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?"
