My wife knew that I liked to dress and would often help me. Usually it just consisted of dressing up and watching TV or maybe having hot sex. Once she had me dress and took me for a drive to the park where she made me walk around and pose for pictures. She’d also take me to the local thrift stores where we’d buy new things for Michelle. In bed we’d often talk about me dressing up and going someplace in public like a club or show. It seemed to make us both hot and the sex we had afterwards was fantastic.
One weekend we had to go to Providence for a friends wedding. My wife told me she was going to have me wear a corset, stockings, garters, and bra under my suit and only I would know. She also told me that she had hired someone to come do her hair and makeup Saturday afternoon for the wedding as she wanted to look especially gorgeous. We went up on a Friday afternoon so we’d be all set for the wedding Saturday evening.
We got there Friday after lunch and were fooling around in the room a bit. She asked me to shave her “down there” which I always enjoy doing for her. After I finished she said it was her turn and proceeded to shave my cock and balls nice and smooth. When she was done she said she wanted to do more and proceeded to shave my legs, then ass, and finally all of me! Took her a while but was very sensuous as she touched me all over. I took a shower and felt so smooth.. maybe I could have her do it again after it all grew back. I got my jeans and t-shirt back on and was relaxing with a beer when there was a knock at the door. Sue answered and it was the lady that was to do her hair and makeup, seems like there was a mixup on the date. Sue invited her in for a glass of wine anyways and after checking realized that she had made the mistake. She told her that she’d pay her for today AND tomorrow if she could come back tomorrow before the wedding. They were discussing that as I got up to use the bathroom. When I returned they were both quiet and sipping their wine. They both looked at me kinda funny and before I knew it I was the one having my hair and makeup done. Sue had brought some of my things including a wig. It was fine with me and Peggy proceeded to give me a makeover while Sue watched and learned some new techniques. Before I knew it she was done, I was looking pretty hot and my wig had been styled and pinned to my head. Peggy left and Sue got a camera and started taking some pictures telling me how hot I looked. She unpacked my girl clothes and had me dress for her. Black frilly skirt with a bit of a petticoat underneath, white lace top and a silver wraparound jacket. Topped off with some rhinestone stripper earrings and a necklace and backseam stockings and black 5” pumps and I felt hot too!! Sue told me to relax and have a glass of wine as she wanted to dress up too. Soon we were both looking pretty hot and relaxing with a glass of wine.
We had dinner sent up and watched TV a bit, a couple of girlfriends relaxing for the evening. Around 9 pm Sue told me to kneel on the bed and she reached under and tied a ribbon tight around my balls and lead it up under my skirt letting it hang out the back, under my jacket. I stood and she came over and reached back giving it a tug almost sending me through the roof, I figured it was playtime but suddenly Sue said “Let’s go for a walk”, I hesitated and said “Are you sure?” “Of course silly, you look great” Sue replied and off we went. It was a bit chilly and we had walked for about 30 minutes when Sue hailed a cab, I figured for the walk back. She gave the cabbie a note and told him to take us to that address. I didn’t recognize the area we headed to but wasn’t concerned until the cabbie dropped us off at an address I didn’t recognize. The sign on the place said “Dark Lady”. She said “Lets have a drink” and pulled me along. We went in and when our eyes adjusted found a small but crowded place with a bar in the middle and an upper landing to the left with some tables and a few couches. I noticed a few other dressers there and turned to Sue with a bit of a puzzled look. She pulled me too her and said “I heard about the place online and wanted to bring you here, enjoy yourself Michelle”. We found a small table with two stools and sat down. After waiting for a bit it was clear that the waitress was gonna take a while so Sue suggested I go to the bar and get a couple of glasses of wine. I got up to the bar and was waiting for the bartender when I felt a hand go up under my skirt. I looked to my left and this gorgeous guy was looking straight forward even though I felt him squeeze my thigh. I gave the bartender our order and spread my legs just a little… the hand moved up and started to tease my bound balls. It felt sooooo good but soon the drinks where in my hand and I was headed back to the table. When I got back there was a guy sitting on my stool talking to Sue. He excused himself and got up letting me have the stool back but continued to stand to my left with Sue on my right. We started talking and before I knew it his hand was on my knee, then it slid up a bit as he lightly caressed my inner thigh. I spread my legs slightly and felt Sue lean over towards me. I wasn’t sure if I wanted her to see what he was doing but soon his hand had reached my bound sissy balls and gave them a big squeeze. I moaned loudly and tilted my head back as I spread my legs a bit more. His hand then moved to my sissy cock and stroked it a bit. I moaned and squirmed a bit, but didn’t want Sue to know what he was doing. I felt Sue move a bit closer, put her arm behind me and lean in as if to tell me something. He was stroking me and I was having a problem keeping quiet when Sue whispered in my ear “That’s a good girl, let him do what he wants” just as she pulled hard on the ribbon tied around my balls. I gasped and fell forward a bit as I spread my legs more. He was stroking me harder now and as I lifted my head I could tell that a few guys at the bar were watching what was going on. I thought I was going to shoot right then when he suddenly stopped stroking me and I was able to recover a bit and take a sip of wine. Sue suggested that I needed to go to the “ladies room” and “freshen up” a bit so I took my purse and headed that way. There were a couple of bathrooms which were his or hers. When I got there and started to open the door I was suddenly pushed inside. When I turned to see what was going on I found the guy that had been teasing me locking the door behind us. He pushed me over and sat me on the toilet then proceeded to take his cock out and aim it at me. He pulled my mouth onto his big cock and proceeded to fuck my face until he came as he told me that I was a good slut just as Sue had told him! He made me swallow! Once he was done he slipped out and I bolted the door behind him, I could hardly believe what had happened and that Sue was a part of it. I freshened up my makeup and headed back to the table.
I was relived that Sue was alone and sat. She asked me if I was enjoying myself and I confessed to her that I was. The waitress came by with two fresh glasses of wine and I reached for my purse and the waitress said “already taken care of, complements of the gentlemen at the bar”. Sue and I looked over and there were two good looking guys watching us… I think they had seen the action before. We raised our glasses and mouthed “thank you” to them. Before I knew it they had come over to us. One standing to my left and one behind me between Sue and I. We started talking and before long, Bill, the guy to my left leaned in and told me that he and his friend Tim had enjoyed the show earlier. I blushed a bit and took a sip of wine just as I felt his hand touch my leg. He didn’t tease me or brush against it but went straight for my sissy cock and started to stroke it, I felt a pull on the ribbon at the same time and turned to look at sue but both of her hands were on the table and she was smiling at me. Tim was behind me and pressing against me while pulling the ribbon tight around my cock as his friend Bill stroked it. I felt something poke at me and realized that Tim had his cock out, under my skirt and was sliding it along the crack of my ass. I leaned forward a bit and his cock slid between the stool and my ass sliding in and out. In this position there was no way he could enter me but the effect was almost the same. The two of them were driving me crazy. I tried to act a bit normal and take a drink of wine but I noticed that there were several guys now gathered around the table we were at sort of shielding the view of what was going on from others. Bill pulled my head down towards him while Tim pulled on the ribbon causing me to have to get up from the stool. I was pushed and pulled and found myself lying over the stool with Bill’s cock in front of me. I knew others were watching but didn’t care. I felt someone push a bottle under my nose and I took a big sniff of poppers. The rush hit me and made me really feel like a slut. I opened my mouth and took Bill in deep just as I felt Tim enter me from behind. I didn’t know where Sue was but didn’t care. I heard others say things like “Take the bitch” and “Oh yeah” and even “I want some of that”. I knew I was a slut and couldn’t stop