First Time Porn Stories
Page 451

#1 - Nikki's First Experience

I had recently started my transformation and was just past 18. I was at the stage where I was just starting to dress as a female in public and friends convinced me to go out. At the local pub over the course of the night my friends all found someone and I had resigned to the fact that I probably wouldnt find anyone until a young guy in his mid 20’s approached me. He said my friends has told him about my change and he was very complementary saying I looked pretty convincing. Over the next hour or so we spoke in the pub about everything from jobs, hobbies and eventually if we were both single wh... Continue»
Posted by Nikki_93 4 years ago  |  Categories: First Time, Shemales  |  
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the first time i had sex

I went to an all girls catholic high school, though I'm not catholic and not that it matteres my parents thought it was the best choice for me. The summer before my junior year I went on a tour of a popular teacher's college. There I met KiKi, I very hot, very sexy, very bisexual student at the teachers college. I took a liking to her and we exchanged numbers, you know...just incase I had any question..

We spoke over the phone alot, we became fond of eachother. We would do each otheres manis and pedis, hang out at the beach, anything. One day I went to her house for my routine manicure. The... Continue»
Posted by bOObsLikeMine 3 years ago  |  Categories: First Time, Lesbian Sex  |  
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Paying off a beggar....

(This story is entirely fictitious)
I was 16. The story is set in India.
Just like every other day, i had gone to a public park for a jog. Since it was india, the park had many homeless people. while jogging, I noticed a hot girl in rags, who seemed to be almost as old as me. She was searching for food in the dumpsters when I noticed her, and the wildest of fantasies popped up in my head.... would she let me bang her for money...?
I crossed her and continued my jog with the fantasy in my mind. After completing a round of the park, i returned to that spot, motivated to try and pull it off. B... Continue»
Posted by immalad 3 years ago  |  Categories: First Time, Hardcore, Taboo  |  
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Young love when serious os great

My first love and further sexual deep experience
Just 16 my mother and father decided to take me on a holiday > yes a holiday but one of some difference.
Dad booked us on what was known as a coastal freighter calling at all the coastal ports in South Australia (the names not important).
To make sure I would not get bored they invited Margaret 16 year old daughter of a great friend with whom dad worked.
Lovely girl always happy and who was pleased to be invited as we had been friends for a while at school.
Now she was a lovely shaped girl mature for her age, well developed breasts, long h... Continue»
Posted by Ihaveituwantit 1 year ago  |  Categories: First Time  |  
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Nursery nurse turned sex slave

A few years back my baby daughter started at day nursery. Over the first few weeks you start to get to know the staff, particularly those who were caring for her. Each c***d is assigned a key care worker and your point of contact. Most of the girls there are in their late teens early 20's and all shapes and sizes. Our key worker Jessica was a large girl with very large breasts, certainly from day one the thought of a tit fuck had crossed my mind. The weeks had turned to months, and you have idle chit chat when you drop off and collect your c***d.
One Tuesday I was working at home when there ... Continue»
Posted by DavieD71 1 year ago  |  Categories: First Time, Hardcore, Masturbation  |  
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My Little Bitch Pegged

I really am a little butt slut.

Whether it's her finger in my ass while she gives me one of her fantastically intense blowjobs, or her strap-on shoved inside of me as she makes me her bitch, I just love it when she gets to work on my ass. She doesn't do it often, but when she does, she goes all out. I just can't get enough of it; I love every aspect of the act.

The role reversal, where she takes control and I'm the one that spreads my legs and she fills me up instead, is a wonderful treat. The feeling of being deeply fucked by a vibrator or even a finger, that jolt of pleasure that's s... Continue»
Posted by 425olds 10 days ago  |  Categories: Fetish, First Time, Hardcore  |  
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Cuckold

I was chatting with a couple from Canada, who contacted me on a swinger's web site. John and Sheri were a little over 15 years older than me. They said they spend the winter in Florida in the town where I live. They wanted to meet when they came down for the winter.

When John and Sheri arrived in Florida, they set up a meet at a local restuarant. I went to the restuarant and met John. He said Sheri sends him to check out the people they meet. After talking with John for a while he suggested we go to his house and meet Sheri. I followed John to his house and met Sheri. She was absolutely go... Continue»
Posted by h52202181 5 years ago  |  Categories: First Time  |  
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Grocery Store checkout

On my way home last night I stopped at a local store to pick up a few items one of which was a box of Magnums, you know rubbers, anyway I'm in the checkout line and the clerk a good looking middle age woman gives me a big smile and says as shes scanning the rubbers "Aren't these the large size" I smile back at her and say "yes thats right" another smile from her and she gives me the total of my purchase as she looks at my crotch and winks..Wait it gets better all I've got is a 5th of Absolute Vodka and the Magnums and this cute little girl whos bagging my items says Sir do you need help out wi... Continue»
Posted by pedroguy 4 years ago  |  Categories: First Time  |  
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Closest I ever got to sucking cock

This took place over 10 years ago. I won't explain the circumstances but let's just say I was in an environment where this was a possibility. At that time in my life I was (and technically am still) 100% straight. I was a a coed group for over a week, traveling through the province, city to city.
While in Toronto, I joined a few of my friends who were in the group to visit a local gay bar. Nothing much exciting happened there. Actually I received more attention from the fag-hags (who assumed I was gay) which really pissed off one of my gay friends who had been telling me he wanted to tea... Continue»
Posted by wantingtobi 3 years ago  |  Categories: First Time, Gay Male  |  
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My First Time

Our house was small and with everyone at home, it was always a lively, bustling place to be. The only problem with this, was that as a s*******n year old lad, with raging hormones, I had little chance for any privacy.

For a small terraced property our house had a very long garden. My dad took great pride in how it looked and would spend his weekends ensuring it continued to look at its best. At the very end of the garden, hidden behind a row of conifers was my dad's garden shed and behind this, he had built for me a small covered play area. This ofcourse was built for me when I was younger,... Continue»
Posted by dekkard69 2 years ago  |  Categories: First Time, Gay Male, Masturbation  |  
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First Time Anal

I have always been intrigued to see how it would feel having some kind of toy or dick in my ass.

I am a 24 year old male who has only ever been with girls but has always had an urge or a curiosity for guys. My girlfriend is sometimes a bit shy when it comes to the bedroom department where as I am always horny and always up for trying something new and different. My girlfriend knows of my feelings in regards to men and is 100% fine with them.

Recently I brought up the idea of anal play. She is against any anal being performed on her but said that she would try it on me if I was really wan... Continue»
Posted by thehearts 6 years ago  |  Categories: Anal, First Time  |  
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In flight service

Flew back from New York last week with Delta airlines. Flight was nearly empty, so plenty of room to sit. Had a row of three seats to myself. On the other side of the isle was an attractive lady also travelling alone. We got chatting, I said I had been in New York on business. she had left her husband there, he was something to do with the red bull air race.
Turned out she lived only an hour away from me in the uk. After dinner (it was a night flight) the cabin staff turned down the lights for people to get some sl**p. I asked if she wanted to sit with me so we could chat more easily, she did... Continue»
Posted by kwacker 6 years ago  |  Categories: First Time, Mature  |  
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My First Guy

Well this is a true story it happened to me about 22 years ago I was about 30 years old, had been experimenting with shemales but I meet this guy we'll call him Greg at a gay bar he was huge about 6' 8" tall with hugh arms big chest he probily weight in at about 280 lbs and small hips but with the best looking cock I'd ever seen on a guy it was at least 12" long, about 4" in diameter he was dress in short shorts and a t-shirt that he almost busted out of. His cock was almost showing out of the top of his shorts, my mouth was watering so bad I had to get a paper towel to catch my drewal. I walk... Continue»
Posted by rafael0058 5 years ago  |  Categories: Anal, First Time, Gay Male  |  
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Karen My Best Friends s****r

Karen My best friend’s s****r

I had always had a crush on Karen and was always trying to get a look down her shirt or up her short skirt when I was over at Bill’s house. I was 15 years old when I first meet her and from that day on I knew that one day I would see her naked body and hopeful get to use my man hood on her.
Karen was 4 years older than me , but always treated me like I was special , She was so bubbly and smiled all the time . She would hug me whenever she saw me and I was always willing to feel her firm breast crushed against my body. Karen always wears the sexiest out fit... Continue»
Posted by bigcityguy 5 years ago  |  Categories: First Time  |  
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Dirty lesbian fun with a friend of mine ;)

Kelly is my name and I have a very exciting love affair with my woman Jen. Ive been blessed to have a thick 6 inch cock and a tight pussy. She loves it when i kiss on her gently as she moans grinding her warm pussy on me. Her sweet skin and red hair drives me insane along with her big giggly ass shaped like the perfect apple. Straddling me as I sit on the sofa she slaps my face with her big tits as i smile my fingers play with her wet cunt. I can feel her hands on my thighs slidding up to my semi hard cock dripping precum clear and slimmy. Sitting back she undoes my pants and jerks me as we ki... Continue»
Posted by kellyworthing 5 years ago  |  Categories: Fetish, First Time, Lesbian Sex  |  
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My wife's first blow job.

When my wife and I started dating I was 22 and she 16. I did not want to rush into intercourse right away with her. She wanted me to take her virginity but wanted her be sure she was ready. So instead we fooled around a lot.

She gave me her first blow job one October Saturday after noon in 1989. We had kissed quite a bit all day and I even licked and fingered her virgin clitoris during the course of the day. By night fall we drove back to her parents house and parked in their dark drive way. We began to kiss pretty hot and heavy. It was then when she reached for my cocked and began to jerk... Continue»
Posted by mikeandcindy 4 years ago  |  Categories: First Time  |  
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TRAIN RIDE

OK THIS ISNT MY STORY BUT VERY HOT , i HOPE THE ORIGINAL WRITTER DOESNT MIND

I recently had the pleasure of taking a leisurely trip by train, across this great nation of ours. It was three nights on the train and the experience proved to be much more interesting than I had anticipated. It was the morning of the second day when we were stopped in Saskatoon and I opened my eyes. I realized what I had done.

I had my own cabin and although it was small, it was large enough to accommodate a fold down bed, which was extremely comfortable. When I retired the night before I was very tired and fo... Continue»
Posted by rackem28 4 years ago  |  Categories: First Time, Mature, Taboo  |  
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u*********s Girlfriend Fucking

I wanted to fuck my girlfriend so badly but i never got the chanse to say it.
I was still a virgin so my cock was loaded everytime we were playing with eachother but we never even got to the jerk off part.

One day she was going to come over and i knew i wanted to fuck her. Nobody was home that day so i could do what i want.
I got some sl**ping pills and put them in her drink. As we sat on the bed i gave her the drink. After 20 minutes she felt sl**py and before i knew it she was asl**p.

Horny as hell i quickly put her in the perfect was. Arms and legs spread so i could have my way with... Continue»
Posted by TSRMA 4 years ago  |  Categories: BDSM, Fetish, First Time  |  
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Cuckold Husband With Small Dick Watch's Wife

True Story as told by Contractor

You have contracted me to put in a new hardwood floor. I've been working for two days, watching you every minute of every day because I can see that you have tits that I would die for. I think hubby knows I've been watching in fact I know he does. I was talking to him about the flooring when you walked by in nice jeans that really showed your ass off nice and a blouse that was maybe two buttons to far unbuttoned.

As you walked by I just instinctively looked at you and hubby was talking to me. I said to him I'm sorry I won't do it again. I had stared you ... Continue»
Posted by TheSnuffy 4 years ago  |  Categories: First Time, Hardcore, Voyeur  |  
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Supplementing my Income

Part 1

A year ago, I lost my job of 10 years. In the beginning, I was out looking for work everyday but as time went on, I lost my motivation. Eventually after no luck job hunting, I just gave up. My wife had a full time job and I was collecting unemployment which helped but we were still hurting financially. Instead of getting depressed, I found a new passion that took my mind off of our financial situation and the fact that getting a job was becoming a dream. That new passion was lifting weights and working out. I had a gym membership that I never got to use when I was workin... Continue»
Posted by jpscorp 4 years ago  |  Categories: First Time, Gay Male, Mature  |  
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