A/n- Continuing this series again! This one is a bit longer than the last two, I had a few more ideas for it! Enjoy Teddie getting pegged! XD
The Commission Files- File #a1546 Teddie and the Girls Part 3
Characters: Teddie (Persona 4), Chie (Persona 4), Yosuke (Persona 4)
Based on: a commission by marubokoo on Twitter/X
Teddie and Yosuke were eating lunch together on their couch, watching some random game show as they did so. They weren't really paying that much attention to it until one of the contestants, a young woman, had to kiss one of the other contestants, another young woman, for a challenge. This sparked something in Teddie's mind that he had forgotten about for a bit and he decided to tell Yosuke about it.
"Oh yeah, that reminds me." Teddie started out after slurping up his noodles. "What you said about Yukiko and Chie only liking sex with other women isn't correct. Yukiko told me that they are both...oh what's the word she told me...oh yeah bitextual!"
"I think you mean bisexual." Yosuke corrected him. "And huh, I didn't know that." There was a short pause before Yosuke shook his head clear and looked at Teddie intently. "Wait a second, how did you find out? How did you get on that topic with Yukiko?"
"When I was at the inn with her a few weeks ago." Teddie answered simply before taking another quick bite of food. "I figured that she was just lonely and invited me for company because of what you said, but nope, she wanted to have sex with me. And we did! Multiple times actually!"
"You little...!" Yosuke started off a bit heated because he was obviously jealous of his friend's ability to sleep with their other friends. "Jeez, when we all made that deal I never expected you'd get laid so much. I figured it was just a way to get you to ease up on the joking and they'd never use the other side of the bargain."
"Well, maybe you should start actually asking questions and learning the truth about things." Teddie suggested. "Both Rise and Yukiko both have told me that you're very misinformed about things you tell me. Maybe you should stop assuming things and search for the truth more often." He then chuckled. "Kind of like how we kept searching for the truth behind the TV world and the murders."
"Look at you, growing up so fast." Yosuke said a bit sarcastically, but deep down he would admit that Teddie was pretty right on the money with what he said. "I guess I've just been so busy with work I haven't had the time to keep up with everyone. I figured I knew it all, but what's life without change right?"
"Exactly!" Teddie agreed. "And it's not like you're starting at zero either. Just ask to hang out sometime or whatever, I'm sure they'll make time for you." After saying that Teddie's cellphone rang and this time he actually looked to see who it was. "Oh, it's Chie! I wonder what she wants."
"Well, answer it." Yosuke told him. So Teddie answered the phone with his usual energy.
"Chie! How wonderful it is to hear from you again! How's the police training going?" He asked with a big smile that could be heard through the phone.
"It's a lot tougher than I'd imagined honestly." Chie admitted. "Not a lot of time for kicking and punching, I'll tell you that much. But I'm learning lot of interesting things like how to search for clues and how to talk to suspects. I'm starting to feel a bit like Naoto actually. I wonder if she got any training like this or if she just picked it up naturally from her grandfather."
"Well, it's good to hear you're in high spirits!" Teddie replied cheerfully. "But I'm sure you didn't just call to check in on little old me. Is there something going on I need to know about? Yosuke is here with me too if it's something important."
"No, no, it's nothing like that." Chie assured him. "I was just wondering if you could come over to where I'm staying so we could spend some time together, doing certain things if you catch my drift. Are you free for something like that?"
"Yeah, I'm free." Teddie confirmed. "Did Yukiko tell you about the thing I wanted to try out?"
"She did, and that sounds totally fine with me, but you have to give me what I want first. Deal?" Chie asked.
"Deal!" Teddie confirmed.
"Alright, I'll text you the location of where I'm staying and keep my hand inside the TV so you can sense it better." Chie noted. "And make sure you're wearing clothes when you get here, I like to do a little foreplay to get myself ready."
"Sounds good to me! Should I come right away or should I wait a bit?" Teddie wondered.
"Let's say about 30 minutes from now, that should give me enough time to get ready." Chie stated.
"Alright, I'll see you then. Bye!" And with that he hung up. Even hearing just half the conversation Yosuke could tell what was going on, though he was trying to stay calm about it.
"Just don't come home naked again alright." He sighed before getting curious about one thing Teddie said. "What's this thing you told Yukiko you wanted to try out?"
"Well, she said that her and Chie have these belt-like things with fake shafts on them, and I wanted to see how that worked." Teddie answered like it wasn't strange.
"You want Chie to peg you?" Yosuke asked a bit in shock. "I don't know why I'm surprised actually, that totally sounds like something you'd be into."
"I know right?" Teddie agreed. "Well, I'm going to finish this food off and then head over to where Chie is. So don't wait up for me or anything." And that's what he did. About half an hour later he was walking through the TV world when he saw an arm with a familiar green and yellow pattern on it so he started walking towards it. When he got closer to the opening he stuck his head out to see what the room looked like.
"This is a pretty nice place they have you staying in Chie." Teddie noted as Chie pulled her arm out of the TV.
"It's nothing like back home, but it's suitable." Chie noted. "Do you need me to help you get through or do you have enough leverage from where you're standing?"
"I can get through, I just didn't want to surprise you too much." Teddie replied before pulling himself all the way through and dusting himself off. "Well, you've certainly decorated the place a bit."
"That was mostly Yukiko when she came over a while back." Chie explained. "But it does make it feel more like home." There was a bit of an awkward silence after that because Teddie was waiting for Chie to tell him what she wanted to do and Chie wasn't quite sure how to proceed. But eventually she got the nerve to speak up. "So, uh, how does this work exactly? Like how have the other two times went with you?"
"I'm here to do whatever you want me to Chie." Teddie explained. "So whatever you feel like doing I'll help you out with it! I'm up for anything!"
"Anything huh?" Chie mused, thinking about what she wanted to do. "Alright, I think I know where to start. Strip down to your underwear Teddie!"
"Your wish is my command!" Teddie replied enthusiastically before starting to shed his clothes. He was too preoccupied with doing it though that he didn't realize Chie was doing the same. So when he turned to face her again his mouth started to hang low for a moment for he got control of himself. "Wow Chie! Your training has made your body even more lovely! I really love how your stomach looks with those abs too, really strong and powerful looking!"
"You pretty good as well Teddie." Chie replied with a bit of a blush at Teddie's up front positivity. "I always knew you were handsome, but you really made that body of yours pretty well."
"Only the best for my wonderful friends and admirers!" Teddie said with cheer. "Alright, what now?" Chie bit her lip a bit in nervousness before telling him what she wanted him to do.
"Teddie, I want you to hold me close and start making out with me to start out." Chie told him eventually.
"Making out? Like kissing?" Teddie wondered. "Alright, but I have to warn you that I'm not very practiced with it. I didn't really do that much kissing with Rise or Yukiko."
"That's alright Teddie, I'd rather you start slow anyways. I like it when things like this last a while, that's why I called you here so early." Chie explained.
"Oh, that makes sense, you're the opposite of Yukiko." Teddie commented before stepping closer and wrapping his arms around Chie to bring her closer to him. "Well don't you worry, I'll take it nice and slow." And with that he tilted his head slightly and moved in closer to give Chie a tender kiss to start out with. "Is that good?"
"That's very good Teddie." Chie confirmed, her voice relaxing a bit. "Keep going, just like that."
"Of course." Teddie replied back softly before kissing her again. Her lips were maybe not as full and smooth as say Rise's, but Teddie enjoyed the feeling of them nonetheless. Chie for her part was surprised that with all the energy Teddie exuded all the time he could hold himself back like this and be so soft and tender. But he had surprised her before, and this time was no different. So they went on like that for a couple minutes just standing their kissing in each other's warm embrace before Chie spoke up again.
"You know Teddie, you can start using your tongue whenever you like." She noted. "And you don't have to keep your hands in the same place the whole time either. If you want to explore a bit that's fine with me."
"You're supposed to use your tongue when you kiss?" Teddie wondered to her.
"Sometimes." Chie confirmed. "Here, open your mouth a bit wider." So Teddie did so and Chie proceeded to kiss him this time, slipping her tongue into his mouth to show him what she meant. Teddie's eyes lit up when she did so and he got the idea pretty quickly as he had with the things Rise and Yukiko had taught him, and soon enough he was tongue kissing with the same confidence he had with everything else. And that wasn't all, he started moving his hands slowly all over Chie's body as well, feeling everything it had to offer. Of course he had to feel those abs of hers, but her arms and what he could reach of her legs were quite impressive as well. And his touch was so light and graceful that it was sending shivers and goosebumps all over Chie's skin. Eventually his hands landed on her back, right where the clasp of her bra was.
"May I?" Teddie asked slightly out of breath as he pulled back from their kiss a bit.
"Go for it." Chie replied. So Teddie slowly undid her bra and let it fall to the floor. At first he felt her breasts against his chest and her nipples tickled him a bit, but slowly he moved his hands around to Chie's front so he could fondle them properly.
"Mmmm..." He moaned playfully as he felt her up. "Your chest is much more firm and muscular than Rise's or Yukiko's. I really like the difference on how they feel."
"That's sweet Teddie." Chie breathed, blushing a bit again at his honesty. "I like how you're handling them, nice and soft like that. You've really surprised me and I'm really starting to enjoy myself."
"Then I'm doing my part correctly!" Teddie replied with more cheer before they went back to kissing more. A bit later Chie's hands started to drift down Teddie's chest and stomach and ended up at the edge of his underwear. She could tell he was really into all this since his dick was almost peeking out of the top.
"I think something down here wants to be free, should I let it be?" Chie teased Teddie.
"Probably, he's been so stuffed up in there, and not in the fun beary way." Teddie joked back before Chie slid his underwear down to reveal his very erect cock.
"Impressive, I can see why Rise and Yukiko enjoyed themselves." Chie commented. "Alright Teddie, I want to do something different now."
"Sure thing, what is it?" Teddie wondered. Chie didn't tell him at first, but instead turned around in his grasp so her back was against his chest now.
"I want you to rub your dick in between my thighs." Chie eventually told him. "I think you'll really enjoy the feeling of it. And we can keep kissing if you want to as well."
"Oooh, I can definitely do that!" Teddie replied enthusiastically. So Chie spread her legs a bit and Teddie slid himself right between her thighs before she closed them up again. He started thrusting like he would normally and Chie was right that it felt amazing. It was almost like the real thing except he wasn't inside her.
"Yeah, just like that Teddie." Chie moaned slightly as she felt Teddie's cock tease her clit and opening through her panties. "Go back to grabbing my chest too okay?"
"Of course!" Teddie smiled before placing his hands back on her chest before they continued kissing even more. Teddie didn't mind that things were going slow like this, he was just happy he could make Chie feel good and happy, just like with Rise and Yukiko. He did however have to slow down a bit himself or he was liable to go off prematurely. If Chie was the first girl he had been with he probably wouldn't have lasted long. Either way after a bit of grinding like that Teddie was wanting just a bit more so he moved one of his hands down to Chie's panties and looped one of his fingers around the elastic.
"I think it might be time for this last piece between us to hit the floor. What do you think?" He breathed into Chie's ear, making her shiver a bit.
"Do it." She breathed back. So Teddie pulled back a bit to get his dick out of the way before slipping the last piece of clothing either of them had on off. He then went back to grinding between Chie's thighs, though something felt strange to him. He was expecting her to be much wetter down there than she was. He was a bit concerned so he even used his fingers to feel her down there to make sure he wasn't mistaken.
"Chie, are you sure you're enjoying this, it doesn't feel like it down there." He wondered with some concern.
"I'm loving it Teddie." Chie noted. "Like I said, I like it when things are nice and slow and last a while. Well that's because it takes my body a bit to get ready for things like this, but once I am I can go for a long time. You're doing a great job Teddie, but I do appreciate the concern, it's very sweet."
"Well, if you say so!" Teddie replied trusting that Chie knew about her body better than he did. "Because I'm really enjoying this too, it's very intimate and romantic feeling."
"Good, I'm glad you're feeling good too." Chie noted. "Alright, onto the next phase! Teddie, I want you to lay on the bed on your back!"
"Okay!" Teddie cheered before jumping on the bed dramatically and comically and getting into the position Chie asked. He figured that she was going to get on top of him, but he didn't consider that she would be putting her butt right up towards his face. "Uhhh, isn't this the wrong way?"
"Not for what I want." Chie stated. "This is called the 69 position. Like this you can lick my clit and pussy to get me more prepared while I suck your dick to keep you hard."
"Is that why Yosuke always says 'Nice!' when that number comes up randomly?" Teddie wondered.
"Probably, knowing him." Chie replied, rolling her eyes. "But yeah, that's about it, any questions you have Teddie?"
"Nope, I think that explanation was simple enough." Teddie noted as he placed his hands on Chie's butt to keep the both of them steady. He figured he would just start and if Chie wanted him to go slower or faster she would tell him, so he slowly started licking her clit back and forth. It worked wonders because before she started sucking him off Chie let out some more and longer moans than she had been before. Not so surprisingly this was the first blowjob that Teddie had ever gotten so he was getting used to the feeling as well. The warm wetness of Chie's mouth reminded him of being inside the other girls, though her actions with her tongue were really what got him going. He quickly understood why a guy would love a girl to do something like this for him. It made him want to give Chie more so he started to lick her faster, slightly poking her opening with his tongue every now and then.
And that's how they went for another while, when Teddie would up his intensity then Chie would reply in kind and their moans continued to grow louder and longer with each passing moment. Eventually though Teddie could feel he was at his breaking point and he had to let Chie know.
"Chie! If you keep going on like that I'm gonna cum!" He moaned a little desperately. Chie didn't want him to finish just yet so she stopped sucking on him and shifted around so she could face him.
"Hah, that was great Teddie!" She breathed. "You're a really fast learner, I appreciate that! And I think I'm ready for you now because of it. Are you okay staying on your back like this?"
"I think so." Teddie breathed back. "Just give me a moment or two to steel myself so I don't go off the second I go inside. I don't have your stamina Chie."
"Of course." Chie assured him, letting him breathe for a few moments before she laid back on top of his body, teasing the tip of his still erect cock with her pussy. "Are you good now?"
"Yeah, I think I can last a bit longer now, though don't be disappointed if I don't last too long." Teddie noted.
"Hey, I've got you here all night right?" Chie asked. "And once I get going I keep going, so you'll have time to rest up. I even got some snacks you like to eat in between each time."
"Really? Wow, you're so thoughtful Chie!" Teddie beamed. "Alright, let's get started then!"
"I knew that would cheer you up." Chie chuckled before pushing herself down onto Teddie's cock and taking the whole thing inside her on the first go. She moaned loudly with satisfaction once again and once again they were off to the races. Again they started slow, but now that Chie was ready she was willing and able to pick up the pace quicker than before. Teddie had to put his hands back on her butt to keep her from falling off, but he had something else he wanted to feel dangling right in front of his face.
"Chie? Can I suck on your breast to see what it feels like?" Teddie asked through his moans.
"Go for it Teddie! I think you'll really enjoy it!" Chie replied. So Teddie moved his head slightly and started licking her nipple slowly at first, but eventually he put his mouth around it and started sucking on it like it was one of those drinks that come with it's own straw. He loved the texture and the slightly salty taste of her sweaty skin and it really got him going even more than before. "Ahhh, I told you it would feel good." Chie moaned as he continued to practically make out with her chest. Though as Teddie predicted he wasn't able to last to terribly long because of how Chie had been treating him before, and he was gonna let her know.
"Chie! I'm really gonna cum this time, I can't hold it in!" He said before doing just that! His dick twitched and convulsed and started to spurt his Shadow seed into Chie's body.
"Mmmm, that actually feels really good!" Chie moaned as she had a small orgasm herself. "I've never actually let a guy cum inside me like this. I guess that's just one of the many positives of you being a Shadow Teddie."
"I'm glad I could let you experience that." Teddie replied in a daze as he tried to catch his breath. "Can you get me some water though Chie, I'm parched."
"Sure thing Teddie, I'll even get some towels to clean up with." Chie noted as she got off the bed. She got Teddie his water and he drank it quickly before helping him clean off.
"Thank you." He breathed once it was done. "Oh, and don't worry about me taking a long time getting ready again, Yukiko told me that I do it much faster than most guys."
"That's great! Though I should give you a bit more time since you're gonna be trying something new." Chie noted.
"Good point." Teddie agreed. "While we wait, can I ask you a question about something?"
"Sure, what is it?" Chie wondered.
"Why do girls have breasts? Is it just for guys to play with and suck on, or do they do something special." Teddie asked.
"Oh, that's a simple one. Women's breasts are used to feed young children after they are born." Chie explained. "When a woman gets pregnant her chest starts producing milk for her baby, getting slightly bigger in the process. And when the baby is born it sucks on the nipples to get the milk out."
"Hmmm, so that's why it felt so natural to want to do so." Teddie mused. "I wonder if I'll ever get to taste it though, seems like you have to go through a lot of trouble to do so."
"Well first you'd have to get someone pregnant Teddie, so you're kind of boned right off the bat." Chie teased. "But there are some women who like having sex while their pregnant. Don't ask me where to find them, but they do exist."
"Eh, I'm not that interested in it." Teddie admitted. After that he got a few snacks in his belly and then felt like he was ready for more. "Okay, I think I'm ready now. What position should I get into?"
"Hmm, I think it would work the best if you were either on all fours or laying on your stomach, your choice." Chie suggested.
"I think I'll lay on my stomach, just so if my body does something weird we won't fall out of the bed." Teddie noted before doing just that. Chie watched for a bit before going and putting her strap-on on and also getting something else. "Oh, I just thought of something else to ask." Teddie commented when he felt Chie get back on the bed. "Since you have to stick that into my butt, do girls like buttsex or just guys?"
"Some girls like it, and some don't." Chie noted. "And some girls do it a lot because they don't want to accidentally get pregnant but still want sex. And just for future reference, just call it anal sex or 'anal' for short. Saying 'buttsex' is a bit childish."
"Ah, thank you for letting me know. Man, you girls know way more stuff about sex than Yosuke does, I'm glad I have people like you to help me learn." Teddie replied genuinely.
"Well, Yosuke could know more if he took the time to learn, but he doesn't." Chie commented. "Either way, let's start. Just like with me I need to get you ready down there first."
"At the risk of sounding gross, you're not gonna lick me down there are you?" Teddie wondered.
"Thankfully no, but be careful because some people are into that as well." Chie stated. "I have this lubricating oil with me and I'm gonna spread it around your hole and the shaft of my strap on. I'll make sure to use more than usual and go slowly since it's your first time."
"I appreciate that." Teddie noted. So Chie started to lube him up and he couldn't help but laugh because it kind of tickled when she did so. "That feels good, I can feel my skin softening up with that oil."
"Good, that means it's working." Chie explained. After that she lubed up her shaft and slowly got on top of Teddie, the tip gently teasing his entrance. "Alright Teddie, are you ready for this?"
"As ready as I'll ever be." Teddie answered with a thumbs up. So Chie slowly but surely pushed the tip of the strap on inside him, causing him to gasp for air at the action.
"You still good?" She asked afterwards.
"Y-Yeah, just a bit of a shock, that's all." Teddie noted. "I'm starting to get used to the feeling, you can keep going."
"Alright, if you say so." Chie replied before pushing inside a bit more. Teddie gasped again, but lighter this time. Then she pushed in more and he didn't make a sound. Then she pushed in the last bit and Teddie gave off a soft sounding moan of pleasure.
"Ohhhh, yeahhhhh! Right there is the spot!" He moaned some more and Chie could tell that he was quickly getting used to this like he had everything else.
"Like this?" She teased pulling back just slightly and then pushing back in again.
"Yes please!" Teddie moaned a bit louder.
"Certainly!" Chie replied before starting to thrust back and forth at a gentle pace. She hadn't expected Teddie to be this into this, but she was glad that he was enjoying himself. Eventually she felt comfortable enough to lay down on Teddie's back and push her chest against it while she could whisper in his ear. "How does that feel Teddie?" She teased.
"Heavenly." Teddie moaned some more. "This feeling is so different but it's also really exciting! I'm really glad you were willing to try this with me Chie!"
"What are friends for?" Chie replied genuinely. "Now the real question is, do you want me to continue slow like this or do you want me to go all out on you?" Teddie thought about it for a bit. Going slow was a good feeling and he would probably last longer that way, but if Chie started pounding him hard he'd finish faster and then he could go back to making her feel good as well.
"Show me what you can do Chie!" He said confidently. So Chie stopped being gentle with him and started going at him at the speed Yukiko liked her to keep when they did things like this. Teddie almost yelled in pleasure and he tried so hard to keep a hold of himself for as long as he could, but just a minute or two later he was cumming hard on the bedsheets. After that he and Chie cleaned up again, changed the sheets, and had some more snacks before going at it a couple more times. Each time Teddie lasted just a bit longer and he was glad for this type of stamina training Chie was giving him. Eventually though the two of them were too tired out to go any longer and all the water and snacks were gone so they ended up just cuddling in bed, looking outside at the moon and stars.
"Can I stay and cuddle with you tonight Chie, I don't feel like I can make it home safely after all that." Teddie asked as he felt sleep trying to take his consciousness.
"Of course you can Teddie, what's a fun night between friends without some warm cuddles?" Chie replied. "Especially with someone so good at bear hugs as you."
"Yay!" Teddie replied slightly weakly as he snuggled up to Chie and held her close. "Thank you for letting me come over and try new things tonight Chie, you're a really good friend."
"So are you Teddie, you're willing to come over and do strange things with me and Yukiko and we really appreciate that. You're a special guy Teddie." Chie said back before turning to face him and placing a kiss on his lips. Not a making out kiss or a friendly kiss, an actual slightly romantic kiss. "Just make sure you're still here in the morning, I might have something else special for you."
"Of course, what are good friends for!" Teddie whispered back. "Goodnight Chie, have some beary sweet dreams."
"Goodnight Teddie, you do the same."
