Best Wingman Ever

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Okay, I'm just going to go the loo, then I'm ready to go." Jasmine spoke, now more confident than before.

I got up to let her out of the booth, and couldn't help but watch her ass as she walked away.

Sarah looked up from her phone once Jasmine was out of earshot and flashed a smile at me, "It's on."

"Holy shit, really? She's coming back to ours?" Everything suddenly seemed to get a lot more real as I realised I might actually get to have sex with Jasmine.

"Yep. After we get back to ours, I'll make sure you two are good to go and comfortable and everything, and then I'll leave you be."

"Oh my God, thanks Sis. You're the best wingman ever!"

"And don't you forget it! Now drink up, the taxi's just around the corner, so it should be here by the time she gets back."

I downed my drink, then saw Jasmine appear under the archway. Sarah and I got up and made our way over to her before heading outside. Right on cue, a black cab pulled up and Sarah opened the door and gestured for Jasmine to get in the back first. I then followed and sat next to Jasmine on the back seat, as Sarah sat on my other side.

The taxi ride would only take a few minutes, and if it were just Sarah and I, I'm sure we would have walked it, but I was now impatient to get home and finally break my dry spell.

About a minute or so after setting off, I felt a warm hand rest itself on my thigh and looked over to where it came from. Jasmine's eyes locked with my own, and I leant in for a kiss. She still tasted of gin and tonic, and as we continued making out, I felt myself getting hard again.

We pulled up outside of our house and got out of the taxi. I extended my hand to help Jasmine out of the car and walked with her hand-in-hand into the house. Sarah turned the light on when we got inside, and as soon as the room lit up, she noticed the bulge in my jeans.

"Woah, easy there Tiger! Save it for the bedroom!"

I felt a bit embarrassed that my sister had noticed my erection, but with the anticipation of having sex with Jasmine, it soon passed.

We moved into the living room, and Sarah invited Jasmine to sit on the sofa. "Anybody for a drink to help loosen up?" my sister asked, probably more to help ease the tension than anything.

I suddenly felt overwhelmed at the thought of what was about to happen, and knew a moment to myself would help me to collect my thoughts. "I'll get them!" I quickly said, and hurried into the kitchen.

I knew there were both gin and tonic in our parent's drinks cupboard, and since that was what Jasmine had already been drinking, it seemed like the best thing to make for everyone. After pouring drinks, I gave myself a little pep-talk before heading back into the living room. I knew I was only nervous because it had been so long since I'd last had sex, and that Jasmine was definitely the most attractive girl I'd ever had a chance with, and I calmed down as I picked up the first two glasses.

I walked into the living room and froze. Jasmine and Sarah were sat next to each other on the sofa, kissing passionately. Jasmine's hand was slowly creeping up my sister's leg towards her pussy, as the only sounds in the room were those of wet lips pressed up against each other.

My heart dropped as I felt as though my sister had betrayed me. I thought Jasmine was meant for me, and now my sister had stolen her while I was out of the room for two minutes. I'm not sure how long I continued to stand there for and watch, but although I felt betrayed, I couldn't help but think it was also one of the sexiest sights I'd ever seen.

Jasmine stopped what she was doing and pulled away from Sarah. She looked over to me, then patted the sofa next to her as she flashed me a seductive smile.

I went into autopilot as my legs carried me towards her. I put the drinks down on the coffee table, and sat down next to her. Without hesitation, Jasmine switched over and started making out with me. I could now taste a hint of cola on her tongue, and realised it was from my sister's long island iced tea she had been drinking at the bar.

I felt a hand begin stroking my hard-on through my jeans, and opened my eyes as I continued kissing Jasmine to see her fondling me. I noticed her other arm was stretched out the other way, now rubbing between Sarah's spread legs as she watched Jasmine and I.

Surely my sister would somehow excuse herself soon? She told me at the bar that she'd make sure we were comfortable and then leave. We were more than comfortable, and I didn't really want to take things any further while she was still in the room. I'm sure she hadn't planned on this to happen, but she needed to go now.

I focussed back on Jasmine to see that her eyes were still closed, then I looked back towards my sister and tried to communicate silently with my eyes that she needed to go. Sarah did nothing but continued breathing heavily as Jasmine rubbed her through her jeans.

I knew I needed to do something, or would risk Jasmine getting bored of just making out with me, so I reluctantly made my next move despite my sister still being with us. I was determined not to be the one to leave, while my sister got to have sex with the most beautiful girl I'd ever made out with.

I moved my hand to Jasmine's thigh and slowly worked my way up towards her pussy. I felt the fabric of her underwear as I reached my target, when suddenly her own hand moved higher and started grabbing my belt buckle. I momentarily removed my hand from her to unbuckle and unzip myself to give her better access, and then rushed to put it back.

The feeling of bare flesh greeted me as I replaced my hand, and I was confused as I could no longer feel Jasmine's underwear. I quickly realised the feeling of skin was Sarah's hand, as she had started returning the favour and massaging Jasmine through her underwear.

With Sarah making new contact with Jasmine, Jasmine went back to making out with Sarah, leaving me to myself, but with her hand now inside my underwear fondling my bare cock.

Although watching the two girls making out and play with each other was an amazing sight, I knew I still had to get rid of my sister. I had an idea to move things along, and leant over to whisper in Jasmine's ear, "Why don't we move into the bedroom?" I placed my hand on her magnificent breast and gave a gentle squeeze as I spoke. I was hoping as we moved upstairs, Sarah would break off into her own room and I could be alone with Jasmine.

Jasmine broke off her kiss with Sarah, turning towards me and giving me a quick kiss of my own before replying in a whisper, "Okay."

She stood up, then reached out to Sarah and took her hand, "Come on, you too."

My sister looked towards me with an expression I hadn't seen before, but I knew it meant something along the lines of "I know you want me to fuck off, but I can't help myself and can't do anything about it."

Sarah rose from the sofa, and Jasmine reached out to take my hand too. Leading the way, Sarah headed towards the stairs, Jasmine and I following hand-in-hand, and I knew I had to make a decision before we reached the top.

Clearly my sister wasn't going to give up and leave us, so it was up to me to either leave them and spend the rest of the night alone in my own bedroom, or stay with them both and potentially see my sister in a way a brother is never meant to see.

My mind went into overdrive as we ascended the stairs. With each step, the pressure became greater to make a decision. As Jasmine got to the top step in front of me, she looked back and our eyes met.

I knew then, I was going all the way.

Sarah led us into her bedroom and over to her double bed. Jasmine let go of my hand as Sarah sat down and then laid back, bringing Jasmine with her. I stood and watched as my sister laid on her bed, making out with a beautiful woman straddling her hips with her hand under her top, massaging her breast.

Jasmine pushed herself up, then stretched up and grabbed the hem of her shirt. She removed it in one smooth motion, her long black hair getting caught in it momentarily, then crashing back down like a wave flowing down her back. She reached behind herself and unhooked her bra, before releasing her generously sized tits.

My mouth seemed to go dry as Jasmine's magnificent chest came into view, and I'm sure the same happened to Sarah as she froze underneath her.

Jasmine reached down to the hem of Sarah's shirt and started to eagerly pull it upwards. It was a bit more of a struggle to get Sarah's top off as Jasmine sat on top of her, but eventually, after a bit of giggling, the girls managed to remove it. What did make things easier however, was Jasmine finding out that Sarah's bra unclipped at the front, just a moment later.

"Ooh, easy access!" Jasmine playfully teased as she reached out and simply unclipped Sarah's bra.

I watched as my sister's bra flopped open, revealing her breasts. They were something I was never meant to see, but after seeing them now, I can say it should be a crime to keep those beautiful mounds hidden from the world.

I found myself staring, and then suddenly realised both girls were looking back at me.

"You're the odd one out over there!" Jasmine called over softly.

I hastily pulled my shirt up and over my head, then walked over to the bed where the girls were and sat down next to them. I couldn't help but keep alternating my gaze between the chests of each of them, but then Jasmine brought her hand to my face and pulled me in for another kiss, forcing my gaze away from my sister, at least.

"I think we need to get rid of these, too." Jasmine pulled back and laid her hand on my thigh again, then stroked it up my leg, over my excruciatingly hard dick, and up to the waist of my still unzipped and unbuckled jeans.

I didn't need asking twice, and stood to pull my jeans off as Jasmine and Sarah watched me. I was now just in my boxers, and hesitated to remove them in front of my sister, despite my painfully obvious erection making a tent.

Jasmine stayed straddling my sister, but turned around to face me, "I'll get these shall I?" she asked, looking up to me with her big brown eyes.

She hooked her fingers into my waistband, and pulled it outward and down, over my erection. Once they were pulled down far enough, Jasmine let go of the boxers and they fell to the floor.

"That's better," Jasmine cooed, "now lie down."

I awkwardly laid lengthways on the bed, trying not to touch my sister, which seemed inappropriate as we were both in certain states of undress. Sarah seemed to have the same idea and moved out of the way after Jasmine had got off the top of her.

I got more comfortable now that more of the bed was free, and Jasmine kneeled down beside me. She took my now free dick in my hand and started slowly stroking me, as she moved up on her knees and came in for another kiss. I was in heaven as I felt her hand wrapped around my dick, and tasted the sweetness of her lips.

Suddenly she let out a small yelp as she stopped what she was doing.

Sarah had taken the opportunity to remove Jasmine's skirt and underwear as she was on all fours bent over me, which Jasmine clearly wasn't expecting. Jasmine quickly helped Sarah complete her task of getting her naked, then immediately got back to stroking and making out with me.

Jasmine let out a long, sensual, moan into my mouth, and I opened my eyes and glanced down to discover that my sister had started eating her out while her ass and pussy were exposed and pointing upwards. I let out my own small moan at the thought of what was going on so close to me while I was being stroked, even if I couldn't really see it.

Jasmine took my noise as an invitation to take things further, "You want the same?" she asked.

She swivelled slightly on her knees, to bring her head in line with my cock, and sucked the tip straight into her mouth. This time my groan was louder as her warm, wet, lips enveloped my dick, and she started pumping my shaft.

Now I was no longer kissing Jasmine, I was able to lift my head up to get a better view of what my sister was doing, as she continued to feast on Jasmine's exposed cunt.

Sarah was knelt on the floor still wearing her black skinny jeans, using both hands to spread Jasmine's cheeks as she messily slurped away from behind. She opened her eyes and caught me staring at the lewd spectacle, before pulling away and smiling at me while biting her lower lip. Keeping eye-contact with me, she let go of Jasmine's behind, before standing up. She undid the top button of her skinny jeans, then unzipped the front and, without hesitation, hooked her thumbs into the waistband and pulled them down, taking her underwear with them.

Sarah stepped out of the pile of clothing at her feet and stood back up, completely naked. She did a quick twirl to show me her plump, round ass, then stood facing me for a moment so that I could take in the entirety of her exposed front.

Her breasts now hung from her body, but were incredibly perky for their impeccable size. Her stomach was flat and toned, no doubt partly due to the exercise from all the sex she said she'd been having. Her hips gave her exquisite curves which led down to her long, slender legs, and in the middle, her immaculately sculpted pubic hair presented as a landing strip that pointed down to her swollen, pink lips.

The sight before me was almost too much as Jasmine's tongue worked me closer to orgasm. I involuntarily threw my head back and closed my eyes as an electrical charge shot through me. I moved my hands down to stroke Jasmine's hair, and told her, "You're going to make me cum."

She looked up at me and smiled, "We can't have that yet can we?"

Sitting up, she looked backwards towards Sarah, who was still stood behind her, and an excited smile spread across her face as she took in the beautiful body I had just witnessed for the first time too.

"I think it's time for your turn," she smiled at Sarah.

Sarah took her up on her invitation and laid on the middle of the bed perpendicular to me, as I sat up to make room for her. Jasmine straddled Sarah once again, but this time facing the other way so they could sixty-nine. She shuffled back slightly until she was in the perfect position, Sarah opened her legs for her, and she started to devour my sister's spread pussy.

I watched as the two beautiful beings pleasured each other in front of me. The room filled with lustful moans and the wet sounds of tongue on pussy. Even though I wasn't a part of the action in the moment, I was more than happy to have a front row seat to what was surely the sexiest thing to ever happen on this planet, as I leisurely played with myself, backing off if I was getting too close to cumming.

The erotic display went on for another few minutes or so, before Jasmine once again was the one to change things up.

"Come here," she beckoned me, "stand in front of me."

I got up off the bed, then gulped as I stepped in front of Jasmine's face and realised that also meant standing between my sister's wide open legs.

Looking down at the explicit view before me, I stared at my sister's spread lips, shining in the light of the room as they practically dripped with wetness. Jasmine grabbed my hard dick and swallowed it into her mouth again. There was something extra dirty about knowing that the tongue that was now tickling the underside of my shaft had just been inside my sister's cunt just moments before.

Jasmine moaned around my dick as Sarah continued to eat her out. She expertly multitasked as she fucked my sister's open pussy with the fingers of one hand while steadying herself on the bed frame with the other as she sucked my cock.

Pulling her fingers out of the wetness below her, she leaned back from me, as she used the hand that had just been finger-fucking Sarah to grab my dick and lower it towards the forbidden pussy of my sister.

Time slowed down as my dick got closer and closer to penetrating my sister's gaping entrance. I couldn't really fuck my own sister, no matter how good her pussy looked, practically begging to be filled up as it was spread wide open in front of me.

I quickly reached down to take Jasmine's face in my hand, and gently pulled her up to me, "No," I whispered, "I want you."

Jasmine smiled up towards me, then rose up on her knees and kissed me intensely. It didn't last long this time, before she laid down on the bed and turned towards Sarah, "Sit on my face," she instructed her.

Sarah did as she was told, as I positioned myself between Jasmine's now spread legs. It was the first time properly seeing her pussy, as it had always been side on with my sister's face buried in it before, and for a moment, I caught myself comparing it to my sister's. While Sarah's was pale and puffy, Jasmine's was quite the opposite, her cleanly shaven dark skin contrasting with her pink inner lips.

I lined the head of my dick up with Jasmine's warm awaiting pussy. Pushing forward, I felt just how wet she was. My sister had done a really good job of getting her ready for me. Jasmine's cunt seemed to pull me in deeper by itself, hungry to take in every inch as it swallowed me.

Feeling her surround me, I had to pause for a moment to catch a breath, and looked up to where my sister was, happily sitting atop Jasmine's face. I could see Jasmine's tongue working away at Sarah's exposed pussy, lapping up the sweet juices as they coated her face and chin. My sister opened her eyes, looked towards me, and smiled. I knew we'd do a little bonding tonight, but I just expected it to be over a couple of pints, not by fucking the same beautiful girl at the same time.

I could feel Sarah's eyes look over me, as her gaze drifted down towards where my dick disappeared into Jasmine's wet pussy. I did the same and took another opportunity to stare at my sister's naked form. Knowing my sister shouldn't be seeing me like this, and vice-versa, I felt a little flutter of naughtiness in my stomach, heightening my sense of lust and desire. I pulled back far enough to let my dick slide out of it's warm resting place, before grabbing it and stroking it in a lewd display for my sister.

Sarah beamed in wonderment at the show I put on for her, apparently getting the same thrill from the taboo act as I did. I plunged my hard cock back into where it came from much harder and faster than before, and a harsh, guttural sound came from Jasmine's mouth, muffled by Sarah's cunt as it pressed into her face.

This also seemed to have an effect on my sister, as she threw her head back in ecstasy and breathed out the words, "Gonna cum!"

Sarah's passionate outburst spurred me to up my rhythm, and I started pounding ruthlessly at Jasmine's cunt as my sister's orgasm built.

As I pounded away at the pussy before me, I almost forgot about the rest of Jasmine, and I focussed solely on my sister. Right in front of me, she rocked her hips, grinding herself into the eager mouth below her as she cried out in pleasure. I wished it was me making her scream like that, and fucked Jasmine harder in some sort of attempt to contribute to my sister's orgasm.

Sarah fell forward, weakened by the intensity of her climax, and her hand clutched at my own where I was holding onto Jasmine's hip. She fell against me, her face pressing into my chest, and I slowed down my rhythm so as not to hurt her.

Sarah stayed collapsed against me for a moment as she caught her breath, before looking up at me with a contented smile. I used my free hand to gently push back the hair that covered her face, "You okay?" I silently mouthed at her. All she could do was nod, before she struggled to push herself up and flop down to the side.

Keeping my dick inside her, Jasmine leaned over towards Sarah, took her face in her hand, and pulled her towards herself. She kissed her again, as if to thank her for cumming for her, then broke off and laid back down to finish getting fucked.