First Time Porn Stories
Page 495

Homecoming week... pt 2

The rest of the week was pretty frustrating as Megan’s and Christie took every chance they could to tease me around school.
I managed to survive the week of football practice with Christie and the squad practicing around in short shorts and sports bras. Christie was a huge tease as she would often talk dirty to me during our nightly calls and even email some naughty photos. She told me not to jack off all week because she wanted me to save it for Homecoming.
Through it all, I received good news on Thursday practice as the coach told me I was starting at Strong Safety cus Danny, our st... Continue»
Posted by dontbhatin 5 years ago  |  Categories: First Time, Hardcore  |  
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Another business trip (True)

I went down to the restaurant in the lobby for dinner at about 7ish. The place was pretty busy with mostly business dinners and office after work social gatherings. There was a group 6-7 of women sitting a table. As I went through dinner I noticed I kept connecting eyes with one woman in particular. She was a mid-30s, attractive business professional type, just above her shoulder brunette, about 5'7"ish great body in a girl next door type of way, slim to average but proportional. I thought that maybe it was a coincidence but after a few more glances I could tell she too was looking in my direc... Continue»
Posted by hunknhot 3 years ago  |  Categories: First Time, Masturbation, Mature  |  
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Why do I think my daughter is Attractive #4

Although I fell asl**p fast spooning my wife , when we awoke later that day , I realized that I unwittingly created a new dynamic in the househould. I had introduced my sexuality to my own daughter and she was willing , to say the least! Nia was an outgoing girl and she had no problem being herself. Before dinner , as my wife was preparing the food , Nia was on the couth craddled under my arm watching the football game with me. Asking me questions non stop she was always inquisitive. My wife Amy shouted from the kitchen.."10 mins guys". Our TV room was around the corner and could not be see... Continue»
Posted by KinkyNick420 4 years ago  |  Categories: First Time, Taboo  |  
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Part 1, The Succubus with a Cock

Part 1, The Succubus with a Cock
His cock felt so good between my lips. I savored every inch with such great passion he moaned and f***ed my head farther down his shaft. I gagged many times but I was getting better at deepthroating. His balls were coated with my saliva, and soon the couch we were sitting on became wet to. I really did enjoy big cocks in my mouth. I had really acquired a taste for it if you’ll excuse the expression.
But it did not begin here, I stated with a surprise and then I was forever changed. One single act started me down a path that I could not return from. If given t... Continue»
Posted by decarabria 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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my life. the early years

My Life
Chapter one
The early years
I was born in the early sixties on a farm about two miles from anywhere, I never knew my mother because two days after giving birth to my younger b*****r something happened and she was rushed into intensive care where they tried everything to save her but she slowly slipped away. At this time I was only three years old and to be truthful have not many memories of her only what I’ve been told by either my dad or my three older s****rs, my s****rs bought up my b*****r and myself because dad had to run the farm and get enough money to buy us things, we were... Continue»
Posted by ken256 4 years ago  |  Categories: First Time, Hardcore, Taboo  |  
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A Weekend of Firsts Part 1

I should probably start off this story by saying that all of what I am about to put is in fact real and happened to me a few years ago when I had just turned 20 and is not exaggerated in anyway. In fact I'll have to keep some of what happened out of the story so I stick to the rules.
I will try articulate it as best as I can. Hopefully I won't get too descriptive and make it too long.


This night started like most nights when I lived at home, desperate to sneak away have sex and come back without anyone noticing, so I decided to jump onto a gay hook up site that I had visited before. Usu... Continue»
Posted by petevack 3 years ago  |  Categories: Anal, First Time, Gay Male  |  
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first time hubby shared me with another guy! (plz

hubby always liked it when i flashed him around the house and let him take pictures. but one day he showed me a website where girls can post their pictures and guys can comment on them. so i submitted a few that he took of me, and instantly we got hundreds of comments from guys around the world telling me so many sexual things and fantasies they had with me. it turned me on alot, and i mean ALOT! my panties were soaked and the first words out of my mouth was "FUCK ME!". but this day in particular my hubby was in a rush to buy a bottle of liqour before the store closed.

so we got to the liqo... Continue»
Posted by discreet4rmlanc 3 years ago  |  Categories: Fetish, First Time, Group Sex  |  
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My first stranger.

I practiced dressing hundreds of times before I went out in public. I went out in public dozens of times before I tried to pick up someone. I wasn't attracted to gay men - I liked men who appreciated me for my feminine side, so because of that I only wanted to be with a straight guy. Obviously this proves difficult, since straight guys don't want their girl to have a cock. I have found that usually they are so turned on by the time they find you have a cock that they don't care.

This is the first time that happened to me.

I finally decided I was ready to try to pick up on a guy.
... Continue»
Posted by hotchickinchitown 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Me and the Boys Doggy Roleplay

Hope you like this one. Names have been changed to protect the non-existent.
We were all sitting in my bedroom. Me and Johnny on my bed, and Billy and Jimmy across from us on my b*****rs bed. It started off as a sorta straight circle jerk. We had all started masterbating together recently and it gave us a chance to compare notes.
Johnny asked me if I ever wondered what it would be like if someone else jacked me off, the feel of a different persons hand doing all the work. I told him to give it a try, and to break the ice, I reached over and grabbed his hairless hard cock. He let out an "ugh... Continue»
Posted by badboy4320 2 months ago  |  Categories: First Time, Gay Male, Group Sex  |  
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working out with Colby and free weights

I was a nieve k** as you will soon see, I am straight but this is the story of how an upper classman at my boarding school taught me how to get muscular and cut. Colby had a great body that all the girls shrilled about and all the guys wished they had. Colby was our dorms leader and one day I asked him if he would show me how to work out and get results like his. He told me I had to be serious and willing to work hard and I had to earn his trust and respect. I was so excited that he at least was willing to consider helping me out. There where a lot of rules some of which as a shy k** like me w... Continue»
Posted by str8guise 6 years ago  |  Categories: First Time, Gay Male, Masturbation  |  
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I was fully straight before this incident

This is a true story..


It was back in college days, i had lesson and asked teacher if i could go toilet. He allowed me and off i went.

I had to go to the main reception to get toilet keys (toilets neve stayed open during lesson times). Got key and unlocked door and entered toilet.

As i was washing my hand another boy David a year below me came in, he was just washing his hands looking at me, i thought nothing of it, then Ben a boy a year older entered toilets as well. He was a big guy and everyone was scared of him, including me.

David the younger boy just smirked at me and start... Continue»
Posted by madmax2k12 3 years ago  |  Categories: Anal, First Time, Gay Male  |  
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FUCKING AT THE BAR AFTER CLOSING

I JUST WATCHED A VIDEO WITH VANESSA CHASE THAT BROUGHT BACK A VIVID MEMORY OF A NIGHT THAT I FUCKED LORI IN THE BAR AFTER CLOSING TIME. I WAS TENDING BAR AND LORI AND HER 'OLD MAN' (HE WAS 50 AT THE TIME, SHE WAS JUST 21), ANYWAY THEY WERE REGULARS AND SHE ALSO PLAYED 3RD BASE ON THE GIRLS SOFTBALL TEAM THAT I COACHED. WE SPENT A LOT OF TIME FLIRTING AS I GOT TO SEE HER ON AN ALMOST DAILY BASIS. SHE AND HER BF ALWAYS TOOK THE TWO SEATS AT THE END OF THE BAR NEXT TO THE STOREROOM. MANY TIMES THE JOINT WOULD BE PACKED AND SHE WOULD BE STANDING AT THE BAR OPENING AND I'D HAVR TO SQUEEZE BY TH... Continue»
Posted by vukey 5 years ago  |  Categories: Anal, First Time, Taboo  |  
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MY ONE AND ONLY TIME!!

If you have looked at my video collection, I love shemales. I have always wanted to have sex with a shemale. I think it would be the best of both worlds.

I have only had one “gay” encounter. It happened when I was in the 4-t h grade. I was swimming at my friend Jimmy’s apartment complex. We went there after school for a swim as it was a very hot Florida day. We swam, goofed around, just had a general good time before the afternoon cloud and thundershowers came in. They came, so we got out and decided to get changed.

We walked into Jimmy’s bedroom. He immediately dropped his suit,... Continue»
Posted by abigfan 10 months ago  |  Categories: First Time, Gay Male, Taboo  |  
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my next door neighbor

During the summer, my lady neighbour & I bantered back and forth over the fence in the back yard.

She was a good looking married woman, with longish hair to just below her shoulders, and always had it shaped like a V, and a she sported a body, that just begged to be man handled. I dont know if I was flirting or just being nice. Its was just nice to have a good looking woman talking with me.

Brad, her hubby, was a great guy, very straight, and liked his beer. Great neighbour, helping with cars, and various other man things around the hourse. He worked a lot.

After she came home from wo... Continue»
Posted by silverfox62 4 years ago  |  Categories: First Time, Mature, Taboo  |  
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Mother says it's alright (Not true story)

I am not author of this story.

My mom and I live in our small cozy home in a village out on the countryside, never met my dad and hardly ever had any f****y over as far as I can remember. Basically it was just my mother and I, we had no problem with that since we had such a fantastic relationship; she was loving and caring. My mom is in her late forties with a chubby figure and long blonde hair, with a smile which immediatly lit up the room. I'm an average looking guy who is going to school and has always felt a deeper connection to his mother but could never make sense of it. That w... Continue»
Posted by PornApocalypse 3 years ago  |  Categories: First Time, Mature, Taboo  |  
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Mission Accomplished: A True Story of a Young Man

Mission Accomplished: A True Story of a Young Man's Anal Deflowering

As a relatively inexperienced, bi-curious young man of 19, there came many occasions where the rage of my hormones took over, and I would go on the hunt for cock. I had zero interest in having a gay relationship. I wanted one thing and one thing only. I was hungry for it and nothing was going to stop me.

This is the story of one of my cock-frenzied manhunts.

I had tried on several occasions to lose my anal virginity without any luck.

I was very closeted, so these past missions were riddled with the buzz of... Continue»
Posted by Shadinger 3 years ago  |  Categories: Anal, First Time, Gay Male  |  
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Early experience with a guy (Pt 3)


After my second experience round at Ted's I knew the only boundaries were the ones I set myself and was entirely easy about what we'd done and the fact that he was as old as he was, and I was as old as I was, didn't bother me. I couldn't wait to go round and see him again and see what happened next, the mystery of what could possibly be in store was so exciting I got a tingling sensation when I thought about it and my penis stiffened.

I couldn't go round again until the following weekend, my f****y were in town shopping and I was pretty much left to myself. Although it had been six days ... Continue»
Posted by davidW1967 1 year ago  |  Categories: First Time, Gay Male, Masturbation  |  
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Fucking Melissa's Hairy Pussy

Melissa was my employee for about five years. We hit it off immediately from day one when we both started at the same company. Immediately I thought she was cute. She had long auburn hair, light skin with freckles, a fat belly, thick thighs and small tits. At first I really had the hots for her as I absolutely am attracted to, and love, chubby girls, especially ones like her. We became best friends despite me being her boss. In fact, she became my right hand girl and I couldn’t have done a lot of my job without her.

I would “innocently” flirt with her at times and she’d do the same, all in ... Continue»
Posted by naturalwomanlover 1 year ago  |  Categories: First Time, Hardcore, Masturbation  |  
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The day I found out I was a bottom when it came to

I invited my friend round one day after school just to play xbox, hang out and smoke some weed.
We sat down on my bed and watched tv before switching on the xbox. I bent over to turn it on and he put his finger against my asshole. This didn't bother me as we are both comfortable with our sexuality and are always naked around each other.
As we started playing i noticed he had a raging boner, he has a MASSIVE dick, its bigger than most things in porn. At least 10 inches. When we play xbox the winner always makes a bet for the loser. I won our game and I dared him to let me suck his cock, as I ... Continue»
Posted by wantingboy 5 years ago  |  Categories: Anal, First Time, Gay Male  |  
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Watching Girlfriend taking an 11.5" cock Part

For the next three weeks everything seemed normal on the surface. Life was routine in most respects, except I was looking and contacting suitable guys online from swinger/contact ad sites.
I eventually contacted 2 guys and asked for proof shots or videos.

I got an instant reply from one guy called Simon, and a video enclosed in an email called 'Proof'. I eagerly opened it up and As I watched, a pair of hands reached out to fondle the obvious bulge in his trousers. She wasted no time unbuckling his belt, unzipping him, and pulling his slacks down, revealing tight white boxer briefs that ba... Continue»
Posted by donna32a 1 year ago  |  Categories: First Time, Hardcore, Voyeur  |  
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