Who is Jessica

Hello everyone! Thanks for checking out my story. This is my first attempt. This story is a slow burn so this is mainly just set up but it will get very hot I promise.

This is a work of fiction. Names, characters, businesses, places, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental.

Have you ever had one of those moments in life where you know that by making just one decision your entire life will change so drastically that you'll never be the same? That happened to me as I knelt on the floor, dressed like a whore, and stared at my fathers hard cock.

Yeah I know it's a cliche and click baity intro but I really had no idea how else to start this story. Plus it's true, it did happen to me, but I guess I should explain how I got there.

My name is Jessica, but when this story takes place my name was Shawn. I've learned a lot about myself over the years and I'm so happy with the way my life has turned out so far but it's been a wild ride. I was born into a pretty well off family. My parents were in their early 20s when they had me and they got a lot of help from my grandparents on both sides so we never truly struggled when I was younger. We weren't rich by any means but we were comfortable.

My dad was a whiz at numbers so he rose through the ranks of an accounting firm pretty quickly and my mom was good with people and became a therapist. She was a wonderful woman and so sweet and understanding. We had an amazing life together until 6 years ago when she died in a car accident.

No one was at fault, it wasn't a drunk driver, it wasn't negligence, just one of those freak accidents that can happen. That didn't make it any better though, and with no one to be mad at, I got mad at everyone. I lashed out at everything and everyone. I pushed my friends away, I took out my anger on strangers and I even got into fights at school. These never went well for me considering I was, and still am, small for my age. I'm 20 now and still just barely 5'3" and 125 lbs soaking wet.

Most of all, my relationship with my father suffered. All he ever wanted was to help but I pushed him away more than anyone else in the years after mom's death. I Feel so bad about that now but there's no going back to the past so I just have to make up for it now.

A few friends stuck by me, even with me pushing them away. None more so than Derrick. He is my best friend in the world and without him I probably wouldn't be here today. Derrick is my neighbor and we grew up together. Hell, we were inseparable since we were toddlers. Derrick's parents were about the same age as mine, maybe a bit older I've never asked. They are pretty good friends as well, but I guess that's to be expected with kids who are best friends. My dad and Derrick's dad get together with some other guys once every month for a poker game. When mom was here, her and Derrick's mom would play Go Fish or Rummy or something while the guys played poker. Not that they weren't invited, it wasn't like that, they just didn't like poker.

Derrick helped me so much growing up. He was a lot like me when we were kids. Small, nerdy, shy. That all changed when puberty hit. He shot up like a rocket, while I stayed short. He got into sports while I got into video games. He got more confident while I got more reserved. Although we went through puberty very differently we still remained best friends. If not for Derrick, I would not have made it through the years after moms accident. It was his support and platonic love for me that finally made me strong enough to accept my sexuality. See I wasn't just going through the loss of a parent I was also struggling with my sexuality.

I knew I didn't like girls for a long time but I couldn't accept the fact that I was gay. I live in a small town and people here can be kind of judgy about sexuality. So I repressed it as best I could but that never works. Derrick gave me the courage to come to grips with myself and come out to him. When I did he just smiled and gave me a big hug and slapped me on the back. It was all I needed. After I came out to him my life once again changed drastically. Just having one person who I could be my true self with made all the difference.

In the years after I came out to Derrick my life got better. I stopped pushing people away and started acting more like myself again. I was able to process my mother's death, even though I'll never be over it. My relationship with my dad got better, it didn't get back to like it was before mom but it was good. I started doing better in school again and life was pretty uneventful...that all changed when the fire nation attacked...I mean, when I turned 18.

The day of my 18th birthday finally arrived and I smiled as I opened my eyes. I loved it when my birthday fell on a weekend. I raised my arms over my head and stretched while yawning. My elbow hit my phone as I lowered my arms and I grabbed it checking to see if I had any birthday wishes. I had a few from some friends and family and I had one voice message from Derrick. I smiled and hit the play button.

"Eyyyy brother!!" His voice came from my phone, drunk and yelling. He must have been at a party last night. "Happy birthday! You're finally a man!" I rolled my eyes at that. Derrick was just 4 months older than me but to hear him talk about it, it seemed like 10 years. "Listen listen now that you're finally at the big boys table I think it's high time you tried to...GET SOME!" He yelled from my phone louder than before. I again couldn't help but roll my eyes. He lost his virginity about a year ago and ever since, he's been telling me to "get some" yet that wasn't really possible for me. As I said before I live in a small town and I wasn't ready for anyone but Derrick to know about my sexuality yet, so dating was not in the cards. Anonymous hookups were also an absolute no go so that left me very sexually frustrated.

I put my phone down as the voice message ended and as always any time Derrick mentioned "getting some"' it made my mind wander. I started to fantasize about what it would be like to have sex. Never with Derrick, our relationship wasn't like that, but other guys at school. Even some teachers made it into my brain. I had a thing for hot older guys. What can I say? It wasn't long before I grabbed my phone again and pulled up one of my favorite things in the world. Sissy porn.

I found sissy porn a while back and have been obsessed with it ever since. It was so fucking hot to me. I also knew I was sexually submissive from watching porn. Any video, any story, I always wanted to be the one in the submissive role. I also saw sissy porn as a way of affirming my homosexuality, I know that's not the most healthy thing in the world but it's what I had.

I loaded up one of my favorite sissy hypnosis videos and put in my ear phones. Within minutes I was naked and squirming on my bed watching a video telling me to suck cock and I wanted so badly to do it. My mind flashed to the plan I had for the day as I slowly stroked my cock. It, like the rest of me, was not the biggest. At only 4 inches hard. I knew I was better suited for a submissive role on that account too.

I was panting hard and stroking my cock faster and faster and when the video showed a large cock cumming on a sissy's face, I erupted myself. Spraying my flat belly with my cum and biting my bottom lip to keep from moaning out loudly. As I laid in my bed breathing hard in post orgasmic bliss I knew I had to follow through with my plan.

The plan was, the day I was allowed to go, I was going to a sex shop in the city about an hour from my town and getting some toys to play with. I wanted so much stuff and I had been saving up from the part time job I had and today was finally the day.

I quickly got up and hopped into the shower to clean myself off and got dressed. I found the goth style when I was going through all the shit and I really liked it so even after I started coming out of that black hole I still kept the look. I put on a pair of black pants that had too many zippers and a black metal tee shirt and grabbed my backpack. I quickly ran downstairs barely able to cover my excitement but Had to hit the brakes when I saw my dad in the kitchen

"Morning birthday boy!" He said with a wide smile holding a cup of coffee. "I was thinking I'd take you out for a nice breakfast. Whatcha say?" He said, looking at me. It made me feel bad to say no but I really wanted to go to the city.

"Umm sorry dad I actually have a really big test coming up and I need to go to the library and study. But how about dinner?" I said, trying to appease him. He looked me up and down and gave me a small smile that said he was reading into things more than he should. It was a common thing for him to try and find hidden meaning in things people say. During my black hole days he would often be able to see through me and see I was having a particularly bad day. It always made me even more mad when he did that.

"Dinner sounds great kiddo. How about Pioneers Legacy at 7?" He said before Taking a sip of coffee. My eyebrows shot up so fast I thought they might launch off my forehead. Pioneers Legacy was the nicest steakhouse in the area, and We only ever went there for super special occasions.

"Are you sure dad?" I asked and he waved a hand at me almost before the words were out of my mouth.

"Of course Shawn! It's your 18th birthday, it's a huge milestone in your life. We need to celebrate it properly!" He said, raising his voice a bit. I couldn't agree with him more but I think my plans were a little different than what he was imagining.

"Wow! Ok, yeah that sounds great dad!" I said and ran over to him and gave him a hug. I made a conscious effort to be more physically affectionate with him since I was such an ass for years and as sick as it may be, my father sometimes made it into the fantasies I was talking about earlier. I couldn't help it, the man was very attractive. He was only 41 and he was in amazing shape. It also didn't help that he was much larger than me, standing at 6'3" and 220 lbs of pure muscle he was every bit the manly man you'd expect. So every now and then getting a little physical with him was definitely something I was interested in.

The hug didn't linger but my mind wandered for just a brief second to that impossible fantasy situation. I pulled myself away before I could get too far down the rabbit hole and waved as I went out the door. "Bye dad, love you, see you tonight!" I said and headed into the garage and into my car.

Within a few minutes I was on the road, headed to my destination and I could not contain myself. I was so excited I was practically bouncing in my seat. I turned on some music and rocked out the whole way to the shop but when I got there they weren't open yet. In my excitement I failed to remember stores like this didn't open until later in the day. Luckily the one I wanted to go to opened at 12 and it was almost 11 already.

I decided to walk around the city a bit and check out some other shops. The local college campus was right down the street so there were plenty of stores that catered to a younger crowd. I stopped in a store that had a number of little stalls inside it where local artists could sell their stuff. There were a ton of cute things but I couldn't afford to spend money on anything else but sex toys.

I stopped into another shop. This one a gaming store that had a lot of fun stuff for nerds, which I definitely thought of myself as one. They had games like DnD and Magic the gathering as well as board games, other tabletop stuff and merch. I had gotten into Magic The Gathering a few years ago, I wasn't any good and didn't spend much time or money on it but I knew enough to look like I belonged.

I was looking at a few cool dragon statues the store had when I heard a voice behind me. "That's a nice pin you have there." I froze for a second before turning around. Not expecting anyone to even notice me, let alone speak to me. Standing there however, was one of the most attractive men I have ever seen in my life. He couldn't have been that much older than me but I was struck by the air of maturity and confidence he put out, especially in this kind of store. Most guys who came in these places were, let's just say less than confident, but not him. He flashed me a half smile and I felt my cheeks heat up and I stammered "o..oh th...thanks umm which one?" I said as I had 4 or 5 pins on my backpack.

"The Elden Ring one, it's my favorite game" he said with a little chuckle that made my stomach do flips. Elden Ring was a video game that came out in the last couple years. It was famous for being very hard but also one of the best games ever made. I smiled and nodded back

"Oh! Cool yeah it's my favorite too!" I said and suddenly I felt...relaxed. I don't know why but I started talking more and before I knew it we were deep into a conversation about the game. Talking to strangers, especially about nerdy stuff, was way outside my comfort zone but this guy made it easy. We started talking about other things too like different interests and hobbies. It was one of the most fun conversations I've ever had with a stranger. After just a few minutes he kind of jumped and pulled his phone from his pocket. He was getting a call and ignored it but then looked at me.

"Damn I gotta run but it was really fun talking to you. Do you go to Northeastern?" He asked. Northeastern was what all the locals called the college down the street and if I had not been accepted to a college a few states away that's where I would be going.

"OH ummm no I'm still in my last year in highschool but I'm actually heading to school out of state." I said blushing a bit. Telling this greek god of a man i was still in highschool felt...I don't know? Pathetic? Somehow. I caught myself sort of wishing I hadn't been accepted after all.

"Oh, well, that's a bummer. I guess I'll see you around. I'm here a lot if you ever wanna stop by while visiting family. Who knows, maybe we'll bump into each other again." He said with that little half smile I couldn't stop noticing.

"Yeah! That sounds great! I will definitely stop by" I said, before catching myself. "I mean you know when I come back to visit or whatever." Fuck i was being awkward. Every fiber of my being wanted to give him my number, to keep in touch with this man but I knew it was futile. I was going to college half the country away and I lived an hour away already. It would just be an online relationship if anything did ever come from it and I didn't need that in my life right now.

He nodded and gave me one more half smile before he walked away and I couldn't help myself but to watch him until I couldn't see him anymore. I blinked a few times as if coming out of a transe and checked my phone. It was 12:37. I had been talking with him for over an hour! I couldn't believe it, it felt like 10 minutes. The shock wore off quickly though when I realized the real reason I came to the city was open now.

I quickly walked back to the sex shop a few blocks away and took a deep breath before walking inside. This was it! The moment of truth! I walked in and I was very surprised. It was not at all what I had imagined. It was a lot brighter than I thought it would be, and cleaner. The only real frame of reference I had was either porn or tv shows and they never seemed this nice in those.

A pretty woman, probably in her early 30s, walked out from behind the counter and approached me. "Hey there, welcome In. Do you have an ID and we also don't allow backpacks in the store. I could hold it for you at the counter until you check out though!" She said, all bubbly and sweet. I nodded and fumbled in my pocket for my wallet. Through no fault of this woman I was suddenly very nervous and struggled a bit to get my ID out. I handed it to her after a minute of struggling and she smiled widely "oh happy birthday sweetie! Welcome to adult life hehe" she giggle and handed my ID back and put her hand out for my backpack

"Th...thank you." I said in a very subdued voice and handed over my backpack. In my head I knew this would be awkward and embarrassing but it took all my willpower not to sprint out of there. The woman took my bag and smiled at me again

"No reason to be nervous honey, no judgment here. Do you need help finding anything?" She said in a softer voice and a look that told me she really meant what she said. I shook my head rapidly from side to side.

"No umm no thank you I'll be ok" I said, my voice soft but tight with nerves. She nodded and walked away back to the counter. I slowly started making my way into the store proper and was amazed By the rows and rows of sex toys. All sorts of different styles, sizes, colors, uses. It was very overwhelming. It took me a few minutes to adjust to just being there.

I had a mental list of the things I wanted and I took a few deep breaths and steeled my nerves and set off to find everything. It took some time but I found nearly all the stuff on my list. With my arms laden with things I went to the counter knowing this was going to be the worst part of the whole ordeal.

The woman who took my backpack was standing at the register, she's probably the only one working today, and she smiled as I approached. I dropped my assortment of goodies on the counter and she looked at them. Her smile never wavered and her eyebrows raised just a touch but she made no other mention about the things I had brought.

As she rang up my new toys and put them into a thick black plastic bag I went through my mental list again to make sure I had everything. Two realistic looking dildos. One larger and one smaller with a suction cup base. A few butt plugs ranging in size. A pair of handcuffs. A ring gag. A collar. A small leather paddle. A chastity cage. Nipple clamps. A few pairs of skimpy panties and finally two sex costumes. One being a school girl outfit and the other being a nurse's outfit.

I kept looking at the woman as she bagged my stuff, waiting for the laughter and judgment to come but it never did, instead she looked at me once she was done ringing my stuff up and smiled.

"So, I know this can be embarrassing but I want to make sure you get everything you need. Do you have lube or toy cleaner at home?" She said without a hint of judgment in her tone and I looked at her blushing deeply but confused. Of course I had heard of lube before but toy cleaner? "I'll take that as a no." She reached behind her and grabbed a few bottles and put them on the counter.

"ok so there are a couple options for lube. You can go water based, it's a little less slick but feels more natural. You would need to use more of it but it doesn't stain and it wouldn't have any effect on your toys." She said holding up one of the bottles. She put it down and grabbed a second one. "This one is a silicone based lube. It's slicker, thicker and lasts longer. The downside is it would stain if it got on your sheets, and it may have an adverse effect on your toys over time, breaking down the silicone in the dildos." She said ending the little lecture as I stood there with my face on fire. She looked at me expectantly and I slowly reached out and pointed to the water based lube. I didn't want any stains or anything I would have to explain to my dad.

"Good choice." She said and put the other lube away and grabbed a larger bottle and a medium bottle of the lube I chose. "I'm going to throw the large one in for free for you. Just be sure to use a lot of it as you first start out." She said as she rang up the smaller bottle and put them both in the bag. "Now this is a toy cleaner and it's important to use this after each session to keep everything clean and safe." she said and put that bottle in the bag without ringing it up either.