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So for the first time in eighteen years I was single. I was only thirty-four, but I had been with my husband since the age of sixteen.  I h...

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So for the first time
in eighteen years I was single. I was only thirty-four, but I had been with my husband since the age of sixteen. 

I had no idea how to meet guys because I'd never had the need. 

Anyway, I wasn't looking for a serious relationship - yet. I just wanted to enjoy being single for a while and explore my sexuality.At first I decided to play on the Internet a little bit because I just didn't feel ready to meet anybody in real life. 

One night, out of sheer boredom, I googled "sex chat rooms" which led me to Sexy Time Chat. At this point I didn't know what Reddit was, as I had found the chat site through Google not Reddit.

I was a little timid at first chatting with different guys but, each time I did it, I got bolder and bolder. It really helped me discover things about myself and my sexuality. It also made me a lot more confident. 

A lot of the guys would ask for pictures or to cam and for months I would always refuse. 

I couldn't imagine sending dirty pictures of myself to a complete stranger let alone getting on camera, live, and touching myself while somebody watched.

Well, over the months, I developed really good friendships with two guys. Yes, we had amazingly sexy conversations and role-plays but we also talked about every day normal stuff also. 

During one of my hot and steamy chats with one of my guy friends, out of the blue, I took a few pictures of my dripping wet pussy and sent it to him. Hell, I figured after his amazing work at getting me so worked up and wet, he at least deserved to see what he did.

The response I got from him was so amazing and it made me feel so confident and good about myself. He had mentioned Reddit and said I should post the pictures to gonewild. 

I laughed it off and told him I could never do such a thing.

But, for the next couple days, I just couldn't stop thinking about it. It was so nice to have him tell me how hot I looked and I was curious to see what other people would say.

For the next week or so, I would go on Reddit and look at the different sub Reddits and look at what other girls and guys were posting. 

Eventually, I got up the nerve to make my own account. It took me about another week after making the account to post the pictures. I posted the same pictures I had sent to my friend, a few close-ups of my pussy, dripping wet.

Within moments my little envelope turned orange. I nervously clicked on it and the responses I got were amazing. Some of the guys, and a few women also, were so creative with their responses. 

Some of them wrote me little stories, telling me exactly what they would like to do with my pretty little pussy. 

Others sent me dick pictures, and some even sent me videos of them jerking off to my picture. 

I was addicted.

I tried to respond and thank as many people as I could and, to this day, I have friendships with some of those guys and a few girls, too. Well, all this attention made me confident and emboldened me enough to want to meet somebody in real life. 

I was having so much fun on the Internet but it just wasn't cutting it anymore. To be frank, I needed a real man. Desperately!

One friend from Reddit had told me about a hook up site called Adult Friend Finder. 

He said he'd had some good luck on it and told me to give it a shot. 

As soon as we were done chatting, I googled AFF and set up an account. I didn't know it then, but I was set for the most sexy, hot and slutty time of my life! Believe me, my time on Sexy Time Chat was incredibly sexy, but this next part of my story... well...

Making my account, I agonized over the username (I wanted something sexy yet not corny), and added a bunch of pictures to my profile. 

Within moments my phone started going crazy! I was getting tons of both private messages and requests to IM. I felt like a kid in a candy store! Again, a lot of the guys were very creative, sending me sexy stories and pictures. Some were pretty creepy too!

I was looking through my incoming messages when I stumbled upon one that really caught my attention. I think it was the picture I was more attracted to. He was very good-looking with a really nice full beard. And I totally have a thing for beards.


I responded to his message with a few extremely sexy and X-rated photographs. We started talking about meeting and hooking up. Due to his work schedule it was going to be a few days before we could meet.

During this time I told him about what I wanted to do: how I wanted to have fun, experience new things, explore my sexy slutty side. He was more than happy to get me started.

He'd picked up on my submissive nature during our dirty talks and dominated me from the start. He told me what I was to wear when he came over (I had told him about these cute thigh highs I had just bought and a sexy nightie). 

He also told me what I was going to do when he got here, making it clear that I was his slut and he was going to use me accordingly. 

I had never been more turned on, and incredibly nervous, in my life.

The day finally came. I was shaking the entire day. I got ready, doing my hair and make-up, 

dressing in what he had instructed, and then put on my robe and sat on the edge of my bed and waited...

Finally, the knock came on the door. 

I honestly thought about hiding and not answering it; I was so nervous! 

But I forced myself to stand and walk to the door. I opened it and let him in. He was even better looking in person and seemed so nonchalant about the whole thing while I was hyperventilating. 

I walked towards my bedroom - I don't even think I said anything at this point - and he followed.

He shut the door behind us, turned towards me and told me to take off my robe. I slid it off my shoulders to reveal the thigh highs and nightie. 

As he was looking me up and down, he started to remove his clothes. He sat on the edge of my bed, looked at me, and told me to kneel in front of him and suck his cock.

His words, his demands, filled me with an animalistic lust and desire.

I dropped to my knees and took his cock in my mouth eagerly, almost desperately. He was propped on his elbows, watching me slide my mouth and tongue up and down his shaft. 

With his hand in my hair, forcing me to look at him, he asked, "You want me to fuck that pussy, don't you?"

I couldn't even speak; all I could do was nod. He told me to stand up and get on the bed. I don't think I've ever moved so quickly in my life. 

He got behind me, bent me over and slid a finger inside my pussy. He played with my pussy and clit for a minute, before I felt the head of his cock pressed against my opening. 

Suddenly he pushed every inch inside, fucking me hard and fast. 

Not even two minutes in, I had squirted and cum. He didn't slow down. By the time he was done that first round, I had squirted four or five times. And this was only the beginning.

I took him into my mouth to get him hard again in between him fucking me. And he ended up fucking my pussy one more time before taking my ass. He completely and thoroughly owned all of my holes that day, making me squirt ten times. I was off to a good start.

We were talking afterwards and Reddit came up. 

He asked me if I had ever heard of the sub-Reddit randomactsofblowjobs. I told him I hadn't and he explained to me what it was about. 

Girls could post ads on there wanting to fuck guys in their city, and guys respond to the ads. It sounded like the perfect next step in my journey.

Story by Kassie

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