This Halloween, I decided to get dolled up and head out as Lisa for the night. I figured Halloween was probably the safest night to go out dressed up without fear of being ridiculed. After putting on a pair of knee socks to get in the mood, it was time for some blush, mascara and eyeliner as well as very decent lipstick. I bound my hair to a ponytail but left one streak falling down the side of my face. For a little extra cuteness, I put on a heart-shaped choker with heart-shaped earrings. Then I put on my short flowery powder blue skirt that went halfway down my thighs in the front, but my chubby always hikes it up a bit in the back. Lastly, I put on a cute Blue’s Clues t-shirt and of course my light pink Skechers sneaker boots. Done!

I walked out of my building confident as Lisa. I headed down the block to one to one of the gender friendly bars in my neighborhood that I knew was having a Halloween party. At the door and it was was a bit crowded, but I found a seat at the bar and ordered a Southern Comfort on the rocks. As I was sipping my drink, suddenly a shot glass gets pushed in front me, I look up and it’s one of the bartenders smiling. This guy was buff as fuck, had an adorable beard, and being well over 6 feet and me sitting down, he was towering over me. He leaned on the bar, kept smiling, looked at me and said, “thought you could use a shot.” Responding, I tilted my head and smiled a “thank you.” He asked my name and if I was from the area. I told him that I lived nearby. He was curious as to why I was out alone, which I immediately read as him hitting on me. Wow! At that point, I took the shot and placed the glass on the counter complete with a lipstick mark. He looked down, picked up the shot glass, and what he did next turned me on beyond belief – he held it in his massive hands, stuck his tongue out, and licked the rim where my lipstick was. Wow again! it was the hottest thing I’d seen a guy do at a bar. The bartender at the other end of the bar yelled out, “B, need your help.” He looked at me and said, “You’ll stay, right?” I said, “Of course, B” to which he replied, “It’s Bryan, everybody just calls me B. See you later, Lisa.”

I got comfortable at the bar while Bryan helped the other bartender and nursed my drink, I was about to order another Southern Comfort, bit one pushed down to me. Then I saw a smiling Bryan. He’d wink at me every now and then, which had my little clitty twitching like crazy. After about 20 minutes, he made his way back to my end of the bar. Standing in front of me, he unbuttoned the shirt he was wearing and took it off revealing a tank t-shirt that only further made his muscles known. Oh, I forgot the eye-patch he put on, now I see he was doing the Kurt Russel “Big Trouble In Little China” look. As he shifted to toss the shirt behind him, his tank came up a little and I saw the hairy trail heading toward something I really wanted at this point. I think he caught me staring at his crotch, which was confirmed when he grabbed his crotch, smiled at me, and winked. He laughed, so I laughed but mainly out of nervousness about what could happen. At the same time, I knew he was bartending so it would probably just be a game leaving me untouched.

I watched Bryan serving the other girls and noticed he kept looking back at me almost as if to assure me that I was the one he was most interested in. The bar got busy, and Bryan was serving all of the people who had come in since I’d gotten there, but he still made it a point to make eye contact with me every now and then and to stop by to check-in on me. A little after 11:30pm, Bryan swung over and said, “hey, I gotta take my dinner break in five, you up for a walk?” I don’t think I said anything audibly and merely nodded my head. He smiled and said, “great, meet in the alley on the side of the bar.”

At that, I downed the rest of my drink and headed to the alley. It was as much as an alley as it was the small side door that the kitchen staff probably used to haul in supplies and to take out trash. Bryan came out with his tank top, eye-patch, and a pair of sweats on. I told him “Big Trouble in Little China” was one of my favorite movies. He just walked right up to me, leaned down and kissed me on the cheek. I could feel myself turn red. He said, come on, I live just around the corner. I froze. He grabbed my hand, and I was still frozen because this guy wanted to take me to his apartment, which got me nervous because Bryan may have had no idea that I’m a boy underneath this outfit and that I have a raging hard on in my panties. He smiles and says, “come on, just some Halloween fun.”

We walked into his building and headed up two flights of stairs, which was which I mousy followed . He unlocked his apartment door and invited me into what was a relatively nice apartment but a bit messy. He told me to sit on the couch and that he’d be right back with some drinks. He came back with two drinks and had added a pair of devil horns to the top of his head. I giggled, but he didn’t. He put the two glasses down, asked me if I wanted a sip. I picked up a glass and as I did, he came to stand right in front of me. I gulped a heavy sip of the drink and could see that he had developed a raging hard on. I gulped air this time. As I put the glass down, he leaned in toward me and suddenly grabbed my hair, pulling on it rather hard. I yelped, which seemed to turn him on. He said, “I was hoping a sexy little bitch girl like you was going to come in tonight. Daddy needs his needs taken care of. You gonna be a good girl and help?” I couldn’t produce words, so I just nodded. He smiled, pulled my Blue’s Clues shirt up and spit on my budding little tits. I was so turned on, but also scared as fuck.

Bryan grabbed my hand and told me to rub his cock. I could feel his cock growing. It was decent length, but insanely thick and he had really big balls. He looked down at me and said, “Suck it, bitch.” At that, he released my hand so that he could yank his sweats down. His big white cock flopped out and he immediately pushed my head toward his cock. I took the head in my mouth, which immediately had him moaning and calling me “good girl.” I kept bobbing up and down on his cock, used my tongue to tease his cock head and played with his balls with my hands and tongue. He ripped – literally ripped – off his tank exposing a well-defined six pack and these awesome pecs. As I sucked his cock, looked up and asked him, “Do you like it Daddy?” He said, “Fuck yes, my little bitch does a good job sucking Daddy’s cock.” I continued sucking him and noticed that his hand was fondling my nipples through my t-shirt. He said, “Daddy wants to play with Lisa’s tits.” Once again, I was fucking terrified because I wasn’t sure this guy know I was trans, that I am a femboy. Before I can say anything, looks at me and pushes my head off of his cock and then roughly pulls up my t-shirt. He looks down and tells me to lift my ass off the couch. I tell him that I’m comfortable like this, but he demands it. Once I lift my ass just a bit, he immediately reaches down and yanks my skirt off.

At this point, my panties are exposed with a massive wet spot from the precum he caused! He clearly understood what was going on at this point. I started to say, “I’m sorry,” but he grabbed me by one of my arms, forced me up, and yanked me over to his bed. He forced me face down over the side of the bed and said, “You fucking little faggot bitch! Getting me hard, sucking my cock!” He kept me in this position with his forearm against my back. I seriously thought he was going to beat the shit out of me. I almost started crying while telling him how sorry I was and that I wouldn’t tell anyone.

He just kept saying “faggot bitch” and then he said, “fucking faggot wants dick on Halloween. Ok, faggots gonna get it!” Suddenly, he yanked down my panties, I heard him spit, and then I felt his cock up against my smooth tight asshole. I said, “Hold on, we need a condom.” He said, “Not tonight sweetheart, you wanted to get fucked up the ass, so you get my cock as-is baby” He held me down harder and then slammed his cock in me. He was like a dog in heat pounding my hole. He started saying things like, “You like this huh faggot?!” “Daddy’s gonna get your faggot pussy pregnant bitch.” I was confused, scared turn on. He kept pounding my ass, grunting, and moaning. I couldn’t hold it anymore, I was going to cum. I yelled out, “I’m cumming Daddy,” to which he replied “Mmmm you fucking whore, yes let it out you bitch.” I came into his comforter as I was still face down on the bed. I felt him picking up his pace, his massive balls slapping against my ass, and sweat dripping off of his muscles onto my back. He said, “I’m gonna fucking drop my cum in you bitch, I gonna give you my babies… you ready? You fucking ready for daddy’s babies?” I merely replied with, “please Daddy.” At this point he leaned over my body holding my shoulders as he slammed his cock in me. He moaned and said, “Here it comes, Daddy’s cumming in your ass… fuck, I’m cumming… ahhhhh.” He collapsed on my back and continued to breathe heavily for several minutes. He got up and pulled his cock from my ass, and said, “get the fuck out.” I was so startled that I got my shit together as fast as possible and slipped my shirt and panties back on while he watched from the kitchen counter sipping his drink. He said, “I like that tight sissy pussy and I like thinking about you walking around with my sperm in you.” He walked over, slapped my face and said, “You’re lucky I only fucked the shit out of you, so after tonight never come back to my bar.” I nodded and almost ran out.

This was a fucking scary experience, but I’ve fantasized about it for the past three nights and have even WALKED by the bar a few times. So much for “safe” bar.