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From Online Dating to Real-Life Cuckolding
03/02/2014
I was on a dry spell, so my friends suggested that I sign up for a popular dating site.

In less than a week, I was found Jessica. She was an average-looking brunette from Canada who just moved to my area for work.

Within a few messages the conversation turned sexual and within a few hours I was at her place fucking.

Jessica lived up to her hype, skillfully sucking my cock before bouncing a great as on my cock as she rode me. We fucked for hours upon hours until I had to go to work very tired, but satisfied.

We became regular fuck buddies in the following weeks. During that time, she would share the messages she got from guys on the site—some were mild while others were downright perverted from the first message.

I encouraged her to respond to any guys she found interesting but she never took it farther than the messages. Soon she had to go to Vegas for a work conference that lasted a week.

I told her to have “fun” there and let me know how it goes. That’s when she told me that at last year’s conference an attractive black coworker from a different region had hit on her.

Jessica never did anything because she didn’t want to be known as a promiscuous girl at work. She also had never been with a black guy and was hesitant to do so. I encouraged her to go for it and keep me updated as it goes.

A few days later, I get a text from her that reads, “He’s here.” I ask her if she’s going to go through with it and she replies, “Maybe ;-).”

In the afternoon, she sent me a text that they’re going to get drinks and she’s excited. In the spur of the moment, I tell her she should record the action and send it to me when she’s done.

A couple hours go by and I don’t hear anything. Wondering if she actually hooked up with him, I get a text from her. It’s a picture of her mouth and hand wrapped around a huge, black cock.

I quickly respond to ask how it was. I get nothing back.

I was so aroused, I was jerking off to the picture within minutes. I don’t know how many times I masturbated that night out of excitement, but eventually I fell asleep with my head spinning.

Early the next morning, I get a call from Jessica when she excitedly says, “Last night was amazing!” Before I could even get a word in, she launches into a recount of the previous night.

They had met during the conference and had small talk until she told him that she had been thinking about him all year. With a quick smile, he asked her to meet for cocktails at the end of the day.

They met at the hotel bar and kept it civil with other coworkers around. A few drinks in and she was rubbing his cock through his pants under the table.

He took the cue and the headed up to his hotel room. As soon as they got into the elevator, she started making out with him as they felt each other up. It wasn’t long until his hands were down her pants, feeling her wet pussy.

They rushed down the hallway to the room. As soon as they got through the door, he slammer her against the wall and began making out with her while he fingered her.

Jessica couldn’t wait any longer and dropped to her knees. She whipped out his cock and it was long, thick and hard.

She went to town, telling me everything about him was perfect. His cock was thick enough to stretch her mouth, but not too big that she couldn’t get her mouth around it.

Jessica didn’t think she could take all of him, but he gave her no choice. He had her head pinned against the wall and he was face fucking her.

She was surprised she was able to take it all and said she had never gagged and chocked so hard in her life. What surprised her even more was how much she liked him using her and how horny it got her.

Amid shifting from his cock to sucking on his “large and perfect balls,” she asked him to take a picture. That’s the one she sent me.

I guess they had an impromptu photo shoot as she engulfed his cock with her mouth. He then told her that he was going to put on a show.

He picked her up and tossed her on the bed before walking to his luggage. He pulled out a video camera and set it on the dresser, adding, “It’s show time.”

Jessica said she felt the thrill and decided she was going to give it her all too. As wet and horny as she was, it was still a shock as he started to slide his cock into her.

It took a few strokes and soon he was all the way into her. She had never had a cock go so deep.

He noticed and asked her if it was the biggest cock she’s ever had. She told the truth, and that pleased him.

The floodgates opened and she told him everything. He was the first black guy she had ever been with and that her fuck buddy told her to fuck him.

That was all the fodder he needed. While he fucked her all night, he kept calling her a dirty slut that wasn’t satisfied until she got his nice, black cock.

Jessica went with it, agreeing with him. She told him that she was going to send me that picture of her blowing me. She was going to tell me how well he fucked me, and how much better he was than me.

Jessica doesn’t remember how long they fucked or how many times. She didn’t realize until the morning that he didn’t use a condom and pumped her full of his cum all night.

Even though she wasn’t on birth control, she said if she did get care if she got pregnant from him because it was a hot night. When she was getting ready in the morning, she asked him for a copy of the video.

He refused. He told her was going to keep it until next year as a guarantee that they would fuck again at the conference.

Jessica happily agreed. She really didn’t need that as motivation as they fucked every chance they got—in the bathroom during breaks in the conference to every night in the hotel room.

She came back a happy girl and that’s when our cuckold relationship began.


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