First Time Porn Stories
Page 490

My CD friend

This story is fiction.

~~~~~~~~~~~~~~~~~~~~~~~

I had been chatting to people on a ts chat room as I had recently become accustomed to do, when I received a private message from a local cross dresser. She asked me where I was from, how old I was etc and we found out we lived a few towns away from each other, both young guys and both really loved wearing women's clothes.

Admittedly she was much more experienced at it than me, having access to girlfriends, s****rs and mothers clothes and had even ventured out fully dressed once!

Eventually after some light chat, swapping dressing up s... Continue»
Posted by shyadam89 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 548  |  
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Crossdressing b*****r part 1

It has been two years since my parents died in a car crash coming back from holiday. My younger b*****r, Greg, went to live with our grandparents until my grandfather had a stroke. When my grandmother couldn't take care of my b*****r, as well, he moved in with me. Things were going fine, with Greg attending the local Polytech, like me. I was earning a teacher's degree, and Greg was studying carpentry.

Several months passed, and I noticed strange things happening around the house. It seemed that my underwear drawer was open all the time, so I went upstairs to ask Greg if he knew anything abo... Continue»
Posted by longG69 2 years ago  |  Categories: First Time, Taboo  |  Views: 1596  |  
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My Daughter's Home Cooking Part II

My first encounter with my daughter all those years ago left me ashamed and exhilarated all at once, I mean there she was in my bed sl**ping soundly having just given me the best blow job of my life up to that time, a thousand times better than any her mother had ever given me. The father part of my brain kept repeating , "What the fuck did you just do?" At the same my cock kept reiterating "Give me more". I wanted to think that evolution, societal norms, and remorse would get me back to the straight and narrow, but she had given me a taste of the apple and I wanted to go all the way to the ... Continue»
Posted by jackevermore 2 years ago  |  Categories: First Time, Mature, Taboo  |  Views: 3780  |  
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Black Daddy Cock Master

There was an adult theater on my way home from work, I'd gone in once just to see what it was like. I'd since read about these theaters on the internet that you could get a hand job or maybe a blow job, sometimes see women in there playing around. So one Friday night, my wife was out of town, I thought I'd check it out again.

I sat down about two thirds of the way back. After a few minutes I saw a guy walk through a doorway I hadn't noticed and a few minutes later a another guy come came out. Curiosity won and I walked over and found myself standing at the front of another theater. I couldn... Continue»
Posted by lookin02 2 years ago  |  Categories: Anal, First Time, Gay Male  |  Views: 4082  |  
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Fun with Kevin

Kevin and I walk out to my car. I ask him where he is parked and he had shown me this large 4x4 truck. It's at least 4 foot off the ground. I told him that I will leave my car here and we can ride in his truck.

Of course I'm not able to lift my leg that high, so Kevin offers to help me up. He grabs mey waist and heaves me up. As I'm getting in the seat, I turn to Kevin with my legs spread apart, and tell him thank you. He then takes his hands and runs them up my thigh, all the way to my wet panties.

Kevin told me, I need to get those off and let my pussy air out some. So, I lift up ... Continue»
Posted by loloishorny 2 years ago  |  Categories: First Time, Gay Male  |  Views: 756  |  
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My first flogging

 Flogged for the first time

As a young man of 18 years in the late 1950's I was chatting in the office with a male
colleague , I mentioned how much the flogging scene in the film Mutiny on the Bounty had
excited and really turned me on, he smiled and said “Oh really” A little later he asked if I
would like to experience it , he would arrange it for me, I was to arrive at the office the
following Saturday wearing slacks and casual shirt. As I went back to my digs I was full of
trepidation and excitement , it was nearly impossible to sl**p that night wondering what i... Continue»
Posted by 4flogging 2 years ago  |  Categories: BDSM, First Time, Gay Male  |  Views: 479  |  
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Sissy Boy/Girl's First Steps


Hi,

My name is Lara and I am a Sissy! wow that was easy, but how did I become one now that was hard, a hard road. It all started out in the summer of 87 I was 17 lost and looking for a job. My mum who knew I was going to be a soft boy, I mean I was still sucking my thumb and had been caught many times in my s****rs clothes from knickers to dress's, my mum would just smile and tell me she loved me. My Father had taken to the way of just ignoring me.

Then one day my mother came into my bedroom, I was in my s****rs underwear masturbating over pornographic pictures of naked men, my mother ... Continue»
Posted by SissyLara 2 years ago  |  Categories: Anal, First Time, Gay Male  |  Views: 1297  |  
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Help with Biology Homework Part One

(This is a fiction story that is hinting the fact that it might have actually happened)
Now, when I say this happened a few years ago, I mean it happened before I was considered ’Legal’. I won’t say how old, or even real names, let’s just say my name is Steve, and the girl in the story will be Jessica.
Now, most people at age xx only think about sex, me on the other hand, being a scrawny 5’1”, white-as-hell nerd, I knew that sex was the last thing on my mind. Then I met her, she was the head cheerleader of our school, auburn hair with some purple highlights, blue eyes, if I had to ma... Continue»
Posted by Sexyteendude4u 3 years ago  |  Categories: First Time, Taboo  |  Views: 2270  |  
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Dinner with a View

I'm on the road - again. After a full day of client services, I stopped at a restaurant (more like a truck stop) for a bite to eat. This is a place I dine semi-frequently, so I know some of the staff.

On arrival (late afternoon), I noticed there were very few customers. As such, I sauntered up to the counter and asked if I could be served there. A very nice, very slender, very young server flashed a big smile and said "Well, sure - come on over!" I seated myself and prepared for service.

The server, Lara, approached me - regreated me - and took my drink order. When she returned, I was ab... Continue»
Posted by goinstrong 3 years ago  |  Categories: Fetish, First Time, Voyeur  |  Views: 1251  |  
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My first MMF: why I keep on cruising

I gotta tell you about my one and only
there is this crusing spot along the Trans Canada highway not too far from where I live
I pulled in to a truck pull off area, it was early evening about 7:30 or so, on a November evening
When I stopped there was a car, parked ahead.., brake lights flashed on off in tell tale fashion

I turned the interior lights on and off in my van and soon this guy came back to my vehicle to join me
Because it is a rather busy and open highway I wasnt really too comfortable there

but the little head, took control
He soon was touching me I stroking him.. ge... Continue»
Posted by NBRay84 3 years ago  |  Categories: First Time, Group Sex  |  Views: 1334  |  
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Younger 2!

I have a niece that is 4 year younger than me, Which in my other story, is one of my niece's younger s****r's.. I would go out to Syracuse every weekend, or else she'd come to my house, We would make a fort on the bottom of the bunk bed, we would always play uno, and every time we had to draw a card we would have to take of an articular of clothing and after we ran out of clothing we would crest each other's body's. I always loved holding her close, and going down on her wet pussy, it always tasted so good! I remember the first time we had sex. It was great! I was so happy the day they moved t... Continue»
Posted by Tizzletina 3 years ago  |  Categories: First Time  |  Views: 1557  |  
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Me, My mom, and My Aunt

This is part III of my story


They didnt want to sl**p next to each other because it would be weird. So i was in the middle of them Cherly who was asl**p when my aunt D came into the room and wispered “ Allasay? Dan? are you awake?” Allasay said “Yes mom what is it?” She said she needed us in the living room for a min. It was dark when i came down the steps so allasay clung to my bare back. We got down the steps. There was a light coming from the bathroom, I knock it was my mom. She said aunt D was in the RV. We walk outside to a warm night. We opened the door to the RV. Ill never forget i... Continue»
Posted by bigDkaz 3 years ago  |  Categories: First Time, Taboo  |  Views: 4073  |  
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Younger!

I can remember way back when i was younger. I remember my two niece's an i going into my bedroom and laying in my bed all next to each other, Watching porn on HBO, we weren't that old.. We all took our pants off, and each one of went down on one another, and fingered each other, We would do that every weekend, all day.. I loved doing it! The thought that we could get caught at any moment by are f****y member's and we didn't care. Then my one niece had a little b*****r, By the time he reached 5 he joined in with all of us along with another one of my niece's, We never thought anything wrong abo... Continue»
Posted by Tizzletina 3 years ago  |  Categories: First Time  |  Views: 1624  |  
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First time for Krista

Tina and Tim the great next door neighbour.

We have lived in the same house for over 10 years and have enjoyed the good times with friends and f****y over the years. But last year was a year to remember and one that changed the way I think about what a good neighbour will do for you.

It all started when the house next to ours went up for sale and a new young couple moved in. They had 2 small c***dren and seem to fit right in with everyone. My wife and I our on our second marriage and our k**s don’t live with us full time. They are also older so they really don’t spend much time at th... Continue»
Posted by bigcityguy 3 years ago  |  Categories: First Time, Taboo  |  Views: 2439  |  
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Bachelor Party Fuck-Up

Ever think you have the perfect ideal to take care of a problem. You know one of those ideals that makes perfect sense in you head, but when you go through with it falls apart or worst it fucks everything up. Boy did I have one of those. Here is how it all went down.

It was the weekend before Rob, my cousin's bachelor party, Katie the bride to be and my best friend, found out about the plans by read an email detailing the plans and came to me.

The email talked about how my b*****r Tim was going get some his buddies and Rob's buddies together and take Rob out for happy hour and hit a few ... Continue»
Posted by longG69 3 years ago  |  Categories: Anal, First Time, Group Sex  |  Views: 2433  |  
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sex with a stranger

i follow you home from the supermarket,i make my way round the back of your house,im so horny.luckily the back door is open and i make my way through to were i hear you are in the house.
the kitchen.
you are putting the shopping away,youve loosened your skirt and your bra straps are loose,just of the shoulders.
i watch as you bend over the shopping and there only one thing on my mind....im going to fuck you.

i make my move and grab you from behind and cover your mouth.you try to resist but im to powerful.i move one hand down to your tits,your nipples are hard and you kind of sigh when i ... Continue»
Posted by wankersoffagain 3 years ago  |  Categories: First Time, Mature, Taboo  |  Views: 540  |  
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MY SUB TURNED

ARRIVING HOME AS USUAL I OPENED THE FRONT DOORLOOKING INTO THE HALLWAY NO SUB SLUT.MUST HAVE HAD A BAD DAY I THOUGHT AS SHE IS ALWAYS KNELT ON THE FLOOR NAKED WAITING FOR ME.
ON THE RARE OCCASIONS SHE IS NOT I KNOW WORK HAS GONE BADLY SO TEA WILL BE COLD SANDWICHES OR SOMETHING PLAIN AND I FEEL LIKE A DESPARATE DAN PIE SO HUNGARY.
I WENT INTO THE LOUNGE AND LOOKED ROUND THE DOOR SHUT BEHIND ME AND THERE SHE WAS BEFORE I COULD SAY ANYTHING SHE SLAPPED ME HARD ON THE FACE BOTH SIDES, AS I RAISED MY HANDS TO MY FACE SHE QUICKLY PUT HANDCUFFS ON MY WRISTS.SHE SLAPPED ME AGAIN AND THEN BENT DOWN ... Continue»
Posted by gram510 3 years ago  |  Categories: BDSM, Fetish, First Time  |  Views: 605  |  
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Grandfather's visit...

My Grandfather came up to visit from Jamaica over the holidays. He stayed with my mom and I in NYC. My Grandfather was a successful businessman and had a thriving professional business, in Buff Bay, Jamaica. He was 62 and had the physique of a much younger man.
Since my Grandmother's death he travels abroad often, and lives as a bachelor. He is a big man. Standing 6'4 and weighing about 220 lbs. His skin is tanned a rich dark pecan brown with a thick neck like a football player. His hands are huge and neatly manicured. Always a fancy dresser he was known for his attire.
... Continue»
Posted by mschoclate 3 years ago  |  Categories: First Time, Mature, Taboo  |  Views: 2335  |  
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mom sold me to her boss. part 1

my mom told my that we were going to a office costum party, and i had to dress up as a girl . she gave me fishnet's ,the sexiest panties, a skin tight mini skirt, padded bra,wig high heels, I love dressing as a girl but did she know that? we did my make-up so good! as soon as we get to the party she introduces me to her boss(Mike) as Brandy, Mike brings me a mix drink and leds me to his office. Mike grabs me and starts forcing me into kissing him, he pulls back and push's me to my knee's his cock was so big. I tell him im a boy not a girl,his black cock is in my mouth I dont know how but I was... Continue»
Posted by 912anika 3 years ago  |  Categories: First Time, Gay Male, Taboo  |  Views: 2361  |  
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my cousins girlfriend

Also true

I love my cousin i really do but he started dating this girl named Kayla and things began to change. She had 36 dd (told me herself) a beautiful ass and she was pretty. They began to have problems and my cousin moved away to Utah, why i don't know but he did and that's that. I saw my chance and i asked her how she was taking this. To my surprise she said she was glad because she actually liked me instead. We began to talk about sex and what they did she told me they never had vaginal sex only oral.

I felt bad for her but then she said her parents will not be home for several h... Continue»
Posted by bbwpussy6 3 years ago  |  Categories: First Time  |  Views: 1003  |  
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