So I get off work at 6:45, just working a 1/2 day and head t..
🕑 Added 2023-10-22 22:25:04 +0000 UTC
So I get off work at 6:45, just working a 1/2 day and head towards the city to pick up my cross dressing friend Jenny. I haven't seen her in months, since like April and I was really excited. Also kind of awkwardly nervous. But that's okay because I think she was too. So we're both in boy mode and driving down to another city. We're going to check into a hotel for two night's and have some amazing Kinky fun. It was about an hour and a half drive filled mostly with small talk until maybe the last half hour when I got her to pull her pants down so I could stroke her Dick. I really wanted to lean over and suck it but unfortunately I had to drive. We get to the hotel Around 9 or 930 and the parking lot is absolutely packed. I mean, I did expect it to be. We are going with our other cross dressing friend who will be referred to as A and her wife who will be referred to as Mistress. A was the one who made the hotel reservations. On the website it was sold out but A talked to the guy in charge and they said they had 10 rooms left. Considering we didn't make plans until like a week or 2 beforehand and after having been here, I'm surprised they had any rooms left for us. And thank God they did because holy shit I have had the time of my life.
We get checked in and head to our room and there are sexy scantily clad people everywhere. DJ in the middle of the atrium where all the rooms face, thumping music that can be heard behind closed doors. We step into a crowded elevator with our bags and suitcases. Everybody has smiles and really friendly. I turned to face the door like you normally do and the girl behind me starts rubbing my butt. I remember she introduced herself but I couldn't tell you what her name was. This entire experience is my motivation to stay healthy and exercise. My ass is going to be climbing stairs everyday. We get into our room and start getting our girl on. Our friends are out to dinner and we're not sure when they will be back. So once we were ready we decided to head down to the main floor and join the party. It wasn't packed to the point where you can't walk around but there were a lot of people there. The very large dance floor was crowded but still enough room. There were even a couple large light up dance cubes. Those things that the hot girls stand on top of and dance around being the center of attention. Yeah, hold on I'll get there. So we made our way to the dance floor and I found out that Jenny is not particularly fond of dancing. I get it. In my male identity I would never dance. He doesn't want people pointing laughing or judging. Crystal doesn't give a fuck, plus she knows that everybody or almost everybody loves her boobs. So my solution was, I sat Jenny down in a chair that bordered the dance floor and started dancing as sexy as I could right in front of her. In hindsight, I realized those chairs or couches were actually reserved and I probably should not have been in one. But hey, no harm no foul and a bunch of people got a pretty sexy show. So being that I was bobbing around and only once in a while making Eye contact with a few people that I thought were really hot, I wasn't paying attention to the room in general. However, Jenny was. And she told me that EVERYBODY was loving me. I'm pretty sure that I was wearing my LED buttplug. Not that giant hand, just the buttplug. So all that sexy bending over I was doing, definitely Jenny and hopefully many other people saw my colorfully lit butt cheeks. After a bit we decided to go back up to the room and check our phone, see if our friends had shown up. An unbelievable amount of things have happened in the last 2 days so some of the details are a tad bit fuzzy. I think our friends showed up while we were freshening up. Mistress disappeared for a few minutes and reappeared wearing a little black something or another with fishnets over her boobs. A stayed in boy mode because it was starting to get a little late and it does take a decent amount of time to change a boy into a girl. We all went back downstairs and I can't remember exactly what we did. Oh yeah, I think we checked out the group sex room for a minute but didn't do anything. We probably wandered around and took a look at the pool and maybe something else but eventually we ended up on the dance floor and even got Jenny out there bouncing around ❤️.
The party was starting to die down a little but there was still a lot of people there, it just wasn't packed. And this is where I first ended up on top of one of those lit up dance cubes. Hahaha. I am such an attention whore. Wtf is wrong with me? *sigh*
The main party on the first floor started dying down and we transitioned to the after party on the fifth floor. This place is absolutely amazing. Every floor has a rather wide bridge that connects one side to the other. That's where the party was on the fifth floor, and they had a buffet table filled with hors d'oeuvres. Some dancing some munching, a whole bunch of "oh my God I love your boobs". I don't remember when the first person said something about my boobs. I don't remember how many people said something. But it was a very frequent occurrence from the moment I first stepped out of the hotel room. There was at least one guy and I'm thinking maybe more that was trying to chat up myself and Jenny. Felt kind of like it was an option on the table but not super intriguing, at least not to me. Sure I wanna suck a Dick, even one that didn't come with me. But I wasn't in a hurry to suck the first one that came along and offered. After that we went back to our room and did a little oral and kissing before A and mistress headed off to their room. Jenny and I however stayed up for a little while. We ended up on the bed watching some of my videos that I haven't released yet. I was using a vibrator on my little penis like I do. Confessing my sissiness while using a vibrator to masturbate my penis while watching a video of myself running around naked in public next to another Sissy stroking her Dick watching me and my videos. When I got close I told her and she repositioned to get her mouth on my penis. I came inside her mouth while she was sucking and what an amazing sensation that was. Like I didn't just come into her mouth. She wasn't just sucking. Anyone taking the time to read this probably knows me well enough to know that I don't have a cum shot. At best I have a cum ooze and normally it's a cum dribble. But in this moment, at this time, my Sissy friend getting a good seal around the tip of my Dick including my Prince Albert hole, produced an amount of suction that launched the semen up the shaft of my penis at speeds I haven't felt since long ago when I was a pervert trying desperately to deny being gay. She immediately came up to kiss me. She had swallowed the vast majority of it but I could still taste my cum on her lips and tongue. God that was hot.
She wasn't quite ready to release her tensions so we snuggled up and fell asleep.
