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Taught by Mom's Best Friend

Posted by: Age: Younger than 20 Posted on: 8 comments
25 likes 12662 views Category: Masturbation Male-Female Tags: mature, young man, teaching, handjob, curvy, older woman
A young man desperate for sexual interaction gets taught a sexy lesson by his mom's best friend.

When I was younger my mind was completely taken over by hormones. I had a few girlfriends but up to that point I had never gone further than French kissing. I was a single child raised by a single mom, and had a good relationship with my mom. She had me when she was 20 and worked like hell to provide us with a good home. She talked to me about sex at an early age, and always talked about masturbation as a normal function of life, probably to help me avoid making the same mistake of having a child at a young age. I masturbated every day since about the age of 14, but I started to crave sexual attention. I was desperate to have any kind of a sexual interaction with any female. Back then I was shy when it came to girls, and I thought the day would never come when I would actually be able to see a naked female body in real life. At that age it was all I could think about, and I was so desperate to have any kind sexual interaction. One day I came across an erotic story online about a middle aged woman who taught a shy and eager young man how to masturbate for the first time. For years she tutored him meticulously in the intricacies of foreplay and mutual masturbation, and eventually introduced him to sex and the art of making love. She let him try whatever he wanted on her and in exchange she received a devoted student who she trained to be the most perfect human sex toy. After I read that story I started fantasying about older women teaching me about masturbation and sex. I would fantasize about almost every adult woman I knew, including teachers, co-workers, and all of my mom's friends. I focused a lot on my mom's single friends to make my fantasies seem like a more realistic possibility, and especially my mom's best friend Becky who would often complain of how she needed to get laid. One evening my mom and I were watching a movie in the living room when a heavy sex scene came on the screen. I was sitting next to her on the couch wearing mesh shorts not more than two feet away. Uncontrollably I got a hard on in seconds, which was more than obvious with the shorts I was wearing. I became panicked that my mom would look over and see the erection in my shorts. I began to sweat from being embarrassed, nervous, and scared. I guess my mom saw me looking down at my bulge and the terrified look on my face because she nonchalantly said "don't worry, its normal, just watch the movie and don't worry about it." Later that night I started to think about how I had gotten an erection while watching the movie with my mom. Then it dawned on me that my mom had seen my hard penis bulging in my shorts, and had actually referenced it. I realized that by "it", she meant MY penis. I was a little creeped out, but also very turned on that a woman (albeit my mom) had actually observed and acknowledged the condition of my penis as being in a state of arousal. The fact that my penis could get the attention of a middle age woman eventually outweighed the fact that it was my mom, and I started becoming "accidentally" aroused in front of her more often. Soon my desire for sexual interaction had made me bolder, and I often would wear mesh shorts around the house with a raging erection. My penis was about 71/2 inches and at that age once it got hard it was almost impossible to lose an erection without masturbation. Often I would give myself an erection and pretend to try to hide it when my mom came in view of it, which only made it more obvious that I was excited. Although I fantasized of her showing me her naked body, I justified it in my head as her showing me for actual "educational purposes", so not to feel bad about my twisted desires. Honestly, I don't know what I was hoping to accomplish by showing off my erections, I didn't really have a plan, I just wanted the attention of a woman. One afternoon I was masturbating in my room to a porn magazine when I heard my mom's car pull into the driveway. I knew she would come up to my room to say she was home, so I quickly hid the magazine and got dressed. Wanting to show off my erection when she came in my room, I didn't put underwear on so the bulge of my penis would be more visible through my shorts. When she knocked on the door I told her to come in as she found me laying on my bed reading a book for school with a massive erection staring straight at her. I swung my legs over the edge of the bed and sat up in an awkward way pretending to try to hide my erection. She said hi, looked down at my shorts, she then paused... "So I think we need to talk about why you have an erection all the time" I was so possessed by my desire for sexual interaction that I guess I had never thought about the possibility of how horrible and embarrassing it would be if she actually confronted me. I started to realize that I was about to enter this uncomfortable reality. Still sitting on the edge of the bed, I started to hunch over with my eyes falling to the floor like bricks. I quickly mumbled that I was sorry and didn't mean to, hoping that she would just drop it and go away. "You shouldn't be sorry, it is perfectly normal, and it doesn't bother me that you have an erection while in your own room, but I am concerned that every time I see you, you seem to have an erection and I am worried that you are in the same state at work and school, where it is not appropriate." At that moment, I panicked. I was mortified that she had actually called me out for parading my erections in front of her. I was desperately trying to think of an explanation for my deviant behavior. Adrenaline was shooting through my head and I was stuck somewhere between shock and arousal. There was no way that I could actually tell the truth and admit that I had been purposefully exposing my erections to her. Trying to think of a way to explain my actions, I decided to pretend that I didn't know how to control it. Stupidly, in my disoriented and aroused head the story of the older woman raced through my mind... maybe she would even teach me how to masturbate if I pretended not to know how... Thinking that I should not have removed my underwear to make my erection more obvious, I thought of a clever rebuttal to her concern of public presentations. Trying to buy sympathy at the same time I sheepishly replied, "It is not a problem when I leave the house because I wear two pairs of underwear. It does not show as much then." With a completely dumbfounded look on her face she said "What? You wear two pairs of underwear?" "Yeah... it gets too hot, so I only wear 1 pair around the house" She paused as she thought about what she wanted to say next. I could tell that the 2 pairs of underwear line caught her completely off guard. She stammered as she continued, "I am confused... What is the problem? Why is that necessary?" "Because it won't go away" "What do you mean? Doesn't it stop after you take care of it?" Realizing that she may have seen stains on my sheets and underwear when doing laundry, I abashedly said, "I can't really take care of it... Well sometimes when I sleep... it will happen on its own... in my sleep... and then it is better the next day" "What? ... Why can't you take care of it while you are awake?" she asked in a calm and very concerned voice. I am actually not sure if it was an epic performance of acting, or if my rattled emotions got the better of me, but at that moment my eyes started to fill with tears. Looking at nothing but a spot on the floor my voice cracked while replying, "I have tried to masturbate, but it doesn't work for me. I just can't... and after it hurts even more" "It hurts?" She asked in a sympathetic voice. "Yeah... They hurt... My... testicles, get sore" She was at a complete loss of words, I could tell she felt bad but had no idea what to say. "It's ok. Don't feel bad about it. This is part of growing up, and we'll figure it out. Maybe we should take you to see a doctor?" Horrified at the suggestion of seeing a doctor, I then realized I had taken my game too far. Acting frustrated and embarrassed I crassly responded, "And tell him what? No! This is embarrassing enough. I will just deal with this on my own." She calmly responded, "I want you to know I am not concerned about you having an erection here at home, but if you are uncomfortable all the time, we need to figure out a solution to this problem. Let me think about this, I'm sure there is some way to make you more comfortable. We may need to take you to doctor though." I gave her an angry look of protest, and she said "I know you don't want to see a doctor, but it is crazy for you to go on like this." After she left I felt extremely stupid and embarrassed. I had let my crazy fantasy cloud my head and I certainly did not get the response that I had wanted. I felt like such an idiot. What really did I expect? Of course her answer would be to go see a doctor, and now I could not just say "never mind, I figured it out" as she would clearly know that I had made the whole thing up. I was mortified with the situation that I had put myself in. Worse yet, I thought about what a doctor might say, and if they might expose my flawed story as a work of fiction. The mere idea of trying to defend my position of not being able to masturbate made me want to die. Later that night the phone rang. Looking at the caller ID I saw it was my mom's friend Becky. Becky and my mom were inseparable, they did everything together. Becky was a little younger than my mom, about 30 years old. She had a pretty face, mid-length light brown hair, was pretty tall about 6'1" in height, and weighed roughly about 190lbs. She had a magnificent voluptuous body with a more than healthy ass and breasts the size of cantaloupes. Since my mom normally told her everything, I knew there was a good chance that my mom would tell her about my problem. I needed to listen in on their conversation, as I had to know what my mom was thinking so that I could figure a way to get myself out of this situation. Back in the 90's cordless phones used FM frequencies that could be picked up by a radio that was close by, so I quickly closed my bedroom door, and ran over to my boom box radio sitting on my bookshelf. I turned on my radio, pressed my ear against the speaker and started scanning the dial until I was able to pick up the frequency of the cordless phone that my mom was using. When I picked up their conversation Becky was in the middle of telling my mom about her nightmare moving experience from the last weekend. She was moving to a new condo across town, and had to be out of her old place, but there was an issue with the new place that prevented her from moving in. So all of her stuff was currently in a truck and she was staying in a hotel until the following weekend when she could move into her new place. As a single woman with no family in the area, she felt horrible asking her friends to help her move for the second weekend in a row, but she would have to ask someone because there was no way she could do it on her own. To make matters worse it was supposed to be 95 degrees on Saturday, which would make moving even more miserable. My mom said she had to attend a work function on Saturday, but she had no problem forcing me to help her out. "Really? He wouldn't mind? That would be great!" Becky said. My mom laughed and said "he doesn't have a choice, so he would be happy to." As if she was thinking out loud my mom said, "it is going to be really hot..." My mom then paused and said... "So, I should probably warn you about a little problem he is having". With my mom providing another long pause Becky interjected, "Oh, Is he okay?" "He is fine... sort of... you are not going to believe this... seriously... you won't" she said while uncomfortably laughing. "What is it? What's his problem?" Becky asked curiously. "Well recently... he sometimes... gets noticeably aroused" she said giggling. "Yeah... Of course he does, he is that age. At that age sex is all I could think about too. Hell, it is still all I think about now", she joked. "I know it is. Whore!", my mom teased. She continued, "I am really kind of concerned though, it seems like every time I see him he is aroused, and sometimes it lasts all day. I confronted him about it this afternoon because he has been walking around the house like he has a flashlight stuck in his shorts", she said laughing. Becky responded while giggling, "Come on, it can't be that bad, it's normal, boys just do that." "Yeah, well... he just told me he wears two pairs of underwear to hide his erection when he leaves the house" "Oh my god! Are you serious? Is it that obvious?" Becky exclaimed. "It is really obvious... But there is more...This is the part you are not going to believe... he actually confessed that doesn't know how to masturbate." "WHAT? No way! I thought that guys were born doing that?" Becky exclaimed while laughing. "He said he has tried and it doesn't work for him.... Whatever that means... Strangely, I actually believe him, he was pretty upset to admit it" Still giggling Becky said, "You are right, that is unbelievable" Lowering her silly laughing my mom continued, "I actually feel really bad for him, he is so embarrassed, and he admitted that he is actually in a fair amount of pain from not being able to release. What do I do? I suggested that we take him to the doctor and he about died of embarrassment just thinking about it". Becky, still finding it hilarious, couldn't stop laughing while saying "Doctor? He doesn't need a doctor, he just needs someone to give him a hand job and show him how it is done. " "BECKY!!! That is MY SON you are talking about" my mom exclaimed. "For 15 bucks I bet you could get a girl on South Street to show him how" Becky joked. "Shut up! I am not getting a prostitute for my son!" "You know... if he helps me move this weekend, I will kind of owe him" she said giggling in a sarcastic voice. "I don't want to think about anyone helping him with, or showing him anything!" pausing she then said "and if they did, I would never want to know about it." They went on to talk about other things, but I was so shocked by what I just heard that I had practically climbed the bookshelf with the radio on it. I could not believe that my mom just had a conversation with her best friend about MY penis. Moreover, Becky had just offered to show me how to masturbate, and although not directly, my mom seemed to give her permission. At the time I knew Becky was joking, but just hearing her say that made me so excited that I unconsciously started to masturbate with my hand inside my shorts. Almost as if something had taken over my body I was so frantically stroking myself I didn't notice that I was still standing in the corner facing the bookshelf with the radio, or even that I still had my shorts on. I remember feeling a stream of cum oddly splashing out what seemed like 30 seconds before I actually orgasmed. The orgasm was so strong and intense that the rest of my body nearly went numb. Uncontrollably, I kept the frantic pace of stroking way past the orgasm to the point where sensation was so intense that it actually made my knee buckle and I collapsed to one knee. I felt cum dripping all over my foot and it was then that I realized that I had forgotten to take my shorts off and came inside of them. I opened the front of my shorts with the other hand and saw a sloppy mess of cum stringing from my shorts to my cum-covered hand. With an amount of cum that only a young man could produce, there was so much cum dipping down my thighs and legs that I literally had to take a shower... Later in the day I nonchalantly agreed to help Becky move when my mom asked me. Out of all my mom's friends, Becky had always been my favorite. She had such a nice, fun loving personality, she was hilariously inappropriate and was always joking with me. Her curvy voluptuous body would torture me, as she would always wear low cut shirts, and clothes that hugged her awesome curves. She played volleyball in college and although she had gained a few pounds since, she still worked out and could be described as athletically curvy. As for me, although I was about 5'9 and 170lbs at the time, I was a 3 sport athlete in great shape, and made the varsity basketball team in my freshman year. I wanted to impress Becky when helping her move so I wore a sleeveless shirt to show off my arms, and I had practiced wiping sweat off of my face with my shirt in the mirror as to perfectly flash my abs to her. I also wore Umbro brand shorts that were a popular light weight nylon that did nothing to hide an erection. I even ironed the flaps on my boxer shorts open, so not to provide any resistance from showing off an erection if the opportunity were to arise. When I arrived to help Becky unload the truck she was wearing work out attire with spandex shorts and a tank top with a sports bra underneath. Her cleavage was completely visible which made the moving worth it already. In the morning I worked as hard and as fast as I could unloading the moving truck. I wanted to impress her with my work ethic while showing off how athletic I was. She was shocked that just the two of us we were able to unload the entire truck in a couple hours, and she was almost glowing when I insisted that I would help her unpack and move whatever she needed inside. We ordered a pizza for lunch, and while she was 15 years older than me, she was very easy to chat with and was always joking with me. During lunch she became rather flirty teasing me about how I must do well with the high school girls (which was anything but the truth). We were both drenched in sweat from moving in the heat and after lunch she decided to take her wet tank top off while we were unpacking inside. Now wearing just spandex shorts and a sports bra, it was hard not to admire her amazing curves. I am not sure if she was doing it on purpose or not but it seemed like every time I turned around she was bending over to pick up another box or leaning forward to expose her cleavage. It did not take long for me to feel my penis getting hard inside my shorts and while wearing nylon shorts and ironing open the flaps to my boxers seemed like a great idea in my fantasies, in reality I became very embarrassed when I started to get hard. I went to the bathroom several times to try and reconfigure to make my erection less visible, but there was nothing I really could do and it was extremely obvious once I became fully hard. Becky pretended not to notice, and she continued to flirt and joke around with me. Additionally, she was clearly not self-conscious about bending over in front of me or bumping into me (she playfully hip-checked me several times when we both were entering a room at the same time), so I kind of got the feeling that she was enjoying my attention. Once I saw that she was okay with me being completely aroused in front of her, I quickly overcame my embarrassment and started to enjoy it. For the next two hours we unpacked most of the boxes in the main living spaces, and I casually walked around her condo with my very obvious erection pointing straight out. I even caught her glancing at it a few times and I started to think that her momentary pause when bending over to pick up a box was for my benefit. Not only was her ass very large, but in her spandex shorts I could tell it was also very toned as I could clearly see the sharp curves of her lower butt cheeks. Watching her bend over all afternoon, I can confidently say there was not a minuet that went by when I was not hard as a rock. We were almost finished for the day when she asked me to help her put some boxes on the shelves in the attached garage. I didn't think about it until I saw how high the shelves were and she asked me if I would get on the ladder so she could hand the boxes up to me. Once I got up on the ladder, my crotch was almost perfectly at her eye level, and while looking down at her I couldn't look at her face without also staring down her bra at the same time. "Must be a nice view up there" she said with a sly smile. "View? What view?", I said while trying not to look down at her. "Please. I am not stupid, clearly something has you excited" she teased. "Oh. Yeah... Sorry... it is hard not to look at those [her breasts] from up here." "It's okay, my view from down here is pretty nice too", she said while raising her eyebrows and looking right at my erection. She then looked up at me and gave me a wink while saying, "Just try not to hit me in the head with that thing, you might give me a concussion." Joking back I said, "I will try not to, but it sometimes has a mind of its own" "So are you saying that you have a 'hard time' controlling it?" she said laughing (she seemed very pleased with herself for her clever pun and triple entendre). "Well... I manage... I guess", I said in a sombre and self-defeating tone, trying to gain sympathy for my fake problem. She handed me the last box and said, "Well, I really appreciate you helping me out so much today, so if you promise to never tell a single sole about it, especially your mom, I will help you to 'manage' today." "Okay", I said nonchalantly, not really knowing what exactly she meant by that. After she helped me down off the ladder and I almost hit her in the shoulder with my erection on the way down, we went into the kitchen to get a drink of water. She thanked me again for helping her, and told me to go sit on the couch while she went to look for something. She came back with a large beach towel and a bottle of baby oil. Honestly, I was confused with what the baby oil was for (ha ha). As an adult, looking back on it now, it should have been obvious what she was doing, but I remember not being sure of what her intentions were. She had me get up and she laid the towel down to cover the couch. "Now if I am going to help you this ONE time, you have to swear that you won't tell anyone. Seriously, I could get in a lot of trouble. So you have to swear to me that you won't tell your friends or anyone else ever, and no matter how much you want to brag that an actual woman jerked you off, you have to absolutely swear this stays just between us" I couldn't believe that she just said she was going to jerk me off. Was this actually going to happen? I was stunned that my fantasy was actually going to come true. It was all I could do to barely mutter the words "I swear". I was also very glad that while she was trying to help me with my fake problem, she did so without the embarrassment of acknowledging that my mom had told her about it. She made it seem as if her offer was purely in fun, and a reward for helping her without any knowledge of my mother telling her anything. "Now take your clothes off and sit down", she said. I quickly took off my shoes and socks, pulled down my shorts and boxers, and sat down on the couch. "Un-huh... The shirt too" she said as if she caught me trying to get away with something. So I pulled off my shirt, now sitting completely naked on her couch with my penis straight up in the air. Then to my surprise she took her sports bra off and showed me the most magnificent sight of my life. I could barely believe what I was seeing. I had never seen breasts in real life before, never mind that hers were at least D cups and perfect in every way imaginable. When she pulled the sports bra off, and her breasts escaped the last fraction of tension from the elasticity of her bra, I will never forget the way her breasts bounced up and down before settling to their natural hanging position. My jaw must have dropped open, because she smiled and said "you have never seen a pair of tits before have you?" I couldn't speak. I just shook my head no. As she kneeled before me she said, "You can touch them, but for women with larger tits, they are sensitive, so be gentle." As I reached out and touched them for the first time, I was in heaven. I gently slid my fingers down the front of her breasts, over her perfect half-dollar shaped nipples, and down around underneath them. I then held each breast in each hand for a few moments before continuing my exploration of the most amazing treasure in the world. She was just smiling and watching my face as I could tell she was enjoying having someone looking at her body as if it was the most precious and beautiful thing that they had ever seen. She let me continue exploring her breasts for what seemed like a long time, it must have been at least 6-7 minutes, as I didn't miss running my hands over a single centimeter of her chest. I could have continued for hours but once I seemed mostly stratified she said, "Okay, I want you to lean back." She reached for the bottle of baby oil and asked, "Have you ever tried baby oil before? It really helps to make it slick so your hand can slide up and down much easier." Without waiting for a response she very slowly dribbled the baby oil over the head of my penis and watched it for a few seconds as it slowly dripped down the shaft of my cock. She must have enjoyed this process because she took her time and did it 3 or 4 times, only dribbling a few drops each time, then stopping to watch it drizzle down until my dick was completely soaked in baby oil. "Baby oil can get messy, but the more you use the better it feels, so you want to coat your entire penis", she instructed. She made it seem like she was giving me instructions on how to use baby oil, but we both knew she was really trying to teach me how to masturbate. It was exactly like I fantasized in my head hundreds of times. As she started to rub my penis she choreographed her movements. "Then you just want to slowly rub the oil on with your hand, make sure you rub it all over the entire length of your dick with long strokes. Get down all the way to the very bottom of your base and come up all the way to the tip. As you start to reach the tip make sure your hand is tight enough so that your hand gets caught a little by the undercarriage of your tip. Right underneath the tip is the most sensitive spot on the penis, and you want to make sure you get good friction there, so keep your hand tight enough so it almost flicks your tip of your cock on the up strokes." She then pauses and reached for the baby oil again as she starts to drizzle it on her breasts. "Okay, as I rub baby oil on my tits I want you to try on your own what I was just showing you. Go very slowly though. Just relax and enjoy watching me rub my tits. I want you to relax and let the orgasm build up. She then closed her eyes and rubbed the baby oil all over her breasts. I slowly jerked off as I watched her hands slide all over her amazing mounds. As she pushed up her tits and let them fall I watched the vibrations flow back and forth as they bounced back down. She then opened her eyes and saw me wide eyed and stroking. "I can tell you really love my tits" she said with a confident smile. Then reaching for the baby oil again she said, "Now pull you penis all the way back and hold it against your stomach. While doing those long strokes with your right hand, you can also use the oil to rub the your testicles with your left, but just hold your penis against your stomach for now and I will pour a little more oil underneath on your balls" She again dribbled it on the under part of my shaft and watched it as it flowed down to my balls. Reaching all the way underneath she took my balls in her hand and gently started to rub them. As she gave them a gentle squeeze she said, "I love holding a man's balls in my hand, it makes me feel so powerful." Then she took my penis out of my hand and pulled it off my stomach, as she started to stroke my cock with one hand and rub my balls with the other. "Does that feel good honey? Can you feel the cum building up in your balls? The next time you are alone with your cock I want you to masturbate yourself just like I am doing to you now, and I want you to close your eyes and pretend it is me that is stroking your cock. I want you to think about me rubbing oil all over your hard dick and I want you to think about how you were masturbating yourself while watching me pouring oil on my tits." "Now I want you to take your left hand and rub your balls while I stroke your cock" As I replaced her hand with my hand and started rubbing my testicles, she took her left hand and put it down the front of her shorts. As her fingers first went inside her shorts she let out a little sigh as if she was finally able to scratch an itch that had been bothering her for some time. I could not believe it, as she was now masturbating herself while she held my penis in her hand. I tried to lean forward a little to maybe get a peak down her shorts, but her spandex shorts were too tight and all I could see is the outline of her knuckles through her shorts. After a few minutes she started to really speed up the pace that she was rubbing herself as well as the pace that she was stroking me. Looking at her as she stroked me, with oil all over her tits, with her hand in her shorts rubbing her pussy with the same hand that was rubbing my testicles a few moments earlier, I felt the blood run out of my head, and felt my testicles start to tingle. "Becky" is all I said, and she read it on my face that I was getting ready to cum. "Honey, I want you to cum for me. Just relax and don't hold back, I want you to cum as hard as you can." She started furiously stroking us both with both hands. She was so into it, her hands were moving so fast in unison on both of our genitalia. I said her name once more, and she leaned her chest into my cock as she stroked even faster. I remember hearing the oil squish in her hand and a light slapping sound as the tip of my penis was banging against her breasts. My penis was rubbing all over her chest and as she stroked me and I felt my cum start to release. The first shot of came out with so much force that it splashed off her chest and back onto my shoulder. Surprised by the force and amount of cum, she let out several "oh" sounds as came. I came so hard that her chest, neck, and stomach were covered in cum. After she milked the last drop out of me, she put her hand on my knee to hold herself up, smiled at me and said "hold on, I'm almost there." Then she closed her eyes and leaned back as she went to town rubbing her pussy inside of her shorts. It took her several more minutes for her to get there, but I had no complaints as I just sat there and watched in amazement. Watching her masturbate while her front was completely covered in my cum was almost better than the actual orgasm I just had. Her eyes were clinched shut, and she was so concentrated on fucking herself as her fingers were flying inside her shorts. I felt her hand squeeze down tight on my knee, and she bit down on her bottom lip. Then she started to uncontrollably shiver and shake as she made several high-pitched squeals. In awe, I intensely watched as I witnessed my first female orgasm. ------------------------- If you liked this story, feel free to add me as I am working to finish a couple others in the near future.

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