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OverLooker's Bondage Adventures - Emma & my gift to Mark


I hope you enjoy and please comment.

It was nearing the birthday for one of Emma's close friends. Her friend was turning 16 years old and Emma wanted his 16th birthday to be one he would remember for ever. The boy's name was Mark and he was a pretty good looking boy. I had heard stories of Mark's sexual exploits and met him a few times but sadly never got to experience them that is untill his 16th birthday. Mark was a fan of bondage and perfered being the dominate and Emma knew just what to get him for his birthday.

Emma planned a nice party for him and asked me to help with presents and everything so I went to her house the day before to help her wrap up all the gifts. I showed up around 11:30 AM and we wrapped boxes and packages for a few hours before taking a little break. We finaly finished and Emma said I did a good jobnas she wasted no time pulling ovv her shirt in the middle of her kitchen. She teased me a bit and got me all hard. She stripped me down to nothing and ziptied my wrists behind my back followed by my ankles. I laughed and got turned on untill things started to head south.

Once I was nude and all zip tied up she laughed and explained that I was going to be the last and final gift for Mark as she hogtied me. I complained of course but once Emma jammed the rags in my mouth and secured them in with tape there really wasnt much I could do. So there I was on the kitchen floor of Emma's house naked, hogtied with zipties, rags jammed in my mouth and tapped in. She added the final touch which was a nice cardboard sign around my neck that said 'Fuck me' in red sharpy. Emma rolled me into a large boc by the door and left me there all night untill the party the next day.

Emma's parents drove her to the party along with the gifts including me completly unawarwe I was even inside one of the many boxes. Once there Emma and some friends carried all the gifts and me inside and carried me in to Mark's room. I could hear all the kids laughing and playing games for a few hours then the party started to die down.

Emma was the last person to leave but she didnt until Mark saw the best gift she got him. They made their way to Mark's room and opened the door to see a big brown box in the middle of the floor. Mark asked what it was and all Emma said back was to open it. He ripped open the box and there was cute little me naked, hogtied, and gagged with a fuck me sign around my neck. Mark laughed and kissed Emma. He thanked her and asked her If she wouldnt mind waiting in the other room while he played with his toy. She smiled and walked out of the room as the door closed. Mark took off the sign and undid the hogtie before tossing me onto his bed. He bent me over and slapped my ass a little making it red. He lubbed up and slid himself inside me nice and slow. It felt wonderful to have Mark fucking me on his soft bed.

Two hours later Mark walked out of his bedroom covered in sweat with the largest grin on his face. Emma untied me and gave me some clothes to put on while we waited for her parents to pick us up. Her parents assumed I got my own ride and they counldnt pic me up then never even relized that they drove me to the party too. I made Mark the happiest on his Birthday.

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"Will you stop trying to act like my mom! Your not!" Jake said to his step-mother as he stormed up the stairs the sound of his door slamming echoing down the hall.

"That boy can be so emotional" Clair said sitting down at the kitchen counter taking a deep breath.

"Dont worry about it Clair he probably just had a long day. We are teens and were prone to outbursts." Chelsey said with a giggle as she looked down at her phone.

"Your probably right. It still hurts to not feel like part of the family" Clair said with a sigh.

"You and dad have only been married a month. Give it time" Chelsey said patting her step-mom on the back.

"I just with your father hadnt had to leave on a business trip this soon after our marrage." Clair said.

"Oh well. I'll be home later tonight." Chelsey said heading out of the room.

"Where do you think you are going?" Clair questioned.

"I have a date. I'll be back before midnight" Chelsey explained looking at herself in the mirror running her hands through her brown hair with blonde streaks and fixing up her tight pink tanktop to show off her small but perky breasts and tight jean shorts to show off her tight butt.

"Its a school night you really shouldnt be out so late" Clair protested.

"Its fine. Dont worry about me" Chelsey said heading out of the kitchen and out of the house before her step-mom could protest further.

"These kids are to much to handle..." Clair thought to herself.

- - - - - - - - - - - - - - - - - - - - - - - - - - - -

"Jake? Honey? You in there?" Clair asked knocking on her step-son's door knowing full well he was in there from the sound of video games.

"Just a minute" Jake replied.

Clair heard some movement in the room and a minute later Jake unlocked and opened his bedroom door.

"Yes Clair?" Jake asked brushing off his black t-shirt.

"Are you ok?" Clair asked looking at the beads of sweat on his forehead.

"Yes just fine. Sorry about before I didnt mean what I said" Jake replied running his hand through his dirty blonde spiked hair.

"Thats ok I know you didnt" Clair said with a smile. "Can I come in for minute?" she asked.

"Sure" Jake said hesitantly.

Clair walked into the room and could hear the static from speakers but saw the television was off. She saw that the computer was running and walked over. In an attempt to relate to Jake she decided to see what game he was playing.

"So what game are you playing?" Jake's step-mom asked moving the mouse.

"Wait-" Jake said but it was to late and Clair froze with shock.

Jake had not been playing a game on the computer at all. Clair saw the open internet tab of a video with a boy tightly bound and gagged by a woman. The title of the video read 'Dommy Mom' and she saw other tabs which read 'Incest Bondage' and 'Mom Walks in on Brother And Sister'. Clair's eyes then looked down at the table where she saw pictures of Chelsey in her cheerleading outfit. Some of which were covered in a white goo.

"J-Jake" Clair muttered still not sure what to do as her mind raced to fix her situation.

"Clair its not what it looks like! Thats personal." He rambled.

Finally Clair’s mind clicked and she turned around.

"So you like bondage? You wanna get dominated?" She asked a sparkle in her eye.

"W-what?" Jake said surprised and confused.

"I bet you want me to tie you up and play with you right now" Clair said getting closer.

"Clair- I- your my-" Jake rambled some more his erection clearly showing as his face turned red.

"Your step-mommy" She said grabbing his cock through his pants and pinning him to the wall.

"Cla-" Jake moaned as his step-mother stroked him.

"Thats a good boy. Now tell me what you want." Clair whispered into his ear as Jake's cock slipped out from the cover of his pants and boxers and into plain view.

"Stop it. This isnt right!" Jake said pushing Clair away.

"Dont be all high and mighty now baby. Not after what I just saw on the computer. And dont you dare try and defend those pictures of your sister" Clair said her eyes fixed on Jake a gleam in her eyes.

Clair began to unbutton her blouse exposing her bra shielded breasts slightly. Jake felt torn in half as his body wanted one thing while his mind knew not to want it. Clair walked back to him taking off the last of the blouse's buttons and pressing herself against her step-son. Jake being 6 feet tall looked down at his step-mom ahs she looked up at him. Jake looked at his step mother her shirt now undone her nicely sized breasts pressing up against him as she looked up at him with her deep blue eyes the bands of her short blonde hair covering bits of her face.

"The longer you deny what you want the longer you want get what you desire" Clair said grabbing Jake's manhood again and teasing him.

"I- i - i w- want you to dominate m- me. Bind me up. Gag me. Make me your little s- slut" Jake whimpered as Clair kept on stroking her breasts pressing against him.

"Ok honey just give me a minute" Clair said as she stopped stroking Jake and walked out of the room.

Jake took a deep breath as he tried to recover and understand what happened. After a few minutes Clair walked back into the room wearing a matching pair of red laced bra and panties and holding a roll of silver tape. Clair began to remove Jake's clothes with his held down to his boxers. She then bent him over his own desk accidently hitting the play button on the computer which resumed the femdom bondage video. Clair used the tape and bound Jake's hands behind his back as moans and grunts were heard from the computer. Clair then forced Jake to his knees on the floor. She grabbed his socks from the floor and grabbed his hair pulling his head back to jam the socks inside. She then wrapped the tape around Jake's mouth and head several times.

"Dont you look so cute" She said looking down on her bound and gagged step-son his green eyes looking at her from over the tapegag before a strop of tape was placed over them as well.

"Mmmmpppphhhh!" Jake moaned as he felt Clair's hands on his cock.

"I but you wish Chelsey was here too" Clair said standing Jake up and spanking him.

Jake continued to get spanked until his ass was red. He then felt Clair probing his ass with her lubed finger. She spread the lube with a smile.

"Mmmmppppphhhhh!" Jake moaned as he felt her finger enter him.

For several minutes Clair slid her finger in and out of Jake before adding a second finger and then a third and fourth. Eventually Jake heard a vibrating noise only to feel Clair's personal vibrator slide into his ass. Jake moaned and grunted feeling the socks in his mouth become soaked with saliva as he was punished by his step-mother.

"I cant wait for Chelsey to get home and see you and know what you were doing with her pictures" Clair said with a grin causing Jake to get even harder and squirm at the thought.

- - - - - - - - - - - - - - - - - - - -

"I had a wonderful night" Chelsey said as she unbuckled herself and leaned in to kiss her date in the driver's seat.

"Glad you did. Any chance of getting an invite inside?" The boy asked lifting an eyebrow and smiling.

"Not this time. My brother is home. But if you play your cards right maybe youll get lucky next time." she said seductively before opening the passenger side door and getting out.

Chelsey looked back at the boy and said goodnight and then headed over to her house making sure her date got a good look of her rear as she walked. She grabbed her keys from her bag and unlocked the door and walked inside watching her date pull out of the driveway and drive off out of the corner of her eye. She stepped inside and locked the door behind her.

"Hello Chelsey. How was your night?" Clair said as she walked into the front hall from the second floor stairs.

"It was nice but I'm a little tired" Chelsey responded.

"Well as long as you had fun. I would have liked you to be home earlier though. Your brother and I had a long talk while you were gone." Clair said.

"Thats good. I told you he didnt mean it" Chelsey said with a smile.

"Yes well he really opened up for me when we started talking" Clair continued. "I have something to show you before you head to bed though. How about you go put your purse away first." Clair asked.

"Sure thing I need to charge my phone anyway. Its at 4%." Chelsey said.

The two women walked up the stairs stopping in Chelsey's room so she could put her purse away and charge her phone. She also put on her alarm for school in the morning.

"Now I caught your brother with these pictures. There were also some pictures of me but I dont think you want or need to see those" Clair said handing Chelsey the cheerleading pictures of herself some still with white goo on them. "Your brother was... pleasing himself to them" Clair said.

"What?!" Chelsey exclaimed shocked as she looked at the pictures.

"I already talked to him but I think you need to see him as well. This isnt something that can wait. He is in my room now." Clair said.

Chelsey was shocked not knowing what to say with this information. She then followed Clair to her and her husband’s bedroom where she expected Jake to be sitting waiting to be yelled at and apologize. Clair opened the door and let Chelsey walk in first so Clair could close the door behind them and lock it.

Chelsey took two steps into the room and stopped her eyes wide and jaw dropped. On Clair's bed was Jake but not anything like Chelsey had expected. Jake was completely naked on Clair's bed. His hands were bound to the head railing of the bed as were his feet which were bent upward exposing his rear which had a large red studded vibrating dildo inside of it. Jake's mouth was covered in tape and his penis was fully erect. His bright green eyes stared right at Chelsey as he struggled.

"Mmmmmpppphhhhh!?!?! Mmmmppppphhh?!?!" Jake screamed as he struggled against his bonds sweat running down his gagged face.


"I though he should be punished for what he did" Clair said as she pushed Chelsey further into the room closing and locking the bedroom door behind her.

"Wha-" Chelsey said before Clair cut her off.

Clair grabbed Chelsey forcing her down to the hard wooden floor of the bedroom. Clair grabbed her step-daughter's wrists and bent them behind her back pulling a small roll of black electrical tape out of her pocket that she had taken from her husband's toolbox specifically for Chelsey.

"Ow! What the hell are you doing?!" Chelsey cried as Clair kept her captive's arms bent as she wrapped the black tape around and around wrists.

"You know your putting up much more of a fight then he did" Clair said nodding over to Jake who could do nothing but watch Clair take control of his sister which only made him more excited with no way to hide it.

"You bit-Mmmmppphhhhhh!" Chelsey started to yell before Clair pulled her head back and jammed some kind of rag into her mouth and began wrapping the electrical tape around her head keeping the cloth inside.

"How do your brother's dirty boxers taste?" Clair said with a chuckle as Chelsey struggled on the floor.

Chelsey was then forced back up off the floor onto her knees. Clair's left hand grabbed Chelsey's left perky breast under her pink tanktop while her right hand slid under Chelsey's shorts. Chelsey continued to struggle.

"Be a good girl now. I though this would help us bond" Clair said as she held Chelsey in place on her knees.

Clair grabbed Chelsey's pink shirt and lifted it down to her wrists bound behind her back and expose her bra and perky tits. Chelsey began to blush as she looked up at her brother who stared back.

Clair got up off the floor and made her step-daughter stand up and walk over to the bed. Chelsey was then pushed and bent over the bed. She then felt her shorts and panties being pulled off and looked back to see Clair smiling. Clair then walked over to her bedside table and opened the draw pulling out two large rubber dildos similar to the one inside Jake.

"Mmmppphhh!" Chelsey screamed as she struggled against her tape bonds.

"Now now dont pretend like you dont want this. I know how much of a tease and slut you are at school" Clair said as she coated the two dildos with lubricant. "Do you have a preference which one I use where?" Clair said with a chuckle knowing Chelsey could answer through her gag.

"Mmmmppppppphhhhh!!" Chelsey moaned into her gag of Jake's boxers and tape as she felt the first dildo slide inside her pussy.

"See I knew it. You probably give it out to any boy that asks" Clair teased with a slap on the butt.

Chelsey then began to squirm more as she realized where the second dildo was going to end up. Moving her butt back and forth trying to make the target harder to hit.

"Mmmmmpppppppphhhhhhhhhhhh!" Chelsey squealed as she felt the rubber cock covered in the cold lube slowly slide itself into her ass.

"Look at your older sister Jake. Look at how weak and helpless she is." Clair said as she started to stroke Jake some lube still on her hands from the dildos.

"Mmmppphh" Jake moaned and blushed as he looked down at his sister who was bent over the bed bound and gagged with toys in her pussy and ass.

Clair watched as the two struggled against their bonds trying to fight the surge of pleasures they were getting. After some time Clair began removing her pants to reveal a large rubber strap-on cock she had on.

Clair grabbed Chelsey and began taking off the electrical tape around her head taking some strands of hair in the process. Once the tape was off Chelsey spit out her brother's boxers which were now covered in her saliva. Clair turned Chelsey around and back onto the floor on her knees the strap-on directly in front of her. The rubber cock was thrusted into Chelsey's mouth and down her throat repeatedly making the cock wet. Clair then put Clair back onto the bed and removed her dildos.

"Why dont you help out your brother out" Clair said as she moved her step-daughter's head next to Jake's throbbing manhood.

Chelsey looked up at her brother for a moment. She felt the vibrator being taken from her pussy and Clair from behind with the strap-on. Chelsey could feel Clair get into position putting her hands on Chelsey's hips and the tip pressing against her opening. Chelsey found herself sucking on Jake before she could think and Jake continued to struggle now having his sister's mouth around his cock on top of the dildo in his ass. Chelsey felt the lubricated strap-on penetrate her making her moan her mouth filled with her brother's cock.

"Chelsey, who is your mommy?" Clair asked as she slid in and out of her step-daughter.

"Oo aare" Chelsey moaned as she chocked on Jake's cock in her mouth.

"Jake, Who is your mommy?" Clair asked again with a smile.

"Mmmmpppphhh (you are)!" Jake screamed into the tapegag.

"And dont either of you forget it" Clair ordered thrusting her strap-on deeper into Chelsey's pussy.

Sweat dripped down all of their bodies as their incestual bondage orgy continued. Chelsey continued to take Jake's cock in her mouth feeling the large vibrating dildo still in her ass as well as Clair's rubber cock moving in and out of her wet pussy. Clair looked down on her husband's kids with delight at their situation. Clair took her hands off of Chelsey's hips and slid her left hand down her young body cupping her step-daughter's left breast pinching her nipple. With her right hand Clair touched herself grabbing her own right breast in pleasure.

"Ohhhhh!" Chelsey gargled as Jake's cock pulsed and exploded in her mouth his white load dripping down her chin.

"Swallow!" Clair ordered pushing Chelsey's head into Jake's groin his cock going down her throat once more.

Chelsey swallowed as Clair ordered. Jake breathed deeply as he looked back at his sister his cum dripping down her face. Chelsey was then grabbed by her neck and lifted back up to her knees. Jake looked as his sister and Clair in amazement. Clair held Chelsey tight as she fondled her tits and turned her head forcing her tongue into Chelsey's mouth getting some of Jake's cum on her face as well.

"Mmmppphhh!" Chelsey moaned surprised feeling Clair’s lips against hers.

Clair finally let the girl go and pulled the rubber cock out of her letting her fall to the bed covered in sweat and seamen and panting. Clair pulled out the dildo still in Chelsey's rear and walked back over to her husband’s nightstand and opened the draw. She pulled out a squishy stress ball and walked back over to her female prey.

"C-Clair. Please. Ill be good. Just dont gag m-me" Chelsey panted trying to catch her breath and recover.

"No where is the fun in that?" Clair said with a laugh grabbing Chelsey by her hair and jamming the ball into her mouth.

"Mmmmmmmpppppphhhhhh!" Chelsey screamed as Clair grabbed the roll of tape she had used on Jake and began to mummify Chelsey's mouth.

"Good girl. You look so cute." Clair said ripping the tape from the roll.

Chelsey was to weak to struggle or put up any more of a fight as Clair lifted her up off the bed and leaned her against the bed.

"Now I have some plans for your brother so you can rest for a bit" Clair said taking a strip of tape and putting it over Chelsey's eyes.

All Chelsey could do was lay there bound gagged and blinded with tape and listen to the moans and squeals of her brother as Clair did whatever to him. Clair crawled back onto the bed and slowly removed the vibrator from Jake's now less tight ass. Clair then cut Jake's legs loose which took a lot of pain away from the captive boy who had been like that for some time.

Now honey you do everything I say and nothing more unless you wanna be punished more ok?" Clair said pealing the tape off of Jake's wrists but keeping his gag on. Clair made Jake stand up despite the pain he was in from his anal dildo fucking only a minute before.

"Stand and dont more" Clair ordered.

Jake obeyed afraid of the consequences if he didnt. Jake was then lead into the personal bathroom attached to the bedroom. Clair then took one of her razors and some cream and began to shave Jakes entire body. Jake remained motionless worried that his movement might get him cut. He felt the blades slide down his skin from chest to ankles. He got the most tense when the blades were near his cock which was still erect even though he had already cum. He could not help but stay aroused as his sexy step-mother took advantage of him and his bound and gagged sister. It seemed like a dream come to reality. Once the last bit of hair was shaved off of Jake with the exception of his head Clair lead him back into the bedroom.

Jake's step-mom then opened the closet and looked through the wardrobe. She pulled out all sorts of clothes tossing some onto the bed while others she put back into the closet. Finally she had what she wanted all lined up on the bed. Piece by piece Clair ordered Jake to get dressed in the clothes she had just picked. First was a short little black cocktail dress, next was a pair of tights, and then blonde hair extensions. Clair then took the liberty of adding some makeup and perfume here and there to finish up. While all this was going on Chelsey who was in utter darkness due to her tapped eyes could only hear what was going on. She had no idea what Clair was doing to her brother or what to expect next.

Finally after what sounded like a short scuffle followed by what sounded like her brother squealing through his tape gag Chelsey heard Clair laugh and movement in front of her. The tape was quickly and somewhat painfully ripped off Chelsey's eyes taking some hair from her brows and lashes with it. Chelsey blinked several times as a few teardrops formed and slid down her cheeks. Once her eyes were adjusted she looked straight ahead to see a pair of nicely shaven legs in tights. At first she thought Clair had changed into different clothes but as she looked up she knew that was not the case. Her brother Jake was standing in front of her his body shaved smooth. He was wearing a tight little dress and tan tights. His hands were tied in front of him with a silk scarf and he was still gagged with several layers of duct tape. Jake's makeup showed his rosy cheeks and bright eyes and the extensions didnt look to bad either. He would have made a convincing girl if he wasnt to tall and flat chested.

"You like it?" I think hes really cute." Clair said taking a seat on her bed and admiring her work.

"Mmmppphhh" Jake moaned blushing and looking away.

"Yes you are a pretty girl," Clair said with a chuckle.

"Mmmmppphhhh!" Jake moaned as his step-mother pushed a button on a little remote in her hand causing Jake to blush.

Chelsey realized Clair had attached little bullet vibrators to Jake's cock and anus making him want to fall to his knees in pleasure. Chelsey couldnt help but get slightly aroused seeing her helpless brother being toyed with by Clair. Clair then grabbed Chelsey and stood her up bending her back over the bed.

"Now Jakey. I'll let you pick which one you want. Front door or back door." Clair said giving Chelsey's bare bottom a slap.

This time around Chelsey wasnt that worried since it was her brother and not Clair. She understood they were in a tight spot and he had to do it she relaxed and waited for him. Clair poured lube on Jake's cock after taking off the bullets and Chelsey felt him slide into her.

"Good boy" Chelsey heard Clair say as he slowly slid back and forth. "But lets make this a little bit more fun." She said walking over to Chelsey and pinching her nose cutting off her air.

"If you dont go the speed I want she dosent get air" Clair said cheerfully.

"Mmmmpppphhhh?!?!" Chelsey screamed trying to breathe.

"Better go faster" Clair said followed by Jake picking up the pace.

"Now slow" Clair ordered and again Jake obeyed.

"Deeper" Clair commanded and again her step-son did as told.

"Harder! I didnt say slower!" Clair yelled.

For over half an hour Clair barked orders till Jake finally exploded and pulled out. As Jake fell back he heard some birds chirping outside and looked out the window through a crack in the blinds to see sunlight. Jake then looked at the clock to see that it read six twenty-seven AM. The entire night had passed them all by and the sibling's alarm clocks would be going off within the hour to wake them up for school.

"Wow would you look at the time. I need to make a call real quick." Clair said pushing Jake to the ground next to his sister.

Clair grabbed her cell phone and walked back over to her step children who looked up at her both bound and gagged Chelsey in the nude hair a mess and sweat and cum still on her while Jake was dressed as a girl his boner poking out from under the little dress.

"Yes. Im just calling to say that my kids Jake Mitchell and Chelsey Mitchell will not be coming to school today they both got some kind of bug or food poisoning.-"

"Mmmmpppphhhh?!?!" Clair's captives screamed not being heard by who was on the other line.

"Yes thank you I will make sure they do that. You as well." Clair said hanging up the phone.

"Now get some rest. We are going to have a long day. Or maybe a weak. You know how unpredictable cold can be." Clair said with a laugh walking out of the room leaving her hostages alone tired weak and defeated.
A Little Family Time
* WARNING - - - ADULT CONTENT - - - WARNING*

Jake and Chelsey and their step-mother Clair get to know more about one another then they would have ever expected while their father (Clair's new husband) is out of town on business.

-Please feel free to leave your comments and feedback it would be much appreciated-
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:iconsodiepawp:
SodiePawp Featured By Owner 2 days ago
Thanks so much for faving! :aww:
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:icontanaraq:
tanaraq Featured By Owner 4 days ago  Hobbyist Traditional Artist
Thanks for the watch! ! ! !
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:iconburnup19:
burnup19 Featured By Owner 5 days ago
Thanks for the fav.
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:iconmistermistoffelees:
MisterMistoffelees Featured By Owner Jul 26, 2015  Hobbyist General Artist
Thanks for the 70K fave, OverLooker!... :D
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:iconpfefferschwarz:
Pfefferschwarz Featured By Owner Jul 23, 2015
thanks for faving and commenting!
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