Rikki, My Sister’s Friend and More

Rikki, my sister's friend and more...

Jackie's best friend, Rikki, was always around when we were kids. At three years older than Jackie and Rikki, my 21 to their 18, there was enough of a difference in what we did and who we did things with but close enough that we spent time together, too. I wish we would have done much, much more but her clues weren't enough when we were younger. I consummated a long lust over Jackie during the summer after finding out she was as interested in me as I was her. She had found my forum, BrothersInSisters, and found out that I was the admin there. She was a smart girl was our Jackie. After taking her cherry, I sent her back to college with a belly full of cum and the other two holes well used in the short time we had together.

In the meantime, Rikki had asked to meet with me to discuss business ventures. I gave her some tips before Jackie had left when she said she didn't want to go to college yet. These tips paid off and Rikki said things were going very well for her but she'd like to expand. She wanted to stop by to talk about it.

I lived in the pool house behind my parent's place. I used this opportunity to save money for my own place and to enjoy a simpler life. It worked well as I saved more than expected and did much of the work around so everyone was happy with the arrangement. My parents were off on one of their long trips so I had the place to myself. Rikki's text came through to let me know she had arrived.

"Hey, Andy, great to see you again!" She followed this with a big huge that lasted longer than one would expect. I stayed with it as she felt good in my arms.

"Rikki, you get better looking each time I see you."

She really did. Whatever she ate and did for exercise did nothing but good. Her jean skirt and white blouse complimented her tanned skin and beautiful features. She was a lovely lean girl that still looked like the middle distance runner she was in high school. As Jackie told me, she was still fast and in contention for more. She did a twirl to show off a bit more with her ponytail swinging out as she did.

"Come through the house and into the back to my place. Can I get you anything to eat or drink?"

"A coffee would be great. I know you always have the good stuff."

I nodded and asked if she was feeling bold to try something new.

"I love trying new things in my mouth, Andy, you should know that."

Wow. How to respond without seeming really, really, really creepy?

"Wait till you try this new bean then."

Lame but safe. You'd hardly believe that I had fucked my younger sister and stuck the same tongue into her just a week before.

"It will explode with taste in your throat."

She smiled widely. "Oh I hope so. J loved the taste ... of your coffee ... and told me to try it, too!"

Alright ...

Coffees in hand, we went out to my place. She had her laptop out and talked about her newest app idea.

"I want to call it, 'LuvrRunr', a dating app for runners who want to get their heart rate going in many different ways!"

She explained the concept of how people who ran in similar places had similar interests and would be good matches. She had all the concepts mapped out and any questions I had, she answered quickly.

"What do you think?"

"I think you are going to make some big bucks when it takes off."

She sat and smiled.

"I want you to come in as my partner. I need your skill set and I want someone to work with on this and other projects. I know you have a bunch of your own projects on the go but I'd really like it if you came on board with me."

"I like the idea and I like that you have thought this out. I do think it will do very well once it gains traction, too. I do have some other projects that will take my time but I can certainly work with you on this."

"That's awesome. I think it's going to work out great."

She launched into colour and text ideas for the site and app that we discussed and made some changes to be more vibrant and appealing to the demographic. Hours went by as we iterated and by the time we finished, the sun had set.

"Wow, I have never worked this long with someone without a break or moving."

"We can order in some food or I can put something on the grill if you'd like."

"What I'd really like is a quick swim. Would that be okay?"

"Sure. I'd say grab one of Jackie's suits but Jackie is a fair bit bigger than you. Do you have a beach bag in your car?"

"Are you okay if I just do panties and my bra?" She looked me directly in the eyes while she waited for the response.

"I've seen you in everything from Girl Guide outfits to tiger onesies to those naughty school girl outfits you wore last Halloween so I doubt there isn't much I haven't seen before, Rikki."

"You remember all of those costumes, eh? Anything else you remember seeing and liking?"

"Your track singlets are good, too. Like a second skin ..."

"Oh, you liked that? I would wear my undersized older ones 'for good luck' or wore one size smaller. I wondered why you always came to the track meets ..."

That did explain why she was always having to dig the bottom out of her bottom and despite being a small girl, she was always ripe looking. It certainly was why I went to the events.

"The girls I ran with all wanted to be the hottest. One of those bitches even got a seamstress to recut the bottom so it instantly formed a thong back when she ran. In three strides, her ass was completely out and jiggling. The judges and time keepers certainly didn't argue or enforce the rules so we all started to wear a size or two smaller for the same effect or better. For one, I cut out the lining in the crotch and ran without ..." Blushing, she stopped herself, realizing she had gone too far in the description. "Uh, maybe let's just swim ..."

I could tell she got excited about what she had done.

"You can change in the house if you want or use my bathroom."

"No need."

She slipped out of her shorts and top in seconds standing there in the laciest wisps of lace.

"Ready if you are!"

She turned to show she still enjoyed showing her ass and dove into the pool.

"Coming?"

I shook my head and went into my place to grab my trunks. By the time I came out, she was lying on a floating lounger in all her glory.

"This is fantastic. The breeze is so warm tonight."

She arched her back and wiggled her toes.

Her pert A cups and navel piercing raised slightly as she arched. She looked fantastic lying there on the floatie. I drank in her body and realized how hot she actually was. She saw me looking and rolled off the chair to swim beside me.

"Thanks for all the help, Andy, you literally helped me to be who I am today."

She tread water in front of me as she spoke.

"It set my path for going forward and this app is going to be even better with you with me."

The pool lights glowed and highlighted her smile. We swam around a bit and carried on like kids, chasing each other and trying to dunk the other under water.

She swam to the side and climbed the ladder to get out. I followed her and offered a towel.

"I'm going to take off these wet things and give them a quick rinse."

I thought she was going to wrap herself in the towel but she simply unhooked her bra and thumbed down her panties to stand there naked. She went to the outdoor kitchen sink and rinsed off her panties and bra and hung them on the drying lines we had for towels. Walking over to the shower, she rinsed off the pool's salt water then stood there, dripping, in the warm evening. She wrapped her hair in the towel but remained nude.

"I know you used to look at J and I when we were younger. I still remember the boner you got when I was Catwoman one Halloween and had to sit with the candy bowl on your lap until we went out trick or treating. I remember digging around in the bowl with my fingers almost touching your cock as I 'looked for the Tootsie Roll' while you sat there looking at me. I wanted to give you a treat but J wouldn't let me. I even told her we should both treat you ... but she just couldn't do it. I used to give her ideas of how she could show off for you to encourage you to do something but it just stayed like teasing."

The night with the candy bowl was brutal. She had her hand in there and pressed down for what seemed like an hour as she 'looked for a treat'.

She reached out and grabbed my stiff cock while she spoke to me. "Mmmmmm, this is a candy bar I am going to enjoy. How many licks to the center of your Tootsie Roll, Andy? Bet you got bigger since then."

"Remember all those sleepovers we did?"

I certainly did. They were up for hours and hours, laughing and giggling.

"We used to do dares where we'd run out of the room wearing various items to see if we would get seen. Sometimes it was our bikinis, sometimes our panties, and sometimes nothing at all. We used to run down and do a little dance outside of your door to see if you would notice and come out to see us. You never did though."

I had no idea that's what they were doing. I thought they were just being annoying to attract attention so ignored them.

"We did a dare once with a carrot and a timer to see who could suck the carrot for one minute outside your door lying on the floor with legs wide and up on the door frame of your room. If you had opened the door it would have been full exposure with nowhere to run."

Well, damn. Sounded like the girls wanted this as much as I did if not more back then.

"The closest you ever came to doing anything was when you were pushing me on the swing when J took me along on one of your trips in the summer. We had stopped along the way at a park to stretch and pee and I wanted to swing a bit so bugged you till you pushed me. I was wearing a small skirt and no panties because we were trying to flash you in the car but you were either reading or using your handheld game and never saw what we did. So I got on the swing but let my skirt hang to the back so it was just my ass on the seat. It was one of those old wooden one that was like a plank you sit on with chains holding it up. You were pushing me and as I swung up, my skirt would fly up showing off my ass. I know you liked it because you didn't even hear your dad calling to get back in the car."

I did remember the car ride and I did remember checking them out. Both wore skirts and no panties but at the time, thought it was just their 'thing' to do. I liked it and tried to be looking down at my book or game when they moved so I could 'catch' them in action. I saw a lot of both on that ride. I knew why I caught them so many times now. As for the swing, it was a memory that I jerked to many times. I'd guess I spilled about a quart of cum to Rikki's tight ass revealed in front of my face over and over again especially because she let her ass hang over the edge of the swing.

My cock was rock hard from the memory and Rikki's hand. She undid my drawstring and slipped my shorts down. She engulfed my cock with her mouth and slid halfway down as she knelt.

"Mmmmmmmphhhhh ... so good. A bit salty though. Let me blow you while you shower."

She took my cock in hand and led me over to the shower. I got the water going while she knelt in front of me sucking my cock. It was a great blowjob, completely relaxed and passionate. I shut the water off and we moved over to the lounge where I had fucked my sister in all her holes. I lay back and let Rikki continue to blow me.

"Fuck, why didn't we do this sooner, Andy?"

Tell me about it.

"I know you fucked J, Andy. She told me all about it. In detail."

At that, my cock exploded in her mouth.

We cuddled on the lounge in robes in the cooling evening. We sat there with a shared secret. Not only had I fucked my sister every which way but her best friend knew about it and had just sucked my cock. It was a night of unexpected turns.

"Not only did you fuck your sister but you also took her virginity. You fucking popped your sister's cherry! That's so fucking hot in so many ways. I want you to fuck me, too, but unless we get married, you only get my ass and mouth. I am keeping my virginity for the guy that marries me. If you can live with that, I'm going to be on that cock regularly. I'm not a slut but I like showing off. You are only the second guy I sucked off and I have only had toys and vegetables in my ass so I am pretty fresh with a low body count."

She was matter of fact in all this and I agreed. No pussy but two other holes available? Count me in.

She rubbed my cock as she spoke and I was hard in her hand.

"Do you have some lube? I have a hole ready to use."

I went and got the Astroglide from the bathroom. When I came out, she was on her hands and knees wiggling her ass around. A good girl, she had put down a towel to cover the lounge cushion. Like Jackie, she wanted it outside, too. My already hard cock stiffened more as I dripped and rubbed the lube on her. Unlike Jackie, she kept a nice patch of pubes neatly trimmed in a landing strip. While she said I couldn't fuck her, that didn't stop me from tickling her clit as I applied the lube. The deep intake of breath let me know she liked that. I lubed my cock and knelt behind her.

"Go slow please, I haven't played much back there lately."

I rubbed her hole with my head and slowly pushed forward.

"Please, slow, slow ..."

I could feel her pucker open as my penis pushed forward.

"Fuck, fuck, it's in, slow, please..."

The head was barely pressing against her ring as I paused and let her get used of it. Hand on her hips, I waited for her.

"Push back when you want me to keep going."

I felt her wiggle her hips and push back a bit so I applied some more pressure. My head slipped in fully and she dropped her chest to the lounge.

"Fuuuuuuuuuuuuuuuuck yes."

Hands on her hips, I slowly pushed forward.

"Yes, yes, yesssssssssssssssss."

I was in. Now it was the rest of the shaft to go.

"Squeeze some more lube on your cock and my hole, Andy."

It was nearly dripping by the time I finished and she was loving it.

"Okay, start pushing it in."

Inch by inch, I pushed in.

"Is it all in ... ohhhhhhhhhh ... still more???? ... ohhhhhhhh ... you must be ... fuuuuuuuuck ..."

I still had a good two inches to push in but I slid back out to give her the shafting she wanted. A couple of inches at a time and she was mewling with pleasure.

"Get it all the fuck in, Andy, balls fucking deep."

Surprised to hear this, I thrust forward and had my balls against her pussy in one fast stroke.

"Fuuuuuuuuuuuuuuck you are all in me."

I grabbed her hips and gave her a hip bump to get a tiny bit more in. With my thumbs spreading her cheeks, she was opened as wide as she could get.

"What the fuck was that ... that's great."

So I pulled out a couple of inches each time as I fucked her with the full shaft. She was moving in time with me and thrusting her hips back to meet me.

"I wanna ride, Andy, flip over."

I was on my back as she rotated around with me, cock still buried. She was facing away so I could watch my cock sliding in and out of her hole as she used her thighs to ride.

"This is so good and so much better than the cucumbers J and I used together. Ass to ass was amazing ... when she gets back, you'll see how hot it is."

I twitched but controlled the wave of excitement from that statement.

"Can I squat and fuck you?"

With no argument from me, she was squatting down and riding my cock in seconds.

"This is soooooooo ... fucking ... good."

I reached up and stroked her nipples as she slipped up and down my shaft.

"Lightly, touch them lightly they are so sensitive ..."

When I squeezed them, she shuddered and let out a moan. "I'm so close Andy, bend me over that table and pound me."

She stood and walked to the table pressing her tits against the glass and spread her legs apart pulling her cheeks wide.

"Come fuck me like you should have years ago ... hard, fast, deep!"

I thrust in once I lined up. I was balls deep in less than a second and started to hump her hard. The table slid along the concrete until it came to rest against a planter. From there, there was nowhere for Rikki to avoid the cocking I was giving her. I pounded away as she made little noises and wiggled. After she took all she could, she stiffened and grabbed her nipples.

"Cummmmmmmmmmmmmming ..."

Twisting and twitching, she rode the orgasm as I continued to fuck her hole.

"Cum in me, sister fucker, cum in me ..."

Like the explosion in her mouth, I drove deep and blew my first squirt deep in her asshole. This set Rikki off on another orgasm while I continued to blow ropes of cum into her hole. Spent, she lay over the table as I slipped my flaccid cock out. She puffed out a bit of air along with some of my cum. As I watched it run down her thigh, I had to remind myself of my good luck.

We both showered before we had a bite to eat. The pizza arrived and we sat around the pool deck enjoying the night while wrapped in robes.

"I knew it was going to be good but not that good, Andy. I'm glad you were first in my ass and took that cherry. I've got a secret for you, too."

There was more?

"Remember when I said you were my second blowjob?"

I nodded.

"Well, that wasn't quite true. I actually sucked you off before while you were sound asleep. When you came back from a night out with your friends, J and I found you mostly passed out on the couch half undressed. We tried to help you up to your room but you were out. When we were lifting you though, you got rock hard. J and I took turns sucking you till you came. Three sucks then she did three. I managed to deep throat you on my first try, J couldn't. When you started twitching and your balls pulled up, we both licked your shaft and shared your cum between us. You were my first blowjob."

Holy shit. I had always wondered why they looked at me like that after that night out. I thought I had done or said something to them. Turns out, they had done something to me. No lie, I wished I had been more with it.

"I think J still has the pictures of you rock hard. I know she jilled hard to them for a long time after."

Pictures, too?

"I'm going to Facetime her so you can see her reaction when I tell her you know ..."

Well, this was going to be something ... fuck.

"J, are you alone? Yes? Guess what, I just got reamed by Andy the same way you did!"

"Rikki, you are such a slut for him. Did he cum up your ass?"

"It's leaking out now, J."

"When did you get home?"

"I'm not home, I am here with Andy!"

"Fuck, no way. Did you tell him how much you wanted him all these years?"

"Yep, then gave up both my holes just like that."

"Hi Andy!"

"Hey, sis. How's college?"

"Boring as shit. I need to get back there to start up with the two of you on something."

"Hey, J, I told him about my first blowjob ..."

"Fuck, no, you didn't. Andy, I'm so sorry, you just looked so fucking suckable. Fuck, sorry, sorry."

"I just wish I was awake for it."

Rikki had knelt in front of me and opened my robe while I was talking to Jackie. For the third time that night, my cock was buried in her mouth as she sucked me hard.

"Let me flip the camera, Jackie, so you can see Rikki saying sorry."

"Fuck, yes, suck that cock, Rikki!"

Jackie had put her phone on the desk so she could show her own skills with her fingers. She was wet and slippery and before long, her moans and patter had me ready to blow as well.

"Jackie, I am close to cumming. Get that pussy gushing for me when I do."

Rikki redoubled her efforts and it wasn't long before my cheeks tightened.

"Jackie, here ... I ... cum."

As I jerked with a spasm, she did, too. She rode her fingers fast and hard and by the time she was done, Rikki had every drop sucked out of my cock. She was sitting on my lap as we watched Jackie come back to her senses.

"Oh, fuck, I need to get back there. Andy, buy your house and Rikki and I can move in as 'roommates'. That would be fucking awesome."

Rikki nodded in agreement.

"Rikki, did you let him fuck your pussy? You know she virgin in one hole, right?"

"That's for my husband to take, J, you know that. Andy's fine with my mouth and ass unless he decides that ..."

Both girls started to giggle.

"Let me guess, is there another plan involving me and who I marry?"

"Well, you can't marry J, right, but you could marry me and have your spinster sister live with you till she finds Mr. Right. Of course, we'd stay in with J so she didn't get lonely in the evenings or weekends. Imagine how much fun vacations would be ... or a hot tub ... or the sauna ... or ..."

She was a ball of energy that never stopped.

"Andy likes that, I can tell."

"Rikki, let me see Andy lick you a bit."

Well, once again, I did not expect to put on a live sex show for my sister over Facetime tonight but ...

Rikki bent over feet wide apart and wiggled her butt.

"Get yer hot pussy, hot pussy right herrrrrrrrrrrrrrrrrrrrrrre!"

The girls loved ball games so Rikki teased Jackie about her game story with me. But the advertising was true, it was hot pussy and it was right there. With the phone leaning against a glass, I licked and sucked, and ran through some sexual tips I read about on Literotica. Jackie was jilling while she watched her friend's pleasure.

After she grabbed the phone, Rikki stared into the screen and told Jackie, "When you get here, we can do this because I am going to be eating you out every single night. Andy can fuck one of us while the other munches pussy."

I heard Jackie moaning as she sped up the pace. Rikki held the phone over her head so Jackie could see me in action.

I popped up and said, "I miss you sis but Rikki tastes so good, you'll be here soon so don't worry", then got back to my job.

Looking for a reaction from Rikki, I darted my tongue into her asshole. She jumped and almost dropped the phone.

"Andy just tongued my asshole, J! Fuuuuuuuuuuuuuck did you try that with him?"

"That's for Thanksgiving. Maybe we should dress as turkeys and get our holes stuffed, too!"

My cock was rock hard again after all the conversation so grabbing the lube off the table from earlier in the day, I lubed up and pushed it into Rikki's ass.

"J, he's in my ass with his cock. Andy, take the phone and show her."

I panned around Rikki's body to show Jackie everything. By the time I was down to the actual fucking, Rikki moaned she was going to cum.

"You are going to wait till I tell you to, Rikki."

She moaned louder with that.

"I'm going to fuck you good for Jackie first so she can see how that asshole takes my cock."

Both girls moaned at that and Jackie was feverish in her pussy play.

After I pounded her back hole while Jackie watched, it was time to cum.

"Jackie, I want you to cum with us too."

She nodded wildly and kept going.

"Rikki, I am going to count down from five so you girls can cum together."

"Five."

Rikki was squeezing my shaft making a tight hole that much tighter.

"Four."

Jackie was yanking her nipples and was kneeling as she thrust fingers in.

"Three."

Rikki was starting to hum in time with my strokes.

"Two."

Jackie had dropped the phone but her sounds came through clearly as she worked herself into a complete lather.

"One ... cum ... NOW!"

Rikki's contraction around my cock pulled me forward as she arched her back and shook. Jackie's screams could be heard through the small speaker.

As I drank this all in, my own load boiled out and shot deep inside Rikki deep, dark hole. After thrusting a few more times, I stood there, camera in hand and wondered how this came about. More importantly, I wondered why it hadn't happened sooner.

Oh well, two nubile eighteen year old girls who wanted to be roommates with me seemed okay, too.

I slipped out and went with Rikki for the final shower of the evening.

Jackie had signed off wrecked and I needed to recover as well.

Rikki stayed the night in my bed.

Rikki spent most of her time with me after that. I set up some house viewings that she came to with me.

Jackie was on video at each showing to help decide.

It was a good start to what came next.