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casual fun with a friend
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So, next week I have arranged to go and visit one of my old friends, someone I haven't seen for almost 15 years. Despite this however, she and I have always remained in contact and been comfortable enough being totally open and honest with each other.
I don't know if it is a good or bad idea, but there is a part of me that is contemplating making an attempt at something.
I'm considering asking her at some point in the evening once we have both had a few drinks beforehand if she would be bothered or would mind if I undressed in front of her and let her watch as I masturbed. Either that or possibly suggest something more, asking her to watch me mastubate while I was riding my dildo in front of her. If she agreed, as she was watching, possibly suggesting she removed her own clothes one piece at a time as I suggested them. It would give me the ability to then finish over her amazing chest (yea, I have already seen her chest in the past with nothing else happening). That is, unless she decided to make me finish in her mouth. Dream scenario, we continued for the rest of the night having dirty fun in a casual mindset. Things being kept entirely between two friends behind closed doors |
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Update to this since I visited her
For the first few hours of me being there, her friend was visiting her as well and we all had a few drinks together.
Once they had gone home, we had a chance to talk openly between just myself and her where it didn't seem like any conversation was off limits. She had already seen a few intimate photos of me earlier in the evening when the subject was brought up (i did get a good compliment about the size and girth of it). I jokingly said it's been a few years since I last saw her topless, with her responding by immediately pulling her top and bra down to show me.
As the end of the evening came around, she told me I could sleep in bed with her on the other side (why do women all have a specific side of the bed they sleep on?). She kept making a point of saying how tired she was, which I took as her saying that nothing was going to happen with each other that night.
As we went to climb into bed, she pulled her dress over her head leaving her in just a bra and little blue thong which I forced myself to not look so it didn't make things weird. After I had pulled my clothes off down to only my boxer shorts, we both climbed into bed and talked for a bit longer before she drifted off to sleep, rolling back and forth between laying on her back and on her side facing me
After about twenty minutes, I was hugely turned on from taking sneaky looks under the duvet at her body and began playing with myself. Obviously I must have gotten carried away because she woke up from the mattress shifting, catching me with my boxers pulled down and my hand wrapped around myself.
After apologising profusely to her and trying to think of something to say, she sat up to reach behind her so she could unclasp her bra and remove it before laying back down, telling me "you may as well have a proper view and a better choice of where you can finish". I straddled her body and continued before finishing over her stomach and chest with her immediately saying "right, maybe now you will go to sleep and let me do the same!"
The next morning, it wasn't weird or awkward between us, but as I was leaving, she said to me "I'm surprised you didn't try finishing in my mouth!"
I'm seeing her again in a few months, I know what I'm gonna be doing! |
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If anything does end up happening with her at some point, it I asked her permission and she was ok with it, are there any bi men on here either very close or reasonably close to where I am who would be up for afterwards meeting up with me at his house for the night so we can watch the videos she and I made while he and I are having fun together? |
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It's looking like there might be a slight change to the arrangements now, she phoned me a couple of days ago and asked if I wanted to go away for a few days together staying in a caravan and going for walks in nature. Confined space inside a caravan, a few drinks with each other, I am extremely confident we are going to end up going for it with each other. If I think it's a possibility, I will ask if I can take photos and videos as it's happening so I can post them on my profile form you all |
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Adding a new comment to this thread so I'm able to find it when it needs updating... Latest development, after a conversation between myself and my friend, it's pretty much a guaranteed thing that something will happen between us. She accidentally let slip that she had suggested staying in a caravan somewhere away from where we both live in case we got a bit naughty after a few drinks without sobering up because of panic that someone might hear us |
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