A/n- I really love writing Matthew/Leila, they just have such an energy I love, even if some of it is just my headcanons. Either way this happens in a modern AU since I'm pretty sure No Nut November wasn't a thing back in medieval times. Also, since the date is getting close, once Engage comes out this series is probably gonna go a bit dry since I'll be playing that with my free time, plus Persona 4 and 3 come out the day before and I want to play those as well, but after that I should get back to writing.
The Commission Files- File #254 Temptation
Characters: Matthew, Leila, Mark
Based on: a commission by henchan45 on Twitter.
The date was November 30th and Matthew, Mark, and Hector were hanging out at Hector's house. They didn't have classes tomorrow, but even if they did Hector lived pretty close to the campus of the college they all went to. It was about 11PM when Mark got a message on his phone.
"Hey, I gotta take this real quick." Mark said getting off the couch and handing his controller to Matthew. He went into the kitchen and called the person who messaged him. "This is Mark, are you in position?"
"Yes, everything is set for my little 'surprise' I have in store for him." The woman on the other end replied. "Are you sure you can get him back here in time?"
"Yeah, of course." Mark said confidently. "I kind of tipped Hector off to it and he's helping. I didn't tell him the specifics or anything, just enough so he'd help."
"Good. And thank you Mark, I appreciate you doing all this for me." The woman told him.
"No problem, I may think No Nut November is stupid, but if it's gonna help a friend pull a prank and end up making a funny story, well how am I gonna say no to that." Mark noted with a chuckle. "I'll let you go and get him over there ASAP though. Have fun with him." And with that Mark hung up and went back into the living room with the other guys.
"Who was it?" Hector asked, playing along.
"It was Lyn." Mark lied. "She needs me to come over to her place for some reason, so I gotta dip. Sorry guys."
"Hey, not a problem." Hector noted. "I actually have a date early tomorrow so I was gonna hit the hay soon anyways."
"I guess that means I should get going as well." Matthew said standing up and stretching a bit. "Thanks for inviting us over Hector, I had a good time."
"Yeah, me too. Don't be a stranger you two." Hector told the pair before they left. But before Mark and Matthew parted ways Mark tossed Matthew something small.
"Here, you might need this tonight." Mark joked before hurrying off. Matthew was a bit confused and didn't have time to respond before Mark drove off. He was even more surprised when he saw what the item was.
"A condom? Mark, you are so weird some times." Matthew commented to himself before he got into his own car and drove back to the dorm rooms where he lived for the time being. When he got to his room he shared with his friend Guy it was shortly before 11:30. He opened the door quietly, knowing that Guy liked to go to bed early, and tried his best to move around the room in the dark silently, which he was pretty good at all things considered. He made it over to his bed on his side of the room and flipped on the light that he had on his nightstand. It was safe to say that he wasn't expecting what he saw when he did that.
"L-Leila! W-Why are you here? And why are you naked?" Matthew stuttered as he took a few steps back. He accidently tripped over something and flopped down on Guy's bed, feeling that he wasn't in the room with them. "And where is Guy?"
"What? Can't your girlfriend come over and give you a surprise every now and then?" Leila teased him. She was just laying out on his bed, letting everything show without any shame in her face or voice, which was pretty normal for her in all honestly. "As for Guy, a friend of ours set him up with a date tonight and he shouldn't be back any time soon." Said friend was of course Mark, who had set him up with his friend Priscilla who was looking for someone to meet.
"Okay, that all makes sense so far." Matthew said sitting up in Guy's bed, trying really hard to not look at Leila's hot and sexy body but failing. "But you know the date, we still have our little bet active, at least for the next half hour or so."
"Oh, I'm quite aware, and I'm quite impressed that you actually made it this far into the month." Leila teased him any more. "That's why I want to take things to the next level. I'm willing to go double or nothing on our bet, but you have to play along for it to count."
"Double or nothing eh?" Matthew wondered. They had bet that whoever won the bet, whether Matthew could actually get through the whole month without having sex or jacking off, wouldn't have to pay for their dates for the next month. Matthew was actually in the process of saving up for an engagement ring, so the extra money would be nice, but could he handle it, even for a few minutes. "What would I have to do?"
"Get naked and let me have my way with you." Leila responded confidently. "By the time you do I'd say I'd have about 20 minutes to work you over. If you don't cum then you'll win, but I can do anything to get you off, including sex."
"And when the clock hits midnight?" Matthew wondered.
"Then we can fuck all night without restraint, kind of a win-win don't you think?" Leila asked. "But that's if you accept, I'm not laying here naked for 20 minutes not doing anything, as much as I love teasing you."
"Well, since you went through all this trouble, I guess I could go along with it." Matthew replied with a smirk as he started to undress. "But don't think I'll be an easy mark, you're gonna need to pull out all the stops." Quickly he was naked as well, and as much as he didn't want Leila to get confident seeing it, he was actually pretty hard already.
"Oh, I'm sure I will, now get over here and sit on the edge of the bed." Leila ordered him. So Matthew did as he was told and sat on the edge of his bed. Leila got off the bed and kneeled in front of him, looking at his erection with a smirk. "So hard already, you really love seeing me naked don't you?" She teased him before beginning to stroke him up and down gently with her right hand.
"Hey, what can I say, having a woman as sexy as you as my girlfriend is quite a boon." Matthew replied before beginning to moan slightly at her touch. "It doesn't hurt that you're willing to do so much and experiment as well."
"Well, it's just because I like you so much." Leila told him with a wink, which was actually true. She felt very comfortable and safe with Matthew since they had been friends ever since middle school. With anyone else she'd be much more introverted and closed off, but she could be herself with Matthew.
"Lucky me." Matthew winked back before Leila started to get a bit serious. If he was being honest with himself Matthew could just cum right here and be over with it, he was really pent up and having Leila right there like that and knowing if he did he could just get to the good stuff faster was tempting, but he had a bit of pride in himself and he had a reason to try and win this bet. So he was going to hold on as long as he could.
"Hm, I honestly thought you'd give up here." Leila teased him after a bit. "Well, let's see how you handle this." And with that she moved her hand away from his shaft and then moved her chest in to replace it. She adjusted herself so his cock was safely between her breasts before wrapping them around it and starting to move up and down.
"Gah, so warm!" Matthew moaned when she started to give him the titjob. This was another thing he missed. Since the weather had been getting colder he missed just getting to lay in bed with Leila after sex, or just feeling the warmth of her body against his as they were intimate with each other. But he gritted his teeth and held on for a bit longer, even when Leila started to rub him even faster and harder. She even was giving his tip a little kiss each time it popped up out of her breasts, which was really hard to hold back from.
"You're being a bit stubborn tonight aren't you?" Leila asked, practically talking to Matthew's dick and not to Matthew himself. "Too bad for you I'm not even close to being done." So it was time for Leila to kick it up yet another notch. She moved her chest away from Matthew's dick and then moved head in closer, sticking her tongue out and sloppily licking the shaft up and down just how he liked it.
"Gods damn! I know it's just because I'm sensitive from not doing this for a month, but damn!" Matthew groaned as he had to lay back onto the bed and grasp onto the sheets to hold on for dear life.
"And just think, I'm a month out of practice too." Leila teased him before moving in even closer and taking his shaft into her mouth. And she was telling the truth about that. It could have been easy for her to hook up with someone else during the month, especially since everyone in the area had an unwritten rule that casual sex with Mark and/or Lyn didn't count as cheating, but she didn't really feel that was fair for Matthew. Of course she pleasured herself a few times, but that was different since the bet was for Matthew not to get off, not her. So she had been looking forward to this night ever since she planned it with Mark a week ago.
"You have to be lying, your mouth is feeling as good as ever." Matthew groaned again after a while, gritting it teeth right after.
"Think what you will Matthew, but you know that you're the only man for me." Leila responded when she stopped to take a breath. She looked over to the clock on Matthew's nightstand and saw she still had another 10 minutes to go before midnight. "You don't happen to have a condom on you anywhere do you?"
"There is one in my pants pocket, Mark gave it to me for some-" Matthew stopped midway through his sentence and sat up to see Leila bending down and searching through his pants, her ass looking nice and full as always. "You two planned this together didn't you?"
"Perceptive as ever aren't you?" Leila teased him turning around and opening the package to the condom. "But yes, Mark helped me come up with this idea and how to implement it. Didn't even ask anything from me in return."
"Mark is a strange guy." Matthew commented. "But I guess he's a good friend so it balances out."
"He also is a treasure trove of sexy techniques, like this." Leila replied before putting the condom in her mouth and kneeling down in front of Matthew again. She started blowing him once again, but she expertly slipped the condom onto his shaft as she did so, not cutting it with her teeth even once.
"H-How did you learn to do that?" Matthew moaned, laying back on the bed again. "You've never done that before."
"Well, I had a bit of trouble finding a cucumber that was the size of your dick, but after I did just practiced with it until I got it down to perfection." Leila responded as she stood up, confident that the condom was on correctly. "But do you really want to hear about that, or would you rather be feeling this?" She added before turning around and slowly squatting down on Matthew's dick, slowly allowing it to slip into her pussy. She spread her legs and went into a kneeling position on his legs so he could get as deeply as he could and she put her hands out onto the bed to keep steady since she felt Matthew wasn't going to hold onto her because it would cause him to go off.
"You're the Devil! I'm dating the Devil in disguise!" Matthew yelped out, saying the first thing that came to his mind so he wouldn't just immediately cum from the feeling of being inside Leila's body after a month away from it.
"I'll take that as a compliment." Leila teased him before starting to bounce up and down on his cock. She was used to Matthew bucking his hips and grabbing hers to make it feel better for her, but it wasn't happening. Matthew wanted to do those things of course, but he knew the second he let himself go and start enjoying this to the full he was gonna explode in more ways than one. "You're really holding on for this long? You must really want to win this bet. What's got you so determined tonight?" Leila asked, looking over to the clock and seeing she only had about 3 minutes left before midnight.
"I'd love to tell you Leila, but it's a bit of a secret." Matthew strained out. "Just know that I'm trying to save up some money for something, and winning this bet will go a long way to that. And that it's something I'm pretty sure you'll enjoy."
"You, keeping a secret from me?" Leila mused. "And going this far to keep it? Must be important. Let's see if I can get you to spill the beans anyways." After saying that she lifted herself off of Matthew's dick, took the condom off of it, and then slammed herself back down on his shaft, much to Matthew's surprise.
"L-Leila, why did you do that?" He wondered through his moaning and groaning in pleasure. "Is it even a safe day for you?" Leila just chuckled slightly darkly at his concern.
"Looks like I've kept another secret from you." She teased him. "I've been taking contraceptives for the last couple months. So you don't have to worry, you can cum and fill me up as much as you want."
"But why?" Matthew said with a gasp, trying to hold on for just a few more minutes, his hands hovering around Leila's hips, ready to hold her down and fill her up to the brim with his seed. "This can't be for the bet if it's been for this long."
"Because, I've heard through the grapevine how you've been wanting raw, unprotected sex with me." Leila replied, turning up the jets even more. "And I finally decided I trust you enough with that to do it. I just wanted to spring it on you at a good time and this seemed to be a good time."
Matthew didn't have time to think right now about who would have told Leila about his desires, he really didn't have much time to think about anything at the moment. He quickly glanced at the clock and saw it was 11:59, he only had a few seconds left to hold on and he was going to do it. But Leila wasn't going to stop either, she started bouncing as fast as she could on his dick, shaking her hips on the way down to hit all his sensitive spots along with her own. She was actually on the edge of cumming as well and she knew if she felt Matthew go off she would as well. The last few moments before midnight were full of tension, but what Leila didn't know was that Matthew had set his alarm to go off at midnight, so when the clock struck the next day she was quite surprised. So surprised that she got so distracted that she came right then and there, tightening up around Matthew's shaft.
"MATTHEWWW!" She moaned out in the moment.
"LEILAAAAAAA!" Matthew moaned out with her, finally grabbing her hips and pumping his seed as deeply as he could, the tip of his dick kissing the entrance to her womb and flooding it with all his hot and sticky cum. It was pretty much a perfect intimate moment between the two of them, and Matthew finally had come out on top for once, sort of. Leila was still in control as usual, but he had won the bet. But he wasn't going to rub it in because for one his mind was too blank to do so, and for two it would be kind of rude after Leila set all this up just for the two of them to share. Eventually Leila's body slowed down and she stopped bouncing on Matthew's dick, allowing it to slip out and rest between her legs shortly before she turned around and laid down on Matthew's chest, resting her head in the crook of his neck.
"Looks like you won." Leila said with a heavy breath as she cuddled up with him, enjoying the warmth between them since she had been missing it as well.
"Just barely." Matthew replied, similarly out of breath. "You really pulled out all the stops Leila, and I have to admit it was pretty hot. You even caught me off guard with that last one. You really started taking the pill for something I wanted?"
"Yeah, of course I did." Leila noted. "I love you Matthew and I want to do things that make you happy. I know I tease you a lot and everything, but deep down I think you are a wonderful man and boyfriend and I'd do a lot for you if it meant making you happy. Because you are at your best when you're happy. You're silly and charming, clever and a genuinely helpful person. And I love that about you.
"You're so amazing." Matthew said softly. "You're so confident and put together, and you fell for a guy like me. Well, as I always tell you, I'd do anything to make you happy as well. Not just because you're also your best when you're happy, but just because I like seeing you like that. You're more outgoing, you show me your sensitive and vulnerable sides, something that no one else gets to see, and that makes me feel special. And I love that about you.
"Well, you did quite a bit of work to worm yourself into my heart, even if you didn't realize it at first." Leila teased him. "But yeah, you make me feel safe enough to bare my heart to you, and you're the first person outside of my family that I've done that for. So consider yourself special, because I know I do."
"Hmm, thank you Leila, that really does make me feel special." Matthew replied, holding her a bit tighter against him. "So, were you being serious when you said you wanted to fuck all night?"
"Are you kidding, I haven't had you in bed in a month! We need to make up for lost time!" Leila noted with a smirk. "I'm draining those pent up balls of yours until you can't go anymore!"
"I feel like I'm in danger." Matthew joked as he gulped from intensity of her words.
"Don't worry, I'll be gentle. To start out with." Leila teased him. "By the way, are you gonna tell me your little secret? The one you need the money for?"
"Eventually." Matthew replied with a smirk. "Give me about two months, and then I think I'll be ready."
"I'll keep you to that." Leila noted with a wink.
"I hope you do."