[MF] former coworker wants me to have sex with her…with some interesting conditions [UPDATE 2]

[Previously](https://www.reddit.com/r/gonewildstories/comments/ku68ug/mf_former_coworker_wants_me_to_have_sex_with/?utm_source=share&utm_medium=web2x&context=3)

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Well, I did it. We didn’t really have much contact after the texting conversations, besides a few clarifying things and logistics. Saturday Cass said she couldn’t wait to have me over, Nick goaded me into telling him I was hard thinking about Cass. And then I was headed over to their place.

I texted Nick to let me into their building and he came down to the entrance and greeted me. We didn’t say much but as soon as the elevator doors closed we had this exchange:

Nick: You gonna give her a good fucking?

Me: I’ll..do what I can.

Nick: She’s super fucking wet right now.

Me: …Good.

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Then he led me into the apartment and asked if I was ready. Remembering the rules, I nodded. I hadn’t even seen Cass and I was hard. It was like double the nervousness of a first time. He told me to wait there and he went off into the bedroom, down the hallway. I looked around their apartment and saw the spot they zoomed me from.

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Nick came out of the bedroom, closing the door behind him. He had me follow him back to the bedroom and opened the door to reveal Cass. The bed faced the door and she was perched on the end of it, ass in the air. She had a hoodie on and was face down. And naked from the waist down. And he wasn’t kidding, from six feet away she was visibly wet, I could see it trickling down her thigh.

Nick had gone and sat down on the side of the room and was watching me take it in. He gestured to me and I stepped forward and put a hand on her ass, gently feeling her. She was warm. I could also tell she had been spanked because there was definitely some characteristic redness (the fact that they said no *excessive* roughness made me think some roughness was okay; I had confirmed this with Nick). At this point I was reasonably sure they had been at least fooling around before I showed up, and that was a weirdly huge turn on, like he had been warming her up for me.

Anyway back to her ass. Super great remember? Great shape and fullness. Good amount of jiggle. Perfectly waxed. I started massaging with both hands and she gyrated a bit and pressed into me. I could hear her breathing. I pulled her cheeks apart and took a good long look. She pushed her ass up a bit more to facilitate this, she knew I was looking. I stuck two fingers in her pussy and felt her wetness. She responded by pushing into me. It occurred to me I should work her clit so I used her wetness as lube and rubbed her clit with one hand while I fingered her with the other. She was pretty into this, grinding into me.

I was determined to make her cum which was annoying with this awkward angle. I essentially had an arm wrapped around her to come at her from the front while I fingered her from behind. Luckily she came relatively quickly. Normally I’d feel cocky about this but she was definitely most of the way there when I got there. After she stopped tensing up Nick placed a condom on the bed next to us.

I took this as a signal and not wanting to overstay my welcome pulled my pants down, and, after a moment of deliberation, off. I was a little soft after focusing on using my hands so I pumped myself a little, with her juices still on my hand. I could tell Nick was watching me but with an expectant pussy in front of me it didn’t really bother me. I fingered her a bit with the other hand to make sure she was still ready (yes).

I pulled out my own condom. I am a little bigger than average and normal sizes don’t work very well. I knew Nick was watching me do this but I didn’t look at him. Of course I couldn’t help but think about his size but I returned to the task at hand and rolled the condom on. I positioned myself behind her and rubbed my tip along her lips before pushing in.

From fingering her I knew there was barely going to be any resistance. If I wasn’t wearing the condom I probably would have gone all the way in in one thrust. Didn’t take much with it though. I gave her a few slow, deep pumps before I really started fucking her.

My height and the height of the bed were lined up nicely that I could really go to town. She was pushing into me too, and moaning a lot. I spanked her lightly and she made a positive noise. I spanked her harder and she made a louder noise. I looked over at Nick and he didn’t seem to object. I noticed he was feeling himself through his pants. At this point he could’ve been jerking off and I wouldn’t have minded (surprising myself) but he was clothed the whole time.

Doggy style and a condom is like a combination for me to last forever. It’s usually the position I switch to when I want to last longer. So yeah I’m pounding away with her, taking breaks to last longer, for what felt like 15-20 minutes and Nick asks me if I’m close. I look over at him and shake my head but take it as a message to try and finish.

So I continue fucking and spanking her, really straining to cum. Her moans are a huge turn on, I think she was overcompensating because she also wasn’t supposed to talk. I just imagined cumming inside her, fucking her from the front while she begs me for it. I imagined all the things I wanted to do with her, having my way with her. Soon enough I was able to cum and finished with my full length in her. I stayed inside her for a minute while we caught our breath before pulling out.

As I was pulling the condom off Nick came over and held up a little trash can. Knowing I had to leave, I pulled my pants back on and followed when he gestured me out of the room. He thanked me for coming (pun?) and for following the rules and said he’d text me later. I saw myself out.

Later that night I got a text from Cass:

Cass: Glad you could make it tonight! We had fun. Talk to you later.?

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So yeah. Pretty fun and hot experience. A lot of people seemed to be annoyed by the rules, please tell me you would have said no because of them. It’s a great deal either way lol. Anyway we’re already talking about next time and several of those rules will not apply… stay tuned.

Source: reddit.com/r/gonewildstories/comments/kvkpnj/mf_former_coworker_wants_me_to_have_sex_with