Lucy's Story: Roleplay with My Dad

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Nailing this Halloween.
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So a long long long long time ago I had promised some random Anon I would try role playing with my dad. Something that I have never done before. Well, Halloween finally came and went which meant costumes were on sale and it was finally my chance to do it. He recommended I do a cowboy and Indian theme which seemed interesting, but of course I didn't really have the costume for it so I never actually attempted until now. Just a few days before Halloween I had decided it was finally time to give it a try and went shopping with my sister and brother for some costumes. Needless to say, I finally got around to purchasing the costumes and did my first "attempted" role play with my dad and brother.

It was the Friday before Halloween and everything was ready. Just two days before, I had went shopping with my siblings. More specifically; costume shopping. Although I needed a costume for the Halloween party on Monday, my real intentions was to purchase one for the purpose of role playing. I had never role played in my life before and I honestly didn't know what to do or expect. The closest I probably got to role playing was playing as Lady Macbeth in my English play. How different could it be right? The concept seemed simple enough; just pretend you're somebody else and act it out. It didn't seem that hard but I was hesitant to believe it would be that simple. Luckily though, finding the costumes I needed was a breeze although a bit pricey to be honest. I found a pretty nice looking Native American costume among the countless of other Native American costumes that were in the store. Surprisingly, there were multiple different variations to choose from. I went with the cheapest one they had to be truthful. Which still wasn't very cheap. The costume was made from a material that closely resembled leather but undeniably fake leather. I doubted they would sell me real leather for $40. Despite the price, the costume was fairly nice and simple.

It was a dark brown hide leather dress that went just to my knees with a single strap going over my right shoulder to hold the dress together. The bottom portion of the dress primarily consisted of a skirt that was cut at a slight diagonal with a bunch of tassels dangling off at the end. There wasn't much else to the dress except for a few turquoise blue diamond shape patterns outlining the neckline of the dress and the arms. Besides the dress, a braided belt with colorful blue and white feathers came included too; just to wear along with the dress. There was also some tanned leather bracelets for your wrists with more tassels dangling off and a braided blue and white head band. Overall, the costume seemed fairly simple. Sort of similar to what Pocahontas wore except much more bland and basic in my opinion. Disappointingly though, for $40 dollars no boots or shoes came included. Kind of a rip off if you asked me. Luckily though, I had some old cowboys boots at home which I intended on pairing with this dress to compensate for the lack of shoes. For a simple costume like this, it was definitely on the more expensive side but ultimately I was hoping it would all be worth it in the end. After picking out my costume, I went around and also found a cheap $7 dollar cow boy hat for my dad to wear. Frankly, I didn't think he would be willing to wear a costume. I was lucky enough if I managed to convince him to wear the hat alone. Either way, I bought the hat without consulting my dad before hand and just hoped that he would be willing to wear it. If not then there went $7 down the drain.

Now at the time I went costume shopping with my brother and sister, I really had no idea or intention that my brother would be joining me as well. If I did, I probably would have forced him to follow the same theme as me. Regardless, they each bought what they wanted and it was what it was. For my sister she bought herself a cute little Minnie mouse costume. Surprisingly she had somehow managed to convince her boyfriend to go as Mickey mouse and together they matched as a couple. It took a while for her to find it but in the end she managed to find all the components needed for the costumes. It was pretty simple in fact, more simple than mines even. All her costume really was, was a headband with black semi-circular mouse ears and a red-white polka dots bow between the ears. It came with a matching red skirt with white polka dots as well and some white gloves. Although the costume came with a red blouse, my sister had no intentions of wearing it because of its "ugly" style. Instead she opted to wear her own sleeveless black blouse in replacement. Either way I was certain it was going to look just great on her. Unlike me and my little sister however, my brother had went in the opposite direction and bought something extremely different instead. One of the things you should know is that my brother's not really the type of person who enjoyed dressing up to much. To him it was just a waste of energy and time.

Unfortunately he needed a costume to go to a party as well. Rather than buying a full set costume like us, he went and picked out a fairly creepy zombie-like clown mask. The mask was basically a clown grinning with smears of blood and ripped flesh wounds across his face. There was clumps of frayed rainbow hair sticking out at the top as well; adding to the appeal of the mask for my brother. I honestly didn't like it but that didn't stop him from buying it. He argued Halloween was a time to be 'scary not cute.' That was a valid point. Not able to argue against his logic I just let him be. In the end we each managed to get our own things and the real fun was finally going to begin. When we got home that day, I spent a few thoughtful minutes deciding on how I was going to ask my dad about this. 'Hey, dad. Are you busy this Friday? Want to wear fuck your little daughter while wearing our costumes because I want to try role playing with you' I played it out in my head. It sounded stupid asking him upfront like that but there really was no other way to ask him about it. It was hard trying to come up with the exact words to say in order to avoid sounding weird but really there was no way around it. Most of all it was going to be hard explaining why I wanted to try this all of a sudden if he asked me. Regardless my mind was set and I intended to make it happen no matter how awkward it was going to be.

Around 6PM he came home. Looking drained, I gave him some time to shower and eat before I decided to finally ask him. He was sitting at the dinner table with a cup of tea, reading the news on his iPad. I sat in the chair next to him and tried to get his attention.

'Hey dad?' I tried drawing his focus towards me.

'Hmmm?' he heard me but didn't look up from his iPad.

'Are you busy after work this Friday?' I asked him anyways.

'No I don't believe so, why?' he scrolled on his iPad. That's good then I thought to myself. The easiest part of asking was over now. Now it was time to ask the real question.

'Do you want to have sex on Friday then?' I bluntly put it. Normally when we had sex, it was usually him asking me and not the other way around. No doubt he thought something was slightly unusual. He raised a brow but didn't bat an eye towards me.

'Sure sweetie' he replied back not really interested.

'Can you also do something else for me while we have sex?' I asked him some more.

'What do you need?' I hesitated to tell him for a few seconds unsure if I should back out while I still can.

'Well, I was wondering if we could try something new?' I finally grabbed his attention. I watched as his finger turned off the iPad screen and his body shifted to face me. He had a surprised but slightly interested look on his face.

'What do you want to try exactly?' he asked me back.

'Don't laugh okay? Just listen to me first before you start laughing at me okay, dad?' I felt a bit awkward with what I was about to say. He nodded his head understandingly and quietly listened. Here goes nothing I thought to myself. 'I was wondering if we could try role-playing a bit while we're having sex on Friday' I told him forwardly. He chuckled a bit as I told him my plan. I looked up at him to see his reaction. Brows raised high and lips slightly pursed. It was hard to tell what he was thinking.

'Are you serious?' he looked at me confused by my request.

'Yeah' I shrugged.

'Why though? Did your brother put you up to this?' he thought I was joking. 'Are you pulling a joke on your dad again?' he sighed with a hint of disapproval.

'No dad. I'm serious' I shook my head adamantly. 'I'm actually wondering if you could try it with me on Friday' I assured him I wasn't joking around. 'If you don't want too its okay too' I quickly added just as his facial expression indicated he was lost.

'No, it's fine. I'll try if you want' he replied back quickly. 'It's just that you normally don't come to me that often for sex, especially "role playing" sex. What gives?' he asked me curiously.

'I just want to try. I read about it somewhere on the Internet and it sounds kind of fun' I partially lied to him.

'Uhuh' he nodded skeptically.

'If you're busy or if you don't want too it'll also be fine with me' I still gave him the option of backing out it if he wanted.

'Nope, I'll try it just for you' he shook his head reassuringly that he would be alright trying it with me. 'Friday night then?' he doubled checked with me.

'Yeah, Friday night whenever you're not busy.'

'Hmm okay then sweetie' he let out a soft unbelievable chuckle as he went back to his iPad.

That was the end of that. For the mean time anyways. I left him and headed back into my room. Surprisingly, I did not expect my dad to agree that easily. Perhaps it was so easy to convince him due to the fact that I had intentionally left out what type of role playing we were doing and neglected to tell him that he needed to wear a cowboy hat. He probably assumed it was just regular sex with a bit of acting. Maybe once he found out on Friday he would give it a second thought and change his mind.

Either way, it was done and I had successfully managed to get my dad on board for now. Now all I had to do was wait for Friday. To be honest, I should have spent those two days researching or familiarizing myself with the type of role playing we were doing. Unfortunately I did not and when Friday came, I was clueless how to even begin. I got home from school that day, feeling exhausted and tired like I usually do. I was a bit excited for Friday to come but when it actually came, most of my excitement faded away thanks to school. All I really wanted was to just pass out and sleep but a part of me felt bad for my dad if I fell asleep on him. My dad was going to be home in an hour, so I decided to use my time wisely for once and went to take a quick shower. Taking that refreshing shower was mostly what I needed to bring my energy back up. Although I still felt tired, I was fairly sure I had just enough energy for the night ahead. My dad came home shortly after. He quickly came into my room and checked up on me to see if we were still game. I was if he was. Oddly there was a huge grin on his face as if he had been looking forward to this the whole day.

'I'm still okay with it if you are' I told him.

'Tonight at nine then?'

'Okay' I nodded my head excitedly.

'Don't pass out on me now, sweetie' he laughed just as he made his way out. I tried to keep myself busy in the mean time. Homework, texting, listening to music, anything to keep myself awake. It felt like an eternity waiting for nine o'clock to come. At around six, I gave up trying to study and went downstairs to eat dinner with my sister. The house was mostly empty. Just me, my sister and my dad today. My brother was off hanging with his friends somewhere so I had no idea when he would be back home. On the other hand, my mom was still at work until eleven. It was kind of quiet in the house today to be honest. Nothing exciting was going on except for maybe tonight.

That was the only thing I looked forward too and was keeping me awake. Dinner went by quietly with my sister mostly on her phone ignoring me. By the time I finished, it was only seven. The next two hours were probably the longest hours of my life. My eyes were constantly closing and my head kept drooping every few minutes as I was on the verge of passing out. Another shower felt like a good idea. If only I had the energy to get into the bathroom though. Time seemed to go on forever. I wasn't even sure what time it was anymore until my dad showed up into my room.

'Are you sleeping?' he checked up on me.

'No' I sat up straight, stretching my limbs to stay awake.

'It's nine now' he pointed at the clock.

'Oh, it is' was all I said. He looked at me, waiting for me to say something. I looked back waiting for him to take the lead. Somehow a part of me forgetfully thought this was all his idea and not mines.

'Here or in my room?' he finally broke the silence. My sister was busy in our shared room so I didn't wanted to disturb her from whatever she was doing.

'Your room' I suggested.

'Alright' my dad walked back out of the room. Grabbing the costumes and some supplies in my drawer I followed right behind my dad as he led me into his room.

'What's that for?' he looked at the bag I was carrying.

'The costumes' I opened the bag for him to see. He took a look inside and pulled out the white cowboy hat he was going to be wearing shortly.

'For Halloween?' he tossed it back in the bag.

'No... For us, dad' I corrected him. His eyes shot up and he looked perplexed by what I had just said.

'Hold on, what do you mean?' he stopped at the door of his room.

'We're role playing dad. We have to dress up' I smiled at him guilty. He scratched his head like he was lost.

'You didn't tell me we were dressing up for this' he replied.

'We're role playing, dad. Of course we have to dress up!' I grinned as I pulled out the dress I was going to wear.

'I thought we were just going to pretend' he interjected.

'That's not any fun though' I added. He gave me this slightly annoyed glare and shrugged. I probably should have told him first I thought in my head.

'How much was it?' he opened the door to his office for me.

'Cheap' I lied, scared that he would start yelling if I told him the truth.

'Do you not want to dress up?' I started worrying that he was going to be grumpy all night about me not telling about the costumes.

'What am I wearing?' he asked me with a tint of annoyance.

'Just a hat' I promised. Originally, I intended to make him wear this nice leather jacket he had in his closet as well but from the look on his face, I didn't think it was going to happen.

'The cowboy hat?' he walked into his room.

'Yeah, just the cow boy hat I promise' I pulled it out the bag and tossed it to him.

'What are we even acting as?' he looked at the hat with an unamused look.

'Cowboys and Indians' I clarified for him.

'Let me guess. I'm the cowboy who's going to save an Indian princess from being run over by a train?' he looked at me predictably.

'Uh not really' I shook my head as I stepped into his office.

Although he called it an office, it wasn't really an office. It was just the guest room with a desk inside. Somehow, my dad had managed to take over the room and converted into a "mini" office. In one corner of the room he had his personal desk with his laptop on it and a nice white office chair behind it. He had also set up his own cabinet with personal files and documents he used for work. Perhaps his greatest modification to the guest room was the addition of a 42 inch flat screen television that he mounted right at the wall facing his desk and the queen sized bed. Whenever there was a hockey game he needed to watch or when the television in the living room was in use, this was his go-to place. For the most part, my mom didn't mind him using the guest room as his own personal office as long as he kept it clean. And he usually did; taking great care to keep it clean and ready to be used by guests if needed. Or for sex in our case.

'Are you going to tell me what we're role playing about then?' my dad went and sat on the bed.

'Give me a second' I reached into the bag to find the supply I had taken with me from my room. 'We're doing cowboys and Indians except reversed' I told him.

'Reversed?' he raised a brow, waiting for me patiently.

'I'm going to be the Indian warrior taking back my land from you' I awkwardly tried explaining to him what we were doing. To be honest, it sounded a lot better in my head than it did trying to explain it. Basically what I had in mind was a simple scenario. I was going to be the Indian warrior who had just captured my dad; a cowboy, trying to steal my land and I was going to make him pay. I knew it sounded a bit racist and ridiculous but that's what I went with.

'They're called Native Americans, not Indians. Also cowboys didn't steal the Native Americans land' my dad corrected me.

'I know, I know, I know' I rolled my eyes at my dad's correctness. Being that we were Canadians, we called them Native Americans or First Nations here but for the sake of role playing, I wanted it to feel like we were in the past again. I already knew that having my dad be a cowboy who was stealing land made zero sense but I told him to just go with it. I spent a few good minutes just standing there, explaining everything to my dad while he kept correcting me about everything I said.

'If this was real, I would have probably shot you or you would have died from polio, etc...' he went on and on about everything wrong with this scenario. Every time he corrected me, a part of me died. It was a lot more challenging than I though it would be trying to get my dad just to play along with it. By the time we finished 'clearing' things up, the scenario was tweaked slightly to fit with my dad's standards. I, the young Native American warrior had caught my dad, who is the outlaw cowboy trying to steal from my people. More specifically he stole my ancestors sacred ancient jewelry. A jewelry passed down from generations to generations. Whether or not that really happened historically, I did not care. Luckily though, I had just caught him before he was able to get away with it. Thus, it was time to make him pay for what he did. Through sex of course. Overall, not much was really changed besides what I had mentioned. As long it meant my dad was happy then it was fine by me.

'Are you sure you really want to do this, dad? If you don't I can always ask Big Bro to try with me instead' I made sure my dad was alright with everything one last time.

'Yeah it's fine, sweetie. I think I can handle a little role playing' he chuckled unsure if he really could. It was finally time to start.

'Put on the hat' I eagerly told him to put it on. He gave one last unamused shake of his head and put it on. I stared at my dad with a huge stupid smile. A part of me stood there desperately holding back my laughter while another part resisted the urge to take a picture of my dad wearing the hat and send it to my mom. Surprisingly though, he did kind of look like a cowboy. Somehow with his white cowboy hat and the big brims sticking out from both sides of his huge head, he looked like he fitted the role. Paired along with his copper red sweater and his blue jeans, he sort of looked like he could have been living in the western country side. A modern day looking cowboy I thought to myself. It didn't look great but it fitted him well at least.

'Sit on the chair' I pulled my dad's office chair to the center of the room.

'Why?' he got up and sat on it anyways. As he sat down I pulled out a golden ball of yarn from my bag. 'What is that for?' he stared at me as I came closer to him.

'To tie you up okay, dad?'