First Time Porn Stories
Page 472

First Time for Everything

I was 21 and I had been crossdressing for a while. I had no idea I would later transition and become a transexual. Back then, it was all about the excitement of doing something apparently taboo, which really excited me. I felt dirty and embarrassed afterwards (thanks to my catholic upbringing), but I still loved it. I had started wearing my mom's and my s****r's clothes since I was 10 but I was growing taller and they were not. Had a problem with the shoes too. Dressing as Santa Claus for a 3rd Grade Christmas party at school gave me the opportunity to wear Mom's black boots in public, that wa... Continue»
Posted by latinCharm 3 years ago  |  Categories: Anal, First Time  |  
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Tha Pinup

Hello everyone hope you enjoy this story. Well I was out with tha fellas one night. You know just chillin thowing back some shots
and bowling at the same damn time. Lol, for the ones that get it, but anyways as I was getting
up for my turn. I seen one of the baddest chicks in there we made eye contact so I waved, she
waved back. So I was like "ah shoot" but I kept it cool she was with her girls a couple lanes down.
I didn't go over there right away bc I didnt want to come on to hard even though I wanted to
"tear dat ass up" as curtis payne would say ;-). As we continued to bowl we wo... Continue»
Posted by Plumppussy 3 years ago  |  Categories: First Time, Mature, Voyeur  |  
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The Convertable

This couldn't be more cool. A sunny day driving around with her older cousin Todd in his excellent convertible. She might have just turned eighteen, but she felt so grown up. Todd was almost twenty two. That was older than anyone she knew.

Pam brushed her hair out of her face. She liked the way he looked at her. It made her feel like he wanted her. It was weird to think something like that of her cousin, but he was a cute guy, after all.

She kept thinking about what Melanie told her when they were driving home from her boyfriend's house. Somehow they started talking about guy's things. M... Continue»
Posted by pornaholic63 3 years ago  |  Categories: First Time, Hardcore, Taboo  |  
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Lemonade & Whiskey

Part 3 of many, Enjoy

Ethan ran upstairs to his bedroom to get dressed. He put on a pair of boxer shorts. His thing was not as hard as before, but it hung out the left leg of his shorts. He put on his jeans and looked at himself in the mirror. His thing clearly stood out against his left leg. He sighed and took the jeans off.

Somewhere in his dresser was a pair of jockey shorts he no longer wore. He found them buried in the bottom drawer. He took off the boxers, put on the jockeys, and put the boxers back on over them.

Immediately, he was uncomfortable. The jockeys were too tig... Continue»
Posted by pornaholic63 3 years ago  |  Categories: First Time, Hardcore, Mature  |  
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Greek Salad

Chapter 2

Greek Salad


I opened my email box as usual to find the normal quantity of spam. As I scanned the addresses I noticed one from my friend, Aunan from Greece. Aunan and I had been emailing each other for several months after we found out we had a mutual interest, namely my wife, Ann.

I had sent some intimate photos of her to him as I found the thought of another man seeing her naked and masturbating over her, extremely erotic. Aunan had immediately taken to Ann and shown how much he liked her by emailing me video footage of himself wanking while looking at her photos on his ... Continue»
Posted by cuckold100 3 years ago  |  Categories: First Time  |  
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My wife's first time at 15- a true story

This story is completely true. It took me over 20 years to get it out of my wife Jennie.

When she was 15 she was getting pretty horny and was sick of being a virgin. She had a friend, Bobbie, who felt about the same way but had the advantage of being 16- old enough to drive.

One Friday night Bobbie drove them to a club that featured beer and rock music. They both looked hot, in different ways. Jennie was thin, with small breasts and a tiny waist over long legs. Bobbie had big tits but a thin waist and a nice tight ass. They were both wearing short skirts

They had to flirt with t... Continue»
Posted by man4all4 3 years ago  |  Categories: First Time, Group Sex, Hardcore  |  
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My first online date

This is about the first lady I met online. This is right about the time in my life when I found out my wife was having an affair; we were separated and going through divorce proceedings.

There was a website called Kiss.com. They went out of business. But, this was about 10 years ago when I discovered my wife was cheating on me. I tried to save our marriage. I took her to counseling and she freaked out and would not try therapy so I ended up getting a lawyer and starting the divorce proceedings. Anyway, the first part was we had to be separated. So since I was separated, I was no lon... Continue»
Posted by jonsampson 3 years ago  |  Categories: First Time, Hardcore, Mature  |  
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Apparently my GF is a slut pt 2

I asked my GF to explain "the pics" that she was talking about in the previous story, and this is what came out...cant tell if its hot or too slutty for all this to have happened...

My first month at school my freshman year I met this guy who I ended up being friends with. But when we first met, we used to fuck and one night he took pictures of me with my top off.
I didn't think much about it, but about a month later I heard he'd shown some of our other guy friends. Suddenly I had some asking me for blow jobs. At first I didn't know what to do and just laughed about it, but then some would... Continue»
Posted by iceman1012 3 years ago  |  Categories: First Time, Group Sex, Hardcore  |  
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Cheating s****r in law and me

This was sortaa thing that just happend but just shocking because i didnt think she felt the same and was the kinda person to actually go through with it. I knew my s****r in law for many years since i was a k**. She has been with my older b*****r for years. I always thought she was sexy as hell. When she stayed over night at my parents house she would always tell me im very cute and when i grow up im gonna be trouble to a lot of girls. Sometimes my b*****r would go out and she would be over during the night and i would see her in some very sexy clothes. Sometimes i would see her come outta th... Continue»
Posted by Raves415 3 years ago  |  Categories: First Time, Taboo, Voyeur  |  
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My GF's gangbangs

So this is another story from my GF's college years...she asked me to share it because of how hot it was to her. We'll share more if we get good comments.

I was a freshman in college I went to a party that turned out to be me and a bunch of guys...one of them had a video camera he kept taking video of the party. Then one said they had an idea...they wanted me to strip on tape. I was pretty d***k and somehow thought it was ok, and it was kinda hot to have all those guys (I think 12-ish) watching me. So I started taking off my pants, panties, then my top and bra and before I got fully undress... Continue»
Posted by iceman1012 3 years ago  |  Categories: First Time, Group Sex, Hardcore  |  
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Teaching Sally 2

My former student Sally and I were in a motel room and I had just had her watch me in the mirror while I took off her clothes and caressed her sexy body.
“Sally I want you to lie down on the bed on your stomach” She shivered when I told her this.
I quickly took off my clothes. I could not help but state at such an awesome ass. I climbed on the bed and started to lightly caress her back slowly moving down to her ass but I skirted by it caressing her legs. I ran my hands lightly up and down her legs. She spread her legs and I could see her juices glistening on her pussy lips. But I did ... Continue»
Posted by rich_7 3 years ago  |  Categories: First Time  |  
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My First Male Experience

This story is a work of fact and not a figment of my, sexual, imagination.

My first experience with another cock as a sex object (rather than playing with my own or seeing other guys’ cocks in the gym showers) happened when I was 18 years old whilst on holiday in Atlanta, Georgia. It happened on a f****y exchange visit whilst I stayed with a cute couple in their late 30s. He (Herb) was athletic, tall and tanned and she (Lucy) was shapely, without being model-type beautiful, but a nice cute girl all the same. They were friendly and I quickly settled into their home.

However after ... Continue»
Posted by PurplePal 3 years ago  |  Categories: First Time, Gay Male, Masturbation  |  
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Teaching Sally part 1

I am a high school teacher in a small town. I consider myself average looking. But for some reason it seems a good number of the female students in my classes delight in teasing me. There are days when some of them would wear low cut tops and low cut bras. Occasionally (if I am lucky) one or two would “forget” to wear a bra. These are the days I would spend time in class walking around checking their work and peeking down their blouses. It made me so hard and I know some of the young ladies noticed. Other days some of them would wear short skirts with cute panties. And again sometime... Continue»
Posted by rich_7 3 years ago  |  Categories: First Time  |  
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Hidden Erotic Desires

We all have those hidden desires, those unfullfiled sexual fantasies.....Would you let losse your inhabitions if you knew no one would ever know?



Karen had just received a text from her friend saying that her train had broken down and she wasn’t going to be able to meet for a drink



If she had received the text five minutes earlier she could have saved herself the £7.00 she’d handed over to the barman who had just served her a large glass of wine. Although he was quite fit and it was a very nice glass of Sauvignon Blanc, her favourite



She thought she may as ... Continue»
Posted by TWervas39 3 years ago  |  Categories: Celebrities, Fetish, First Time  |  
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A night at work

Many years back I worked security in a night club and during the week they always did little things to get peole in during the week. It was a Tuesday night nothing really goes on in this small town durning the weekend. So the owners decided with a radio station to do a karaoke competition and just my luck I was stuck working. So the night went well and around 11 pm the competition was over. A large group of peolpe stayed as I was talking with a regular from the bar this cute little chubby girl come up to me and asked if she could by me a drink. She had to be 5'4" sand blonde hair maybe 190 pou... Continue»
Posted by yogi49 3 years ago  |  Categories: Anal, First Time, Taboo  |  
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Enjoying Big Butt in NYC

I am a white male and I live in New York City, the big city. I had subscribed to several dating web sites. For me, because I travel a lot, having access to these sites is a blessing. On one of the normal sites, I was contacted by a lady. Come to find out, after some emails, that she lived close to me in the same neighborhood. It seemed she wanted to meet someone close, did not matter to me. So we met for drinks and a bite to eat after several failed attempts to meet up. She was 4 years older than me, being real, she sort of looked it a bit, she could have made herself look younger for sure. It... Continue»
Posted by buzzthe 3 years ago  |  Categories: First Time, Hardcore  |  
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Enjoying a Big Ass in NYC

I am a white male and I live in New York City, the big city. I had subscribed to several dating web sites. For me, because I travel a lot, having access to these sites is a blessing. On one of the normal sites, I was contacted by a lady. Come to find out, after some emails, that she lived close to me in the same neighborhood. It seemed she wanted to meet someone close, did not matter to me. So we met for drinks and a bite to eat after several failed attempts to meet up. She was 4 years older than me, being real, she sort of looked it a bit, she could have made herself look younger for sure. It... Continue»
Posted by buzzthe 3 years ago  |  Categories: First Time, Hardcore  |  
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My first time pt2

So as I left off everyone was on their way outside to watch the fireworks, I walked out with my friends and on the way to my friend truck my mom and her friend stopped me to sit with them on her tailgate, as much as I really did not want to sit between my mom and her friend with a raging hard on I did anyway until the fireworks were over.

As they finally finished up I told my mom that I was going to stay the night with my friends at one of their houses and told her I'd be home the next day, which I thoroughly intended and attempted to do.

But just as we pulled into the driveway and start... Continue»
Posted by RedRaptor22 3 years ago  |  Categories: First Time  |  
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Crazy Lady Part 1

I was in the Supermarket and walking down an aisle I saw this woman from the back.What caught my eye was her hair.It was long,down to her ass and a beautiful dark shiny brunette color.Then I noticed the skin tight jeans,They were black with sequins on the pockets,down the side,a lot of sequins.She was wearing high heel boots that ended just above her calf.She was pretty skinny and it looked good.I lost her but then saw her coming towards me in another aisle.The first thing that caught my attention this time was her face.I don't like to use the word ugly because we are all more than our looks.L... Continue»
Posted by jaimie49 3 years ago  |  Categories: First Time, Hardcore, Mature  |  
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a girls view everything has a Horn in Africa

I could hear the water run, so I got up and made my way across to the window and peeled back the curtain, just enough to be able to see out, and not attract attention to my action.

I could feel my heart thump in my chest, I had anticipated this moment since I had arrived here, and now it had.
I looked down onto the area where the water ran, bathed in the hot afternoon sun, reflecting from the wet stony floor, and onto the bodies of four young black men, of varying heights and body sculpture.

My eyes were drawn up their long muscular legs and stopped, no need to go further, and there th... Continue»
Posted by MarieL 3 years ago  |  Categories: First Time, Group Sex, Interracial Sex  |  
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