On Halloween, I decided to get dolled up and head out as Jenna for the night. I figured Halloween was probably the safest night to go out dressed up without fear of being ridiculed. I decided to go all out – I took off from work and decided to start the day by heading down to Macy’s.
My first stop was to the lingerie section to buy myself a new bra and some sexy panties to go with it. I meandered up the escalator to the women’s clothing section and picked out a sexy pink skirt and a tight top with a cute graphic print of Care Bears (LOL). I also treated myself to a pair of pink open-toed heels. I have super tiny feet for a guy (7 in men’s) and narrow, so finding a pair on the sale rack was easy enough. I paid for everything and then made my way down to the Mac counter for a makeover.
I’m pretty comfortable doing this on my own, but felt this was enough of a special occasion to warrant having it done by a true professional. Sitting in the chair, the artist asked me what type of look I was going for – I told her let’s go for Halloween prostitute. She looked at me, clearly got the point, smiled and immediately started to work her magic with the brush. She taught me each step so I could replicate it when I got home. When she was done, I wanted to put my own cock in my own mouth – it looked so sexy! With my makeup done and the bag with my outfit in tow, I hurried out of Macy’s, hailed a cab, and headed back uptown.
When I got home, I rushed into my apartment, started to run a hot bath, and stripped off all of my clothes. I live on a high floor and love leaving my blinds open because this guy across the way always stares even though he clearly tries to pretend that he’s not. I slipped into the tub and listened to some music as I gently cleaned my body. After a relaxing bath, I turned on the shower and shaved to ensure I’d be perfectly smooth for the evening’s festivities.
Hopping out of the shower, I started to work on my hair. I had been growing my hair out for a while at this point, so it’s naturally long and curly. I laid out all of the makeup I bought along with my brushes and got started on my face. By the end of it, I clearly saw Jenna in the mirror. I looked down at my bare nipples, reached over, grabbed my bra and put it on. I slipped two silicone breasts in and then gently slid my panties up my legs, over my girl stick, and up over both of my ass cheeks – my squats have definitely been paying off. Next, I put on my skirt, Care Bears shirt, and fishnets. I finished the outfit by slipping into my heels. I stood in front of the mirror and said, “hey girl!” I felt sexy and ready to head out. It was around 10pm, so the night was only starting to get busy.
I walked out of my building confident as Jenna. I headed up the block to one of the sports bars in my neighborhood that I knew was having a Halloween party. At the door, the bouncer gave me an up and down and merely waved me into the bar – phew, no ID check. I went to the bar, ordered a bourbon on the rocks and whipped out my cell phone. I logged into Grindr to take a look, but nobody really piqued my interest. 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 was 6’1” - 6’3”. At 5’5”, I could feel him towering over me. He leaned on the bar, kept smiling, looked at me and said, “thought you could use a shot.” Responding, I felt on the verge of squealing but was able to clearly articulate 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 so I decided to go all out on being Miss Flirtatious. 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. I think he felt all of the oxygen in my body flow out and my knees shake, because it was the hottest thing I’d seen a guy do, especially for me as Jenna. 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 Brandon, everybody just calls me B. See you later, Jenna.”
I chilled at the bar while Brandon helped the other bartender at the opposite end of the bar. I nursed my bourbon and noticed how Brandon kept his eyes on me. He’d wink at me every now and then, which had my girl stick 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. As he shifted to toss the shirt behind him, his tank came up a little and I saw the 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 a state of anxiety about what could happen. At the same time, I knew he was bartending so it would probably just be a game leaving my pussy untouched.
I checked in on Grindr again, but once again found men who were not of interest to me, plus I had Brandon stare at. I watched Brandon 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 Brandon 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, Brandon 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 bourbon and headed to the alley. It was really much of an alley by New York City standards as much as it was the small side door that the kitchen staff probably used to haul in supplies and to take out trash. I leaned against the cleaner of the two walls and waited. Brandon came out with his tank on and a pair of sweats. Did I mention how much I love a man in sweats? Anyway, he 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 Brandon has 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 remarkably easy given my heels. He unlocked his apartment door and invited me into what was a relatively nice apartment albeit unorganized to the extreme. 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. 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 hair back and spit on my tits. I was so turned on, but also scared as fuck.
Brandon pulled on my hair, while he 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 entire thing in my mouth on the first go, 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, he flexed his pecs, which turned me on so much. I 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 silicone breast through the Care Bears shirt. He said, “Daddy wants to play with Jenna’s tits.” Once again, I was fucking terrified because this guy has no clue that I am boy – albeit a femboy. Before I can say anything, his hand thrusts through the neck of my shirt and it’s too late. He pulls back his hand with a silicone breast, looks at me and then the breast, drops the breast, 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. You think this is funny? Getting a straight guy hard, sucking his cock, and not telling him you’re a fucking dude?” 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 started crying and 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 but not how she wants it.” I noticed how he said she and realized I had no idea where this was going. Suddenly, he yanked down my panties, I heard him spit, and then I felt his cock up against my smooth tight hole. I said, “Hold on, we need a condom.” He said, “Not tonight sweetheart, you’re going home with me in you.” He held me down harder and then slammed his cock in me. He was like a dog in heat pounding my pussy. He started saying things like, “mmmm, tight pussy” and “that’s a good girl, Daddy’s gonna get your preggy on Halloween.” I was crying but also incredibly turned out. 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?” 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 tight pussy… 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, slapped my ass, and said, “get dressed faggot and get the fuck out.” I was so startled that I got my shit together as fast as possible and slipped my clothes back on while he watched from the kitchen counter sipping his drink. He said, “I like that pussy and I like thinking about you walking around with me swimming inside.” He walked over, slapped my face and said, “You’re lucky I only fucked the shit out of you, so after tonight don’t come back to the bar.” I nodded, slipped on my heels, stood up and ran out. I headed home as quickly as I could.
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.
My first stop was to the lingerie section to buy myself a new bra and some sexy panties to go with it. I meandered up the escalator to the women’s clothing section and picked out a sexy pink skirt and a tight top with a cute graphic print of Care Bears (LOL). I also treated myself to a pair of pink open-toed heels. I have super tiny feet for a guy (7 in men’s) and narrow, so finding a pair on the sale rack was easy enough. I paid for everything and then made my way down to the Mac counter for a makeover.
I’m pretty comfortable doing this on my own, but felt this was enough of a special occasion to warrant having it done by a true professional. Sitting in the chair, the artist asked me what type of look I was going for – I told her let’s go for Halloween prostitute. She looked at me, clearly got the point, smiled and immediately started to work her magic with the brush. She taught me each step so I could replicate it when I got home. When she was done, I wanted to put my own cock in my own mouth – it looked so sexy! With my makeup done and the bag with my outfit in tow, I hurried out of Macy’s, hailed a cab, and headed back uptown.
When I got home, I rushed into my apartment, started to run a hot bath, and stripped off all of my clothes. I live on a high floor and love leaving my blinds open because this guy across the way always stares even though he clearly tries to pretend that he’s not. I slipped into the tub and listened to some music as I gently cleaned my body. After a relaxing bath, I turned on the shower and shaved to ensure I’d be perfectly smooth for the evening’s festivities.
Hopping out of the shower, I started to work on my hair. I had been growing my hair out for a while at this point, so it’s naturally long and curly. I laid out all of the makeup I bought along with my brushes and got started on my face. By the end of it, I clearly saw Jenna in the mirror. I looked down at my bare nipples, reached over, grabbed my bra and put it on. I slipped two silicone breasts in and then gently slid my panties up my legs, over my girl stick, and up over both of my ass cheeks – my squats have definitely been paying off. Next, I put on my skirt, Care Bears shirt, and fishnets. I finished the outfit by slipping into my heels. I stood in front of the mirror and said, “hey girl!” I felt sexy and ready to head out. It was around 10pm, so the night was only starting to get busy.
I walked out of my building confident as Jenna. I headed up the block to one of the sports bars in my neighborhood that I knew was having a Halloween party. At the door, the bouncer gave me an up and down and merely waved me into the bar – phew, no ID check. I went to the bar, ordered a bourbon on the rocks and whipped out my cell phone. I logged into Grindr to take a look, but nobody really piqued my interest. 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 was 6’1” - 6’3”. At 5’5”, I could feel him towering over me. He leaned on the bar, kept smiling, looked at me and said, “thought you could use a shot.” Responding, I felt on the verge of squealing but was able to clearly articulate 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 so I decided to go all out on being Miss Flirtatious. 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. I think he felt all of the oxygen in my body flow out and my knees shake, because it was the hottest thing I’d seen a guy do, especially for me as Jenna. 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 Brandon, everybody just calls me B. See you later, Jenna.”
I chilled at the bar while Brandon helped the other bartender at the opposite end of the bar. I nursed my bourbon and noticed how Brandon kept his eyes on me. He’d wink at me every now and then, which had my girl stick 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. As he shifted to toss the shirt behind him, his tank came up a little and I saw the 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 a state of anxiety about what could happen. At the same time, I knew he was bartending so it would probably just be a game leaving my pussy untouched.
I checked in on Grindr again, but once again found men who were not of interest to me, plus I had Brandon stare at. I watched Brandon 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 Brandon 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, Brandon 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 bourbon and headed to the alley. It was really much of an alley by New York City standards as much as it was the small side door that the kitchen staff probably used to haul in supplies and to take out trash. I leaned against the cleaner of the two walls and waited. Brandon came out with his tank on and a pair of sweats. Did I mention how much I love a man in sweats? Anyway, he 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 Brandon has 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 remarkably easy given my heels. He unlocked his apartment door and invited me into what was a relatively nice apartment albeit unorganized to the extreme. 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. 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 hair back and spit on my tits. I was so turned on, but also scared as fuck.
Brandon pulled on my hair, while he 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 entire thing in my mouth on the first go, 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, he flexed his pecs, which turned me on so much. I 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 silicone breast through the Care Bears shirt. He said, “Daddy wants to play with Jenna’s tits.” Once again, I was fucking terrified because this guy has no clue that I am boy – albeit a femboy. Before I can say anything, his hand thrusts through the neck of my shirt and it’s too late. He pulls back his hand with a silicone breast, looks at me and then the breast, drops the breast, 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. You think this is funny? Getting a straight guy hard, sucking his cock, and not telling him you’re a fucking dude?” 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 started crying and 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 but not how she wants it.” I noticed how he said she and realized I had no idea where this was going. Suddenly, he yanked down my panties, I heard him spit, and then I felt his cock up against my smooth tight hole. I said, “Hold on, we need a condom.” He said, “Not tonight sweetheart, you’re going home with me in you.” He held me down harder and then slammed his cock in me. He was like a dog in heat pounding my pussy. He started saying things like, “mmmm, tight pussy” and “that’s a good girl, Daddy’s gonna get your preggy on Halloween.” I was crying but also incredibly turned out. 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?” 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 tight pussy… 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, slapped my ass, and said, “get dressed faggot and get the fuck out.” I was so startled that I got my shit together as fast as possible and slipped my clothes back on while he watched from the kitchen counter sipping his drink. He said, “I like that pussy and I like thinking about you walking around with me swimming inside.” He walked over, slapped my face and said, “You’re lucky I only fucked the shit out of you, so after tonight don’t come back to the bar.” I nodded, slipped on my heels, stood up and ran out. I headed home as quickly as I could.
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.
