Tangled Tentacles Ch. 1

Jack stood at the outside of Tiffany’s house, today was his fourth date with her and he was going to ask her to go steady with him!

Jack had been out of the dating scene for some years, a combination of school, working 2 jobs and pretty much life itself saw that his love life suffered immensely.  He was finally done with school, had a semi decent job and was ready to try to find his certain someone. The only problem  was the area that he lived in was more rural and had more couples then singles, meaning finding a girl was pretty damn hard.  Invoking the power of the internet, Jack eventually found and posted on a local singles posting site.

The single reply to his ad ended up being Tiffany, she lived on the far outskirts of town in an old small rental house. What really shocked him was the fact that she was a Tentacle Mamono! A bit of a surprise for sure, but Jack didn’t care, he was decently open minded and her tentacles interested him.  The first date went  well enough, just coffee and chatting. The second was a trip to the local zoo, he found that he was really starting to like her.  The third date was dinner and a movie, afterwards Tiffany admitted to him that she liked him, they shared a kiss outside the theater. Jack honestly wanted more but she said that there was something she wanted to discuss with him next time before anything were to progress.

Now as stood outside her place, he was waiting patiently for her. He text her twice already and there was another car other then hers in the drive way... Jack started to get suspicious. Placing his hand on the door knob he paused, was it really ok just to barge in? A yell from the inside answered his own question. Opening the door, Jack rushed to the sounds of distress. Pushing the bedroom door open, he could not believe his eyes.

There on the bed was a naked human woman face buried in Tiffany’s crouch, licking and sucking at the nectar coming from her dripping opened slit. Tiffany herself had two of her own tentacles buried in the mystery woman’s pussy and ass together. She seemed not to notice him as she thrusted her tentacles in and out of each hole, causing the woman to moan every time she did. The musky smell of sex in the air was overpowering as Jack watched the two. Caught between two warring emotions of betrayal and arrousal, Jack finally spoke,

“Tiffany, w-what’s going on?!”

“Jack?!” Tiffany said, finally seeing him, “Oh my Maou, what are you doing here?!”

“We had a date today, remember? I’ve been texting you... Tiffany, why are you cheating on me? I thought you said you liked me?” He asked heartbroken as the tentacle girl continued to fuck the oblivious woman still between her legs.

“I do! Oh Jack I’m sorry, I forgot about today, I wanted to explain things before all of this...” Tiffany said sadly.

“Explain what? That your cheating on me?” He cried angrily.

“Jack, I’m bisexual... Angela here is my girlfriend, we’ve been dating for almost a year. I really wanted to have a boyfriend too and Angela agreed so that’s why I answered your ad. Look I really really like you, when you told me you were open minded I was hoping you would agree to being in a relationship with me as my boyfriend and still be ok with me having a girlfriend too.... I’m so sorry...I’ll... I’ll understand if you want to break up.”

Jack stared at the scene in front of him.  A part of him was screaming to just walk out, that he could find someone else, have a normal relationship with none of this crazy extra crap. A stronger part of him however kept his feet glued to the floor. He really did like Tiffany, what was going on infront if him was straight out of a porn, it had been a VERY long time since he had been intimate with anyone...

Sensing his hesitation, a sly smile spread across Tiffany’s face. Pulling a dripping wet tentacle out of Angela’s pussy she used curled it at him in a come hither gesture.

“Do you wanna fuck her pussy?” She asked seductively, “Shes very tight... she hasn’t had a real guy in so long, I know she won’t mind, will you?” Tiffany asked down at Angela that was still drinking the Tentacles pussy juice. Angela simply moaned into the tentacle girls pussy in answer.

As if hypnotized, Jack slowly walked forward. Not bothering to answer, he quickly stripped out of his clothes and positioned himself behind Angela.  Grabbing onto his hardened cock he staged it at her soaked entrance.

The same voice in his head told him he was crazy for having unprotected sex with some woman he didn’t even know!  But he had gone too far... he needed this, it had been such a long time since he had sex...

Jack looked up to Tiffany as if asking for permission to begin, but was taken back when the same tentacle that was fucking Angela wrapped itself around the base of his manhood and pulled him into her.

Angela moaned loudly at the new intruder in her pussy, Jack moaned along side her as well. Tiffany was right, she really was tight. He also felt something else along move along side his cock in her, looking down, he saw Tiffany’s other tentacle still in Angela’s ass thrusting away. The feeling of having something else penetrating along side him was unlike anything he had experienced before with sex.

“Ohhh I think you’re bigger then the tentacle I was using to fuck her with!” Tiffany giggled.

“Isent it kinda messed up I’m having sex with your girlfriend first instead of you?” He asked in a moment of clarity out of the sex filled haze clouding his mind.

“Mmm yeah, kinda,” Tiffany said almost conversationally to him as they both fucked away at Angela’s willing body, “But I really want you to be ok with all of this and I figure all of us fucking together would be a really good ice breaker.”

Jack couldn’t argue with her point. This whole thing was something out of one his old teenaged fantasies.

“I promise me and you will have a whole day to ourselves to fuck ok?” The tentacle girl grinned mischievously at him.

“Okay,” Jack breathed, content with her promise, as he continued his assault on Angela’s pussy. Looking down at her, he saw that Angela was now fellating one of Tiffany’s tentacles that was shaped suspiciously like a penis.

“This is so fucking hot,” Tiffany said suddenly. Jack looked over to her to see that she had inserted a tentacle of her own into her pussy.

“Fucking my girl alongside my new man,” Tiffany moaned aloud, “dream come true!”

As they fucked for what seemed like hours, the room continued to fill with the musk of sex, moans and grunts. Poor Jack’s will power finally failed as he felt a powerful orgasm rushing to get out.

“T-Tiffany, I’m gonna cum soon...” He warned,

“Where should I cum?”

“Right in her pussy sounds about right.” She hummed turning her attention over to Angela’s abused posterior.

Angela growled in protest as she bit down on Tiffany’s cock tentacle in her mouth.

“Ow! What did I tell you about biting? You know I can’t help that I have a pregnancy fetish, it’s a Tentacle girl thing! Look I promise I’ll clean you out after, you won’t get pregnant ok?”

Anglea glanced up at her tentacle lover in thought before nodding her head. Poping the tentacle out of her mouth, she warned, “You better get all of his cum out!”

“I promise babe, I will!” Tiffany assured.

Jack felt the tentacle still around his cock begin to twist and squirm causing him even greater pleasure. With a moan, Jack came heavily in Angela’s battered pussy.

“Fuck, he’s shooting a gallon of cum in me!” Angela complained, “You better get all of that shit out, Tiffany!”

Shot after shot, he erupted his backed up load until he collapsed off her, spent.  Tiffany pulled herself down  as Angela collapsed herself on the opposing  side. Sandwiched between her two exhausted human lovers, the Tentacle girl sighed in happiness.

“The cum...” Angela reminded.

“Oh yeah, oops must have forgot,” Tiffany laughed as she brought up a strange looking tentacle, “Now this is really just designed to suck cum out of a dick, but the principal should still be the same...”

“What do you mean, the principal should still be the same?” Angela asked as it attached itself onto her leaking, swollen red pussy.

“You promised that you would-“ Angela’s  protests  were cut off with her own loud moaning as the tentacle began to viciously suck the sperm out.

Jack turned to watch the process, well aware that it was causing his flaccid, juice covered penis to harden.

“Shit, it’s too much, it’s TOO MUCH!  Stop! Stop please!” Angela begged as Tiffany suctioned the cum from her.

Arching her back up, Angela let out a loud, throaty moan as she climaxed. Eyes rolling into the back of her head, she passed out onto the bed. Removing the suction tentacle, Tiffany smacked her lips together as she finished with Angela.

“Damn your cums taste delicious together, I could get addicted to that kind of cocktail!”

“You can taste... from your tentacles?”

”Uh huh,” Tiffany said staring at his now hard cock, “ So, question, and I think we kinda bypasses this earlier but do you wanna be my boyfriend?”

“I don’t think I have a choice at this point!” Jack laughed.

“We all have a choice Jack, that’s what I was always taught. I want you to be mine but you need to say yes first.” Tiffany spoke as coiled her suction tentacle around to be dangerously close to his hard on.

The same small voice of reason clambered for attention in his mind, telling him to GTFO from this tangled mess! Jack squished it down with a vengeance, he was tired of being reasonable, of doing what everyone thought was the right thing- work hard, go to school, be responsible... This time he wanted to be selfish! He wanted to do what he wanted!

Craning his head over, he kissed Tiffany gently and said, “I’m all yours.”

Squealing with delight, she returned his kiss as the tentacle shot out to attach onto his cock. Jack immediately felt a strong pleasurable suction as well as hundreds of tiny tongues licking his shaft as they made out.  Breaking the kiss, Tiffany licked her lips as she said,

”Mmmm her juice off your cock is just as delicious! A little salty but sooo good!”

Even though Jack had just cum, he was no match for her as he felt the familiar pressure building inside.

“You’re amazing,” he breathed, staring into her eyes,  high off the pleasure she was giving him.

“You are too,” She said blushing shyly, as she kissed him again.

With the pressure in his cock finally unbearable, Jack moaned into Tiffany’s mouth, as he  released into his new girlfriends appendage.

Breaking the kiss, Jack was left panting for air as he recovered from the intense ordeal.

“Damn even your straight cum tastes good, I really know how to pick delicious tasting humans,” Tiffany joked. Looking down she saw that he had dozed off, cuddling next to her. A gentle smile spread across her face as she looked over to see that Angela had also cuddled next to her on the other side. Reaching down with a tentacle, Tiffany pulled up the bed sheet around the trio.

“Nap time my loves,” She said quietly as she spread her tentacles out, embracing the two as they slept.  Later she would make some food for them, they would for sure be hungry but for the mean time, she enjoyed the feeling of her lovers snuggling around her.