(Jessica)
As I approach him, I notice there’s enough room to lie down and rest my head on the pillow he’s using. “Do you mind if I lie down and put my head on that pillow?”
(Dylan)
Shit. I can’t say no or else she’ll know something is wrong. “Sure.”
(Jessica)
As I lie down on my right side to face the TV and put my head on the pillow, I notice a shift under the pillow. I hope I didn’t just crush his balls. “What are you watching?”
(Dylan)
I don’t know what the hell I’m watching. I put it on in a rush to not look suspicious. “Just flipping through different channels. Starting to get tired, actually.” I checked out her whole body from this position and was mesmerized by her shapely ass. It’s not too big, but certainly thick so that her shorts are struggling to win their battle of not tearing.
(Jessica)
“Oh. Are you going to bed soon?”
(Dylan)
“Probably.”
(Jessica)
“Do you mind if we talk for a minute?”
(Dylan)
“No problem. What’s up?”
(Jessica)
We talked for about 5 minutes. It was short, but nice to check in and make sure he was okay handling the idea of preparing for his future. I remember that point in my life and being nervous about my unknown future. So just to let him know I was there to help, I felt better.
(Dylan)
We talked for a few minutes about college, even though I didn’t have a lot of answers. Knowing that she wanted to be supportive was nice. But at the same time, the weight of her head on my dick has done my erection no favors. And I can smell her hair from where I am. It smells good, like fruit. My thoughts are pretty much on one track at this point and I don’t know how much more I can take without acting on them.
(Jessica)
“Do you mind squeezing the back of my neck a little? It’s really stiff from standing and presenting all day.” My neck is killing me, along with the area between my shoulder blades. Some pressure should help as long as he’s not in too much of a hurry to go to bed.
(Dylan)
Oh no. “Sure.” This has to be an evil joke on me. I lift her hair a little so I can get my hand around the back of her neck and start squeezing. Her skin is really soft and somewhat cool. She moans and pushes her shoulders back. At this angle, I can see the top and part of the side of her left breast since her loose shirt fell toward the side she’s lying on. This is the most of a breast I’ve ever seen in-person. It is awesome.
(Jessica)
This is feeling great and just what I needed. I accidentally let a moan of pleasure out and adjust my shoulders to feel the squeeze deeper in my upper back. I also notice I’ve gotten goosebumps as my son continues squeezing my neck. It feels so good, but is a little too strong at times. “Baby, not so hard all the time.”
(Dylan)
I take Mom’s request and lighten up a bit and start mixing squeezing with rubbing as I go higher up her neck and behind her left ear. She moans again and I’m getting hornier by the second. This feels like more than just a neck rub to me. It feels sensual. “Better?”
(Jessica)
“Mmm-hmmm.” It’s at this point that I start feeling flushed. I know I haven’t had sex or masturbated in a few weeks, but the thought of allowing my son’s touch to turn me on terrifies me. But still, with my sex drive being over-the-top lately and not having sex for nearly a month, my senses are overcome. I should have left right there, but I couldn’t pull myself away.
(Dylan)
I run my hand down her neck and around to the front of it. She lifts her chin to give me easy access and I lightly squeeze. Without ever doing this before, I had no idea a woman’s neck could invoke such a sexual desire inside myself. I’m feeling brave and overwhelmed with wanting to feel up my own mom that I slide my hand back up to her left shoulder. I find the top part of her breast that was exposed and started rubbing the area between that and her clavicle. My heart is pounding and I think for sure she’s going to stop me. But she doesn’t. She just closes her eyes and tilts her head back against my stomach.
(Jessica)
I’m pretty sure he’s trying to see how much he can get away with. That realization makes me ask myself how much I’m willing to let him get away with. After all, this is my son and anything past this point could make our relationship very awkward for the rest of our lives. I’m so conflicted with mixed emotions of horniness, responsibility, and confusion. I feel like a hormone-raging teen again. Would he actually want to do something more than this? A moment later, he answers my question.
(Dylan)
With my mom seemingly accepting of the exploration, I slide my hand down the inside of her shirt and brush against the exposed side of her tit. I decide to hold it firmly and start squeezing.
(Jessica)
“Shit.”
(Dylan)
She either likes it or is about to disown me. Right now, I don’t care if I’m disowned. This feels amazing and I want more.
(Jessica)
This feels amazing. Not only because I’m horny, but also because my son and I are saying so much to each other without having to speak a word. I can feel we both want this at this second, but we’re also hesitant. We both need another person’s touch, but aren’t sure the pleasure we’re experiencing is worth the price we’ll pay in the long-run. But God, I’m so horny. I can’t think straight. What does my son want to do to me?
(Dylan)
My mom turns her head to look up at me with her gorgeous green eyes. She looks conflicted and hesitant, like she’s trying to see my soul for answers, but also like she’s approving of more. She hasn’t told me to stop. She looks down and turns her head back away, closes her eyes, and inhales deeply. I decide to grab as much of her left breast as I can in my left hand. It’s bigger than I previously thought and quite a bit doesn’t fit. As I start to squeeze and massage it, she moans again and shifts so that she’s now on her back. Her eyes are still closed, but I see a slight smirk come across her face. She’s loving it, I can tell.
(Jessica)
I decide to enjoy the moment and let us both experience something we want. Our relationship will be different moving forward, I know that. I hope he knows that. I sit up for a moment, pull my shirt off, and lay back down looking at my son’s face wondering what he’s thinking. I see his eyes get huge like he’s never seen tits before. Has he not? Or is he reacting that way just because they’re his mother’s tits?
(Dylan)
Holy shit. Mom’s tits are beautiful. They got caught in her shirt as she pulled it up, then escaped and fell with heft. So big and soft with erect pink nipples and little bumps around the nipples. I think she’s turned on. I can’t believe I’m feeling up my mother’s tits. This is unreal. They’re so big that they fall slightly to the sides when she’s on her back. I decide to use both hands and push them together to create the best cleavage I’ve ever seen. “I’d love to put my dick in there.”
(Jessica)
“Oh yeah? You’d like to titty fuck your mother?” I can’t believe he just said that. It was very assertive and unlike him to be that forward about anything. I think I know which brain is thinking for him now. The question is, am I willing to go that far? Yes, I’m horny. But I’m also his mom. I need to decide right now when enough is enough instead of leading him on.
(Dylan)
I really do want to titty fuck my mother. She’s hot, I’m horny, and we’re already in this position with her shirt off. The way I see it is I’m going to at least get a titty fuck from her. If my mom and I start being sexual with each other, I’ll never move out. Please, don’t let this be a one-time thing. I then realize I never replied as she rolls back onto her side facing away from me.
(Jessica)
My question probably caught him off guard or made him realize what we’re actually doing right now and scared him away. That’s why he didn’t reply.
(Dylan)
I’m going for it. I pull the pillow out from under her head so that she’s now resting on my stomach with her face a few inches away from my pant-covered dick.
(Jessica)
“So THAT’S why you had the pillow there.” Shit. He plans to take his dick out.
And I plan to happily greet it. I’m all-in and can’t stop myself at this point. I know this is wrong, but fuck it. I want to see what my son will do to me if I let him loose. I’m letting him control the situation and keeping my head still. I can tell his dick is big, just not how big. I won’t lie, I’m getting very excited for what’s to come like I’m a young lover experiencing new passion for the first time again. I stay there breathing heavily from excitement onto his covered dick, waiting for his next move.
(Dylan)
I can feel my mom’s hot breath on my covered dickhead and it’s turning me on so much. Will she actually let this happen? As a virgin, I don’t really know what I’m doing and can only hope it’s not too obvious. I’m still nervous and don’t know how to handle possibly losing my virginity to my own mom. How would I explain that to people in the future who ask how I lost it? Like girlfriends or a wife. My leg starts shaking uncontrollably from anticipation. What the hell?
(Jessica)
I can tell he’s nervous. Poor kid’s leg is shaking a mile a minute. I need to lead him a little to make him comfortable. “Dylan, are you okay?”
(Dylan)
“Yeah, just nervous.”
(Jessica)
Did he and Lisa never have sex? “Sweetie, are you still a virgin?”
(Dylan)
Well, I guess it was obvious. Damn it. This is embarrassing. While scrambling for an answer and trying to figure out how to respond, enough silence passed to the point of the question being answered on its own. Not only am I telling my mom I’m still a virgin, but I’m also telling it to the topless woman in front of me who I’m hoping to eventually get completely naked. “Yeah…”
(Jessica)
This pushed my desire over the edge. Not only am I messing around with my son, but he’s also a virgin. This is a special moment and I intend on making it great for him. “Oh, Dylan. That’s good. Let Mommy take care of you.” With his pant-covered dick still inches away from my face, I scoot forward to start kissing it. I wrap my mouth around the panted shape and slowly pull my head back. The taboo and forbidden nature of what we’re doing has me so turned on. I can’t wait to unwrap his cock from those pants and see what I’m working with.
(Dylan)
When she called herself Mommy, my dick twitched a little. Just hearing her tell me to let Mommy take care of me made me want to rip her shorts off and start plowing her as hard as possible. Then when I felt her warm mouth on my pajama pants press against my dick, I had to restrain myself from pushing her head down. Jesus, I can’t believe this is happening.
(Jessica)
“Pull your dick out of your pants for me, sweetie.” There’s no mincing words or delaying anything anymore. I’m going for it now.
(Dylan)
God. Nobody else has seen my penis since this very woman telling me to take it out now took care of me when I was a child. What if it’s smaller than Dad’s or not big enough? What if she laughs? That’ll ruin me for life. Still, there’s no going back now and I so desperately want her to touch it. So I reach into the pant hole and pull it out. There it is, my erect cock inches from my mother’s face. I feel so exposed and vulnerable.
(Jessica)
Hell…yes. My boy has grown into quite a man and I can’t contain the big grin forming on my face. When he pulled it out, it bounced back about an inch after the head got caught on the edge of the pant hole. Here it is, my son’s hard cock standing straight up just inches from my face. I’m giddy to see how big it’s gotten since I last saw it all those years ago. And knowing it’s a virgin cock that belongs to me now is even sweeter. I just look at it for a minute, comparing it to Trevor’s since his is the only other one I’ve ever seen in-person. It’s about the same length as Trevor’s 7.5 incher, maybe an inch longer. But it’s MUCH wider than my husband’s. Knowing that Dylan isn’t done growing, my excitement level continues trending upward. If tonight isn’t a one-time occurrence, I might eventually have a fat 9″ pole all to myself in a year or so. His balls are still contained in his pants, but I’ll tend those later. All I can manage to say with my head still swirling with thoughts and different emotions is, “Beautiful.”