Halloween Rabbit Holes

I had seen some men, one man many times, and was having a lot of fun. The one guy I was seeing constantly was 58 a bit of a belly, but an amazing cock. After a bit he had gotten me into cross dressing. It started with panties. Then stockings and heels. Leading to bras, skirts, and wigs. Eventually I was putting on make up, eye lashes, lipstick, the whole nine yards.

Halloween was coming up, and naturally I was over excited due to my new favorite pass time. The only bummer was when I asked my playmate what his plans were for the night he told me that he would be out of town for work that evening. Seeing my obvious disappointment, he told me we would play soon after, and would have something extra special for me to wear.

Little did he know I had already gone about building a sexy, slutty Halloween costume. I had decided I wanted to take a run at being Jessica Rabbit. I already bought a full red wig, the shiny red dress cut to expose my entire leg (and maybe a bit of my ass). I had the arm length purple gloves and the sexy red high heels. Adding my own touch I went with a light purple lace thong and bra.

I was disappointed I wouldn't be showing it off for him, but I did not want to waste the opportunity to wear it. So after much personal debate I told my self I would go to the gay bar for Halloween, even though I had never visited one yet.

The night arrived and I shaved the little amount of hair I do have (lucky me). I got my make up done, a bit sluttier than usual hehe. I slid into the thong, which always got me so excited feeling it nestle against my tight little asshole, and compress lightly against my little girly dick. This was followed by the bra, the dress, and the heels.

I checked myself out in the mirror as I fixed the wig to my head. Very happy with how slutty and passable I looked. I was very excited, and I was pretty sure it would have a similar effect on some guys at the bar.

I called a cab and headed to the bar. The cab driver gave me a once over, obviously checking me out, but showing no signs that he figured out I wasn't really a girl. Which in turn left me very satisfied with my work.

Once there I headed in and went straight to the bar. Feeling a bit nervous I ordered a drink, vodka cranberry, and sat down to survey the place. It was pretty busy, many in costume, many not. It was a pretty good group, lots of younger guys, but enough older men to keep me happy as well. After a few minutes of sipping at my drink, the bartender who served me started to talk to me. He was nice and good looking, but way too young for my liking. We talked for a bit, I eventually let him know I was into older. He sighed, and told me good luck, that I would make someone happy that night. He bought me another drink and went back to his duties.

About a half hour or so had passed and I was working on the second drink when a man came up to the bar and sat beside me.

'Well well, aren't you a sexy thing!' he said as he sat down next to me.

'Thanks.' I said sheepishly and blushed a little.

'How are you doing tonight?' he asked grinning 'What brings you here, especially looking like that?'

'Well...' I stammered a bit through the first few words nervously '...well, I had gotten the outfit for someone else, but they were not available tonight... So I decided to wear it anyways and come here.'

'Wow, that is very unlucky for him. But I'm not complaining.' He said excitedly. 'Do you come here often? I don't recognize you, but that could just be your costume, its amazing by the way!'

I smiled at him, I was happy to be getting his attention and praise. He was fairly good looking, not really muscular but solid build. He was about 60, and looked to have a decent bulge inside his pants.

'I haven't been here before.' I replied. 'I decided to come sort of on a whim.'

He smiled even bigger, reaching across himself to offer me his hand for a hand shake. At the same time he very smoothly lowered his other hand and rested on my exposed leg.

'Doug here honey.' He said warmly, gauging my reaction to his hand.

'Jessica.' I smiled, shook his hand and moved my leg so his hand inched higher. I was very excited, and surprised that he came on to me so suddenly and up front, but I was not complaining.

We small talked for a bit , his hand travelling the length of my leg. Eventually he had guided my hand to his leg, and it drifted toward his crotch. We had another drink and chatted mostly about sex well I massaged the meat he had hidden in his pants. It had become hard and I was not disappointed, it was a good size 7-8 inches by my feel.

I was lost in the moment, only half paying attention to what we were talking about, as my hand worked and played with his cock through his pants. I was startled a bit when his tone changed from the quiet whispers we had been trading.

'So would you like to go somewhere?' He asked.

I looked up a bit shocked. 'Um, sure.' I managed out. I came here knowing that it would lead to something of the sort, but was still nervous (and excited) now that it was happening. 'Do you have a place in mind?' I asked.

'I am afraid I don't have that much time myself.' He replied. 'My truck is outside though, I have a pretty secluded parking spot.'

'Alright, that will have to do then!' I said, trying to stop myself from sounding to excitable.

He stood up and offered his hand, which helped me rise and then found it's way around my waist. His arm around me, his hand on my ass as we walked out, I could feel a few of the patrons checking us out as we left.

He guided me to his truck, a large black one with a big cab in the rear. He opened the passenger side rear door, and helped me into the truck making sure his hands were all over my ass as i climbed up. Once I was in he hoisted himself up and slid onto the seat next to me.

He did not waste much time as he unbuckled his pants and had them around his ankles in no time, exposing a nice cut 8" cock. He was already pretty hard, and I was definitely tenting my tight purple panties, and slim fitting red dress.

I shifted to my knees beside him on the seat, and assumed the position ready to suck every last drop of cum from his cock. Beginning with my hands, in the smooth purple gloves, I stroked his hard thick shaft slowly, while massaging his full meaty balls that hung so deliciously from his pole.

Although I'm sure he liked my massage, it wasn't long before his hand found the back of my head and gently guided it down to his cock. As my head dropped his hand floated to my back side, where he pulled the dress up.

As my tongue swirled for the first time around the head of his cock, lapping at the river of precum oozing from it, I could feel his hand slide into my panties his fingers striving for my hole. I swirled my tongue once more, and began to slide my mouth down his cock.

'Ohhh girl, that is a great mouth, how do you like Daddy's cock!?' He exclaimed.

'Mmmmmm' I moaned as I slid my mouth back up his cock and off, a nice trail of spit following from his daddy meat to my mouth as I raised my head. 'I love it Daddy, it tastes sooo good.' I cooed to him before returning to his dick.

My head bobbed up and down generating a good rhythm, only stopping to lick his heavy sac, or slurp my saliva mixed with his precum off of his shaft. Gently kneading his balls as I swallowed as much of his cock as i could at a time.

As I got more into it, he rubbed more and more on my pussy driving me wild. I could feel my own little dick oozing in my panties.

This went on for a while, him dirty talking me while I bobbed all over his cock like a cum starved slut. Stopping only to continue to lick and suck his beautiful balls, and to run my tongue along his shaft to collect my generous amount of spit and his generous amount of precum. His hand moved back and forth from my cheeks to my hole, eventually dipping a finger into my tight asshole.

I moaned hard on his cock as it slipped in, and it drove him over the edge.

His thick impossibly hard cock exploded into my face, since his finger in my hole had caused me to pull off. A huge stream of cum splashed over my forehead, down my nose and over my lips. Not wanting to lose anymore of his cum I clamped my lips around his mushroom head.

For the next minute or so I held my mouth there, rolling his balls in one hand and slowly stroking his shaft with the other. Emptying every last drop that could be milked from his cock.

My mouth felt very full, and I could feel the rest of his load slowly sliding down my face. I pulled off of his softening member, and looked up at him in the dimly lit truck. I opened my mouth so he could see his gigantic load before I swallowed it. I closed my mouth and swallowed his seed.

With a smile I ran my tongue over my red painted lips (or atleast what was left of the red) and smacked them when I was finished. 'Thank you Daddy.' I said as I gathered the larger globs of cum with my finger, sucking it clean every time I could find a satisfying amount. 'That was fun' I giggled.

'Oh honey was it ever!' He sighed back to me. 'I will need to keep an eye out for you.'

I smiled back at him with my cum glossed face.

'I am sorry that we can't have more fun, but I need to be going' He said earnestly, showing an obvious disappointment that the night could not continue.

'I understand' I replied a bit sullenly as I straightened my panties and dress out. 'I'll watch for you too!'

He chuckled a bit 'Might wanna clean your face, and touch up your make up a bit if you head back in there tonight.' He laughed a bit more 'That is going to attract some attention looking like that.'

'Maybe not the worst thing!' I laughed back. 'But thanks' I smiled.

He opened the door let him self out and extended his hand to me to assist me down in my heels. He gave my ass one last squeeze.

'See you around Jessica'

With that he circled around the truck and hopped in the driver seat. He waved again right before he pulled away. I gave him a soft smile and a wave back.

I let out a deep breath, collected my thoughts, readjusted my penis in my precum soaked panties, and made toward the club. Getting to the bathroom to spruce myself up being my focus.

'Did you have some fun in there?' A voice from behind me called out.

Startled, I nearly jumped out of my skin. I turned around cautiously to see where the voice came from.

'I'm sorry, I didn't mean to scare you' The voice followed up. 'I just saw you and that man get out of the back of that running truck parked in the shadows, and thought you might have had some fun'

I smiled nervously at the man, a bigger guy, for sure in his sixties. 'Maybe' I said sheepishly.

'Well I sure hope you did, he certainly did with you looking like that.' He said to me kindly. 'I was just heading into the bar over there, maybe you would care to join me?' He asked, showing an obvious desire for me to reply in the positive.

I scanned him up and down, a heavier set man about my height, wearing a blazer and khakis. I guessed his age around 60-65. I decided to myself that I was still very horny having not cum myself. I could feel my previous daddy's cum drying on my face as I stood there deciding.

'Ok, I'll join you mister. But I need to head to the washroom quickly first' I smiled wide at him as I moved closer to him and even let him place his hand at the small of my back as we headed back into the bar...