So it’s been a few months since New Years and I just wanted to update since lots of things have gone down. As I mentioned in my last update her FWB got her a set of buttplugs and she started to wear the small one around new years time. For context we have never done anal and I haven’t even been able to put a finger in as she brushes it away.
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So since January or so she’s been using the plug way more frequently than I could have expected. I mean even when the 2 of us would go to a movie date or bowling for example she would go to the bathroom first to put the plug in or even ask me sometimes. That’s as close as I got to putting my finger in her ass was via helping her push the plug in. They kept seeing each other and also kissing was gradually accepted in so that’s a thing now.
Sometime in February she switched to the medium plug and after some adjustment she would just casually be wearing it for events after work, or meeting my friends with it in her. And when we would go fuck after she would keep it on. I’ll have to say she definitely felt tighter with it on.
Then in March she graduated to the biggest butt plug size which was hard to get in and I had to help her a few times but over the course of the month she adjusted to it. Deep down in my heart I knew where this was going in the end but I just stayed on the ride.
April came along and it was my birthday and to my surprise she invited him as well. He had integrated into her friend group and kinda mine by this point so it didn’t stick out too much. Birthday went along fine but turns out even for that she wore the butt plug. A week after this point she came home and told me she had news for me.
She had gone over that weekend to see him while I was working overtime and as usual had her butt plug in. Well this time as he was fucking her from behind, he said it was time for anal to which she just nodded? And he took out the big buttplug and put on some lube and slid in. She said he was slow and careful but thanks to months of practice she was able to take him. I was just sitting there stunned as she causally just explained to me how she lost her anal virginity to him when I couldn’t even get a finger in. She said he fucked her ass in doggy for sometime before flipping her to missionary and continuing anal that way. It was just surreal to hear this.
Later that night I tried to initiate stuff and she just said not today as she was too sore but offered a handjob which I took. Felt kind of pathetic that I was just getting a handjob while she had just gotten ass fucked…
That was in April and since then.. they have been doing anal every other time it seems like. She’s gotten comfortable with it. I asked when I’ll get to try it as well and she just says we can discuss it later maybe Christmas time. There’s more that’s happened since April and now but I’ll post that another time…
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