Toby paused reached down between his sister's legs and gently caressed her though her shorts as he continued, "... I'm offering to help you... as long as you let me rub myself on you, between your legs and ass when I get myself off... It's no more than what we've done before... except I'll be taking care of you and rubbing myself on you."
Terri could feel her lady parts tingling and starting to tighten up as she pushed her glasses back up the bridge of her nose looking into her brother's eyes saying, "Ok... but no penetration. I'm still a virgin and I want to stay that way."
Toby smirked when he replied, "I won't put myself in your pussy... but if you want my help... You'll let me cum in your ass."
Terri shook her head saying, "No... it'll be too painful..."
Toby stepped back and turned around raising his hands midway into the air saying, "Ok... I guess you don't want to become a career gamer... besides you and I both know Mom and Dad do anal all the time and she loves it. You and I have both seen it when we use to spy on them and their swinger friends."
Terri nodded and reluctantly said, "Ok... but if it hurts too much or I tell you to stop, you stop."
Terri didn't see Toby smirk as he secured the bolt on the door before saying, "We don't want Mom or Dad catching us do we?"
Toby had a firm erection the entire time they got ready and setup Terri's game console. When things were all set, both were naked and Terri was lying on her stomach on an ottoman and Toby was sitting on the sofa behind her.
He stared at her ass and pussy stroking himself as she started the game and quickly proceeded to race through the first three levels. Toby reached down to caressed and rub her furry outer lips as he watched her work her way through the next several levels.
When she reached level ten she started to play even better, "It's working... your hand feels really good and I can really focus on the game... it's like what you're doing is enhancing my senses and my memory of where things are and what's next. Don't stop... rub my clit... gently... get some lube if I'm too dry."
Toby stood up and walked over their shared bedroom. In the night stand between the two beds he found a bottle of lube and returned to see Terri squirming on the ottoman as her hands gripped the control, twisting it in the air mumbling at the game as she played.
He stood next to her face and said, "Pause it."
She did and turned her head to see his cock dangling in her face. She kissed the tip and he pushed forward forcing it into her mouth. She sucked on it, surprised by how good it felt in her mouth.
After moving it in and out of her mouth three times, she pulled back and resumed her game saying, "You taste pretty good and if what we're doing gets me past that index score I'll give you a blow job when I get my invitation."
"Not if, when..." Toby said before returning to his previous position behind her on the sofa.
He resumed his efforts after putting some of the lube on his finger. He then resumed watched her score climb fast as he circled his sister's hardening clit.
Terri muttered at the game then clearly said, "Put a finger inside me... I need more..."
Toby did not need to be told twice as he slid his thumb inside his sister while his finger continued to circle her now slimy clit.
"It's working... that's the highest score I've gotten at this level... don't stop," she begged before returning to her self-narrating mumbling of the game on the screen.
Toby had never felt the inside of a woman before and he was amazed at the feeling of her hot slippery tunnel. The texture inside her was amazing and so warm around his thumb. He could feel his already hard cock throbbing and the pre-cum streaming down his shaft.
Toby knew there was a pause between levels and he used the next one to squeeze some lube into sister's butt crack. It took a bit of contortion on his part to continue to finger her pussy and to spread the lube around her asshole. He also did his best to feed some of the lube to her tight backdoor without penetrating her.
At the next level transition he finally pushed his finger past her bright pink rosebud.
She yelped and he asked sincerely, "Does it hurt, should I stop?"
Her fingers flew across the controller as she said, "Are you kidding... look at my score..."
She mumbled a few choice words at the game then continued, "... that's the least number of levels I've ever gone through to get that high of a score... don't stop... I'm almost to the index score."
Toby did not stop. In fact he was working his sister's pussy and ass as he watched her play. His involuntary motions were almost in harmony with her arms as she moved the controller around.
Suddenly she screamed, "You DID IT!... I passed the index... I'm going to get an invite..."
Toby pushed hard into his sister's holes as he quietly yelled, "Don't Stop... keep going..."
Terri kept playing taking her score higher and higher.
Toby gently removed his thumb from her ass and used his now free hand to coat his cock with lube and stroke it as she played on.
Terri ignored him when he pulled his hand away from her pussy and used both his hands to spread open her butt cheeks. He continued to watch her score climb as he rubbed his cock between her cheeks, squeezing them around his shaft, and waiting.
The moment she cleared the level she was on, he pulled back and pushed the head of his cock against her brown knot. Terri's head dropped to the ottoman and Toby felt her push back driving his cock into her anal cavity.
Terri moaned and grunted until the game sounds announced the start of the next level. She looked up and returned her attention to the game as Toby slowly worked his cock in and out of her tight ass.
Terri was on the edge of the most intense climax she had ever given herself. It was already better than the first time she saw her parents making love, or the first time she watched Toby masturbate and cum all over himself.
She cleared those distractions and the building climax from her mind and continued her game.
Terri's reflexes were faster than they had ever been and she was playing the best game of her life as her brother fucked her ass with his hot throbbing cock.
The game chimed a sound Toby had never heard before and he grunted, "What was that?"
Terri panted, "I just set the high score... the net high score, not local..."
"SHIT!" Toby grunted, "That's great, but not as good as your ass feels around my dick... this is fantastic... you have to let me do this again... please..."
Terri continued to push the high score higher and higher as she said, "Only if I'm gaming... this is the best I've ever done... and... oohhh... you feel so good in my ass... don't stop... and don't cum until I get to level forty two... please..."
Toby panted, "What level are you on now?"
Terri grunted, "Thirty eight. Level forty one is the highest anyone has ever gotten... I've got to get past it..."
"Go for it," Toby panted, "I think can hold back that long...but not much longer than that... you're ass feels so good...aaahhh..."
Terri played as fast as she ever had, faster than she ever had. Her lightening reflexed pushed her beyond level forty one as Toby held his head down and watched his cock pulling back then disappearing again in-between Terri's butt cheeks.
The couple found the perfect rhythm of her game playing and his hips rocking against her butt cheeks. The harmony of their motion and the briefest of distractions caused, Terri to close her eyes and moan, "OHHHH FFFFUUUCCCCKKKKK I'MMM CUMMMING..."
She dropped the controller to the floor and both of them heard the end of game tonal pattern as her character died. Neither of them cared as she screamed out her orgasm and her body spasmed under her brother's weight as he grunted and thrust hard and deep into his sister's ass.
Terri thought her climax had topped out and she was starting to descend from the most intense climax she had ever felt when her brother's hot cum filled her anal cavity.
The heat from the gooey cream in her ass forced her climax beyond its previous peak and her body naturally pushed back hard against her brother's anal penetration.
The pair grunted and moaned through their mutual orgasms until she went limp and dropped to the ottoman panting. Her arms were dangling to the floor as he leaned back, pulling her with him, as he sat on the edge of the sofa.
Toby held Terri's hips tightly and pressed her ass to his groin trying to keep his deflating erection inside his sister for as long as possible.
Terri struggled to look up when Toby exclaimed, "Fifty Three!... Sis you made it to fifty three! No one's going to come close to that... there's no way you're not getting invited to the tournament now."
Terri nodded before saying, "But... there's no way they're going to let you fuck my ass like that when I play at the convention."
Toby replied, "Well... we will just have to do this over and over again until you can do it without my help..."
"I like that idea Toby, but... not in my pussy..." Terri got very quiet as she said, "I want to save that for Dad... I want Dad to my first... is that weird... or sick?"
Toby moved forward, pushing his mostly limp cock as deep into his sister as he could as he moved on top of her back. He pressed his flesh to hers as he whispered, "I'll help you with Dad, if you help me with Mom... after all they are swingers... incest is just a small step from there and we can keep our activities in the family."
"There's a reason why you're in college and I'm not big brother," she replied, "... you're so smart, and... I'm hungry."
Toby kissed Terri's upper middle back before pushing himself up and out of her. He spread her cheeks apart and watched her gapping ass slowly close as she picked up the game controller. She pushed her glasses back into place and navigated through the screens looking to verify her high score and level had registered as Toby said, "I'm going to take a shower. Order be me a burger and a soda."
Terri quietly said, "Toby... Thank you... you were right, I needed a distraction and with your help I did better than I thought I could... there are already people claiming I cheated on the message boards. Do you know how good that makes me feel?"
Toby leaned down and kissed his sister's cheek before saying, "Almost as good as I feel from helping you."
He whispered into her ear, "I will deny I ever said this, but I love you Sis. Not like a brother... I mean I really love you."
Toby turned around and walked away quickly as Terri rolled over and basked in her Brother's secret comment for a few moments.
Terri found her hand drifting down to her fur and when she realized her fingers were stimulating her clit she stopped and quickly stood up.
She looked around to see if her brother was watching her and she blushed when she saw he was.
Toby smiled at her before disappearing into the bathroom.
She was still somewhat embarrassed and surprised to find she was looking forward to their next encounter as she reviewed room service menu.
After ordering from room service she stepped into the bathroom and joined her brother in the shower wondering what their parents would think of their act of anal incest and if it was any worse than what their parents were doing with their swinger friends.
At the moment Terri's mother Tanya was resting her head on their father's thigh as his penis drifted back and forth on her face. He was sitting on the bed with her laying between his wide open knees. She was laying on her side and behind her, one of the largest, darkest condom covered cocks she had ever had filled her anal cavity.
Tony was holding her leg to his side and he watch her struggling to suck his cock in between her full body expressions of painful pleasure.
Tanya was almost catatonic from the intense sensations she was experiencing and her yipping moans after each thrust into her ass made Tony's cock harder or forced more pre-cum out the tip of his penis and onto her cheek.
Uncontrollable tears of pleasure streamed from Tanya's eyes as their swinger friend Heidi screamed, grunted and moaned from the other bed. Heidi was sandwiched between her husband, Hugh, who was moving his cock in and out of her ass, and another other dark skin hotel entertainer filling her cunt with his massive member.
Another swinger friend, Conrad, was recording everything on their phone, including close ups of the large back plastic covered cock spreading Tanya's ass and filling her up. She struggled through another climax before she pulled herself closer to Tony's cock and kissed the golden drops from the head of his cock.
Tony grabbed the back of her head and forced his cock into her mouth until it pressed against the back of her throat making her gag as she climaxed from the massive intrusion into her ass.
Heidi screamed again and Tony looked over and watched and listened as Hugh grunted his climax into Heidi's ass. Hugh pulled out of Heidi's ass and she rolled off her big black cock huffing and puffing as she recovered.
Tony and Tanya's anal penetrator moved her nearly limp body over to and on top of the other black entertainer. The two men spread her limp legs open and Tony worked the lower monster cock into Tanya's cunt. She was too weak to resist, but she had enough energy to grunt as she was forced to fill her cunt with the rubber coated cock.
Tony moved around and stood over the man under his wife. The other entertainer moved up behind Tanya and pushed his massive member into her ass well lubed ass.
Tanya raised her head to scream and Tony took advantage of her open mouth by forcing his cock as deep into her mouth as he could. Her screams were quickly muffed by his cock pressing against the back of her throat.
Heidi was still recovering from her ordeal as Hugh and Conrad moved her to the edge of the bed so Conrad could feed his cock into her mouth as he continued record Tanya's DP and cock sucking event.
Tanya body was almost limp again but she did not try to free herself or resist. The pleasure she was experiencing was far better than the exhaustion or the occasional moment of pain of her ass being spread open wider than it ever had been before.
She looked up with her eyes at Tony and he knew she was enjoying her sexual abuse.
The entertainer filling her ass thrust hard into her several times as he grunted out his climax filling his condom with his cum. Tony was next and Tanya felt him start to erupt and forced herself to take his cock as far down her throat as she could swallowing ever drop of cum he produced.
The man filling her cunt grabbed her hips and thrust violently into her as he filled his condom until his cum squirted out around the edges of his shaft.
Tanya release her oral capture of her Husband's cock as her head fell to the chest of the man underneath her.
She opened her eyes just in time to see Conrad thrusting his cock into Heidi's throat as he forced her to gag on his spewing cock.
Heidi swallowed and took a breath before sucking Conrad's cock clean.
Tony dropped to the side of the bed next to his wife. She struggled to pet his cock whispering quietly, "Damn that was good... I want to do that again... not now... but again sometime... fuck that was good..."
Heidi looked up past Conrad's deflating cock saying, "Me too... I loved to get DP's and boys... those are some nice sized cocks..."
The man that was in Tanya's ass backed off the bed working his condom off saying, "Just ask for us next time you all are in town... I know I enjoyed myself...thank you."
The one Tanya was laying on asked, "Mam... Would you like us to stay... I'd kind of like to enjoy you from behind... if you're up for it."
Tanya pushed herself up and smiled saying, "You're so nice, but I don't think my ass can take anymore tonight... God you two were amazing."
She looked over at Tony saying, "Thank you honey... they were both a wonderful surprise."
Tony nodded back and smiled as he said, "I know you've wanted to try something like that... and man was that hot to watch... I love to see you cum that long. It's like your brain gets detached from your body and your body just does not stop climaxing."
Tanya nodded saying, "It was almost as good as the first time you and Hugh fuck me like that... More intense this time, but you Hugh and Conrad are special."
Her head flopped back down and she slowly wiggled herself off the deflating cock in her pussy before rolling over limply onto Tony's lap.
She watched with exhausted arousal and desire as the two monster cocks and the men they were attached too departed.
She looked up at Tony saying, "My ass and pussy are still throbbing... thank you again... you are a wonderfully understanding husband, lover and father."
The five friends snuggled and caressed as they replayed the recording of their activities. The ladies were too sore to be penetrated again, but the men wanted some relief after watching the video.
The two women were moved together on the edge of the bed and the three men took turns masturbating onto the women's stomachs, chests and faces. None of them had very much left in their balls. But, all of them managed to deposited a few satisfying drops onto women's bare skin.
After resting again, showering and saying their good byes, Tanya and Tony made their way back to their room. It was late and the found both Terri and Toby in their beds sleeping. Tanya and Tony stepped into their room, stripped and cuddled under the sheets.
Tanya said, "Tony... do you think our kids are going to be as... sexually active are we are? Should we talk to them about it?"
Tony said, "Well, you know I was about their age when my Sister and I started... experimenting... I think maybe we should."
Tony paused and asked, "Do you think they'd want to with us? I mean... we're their parents and it's not illegal anymore... if they did, we could save a lot of money on club dues and keep our activities in-house if you know what I mean."
Tanya pinched one of his nipples as she said, "Leave it to you to take something loving and tender and turn it into a way to save money... Really... You want to have sex with your daughter because it's cheaper than taking your hot, swinging wife to a sex club."
Tony said, "That's not what I meant... and yes... I do want to make love to her... just as I make love to you, often and intensely and with all the love I have in my heart for both of you... Besides, I've seen the way you've been looking at Toby in his swim trunks while we've been on this vacation trip."
Tanya thought for a moment before saying, "If the topic comes up... we will talk about it as a family. I don't want to repress their sexuality or their sexual desires, but I want them to be safe. They are both adults and can make their own choices... so... I don't want to push them into anything, like our lifestyle, if they don't want to do it."
"Agreed," Tony replied, "But if the topic comes up, I want to tell them about me and my sister and you and your father... it's only fair they know everything."
Tanya nodded as she rested her head on Tony's shoulder. She reached down to his groin and rested her hand on his limp cock saying, "If wasn't so sore I'd be doing you right now."
Tony smiled saying, "If I wasn't so exhausted I'd be doing you right now."
***********************
Toby spent the night dreaming of various pleasurable and intense sex acts with his sister and his mother which resulted in a very firm, almost painful erection when he woke.
Without opening his eyes he reached under the sheets and slowly worked his underwear off before he started to caress and stroke his own penis. That was when he became aware of squishing noises coming from the other bed.