I'm not 100% okay with how this chapter came out. Just a warning this chapter contains smut. So feel free to skip if you want. Also this is my first time writing smut so sorry if it's terrible.
It was almost 7 o'clock about time for when Anna was supposed to come over to his house. He made sure that he had the house to himself. Sam was going to hang out with Ruby. He really didn't like the idea of Sam hanging out with that girl. Something about her just seemed a little bit off but he would never tell Sam that because he knew that if he do they would end up getting in a big argument and he didn't feel like getting to it tonight. Bobby was going out somewhere Dean wasn't exactly sure where. Probably out somewhere with Rufus.
Whatever, It didn't really matter. He had everything ready for Anna. He had some candles going, some romantic music going to help set the mood. The doorbell rang and Dean ran to go answer it.
"Hello." He said answering the door.
"Hi Dean." Anna replied as she went inside the house
Anna was looking really hot. Her hair and makeup were the same but the outfit was wearing left nothing to the imagination. She was wearing a plain blue tank top that exposed several inches of her stomach and a short miniskirt.
"Would you like something to drink?" Dean asked her
"No thank you." She said sitting down at the couch.
"All right." he said joining her on the couch feeling awkward for some reason even though he's done this a hundred times before.
Suddenly Anna pressed her lips against her wrapping her arms around her neck. Dean immediately responded by lightly grabbing her hair and having his tongue demand entry into her mouth which she granted. He moved his hands to go around her waist and forced her to lean back against the pillows that were on the couch. He pulled his lips off with a soft smack and pressed them against her neck. Anna let out a low moan as Dean continued to kiss his way down her body and peeled off her shirt and lacy black bra when it got in the way.
"Wait Dean." Anna said lifting her head as Dean had one of her breasts in her hand
"Yeah what?" He asked
"Take your shirt off." She said
"No problem." He said with a smile as he peeled his shirt off as well.
"There that's better." She said as she leaned back down.
He continued to play with one of her nipples eliciting some moans from her when he pinched it. After playing with both of her nipples. He kissed his way down her stomach and slowly edged down her skirt. She leaned back up when her skirt was fully off and said "Pants off now."
"Sure thing." He said as he undid his belt and slipped off both his pants and his boxers. Anna lowered her panties until they were completely off. Dean slowly one finger into her and then slowly added some more. Until he had three fingers in her and she was letting out moans intermixed with "Oh god" and "Faster".
She whined when Dean removed all three of his fingers.
"Just hold on a second." Dean said as he ripped open over a condom packet with his teeth and put it on his cock and then slowly started to thrust into her.
"Oh god." She moaned as her hips rose to meet her thrusts
"Sorry wrong person." He joked as he got deeper into her.
"Faster." She cried
He shoved his hips harder against her ,rocking her whole body with the force of his thrust and drawing a cry from her not that was hard. Some of the sounds that she was making sounded downright pornographic.
"Oh god. I'm going to-" She moaned as her body started shaking.
Dean let out a gasp and made one more thrust before he reached his orgasm as well. He slowly pulled himself out from Anna.
"That was amazing dean." Anna said after she recovered from her orgasm.
"Yeah?" he asked
"Yeah." She said "Is it cool if I spend the night?"
"Sure." He said "You still remember where my bedroom is right?"
"Of course." She said with a giggle.
Later when they were cuddling. Something didn't quite feel right to Dean. He couldn't put his finger on it and when he finally drifted off to sleep. Brown hair instead of red seemed to be the one thing that he remembered.