First Night Out Ch. 01

"Tonight is the night."

This is what I told myself as I was looking at the mirror, contemplating on whether or not I should push through with my plans for tonight or not. I tried keeping myself busy while at work but my mind kept lingering back to the thought of my plans for tonight.

Just a little background, I have been a secret sissy for about a year already now and if you've read my previous stories then you would know that I've had my fair share of experiences already with trans women and I've only had sex with them because of my obsession with the female image and despite me being a bottom for them, I would normally be a top when it came to my gay experiences.

Recently though after watching numerous videos of hypnos, I've slowly become more open to the thought of me dressing up for a real man to do things with me, whether they be as mild as catcalls or groping me or maybe going as far as going down on him and maybe even letting him fuck me if my mind and body would permit at that moment.

So when I got home from work that night, I looked at myself in the mirror and reassured myself that tonight was going to be the night that I push through with this plan. At first, I thought I could make it easier for myself by downloading Grindr on my phone but when I first posted myself there, all I got were requests from different guys asking if we could just do phone sex which wasn't really looking for since I wanted the real thing.

I left my phone on my bed to wait for any more responses while I fixed myself up. I brought out the entire ensemble of clothes that I was going to wear for tonight. Since I was going out at night, I didn't really want to wear anything flashy and I wanted to kind of blend in with the night if you get what I mean. All of the clothes I brought out were black, except for some frilly pink panties so I can add a bit of color in my outfit.

My outfit consisted of a black cotton halter top that I got for one of my exes and it conveniently fits me now, a black pencil skirt that stops just below my panties, a black garter-stocking set that would shape my long slender legs perfectly, some fishnet forearm gloves to make me look a little bit more playful, and of course a pair of black 4 inch heels that not only makes me taller, but makes me feel hotter in general.

Before I got into my clothes though, I took a shower first where I cleaned myself from top to bottom, inside and out. It feels so different taking a shower than when I normally do before work because I have this lingering thought that I'm going to be a sexy sissy slut by the end of this night and just feeling the water trickling down on my smooth body felt like hands groping me while I was naked and vulnerable.

When I got of the shower and dried up, I played some sissy hypno affirmations to listen to while I got dressed up.

"You are a sissy slut."

I got into my pink frilly panties and made sure that I took a quick glimpse at the mirror as the panties hiked up my ass and gave me ass a cute but toned look.

"You need cock."

Next I put on the garter-stocking as the patterns of the stocking hug my long legs, I couldn't wait to see myself wearing them outside standing on the side of the road.

"Dress up just to get messed up, that's right sissy!"

As I was about to put on my halter top, I stopped myself and remembered that I just recently bought fake breast fillers and I contemplated at first on whether or not I should wear them to complete the look and since I had already planned the whole thing for me to turn out to be girly, I decided on wearing them along with my halter top.

"There's no turning back now sissy, embrace who you really are!"

With the gloves as my final piece of clothing, I had my outfit complete for tonight. Covering up my face and looking at my body from the mirror, I would definitely be interested in a woman dressed like me tonight.

I won't really go into the makeup routine I had since it was still fairly simple, I focused a lot on my eyes since I was also going to wear a mask to hide most of my face anyways. With my make-up done, there was only the wig that I was going to wear since I had two of them; one that was blonde and the other brunette. Since I was going out at night and I had a pretty dark outfit already, I went with the blonde one to make myself stand out a bit more.

When I returned the brunette wig back to my wardrobe, I noticed a metal shine from one of the drawers and when I opened it, it turned out to be an old pink plug that I used to play with and even wore on some occasions. I thought about it and since I didn't really know where the night was going to lead, I decided to wear it anyways since I had nothing to lose and pleasure to gain by wearing it.

Going back to my phone, there were so many messages while I was busy dressing up and although it was a bit of a hassle to scroll through them, I did end up finding one that took my interest.

He sent me a message saying, "Hey sissy, I'm looking for some quick action and since you said that you didn't really have experience doing this I thought I could show you some tricks. Hmu if you're interested."

It wasn't really the sweetest chat but then again he did take into consideration how I'm really new to this and he might just be what I need to slowly get myself into this.

I replied, "Hi Daddy, yes I'm really new to this and I want someone to show me how to be a proper sissy slut but in a nice way :)"

He replied almost immediately saying, "It's good that you replied to me then, I'll take care of you as long as you'll be a good girl. You can do that right?"

It hit me like a shock. I didn't know if it was the hypno affirmations I was listening to a while ago but I really thought I still had them on when he called me a good girl which made me feel giddy for some reason.

I replied, "Yes daddy, I can be a good girl for you. Where can we meet?"

Just typing that alone made me shiver with excitement. He then replied, "I'm actually out right now but we can do it in my car or even in an alley if that's your thing. I'll send you the address and just tell me when you're here, I'm sure I won't miss you when you do get here though ;)"

Once he sent me the address, I immediately got my stuff and took one last look at the mirror before leaving, a sissy slut from top to bottom excitedly staring back at me. Once I was outside of my house, I already felt the cool air of the night going through my stockings and even hiking up my skirt, feeling the coolness go all the way up to the plug I was wearing.

I got into my car and started driving towards the address given to me by daddy and as I was driving, I could feel some of the people in their cars that would stop beside mine in traffic staring at me and I even exchanged some glances and got a few smiles from some of the men who would take a look at me. I was just imagining what they saw, a sissy slut dressed to the nines driving her way to meet her daddy.

When I got to the address, I chatted up daddy and it took a while for him to reply but when he did he said, "Hi sissy, I was wondering if you were going to show up tonight. Wait for me at my car, it's a black pickup truck you won't miss it."

He also gave me the license plate to look for so I got out of my car and started looking for his car. The area that I was in had lots of bars and nightclubs lined along the main road, I wouldn't really call it a red light district but just a popular spot for drinking and picking up girls as well. I remember walking on the pavement with my heels making a clacking sound each step I made; how tall and sexy I felt as I swayed my hips; and the stares and glares I would get from men and women alike, the stares from men who lusted for me and the glares from women who felt like I was stealing their piece of the pie.

Once I found his car, I chatted him again that I was already there but I wasn't getting any replies from him anymore. I looked around and saw that there was a pretty loud bar with a balcony nearby and I was guessing he was still partying it up there. So I decided to be a good girl and wait for my daddy but slowly time passed and I hadn't noticed that I've been waiting for an hour already and still no reply from him.

I was getting nervous already since things weren't going as planned so I decided to go inside to look for him. The bouncer didn't even ask for my ID or anything, he just looked at me up and down and nodded his head, he then gestured me to go in.

I don't normally go out, let alone to places like these so I was a bit shy moving around the place. Thinking about if someone I know will recognize me, how some of the guys in here are giving me looks that were seductive but felt dangerous as well. I decided to head to the bar and get myself a drink to try and calm down from all that's happening. A few guys tried approaching me but they came on a little too strong for me so I just shook my head no whenever the came up to me.

I must've drank at least 3 glasses of whatever cocktail I was getting and I hadn't noticed because it was one of those sweet cocktails that you don't even taste or feel the alcohol that much but once you stand up, oh you feel it alright. My vision was getting blurry and I was getting overwhelmed with all the noise from the bar so I decided to go out and get some air.

I don't know how long I was in there but probably not that long since when I got, the car that I was chatting with earlier was still parked out front so I figured that he was still inside. Checked my phone again and still no reply from him. I stood around for a bit before deciding that I should just call it a night, besides I got to drink out without anyone that I know catching me while dressed up for the first time so I guess that's a win.

I started my long and slow walk back to my car as I passed some other bars that were still lively, I also passed by some people who were either looking for the next place they were going to hit up or were already on their way home as well. I didn't really pay attention that much to the people but I was pretty sure that I was getting a few stares and even some catcalls from different guys which was slowly building back the fire inside me that I had when I started this night.

I reached a corner spot on the street with a lamp post directly above it and I decided to rest there since it was visible and I was just a few feet away from my car, without realizing what I must've looked like on that corner.

I only realized it when I was already caught in the moment. A car that was parked a few inches from the corner suddenly flashed it light and at first I didn't really pay mind to it since it could've been just a car starting up or something. He flashed his lights again and I still didn't pay attention until he started flashing erratically and I saw a hand come out of the car window on the driver's side waving me to come over.

I don't know if it was just me being tipsy or me slowly getting turned on on my way back to my car or just a little bit of both, but I didn't even hesitate as I fixed myself up and made sure everything was in order before walking towards his car. I got greeted by a young middle aged man, somewhere in his 30's. He wasn't ugly but he wasn't all that good looking either, he looked like he had quite a few to drink since his eyes were blinking pretty slowly and his eyes were wandering all over me.

As I was standing there he suddenly broke the silence and said, "Hey cutie, how much do you charge for say, a blowjob?"

I was caught of guard. Like I said earlier, I didn't really know what compelled me to just come over here without really thinking about the overall situation that's going down. I fidgeted for a while and looked around almost like to see if anyone else was seeing this actually happen. I thought of all the stories I heard about street hookers and what they did with their clients and how much they charged. I didn't really want to offend him by giving him an expensive price but I also didn't want to lowball myself especially that this is the first time this is happening to me and I didn't even plan on doing this at all.

I didn't want to speak up either since I hadn't really practiced my voice yet and I'm pretty sure this guy is drunk enough not to realize that he's actually asking for head from a guy dressed up like a sissy slut. I was panicking inside so I just raised my hand and showed him five fingers.

He looked at my hand and then looked at me and asked, "50?"

I just nodded my head in agreement and he looked like he was thinking about it but then he took a look at me again, up and down completely, and then waved his hand inside to tell me to come in to the passenger seat.

"Holy Shiiit! This is actually happeniiiing!" was what I thought as I walked around his car towards the passenger side and opening his door and making sure that I entered his car with my ass first before anything else which made him shift in his seat and he also adjusted his pants after.

I didn't really know what to do from there so I just reached over to his leg and started rubbing there while I looked at him and when he looked back, I smiled behind my mask so my eyes scrunched up a little trying to make myself look cute for him. He then took my hand from his leg and placed it on his growing hard on. I was so hot at this moment, just to feel him getting hard because of me and what I was about to do to him; what I would do to feel that every single day.

He just sat there quietly looking down at his crotch and from time to time glancing up at me as I fiddled with his belt and button to open up his pants. When I finally got them undone, I opened his pants up a bit and started groping his underwear.

Have you ever felt a man's dick straining against the fabric of his underwear? It felt so empowering in a way for me. The girth of his dick giving my hand a hard time to grope it completely, as I massaged his dick up and down I could feel the blood rush through his veins as they almost popped from how hard he was getting. Stroking him up and down and then cusping his balls to make him moan and suck in some air for me.

I was almost in a trance. I can still pick up on how he was reacting to what I was doing and the fact that there were some people passing by the car who could've definitely seen what I was doing to him and yet all my focus was still on his dick, growing more and more as I stroked him. After a few more strokes, I looked up at him as if I was asking for permission to pull down his underwear to reveal what I've been waiting for. He looked back at me with this lustful eyes while he was biting his lower lip and then he nodded in approval.

I shifted while in my seat so that I had my left leg raised on the seat so I could have a better angle while sucking his cock. I took the garter of his underwear and lowered them up until his balls and there it was standing in attention. It was a good five inches at least and it wasn't too thick that it would've made my jaw sore from just a few pumps but thick enough that my mouth would feel full with each stroke into my mouth.

I didn't look at him anymore for permission, there was just an insatiable lust inside me right now that wanted to devour this cock in front of me. All those voices and captions that I've read and heard from the sissy hypnos seemed to come back to me at that moment; I want cock, I want to suck his cock and make him cum, I want to be a sissy cocksucking slut.

I grabbed his dick with my left hand and started stroking it for a while, admiring whenever the head would disappear in my palm and pop out back again. As I kept stroking him, he slowly started to leak some precum from his slit so I took that as my signal to start. I raised my mask up enough to let his dick in and when I was close enough to his dick, I gave it a lick and I looked at the streak of precum clinging from his dick towards my tongue and I lapped it up too after.

I admired his dick one more time before I started kissing his dick and I was almost making out with it at one point. After that, I gave the head a few licks on the underside before closing my mouth on it entirely. I couldn't hold myself back from moaning during that moment, taking in the moment I first took in a real man's cock into my mouth and I wasn't done yet.

I adjusted from my seat again so I could push myself and lean lower into his crotch as I started bobbing up and down his dick, slowly making it easier for me as my saliva coated his dick. I was moaning and slurping like the little slut I was and it made me giddy whenever I would take his dick back in my mouth and he would moan as he held my hair or just groping my body in general.

I was really getting into it now when i adjusted from seat again to the point that I was kneeling down on his passenger seat with my ass basically aimed at my window so if anyone was passing by, they'd get a pretty show of a sissy slut sucking cock while she showed off her plugged ass to everyone else.

I shifted my position because I wasn't taking in the entire thing inside my mouth so I wanted a better angle to try and deepthroat him. He must've understood what I was doing because I felt his left hand grab me by my wig as I was slobbering up and down his cock. When I was at an upstroke and about to go down, I held his dick with my hand as I slowly inched my way down his crotch until I started feeling his pubes tickle my face but I wasn't all the way down yet. That's where he came in and pushed my head down even more until I was now buried into his pubes.

He groaned and said to me as he held me down, "Oh yesss! This is what I've been looking for all night, a good bitch like you knowing her place and sucking my dick like a lollipop."

Oh my God, I couldn't tell you how turned on I was by this. A man holding my head down on his dick as I deepthroated him willingly with tears starting to roll down my eyes all the while as his other hand explored my body and often lingered on my ass. I was so tempted at that moment to just take off the mask and enjoy the moment completely but it was also a bit of a turn on to have a mix of my saliva and his juices stuck on my mask like that.

I only got to raise myself up a little bit from him to breathe when he suddenly started pushing down on my head again. I wasn't really prepared for this and I had a moment where I tried to fight back and I even tapped on his leg to tell him that I was having a hard time breathing but he didn't care. He was already lost in the lust and was going to do anything and everything to get his satisfaction satiated and he just so happened to have the perfect fuck doll to do it to.

He started fucking my mouth like a pussy, hammering his dick in and out of my mouth while all I could was sit there and take it like the sissy slut that I was. I was choking and grasping for air but at the same time it was this very feeling that was also turning me on. The fact that I was getting face fucked like I was nothing but a cheap fleshlight all the more fed into my sissy persona and it just fueled the flame of being horny inside me.

I don't know how long we went at it, all I know is that from time to time he would give me a few seconds to catch my breath and he would get right back to fucking my mouth pussy. The sound of his dick hitting the back of my throat with the familiar glug, glug, glug sounds that I've always heard whenever I watched porn. The feeling of his dick going inside my mouth with my throat adjusting to the shape of his head as it passes through the opening of my throat. Everything about this experience was just bliss.

He was groaning a lot more and his grip on my head was starting to tighten so I knew what was about to come. I tried to push off of him because I wasn't really sure if I would be able to swallow it all but he just held me head in place the entire time, from thrusting violently to patiently and intentionally stroking his dick with my mouth pussy.