round tits and suckable nipples, wide curvaceous hips, and an ass that begged for anal, full red lips, but mostly importantly, the cock. It was the variety also, the likes of Sarina Valentina, her cute little cock just accentuated her femininity. Or the contrast of a divine goddess like Mia Isabella with a gorgeous monster cock that any man would beg to have…. And have in him!

This led to me beginning an interest in crossdressing, I started simple. I wore my mum’s thongs and it felt like heaven. I felt almost comfortable after a while, even in a non-sexual way. I then experimented more, wearing her bras, taking her fishnet stockings and pairing some heels in them. I looked a decent crossdresser, but I needed more. When I stroked my pretty 5-inch cock on my bed in her clothes I was in ecstasy. I used to go online in chatrooms and cam there. I felt like such a desirable slut when the older daddies would tell me how sexy and fuckable I looked. Telling me they wanted my tight teen ass and mouth for their cock. I would stroke my cock and finger fuck my hole to orgasm, sometimes they would instruct me to taste it. I would slowly suck my finger and taste my sweet cum. I used to also come across other CDs and even more convincing TVs. That’s when I realised I needed the next level. The chance came eventually, my parents were gone for two whole weeks during summer. They were going out of state to visit family, I wasn’t too interested, and besides had much hornier plans in thought.

They left early Monday, around mid-day I locked the front door, and went upstairs to their master bedroom. I went to their shower and ran the water. My mom had various shampoos, conditioners, essential oils, and better yet, hair removal creams. I shaved my entire smooth and applied cream to my soft white skin. I then went to my mother’s drawer. I shifted through until found my prize. I took out a black and red corset and snuck into it. Then some garters and clipped those in. Each snap of the clip sent a resounding twitch through my body. I finally paired it with a set of red fuck-me-senseless-heels. There was more yet to be done, I had been preparing. Having discovered the pleasure of anal play and stretching my tight teen fuck hole. I took a plug and inserted it in my waiting ass. The final inch going in was so satisfying. Then I sat down to her vanity. From there I straightened my hair, applied foundation, and red lipstick. I finished off with my mascara and eyeliner. I took a look in the mirror, tucking my cock I was very passable. I returned to my room.

I opened up craigslist and browsed. Today was different! I used to look through the ads, get horny and stroke cock with a dildo or plug in my ass dreaming of answering all of them. The horny fit twinks and the thought of filling their tight hole with cum. Or getting my own hole fucked by some sexy fit daddy. Today I finally answered some.
I found one in the W4TV section. The women named Michelle was a knock out, a pure MILF. Round big tits, curvy hips and a gorgeous face with a fiery head of brick red hair. Her ad was very simply.

Seeking younger girl to play with, must be horny and willing for mommy, mommy knows her little slut has been taking her clothes and needs to learn mommy is not happy.
I was in lust, I urgently snapped a few photos, some classy with my makeuped face and wig, others, exposing my tight pink hole to her. Her response came some time later.
It was just her number. I rang, and she answered a sensuous and enticing voice. She gave me an address which was only four blocks away and told me to be a good girl and come quick.

This is just an intro, thoughts so far, should I start faster or continue?

All comments appreciated

xx

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Tranny Pickup

on Chicago's state street. At the moment his trousers and shorts were around his ankles, his dress shirt was pulled up and he was reclining in the girls couch. But something wasn't quite right. He was beginning to suspect that the she whose mouth was engulfing his cock was really a he. Paul was in the bag thought, and after all 'lips are lips.' What ever the gender Paul was getting the blow-job of his life, she was sucking his nuts, alternately with deep throating him. The...

3 years ago
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Tranny In Toronto

Introduction: Read My Intro Story First Before This. Click on my profile name and youll see it. Craigslist Ad: Married Couple Looking For Fun Time – mw4t – 40s (Toronto) We are a married couple, looking for a bisexual trans for some fun. We host. Message if interested with times youre free. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ To: [email protected] From: [email protected] Subject: Re: Married Couple Looking For Fun Time – mw4t – 40s (Toronto) Hi, my names Lizzie Elliott....

3 years ago
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Tranny Surprise Part 2

Things were off to a good start with Dani. We have been texting each other throughout the week just talking and setting up another date. We decided to go to the local fair I picked her up around 530 and she wasnt quite ready yet so she let me in hugged me and went back to finish her hair. I sat on the couch and played with her cats for a minute, she was back in no time and she looked great! ‘Wow Dani you look really pretty in that sun dress.’ I said. ‘Thank you’ she replied with a big smile....

4 years ago
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Tranny in Toronto Chapter 5

Introduction: Hello everyone, I apologize for not writing any recent / new stories. Ive been really busy with stuff. Heres a quickie. Helen is a good friend of mine. When the following occurred, Helen and I had known each other for only a couple of weeks. We met at a party a mutual friend of ours was hosting and we instantly connected. To describe her, she was smoking hot. She was a blonde in her late 30s with piercing blue eyes, huge tits, firm ass and I believed to be a closet lesbian. She...

1 year ago
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Tranny in Toronto Chapter 3

Introduction: Read Past Stories Before This One. I stood outside Tim Hortons with a small coffee in my hand, sipping away on a cool windy day. I looked at the cars driving by me, just waiting for the white van to show up. Two men from Craigslist messaged me and asked me for a Sunday afternoon fuck. I agreed to my first MMF threesome. They called it a MMT threesome and were really excited to fuck a prostitute, and not only that but they wanted a shemale really badly. They told me to come to...

2 years ago
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Tranny Surprise Part 1

After being cheated on for months here I am alone in a bar having a drink. I dont understand whats wrong with me im above average in looks, im fit, im successful for my age. Its time I move on though and so far no girls ive dated have been worth a second date. As I look around the bar I see her. I immediately start to stare. Looks like she was there with a couple of her friends. I order another beer and decide to scope it out for a little bit. I just couldnt get over how pretty she was. She...

4 years ago
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Tranny used in the woods

I just had to share this as I realised one of my ultimate fantasies at the weekend.A couple of weeks ago I met a guy online (Mark) and we met up and had some fun together. A few days later he got in touch again and said he was going dogging and he wanted me to join him. I do this from time to time, so we made arrangements to meet at his house for me to get ready and then go out on the Friday night to a known dogging location not too far away.I thought it was going to be just the two of us, but...

4 years ago
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Tranny Surprise Part 2

Things were off to a good start with Dani. We have been texting each other throughout the week just talking and setting up another date. We decided to go to the local fair I picked her up around 530 and she wasnt quite ready yet so she let me in hugged me and went back to finish her hair. I sat on the couch and played with her cats for a minute, she was back in no time and she looked great!"Wow Dani you look really pretty in that sun dress." I said. "Thank you" she replied with a big smile.We...

3 years ago
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Tranny Surprise Part 1

After being cheated on for months here I am alone in a bar having a drink. I dont understand whats wrong with me im above average in looks, im fit, im successful for my age. Its time I move on though and so far no girls ive dated have been worth a second date. As I look around the bar I see her. deleted

1 year ago
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Tranny orgy continued

Debbie, my red haired, large titted, big hipped, cock sucking, golden bushed girlfriend now knew I loved to suck shemale dick and having them fuck me in the ass. Sex between the two us became more intense and we were often joined by the gurls across the hallway. Life was good and shortly Tanya and Bonnie informed us they were having a party that would include Shemales, sissy me and cross dressers. It was to be an orgy! On the night of the occasion, we were the first ones there. I wore a speedo...

4 years ago
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Tranny orgy

You can live with someone and never really know them.I was running a car wash in West Palm beach and every day I would take lunch at a cafe down the Blvd. The food was good, and cheap and I had the hots for Debbie, this built to the hilt redhead chick working there. She wasn't any great beauty but she had a body to die for. 36 DD tits. big hips and thick legs. Just my type. After a couple weeks I got the nerve to invite her to TGI Fridays for some drinks.After a few, she started talking about...

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