First Time Porn Stories
Page 19

Humiliation 2 the ex

As difficult as it might be to believe, things after my huge embarrassment at the hands of my girlfriend, the large black man known as Link, and my closest friends, things had actually blown over. My girlfriend has not cheated with anyone else, (that I know of), and the whole affair is no longer even mentioned in our home. I thought, maybe, just maybe it is all over, but I was dead wrong.
One day, as I came home from work, my girlfriend was on face book, as usual, and I figured it would be another normal day. But, instead of sitting down to dinner as usual, she says to me, I am going out by m... Continue»
Posted by Drsmiley82 1 month ago  |  Categories: First Time, Gay Male  |  
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Room 209: First Sex as a Crossdresser

crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – bra

I've been crossdressing for much of my life, as far back as I can remember. I would even go to sl**p as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight for some time so I have breasts. As a man, I have to minimize them all the time. As a women,... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: First Time, Fetish, Shemales  |  
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FANTASY FULFILLMENT THEATER

CHAPTER ONE
CINDY

I was planning a trip to England and I began researching for some unusual things I might do there I came across an ad in the in the travel section for the Fantasy Fulfillment Theater. It was two lines, “Travel adventure, make your fantasy come true.”
I sent an email to the address provided and received a response in the form of a registered letter. There was a release, all matter of confidentiality stuff, an authorization for a performance bond guaranteeing my personal satisfaction and insuring against the release of my private information. I also found a fantasy request... Continue»
Posted by justluvtrans 1 month ago  |  Categories: Fetish, First Time, Masturbation  |  
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My First Cock

femdom – anal – male submissive

When I first met Jeanette, I thought, what a wildcat. She was beautiful and wild. Our very first night together I felt like she fucked me rather than the other way around. She made it clear that she loved being on top, and truth be told I loved it too. She aroused some deep passion in me, and I never wanted a woman more than I wanted Jeanette.

One night after foreplay that I wished would never end, Jeanette began bringing out a number of silk scarves from a drawer, saying, "I want to tie you up. Will you let me do that to you?"

She had already ca... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Anal, First Time, Gay Male  |  
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No Sermon While On This Moumt by Bingville

Joan and I have been married for more than twenty years. Our love life is still maturing. Other than acting out and verbalizing our respective fantasies, we have remained mutually exclusive. I think that a threesome with the right other man involved would be something which Joan would find habit forming. She claims this is something that she would never do, but really becomes aroused in our love making by the idea of fucking a former lover, fucking someone we both know who she finds attractive or, most of all, fucking someone with a big thick dick, black or white.

Joan still communicates by... Continue»
Posted by majfred 1 month ago  |  Categories: First Time, Group Sex  |  
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Chubby Freshman Chapter 3

Chapter 3
After his encounter with Richard a mature gentleman, the chubby college student displayed much more confidence with his courses in school and also around the guys at the dorm. One guy even asked if he had a girlfriend however others had continued to make crude remarks but he just shrugged them off. He carried himself with confidence and of course continued masturbating and thinking about older men. He even had even thought that the head of the History Department, a mature gentleman was interested in him. He had met him at a social for the Department when a professor had introduced t... Continue»
Posted by colourfast 1 month ago  |  Categories: First Time, Masturbation, Mature  |  
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Elders Meeting – Elsbeth

Elders Meeting – Elsbeth

There was a bit of a crisis in the Upland Rustic Church. Pastor Daniel and the two church elders had been making plans for months for their annual Elder’s Retreat and the Pastor’s assistant had just gotten pregnant. Who was going to take notes and run errands at the Pastor’s cabin in the mountains? It would not be seemly for the Holy men to look after themselves.

The Pastor’s assistant, Lily, was unmarried and just turned a teenager and those facts cast a big shadow over the church and the Retreat. Who was the father? The possible list of boys was so very sh... Continue»
Posted by tankengine123 1 month ago  |  Categories: First Time, Taboo  |  
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at last

some time back I posted a story about how i used to try and get 'caught' wanking off in B&B's/motel's that sort of place.

Someone recently asked me if it ever worked. Did i ever get caught and it lead to full on sex? Well not quite......now read on

It's been some years since I started this game and up until this event the best I'd ever had was some chalet maids stay and linger (watch) as I wanked off. But no-one actually said, "let me".

Skip forward many years to just a wee while ago. I was in a northern town, on business, staying in a mid range sort of place, saving a few pennies ... Continue»
Posted by merlinnz 1 month ago  |  Categories: Fetish, First Time, Masturbation  |  
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My Friend Tracy's First Lesbian Encounter

This story was told to me by good friends. They are a 15 year married couple, they are both bisexual now, but that only started over a year ago when they went on vacation to Caye Caulker in Belize. I hope I do it justice. The event is true but it is in my own words. I will be sure to have them read this over prior to me publishing it.

David and Tracy arrived in Caye Caulker in December of 2014. They had rented a nice cabana by the beach that offered a great view over the water. They were on the second floor of the cabana with a separate accommodation below them. Both accommodations w... Continue»
Posted by Angelsmith 1 month ago  |  Categories: First Time, Lesbian Sex  |  
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My Son's Best Friend

Jack was my son's best friend. They have been friends for many years. I have always had a thing for Jack and he has had one for me. The whole time he was growing up I would flirt and tease him. I would flash him my tits and my pussy. He would blush after he got an eye full. When the boys hit puberty the got very good looking and horny. Jack and I continued our harmless fun. I was only twenty years older than them and really enjoyed the thought of Jack having nasty thoughts about me.
Well then my husband got a job offer in another city, it was too good for us to pass up. We were going to ... Continue»
Posted by zimabean 1 month ago  |  Categories: First Time, Mature, Taboo  |  
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The library

Mr. Donaldson (Gary) (32), was a library executive assistant at a old library in a small town. The head librarian was a strict lady Gertrude Tunney (64) who had been there for years and was very prim proper conservative who ran the library with very strict rules. Her library employees were Mr. Donaldson, Diane Jenkins a redheaded 20 year old and Jane Foote a 19 year old brunette. They all wore very formal clothing and acted in a very prim and proper way. Mr. Donaldson was a nudist and a art/erotic photographer on the side and did not like the strict nature of Gertrude's dress code. Gertru... Continue»
Posted by barefoot123 1 month ago  |  Categories: Fetish, First Time, Hardcore  |  
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An amazing first with friend and her cousin ... Pa

While they were catching their breath I was busy fondling and caressing them both. After a few minuets Amber asked what I had in mind next and I reminded her that she had told Amber that she needed to suck my cock!!! Amber blushed and said she would love to but had never done that before and Jamie said that she guessed she'd just have to teach her then. She told Amber to lay down next to me, pay real attention and watch closely. Jamie got between my leg and reached out and wrapped her hands around my rock hard shaft. Then she bent down and kissed the head of my dick before licking all around i... Continue»
Posted by luvcuntlickingsluts 1 month ago  |  Categories: First Time, Group Sex, Hardcore  |  
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A canoeing day that went wrong/right.

A canoeing day that went wrong/right.



The events that got me into this position are unimportant. What is important is that I’ve been backed into a blind date, so my canoe buddy can get into a perfect 10 blonde’s pants. He has covered for me in the past. So fairs, fair. The 20 something brunette in the front of my canoe has a pain face and has dressed in clothes that do not show her figure at all. The only thing in her favour is that she hardly says a word and obviously knows how to paddle. I can’t wait to get this ‘date’ over!
The trip went without event until the last weir. John and ... Continue»
Posted by CanoePirate 1 month ago  |  Categories: First Time, Sex Humor, Voyeur  |  
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Pilots Strike

We would never have met Johnny if it hadn't been for the airline pilots strike in '89, normally we would have flown from Adelaide to Melbourne for a wedding but due to the strike we had to drive. Which meant we ended up meeting Johnny, more unusual was because it was a friend that asked us if we could give a lift to a friend of his son, complicated but we ended up picking the guy we had never met from Fullarton, which was out of our way and taking him to Melbourne.
Johnny was an 18 year old university student, well presented, however I think that was because he was going to his s****rs weddin... Continue»
Posted by petercee 1 month ago  |  Categories: First Time, Taboo, Voyeur  |  
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My First Threesome

So the other week I finally ticked a threesome off my to-do sex list. It didn't go down exact how I had imagined it would but I still had a lot of fun. I always imagined having a threesome with two girls, not with another guy. But when my best mates nervously asked me if I would like to try one with his hot girlfriend, what is a bloke suppose to do?

I'll skip the boring part of the story about how this came to be and just get into the juicy part. So I went over to their apartment one night to suss out if it was going to happen or not. It was a little awkward at first arriving know what we ... Continue»
Posted by AussieBob93 1 month ago  |  Categories: First Time  |  
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Me and my sexy teasing teacher!

This is a story about me and my sexy teacher most of this is true but I hope you enjoy it as much as I will ejoy sharing it! Please add me for more and message me and suggestions!

My absolutely stunning English teacher the lovely miss. Steele my maths teacher! Ever since I first joined that school in year 9 in my adolescence, my hormones absolutely raging! Sitting through her lessons watching her beautiful figure lot across the room with its magnificent grace, it made me desire her every hour of everyday! Her voice sounded like bliss even when telling me off she sounded like and angle her v... Continue»
Posted by thegentleman97 1 month ago  |  Categories: First Time, Mature, Taboo  |  
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Trying Something New

Ive always wonder what it would be be like to have my cock sucked by a guy so I decided to try it. He was an interesting man that I had worked with some years ago and we had always been good friend so when he invited me to take in a Chinese down town I was happy to accept. Gill is quite tall and I guess handsome in a rugged fashion, a few years younger than me and has kept himself in shape.
We were drinking in a bar after the meal and I raised the subject about women... did he have a girl or was he still on his own. He didn't reply straight away but after a while he look at me and said.. "W... Continue»
Posted by bardeen 1 month ago  |  Categories: First Time, Gay Male, Group Sex  |  
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The Genesis of My Inadequacy

This is a true story from my younger years, which like the rest of my posts, dissolves into self-loathing rhetoric, lol. I was around thirteen at the time, and I had just moved down the highway, a move of about ten miles, but I found myself assigned to a new school. Some quick context from those who might be reading this and not have seen my page: I have a really tiny penis, I’m a total loser, and I’ve accepted that.


My new school was only a little bigger; still small though, and still in a pretty conservative area, but the culture was totally different, as far a sex goes.

My neigh... Continue»
Posted by spardi06 1 month ago  |  Categories: Fetish, First Time, Voyeur  |  
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First time with a man

This as all my stories is a true story about the first time I got with a man

I was 18 and living with parents, they had gone away for a week so had the place to myself, I had a girlfriend at the time but she was in uni and too far away too get back, one night I was horny as hell, I needed to get some action I started talking to a few girls over Facebook to see if I could get someone too come over but no luck, I was getting more and more horny so thought fuck it put some porn and started to wank, I've the last year when watching porn I had become curious about cocks I have never found men a... Continue»
Posted by basingstokeboy 1 month ago  |  Categories: First Time, Gay Male  |  
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Мой первый мужчина

Привет. Я расскажу реальную историю о том как я стала женщиной. Сейчас мне уже почти сорок лет, но события того лета до сих пор свежи в моей памяти.

Мне было 18 лет и я был высоким и стройным юношей. Но широкие бёдра и узкая грудная клетка отличали меня от моих атлетически сложенных ровесников. Я был романтичным и нежным и в отличии от них не интересовался футболом и мотоциклами. Я любил читать и смотреть мелодрамы и любовные истории, а на красивых и сильных мужчин смотрел с замиранием сердца. Так как я с детства считала себя девочкой, то повествование буду вести именно так.

Один такой м... Continue»
Posted by miss_slonik 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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