When I was younger my mind was completely taken over by hormones. I had a few girlfriends but up to that point but 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 twenty 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 fourteen, but I started to crave sexual attention. I was desperate to have any kind of 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 of 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 fantasizing about older women teaching me about masturbation and sex. I would fantasize about almost every adult woman I knew, including teachers, coworkers, 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, 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 one pair around the house."
She paused as she thought about what she wanted to say next. I could tell that the two 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 thirty years old. She had a pretty face, mid-length light brown hair, was pretty tall about 6'1" in height, and weighed roughly about 190 lbs. 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 nineties, 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 he 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 fifteen 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 thirty 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 cumcovered 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.