Shopping with My Aunt and Mom

My name is Alan and I'm an 18 year old senior in high school. My mother Ruth and my Aunt Sandra raised me, my father had never been in my life whatsoever. Being raised by two strict consecutive women made my upbringing much more different than most of my peers.

I wasn't allowed to join any extracurricular school activities. Clubs or parties were out of the question, even if I had ever been invited. It was go to school, come straight home do my homework and sit with my mom and aunt until bedtime.

Since I wasn't allowed to participate in any school activities I had little opportunity to socialize. There was no way to make friends. I attended a super strict school system. There was no talking in class or in the hallways when changing classes. I was severely shy to begin with, which didn't help my situation. I basically accepted my life as it was and took it day by day.

In my senior year I was called into my guidance counselors office. I was told that an error had been made in my curriculum. It seems through all my precious years of high school the school had failed to assign me a physical education class. In order to graduate I was required to have a physical education credit.

My counselor explained the situation and gave me a handout syllabus about the requirements of the class. Included in the list of items needed were gym shorts, white tee shirt, tennis shoes and socks and finally an athletic supporter.

As my mom and aunt were perusing the supply's list, it was determined we needed a shopping spree.

The next Saturday morning we were off to the small shopping center in town. We had one big department store in town that would carry everything on the list.

My mom, aunt and I strolled into the store to gather my supplies. My mom saw a familiar face and headed toward her. It was our neighbor Miss Smith, she was a 50 something spencer lady who lived alone two houses down from us. She was a long time clerk at the store.

Miss Smith smiled and greeted us with, "Good morning neighbors, how can I help you folks?"

My mom handed her the list of items needed and said, "We need all these items, would you be able to assist us? Alan needs these for a physical education class in school this year."

Miss Smith glanced over the items looked up and answered, "Yes, of course, I believe we have everything you need in stock. What size shoes do you wear honey?"

I responded, "I wear a size 11, Miss Smith."

She started walking and gathering things as she went up and down the clothing aisles. "Why don't you all go on over to the changing rooms, they are in the center of the store, I'll meet you there in a few."

"Changing rooms," I asked in a surprised tone?

"Yes indeed," my mom quickly retorted, "We're going to make sure everything fits correctly before I buy anything. I'm not making another trip to exchange something that doesn't fit when we can see if it fits while we are here today."

My aunt Sandra nodded her head in agreement.

I submissively shook my head yes and just lowered my head. I followed mom and my aunt to the center of the store.

There were several booth like changing rooms. They were the type with the two curtains that you pulled together to close while changing clothes. Several chairs were near the changing rooms, more than likely for grumpy husbands waiting for their wives to decide which outfit to buy.

Miss Smith arrived with a pair of solid white tennis shoes and white socks. "Here start with these and I'll be back with more in a jiffy."

I sat in one of the nearby chairs and slipped my shoes and socks off in order to try on the new ones.

Mom asked, "How do they fit Alan?"

"They fit very well," I responded.

Mom and aunt Sandra came over to inspect the fit. Each one was feeling all around the shoes trying to find a place where they did not fit properly. Fingers were pushing on my big toes to see how close they were to the end of the shoe. Another finger felt between the shoe and my heel for snugness.

"Seems like a fairly good fit," my mom stated, with aunt Sandra nodding in agreement again.

Miss Smith returned with several white tee shirts in hand. "I forgot to ask your shirt size so I brought a couple of different sizes. Here why don't you try these to see how they work for you."

In the changing room I removed my shirt and hung it on one of the hooks. I put it on pulling it down over my torso. It was so tight it was like a second skin. I stuck my head out of the curtain and announced, "It's way too small."

Mom waved for me to come out so she could see.

I didn't want to be seen in anything so tight. I felt embarrassed about stepping out into the center of the store like that.

"Come on, lets see," mom demanded.

I stepped out and both aunt Sandra and mom shook their heads.

"Well that won't do, it's too tight."

Miss Smith arrived then and took a look. "Oh my, I really misjudged that didn't I? Wow I can't believe I was that far off, I must be losing my touch," she laughed.

Mom, not laughing, said, "Why don't we get all his measurements so there won't be any more guessing games?"

Miss Smith grabbed her measuring tape and waved me over to where she was standing. She checked the list that my mom had given her to make sure she remembered everything we needed.

"Ok Alan take that silly tight tee shirt off and I'll get your chest measurement."

"Right just let me go back to the changing room and..."

Miss Smith cut me off asserting, "Don't be silly there no need for that!" and with that she took hold of the sides of my tight tee shirt and whoosh it was over my head and off.

"Now that's better," Miss Smith sighed. She then told me to raise my arms so she could wrap the tape around my chest. "Ok great, got it," she announced. "Now I need to get your waist measurement." She tried to wrap the tape around my waist but couldn't because of my belt and high waisted pants.

"You're going to have to remove your belt sweetie, I can't get a proper measurement this way."

"No I don't think I need to do that, just get an approximate measurement," I insisted.

Mom stepped in saying, "Alan do what Miss Smith asks of you, she's a professional and knows how to do her job!"

"But mom?" I said.

"No buts about it, do as you are told," mom demanded.

I slowly unbuckled my belt and pulled it through the loops in my pants. When it was done I dropped it to my side.

Again Miss Smith tried to measure my waist.

"I still can't get an accurate measurement, these high waisted pants are making it impossible."

"Alan just un snap the waistband of your pants so I can correctly get your measurement."

Before I could object, my mom shot me a stern look meaning do as I was told.

I fumbled with the snap that hooked my waistband together. Pulling it apart I could feel my embarrassment spreading all over my body in red splotches.

"Still can't get your measurement," Miss Smith muttered. She then reached up with both hands and grabbed my zipper. She opened it enough to slide my pants down below my waist.

I was shocked, surprised and astonished. Nobody had ever touched that area of my body. It sent a wonderful tingle through me but at the same time embarrassed me immensely.

Kneeling in front of me Miss Smith seemed satisfied with her measurement and started to get up but stopped short.

About that time my pants suddenly fell to the floor around my ankles. Miss Smith had obviously left the zipper lever up and it had just unzipped by itself.

I froze, this could not possibly be happening! I started to reach down to pull my pants back up but I felt Miss Smith's hand stopping me.

"It's alright Alan, I need to get your inseam measurement anyway and this will make it much easier and accurate."

"Bu...but my pants," I started to say.

Mom cut me off saying, "Alan, do as you are told. I'm tired of all this disrespect you are showing Miss Smith!"

I looked at her in disbelief, I couldn't believe what I was hearing. I was standing in the center of our local department store with no shirt in my tighty whities and my pants around my ankles. I was totally embarrassed and must have been as red as a beet.

Miss Smith took that as her clue to continue. "Now Alan I'm going to measure your inseam so we can get a proper fitting gym short." She then took her measuring tape and extended her right hand up between my legs. I felt the touch of her fingers on my ballsack.

What the fuck was happening. I had never been measured before and did not know this was a part of the process. I had all kinds of feelings going on inside me. Scared, embarrassed, excited even aroused. Having never been touched anywhere near my private's and it didn't take much to set me off. I could feel my cock coming alive. Growing both in length and girth.

I heard Miss Smith say, "Ok Alan you can pull your pants up, I think I have all your measurements."

I grabbed my pants and swiftly pulled them up and snapped. I was still overcome by everything that had just taken place. I had been standing in the store in my underwear with my pants around my ankles.

Nobody else seemed the least bit bothered by the last several minutes, which did make me somewhat more comfortable.

Miss Smith had been off gathering articles of clothing while I was pondering what had transpired.

"This is an athletic supporter Alan," she explained handing me the item, "and it is worn underneath your gym shorts you won't need your tighty whities. Now just hop in the changing room and let's see how well my measuring skills have worked." u

Still in somewhat of a daze I stepped into the booth and removed my pants. While pulling down my underwear I heard my aunt Sandra say, "Honey you might want to close the curtains before you are completely naked."

Astonished, I looked over my shoulder and saw that in all my confusion I had completely forgotten to close the curtain. Luckily the way I was standing only gave my viewers the left side of my body. With the speed of light I closed the curtains and took a moment to collect myself. Thankfully no one saw anything but my left butt cheek, if that, and that was way too much for me.

After removing my undies I slid the jock strap on. It felt funny, there was no back to it. My ass felt so exposed, I could feel the air circulating around it. My cock was still stirring from being nearly naked and having my balls touched. I stuffed my semi erect penis into the jockstrap. It made a noticeable bulge when pointing down so I adjusted it to point up against my belly. I then stepped into the gym shorts. They seemed very short to me but then I never wore shorts of any kind, mom frowned them.

"How's it coming in there Alan?" Miss Smith asked from outside the curtain.

"I'm almost ready just give me a second," I answered. "I need to put the tee shirt on before I come out, can you hand it to me?"

"Nonsense, come out so we can get an idea of how well the shorts fit," said Miss Smith.

Aunt Sandra and mom echoed the same sentiment.

I stepped out of the booth and was motioned over to where all three women were standings.

Other shoppers were coming into view as the day progressed. I could see shoppers in different departments from my vantage point.

"Oh yes I think I did a great job on sizing up the fit of the shorts, don't you agree ladies?" Miss Smith gleamed, looking toward my mom and aunt.

"Yes they seem to fit very well, let's have a closer look," my mom said to aunt Sandra. As with my shoes they began inspecting the gym shorts. Mom and Aunt Sandra began feeling all around the shorts making sure they fit. They were rubbing around my butt to see if there was enough give for proper movement. Then they started sticking their fingers in the waistband and running them around testing the elasticity.

They were getting dangerously close to my penis. I just kept hoping one of their fingers wouldn't graze the tip.

This feeling around and poking was making my cock stir again, the feeling was amazing. I was subconsciously loving the arousal. My penis was growing with each touch I felt.

Suddenly I snapped back to reality, it was my mom and aunt touching me, how sick was I? That should not be arousing me. I couldn't believe it.

The inspection finally stopped and I assumed we were ready to pay and leave. Yeah, I thought, "I could get dressed and go."

My mom announced, "Now let's see how well the athletic supporter fits."

I swung around to face mom and shouted, "Mom you can't do that!"

"Young man you will NOT tell me what I will and will not do!" She said gritting her teeth. "I am your mother and sole keeper and am in charge of you till you are 21. You will do as I say with no questioning or back talking."

I had never seen my mom so angry and upset but then I had never defied her before.

She angrily stepped in front of me, stood there for a minute, looking me directly in the eye. "Do we understand each other young man?"

"Yes mom," I answered trembling a bit as I said it.

"Miss Smith please remove the gym shorts so we can examine the athletic supporter," mom demanded.

Miss Smith moved in front of me and squatted down. She grabbed the sides of my gym shorts waistband and slowly pulled them down to my ankles. This revealed an 18 year old guy standing in the center of a department store in just a jock strap.

I was dying of embarrassment. I could not believe this was happening. How humiliating. My ass was completely visible to anyone who happened to be behind me and looked my way. I didn't dare look anywhere besides straight ahead for fear of eye contact with someone..

I finally had the courage to look down at my predicament. Oh no, I could see the head of my penis barely peeking out of the jockstrap waistband. Nobody could see it unless they had my vantage point.

My mom and aunt surrounded me checking out the fit.

"Miss Smith, are all the athletic supporters this open in the back?" asked my mom.

Oh my god my mom was looking at my almost naked ass. She was seeing everything. She could see my ass crack with the fine hair creeping out of it.

I was trembling with embarrassment. What the hell was happening?

My aunt stood in front of me inspecting the garment. She reached down and felt the pouch, containing my cock and balls.

"What type of material is this made from?" She questioned.

Miss Smith took hold of another section of the pouch and replied, "it's a blend of elasticized cotton and spandex, if I'm not mistaken."

"Ruth, check the label in the back to be sure," Miss Smith suggested.

I felt a pull on the waistband from the back, my mom was going to check the makeup of the jockstrap material. "That's ok," I thought she couldn't reveal much more in the back.

My aunt and Miss Smith now moved to the waistband checking the fit. "Does this part have a lot of give?" my aunt asked.

"Oh yes, it's extremely flexible, let me show you," said Miss Smith. She grabbed it in the center, below my belly button almost grabbing my penis head, and pulled it straight out. This revealed the head of my penis to them.

Holding the gap open, Miss Smith uttered a huge gasp and kept looking down at the tip of my penis.

My mom quickly returned to stand in front of me with my aunt. Now all three women were gazing at the head of my semi erect penis.

"Oh my goodness Miss Smith, what's wrong?" Mom asked, looking between me and Miss Smith.

"I'm so sorry I shouldn't have been so rude," she said.

"Whatever do you mean?" my mom asked.

"I had no idea there was a problem with his...his...you know his malformed penis," she whispered.

My mom gave her an uncertain look and said, "Malformed?"

"Oh dear yes, it has a covering over the end of it, like a cloak or hood." Miss Smith again whispered.

My mom and aunt looked at each other for a few seconds pondering what Miss Smith had just said.

"Miss Smith," my mom asked, "How familiar are you with the male body?"

"Well never having been married I don't have much first hand knowledge. But I saw my older brother once getting out of the shower and drying off. He was naked and I saw his penis but it didn't look anything like Alan's. The tip end of his was pinkish and mushroom shaped, not covered in a hood."

My aunt and mom chuckled and mom said, "Dear your brother was circumcised."

Miss Smith gave them a most confused look, as if someone had asked her to wear her shoes on her ears. "I don't understand what you are saying, aren't they all alike?"

Aunt Sandra chuckled and said, "Similar but not exactly the same."

Miss Smith still had a dumbfounded look on her face and moaned, "I guess I'm just stupid about things like this, I have no experience to go on."

Mom shaking her head said, "Well there is no time like the present to set you straight."

I had just been standing there mesmerized by what was taking place around me not really absorbing the conversation.

I was rocked out of my stupor when mom took hold of my jockstrap and gave it a yank, it slid down to my mid thighs.

"Mom," I screeched, "What are you doing?" I could not believe her actions.

I was now standing in the center of the store completely naked with the exception of the jockstrap around my thighs. It didn't seem real, it couldn't be real! My mom, my aunt and this sales lady were all looking at my naked body, noooooooooooo!

Mom said, "Be still, were only helping out Miss Smith with a quick anatomy lesson. Now stand still for just a moment and we will be done and we'll head home."

My aunt started talking, "Some men are circumcised and some are not. Circumcision is the removal of the penises foreskin, usually done at birth. There are many reasons for and against the process. One of the best reason to keep the foreskin is for the man's pleasure."

"I'm not understanding this at all," Miss Smith languished.

At that point my aunt looked at me and started reaching for my penis.

No, no she's not going to touch it, please don't let her touch it, please!

She grabbed my penis and started explaining.

"The foreskin covers the head of the penis. The head is that pinkish mushroom part of your brother's penis you saw."

My aunt then took hold of my penis with her other hand. One holding the shaft, the other she used her index finger and thumb to retract my foreskin revealing my plump head.

"Oh god tell me this is a dream!" My aunt is touching my penis while my mom and a neighbor are watching! I am totally on display for anyone in the department store to see.

"Now does his penis head resemble the one you saw when your brother was naked?" My aunt asked Miss Smith.

She bent down for a closer look and replied, "Yes it does but I don't remember his being so, well, as bulbous as this one."

Now they are discussing the details of my penis, how humiliating, and with each moment my aunt continues to hold my penis I can feel it grow.

I can NOT get an erection, no no no no way! It's bad enough to be in the situation I'm in now, I do not want it to worsen.

"You were saying that one of the reasons to retain the foreskin was for the man's pleasure, how could that possibly be?" Miss Smith questioned. "I guess I just don't understand the mechanics of it all."

My mom chimed in, "By keeping the foreskin intact the friction caused when it is pulled back and forth over the head is very pleasurable for the man."

As my mom is explaining this to Miss Smith my aunt is demonstrating the action my mom is detailing.

My aunt is starting to masturbate me! Again my aunt was starting to masturbate me in the middle of a department store! My penis was growing by the second. My bulbous mushroom head was swelling to its mammoth size.

"Oh my goodness, what's happening to it?" Miss Smith questioned, not taking her eyes off my rapidly growing penis.

Mom continued her lecture, "This pleasurable action stimulates the brain to send more blood flow to the penis. This causes it to expand and become erect and hard, normally in preparation for sexual activity."