First Time Porn Stories
Page 481

My wif intorduces me to anal via strap on

My introduction to the joys of a strap-on dildo came in a roundabout way. My wife and I were attending an outdoor party at our health club in northern California. It was a nice warm evening and a great band was playing.

We were drinking wine and enjoying the music. My wife seemed to be particularly intrigued with the lead singer, a sultry brunette with long curly hair and a husky sensual voice. I had my arms wrapped around her and she was leaning back into me. I casually asked if she was enjoying the music. "You bet I am, that singer is so hot." My wife had never previously expressed any in... Continue»
Posted by etobicoke4fun 2 years ago  |  Categories: Anal, Fetish, First Time  |  Views: 1295  |  
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Curious Girls Deserve Spankings~

He let out a long sigh as he shut the door with a soft slam. It was a long day at work, and yet again he returned to a quiet home. The lights were all off, making him flick on the lights to break up the darkness. It illuminated his small house, the messy table and old couch coming into view. The only people that lived here was himself and his daughter, who he went to work for every single day. He wanted nothing more than to make the little girl happy and comfortable, even if her living arrangements were sub-par.

He glanced at the dirty dishes resting in the sink, and the food the girl must ... Continue»
Posted by pomf_pomf907 1 year ago  |  Categories: First Time, Masturbation, Taboo  |  Views: 4133  |  
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Loose Wife in Party By My Mistake

The party had been a disaster. My wife Neha, didn't want to go but it was my boss so I insisted. I also begged her to wear something sexy to get into his good books. That was a big mistake. The dress was far to revealing, low cut which showed off her superb breast and of course I stupidly told her not to wear a bra. When I caught my boss pulling down her top all hell broke loose. Neha by then had d***k far too much and my boss took advantage. I pulled her away from him and we left in a hurry to the sounds of my boss and his friends laughing. We drove in silence, I was too angry and Neha was in... Continue»
Posted by cuteb0y25 1 year ago  |  Categories: First Time, Hardcore, Interracial Sex  |  Views: 4986  |  
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First time... kind of.

I was a soccer player in my highschool very fit decent looking white guy..I went to a religious based highschool. Boys wore ties and sport coats. Girls wore skirts and sweaters. I was a very shy guy, but I could talk a good game with girls when I tried. I always was interested in this chick In my history class(final class of the day). I would trying to flirt with this girl and finally I said "truthfully I wanna go on a date with you sometime" she replied with "truthfully you aren't my type." I was shocked! I was decent looking, fit, and smart. But she shot me down. I got shot down in front of ... Continue»
Posted by Placebo_Effect 10 months ago  |  Categories: Anal, First Time, Interracial Sex  |  Views: 4153  |  
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My c***dhood Friend

It was one of those hot summer muggy days when a c***dhood friend of mine came to visit me. As he entered my home, he started to complain about his wife. G said that she just wasn't as horny as she once was and that their sex life had dwindled from everyday to 1-2 times every month. I could see the frustration in his face as he looked at me. We talked alot about his wife and then we began to chat about things we'd done years ago and laughed at them. G asked me then if I had any porn mags or videos and I showed him both. He said he wanted to watch the video called Cum Shots. As the video starte... Continue»
Posted by rickk1 6 months ago  |  Categories: First Time, Gay Male  |  Views: 2302  |  
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Taken First Time

I’d been thinking of it for a while, when I finally got up the courage to join a website and start looking for a guy for my first time. I was a sophomore in high school and just got my driver's license. I was shy and curious. I wanted someone who’d take charge and I guess ‘break me in’. I spent a while surfing and chatting to a few guys, getting a clear idea of what sort of guy I was looking for.

I was surfing the chat room when I was private messaged by an older guy. He was in his late 40’s and there wasn’t much information on his profile. He started asking who I was looking for and we go... Continue»
Posted by kbking70 2 years ago  |  Categories: Anal, First Time, Gay Male  |  Views: 2534  |  
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The Raft Trip

Dan and Shelley had met each other at the Mormon church that they attended outside Salt Lake City.Their marriage was great and produced two offspring a son and daughter who were now twenty-five and twenty-seven years old both c***dren had left home with marriages and careers in nearby states,so when Shelley's s****r asked her if she and Dan could look after her eighteen year old daughter Kylie she had reservations about accepting because her and Dan's c***dren had left the nest a couple years ago and they were enjoying the new found freedom of being alone with one another to pursue the common ... Continue»
Posted by goo4u 3 years ago  |  Categories: First Time, Lesbian Sex, Taboo  |  Views: 1254  |  
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My Friend Lisa Fucking Me With A Strap On (True)



This is a true story of mine I thought I'd share with all of you. It was my first time getting fucked with a strap on. Its a shorter story but I hope you enjoy guys and gals.


My friend Lisa (Pic attached) has always been a close friend of mine that luckily I have been able to have sex with here and there. I have always thought Lisa was very sexy and the fact that she is kinda of kinky in bed was even better. This story is based on one sexual experience we had together that I will never forget. One Friday night Lisa and I were... Continue»
Posted by xXSecondCitySaintXx 3 months ago  |  Categories: Fetish, First Time, Hardcore  |  Views: 4640  |  
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Sissy finds black cock

My gorgeous petite wife walked up in a flirty barely there dress that showed off her big breasts and curvy hips and it did nothing to improve my mood. It added to my depression.

Gina was so pretty a dozen times a year some idiot would bump into her car just to get to talk to her. Cops incessantly pulled her over and made excuses to get to see her license for her address. Our insurance agent thought they should create a new risk category called 'too gorgeous to drive.' He called three times a month to talk to her about it.

They kept her in the high roller area at the casino where she cock... Continue»
Posted by kinkybipaul 1 year ago  |  Categories: First Time, Gay Male, Taboo  |  Views: 9952  |  
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Younger for Older

I had been fantasizing about older men for a long, long time but couldn't seem to summon the courage to just go ahead and do something about! I considered myself mostly straight, but with a fetish for older (55+) white men. At the time I was only 26, and even to this day I would not want my friends and f****y to know, so that explains my hesitancy in taking that first step in fulfilling these sexual fantasies.

One day while surfing the internet for porn, I stumbled upon a website that catered exclusively to my particular tastes. This site's mission was to connect older men with boys like m... Continue»
Posted by jaywoolf 4 years ago  |  Categories: First Time, Gay Male, Mature  |  Views: 1223  |  
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My Night In Paris

So I Was In Paris France Last Year Hanging Out With My Best Friend Maya Now Maya Has Been My Friend For About Ten Years Now And Me And Her Had Always Been Close Sometimes we would Cuddle Kiss and a Little Bit More, Even Tho She Had a Gf at the Time and One Night I was At her Pine House she She Asked Me To Come To Her Room she Took MY Hand and Just Kissed Me and not Just a peck on the Cheek i mean like Kiss Kiss French Kiss it was amazing she told me, iv been wanting to do that for a long time i smiled at her and held her close then i started to rub her legs lifting her shirt up and taking off... Continue»
Posted by MissRawr 2 years ago  |  Categories: First Time, Lesbian Sex  |  Views: 612  |  
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exposing at the beach...first time...part 2

In part 1 I wrote about my first time exposing my breasts and then my pussy to some passers by and then to three young men who worked at the upscale resort in the caribbean. The beach was small and had no vendors, cruise ship types, just upper scale guests..many european, french, german,italian and some americans like us. Since it was french most of the girls were topless so I did not want to stand out so to speak and I took off my top too..(see photos in my profile). We were down at the end of the beach near a cove you can see in the photos. I felt more comfortable and even went to the wa... Continue»
Posted by pl246 2 years ago  |  Categories: First Time, Mature, Voyeur  |  Views: 858  |  
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The story of how i began crossdressing

This is copied from my blog http://cdcutiepie.tumblr.com, so the main updates will be there
i did think it would be nice to have it up here as well though :)

Entry #1:

I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :P


I decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there)

She told me she’s looking for a slave to entertain “them”
Thought it was a spelling... Continue»
Posted by CutiePie89 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 2069  |  
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my new babysitter

The new babysitter

At this time i want to tell you a story of when i got a new babysitter.

one evening my parents chatting and came up with the idea of going out on a romantic dinner for two being they were married for about 11 years and didn’t get the chance to go out much for some alone time for a long time now,
being i was sick often and had
and therapy and other activities and a baby s****r my mom had her hands full.

my dad brought up the idea of perhaps having dinner just the two of them
meantime i stayed him with a babysitter so they planed it out for a few days now.

my mo... Continue»
Posted by huezo 9 days ago  |  Categories: Anal, First Time, Mature  |  Views: 5319  |  
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Mum, Dad, John, and I. Good Ending (Wink!)

I tiptoed past my parents bedroom in the early hours of the morning, terrified they might hear me, there was no mistaking what they were doing, 'How silly', I thought, 'too much noise, John, daddies friend might, who was staying over, might hear them also', but that thought was banished, as I could hear snoring through the living room door, 'John sl**ping', flashed through my mind, as I turned left and dove into the toilet.

My b*****r was staying over with our cousins, but I declined when asked to go, instead opting to stay home instead, Mum was perturbed, but Dad was relaxed.

I sat ther... Continue»
Posted by MarieL 2 years ago  |  Categories: Fetish, First Time, Taboo  |  Views: 3085  |  
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That Night


NOTE: This is a work of fiction. Any
resemblance between the characters and any person
living or dead is an amazing fucking coincidence. I
mean really, I don’t know you or your s****r, so how
was I to know anything about what the two of you did
together? This story depicts i****t between
consenting adults and probably doesn’t break any law
in the world, unless you live in one of those uptight
super-religious countries, but then you’d probably be
breaking the law just by being on the internet to
begin with. So relax and enjoy the story.

That Night


My s****r and I ... Continue»
Posted by adel5000 3 years ago  |  Categories: First Time  |  Views: 769  |  
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My Deflowering

This story is an excerpt from a book I read, and if you like it half as much as I did, comment, friend me, and I will give you the title and author. It is a long passage, but you will be glad that it is. read-on, and enjoy.
I was in a girls finishing school, renowned throughout merry Olde England as the finest disciplinary establishment in the country, if not the world. The occasion was of my deflowering, a ritual that Rev. B., the headmaster reserved for himself. I was led to the chamber by the head mistress, and here we go.
Seeing I would not knock, she did so for me at the gruff growl f... Continue»
Posted by vince68 2 years ago  |  Categories: Anal, BDSM, First Time  |  Views: 880  |  
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The Night I guided my Nephew Inside me

We live and learn, and even I, with my misconception about boys getting erections and producing sperm, was surprised to wake up with my bare thigh covered, my nephew had got off, humping my leg and marked me as I slept.

That's the synopsis, here is the story.

During the night I was alone in my bed, and as my husband was away on work duty, my s****rs boy, had a stay-over with me and my son, his cousin, and they in turn slept in his bedroom.

They had gone to bed and I relaxed before going to my own bed, with a drink.
As I drank, I noted it was late, after midnight to be exact, so I fl... Continue»
Posted by MarieL 2 years ago  |  Categories: First Time, Masturbation, Taboo  |  Views: 8326  |  
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My son’s girlfriend

Well let’s just say I’m the mountainman66 I got that nickname so long ago I don’t even remember why. I’m a big old boy somewhat built like a tank, a water tank.



And like any good story worth telling, you have to have a protagonist and an antagonist.



But with this story you get to decide who is who.



It all started with my divorce, it left me somewhat high and dry, and not really caring about the opposite sex. Now who ever come up with that line had it right on the money. Opposite sex, what a laugh. More like obstinate sex.



BUT I’M NOT BITTER!



Okay now back to... Continue»
Posted by MountainMan66 2 years ago  |  Categories: First Time, Hardcore, Sex Humor  |  Views: 1276  |  
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Young Boy One Night Stand

Let me tell you about the young boy I had the one night stand thing with when I was a single mom. It's pretty funny because leading up to that night... there was a lot of sexual tension.... flirting... looks... etc. And after that night... we act like we don't know each other.

So this was when I was newly divorced so I had a newborn and a two year old at home so I didn't get to go out much! But sometimes on the weekend, I would go to visit my friend Debbie and I would go out. One of our good friends has a band and we would go to whatever clubs or bars that his band was playing at that nigh... Continue»
Posted by tplayer82 7 months ago  |  Categories: Anal, First Time, Taboo  |  Views: 4104  |  
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