First Time Porn Stories
Page 19

My real s****r asked me to draw her naked

My s****r loves the movie Titanic, I guess she was watching it recently because she texted me last weekend and asked me for a favor but only on the condition that I agree beforehand. I was a...bit..skeptical at first but when she told me I realized it wasn't because the favor was something I wouldn't want to do...but because she was testing my dedication, obedience, love..and affection, testing if I would do anything for her no matter what.

Her request was to, like in the movie, draw her naked. I'm a halfway decent artist, doing digital art professionally and what not. I began to wonder if... Continue»
Posted by MichDye 29 days ago  |  Categories: Fetish, First Time, Taboo  |  
  |  3

Big boy

This boy that lives in my apartment building turned 19 last year and was going to graduate high school this year. He lives with his uncle, but his uncle's always at work. From time to time I catch this boy looking at me with those perverted little boy eyes. Staring at my boobs popping out of my shirt. Knowing he was looking at me, I'd tease him a bit. Bending down infront of him, Winking at him or blowing him a kisses. It's so funny because he's so shy. I bet he's even masturbated thinking about me before. I can only imagine what he'd do with me if I'd gave him the chance.

I was getting gr... Continue»
Posted by Pattybridges1915 29 days ago  |  Categories: Anal, First Time, Taboo  |  

My Ex Girlfriend's mom, Sarah

I hadn't heard from Cindy for 2 or 3 weeks, I had left messages, had not received any call backs. Sarah, Cindy's mom had tried at times to get Cindy on the phone with no success, Cindy just would just say "Tell him I am not home!". Sarah finally asked me what was going on? I told her that Cindy had more or less broken up with me over some crap reasons that I didn't understand. Sarah tried to get me to talk about it, but I wasn't going to be the one to open a shit can on what she was doing! Several times Sarah dropped by my house because she was in the neighborhood, she knew I was hurting abo... Continue»
Posted by Chartless 29 days ago  |  Categories: Fetish, First Time, Taboo  |  
  |  6

Slave Sanctuary #5: Full Moon-1

Full moon lasts two or three nights for me with my bad eye-sight, we celebrate it by beach beatings
Full moon, I line up my main sexy slaves and tie them with arm and legs spread to palm trees for me

For the full moon ritual I invited two fine friends to help me properly spank and use my main slaves
For the full moon party I line up my all sweet sexy slaves in groups of three or four for fornication

First we see the Swedish section with Sasha, Natalia, awesome Ashtyn offering us all their hot holes
Further on are American attractions with naughty Nadia, lusty Lauren longing for s
... Continue»
Posted by petdyke 29 days ago  |  Categories: BDSM, First Time, Group Sex  |  
  |  5


I thought I’d write this little story of a threesome we had last year. It had lots of good points and a few bad, but I thought this story might help couples in the future deciding wether enter into this way of life and share there wife with another man.

It all started about a year ago when I was researching men’s interest in bedding my wife. You see she is in her fifties now, but has the amazing body of a twenty year old, with a figure of 38D-26-36, yummy and dark hair, and with an intense need for sex. We’ve been married for over ten years now, and even though the first ten years of marr... Continue»
Posted by pixie54 29 days ago  |  Categories: First Time, Group Sex  |  


"I mean, didn't you ever think about doing it with your mom?"
my mother asked. I guess I wasn't so shocked as I ought to have
been, but we had been talking about the different aspects of the
current sexual scene for weeks now. It was only a matter of time
until the discussion got around to i****t.
"Well, ... sure, I guess so" I said, "All guys must at some time
or anoth ..."
"There you go, then!" my mom smiled triumphantly. "And mothers
fantasize about making it with their sons, believe me! Some
mothers actually do it. It's only natural!"
"You not serious! Would you?" I watc... Continue»
Posted by brianbigdogsmith 1 month ago  |  Categories: First Time, Taboo, Voyeur  |  
  |  1


It was a little after nine when the telephone rang. I was in the den,
planning our second honeymoon when my wife called up to me that my s****r
was on the phone and wanted to talk to me.

"Alright, Hon," I yelled out and picked up the black cordless from my
desk and pushed the activation button.

"Yes?" I said, into the phone, hearing the click of Shelly, hanging up
downstairs, as I did so.

"Hi," came my s****r's unmistakable soft, whisper-like voice from the
receiver. She didn't sound very upbeat like she usually did when she
talked to me.

"What's wrong?" I ... Continue»
Posted by brianbigdogsmith 1 month ago  |  Categories: First Time, Mature, Taboo  |  
  |  3


I guess that after we grew up, my s****r and I didn't mind much
about each other masturbating. We had each glimpsed the other
playing with themselves at different times over the years, after
a while it was no big deal. Only this time when I accidentally
discovered my s*s jacking off, it was was an incredible turn on!
Due to the job market, my s****r and I had moved back home while
looking for better jobs. Both of us were in our late twenties,
but mom and dad didn't mind giving us our old rooms back. Linda
must have figured that nobody would be home for awhile, so she
got naked, an... Continue»
Posted by brianbigdogsmith 1 month ago  |  Categories: First Time, Taboo, Voyeur  |  
  |  1


I can't remember exactly when my s****r Nancy and I first began
masturbating in front of each other, but by the time we were in
high school, we would usually come home after our dates with
other people and tell all about what Nancy called "the juicy
details." My s****r is a beautiful brunette with smallish-sized
tits. I'd tell about dry humping my date in the front seat, or
touching some girl's tits; and Nancy would sit back against the
headboard of her bed and slowly bring her knees up, then open her
thighs. As she listened to me describe my sexual adventures,
she'd moan a little... Continue»
Posted by brianbigdogsmith 1 month ago  |  Categories: Anal, First Time, Taboo  |  
  |  1

Playing With s*s

"Alright, alright...I know the drill." Tabitha said to her parents, leaning against the door. She kept the door open until her mom and dad had gotten into the car and drove off. Then she locked up for the night and skipped to the living room, grabbed the remote and switched on the idiot box.

"They gone?" A small voice queried. It was her little b*****r, Logan.


"So..." Logan flipped into the recliner, and twirled around in it for a few seconds. "What do you feel like eating for dinner?"

"Why are you asking? You cooking?" Tab laughed as she loaded a cassette into the VCR.

... Continue»
Posted by brianbigdogsmith 1 month ago  |  Categories: First Time, Taboo, Voyeur  |  
  |  3


Like most guys I like to masturbate in the shower from time to time. I
had just gotten into the shower and lathered up my cock when the bathroom
door opened. I had forgotten to lock it. It was my s****r Tiffany.

"I have to pee real bad," she said, excusing herself as she sat down on
the john.

Since the door to the shower stall was clear glass, Tiff saw me standing
there with my erection in my hand, all lathered up. I tied to turn away,
and I was really blushing. I had never been caught before!

It was real embarrassing, and unexpected. I guess Tiffany was a littl... Continue»
Posted by brianbigdogsmith 1 month ago  |  Categories: First Time, Taboo, Voyeur  |  
  |  3

Punk Slut s*s

"C'mon Billy, it'll be fun," Jenny urged me.
"I'm not sure," I shrugged, "It sounds cool and everything but..."

"Not scared are you?!"


"Then come on then! Come ooon!" Jenny whined, grabbing my arm, "I hate going there alone, it sucks. I can't go with that twat of a boyfriend anymore 'cos he's not my boyfriend anymore since he met that fucking cunt he's now banging."

"So you're dragging me there so you don't look like a sad recently-dumped singelton," I grinned.

"You motherfucker," sniggered Jenny, giving me a playful punch on the arm.

We were in the living room of our... Continue»
Posted by brianbigdogsmith 1 month ago  |  Categories: First Time, Masturbation, Taboo  |  
  |  1


The very first time I had sex, it was with my s****r's boyfriend, Jimmy. I had never seen a real
live boy's dick before, and I wasn't really expecting to.

It was New Years Eve, and Jimmy had come over to see my s****r Amy, while our parents were out at a New Years Eve bash with friends.

The three of us were sitting in the den, watching Basic Instinct on video. Jimmy and Amy exchanged
knowing glances a couple of times, and whispered to each other, and looked at me slyly.

I was kind of embarrassed, so finally I turned to them and said, "Do you guys want me to leave so you can alo... Continue»
Posted by brianbigdogsmith 1 month ago  |  Categories: First Time, Group Sex, Taboo  |  
  |  2


When I relocated on the west coast two years ago, I was virtually penniless.

I had moved to get as far away from my ex-boyfriend as possible. Our relationship had soured, and when I attempted to break up with him, he had grown obsessive and, in a word, scary. He stalked me, called me night and day on the telephone, and showed up at my workplace so frequently that I had been fired. I got a restraining order against him, though that had not slowed him down much. I changed my phone number, but he somehow had got hold of it. I simply couldn't get away from him.

One day at the spa, while ... Continue»
Posted by brianbigdogsmith 1 month ago  |  Categories: First Time, Lesbian Sex, Voyeur  |  
  |  1

wife takes a vacation without me

This is a true story
My wife is a hot little number, like I've described her before she is five foot four and weighs one hundred pounds. Her natural hair color is mousey brown but she bleaches it blonde. She has beautiful blue eyes and her skin tans a wonderful brown.

When we first married neither one of us knew much about sex. Oh we knew how to fuck but that's about all. I had a lot of mixed up feelings about showing off her body. I loved her small thirty four b cup tits and perfect legs , I often talked her into dressing to show off. But if any guy starting paying what I thought ... Continue»
Posted by woreout 1 month ago  |  Categories: Fetish, First Time, Hardcore  |  

The Campground

The Campground

My wife and I love to go to the mountains camping and hiking, specially since our k**s are grown up and we had more time for us, we both are older and settled, she is 47 while I am 49 and live had left some scars in form of some padding on the both of us, I carry my belly while my wife has only few belly but a nice big ass, and some great big breast.
It was getting late when we pulled into the campground, so the only spot available for our camper was beside a small older tent,
the kind that is just for summer camping when there is only sunshine.
We set all our stuff up and... Continue»
Posted by hornytogo 1 month ago  |  Categories: First Time, Group Sex  |  
  |  2

My first time with an older man...

When I was growing up, I would do pretty much anything for a bit of cash in my pocket. I worked in a sweet shop/newsagent every weekend from age 14 through until I had just turned 17. Our customer base was pretty much older men who would pop in during the day and spend as much time as was reasonably possible in the shop buying their sweets and papers, and chatting to the shop owner and me. It was during these years that I learnt how to deal with and appreciate the older man.

My boobs had started to grow before I had started work in the shop, and by the time I left I was sporting a rather ni... Continue»
Posted by niknak_bbw 1 month ago  |  Categories: First Time, Masturbation, Mature  |  
  |  2

My first time with an older man... Part 2

(Part 1 sets the scene... )

Following a steamy mutual masturbation session, Steve called me and asked me to go babysit for him again that night.
I walked out of the door and went home. I'd only been home for 40 minutes and was lying on my bed masturbating again, (He had really turned me on) when he rang me saying he was going to need me tonight for sure... "Perhaps you could stay over again?"

I thought carefully about what to wear that evening. I decided on a skater style dress. I thought it was not too risque but also quite practical. I packed my silky pyjamas, as Steve had ... Continue»
Posted by niknak_bbw 1 month ago  |  Categories: First Time, Mature  |  
  |  7

Case #8: It's Barbie's Fault

Case #8: It's Barbie's Fault
This was the first "Reverse Seduction" case we had discussed in our Group Therapy Sessions. Due to the nature and sensitivity of the topic, all names and locations have been changed.

"Um, I don't think that's such a good idea,Sweetie."
"Please,Daddy? I promised my Barbie that You Would!"
"Sweetie, we're not supposed to do those kind of things."
"Why not? Please? Don't You love Me?"
"Ah,for Fuck's sake!" I said, and quickly clapped a hand over my mouth. I Never swore in front of my daughter.

"Hee hee hee,Daddy. You said 'Fuck'! But You d... Continue»
Posted by dongerdoug 1 month ago  |  Categories: Fetish, First Time, Taboo  |  
  |  6

After 7 months friendship finally my 19 yr old fri

a 19 yr old girl and I became friends in dec 2014. She so cute tiny, 5'0 120-130lbs but all in her breasts. We met first thing that was said by her I have a boyfriend I don't cheat and please no foolin around talking dirty. So for past 7 months odd coffee/lunch texting each other talking on phone nothing dirty said. Last week I broke a dirty rule. She texted me and said why didn't you text back. I said no texting while one of us is naked no nudity talking. She giggled and said I am so funny.

So last night she finished work at 8 instead of 11pm. Instead of her going home she rang my doorbell... Continue»
Posted by Shybutready 1 month ago  |  Categories: First Time  |