First Time Porn Stories
Page 482

A true story: me and a transvestite man - part 2

OK this is the second part of my true story. I was going to leave it at two parts, but I think there's enough to make it three parts, now!

I think I'd best point out that beyond the (I'm told) common early sexual experiences most straight men have as youngsters, with other men of their age, I'd not had any experience of men. You won't, of course, get many straight men who admit to this. But I'm not like most men.

However, this early experience was enough to leave me curious as to what it would be like to have fun with a cock. As you may have read in part one of this story, I was rapi... Continue»
Posted by LookingForSomething 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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wife fantise looking

Ever sense the O’Malley incident our sex life is great, we will probably go out dancing again
We know have a verity of fantasy we share and act out in the bedroom but she is stuck on these one that we tried to act out over the last 3 weeks CONTINULY .She wants to find a guy to do a 3 some ware me and the other man give her a message and crease her. She loves to have her ass played with by massaging it and have me rub my member between her ass checks then she wants the other guy to do the same I know this gets her HOT. She then wants kneel down between us and take both are members and rub he... Continue»
Posted by FREE2694U2 2 years ago  |  Categories: First Time, Group Sex, Mature  |  
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Monica's beginning.

My wife Monica is as slutty as any porn goddess, and it took very little coaxing to get it out of her. She is 31 years old and a very curvy lady at 5'6" 160 with the most gorgeous DD breast ever placed on a woman, and with hips that can make any man beg. 2-3 years into our relationship, our sex life had started to become a little scripted. We both were dying for some excitement, but I never realized that she wanted it more than I did.

She had started a new job and was glad to be working again after a 5 month period of unemployment. She works at a large campus style facility, and one d... Continue»
Posted by jfisher10 2 years ago  |  Categories: First Time, Hardcore  |  
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First Meeting

It was a chance meeting late on a Friday night.I had been at a girlfriends house trying to score.This chick was a real psycho!I had to take at least a gram of coke and a hundred bucks anytime I went over there expecting to get laid.Shed spend all night cleaning her little 2 room flat over in lake highlands while I patiently waited on the couch hoping shed get tired and come sit down.Well after about three hours and half a bottle of sky vodka I'de had enough.Jumping to my feet and saying in a loud vouce fuck this shit I told her to shove it grabbed my coke and hit the door.I drove back towards ... Continue»
Posted by mwnfl 7 months ago  |  Categories: First Time, Hardcore, Voyeur  |  
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summer at home!

Note:this is a fantasy all characters are fake! Hi I'm Dallas an I am going to tell you about my amazing summer I had at home! So I finally got to go see my f****y for summer break I have been so busy between college and baseball I haven't had the time to go visit them for about three years now. They live in Florida and I go to college in Texas so it's kinda hard because traveling is so expensive. So when I finally got home I was greeted by my stepmother and steps****r which I was so happy to see my dad was gone on business in Europe so it was going to just be three of us at the house all su... Continue»
Posted by seeking_fun 7 months ago  |  Categories: First Time, Hardcore  |  
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Hail to Hayley

It was my senior year at highschool and I was desperate to have sex. Every day was like fresh torture as i saw the girls in my class, and imagined stripping them, and fucking them. I was a virgin, and desperate to get off the mark. Sure I'd had the odd girlfriend, but I only ever seemed to date the "good" girls, and was starting to think that a good night snog was as far as I would ever get. Then one day a new f****y moved into the house next to mine.
In the firdt few days I saw the parents and a couple of young daughters, but one day on my way home I saw a 15/16 year old girl going into the ... Continue»
Posted by Gallusguy 4 years ago  |  Categories: First Time  |  
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My experiences in chastity.

My Mistress decided that I should be put into chastity at times when I was not with her and "Off the leash" and she sent me to buy one. The couple who ran the local sex shop were very helpful and showed me their stock. After some discussion, and knowing my Mistress slightly, they recommended the CB6000 as probably the most secure for her. The others they had were metal band types which the lady of the shop said were fine but would allow too much of the skin of my penis to show. She said that my Mistress would prefer me to be completely encased in the transparent plastic of the CB6000, and so i... Continue»
Posted by KCUM 3 years ago  |  Categories: BDSM, Fetish, First Time  |  
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First time Oral!

Back several years ago I had a gay friend named Barry. He was a sweet guy and fun to hang out with. We would do the gay bars in my town about every weekend. Barry ended up meeting and dating an older man named Larry.. Larry was quite well off and had a huge house on the edge of the city.
We all became fast friends with the owners of one of the bars. Gary was telling us one night that he had hired a new DJ.. A straight guy name Jodie. He assured me that he was an amazing looking guy. He was due in town that coming Thursday. The only thing was that the landlady at the apartment he was going t... Continue»
Posted by dripinwet 2 years ago  |  Categories: Anal, First Time  |  
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I was a BIKER GANGS BUTT and SUCK BOY


I am telling this true story because even though I was treated as a filthy cum

sucking, ass fucked sex slave, it changed my life for the better..except NOW I'm ADDICTED to CUM!

I was in high school and had always thought I might be gay but wasn't really

quite sure. I had experimented a few times with a neighborhood boy I was in

grade school with but really all we did was kiss each others cocks and a couple

of times we jerked of together. I had always liked seeing the guys in school naked

in the shower and had wondered what it would be like to get fucked in my ass or
... Continue»
Posted by bifun4u 1 year ago  |  Categories: Fetish, First Time, Gay Male  |  
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From Bromance to Romance

This story is the story of romance and genuine love.
There are alot of erotic firsts in my life but none are as dear to me as my first time with Jacob. We meet our junior year of college. I had just left the rugby team which was a club sport and he was openly gay and had just broke up with a long time boyfriend after he cheated on him. We were both changing and ended changing together. We had common interest like the outdoors. He turned me on to meditation and alot of liberal ideals. Everything about him made me infatuated with him. He has black hair and a permanent five o'clock shadow. A... Continue»
Posted by TaintMisbehavin 1 year ago  |  Categories: First Time, Gay Male, Voyeur  |  
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Graduation PARTY



After graduation Mrs. Haven invited all of us to her and her husbands house for a huge party. Everybody was drinking having a good time, and of course Mrs. Haven looked as hot as ever wearing tight shorts and a skimpy tank top she changed into. I couldn't help but stare at her, for an older woman she was stunning. She stood at 5-6” tall, large breast and descent body that made all the boys turn their heads. I think she noticed, because as the night went on and everyone got d***ker she started sitting on my lap and flirting with me. She bent over a few times in front of me so I could se... Continue»
Posted by gentil9000 5 years ago  |  Categories: First Time, Mature, Voyeur  |  
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God's Great Plan

GOD’S GREAT PLAN
By Al Steiner


My best friend when I was growing up was a k** named Mike Tilden.
Though he was considered to be a geek by practically everyone else, Mike was
an intelligent k** who read everything he could get his hands on. The term
for him these days would be ‘nerd’.

Mike's f****y was a little on the weird side, at least that is my
impression of them today. They were nice people, don't get me wrong, but
they were religious fanatics. His Dad, a bearded, hip-talking leftover from
the sixties could spout fire and brimstone for a half-hour at a time. I
... Continue»
Posted by hard_for_yu 3 years ago  |  Categories: First Time, Mature, Taboo  |  
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First time with an anal plug

I've always enjoyed ‘first time’ stories, so I thought for my first story I would tell one about one of my best first time experiences.
This isn't my first anal experience though… that happened long before (and I may tell that story someday too if this gets a good response from people). I had tried other anal toys before this, some of them were my own creation, but they were all fairly thin and small mainly just to get to my prostate for direct stimulation and that was it. This short story is about my first time with a thick plug and also the first time that my girl was involved. So I’ll star... Continue»
Posted by FearlessAddict 2 years ago  |  Categories: Anal, First Time  |  
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my first time

I placed an add in Craigslist in my area describing that I was a very curious closet CD looking for my first experience. After MANY replies (all of them were either from freak-kind of guys, or someone that quit right away), I got in contact with a guy that seemed to be the right one. I was interested in meeting in the woods in one of the many parks around this area and he agreed on that (after we exchange some pics to “known each other” a little and be OK with what we were looking for).

I arrived in my truck to this very isolated area and I saw a single vehicle parked there (was very nic... Continue»
Posted by pamcdnc69 2 years ago  |  Categories: Anal, Fetish, First Time  |  
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Mother & daughter bond over sex toys.


Veronica lay on her bed and watched as Anita slowly undressed in front of her. The 53-year-old women mesmerized her daughter by gentle exposing her barely contained breasts under her bra. She eventually removed her demin jeans and allowed her daughter to see her fleshy camel toe bulge under her white panties. Anita’s slightly wrinkled skin glistened in the morning light perfectly exhibited her mature figure and this sight was clearly exciting and yet frightening for Veronica.

Anita noticed a slight reaction from Veronica and chuckled “Not bad for an older woman V? – Trust me you are goi... Continue»
Posted by uncleacid 1 year ago  |  Categories: First Time, Mature, Voyeur  |  
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When plan A fails, go to plan B. With a double vag

When plan A fails, go to plan B.
My wife Allison and I are in our fifties and have recently started swinging. When we first met while we were still in the getting to know each another phase we talked about our past lives and experiences including our former partner’s. Rich was one her former lovers. One day Allison received a private message on a social network site. It was from Rich, he has reached out to her by liking some of her posts. Allison and I are open with each other so she told me that Rich contacted her and wanted to get caught up. Allison and I had been going out with each other... Continue»
Posted by floco2015 11 months ago  |  Categories: First Time, Group Sex, Mature  |  
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Hot Horse Ride - # 4

Naughty Nikita needed more merry sexy experiences after I rode her so hotly.
Her horny sexy stallion showed his interest, smelling the feromones from her blond furry fanny. Her sexy smells brought me back to lusty life as well.

While she gazed in amazement at that growing member, I told my nubile lovely looking cutie to get on all fours and arch her spine on offer and open up.
She sweetly obied my orders and expected hornily me to enter her hottest hole.

I didn´t dare to disappoint my merry mare and took her anal cherry as first.
Our moans magnified by the heavy breathing of the stall... Continue»
Posted by petdyke 4 years ago  |  Categories: Anal, BDSM, First Time  |  
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Party

It was a good party. My friends, Ann's friends, mutual friends, and a couple of girls nobody knew, but they brought three bottles of Jack, so nobody complained. They took off soon enough, with a couple of guys, and left the bottles behind. And there was my celebrated cast iron chili, and nobody ever complained about that. All meat, no beans.
As we started around four, everyone was gone by midnight. It was me and Ann, of course, and Romy, her best friend, just the three of us. I switched the music off, found my favorite radio on the web, they were playing some soft music in an unknown languag... Continue»
Posted by verydeluxe 4 years ago  |  Categories: First Time  |  
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Masturbation friendly workplace

It's a new generation and it's no longer taboo. I enjoyed it regularly along with a friend at my first job- night shift with some long dry hours to burn.
True story.

I was 17 then so the urge was overwhelming and often and we had to do something.
I had taken the job printing, sealing and cutting plastic cards and badges. The guy I started working with was older, 22, but very cool and we quickly became friends.

It had only been about a week for me when discovered the boss's porn collection- almost like he meant for us to discover it. We dared each other to this or that and it progre... Continue»
Posted by trevor100a 3 years ago  |  Categories: First Time, Gay Male, Masturbation  |  
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toy time

This takes place 5 yrs after the last story.

Which is 6mths ago. All my stories are true.


I'd been looking forward to Friday all week, not because it's the end of the week, but because I had a annual leave day off work. I woke up nice and early so I could drop my girlfriend at work. After that the day was mine until I had to pick her up again at 5pm...

I rushed home, took a shower, had a smoke and then got out the toys....3 butt plugs in increasing sizes, a cock ring, a inflatable vibrating butt plug and a 8" black suction cup dildo....mmmm my mouth was watering. 

I lived up a... Continue»
Posted by bangoskank2 2 years ago  |  Categories: Anal, First Time, Gay Male  |  
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