Jester Cosplays

As I walked up I caught the end of Daisy saying, "that is if you are interested, but I'll let the two of you talk about it." She turned to include me in the conversation, "And look how quickly she returns to us. Saul and I had a nice little chat. Why don't the two of you head out to the deck while I mingle, it's nice and quiet out there right now."

She immediately started working the room so I opened the door and led Saul out to the deck. As we walked he asked a bit awkwardly, "So was the invite serious about people taking empty boxes?"

I giggled a little, "Yeah we have a ton of them and we aren't sure how long it'll take for us to recycle them with our bin only getting emptied every other week."

"Well I've got my truck here and I can take them all when I leave, the recycling yard isn't too far from my place and I can make it part of my trip home."

"That would be great." I responded as I reached the railing and looked out into the woods surrounding the house. "But I don't think that's what Daisy was thinking we'd be talking about when she ushered us out here. What did the two of you talk about while I was taking care of the flowers, thank you for them by the way. They're beautiful."

He sighed heavily as he leaned onto the railing right next to me, the breeze blowing his cologne towards me. He smelt amazing and I couldn't help looking over to check him out, his features showed him to be in deep thought which looked really good on him.

"You're welcome, I got them from my favorite florist. I like that place because I can walk into their cooler and pick out my own arrangement. But yeah boxes and flowers aren't what we talked about. She told me that you two have discussed the idea that she's ok with you seeing other guys, not that she's a guy but that as Roxy if you wanted to see a guy she's ok with that."

"That came up after our not date." I quietly said.

"You mean the not date that felt a whole lot like a date?" He said with a smirk.

I just replied with a smile and a nod. Before asking, "So you know the whole truth about me now, and how Daisy feels about the idea. What about you? How do you feel about the idea of going on a date with me officially?"

Saul stood up and took a deep breath, "Promise to listen until I'm finished?"

"Of course." I answered.

"Ok, at first I felt really guilty after the not a date because of how much it felt like a date and I knew you were married. I was wrestling with that still when we texted about tonight and then I was really freaked out because I didn't know what that made me. I was really attracted to you and then I found out that you're also Max. It was a good thing that my regular therapy session was a couple of days later, and man did I unload on my therapist."

He finally stopped to take a breath and then continued the whole time talking with his hands, "Doc had some great insights and we talked for a long time. He even let me go past our scheduled time at no extra charge. Together we worked through the fact that I'm attracted to Roxy but not to Max if that makes any sense. Don't get me wrong Max is a great guy and someone I'd hang out with but not date like I would Roxy." His hands gestured to two sides then came together, "But you are the same person with different expressions. I came here tonight ready to say I'm good with our friendship and deal with being attracted to you. Then Daisy said everything she did and threw me for a loop, dating you while you're married to her would mean, I don't know what it would mean, Fuck my brain is going to explode." He flopped down into one of the chairs on the deck rubbing his temples.

I waited a moment to make sure he was done, "How about it means we stay friends with potential for more, friends with possible benefits? Obviously nothing exclusive, we could see other people but enjoy being with each other."

At the idea of friends with benefits he sat up, "That could work. Since talking with my therapist I've been reading some things and ... well watching some things that I wouldn't have before. I'm definitely open to that idea, but some of the stuff was rough. I wouldn't be interested in anything like that."

I offered him a hand up and he took it, "Tell you what, I've got a busy couple of weekends coming up, how about after those we go on a date and see what happens?"

"Sounds good to me." he said, taking my hand but lifting himself up, "So what do you have going on?"

I explained about the Gala for the Magnolia opening and then about the convention the weekend following. He was interested in the cosplay so I pulled out my phone and showed him pictures from last year and the pictures of what Daisy and I had ready to go for this year.

As I was showing him I had the thought that I hadn't posted much about them on my social media but now that the truth was out I should post it. So while we went inside I posted them making sure to tag anyone I could think of as well as the location and event talking about being excited to be there in a couple weeks. I added a short version of how the Bowsette cosplay brought me to the realization that I was genderfluid with the post.

The rest of the party went well and true to his word Saul left with all the empty boxes. Seeing him lift half the pile in a single trip and his biceps flex as he carried them out was exciting. I'll admit I was freely checking him out, Daisy caught me and teased me kindly with a nudge. After everyone was gone I updated her on how my talk with Saul went.

As I was wrapping up some of the clean up Daisy came over and gave me a kiss on the cheek, "I snuck into our room while you and Saul were talking. I left you something on the bed I want you to put on, I'll be waiting in the living room for you."

I entered the bedroom and saw sitting on the bed was a dark purple sheer bustier, a matching garter and thigh high stockings, as well as a matching thong. Next to them was a note from Daisy giving me instructions on how to put everything on. The note ended with instructions on the order to put everything on, "There's mixed opinions on if the garter goes over or under the underwear, I want you to put it over the garter tonight."

I took my time getting undressed before following the instructions putting on the garter first and carefully pulling up the stockings and clipping them to the garter. The bustier was a little tight but I liked how it squeezed. I pulled up the thong at last and got my cock tucked as much in the front as I could but the sheer fabric on it felt so good I was already getting hard.

As I started walking to the door inspiration struck and I quickly retrieved my purple heels for the gala and slipped them on. As I left the closet where the heels were stored I passed through the bathroom and caught my reflection in the mirror. I took a moment to check myself out and make a couple of minor adjustments to the way everything was fitted.

When I entered the living room I walked to Daisy who was sitting in a chair facing the room grinning broadly. I made sure to cross my steps to give myself an exaggerated sway as my heels clicked across the floor. I stopped just out of reach and looked into her eyes, "I like the new outfit. Thank you."

She looked me over, checking me out before returning to looking in my eyes. "Looks good on you, and I like the addition of the heels. But just how thankful are you?"

I took her meaning and stepped forward sitting on her lap starting to kiss her, darting my tongue into her mouth with both hands on the sides of her face. Slowly I slid a hand down to cup her breast, gently massaging it. As I moved my kissing to the other side of her neck moving my free hand behind her back to pinch the clasp of her bra.

As I moved down her body, Daisy gently rested a hand on my head and pushed me lower. I took the hint and followed her guidance until I was on my knees between her spread legs. With a little shifting she pulled her bra from under her dress and dropped it on the floor watching me as I began kissing her thighs as she shifted in the chair until she was resting on the edge of the seat.

She took a handful of my hair and pulled me close while flipping her dress over my head with her other hand. The pleasant aroma of her pussy filled my nose as I saw she had already removed her panties. Immediately I began kissing it, giving a gentle lick occasionally. I didn't need her to keep holding my head in place but it was hot and encouraged me further.

My kisses were joined by more licks as I enjoyed her, once I tasted more of her cum I began tenderly sucking on her clit while slipping a couple of fingers into her. The entire time I ate her out and fingered her she kept a hand holding my hair keeping me in place.

Her moans began echoing in the room and I could feel my cock twitching. It always turns me on to realize how much pleasure I'm bringing her and the mesh against my cock felt amazing everytime I even slightly shifted. I added a finger to her pussy and a cum covered pinky into her ass. Her hand left my head and I could hear her gripping the arm rest, that is before her legs wrapped around my shoulder and pulled me close and clamped around my head blocking out most noise.

I could still hear her muffled moans as she came, unconsciously squeezing me tightly with her legs. It felt amazing and although I knew I wasn't in any real danger I figured that would be just about the best way to go. I couldn't move my hand very much as tight as she held me but I could wiggle my fingers inside of her while slowing down with my mouth on her pussy.

When her legs finally relaxed and rested alongside me, she leaned forward and pushed me back a little kneeling between the chair and me. We kissed on our knees together and her tongue darted in my mouth as if she's trying to taste more of her in my mouth.

She backed away from the kissing and almost breathlessly said, "Stand up."

I did as she said, but as I stood she grabbed the thong and pulled it down my legs freeing my swollen glistening cock. She quickly began stroking me, spreading my precum down my cock before taking me into her mouth. She stroked with one hand as she sucked me, bobbing her head back and forth. Her hand was quickly covered by a combination of my precum and her saliva, which she swapped for the other hand using the lube we generated to slip a couple of fingers into my ass.

I felt as she pressed my prostate and I almost instantly came filling her mouth with my cum. But she kept sucking and playing with my prostate, milking everything out of me she could get. My legs were turning to jelly as my cock softened and stopped twitching. She stood up and gave me a big kiss pushing my cum into my mouth and covering my lips with hers until I swallowed my load.

The salty after taste was still in my mouth as we showered later and got ready for bed, but it was washed away while I brushed my teeth. As we got into bed I rolled over and kissed Daisy on the cheek, "Thank you again for the new outfit."

"You're welcome, maybe it's something you could wear on a date sometime if things go well with Saul."

I went to sleep with visions of what a date with Saul might look like, my thoughts drifted into dreams and I'm not sure when the dreams took over my imagination. Those were some wonderful dreams and I didn't want to wake from them but morning came anyway.

However the morning did bring a flood of messages and comments from my social media posts. The support I received was overwhelming, yeah there were a few negative comments and messages. I blocked those that sent messages, and didn't need to do anything with the comments because they were being addressed in the replies.

One message that I was excited to see was from a Mike Stein. He let me know that he was the Mike from last year's convention and was excited for me to be out. We chatted a little bit about the critter meetup at this year's convention and I told him how Daisy and I were attending that day both as Jester. He talked about how he wanted to be Fjord and had some of the armor but needed more things he didn't have time or money to finish.

I created a group text with him and Daisy after getting his number, in the chat we discussed meeting up at the hotel so we could loan him some of the items from my Fjord cosplay and help him get the green body paint on. He was staying in the same hotel as us so that worked out perfectly, he was volunteering with security again on the second day of the convention in exchange for his tickets.

When I asked what his cosplay was for the third day he said he didn't have anything planned and was just going to wear an anime T-shirt and check things out. That led to the three of us talking about what our favorite animes were and us telling him about our Erza cosplays.

Out of the chat Daisy and I agreed that it would be more fun for us if we wore our Erza cosplays on the third day and planned to do the T-shirt idea ourselves on the second day. One thing led to another and we spent the week approaching the gala working on a surprise for Mike we planned to give him when he came to our room to get his Fjord cosplay on.

As the Gala approached, I spent my work hours visiting the site a couple of times, even pitching in to help sweep the floor before a meeting. It was leaning against a wall and I saw some dirt that needed to be cleaned while I was waiting for others to arrive for the meeting. I didn't have to, but I wanted everything to be all set for the gala.

Our whole team took that Friday off to get ourselves ready for that night. Daisy took the day off as well, so we went to Tips and Toes to catch up with the girls there before going to get our hair done. I did go with the extensions Daisy suggested which resulted in a wonderful updo. By the time we left the house that night we were all dolled up. The odd item we were carrying was a duffle bag with my change of clothes for me midway through the night.

We arrived early enough to find the room I planned for my change and leave the bag in the room. Walking to the main room for the event felt magical in our dresses, the lights twinkling above us. The entire night was wonderful, Daisy and I danced for a few songs and got a bite to eat. After eating we returned to dancing. I shared a dance with Dan and Jeff from work, as well as a couple of my contacts from Magnolia. During the dances we talked about work and how great the new building looked.

Halfway through the night Daisy and I slipped away to the room where I stashed the bag. With her help it was a quick change. I was thankful she packed the make up wipes and that she was there to give me a once over and get the spots I missed. It was maybe 20 minutes after entering the room we were exiting as I tied my tie, my dress and breast forms stashed away in the bag still in the room.

I was adjusting my tie as Daisy pulled the door closed behind us, and a security guard heard it looking our way. He gave me a wink and a sly smile, I attempted to clarify we weren't doing anything but he walked away before I could say anything. As we returned to the party I glanced at a few couples sneaking off and realized it was pretty normal.

By the time the night ended we were both exhausted, after the change we danced some more and I had some dances with Gina and Prema as well as a couple of ladies from the Magnolia team. After the dancing and a few speeches from the Magnolia leadership on the future of the company we returned to the room with my bag. I was bending over to pick it up when I heard the door lock behind me.

"You up for a quickie?" I heard Daisy ask from behind me.

I turned around with excitement in my eyes and saw it reflected in her eyes. I tossed the bag to the door behind her and picked her up, sitting her down on the conference table. While I carried her, she unbuckled my belt and unzipped my pants. With a little help from me after setting her down she hitched up her dress while spreading her legs wide enough for me to step up.

As I stepped close to her I pulled my cock while watching her pull her panties to the side. There was a little bit of fumbling at first but we managed to position ourselves and I entered her slowly pushing in and pulling out. My penetration was shallow at first but with each thrust I entered her further.

In only moments I was fucking her hard on the table. It was quick and passionate as we christened the conference room. Daisy bit her lip to keep from making too much noise, and to keep myself from being too loud as I came I kissed her, pushing my tongue into her mouth as my cum filled her pussy.

When I felt my cock stop pulsing I pulled out of her and slid her panties back over to her pussy. She leaned back on her hands as I buttoned up both of us grinning like fools. I picked up the bag as she got to her feet and we slipped out of the room. No one saw us leave that time and we made our way to the parking garage then on to home.

The next Monday I met with new clients for an initial concept meeting. I had the honor of helping a non-profit use their new building grant to create a safe place for young people to be themselves and even for some who needed a place to stay for a while after being kicked out of their own homes for coming out. It was a wonderful meeting and I left with ideas already flooding my mind.

We wrapped up our surprise for Mike with plenty of time to pack it up with our other items for the convention. We both took an extra long weekend leaving for the convention Thursday morning. Before we left I glued on my more long term breast forms. I knew for sure this would be a long weekend as Roxy and didn't want to bother with the forms I pulled on over my head.

The drive was wonderful, we listened to a book on the trip called "Dreadnought", about a trans girl who got superpowers giving her the transition she wanted. She had family and friend issues to deal with along with fighting bad guys. We weren't able to finish the book before we arrived but given how much we had left to listen to we would finish it on the return trip.

After checking in to our room we got settled in hanging up our cosplay supplies, not just clothes but weapons and armor too, before heading to get a bite to eat. We messaged Mike and let him know we were checked in but getting dinner. We gave him our room number and set up a time early in the morning for him to come by and get ready. We called it an early night in an effort to get as much rest as we could.

Our alarms went off too early the next morning, I rolled out of bed first and took a shower ending with some very cold water to wake me up. I was drying off before pulling up a pair of panties as Daisy came into the bathroom and got the shower going for herself. My Jester cosplay had a small but thick petticoat so I didn't bother with the gaff.

I got my bra on before brushing my teeth and put in my tiefling fangs. I was checking the angles in the mirror making sure they were a good fit when I heard a knock at the door, a quick check of the peep hole and I saw it was Mike carrying the parts of his cosplay he had brought.

By the time I had the door half open in my excitement I remembered that I was only in my bra and panties, the wide eyed look he gave me was the give away. With a squeal I quickly shut the door and retrieved my fluffy robe, I tied it in place and reopened the door to let him in.

"Sorry about that, I was so happy to see you that my mind blanked." I apologized as I opened it.

I caught him making a quick pants adjustment as he walked in, "Happy to see you too Roxy." There was a bit of a chuckle in his voice.

I leaned into the bathroom and let Daisy know that Mike was here so she didn't make the same mistake as I did. When I caught back up to Mike he was checking out the cosplays on the hanger, "You two are incredible with what you can make."