Virginity Lost In An Online Hookup free porn video

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My name is Jason and I was a 26 year old virgin. I've always been interested in sex and constantly horny, but the opportunity had never presented itself. That was until last night when I was perusing a dating/ hookup app, and the local guys.

Let me start out by describing me before getting into the action. As stated, I am a 26 year old, white male. I stand roughly 5 feet, 10 inches tall and weigh in at 135 pounds. Now I don't frequent the gym, but I do keep in good shape, resulting in toned arms and chest, and a little definition in my abs. Moving south, I have a 6.5 inch cock which is nice and thick, and a tight round bubble butt that guys just love. I keep my cock and ass shaved so that they are nice and smooth and presentable.

Now I've always been sexually attracted to both males and females. I've always dreamt about and gotten excited at the thought of bottoming for a guy. I had toyed with the possibility of doing this multiple times, posting online and frequenting dating/ hookup apps, but nothing peaked my interest enough to pull the trigger. That was until last night when I started talking to a 19 year old in my area.

I started chatting with this young man and he told me how he had never done anything with a guy before either. He was not a virgin as he had dated and fucked girls in the past, but he was looking to have his first experience with a guy. Through the chatting we determined that we were interested in each other and decided to swap pics. He too was a white male with some nice definition in his torso and arms, a nice long thick cock with a monstrous mushroom tip, and a pretty taught ass to top it off. We talked for a little while about what we were interested in doing and decided it was time for us to meet.

Knowing that I was going to be bottoming, I went to get ready. I made sure that I shaved myself smooth everywhere. I cleaned my chest, back, cock (so that I had my landing strip), and my ass. I then went through the process of making sure I was clean and ready to go and it was time to warm up.

Now since I have never had sex before, I had to keep myself satisfied in other ways. That is why I have my dildo. 6 inches of ribbed pleasure which allowed me to get off, and in this case warm up for what was about to come. So once I was clean and ready to go, I lubed up my ass and slide down on top of my dildo. I grinded on in and bounced up and down slowly just to get used to it again, and then began to ride it with some vigor, stretching my ass out. As I was really getting into it I heard a knock at the door and yelled for the person to come in. The gentlemen obliged and walked in to the sight of me with a dildo up my ass.

He was immediately excited and wanting to have some fun. He placed the lube that he had brought with him down on the table and I told him to pick up the camera and phone that was there. I love recording when I play so I already had a computer set up capturing the action and these were for him to capture a POV perspective. He picked them up and walked over to me, ran his hand down my back and rubbed my ass. He got down on his knees to get a closer look of the dildo up my ass and felt how wet I was with his finger. It was all too much for him now and he was ready to go. He stood back up, walked in from of my and began to unbutton and slip off his pants.

As his pants fell to the floor, he exposed that delicious cock I had seen in his picture. It was just what I was craving. While still bouncing feverously on the dildo I reached out and grabbed his now semi-erect cock. I began stroking it as I moved it closed to my mouth. As it reached my mouth I stuck out my tongue and began teasing him by flicking it in his pee slit. He loved it and when he couldn't take it anymore he grabbed the back of my head and shoved it all the way in. I sucked his cock with long, slow strokes and began to get a rhythm going; up and down on the dildo, while in and out of the cock. I had to have sucked him for at least 15 minutes, getting it all wet, sucking on his balls every now and then and flicking my tongue in his slit. Eventually I couldn't wait any longer, and I needed that cock in me.

I pulled his cock out of my mouth and told him to sit down on the couch. He sat down and rubbed his now wet cock as he watched me take a few more bounces on my dildo. At this point it was not necessary, but he lubed up his cock as I got up off my dildo and slowly made way over to him on the couch. I needed his cock in me so bad, but there was still time to tease him once more. When I got to in front of him, I turned around, bent over, spread my cheeks and showed off my tight, yet stretched, asshole for him. He loved it and took his lubed up fingers and inserted them, just to get a taste. It was enough of the foreplay though, and time to get to the main event.

I straightened up, turned towards him and slowly lowered myself onto his cock. There was little resistance as I slowly rocked back and forth and up and down on his cock getting used to this new sensation. All while doing this my rock hard cock is rubbing against his stomach and chest. He was in sheer bliss, just laying back and enjoying it. Then he popped up, out of his slouching position and I felt a hand on each of my ass cheeks grabbing a handful. Each hand gives my ass a spank and then spread my cheeks wide, providing a great view of his cock deep in my ass for the camera's which are now placed in front of us. With my ass cheeks spread wide and my ass taking all of his cock deep, he decides it is time to pick of the pace and begins fucking my faster, harder, deeper. My legs and feet, which were perched bent on top of his legs, now fall to the side as he is in complete control and I am lost in ecstasy. After doing this for a while he tires and his pace lessens. That is when I moved back into control.

I spin around with his cock still inside me, plant both feet on the ground and continue to bounce on his cock hard and fast. I make sure his cock is pounding me and being buried in my ass. He likes the view, as I am bent over, and he smacks my ass as I take care of his cock. His stamina was amazing and I was shocked he hadn't cum yet. I decided it was time to give him a bit of a break though. I got off his cock and positioned myself on the floor, face down ass up. While doing this, I reached being me and spread my ass wide beckoning him to come over. He obliges, gets down on his knees and begins to like my hole and tongue fuck me. It drives me crazy and I want his cock again, but he isn't done teasing me; it's his turn to do it now.

To tease me he positions his mushroom tip against the entrance to my hole. He beings slapping his tip against my hole and sticking just the tip in and out of my hole. I beg him to give me all of his cock and eventually he obliges and plunges his entire length balls deep into my ass. He decides he is going to use all of my ass now and he is going for goal. He pounds away at my ass so hard all you hear is the sounds of bodies slapping together and moaning. He pushed my shoulders down for leverage, grabbed my hips and shoved his cock in me as deep as he could. I could feel the amazing sensation of his taught ball sack slapping against me the whole time.

I could tell he was getting close as he grabbed my ass on either side and began going as fast as he could for as long as he could possibly stand it. I told him to fill my ass with cum and he buries his cock deep in me one last time as I feel him explode. I feel rope after rope of hot, sticky cum shoot out of his cock and coat my ass. I couldn't believe the size of it or ow long it took him to get it all out. Eventually though he finish, removed his cock from my ass and came around to the front of me. He put his cock in my mouth and I sucked him clean.

Needless to say we didn't just do it once last night... It may have been my first, but it won't be my last, especially with him.

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It was very difficult for my father and me when my mother left us when I was only twelve years old. She was very beautiful and sexy looking, and probably still is. It turned out that she's a real slut and cared more about finding a lot of different cocks to fuck than she cared about us. Dad does his best and makes many sacrifices to be the best parent he can.My name is Ashlee, and I’m now sixteen years old and Dad is forty. We live in a comfortable condominium in the Little Rock area. Dad works...

Teen
3 years ago
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Lost My Virginity With An Aunty Whom I Met Online And Had A Rough Sex

Hey, I am prajwal, I have been reading stories on iss from a month and I feel I must share my story also. Here we go I was 19 when this happened, I am 6 feet tall and good looking guy, and this aunty I met online her name is Raksha , she is 29 years old and she has lost her husband in an accident, She is 5.7 feet tall sexy ,fair and had a very curvy figure. Her breasts were 36d size, and she had some nice ass and sexy naval. Beginning Back in April 2015 I was a bored student and I always...

2 years ago
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An Online Relationship

Thanks to Demorie for her encouragement and assessment. Dave looked at the Bulletin Board — Personals. And one in particular caught his eye. It was simple, appearing innocent, and yet appealing. Nothing sexual in it, but Dave felt something sensuous and refreshing. The Post read:: ‘Female college student looking for online emailing’. All the other posts were the usual: ‘Looking for erotic chat’, ‘Looking for a fuck buddy’, ‘Mutual masturbation in (you name the state or city)’, ‘Do you like...

2 years ago
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First Time Fun With An Online Girlfriend

Hi, friends. I am 35 m from Delhi. Who travel across India for work and pleasure along. I have been a reader of this site for more how long myself don’t know. I am a horny single guy (yes not married yet) and been having fun from 18 years age. Experience do counts hehe. No, I ain’t a tom cruise I am a normal Punjabi Indian man heavy built with an average tool who loves to satisfy his partner to the core. Love giving and getting oral fun. Experiments with food items etc. I am in for online phone...

2 years ago
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Virginity Lost In My First Gangbang

Hi, am Samarpita and this is my first story in ISS. I have been a huge fan of ISS and am gonna share my real life experiences. First I’ll tell about myself, am a girl from Rajasthan but was raised up in Canada. Am still a resident of Canada but I frequently visit India. My age is 20. And my structure is 38-29-38. I have a nice round and big ass and big tits with dark brown nipples. I generally don’t like to wear inner wears right from childhood. Now back to the story, I was in my home town in...

3 years ago
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An online friend from the USA visits London

Another day of heavy rain in London.  I listened from my bed as the latest storm drove rain into the window. Outside I could hear the wind howling. Without even opening the shutters I knew it was going to be grim.My mood was not improved by the radio news. Coronavirus, Trump and the latest post-Brexit fuck-up from our incompetent government.If all that wasn’t enough I had just been dumped again, by WhatsApp this time, a first for me. I was done with online dating, it was a disaster for me....

Mature
2 years ago
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From Math Teacher to Online Whore

I was still single. I had just broke up with a girl at the beginning of school. She caught with her Mom having sex. She walked in her Mom bedroom to see me fucking her Mom in the ass. Damn her Mom could fuck. After that she started some rumors around school I was a bad guy. No harm. I was not looking to get tied down. I was over skinny high school girls. I was more into curvier ladies. The bodacious hottie with the voluptuous curves. The wider the ass and the bigger the boobs was my new...

4 years ago
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Online Crush

I first met her about 8 years ago. I met her online in a video chat room. I had met other women in chat rooms, but none that I ever really connected with. You see I’ve always felt a tad bit silly visiting those sites. I even assumed that I wouldn’t meet anyone that I would like, although I realized that that view was indeed a bit hypocritical. Rather, I would lurk and read the dialogue, but it quickly bored me. However, this woman was different. She was quick-witted, she was bright and she...

2 years ago
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From Math Teacher to Online Whore

Introduction: She wanted to earn extra money after class I had to stay after school. I was beating the erasers on the chalk board in detention. I looked up to see the male teacher was falling asleep. It was close to 4pm. I only had a few more minutes before the last bell to go home. I had just moved in my Grand Mothers basement about a week ago. She was always out playing Bingo or at church. It was a good thing. My parents were no longer in the picture. I was going to drive my old clunker home....

4 years ago
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Kerries Journey Chapter 2 I explore online

At the time I had just turned forty. That milestone, for some reason, had me beginning to wonder whether, as good as my sex life was with my husband, Tom, there was more to sex than I had experienced.Certainly the massage in Phuket was the first time a woman’s touch had aroused me. And, how I came and came again! Even in my late teens, I had not, as many girls do, experimented sexually with girls. I didn’t mind if they did but, for me, sex was something you did with boys. Not that I was that...

Bisexual
3 years ago
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Online Shopping With Mom

Hello this is prasad from Mangalore. I am MBA and working in MNC in Mangalore. I am only son to my parents and dad is working in Nationalized bank as chief manager. Currently my dad working in Gujarat and mom and myself stay in Mangalore. we stay in our own house. since i am only son i got all the privileges at home and can i say happy family. My age is 27 and my mom is 49 and dad age is 5 5. My Mom is graduate and she is housewife and she is kind of innocent. She got 36 B- 36- 38 figure, fair...

Incest
4 years ago
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Online Friend Sonia Fucked

Hello People this is Luvbunny once again here to share my story with you guys. This happened with me in 2010 December and I met this beautiful South Indian Kerala lady or should say girl online via website chatting and her name is Sonia 29 years of age when we met. She is about 5 feet tall typical south Indian skin colour black hair till shoulders black eyes soft lips, bust size 32 C flat tummy and cute little ass but married lady. I use to surf a lot online to meet girls online but never got...

2 years ago
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The Limitations of an Online Relationship

They met in an online, sex chat room. It was Andrea’s first visit and she almost left thirty seconds after she created her profile. Six private messages popped up on her screen.Hey beautiful. Want 2 fuck?I’m 9 inches and ready to go.Hard and hot 4 u. Hi, Baby. A/S/L?Do u cbr?Gonna cum all over you. “What am I doing?” Andrea said aloud in her empty apartment. This was sleazy. Maybe not as bad as going to bar and picking up a random stranger, but close. Nonetheless, she was here because she would...

Seduction
3 years ago
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Meeting my online daddy

I met Mark online. I'd joined a gay chat room. I had been fantasizing about being with a man for a while and this was a harmless, anonymous way to explore my interest.To begin with, I was very shy and didn't know how to respond to the occasional message that came my way. Then I got into a conversation with a guy who made all the running. I only had to go along with his messages.I've discovered that the best cybersex is to be had by going along with the person you are playing with. Unless it...

4 years ago
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From Online to Bliss

We first started chatting online and both of us had fantasies of having sex with someone we met online. We are both married and were both going though a pretty dead period in our married lives. I was about 55 and she was in her early 40's. We were both looking for fun online but during our long chats we came to the conclusion we should meet and test the waters. So this was an adventure. The first time we met we arranged to meet outside a major bookstore in T*****o. After a delay, in which I...

3 years ago
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The Hookup

It had been another long day of endless meetings before the conference finally ended. I was downstairs in the hotel lounge nursing my beer when, to my surprise, the hot blonde that I’d been watching appeared beside me. Smiling, she reached into her jeweled purse and pulled out a hotel room keycard. Biting her bottom lip, she put it in my shirt pocket and patted it. ‘Give me ten minutes,’ she said, and then turned and left without another word. Ten minutes later, I was standing in front of the...

3 years ago
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Convenience Store Hookup

I stopped off at a convenience store just north of Dallas on my way up to Oklahoma to get some gas and a bite to eat. It was about eight in the evening and my goal was to make it across the Red River and to my destination before nightfall.I filled my tank at the pump and then stepped into the store to grab some snacks for the final leg of my trip. There was no one at the counter, so I called out asking if there was anyone there. No one answered, so I waited a few more seconds and repeated my...

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