A Mother’s Direction

I like to think I’ve been a good single mother. For the past four years since my husband passed, I’ve been on my own raising my son Tyler, who will be turning 16 tomorrow. I have a good job that takes care of everything, my son makes all A’s and B’s, and participates in multiple sports. Overall, he’s a great kid and I am extremely proud of him. So with everything considered, I think I’ve done good in this single mom life. The only thing where I’ve been lacking on is the sexual side of his life. Been lacking in my life as well, but I don’t plan on trying to date again until he’s a couple of years older. But with Tyler, there’s a lot of fatherly talks in the sexual realm that I just haven’t worked up the courage to have with him. It’s very awkward for a son to talk to his mother about sex, and it’s quite awkward for a mother to do the same with her son. I’ve taught him about the science of it all, you know, how babies are made. I’m not 100% sure he understood what I was saying. The conversation didn’t even last five minutes as I was just trying to get in and get out. I also haven’t checked behind him any. Checking his internet history, looking under his mattress, stuff like that. I want him to have his privacy. And I guess a part of me hopes he can figure out all the sex stuff on his own. I honestly don’t even know if he masturbates yet or not. I know I should more and be much better than this, but we have a great relationship, and I’m afraid that I could jeopardize that by with how I deal with sex when it comes to him. Anyways, the story starts here, the day before his 16th birthday.

I stared at my ceiling and let out a sigh. I had woken up at 5:30 AM, and tried to go back to sleep, but to no avail. Now it was almost 7. It’s Friday, and I only work, Monday-Thursday, so I can stay in bed however long I want, but I got so frustrated from just lying in bed trying to go back to sleep. I had been craving a good, greasy fast food breakfast, so I decided to get up and get dressed, and go pick some up. I would most likely be back before Tyler even woke up. It’s summer vacation for him I don’t think he’s been up before 10 since school left out. I finally got up and took off my nightie. I stared in the mirror almost in disgust. “Ugh, where did that amazing body I had go to” I thought to myself. Even after Tyler was born, I kept up my looks very well. I had a trim tummy, decent 36 c tits, and a nice sized firm ass. But what the hell was I looking at in the mirror? I let out a sigh as I took one more look at my stomach that pushed over the top my panties, my breasts that now sagged and pointed to the ground, and an ass that been the receiver of all of my unhealthy eating habits. I threw on a new bra, t-shirt, and denim shorts, grabbed my keys, and headed off for food. About 25 minutes later, I was home again. I set the food on the kitchen table and went to Tyler’s room to wake him up. If I didn’t wake him up, he’d sleep till the afternoon. I got to his door and gave the customary knock. No response, so I opened his door only to get an unexpected sight. Tyler was still asleep, but his covers were thrown off his body and he slept on his back in just his underwear. And he had one strong case of morning wood. I stared at it for a few seconds, guesstimating it was around 4 inches, which I assumed was around average for his age. I then got upset at myself for thinking about the length of my son’s penis. Instead of creating an awkward moment, I walked out of his room and shut his door back. Then I yelled loudly “Tyler, wake up, I got breakfast!!!”

A few minutes later, Tyler came down to the kitchen and we both sat the table to enjoy our breakfast. Generally our meals together consist of me bringing up whatever topic of conversation, and we have a good talk. This time however I was struggling to get the image of my sons underwear tent out my head. I couldn’t believe myself. It’s my son for God’s sake. And I didn’t even see his penis, just the tent in his boxers. But somehow, I was still flustered, and kicking myself for thinking this way. My God I needed to get laid. If this is how my brains reacts just to seeing my 16 year old son’s covered erection, then apparently I have been neglecting certain needs I didn’t realize I had. I’ve had a very healthy masturbation life, with quite a chest full of toys that all get used often. But I guess I need to get out and get the real thing every once in a while. That’s exactly what I was taking away from this.

“Thanks for getting breakfast Mom” Tyler said breaking me out my own train of thought.

“Oh no problem sweetie. So what do you planned today?” I asked.

“Not much today. I figured cus we’re going out tomorrow with Brad and Casey, I would chill around the house today” Tyler said as threw he away his trash and cleaned off his spot at the table. “What are you up to today?”

“Sounds like a good plan. I think I might do the same. Driving you and your friends all over town tomorrow for your birthday is going to take a lot of energy, so I better rest up” I said half-jokingly.

We continued with some more small talk, discussed where we would eat, which movie we would go see, and got the schedule figured out for his birthday. After all that, he retreated to his room to play his xbox, while I cleaned up around the house some. It had been a couple of hours since I had last thought about what I saw this morning, but the image came back and hit me again. Didn’t take long and my nipples started getting hard again and I could feel my pussy getting damp. I let out a very frustrated “Ugh” before heading to my room to take care of myself. I decided that this wasn’t going to be a quick session, but at least an hour long masturbation marathon. I went into my closet and pulled out the large chest and took a nice long look at my myriad of options. I always give my nipples attention first, and I was in the mood for some light pain, so I grabbed the magnet balls. I took a pair and placed them on both sides of my right nipple and immediately gasped as I let go and felt the pressure of the magnets push against nipple, squeezing it, pushing it likes a pimple that needed to be popped. I gave it a flick, and winced from the pain. I took the next pair and placed them on my left nipple. I laid down for a minute and gently rubbed the tops of my nipples, enjoying the pain and the pleasure running through my body. Next up had to be my Wattenberg pinwheel. I laid back down and ran the wheel over my stomach first. Then to my thighs. At this point, my pussy was drenched and was aching to be taken care of. But not yet, the buildup is half the fun. As I ran the wheel, feeling the spikes dig into my very sensitive skin of my under breasts, the image of my sons erection entered back into my head.

“Damn it, do not think about your son while pleasuring yourself” I said to myself. I kept running the wheel along my tits, but I still couldn’t get the image out my head. “My god what is wrong with me” I sighed as laid out my arms in defeat. How in the hell could I do this while an image of my son is in my head? But fuck I needed release. I was in desperate need of getting.

“Fuck it, if he enters my head, he enters my head. Not like I’m actually doing anything wrong” I justified to myself

I returned to the wheel, running it along my tits, not touching my nipples yet. After a few minutes of teasing myself, I finally took the wheel and hit my left nipple with one of the spikes. The combination of the magnets still pushing against them and spike digging into the top almost made me yell out loud, the feeling was so intense. I repeated this multiple times before turning my attention to my inner thighs, running the wheel up and down, right outside my outer labia. By the time I put the wheel down, I was practically bucking my hips driving myself almost to the point of insanity. But I still wasn’t there yet. Before I give my pussy the attention it needs, I still needed to take care of one more area. I reached into my chest and pulled out one of my several butt plugs. Don’t want my stuffed ass to get all the attention of my brain, but I want more than just to feel poked. A solid black, medium size one will do just the trick. I grabbed the ass relax lube and covered the plug, then put a good dab of it on my finger and slowly inserted one finger into my schpincter. My late husband and I started having anal sex quite often after Tyler was born. Neither of us wanted any more kids, so we started experimenting with anal. I had hated it at first. It was uncomfortable and a little painful. But after a few times, the pain wasn’t there anymore, and I started to become comfortable with discomfort, if that makes any sense. After he passed, I tried a couple of my dildos, but they just weren’t doing the trick.