First Night Out as a Sissy

It was the first time I dared to act on my fantasies but the timing was most certainly perfect! Feeling the urge to explore my sissy side out in the world, I decided I’d hit the local sports bar in hopes I’d find a man that I could make want what I had to give.

After taking my time doing all the preparation for a confidant night, I put on my favorite panties and my tightest jeans (the ones I would never dare to wear outside until this night). I was getting so excited with anticipation of making my fantasies come true that I could feel I was having a hard time breathing. As I looked at my perfect ass in the mirror I closed my eyes and imagined catching someone’s eye; I imagined what they think and say and moreover what they’d do if I let them.

I arrived at the spot I had often scouted and I could see it was mostly guys there and some not so hot chicks. I sat in my car excited but scared trying to work up the courage to go in. I knew once everyone inside saw how tight my pants were and how they’d likely see the lines of my panties, they’d immediately know what I was there for.

I sat there in the car coaching myself about how this was what I really wanted, to find the right guy and please him like no woman could. My fantasy was to become a real butt-slut. I knew I was already one after years of fantasizing, but this was going to be the night I’d prove it. Although I was more than happy as a man, deep inside I knew I was a sissy and tonight I wanted to be a sissy and not be seen as a man, but rather as a sexy sweet piece of ass.

Since I had been in the parking lot a bit, I couldn’t help but notice a car full of guys pulling in across the lot. Determined to act on my desires, I purposely timed my exit from my vehicle into the bar so that I’d have them right behind me. Close enough that they could get a good look, put far enough back that they could see it all.

Immediately I could tell I had their attention; they were talking and laughing in the middle of a good time and all of a sudden they got quiet. Being the tease I am I stopped for a moment as if I was looking for something and stood in my favorite pose (one leg bent and slightly turned so that they could see the shape of my ass). I really don’t have the big butt I wish I had, but I do have a really nice butt. So many girlfriends had told me throughout the years about how they wished they had my butt. It always made me happy to hear and I always wished I could hear a real man tell me how much they liked my butt too.
I couldn’t resist looking back at the guys and I could see there was four of them. They looked so handsome, clean and athletic I couldn’t help but smile with the sudden thought of how well each of them was likely hung. It was clear to me I had their attention, they kinda had that look on their face of “daaaaaaammmmmn” but also like they couldn’t figure out why they were checking out a guy (LOL). I loved it! I was so happy inside because I finally felt like I could attract sexy men and catch their eye.

I walked in but was immediately disappointed that they went to the other side of the bar. They seemed to know one of the waitresses; they all seemed happy to see each other and I could feel myself getting jealous. My initial joy had suddenly changed to disappointment and my confidence suddenly eroded.

It was my plan to stand at the bar to be certain everyone could see what I had, but instead plopped myself on a stool pouting like a true sissy. After a few drinks, I couldn’t help but notice one of the guys step outside. I thought to myself, “what the hell, why not” and went out a few moments behind him. I was kinda embarrassed that I ran right into him just outside the door and quickly fumbled for my phone like I needed to make a call. I stood with my back to him hoping he was checking me out and after a few minutes I pretended to end my call and fidgeted with my phone.

Suddenly I heard someone asking playfully “are you following me?” I didn’t realize it was “my guy” and that he was actually talking to me. Not receiving an answer he came up behind me and asked again “are you following me?” I was so shocked that I had made it that obvious that I felt myself immediately blush badly. I kinda laughed and replied “umm no” in a way that made it obvious I was. I was so embarrassed that I couldn’t even look him in the eye. His response was simply out of my dreams when he said, “aww, that’s too bad, I thought you were shaking that ass for me.” I was overcome with excitement and could feel myself getting dizzy with passion thinking to myself “wow – this is really happening.” Not knowing what else to say and wanting to be sure he got the ‘right idea’ I went full into full sissy mode and said “baby if I was shaking it for you, you’d know it”.

For a moment I thought I had made a big mistake because he grabbed me by the wrist and confidently said “come with me baby”. We went off to the side of the bar by a little alleyway leading to the parking lot and just stopped and stood there a second. I felt so sexy that a man like him was being so aggressive with me as if he wanted me so bad he couldn’t stand it. After a momentary stare of passion between us, he pushed me up against the wall and started to kiss and suck on my neck. The feeling of his hot breath on me and the roughness of his slight beard was so exciting. I pushed myself away from the wall a bit and pushed his hands down to my ass. I would feel how large his hands felt on my tiny sissy butt and he went absolutely mad with passion.

I could feel his now super hard cock between us and I pushed my leg up against it and rubbed it firmly with my thigh. I could feel his length and girth through the tight pants I was wearing. After a moment of teasing him, he spun me around so he was behind me and I raised my arms above my head and placed them on the wall in full submission while he yanked my hips back onto his oversized cock. I was more than happy to grind my sweet ass on that dick and when he reached down and put one hand on my sissy ass as if to spread me I just about died. By now he was starting to talk dirty to me, but not so much that I felt dirty, instead he made me feel so sexy telling me how he was going to make me his bitch.

Just then, he reached around me and started to try and undo my pants – I got to admit I got pretty scared and quickly turned around telling him “not here, not like this.” He made it a point to show how frustrated he was by putting his hands on the wall roughly as if to corner me. But instead of getting mad he rubbed his finger in my lips saying “but I want you baby.” I realized it was my turn to take charge and grabbed him by the wrist and led him to my car. I knew as long as no one was watching us they could never see us once we got into my car with my overly tinted windows.

We got to my car and I got into the back crawling across the seat making certain he could get a full view of my sissy ass to see how willing I was going to be. My message was received because he began to rub his hand firmly up and down my butt crack pushing his thumb right up against my sweet hole. I begged him to get into the car with me telling him I wanted to show him something. He hadn’t even closed the door yet and I was still on my knees already wiggling my sissy ass out of my tight jeans trying as hard as I could to leave my panties up. Seeing I was trying to give him a show he began to pull my pants down nice and slow, mostly holding them in place as I rose on my knees holding onto my panties while wiggling my sweet little ass out of those jeans.

Suddenly I felt his hands leave my body feeling and hearing him just flop down on the seat. I immediately turned to find out what was going on and he said he was trying hard no to cum. Just hearing him say the word ‘cum’ got me going and in my sweet sexy sissy voice I told him, “baby, try all you want to stop it, but you’re going to cum, that I can promise you!” I reached down between his legs and found his swollen cock ever so hard in his pants. Together, we lowered his pants and his cock flipped up as the elastic from the waistband of his boxer briefs passed over his enormous dick. This was the guy of my dreams! Sexy, handsome, rugged and well hung! His huge dick took my breath away and I made it so obvious I was admiring his beautiful cock loving the way the bright light over my car illuminated his just right that I could see he was getting wet. He was so long and had so much girth I could hardly imagine this was going to be my first fuck.

I began to rub my mouth up and down his cock, grabbing it hard at the base causing him to surge with passion. I reached down between his legs and made sure I could have full access to his large and well- trimmed balls. As I took his balls in mouth still firmly squeezing his massive meat he rose up to help me get my mouth around his sack. It felt so warm, so soft, so smooth and I couldn’t help but stare at all that dick that was about to be mine. It looked so muscular with well-defined veins pumping that dick full of blood. Knowing I was the reason he was hard was the stuff of my dreams. After taking my time with his balls, I sucked my way up his shaft making sure he could feel the warmth and wetness of my sissy mouth.

As I got about halfway to the top, I could taste and feel all of his wetness from my attention. As much as I wanted to lick it all up, I took has hand and had him wipe it up with his finger. I could see his fluid glistening in the light as I carefully guided his well lubed finger moistened with his juice and placed it on my tight virgin but eager ass. As he rubbed and rotated his finger to spread his wetness on me, he slowly pushed his finger into me while I tried as hard as I could to get all of that dick into my tiny mouth.

I whimpered like a sissy as he pushed his whole finger into me after several attempts to get passed my tight sweet butt hole. His finger hurt me so much I had to stop sucking on that dick to try and relax. Just then, he pulled it out of me and rubbed his finger on my lips. The scent of my ass got us both excited and we kissed while sharing the taste of his wetness and the scent of my ass all over his finger. I could tell he was ready to cum and not wanting to miss a drop, I went back down on him. I squeezed my lips as tightly as I could wanting him to imagine it was the tightness of my sissy ass. All of a sudden he started to quietly scream “I’m going to cum! I’m going to cum!” as if he was trying to warn me in case I didn’t want his load. I never took my mouth away while he squirted over and over into my mouth. I wanted him to see me take his load, but the way we were positioned would have meant I would have likely missed some.

I wasn’t willing to miss a drop so I waited till I was certain he had given me all he could and carefully took my mouth away. I wasn’t until then that I realized how much he had gone, I could feel him spilling out of my mouth down my chin as I showed him I had his whole load. The taste was so sweet and was just the right thickness and the scent of his cum drove me crazy. It took me almost three swallows to drink his hot load and I just laid across his lap never wanting the taste that I was tasting and the feeling I was feeling to ever go away.

Just as we were both coming back to our senses there was a hard knock on the window and a bunch of laughing. Ugh, I was so embarrassed; his three friends had just busted us. He pretty much threw me off of him and yanked his pants up getting out of the car. I was trying not to let them see me wiping the cum off my chin but that was pretty much a wasted effort. His friends began to taunt me saying “I knew what you were here for” as they walked their friend back into the bar, not even bothering to close the door. I got pissed for a second but then I got to admit, it felt so sexy to feel like a whore that had just been used.

I laughed and laughed while I pulled up my pants and cleared myself up. I lost my breath so many times wiping the cum from my chin while tasting and smelling what remained of his load. So I sat there getting a grip deciding I would just go home after a great but incomplete night (I still wanted him in me). I got into the driver’s seat, stated my car then realized the bartender kept my credit card!

If you like this story then I’ll have to tell you how the second half of that night went…..