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I [27F] secured my friend [29M] into sleeping with me (long)
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Not long ago, I [F27] asked reddit how to instigate something sexual with a friend [M29]. After some overwhelming support, I decided to take everyones advice.

We were both at a group gathering, and I was trying to find a good time to strike up some suggestive conversation with him. I managed to catch him with one other of our friends so I took the chance to ask them both (only caring about his answer) to help me with a dating app profile. I told him it didn't know which photos I should use for my profile and wanted his advice as a man. To my surprise, he told me that there was a photo on my instagram that he said was a good photo and should use it. I was happy to know that he was able to recall something like that off the top of his head and he even helped me pick a couple more that he liked.

I got to talking to him about dating and the like and told him I wouldn't even know what to wear on a date these days. He perfectly replied by telling me that since the weather is warmer it's the perfect time for summer dresses which he likes on women. Bingo!

After the gathering, we occasionally texted mostly about the nuisance of dating and trying to give advice. We never would usually text much before this, so I could feel this common interest in dating bringing us closer together. We had talked about how we were in a bad place for a relationship but at the same time, had needs. I started to learn what he likes in women, most importantly the way the dress. The reason why he suggested a summer dress is because I now know he loves to see women's legs in dresses and skirts.

Skipping to the next time a few of us hung out, I knew he was coming so I of course wore a skirt to try and show off my legs. I feel that it worked by a comment he made along the lines of "you must have wore that because you knew I'd like it". Like he read my mind, it's exactly why I wore it so I told him something like I couldn't ignore his good advice. We shared a few flirtatious words and looks over the course of the day. This lead to more frequent and personal texting.

I eventually made a comment that I think broke the camela back. We were texting about me not taking much interest in many men on apps and I made a comment like "if they had a body like yours, they'd at least get a solid chance". This comment opened up doors from him as his comments became much more personal and specific about me. When telling me about how he likes women showing their legs, it became how he liked it when I showed my legs. He became much more complimentary and flirtatious and I naturally followed. It took a week or so of solid texting until he asked me for drinks just the 2 of us. We would only ever hang out in our friends group so this was the chance I was waiting for, and I feel like he was too.

We met for drinks last weekend and I made sure to put on my favourite summer dress to make sure I caught his attention from the start. We ate and drank while I gave him as many hints as I could. Sitting close, touching his arm or leg when I laugh or during conversation. I could tell he was picking up on my hints when he would lean in to talk and put his hand on my waist. Slowly but surely, the drinks were setting in and there was obviously tension. We were getting close to ending our night and I was mentioning I had a lazy day the next day waiting for me. He said he had the same and that we should be lazy together before offering to have some "lazy drinks" at his place. I didn't hesitate to agree and went home with him that night.

We wound up at his place, having a couple more drinks on his couch. Flirting and laughing into the late night. Eventually I must have given him a look because he smile at me in a way that looked like he had something in mind. I couldn't help but smile back at the look he made which gave him all he needed to kiss me. Our first kiss was breathly and tasted of a sweet alcohol. We got a little touchy with each other while we kissed and he was brave enough to feel my breasts, which I was more than accepting.

He eventually lead me to his room where he was quick to lay me down and mount me to continue kissing me. Before long, he kissed down my neck and stomach over my dress. His hands were caressing my thighs under my dress until he reached up to pull off my panties. I did nothing but lay there with a smile as I felt him pull my dress up and slide his face between my legs. The feeling on his mouth and tongue was what I needed to feel for quite some time that it didn't take long for me to feel the myself on the edge. I told him i was cumming but he didn't let up for a second until I was squirming trying to escape the overwhelming feeling of ecstacy. Not even had caught my breath, I pulled myself up to kiss him turning him to sit on the end of the bed so I could kneel before him. I wasted no time in undressing his bottom half to show his already very hard member. I rubbed it to get the feel of it in my hand but couldn't stop my desire from putting it in my mouth.

I sucked on slowly, taking in his taste and his size/shape in my mouth. The sounds of his moans were incredibly arousing, giving me all the encouragement I needed to pleasure him. I held the back of my head where I felt some slight pressure as he pushed me down. With that, I was moving his hips pushing into me. I knee what he wanted and wanted to give it to him.

I did all I could to push myself down on him, feeling his tip rubbing and probing the back of my throat. Unfortunately, maybe because I'm out of practice but I struggled to take even half oh him in my mouth. His tip touching the entrance to my throat was enough go make my gag reflex active. I don't know if he liked it or not, but I felt him trying to push through my limits and I did all I could to swallow him, but to my and probably his disappointment I couldn't take it any further.

After some time of oozing saliva all over his hardness, he pulled me up to him kissing me we funbled to undress each other. We eventually exposed our naked bodies to each other for the first time and spend some time to touch, kiss and lick eachother bodies like a naked greeting.

He paused to get himself out a condom and I knew this was finally it. What I had wanted was finally here. I took the condom from him and let him lay down before rolling it over him. I straddled him, rubbing his tip against my opening while we hungrily looking into each other's eyes. I sat on him, sinking him inside me. It may be because it had been a long time for me, but the feeling of him going in me was enough to make me shake in pleasure.

I played over him, on my hands and knees sliding over his length while his hands explored my body hovering over him. The feeling of him first sliding back and forth inside me feels so memorable I can almost feel it while I write this. My excitement to feel him inside me helped me build the pleasure easily. I sat up in him, grinding across him listening to the wet sounds of us being connected. His hands held my thighs firmly, guiding them back and forth until I felt myself cumming again for him.

I was puffing and panting after I came and felt so sensitive to continue riding. He could tell as I slowed right down so he took the initiative and rolled onto of me. I wrapped my legs around his waist and my hands around his body when he wasted no time pushing inside me. He moved somewhat slowly, hugging and kissing while he fucked me. Our heavy breathing made short work of kissing and he had found his rhythm thrusting into me. He would occasionally slow down, looking at me and touching my body and I assumed he was close but didn't want it to end. I did all I could to squeeze him internally when he pushed inside me to make him feel as good as possible. While he was thrusting a little faster, he asked me if he could cum on my body instead of in the condom. I'm not sure why but the fact he asked me that felt very considerate and sweet. All I could do was smile at him as say "of course, you can cum anywhere".

As his speed and moans got faster, he pulled out of me suddenly and snapped the condom off quicker than I'd ever seen someone do. I took my question and grabbed his dick, rubbing it firmly while he groaned loudly. Kneeling above me, between my legs still, he throbbed in my hand as I watched his well deserved cum shoot across my stomach, some reaching up on my chest. I have to admit I missed the feeling of warm cum on my skin while I rubbed a pulsing hard dick.

We laid for a while to catch our breath before he let me shower. I ended up spending the night there and the next morning we both agreed to keep this a secret from our friendship group.

We have continued to text and develop but that is a story for another time. This has been much too long as it is

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2 weeks ago