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I know the title leaves little to the imagination but my son and I played a round of truth or dare yesterday that may have escalated a bit.
We were sitting around wathcing TV so that was nothing out of the ordinary but it seemed like something was bothering him so I thought I'd ask what's wrong. At first he was a little reluctant to give me an answer but eventually told me that he broke up with his girlfriend and was feeling pretty down. I tried cheering him up a bit that he'd find someone better, you know the standard stuff but was also curious on why they ended their relationship. We never ahd an issue with being open to each other so I just asked what happened and he danced around the topic a bit until he eventually said that she thought that the sex was kind of lackluster which was apparently embarassing to him.
I tried to make it as casual as possible and said that it's nothing to break up over and mentioned that his dad was the same yet I still stayed with him. This at least got a chuckle out of him but curiousity made me ask for specifics and suggested that he could ask anything embarassing in return. He asked if it was a truth or dare type of thing and i said I'd be cool with that. He then answered the question saying that he is more the sensual type but his former girlfriend was rather into wild stuff apparently and asked me for truth or dare.
I picked truth and he asked what I'd prefer and I said that for his dad and I it was the other way around which seemed to suprise him. The questions got slightly more explicit each round ranging from preferences to weird stuff each of us have done and you could really feel he tension growing. I was the first one picking dare and he said that he earlier metioned that he is rather fond of big boobs so if it was okay with me, he'd dare me to flash him. I'm not particularly prude so being nude around others like in a sauna is totally okay with me and I would never back down from a dare so I casually lifted my shirt. I didn't wear a bra so they popped right out and my son looked like a deer in the headlights. After a few seconds of silence I pulled my shirt down again and my sons head was bright red and but tried to remain calm and said that they'd look great. I thanked him for the compliment and said that if he went to the sauna with me, he would have seen them sooner if he wanted that.
He then said that he'd be curious but always stayed away from saunas because he tought he was too small if I knew what he meant. I got it and said that he'd probably exaggerate and joked about having an idea in case he picked dare next. He did and I obviously asked if I could see his dick so he got up and pulled his pants down and exposed his already hard cock. I gave him my honest opinion that it was completely adequate so not small but also not overly large either which is imo the perfect size. I told him that his girlfriend would definitely miss out and that it would look pretty nice. He said that he was always curious on what other women would think and I said that I'd have no problem to be the judge of it.
It was gtting rather late and I didn't want to do anything anyone of us would regret later so I said that we should probably call it quits for today and that he should get himself and his "friend" to his room as it would scream for attention. He agreed and thanked me for the opinion and not being weird about it. He pulled his pants back up and hugged me before leaving for his room where I'm sure he masturbated. I don't blame him as I did the same later just from the tension.
Uff. That was pretty hot, and also a pretty cool move on your side to build up his confindence snd self-esteem. Top-notch mom.
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