On the Pill: Chapter 2

 On the Pill: Chapter 2 by Lou Bealy

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For maximum enjoyment, you should read part one first


Michael could hardly believe the events of the previous night. He could hardly even process it. The idea that just a few hours ago he was a hot older woman getting the business from his best friend was too fantastical to believe. He would probably have just written it off as a freaky dream, if not for the evidence that still remained. His nipple had red teeth marks all over it from when Frank had been sucking and chewing on it. He still had dried and sticky cum all over his groin and belly that he knew had to be Frank’s. This evidence forced him to confront what he had done while under the influence of female arousal.


It had been fun, but now he questioned why he so easily gave in to his baser desires and let another man fuck him. Once it had occurred to him to relieve his horny state by inviting Frank over, he had barely resisted the idea at all.  He shook his head, thinking that it didn’t mean anything about his sexuality. His revulsion to the idea of being intimate with another man was still every bit as strong as it ever was. No, he concluded, he wasn’t gay just because he had had sex with another man while in a woman’s body. There was nothing gay about a man and woman fucking.


Michael just hoped that Dad didn’t notice the missing pill. As curious as he was why his dad even had such a thing, he didn’t want to have that conversation. He was still weirded out by his own actions while on the pill and didn’t really want to hear about whatever debauched activities his dad was getting into while on those pills. He just hoped it was with Mom.


That thought gave him pause. Did his mom even know about them? Was Dad cheating on her? Michael knew that if he brought up the pills at all, it would provoke a conversation that may lead to the missing pill. So he decided to let sleeping dogs lie.


He tried not to stress out about it, and simply concentrate on finalizing his move. He still had to switch his credit cards and car payment to the new place, go back to his apartment to clean and then organize his new living space. That was in addition to returning all of his mom and sister’s clothes back to their original state, or as close to it as he could replicate. He had been too busy having fun as a hot MILF all the previous day and now had to rush to get it all done before he had to go back to work. His continued preoccupation with the previous night’s events did not help his productivity either. By the end of it, he was totally exhausted but relieved that he had gotten most of it done.


He finished just in time before his parents and siblings returned from their trip. They all sat down to a pleasant dinner together, which was nice because with everyone’s busy schedules it had become something of a rarity to have a family dinner. Michael barely touched his food, his fatigue and nervousness at the situation suppressed his appetite. If his mom or his sister Catherine had any inkling that he had rooted through their things and tried a bunch of their clothes on, they didn’t show it. He wondered if it were just too awkward to bring up, or if he had truly gotten away with it. The same could be said about his Dad. He was quietly eating his dinner and not adding much to the conversation of the events of their trip. He was normally very quiet and reserved, so this wasn’t a sign of anything one way or the other.


To his dismay, Michael would get no assurances that his escapades had gone unnoticed. It just hung over his head for the rest of the evening. He didn’t say much, and just let his family talk about how much fun they had with his aunts at the coast. He almost wanted it to be brought up by someone, at least he could stop worrying about it then.


“Are you okay, Michael?” asked his mom, with notable concern in her voice. “You’ve barely touched your spaghetti. Does it taste okay to you, Paul?” she asked Dad.


“Tastes good to me.” replied Paul, slurping up more, happily eating one of his favorite meals.


Michael sighed. “No, no. It’s fine. I’m just tired. I’m going to bed after dinner, I think.” He avoided eye contact and hoped that none of them asked anything else about it. He knew that his poker face sucked, as had just been demonstrated.


He made it through the rest of the dinner without anyone paying him much attention. Afterward, he made his way back upstairs to his room and plopped on his bed without even taking his shoes off. He tried to sleep, but despite how exhausted he was, images of the previous day kept running through his head. He remembered how sexy he felt as that older woman. He had loved the feeling of his friend’s thick cock slipping inside of his wetness, the novel pleasure was unlike anything he had felt.


That particular moment, the moment of penetration kept replaying over and over in his head. He realized that his cock was rock hard and immediately reached down to open his jeans and stroke it. He quickly brought himself to a leg-shaking orgasm. Somehow, it didn’t feel right. It had actually been a little underwhelming, he realized.  It was probably his most powerful orgasm that he could remember, but for a moment he felt like something was missing. He stopped that line of thinking before it went somewhere he didn’t want it to go. At least his orgasm made it easier to sleep, as it usually did.


* * *


The week went by, and Michael got settled into his new living arrangement. No one brought up any missing pills or rearranged clothes, so he figured that after a week with no confrontations he was in the clear. Despite not having to worry about it anymore, his mind kept returning to the pills. He couldn’t stop thinking about wanting to try them again.


Michael searched online for “Alterex” again and this time was able to find what appeared to be the manufacturer's website, though it had to have been translated and retranslated in some foreign languages because it was hard to even make sense out of it. It said that it could only be purchased from “the sellers of the authorization”. He figured it must mean authorized dealers or something to that effect, but it didn’t give any indication as to where that might be. After some time of fruitlessly trying to find one of these authorized dealers, he gave up.


He stomped to his bathroom in frustration, very annoyed he couldn’t find out how to get any Alterex. When he pondered why he was so irritated at not being able to find it, he told himself that he wanted to know out of sheer curiosity. But he knew on some level why he wanted to find it. He wanted to feel that sexy feeling again. He had been fantasizing about it all week each night while masturbating. He recalled how he would try and remember what it felt like to be fucked like a woman and he would usually cum shortly thereafter. He would then feel ashamed as he cleaned up. He knew he had to try another pill, but he would have to wait for the right moment. Having a house full of five people made it very hard to get any kind of privacy or solitude.


Luckily his family members all had plans for the weekend. Catherine announced she was taking a drive down the coast to look at colleges, and Mom was going with her. Grant was going to catch a ride with a friend and be in Florida for most of the weekend. Dad said he was going to go to hang around for a bit and then maybe see a  movie at the theater.


Michael didn’t want to risk his family coming home unexpectedly and catching him in his female form. The whole scenario played out in his head. He would have to explain who he was if they even let him. If his mom or sister caught him, they might even call the cops on him. He chuckled to himself as he imagined sitting in a cell all night before the pill wore off the next day and a guard finding him wearing a teddy. No, a hotel room in the next town over was a much better idea. He did have to hurry, though. He wanted to be sure he was back in his male form by the time he had to work, so the sooner he got a chance to take another Alterex, the better.


He would just need to sneak into his parent’s room and get a pill before he had to leave to go check in at the hotel. He waited for the right moment to dart in and grab it. By this time, everyone else was gone except him and Dad, who was still getting dressed and ready for his movie.


“You need something, Michael?” asked his dad while buttoning up one of the standard white dress shirts that he always wore. He was so slight of stature that he wore a medium dress shirt, that was still a bit baggy. Michael definitely took more after his mom's family than his dad’s, being taller and more barrel-chested. He must have noticed how Michael kept walking by his room and peering inside.


“No, I was just-” Michael thought fast. “-wondering if you could help me. My car is making a strange noise. Can you take a look?.”


Dad chuckled and finished getting dressed. “You think I know anything about cars? Take it to the shop. I have a few more things to take care of here before I leave. Maybe appreciate a little bit of quiet for once, since everyone will be gone.” he chuckled.


“Could you just listen to the noise? It might be serious.” he pleaded. “ I don’t want to get on the road and have a problem.”


“I’ll be right there, ok?” he said while putting on his expensive watch, one of the few displays of vanity he allowed himself. It looked huge on his thin arm.


Michael noticed that the drawer that the pills had been in was wide open. He immediately got nervous that his Dad would mention the pills then and there.


“I have to go, I have an appointment waiting on me. Please?” He needed to get that pill and go, why did his dad always have to make things so difficult?


“Okay! Okay!” Dad shook his head and laughed. “Where are you going, anyway?” he wondered. “Going to have some fun? Maybe some new experiences?” he grinned.


“I…” Michale again had to think fast. He hadn’t really expected them to ask or care where he was going. “I have a date with a girl I met online if you must know.” he added with a hopefully convincing indignant tone. He didn’t know what else to say, he wondered if Dad was insinuating what it sounded like he was.


“Ah, I get it.” Dad laughed. “Sure. Let's go start it up.” he started down the stairs.


“Here.” he handed over the keys. “I’ll be right there, I forgot something.” he turned to walk towards his room but stopped as soon as Dad turned the corner. He darted into his parent’s room and rooted through the open drawer. He didn’t even look at the blister pack as he popped out another pill and shoved it into his pocket. He quickly ran downstairs to catch up with Dad.


“Okay, let’s see what we got here.” Dad said, putting the key in and starting it up. "I don't hear anything weird." he said, listening closely.


“Huh. It was making a noise before, of course, it won’t now.” Michael tried to sound irritated. Dad still hadn’t said anything else about the pills, so he was starting to relax.


“Yeah, I know how that is.” Dad chuckled and after a minute or so of no strange noises, shut the car off.


“Well, thanks anyway.” Michael said, his hand in his pocket grasping the pill. If Dad suspected anything, he didn’t mention it. Michael allowed a little hope that he had gotten away with it.


Michael finished getting ready, packing a few clothing items that he thought would fit, like a bathrobe, sweatpants with a drawstring, a large hooded sweatshirt with a zipper in front. All of it should fit, he hoped. He planned to go pick up some fitting clothes at the Walmart nearby the hotel after he had transformed.


 It was a seedier motel, that he knew must be a frequent hangout for prostitutes. If for some reason someone had a question why a woman that was not on the reservation was in the room, they would surely assume that she was a prostitute. Especially with the type of clothing that Michael planned on buying. He had not forgotten how sexy he felt looking into the mirror with his mom’s lingerie on, as much as he would never admit it to anyone.


Once he got on the road, he ate the pill, wanting to maximize his time at the hotel as a woman.


He stopped at a gas station a few miles down the road from the hotel and when he went to the pump he realized that he had forgotten his wallet.


He cursed. He wouldn’t be able to check into the hotel without his ID. He angrily turned back and headed home, hoping he had enough gas to get there, and back to a fill station.


He pulled into the driveway and ran inside, through the garage. He noticed Dad’s car was still there on the way in. He ran down the stairs, still cursing at himself for being dumb enough to leave his wallet. He had been in too much of a hurry, he figured. Once in his room, he quickly found the wallet. He had left it in the previous day’s pants.


On the way back to the car, he noticed a sound coming from upstairs. It sounded like groans of pain or something. He didn’t know if it had been going on the whole time he was there, and he just hadn’t heard it.


Maybe it’s the sound of sex, he thought to himself and chuckled. He knew Dad wouldn’t have the balls to cheat on Mom. Who would he cheat on her with, anyway? The man had like zero game. It was a wonder he had ended up with a smoking hottie like his Mom May in the first place.


He was confused at what the moans coming from upstairs could be, so he headed up to check it out. He decided to be stealthy, just in case it was Dad cheating or masturbating or whatever the hell he could be doing. 


Michael arrived at the door and peeked through the crack. He saw his Dad on the bed, naked. He was writhing back and forth on the bed, seemingly in pain or something. His skin was flush red like he had just run a mile, and he was soaking in sweat. He was moaning as he squirmed around on the bed. It was a truly bizarre sight. Michael just stared for a moment before opening the door slightly.


“Are you okay, Dad?” he yelled in.


“What? Michael? Go away!” he yelled in surprise. His voice seemed higher pitched than normal.


Michael immediately knew what was happening. He stepped into the room and threw the door open without even thinking. He wanted to see this. He hadn’t been paying attention when it happened to him, though he remembered how much he squirmed with discomfort while he was trying to win the game. He sat on a chair in the corner and waited for what he knew was coming.


“What are you-” Paul suddenly stopped. They both watched as his body began to change. He clutched his stomach, the feeling of his insides shifting around was almost painful and definitely unpleasant. He moaned in what almost sounded like a woman in the throes of pain (or pleasure).


His hair began to lengthen out and change color, quickly reaching his shoulders. It brightened from a darker blonde to a bleach blonde. At the same time, his nipples began to expand until they were the size of quarters. The flesh behind the feminine nipples began to rapidly expand, forming feminine breasts.


They both watched as Paul’s slight frame began to take on more of a womanly shape. His hips began to accumulate fat. His breasts continued to grow. His ass expanded until it was nice and round, Michael noted as an ass man. Lastly, his face became more feminine, or at least that was the last thing that Michael noticed. He had been staring at Paul’s body, but concentrating most of all on his crotch. He saw his average sized cock slowly shrink away until he was a full-fledged, voluptuous, big-breasted older blonde woman. His height remained more or less the same, but he was otherwise totally transformed.


Michael had a raging hard-on, watching a beautiful big-titted woman emerge from his skinny nerd of a Dad was the hottest thing he had ever witnessed, as taboo and wrong as it was. Maybe that even enhanced it, he wondered.


“Michael…” said Paul finally, in a husky yet feminine voice. He reached down with his small, feminine hands and grabbed the blanket on the bed and pulled it over her body. He stopped, seemingly not knowing what to say.


“What the hell just happened, Dad?” Michael tried to pretend that he didn’t know.


“Cut the shit, Michael.” His deep but feminine voice had a stern tone that he was used to his Dad using. “You took the pills, didn’t you?” His green eyes narrowed. “I’m missing two of them.”


Michael thought for just a moment about whether he should tell the truth, but the look this pretty MILF was giving him was all too familiar. He had never been able to lie to his parents, he wasn’t good at it. He had not needed to lie to them much, either, being a good kid for the most part.


“Yes.” Michael croaked. Embarrassment burned on his cheeks. Despite his dad being the one to have the pills in the first place and was currently in female form, he was still ashamed he had used one of those pills. Most of all, he was ashamed he had stolen them. He assumed that they were expensive.


“I thought so.” the pretty older woman chuckled and patted the bed. “Come here.”  

Michael couldn’t believe what he was seeing. His Dad, he had to keep reminding himself it was him, was staring at him with a come hither look. She- no he was biting his lip and rubbing his large nipples.


“Why?” Michael asked nervously. His cock was still rock hard but he definitely did not want to acknowledge it.


“Just come here. You’ll like it.” Paul said seductively.


“Dad, we shouldn’t-” Michael protested half-heartedly. 


“It’s Paulina right now.” the beautiful MILF corrected. “And yes we should. The pills make me so horny…” Paulina giggled then added, “I know you know what I mean.”


Michael did, in fact, know exactly what his Dad- now Paulina- meant. He didn’t remember the last time he got laid, and this beautiful creature was practically demanding it. He hadn’t had any romantic encounter (in his male form) since long before breaking up with Kelsey and needed this. He sat on the bed, his erection creating an obvious bulge in his jeans. Paulina looked right at it.


“Dad-”


Paulina.” She corrected.


His protests died in his throat. He didn’t know what to say anymore, he was so conflicted. There’s no way he was going to… do anything like that his Dad, even if it was while he was in the body of a gorgeous MILF.


They sat for a few moments, staring at each other and silently struggling with themselves. Michael grappled with the knowledge that this woman was his Dad. Paul was struggling to remember what the consequences of giving in would be. He was horny enough to fuck his son, even if it was as a woman and could hardly think about anything else. Neither of them moved, each hoping the other would balk.


After a long and uncomfortable silence, she made the first move and scooted closer to him. She reached down toward his crotch with her slim, feminine fingers. She flipped her body back for a moment, throwing the blanket aside and once again revealing her curvy body.


Michael flinched as she grasped his cock through his pants, squeezing his aching bulge.

“What’s wrong? You know you want it.” she said in a low, seductive voice. “I definitely do…”


“I-” his words caught in his throat as she began to stroke his clothed cock. He closed his eyes and just enjoyed the attention for a moment. He could smell her body odor, and it was quite alluring. He always loved the scent of a woman. He could smell her arousal as well, which made it just about impossible to think straight. A moment later he felt her mouth on his.


Michael fell backward onto the bed. She leaned over him, their mouths still pressed together. Her tongue pressed between his lips, and he let it enter, entwining with his own tongue. Michael felt her climb on top of him, straddling his lap. She leaned down and rubbed her huge round tits across his face. He caught a nipple in his mouth and sucked on it for a moment while reaching up to squeeze both of her tits. He switched to the other nipple and sucked on it too, loving the feeling of the soft flesh in his mouth and hands.


“Mmm… yeah, baby, just like that.” she cooed.


After a moment, she pulled her nipple from his mouth and climbed off. Michael was about to protest when he opened his eyes and saw her unbuttoning his pants. He lifted his ass off the couch and she yanked off his jeans. His boxer shorts followed directly.


There was something red hot about the way she made eye contact with him while holding his cock. She grinned and slowly lowered her lips around the head, her tongue began running along the underside.


“That’s it…” Michael moaned. “Just like that…” he lay back on the bed, in the midst of what had to be the best blow job he’d ever had. “You’re good at this…” he whispered. There was no way that this was the first one that Paulina (or Paul?), had given, he concluded. He slid his hands through her hair and grasped her head. He began to fuck her mouth, his hips gently moving back and forth before gaining speed.


Michael’s hips slowly picked up speed until she made a choking sound with each thrust as his cock hit the back of her throat. He felt her orgasm coming, and his began to go into overdrive. He was just at the threshold of orgasmic bliss when she stopped and stood up.


“Wha-?” he began to protest before she shoved her tongue in his mouth again. Normally, he was a bit too squeamish to allow a girl to kiss him or anything right after a blowjob. This time, even if he could have complained with her tongue in his mouth, it didn’t even occur to him as a problem. He had no time to think about it since she was already climbing on top of him. He felt her grasp the base of his cock and give it a good squeeze, before lowering herself onto it.


“Yes…” Paulina breathily whispered in her deep sultry voice before once again shoving her tongue in his mouth. She let out a long sigh as his cock disappeared into her hungry pussy.


He moaned the feeling of bottoming out inside her sent a shiver down his legs. She began to rock and forth, his cock slipping in and out of her with increasing speed. Their tongues danced around their mouths in rhythm with the frenetic motion of their hips. They never truly found a good rhythm and it became almost a race. They were both just slamming into each other as fast as they possibly could.


Michael came a moment later, almost without warning. He squeezed her hips and thrust in as hard as he could, as he painted her insides with cum.


Paulina continued to thrust her hips back against his now stationary cock, and then finally came herself. Their lips finally parted and she cried out in ecstasy before mashing her face back onto his. He felt her pussy to spasm and contract on his cock as she came.


Neither spoke for a while. They just lay there for a while with her on top of him, both of them out of breath and dripping with sweat. Eventually, she climbed off and plopped next to him.

Paulina cleared her throat and finally broke the awkward silence. “That was fun.” she declared and then giggled. “We should do it again.”


Michael wanted to argue, say they could never do it again, that they really shouldn’t have done it at all. But all that came out was, “How many pills do you have left?” Then he thought out loud, “Where’d you get them, anyway?”


“Four, I think.” she explained. “And I got them from Frank.”


“Frank?” Michael asked, perplexed.


“Yeah, the elder Frank, I mean.” she laughed. “Not his kid.”


“Right.” Michael felt silly for momentarily forgetting that Frank shared his Dad’s name.


“Anyway, we were watching the game, and just talking shit about our wives, you know? How they won’t put out as much as they used to.” She cuddled up to him and continued to explain.


Michael almost didn’t notice how strange it was to be having this kind of talk with his Dad at all, much less while he was in a woman’s body.


“So we were bored and he asked if I wanted to try something. I said I’m not into a gay shit or anything.” She laughed. “But he took a pill and a few minutes later, he was a buxom blonde who wanted to fuck!” she squeezed him for emphasis. “Afterward, he gave me the number for his guy who had them. I bought a MILF variety pack, which was the best bargain.”


“Does Mom know?” Michael wondered.


“No, and we should keep it that way.” she said sternly.


“Isn’t it, you know, cheating on Mom?” he said, starting to feel really guilty.


“Of course not, silly.” she laughed. “I’m not seeing any other women. Hell, Paul isn’t seeing anyone. What does it hurt if Paulina gets some ‘D’?”


“I dunno…” Michael wanted to take the easy excuse to ignore what his Dad was up to, that it wasn’t really him. But a part of him didn’t think a technicality like that really meant anything.


“I’ll share the pills.” She sat up and looked him in the eye, grinning from ear to ear. “I know you liked it, otherwise you wouldn’t have taken another pill. They cost a few hundred bucks each, and I’d be covering it. I’ll even get more when these are gone and share them with you.” His dad turned female lover was still smiling, but there was definitely a sense of desperation. It was pretty clear what she was thinking, that it would be awkward to try and explain any of this to May, and even worse to have to explain to the Judge at their divorce proceedings that would almost certainly follow.


Finally, Michael returned Paulina’s smile. He reached over and fished the pill out of his pants pocket. “Do you know what this pill will turn me into?”


* * *


The next few weeks went by excruciatingly slow. After the first week, Michael was hoping he would have another opportunity to take a pill, but his family was there all weekend. He couldn’t book a hotel room again, because he had failed to cancel his reservation and was already charged for the last one. Either he would have to wait another few weeks to do it again, or his family would have to leave.


During this time, he found that was also pretty uncomfortable being around his Dad, knowing what they had done. He tried to avoid seeing him at all, aside from the odd family dinner they had every few nights. None of the rest of the family seemed to notice the tension between them, mostly because it consisted of Michael not talking to his Dad at all when they had to be together and completely avoiding him the rest of the time.


Eventually, Dad came into his room after dinner on Wednesday night and kind of cornered him while he was in the middle of a game.


“Look, I know why you have been avoiding me.” Dad sat on the bed. “I get it. It won’t happen again… unless you want it.” Michael threw his headphones down and stood up, but before he could say anything, Dad continued. “Remember the timeshare that your Mom and I got? Well, I’m taking the day off on Friday and heading down there. It’s only a few hours down the coast. I’ll bring the pills.” He grinned. “I’m guessing you still have the second one and haven’t had an opportunity to use it. I know you’ve been thinking about it, though. I know I couldn’t stop. Still can’t....” his voice drifted off.


“I… haven’t had the chance, no.” Michael admitted. He knew he couldn’t deny that he had been thinking about it. Dad would see right through him.


“You want to come?” Dad asked, letting the double entendre just hang out there.

Michael sat for a few moments, feeling very conflicted. He knew what they had done was messed up, even if he accepted that what they did while on the pills didn’t count as gay, or incest, or anything like that, it still felt wrong somehow. Dad had cheated on Mom, at the very least. At worst, he had cheated on his wife with his son.


But it had been the sexiest experience of his life being a woman. And the sex with Paulina had been great. He was getting hard just thinking about it.


Michael finally returned his Dad's grin. "So what all comes in the variety pack?"


To be continued in part 3!


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