Finally getting to [m]eet my online mil[f] – Precursor

*Obligatory names changed disclaimer*

I met Rachel through an adult chat site, she noticed a common interest (pretty mundane, non-sexual interest) and messaged me about it. I looked at her profile and saw she was quite a bit older (46) than me (22), which I was thrilled about. I’ve always had a strong attraction to older women and much preferred chatting with them online. However, I’ve found them to be the hardest to actually find and get the attention of. So, initially I just assumed it would be a pretty brief conversation so didn’t get my hopes up too much.

We ended up speaking for a few hours that first day, in the beginning about our shared interest and other harmless chat, then more towards the reason we were both there. We decided to swap a few pics. At that point I was nervous, we were having a good talk but before seeing her pics I was expecting either someone I didn’t really find attractive, or to be sent a slew of fake pics. When I finally got her pics my excitement grew even more. She looked like an attractive mother nextdoor. First all her pics were pretty casual which was awesome. She had a beautiful face, thick figure that still looked fit. She definitely looked like a mother who would catch your eye, or mine at least. I sent some of me back and there seemed to be a mutual attraction.

I told her of my attraction towards older women, which fit well with her attraction towards younger guys. She was married, and from what she told me by no means in a marriage lacking sex, but one that was little more than routine. The more she spoke about her desires sexually it seemed like she really liked the maternal dynamic between a woman her age and a guy my age. That’s not to say she’s looking for a “son”, but rather someone a little less experienced, someone who was still curious, eager to experience new things, open to some direction. I wasn’t a virgin, but by no means did I have a ton of experience either. The few previous experiences I had were while in relationships.

That first conversation ended without any sort of sexual playing or anything, yet I found myself more excited by than than other chats I’ve had were the other woman and I had played. We exchanged usernames on another chat app and said we’d continue our chat another time. I was trying not to get myself too excited by this new woman. This was some random chatroom, speaking to someone online, just once…so odds were certainly not in my favor of anything real coming from this. But still, I couldn’t help but checking the app repeatedly seeing if I had gotten a message from her, which finally came.

Over the next few months we spoke quite often. Some chats just about what’s going on in our lives, others more sexually playful. Eventually we got to the point of skyping. Finally seeing for certain this woman I’ve been chatting with was who she said she was, seeing her live…it was amazing. Even after having spoken for months, I really didn’t want to do anything to screw things up. My heart was racing like crazy and I didn’t really know what to say, what to do. Fortunately, those maternal instincts seem to kick in and she was really awesome, helping me settle down some. Before long even skyping got to become pretty playful. Seeing her in her own bed, undressing for me. Finally being able to see her beautiful, thick, naked body for the first time. Allowing her to see just how excited she makes me. Playing together, seeing what I had been fantasizing about for so long, her on her bed, legs spread, toes curling as she would cum watching me stroke myself. Watching her bring her lips close to her cam as she told me in such amazing detail how she’d make me cum in her mouth. It all seemed too good to be true.

Through all this, we would frequently talk about the hypothetical of meeting. She lived about 8 hours away, so it wasn’t anything that was terrible convenient, but it was possible. It’s something she’d ever done (being with anyone else since dating her husband), but it was fun for us both to talk about. I think in part that was because it just seemed so unlikely, she was married with kids (who had moved out) and never traveled alone. For me it was difficult to find the time to get time away from work. But the more we spoke about it, the more there was this sense that it was meant to happen.

After about 7 months of chatting, the opportunity finally arose! She would be visiting my area with a friend. Certainly not ideal, but she was sure we could make it happen. Holy shit, was this really going to happen? Did I just like the fantasy of it or was this something I was really ready to make a reality? Then she tells me the weekend they are coming out….FUCK, I’m out of town for two weeks including that weekend. I was actually really pissed. All this time, finally the opportunity comes around and…I’m not around. I told Rachel, who was also a bit upset. I think she finally convinced herself this was something she DID want, and it was all for nothing. To her credit, she was actually the one that calmed us both down, putting some perspective around this. The fact that we were BOTH this upset, well that should speak volumes to what this means to us. She was right, no longer was this just a fun fantasy, this was something I wanted…badly.

Over the next few months, things kinda continued as they had before. The only difference was some bitching about a missed opportunity, and how serious things had become. We both kept looking for chances to make something happen. Finally she found an opportunity. In my area was a 2 day convention related to an interest of hers. She didn’t have a full time job but did a lot of volunteer work. The convention that was being held was in the same area of work that she was involved in volunteering. Seemed like a stretch, and she didn’t consider it a done deal by any stretch, but she started floating the idea past her husband. Eventually, I got the message, she had her flight and hotel booked for the trip!!

I really felt the introduction to us meeting was worth telling, since for me this was much much more than some random hookup. I didn’t, however, expect to write so much about it. Personally I do terrible presented with an extremely long story to read, so figured I’d end things here. After reading others stories here I wanted to post an experience of mine since it’s something that really still excites me to think about. What I’ve posted so far I think has accomplished that for me. If others would like to hear the continuation, than I’d be more than happy to share. If not thanks for letting me share this much.

Source: reddit.com/r/gonewildstories/comments/4ebsdp/finally_getting_to_meet_my_online_milf_precursor