A Very Hot and Sleepless Night

BY : Gold4sun
Category: Celebrities - Misc > Het - Male/Female
Dragon prints: 2251
Disclaimer: This is a work of fiction. I do not know Debby Ryan and I do not make money from this writing.

A Very Hot and Sleepless Night

Debby Ryan tried to fall asleep, but it was helpless, she just wasn’t tired right now. Maybe it was because she and her best friend Monica had shared a bottle of wine just before they went to bed, her mind was still reeling from all that took place during the day and with her mind working overtime, she found it impossible for sleep to overtake her.

Or maybe it was just the fact that she was sleeping on a blown up mattress on the floor.

Monica had asked Debby to sleep over at the very last minute and they had to call Monica’s older (and hot) brother Shelby to pump air in the mattress, Debby never got tired of looking at Shelby work out with his jet black hair pulled back behind his ears.

She also had to borrow a nightie, a bra and panties from Monica since she didn’t bring any extra when she came over and she also didn’t want to wear the same pair for the entire night.

Debby sat up on her mattress and looked up at Monica who was sleeping in the bed next to her. Her eyes were closed and Debby had to wonder if she was asleep.

“Hey Monica” she whispered. Monica didn’t open an eye, she didn’t move nor did she speak. “Monica are you still awake?” Debby asked in the same low voice as before. Yet again Monica did nothing but sleep in Debby’s face.

It was clear that Monica was out like a light. Debby didn’t know what she could do to fall asleep since she ran out of idea; she got out of her mattress and went out into the dark hall. She headed towards the living room, since she couldn’t fall asleep, she might as well watch TV, there was most likely nothing interesting playing at this hour, but that might just help her close her eyes and fall into darkness.

As she walked through the dark hallway, she saw a beam of light coming from inside of Shelby’s room from the bottom of his closed door. Debby was surprised that he was still up at this time of the night. As she got close to the door she stopped and stayed in front of it.

Debby had a crush on Shelby for years, but she didn’t know if he liked her as well. He was a few years older than her and she had a feeling that he would always see her as Monica’s friend. She questioned if she should knock on his door and see if he was willing to chat with her for a while and maybe if she got lucky, they could share a kiss?

Then she heard him moaning.

Debby slowly opened the door, just a crack so she could see inside of Shelby’s room. She saw Shelby sitting on his bed completely naked; his long black hair was pulled into a ponytail so it didn’t get in the way of his handsome face. With one hand he held a picture and with the other hand he stroked his massive cock.

Shelby didn’t hear his door open because he was in another world with how great it felt as he moved his hand along his cock. The last time he got laid was five months ago before his girlfriend dumped him for his best friend, he didn’t really mind since he was never that much into her. He liked another girl a lot more than his girlfriend; he was mostly just with her to pass the time while he tried to gain courage to ask the girl he truly liked out. But the thing he missed the most about his girlfriend was the wild sex they had every other night. That was why he stayed with her for so long.

Debby couldn’t take her eyes off of Shelby’s mighty rod. Her eyes were locked on and even if her brain told her to look away, she just couldn’t bring herself to actually do it. Just looking at Shelby masturbate turned Debby on, she quickly slipped one hand up her nightie and into her panties as she watched Shelby.

As Debby started to get in the mood, she accidently put too much pressure on the door, which caused it to fly open. Shelby jumped as the door to his room opened up and he saw Debby looking at him with her hand in her panties.

Shelby quickly grabbed his pillow to cover himself up as the picture he was looking at fell to the floor and slipped under his bed. Debby grew bright red as she took her hand out of her underwear and hid it behind her back.

“Um…hi” she said, unable to think of anything better to say

“What are you doing here?” asked Shelby

“I…um…was looking at you” said Debby

Shelby stood up and walked closer to the door keeping the pillow over his cock. “You were spying on me masturbating and it turned you on, didn’t it Debby? I saw your hand in your panties so don’t try to deny it”

Debby’s face got even redder if that was even possible. She wanted to say something, but she had loss her ability to speak. She just nodded her head to agree with what he told her.

Shelby took her hand and pulled her into his room before he closed the door. Debby felt her heart rate increase, she was still a virgin but if Shelby wanted to make love to her, she wouldn’t think twice about losing her virginity to him tonight.

“That was not cool” said Shelby “looking into my room without telling me. What do you think your punishment should be?” he asked her.

“I…” she couldn’t say anything else. She was too shy due to what Shelby saw her doing and just being in his presence made her dizzy on a daily basis.

Shelby looked at her. He took the pillow that hid his cock and tossed it back on the bed. The minute it was gone, he saw that Debby’s eyes scanned his member. Shelby smiled “You like my dick?”

Debby nodded her head.

Shelby walked over to her; he stood so close to her that Debby could feel his hard cock pressed against her leg. She felt Shelby rub his dick against her leg, as he took her cheek into his hand (the hand he was stroking his cock with) and took her lips into a kiss.

Debby felt like her heart would stop. She had kissed a few guys before and she and Monica had also kissed once to see how it was like to kiss a girl. It was nothing new to her, but it was the first time that she kissed her crush Shelby and it was everything she thought it would be, it was hot and it was sexy and it was exciting due to the fact that his cock was pressed against her bare leg. He kissed so well that Debby felt like she was an amateur compared to him.

“Don’t lie to me” he said to her

Debby shook her head “I won’t”

“So tell me, how should I punish you for your crimes?” he asked her

“I…” she looked around his room nervously before looking right back at him “I think that you should fuck me and take away my virginity” she said. Her heart rate was in overdrive and she couldn’t believe that she was actually able to say that to him.

Shelby arched an eyebrow “so you think you should lose your virginity?” he asked just to make sure.

Debby didn’t say anything, she just nodded her head.

Shelby walked over to the bed and sat right back where Debby had caught him masturbating before “Come on my dick” he said to her.

Debby was so nervous; she was actually going to lose her virginity to her crush and best friend’s brother. Her heart was racing and she didn’t think it was going to stop anytime soon. She pulled the nightie off over her head and Shelby slowly stroked his cock to keep himself hard while Debby stripped in front of him. She then unhooked her bra and let it fall off her shoulders to the floor.

“Stop!” he said all of a sudden. Debby stood there and Shelby looked at her breast, he never noticed that Debby Ryan had such nice tits on her body. After a moment or two of looking at her he told her to continue stripping for him.

Debby went over to Shelby and stood right next to him. He looked over at her as he slowly stroked his member. Debby slowly pulled her panties off and Shelby looked at her pussy. He placed his hands on her hips and brought his mouth over to her pussy and gave it a few licks. Debby closed her eyes and moaned at the pleasure that Shelby’s mouth delivered to her body.

Shelby stopped and looked up at her “Get on” he command her to do.

Debby got on the bed and got on top of Shelby, her heart was still racing and she didn’t know when or if it would ever stop. Debby took his cock in her hands and held it still as she came down on it. Shelby’s cock went inside of her and she had to hold back a scream. He was so huge, she didn’t know if all of him would fit in her, but Shelby had other plans as he held her hips again and thrust inside of her. Debby had to hold back a scream as she didn’t want to wake Monica.

“Yes, you’re so tight” he said to her. Shelby started to pump inside of Debby; she closed her eyes and moaned as she started to move her hips along with his thrust in her body. She wrapped her arms around his neck as they moved together and she brought her lips to his mouth and kissed him. She felt his tongue invade her mouth and it shocked her at first since she never kissed using her tongue before, but she knew how skilled Shelby was and accepted it and used her tongue with his and it drove her crazy how hot it was to make love with him and kiss with him. She would never forget this amazing night that she shared with the first man that she could say that she really loved.

“I love you” Debby said all of a sudden. Shelby heard her and continued to pump up into her body. Debby didn’t mind, she knew that he heard her say it and she actually couldn’t believe that she had the guts to say it. But she was having sex with him and so she figured that she should just tell him the truth that she would never love another man the way that she loved him right here and now. No love could be better or hotter than this moment with this man.

“I’m getting close” Shelby told her

“So soon” said Debby, her tone made her sound disappointed and she was because when Shelby came she would no longer be a virgin and her first time would come to a close.

“I was masturbating for well over ten minutes before you showed up” he said to her.

“Hold it inside for me baby” said Debby as she gave him a light kiss

“I’ll try sweetheart” he told her and that made Debby blush because Shelby called her sweetheart. She wished on her birthday cake every year for him to call her that and it seemed that eight years’ worth of birthday cake wishes came true in the end.

“Yes, this feels so fucking good” shouted Debby, Monica was the farther thing in her mind right now and she didn’t care if her best friend heard her and woke up and she surely didn’t care if Monica opened the door and caught them

“I can’t hold it inside any longer” said Shelby as his cock went inside of her

“Please…for me” said Debby

“I’m at my limit” Shelby told her. He pushed up into Debby and shot his head back as he had his release inside of her. Debby moaned as she felt his seed enter her womb and just remembered that they foolishly forgot to use a condom meaning that she could get pregnant. But as the cum continued to spill into her, that thought soon left her mind and the haze of lust soon came over her.

“That was amazing” said Debby as she lean against him

“You said it sweetheart” Shelby said, he seemed to just notice her tits and using both his hands pushed them up and to his mouth as he licked her nipples and heard Debby moan again.

Debby pulled herself off of his manhood and lied on the bed right next to him. Shelby kept his hands on her and rolled his tongue over her nipples in circles and Debby found her eyes rolling to the back of her head. She couldn’t even think straight anymore. All she could think about was pure pleasure and sex.

“I need more” she moaned out

“You want more punishment?” Shelby asked her


“Then how about you suck my penis”

“Of course” Debby told him, she pushed him slightly so he was back in the same position that he fucked her in, as she went in front of him, placing her face right in his groin and stretching her legs over the edge of his bed.

“Use that tongue sweetheart” Shelby said to her as he passed his hands through her brown hair.

Debby started to lick him; her tongue started from his balls and moved up through his length to the top of his dick, then she rolled her tongue all the way back down to his balls. He still had small amounts of cum that covered his penis and was stunk in his public hairs and Debby was more than happy to use her skilled tongue to collect what was left behind. Taking his cum onto her tongue, she looked up at Shelby and showed her tongue to him before swallowing the seed that he gave her. Debby then went on with her work of licking his pole. She used her hand to hold his dick up and started to kiss his balls, her nose buried in his public hairs, she got the scent of him and it drove her wild.

“This is the life” Shelby moaned as he loved the feeling of Debby giving his balls love. His now ex-girlfriend never kissed his balls when she sucked his cock in the past. It felt hot and he wanted more of this in the future. He placed a hand over her head and stroked her hair. Debby found it was cute even if it was one of the only things her mind could think about at the moment.

“I love your balls” he heard her say.

“I love what you’re doing to them, don’t stop sweetheart, you’re getting me hard again” he said to her.

“Cum all over my face” Debby said and then she kissed his balls again

Shelby grabbed a handful of Debby’s brown hair and pulled her head up, he leaned over and kissed her on the mouth “I’ll need more than that to cum”

“I’m on it” Debby smiled to him and returned to his cock, she opened her mouth wide and took the entire cock into her mouth and moved her mouth back and forth along his length. Shelby was in a daze at how skilled Debby was for a virgin. His ex-girlfriend was known as a slut and had given blowjobs to other men before, after and during her relationship with Shelby and she was nowhere as good as Debby Ryan.

Debby moved her mouth to the deepest level, her lips were so close to his balls and Shelby was surprised that Debby was able to deep throat him this way, he could feel her tongue rolling in circles around his cock and it drove him wild. He felt like face fucking her and he knew that if he asked her, Debby would agree, but he chose against it and decided to save it for another day.

Debby pulled away, but kept the penis in her mouth, only the tip of his cock remained in her mouth. He felt the high amounts of drool which covered his stick and he felt her tongue rolling in circles around the tip of his penis. He knew that he was so close at coming. How the heck was Debby a virgin with this much skill?

“I’m…I’m close” he told her since he knew that Debby didn’t want to drink him and wanted the load across her face, he was ready to deliver it to her.

Debby let go of his cock and blew over it, his cock was covered in her saliva and feeling the cool air of her breath over his cock made him feel good. He took the cock in his hands and started to stroke it at a quick rate, Debby had her mouth open and her tongue sticking out awaiting his load to cover her. Shelby knew that he was close, he was near his limit. He shot his head back and gave a short yell as he had his second release of the evening.

His cum shot out of his cock and landed on Debby’s face, some landed near her right eye and some also fell onto her tongue. She rolled her tongue around her lips and swallowed what she had. She used her fingers to scoop what was by her eye and then sucked on her finger afterwards.

Then she came up to Shelby and kissed him and cuddled next to him.

“That was the best punishment ever” she said to him as she passed her hands over his six-pack.

“If your ever sleeping over again, be sure to come spy on me again sweetheart” he told her as he kissed her forehead

“And you’ll punish me the same way?” Debby asked him

“Of course and maybe I’ll even be a little bit more rough next time” he said

“Great, I can’t wait”

Three hour later Debby got back dressed and returned to her blown up mattress in Monica’s room. She had no trouble falling asleep after that even if it was five in the morning.

Less than two hours later, a pillow hit her in the face, Debby woke up in a start, she had black bags under her eyes since she barely slept last night.

“Whoa, what happened to you?” asked Monica

“I had trouble falling asleep” Debby told her friend “But I’m going to get you back for waking me up so early” she took her pillow and hit Monica across her chest.

The two girls started to laugh as they hit each other playfully with their pillows. The door suddenly opened and Shelby came in “will you two keep it down I’m trying to sleep down the hall”

“Well, excuse me” said Monica; her tone implied that she didn’t really mean it.

Debby didn’t say anything to him, the thoughts of the hot night they shared together danced in her mind, her eyes went down to his groin, she noticed that even now he had a small erection going which just made her more excited for the next time that he would punish her for looking at him jack off to that picture…come to think of it she wondered who was on that picture. She just had to guess that it was maybe from a dirty magazine.

“Now get out of here you pervert” said Monica as she pushed her brother out of her room “I can’t stand that guy”

“Is your brother always hard?” Debby asked

“Pretty much, he must have been on his computer watching porn this morning” Monica say

Or was he thinking of the hot night we shared together Debby thought, but knowing how Monica and Shelby never got along, Debby found it was wise to keep the loss of her virginity to Shelby a secret from Monica

Later that day when Shelby was out of the house and Monica was taking a shower, Debby opened the door to Shelby’s room. She had seen were the picture fell under his bed and she just couldn’t help it but she wanted to know who Shelby was masturbating too. If it was a porn star or some bimbo from a sexy magazine she won’t really mind that, but if it was another girl like the slut that lived next door to Monica who would go swimming in her pool topless, that would be a different story.

Debby looked under the bed; unfortunately Shelby had already removed the picture. Debby let out a sign, she knew that she was acting like a jealous girlfriend especially when she and Shelby were not even dating or anything, they just shared a hot and magical night, but she would like for it to turn into something more in the future.

A thought came in her head, she looked at the drawer right next to his bed, if this was a picture that he usually masturbated to, she would guess he would keep it handy in an easy to reach location. She opened the drawer and sure enough she was right. The picture was right there on top.

Debby was shocked at what she saw!

The picture that Shelby was masturbating too was a picture of her, Debby Ryan!

“No fucking way” she whispered out. This changed everything. He was into her as much as she was into him. Now she knew that they had a chance at being together, she couldn’t wait to tell him that she found that picture and she was ready to accept the punishment he would give her.

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