Mia's Coffee Date Leads To More

"Mia. Mia. Mia." Tanya repeated, rocking Mia back and forth, having moved the thin body back onto the master bed easily. She hadn't awoken since Tanya had gotten home, not except for sleep walking groggily, which quickly ended when Tanya brought her back to bed.

Mia woke up, still closer to sleep then reality, and felt herself being pulled up, and the brought along. Perhaps she had taken too much of that medicine? A hit of cold water woke Mia up completely, and the feeling of makeup running down her face got her up easily, with Tanya helping support Mia until she was fully awake.

Simon stretched, confused where he was, but happy to see Tanya. The last thing he remembered was being in front of the TV, and then....nothing much else.

"Tan-tanya? What time is it? I'm exhausted." Simon asked.

"Early morning babe. Here babe, keep still." Tanya said, rubbing all of Simon's body with the nair once more, and shoving her finger easily up his butt, with her free hand going down to his dick and pumping it dry. Simon, in cloud nine, was little more then putty in his girlfriends hands, allowing her to pretty much do whatever she wished until she brought him out of the shower.

"Tanya? I'm, um, face feels funny still." Simon said, sitting on the toilet, looking half the part of feminized boyfriend, the other half a hungover party animal.

"You'll be okay hun." Tanya said, not used to such a sensitive boyfriend, smiling. "Open your mouth, you need to take your meds from the doctor to get better."

Nodding, Simon stuck his tongue out, accepting the pain medication, and Tanya rubbing the creams over his face. "Th-thank you. Sorry Tanya. I swear, I feel crummy, I'm really not trying to act."

Tanya smiled at his lack of confidence. "It's alright. Here Simon..." She said, navigating a pair of panties up his legs and pulling him out into the kitchen; Simon was starving, and accepted the coffee and eggs like it was the best food he'd ever eaten.

"Baby, I feel a lot better, I'll, uh, get to my job search. Hey I need to go take my medicine really quick." Simon said.

Tanya raised an eyebrow. Was his memory failing him? Beating her boyfriend to the bathroom with the pills, she realized it said not to ingest any of them with excessive amounts of caffeine, so perhaps that was effecting him. Odd, she'd never heard of a restriction like that. Simon, much more docile then normal, sat on his laptop, scrolling aimlessly. A ring of the doorbell alerted both of them.

"Mia, hold still, Gabriele has to put foundation on you." Tanya replied. She'd called off work for this. Gabriele had worked, on the phone, designing a costume. He and Tanya went back far, to the same school as Simon, and they were able to help one another out. Tanya had massively helped him on one of his last projects, and she had collected her favor twofold.

"Tan-tanya....my hair feels funny. Like, super duper heavy." Simon complained, and Tanya rolled her eyes. They'd taken the wig off, Gabriele horrified she'd even used a wig; in short order, they had blonde hair down to Simon's roots, with extensions weaved so deeply it was indistinguishable.

"Baby, come on, Mia voice. Remember, you're getting into character." Tanya said. Simon smiled as he felt a hand on his dick. It was empty from their morning escapade, but some light touches from her hand kept him focused.

"Remember, eyes closed." Gabriele's higher pitched voice said.

As the sun rose, the two got to work on every corner of Mia's body, and before the clock had even hit 7, Mia felt like a new woman. Very much like a woman. Too much like a woman for Simon's comfort. At first, he tried not to imagine why it felt like the sandbags on his chest were back, but once he felt padding incase his butt, his eyes fluttered open, and he briefly looked down, realizing he had....boobs? What?

"Wh-why do I have boobs?" Simon asked.

"Mia. Stop peaking." Tanya said, giggling. Her boyfriend had been so willing, it was insane; the Simon of 5 days ago was lost to the sands of time. Gabriele had kept mostly quiet, but he even gave a girlish laugh, before they put a bra on him, complimenting his lacy panties.

"Eyes open." Tanya said. She and Gabriele helped Mia sit up.

"Mi....mi god!" Mia said, staring into the mirror. Clad in only the bra and panties, Mia had a pair of very realistic prosthetic breasts, much to size Simon would've loved (on any person other then him), combined with a rear end which would look deadly once he was in fitting clothes; the blonde hair, which went down to his breasts, complimented the cherry red lipstick well, and not only did Simon disappear from the mirror, Mia the MILF took center stage.

"Alright, that's part one, Mia, stay standing, your corset's next...." Tanya said.

The next hour was misery for Mia. Squeezing into the corset was horrid, and Tanya promised Simon & Mia both would be going on a diet, while getting her toenails and fingernails painted wasn't the most pleasant, especially as she had to wait for them to dry. Once everything was finished, Mia got dressed, a pair of pantyhose first coming up her legs, then a silver dress, and platform heels. 10 minutes of training later, Mia was versed in just enough heel ability to not trip on her own face, but not enough to look a bit off balance.

"So-so....Senorita Tanya, why must Yo do this?" Mia asked, sobering up from the morning, and seeming to lose the appeal of bouncing her own fake breasts and other new experiences.

"Pictures for my dad. Remember, that's why were doing all this." Tanya said. Getting a photoshoot done in a very quick amount of time, Tanya sighed, and dismissed Gabriele, who looked near dead from exhaustion. "And you have a coffee date you'll be on time to if you rush that cute little butt out the door."

Simon had argued. Mia had whined. Tanya didn't listen to much of it. After pulling up Mia's dress, and giving her one of the best blowjobs of Simon's life, (and he even gave her time to let it out of her mouth), their were no complaints, just Mia taking the offered silver purse, and getting in the car. They made it 5 minutes before Senor Eric was due to arrive.

"My goodness, if that is how beautifully you dress for just coffee, I'd love to see your fine dining dressing." Eric, the doctor from two days prior, said with a cocky smile as Mia sat at the cafe table, looking nervous.

"Flattery will get you everywhere, Senor Eric." Mia said with confidence.

"Please, flattery is phony, my comments just speak a known truth. Now, what might I get you?" Eric asked. Mia wondered what she would get.

"Si, Yo, um, how might you say it, a muffin and el latte, extra sugar and cream." Mia asked, and Eric soon was back at the table, with Mia sipping the sickly sweet drink, enjoying how it pepped her up.

The two began to converse, trading playful flirting, and Mia learned more and more about the (noticeable bachelor) middle-aged doctor, and his practice. He was very much a career man, loving to talk about it, and Mia enjoyed the flow, finding new ways to talk with him and use (Simon's meagre) spanish. Still, she was quite worried, her finger tracing the outside of her cup. On the one hand, it felt amazing, to act and be well, damn good at it. A man playing a woman convincingly was hard enough. But enough to get past a horny man? That was damn well Oscar level acting. At least, that's what the egotistical part of Simon felt.

Meanwhile, the other side of Simon, the worrier, was keeping that all in check, and showing itself on a silver platter to the doctor. Eric ended their conversation on family and let his hand take hers, squeezing it, and giving her a genuine heart melting smile.

"Mia, Senortia Lozeno, you are nervous over something. What bothers you dear?" He asked.

"N-no! Senor Doctor, nothing bothers mi!" Mia stuttered out.

"Mia, please. I'm a doctor who deals with embarrassing skin conditions. What might be wrong? First date jitters?" Eric asked. He understood first date jitters, but for a woman as beautiful as this, it was odd; he, in his own opinion, should be the one with butterflies in his stomach, not her.

"S-si. I apologize Senor Eric, it is, you know, dificil to get back into it." Mia responded.

"I understand completely." Eric said. "Now, how about we leave the coffee behind and see a bit of the city?"

"Yo, si, uhm. Verdad, Senor Eric." Mia responded with a blush as Eric's hand did not leave hers, and the two left the coffeehouse, Mia unable to even lose his strong grip.

"Please. Just Eric." The doctor said, feeling the first date go well enough that he was walking the city hand-in-hand with the beautiful woman. Still, his worry over her anxiety grew as she stumbled on the heels, and eventually, as they walked across the street, she wobbled, toppled over slightly, and felt her left heel snap, nearly falling to the ground if not for Eric's tight on her rear and hip.

"O-oh....Hijo de puta! Fuck! Bastardo heel..." Mia muttered. Eric got her into a nearby seat.

"Mia, it's alright, okay? We'll get you a new pair of heels. My treat." Eric said, seeing the telltale sign of a woman near tears.

"N-no. Don't waste your time Eric" Mia responded, trying to play it up, seeing how far her act might go.

"Stop. You're okay. Here, no need to cry, let's get you new heels." Eric said, wiping the tears from her eyes, and bringing her along with him down the street, hand grasping her hips, making her walk assured, even barefoot on the concrete. They stopped in a nearby store, and Mia allowed Eric to spend his effort finding the right size, and strapping the heels on. They were taller then the previous heels, something Mia was sure Eric knew, and when they left, Eric kept a much tighter grip on the woman. The bill was in the hundreds of dollars.

Mia, just letting the date flow, realized it had to be close to mid-afternoon as the two sat for a rest in a park, Eric rubbing his hand on her palm.

"Er-eric....thank you. Quiero to pay you back...Please." Mia said with a smile.

"No, no paying back. If you'd like to return my help, might you listen to me with open ears for my advice?" Eric asked.

"Si!" Mia said, nodding.

"You're an anxious woman. I don't mean this meanly, just stating it, and how common it is for woman as mature as yourself to be anxious and worried. Do you understand?" Eric asked. Mia had been looking at the ground, and he used his free hand to bring her chin up, while she nodded in response. "It's okay to be anxious. We even have medicine that can help you with it. I know we were just getting coffee, but the Doctor part of me, not even the dermatologist part, just the part that wants to help you, wants me to get you that help."

"S-si. I appreciate it..." Mia said, her words cut off as Eric kissed her lightly, pulling back from the whole kiss after a second or two. Completely caught off guard, Mia went through the motions afterwards, and followed Eric to his car, completely befuddled at the kiss she had just received. Was her acting that...amazing? Truthfully. By the time she was out of her head, Mia was back in the Doctor's clinic, the place long closed on a Friday, sitting with him. He came back after a few minutes with a small bottle.

"This is only a sample. Next week, when I see you, I will get you a full prescription. For now, this will tide you over. I'll see you on Monday, and hopefully, for our second date....?" Eric asked.

"Mhm! Cuanto? Tuesday?" Mia asked, taking the pill bottle.

"Yes. That is quite perfect." Eric said, allowing her time and water to take the first of the pills, and then driving her back. As she left his car, he kissed her, and Mia leaned over, imprinting her red makeup on his neck.

Tanya was passed out by the time Mia returned, having been up just as long as Gabriele, and even more exhausted. Mia, feeling heavenly and just a bit drowsy, sat on the couch, going into the dating app briefly, and seeing messages from the two men she had dates with tomorrow and Sunday.

Senor Andrew: Hermosa, I have reconsidered how best you can use your heels; how about we take you shopping, go to dinner, then go dancing? I thought it might help you forget the broken heel.

Jeremeiah--Conqueror: Be ready by 5 tomorrow, senorita. No makeup or time wasting.

Typing out on her phone, Mia responded to both men, and as if like clockwork, they responded back to her in a few minutes; she was making a salad as she typed to them, the fridge seeming somewhat bare when she looked for anything.

Mia: Si, adora la dancing! I cannot wait to see your moves Senor Andrew.

Senor Andrew: I'll be glad to show you them, hermosa. Perhaps guapo is another nickname you deserve.

Mia: Si, senor, Yo tengo be ready by 5.

Jeremiah--Conqueror: Good niña.

As she finished her meal, Mia enjoyed the floating sensation, scrolling through horde of men, men, men. Dick pics, dry lines, other, tinier dick pics, dumber pick up lines. Aimlessly scrolling through her phone, Mia uploaded the photos of her from today, liking them, and soon enough, she was back checking different tabs, before she felt just about ready to pass out. Checking her dating app once more, she got one messaged that peaked her interest, then another.

Princeof'78: Senorita, your blond hair is beautiful. I hope I might see the brilliance of it in person.

Mia: Quiza, senor. If I got to ride in your hot rod.

Mia checked out the man's page. He was an older man, older then even Mia's supposed MILF age, probably close to his 50s. However, his sportscars were beautiful, and he clearly was proud of them, his stocky build sitting in them making up nearly all his photos; those that weren't of cars depicted a plane.

Princeof'78: A joyride is always on the table. Next week?

Mia: Ok, monday?

Princeof'78: I'll mark it on my calendar chica ligera. Don't forget.

Mia looked over his profile, swearing that something about the man looked familiar, but could not remember it, her drug induced haze making straight thinking hard. She spent the last of her effort looking up the word 'chica ligera', and realized the man had called her a beautiful young woman. Hphm. These horny older dudes certainly knew how to put it on thick.

Collapsing into her pillow, Mia allowed Tanya, who was half-awake, to cuddle into her tightly. She slept peacefully, forgetting to even get out of the dress.