Part 1
So I just have to tell someone about this; it's been happening for a while, and I've been very private about it in my personal life for obvious reasons. So, I'm going to use this as a confession and advice post because it's been bubbling in my chest for quite some time.
For reference, he's 21 and I'm 38. Due to the closeness of our ages, we've always been a very close mom/son duo for his whole life. We live alone with one another and do almost everything together where we can. Clearly, he's a bit older now, so he has his own things going on, but even with all that, we still spend a lot of time together, mostly because we like each other's company. A few months ago (when the weather was warmer), we were going to a pool party with some of my friends, and I was trying on bikinis when he walked into my room. Before this, I had noticed him sneaking glances at me but assumed it was just normal hormonal kind of stuff, so I brushed it aside. He sat on the bed with me just talking about the party, but his glances were closer to stares at my body while we spoke, specifically at my more 'alluring' areas (hips, breasts, etc.). He asked if I'd chosen a bikini yet, and after I shook my head, he said something along the lines of, 'Can I help you choose?'
I couldn't tell you exactly what came over me, but his looks definitely made me think he liked my body, so I decided I'd play along. I nodded to his ask and told him to look away while I was getting changed. He laughed, saying it wasn't anything he hadn't seen before (which was true, but I had not been naked around him in a very long time), so I kind of squinted at him in a flirty way and considered it till I thought, 'Fuck it, it's just him,' and took the bikini top off while covering my boobs to the best of my ability. I had to let them go to put the top on, so he saw them and my nipples, and when it came to the bottoms, I did turn around but looked to see him looking at my ass till I got another pair on. I tried 3 on until he said he liked one, and that was that. We went to the party and didn't discuss it at all.
The next week or thereabouts, he was talking about my figure more, getting bolder each time and always in a positive way. Nothing like 'you're so hot,' but more subtle, which did make me flirt back in the same way. He's quite attractive, so it came easy, but nothing that would trigger a 'talk,' so we just gave in to the casual flirting. I thought long and hard about whether I was doing the right thing that week, but we were both enjoying it, so I didn't think it would lead anywhere and probably fizzle out. That was until he started wearing less clothes around the house. Normally he was a shorts-and-shirt kind of guy, and I'd catch him in boxers when he was coming out of the shower or whatever, but he started wearing just boxers more consistently. I made some comments about it when he first started, but it wasn't negative, more an observation, and he said it was more comfortable. Who was I to tell him what was comfortable? Honestly, I really enjoyed getting my own looks at him, and as a bit of a 'bonus,' sometimes he'd clearly have an erection but make no moves to hide it from me. One night I said, 'You're going to take someone's eye out with that thing,' and pointed to it, but he said, 'If only,' which did make me pause, but nothing was said about it. It was a lot of fun really, that casual flirting.
This continued over the weeks until we both got really comfortable with him like that. He was walking around the house confidently, boner or not, and I got very accustomed to seeing it booming when he stepped. I was still wearing my normal at-home clothes, but his erections were definitely getting more frequent and noticeable while he looked at me. It had me very curious looking at it covered that much, and I started to wonder more and more what it'd look like because it was quite impressive, but I had no real way of finding out, so I just continued with the indirect flirting. All that flirting came to a head one morning when we went out to a brunch he had a birthday voucher for with some friends of his. He had a girlfriend he'd split with, so he invited me in place of her, and during the brunch he stroked his foot on my calf under the table. It was a bit of a shock, but I was cool, and when he was done, I took my heels off and did the same for him.
We got home, and after a shower, he started walking around in his boxers again, but his touch was still burning into my leg. When I saw him getting hard and he was adjusting, I was staring at it, and he saw me, so he grabbed it in his hand and shuffled it around a bit. I got a little closer to him and said, 'Looks bigger today than usual,' which I almost caught myself before I spoke, but it kinda slipped out. He asked me if I wanted to, and something took over, so I nodded at him, not looking away from his boxers. He fumbled for a little, working himself up until he pulled them down and his cock came bouncing out while I covered my mouth with my hand and had this rush of heat and needles going down my body from my head.
I got even closer to him while still looking, and despite a part of my brain protesting, I asked him if I could touch it. He said I could, so I grabbed it with both hands. I was honestly thinking I could just touch it and go back to life as normal, but once it was in my hands, it was hard to not continue. I started stroking it and telling him how big it was, and that made him talk about my body, and he brought up the bikini afternoon, saying how hot he thought I was, especially seeing my ass and boobs. It's a bit of a blur because I couldn't really believe it was happening, but when he talked about me like that, I stroked him faster, and it felt like he got even harder. He asked if I liked seeing his cock, and I nodded, and despite that part of my brain fighting the urge, I whispered in his ear asking if I could suck it. He agreed, so I got on my knees in front of him and sucked him off right then and there. At one point he asked if I could take my top off, so I did before going back to sucking, and I pulled him out so he came on my chest.
The level of guilt was immense. I stood up, and clarity hit as I wiped myself off, but it was quite awkward the rest of the day as the adrenaline wore off. I apologized to him, and so did he, so we agreed it'd just be a one-time thing, and life went back to 'normal' for a while. A few more weeks went by, and the awkwardness and guilt remained high for a while but leveled as time passed, and my brain started framing it in a more positive light. It had happened; we couldn't change that, and he was still the person I loved more than anything in the world, which helped push that guilt aside, but I also had to live with the fact that despite all the feelings I was having, I still really, really enjoyed it while I was doing it, so it was a wrestling match inside me. It just filled my mouth so good, and I don't know, I'll start rambling if I continue.
One night a little later on, he came out of the shower in just boxers again, which was a change since after the first time he'd gone back to shorts for those weeks. By this time I was much more level-headed feelings-wise, so I was happy to see him like that again, and I made some flirty comments like, 'There he is,' when I saw him. The erection followed, and he saw me looking, so he said being in underwear was very comfortable and said he'd be okay if I was just wearing underwear too. It was obviously very hard for him to say that because he said it so unnaturally, so I knew he was nervous, but I woke up when he said that. I considered it for a little while and just flat out said, 'Do you want another blowjob?'. He agreed, but we talked about what happened last time, and we admitted to each other that it'd been on our minds constantly, and it was enjoyable despite the negative feelings. I brought him over to the couch and pulled his boxers off but also took my top and bra off so he could see my boobs again. Rather than kneeling in front of him, I lay across him and had my head on his stomach, and sucked him off that way. Halfway through I thought, 'Where's he gonna come?' but when he was nearly there, I took my mouth off and sat up to jerk him off onto himself. We wiped off, and interestingly there wasn't that same level of guilt afterwards.
A few days later the same thing happened; a few days after it happened again, but he asked to grab my boobs while I sucked, which I agreed to, and suddenly it became a daily thing. We'd get home from work, and through the night we'd lay on the couch watching TV, and I sucked him off till he came. It got easier to fit him in my mouth the more we did it, and I learned what he liked about it after I started asking him what felt the best. A few days into this, he asked if I wanted some help too, but I said, 'Maybe soon,' because I wasn't ready to take that step just yet. It's been a really nice and new way of showing my love for him and almost therapeutic in a weird way. A few days into this, I started taking my bottoms off at his request before we got started too, so he got to see my full naked body before we started. The first night I took my pants off, I did it while facing him so he got a look at my pussy, and when I lay down, he put a hand on my ass and squeezed it while I sucked, telling me how hot I was so that kept up. I've not been clothed while doing it since. After a week or so, I got a little sick of having to get stuff to wipe him down and told him to come in my mouth, which he did, holding my head over his cock, and I'd swallow the load. I even started wearing my hair up right after the shower because I knew what was coming, and he'd hold onto that to guide me up and down his cock.
Obviously, ly my head is a bit scrambled by the fact that we're doing this, but I love him so much and am really enjoying doing this for both our benefits. His cause he gets to come, and mine cause I love doing this for him. I know this can't last forever, so I'm trying to make the most of it while it's happening he's been asking to help me more and more, but I keep saying 'no' because I haven't been ready for it. Usually, I'll be horny while doing it but take care of myself on my bed afterward. A night ago I felt especially horny while doing it, and because I'm more accustomed to his cock by now, I know what makes him groan, and I couldn't keep my fingers away from myself. I got onto my back, still with his cock near enough my mouth to lick, and started masturbating in front of him. He talked to me while I was talking again about how hot it was, and I came before getting onto my knees to finish him off. He asked to come on my boobs, so I jerked him off till he did, and we talked about it. He thought it was really hot, and I couldn't deny him that; it was, and I was so worked up. He asked if he could help me out tomorrow, and in the moment I said yes, but this seems to be leading to an inevitable conclusion. Like I'm still grappling with a bit of guilt, etc., and a blowjob is just a blowjob, but it's way more intimate with him than anyone else I've ever given one to.
Tonight, we took that next step, and when I got onto my back, he reached down with his hands and rubbed my pussy. I tried to come with just his help, but I was in my own head a bit much, so I finished myself off while he grabbed my boobs. He really, really liked it, and I'll say I did too, like a lot, but I guess my question is, will continuing this just wreck our relationship entirely? I can see both negative and positive sides to what we're doing, and it's hard to reconcile because once we keep this moving, obviously we can stop, but it'll be hard because we're both having fun with it.
Thanks for reading. I know that was a book, but I needed it off my chest.
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