Featuring:David and Henry find themselves getting up to no good, with a virginity being lost. (David's POV) I was on my way back from the convenience store, after buying two Valentines Day cards, one for Kathryn and one for Mary Margaret. However, when I left the store and was making my way over to the car, I spotted Henry walking down the sidewalk. He was wearing a various shaded blue, plaid jumper, over a pale, light blue shirt. Then on top he had a black raincoat on and a brown scarf. "Hey buddy." I smiled. "What are you doing walking around this late?" "I was looking for Emma. Do you know where she is?" Henry asked. "I believe she's trying to find someone who broke into Gold's house. How about I take you home?" I offered. He thought for a moment, then reluctantly sighed. "Okay." He nodded. So, he got in the passenger's seat of my truck and we headed off As I drove, I couldn't help but notice Henry was staring at me. I felt a little bit self conscious.
"Everything okay, bud?" I asked. "Yeah, you're just... Very attractive." Henry said, casually, making my eyes widen. "Oh, well, umm... Thanks, Henry." I said, awkwardly. "Really sexy, too." Henry added, before reaching over and suddenly groping my chest. "Woah, Henry. I don't know if you should be doing that." I told him, nervously. "No? What if I did this?" Henry then lowered his hand onto my crotch and gently squeezed. "Shit, Henry! We shouldn't do this!" I gasped, though I was becoming increasingly more attracted to him. "We shouldn't... But I want to, anyway." Henry said in a very calm, cool tone. "But Henry I'm so much older than-" But before I could finish, I heard a zip. Henry's hand slithered through the fly of my jeans and groped my hardening cock. "Ohhh, Henry..." I groaned, trying to focus on the road. "Come on, David. I really want this." He told me, rubbing my cock through the briefs. "We can't do it here, Henry. People will see us. And we can't do it at your house because your Mom will be-" "Mom's not home. She won't be till late, tonight." Henry corrected me. "Are you serious?" I asked, seeing the opportunity. "Yeah, I am." Henry smirked. I put my foot down on the pedal and sped over to Henry's house. When we arrived, we both eagerly jumped out the car. Henry seemed oddly casual about this, like he had done this before. He took my hand and brought me to the door. I watched as he took the keys and fumbled them against the keyhole, desperately wanting to get in as quick as possible. The door opened and we both came into the massive house, with a very white interior. (Henry's POV) I had wanted this since the moment I laid eyes on Prince Charming. He was like the hottest guy in Storybrooke. He was wearing a grey top, under a blueish, paid shirt and then that was under a black coat and a pair of black jeans. I walked over to him as he looked around the house. "You are so hot." I said, simply, before pushing the cost off his shoulders. He helped me pull it off his arms and let it drop to the floor. "If we do this, Henry, nobody can know about it." David told me. "I know. Nobody will find out." I assured him, unbuttoning his shirt, right in the middle of the hall of my house. "And you're sure you wanna do this?" David asked, seriously. "Oh, I'm definitely sure." I smirked before letting his shirt fall to the floor as well. "Well, if you're sure..." David said before suddenly pulling his own shirt off and then before I knew it, I was being pinned to the wall and his lips were attacking my own. As his tongue forced it's way inside my mouth, his hands ravished my body, forcing my coat straight off my body. It fell to the floor and soon, he was pulling at my jumper. I raised my arms and his lips broke off from mine, so he could pull it straight over my head and throw it over his shoulder. He resumed his forceful kissing as I felt up his incredibly muscular body. His hands began fumbling at my shirt, unbuttoning it as quickly as possible. Soon, that as well was dropped to the floor. He stopped kissing me for a moment, to check out my young body. "I can't believe I'm doing this." David muttered. "Believe it." I said before taking one of his nipples into my mouth. I began suckling the perky nub and flicking it with my tongue. "Ohhhh yeah... Good boy." David said, gripping my hair. Then, a few seconds later I felt his hands grip my ass then lift me into the air! I wrapped my legs around his waist and my arms around his neck. "We're going to your bedroom." He whispered in a deep voice. (David's POV) I wasn't entirely sure what came over me as I carried Henry up the stairs as he kissed my chest, but I wanted him. Eventually, I kicked open Henry's door and dropped him onto the bed. I then quickly got on top of him and resumed making out with him, hungrily. His hands ran over every inch of my skin and his hips thrusted into me, desperate for some friction. I barely knew the kid, yet here I was, sucking on his bottom lip, on his bed. "God, please, fuck me." Henry whimpered, sending goosebumps all over my skin. "What's that, baby?" I whispered into his ear, before gently nibbling the lobe. "Fuck me, Daddy. I need it!" He begged. (Henry's POV) I watched as David got off me and the bed, and stood over me. His body really was incredible, but the fire and lust in his eyes are what made my cock throb. Suddenly, he began unbuckling his belt in front of me, making my throat go dry. "Oh, I'll fuck you, Henry. Just remember, you asked for it." He said, before his pants finally fell around his ankles, along with his pair of white briefs. David's 10 inch monster was released and standing proudly. I gulped. Then he reached down and begun unbuttoning my pants and soon pulled them off me with one quick motion, along with my boxers too. We were both naked in my bedroom. "Turn over." David commanded. I did as he asked and turned onto my stomach, giving him a full view of my butt. (David's POV) My dick was already leaking precum as I stared at the young boy's incredible ass. Without thinking, I gave it a loud slap and watched it jiggle. "Fuck yeah..." Henry winced before I ran a finger down his crack, between the cheeks, and watched the boy shudder. "Oh my God, Daddy..." Henry said again, and I don't know why but every time he did it was like I needed him even more. Without anymore hesitation, I went down to my knees, spread his cheeks apart and buried my face into his ass. "Oh shit!" Henry gasped as I began eating out his hole. "Oh yeah, David... Eat me out, Daddy." Henry moaned, which only made me hungrier. My tongue pushed it's way inside, my hands spreading his cheeks far apart. (Henry's POV) I was biting my bottom lip as I felt the older man ravish my asshole. I was in ecstasy as he buried his face deep into it, either licking my hole or fucking me with his tongue. "Da-David... Fuck... Mmm David, I need you inside me.." I whimpered. "You want it, boy?" David growled, kissing my ass cheek. "Yes, Daddy. I need it!" I begged. David suddenly grabbed me and forcefully flipped me over so I was on my back. He got on top of me and smashed his lips against mine. Our dicks rubbed together as they both leaked precum, meanwhile my hands felt all over his muscular body. "Do-Do you have any lube?" David whispered, pressing his forehead against mine. "Bedside drawer." I nodded. I had stolen it from my Mom's bedroom the other day, wanting to jerk off with the same lube Graham used. (David's POV) I didn't even bother questioning the fact that Henry had lube as I opened the drawer and pulled out the bottle. "Hands and knees." I instructed him as I began squeezing out a lot of lube onto my hand, on my knees. Henry eagerly did as I said and I got an amazing view of his tight hole. I began rubbing the cold lube into Henry's crack, which made him hiss. "It's cold..." He whispered. "Don't worry, baby. It'll heat up soon enough." I told him before kissing his ass cheek. Once I was happy with his asshole being generously lubed up, I began putting a load onto my dick, too. I knew this was gonna be tough for him. "Listen. This is gonna hurts to start with but it will get better." I warned him before pressing the tip of my cock against his asshole. "I know..." Henry said. So, I slowly began pushing my dick into his hole. (Henry's POV) My eyes clenched shut and my fingers gripped the bed sheets as I felt him enter me, more and more. It felt like my asshole was on fire! I felt his lips soon kiss my back and shoulder, trying to soothe me, and it somewhat worked. "It's okay, baby. Just relax." He whispered as I felt him throb inside me. (David's POV) I decided to only fuck him with half my dick, as I feel like I'd puncture an internal organ if I put every inch inside him. I gently nibbled his earlobe as I slowly thrusted my hips, back and forth. He felt incredible. It was so tight! It was so much better than Katheryn! It was better than Doctor Whale, too! I had to stop myself from slamming everything inside him, as the feeling was so intense and incredible. "Fuckkk, Henry... That's gooooood..." I groaned, still gently moving my hips. "Fuck me, David." Henry muttered. "Faster." So I did. I gradually picked up the pace and watched Henry's ass repeatedly swallow half my dick. "Shit, Henry! You're so tight!" I growled. "It feels so good, David! Oh, fuck me, Daddy!" Henry moaned out. (Henry's POV) I was in heaven. One of, if not, the hottest guy in our town was fucking me on my bed and it felt amazing! And not only that, but if my theory was correct, he was also my Grandad! At first it hurt like hell, but now it was just pure pleasure. And I knew David hadn't put everything inside me, and honestly I was somewhat glad, because I felt like I was taking more than enough already. "You like that, Henry?" I heard David mutter as his nails gently dug into my hips. "Oh, fuck yes, Daddy. I love it. I love it so much!" I moaned before I felt him kiss my shoulder. "If you ever want to do this again, you'd better fucking call me." He whispered in my ear, sending a shiver down my spine. "I will, Daddy." I promised him before he resumed kissing my shoulder, as half his dick continued to plunge inside me. Suddenly, I felt him pull out of me, making me whimper, before he man-handled me and made me lay down on my back. "I wanna see your face." He told me before lifting my feet upwards, over my head, and aimed his cock at my hole again. "Oh God..." I whimpered as he re-entered me and my nails dug into the bed sheets. (David's POV) I resumed fucking Henry on his bed, enjoying the intense pleasure as I looked into his face. We were both really sweaty by now and his hair was sticking to his forehead. "Oh my God... You're so fucking hot..." Henry moaned, reaching up and groping my pec. "Mmmm, you are too, baby." I purred before taking Henry's dick in my hand and beginning to stroke it. His back arched and his nails suddenly dug into my chest, making me hiss through my gritted teeth. "Oh, shit! I'm gonna cum, Daddy! I'm gonna cum!" Henry moaned, loudly. "Do it, Henry. Cum for me. Cum for Daddy!" I grunted, still resisting the urge to plow everything I had inside of him. It wasn't long before he was crying out in pleasure and his cock began shooting his white load all over his stomach and on my hand. Seeing his body spasm beneath me was quite an amazing sight and I knew I was close, too. (Henry's POV) I had just about finished unloading onto myself and I barely had a chance to think when David pulled his cock out of my ass. I knew what he wanted as he began crawling up my body. He straddled my chest and his cock was standing, throbbing, directly in front of my face. "Suck Daddy's load out of him." David instructed me, sending more chills down my spine. I opened my mouth and took as much of the cock as possible, though I definitely couldn't take the whole thing. I sucked as hard as I could and bobbed my mouth up and down, desperate to taste his jizz until finally- "Aarrrrghhh! Fuck yeah! Swallow it! All of it!" David moaned loudly, gripping my hair and forcing me to swallow every load he shot. It seemed almost endless the amount he shot, slowly filling my entire mouth. When he was finally done, I managed to swallow ever last drop. "Holy fucking shit..." David panted before sitting down next to me, his back against the headboard of the bed. (David's POV) "That was the most amazing thing ever!" Henry beamed with a massive smile. "Let's do it again!" He said before getting up and straddling my hips. Although I was tempted as I stared at his cum soaked body, I knew I couldn't. "Woah, there, dude. I can't." I told him, gripping his waist so he wouldn't try it. "Why not?" He pouted. "Because I need to see Mary Margaret and I can't be out too late otherwise Katheryn might get suspicious." I reasoned. "But I want to do this all... night... long..." Henry whispered, seductively, before kissing me and wrapping his arms around my neck. I couldn't help but let him make out with me for a bit, loving the taste of my own cum in his mouth. However, I eventually had to break off. "Mmm... I'm sorry, Henry. If I could, I would fuck you all night." I told him before lifting him up off me and placing him beside me. "Promise me we'll do this again?" Henry asked as I got up off the bed. "Of course we will! I promise." I told him, wanting this as much as he did, as I pulled my boxers and pants back up my legs, my semi erect cock in slight discomfort. "Maybe next time I could ride you!" Henry said, excitedly, as I looked for my shirt. "Maybe, dude. Hey, what happened to my shir-" "It's downstairs." Henry reminded me, with a smirk. "Oh... Right." I said, smirking too. "Well, I gotta go, Henry. Thank you for tonight." I told him, who was still naked and covered in his own cum, laying on the bed. "Thank YOU! Best night ever!" Henry grinned. I chuckled before leaving the bedroom and making sure to pick up all my clothes on the way out the door. As I got in the car I realised it really was the best night ever. But I was in a really fucked up situation. I was cheating on Katheryn with Mary Margaret, whilst also now fucking a random kid! I felt a mixture of shame, guilt and excitement as I began driving away.
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