First Time Porn Stories
Page 461

First time with a Daddy bear

We chatted back and forth on Squirt.org for a few minutes. This was to be my first online cruising hookup, and I was unfamiliar with the protocol. I was afraid to come right out and say, “I just want to suck your cock, man”. I don’t know why I was afraid; after all, Squirt is a gay cruising site! Anyway, after a few minutes of asking each other what we were into, I got up the nerve to type: When and where? We exchanged phone numbers.

His name was Bill, and he was a sexy older bearish daddy type. I told him I wasn’t very experienced, and this was my first time going to another man’s ho... Continue»
Posted by pbg732 3 years ago  |  Categories: First Time, Gay Male  |  
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A New Beginning

Lindsey groaned in frustration. It had been so long
since she had felt a real hard cock inside her pussy.
Damn! What was the matter with him, she thought as
she looked at his shamed face. He hadn't even been
able to cum himself. For years, she had overlooked
his reluctance to initiate sex and invariably when
she did start it, it was unfulfilling and strained.

Her husband, Steve, refused to go to the doctor. No
doctor- no prescription. No prescription- no viagara,
or anything else. Well, she was fed up with his limp
dick! His trying to please her with his tongue was no
l... Continue»
Posted by griffen1 1 year ago  |  Categories: Anal, First Time, Gay Male  |  
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Her Son Liked to Watch - BBBBTS

Buck's Big Boob Bed Time Stories....BBBBTS


Beep! “The coast is clear” I looked down to see a text on my phone. I was waiting around the corner with some of my friends. We were waiting for Richie Mom to leave for the night. It was his turn to host a small poker party. We had a few cases of beer, some cheap cigars and a few pizzas’ for the poker party. I gave Bill the signal to move out. There were 5 of us stuck in a small mini van. We turned the corner and all got out in Richie driveway.

“Dude’s! What’s up?” said Richie. He had the door to his house open. We all walked passe... Continue»
Posted by therealbk 1 year ago  |  Categories: First Time, Mature, Taboo  |  
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A portable bed room (RV)

OK this will be the third time that I have actually seen Dana. We first me on line on AFF so we both kind of new that this might happen (OK my dream her selection).
Our first meeting was just a look see since she arrange to have lunch near by and suggested that I could have lunch there also. It went great with them sitting in a table next to me. We could have talked but like k**s we texted each other with me getting fresh and suggesting that I was imagining see her nipple through her blouse since I was sitting to the side of her.
Long story short we got to have a lunch date. That went gre... Continue»
Posted by Christian-Grey6 2 months ago  |  Categories: First Time  |  
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It's All About the Panties - Chapter 1

CHAPTER 1

It’s All About the Panties

Logan

My story starts in the summer. That glorious time of year when there is no school and no responsibilities. Specifically the story starts in the summer when I was f******n. The summer began, as they always do, with that giddy, free, ecstatic feeling knowing that I could do as I pleased. No deadlines. No homework. I could stay up late, or even all night. I could sl**p in. I could goof off with my friends all day long. I could even do my chores at my own pace. There is very little that can dim the bright prospect of that 3 month part ... Continue»
Posted by bbuster 4 years ago  |  Categories: First Time, Mature, Taboo  |  
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First time gay

This is my best mates first time with another guy.

His name is David. He is 23 living in Dublin and he was talking to me and all and asked me what was it like for me to say I was gay. So I told him it was hard but when I said If you dont like me for been gay you dont have to be my friend you dont have too. I asked him why he is adked ? and he said I want to know if Im gay or bi.
He was down with his best mate having a few drink and his best mate is gay. So a few words and my mate David ask his best mate a few questions like.

Whats it like to give a blowjob?
Does anal hurt?
Whats it l... Continue»
Posted by emmamad1 3 years ago  |  Categories: Anal, First Time, Gay Male  |  
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Two couples first time


Both couples were nervous, but especially the women. Both men had fantasized about this, but never thought it would actually ever happen. Neither one of the men could even pinpoint when the fantasy of sharing their wife with another man first entered their mind, but the time for this fantasy to come true was drawing near.

The odds of this occasion even happening was infinitesimally small. Dan and John were the first two to make contact and over the internet of all places. They had both found it exciting posting their respective wife on the web. They both were similar in that they po... Continue»
Posted by boberickson1965 3 years ago  |  Categories: First Time, Group Sex  |  
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Who's Getting Anal

Boy or Girl Anal? You decide?
He gently put me on all fours near the edge of the couch so I could present him the gift of my fine small ass. He knew exactly what to do. He got some Astro-Glide and moved his cock up and down my ass crack while gently inserting a finger into my awaiting opening. I was not used to anything in my ass and squirmed from his gentle probing; soon I could accommodate his finger. Then a strange feeling came over me when he began making an in and out motion which began to feel pleasurable. Soon I could tell the pleasure was overtaking the somewhat painful feeling of the... Continue»
Posted by captjim51 2 years ago  |  Categories: Anal, First Time, Hardcore  |  
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A WIFE AND NOW A STRIPPER

THIS STORY COULD IT BE FICTION OR REAL YOU DECIDE

A WIFE AND NOW A STRIPPER
When I married my husband Tom he had a very successful business in real estate and I was his very sexy wife who loved to dress up and look amazing for my husband when we entertain his clients,
Tom use to say I was the fantasy of all men and without my good looks and sexy body his business would not have been as good as it was,
With a 38”DD bust and my long sexy legs with long natural blond hair it was no wonder men would drool over me,
My husband loved it, as he knew I was his and no one else could fuck me on... Continue»
Posted by bobbyblue53 1 year ago  |  Categories: First Time, Hardcore, Sex Humor  |  
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Final Payment

I had been having some trouble with my computer at home and a friend from work offered to come home with me to see if he could straighten it out or at least tell me what was really wrong with it. Tony is a good guy like that, always willing to help out if he can. He is also a very big black man and, though I didn't know it, I was about to find out just how big he really is.

Let me start at the beginning. I have a stepdaughter who used to be a real pain in the ass. Always giving my wife and I grief over something. That is until a few months ago. She had a problem, (I created it for her thoug... Continue»
Posted by XXXNoBounds 1 month ago  |  Categories: First Time, Hardcore, Taboo  |  
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'Bored' Meeting

It was just another boring "last Thursday of the month" board meeting, and he really wasn't looking forward to the typical petty bullshit, the accusations of over spending, the idiotic questions of fiscal responsibility, blah blah blah. So as he slumped into the cafeteria style chair he wondered how long he would go without yawning, or at least without yawning with his mouth open. Jake hated these meetings even more than the obligatory semi-monthly meetings at work with his superiors, who he considered all to be self-praising blowhards. Or maybe that was blow hard; "Yeah blow me," he thought. ... Continue»
Posted by XXXNoBounds 1 month ago  |  Categories: First Time, Hardcore, Mature  |  
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Bicurious to orally bi

This is a true story of my journey from being a straight guy to loving the feel of cock. This being the only place that I can share it, it is not something that you can talk with your friends with over a pint lol. I hope you enjoy.

It all started in my mid 20s (I am 40 now)when I read a letter in a porn magazine that stuck with me. Basically a straight guy sucked another a guy and to his surprise he enjoyed it and said it was nice. When watching mmf porn,I started to think that the pleasure can be maximised if they all touched and enjoyed each other. I was very curious about it but shocked ... Continue»
Posted by curiousguy7 5 years ago  |  Categories: First Time, Gay Male  |  
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Unfaithful Wife with the Boss

As hard as I’d tried, I was fighting a losing battle, trying to stay faithful to my husband.
I’m what you would call a Jessica Rabbit. That is that I have very large firm breasts (36 DD) a very small waist (23) and a very curvy butt (36).
All of this is very firm and is exercised regularly to keep it trim.
Before I met my husband I used to podium dance in Nightclubs and on the odd occasion would earn extra money doing the odd striptease normally for private functions, Rugby clubs or Bachelor parties.
Once I met my husband I left that hedonistic lifestyle behind and settled into what I t... Continue»
Posted by neilmc123 3 years ago  |  Categories: First Time, Hardcore, Mature  |  
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Jane rides the subway......

Jane was wearing a dark long flowing dress, spaghetti straps, open from the neck line all the way down to the small of her back, six white buttons down the front. She wore black Steve Madden Deja Vu platform shoes, red lipstick and a splash of smokey grey eye shadow.

She was quickly walking down the street, as if she was late for an appointment. She was clenching her small purse in one hand and a ticket in the other. She walked down the stairs into the subway station. She could feel the warm air on her silky legs rising up as she walked further towards the platform. Jane looked left, then r... Continue»
Posted by jonzi 2 years ago  |  Categories: BDSM, First Time, Voyeur  |  
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Sophie's First .....

As he sat on the sofa he wondered what he was going to do today. It was two days before his birthday and he had the day off. He could have spent all day chatting on the computer with a friend having fun but she had told him the week before that she wouldn’t be online that day because she had some important f****y business to sort out. Oh well, a day watching the dross that they show on daytime TV or maybe even a couple of DVDs would be in order.

He missed Sophie and the fun they had enjoyed online chatting and hoped that they would be able to meet soon; they had exchanged addresses so as to... Continue»
Posted by russ007uk 4 years ago  |  Categories: Anal, BDSM, First Time  |  
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Vacation

Gone to the mountains for a vacation with some friends. We had a two bedroom condo with the most beautiful view. There was my female friend Kristy and the other couple, Steve and Megan. Kristy's parents spent two nights with us. So I gave them our room, nothing with them being my friends parents. More of how sl**ping on the pull out sucks, plus Kristie's mom is extremely hot for 62 years old grandma. Plus I want to smell her moms sent in my bed mmmmmmmm. She has this sweet smell without using any perfume.

That first night we all were getting cleaned up and ready for bed. I had on loose cott... Continue»
Posted by Gehld 4 years ago  |  Categories: First Time, Mature  |  
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Thursday Game Night

This is my first year in college and Im sooo nervous. New city, new people, new bills. Thank goodness my parents are able to send me an allowance or I would definitely have to get a new job...... or a job.... lol. My roommate is from New York. She is here on a full scholarship.... the brainiac kind. We make small talk and she seems nice enough. She asked if I needed a tutor..... and lord knows I did. So she offered to help me out...... shit I was grateful. I told her I would be able to pay her something every now and then. She said no worries we'll work something out..... cool.

Weeks have ... Continue»
Posted by MZSHUGAWALLZ 2 years ago  |  Categories: First Time, Lesbian Sex, Masturbation  |  
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Part 2 - What my future wife likes

One of the first nights we were having sex, she was sucking my dick and I told her she was really good at it. She asked me how many girls had sucked my dick. I said five or six but she was by far the best. She said it was because of all the practice she has had. I asked her how much practice had she had. She did not hesitate a bit and answered that she had been sucking dick since she was in the 8th grade, and that she had sucked a lot of dicks, too many to remember them all. When she said that I almost came in her mouth. She sensed this and said “Oh, you like that do you.”

She then st... Continue»
Posted by rnb 1 year ago  |  Categories: First Time, Hardcore  |  
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Bad Teacher Ch. 10

Chapter 10: Alone at last

After some troubled days at the Grants household my plan came through. Peter and Carmen had had some prolonged discussions about Carmen's pregnancy but in the end Peter accepted a trial separation. Tony was baffled at the news and not to keen on staying in a house with a pregnant woman. He told his mother that he loved her, but that he wouldn't want to move, so he would keep on living with Peter at the house before moving away to college. But he would visit Carmen and they could also talk at school.

I had already told my mother about the trouble in the Grants h... Continue»
Posted by Itheswag 4 months ago  |  Categories: First Time, Mature  |  
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My first encounter with a man

As usual when I was travelling I was sitting in my hotel room working. I finished my work while drinking a beer or two, as the tingling feeling started to grow. In my suitcase I had packed my outfits and my toys ready for some hotel room action. Although; action meant myself, porn and self-satisfaction.

I took a shower and washed away all the dullness of a day on travel. I was stroking my cock and balls gently feeling the hairless skin glowing, and my cock started to grow. Since I was eager to save up for a massive load I finished the shower and started to get dressed.

The black panties ... Continue»
Posted by theevilothertwin 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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