Always competing

I like hanging out with Cindy and Sandy. They are cute and funny and absolutely stunning. I have a lot of fun hanging out with them. I have thought about hitting on Cindy – or maybe Sandy … but haven’t done it, because I’m afraid it could ruin the friendship we have going now.

Here they are, arguing as always.


“No, I’ve finished first 3 of the last 4 times” Sandy laughed, referring to a recent track race in school. “But I was ahead of you with several minutes last time” Cindy responded. They were always trying to be best at everything and kept arguing about who was best.

“Which one of you is the tallest?” I asked them, kind of blowing at the fire.

– “I am”

– “No I am”

– “Well, that’s because you’re wearing your heels”

– “Let’s let Howard be the judge of that” Cindy said and pointed at me.

"Sure, I’ll do it” I said, “Stand up”.

They both stood up and looked at me in anticipation.


“Let me take a picture and I think it will be clear to you” I said. I took the picture and showed it to them. “I think it’s pretty much clear that Sandy is the tallest.” I said.

“Damn you Howard, how can you do this against me!” Cindy yelled.

“Well, I have to be impartial and Sandy really is the tallest”.

They both stood for a few moments, Cindy mocking Sandy for not being the tallest.

“Hmm, I wonder who is wearing the shortest skirt – it seems Cindy is, but maybe it’s because your shorter than Sandy” I said.

“No it’s not!” Cindy exclaimed “Sandy is such a chicken, afraid of showing off a little thigh”.

“Let’s see” I said “Turn around”.


They both bent forward slightly to make it seem like their skirts were shorter than they really were. "You were right, Cindy, you ARE wearing the shortest skirt”.

“That’s no fair!” Sandy yelled “It should be relative to your height, my skirt is shorter when you take into account that I’m taller.”

I took a picture and showed them. “Look, more of Cindy’s thighs are visible, so her skirt is really shorter, whichever way you look at it” I explained.

Sandy was not happy. “Maybe it’s because her ass is bigger” she mumbled.

“It’s a draw I guess” I said … “but don’t be so sad, Sandy, if you were competing on breast size, you would be the clear winner” I said.

“ABSOLUTELY NOT!” Cindy said and pulled up Sandy’s shirt as well as her own. I snapped a picture for easier comparison.


“Well, girls, I guess you both have small breasts – it’s a draw again, I think”

“Damn you, let me see that!” Cindy demanded.

She looked at the photo and concluded “My breasts are bigger”. Sandy shook her head “Bullshit, they are just hanging more than mine” she said.

“Girls, girls – calm down. Let me decide, I’m impartial and I say that they are the same size”.

– “Damn you Howard!”

– “Yes, damn you!” Sandy agreed.

“It’s OK Sandy, don’t be sad – you kind of won, as you pointed out, Cindy does have a bigger ass than yours, so we can call you the winner if you like” I said. Sandy smiled a “ha” at Cindy, but Cindy stroke back and showed me her ass.


“Are you saying this ass is big!?” Cindy demanded to know. “I think so, Cindy, bigger than Sandy’s anyway” I said but elaborated “But maybe it’s just the panties that make it look bigger. I’m not sure…” Cindy resolutely dropped her panties and when Sandy saw this, she got right next to Cindy and dropped her panties too.

I took a few pictures for evidence.


“Uh oh, I guess I was too quick there” I said. They both looked at me, waiting for me to explain.

“I’m sorry girls, it could be another draw” I said.

“You sure?” Cindy asked.

“Well, no” I responded “In fact I do think your ass is the same size, but Sandy’s pussy looks tighter, so I think she should be deemed the winner. Yes, that’s it – Sandy, congratulations, you win!!” I said.

“What!?” Cindy protested. “How can you tell anything about how tight her pussy is?”. “It’s obvious to me too” Sandy argued “Your sloppy lips would not touch any cock that entered your pussy – ha!” Sandy mocked Cindy about her big vagina.

“OK, OK, girls, I have a way to decide this once and for all – and this time it will not be a draw, I promise!” I said. Both girls nodded.

“There is only one sure way to test it – I will put my penis in each of you and it will be very clear to me whether Sandy’s pussy is the tightest."

“Well it isn’t!” Cindy said again, “bring it on” she said and laid on the couch with her legs spread. I didn’t let this opportunity pass me and immediately went to the couch, let my pants drop and started inserting my cock in Cindy.


I moved my cock slowly into Cindy and wiggles it around a little in there. Then moved it out and back in a few times.

“OK, your turn” I said to Sandy. Sandy took Cindy’s place and let me put my cock in her. However, just as I was about to put it in Sandy’s open pussy in front of me, Cindy put my cock in her mouth and started sucking it. “You’re cheating” Sandy yelled, referring to the fact that if my cock was freshly sucked, it might slide easier and Cindy’s pussy might feel smoother and therefore bigger.

I agreed that she was cheating and removed her head from my cock, which is what the picture below obviously shows.


I finally got her mouth away from my cock and inserted it into Cindy. It went in smooth but I could feel that it was quite tight.


Now, as I was inserting my cock further into Cindy’s pussy, I wiggled it around and was trying to feel whether this was tighter than Sandy’s. Really hard to tell, actually, they were both tight cunts.

"So?” Cindy asked. “Wait, I am not sure yet” I explained and moved my cock a little more in and out of her pussy.

As I felt around in her pussy with my cock, I could familiar feeling rushing through my body. Oh, I was gonna cum in just a few seconds, no point in stopping now.

“So, who’s the winner?” Sandy asked! “Yeah” Cindy said “You promised you would name a winner!”

I fucked her a little more and then could feel the cum flooding out of my cock and into Cindy’s pussy – as I finally declared the winner to Cindy and Sandy: “I win!”

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