When I was sixteen, my mother had finally had enough. She threw my drunken, non-working father out. Oh, he thought he was so cute with his English accent, and tall, skinny good looks, but she had always been the one earning the money. She’s the one that developed that sewing app, so we had plenty of money.
My mother is fun-loving, but direct, and perhaps a bit eccentric. She was always easy to talk with, although sometimes what she said could be shocking.
Like, a year after Dad left, she told me, “I just kept him around for the sex.”
When I turned eighteen, my mother went kind of crazy. I mean nutty even by her standards. What am I talking about?
She suggested we masturbate together. I was embarrassed by the request. Oh, sure I jerked off all the time, but always in the privacy of my room. She never caught me or anything like that. I don’t think she’d seen me naked since I learned to take my own baths around age five.
Recovering from the shock of that request, I teased her a bit. “Oh, you just want to do that because you’re not having sex with Dad anymore.”
“True, and I haven’t been dating. I hate to say it, but none of the guys I’ve come across even measure up to your father’s low standards.”
“That’s pretty bad,” I answered laughingly.
In a way, I was kind of surprised. My mom gave birth to me when she was only 17 years old. She’s skinny and very pretty. She could be mistaken for my sister. Really. It’s happened. I’ve seen guys flirt with her. But she’s just not interested. I think her experience with Dad kind of turned her off to men. She probably thinks of all men as useless worms, only good for putting penises into women, and she deserves something more.
Like a bulldog with a rubber bone, she wouldn’t let go of the idea of masturbating together with her son. She brought it up several times over the next couple of weeks. Finally, in a surprisingly horny mood after hanging out innocently and frustratingly with a girl from college, I relented.
We got off to a hesitant start. I expected her to have a plan. To take the lead. Finally, it was decided that we’d play strip poker. We rummaged around the house for a deck of cards, and came up empty. So, we decided to flip a coin. Heads, I would take something off. Tails, she had to remove an item.
We were neck and neck as our shoes and socks came off. Then I lost my shirt. She complimented me on my skinny but strong chest and abs. Then she lost her shirt, but she had a bra on, so I didn’t get to see much. Oddly, I was looking forward to seeing my own mother’s tits. Weird, eh?
Now here’s where I got kind of embarrassed. Actually, really embarrassed. You see, in rapid succession, I lost my shorts, then my underpants. I was feeling all sorts of emotions. I did want to see my own mother naked. It was more of a curiosity than a horny thing – I think. But, I didn’t want her to see me. I mean, I was already half-erect. How could I possibly let her see me with an erection? That would be like admitting I find her attractive, and that I was enjoying her little game and looking forward to what was to cum, er… come. Well, it was just too weird, right?
I mean, how fucking bizarre! Playing strip poker with my mother? While the whole process took only a minute to think over, I kept turning it around in my little pea-brain. It was her idea after all. This is what she wanted. That was enough to sway me to hook my thumbs in my underpants and pull them down and off. I was more erect than I had realized. My penis was sticking straight up. Oh, it’s nothing special. Not eight inches or anything like that. But a good solid six inches I guess.
So there I was totally naked, and what did my mother do? She immediately stepped out of the remaining bra and panties she had on. There was my own mother, actually quite good-looking. She’s not nearly as tall as me, skinny but not too thin, with good firm tits, and a trimmed hairy patch in her crotch region. I found her attractive but not like fuckable or anything.
Then, she turned around, and I saw her firm butt. I mean, that woman’s butt, my own mother’s butt, was as firm as any 18-year-old girl. Firmer than most, actually.
That sent me. I mean, it totally fucking sent me. I loved seeing my mother’s ass, and my penis became harder. So much so that the glans was glistening like a mirror, something that seldom happens with me. My embarrassment evaporated immediately. Suddenly, I was proud for her to see me with my rock-hard erection. I couldn’t help but touch my penis a little bit. I wasn’t wanking, but it was like a reflexive grab and hold, maybe even with a little, slow, short stroking up and down. Right there with Mom watching!
Meanwhile, my crazy mother started holding and shaking her tits. She walked right up to me, and pressed those magnificent breasts right into my face, rubbing them on my cheeks.
I ejaculated. I didn’t mean to. It just happened. She noticed. She expressed momentary disappointment, then started laughing. It was contagious, and I started laughing also.
Now, I’m a good son. I couldn’t leave her standing there unorgasmed. After I calmed down a bit, I gestured for her to lay down on the sofa. I kind of hesitantly reached in and touched the hair over her vagina very gently.
She went “Oooh,” in a very appreciative way, letting me know there was no doubt I was on the right track.
I’m not super-experienced with women. In fact, I’ve only been to bed with two women. Girls, actually, that I knew from school. In both cases, it happened only once. With both girls, we did it in near total darkness. We were nervous, and ended up being about as straight-laced as one could get. In other words, we hugged and kissed for a while. Then I put on a condom, and pressed awkwardly into their vaginas.
The first girl was wet in that region already, so it was easy to get into her. I came right away. She guided me to licking her clit, which gave her an orgasm.
With the second girl, she wasn’t self-lubricating. I tried and tried to get it in her. We were both incredibly inept, until she suggested that we use some oil or something. We found some hand cream in her bathroom, and with that, I was finally able to slide in. I might have lasted 30 seconds at most. It was just enough time to discover how glorious it feels to be kissing and hugging all up tight with a woman and have my penis buried deep in her vagina. Heaven, really! Bang, I came. Big surprise, eh? I was all set to lick her clit also, but somehow she didn’t want anything more. We dressed, and she went home shortly thereafter. With both girls, I initially thought we’d get closer. I wanted to really get to know them, to go on dates, to hug and kiss, but in both cases, it was one time sex only.
So, there I was kind of sorting my fingers through my mother’s crotch hair. I guess I was looking for her clit. She gently grabbed my head and placed it where I could find her clit with my tongue instead. After fighting my way through the curly hairs for a minute, I dialed in on my objective. I tasted her girl cum. Or should I say mother cum? You know, the liquid that girls get. It was nice, not yukky like you might think it would be with one’s own mother. I was in wonder that I came out of that very slot right below her clit. This was the first woman I was with who had had a baby. I thought the slot would have been enlarged, but no, it was just regular. I couldn’t resist, I pressed my tongue as deep into the slot from which I came as I could, and she came. I mean, as I was probing into her tunnel, she started shaking, and kind of moaning, and I knew she was being hit with a big orgasm.
It took her a long while to calm down while I held Mom in my arms. The next thing I noticed is that daylight was streaming in through the curtains. I was spooned up behind my mother. As I was awakening, I felt a mix of emotions. I was calm, joyous, and happy, but also a little freaked out.
After coffee that morning she and I talked about what had happened. First, she apologized, practically in tears. She was concerned that she had psychologically damaged me. I reminded her that I was 18 years old, had fucked twice in my life so far, and could come to my own conclusions. That seemed to calm her. I told her I did enjoy the experience very much, but it did weird me out.
At the end of the conversation we decided that we might do it again, and that we’ll never go any further. As much as she’d like to have me fuck her, she has decided that’s just too weird. I agree, and don’t feel a need to do that.
Update: We have played again, but it’s different than with my new girlfriend. With Cindy, it’s full-on fucking, loving, and a very nice thing. With Mom, we’ve kind of resolved to simply masturbate in each other’s presence. She’ll finger herself to a nice orgasm, and I’ll totally wank in front of her. We’ve done it while watching erotic movies on TV, and once on my 19th birthday, and one other time on her 36th birthday. One time, I was naked and wanking while sitting on a kitchen chair while my mother was making a pie crust from scratch. We talked, I wanked, and before long I was squirting cum into my hand. She had a twinkle in her eye as she watched me do that.
All in all, I know my relationship with Mom is unusual. Cindy knows about it and is fine with it. However, lately, Cindy has been hinting that she’d like some sort of masturbatory three-way with us. Mom and I are closer than ever. We aren’t hurting anyone, even ourselves. We know the limits. We’re also realistic. We realize that what we’ve been doing is good clean fun, but nothing more. I believe my mother would like to do something with Cindy, so I’m really looking forward to the three of us getting together.