Share A Drink With Elizabeth

"Ugh, I'm still sore from last time," Stephany groaned. "Can we skip today and just play again next weekend?"

"How about we spin first and then decide?" Jeff argued. "Besides, you can always spin the safety bottle."

"Alright, alright," Stephany said after giving it some thought. "This time you're spinning the bottle, though."

"That's fine," Jeff said, grabbing a bottle. "You want to share it again or drink it by yourself to numb your soreness?" he asked laughingly.

"Sure, I'll have it," Stephany said. "I could use a liquid painkiller."

Jeff poured the beer into a single, glass tankard and gave it to Stephany. He then placed the empty bottle between them on the floor and spun it. Once again, it came to a halt, facing mostly toward Jeff.

"Next time it should land on you. These odds are rigged," Jeff joked, grabbing the bottle. "Today's winner is..." he said dramatically as he slowly removed the paper from it. The smug smile on his face made way for a look of confusion. "Elizabeth? Oh boy..."

Stephany giggled and curtsied. "Your Highness."

"Yeah, let's not go there," Jeff responded with fake retching at the thought. "I hope you can also imagine someone else when you hear that name."

"Hm," Stephany hummed in thought as she took a sip of her tankard. "Honestly, I'm not sure," she said. "It strikes me as a very 'girl-next-door' kind of name."

"So..." Jeff hesitantly said.

"So," Stephany said. "We can just take it easy with that one. No need to spin your safety bottle... Unless you insist on making it sexual." She giggled.

"No, no," Jeff quickly replied. "A casual play sounds good to me!"

"Alright," she said. "In that case, I guess we can do it today then, instead of next week. Let's just have a fun, casual day indoors." Stephany finished her tankard, got up, and started walking out of the living room.

"Where are you going?" Jeff asked.

"The bedroom, of course," Stephany replied. "I'm going to have to check my wardrobe to see if I have anything that could resemble Ellie's style. Because you 'are' going to become Elizabeth, those are the rules." She giggled as she left the room.

Jeff gulped and mumbled to himself, "Maybe we should have shared that beer after all..." He poked his head out of the doorway and said, "I'll calm my nerves with some phone games on the couch while you do your thing!"

"Nuh-uh!" Stephany replied from the bedroom. She jolted into the bathroom and returned to the living room with a body trimmer and handed it to Jeff. "You, Ellie," she said sternly, "can help prepare yourself by trimming those unsightly body hairs down."

"But," Jeff stammered.

"No buts," Stephany said. "Ellie is not going to half-ass her looks when she goes out to visit her friend."

"Yeah, but, what about work?" Jeff asked, concerned.

"I'll go easy on your eyebrows," Stephany said, comforting. "But the body hair has got to go. If anybody cares enough to ask, you can say you lost a bet with me or something. It'll grow back soon enough, don't worry. Or did you think I only shave my body once a year?" she chuckled and left the room again.

Great, Jeff thought as he took off his shirt and started trimming his upper body. Hopefully next time, it'll be her turn to do the role-playing. At least we'll be taking a few days off after today... In hindsight, with these stakes, it's a bit too risky to play this game on both weekend days, but I can't back out now. At least it's not going to get sexual. That would be so awkward. Jeff shivered.

"How's it going over there?" Stephany asked from the bedroom.

"Just finished my upper body, moving on down now," Jeff replied.

"Alright!" Stephany said. "Just, please, only trim your legs and then use a razor in the shower for your more private areas. Hygiene reasons."

"As if I was going to let an electric blade get anywhere near my groin!" Jeff replied.

"Better safe than sorry," Stephany commented. "I'm nearly done here, too. I put together a few outfits, and then I'll let you choose what you'd feel most comfortable in."

"Is it too late to run out the door and hide for the day?" Jeff joked.

"I mean, if you're not going to be Ellie today, then we'll just have to do it tomorrow," Stephany said matter-of-factly. "Should I call your boss to let him know about his new female employee?" She giggled.

"Today's fine!" Jeff quickly replied.

"Glad to hear that, Ellie," Stephany said laughingly. "When you're done trimming, join me in the bedroom to pick out your outfit before you head for the shower."

Jeff finished trimming his legs and approached the bedroom. "Should I be afraid of what I'm about to see?" he teasingly asked as he entered the room.

"They're just clothes," Stephany said and laughed. "If that scares you, wait till you see the makeup kit!" She pointed at the bed, where she had laid out several clothing sets. "So, for the first option, we have some regular blue jeans, you can choose between either the full-length or short jeans, accompanied by a white blouse and white heels."

"You do remember I'm two shoe sizes bigger than you, right?" Jeff asked.

"They've got some extra space. I'm sure we could squeeze you in there," Stephany answered. "It might be a little uncomfortable, but it's just for a single day, you can handle it!" She moved on to the next set. "Up next, we have something a little more girly. A short, lightish-red dress, with a black jean jacket, black pantyhose, and black pumps."

"Not gonna lie, it does look kinda nice. You should wear that set sometime!" Jeff said.

"Duly noted," Stephany chuckled. She moved on to the final set. "If you want to be truly boring, you could also go super basic and choose this outfit. Simple blue jeans, white sneakers, and a grayish cashmere sweater."

"I mean, I know I complained, but I can hardly role-play Elizabeth if I don't 'feel' like an Elizabeth," Jeff said. "I'll probably regret saying it later, but even though the last set is the safest and easiest way out, my gut says it should be one of the first two options."

"I was hoping you'd say that," Stephany said happily. "You won't regret it! I'll turn you into a real cutie!"

Jeff blushed. "Me? A cutie? Have you seen these shoulders and arms?" he asked with a hint of sadness.

"That's why I made sure to include ways to cover it up a little," Stephany said. "You'd hardly notice them! I'm more concerned with hiding that package of yours." She giggled.

"Wh- What's that supposed to mean?!" Jeff stammered, blushing even harder now, doing a double take to ensure he wasn't sporting a boner unbeknownst to himself.

"Well, you've got to change underwear too, of course!" Stephany elaborated. "And I don't want you to rip through my undies!"

"Oh, like that," Jeff said.

"Thankfully, I've got some medical tape that I can use to tape it all down and flatten it a bit," Stephany said matter-of-factly. "That's why you need to make sure it's all shaven smooth down there. Otherwise, the tape removal is going to hurt even more at the end of the day."

"Noted," Jeff said, slowly exiting the room by walking backward. "I'll head to the shower and take care of that, then. I'll leave the picking of the underwear to you, lest I faint before we've even started."

"Sure thing, cutie," Stephany chuckled. "Oh, and use my shower products! Ellie is not going to smell like 'Woodland Enigma'."

"Actually," Jeff said. "It's 'Wild Temptation'."

"Same thing, different name," Stephany said and shrugged. "You're using my Fruity Passion soap today. And when you've dried yourself, use my deodorant and perfumes." She paused. "Actually, I'll use those on you, lest you empty my entire bottle."

"Probably for the best," Jeff said with a chuckle from the bathroom as he closed the door behind him.

Stephany returned to the bed and looked at the clothing she had laid out.

"Hm," she pondered. "Basic girly or cute girly?" as the words left her mouth, she realized that going with the latter was the only real option, and put the other two outfits back in her wardrobe. "Alright... underwear," Stephany said aloud as she opened her drawers. "Well, given the dress, red would make the most sense, but that's also more... sexual? Black might fit better in that case, and the rest of the outfit is black too..."

Stephany took a moment to weigh her options, but eventually decided to stick with red, as it would be less likely to show beneath the dress. "Ellie can be cute and sexy," she smilingly said as she picked out a red slip containing a simplified, monochrome print of butterflies and combined it with a simple red push-up bra. She may stand out a bit more than a 'girl-next-door' would like to, Stephany thought. But I have an obligation to make Ellie feel like a woman today, even if that means using some encouragement.

"How's it going in there?" Stephany shouted.

"Almost done!" Jeff yelled back. Not long after, he turned the shower off and dried himself. He opened the door and motioned for Stephany to bring his outfit for the day.

Stephany energetically jumped up from the bed, grabbed the clothing and underwear, and rushed off to the bathroom, where the placed them on the top of the laundry machine.

"The more time that goes into this, the more I'm glad we're not making it sexual this time," Jeff said, looking at the underwear Stephany choose for him.

"I mean, if you were a little more confident, it could have led to you doing me," Stephany teased. "But if you're just going to be shy and submissive like that..." Her face displayed a smug grin.

"I'm just not used to... this," Jeff said, holding the red slip. "At least, not to wearing it myself."

"If you hold it next to your face, I'm quite certain it could act as camouflage," Stephany giggled. She grabbed the medical tape from the mirror cabinet. "Alright, time to conceal your firearm," Stephany joked as she kneeled in front of Jeff to start applying the tape and apologized. "It could have been a once-in-a-lifetime opportunity to say that, I had to take it."

"I'm happy at least you're having fun," Jeff said, embarrassed. "Can you hurry it up a little?"

"Is Ellie afraid she's going to get an erection?" Stephany teased.

"Oh shush, you know I'm just easily aroused when you touch me there," Jeff blurted out.

Stephany giggled as she continued applying the tape. "And... Done," she said reassuringly a few moments later as she finished taping Jeff's scrotum and penis to the skin, making it look as flat as she could. "Next time, I'll buy some pads to help with the flat look," she said. "But for today, this will have to do."

"Next time," Jeff repeated. "Let's hope that's going to be many months away."

"Loser accepts their defeat without complaints, those were the rules," Stephany said matter-of-factly. "You had your fun yesterday, now it's my turn." She smiled. "Now put these on and see how they fit," Stephany said as she handed Jeff the red slip and bra.

Jeff hesitantly put them on and said, "A bit tight, but they fit."

Stephany walked around to Jeff's backside and checked the fit. "Looks just fine to me, Ellie," she said and slapped his butt.

"Hey!" Jeff shrieked. "I thought we were going to keep it casual today?"

"We were going to keep it non-sexual," Stephany corrected. "A little bit of flirting and teasing my cute little Ellie still seems within the realm of allowed activities."

"Ellie will remember this," Jeff said.

"Oh, so Ellie is a gamer too, now?" Stephany giggled as she sprayed some perfume on Jeff and handed him the dress and pantyhose. "Put on the maid outfit, gamer girl."

"Maid outfit?" Jeff responded confused and paused. "Oh. Right. I sometimes forget you speak meme, too." He rolled his eyes but proceeded to put on the clothing regardless. "Hey, Steph?" Jeff asked. "Are you sure this dress is long enough?"

"Barely, but, yes," Stephany replied. "It was not meant for someone your size, but it still works out, your ass is covered."

"Barely," Jeff repeated as he shifted about. "I can feel the breeze coming through."

"Want to go out and buy a bigger one?" Stephany teased.

"As a matter of fact, this dress fits perfectly!" Jeff quickly replied.

Stephany giggled. "Glad to hear that, Ellie," she said. "Now let's get back to the bedroom, so I can do your makeup and finish your look."

Stephany grabbed Jeff's hand and led him to the bedroom, where she brought him to the bed. "Sit," she instructed, as she gently pushed him onto the bed. She walked off to grab her makeup bag and opened it to reveal several small glass containers containing liquid makeup, brushes, pencils, and other items Jeff could not decipher.

Jeff anxiously let Stephany apply the makeup to his face, apply and brush powders, curl his eyelashes, rework his eyebrows, which she promised not to overdo, and draw around his eyes with an eye pencil.

"Are we done now?" Jeff asked. "My back is starting to hurt."

"A small price to pay for beauty," Stephany argued laughingly. "But, yes, I'm pretty much done. Dare to take a look?" She stepped aside so that Jeff could look at himself in the standing mirror that was behind her.

"That's... me?" Jeff asked, astonished. "I knew makeup could make a lot of difference, but, damn! I never imagined it could make me look even remotely girly!"

"Thank you," Stephany said with a curtsy. "So, I take it you like it?"

"I mean, it looks amazing, and it's perfect for Ellie," Jeff answered. "But I don't see this as a style for 'Jeff'. So I'm feeling a little conflicted."

"Well, luckily Jeff isn't here today," Stephany giggled. "So I'm glad to hear Ellie likes her look... One last thing, though!" She rummaged through the makeup bag and pulled out some lipstick. "These don't smudge easily, and they match your outfit," she said as she applied the lipstick to Jeff's lips.

"So, now we're done?" Jeff asked.

"The day won't be over any faster if you keep asking," Stephany replied. "Your makeup is done, but your hair still needs some work."

Stephany walked over to her wardrobe, where she opened a box containing various blonde and brown wigs. After removing a few, she found one she was satisfied with.

"This'll do nicely," Stephany said, holding out a dark blonde wig, its hairs were long and wavy. "Thankfully, your hair is short, and its color is similar to this wig, so we can just put this over your natural hair without having to make any adjustments," she said as she walked behind Jeff to pull the wig over his head.

Jeff had mostly just kept staring at himself in the mirror while this happened, trying to process how his appearance had changed so drastically in just a single day. It was like he stared at a completely different person, yet, he was staring at none other than himself.

"There," Stephany said. "Now you're done." She grabbed the black jacket that she had left on the bed and handed it to Jeff. "Now put this on along with the pumps and then Ellie will be fully dressed," she said with a smile.

"Indoors, though?" Jeff hesitantly asked as he took the jacket from Stephany.

"We can also go outside with it if you want," Stephany said and giggled. "Just put it on for the looks. If it gets too warm, you can take it off later."

Jeff put on the jacket and, with some assistance from Stephany, squeezed into the pumps, which, surprisingly, were a bit tight, but not tight enough to be uncomfortable.

"What time is it even?" Jeff asked. "I feel like we've spent half our day on just the preparations."

"Well, there's still natural light coming through the window, so it can't be that late," Stephany reasoned as she grabbed her phone to check. "Oh. It's nearly 6 already."

"I guess we'll be ordering today, then," Jeff responded. "Pizza?"

"Sure," Stephany answered. "And then we'll just watch some TV for the remainder of the day, nice and laid back."

"Say no more," Jeff said as he rushed to the living room to drop down on the couch. A long drawn-out sigh of relief escaped his lips. "Much better," he said.

"Stephany casually walked after him, absentmindedly browsing her phone. "Which pizza would you like, Ellie?" she asked as she sat down next to him.

"Uhm," Jeff said, directing his gaze at the ceiling as if the answer to her question was there. "Meat lovers," he finally said.

Stephany chuckled and slowly brought her hand to Jeff's inner thigh as she teased, "So Ellie is a meat lover, huh?" She gently squeezed his thigh as she stared into his eyes with a longing gaze.

Jeff turned red and froze up. "Steph!" was all he managed to say.

Stephany released her grip. "I'm just having a bit of fun, darling," she said laughingly and added, "I think I'll just upgrade it to a family-size pizza. I'm feeling like a meat lover too tonight." She brought her face closer to Jeff and kissed him on the cheek.

Jeff wobbled around on the couch trying to contain his nerves. "If you keep this up, that tape is not going to hold," he said.

"Let's hope it does," Stephany said. "Because you're going to open the door to accept the pizza when it arrives. I already ordered and paid online, so Ellie is going to have to open the door and bring that pizza in." She giggled.

Jeff's breathing became noticeably louder, but he remained speechless.

"I'll stop teasing you for now, for Ellie's sake," Stephany said. She threw her arm around Jeff's shoulder and gently pulled him towards her. "Here," she said reassuringly. "Lean your head against my chest, like I usually do to you. Feel my heartbeat? It's calming, isn't it?" She gently planted a kiss on the back of Jeff's head.

"Hm-hm," Jeff eventually hummed as he slowly calmed down again while they watched an episode of SuperHeroes.

Shortly before the episode finished, the bell rang, and Jeff jumped up. He knew what it meant and that it was his cue to greet whoever was at the door and bring the pizza in. He anxiously waddled his way over to the door and opened it. A person was standing in front of him, Jeff had already directed his face down to evade eye contact and instead focus on the pizza box and remove himself from the embarrassing situation as fast as he could.

But there was one issue. The person in front of him was not holding a pizza box.

"Hi!" a friendly voice said. "Is Stephany home? I was supposed to return some music CDs to her last week and I kept forgetting, but I saw her car on the driveway and I happened to still have them in my bag, so I thought I could drop by and deliver them!"

Jeff was not prepared for this interaction. His fight-or-flight response could not decide and instead froze in place like a deer in headlights. Thankfully, Stephany remained nearby to assist if needed, so she was able to quickly interject herself into the situation and take over.

"Hey, Kayleigh!" Stephany said. "Sorry, don't mind Ellie, here, she's a bit socially awkward. We were expecting a pizza delivery, so she probably froze up when she was met with a different outcome than what she had prepared herself for."

"Oh, it's fine," Kayleigh responded. She grabbed a couple of CDs from her bag and handed them over to Stephany. "Here you go, dear. Sorry for being so forgetful! And my apologies to you too, Ellie. I didn't mean to startle you." She gently put her hand on Jeff's shoulder as a means of comforting 'Ellie'. "Have a nice evening, you two!" she said as she turned to walk off again.

Just as Stephany was about to close the door, she noticed the pizza delivery car approaching from the distance. It drove up to the building and came to a stop.

Stephany grabbed Jeff's hand and said, "Sorry about that. I wasn't expecting that one either. But on the plus side, I don't think she recognized you."

"Do I still have to take the pizza?" Jeff asked anxiously.

"I'll do the talking and the interactions, just stay here with me and look friendly, that's all you'll have to do, darling," Stephany said reassuringly.