First Time Porn Stories
Page 17

Tiny Dick Loser: Experiences with Women, Part 2

I found my second girl, Angela, in the same manner, just about a month later. I suppose you could say that my experience with her was better. She was very pretty and had huge tits. Overall, she was much better looking than the first, although she was shorter, maybe 5’2’’ and she was fatter; she was practically round. She also had her own car, which helped.

Thing going in a similar way. For normal guys, I’d imagine there’d be some kind of confidence boost after losing one’s virginity, but obviously, my first time didn’t give me much to be proud of. So we sat and had awkward conversatio... Continue»
Posted by spardi06 25 days ago  |  Categories: Fetish, First Time, Hardcore  |  
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The civillian

I shadow wrote this story for a friend. The two of us hope you enjoy it.

When I finished high school I spent a few months working, before being drafted. Aside from a short period of training, during the first half of my term I spent most of my time behind a desk. I did spend a day a week doing guard or drill duty, to keep in shape and keep my field skills fresh. When things escalated and another unit was in need of a new sergeant, I was promoted and got reassigned. Still behind a desk, but now assigned to a war zone, I did spend a lot more time in the field. I had to go often to an improvi... Continue»
Posted by GalFa 25 days ago  |  Categories: Anal, First Time, Shemales  |  
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My First Time as Sara... Pt. 01

crossdresser – sissy – virgin – sissy boi – anal – lingerie

I only knew Steve as my landlord. To be exact, Steve was the only son of the two people that owned the small apartment complex I am currently living in as of right now.

My reason for moving here was out of necessity than anything else. Three months prior to moving in the 20 unit complex I lived on the other side of town with my then fiancé Sara. We're both late 20 something k**s that moved in together after collage and while the first couple of years seemed grand, it was bad things that were under brewing in the relation... Continue»
Posted by naughty_bi_interest 25 days ago  |  Categories: Anal, First Time, Shemales  |  
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Janitor and Carole

Janitor and Carole

Carole was naked and straddling Marcio’s hard stomach. The teenager slid backwards taking his cock deeper inside her. She jumped and squirmed. She kicked but she could not escape… not that she wanted to; she didn’t. She liked to bounce on him like this. It made her tingle all over. She was so happy, she felt like cheering. She placed her slender hands on his big muscular chest and rode him HARD and FAST. Sweat dripped from both of them. Carole’s sweet puss was soon being pumped full of cream. Her pussy hiccupped with pleasure. Marcio’s cock stayed hard as she rode... Continue»
Posted by tankengine123 25 days ago  |  Categories: Anal, First Time, Taboo  |  
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Wife takes daughters friends virginity ;) 2

I woke up the next day very early around 5am and my wife wasn't in bed. I went out in the hallway and saw Anthony going downstairs. I was very curious so I quickly grabbed the video camera and went downstairs. I heard muffled voices coming from the kitchen so I turned on the camera and went behind the kitchen door and videotaped though the door crack. I heard my wife saying in a low voice so as not to wake up anybody, "Hi Anthony, what are you doing up so early?"

Anthony said, "Hi Mrs. C., I'm still all wound up from last night."

My wife looked embarrassed and turned bright red, "Anthony... Continue»
Posted by sexozingguy 25 days ago  |  Categories: First Time, Mature, Voyeur  |  
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Wedding Night – Olive and Liam

Wedding Night – Olive and Liam

*Olive’s story…
Olive was a sweet little femboy standing in front of the bathroom mirror getting ready. His makeup was completed and his large beautiful dark eyes shone brightly as he examined himself. His true love waited on the other side of the door. The man was taking Olive on a special trip tomorrow to get married. But the wedding night was tonight… in just a few minutes in fact. He was so excited he could hardly breathe. He was wearing the special outfit that Liam bought him.

Olive felt so beautiful. His tiny little pecs were covered by a sh... Continue»
Posted by tankengine123 26 days ago  |  Categories: Anal, First Time, Taboo  |  
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Finger Training - Eddie

Finger Training - Eddie

Finger training was just the beginning for sweet Eddie.

Rocco held out his large powerful hand with the palm up. Eddie looked at him shyly and flushed. Eddie’s face was pink and warm. It glowed with health… and with shame. He had never been nearly naked before and the fact that Rocco was completely naked, caused his eyes to lower. His downcast eyes immediately rose. He was startled. He had caught sight of Rocco; an important, very scary part of the man. His (what had the man called it…) COCK. Eddie had never seen an adult one. Even this short, unintent... Continue»
Posted by tankengine123 26 days ago  |  Categories: Anal, First Time, Taboo  |  
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Repos of my Fantasy

This is how the fantasy goes

I arrive at the Hilton Garden Inn before nightfall. In advance, I had made reservations for a handicap room as these rooms have a nice big walk-in shower and me being handicapped as well. From inside one of the bags that I had packed, I pull out all of the interesting toys that I brought. I set up everything on the table, the night stand and the dresser before you have a chance to arrive. You arrive about an hour later than I do from a long drive to meet me for what has been a long over-due rendezvous.

As you enter the room, you notice under a metallic meas... Continue»
Posted by big_bruno 26 days ago  |  Categories: BDSM, First Time, Group Sex  |  
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My short dick is a favorite

If you have read my stories you already know that I'm a married man that has a wife ( Linda ) that fucks around. Up untill last Friday my small think penis was never useful to my wife. Once I talked her into going outside the marriage for sex she hasn't had a need for my extremely small dick. As a matter of fact she started buying me different styles of chastity devices and keeping me locked up for a month at a time.

This was what I had excepted as being normal. I enjoyed hearing her tell me stories of her adventures with both white and black lovers. Last Friday as she was getting dressed ... Continue»
Posted by woreout 26 days ago  |  Categories: First Time, Hardcore, Voyeur  |  
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she was late

She was late, which was unusual but not worrying but there had been no text or call, we’d been seeing each other for a short while but nothing serious, yet.
Suddenly the there was a knock at the door, it was her! As I opened the door for her I saw she was dressed in a dark blue wrap over dress, displaying a very bountifull creamy cleavage, tights (or perhaps stockings??) with dark heels, hair brushed back but loose and with full make up – “sorry sorry, I got held up at work then rushed to get ready as I know you hate lateness and I wanted to get over here so quickly” she said as we embraced,... Continue»
Posted by mawhite 26 days ago  |  Categories: First Time, Mature, Voyeur  |  
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Growing Up In The Country.

The events that are unfolded here are all real and not just a part of my fantasy world that I must admit I do often sink into.

I was born and lived in a small Village in the countryside of the East of England, and it was not too long after the war so most of the people around us were sort of poor (like us) and many were farmers too.


Life was easy going and as a teenager who needed pocket money ? I was doing my daily "Paper Round" delivering news papers and magazines to many of the local farms that surrounded our house in the small village, and this was a Monday to Friday task th... Continue»
Posted by aquaman2015 26 days ago  |  Categories: First Time, Mature, Taboo  |  
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My first Creampie

“My parents are going to be gone for the whole weekend.” My boyfriend Michael said walking up to me at my locker after class on a friday.

“Alright, well what time do you want me to come over tonight?” I asked with a smirk, knowing full well what was going to go down tonight.

“They’re leaving at 6:00, so anytime after that would be fine.” Michael said smiling.

“Okay sounds good, I’ll see you then.” I say before leaning in and giving him a kiss and headed to volleyball practice.

During practice I had a hard time focusing, thinking about what would be happening later that night. It l... Continue»
Posted by creampielover96 26 days ago  |  Categories: Fetish, First Time, Taboo  |  
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One night with Kaley Cuoco (and Penny)

I went to comic-con for work and it was no fun at all. My bosses had kept me too busy wasting my time to actually enjoy anything, then dumped me off at the hotel once they had scored tickets to some movie studio party. Up in my room I felt useless and abandoned. I drank a couple of the small liquor bottles from the mini fridge before I decided to go down and drink in the bar like an adult.

A while later I was a few drinks deep and feeling pretty high when I felt a hand on my shoulder. I turned to find a pretty blond smiling at me. Just beyond her I could see two well groomed guys dressed fo... Continue»
Posted by XXXNoBounds 26 days ago  |  Categories: Celebrities, First Time, Group Sex  |  
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Jennifer Lawrence and an old high school friend go

Dominic Bryan sat down in the log cabin hidden away in the Los Angeles countryside. His ears picked up as the sound of a car rolled up the drive, collecting gravel in its treads as it went. He stood up and moved away from the desk, peering out of the large window, Dom saw a big green SUV slow to a halt outside of the resort. Two people got out of the vehicle and walked to the back of the car. The larger woman opened the back of the car and hoisted a large bag out of the back.

That must be the Hollywood star that Dom was going to have to look after for the weekend. He ran a hand through his... Continue»
Posted by XXXNoBounds 26 days ago  |  Categories: Celebrities, First Time, Hardcore  |  
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Avril Lavigne at a club

I didn't really want to go to the club tonight, but I had promised Crystal that I would be there. I was tiered and a bit depressed as my life wasn't going in the direction I wanted it to. Crystal knew this and that was precisely the reason why she wanted me to go out tonight.

So when 10:00 pm hit, I put on my tight jeans and grabbed a shirt from my laundry pile (not a really good one because this club was mostly teenagers, so there wasn't a dress code) and then I got into my rust mobile and drove the few minutes there.

As was normal for this time of the year, there was no line up and no ... Continue»
Posted by XXXNoBounds 26 days ago  |  Categories: Celebrities, First Time, Hardcore  |  
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Wife takes daughters friends virginity ;) 1

My wife (Linda), daughter (Caitlin), her friend Anthony and I were playing Scrabble when I noticed Anthony's eyes were looking at Linda's crotch every so often. Linda was sitting on the couch across from him and he was sitting on the floor so he was eye level to her crotch. Caitlin and I were on the sides and had no direct view of what was happening. She was wearing a skirt and it looked like he might be able to see up the skirt because her legs were spread. I pretended to get up to go to the bathroom to get a view of what Anthony could see. As I walked behind Anthony I pretended to pick somet... Continue»
Posted by sexozingguy 26 days ago  |  Categories: Anal, First Time, Mature  |  
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First Threesome Ch. 2

male bisexual - oral sex – blowjob – cum – threesome

I ran back into my office as the phone rang. "Hello," I said in my normal business tone.

"Hi," he said.

What the fuck?!?! He was calling me at work!!!

The call startled me. It's not as if I'd forgotten last weekend's events. How could I? They were probably the most intense, and troubling, sexual episodes of my life. I'd been thinking a lot about them these last few days. And Lynn and I had talked about them a little, too. My thoughts were typically tortured but the conversations with Lynn tended to ease my worries.

I'd ... Continue»
Posted by naughty_bi_interest 26 days ago  |  Categories: First Time, Group Sex, Gay Male  |  
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Between the Devil and the Deep Blue Sea: Part 5.


The weekend just gone was the first ever in my mundane life to drag. It started with a row with mum. Being busy at the Saturday job helped, but Sunday lasted an e t e r n i t y. As I counted every second, I remembered the happenings of the past week and what might happen or the possible old games and activities I could recycle for my rude fun with Eric.

The long summer had broken and the new week started on a much cooler autumnal note. Mum had finally bought my crisp, new navy school pinafore and thankfully it was nice to not have to squeezed into the tatty old one. To rub salt into the w... Continue»
Posted by JudyB 26 days ago  |  Categories: First Time, Hardcore, Voyeur  |  
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Roly-Poly Jessi

Roly-Poly Jessi

The wholesome teen slid a slender dildo into her pussy with one chubby hand. Her roly-poly body jiggled and shook as she stroked; sending the dildo in and out. The other hand was behind her rounded bottom with one of her fingers deep in her hungry ass. She moaned and groaned… interrupted by several short bursts of giggling. She peeked at her laptop; her secret boyfriend was watching intently, eyes wide.

She opened her chubby thighs so her neighbor could see her better. She hoped he could see how wet the dildo was. She moved the dildo from her pussy hole to her ass ho... Continue»
Posted by tankengine123 26 days ago  |  Categories: Anal, First Time, Taboo  |  
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Finger Training - Emily

Finger Training - Emily

Finger training was just the beginning for sweet Emily.

He held out his large powerful hand with the palm up. Emily looked at him shyly; she flushed. Her face was pink and warm. It glowed with health… and with shame. She had never been nearly naked before with a man and the fact that he was completely naked, caused her to lower her eyes. Her downcast eyes immediately rose. She was startled. She had caught sight of him; an important, very scary part of him. His (what had he called it…) COCK. She had never seen one. Even this short, unintentional glimpse... Continue»
Posted by tankengine123 26 days ago  |  Categories: First Time, Taboo  |  
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