Tales Of A Loving Son – Our First Time

By: Antony

Well, the first post. There’s really no better place to start than me and my mother’s first time together. I suppose I’ll stick in a bunch of background information so I can paint a picture of the situation. Here it goes.

My father left when I was 12, my parent’s marriage didn’t really end on any bad terms, it was a mutual separation, they just didn’t love each other. Really they stayed together for me, they wanted to bring me up, at least in my early childhood years, in a “normal” household. I respect and appreciate that. My mom got almost full custody of me (I saw my dad maybe once or twice a month, there was no set amount, that’s just how much it ended up being), not because my dad wasn’t a good guy, he was and still is. It was just he has a job where we might be called at 3am and have to go halfway across the country at a drop of a hat. That’s no way to raise a kid.

So, I lived with my mom. It was just her and I, they hadn’t had any other kids besides me. She took the divorce very well, mostly due to the fact that I think they had been planning it for years. Seeing her happy, made me happy, so we were both happy together. She dated almost immediately, but nothing seemed to stick longer than a few weeks, she just couldn’t find the right guy.

Back when I was a kid, my mother was my first crush, and she never left my head. I had always been so physically attracted to her. She was my first everything when it comes to exploring myself. She caused my first boner, I was thinking of her the first time I jerked off, and she was who I was thinking of the first time I ever made myself cum. My attraction never went away and I treated her amazingly, I didn’t wait on her hand and foot by any means, but I did as she asked me to do, without complaining. In the years after the divorce, her and I really did end up becoming best friends. We would take turns making each other dinner, we’d watch TV and movies together on the couch, we did all kinds of things together. Of course, behind her back it was something completely different, I stole her panties and bras, using them to help me masturbate. I even found some sexy pictures of her on her computer that my dad must have taken when they were still together, I copied them on a flash drive and put them on my computer, just adding them to my masturbatory aids.

Us being friends and her dating guys went on for a few years until I turned 15. It wasn’t long after my 15th birthday that I noticed that she had started to become depressed, she didn’t work as hard to dress up when she went out and even staying in, she would just wear sweats with no make up. I still thought she was gorgeous either way, but I could tell she wasn’t her usual self.

So one day I confronted her while we were eating dinner. I asked her what was wrong, she told me how she was feeling bad about herself, she hadn’t found a guy that would stick around for more than a couple weeks and she had no idea why. She was regretting waiting to get divorced, convinced that in waiting those years to do it, she had lost her looks, and any chance of being with a man for an extended period of time. I couldn’t tell her quick enough how beautiful she was, and that there’s no way she had lost any of her looks, that she was more gorgeous every day. Once I finished saying that, I know I blushed because I could feel how hot my cheeks got. I didn’t mean to seem so passionate about it, I thought it must have sounded creepy coming from her son. But she smiled sweetly and thanked me, telling me how much it meant to her, since I’m the one man in her life that will always be around. She leaned over and kissed my forehead before she cleaned up our dishes from the table. I could tell I had lifted her spirits as she almost immediately seemed like her old self. While she rinsed the dishes off, she turned back to me with a smile and asked me if I wanted to maybe do a movie night, which we hadn’t done in months. I eagerly nodded, excited to spend some time with her where she wasn’t down on herself. She told me to go get our favorite comedy and to put on my pajamas so we could be really comfy.

I went back to my room and got out of the clothes I had been in all day, putting on a tshirt and loose pajama pants. As I came out of my room, her and I passed each other in the hall, she told me she was going to get comfortable herself and asked me to get the movie ready for when she came back out. So, I went into the living room, popping the DVD in, switching the sound system to the DVD player, changing the TV to right channel, etc. For a few minutes the menu played through on the TV while I waited for her. Finally she came out of the hallway, wearing a knee-length satin night gown. I had never really seen her in anything like that before so it left me a little dumb struck. It was by no means slutty or revealing, but it was more revealing than I was used to seeing her wear. I know she noticed the look on my face because when I snapped out of it, she was blushing and smiling at me. I acted like I hadn’t been staring, but it was too late. She moved in really close to me, pushing her back into my chest, sitting between my legs as the movie began. I wrapped my arms around her and held her close as we watched, laughing at all of the normal places, saying the lines while the actors said them. It was a really fun night, and then the credits ran and I flipped it off, figuring we’d both be heading to bed as it was pretty late, but we ended up just sitting together and started talking. She asked me how school was going and how my grades were, the usual mom stuff. Then the conversation turned to girls and it went from there


“So is there any girls at your school that you think are cute, or whatever guys say these days?”, she said with a laugh.

I replied with a big smile, “No, not really, there’s not really any girls that interest me at my school”.

From the way I said it, she must have realized there was someone, but I was telling the truth she wasn’t at my school. “Oh yeah?, sounds like there’s someone. Who is she?”.

At this point my mind started racing, trying to think of a good lie, not wanting to reveal that it was her. If I came up with something good, maybe she’d drop it, the more guilty and secretive I sounded, the more she’d pry. I just couldn’t do it though, not under that pressure, not without a lie already decided in my head. So, I just shook my head and said, “It’s no one, really” sounding incredibly guilty of lying.

She turned her body so she was more facing me with a big smile on her face, nodding, “Ok, you don’t have to tell me. Why haven’t you asked her out?”

I shook my head again, looking away from her and told her, “It’s because I’m sure she would never even think about being with me, ever.”

Her voice was so sweet, trying to make me feel better, “Oh, honey, why would she say not be interested? You’re such a handsome, sweet boy. If I was a teenage girl, I’d go out with you in a heartbeat.”

That’s when I did what, at the time, I wish I hadn’t done. I looked quickly back to her and eagerly said, “You would?!”

She must have realized who I was thinking about then, but I could tell she didn’t fully believe it, so she dug a little deeper. “Honey, does this girl know how amazing you are? How passionately you feel about her?”

I shrugged a little, looking into her eyes, “I think she does, but I’m scared to death what she’d say if I admitted my feelings to her”

She smiled sweetly and said, “I’m sure she’s very lonely and wouldn’t be against it, especially now that she knows how you feel about her”

I blushed and managed a nervous smile, looking into her eyes, I knew we were both on the same page now, so I leaned in, hesitantly, and gently kissed her lips, before pulling mine away to see her reaction.

She opened her eyes that she had closed for our kiss, looking into my eyes before leaning back in, kissing me this time. Of course, I kissed her back and it turned less away from a gentle mother-son kiss. I felt her hands rubbing my chest and I felt her tongue slide into my mouth, my tongue responded and massaged hers.

After a few minutes of making out, she took my hands in hers, leading them up to her chest, cupping each of her D-cup breasts. I breathed out into her mouth as I felt them for the first time, taking advantage of it, squeezing and kneading them in my fingers. Another minute or two passed and she ran her hand down my body and grabbed my crotch, finding my cock through my pants, beginning to stroke it through the thick fabric.

It wasn’t long before I had full confidence in what I was doing, taking more control of her. I pulled her nightgown up, revealing her naked body. I began kiss down her chest, between her big tits. That’s when she pulled my shirt off and then pulled down my pants.

My cock now completely hard, she held it in her one hand, smiling wide at me, “Oh wow, my little boy isn’t so little anymore is he?” She kissed my lips one more time before leaning down, wrapping her lips around my cock head. She gently sucked on the head before pushing it deeper in her mouth, bobbing her head up and down. I just laid back and let her, never having a blow job before I didn’t know if she hadn’t lost a beat after getting divorced all those years ago, or if she was off her game and even a bad blow job felt this amazing.

After a few more minutes she took my cock out of her mouth and looked up at my from my lap, “Fuck baby, I need you inside me, I haven’t a cock inside me since your father, I need it so bad”

Looking back down at her, I nodded quickly and told her, “Yes, I want to make you feel good mom, I want to be deep inside you”

So she moved up to her knees, straddling my lap before lowering herself down, my cock entering her. With this being my first time ever, she told me to just let her do everything, and I wasn’t disappointed, enjoying every second of it. She felt so amazing going up and down my cock, her pussy feeling like nothing I had ever felt before around my cock, like I could have never imagined. I loved the feeling of her body slamming down into my lap, driving every inch of my cock up into the womb that bore me. The house seemed so quiet, except for us, our moans, the couch creaking under us, our bodies slapping together.

I felt the pressure beginning to build and I moaned out that I was going to cum, she shook her head, “No baby, just a little longer, I’m so close, hold on if you can.”

So I did, I had practiced holding my orgasm when I jerked off, but I wasn’t sure how well I’d be able to do it now that I was with what was literally my fantasy girl. I managed to and I felt her already tight pussy clench down around my cock, she threw her head back and began screaming my name, “ohhhhhh, oh fuck yes, oh Chrisssss!”

Between struggling to hang on any longer, the feeling of her clamping down, and the sight of her bouncing up and down in my lap while screaming my name, I couldn’t do it anymore. I shoved my cock up inside her as deep as I could as I felt it erupt like it never had before, shooting harder, shooting more than ever. Not able to help it, I must have groaned just as loud as she was screaming as we came together.

She bounced up and down in my lap a few more times before we both slowed down, just holding each other. I have no idea how much time passed but I looked down and my mom’s forehead was against my chest and I heard her crying. I tilted her face up to mine and saw the tears in her eyes. I couldn’t ask her fast enough what was wrong, had I done something wrong, was it not good?

She forced a smile up at me through her tears, shaking her head and told me, “No, no, god no baby, it was amazing. But it shouldn’t have been amazing, what we just did was so wrong, but it was so great
I’ve never cum like I just came with you, not even with your father. I felt so right, but it shouldn’t have”

I smiled back, nodding, knowing what she meant. I wiped her tears away with my fingers and kissed her lips gently, whispering against them, “It did feel right, so right” kissing her again, “I love you so much mom”

She smiled even brighter, only a couple lingering tears, “I love you too baby, I always thought you’d be the only man I need in my life, and now that we’ve done that, I think I might have been right”. She took my cheeks in my hands and kissed me passionately before getting up off my cock, leading me up to her bedroom, where we slept, my arms around her.

From that night on, I never slept in my room again, her room was now our room, and we weren’t just mom and son anymore.