Em Brace
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I turned my boyfriend into a sizequeen!
🕑 Added 2025-08-09 11:04:16 +0000 UTCGirl turns her boyfriend into a sizequeen!
The following is just a fictional short story/fantasy I wrote. All characters are of my own creation and are well above the legal age of consent.
“You did what?!” My friend, Elizabeth asked me as we sat enjoying a coffee on a table outside a local bar.
“I turned Brad into a total sizequeen!” I said, triumphantly.
“Okay, you’re gonna have to explain a little more. When you say sizequeen, you mean like one of those girls who seeks out the biggest dicks she can find?” Liz asked.
“Yup! Somehow the subject of cock size came up and that led to him making some pretty harsh comments about girls who have sex with guys with big dicks. I think maybe he was just trying to justify his own cock size in his head, but he still pissed me off a little, so I decided to see if I could turn him into a sizequeen.” I said.
“Sooo how exactly did you manage that?” Liz asked.
“Oh well it wasn’t easy, it took me months! I had to be pretty sneaky about it, but once I got going I knew I had him.” I began my explanation.
“To start with, I had to convince him to try pegging. Luckily he’s always been happy to experiment with kinky stuff so after a lot of begging and teasing on my part I was able to agree to try it.”
“How did you manage that?”
“Oh I had to make a lot of promises, you know like ;you do this for me and I’ll do anything for you’ all that sexy stuff. I had to agree to buy a cheerleader outfit for him but that was a small price to pay. Of course he had to make sure he signed off on the size of the dildo I used, and of course he picked the smallest one he could find, but that was fine. I convinced him we needed to buy a butt plug to go with it, to loosen him up a little first, so we chose a nice small one of those too.”
“When we got home, I helped him get the plug into place up his ass, you should have seen his face haha. He was walking around all weird all afternoon, it was great! When we finally got to bed that night, I put on the strap on and removed his plug. I started off nice and slowly, gently thrusting in and out so he could get used to it. I made sure to pay lots of attention to his cock, made sure it was reeaally pleasurable for him, so he would be willing to try it again.”
“So that was all it took, a few sexy promises and you have a sizequeen?” Liz interrupted.
“No no, of course not. After the first time was done, I left it for a few days before bringing it up again. The second time took less convincing, I just needed to remind him how much it turned me on and how much he enjoyed it last time and he was willing to try pegging again. I made sure to repeat all the tricks from before, telling him how hot this was and how much I loved that he would let me do this, making sure to keep toying with his dick until he exploded all over.”
“So a few days after that, I asked him if he wanted to do it again, of course he said yes. He acted like he wasn’t into it but I knew he was starting to look forward to the pegging more than regular sex. So I took him upstairs to help him put in the plug to get him ready. What I didn’t tell him, was that I had secretly switched out his plug for a slightly bigger one.”
“Ahhh you went the old ‘boiled frog’ route then.” Liz interjected.
“Yep. And it worked a treat too. I could tell he felt the difference with the plug, but he didn’t say anything, the size change was probably subtle enough that he didn’t think much of it. Anyways, after walking around with the bigger plug in place all day, when it came time for the main event, the small dildo slid in much easier, I made sure he enjoyed this one just as much as the others.”
“After another week or so, I secretly increased the size of the dildo. Again he didn’t really notice the size change, he was just looking forward to the kinky fun we were having, plus he wasn’t used to me initiating so often, haha.”
“So did you just keep on secretly fucking him with bigger cocks?” Liz asked.
“Not quite. That’s how it started. After a few weeks and one more secret size change, I asked him if he wanted to try something a little bigger. Told him it would increase the sensations you know, reach a little deeper, stimulate him a little more. So he agreed, not knowing that he was already taking a bigger plug and dildo than he started with. So we picked out a bigger, wider plug and longer, thicker dildo to use next time. The plug met more resistance obviously, he made such cute little noises as I stuffed it up his ass. He walked around all bow legged for the whole afternoon until I took him to bed and took his ass again with the bigger cock. Of course he loved it!”
“So I’m guessing you secretly swapped out the size again a little later?”
“I did. I repeated the whole process over the next three or four weeks, before asking him once more if he wanted to try something a little bigger. He didn’t agree right away this time, but I kept up the teasing and pegging, making sure he was almost always horny and up for a little ‘fun’, until he eventually caved in again. ‘Okay babe, but just a little bigger this time, nothing too crazy!’ He said as I went online and found a new plug and dildo to use. This last plug was way bigger than anything he had taken before, and he was clearly intimidated by its size, but I was gentle and encouraging as I slowly lubed up his ass and stuck it up there. By the time he had spent a few hours being stretched out by the plug, he was ready for my new ten inch cock! He said it looked bigger than it did in the picture!”
“Hahaha, I’ll bet it did, you sneaky bitch.” Liz said, laughing.
“So that night, I made sure to rock his world with a huge ten inch rubber cock. It took a while to get the whole thing in there, but I managed it eventually. Oh you should have heard him moan as I stretched out his ass. If you haven’t tried pegging before, I would seriously recommend it. He was walking funny for half the next day. Anyway, I fucked him with the ten incher again a few nights later, he was still a little hesitant because of how big it was, but after I agreed to throw on the cheerleader outfit and suck him a little to get him in the mood he was ready to go again.”
“Wow, I can’t believe you actually fucked your boyfriend with a ten inch dildo. I’m impressed.” Liz said.
“And that’s not even the best part. I pegged him with the biggest size we had a few more times after that, always making sure to keep him teased and hard the whole time I was fucking him, maximum pleasure. Then I stopped. Just stopped talking about the strap on altogether, we went back to a little normal, mostly vanilla sex. I could tell he was missing having his ass filled, but I waited until he caved.
“‘Hey, you haven’t mentioned the strap on in a while.’ He said to me one afternoon, all sheepish like he was embarrassed to ask. ‘Awww is someone missing having their ass filled?’ You should have seen his face, all red and blushy. But it was obvious he wanted it. So I told him to get the big plug and put it in for a while, to get himself ready. Of course he was more than happy to. When we got to bed, I had him on all fours and told him to wait while I got the strap on. Only I didn’t grab the big one, I got the first one, the smallest size we had. You won’t believe how easily it slipped inside after weeks of taking bigger and bigger cocks. I made sure to only pay enough attention to his dick to keep him hard and wanting, without making it too pleasurable for him. It only took a couple of minutes before I heard a frustrated little noise coming from him.”
“‘What’s wrong baby? I thought you liked it when I pegged you?’ I asked him, all concerned like. You should have seen his face. I knew what he wanted to say but he just wouldn’t admit it. ‘Doesn’t it feel good anymore? Do you want to stop?’ I asked, that was when he finally caved. ‘No, don’t stop. It’s not that it’s just…are you using a smaller dildo?’ He said. ‘Yeah, I thought your ass might be grateful for something easier to take.’ I said, acting like I was all concerned. ‘Doesn’t this one feel good? You used to love it’. And then he said it. ‘I don’t think it’s big enough.’ I pretended like I hadn’t heard him, to make him repeat it a little louder. ‘It’s not big enough! Can you get the bigger one?’ His face was bright red as he asked.”
“Oh my god Char, you actually got him to ask for a bigger cock while he was getting pegged.”
“Oh I didn’t just get him to ask for it, I made him beg for it! ‘Tell me what you want baby, tell me what it is you need.’ He was too horny and desperate to care after that, so he just let loose. I need you to fuck me with a bigger cock. Please baby, fuck my ass with the biggest cock you have!’ I had done it. I obliged his request of course, I took out the ten incher and fucked him hard and fast until he came all over. I barely had to touch his cock at all. The best part was after, when he had cum and I pulled out and laid down next to him. I looked him right in the eye and said 'congratulations, you’re a sizequeen!’” I think that’s when it hit him, what I had done to him for what he said all those weeks ago. The look on his face was priceless.”
“Man you are so devious, I love it!” Liz said, finishing her coffee and getting ready to leave.
“I know, anyway he should be here any minute now, so I’ll catch up with you later, we may go shopping for a bigger dildo this afternoon.”
“Well let me know how it goes.” Liz said her goodbyes and headed towards the exit, at the same time I saw Brad, the subject of my tale, passing her on the way in.
“Oh hey, Liz.” I heard him say.
“Hey there ‘sizequeen’.” I heard Liz say as she quickly left the seating area.
The look he gave me at Liz’s greeting was fantastic!
End.
Comments
C
You could continue this in a feminization direction and it would be incredible. Turn him into a slut
Caged_Caroleta
Oh surly this has a few more miles on the story.......bugger dildo needs somehow for a chastity cage to go on....then of course each jump in size equals smaller cage 😈
