First Time Porn Stories
Page 496

Chaz's f****y

This is a story in progress of a friend here Chaz Hope he and you all like it ,, more to come as we work it out right now it is all fantasy.

Chaz's f****y

Tim stood there stroking his cock as he watched his mom messaging her tits before she reached down and took her panties off to look at herself in the full length mirror. Tim saw for the first time the prize he had always wanted to see but more he wanted to feel on his young cock. Her reflection showed him the pussy he had always dreamed about and he started stroking a bit faster looking at the th... Continue»
Posted by superboytoy 3 years ago  |  Categories: First Time, Mature, Taboo  |  
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Maria: Training a Slut Pt. 2

It’s after eight o’clock and we’re finally on the road to the beach. Maria is sitting next to me, with her short black dress showing me a ton of milky white thigh. I can see she is trying to lean a little, the butt plug still wedged firmly in her ass. The trip is about three and a half hours, but it won’t be in her that long, because we are going to make a stop on the way… a stop about which she has no idea.

The first part of the trip is pretty quiet. She can sense this isn’t going to be an ordinary drive to the beach. After about an hour she puts her hand on my thigh and says, “Would ... Continue»
Posted by LongBallDave 2 years ago  |  Categories: BDSM, First Time, Hardcore  |  
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Finally!!

“So what’s it like?”, Lia asked.
“What do you mean?”, I replied.
“sl**ping with a girl, I could never do it, even for my husband.”
My first thought was that you shouldn't do if for your husband. But my vagina was clenching and asking why she was asking now. We were tipsy in my spare bedroom surrounded by sex toys and porn on the lap top. Back in the day she had been the girl with all of the toys and active sex life, now a decade later she wants to see my goodies. She also wants to watch porn which is new because she has always been squeamish and hated the lack of romance. So here we are su... Continue»
Posted by wifeluvsbi30 2 years ago  |  Categories: First Time, Lesbian Sex  |  
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Ann The Farmers wife Hay Time Day one 2/3

These are individual stories about a mature farmers wife and me (young virgin lad) back in the nineteen eighties and how we found out about sex and what we got up to over six months

My first time I saw a hairy fanny

A hour or so had past stacking hay, every three trips I made fetching hay bales I went on top of the stack to help Ann build the stack. We were 12 feet up in height now and I had to climb from the tractor cab on to the bonnet and climb up the front end loader to get on top of the stack this time non of the bales had been moved.
When I stood up on the stack I saw Ann wa... Continue»
Posted by nckboy 4 years ago  |  Categories: First Time, Mature  |  
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My Best Friend - pt. 2

Disclaimer: If you haven't read the first part "My Best Friend", I strongly recommend that you do so. It holds pretty much all the information you need to know about the two main characters, and who they got to where they are. Again, if you've come here looking for a quick wank, you'll be disappointed. This story is about the romance between two people. There is sex, and I'll try to make it as exciting as I can, but don't forget my main purpose here.

All characters portrayed are over 18. Any persons depicted, living or dead, are completely of my own creation and not based on actual
... Continue»
Posted by BigStevieAwesome 4 years ago  |  Categories: First Time, Gay Male  |  
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The Lion, The Bitch, and the fucking Wardrobe.

I guess I have always been a sissy. I started crossdressing at a young age and it gave me such a wonderful feeling that I struggle to form the correct words to describe the way it makes me feel. It just felt right, and ohh so sexy! Like I said, I have always been sort of a sissy, and my father couldn't have been less plesed. I think he had his suspicions that I might be, uhhh... different before he found my lingerie and stilleto shoes, but once he knew for sure thats the first time he hit me. He made me promise, at pain of... pain, that I would never do any of "that faggot shit" again.
... Continue»
Posted by redk1 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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WALKER1

Ivan was now 15. Ever since he was about 5 years old, he's had problems
with sl**pwalking. They keep telling me he'll grow out of it. It has
lessened as he's gotten older, but I've noticed stress seems to bring it
back. It was so bad when he was younger we had to have special locks on
the doors so he couldn't leave the house during one of his episodes.
Tonight I was awoken by a sound in the living room. As I crept carefully
into the living room, baseball bat at the ready, I heard Ivan's voice
mumbling. I set the bat down and carefully approached the chair where Ivan
was sitting.
... Continue»
Posted by john1195 1 year ago  |  Categories: First Time, Gay Male, Masturbation  |  
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Relationship Counseling

“It’s been so long since I had your mouth on my dick,” crowed five-foot-nine-inch, medium build caramel-skinned brotha as he pushed down on the head of the sissy cock sucker.
“You like it,” mumbled the thirty year-old big booty flame.
“Yeah,” he replied pushing the faggot back down his eight inch tool. “You ready to feel it in your ass?”
“Mmhmm,” Jayshawn Terry.

The five-foot-ten-inch, one-hundred-seventy-pound host stood up and grabbed his admirer’s hand. He led the guest down the hallway to sole bedroom in his apartment. He hopped onto the bed and began gyrating his ample, fleshy derri... Continue»
Posted by faggyboi 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Her First Threesome

"I've made up my mind", you tell me. "It's Rhett "   "You're sure? " I ask   "Yes, I'm sure.  Rhett will be the one" .   "OK, best you make the phone call then and give him the news.  Set it up for this Saturday  evening.  I'm pretty sure he's going to arrange to be free"     So you make the call to Rhett, letting him know that he is invited to join us for our first ever  threesome.  We've talked about it for a while now, and recently placed a contact ad looking  for a male to join us.  The idea has always excited me, and you decided that it was something  you're willing to try.     Out of sev... Continue»
Posted by dayvette 3 months ago  |  Categories: First Time, Group Sex  |  
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3 makes fun

My son and I had been having great sex for years till he decided he liked a cock better than a pussy. I really like a young innocent boy. My son was the one who would find them for me and bring them home. It usually ended up in a hot 3some. The last one was a street boy that stayed with us for a while and I got him first. The first night at our house when he was sl**ping i went to his bed naked. He was clad only in boxers. I got into bed with him and started kissing him and he did not know what he should do. "I am going to teach you to fuck like a man."i told him. "Take off the ... Continue»
Posted by palygirl 5 years ago  |  Categories: Anal, First Time  |  
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MEMORIES OF THE Y

Every weekend my f****y went to the local YMCA to going swimming. We packed a lunch a would make a whole day of it.
I got bored with the pool and started hanging around in the locker room to watch the men shower and change. One afternoon I was in there alone watching a man who was in his forties. I'd been watching him lathering up his body. Below his paunched hairy belly dangled a short stubby cock. He must have realized that I was watched him because he walked towards the toilet stalls at the far end of the locker room, beckoning to me. I was nervous to respond but my curiousity stren... Continue»
Posted by slappywag64 4 years ago  |  Categories: First Time  |  
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Banana Apprentice

Lately after a full day of stimulation and teasing my mind, vag and clit, for the first time I used a banana to rub at the same time my clit, my puss, its lips and my ass. The curve of the banana perfectly fitted my middle straight line starting from my upper clit reaching the middle of my ass hole. I placed myself doggie style on my bed, side head on pillow and my right hand holding the banana from under my tummy. I let my hips moved front and back to feel the banana rub all my parts at the same time. My middle ass-entry part that was not totally covered started feeling tickled and excited pu... Continue»
Posted by HeZe 4 years ago  |  Categories: First Time, Masturbation, Mature  |  
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Bernie, a fun fuck buddy

When I was younger I had a pretty wild sex life and met a few women along the way to join in on the fun. 
In my mid 30's I was dating this woman, Bernie. She was a few years older than me, a single mom, rubenesque, 40D's long blonde hair and quiet the appetite for sex. Bernie and I had a few 3ways, couple swap and went to an orgy. Other wise we kept it one on one.
One weekend Bernie and I went to a BBQ a friend of hers was having. As the night set in and my buzz kicked in. 
I noticed this woman and couldn't stop looking at. 
She was married, in her late 40's maybe 50, 5'9" dirty blonde, th... Continue»
Posted by rogue-1966 3 years ago  |  Categories: First Time, Group Sex, Mature  |  
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Cheating with Cathy

Cathy the 40 year old blond

Here’s a story about the first time I cheated on my future X. The future X and I were going through a rough patch, the usual stuff that all couples go to war over;

Money and sex.

Sex and money.

Like I said the usual stuff that couples fight over and it’s funny that money goes with sex as sex goes with money. If you don’t have one you won’t get the other.

Well here I was working at a big box hardware store chain as a sales clerk, low pay as low as the sex drive of the spouse, and I was also having the 10 year itch. I started to notice the women that c... Continue»
Posted by MountainMan66 3 years ago  |  Categories: First Time, Hardcore, Mature  |  
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Have A Seat (parts 1 and 2)


This is from Part 1.. you can skip past the bold font if you already read it..

I was hard at work one day when I heard my name announced over the company intercom. Great, another trip to the office, what the hell for now? Detaching myself from my duties, and pissed because I'm sure I won't get them accomplished in a timely manner now but whatever I guess, I head towards the office. I go in and have a seat, and boss #5 or whatever she is, too many bosses for one job I'd have to say.. Anyway she tells me I'm being called in for my job performance. Just what I need, being told by a girl 10 y... Continue»
Posted by Jester2069 3 years ago  |  Categories: Anal, First Time, Taboo  |  
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Fernando's First Time

Why does it seem that so many good looking men are married or living with ugly women? Maybe its just me, but it seems that wherever I go, I see these hot looking dudes chained to women who aren’t very hot and don’t seem to realize that the man they are with is fucking awesome. My roommate’s nephew is a good example. His name is Nando, short for Fernando and he’s spent a few nights on the sofa at our house. He’s Hispanic, 28 years old, about 5' 10" tall, beefy, solid, muscular build at maybe 240 pounds with the most handsome masculine yet beautiful face. He keeps his hair buzzed and has a faint... Continue»
Posted by BigSteveHouston 11 months ago  |  Categories: First Time, Gay Male, Interracial Sex  |  
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My first anal

'You never' I said, 'with him?'
'Well it was only a few times' Claire said, 'it wasn't like Craig was constantly fucking my ass'
'Mmmmm well you certainly are a dirty little slut so I wouldn't put anythng past you'
'and don't you love it' Claire replied 'You must have tried anal before, surely'
'No - had a bit of assplay with a few ex's but never actually fucked any of them'
'Well your cock is much bigger than his - not sure my poor little hole would take it' she said, rolling out of bed and slipping on her dressing gown.

A few days later I came home from work. I couldn't see Claire ... Continue»
Posted by dave31419 3 years ago  |  Categories: Anal, First Time  |  
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Cum Cunt

I've fantasized over and over again about tasting her sweet pussy on my tongue. Staring at her from afar, being teased from her sweet perfume! My pussy was drenched from her mere presence.

Being interested in women hasn't been good for my career. I've lost three promotions, two jobs, and one best friend because I couldn't keep my hands to myself. I guess it's the act that turns me on much more than the thought itself. Well up until now. This time I will get what I want, how I want it, and when I want her!

"Hey, Avril, are you coming to the office party tonight?" Umm the way my name roll... Continue»
Posted by lubr1que 3 years ago  |  Categories: First Time, Lesbian Sex  |  
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Talking about losing my virginity... (Sexomatic)


I was one of those lucky and fortunate guys, that was taught everything. The girl practically taught me all that she knew to teach me (the basics). My first time was a mind blowing experience that made me the "nose wide open" boy that I am today, HA! I never knew I could make a girl scream to the top of her lungs. Sweat poured from her body like we were working out. As we rubbed our bodies together it felt as if we were one. As I merged she would scream and I purged I moaned. Sad that we are not friends today. We can never be though we both moved on and have families of our own. She contacts... Continue»
Posted by choco-sexo 2 years ago  |  Categories: Fetish, First Time, Hardcore  |  
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step b*****r step s****r

it was a friday night mom and dad decided to go out for the evening leaving sam and anna alone for the evening sam always thought that his step s*s was hot but never had the balls to tell her instead he would just peep on her every chance that he could like when she was in her room undressing getting ready for a bath well one day anna forgot to shut the door not thinking anyone was home she went to the bathroom to get in the shower and b4 she did she began to masterbate on the toilet her step b*****r came around the corner and caught her playing with herself he became very hard but was embars... Continue»
Posted by dblac2 5 years ago  |  Categories: Anal, First Time, Sex Humor  |  
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