First Ass I Fucked Was Also My First Tranny! free porn video

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Me again, I haven't shared any of my stories in a while but was chatting to an old friend about this one last week and thought I would share the story. Again names have been changed to protect identity, all my stories are true and I am not a author, just a horny guy with some horny stories. Thanks.

I was 20 years old and had been playing with guys and gals for many years now (check old stories). I had arranged a night out with some of my friends to celebrate a birthday so put on my new shirt, jeans and shoes and hit the town! Now I don't really drink much so it doesn't take much for me to become merry. The drinks and shots were flowing and it was a great night, chatted to a few girls and had a dance. It had gone midnight and we were in the gay part of town in one of the busy bars. Now non of my friends know I play with guys even though two of them are gay I have kept this private and was happy with that. Anyway, I was pretty tipsy and was dancing away when I caught they eye of a girl at the bar, she was stunning. 5ft 8, long dark legs, dark hair down her back, nice tanned skin, dark eyes, plump lips and an amazing pair of tits that were almost busting out of her little white dress, which clung to her figure like lycra. She was out with some of her friends who were also sexy but she was stand out and my head wasn't the only one that was turning. I saw one of my friends approach her and begin to chat with her, I was gutted, I wanted to talk to her. After a few minutes he left her and made his way over towards where we were gathered. "Who is she?" I asked. "Keen are we? She's called Laura, shes local apparently and just on a night out with her mates, she seemed really nice but wasn't interested in my advances" he replied. "I will leave it then, shame as she is stunning" I said taking another shot and standing to go hit the dance floor.

After 20 minutes I had lost sight of her and brushed it off as a lost opportunity, I decided to go outside for a cigarette, as i left the back door into the smoking area, I was stopped in my tracks as there she was, alone on her phone. I lit up and stood under the heater and got my phone out to check messages. She hung up the phone and rummaged around in her bag, she approached me and said "Have you got a light babe, I cant find mine anywhere" I tried to play it cool but no doubt looked like a rabbit in headlights. "Yea" I said as I lit her ciggie, she lent in and I got her scent, it was incredible, not to mention the great view of her impressive cleavage. "Hi, I'm Laura" she said, "Alex" I replied. We chatted for a couple of minutes quite flirty it was getting when her phone rang and she excused herself to take the call. I went back to the group and thought fuck it, hammered another drink and danced my ass off. After half hour i felt a tap on my shoulder it was Laura, she said "sorry about that it was the dickhead ex, can I make it up to you with a dance?" I felt like it was Christmas! "Hell yeah!" i replied in my now drunken state, for the next hour we danced and were all over each other, I kept getting a thumbs up from the group and her friends were nowhere to be seen. My friend approached me to explain that they were taking off for the night was I coming, I looked at Laura and she smiled "Go ahead buddy, I will catch a taxi in a bit" I told my friend, I think he already knew the answer.

Just after he left Laura grabbed me close and said "Are you going to kiss me or what?" I lent in and we locked mouths our tongues explored each other and my hands wandered to her ass, she replied by grabbing my semi erect package. I jumped slightly, she pulled her mouth away and said "My place? It's just around the corner" I didn't even have to answer the smile on my face said the lot. As we stumbled around the corner to hers stopping every 30 seconds to make out I was becoming hornier by the second and my semi erect cock was now rock hard. She grabbed it again and said " this needs taken care of get a move on and I will show you how good these lips are". The pace picked up quickly and before long we were at her apartment and bundled into the lift, she pressed the button for the 9th floor and as the lift doors closed she dropped down and opened my jeans. Before we had gotten to floor 2 she had my hard cock at the back of her throat like a pro, I was in heaven, she cupped my balls as she worked my cock fast with her mouth, this wasn't her first time! As the lift dinged to say our stop, she rose up and kept my cock in her hand as she led me out of the lift into her passage and walked to her door. She opened the door and we fumbled inside, she closed the door, pushed me against the wall and dropped to her knees and resumed sucking me, this time lowering my pants to the ground and sucking my deep and fast with no hands, skull fucking herself on my cock and I could see her hands wandering on herself. It was too horny and I soon felt the urge. "Slow down babe, I am gonna shoot" she didn't, if anything it spurred her on, she pulled my cock out and grabbed it with one hand stroking it hard, she took my balls in her mouth as she stroked me. I moaned loud and warned her again "I'm gonna cum" she looked up at me in the eye with my balls in her mouth stroking my rock hard cock and said "good, shoot on my slutty face" with that I let out a jet of cum over her face, she pulled back and opened her mouth as she wanked me hard, milking every jet. I must have been very horny as this was a big load for me it kept cuming and cuming as she moaned with each jet on her face. She took me back in her mouth and sucked every last drop out until I went soft. She looked up and pulled my cock out "thanks you for that" she said, as she scooped my cum from her face and licked her fingers clean, "you have a beautiful cock, I knew I wanted it the moment I saw you in that bar". I was weak at the knees and still drunk but mumbled back " thank you, you're incredible. Why don't we get in your shower and round two will be on its way shortly I cant wait to see those tits out in the open. She stopped and looked at me funny, "sorry, if I said something, I just think you're stunning in every way" I said, trying to work out the expression on her face.

She stood and walked into her front room "Alex, I don't think its a good idea to go any further" she said as she walked. I pulled my trousers back up and followed her "why? Was it what I said? Was it because you made me cum quick, its not always like that just you're so horny!" She sat down on her sofa " Alex I am not who you think I am and if I try to explain I know you will bolt faster than anything, guys I meet always do when they meet or see the real me". She looked upset, so I walked towards her and sat next to her, I took her hand and said "Listen, you are one of the sexiest girls I have ever met, nothing would make me leave you now, I want you bad". She smiled and said "well don't say I didn't warn you" she stood up and walked towards the middle of the floor, she undid the back of her dress from behind teasing me, she let the top part fall down and turned to face me with her hands covering her boobs, they were obviously fake but were beautiful and big, not too big but a nice size indeed, she let go as they held perfectly with the most beautiful small nipples. I gasped and felt my cock twinge, she turned around again and slid her bottom half down showing me the top of her ass crack and white french style knickers, she turned back around and said "you ready?" I sat there enjoying my show and nodded. She grabbed her knickers and dress and slid them down expertly and slowly with her hands covering her pussy. I smiled, she removed her hands and my jaw hit the floor. Between her legs was a cock! A clean shaven, uncut, semi hard cock. I sat there, didn't know what to say. She broke the silence and said "feel free to go, I understand". I didn't say anything, little did she know that I was into cock and this was incredible. I stood up and walked towards her, she backed off a little. I grabbed the back of her head and kissed her hard with both my hands on her head, I felt her cock hit my leg and my cock was stirring.

I pulled away and she smiled, I grabbed her tits and sucked them one by one as she let out a moan, I dropped to my knees and took her semi hard cock, it was thick and well looked after, I took the whole length and worked it hard grabbing her balls and letting my finger run back to her ass, she let out a moan as my finger ran over her ass. Her cock got hard quick and it was a good 7 inches and thick she began moving her hips to fuck my mouth as I rubbed her hole. I pulled out and stood up kissing her again letting her taste her dick. She dropped again and undid my trousers and pulled my hard cock out and devoured it. This time i took control and grabbed her head and began to fuck her mouth, she loved this and moaned loudly. I could see her pulling her cock and rubbing her ass, she looked amazing. I pulled out and pulled her up by her hair and we kissed again. I looked at her and said " I have never fucked an ass before but your young hole is getting it tonight" she smiled and kicked off her heels. She walked over to her sofa and got on all 4s, she spat into her hand and rubbed it on her ass letting a finger dip into her hole, she let out a moan as she lowered her head onto the sofa and pushed her ass in the air. "what are you waiting for" she said. I stepped out of my pants and pulled off my shirt. I walked towards her and lent in, I licked her ass, it was smooth and amazing, I slapped her cheeks as i pulled them apart getting a real taste for her ass. It was incredible she moaned like crazy and muttered " fuck me". I stood up and rubbed some spit onto my cock, i slapped it onto her hole and rubbed it up and down teasing her before pushing the tip in slowly, she moved back slowly until my whole 8 inches were in her. She moved out and back in a couple times slowly, I was happy to let her take the pace until she was fine. "All ok?" I asked slapping her ass a little. She moaned back with a "mmmm" which I took as yes, "good" I said "now its my turn" with that i pushed my cock in her deep making her moan and lift her head, I pushed her head back down and said "stay down girl and take this cock" I slammed into her again and went to town fucking her , she felt amazing. My cock was loving her hole and she was loving my cock. We fucked in that position for a good 10 minutes before i pulled her up and pushed her against the wall, I grabbed her boob with one hand and hair with the other. I fucked her hard as i whispered in her ear and kissed her neck. I felt the urge coming and went faster "I am gonna shoot soon" she loved it and said "yes please, fill this ass up baby". Next thing I knew I was unloading fast and hard into her ass, I held deep until my whole load was in there. As i pulled out I head some of my cum hit the floor, she quickly put her hand there and caught the rest, she rubbed it into her rock hard cock. "I needed that! she said. I kissed her deep, she was still rubbing my spunk into her hard cock and I could taste my cum in her mouth.

"Now" she said, "how about I get a turn of that ass of yours" I smiled and walked over to the sofa and adopted the same position she did, I put some spit onto my hole and looked at her and said "what are you waiting for?" she laughed and said "I am gonna fuck that pussy hard and fast". She approached me and slid the tip onto my hole, no waiting around she slid in inch by inch then pulled all the way out again, she did the same again and I let out a moan. She went crazy and as stated fucked my ass hard, she was holing my shoulders pounding my ass calling me a slut and slapping my ass, she pushed my hips down so i was lying on my stomach and straddled my hole and hammered away again. She was loving it, she pushed my head into the sofa as she started yelling "I'm gonna cum" with that she pulled her cock out and I felt a spurt of cum hit my hole, she stepped over and grabbed my head by my hair and pulled my face out of the sofa and spurted me with cum on my face as she wanked it over me. Her other hand was rubbing my hole with her cum as she milked every drop onto my face. she collapsed after and we lay there in a heap as i cleaned her cock off.

The rest of that night and the following day was spent the same way. We became fuck buddies for a few years until she moved to the middle east. I have seen her since but shes attached now. It was an amazing night i will never forget.

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I met Charkara (her real name) through an adult dating site. You can find her pictures on my xhamster page titled, "My First Tranny". We corresponded through the dating site quite regularly before we decided to take it to next level and exchange phone numbers and email addresses. We talked on the phone getting to know each other, what we liked to do sexually, etc. She came off as a total freak willing to do most anything which was an extreme turn-on for me. We then begun having phone sex...

4 years ago
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The Trucker and The Tranny

The Truck Driver and the Tranny fiction by [email protected] This is a work of fiction for mature readers, containing explicit sexual acts which may be illegal in some backward parts of the world. If it's illegal where you're reading it, you should MOVE! If you're too young to be reading erotic and explicit sexual fiction, don't go any further. I was working as a truck driver, moving periodically to new areas of the country (mostly around my hometown of Nashville, TN) in...

1 year ago
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Hotel Pool Tranny

As I headed toward the office, I could see the pool, and immediately thought about taking a swim after checking in. After getting my room key, I decided to cut through the pool area. It was a large pool for a hotel, there were plenty of chairs, and it looked very clean and inviting. Casually looking around, there were only a few people, and as I continued toward the other end where my room was, there was an attractive younger lady that caught my eye. She was laying on one of the loungers by...

1 year ago
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Cousin Waseem

Dear readers, you must have read many incest stories till date but I am sure you must have never come across a sister fucker cousin, like ours. Just read it and then give your comments. Actually, we belong to eastern Uttar Pradesh and live in a joint family. It may sound strange but we were 3 sisters,myself being youngest. After lot of prayers my youngest Uncle was blessed with a boy. My father and other uncles must have been inspired by this feat and thinking the fortunes will turn in their...

Incest
1 year ago
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Cassia III

Cassia III By: Ryker Several months later, the changes to my body were progressing. When I looked in the mirror I saw more female than male, and my emotions were a mess. No one looking at me would ever think I was a man without looking between my legs, especially with the "all natural" D-cup breasts hanging from my chest. Now it was confirmed my balls and cock have shrunk, just a little bit. I cried myself to sleep the first few nights after I realized it, and Cassia even comforted...

3 years ago
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Cassia IV

Cassia IV By: Ryker As time went by, I'm not sure how long, but it was several more months, the changes to my body were slowing down. My breasts were a large D-cup or maybe a small DD, and my penis and testicles only shrunk a little more. It was still hard to accept it. Miss Cassia said her treatment was nearly complete, and I was nearing the final stages. Unfortunately, I was still settling into my new emotions, and it was still very hard to handle. I cried often, sometimes for...

2 years ago
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Cassia II

Cassia II By: Ryker ___ When I woke up the next day, the first thing I noticed was that the pain still burned in my ass. I looked around and saw that Cassia was gone, but the lights on the metal ring around were out, and a handwritten note was sitting on the floor beside me. It read, "You are late. I will forgive you this one time since I don't need you this morning, but from now on you will wake by 7 am to start your duties. Go downstairs and get ready just like yesterday -...

2 years ago
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Assassins Creed Brotherhood The Portuguese Parisian Assassin Comes to Roma

(Outside The Tiber Hideout) John's Horse Laid Dead beneath his Arrow-Ridden Body, but Still He Clung to Life, His Belief in the Creed in the Assassins Brotherhood Unbroken and Unbeaten, He Crawled through the streets, bloodstained Robes and Stab wounds all red and bleeding red. He Finally Collapsed in front of the Tiber Bridge. (Inside the Tiber Hideout) John Awoke to A Sweet singing, he tried getting up, but he felt several Stitches Pull and the Pain Causes him to groan and pass out. John had...

2 years ago
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Cassia V

Cassia V By: Ryker Two weeks later, I could tell Miss Cassia was getting ready for something to happen. Part of me was concerned, and I wanted to ask her, but when I broached the subject, she told me not to worry about it. She was already annoyed with me from when I previously begged her to let me cum. When I grew more concerned, I asked again. "Damn it, Marisa! Do you only think about yourself!?" she yelled at me. She started using my name more often instead of "sissy" except...

2 years ago
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Cassia I

Cassia I By: Ryker "Aww, don't feel too bad, sweetheart. Most men don't realize what I have hidden in my panties until it is too late for them." "MMPPHH!" I screamed into my gag as I struggled against the cuffs binding my legs and arms. She ignored me and continued. "Still, I overpowered you quite easily. You really are a pathetic wimp, and now you are going to pay the consequences for that." So let me tell you how this is going to work. By day, you will be my live-in maid...

1 year ago
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Cumming Clean With Cassie by loyalsock

I didn't always like oral sex. Don't get me wrong - Ilike to eat pussy, and the ladies tell me that I'mreally good at it. What I mean is that I wasn't muchturned on by a blow job. It felt good, yes, but itwasn't something that would float my boat, so to speak.Until I met Cassie.The way Cassie does it just drives me wild. One thingthat helps is that Cassie has braces on her teeth. Ihave always thought braces were sexy. The other thingis that she doesn't just jump right in and expect me tocum in...

3 years ago
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Nisha Massi

Hi to all the fan of ISS..I have been reading these stories ever since I started using internet. I would appreciate it if the ladies send their comments at Though I have been reading these stories for over 9 years now..I am writing a story for the first time. Firstly about myself….I am Rahul Mittal, 25 year unmarried guy with unusual sexual appetite..I masturbate twice or thrice everyday sometimes even 5-6 times especially on Sundays…I am 5’6” weatish complexion, slim built…I belong to a well...

Incest
4 years ago
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Cassis ass

Cassi and I had anal sex once before when we first started dating. But after the first time we didn't really do it or chat much about it for a while. Then the night after movies we chatted a lot about it and eventually with a bit of help from my stepsister we managed to have some alone time together at my parents house.Cassi and I rather quickly made our way to the bedroom where we undress each other. Once naked I laid her down on her back and made my way to between her legs. I started muffing...

2 years ago
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December holidays part 10 my ex girlfriend Cassi

Laying in bed Monday evening home alone I texted with my girlfriend Jessica chatting to her as well as messaging my ex girlfriend Cassi confirming that she would still be sleeping over tomorrow night. Cassi replied back most definitely baby I'm looking forward to seeing you and spending the night together.I was too excited to fuck her sexy body again and soon while laying in bed a fell asleep.Waking up the next morning just before 8 I got up and made myself breakfast and while eating I message...

2 years ago
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Cassi and I

It was a Thursday night and still being single and a bit lonely, not getting as much sex as I was use to having a girlfriend, I decided to message Cassi to see if she would be keen to meet up for the day. She was indeed keep and as we chatted she said she would meet by my house just after 9 tomorrow morning. She seemed rather excited and we continued messaging each other for a while before saying goodnight. I almost immediately fell asleep after my last message to Cassi. Waking up Friday...

1 year ago
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I And My Massi First Time

My family consist of my father,my mom,my sister and myself aman.My father is 51 and my mother is 38.My age is 20.My massi name is meenakshi and she is 30.I was very normal guy until I get a chance to fuck my mother.My mind got corrupted and I started fantasizing around woman around me.   Slowly I dived into world of incest taboo porn especially massi and her sister son.First I watched son and mom porn but I got a chance to fuck her now I want my massi.It simply blew my mind I started imagining...

1 year ago
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Fucking My Massi Shilpi

I was 18 years old ,5’9″ ,slim smart handsome virgin and endowed with a 7.5 inches long dick with a big crush on my mother’s sister Shilpi ,whom I used to call Massi ,she used to live in the same town as us and she had 2 sons at that time. The elder one being 6 years and the younger 2 years and it was my summer vacations and my cousin who was very fond of me insisted that I stay in their house and my parents also said yes to the same and I played with the young kids throughout the day and then...

Incest
3 years ago
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The Classifieds by loyalsock

Blair Hutton wiped the sweat from her shaking hands and gingerly reached for the doorbell. She knew that what she was about to do was risky at best, and dangerous at the worst. Only yesterday morning she had been looking at the classifieds in the local under ground newspaper when her eye caught an intriguing ad, "Wanted, attractive woman to service me orally while my wife watches and maybe participates. All the oral sex you can handle. If interested, contact Eric at 555-3999." Immediately upon...

1 year ago
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Mona massi Jerking to fuck

Note : This story is completely fictional! I had just shifted to Mona massi's house for my further studies and had started believing that very soon Mona massi would be in my arms.But it was just my desperation to get her and did not look realistic.She was a very free and bubly character and moved around the house freely in her nighty and sometimes even in her saree and peticoat.And looking at her sexy body was all that i could settle for at that time.She had a magnificient body.Very feminine ,...

Incest
2 years ago
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I caught massi

This is from the times when I had just turned 18 and had shifted my base to Delhi i. e mona massi”s place for my studies. mona massi was a very sexy lady around 39-40 years old. One whom i had been dreaming of fucking ever since i started jerking.actually she became my dream girl when i accidently saw her nude bathing in our village bathroom.and ever since that day i have failed to spot some body sexier than hers.she was a perfect figure thin waist like pamela anderson with beautiful sexy...

Incest
2 years ago
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Cassy Gives Herself

Before being married, I was living in a house with two artist students. My then girlfriend lived in her own house share. Ours was a very large house with spare rooms we’d use for studio space, open areas for communal get togethers and all in all we were a happy group of three young guys, committing to our creative lives and generally having a good time. We decided after some time that one of the smaller, unused rooms may as well be used for another flatmate to reduce our expenditure. The word...

1 year ago
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WHEN I BECAME A WOMAN Chap 6 CASSYSCHOOL CONTINUES

Over the next week, Cassy found herself with questions, anticipating another round of Daddy and Mommy’s education. She stood in front of the full-length mirror in her bedroom trying different clothes, stripping slowly, looking at her body from all angles while she played with what Mommy told her was her clit, which was short for clitoris, that little nub of skin at the top of her pussy. She quickly realized amazing feelings came from there as she rubbed it. Over the week, she had closed...

1 year ago
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Hubby Massage By Wife Along With Masseur

Hi ISS readers!!! Though i have been reading stories on this site for close to a decade, this is the first time trying to post my own experience. Bear with me and request to provide me with feedback to improve so that i can keep sharing my experiences in an interesting manner!!.. Little brief about me, For the purpose of reference – call me Sathish !!!.. I am 32 yrs old and work in an IT MNC domiciled in Chennai. I Love Sex and hardly i remember a day where i have spent with watching something...

1 year ago
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Mona Massi caught red handed

Note : this story is completely fictional! This is from the times when I had just turned 18 and had shifted my base to Delhi i.e Mona massi's place for my studies.Mona massi was a very sexy lady around 39-40 years old.A perfect indian milf ,one whom i had been dreaming of fucking ever since i started jerking.Actually she became my dream girl when i accidently saw her nude bathing in our village bathroom.And ever since that day i have failed to spot some body sexier than hers.She was a perfect...

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