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Published:
2021-11-11
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2023-01-12
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11/?
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BL Prompt Requests

Chapter 6: Leon/Pob - First Time Pt. 2/2

Notes:

Prompt: Can I please ask for a LeonPob story from Don’t say no the series. Could you write a more detailed story about their first time based on the show?

(See the end of the chapter for more notes.)

Chapter Text

For Lilylove

Pob is now feeling a little brave after his orgasm moves to strandle Leon. He swings one of his legs over Leon’s hips. His dick lay soft next to Leon’s still hard cock. He makes eye contact with Leon and he can see the same expression from before filled with desire. With both of his hands he grabs his boyfriend’s hardness. And strokes him just like Leon did to him before.

Since he has no experience trying to pleasure anyone other than himself he touches Leon how he would touch himself. He grips the base of his cock with and strokes him up and down. The motion causes a bit of precum to spit from the tip. With Leon groaning beneath him Pob uses his other hand to play with the precum on the tip of Leon’s cock spreading it around the head. Leon moans even louder and his hands move to grip Pob’s hips.

Pob continues to stroke him and uses his other hand to massage Leon’s balls. Leon wants to keep watching Pob. He looks so cute. His face is still flushed from his previous orgasm but he has this look of concentration like he's working on some project. His lips set in the pouting expression and all Leon can think about is having those same lips wrap around his cock. The image alone almost has Leon blowing his load. Though he wants to continue to watch his boyfriend he feels like he won't last if he keeps looking. Leon grips Pob’s hips tighter and closes his eyes with a low groan.

Leon’s groans grow louder as Pob continues to stroke him. The excitement of being able to please his boyfriend for the first time has Pob’s spent cock starts growing again in interest. He’s never been this aroused before. He swipes his thumb over the head one, two, three times.

“P’Pob stop… I’m gonna come.” Leon says breathless.

“Isn’t that the point?” Pob says but he stops stroking Leon’s cock.

“I want to come when I’m inside of you.” Leon whispers and he sits up and wraps his arms around Pob’s waist. Pob blushes at the words. He let’s Leon roll them over so he’s on his back again. Pob’s legs spread as Leon settles between them and their erections are bumping against each other. The lips meet again in a sweet kiss. Leon rolls his hips and creates more friction between their erections.

Leon sits up on his knees and grabs the bottle of lube from the table near the bed. It’s a sight Pob thinks he’ll never forget. Leon's skin flushed a light pink, his hair falling in his eyes a bit. Pob did his research on anal sex. He knew what the lube was for and he started to get nervous. He knew that it would hurt the first time even if he was properly stretched. And he held Leon’s cock he was prepared for some sort of discomfort.

“P’Pob I think it’ll be easier if you are on you hands and knees” Leon says.

“Ah ok” Pob rolls over and pushes up on his hands and knees. Pob made sure that cleaned himself down there but it’s still so embarrassing having Leon see him open and up close like this. He pushes his face in the pillow and hides from the embarrassment. He can hear Leon groan from behind him. The sight of Pob basically presenting himself to Leon has him gripping the base of his cock to help his erection die down a little. He’s so hard right now he could probably hammer nails. Leon moves to settle behind his boyfriend and massages the flesh of his ass and thighs.

Leon rubs a dry finger lightly around Pob’s hole. Pob sighs softly at the intimate contact. Leon begins to stroke his boyfriend’s hole thinking about all the things he wants to try with him. Like for one he wants to replace his fingers with his mouth and tongue and leave kisses all over Pob’s fluttering hole. But he knows Pob is not ready for that or the dozen other ideas running through his head. Leon grabs the lube and coats his index fingers with a generous amount. He wants to make sure that Pob feels as little discomfort as possible.

Leon goes back to stroking his boyfriend’s hole with his lube up fingers. Pob grasps, “It’s so cold.”

“I’m sorry baby it’ll warm up in a bit.” With the assistance of the lube the slide is much smoother.

Leon grabs Pob’s hard cock into his hands and strokes him up and down. Slowly at first then slightly faster as a way to distract Pob. Leon pushes his lubed finger slowly into Pob. Even with Leon still stroking his cock Pob gasps at the intrusion. He tenses up at the discomfort.

“You have to relax,” Leon whispers against his thigh. Pob takes three deep breaths as he feels Leon’s finger pushing deeper inside. Leon continues to work that one finger in Pob until there is little resistance. He grabs the lube and adds more to Pob’s crack. Pob whines at the cold. Leon begins to push a second finger into Pob. Pob whines louder. Leon hands moves to stop stroking Pob and massage his thighs instead. Leon works the two fingers into Pob slowly.

“Hurts” Pob says into the pillow.

“I’m sorry baby. Should we stop?”

“No, please I want this....I want you.”

“Ok just relax.” Leon says, kissing the back of Pob’s thighs.

Leon scissors the two fingers he has inside of his boyfriend.

Leon’s dick is only a bit longer than average but where he lacks in length he makes up for in girth. One of the biggest reasons he was so nervous about making love to Pob. He’ll need to work him up to at least four fingers so Pob won’t feel any discomfort. Leon crooks his fingers inside Pob searching for Pob's prostate. When he hears Pob moan the loudest he has the whole night he knows he found it. Leon pulls his fingers back and pushes back in hitting that same spot again.

“Oh Leon…ohhhhhh” Pob continues to moan loudly, hands moving to grip the pillow underneath his head.

Leon continues to massage Pob’s prostate. The feeling is so good Pob doesn’t even realize that there are now three fingers inside of him. The discomfort of the stretch caused Pob’s cock to soften a bit but now with the stimulation of his prostate his cock is almost fully hard again. He feels the cold dripple of lube falling down his crack. Though he didn't feel the third finger enter he definitely feels the fourth. Pob groans into the pillow he doesn’t say anything because he's scared Leon will try to stop. But the stretch of the fourth finger fucking burns. He moves to stroke his cock to distract himself from the pain.

“I'll do it” He barely can hear Leon as he pushes Pob’s hands off his cock. Leon begins to stroke him while slowly working the four fingers inside of him hitting his prostate everytime. Pob continues to groan in the pillow.

“How is it P’Pob? Are you ok?”

“Yes” Pob’s voice cracks, “I’m ok it feels good… so full”

Leon is still four fingers deep in Pob but the stretch has lost the slight sting from before. Based on his research Pob thinks he’s ready for Leon’s cock.

“Leon, I think I’m ready.” Pob says, pushing himself back up onto his hands.

“Just a little more baby I don't want to hurt you.” Leon kissing the flesh of Pobs ass. Leon keeps fucking Pob with four fingers adding more lube. It’s getting a little messy and Pob moans are growing louder with the continual stimulation to his prostate. Since finding his prostate Pob’s cock has started to leak again. He can feel his orgasm approaching again.

“Leon stop, I'm gonna cum again” Pob breathes out.

“Then cum baby. I want you to cum again.” Leon whispers against the flesh of Pob’s thighs.

“Leon... if...if...if I cum now I don't think… I don’t think I can again” Pob struggles to get out with Leon with Leon still fucking him with four fingers. Leon removes his fingers from Pob. He watches as Pob hole clenches around nothing. Leon knows for a fact that everytime he closes his eyes he’s gonna see that image again. He can’t wait to feel that around his cock. Leon has never been this hard in his life. He really wants to make this good for Pob but he doesn’t think he’ll be able to last.

With Leon’s fingers no longer inside him Pob slumps back down on the pillow with a sign.

“How are you feeling?” Leon asks.

“I’m good. It just feels a little weird being empty now.” Pob says honestly. Leon can't deal with this. He knows Pob is not doing it on purpose but hearing those words coming from Pob’s mouth makes his cock throb.

“P’Pob can you turn over for me. I want to see your face.” Leon moves back to give his boyfriend room to roll over. Pob is laying on his back and is hard cock laying against his stomach. Leon wants to put it in his mouth and make him cum but not more than he wants to be inside of his boyfriend. Next time he reminds himself. They have plenty of time. Leon grabs one of the extra pillows on the bed and puts it under Pob’s hips. He doesn’t want his back to hurt later. Leon settles back between Pob’s thighs and kisses him again. The couples kiss softly again, tongues swirling around each other. They keep kissing until Pob pulls away.

“Leon, I'm ready” he says making eye contact with his boyfriend as he moves his hips to brush his erection against his boyfriends. Leon feels a lump grow in his throat.

“Ok”’ he nods.

Leon pulls back and grabs the condom. He gives his cocks a few strokes as he takes in the site in front of him. He groans as he opens the condom and rolls it on. He grips Pob’s thighs and spreads them wider. He can see Pob’s hole still glistening with lube. He adds more to his cock and gives a few more tugs. With Pob’s legs spread wide Leon grabs his cock and rubs it against Pob’s hole. They both groan and Pob’s eyes close at the sensation. Leon continues to rub his cockhead against Pob’s tight hole.

“Leon… please” Pob begs.

Leon, never one to make Pob beg, pushes his hips forward into his boyfriend. Once the tip is inside Leon tenses up. No matter how much he tried to stretch Pob he knew it would be tight but nothing could have prepared him for this. It had always been a rule of Leon’s to avoid virgins. Too much responsibility, he always thought. He never felt something so warm and tight around his cock before. He pushes the rest of the way in. Leon throws his head back and groans loudly. He grips the back of Pob’s thighs tightly. It’s only just started and he feels so overwhelmed already. His cock throbs inside Pob’s tight heat. He waits a while to give Pob time to adjust. Only after he feels Pob push his hips toward him to feel Leon’s cock deeper does he move. He pulls back a few inches and pushes inside again. The couple moans in unison.

Leon adjusts his angle aiming for that spot inside Pob to make him see stars. He knows he already made Pob cum once tonight but he wants to make him go again before he cums. He knows he found that spot again when Pob moans so loudly. He keeps that same angle and makes sure to keep hitting Pob’s prostate.

Pob’s never felt anything like this before. It’s so good he can’t focus on anything but Leon fucking him. Pob’s moans grow louder and he locks his ankles around Leon’s back and grips his shoulders pulling him. Pob buries his face in Leon’s neck.

“Does it feel good?” Leon pants into Pob’s ear.

“Yes you feel so good inside me,” Pob says, coming to his senses a bit. He feels Leon’s cock twitch inside of him at the words.

“It’s so good Leon. I love having you inside me.” Pob whispers, kissing the lobe of Leon’s ear. Leon moans and starts fucking into Pob a little harder.

“Leon, I love it so much. I love you so much. You're doing so good. You're making me feel so good.”

Hearing the praise from Pob snaps something in Leon. He sits back on his knees and pushes Pob’s thighs back even more. Pob is nearly being bent in half but can hardly care. Leon thrusts back in hard and fast. Still abusing Pob’s prostate. The couple locks eyes and Pob can see that desire has taken over them. Leon is still going fast and hard. Pob’s not sure how much more he can take. Pob wants to keep talking and praising Leon but all he can manage is sobs of the other man’s name. His eyes are a little blurry with tears.

It becomes too much for Pob. Leon is hitting his prostate on every thrust. Pob’s body can barely take this abuse anymore. Without warning his orgasm hits him. With nothing close by to grab, Pob hands grip the pillow underneath his head.

“Leon… ahh” Pob sobs, eyes still blurry with unshed tears.

Pob begins to whine as he's being fucked through his orgasm. His cock still shooting thick ropes of cum on his stomach. It feels like hours have passed after he's finally done cumming. But he’s not given any time to recover immediately after his orgasm finishes Leon’s starts. With a low groan Leon cums into the condom still gripping the backs of Pob’s thighs. He slumps over Pob as they both try to catch their breath.

Leon pulls out of Pob. His hole looks red and irritated. Leon looks to his boyfriend and sees there are tears in his eyes. How did he not see that his boyfriend was hurting? Had he been that caught up in the moment?

“P’Pob, are you ok?” Leon asked. Pob doesn’t immediately respond and that only skyrockets Leon’s concern. “Oh P’Pob, I’m so sorry. I didn’t mean to hurt you…” Leon was cut off.

“Hurt me? What are you talking about? It was wonderful, perfect, amazing. I’ve never felt that good before.” Pob says.

There is visible relief on Leon’s face.

“You didn’t hurt me. You were perfect.” Leon blushes. Pob could get used to this side of Leon.

“We should shower and get cleaned up” Leon says, leaning over to kiss his boyfriend.

Notes:

Little did Leon know this would be there first and last time. Jkjk

I wanted to use that line as the ending but I thought you guys would hate it. Also sorry for the abrupt ending. I ran out of ideas. And yes there needs to be more Leon/Pob content out there but I never thought I would be the one creating it. This prompt was a monster my originally idea was just that Leon spends a lot of time fingering Pob to prepare him but it's totally something else now haha

How are you guys feeling about my writing? I feel like I’m putting in too many useless details.
It was fun making this though. On to the next prompt.

P.S. Did you catch Leon's praise kink in the end? Haha I kinda got that idea from their break-up scenes. How Pob told Leon that he want to settle down in one place and be loved and that's why they have to break up blah blah blah

Also this was fucking over 3,000 words not at all what I planned