Confession of a Chronic Masturbator

Confession of a chronic masturbator...pt.1

I'm a 34-year-old single mother with an 18-year-old son. Yes, I was a teen mother and never married. I raised my son at my parents' house until he was 8 and I was 24. I got a great job at 20 and was able to save enough to live on my own at that point. I haven't really dated much except for an occasional dinner here and there with some set ups by my friends. My actual sex life ended when I got pregnant. I have been ok with that because I masturbate on a regular basis, usually twice a day. There are a couple things about my masturbation habits that I need to share. First, I masturbate almost every day at work. I have a job in health care and my office is off limits to all other employees because of privacy matters. I often sit behind my desk, reach inside my pants and masturbate right there. But at least once a week I completely strip and masturbate sitting on the small settee I have in my office.

Those strip down days are actually my favorite. I have even called a client and masturbated while I talked to them on the phone.The reason I do that is because I need to feel that I'm not alone when I'm masturbating. When I'm playing with myself in my office, I know that there's people only 10 feet away outside my office, and that gives me much better orgasms. The other thing about my masturbation habits that may be unusual to most woman is that when I masturbate at home, I usually have my son watch me.

I know that may sound odd to a lot of people, but like the old saying goes, "don't knock it if you haven't tried it." It originally came about when my son caught me masturbating a while ago. I was in my room and minding my own business playing with my favorite dildo when I heard something. I looked up and saw my son Tommy staring at me in disbelief. I didn't know what to do so I tried to act as normal as possible. I quickly covered up and said, "Sorry Honey, but this is what us lonely woman do, but I'm sure you already know that anyway." He didn't say anything, he just gave me a small smile and went back to his room. I knew exactly what he was going to do, he was going to jerk off to what he just saw his mother doing, and that was kind of sexy to me.

I went right back to work with my mind thinking of how much he actually saw because knowing he was watching me was really turning me on. I suddenly felt an orgasm coming on and something happened that never happened before, I started to squirt all over the bed. The faster I pumped, the harder I was squirting. I pulled it out and to my surprise, I kept squirting. When I finally calmed down and caught my breath, I realized that I just had the most powerful orgasm of my life. I also realized it was so incredible because my son was just watching me masturbate a few minutes ago. I knew at that very moment, that was the only type of orgasm I was ever going to want again. I cleaned up, got dressed and went downstairs. Tommy came down about a half an hour later for dinner.

I said, "Do you want to talk about what happened before?"

He said, "of course I don't." I laughed and walked over to him.

I said, "look, I masturbate, and I know you just masturbated, it's really normal, everybody does it. I guarantee you don't know a single person that doesn't. Every woman, every man, and even older people do, so stop acting like it's a bad thing.

He said, "I don't think it's bad, but most guys don't see their mother doing it." I let him know he was probably right about that, but it's really not a big deal. I'm sure like a lot of teenage boys that I am the main character in his fantasies when he's jerking off. I decided that since we were actually talking about masturbation, I would push the envelope a little.

I said, "I want to tell you something that might help you with all of this, after you left my room, I finished what I was doing and for some reason it was the biggest orgasm of my life."

He said, "Really mom? you felt the need to share that with me?"

I said, "Oh stop it, you're an 18-year-old man and I thought you might like to hear that; besides it will give you something to wank about later." Then I laughed and so did he.

He smiled and said, "Well as long as you don't mind" and both laughed again.

I told him it was probably because I knew he saw me and for the rest of my play time, I was pretending he was watching me, then all of a sudden, Bam, The biggest orgasm of my life.

Tommy laughed and said, "Well I'm glad I could help."

I said, "Listen, I know we're mother and son, but since I was 16, you have been everything to me and I don't think there is a mother and son who is closer than us right, so why not be even closer if we can. I want you to be in there the next time I'm having one of my solo sessions." He looked at me but didn't say anything. I continued with, "I know that sounds crazy, but I think it will help you in the future and I know it will help me. Absolutely nobody but us will know about it, it's our secret to keep." I know he was loving the idea but didn't want to show it too much. I decided to give him an out, or at least some time to think about it, so I said, "Look, tomorrow I'm going to leave my door open, no more hiding so if you want to come in, feel free, ok?" He nodded his head, and I went back to preparing dinner without saying anything else.

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The next day I got home from work at about 5:30 and Tommy was there too. He goes to class 4 days a week, but on Friday's he only has class in the morning. I made dinner and while we were eating, I said, "I'm going up to my room in a little while and I just wanted to let you know that I'll be taking care of some things, or maybe I should say I'm going on a date with myself." He almost spit his food out and we both wound up laughing pretty hard at that. I think it was nerves that made us laugh, but in any case, I think we were both ready for tonight. I finished cleaning up the dishes and went up to my room. Tommy was in the living room watching T.V. and I decided to lure him in. I put on a really cute light blue panty and bra set then I covered it with a robe. I'm really tiny and petite. I'm 5'2" tall, I weigh 105 lbs., and I looked pretty damn hot if I do say so myself.

I went downstairs and walked into the living room. Tommys eyes went right to me so I said, "I just want you to know I'm going upstairs on my date, and I think I might need a chaperone, do you know any volunteers?" He just smiled so I turned away and went upstairs to my room. My room isn't that big, but at the foot of my bed I have a small vanity with a little stool that was going to be his seat for the show, assuming he came in. I didn't have to wait long; he was in the doorway about 30 seconds after I got there. I said, "Sit there, you'll have a front row seat." He sat down, and with both of us looking in each other's eyes, I dropped my robe to the floor. It was the first time my son saw me like this, and I think he liked it. I walked over to my nightstand and bent way down to open the bottom drawer. He had a perfect view of my tiny little ass, and I made sure that I took my time. I grabbed my favorite vibrator from the drawer and stood back up.

I could already see the bulge starting to form in his pants and it was making me very horny. I crawled on the bed with my ass once again facing him. I settled in sitting against the headboard facing him directly at the foot of my bed. Without saying a word I clicked on my vibrator, put it on my pussy and closed my legs tightly against my hand. He couldn't see much that way, but that's what I wanted, I wanted him to use his imagination for a little while. This vibrator has pleasured my pussy a thousand times, but it already felt different tonight, it felt better than usual. I let the vibrations flow through my pussy and without moving an inch, I could tell I was already getting wet.

I was staring right at Tommy as I was playing, and his eyes were firmly planted between my legs. I knew he wanted to see more, so I pulled my hand away, opened my legs a little and looked down. There was a sizable wet spot already forming and I said, "I'm never this wet this fast, it's because you're watching me?" I put my vibrator back on but this time I kept my knees up and apart. I pushed the button, and it went to high. I wasn't long before I felt an orgasm rising up inside my pussy. I didn't want a big one yet, so as soon as I started to cum, I took the vibrator off and just rode out a little one. Tommy's eyes were as wide as dinner plates and that bulge that was forming in his pants was now fully grown.

I took my hand away and saw that the small wet spot that I had on my panties was now at least three times the size. In all the years I have been masturbating, I've never been so wet so fast, it was definitely Tommys presence that was doing it. I looked at him and said, "How am I doing?"

Tommy used one word to answer, "Amazing."

I laughed and said, " I'm just getting started, can you please go in my bottom draw over there and hand me my date for tonight." He got up with his bulge leading the way, so I thought I would tease him a little, I said, "Wow! I guess you are enjoying the show so far." while I looked directly at his crotch.

He said, "Shut up." I smiled at him and watched as he went and opened the drawer. I keep looking at his face to see the expression when he opened it. I saw his eyebrows raise when he reached in and took out my date. It was a 10" pretty thick dildo that has been pleasuring me for at least the last 3 or 4 years. My pussy knew every inch of it and tonight, I was craving it. He held it up and said, "I didn't realize how big this was last night when I saw you, I can't believe it fits."

I said, "you couldn't tell because it was all the way in me when you were watching me, go sit down and I'll show you exactly how it fits." He went back to his bench and gave me his complete attention. I wanted to completely strip down for him, but I thought I would tease him a little more. I discreetly pulled my panties to the side making sure my hand was placed so he couldn't really see anything, and I gently pushed it in. I worked it slow just letting him watch, but all the while my hands were positioned where he really wasn't seeing too much just yet. I laid my head back and just tried to be in the moment realizing I was masturbating for my son. I gave myself another small orgasm, but I was saving myself for later. I pulled out my toy and patted my panties against my pussy to make them as wet as possible, and they were very wet.

I looked at my son and said, "These are really wet and their getting in the way, should I take them off?" he nodded his head, then I said, "This bra is no picknick either, I think they should both go, right?" Again, he nodded his head. I put my thumbs in my waistband and slowly slid them off. I made sure my legs were closed to keep the anticipation he was feeling alive. I threw them to the foot of the bed and as I unhooked my bra I said, "feel how wet those are." He picked them up as I exposed my small, but firm tits to him. I could tell he was torn between looking at my tits and playing with my wet panties. I thought I would help him out by saying, "You can keep those for later when you go back to your room and play, ok?"

He said, "Why do I have to go to my room to play?" I loved the idea of mutual masturbation with my son, but that would hopefully come later, so I said, " Sorry, this is my play time, but if you want to leave you can." He just smiled and slowly shook his head. I was now naked laying on my bed while my son was playing with my wet panties. I knew it was time so I looked at him, raised my knees and opened my legs as far as I could, I couldn't have spread them any further. I picked up my dildo, licked it a couple times and slowly made it disappear inside me.

I said, "now you can see how it fits, right?" He was in such a trance he didn't even answer me. I have always shaved my pussy, and I suddenly realized how good it must look to him. My lips were hugging it, and as I pushed it in and out, my lips held on tight. I said, "I need to cum, so enjoy." I went to work pumping faster and faster while using my free hand to play with my tits. I was really getting into it, and it wasn't just for his him, I was so fucking horny, and I needed to cum badly. I suddenly felt it coming on, so I just kept at it. I started to squirt a little and then the flood gates opened. I was splashing my wetness all over the bed, and I didn't give a shit, I just kept cuming for both of us. When I finally finished convulsing, I opened my eyes and saw my son with an absolutely stunned look on his face.

I caught my breath and said, "Holy shit! That was amazing."

Tommy said, "That was the hottest fucking thing I've ever seen."

I smiled picked up my dildo and while pointing it at him I said, "Hey, watch your mouth, I'm you mother." Then I laughed and fell back to the bed. I laid there naked letting Tommy get a good look at me. I wanted him to see me without being distracted. I turned over on my stomach and I said, "Nice ass too, right?"

Then he said the best thing ever, he said, "nice everything." I got on my hands and knees with my ass and pussy facing him and then got off the bed. I stood right in front of him and said, "I know your busting out of those pants, do you want to do it with me?" He said he did, so I said, " lay on the bed next to me and we'll play together." He got up and walked over to the bed. I said, "hold on, no clothes allowed in my bed, so either get naked with me or go to your room. But just so you know, I'll be here playing in my own bed, not in your room." That was all the motivation he needed. He slid his sweats down followed by his briefs.

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I was seeing my son's cock for the first time in about a dozen years, and it was absolutely perfect. After all this time, just time seeing a cock was great, but the fact it was my son's, and it looked perfect was all I needed to remember how much I missed the feeling of having one inside me. We both climbed on the bed, and I was now lying next to my son, both of us naked and horny. I reached for my vibrator, clicked it on low and put it on my clit. I just wanted to lay there next to him feeling good, I wasn't ready to cum again just yet. I turned my head and look at him, I said, "feel free to join me, and if I like what I see, you might get another treat tonight." Then I turned my head back and closed my eyes. I was lost in my feeling when I heard the sound of my son's hand slapping on his cock. Before I looked at him, I tried to picture what he would look like jerking off.

I had a great picture in my head, so I opened my eyes and turned to look at him. It was an amazing sight; my son was laying nest to me jerking himself off while looking at me. I softly said, "This is amazing", and then I clicked it on high. I felt myself nearing an orgasm, so I took off the vibrator and said, "I have another treat for you." I got up and straddled his legs facing him. His cock was standing straight up in front of my belly, and it took everything I had not to grab it. Instead, I clicked on my vibrator, reached down between my legs and put it on my clit. Tommy now had his mother straddling his legs trying to make herself cum. It's everything an 18-year-old guy could hope for. I said, "I might make a mess, but I promise I'll clean you up, ok?" He nodded his head and picked up the pace of his stroking.

I could feel myself getting near, so I pressed it hard against my clit and yelled, "Cum with me Tommy, cum with your mother." It was literally 5 seconds later when he started shooting strings of cum all over himself. I yelled, "cum on me too." He pointed his cock at me as he continued to stroke himself. It was easy to see he was only 18, because he must have shot a gallon of cum all over the both of us. I couldn't hold out another second, I felt myself squirting all over my son and I didn't care. In fact, I sat up a little so I could spray it on his cock too. The problem was that when I did that, the tip of his cock touched my pussy, and I instinctively sat right on it. To my initial horror, I realized I was fucking my son. It took a few seconds for both of us to calm down, but when we did, I was afraid to move. I was sitting on my son's cock, and I didn't know what to do. We just looked into each other's eyes.

After a short time Tommy said, "Thank you." Then he started to push his hips up and down. With the loss of all control, I let my son fuck me. I rode him really hard because it was the first time in many years that I had a man inside me, and it felt amazing. I really didn't give a shit that it was my son's cock, I just knew that I needed it badly. To his credit, he stayed hard, and I felt every inch of him inside me. I leaned down, put my hands on his chest and rode the hell out of him. I was riding him really hard because I just couldn't get enough.

I looked down at him and I said, "I'm sorry honey."

He just said, "It's our secret to keep, right?" I nodded my head as he pumped his manhood in and out of me. The longer we fucked, the more comfortable I was getting with it. I was so comfortable, that at one point I turned around and while facing his feet I sat back down and let him watch his cock disappear inside of his mother's pussy. I think seeing that plus looking at my ass did something to him because he started banging me even faster and harder. I was holding on to his legs for dear life as he fucked me hard. It was the first time in years that I had a real cock inside of me, and I didn't want it to end. I wanted it so bad that after a few minutes I climbed off and stood next to the bed because I didn't want him to cum too quick. He said, "Did I do something wrong?" I assured him he was perfect, but I just didn't want him to cum again. Tommy said, "I won't, trust me, I'm enjoying this too much."

I couldn't have heard a better sentence, so I said, "Good, then come over here and take care of your mother again." While still standing I bent over the bed, spread my legs a little and squatted down waiting for my son to arrive. He was behind me in no time, and I thought to myself how I must look to him right now. He not only saw his mother naked for the first time tonight, but he's also now looking at me bent over the bed begging to be fucked. This has to be one of the best nights of his life, and I was really happy to be the one to do this for him. I felt the head of his cock press against my pussy, so like any good mother, I pushed back and swallowed his cock with my pussy. I had a death grip on the sheets while my son took care of my needs from behind.

Having someone inside me after so long made my next orgasm impossible to stop. I started to cum, and it was so intense that I felt myself splashing all over my own legs, but I really didn't care, I just let it go and had my best orgasm of my life. As I was cumming, I managed to moan, "Cum all over me again." Seconds later I felt him pull out and suddenly there was warm streams of cum spraying all over my back. It was his second time tonight, and from what it felt like, it was another big load that was now all over me. I stayed in that "just fucked hard" position bent over the bed as Tommy laid next to me. I looked over at him and said, "That was so wrong, but I loved every second of it."

He smiled and said, "Me too." Then he kissed me on the head like he used to as a little boy and went into the bathroom.

I stood up, walked into the bathroom and turned on the shower. I looked at him and said, "Do you want to help me clean off my back?" He smiled again and followed me into the shower.