First Time Porn Stories
Page 494

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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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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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 2 years ago  |  Categories: First Time, Mature, Voyeur  |  
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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 11 months ago  |  Categories: First Time, Hardcore, Voyeur  |  
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Trip to Gay Sauna

Hi, this is a true story that happened to me a few months back.

I had just finished college early for the day and was feeling quite horny, I had found out about a nearby Gay Sauna on the internet and decided to check it out in the hopes of losing my virginity.

Behind a shopping mall in my city centre was a small sauna hidden away on the top floor of a discreet looking building, I buzzed my way in and headed upstairs.

I was greated by a guy who appeared to be in his 30's, he asked me if I had ever visited before and I told him I hadn't, he was telling me about the prices and ... Continue»
Posted by leicboy19 5 years ago  |  Categories: First Time, Gay Male, Masturbation  |  
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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 5 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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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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1st time double penetration

Time for my yearly check up with Dr. Woods. I love my doctor, I have been seeing him for several years. There has never been anything sexual with us, but I have caught him staring at me at times. Any woman would know how that is when a man looks at them a certain way. I also know any woman would love to be his patient! He is 6 foot 2, brown eyes, and silky wavy brown hair that you would love to just run your fingers through! Muscular with 6-pack abs. I’ve heard many women talk about him, but none I knew conquered him yet.
This appointment was going to be different; I was making my husband go ... Continue»
Posted by Ch3rryLove 10 months ago  |  Categories: Anal, First Time  |  
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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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How to make babysitting pay part 3

Shelley made a decision at that point.
She was not going to lose her virginity in a car, it was going to be in a nice bed or not at all.
The husband jerked in her mouth and pumped it full of spunk.
Shelley was surprised at the taste, but she found it quite palletable, and she swallowed the lot.
She moved back to her seat and put her seatbelt back on.
"Two hundred" said Shelley
"What do you mean?"
"If you want to fuck me it will cost you two hundred and it must be in a bed"
"Well you are a quick learner" said the husband, "but ok, I will pick you up next Saturday morning from the bus st... Continue»
Posted by Baby_sitter 5 years ago  |  Categories: First Time  |  
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A Mother and Her Son 2


Sue jumped as if an electric shock had hit her. She quickly pulled the hand from her top. She was trembling as she sat in her seat waiting for the few people in the theater to leave. Finally, she stood on shaking legs and moved to the isle.

As they left the theater, Tommy had to walk behind his mother in hopes that no one could see his erection.

Sue took a deep breath and sighed as she walked up the aisle in front of Tommy. She wondered why he lagged behind her. She gl... Continue»
Posted by iincest 4 years ago  |  Categories: First Time  |  
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Experience of a boy at Indian Wedding

savita009

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It is SOFTCORE but develops into footworship , golden showers and some kinky fetish stuff with an aunt- i****t type


Meeting the Lady at the wedding Ceremony



It was a wedding ceremony …. All rituals and traditions being followed very religiously … a three day long festivity would follow where all friends and relatives ... Continue»
Posted by savita009 3 years ago  |  Categories: First Time, Hardcore, Mature  |  
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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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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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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 1 year ago  |  Categories: First Time, Group Sex, Mature  |  
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Maggie's Journey To Being a Slut

After 12 years of marriage Maggie and Jay had both become bored with their sex life. Both found it tedious and boring. When Maggie finally talked to Jay about her feelings she was actually pleasantly surprised to fing Jay felt the same way and together they immediately started to work on ideas to put some excitement in their sex life. The first thing they did was tell each other their most private and dirty secret fantasies. At first Jay was unsure but finally told Maggie that he gets excited sneaking looks down her blouse or up her skirt. Especially when they're out in public shoppi... Continue»
Posted by fl44bothways 6 years ago  |  Categories: First Time, Mature, Voyeur  |  
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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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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 4 years ago  |  Categories: First Time, Gay Male, Masturbation  |  
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