First Time Porn Stories
Page 478

First Blowjob

I'm a tgirl and have been crossdressing for as long as I can remember. Once when I was 17 I went to a Halloween house party dressed as a hooker. (yeah, yeah, been done before but it's true). I wore a short and tight low cut black spandex dress, a silicone padded bra, black patent 5" pumps, and fishnet stockings. I added a long blonde hair extension to my naturally long hair, and did my makeup on the slutty side with false eyelashes, heavy eyeliner, and deep red glossy lipstick. Big hoop earrings and long fake acrylic nails completed the outfit. I have very soft and feminine feat... Continue»
Posted by KrissyMorehead 6 years ago  |  Categories: Fetish, First Time, Gay Male  |  
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Ruth - continued

While fucking Ruth, I'd noticed two things (other than her great breasts) which
turned me on. First, while grasping her ass I noticed it was considerably
bigger and firmer than I had realized, and secondly that she had a big, thick bush.

After the quick stand-up fuck we sat back, still drinking, where she told me
more about herself. She had married young, been with her husband over 40
years and had only had sex with two men other than him. More about that later.

As she talked, I couldn't help but play with the glorious hair on her cunt,
fingering her hole and ticklin... Continue»
Posted by joebobwahr 6 years ago  |  Categories: Anal, First Time, Mature  |  
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Tranny's First BBC

Sitting on the lounge at my local sex club I was watching the guys go by. You get to notice certain guys going past trying not to look like they are checking you out on the sly (and vice versa) thinking how they can approach me.

Normally it’s just the usual crowd of guys but several weeks ago a big muscular type African guy in his mid 30’s kept going past me and looking at me out of the corner of his eye. After about his third walk past I gave him a little smile. When I could see him coming down the hall the next time, I got up and slowly walked around the corner into the next hallway so he... Continue»
Posted by kbking64 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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Mrs B part 1

I spent most of my school years in boarding school as my parents lived in a different country so I'd only go home at the end of term.
During “Out” weekends I'd often go to friends and one in particular. I'll call him Darren. He had just moved down to the coast with his recently divorced mom.
Mrs B, was about 5'2", a really petite frame and prominent D-cup breasts. She had dark skin and long dark hair and stunning brown eyes. Even though back then she was just a little shorter than me she often wore high heels that made her taller than me.
Over the course of the 2 years that i knew spent wit... Continue»
Posted by Kalahari_Surfer 3 years ago  |  Categories: First Time, Mature, Taboo  |  
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Sometimes it just happens

It started when she asked me to come over to her house to check out her computer. Marcia said her computer was running very slowly, and sometimes it wouldn't even boot up at all. I told her I had the same problems at work and had found some great software that could address the issues. My wife, Patty, and I had known Marcia for many years. She even worked with Patty at the hospital. We had been married for fifteen years (we were in our mid-forties), but our relationship was extremely routine and practically without passion -- just going through the motions. I guess we both knew it, but w... Continue»
Posted by cranfordmason 5 years ago  |  Categories: First Time  |  
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Learning to Love Cum with Deb and Nikki

It was Friday night. I slammed the book shut and said to my girlfriend Deb, “Why the hell did I take Marxist Thought as a senior year elective?” It was late April getting toward the end of my senior year. I’d been studying all week and had hardly spent time with Deb. My balls were blue and I was looking forward to unloading them with her couple of times that night.
Deb’s roommate Nikki was out for the night, probably for the weekend the way Nikki worked. A couple of times Deb and I fooled around late with her in the room. I swear I could hear her mushing fingers into her pussy as we were pla... Continue»
Posted by drtang 3 years ago  |  Categories: Fetish, First Time, Group Sex  |  
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s****r and I

In the late 60’s when I was 16 years old I lived in upstate New York. My dad got transferred by his company to Miami. It was a big promotion for him so he didn’t want to turn it down. We were three k**s in the f****y. There was little s****r my big s****r who was three years younger than me and me. I was in my first year of high school and did not want to leave my friends behind to start in a new school in Miami. It took a lot of convincing but with the help of my grandparents I was able to convince my parents that I could live with my grandparents while going to High School and co... Continue»
Posted by henryh8 6 years ago  |  Categories: First Time, Taboo  |  
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Personal Assistants first Orgasm

I had taken on my PA when she turned 18. Jenny was the daughter of a very good friend. I have a good solicitors practice and employ a wide variety of people. All are good looking though. No old and crusty people will work in my office. People want to look at good people and that sells.

Jennys first day was a big eye opener for her. She wasn't used to a fast paced life and the demands I put upon her. Towards the end of the day I saw her coming out of the toilet all teary eyed. I waited until most people had left and called her into my office. I asked her what the problem was. She was say opp... Continue»
Posted by Sarah-longlegs 3 months ago  |  Categories: First Time, Lesbian Sex  |  
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Breeding Lynn

Chapter 1: Old Enough to Bleed

Lynn was a 19 year old newlywed. Sweet and innocent. I learned that she was a virgin when she got married only months before. Very attractive, friendly and outgoing too. She worked for me part-time at my commercial real estate business and since I was a one man shop, she did just about everything for me from secretarial work to closing deals. I was 45 and divorced with two grown c***dren who were older than Lynn.

Lynn was attracted to older men. Her husband was 16 years her senior and had a big time job with a law firm. Lynn was his fourth wife and his firs... Continue»
Posted by magas911 2 years ago  |  Categories: First Time, Hardcore, Mature  |  
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The OC - Marissa showing Summer what it is like be

Marissa Cooper's eyes blinked open after hearing the voice of her best friend
Summer Roberts.

She had spent the whole night partying with her friends and was d***k out of
her mind. It wasn't unusual for Marissa and Summer to stay out until all
hours of the night but this night had been special because it was Summer's
birthday meaning both of them were finally 18. Ok, so they were still
technically won't supposed to be drinking that they had both matured quickly
and the rich of Orange County could always get what they wanted.

Even though it was Summer's birthday had be... Continue»
Posted by Kate511 4 years ago  |  Categories: Celebrities, First Time, Lesbian Sex  |  
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b*****r And s****rs Bond

I stood in front of the refrigerator with the door wide open. I wasn't really hungry but I was sweating and hot. Grabbing the carton of orange juice I closed the door behind me and drank straight from the carton.

"Mom would kill you if she saw you do that!"

I turned around to see my four year younger b*****r, Chris, behind me. At barely 18 he stood just over 6 foot tall with a muscular frame. He had wavy brown hair and crazy wild blue eyes. I always marveled at how his eyes changed with his mood and they were like a wild blue ocean today.

"Well Mom isn't here now is she," I said sar... Continue»
Posted by loki3663 4 years ago  |  Categories: Fetish, First Time, Taboo  |  
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Big Dick Uncle Mike pt1

This is my true story as I remember it...


My f****y and I finally arrived to our hotel in NC for our f****y Reunion. We settled in after we greeted some of the f****y that had arrived and ate dinner. At was around 8pm when my uncle Mike bangs on the room door
(sounding like the police or an extreme emergency). My father answers the door and damn near cuss out his b*o-in-law for banging on the door like that but they were really close so it was all jokes when he saw it was "Hulk". Everyone called uncle Mike by his nickname "Hulk". They called him that because of his build and demeanor. Un... Continue»
Posted by nympho9 3 years ago  |  Categories: First Time, Gay Male, Taboo  |  
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The Long Drive

"The Meeting"
I was sent to a larger city in my area, to meet with some clients for a huge deal, that would set our company way over the top, higher than it has ever been before, and these African American men are the ones who were making it happen.
Donnell was my boss, and I had always done has he asked, but i was sorta nervous about this trip. not the meeting, but the co-worker he sent along with me, he was very well built, and very controlling, and even when he was being mean, it still turned me on.
we had a 4 hour drive, and left early that morning, in his 2010, luxury car,... Continue»
Posted by Kim_J 5 years ago  |  Categories: First Time, Hardcore, Interracial Sex  |  
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Porn Star

My neighbor, Mr. Brown, is a big dick. I mean major prick. He is one of these guys that gets mad whenever anyone gets on his grass, he yells at people all the time. His wife is a bitch also, she is in her thirties but dresses like she is a teenager.
This day Josh and I had had been at the pool for a couple of hours playing our favorite game-who I would fuck and how. We sit around the pool with our sunglassses on watching all the ladies and tell each other how we would fuck them. Then we get so horny we have to go to our houses and jack off. We had just got to my house when Mr. Brown sees... Continue»
Posted by zimabean 2 years ago  |  Categories: First Time, Hardcore, Taboo  |  
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Youngsville Part 1

Life in the city had never been great. I had always been a little bit of an outcast in school. I never made it into the social life there and most k**s avoided me. I had good grades and was usually the best in my class in all subjects. Could that have been the case? Jealousy? I guess I was smart and a bit of a know it all. My name is Eric and I'm a jack of all trades. I spend most of my spare time tinkering with things in my life, but I have also worked as a craftman in my uncle's workshop and garage. I also have interests in science. I know how to make machines tick, but I don’t understand ho... Continue»
Posted by drfleisch 2 years ago  |  Categories: First Time  |  
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FREAK ON THE CAM

I HAD THE PLEASURE TO EXPERIENCE THE FREAK THAT I NEVER KNEW THAT I HAD IN ME.....I DECIDED TO SEE IF I COULD FREAK MYSELF ON THE CAM...SO I GOT MY CAM OUT AND PLUGGED IT UP....

I DIDNT HAVE MUCH ON BUT MY ROBE...SO I TOOK IT OFF AND STARTED THE CAM...I WAS SO SHOCKED TO SEE MYSELF ON IT....I GOT KIND OF EXCITED...SO I BEGIN TO FREAK MYSELF..

I HAD ICE ON ONE SIDE OF THE TABLE AND MY FRIEND(DILDO) ON THE OTHER SIDE...I STARTED RUBBING ON MY NECK WITH THE ICE...STICKING IT IN AND OUT OF MY MOUTH....

I TOOK THE ICE AND STARTED RUBBING DOWN THE FRONT BETWEEN MY BREAST AND AROUND MY NIPPL... Continue»
Posted by ladytrucka42 4 years ago  |  Categories: First Time  |  
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My First Time With a Guy - True Story

First time was about five years ago. I had always been attracted to women and dated women. Love a hot redhead with some freckles...If only the Little Mermaid was real. At some point I decided to watching some gay, tranny and bi porn online out of curiosity. I have always appreciated a good looking and well built guy, but never in a gay way. More out of a want to work out more. One day I had been watching some porn, a little of everything and decided to meet up with a guy. I figured you only live once and you don't know until you try it. A few weeks later I got up the courage to post on craigsl... Continue»
Posted by chuckdiesel2 2 years ago  |  Categories: First Time, Gay Male, Masturbation  |  
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First time bi

I had never thought of myself as anything other than strait, even tough I had some thoughts about men a couple of times before, but I had always pushed them away, and moved on.

Up until recently I had a up and down relationship with a long term girlfriend, but in the last year the sex had become stale, and then nearly nonexistent. When we broke up I dove into work and had not had time or interest in other relationships, and had not even slept with anyone. Even though I had jerked off it was normally a quick session in the shower before work, or in bed at night.

After a month of this ... Continue»
Posted by sixjoker9 3 years ago  |  Categories: First Time, Gay Male  |  
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Watching My Mother

It was a gorgeous morning outside as I leaned nervously near the top steps of the staircase. My name is Paul, I am 37 years old, and I'd only recently woken up to the joys and possibilities of sex and the female form. I've always been such a shy and nervous person, but I'd been skirting the edges of thoughts about sex for quite some time now, probably a randy boy since the age of 13, but I went to an all boys high school and it took me a very long time for the information to get through to me that girls were good.

I had taken of late to spying on Carolina, my 67-year-old mother, as she was ... Continue»
Posted by VirginPaul 9 months ago  |  Categories: First Time, Mature, Taboo  |  
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Tracy & Me - Pt. 2

PART 2

A few months have passed since mine and Tracy’s d***ken encounter and not a word of it has been mentioned. At least, not that I know of. Stacy and I are still together and Tracy has moved in to her own place. She was still single. Lately she had been depressed because she was still single and spending so much time with Stacy and I was making her jealous. Tracy had no recollection of what happened and I put that memory deep in the back of my mind. We had now taken on a sibling like relationship. She complained to me about guys and asked me for advice. I even hooked her up with a ... Continue»
Posted by chocolatepapi 3 years ago  |  Categories: Anal, First Time, Hardcore  |  
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