For Pete's Place Pt. 04

This is a continuation of a previous story, so I'm anticipating that you've read that as well. But just in case you need a reminder, or for some reason decided to jump in here, this story takes place in a cumshift world. Details about that can be found in my essay about the world rules. This chapter will finally start to see the cumshift world become relevant. Beyond that, also remember that Pete's deal is that Alex is basically a sex toy in exchange for Pete's supporting him, but he only ever demands to cum once per day at Alex's hand, as well as once in exchange for the unlocking of Alex's cock cage.

Thanks to everyone who reads

-AR2

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If you had told me six months ago what my life would be like, I might have believed you. I also might have told you to fuck off, but I understood the very real possibility that I could end up right where I am. The real surprise is that if you told me I honestly wouldn't mind where I am right now, then I would definitely tell you to fuck off, and I might even pick a fight over it. I was very certain that I was only interested in women who had already crossed over, and I was not interested in crossing over myself.

Strictly speaking, that was still true. I was interested in crossed-over-women, and I didn't really want to cross over myself. But after six months of Pete's deal, I was beginning to show the first signs of crossing over, and as much as I didn't want to admit it, I wasn't actually hating it. And, although I wouldn't admit it, sex with Pete wasn't the worst thing in the world either.

The only reason I bring this up now is because, like I said, I was beginning to show the first signs of crossing over. And I only know that because someone else explicitly told me as much.

Pete went out of town for a couple days for some big thing which meant two things: first, he would want big payments before he left and as soon as he got back and second, I had the place to myself for the first time in a while to try to get laid.

I got ahold of Ash, whom I had met months earlier, and let her know the situation. We had reconciled since she believed herself to be the reason Pete had started using a cock cage on me and thus why I now had to occasionally pay him an additional time every few days to remove the thing. We hadn't really said we would hook up again given the chance, but I felt it was a strong possibility.

She came over that night, and with almost no preamble, we were making out. Ash dropped to her knees and took my cock into her mouth, sucking on it until it was good and hard. It had been a long time since my dick was pleasure in any way, in fact I didn't even masturbate with the thing much anymore. I was raring to go, and the well-missed sensation of being sucked off was more than I thought I could handle. Or at least, I thought so for a while.

Ash was sucking my dick for half an hour or more when I decided we were getting nowhere. I was almost disappointed to stop her, and somehow I knew she was also disappointed for having failed to get me off like that too. But rather than lose momentum, I escalated. I pulled her up off the floor and turned her around, pressing her up against a wall. I lifted up her dress, pulled her panties to the side and slid my hand between her legs o gauge her wetness.

She had certainly been wet, likely in anticipation of a quick bj and then some good fucking, but after the delay, she had apparently dried up some. I couldn't have that, so I reached forward and found where I guessed er clit should be and began to massage it for her. She began to moan and her wetness soon returned. As soon as I thought she was ready, I took my cock in my hand and guided it into her.

It felt amazing to be inside her again. I should have brought a condom, because I really wanted to just stand there and fuck her until I busted, and I didn't want to pull out this time. I needn't have worried about it. 10 minutes against the wall got us no further. It felt amazing, but honestly, I was just having trouble getting over that final rise.

We took a break for a while and pulled on enough of our clothes to have dinner. Then we went to the bedroom and laid down to watch tv until the mood hit us again. It didn't take too long. Ash started tracing little circles on my thigh, moving closer and closer to my crotch as she did so. This got a little rise out of me, but I played cool as she got her hand all the way to my dick and started stroking it as it grew in her hand.

Neither of us looked away from the tv as I reached over and began to massage her clit as well. I could tell she was already wet, so I ventured my hand further down to start fingering her, using my palm to continue rubbing her. After a minute or two of mutual masturbation, we turned toward each other and started making out. I rolled on top of her and we tried again to have sex.

She guided me into her and I began to thrust. My hips slapped against hers, but like before, after a certain point, I just couldn't get any further. An idea struck me, and I reached for the bedside table. As discreetly as I could, because I honestly would rather Ash didn't know, I pulled out the dildo and slid it behind my back. I found my asshole with it and, as covertly as I could, slid it in.

Ash caught on almost immediately.

"Is that...Are you fucking yourself with a dildo?" she asked.

"Well, I-" I started. Knowing I couldn't lie, I continued. "Yes. I'm sorry, it just helps me...you know..."

"No, it's fine!" Ash insisted.We had stopped fucking and she squirmed her way out from under me. "Really, I get it. I just thought that...well, if you were going there...Well, you seemed to be having trouble so I had an idea." She fidgeted, not making eye contact as if she had already said an embarrassing idea and was awaiting my approval.

"What?" I asked earnestly. "What's your idea?"

"Well," She said, getting up. She walked over to a cabinet I didn't use and started fishing around. Apparently she still remembered Pete's system after all this time, but I had no idea what she was going for. "I thought we could use this, if it'll help." She turned around with a device in her hand, that I eventually recognized as a stap-on.

The toy part was probably about the size of a regular cock, and I could guess how the straps sat as Ash started to pull them on. There was something on the inside too, what looked like a smaller dildo. I was able to deduce that it was some kind of vibrator or clit-vac stimulator when she turned it on and had to stop to catch her breath for a second.

I was anxious about the thing. Getting fucked by a girl, not ridden but actually fucked with a strap-on, was not something I had ever wanted. Why would I? If I were having sex with a woman, I would want to penetrate her, not have her penetrate me. That said...I had just slid a dildo up my own ass, and she was offering me exactly that. And she was offering to fuck me with it, which would not be unlike Pete fucking me with his cock I imagine, and that was something that...well wouldn't say I enjoyed it, but it did make me cum pretty consistently.

I let Ash get all the way to the bed, crawl in behind me, and take my dildo out of my ass. She lined her own dildo up and slide it into me, and the idea never once crossed my mind that this wasn't one of Pete's payments, I could say no to this if I wanted to. But the thing is, no I didn't want to.

The strap-on easily reached my prostate and the familiar pleasure of being filled wiped my mind of anything not related to orgasming. Ash began to slam her hips into mine and I heard her moan as loud as I did as the toy inside the harness gave her pleasure equal to what the toy outside was giving me. Every few pumps, she would bury it in me and let it sit for a second, and I could feel the residual vibrations from her side of the toy reaching up the end of mine and tickling my prostate before she continued ramming into it.

She had her hands on my hips to plow into me and suddenly twisted them sideways. I rolled over onto my back and she repositioned herself. She hiked my legs up and found my hole again before pressing into me. I gasped when she re-entered me. She let the strap-on sit deep inside me, letting me feel the vibrations running up its length.

And then she began to fuck me again. Pete had fucked me in this position before, and it was good in its own strange way. But looking up at Ash, a beautiful woman, as she fucked me was surreal. We were having sex and I was enjoying it, in fact I was loving it, but she was the one penetrating me. Something about it just seemed wrong in my head, like a wire was crossed somewhere.

But that didn't stop me from enjoying it, because before long, I was finally ready to cum. Like most guys, I usually cum before the woman I'm having sex with, but this time, surprisingly, I didn't. Instead, something that never happened to me before happened, and Ash and I came at the same time. Ash's eyes rolled in her head and she moaned as her climax overtook her, letting the the strap-on buzz gently against my prostate as my cock started to spray cum onto me.

Almost immediately, Ash began to grind into me again, and I was mostly ready for it. But I decided to take a new position, one I hadn't tried yet. I did my best to wrap my legs around her and gave her a twist of my own. She was still coming down from her own orgasm and I moved her pretty easily. I got her onto her back and postponed myself on top of her. If I was going to be the 'girl' in this exchange, I could at least try as much of it as I wanted. And this way I wasn't giving in to Pete, or so I told myself.

It was odd trying to ride Ash, even more so that I was doing it anally as it's not a very natural position at first. I got the hang of it though, and we were both moaning in pleasure before too long, not that I understood if or how my actions correlated to her enjoyment. Still, Ash climbed through her second and then third orgasm beneath me, and I finally reached my own again. My cum shot up into the air before falling back down on both of our stomachs.

I continued to ride for a while after that, but we were only able to get Ash through her fourth orgasm before we both ran out of energy and collapsed. She pulled off the strap-on and turned it off so it wouldn't bother her as we snuggled up to each other. We shared a brief, tender kiss before starting to doze.

"So you're change over is coming along nicely," Ash said sleepily.

I was too exhausted to be defensive, so instead I asked, "What do you mean?"

"Well, you cum from anal now," She started.

"That's not really fair, that's Pete's fault," I said, explaining the whole thing about the cage and having no other way to masturbate.

"Ok," she said in the way people who don't buy your argument but have more points to make say. "Your body is also starting to change. Your dick is probably about an inch shorter than it was last time we had sex. And it's definitely not as thick either."

Now I got defensive. "Well I can't control that, you know Pete dumps a load in me at least once a day. I'm not exactly happy about losing ground in that area either, you know I wasn't breaking any world records."

"It's fine, you're still plenty good with it," she said kindly. "Your body is also slimmer, which was convenient to grab hold of." She ran her hand along my hip and I let her because as much as I hated the idea, it did feel good to be caressed.

"Maybe I'm just eating healthier," I offered.

She gave me a look that said she knew even I didn't buy that. "And your tits bounced when we were fucking."

I was silent for a moment. That was not something I was ready to hear. A shrinking dick sucked, but it was still a dick. Slimmer body I could pass as being in shape for a while, even if I knew it wasn't. But having tits was a distinctly feminine trait. "I...I have tits?" I asked sheepishly.

In answer, she brought a hand up to my chest and cupped one of my pecs...one of my tits. It was definitely small, barely budding, but I knew that's exactly what it was. I could somehow tell from the way it sat in her hand. I had tits now.

I jumped out of bed and rushed over to the bathroom. I had to see myself in the mirror, really look at myself for the first time in a while. I knew Ash wasn't lying, but I had to see for myself. And she was right. It was all just beginning, and I could easily pass for still a man, but knowing what I had been the changes were noticeable.

First, my alleged tits. I confirmed they were there and Ash came up behind me. She reached around me and put her hands on them again.

"You should probably start wearing a training bra," she said, giving them a little fondle. I hated to admit it, but she was probably right. If they grew too much more, I thought they would probably start poking out of my shirts. "I thought I saw them poking through your shirt earlier. I might have imagined it, but I thought I saw them bouncing under your shirt too." Well never mind, there was that.

Ash ran her hands down my body and her hands dipped in ever so slightly at my waist before smoothing back out at my hips. She could definitely grab on to those for leverage, which explained why Pete had had such an easy time of it recently doing exactly that.

Ash ran her hand in along my body until she got to my dick and wrapped her hand around it. I had started to go limp by the time we got to the bathroom, but Ash's hands had gotten me hard again. Disappointingly, rather than the whole head poking out of her hand, now I could just see the glimmer of my precum in the darkness of her closed fist. I didn't want to admit, but I had actually probably lost about two inches judging by that metric.

We didn't have sex again that night, but Ash did show me where the bras were and taught me the organization system. She helped me pick out a training bra and put it on, and then we went to bed.

We had sex a few more times over the next couple days. The last time, I had Ash lock my cock up before we did. It intensified my orgasm a bit, but otherwise didn't change much. Ash left before Pete got back, and he didn't seem to notice anything. Not about Ash being there at least. He pretty quickly guessed that I had started wearing a training bra and when he went for anal that night, he saw my caged cock on full display.

Pete loved the bra, obviously, and it took him no time at all before he was insisting on seeing the bras I was wearing or picking out the bras I wore while servicing him. Honestly, it's kind of surprising he hadn't ordered me to wear a bra sooner, not that I was complaining. He was certainly making up for lost time now though.

I never knew there were so many styles of bras, I'd never paid any attention to them before. They were always just an obstacle before, and now they were a part of my wardrobe. And, not that it should have come as a shock, they actually felt really good to wear. Most style were really comfortable, and the ones that weren't were specifically designed to be sexy. And add it to the list of things I wouldn't admit, I actually really liked those too for some reason.

So that's where we sat a month later when Pete had his Million Dollar Day. I don't know if I've brought it up before, but I really don't understand exactly how it is Pete makes money. I know he trades stocks and crypto and I think he at least partially owns a few small businesses? Anyway, I woke up one morning to Pete celebrating like crazy. Apparently, across his various ventures, he had managed to pull in more than one million dollars in the last 24 hours. He dubbed it his Million Dollar Day and decreed we would celebrate.

And I of course was going to celebrate right along with him, not for a second considering the ramifications.

That weekend, Pete threw a huge party to celebrate. He made a demand of my outfit on Saturday that was a brand new kind of brand new. He actually told me about it on Friday, running it by me in case I decided I would rather move out than participate. Not that there really was a choice there. I still had nowhere to go.

So Saturday morning, I was woken up by Pete and two of his friends. They were pretty girls, but they were here on business. They brought me into the bathroom and set to work. They stripped me down and bathed me, which would have been hot if they had taken their own clothes off and joined, or if Pete hadn't watched the whole thing. They lathered up and shaved every inch of my body besides my scalp and eyebrows. I'd never seen such a smooth cock outside of porn. It was kind of unnerving actually.

They gave me an enema, which I have to say was probably the weirdest experience of my life. I assumed that meant Pete was going to fuck me right after, but no one replied when I jokingly brought up the topic. They rubbed lotion into my body, which again would have been hot in other circumstances. Then they gave me a manicure and pedicure. Also weird, but I have to say I kind of enjoyed the way my hands and feet felt afterword. I wasn't super crazy about the neon paint they covered my nails with though.

Finally, they moved to my head. They brushed my hair, which hadn't been cut since I moved in with Pete. They straightened it, and I found out it went down to my shoulder blades. They pulled my hair away from my face and started doing some make-up. It felt like it took an hour or two to apply it all, then they went back to my hair. They put a wavy wobble in it and then said I was done, with my body at least.

They moved on to clothes, starting with the most intimate. At Pete's special request, and for only the second time ever, they locked my cock up in a cage. Actually, they undid the cage and downsized when they saw how my cock fit in it, which was a bit of a blow to my pride. They put a butt plug up my ass, another new one, this one bigger than the one I usually used and with a glimmering head.

They pulled out a skimpy lace thong, dark black, and slid them up my legs. A matching black, barely-there bra supported my budding breasts. They put a pale white crop top on, one that barely covered my bra and was light enough to be practically see-through as far as my bra was concerned. They put me in a mini-skirt that left my ass almost completely exposed and pulled up some fishnet stockings that should have gone high enough to disappear under a skirt if it had any real length to it. They finished the look off with some neon pink converse sneakers and finally let me see myself in the mirror.

I was...pretty cute actually. Not that I needed to say it again, but I was a man and I had no intention of changing over and becoming a woman. But the girl looking back at me was...well, I would have hit on her. She was definitely asking for it and I had to stop myself from reflexively trying to flex for the babe in the mirror. It was so strange to think that that was me.

The girls made sure I got a good look at myself all the way around (since when did I have such a juicy ass?) before letting me go. They showed themselves out, promising Pete they would appear later that night. Pete took me in in all my glory. He grinned and catcalled and generally looked like a guy checking out a girl. It felt strange to have someone look at me in that context, even stranger to feel that I actually like the way his eyes lingered on my body.

I figured Pete probably wanted to be paid right then and there, but no. He went about his day preparing for the party. I was somewhat anxious as the day wore on and Pete never came to collect his payment. Pete never missed a day, if he was home, he got paid. But the party was fast approaching, and he made no such demands. Meanwhile, I got surprisingly comfortable with my outfit as I walked around the house and felt Pete's eyes on me.

And then the first people started showing up. I was a little shy at first with new people and new eyes on me, but they all seemed either already aware or able to quickly adjust to mine and Pete's arrangements. Many of them checked me out, but most went about the party as if I was wearing jeans and a t-shirt. Before long I got used to their presence and looks too. I probably should have been super uncomfortable with it all, but I found I actually kind of liked the attention. A few beers and a shot or two also helped.