Halloween Weekend 2023 Pt. 03

So we drove to the party. It was held in a rented warehouse that I had been to before. In the past when I sent it was for more S&M scenes. Tonight it was set up with tables and behind them booths that the door could stay open or closed, depending on the desires of the "customers "! The deal was each person entering purchased special Monopoly money. The original money would be given to a Women's survivor charity. While we got there early already most of the tables were filled. There was a mixture of men, women, and trannies. The one that caught my eye the most was a very tall Domme. She was exquisitely dressed in a tight leather mini dress, thigh high leather boots, and black hose. In her 5 inch heels she towered over most there. I found out later she was 6'1" barefoot and 180 lbs of perfection. Her sign read various spankings, humiliations, and pegging. The equipment I saw was very impressive with various whips, floggers, gags, hoods, blindfolds, and dildos of various sizes. I noticed 2 other trannies but offering different services than me. One was a submissive to be punished, 5he other a Domme. Was going to be an interesting party! At the end they would count how much was made by each participant. The highest number would be awarded their choice of using one of the other services.

What I enjoy about the parties here are that the participants are real. An example is that not every man had a giant cock. Most ranged from 5.5 inches to 7 inches with a few larger ones. Also the women were not all perfect bodies. Some fat, some skinny. The idea was that these were real people. I later found out that the party had 20 booths and 200 guests. A great mix. At precisely 7PM the party started. The first two guys I had wanted to fuck my ass. One's wife participated, having me eat her, telling me her was too thighs even for his average cock. Since this was a spit roast they got it for free but since she came so hard they tipped me! By the end of the first hour I had about $20.00 in my bucket. According to Sue I was actually doing good. After several more combinations of blow jobs/ass fucks/ATM time was moving on. Then a guy asked me if I would drink his golden shower. I told him I would try but depended on the taste. I kneeled next to a tall waste basket, opened wide and he let it fly. Tasted ok, drank most of it, then he had me suck his cock. It was about 6 inches long and pretty thick. When he came he held my head and as I swallowed he pissed straight down my throat! He then thanked me and tipped me.

It had reached the halfway point and they did a money count. The Domme was the leader by far with over $750.00 dollars already. In comparison I was fifth with only $140.00. According to Susan she had one guy tip her $500.00 for fucking his ass with a large dildo. Susan told me it was time to inspire me to make more money. The next guy wanted to be sucked, then fuck me. He had the largest cock so far to come m6 way but still only about 7 inches and average width. It took me a good 20 minutes to get him rock hard. I found out later he had cum twice already. Then he started to fuck me. He was one of those who just kept even strokes, taking his time, calling me slut, whore, faggot, sissy, and other humiliating names. Then it happened...Sue started to shock my chastity cage. At first it was a tingle but then she turned it up. As she did so I started fucking him back, spurred on. He also got more into it, pulling back to just the tip, then slam fucking me. After another 10 minutes he announced he was cumming, buried his cock deep in me, and let loose a surprising load. Then he pulled out for me to lick him clean. Now Sue went to town, shocking me as he gagged me on his deflating cock.

People had gathered around to watch the show and when he finally pulled out the applauded us. That started a busy time including at one point being fucked, sucking a cock, and giving two handjobs. Because they were not together they all paid. I also licked clean two ladies, one who had several loads in her ass that sh3 farted into my mouth. All this time Sue continued to shock me till I came myself, a shocking sissygasm! Finally the night was ending with only 30 minutes left to count up our "earnings". The Domme won with over $2,000.00. I came in third with just under $900.00. The Domme announced what she wanted for her prize and that's when I was shocked. She wanted to spit roast with me and her sub! Sue was laughing and I later found out that they were good friends. This occurred on a mattress brought center stage. I was to be blindfolded. I noticed her sub had a small, 5" cock that was thin so I figured this would be easy, especially since my ass was a little sore. I got on my hands and knees, blindfolded, and waited. Then I felt strong hands pulling my face down and I realized that I would be sucking off the slave and she would be fucking me.

As I went to work on his limp dick I heard someone say that the slav3 had already cum 4 times tonight! As I worked his cock I felt fingers putting some lube in my ass. He was starting to harden, in a semi-hard state when he squirted down my throat. He was pissing. He held my head and I knew I had to drink it down. As he continued I felt the head of a dildo on my ass. It felt really wide. As she pushed it wouldn't go in and it hurt but with a mouthful of cock i couldn't say too much. Then someone put a rag under my nose full of poppers. I had not had any all night and now I was breathing them like crazy. All of a sudden my ass opened and the dildo went in. My God, it felt like a fist, thick and really long. She kept pushing till it bottomed out. The pain was unbearable but with my head held down on the cock I was trapped. Then she said "You sissy, faggot, bitch! I am going to fuck you till both my sub and I cum from me fucking your ass!"

With that she went to town, fucking me long and hard. He was still semi hard, giving me the occasional squirt of piss. Finally after about ten minutes and more poppers I started to loosen up. I started to go wild, sucking his cock like it was the last one ever and moving my hips, fucking her back. All of a sudden I felt it. I felt vibrations on my ass when that monster cock was buried in me. She had a vibrator attached to it and had turned it on. Finally I could hear her moaning, getting louder, fucking me faster. Then, by surprise, her sub's cock stiffened and I could feel it pulsating in my mouth, shooting an almost dry loud, 5hen him yanking it out, yelling how sensitive it was. Another minute of her fucking me when she screamed she was cumming, pulling out of me, rolling me over and sitting on my face, telling me to lick her cunt as she came, squirting in my face.

After that she rolled off of me and pulled off my blindfold. The look of bliss on her face was evident. I also now saw the dildo she was fucking me with. It was a Rambone modified for a clit vibrator. A Rambone is 13.5 insertable and about 2.4 wide! Finally she got off of me and Sue helped me to my feet, whispering what a good sissy I was! We left soon after but not before I had promised to sub for our friend. That was the end of Halloween. The next day I rested l my ass very sore.