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25M update on my Mother’s Day plans
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Guiltypleasures5280 is age 25
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So my last post I got some good advice how to progress our situation and have an little update how it’s been going.

Some more back story to where the last bit progressed to over time. After she first walked in on my I started to get a bit more loud and vocal as I took care of myself she “happened to” walk in on me a few more times. And one time she loosely mentioned that she didn’t mind hearing me enjoy myself. So I got a little risky and left the door open one time when I did. A few minutes in I saw her sort of peaking in my door and watching me. When we made eye contact she didn’t leave and just kept watching. Once I finished and came back to reality she was gone. This happened a few more times over a few weeks. Until one time I saw her and sort of sheepishly asked her if she just wanted to come in and watch. I was laying in my bed and she just sat on the edge of the bed watching. She didn’t play with herself but she was definitely enjoying herself. She was quiet except for a few mumbles I couldn’t make out. After that she kept her distance a bit until one night a dinner. While we were eating she got quiet for a bit until she spoke up about it. And I don’t remember exact quotes but basically she just wanted to make sure I was really okay with what happened and that she was completely okay with it as long as I was. Obviously I enjoy it so I let her know and from there it progressively got to a point where instead of me just leaving the door open. I’d openly tell her I was going to and she’d follow me to my room. Then after some time she started to sit on the bed with me and began pleasing herself. After some weeks past. We got to a point where we were both completely nude and masturbating together whether it was in my room, her room or the couch. We still had not ever touched each other and just enjoyed the company and lewdness of the situation. This was as far as it ever got since then and unfortunately hasn’t happened for some time.

Back to the update. I sent my mom a text 2 days ago telling her I was going to come to her place to make her dinner for Mother’s Day and we just sort of got to our usual BSing and talking about life. The conversation started to get a bit dry and so I just decided to be blunt with her and ask if she remembered when she walked in on me the first time. She took a while to respond but she said of course she did. And I mentioned how I was actually glad she did and I miss our time together after that. She took a while again to respond. But said she missed it too and jokingly said I shouldn’t have moved out haha. I didn’t really like further. Just sort of dropped the seed. We talked about it a little more before I had to get to bed for work.

I texted her again yesterday asking if there was anything special she wanted to have and she didn’t have a preference. We talked again for a while and I asked if she wanted to do anything maybe I come over early and have a pool day and I half jokingly mentioned I’d take her to get a massage. But she refused saying there is no need for me to send my money on that and thanked me for the offer. I waited to respond a bit. And mentioned that I’d be happy to give her a back and foot rub. And she responded almost immediately saying that would be really nice.

So that’s really all I have as an update as of this morning. Hopefully I planted the seeds right and we can either enjoy ourselves together like “old times” or maybe progress from there. I’ll be sure to update again before I go over on Saturday and after if you all want to hear about it.

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1 year ago