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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.
________

31

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 would 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.