[MFM] My First Cuckoldress

The first time I fucked a cuckoldress was a few years ago, back in Las Vegas. On my way into town, my local booty call wasn’t returning messages. We had a bit of a falling out, so I was starting to accept that she wasn’t going to be an option. So I turned to the dark realm of Craigslist.

I was trying to post a M4F ad, but hookers liked to knock those down to force men to browse their F4Ms. So I placed a M4MF, posting a pic of my cock cumming, and noting that I wanted to fuck a girl in front of her boyfriend.

This couple was amazing by the size of my cumshot, so we met in the lobby of the hotel I was staying at. He was tall and lanky, she was short and fit, wearing a tight black dress and sneakers.

There were these tiny couches – I sat next to her, forcing the guy to sit opposite and watch me flirt and chat with her. We talked a bit about our travel plans and some other naughtier topics. Occasionally I let my hand brush against her knee or thigh. She never flinched, and he grinned every time.

The rules were I could do ANYTHING I wanted to her, but no kissing and no going down on her. She was to be a fucktoy for my pleasure, so nothing romantic or for her.

When we were all comfortable, I took them to the elevator. The doors closed, and I slid my hand under the edge of her dress, lifting it up over her ass. She didn’t have any panties on. With my other hand, I grabbed under the front of her dress, feeling her wet pussy.

Her boyfriend then pointed out that he didn’t know what floor we needed. We were still on the lobby level, and at any moment someone else could have walked it.

Eventually I gave him the floor number.

In the room, the boyfriend sat down in the corner and quietly started to jerk on his cock. She started sucking my dick immediately, and it was a really good blowjob – to the point that I was ready to cum in the first 10 minutes. I pulled out and started to stroke my cock, making it clear I was about to cum on her face and tits. They freaked out and begged me to take her dress off first – they were traveling and only packed one dress, and didn’t want to clean cum out of it.

She stripped, and I fucked her face until I shot thick ropes of cum over her tits. With the last twitch of my balls, I put my cock back in her mouth and demanded she lick me clean.

I don’t know why, but this always keeps me hard for at least one more load of cum. So when she had me polished and throbbing, I put on a second condom. I put her on her knees and started fucking her doggystyle, then play with her asshole with my finger. It was a fairly loose asshole, taking two of my fingers, which meant I could fuck her anally.

There’s something so cruel about fucking another man’s woman – you really don’t care about if she’s going to want to fuck the next day or not. In fact, I maybe wanted to break her? I was rough with her little asshole, and I liked the way it make me feel. But it wasn’t going to make me cum. I pulled out, and then pulled the condom off for hygiene. She turned around and immediately started sucking my cock again. Seriously, she was an amazing cocksucker.

But then she started to beg me to fuck her again. And I knew what she meant. She was guiding my naked cock into her pussy.

This was hands-down one of the dumbest things I’ve ever done sexually. I wasn’t thinking clearly, between being depressed over losing my FWB earlier in the day to being horny to dipping deep into my primal nature… I started to fuck her raw.

I was all-in now. I laid back down on the bed and made her ride me. I was sure to position her so that her man could see my thick cock stretching out her tight little cunt. And to make sure he got the best possible view, I squeezed her ass tight, spreading her.

She started to beg.

She wanted me to cum inside of her. I couldn’t stop myself.

When I was done, I realized I never told her to wipe the cum off her tits. I noticed some was on her face, too. And there was jizz leaking down her leg.

As she got dressed, her boyfriend asked me if she should wipe the cum off her face. I laughed. I told her to leave it, put the dress on, and walk back to her hotel with her man, so that everyone knows she’s my little cumslut.

They left down The Strip.

Later, when I got home, I got tested and passed. Since then, I’ve been a lot more in control of my hook-ups, and I stopped using Craigslist. But damn if it wasn’t hot to cum inside of her tight little pussy in front of her cuck of a boyfriend.

Source: reddit.com/r/gonewildstories/comments/a0swtx/mfm_my_first_cuckoldress