First Time Out, First Time Fucked. free porn video

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I was looking good even if I do say so myself. Six inch black platform heels, black hold ups, the obligatory little black dress, long red wig and my fave faux fur jacket. I felt sexy, I felt like a slut and I wanted the world to see me.

I hadn’t been out before but I had been building myself up for this moment for months. I had it all planned. Wait until dark, slip on my sweatshirt, tracksuit bottoms and trainers over my stockings and dress, stick my wig, shoes and jacket in my rucksack. I’d have to risk it in case anyone saw the make up but I figured it would be dark enough for no one to notice, especially if I wore my baseball cap low.

I was excited and nervous but taking a peek outside realised it was now or never. I quickly locked the front door and slipped into my car. Within a minute I was off the drive and heading towards the park on the other side of town. It was late out and there wasn’t much traffic, but the nerves were building and I don’t think I would have noticed either way.

I pulled up in a dark area of the park’s car park, not too far from the entrance but far enough away that I wouldn’t be noticed getting changed. I changed quickly, putting on my shoes, wig and jacket. Quick check in the mirror and I was ready.

The first thing that hit me was the breeze on my legs. I had shaved them earlier and the sensation was electric. I could resist running my hand up my stocking clad legs. I could have been happy with that but I was determined to see this through.

I gently eased myself out of the car trying to look as ladylike as I could just in case anyone was around. A quick glance around told me that there wasn’t and I quickly locked the car and headed for the park entrance. The click of my heels on the pavement excited me. It was turning me on to know I was making that sound. I continued into the park concentrating on my walking and swaying my hips. I’d practiced plenty of times at home but this was different and delicious.

The sound of my heels as I sashayed through the gates was extremely erotic. I was so caught up in how much this was turning me on that I didn’t notice him until he stopped in front of me. “You haven’t seen a little dog around here have you?” he asked.

I quickly looked him up and down. He was late 20’s about 6ft 1, athletic with short brown hair and very cute looking.

“Er, no.” I replied in my best feminine voice.

“Actually, if I’m honest I haven’t lost a dog. I just needed an excuse to speak to you. Hi, my name is Simon.” He offered his hand.

I was quite sure what to do. I hadn’t planned on speaking to anyone.
“Erm, hi I’m Sarah”. I’ve no idea where Sarah cam e from but it was the first name that popped into my head.

“Hi, Sarah. What brings a pretty girl like you to the park late at night then?” Simon enquired with a twinkle in his eye.

Before I was able to reply he continued “I saw you getting changed in your car and was curious but as soon as I saw your legs. I knew I had to speak to you.”

“You saw me getting changed?” Shit! I thought I had been so careful. I was beginning to panic.

“Don’t worry. I’ve always been an admirer of girls like you. Your secret is safe with me.” He must have sensed my panic. “In fact I’ve dated quite a few, but I have to say you are certainly one of the sexiest I’ve met.”

I was a bit surprised by his openness but also flattered by his comments. I couldn’t help but blush.

“Thanks, but I bet you say that to all the girls.” I was trying to be modest but I loved the attention.

“Honestly it’s true. Here feel for yourself.” He took my hand and placed it on his crotch. I could feel his hardness through his jeans. He felt big and I could feel him getting bigger as I touched him.

“Wow.” I let out an involuntary gasp.

“See my cock never lies.”

I had never felt another cock apart from my own and it was certainly bigger than mine and seemed to be getting bigger. I wondered how big it would get and what it would taste like.

“Here, come with me.” He grabbed my hand and led me towards the bushes. We passed through a small gap and were suddenly in a small clearing surrounded by bushes and trees. He stopped next to a large tree and turned and kissed me.
It took me a bit by surprise but I responded eagerly as his tongue explored my mouth. I could feel his hands trace their way down my back and rest on my ass giving it a squeeze. I was in heaven and let out a soft moan as our kiss continued. He pulled me into him and I could feel his hardness pressing in to me.

My hands moved to squeeze his cock. It felt so good and so big I just had to see it. I started to unfasten his belt. He realised what I was doing a broke our kiss and to unbutton his jeans. I stepped back as his jeans fell down past his knees releasing his glistening cock. It was the biggest one I had ever seen and must have been a good 13-14 inches long. It looked so good I knew I had to taste it.

I dropped to my knees in front of him with his cock pointing straight at me. Like a school girl unsure about licking her first lolly I stuck my tongue out to taste it. It was slightly salty but also delicious.

“Why don’t you kiss it?” I heard him pant.

I lent forward and gently kissed the tip of his cock. I hadn’t tasted cock before and was unsure what it would be like but here I was wanting desperately to fit it all in my mouth. I continued to kiss his cock enveloping his cock head in my mouth. I began to twirl my tongue around his cock trying to savour the taste of it.

I must have been doing something right because I began to hear him moan and gently thrust his hips forward pushing his cock further into my mouth. His thrusts were gentle but were becoming more rhythmic. I had only ever sucked on a dildo before and it was nowhere near the size of Simon’s cock. I was worried I was getting out of my depth as he thrust more and more of his cock into my mouth.

I slipped his cock out of my mouth and began to kiss along it’s shaft. I kept alternating between taking as much of his cock in my mouth as I could and kissing along his shaft. Although I was enjoying it, and judging by the sound of him so was Simon, I knew that I was also a little scared of trying to deep throat his huge cock in my mouth.

Suddenly Simon lifted me to my feet. “That feels sexy babe but it’s your turn now.” He said turning me so I was facing tree with him directly behind me.
He lifted the hem of my dress up exposing my panty covered ass. He started to fondle my ass and then I felt him move my panties to one side and start teasing my hole with his finger. I loved having my hole played with and Simon’s touch was electric. He stroked and caressed around my hole and suddenly I felt something warm and wet enter it.

It took me a moment to realise that it was his tongue and he was literally tonguing my ass. It was heaven and I couldn’t stop from letting out loud moans and pushing back onto his heavenly tongue.

“Oh, fuck babes that feels so good.” I said encouraging his tongue deeper into me.

He was driving me wild. “Oh, god. Fuck me! Fuck me! I need you inside me.”
If I had thought about it I would have had second thoughts about screaming that out but I was so turned on I just wanted to have him in me.

“Fuck me Simon! Make me your slut.” I was caught up in the heat of the moment.
Simon stopped tonguing my ass and stood up behind me. I could feel the heat of his cock pressing at my boy pussy. I began to push back hungry to get his cock in me.

I had fucked myself with dildo’s before and regularly used a small butt plug on myself but nothing prepared me for the pain I felt as Simon’s cock head pushed into me. I screamed and Simon stopped pulling out of me.

“Do you want me to stop?” He asked.

“No!” I wanted his cock in me so badly. “Just take it slow so I can adjust. I’ve never had a cock as big as yours in me.” It was true but there was also some bravado in my words as I wasn’t sure I could take his cock.

Simon worked his cock slowly into me, letting me adjust when the pain got to intense and get used to his monster. Eventually he was completely buried in me. I had never felt anything like it before. There was still a bit of pain but that was being replaced by a fullness and a feeling of euphoria than I had managed to fit him all into me.

“You okay?” He asked.

“Yes, just take it slow at first.”

He began to slowly slide his monster in and out of me. The pain and concern quickly subsided as the waves of pleasure and lust for his cock I was feeling began to build. I started to push back encouraging him deeper into me and he responded by upping the tempo.

“Yes, babes that feels so good. Fuck me hard make me your bitch.” The pain was gone and I was in pure ecstasy.

“Faster babes. Fuck my little slut ass.” I wasn’t sure where my dirty talk was coming from but it had its desired effect as Simon began to really pound his cock into me. I braced myself against the tree to stop from falling over.

“That’s it babes. Pound my tranny ass.” His cock seemed to grow bigger in me causing waves of pleasure.

“Oh fuck.” Simon called out. He was really pound his monster cock deep into me and as he tightened his grip on my hips I knew he was close to cumming.

“That’s it babes, cum in your tranny slut’s ass. Make me your bitch.” I had never been this turned on in my life but I was desperate to make Simon cum in me.

Suddenly I felt his cock explode in me with spurt after spurt of hot fluid coating my insides. It sent me over the edge with pleasure and I’m sure I blacked out a little. Simon held his cock in me until I regained my composure. Eventually he went softer and began to slide out of me.

“Wow. That was quite a show you two put on.”

We both turned in the direction of the voice…

To be continued.

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Property of Devils Outlaws Part 2

“Wake up slut! It’s time to put that hot little body to work, you got a long day ahead of you,” one of the bikers declared, slapping Hannah roughly across the face. Hannah yelped in pain as she was abruptly and painfully woken up. Immediately the horrible reality of her situation set in and she started whimpering miserably. She didn’t know what time she fell asleep, but it had taken her at least a couple hours and she felt like she’d hardly slept at all. There were at least 15 bikers...

3 years ago
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Property of Devils Outlaws Part 8

Hannah had no idea how she survived the next several days with Big Joe. Over the course of that time, the huge beast continued to take Hannah with him to many different towns and neighborhoods. Her purpose on these trips, of course, was to fuck whoever he commanded her to. Then, in the evenings, she was forced to pleasure the sadistic biker in unimaginably cruel ways. Every single night the Outlaw raped Hannah at least two or three times, and since he was such an anal aficionado, he...

2 years ago
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Timeing

Stuck with tidying the sports storage shed, Lewis moaned and grunted with anger as his mates ran back to the changing rooms to get changed and go home. The only upside was he was alone with miss crow, a young thin sports teacher that was extremely atractive. Miss crow was about 25, 5’3 and had curves in all the right places. Her breasts were DD her waist was thin while her hips were wide for her size. In contrast with Lewis he stood at 6’7 and his shoulders were wide and waist was thin. Even...

3 years ago
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The New Scoutmaster Is a SheChapter 5

Rebecca was at a loss for words when she walked into the last tent in the line and found young Raymond James face down in his bunk sobbing like he had just lost both his parent in an airplane crash. She knew that wasn’t even a remote possibility because the James family was one of those “never go out” families and were the only family in the neighborhood to never light up their porch for Halloween. Of course, that wasn’t a reason to take a dim view of their social skills, it was just...

1 year ago
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The New Scoutmaster Is a SheChapter 13

Summer camp was drawing to a close. It had been a memorable summer with lots of private little unsuspected tingles that made Rebecca start to feel like a teenager once again. She had made quite a few new friends in the younger crowd of seventeen and eighteen year old category and she was looking forward to some interesting sleepovers at her home for her twin’s sex education needs and exercises in social interaction that was not texting or looking at some silly screen like a trained...

2 years ago
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The New Scoutmaster Is a SheChapter 16

Rebecca was slightly depressed because she had suffered some redness on her backside from the oversexed male scoutmasters who pestered her to drop her drawers for them because she was female and definitely not of jailbait age. Of course, her attitude and her appearance were misleading, and she reveled in the attention she received because she looked like one of the underage female scouts and not a scoutmaster in her own right. A couple of the good old boys got carried away by the sight of...

4 years ago
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Property of Devils Outlaws Part 13

Less than 50 miles away from where Hannah was suffering, inside a tavern also owned by the Outlaws, another whore was having a miserable night of her own. Ellen Duffy, the incredibly hot redhead and Miss Washington contestant, was on her back with her legs spread while a fat, greasy Mexican fucked her pussy raw. He was the fourth Mexican in the past 20 minutes to fuck the young redhead, and he was in a state of euphoria as he pounded into Ellen like a savage. “So boys, we got a deal?”...

3 years ago
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Showertime

The sun was just peaking through the over cast sky, pushing its way in through the curtains and across my sleep crusted eyes. I blinked and stretched up, arching my back as the soft cotton sheet slipped down. It felt luxurious and I reveled in the rare opportunity to sleep in with no obligation, school, or extracurricular activity to take my time. Rolling over, my legs rubbed against each other smoothly as they tangled in those worn sheets. I yawned and listened carefully. No sounds permeated...

1 year ago
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Summertime0

A tall slender girl, she couldn't have been much over 18 or 19. Her faded blue hip hugger shorts showed off her narrow waist. Wide hips told me she was blossoming into a well-developed woman. I admired the long, slender legs and the curve of her thighs. I could just make out the crease that separated her butt cheeks from her legs in the frayed bottoms of her short shorts. Her shoes were the clunky-heeled strap-on things that girls wear these days with no socks. She did a quick skip and some...

2 years ago
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Ragtime

Last October at my sister’s 35th birthday dinner, my brother feels the need to inform the entire table of my old thumb-sucking habit. I was really surprised anyone remembered, but apparently the way I went about my little rituals, is strange and fun to bring up at inappropriate times. My family, especially my brother, enjoys watching me squirm and fidget because I am the only one left with secrets apparently. I sat across the table a bit embarrasses but struggled with the comments. I look to my...

3 years ago
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lexis first time0

i had been reading in my usual spot when i heard the familiar rumble of Johns' Harley-Davidson coming up the road. We'd met about month before. i was reading as usually, just trying to get away from the computer for a while and he'd been on a ride. i was at my car getting a water and i complimented his bike as he rode past. He stopped and we talked about bikes for a few minutes before he rode off. Even though i'd been dressing and learning to be feminine for almost 2 years, i didn't think...

2 years ago
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SHOWER TIME1

“Alright, alright… I’m awake.” Sam said in a low, morning voice. “It’s already 8:45 AM!” His father shouted from across the hall. “Come on, you heard your dad.” Mom said in a much lower voice. Mom exited the room, and went to wake up Katie, Sam’s older sister by 1 year. Sam and Katie were really close at childhood; puberty separated them a bit but they still talked all the time. And Katie was a very attractive 19-year-old, she acquired the same incredible genes her mother had. She had a...

3 years ago
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My first Time101

One day while I was at my friend Mark's house, only his brother Jacob(20 at the time with a 8in penis), him and I were at the house his parents had gone out of town and would be back the next night. We played video games for a while then he asked me if I wanted to play truth or dare, I said ok. We played for about 8 or 10 min doing silly boy things and messing around. Then one turn when i said dare he told me "I dare you to take off your shorts and show me your underwear", I was a bit...

3 years ago
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My first Time13

Like lots of things back in those days maintenance was poor and slow and the light bulbs in the bathroom had been blown for about a week. It didn’t really matter most of the time as there were frosted over windows high up in the room that let daylight in so morning and straight after work there was enough light to see to shower and shave. The shower room had a row of 6 showers one side of the room and 6 basins with mirrors above on the other with a bench in the middle to sit on or to put...

3 years ago
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The Timefull Cruise

I appreciate all scores, comments or feedback. I am looking for an editor, as well. I I’m not the type to go on a cruise, but there I was. I’m really more of a ‘see the old fort or castle, stay in the bed and breakfast, drive around the wilderness to see wild animals, go whale watching’ type guy. It was my thoughtful friends that had set me up for an ocean cruise. They arranged the whole thing and then sprung it on me. The girlfriend I’d been with for the last year and a half had suddenly...

3 years ago
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My first Time65

My name is Angad, I am 18 years old, 5:11 ,Indian guy, dark hair, green eyes, fair and very atheletic. My cock is 6.5/7 inches and relatively thick and this is the story of how I lost my virginity. It happened a couple of months ago, my 1 semester at college had just ended and I had come back to my hometown.I went to the bank one day as I had to withdraw cash and deposit a cheque. There was a long line and I was getting really bored so I started noticing all the people around me. At the...

2 years ago
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My first Time91

I was in high school. I met her at an inter-school sports event. Jennifer. Her name was Jennifer. I met her by sheer coincidence, we were asked to take scores for the basketball match and thus sat close. She wore a short sports skirt that exposed her long brown legs. Being a virgin, my attention was not on her firm too-big-for-her-age breasts, or her god-damn-that’s-tight ass that I only noticed when she was leaving, it was on her beautiful warm smile that would most certainly thaw a...

4 years ago
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Sex with my aunt for the first time2

So, we both been waited till we try to sneak. Finally, when she went to take a bath I was waiting inside the bathroom, when she came in and saw me she kind of scream and said ’oh what u doing, if anyone see us together we will be going to be big trouble” I said “don’t worry just lock the door “and she did lock the door. She looked at me with lust and I kissed her passionately for a long time. Kissed her neck and let me felt her boobs for a long time. I sucked her nipples and she was breathing...

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