He held himself and rubbed up and down on your wet area. He bit his lip as he felt how soaked he'd gotten you. He slowly slid into your pussy and held your face as he did. You immediately shed a tear while you moaned loudly out of pain. He took his thumb, wiped it, and leaned into your ear. "You okay baby?" You replied in a high pitched tone of voice, "No.. it hurts." Another tear fell. He wiped that one as well and said "Give me a second." He went and got a towel from your closet to clean the blood that dripped from you and started to lightly rub two fingers against your clit. The pleasure from that caused another loud moan to uncontrollably escape from you. He started to kiss your lips again and while he rubbed your clit, he started slowly sliding into you again. You bit your lip as he pushed into you and he stopped at about half way in. "Better now, love?" He asked while gripping your waist in one hand and holding your face in the other. "Mmhmm," you moaned softly while nodding your head. He started to stroke you lightly making sure to check on you every now and then. The more he stroked you, the less it started to hurt. Eventually it felt good, to the point where you were holding onto the back of his neck and using your legs to push him further into you. August felt what you were doing and his head flew back as he sped up inside of you.
After a few, he turned you around to put you on all fours and slid into you. You moaned loudly again and August gripped your thighs from behind you. He checked on you again and continued to stroke you. He was already close to cuming because of how tight you were, so he was starting to speed up. The faster he got, the more aggressive he began to get. "Move back on it, babygirl." He said still fucking you from behind. You hesitantly started to back up on his dick and slow paced while he anxiously squeezed your ass. "L..like this, baby?" You asked, then moaned at a high pitch tone which turned on August even more. "Fuck, just like that, baybeh." His accent got you wetter. You got used to the feeling and eventually it became easier to move back on him. At one point he didn't even have to touch you.
After a while, he pulled out of you and very swiftly flipped you on your back to start eating you out again. This time he held one of your legs up in the air while the other remained flat and stared to suck on your clit. You stated to grab onto his hair again and pulled roughly while moaning, trying to remember not to moan too loud so you guys wouldn't get caught. August took both of your hands off his head and put them over your head while holding your wrists, still eating you out. Soon after restraining you and making you squirt, he inserted a finger into you slowly. "So you a squirter, huh?" He asked in his heavy New Orleans accent smirking and pausing from pleasing you to kiss your neck. He was still holding you by your wrists which made you go crazy. You couldn't help but scream, and August quickly kissed you to mask the sounds of your pleasure.
Later on you wanted to return the favor to him. As he was putting you in the next position you turned and grabbed his dick. His eyes widened at you. "Y/N, you don't have to-" you started licking and sucking teasingly on his tip. He very calmly yet sensually looked down at you work on him as he bit his lip from the pleasure. You eventually took him further down to where he was halfway in your mouth. Your head bobbed up and down while rubbing his shaft with one hand and lightly played with his sack in the other. August was so turned on he decided to hold your hair in his hand and simultaneously push your head down on him. "F-Fuuck... baybeh..." Right after his exclamation, he came.
You immediately spit his load into your small waste bin. "AUGUST!" He chuckled. "Sorry, babygirl." And with that you got back into the position August initially put you in. He lifted your leg up again and put it over his shoulder. He slid in and fucked you with a high level of aggressiveness. He'd worn you out already, but it still felt so good for you both. About 10 minutes after that he quickly pulled out of you and came on your stomach.
He got the same towel he used for the blood and wiped you off. You were already dozing off and it was 1 AM when he looked at the clock. "Wake up, love." He said while tapping your thigh. He started to put his clothes on and suggested you do the same. You clothed yourself and so did he. August had put on all the clothes he came in and put out on the clothes you were in before he came. "Ya back still hurt?" He asked you smiling. You smirked and jokingly hit his arm. "Oh yeah," he took the towel and put it in your hamper. "Can I stay here tonight?" You gave him some basketball shorts he'd let you borrow from him a while back. "Of course." You replied sleepily. You pulled out the guest bed from underneath yours for him to sleep in and he did while you slept in yours after he changed.