The Next Day

The next day, Aaron got up and was on autopilot. It had only been a little while since he had to take up the role of Erin, but he was surprised that he was really getting used to it. He didn’t even need Sarah’s help to get a passable look with his newly found makeup skills, starting with a layer of foundation, some simple concealer, and then going for a more ostentatious look with deep red lipstick and smoky eye. It wasn’t his fault that Sarah only left out those colors. He was going to be late if he didn’t put his face on, so he just went with it.

Getting dressed became almost second nature. He pulled the inner panties up, making sure to tuck everything back, and got the second layer over, this time a pair of black lace panties. They felt a bit off, almost heavier, especially in the rear, but he shrugged it off. The matching bra went over his chest, and he kept going, pulling a pair of black pantyhose over his freshly shaven legs and a pencil skirt that he could’ve sworn was long enough when he tried it on at the mall, but now felt absolutely slutty, showing parts of his upper thigh. He buttoned up the blouse, swearing to himself as he realized either Sarah or Madison had cut the top buttons. His cleavage was going to hang out again. Tying his hair up in a bun and putting the pair of black heels on, he made his way down the stairs.

He grabbed his purse and started feeling pretty anxious. Sarah had set him up on a date with Ted after work tonight, so he was really starting to freak out at the thought. He knew he needed something to help ease the stress, so he grabbed a bottle of pills from the cabinet, assuming they were his old anti-anxiety pills. He shoved them into his purse and was off.

Erin had a hard time adjusting to his new job. For some reason, no matter how he sat, it never felt comfortable. He tried crossing his legs, but the fabric of his skirt rode up. He also tried sitting with his legs out as he would normally sit, but with his current aesthetic, the message was less “I’m just sitting” and more “fuck me now!”

“Erin?” The voice rang out. It was Brad, and Erin stood up.

“Yes, Brad?” Erin asked.

“Can I have you grab some files for me. The Zybliski twins are coming in today and I need their charts” He smiled.

Erin strutted over to the filing cabinet, and as he went over, he realized what was happening. The cabinets were labeled, with the top row being A-C, and going down from there. He looked at the one at the bottom “X, Y, Z” and noticed Brad’s prying eyes from across the room.

He took a deep breath, trying not to think about the mental undressing that was about to occur, and bent over. He kept his legs together to keep balance and to make sure nothing peaked out, but his skirt rode up, showing the bottom part of his ass cheeks as he reached the climax of his bend. He opened up the file and found the Zybliski folder. Grabbing it, he passed it to Brad, who was looking positively in love. Erin scurried back to his desk. He grabbed a few of the pills from the bottle and swallowed them, taking a deep breath as he got back to work.

The rest of the day was fairly uneventful, with basic filing tasks and appointment setting. This was a pretty normal office, after all. Erin felt pretty good all things considered. Those pills didn’t really help, as they mostly just made him really short of breath and pretty sweaty. The time went by pretty inoffensively, then Ted came in. He was dressed in a pretty nice suit and even Erin had to admit, he looked good.

“Hey babe, ready to go?” He asked.

“Y..yes” Erin responded, almost a little scared.

They went to a restaurant, but this one felt special. Ted was really friendly with the owner and had gotten the couple a private dining suite. It was the kind of candlelit dinner you see in movies, and Erin was stressed as hell. The server brought the wine and Erin took full advantage, downing almost an entire glass before grabbing a handful of the pills and swallowing them with a swig of wine. He wondered why they weren’t working, so he quickly looked at the bottle. The label:

“Libido-Max”

Erin could’ve sworn he threw those away when his wife died. She had been going through the early stages of menopause when she died, and as a result, her sex drive had gone down significantly. Her doctor prescribed a libido booster, which was a fast-acting pill that would get her in the mood quickly. Aaron was concerned but was a bit happy that they didn’t get him super horny back when he was at work. They probably just didn’t affect him. What he didn’t know was that the effect of these pills was amplified when mixed with ****, and Aaron had just drunk a whole glass.

“So, Erin. How was work?” Ted asked, seeing his girl flustered.

“I..it was good.” Erin couldn’t get much out, and just started sweating, feeling something begin to buzz.

The day before, Madison and Sarah decided to have some fun with Aaron. They took a small, egg shaped vibrator and snuck it in the back of his inner panties. It was tiny, but it packed a punch and was now sitting right in between Aaron’s crotch and asshole.

Madison had the remote for the vibrator and sat at a table at the other end of the restaurant, eating. She clicked it on when she saw the couple go into the private room, setting it to increase in intensity slowly.

Aaron was feeling the vibrations and began to bite his lip. He had the strongest urge to moan, but he knew that a sound like that would only make Ted think he was horny for him. Ted saw his girl biting her lip with her eyes almost rolling back in her head and put two and two together.

“Babe, you’re looking pretty hot and bothered tonight.” He said, and Aaron’s focus shifted as he heard the zip of Ted’s fly. Aaron was feeling incredibly horny, but in a weird, directionless way. It wasn’t a specific attraction to anyone of anything, just an urge to get this feeling out, and he knew the way to do it. He looked over at Ted’s cock as it was emerging from his pants and without thinking, he grabbed hold, stroking up and down before going all in, sticking the massive thing into his mouth and bobbing up and down. Aaron wasn’t even thinking; this was just instinct. He was just so horny and had to do this. At the same time, the vibrator had increased in intensity to a point where Aaron needed to get it off of himself. He pulled down his pantyhose and panties all at once, not thinking about what that would look like. He knew what he had to do, and whipped his legs around Ted’s crotch, using his perfectly manicured hand to guide Ted’s member into his tight asshole.

An inkling of rationality entered Ted’s mind and he realized that if he was going to “finish” in this scenario while keeping his cover, he’d have to think fast. His cock had already begun to grow, and Aaron grabbed one of the cloths from the table and put in in front of his dick. As he bounced up and down on Ted’s dick, he felt himself getting closer and closer to the big O, and he felt Ted release his load into Aaron’s ass. He knew what a girl sounded like when they had an orgasm, so he moaned a little bit to give the appearance that “she” finished as well. Aaron came too, but he quickly grabbed the ejaculate in the cloth and held it, pulling Ted’s dick out of his ass and bringing the cloth down there, as if to clean up. Both of their seeds mixed, but to the common observer, it looked like he was only cleaning up for one man.

He wiped himself off and as Ted was still collecting himself, Aaron pulled his panties up, tucked his member back, and pulled the pantyhose back up. He had gotten away scot free. The feeling of horniness had dissipated a bit, but to get the last remnants out of his system, Aaron passionately kissed Ted, making sure to use a lot of tongue. When he pulled off, he felt fine again, trying desperately not to think about what his body had just done, and even more terrifying, that he actually kind of liked what happened.

They ate their food, and it was all a bit awkward, but the couple left out the front door and Ted drove Aaron home. They kissed briefly before Ted let his girlfriend out, and the two went their separate ways for the night. Aaron walked in, trying to act normal before running past Sarah and Madison and into his room. He ripped off all of his clothes and tossed them into a pile. He took a long, hot shower to get the scent off of him, and eventually, he just sat in the running shower, crying. So many emotions went through his head, and he was overwhelmed.

Perhaps tomorrow would hold more answers.