Who is Jessica Ch. 02

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.

"Fuck fuck fuck fuck fucking fucking fuck!" I screamed into my bed. There I was. Doggy style on my bed, my ass in the air stuffed with a plug. Dressed like a slutty school girl and sucking hard on a big fake cock. Of course this would be the moment Dad decided to barge into my room. I knew he saw everything. My room was set up in such a way that my bed was fully visible as you entered the room. My headboard is on the side wall so you see my bed, and anything on it, in profile.

I was so embarrassed and humiliated I couldn't think straight. I pulled the dildo from my mouth and just curled into a ball on my bed and sobbed. Of all the possible ways to come out to my Dad this never even registered. Horrible thoughts of Dad kicking me out of the house or disowning me sped through my mind and I sobbed harder.

I don't know how long I laid there crying but eventually I got my emotions under control and was able to get undressed and back into my boy clothes. I found an old shoe box in my closet and put all my toys in the box and slid it under my bed. No real reason to hide it anymore but it seemed the appropriate thing to do. I sat back down on my bed not knowing what to do now. I finally decided to text Derrick for advice.

I grabbed my phone, my hands were still shaking slightly. "Hey...have your parents ever caught you....ya know..." I hit send on the message. Knowing full well he would ask what I meant but I'm still not confident enough to just come right out and say things like that.

"No I don't know. What did your Dad catch you doing???" He sent back and I sighed. I knew he would make me say it.

"Dad just caught me jerking off" I sent back knowing I couldn't beat around the bush.

"Ohhhh shit that's awkward. What did he say?"

"He didn't say anything he just screamed, slammed the door, and ran away"

"Huh that seems like a bit of an overreaction."

"Well I wasn't just jerking off...."

He sent me a gif of a guy looking confused with a bunch of question marks all around him.

"I went to a sex shop today and bought a few toys and stuff since I'm 18 now and he saw me... using stuff." Once again I was so embarrassed but I needed the advice so I pressed on.

"Ohhhhh...kinky." He replied and I rolled my eyes frustratedly.

"What should I do asshole?!?!?"

"How dafuq should I know dude?? I've never been caught, with toys or otherwise. I don't know what to do here. But it seems like you have two options. Never speak about it again or talk to him."

I slammed my phone down on my bed. That was no help at all. Of course those were my two options but I was hoping for a secret third time travel option somehow. I really did not want to talk about this but was it even possible? Would Dad bring it up? All sorts of questions were flying through my mind.

I looked at the time, it was 5:48 pm. I had been crying and thinking for a couple hours now and it was time to get ready for dinner. I wasn't even sure Dad would still want to go but I got dressed anyway. I wore a nice collared button down shirt. It was a solid royal blue and a pair of black dress pants with the only pair of dress shoes I owned. Thankfully they were black as well. I came out of my room and walked down stairs and into the living room around 6:30. Dad was already dressed and sitting on the couch watching TV. Dad was dressed a bit nicer in a white button down with a light blue sport coat. Khaki dress pants and brown shoes. Leave it to Dad to always look fashionable. Even with my recent humiliation I couldn't help but think how handsome he was.

Dad was a very good looking man. He had a strong jaw and a stubble beard. Salt and pepper hair even though he was only 41. At 6"3 he was tall and he was trim and muscular. He didn't have a 6 pack or anything but you could take one look at him and know he was in amazing shape.

"Hey Shawn, ready to go?" He jumped up from the couch when he saw me. I just nodded and we made our way out to the garage and got in the car. It was only a 15 minute drive to the restaurant but it felt like hours. We drove in silence. Awkward, awkward silence. Once or twice Dad said something about the weather or how he was hungry but I wasn't listening. I was drowning in embarrassment and had absolutely no idea what to say.

We finally pulled up to the restaurant and Dad paid for valet parking. The valet hopped in the truck and Dad put his hand on my back and we walked into Pioneer's Legacy. Our table wasn't ready just yet as we were 15 minutes early and we had to wait. Again we just stood there not speaking to each other for 10 minutes until the hostess told us the table was ready and escorted us to it. The table was small and set for two people with candles, our napkins shaped like swans on our plates, and even flowers as a centerpiece. All in all it was very...romantic honestly.

We sat down and again didn't speak. I kept my eyes on the table and fidgeted with my napkin and utensils. Dad looked around for a bit but finally sighed loudly and said "Ok this can't keep going Shawn we need to talk about what happened."

Here it was, I knew Dad would want to talk about it and not just let it go. "Dad I really can't do that right now." I said, my voice wavering slightly. My emotions threatened to overtake me again and I really didn't want to make a scene.

"I'm sorry Shawn, but we need to get past this. All the books I've read about this make it clear that I should wait for you to come out on your own but it looks like I'm going to need to take the first step. I know you're gay Shawn." Dad said.

I looked up, startled. That was not what I thought he was going to say. "W...wait what? You know that? How do you know that? Did Derrickntell you?" I blurted out, those were just a few of the questions I had.

"No, no one told me. Is Derrick gay too? Are you two together?" He blurted out. Asking a few questions of his own.

"Ew no, Derrick isn't gay Dad. He's the only one I've ever told so if he didn't tell you then how do you know?" I said, looking at him intensely.

He sighed and rubbed the back of his neck. "Well Shawn, I mean you're 18, you've never had a girlfriend, you've never even talked about a girl you're interested in," He sighed deeply again "and buddy... you're not as subtle as you think you are." He said, looking at me with a funny look on his face.

"What does that mean?" I said a little defensively.

"Well, I've never caught you staring at a girl... but I've seen you staring at men." He said looking at me, he seemed to get more confident the more he explained. "We have gone to the beach multiple times and you're never staring at women, but your eyes are glued to the guys. We have watched movies with nude women and you look bored, but a scene with a shirtless man and you're transfixed." He looked at me like he expected me to answer a nonexistent question.

Just after he said this the waiter came by. He was tall and muscular. He had a smooth shaved head and a strong jaw. Very attractive and I looked up at him and stared for a brief second and then looked down to the table. My father chuckled and I looked at him. He had a 'told you so' look on his face and I shot a death glare at him.

We ordered our drinks. Dad got a beer and I got a soda. He had that shit eating grin on his face the whole time the waiter was at our table. When he left a minute later I shot another glare Dad's way. "Ok, fine, whatever. You're right, ok. Happy?" I said in an irritated tone. He just laughed a little.

"Son, you know I love you more than anything and I will always support you. You had nothing to worry about coming out to me. Although I know it's easier said than done." He said looking at me like he's done so many times in the past, with love and support.

I sat there and pouted for a minute or two before I sighed loudly and nodded "I... I know I'm sorry, and thank you, Dad, that means a lot to me." I said looking back at him. Once again I couldn't help but think of how handsome he was. I blushed again and looked down at the table. I couldn't believe he had read books about having a gay child. On one hand it was exactly something he would do, on the other it felt almost like an invasion of my privacy somehow.

"Now about what you were doing..." he said trailing off and my head shot back up to look at him.

"Oh God Dad no please can we just forget about that?!" I said urgently and he shook his head.

"No Shawn, I need to get this out." He said. Dad paused for a second and looked like he had to gather the courage to start talking again. "I read about having a child who is transgender and I just want you to know you have my full support." He said and kind of looked proud of himself.

I was mortified. It was bad enough he knew I was masturbating but now I had concrete proof that he saw that I was dressed like a sissy too.

"Dad I'm not transgender and I'm not talking about this now." I said in a low harsh whisper but he kept going.

"Well you never know Shawn, I'm just saying the books I've read say this is how this kinda thing can start and I just want you to know if you want to dress like a girl around the house it's ok!" He said a little too loudly for my taste.

The waiter came over at that moment to take our dinner order and I swear he looked at me differently. I'm sure he overheard Dad's loudmouth. We ordered our food. Dad got a ribeye and I got a filet. The waiter complemented our order and hurried away to put it in.

"Dad. Not here. Not now." I said through clenched teeth and he finally put his hands up in surrender.

"OK that's all I needed to say, let's enjoy our evening." He said and raised his beer. "To you Shawn. Happy 18th birthday. I love you and I always will." He said, clearly meaning well and to change the subject but I was still so embarrassed. I raised my glass and clinked his bottle and drank.

The next hour or so was spent talking about nothing in particular. The food came and it was delicious. There is nothing better than a good steak. After dinner the restaurant brought out an amazing looking dessert. Thankfully this was a nice enough place that they didn't sing happy birthday so the whole restaurant could hear. I was very happy about that. Every year Dad would tell the restaurant it was my birthday and every year I sat there awkwardly while they sang. It was awful.

We ate our dessert and headed out. The restaurant must have alerted the valet ahead of time because Dad's truck was out front as we came out into the parking lot. Dad tipped the valet and we got in the truck and headed home. A few minutes into the ride Dad spoke up once again.

"So just so we're clear, if it will help, then you can dress however you want. I'll even take you shopping this weekend!" He seemed excited at the prospect. I scrunched down in my seat and tried to disappear

"Daaaad I'm not trans. I just.....I just liked how the girl clothes felt ok. I'm done talking about this. Seriously." I said looking over at him. His face seemed to say that he got the message.

"Ok I get it. Just maybe next time try locking your door huh?" He said with an elbow nudge and a chuckle. Dad reached out to turn the radio up but I stopped him.

"Hey, why did you barge into my room anyway? You never do that." I said looking over at him. This time it was his turn to blush and stammer a bit.

"Ahh well... umm I... heard... gagging... and I was afraid you were choking or something." He glanced over at me. I couldn't have scrunched down any further. My face was on fire. He heard me gagging on my dildo and thought I was choking. Fuck my life.

The rest of the drive went by relatively fine. It was awkward but not nearly as bad as before. I even engaged in a little small talk. When we got home Dad suggested we watch a movie or something but I just wanted the night to be over. I told him I was too tired and headed on up to bed. I texted Derrick again and let him know how the dinner went and he was happy for me that Dad knew now. It did kind of feel good for him to know, although every time I thought about how he found out I died a little inside.

I turned on my computer and started playing Elden Ring to get my mind off things. Next thing I know it's a few hours later at nearly 11:00 pm. I was thirsty and decided to head downstairs to get a glass of water. I left my room, closing my door quietly so as to not disturb Dad. I had to walk past his door to get to the stairs and as I got closer to the stairs I heard something strange coming from his room.

The sound was extremely faint but I could still hear it. Curiosity got the best of me and I very carefully pressed my ear to Dad's door and I could hear a bit better. With my ear to the door I could almost make out what the sound was, and it kind of sounded like a moan. I pressed my ear to the door harder as if that would help but I heard it again. It was definitely a moan, but it wasn't his. It was high pitched and there was a slapping sound as well. It dawned on me then. "Oh shit Dads watching porn!" I thought to myself and blushed again. I quickly but quietly pulled away and went down stairs. My need for a drink was forgotten but I did grab a glass. I went back to his door and very carefully placed the glass against his door and my ear to the glass.

"Oh yeah take it bitch" I heard along with a louder slapping sound. "Ohhh fuck yes spank me Daddy!" I heard a reply. The slapping sound came again a few more times. "Mmm yeah you like that sissy bitch?! You like Daddy's big fat cock" I heard and my jaw dropped. Did he just say sissy? "Ohh yesss Daddy I love your big fat cock in my ass!" I heard again and I couldn't believe my ears. Not only was Dad watching porn but he was watching hardcore sissy porn!

The video kept playing and I heard a few more lines before the fucking sound became more intense. It's then that I realized it wasn't all coming from the TV. I could hear Dad stroking his cock. He must have been going hard because a few seconds later I heard a loud moan and groan. Again this was not from the TV. Dad must have just cum hard. My own cock was rock hard at this point and I scurried back to my room trying to make as little noise as possible. I flung myself onto the bed and tugged off my shorts. I stroked my cock hard and fast and came in under a minute.

I laid there panting, my cum cooling On my tummy and my mind racing wildly. I just overheard my Dad watching sissy porn. Not only that but he came watching sissy porn. Is Dad gay? How Does Dad even know to look up sissy porn? Is...is he attracted to sissies? Is he attracted to me?!

I couldn't sleep that night. My mind was all in flux and nothing made sense anymore. But I knew one thing. I needed to figure out the answers to these questions. I needed to seduce my Dad.

The next morning I decided to put the rough plan I had come up with into action. I hopped out of bed and grabbed my basketball shorts and rolled them up a few times, exposing a bit more of my legs. I had never really had an issue with body hair. I didn't grow much. I even got asked if I shaved my legs once or twice. I then threw on a white tee shirt that was slightly too small for me showing off a bit of my midriff. I took a look at myself in my mirror and decided I looked good. Then I headed out of my room and down stairs.

It was still pretty early and Dad didn't seem to be awake yet. It was Sunday and he did tend to sleep in a bit. I decided I was going to make breakfast and went about making eggs, bacon, and pancakes.

After about 10 minutes of cooking I heard Dad making his way downstairs. I quickly dropped a spoon onto the floor and bent at the waist to pick it up. Dad had a full view of my ass as he came into the kitchen and I heard him stop dead as he walked in. I stayed bent over for a fraction of a second more than necessary and stood back up

"Oh hey Dad. How did you sleep?" I said putting the spoon into the sink and going back to cooking.

"Uhhh, yeah pretty good, how about you?" He said. I couldn't tell if he was shaken by my display or if he was just still waking up.

"Eh, not great. I was tossing and turning all night. Weird dreams...ya know like sexual dreams" I said with my back to him blushing deeply. This was way outside my comfort zone but if my plan was going to work I had to get used to being more sexual around Dad.

"Oh yeah those...those can be a pain" he said and I could practically hear the gears turning in his head. I was never this open about sexual things

"Haha well they weren't really a pain just distracting and... intense" I said, bringing him a plate of eggs and bacon, with a second plate of pancakes. I sat the plates down in front of him and put a hand on his shoulder as I did so. I saw him looking me up and down for a quick second before looking up at my face

"You ok son? You seem different this morning" he said, looking a little concerned.

"Yeah Dad I'm great. I mean, my secret is out. I can finally be myself around you." I said, grabbing a plate for myself and sitting down across from him. I only had eggs and bacon on my plate as I didn't want to get too full.

"Oh well that's great Shawn I'm glad you can be yourself around me now. I just want you to be comfortable." Dad said and took a fork full of eggs and started eating.

"Thank You Daddy, that means a lot to me." I said as casually as possible but I knew it made an impact as Dad started to choke on his eggs. I jumped up and ran over to him and started patting and rubbing his back "Dad are you ok?" I asked a little panicked

Dad nodded and coughed a few more times "Yeah yeah i'm ok I was just surprised. You haven't called me that in years." He said chewing the last of his food and swallowing before coughing a couple more times.

"What? Daddy? Huh, I guess I haven't. Do you mind?" I said trying to act innocently but still rubbing his back slowly, not helping him clear the food but just rubbing his back now.

Dad swallowed hard and I knew it didn't have anything to do with the food. He nodded and looked up at me "No of course not, you can call me whatever you want" he said and held my gaze for a few seconds.

I smiled and leaned down and kissed his cheek "oh thank you Daddy" I said and blushed again going back to my seat. I sat down and looked at him from across the table and he was blushing too. When I got back to my seat I saw that I had dropped my napkin in my haste to get up and help Dad. I sat down and bent over in my chair and under the table to retrieve it. That's when I noticed the massive bulge in Dad's pants. My jaw dropped. It was huge! He must be packing at least 7 inches in his pants and just the thought got my body tingling.

I sat back up and acted like I hadn't seen anything. We went on with breakfast making casual small talk until we were done eating. I grabbed both mine and Dads plates and took them over to the sink. Dad came over to help me wash up but I shooed him away "I got this you go and relax Daddy" I said with a smile and went back to work on the dishes. He stood there for a moment not really knowing what to do. I usually hated doing dishes so me doing them on my own was even stranger.

Dad went into the livingroom and turned on the TV. I smiled as I heard the TV turn on and some sports show started playing. The guys on TV were talking about someone doing something in football and it was awesome or whatever. I couldn't care less. My plan was working. I finished the dishes and looked at my shirt seeing it was pretty dry which wasn't going to work. I "accidentally" splashed myself a little and smiled.

I walked into the living room and made a show of my shirt. "Ugh geez I got all wet doing the dishes. I need to change" I said. Making sure Dad saw my wet shirt before I peeled it off showing my flat tummy and bare hairless chest. I stood there for a few seconds and looked out the window into the backyard and got another idea. "Oh you know what, I think I'm gonna take a swim" I said and walked out of the room without another word. Dad's eyes were glued to me the whole time.