My Insecure Son

Every mother wants the best for their children, that is a fact. You never know what kind of situation you will be put in but all you can do is hope that you respond appropriately. Sometimes though, this is easier said than done.

My son Tyler is 18 years old. He is what you would consider a "nerd". He was tall for his age standing at 6'2" but more on the lanky side build wise. He preferred video games and sci-fi movies as opposed to sports and partying. I can say I was relieved I never had too much to worry about with him getting into the trouble that most teens do. The one "normal" thing he did still enjoy was girls. Although he was a bit shy and timid he had been dating a girl for about 7 months. However, after noticing a change in Tyler's behavior I decided to sit down and have a talk with him. He had been much more withdrawn the last week. Spending all his time in his room and playing video games hidden from the outside world.

"Tyler, is everything okay?" I asked, sitting down on his bed as he played his video games. He was unresponsive. I walked over and turned off the tv to get his attention.

"Mom, what the hell? I was in the middle of that" Tyler said in an irritating tone.

"Tyler we need to talk. What is wrong with you lately? You barely leave your room and when you do you are moping around like your pet goldfish just died" I said jokingly trying to ease his mood.

"Claire broke up with me" My son finally confessed.

"Oh, hun I'm so sorry. You two seemed so cute together. These things happen though. You are young and relationships at this age rarely last very long." I said trying to reassure my son that this is a normal part of growing up. "What happened? Did she give you a reason why at least?"

"Not really." He murmured quietly with his head down towards the floor. "I think I might know why but she never told me. She just texted me saying she didn't want a boyfriend anymore."

"Well what do you think the reason is?" I asked placing a hand on his shoulder. "You know you can tell me anything hun."

Tyler's father and I had divorced when he was 6 years old and we had always been close but after his father passed away from cancer 5 years ago it really forced us to be open and honest about things he would normally be able to talk about with his dad.

"Well..." He said nervously biting his nails as he tried to find the words. "You know that Claire was my first girlfriend but I was also her first boyfriend. Last week we were watching a movie in her basement and we started kissing and one thing lead to another."

"Oh, I see." I said. "Well hun it is totally normal to begin to discover your sexuality at your age. I know I was doing the same at your age."

"Well neither of us had ever done more than make out with someone before then. After a while she reached her hand in my pants and started taking them off. After she pulled my jeans and underwear down I already had a boner and was excited because it was my first time doing this." Tyler's face began to blush as he explained the situation.

"You have nothing to be embarrassed about Tyler. It is normal to be nervous doing something for the first time." I said reassuringly and patted his back.

"I wasn't nervous mom I was excited. But once my pants were off she didn't seem to be as excited as I was anymore. We kept kissing but she never touched it or anything and after a minute she said she heard someone upstairs and told me pull my pants back up. After that night, she barely texted or called me and seemed disinterested and then dumped me yesterday." Tyler explained the situation, still blushing as he tried to tell me.

"I am so sorry to hear that. Having something negative like that happen the first time you become active can be traumatizing but you must understand that life goes on." I said rubbing his back now trying to console my poor boy. "You still haven't told me what you think the reason is why she seemed to lose interest at that point."

"It's embarrassing mom." He said quietly and looking at me with sadness in his eyes. I could see my son was truly worried about something.

"You know I am here for you and you have nothing to be ashamed about. Tell me what is on your mind." I said.

"Well, I think she thought it was weird when I took my pants off." He said.

"It is the first penis she has seen Tyler, I am sure she thought it was weird, I know I thought the first one I saw was weird. Why do you think that?" I asked. I could see how nervous he was from his body language and I felt terrible for him.

"Well it is really really curved and I don't think it is normal." He said quietly.

"Tyler, is that all? Hun, you have absolutely nothing to worry about. There are plenty of penis's that are curved and it's perfectly normal." I said hoping this reassured him.

"I mean I have seen other guys naked in porn and seen a few that were curved but mine seems to be a lot more curved even. I just feel like it is going to freak girls out and I can't get it out of my head." Tyler said getting increasingly frustrated.

"Don't worry Tyler. There is nothing to get worked up about." I said rubbing his shoulders trying to console him. "Is there anything I can do to make you feel better? You know I am always here for you whatever it may be."

He looked at me for a second and then back down at the floor. "There is one thing but I don't think it is appropriate for me to ask."

"You can tell me Tyler. I promise I would never judge you or ridicule you in a time like this." I said.

He took a deep breath and looked me in the eyes which if you knew my son, you'd know he was serious. "Would you look at it and make sure that it is normal?"

My eyes got wider when I heard his request. Did my son really just ask me to look at his penis? My shy, timid, loner son had asked me to make sure his penis was normal. If he was willing to ask me something like that I knew he must be freaking out about it and thought he needed a second opinion.

"Oh my...I see now why you were having a hard time asking me." I said with a smile trying to lighten the mood. "You know I would do anything for you. I am sure there is absolutely nothing wrong with it but if you need me to look than of course I will."

"Really?" He asked with a little relief behind his voice. "You would do that?"

"Of course I will hun. It wouldn't be the first time I have seen your penis." I said jokingly. "I did use to bathe you ya know."

"I know but this is different." He said. "It only gets really bad when I have an erection and you have never seen it like that."

I couldn't help but let out a giggle. "Hun, not to make this more awkward but I have seen my fair share of erections. I will be fine. Why don't I leave the room and you can get yourself comfortable. Just yell out to me when you are ready."

I got up off the bed and walked out and went to the kitchen and poured myself a glass of wine. If there was ever a right moment to chug a glass of wine, I think this was it. I chugged down a full glass and poured myself a second to sip on as I waited for him to call out. After a few minutes I heard his voice faintly down the hall and I walked towards his room.

"Are you ready?" I asked as I knocked on the door.

"Yeah, you can come in." Tyler said.

I opened the door and walked in to see Tyler standing by the foot of his bed with a towel wrapped around his waist. He avoided making eye contact with me as I walked in and sat at the foot of his bed in front of him.

"Okay Tyler whenever you are ready you can take off the towel. I promise there is nothing to be embarrassed about" I said before looking him up and down trying to process the situation.

Sitting on the bed my eyes were level with his stomach so I knew when he took off the towel it would be right there in front of me. He looked around the room nervously one more time before moving his hands to his towel and untying the knot he had it folded in. One hand pulled one side of the towel open followed by his other hand tugging at the other side and the towel fell to the floor.

My eyes got big and I let out a slight gasp as I looked at what was in front of me. My son's penis was fully erect pointing right at me. My reaction startled him a bit.

"There is something wrong with it isn't there?" He asked worryingly looking down at his erection.

There was a definite hard curve to the left but it did not appear to be anything out of the ordinary.

"No no no Tyler there is nothing wrong with it." I quickly responded trying to reassure him. "I see what you mean about it being curved but I think something other than the curve had her feeling nervous."

"What is it then?" He asked frantically.

My eyes stayed on his package trying to find an appropriate way to tell him. I couldn't break my gaze from it. My shy and timid son had an impressive package. It was not very thick, probably average, but nothing to worry about at his age as he is still developing. The length though is what had my eyes locked on. Mind you, I did not bust out a tape measure but from experiences I have had in the past I would have to guess that he was just over 8 inches long. I have seen my share of unattractive penis's but this wasn't the case with Tyler's. Before me was his long skinny curved shaft with a big round mushroom tip on the end. Everything about it was nice. The skin was soft and perfectly colored. His balls hung rather low and appeared larger than I remember boys having when I was his age. I took a breath and explained my theory to him.

"Well hun I don't know how else to say this without being inappropriate." I said laughing a bit. "To be blunt, you have a big penis. I am guessing that it may have intimidated her."

I looked up and saw his eyes light up.

"Really? You think it is big?" He asked with a giddy tone in his voice.

"Tyler, I know it's big. Look at it for Christ's sake." I said giggling as I looked back down at his hard penis in front of me.

"I thought it might be big from seeing other ones in porn but it is hard to compare on a computer screen." He said as a smile began to creep onto his face.

I was still examining it with my eyes. Moving my head around to observe it from all angles. "Well I can assure you it is much longer than a lot of grown men are. You have nothing to be embarrassed about. Honestly you should be proud that you have a big dick." I said.

I realized right when I said it that I may have crossed the line of appropriateness when I referred to it as a dick, but honestly referring to it as a penis began to sound childish and awkward as I stared at the size of it. My worries that I crossed the line were quickly debunked by his reaction. When I finished saying the line "you should be proud that you have a big dick" I saw his shaft twitch and jump.

"Oh my god!" I gasped out laughing a bit seeing it twitch in front of me.

"I'm sorry mom I couldn't help it. I've never had anyone tell me it is big before and it got me excited." He said nervously.

"It's okay hun I understand. A lot of your confidence is going to come from being proud of your body and being told something like that makes being excited understandable." I said. My eyes still fixated on the long hard on in front of me. I watched as every few seconds it twitched again, seeing the big mushroom swell up a little more right in front of my eyes.

"You should really take care of that thing." I said laughing. "It looks like it needs some attention. I am sure you would enjoy some alone time so you can masturbate." I said as I stood up from the bed and began walking towards the door.

"Well I haven't since that night at Claire's house. Being so close to having her touch it and then what happened after kind of made me not want to even look at it. It just reminded me that she broke up with me because of it." He said as he sadly sat down in his rolling computer chair by the bed.

"Are you telling me you haven't take care of yourself in a week?" I asked.

"No, I haven't. I really wanted to the other day when I had the house to myself but I just couldn't stop thinking about what happened. You don't know how it feels to be so close to having someone touch it for the first time and then it goes wrong." He explained.

"I can kind of understand how that goes but you are right. I do not have a penis so I can't fully relate. Either way something needs to be one before you go crazy!" I said.

Tyler sat quietly looking down at the ground. I felt awful. He looked so defeated and I could only imagine how this has been weighing on him for the past week. His erection had gone down a little bit now laying on his right thigh. I hated seeing him like this. And you can judge me if you'd like but I couldn't stand by and do nothing.

"I'll be right back. Don't move!" I told him and walked out of the room down the hall to my room.

I couldn't believe what I was thinking as I walked down the hall. I was going to help him. I was going to help him get a release in the hopes that it reignited his attitude. My mind went back and forth between how wrong it would be and how much he needed this right now. What if he said no and it made things incredibly awkward? Although I doubt he would say no. He had asked me to look at his hard on and he had to have noticed me staring at it and that didn't bother him.

I have noticed him on several occasions looking at my body around the house. Honestly, I find it a bit flattering that I've still got it. I would consider myself a "milf" in the eyes of society. I was 5'5" and brunette with green eyes. At my age, I had put on a little weight but still had a curvy figure that I was proud of. My 34DD breasts were natural and were always my best asset but doing yoga and getting into a gym routine the last few years had really given me a nice round booty. Having a young guy, regardless of him being my son, checking me out made me feel like my hard work had been paying off.

I wanted him to know I was comfortable. I quickly changed out of my work clothes and got comfortable. I also ha visual stimulation in mind. I grabbed my favorite pair of grey yoga pants that made my butt look nice and squishy and a sports bra that contained my DD's just barely. I opened the drawer of my night stand where I keep my toys and pulled out my bottle of K-Y UltraGel Lubricant. I took one last look in the mirror and left my room.

As I walked down the hallway to Tyler's room my heart was beating out of my chest. Was I turned on by this? I couldn't tell you exactly what made me feel this way all the sudden. It could've been my little outfit I put on that I always feel very sexy in. It could be that I kept picturing his long shaft and swollen head right in front of me and how it was aching. Either way I was finding myself eager to get back in there. I took one last deep breath outside his door and walked in.

"Oh my god Mom what are you doing?" He yelled out as I walked in. I noticed his eyes moving up and down my body. My sports bra showing almost all the cleavage I had to offer and my yoga pants basically painted on showing the detail and shape of my round butt.

"I understand now why you have been so moody and depressed this past week. And it took a lot of bravery for you to be so honest and open with me about it. And now I want to help you." I said walking over by him sitting on the edge of his bed across from him in his chair.

"Help me how?" He asked. He was beginning to sweat trying his best not to stare at my tits in my sports bra.

"Well..." I said slowly while I took out the tube of K-Y lube and placed it next to me. I saw his eyes get big and light up. There was now no need to beat around the bush. He knew what I was there for.

"Are you serious?" He asked me.

I reached out and put a hand on his knee leaning forward a bit to show off my cleavage even more. As I touched his knee I could see his erection start to come back. Slowly growing along his leg.

"You are in a funk." I said. "And you need to get out of that funk. Sometimes all a guy needs is a confidence boost to get him back on his feet and your chance at that was ripped away last week."

His breathing was getting heavy looking at my cleavage as I explained myself.

"You need to get out there and meet someone knew. You need to know that most girls would have loved to pull down your pants and see that you have a big dick." I said as I caressed his knee. Again, me telling him he had a big dick seemed to speed along his erection and it started standing firmer and longer with each passing second.

I got down off of his bed so I was kneeling in front of him in his chair and I grabbed the lube and squirted it into my hand.

"I want you to just relax and sit back and enjoy yourself" I said looking up at him from my knees.

He nodded his head and looked down at me waiting for my net move. I reached my hand with the lube in it out towards his package and wrapped my fingers around the head of his dick.

"Oh my god." He said and let out a moan feeling my lube covered fingers touching his hard dick.

I began massaging the head of his cock, twisting my hand around the big fat mushroom covering it in lube before I slid my grasp down his long shaft spreading the lube down his length. Slowly I moved my hand up and down the length of his big dick covering his long curved shaft in the lube.

My right hand followed up his inner thigh until it reached his big hanging balls. I took them and cupped them in my hand as my left hand continued stroking the lube onto his big dick. My fingertips began playing and massaging with his sack, slightly juggling his balls in my hand as I felt his cock now hard as a rock in my hand.

Once his cock was fully hard and the head was swollen I sped up. My hand now stroking and squishing with the lube up and down his 8 inch cock. I could feel his legs tremble and hear him let out a moan with each stroke. I squirted lube into my right hand and went back to fondling his big ballsack with lube getting them coated in the shiny gel.

"Oh my god mom it feels amazing." He said followed by a string of moans.

"I am glad you like it hun." I said reassuring him everything was perfect. "I never was much of a fan of giving handjobs but it's always more fun when it's to a big dick."

Finally, I saw a smile spread across his face. The first smile I had seen in a week. It was evident he loved hearing me talk about his big dick. The lube covered his entire package now and my hand freely was gliding up and down his long shaft while my other continued to milk his big hanging balls.

It had been about 5 minutes of stroking his gorgeous 8 inch dick and I decided he might need more motivation to release.

"Do you need some visual stimulation to help you Tyler?" I asked as I held his dick by the base letting the length show in my hand.

"You would do that?" He asked. "That would be amazing mom."

"I have seen you checking out the twins before it is nothing to be ashamed of." I said as I let go of his dick and leaned back. I reached up to my sports bra and lifted it off releasing my natural D tits for him to see.

"Holy shit mom your boobs are huge." He said staring at my chest.

I laughed a little and leaned back towards him taking his cock in my hand again. This time holding the base firmly and using my other hand to stroke just at the top feeling his puffy mushroom head squish in my hand with the lube. I could feel my big tits bouncing as I jacked him off. His eyes were fixated on them.

His cock felt massive in my hands. I couldn't take my eyes off of it. The length was so impressive and his mushroom head was perfect. It had swollen up nice and fat and was turning red as I stroked his long shaft. I could feel the veins pulsing in his shaft with each stroke and knew he was close.

"It feels like you are getting close hun." I said while I slowly stroked from the base to the swollen tip.