A Halloween Weekend

~Happy Halloween! The following is a follow up to my last story, A Weekend of Firsts. I recommend reading that one first for a little background on, and a better introduction to, our main characters.~

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A few months ago, I decided to have a weekend in spending time alone with my new battery operated friend while dressed as Tiffany, my en femme persona. Plans changed, however, when my best friend Philip walked in on me masturbating with a dildo while dressed in lingerie and a long, curly blonde wig. To my own surprise, instead of rejecting me, or freaking out, his discovery ended up in us making out and eventually into doing much more. I had thought about losing my virginity but never imagined it would have been as Tiffany and losing it to a man, let alone my best friend. Funnily enough, I had considered myself straight, or as straight as a guy who likes to dress up like a girl and play with vibrators could be. Turns out, I am straight. A straight girl.

For the last few months, I was still living as Tim to my parents', school's, and work's knowledge. But my weekends were a different story. After the first time we had sex and then went out to dinner, Phil stayed with me all weekend. Now, every weekend since, we've been going on "fishing and camping" trips. At least, that's what we've been telling our parents. Secrecy just seems so much easier than dealing with the stress of telling them what's really going on. Every Friday afternoon we load Phil's car with a tent, fishing poles, and "camping" bags. My bags are filled with dresses, outfits, lingerie, makeup, my wig, and anything else I need for our weekend getaways. We used the tent once or twice, but instead we usually hole ourselves up in a motel room where I begin my transformation.

Friday evenings usually consist of me getting ready. I start by shaving all of my body hair until everything is silky smooth. Afterwards, I towel myself off and get my bra and panties on, get my homemade breast forms in, and start my makeup. I finish with dressing up in my outfit of choice for the evening, pulled from my stash and my sister's room, and fix my blonde wig to my head. With everything done, Phil takes me out to dinner and never lets me pay. The real fun starts when we get back to our motel room. We're barely even through the door before our lips are locked. As soon as we're in for the night, shoes go flying across the room, and clothes start falling to the floor.

After a couple months, I've gotten so much better at makeup and other girly things, including walking in heels, and changing my voice. Next weekend was Halloween weekend, and Phil and I were making plans while in our motel room two towns over from our hometown.

"Hey, so I forgot that next weekend the downtown area here is having a big Comic Con themed Halloween party! There's gonna be all kinds of vendors and all the bars will have comic related specials. Most of them don't card, and if they do there's plenty of people willing to buy something for us. Would you go with me? I think there's a couples costume contest too." Phil looked so excited talking about this thing that I couldn't very well say no.

"Okay. I'll go. Couples contest, huh? So what kind of costumes do you have in mind?" His face lit up in excitement as he pulled out his phone and showed me pictures of the Joker costume he already bought for this.

"We don't have to enter the couples contest, so you can go as whatever you want, but if you did want to enter you could go as - "

"Harely Quinn. I could do that!" I said, trying and failing to mask my enthusiasm. I used to watch cartoons with my brother and I remembered seeing Harley Quinn. I fell in love with her even more after playing video games with Phil and seeing the new movies.

"Do you have enough time to order a costume, though? Shipping can take too long."

"I'll make one! There's a Halloween store not far from here, I'll go tonight and buy stuff to make the costume if you want to scope out what bars won't card us." I replied, being excited to go shopping for my first girly Halloween costume. Philip agreed and walked to the downtown area while I drove down the highway to start shopping.

The week flew by and before I knew it, it was Friday. Tomorrow was the big day. My first ever Comic Con and Halloween party where I'd be going as Tiffany and not Tim. We went through our usual Friday night routine, but after dinner, we both got in bed in the motel room and cuddled up together before drifting off to sleep. Saturday morning came, and we decided to sleep in before getting up and getting ready for the party.

Just to be safe, I jumped in the shower and did another quick shave to make sure there were no pesky body hairs, and started getting ready. I pulled out my bag and got to work with my Halloween store purchases. I bought a matching pair of Harley Quinn themed bra and panties and got them on, followed by red and black diamond printed tights. I pulled a black camisole over my chest after putting in my forms. Next, I pulled out the main part of the costume. I bought a velvet Harley dress in red and black with her diamond pattern on the bottom and a see-through mesh top, which is where the cami came in for a little bit of modesty. I slipped on my new black boots with a 2.5 inch stiletto heel, bringing me up to almost 6 feet tall. I also put on a cropped black leather jacket from my sister's room, and black fingerless gloves. I did the standard Harley makeup, making my face pale white while accenting my eyes in black and dark red lipstick. I did dark circles around my eyes and put a domino mask over them. I finished off the look with a new wig, this one was already pulled into pigtails. I took temporary black and red spray dyes to the bottom of the tails and I was ready to go.

I walked out of the motel bathroom with my heels clicking on the hardwood floor. Phil was struggling with the buttons on his shirt but turned his head to see me and his jaw nearly hit the floor.

"Need some help with that, puddin'?" I said in my best Harley voice as I walked over towards him. I buttoned his top the rest of the way up as he looked into my eyes. I could see his pants starting to form a bit of tent.

"God damn, you're hot." He said as he pushed me closer to the bed.

"Slow down a little bit there, Mistah J. Let' the save the fun for after we win that contest and come back for a celebration." I got his green vest from across the room and helped him into it. I took out my makeup kit and did his face in all white as well as did dark smudgy circles around his eyes. I did the red around his mouth and sprayed his hair with temporary green dye. When I was done, we took a selfie together as Joker and Harley, with me up against his chest. He grabbed his purple jacket that matched the purple pants he had on, and we left for downtown.

We got stopped for so many pictures, and of course looked at everything all the vendors had to offer. After that, it came time for the couples contest. We walked up onstage with new his and hers pop guns we picked up at one of the stalls, and a mallet I had gotten from another one. It was exciting, but then came the hard part. We were waiting on the announcements on who had won.

"In third place we have... Rich and Janie as Captain America and Female Bucky!" We all cheered and clapped as they went up on stage.

"In second place we have... Philip and Tiffany as The Joker and Harley Quinn!!" We ran back up onstage and got our prizes before moving aside for the number one spot.

"Last but not least, in first place we have... John and Rose as Green Arrow and Black Canary!!" I froze solid. We knew them. And we didn't just know them, Rose was my second best friend and John was her boyfriend. When they walked up they immediately recognized Phil and waved at him. Hopefully they didn't recognize me. I hadn't told Rose about my other life as Tiffany. I was planning to, but I didn't want her to find out on her own. After what felt like an eternity of picture taking for the winners of the contest, we finally snuck off to the closest bar. Sure enough, they didn't card us and let us right on in.

There were so many other costumed people there, all coming in from the convention outside, mostly because they were doing half price shots for anyone in a costume. Phil and I sat down at a small corner booth when I saw a green hooded figure and a blonde on his arm walk towards us. It was John and Rose. They sat right across from us. I was counting on the mask and hair covering the top half of my head, as well as the poor lighting in the bar to hopefully conceal my identity. After a short conversation, John and Phil decided to leave us at the booth to go get drinks for us. There I was, face to face with my other best friend with no idea what to say. She started the conversation.

"Hi. I'm Rose. I'm friends with Phil and his other friend Tim."

"I'm Tiffany. Nice to meet you." I said in my most feminine voice. Practice was paying off.

"You seem kind of familiar. Have we met before?"

"Probably not. I'm not from here."

"Neither are we. We live a few towns over. I love your Harley Quinn costume by the way. I like that it's kind of original compared to all the others out there."

"Thanks. Phil talked me into it for the couples contest."

"How long have you guys been a thing? I didn't know he had had a GF, He spends all his free time with Tim as far as I knew. Have you met him?"

"Yeah we know each other." It wasn't technically a lie... Rose then asked if we could take a selfie together, since we were both DC girls. What harm could it do? I was confident now that she didn't recognize me. I said yes.

Thankfully the conversation was cut shortly after that when Phil and John came back with no drinks.

"We need to go," John began, "the bartender just tipped us off about an undercover cop coming to check on him. If they check our IDs it's done for."

"At least the night isn't a total loss," Phil chimed in next as he looked to me and grinned. "We need to get back to our room anyway."

Rose giggled and looked to John. "Us too." She replied. "Where are you guys staying?"

"The Days Inn." I replied.

"So are we! We can all walk back together." And we did. About halfway there, my feet were starting to kill me and Phil sensed it. I stopped and took my boots off as he lifted me off the ground and carried me the rest of the way bridal style. I threw my arms around his neck with my boots in my hands. I looked towards Rose and John and saw that he had her piggybacked with her boots in hand too. Luckily, they were on the other end of the motel and it was so dark now that they wouldn't have been able to see that we were here in my car. I know Rose would recognize it and that would take explaining I wasn't ready for. I quickly forgot about almost getting caught when we made it through the door of our motel room. My boots, jacket, and gloves, were all off and immediately on the floor. I was sliding out of my panties and lubing my hole while Phil began taking his costume off. I crawled on the bed on all fours and started to shake my ass for him.

"Come and get it, puddin'!" He almost sprinted to the bed to oblige, and we were in such a hurry to, especially after not having sex last night. Both of us were so eager, we totally ignored the box of condoms on the nightstand. As Phil proceeded to mount me from behind, I felt another new first. For the first time in the few months we had been together, there was nothing between us. For the first time, I could feel the bare head of his cock pressing into my lubed opening. It felt even more intense as I could feel all 9.5 inches of his flesh begin to fill me from the inside. My ass began adjusting to accommodate the girth of his cock as he pushed farther and farther in. I relaxed as he pulled back and thrust back in. He fucked me bareback and doggy style for at least 15-20 minutes before pulling all the way out again. I shifted to lay on my back and spread my legs open for him, covering my own cock with the skirt of the dress and pressing my waiting ass up towards him. I glanced at the condoms and he stopped for a second.

"Should I put that on?"

"Nah. I want to keep feeling all of you inside me, Mistah J." With that he locked lips with me and pushed his pulsing, hard member back into my open hole. He began plunging in and out of my ass with more gusto in each stroke for what felt like hours before he pushed all the way into me, as I locked him in with my legs. I could feel him twitch and pulse as he began shooting jet after warm jet into my ass, and for the first time I could feel him cumming inside of me.

He rolled off of me slowly and we just laid there for a few minutes catching our breath before going to clean up and wash all of the makeup off of our faces. Phil beat me back to bed, but I crawled over him and leaned in close, cuddling up to him. I laid my head on his chest and drifted off to sleep.

A couple days later, on Halloween, my phone went off. It was a text from Rose.

From Rose: (Hey! Missed you at the Halloween Comic Con Party this weekend. You should've come. It was a great time!)

From Me: (I heard. Phil told me he ran into you and John there. Sounds like y'all had a good time.)

Rose: (...)

Rose: (Speaking of Phil, I need to ask you a question. Something's been bugging me the last couple of days.)

Crap. She was getting close. I could just tell she was.

Rose: (...)

Rose: (Selfie she took of us together at the bar)

Shit. Shit. Shit. She has to know...

Rose: (Do you know this girl? Her name is Tiffany and she's apparently Phil's GF. She's so familiar but I can't place her anywhere. All I know is they are definitely intimate. I can tell by the way she looks at him.)

Bullet dodged. She doesn't seem to know. Thankfully. I need to buy some time. No. I don't. She's this close. I need to tell her before it bites me.

Me: (...)

Me: (Yeah. I know her.)

Rose: (You do!? Who is she? Where's she from?)

It was now or never. I had to make a decision. Do I stall her longer? Or do I tell her. I typed my next message and just sat there for a couple of minutes with my finger over the send button. Two words were all I typed and was still deciding whether or not to send. Two small words. All I have to do is press Send.

Me: (...)

Me: (She's me.)

Sending...