Night Shift

by Joanna Angel

  She pulled my panties to the side and quickly played with my clit. She licked the sides of my labia. It felt so good to have her back between my legs. I was already super moist, so she plunged three fingers inside me and bit my thigh. She came back up and kissed my neck; I didn’t care if it wound up being covered in lipstick. I could feel her thick fingers stuffing me, immediately hitting my G-spot, and I began to tremble. I wanted to shout I’m cumming! from the top of the wheel, but I knew that would be inappropriate. She knew the inside of my pussy so well, she knew exactly where to go. She could make me cum so easily, it was like she just had to turn on a switch. She must have ridden the Ferris wheel so many times in high school with her football in one hand and a cheerleader’s pussy in the other, and that’s how she just knew exactly what to do. She took her fingers from out of me and stuck them in my mouth. They tasted so powerful. I could taste the aroused state of my vagina right off of her. I was learning how juicy my pussy got when it was touched the right way. I had never felt this much moisture out of me from anyone who touched me in the past.

  She had to have loved the power she had over my pussy. I can only imagine what it must feel like to be able to make someone lose control over their own body so quickly. She seemed more relaxed. I was drunk from cumming and she was drunk from her own fingering mastery. The Ferris wheel began to go down slowly, people were getting off (not in the same way I had, and I felt bad for those people). I could tell that Bonnie’s insecurities were coming back; I didn’t want people to laugh at her as we exited the park. I took my silk scarf from around my waist and I put it on her head. Bonnie began to laugh.

  “What on earth?”

  “I was the understudy for Tzeitel in my middle school’s Fiddler on the Roof play. I got really good at putting on a scarf!”

  We walked off the Ferris wheel, hand in hand, and we exited the park, while remnants of my orgasm ran down my leg, and Bonnie looking like a sexy Russian babushka. It was time to retreat back to her truck. I wasn’t sure if I would be lying in a mini sleeper under a bridge with Bonnie or Billy that night, but either way, it was the only place I wanted to be.

  To go back and go with Billy to a bar instead, Click Here.

  To see how the fantasy ends, Click Here.

  I called a cab to come pick us both up at the truck stop (I didn’t think the clubs would have parking spaces big enough for a commercial truck) and got a text saying one was on the way. I will admit I was nervous about picking the right bar. Going out in general was not my area of expertise, and choosing a place that would allow Billy to be comfortable in drag for the first time in public was a daunting responsibility. After going through the not-too-extensive list of options around us (TGI Fridays was about the most hip place in the vicinity), I decided that we should drive to an area of downtown Tampa filled with bars and nightclubs.

  “All right, let’s go!” I said. Billy trembled, and didn’t seem to want to leave.

  “Come on!” I tried pulling him and he froze. I kissed him, and his red homemade lipstick transferred from his lips to mine. I put my hands up his skirt and rubbed his thigh, basking in the unique feeling of a garter against a hairy thigh. As I stroked him, he seemed calmer, but I could still see the nervousness on his face.

  We walked out of the truck and the other drivers sitting outside their vehicles definitely did a double take. The looks were inquisitive, but not hateful. I definitely saw one man in particular checking him out.

  “Should I call you something different?” I asked. Billy thought about this for a moment.

  “Yeah! Call me Bonnie,” she said.

  “All right, I can do that!” I replied. We walked hand in hand through the parking lot toward the cab. Even though we had spent the past twenty-four hours together, I was now being reintroduced to someone completely new. It reminded me of my roommate in college who successfully juggled two relationships at the same time. I don’t know how she did it. I could barely get a text back from someone I had sex with and she had scheduled times of when to text who and what. Her cheating involved flowcharts and lots of strategy. Okay, maybe what was going on with me right now wasn’t exactly like that, but the thrill of dating one person by day and a different one at night was intoxicating.

  As we crammed into the cab’s back seat, the driver definitely glanced at us through the rearview mirror a few times, but he shrugged and set off on our path. I snuck my hand up Bonnie’s skirt in the back of the cab and I could feel the beginning of a boner through her panties.

  “The good thing about this bell-shaped maternity dress as opposed to your tight jeans is that you can get a boner out in public and no one will know!”

  She laughed. I kissed her neck. I put my fingers through her wig, getting turned-on by the softness of the fibers. I had always been curious about being with a woman, but never found one that I really clicked with. Being with a woman who also had a cock was the best of all worlds. I was lucky.

  We had arrived and the cab fare of $37 lit up on his meter. Bonnie handed the driver a fifty and said, “Keep the change, hon’.” She whispered it in a very Marilyn Monroe way. I think she was doing her best to try to figure out what her voice should be, and a whisper was better than a manly voice, or an obvious, exaggerated falsetto.

  “Thanks, ma’am, have a good night!”

  I don’t think she heard the driver because she was so nervous and distracted and was in the middle of opening the door when he responded. Once we were out of the car, I jumped up and down like a little girl who had just been offered extra ice cream.

  “What’s going on? You just happy to be out somewhere that isn’t work?” she laughed.

  “Did you hear the cab driver?”

  “No, I handed him his money—did I miss something?” “He called you ‘Ma’am!’ Don’t you think that’s exciting?”

  Bonnie stopped dead in her path and tears welled up in her eyes.

  “You know, I wasn’t even paying attention!” she said, “Thank you.”

  “Thank YOU for letting me be a part of this. I am honored!” And I really was. Between the fisting and the homemade lipstick, this had been a rollercoaster of incredible emotions.

  We walked down Bayshore Boulevard. I didn’t exactly have a destination in mind—it was a five-mile road along the water, with a handful of bars. Truly I had no idea which place was best to go, but the sidewalk was nicely paved and it seemed like a comfortable place for Bonnie to practice walking in her short wedges, and the reflection of the giant Bank of America blue and red lights bouncing off the water paired quite well with her yellow dress.

  We walked past a 1920s prohibition themed bar, complete with a man out front in a brown plaid suit that looked like it had at least eight different pieces to it. He had a Sherlock Holmes style monocle on his face. He appeared to be the door guy.

  “Wanna go in here?” I asked.

  “All right,” she replied. Her long, wavy hair was lightly blowing in the wind. We pinned that fucker on quite perfectly. I was proud.

  “Good evening,” the doorman said.

  “Hello!”

  “How many people are in your party?”

  “Just two of us!”

  “Fabulous!” He had a mini iPad in his hands, with something that looked like a floor plan on it. He pushed in two little circles on the plan with an electronic pen. For someone who dressed like they existed before television was invented, I found it odd that their way of seating tables was so futuristic.

  “May I see your IDs?”

  “Sure!” I reached inside my bag and pulled out my wallet, I opened it instinctually and pulled out my ID. Bonnie trembled. Shit. I didn’t think about identification. She looked at me, she fumbled around, and I felt like I was going to panic, too. I didn’t want our night ruined before we even got in the door. She could show her ID and the door man could probably just do a double take and let her go by. That would be the best scenario. But he could also say, “This isn’t your fucking ID,” and then Bonnie w
ould have to prove she is legally Billy and that would definitely be a buzz kill to say the least. If the man was as old-fashioned as his suit, he could be incredibly closed minded, and have us tarred and feathered in the town square. If he was as modern as his iPad, then he would understand the situation and let Bonnie enjoy her night. Last time I really went out was on my graduation night, to a farewell party at the only LGBT friendly fraternity on campus. I certainly couldn’t predict the behavior of a door guy at an upscale bar.

  “Shit, Bonnie, did you forget your ID again?” I asked. I thought this would be a good save.

  “I’m an old lady, I can’t even remember the last time someone asked me for it!” She laughed at her own joke as enthusiastically as possible, and I jumped in and laughed too.

  “You might be old Aunt Bonnie, but you sure are young at heart!” The turn of the century door guy was incredibly confused. While we weren’t kissing or making out, the nature of Bonnie and my hand holding was a little too provocative for an aunt and a niece. I don’t know why I even said that. I just thought the back story of a girl out on the town with her aunt and she innocently forgot her ID was believable.

  “Please let us in, we drove an hour to get here—she’s definitely of age.” I gave him a sad look, trying to connect with him, hoping he might pick up on it and either have sympathy for the fact that I desperately wanted a night out with my aunt, or I desperately needed to get my new lover identifying with a different gender this evening. Not sure which was more relatable.

  “I was born in 1978, when Jimmy Carter was president. Does that help? Would a twenty-year-old even know who Jimmy Carter was?” She laughed again and the Boardwalk Empire reincarnated door man actually cracked a smile, too. Bonnie was quite a charmer as a lady!

  The door guy looked around, and surrendered. “All right, go in. Just bring your ID next time, and tip your bartender, please!”

  “Thank you!” I said. I almost went to hug him but I stopped myself because I realized that would be kind of strange.

  We walked in like we were Bonnie and Clyde, all confident and cool. Or actually, more like Bonnie and Taryn.

  On entering the bar we found the old-fashioned flapper theme was kept to the utmost extent. There was a lot of exposed brick and dark wood, multiple kinds of syrups, bitters, and herbs, and brands of liquors I hadn’t ever heard of. This was nothing like a frat party.

  On the opposite side of the bar, toward the wall, there were velvet couches and tables and they were enclosed with dark curtains that could remain open or closed, like little pool cabanas.

  “Where do you want to sit?” I asked.

  “Let’s get one of these private tables,” she answered.

  A sexy flapper hostess came up to us, with a fringed dress, short hair, a shiny sequin headband around her head, and a feather in her hair.

  “How can I help you ladies this evening?” she asked.

  “We’ll take one of those tables if that’s okay,” Bonnie said.

  “It’s a three-hundred-dollar food and drink minimum, as long as that’s fine—I can get you set up right away,” said the hostess.

  That was the amount of money I usually budgeted for groceries the entire month! If I’m not mistaken, I thought Coca-Cola cost a nickel in the 1920s. This bar definitely picked and chose what vintage elements to keep and which to ignore.

  “Yeah, that’s fine,” Bonnie said. She handed her credit card to the hostess. While it goes against some of my feminist ideals, I will guiltily admit that I have always dreamed of being properly wined and dined by someone and I was aroused by the fact that it was someone in a dress and pretty lace panties, and not a suit and tie.

  We sat down. The seats were plush and incredibly comfortable. The lighting was seductive and dark, with just enough candlelight to read the menus and each other’s lips.

  “Would you like to start off with a shot of absinthe?” the pretty flapper asked.

  Was that the poisonous beverage that Edgar Allan Poe drank? I wasn’t really into poisoning myself (more than your average cocktail would), but if Bonnie wanted shots, we’d do shots. I nodded at her, indicating it was her decision.

  “Yes, we would,” Bonnie said, “and what’s your name?”

  “I’m Janine! And what’s yours?”

  “Bonnie.”

  “And I’m Taryn!” I said.

  “Nice to meet you, ladies! I will be right back with your aperitif!” Janine said.

  I assumed this was the street name for absinthe, or something along those lines. I was incredibly confused but so excited; I just took it all in and did my best to blend in here, in a long V-neck T-shirt and Converse sneakers.

  She returned with two long, skinny glasses filled with light green liquid. It looked like something out of a science lab.

  “Cheers!” Janine said. Bonnie and I clinked our glasses together and chugged the liquid in the shot glass. It tasted like fresh-cut grass and licorice. It was cool and crisp in my mouth, then burned when it got down to my stomach. I wasn’t hallucinating (at least not yet) but I did feel pleasantly buzzed.

  “So how are you feeling?” I asked Bonnie. “I feel really powerful and beautiful. I can’t believe this is finally happening,” she said.

  “I’m glad!”

  I didn’t completely understand how Bonnie felt on the inside, but I felt like we were both figuring out how to be ourselves in different ways. I could openly buy heels, dresses, and lipstick anytime I wanted and I chose not to. I suppose I took it for granted. For Bonnie, putting on a dress and being out in public made her feel powerful. For me, well, learning that I could squirt liquid out of my vagina while a fist was inside there is what did it for me. I wondered if she would fuck more daintily as a woman. Would she want me to gag on her cock? Or would she be more soft and passionate? Would she always want to be Bonnie? Or would she go back to being Billy tomorrow? I shouldn’t ask. I should just indulge in the moment we currently exist in and let the future reveal itself as it happens.

  Janine came back with three more drinks. She dropped two on the table.

  “What are these?” Bonnie asked.

  “Bartender’s special! Try it!” she smiled and answered.

  It was a short glass with a large ice cube in the middle, a lemon peel and some fizzy liquid inside of it. It tasted like an Orange Crush, but with a lot of alcohol in it. Oddly enough, the first time I ever got drunk was in a park with a few friends, who poured vodka into a half-filled bottle of warm Orange Crush. Apparently all we were missing was a lemon peel and some oversized ice.

  But the drink did taste quite good. I drank it quickly and I liked the way the large ice felt on my lips.

  “Easy there!” Bonnie said. She barely had a sip to drink.

  “Oh—I wasn’t supposed to chug this?”

  “No, silly, you’re supposed to savor the taste!” Janine said.

  “Like a cup of coffee!” I answered.

  Bonnie laughed. “Yes exactly, like a cup of coffee,” she said as she daintily sipped from her glass.

  “So, what are you ladies up to tonight?” Janine said. Was it part of her job to make me feel like she had some kind of a crush on one of us or both of us? Or was that the orange fizz and the light green liquid getting to my brain? She had bright white teeth and matte red lipstick on. I felt like she had a twinkle in her smile, like someone out of an old-fashioned toothpaste commercial. She had on satin gloves, and she too had on a garter and stockings. I didn’t even have panties on. I didn’t know that when I got dressed for work forty-eight hours ago that I would be going to a speakeasy on a date with a cross-dresser. Perhaps I should always be prepared for this type of surprise to come up.

  “Come over here!” Bonnie motioned for me to come to the same side of the table with her. Two people sitting side by side at a table when no one was on the other side is definitely romantic. No one does that unless they just can’t keep their hands off one another. I obliged and made my way over there and jumped right into
her large arms.

  “You two are so cute!” Janine said. “Would you like some privacy?” She didn’t wait for our response and she drew the curtains so they covered the table and we were now enclosed in our own little candle-lit fort.

  “Have fun!” she said, and she did her smile-twinkle thing again. I wondered what kind of toothpaste she used.

  And then Bonnie and I were alone in public, at a table lit by an electric candle. I kissed Bonnie on the neck. It was sexy in a vampire-like way, and it was also practical since it was intimate and didn’t mess up her lipstick. She put her hands up my, um, well I guess we can call it a dress for all intents and purposes. I had goosebumps. I also had no panties on. Being felt up at a fancy bar, and being felt up by a fancy woman was something entirely different than what I was used to; however these days I wasn’t really sure what I was used to anymore. Every hour of the past seventy-two hours had been completely different than the next. It was a pretty drastic shift from my life being exactly the same for about the past eighteen years.

  Her hands were delicate, but large and firm. They were the same hands that touched me earlier, only now they were attached to a torso that smelled like perfume. She continued to slide her hand up my thigh, and I slid my hand up hers. Her ruffled garter tickled the back side of my hand. This one had tiny white bows that fastened the thigh-high and the garter together. They remained fastened tightly even as I rubbed up and down. I couldn’t quite put my finger on why I loved this feeling of lace, nylon, and man all mixed into one, but I did.

  I could feel her cock getting hard underneath her dress and panties. Were we safe inside this enclosed space? Did the $300 minimum include a pass for exposed boners? I couldn’t help myself. I was just so attracted to her; I was so swept away by the absurdity of how we came into each other’s lives and then into each other’s mouths.

  She pushed me under the table and I sat with my knees on the floor and I put her cock in my mouth, moving her panties to the side. She sat at the table like a classy lady and drank cocktails while I shoved her thick cock as far as I could down my throat. I rubbed the lace material up against the skin of her shaft and I could feel her getting harder and harder. She pushed her legs together and squished my head in between her knees. I felt like I was in some kind of awesome sexy headlock, and I will admit that I liked the feeling of the hair on her thighs against my cheek.