Jester Cosplays

('A Bowsette Cosplay' is the first story in what's turned into a series, the second story was 'Erza Cosplay'. This is the third story in the tale of the Dragovans life. I've been checking on the comments on the previous stories, thank you for the support!)

We laid there together while I filled Daisy in on the entire night. When I told her about intentionally bending over to give Saul a view of my ass she pinched my ass cheek. "Such a tease, he totally went home and thought of that while using his hand."

"It's a good thing he's got a big hand because that monster he's got is huge. I got an idea of just how big when I caught him making an adjustment after I bent over in front of him."

"Sounds like you might be more into him than you initially thought."

I sighed enjoying the feel of her arms around me, "Yeah I might just be."

"I know I said I'd be ok with it if you wanted to hook up with a guy and that's still true. But like I said you need to make sure he knows the whole truth about you before you do." she gave me a big squeeze, "I don't want you getting hurt because some guy freaked out at the surprise."

There was a bit of silence before I said anything, "I don't think it's an 'if' anymore but a 'when'. I do want to wait a bit though, you know? For the right moment to come."

I paused for a little bit but she could tell there was more so she just laid there in silence with me until I spoke again. "What do you think about the two of us sharing a guy some time? Maybe for my first time?"

Daisy ran her hand over my shoulder, "I think that's a fantastic idea, I could help prepare you for your first real cock. Once you're ready I could watch while your pussy gets filled."

I turned to face her behind me the best I could, "I don't have a pussy."

She gave my ass a squeeze, "Oh yes you do."

"Oh yeah I do, don't I?"

She pulled my hair to the side and kissed my neck as she wrapped her arm around me pulling me close to her. "Your hair is growing so long. How long do you want to grow it?"

Enjoying her lips on my neck I was slow to respond, "Um a little past my shoulders. Long enough to look great in an updo or in a simple ponytail."

Her hand on my abdomen slid down into my panties to tease my cock, using my own cum as lube as she stroked me until I was hard again. "That long will be really cute on you." Then she stopped completely and slid out from behind me, "Probably should get ready for bed now." she teased before slipping into the bathroom.

I tried to follow quickly but my pants were still around my knees and I nearly fell getting up to pursue her. I rushed into the bathroom pulling my pants up which got her giggling, but I didn't stop until I was face to face with her pulling her close for a kiss. Sliding my hands down her body and opening her pants. My hand slipped into her panties and I could feel how wet she was, she really did like the idea of us sharing a guy.

My kisses on her lips moved to the side of her neck before I nibbled her earlobe, "Turn around" I whispered into her ear. As she listened I pulled her pants and panties down just enough to expose her pussy. She bent over and grabbed the sink in front of her as I pulled down my own pants and panties freeing my hard cock.

Slowly I pressed myself into her feeling the warm embrace around my shaft. Standing there in front of the bathroom sink I began fucking Daisy from behind. Holding her by the hips with both hands guiding us together. As I continued pushing in and out of her I slid my hand around her stomach and up to cup her left breast, with my right hand I moved to gently tease her clit.

I watched her face in the mirror, seeing the pleasure written on the glass. Her eyes were closed enjoying the sensations, slightly biting her own lower lip. So I leaned forward and whispered in her ear all the while continuing to fill her with my cock, "Open your eyes and watch yourself as I fuck you."

Daisy's eyes fluttered open, at first she appeared uncomfortable watching herself but as I picked up the pace thrusting in and out of her the discomfort left and was replaced with desire. Her mouth opened in a moan as I leaned forward to nibble on the side of her neck. As my fingers played with her clit I could feel the shaft of my cock sliding in and out of her.

I gently squeezed the breast in my hand as I felt an orgasm building and moved my nibbling to her ear where I whispered, "Do you see what I see? A beautiful woman getting her pussy filled and enjoying every moment. Cum for me and show yourself what that looks like."

As if she had been holding back her own orgasm, at my instructions I felt her pussy contract around my cock while she let out a cry of delight. Her cumming sent me over the edge and I gave her what I had left after she had already fucked me with the dildo pushing almost everything out.

As I softened I slipped out of her and pushed her to lean more against the sink. I pulled my panties and pants up before kneeling on the floor behind her. She shuttered when my tongue brushed against her pussy giving me the taste of us mixed together. I began to draw my own cum out of her pussy with my tongue taking the occasional moment to suck her clit into my mouth.

"Oh Fuck Yes! I'm cumming again!" was my only warning before her pussy spasmed sending the last of my cum out of her and onto my face. She leaned against the sink catching her breath for a moment before turning around and looking at me kneeling on the ground behind her cum still on my face smiling up at her.

"I see why so many guys enjoy giving cum facials, it's incredible seeing you like this." She reached down and wiped some cum off my cheek and sucked it off her finger. "But let's clean up and get ready for bed."

When I woke up the next Saturday I knew it was a Roxy day and got ready accordingly. The quick pull over fake breasts were incredible for changing day to day but I still kept the ones I originally got that I glued to my chest. I knew those would still be great for times I knew I would be Roxy for longer periods like at the convention in a few months.

When Daisy eventually woke up that morning I was just finishing up breakfast and when she saw me in a sundress with my hair in a messy bun she greeted me, "Good morning Roxy, are you up for a bit of dress shopping for the Gala today?"

"Good morning beautiful, sure sounds like fun. This will be my first time getting a fancy dress."

"Oh you're going to enjoy it, we'll find the right dresses and then hunt for shoes to go with them."

Spending the day shopping for our dresses was so much fun, I didn't even know there were that many options of places to get a dress. I learned a lot about styles and designs, and trying on all those dresses felt magical. The sales woman who sold us the dresses we chose was amazing, her questions about what we were looking for relied less on what styles we were looking for and more about getting to know us.

Only after learning our hobbies and interests then moving on to what the event we were shopping for did she start making recommendations. Realizing we were a couple she recommended complimentary styles and colors, when we explained that half way into the night I would be changing into the dress from a suit she made a recommendation to start the night in the dress then change into the suit. It was the right call and we were even able to purchase a dress shirt that matched my dress from her.

After a bit of shopping we stopped for a late lunch, Daisy talked about making some hair appointments for us before the gala.

"Kham from the dress store was right, it makes sense to go as Roxy first. That way you can have your hair done all nice instead of just pulled into a messy bun. I can make some appointments for that afternoon."

She reached over and played with my hair now grown longer, almost halfway to the length I wanted. "What do you think about getting extensions to get your hair to shoulder length? It'll mean a longer time spent getting our hair done but I think it'll be worth it."

I turned and kissed her palm, "I trust your judgment and a bit of time spent sitting in the salon would be worth it, I'm going to keep taking the supplements though I love what they've done for my skin too."

"Sounds good to me, they've definitely helped as you've noticed." she assured me.

After lunch we went shopping for shoes to match our dresses, a nice pair of heels for both of us. While I was walking around testing out a pair Daisy said with a tease, "You know, with those on you're almost as tall as Saul and they make your ass look amazing. You should get another pair to wear on your next date with him."

I sighed, "I told you it wasn't a date, it was just two friends hanging out."

"Yeah, only he bought you dinner and you shamelessly flirted with him to the point of teasing him with that amazing ass of yours. If it wasn't a date why did I find you on the bed fucking yourself with a dildo moaning his name afterwards." she winked.

I turned red and looked around, it didn't seem like anyone heard her. It didn't seem to be the case but I still answered in a hushed tone, "That was just, um well, it was, it was. It wasn't a date."

"The lady doth protest too much, methinks" she teased holding up a similar pair of heels to the ones I was trying out, these ones black compared to the lavender pair I was trying out. "These would look good with a little black dress."

"Ok that would be a great match up and I'm going to have to try those on. But I'll need to find a dress to go with them, oh maybe for a housewarming party when we move into the new place!"

"A new dress has you buying new shoes, new shoes has you thinking about a new dress. It's a vicious cycle. But yes we should get you a little black dress for these shoes and yes we should totally throw a housewarming party after we move in. I have to show off my wife's fantastic design skills to everyone." Daisy agreed.

"Everyone?" I paused thinking, "What if we doubled it as a housewarming party and coming out party? I mean everyone at work knows and I'm sure word is getting out. How about we make it official?" I proposed while changing into the black heels to give them a try.

Daisy just smiled, "I think that's a wonderful idea. We can invite whomever you want and they can all be there. Maybe we make sure to invite some people who already know and are supportive to help reduce any anxiety that might build up between now and then."

I walked over to her and leaned over to kiss her, a little taller than usual in the heels. "You are incredibly smart, that is a really good idea. I can already think of a few people to invite."

As we finished picking out our shoes we discussed a guest list. By the time we were at the next store looking for the dress to go with my new heels we already had a fairly large list. Large enough that we decided on an open house style where guests could come and go because even with the new larger house it would get tight.

When we found the right dress we made our way to the changing room and I was in love with it right away. The dress hugged my body just right showing off the curves I had worked so hard to build up the skirt held tight to my thighs midway down before stopping. Looking in the mirror and turning around I felt happy tears forming. Sitting in the changing room with me Daisy said, "Babe you look gorgeous, that dress looks so good on you I can't wait to get it off of you." Then with a poke in the side she added, "We need to make sure Saul is on the guest list because I imagine he'll be thinking the same thing."

I blushed again, and couldn't stop the little grin from forming. "I do want to make sure he knows the whole truth about me. And that may be the right time to let him know and get a gauge on how he feels." I knew I must have been flush all over because the air felt cooler than before as I took off the dress and put it back on its hanger.

"And if he's still into you after that we can let him know that it's ok with me if he does date you, he just needs to know that ultimately you're mine. I'm just willing to share." As Daisy said that she also gave me a reminder that I was hers, as on top of my clothes she had set the Dex, a device that was similar to a cock ring with a part coming down and a butt plug with a penis shaped head at the end. It could be controlled by the app on her phone that told it which parts vibrated, at what intensities, the thrusting motion of the plug and how fast it moved up and down.

I licked my lips slightly looking at it and the lube in her hand, "Ok but this time you're driving home."

She giggled loud enough that if anyone else was in the changing room they would have heard, but I still pulled down my gaffed panties and watched while she lubed the plug. My cock was limp from being in the gaff but started to stiffen when she took it in her hand to slide on the ring. I felt the tug of the ring as she angled the plug in to my ass, it felt so good sliding in being filled and having the curved head press lightly against my prostate.

I was savoring the feeling when Daisy pulled up my panties tucking my semi hard cock into the gaff. Her fingers on my cock sent a feeling of delight through me but being tucked tightly away I couldn't grow harder in the confined space. While getting my dress back on I was a little uncomfortable as my cock tried to push beyond its confines until it adapted to the space even though my arousal was so heightened.

By the time I was walking out of the changing room carrying the dress over an arm I had adjusted to the sensations of the Dex in me and around the base of my cock. Mid step I felt it start moving up and down inside of me with a barely audible buzz as it also vibrated. I stumbled and reached out to grab something for support with my free hand.

Mannequin arms are not very supportive, in fact as I lost my balance and fell I pulled the arm off of it. The grand show happened in front of two store employees who immediately came to help reaching down to offer a helping hand up, which I misunderstood and apologized as I handed the arm up to them. They took the arm and set it to the side in order to help me up. "Are you ok Ma'am." one of them asked as they helped me to my feet.

"Yes, I ah just tripped over my own feet. Thank you." I could feel my warm cheeks as I blushed in embarrassment. I quickly made my way to the check out while they put the arm back on the mannequin the entire time I could feel the dex pumping up and down vibrating inside of me. I fumbled with my purse through the check out and could feel my cock leaking so much precum my panties were getting soaked.

When we were all set and walking out the car Daisy took out the car keys and checked her phone. "Oh did I leave that on?" she sarcastically asked, "I guess you're used to it so I'll have to turn it up."

As I watched her fiddle with the settings and felt the thrusting of the Dex increase and the vibrations begin to pulsate at what felt like an irregular pattern. I caught myself on the side of the car as my legs turned to jelly and gave Daisy a playful grin, "You tease." I managed as I slipped into the car. Sitting down pushed the Dex firmly into me causing it to push in deeper with its thrusts.

Before we were even pulling out of the parking lot I was moaning in response to the Dex fucking my ass and pushing into me. I layed back into the seat and began running my hands up my smooth legs. Leaving one hand on the wheel Daisy reached over and rested one on my thigh, "No touching yourself, just put your hands on the armrests."

I didn't want to, but I complied putting my hands on the arm rests of my seat. I sat there closing my eyes and trying to keep myself under composure, but not doing a good job squirming in my seat, squeezing and squeezing my legs. I felt the shift of momentum as we came to a stop, my hopes that we were home already were dashed when I saw we were just at a red light not far from the mall.

Daisy reached for her phone in its bracket and deftly switched to the dex control app. I happily groaned as she didn't turn it off but changed to another pre-programmed setting before turning the screen off and waiting for the light to change. The new setting slowed the vibe and thrusts but didn't stop them, by the time the light turned green though it was building up intensity. The vibrations were at their peak when the thrusting head was at its deepest and backing off as it pulled back.

"Daisy please I'm going to cum right here."

"No you won't, you will hold back from cumming until we get home."

I moaned in protest doing everything I could to obey as a battle between the physical pleasure and mental desire to do as I was told battled each other. I was gripping the arm rests so tightly I was certain I'd leave permanent marks. The sensation of being filled and my prostate being pleasured were becoming too much. With a glimpse out the window I could see we were almost home though, just a couple of minutes and we'd be there.

"You're the worst." I managed to say through moans as we passed our street.

"Oh did I miss the turn?" Daisy feigned ignorance, "Guess I'll have to go around the block. It'll take a little while longer."

I did the best I could to resist but just as our house came into view I couldn't hold it back any more. I tried to hide it as I cummed in my gaffed panties, but Daisy could tell from the moan of delight and involuntary bucking of my hips. I could feel my cum soaking in as the Dex milked as much out of me as it could.

"Naughty naughty, you've gone and made a mess in your panties." Daisy teased with a smile as she pulled into the garage. After parking she turned the Dex off and got out of the car. Before closing the door she leaned in, "Once you've regained your composure grab your new things and bring them inside. We'll figure out your punishment for disobeying me once they're put away."

I sat there catching my breath before getting out and retrieving my things from the trunk. I realized that she had left the garage door open and any of our neighbors could see inside. I also realized it didn't bother me like it might have when I first started my journey of self discovery. I happily grabbed my things and brought them inside and put them away in my closet.

As I was passing through the bathroom back to the bedroom I heard Daisy's voice from the bedroom, "Roxy go ahead and take out the Dex, leave it by the sink to clean later then come in here."

I did as instructed, sliding it out of me, my ass feeling a little empty after the fact. Then I stretched the cock ring and pulled it off feeling the blood that had been held in my cock drain back into me. To take it off I didn't need to remove the gaff but I still did and changed into a comfortable pair of white lace panties before heading to our room.

The chair from our dining room sitting in the room in front of our bed was a puzzling item that I took a look at before glancing at Daisy who was pulling items out of her night stand, "Have a seat." came her instructions without looking.

With a shrug I did as she said, my recently used ass appreciating the cushion on the seat. I watched while Daisy rummaged before she came to me with a handful of restraints. Without saying a word and with my full cooperation she put the soft wide cuffs around my wrists and connected them behind the chair. She followed this up with cuffing my ankles and connecting them with a strap behind the legs of the chair forcing my feet back slightly and resting on my toes.

"Since you were a naughty girl and came without permission in the car, you're going to have to sit there and watch while I make myself cum."

"Oh that's not fair, you intentionally made the drive home last longer than it should have."

She playfully slapped my thigh right below where the skirt of my dress ended, "I don't see why you are complaining you get to watch the show even after you didn't obey."