Caught by Mom....Multiple Times

I’ve been caught so many times, it’s almost a joke around our house. I’m the teenage son of a single mother. Dad lost his life a few years ago in a traffic accident. He left us well off, so money is not a problem.  The first time mom caught me was when I was about 15 years old. I had woken up with an almost painful hard-on. The typical morning wood that men and boys get. Usually I just get in the shower and after ten or fifteen minutes it goes away. Sometimes I would have to jack off in the shower to get rid of it. On this particular morning I had just gotten out of bed and had stripped off my pajamas and was getting ready to jump in the shower. My prick was standing straight up, almost touching my belly and was somewhat inflamed. The door opened unexpectedly and there was mom staring at my hard cock in shock. And maybe awe, since for a 15-year old I was quite well endowed. She stood transfixed for a few seconds and then mumbled an apology and shut the door.  I was red-faced and embarrassed but there was nothing to do but to take my shower, get dressed, and go down for breakfast. I felt some kind of explanation was necessary. I didn’t want her to think I had been jerking off. I started to apologize, and she broke in to tell me it wasn’t necessary and that she knew that men…and boys…woke up with erections. She went on to say that it was normal, and it was her fault for walking in without knocking.  The next time was a few months later. And this time I was actually jerking off. She was going shopping and told me she would be gone for at least two hours. For some reason…wait, do teen boys need a reason to be horny…I don’t think so. Anyway, for whatever reason I was horny as hell that day and when she told me she was taking off, I was looking forward to some serious ‘me time’ where I could jack off at leisure. By now I was an experienced masturbator and could edge for quite some time and produce a massive cumshot. I stripped off all my clothes, slipped a porno tape into the VCR hooked up to the living room big screen TV, laid down on the couch and started stroking my cock. My plan was to make it last for at least an hour. I figured I had plenty of time to jack off, cum, clean up my mess, and get dressed before she got back.  I was watching a tape titled “1,001 Cum Shots” that was super hot. I had to edge carefully because at 15 years of age, it didn’t take much to cum. I took my time and lovingly caressed and stroked my dick for a good 45 to 50 minutes. I realized that I wasn’t going to make my hour target and would have to go ahead and let it fly. I grabbed my nuts in my left hand and furiously pumped my big hard cock with the other. I felt that glorious feeling starting to build and just as the first powerful stream of jism shot out of my cock, the front door opened and there was mom. No way could I stop. I just kept pumping and stream after stream forcefully erupted from my beet red penis, arcing up and splashing back down on my chest and belly. Probably the biggest cumshot of my life to that point. And my poor mother had to see it.  Mom stood transfixed in the doorway. A look of pure shock on her face. But she couldn’t stop watching and I couldn’t stop jacking. Even after the last spurt of semen dripped out of my prick, it just felt so damn good that I kept right on jerking. I slowed my pumping actions to more of a milking activity forcing some more drops of cum to drip out. Mom stepped into the room closing the door behind her. I just lay there, not even making at attempt to cover up. Not that I had anything to cover up with. I had left a box of Kleenex on the floor next to the sofa and I did grab a few tissues and started mopping up the jism splattered all over me.  You would think that being caught by my mother that my hard-on would immediately deflate. No such luck. I think I was actually turned on by her seeing me ejaculate. And my prick stayed rock hard in its reddened state. After I got myself cleaned up, she told me to go take a shower, get dressed and then come for a talk. Oh shit. A talk.  So, I did. The “talk” turned out OK. Very good in fact. She told me that she realized that masturbation was a normal activity for all men and especially teens. I shouldn’t be concerned about it. She said she didn’t mind seeing me do it, and in fact, got a certain amount of enjoyment out of it. She went on to say that since my dad was gone, she really hadn’t had any sexual stimulation of any kind and seeing me spurt out my load of semen was very gratifying for her. And in the future, if I felt like masturbating in front of her, it was ok as long as it remained between us. She went on to say that other people might not be quite so tolerant of a mother watching her son jack off.  Since she was being so open and accepting, I decided to push my luck. I asked her how she would feel about jacking me off? It didn’t shock her as much as I expected. Her diplomatic answer was that we should not make any decisions that either of us would regret. At least not right now. I interpreted that to mean she was open to the idea under the right circumstances.  So, for the next week or so I would mostly laze around the house in nothing but a t-shirt, and if I felt like jerking off, I would. Sometimes mom would watch and other times she would just go about her business. One evening I came to the dinner table in just my t-shirt. It was long enough that it covered my pubic hair but a good two inches of flaccid cock, along with my balls, hung down fully exposed. My mom commented about how nice my dick looked peeking out of the bottom of my shirt. That’s all it took for me to get hard and start jerking off. I was hoping mom would make a move to help me since she had just complimented my cock, but she just watched with a smile on her face as I shot a nice load up over my t-shirt.  A couple of days went by and I came down for breakfast wearing my favorite t-shirt with a serious case of morning wood. I hadn’t taken my shower yet and wanted to get maximum mileage out of my hard-on. Mom didn’t appear to be surprised at all. She didn’t even comment. At least not right away. I moved to help her put some of the food on the table and in our small kitchen it was impossible not to brush against her. I made sure my hard cock bumped against her hip.  But mom just ignored me, and I decided not to push it. In fact, the next day she very clearly laid out guidelines for me. If I wanted to laze around the house in just a t-shirt and socks with my penis exposed, that was ok. If I got the urge to jack off, that was ok too. Just make sure that no cum got splashed on the carpet or the furniture. However, she asked me to limit it to once a day. If I wanted to do more, please do it in the privacy of my own room. She also made it clear that she would not be helping me out in any way. So for the next few years, that’s the way things went. At first, I was jacking my cock in her presence every single day but as time went on, the novelty wore off. I still would masturbate any time I felt like it, but it wasn’t always when she was there watching.  But everything changed a few years later on the day I turned 18. Again, I thought she was out for the day and while I was in the kitchen getting a Coke out of the fridge, I got a sudden urge to beat my meat. I popped the Coke open, took a swig and set the can on the kitchen counter. I unzipped my pants, pulled my pants and underwear down to my knees, and grabbed my already rock-hard cock. By the age of 18 I was now sporting a thick 8-incher that was primed for action. I hadn’t jacked off in several days…unusual for me…so I knew a healthy cumshot was in the works. I stayed right in the kitchen because it had a tile floor and I could spurt my semen all over the floor for easy clean-up. I started stroking my prick when the door from the garage into the kitchen opened up and there was good ol’ mom. When she saw what I was doing, she got a sly grin on her face and stepped right up to me.  I was totally blown away by what happened next. She wrapped her hand around my cock, squeezed it, and gave it a few strokes. “Looks like you could use a bit of help there, Jack,” she purred. She moved around behind me and did the classic wraparound. Her left hand circled around my waist and gripped me tightly. Her right hand held onto my distended cock and pumped away. Soon her left hand found its way down to my balls. She gripped my nuts and stroked my cock like a pro. In no time I was ejaculating stream after stream of hot cum all over the kitchen floor.  Mom plucked a few tissues from a box of Kleenex on the counter. “Here, let me help,” she said. At first, she wiped up the cum off her hand but after that she actually took hold of my penis between two fingers and began to wipe off the cum residue from the head of my cock. I have to tell you, my poor heart was beating so hard I thought it was going to pop out of my chest. And this next part literally blew me away. She milked the upper shaft of my cock right below the head in order to get the last drips of cum out. Damn! I thought I was going to cum again. I almost told her not to stop. God, that felt good. One of the best feelings of my life. Some remaining sensations from my orgasm were still shuddering through my body and her masturbating fingers just heightened those sensations.  This was beginning of a near endless stream of jack-off sessions with my mom. I quickly learned that any time I showed up in the house with a hard on, there was no way she could resist masturbating me to orgasm. I guess she had been saving it up for the past three years until I was of legal age. Being a teen, this meant I was getting a mom handjob every day, and many days more than once. She seemed perfectly happy to jack me off as many times as I wanted. One day she actually jacked me off five different times over the course of the day. And at one point when I was laying on the couch and she was between my legs masturbating my hard penis, with her other hand fondling my balls, she pulled her hand away from my nuts, sucked her middle finger to get it good and wet, and shoved it up my ass. Omigod, I thought I had died and gone to heaven. She jacked my dick and pumped her finger in and out of my ass and just as I started to cum, she swiftly pulled her finger out which heightened my orgasm. Jet after jet of hot semen spurted from my prick. It went everywhere as I writhed around in the throes of orgasm, totally out of control.  As one would expect, at some point, her jacking me off led to her sliding her lips down over my prick and sucking me off. Even though I was 18, nobody had ever sucked my cock before, so I was in heaven. But she limited the cock sucking to special occasions. After having orgasmed down her throat multiple times, I was ready for some serious fucking. But mom drew the line at masturbation and oral sex. She was adamant that actual intercourse crossed some line that she had created in her mind. I pleaded and begged but to no avail. I even told her that because she had given me multiple orgasms that it was only right for me to return the favor. Either with my cock or my tongue buried in her cunt. But she wasn’t having it. She said that sucking me off and feeling my cum spurt down her throat caused an involuntary orgasm on her part, even with no actual contact with her clit. On later blowjob sessions she would strip down to her panties and finger herself to help along or maybe intensify her orgasms. I begged her to at least let me see her pussy but no dice. But despite some minor disappointment, she was such an expert in bringing me to orgasm that I really had no complaint.  But all good things have to end. After another year of constant handjobs and blowjobs, she met a guy and fell in love and at that point the sex between us had to end. I was disappointed, of course but I understood and shortly after that I hooked up with one of my classmates who was a real hottie and loved to give handjobs and blowjobs. So, my sexual life continued right along with no interruption. Plus she even let me fuck her.