A few years ago, I was going through a difficult time. I had lost my job, mostly due to my own irresponsibility. I was working in a factory with a very early start time. After being either a little bit or sometimes very late on many occasions, I was eventually let go. Without any money stashed away, I quickly got behind on my bills and I struggled to make the monthly rent payment.
Although I was searching for a job, I couldn't really find anything that paid a decent wage. Left with few options, I elected to sell my car. That put a little bit of money in my pocket, and I was spared some expenses, including insurance. Since I lived in the city, there were taxi cabs in the neighborhood, as well as a bus route. My roommate had a car that I could borrow in case of emergency as long as I didn't become a burden.
The plan that I had was to settle for a lesser-paying job within walking distance. There were quite a few options, but most were at restaurants, particularly fast-food ones. I had spent some time doing that in my high school years and that certainly wasn't something that I wanted to do again. One of my targets was a local grocery store. I stopped there, one day, to put my application in, as well as pick up a few items. On my way back, I noticed a "help wanted" sign in the window of a shop called "RPM Records". The store was located in an old shopping center and I had never even considered frequenting it before.
Since I didn't have anything better to do, I decided to check it out. The parking lot was littered with potholes and the store was very weathered and worn. The "help wanted" sign was one of those old, plastic ones with a black background and bright orange lettering. A slightly crooked neon sign in the front window read "OPEN" in all capital letters as it made a buzzing sound.
When I opened the door, a bell attached to the back of it jingled. As I looked around, it was clear that nothing had been updated in well over thirty years. An older man stood behind the counter, tinkering with a record player. He stared at me momentarily, clearly thinking that I was in the wrong place, before asking if he could help me. I pointed toward the sign and asked if he was still looking for help. He didn't seem very impressed with me but he said that he was still hiring.
He was looking for someone to cover anywhere between noon and closing on Monday through Saturday. That actually sounded like the perfect schedule for me. There was a brief exchange of conversation that mostly consisted of him asking my age and where I lived.
"So, do you want it?" he offered.
I was a little bit confused by the question.
"The job?" I asked.
"Yeah, the job. What else were we talking about?"
It seemed like I had managed to pass the rigorous screening process. After thinking it over for about a minute, I accepted the offer. I asked him when he wanted me to start and he responded, "Today is good."
I think he wanted me to get right at it, but I told him that I needed to take my bag of groceries home and that I could be back in a half-hour. That seemed to work for him, so I rushed home and was back at the shop in record (pun intended) time.
The owner's name was Tom and he was already of retirement age for a normal job. Everything in the store was very low-tech. Items in the store were labeled with a round white sticker and the price was written in felt marker. There was no inventory system of any kind and the point-of-sale system was just a basic cash register. The price was to be entered manually and then simply hit the "taxable" key. There was a "non-taxable" key, as well, but there were no such items sold in the shop.
Tom gave me a tour of the shop in between dealing with customers. That wasn't too difficult, though, because there were no customers. It was a record shop, so ninety percent of the inventory was simply records. To be honest, I had never even touched a vinyl record before that day. Being twenty-six years of age, that era was a bit before my time. Tom gave me a crash course in the basics, but it was obvious that he had a wealth of knowledge about the product.
The bulk of our inventory was the long play, usually called LP, records. The new, sealed product was kept separate from the used ones and they were further sorted by category. Tom only carried three combinations of genres in the store: Rock/Pop, Hard Rock/Heavy Metal, and Country/Bluegrass. The vast majority of the store was in the Hard Rock/Heavy Metal category. That wasn't a surprise, because it was clearly what Tom liked the best.
Little else was on offer in the store. There was an assortment of framed music posters, all of them vintage, of course. Behind the counter were several disorganized boxes of phonograph needles that were a complete pain in the ass to cross-reference and locate. To say that I was good for little other than running the cash register would be an understatement. Most of my shift was spent standing around, answering the occasional phone call, or packaging one of Tom's eBay orders for shipment. There was one other employee that I sometimes worked with in the evenings, Mike, but he would not be around for long.
To help fill the time, I offered to enter the store's inventory into some sort of inventory program. Tom didn't seem overly excited about it, but he went along with it anyway. Because the only computer in the store was a hundred years old, I brought my laptop in and loaded a freeware inventory program. It took several weeks to get through all of the inventory, at least the inventory that was on display, and enter it into the system. I was the only one who used the program, but it was nice to have some idea what was out there.
By the time I had finished the data entry, Mike had left. He was convinced that the store was going to close soon and he had another employment option that presented itself. Once again, the discolored, old "Help Wanted" sign made its way to the window.
I could clearly see why Mike was concerned. There were nights that I didn't make a single sale. Most of the people who shopped at the store wouldn't buy or sell anything without dealing with Tom. I wasn't authorized to buy used records anyway, because I had no idea what they were truly worth. Additionally, I didn't really have permission to barter on price, although I would sometimes knock a dollar or two off in order to make a sale. Convinced that I had to do something to make a positive impact on the business, I offered to take over the "online sales" division of the corporation.
Although Tom was incredibly knowledgeable, he was not very good at doing listings. There were never any actual pictures of the product included to make the customer feel like they knew the quality level of the item. Tom balked at my request, but I convinced him to let me list one item for sale. I asked him to write some key selling points of the item on a Post-it note so that it looked like I knew what I was talking about. I listed the record, which Tom clearly didn't think I could sell, on Facebook Marketplace. It was "Metallica - Ride The Lightning" in very good condition. I was told to include the words "Megaforce" and "First Pressing" in the listing.
About twenty minutes later, I could see that Tom was getting irritated by how much time I was spending on my phone. His mood changed when I informed him that I had just spoken to a customer in town and he agreed to buy the record for two hundred and twenty-five dollars. Trying to downplay his enthusiasm, Tom asked how much he would have to pay in fees. When I told him that there were no listing or sale fees and the man would pick it up in a couple of hours, I could see the cogs start to turn inside the old man's head.
From that day forward I was presented with a stack of records, each with a Post-it note attached, at the start of my shift. Initially, I was selling about half of my listings, which was about five times as many sales as Tom was making on his online sales previously. After making contact with some specialized influencers on the platform, I was able to do even better. The stack of records that I was being asked to list seemed to get a little bit larger each day. This was about the time that she showed up.
Tom had finally found an employee to be Mike's replacement. It was a very skinny, timid, young woman named Becca. She was incredibly shy and soft-spoken. I did most of her employee training, and it was obvious that she wasn't very comfortable talking to people. The number of customers coming through the door had increased slightly by that time because some of our local online customers were picking up their items in person. That allowed us to sell other items to that customer if they were interested.
I turned over most of the online listings to Becca. She did a good job with them and she was quicker at it than I was. I did my best to take care of most of the physical customers so that she didn't have to experience as many awkward encounters.
As our Facebook sales increased, it became apparent that we needed to upgrade the packaging for our items to be shipped. It was a good excuse to talk to Tom about expanding the online business as I tried to get him to cover an Amazon bill for some sturdier packaging. He happily agreed to both.
When I had unsuccessfully attempted to properly inventory our stock, I had accounted for more than five thousand records. There was also a storeroom full of stuff and there were mentions of a storage unit somewhere. I can't imagine how many records Tom had stashed away through the years.
Becca and I had become pretty busy during the evenings. We probably averaged thirty listings per day, which made for a lot of interactions on Facebook. Becca even started to come out of her shell a little bit. We found that we had a lot of common interests. Both of us were geeks, and we liked all kinds of geeky stuff, whether it was gaming, movies, or television. We would talk all shift long about Marvel Cinematic Universe, Game of Thrones, Star Wars, or anything else along those lines.
She always seemed to be covered from head to toe with several layers of clothing. Whether it was wearing multiple shirts, long pants, or a baseball cap, she always seemed to be completely covered up. Each day I worked with her, I got increasingly curious about what was lurking underneath all those layers. Becca wasn’t terrible to look at either. She had light skin with a few random freckles and long, reddish-brown hair. A subtle dimple dotted her chin and she had lovely blue eyes that I didn’t dare to stare into for too long. Her ears tended to poke out from her long, straight hair, particularly when she was wearing a baseball cap.
In just a few months, the online business that Becca and I had built was about seven times what the entire store was doing previously. Granted, that was a very small number to build from, but we quickly became Tom’s two favorite people in the world. We both got a significant pay increase, which was appreciated.
Every day, Becca and I would hang out together at work for roughly six hours. It didn’t even feel like a job most of the time. Whether we were talking and joking around or jamming to one of Tom’s retro records, it was always a good time. I didn’t even fully realize why I liked being there so much until one afternoon in particular.
Becca had asked me to play one of her favorite songs, Looks That Kill by Mötley Crüe. Sometimes we would jam out to one of the records and play “air guitar” and the like. As I looked down the aisle, Becca had tossed her hat aside and was flailing her hair in all different directions as she pretended to sing into a microphone. She looked so incredibly sexy and it was at that moment that I realized how infatuated with her I had become.
In the following weeks, I tried desperately to get her to notice me as more than a friend. Although she was only a couple of years younger than me, I felt like she perceived me as a “big brother” and nothing else. Her conservative dress was driving me increasingly crazy. Why such a pretty, young woman would keep herself covered up like that, I will never understand.
She became the inspiration each and every time I sought out self-gratification, and there were many. Desperate to finally get her attention, I made arrangements on a Saturday to get my roommate out of the apartment for the night. It took bribing him with a case of beer to pull it off, but I managed to get the place to myself for the night.
I was so incredibly nervous about making a move on Becca. The job and her had become my entire world and I felt like I was risking it all by asking her out. I tried multiple times but kept chickening out. Near the end of the day, I finally worked up the courage.
“Hey, I was, um, wondering if you wanted to stop by my apartment after work and hang out?”
She smiled at me. I could tell that she didn’t know what I was getting at.
“Doing what?” she asked politely.
That didn’t help my nerves at all. I was shaking so much that I think she picked up on it. I really hadn’t thought all of the scenarios through, and my brain was not working at all.
“Uh…Maybe we could just have a beer or something and watch Star Wars and…”
“And what?” she asked.
I didn’t know what to do. It was all going terribly wrong. I wanted to rewind the whole fucking thing and either try again or forget about it. In my panic, I did the unthinkable.
I grabbed Becca’s face with both hands, leaned in, and kissed her. She didn’t seem to respond at all. I was sure that I had totally fucked up.
As I pulled back, she had a surprised look on her face. It was obvious that she had never even considered me as anything other than a friend.
“I, um, uh…Okay,” she stammered.
Holy fucking shit! She said “Yes!”
Fortunately, it was close to the end of the day. I couldn’t stop smiling like an idiot and there were way too many uncomfortable moments between the two of us. We struggled to interact like we normally did. It was obvious that things had changed. I could only hope that things would work out alright.
After work, I got into Becca’s car and we took the one-minute trip to my apartment. Once inside, I grabbed two bottles of beer and led her to the couch. We queued up The Phantom Menace and I awaited the opportunity to make my move. Fortunately, we settled back into our usual groove and started to have some fun. We had each seen the movie a dozen times, so we started a little competition to see who could remember the most lines. We went back and forth for quite a while, many times breaking out in laughter at one another’s bad acting.
I couldn’t take it anymore, I had to kiss her again. This time she responded and we didn’t stop until she was on her back and I was on top of her. Knowing that she had confidence issues, I told her over and over how beautiful she was and how much I wanted her. As I started to unbutton her outer shirt, Becca started to act nervous, once again.
With her outer shirt fully unbuttoned, I could finally see the outline of her body. She was incredibly skinny, perhaps weighing ninety pounds, and her breasts were predictably petite, as well. I had to feel them, even though they were still covered by a snug t-shirt and her bra.
As I glanced at Becca’s face, she seemed like she was in some sort of turmoil. I told her that I would take it easy and that we could stop whenever she wanted. Slowly, I peeled away her layers of clothing until I removed her black, cotton bra.
I was, admittedly, a little bit surprised by her breasts. They looked as if they were just developing, but that didn’t make sense because she was twenty-two. It was something that I had never seen before, but I decided to chalk it up to her tiny physique.
Nevertheless, they were absolutely lovely! My hands and mouth each took a turn exploring them and I had become so completely aroused that I feared an early release.
Becca seemed so nervous. I asked her again if she wanted me to stop, but she shook her head “No.”
I started to rub her crotch and something seemed to be different. Part of it was the way that she responded, the other part was what seemed to be a thick seam of denim in the front of her jeans. Retrospectively, there were a lot of signs, but I couldn’t even begin to see them.
As I started to loosen Becca’s pants, I could hear the chattering of her nervous breathing. I slid my hand slowly inside her panties only to find something unexpected: her small, stiff, little dick.
With my hand wrapped partially around it, I stared at Becca. She looked horrified as she realized that I had absolutely no idea about her gender identity.
“I’m sorry. I wanted to tell you, I just didn’t know how to,” she pleaded, trying to choke back the tears.
I couldn’t find the words to say anything. To say that I was dumbstruck would be an understatement. The longer that my silence went, the more upset Becca got.
She backpedaled away from me, trying to hastily put her clothes back on. Mumbling apologies through her tears, Becca said that she had to go.
That thought shocked me back into reality. I grabbed her shoulders and pleaded for her to stay. Although it certainly made me look foolish, I had to admit that I didn’t have a clue about her gender identity. I told her that I wanted her to stay and still felt the same way about her. Becca started to calm down and I think we both had gained a bit of acceptance of each other's situation.
“I still want to,” I confessed as I stared into her lovely, blue eyes.
“You do?” she asked.
I nodded in response.
Becca suggested that we regroup and try again. She headed home so she could properly get ready and I took some time to figure things out in my head.
It was just over an hour before Becca returned. I spent most of the time pacing around the house. I had convinced myself that she wasn’t coming back.
In the past, I had seen quite a few images and videos of transexual girls. Whether they were tagged as shemales, trannies, ladyboys, traps, or something else, I always found them intriguing. Some I found attractive for various reasons, others not so much. I preferred the smaller, feminine types, such as Becca, mostly because I wasn’t interested in being on the receiving end. Still, I wasn’t convinced that I could actually go through with such an encounter.
When Becca returned, she was wearing significantly more makeup than usual. A Pokémon backpack was slung over her right shoulder and she was wearing a single shirt and a short skirt.
I invited her to come inside as if it were her first time in the apartment. She looked different than I had ever seen her. It seemed apparent that some of her usual apparel was designed to help mask that she was still in transition. There was something about her legs and torso that, although very slender, looked slightly boyish. That didn’t really matter to me, though. She still looked lovely, and she still looked like Becca.
With a smile, I asked her to spin around slowly so that I could take in every bit of her. Slightly embarrassed, she did a quick little runway model performance for me.
Becca told me that she had never had sex before, with either a girl or a guy. She admitted that she had two “boyfriends” hidden in a dresser drawer that she sometimes practiced on, but she had never experienced what a real one feels like.
I think the hour we spent apart did both of us good. We were able to talk more candidly once we had some time to process everything. She even admitted that she had always seen me as a “big brother” type, but that she gets turned on by those porn videos with a "big brother" and his "little sister." There was a brief make-out session that got increasingly intense and aggressive until we decided to move the action to my bedroom.
Becca insisted on a bit of striptease. I think that she wanted to give me a look at exactly who she was. As it turned out, it wasn’t a full striptease, she kept her panties on. She looked increasingly like somebody who was "in transition" as her clothes came off.
“Stop teasing me, Becca, I can’t take much more,” I pleaded.
It had already been a long night and we decided to not delay it anymore. She handed me a small bottle of lube and climbed onto the bed on all fours. I approached Becca, who was wearing nothing but her thong panties, and poked a lubricated finger into her tight, little hole. I felt my jealous cock throb, as it clearly wanted a piece of the action. After fingering her for a couple of minutes, I grabbed Becca and turned her over and onto her back.
“I want to see you and I want you to see me too, Becca,” I stated.
As I lifted her legs, I asked her to hold onto them while I cast her panties aside and guided my cock to its target. I could clearly see the outline of her limp, little dick through her snug panties. She let out a whimper as I breached her tightly puckered hole.
It was a first time for me in many ways, as well. However you choose to classify her gender, it was my first time having sex with anyone not equipped with a vagina. I mention that specifically because my cock had never entered the other hole before.
Although I could tell that she had opened herself up earlier and done some preliminary lubricating, she was still tighter than anyone else I had been with. She moaned with every gentle thrust of my cock, her voice sometimes breaking and sounding more boyish.
While I would have loved to do this particular dance with Becca for hours, the intensity of the moment assured us that our first encounter was going to be brief.
Becca reached her right hand inside her panties and started rubbing herself. I pulled her hand away as I leaned forward, folding her legs back into her body. It wasn’t too dissimilar to my previous sexual experiences except for the fact that I had to pin her back a little bit more, which raised her backside off of the mattress.
I slid my hand inside her panties, exposing what had been Becca’s little secret. I wrapped my hand around it and rubbed the underside of the head with my thumb in a circular motion. As Becca stared at me, I could see that she was not going to last very long either.
Becca’s body tensed up and the back of her head pressed into the mattress as her cock spasmed in my hand. A couple of clear, watery drops of liquid dribbled out and splashed onto her midsection. I felt her hole tighten up as she came. She clenched onto my cock so tightly that she locked the outer layer of my cock in place. There was no stopping at that point. I continued thrusting in very short strokes. The rigid core of my cock slid beneath the skin as my climax arrived.
My cock throbbed as I pumped a hot, creamy load inside of Becca. She lifted her head as the initial blast rocked her hole. I watched intently as she gasped with every twitch of my cock. It was incredible watching as she tried to absorb every subtle sensation of the experience.
Afterward, we cleaned up and spent most of the night in my bed. Although I was naked and Becca was just wearing a clean pair of panties, there wasn’t really any more sexual contact other than some toying and teasing. We barely slept, at all, that night. Most of the night was spent talking and getting to know each other better. As much as the admission of my feelings for Becca and her secret threatened to ruin our relationship, what we had just done seemed to have somehow righted the ship.
The next morning, after getting around and having some fun in the shower, we both got dressed. Becca had just put on one of her more typical outfits when my roommate arrived home. I hadn’t told him exactly why I needed him to vacate the apartment for the night, but he figured it out pretty quickly. He smiled and joked about what we had been up to the previous night. I could tell that he didn’t know Becca’s secret either, because he was flirting with her in front of me.
I walked Becca out to her car and kissed her goodbye.
“See you at work tomorrow. Can I call you later?” I asked.
“I don’t know…Can you?” she joked.
She hopped into her beat-up old car and drove off. I stood there and watched as it slowly disappeared from sight.
