Too Good To Be True Ch. 28

"Well, Cindy is my sister, and Mary has been her best friend since they were like four years old." I began, my cock beginning to stir as I massaged her tits. My other hand started to stray from just squeezing her ass cheek to wandering her crack, which she seemed to like, adjusting so I could reach her derriere better. "She had decided years ago that she'd lose her virginity to me and take my virginity at the same time, and well, she didn't make a move on that until well after I'd had a girlfriend and made that leap. She refused to believe it and still insisted we'd get married."

"That's unfortunate for her, as that's not happening." Berkley purred as my fingers found her anus and began teasing it, my cock twitching almost ready for action again.

"Yeah, but she initially saw the harem as a way to get close to me so she could try to push the other girls out and claim me for herself. Obviously, that didn't go over well with the girls who were already in the harem and they almost denied her entry to the harem." I explained, still teasing her pucker.

"Mmmm.... makes sense." She groaned lightly.

"But Mary realized, I think, that she wanted to be with me more than she wanted monogamy, so she is making the sacrifices necessary to be with me. But she has to prove she can live peacefully with the rest of the harem before they'll let her join." I started using my fingers to gently spread the exterior of her ass.

"Ohhhh.... good to know.... I'll keep an ahhhhhh... eye on her." Berkley moaned as I gently inserted my first knuckle into her backdoor. Berkley didn't care about getting her hands dirty anymore and started stroking my cock, trying to get it ready for her ass faster.

Surprisingly, her ass seemed almost... slick... on the inside. Not slick, like, with shit or anything but smooth and accepting of my finger. I was able to easily get the length of my index finger in her with seemingly no discomfort on her part. I started gently finger fucking her ass as I continued.

"The rest of the girls have at least tried it. Abby is the most opposed to it, but her ass is super tight and she needs a lot of lube to keep it from hurting... I mean, if I was doing this to her without lube, she'd be crying in pain." I informed my panting harem girl.

"Oh, fuck... so you're saying I have a good ass for anal?" Berkley smiled at me. "Maybe we can try it without lube anyway?"

"You haven't taken my dick or anything yet, but yeah. Most of the girls took a while to get used to my finger before they could let me do this. And they all have a discomfort phase they have to work through. You didn't have anything like that?" I asked.

"No, it just felt gooooooooooood." She moaned as I inserted a second finger. "Oh, fuck that stretch feels so fucking good!"

Her hand had managed to get me erect and if I was going to come again, I wanted to do it deep in her bowels.

"You ready?" I asked her.

"I've been ready since you took my panties off." She replied.

I flipped her over planting her face down, and ass up, and made sure the lube was within reach. "You wanted to try it without lube?" I questioned.

"Yes!" She hissed hungrily.

I lined my nasty cock up with her backdoor and slowly pushed the head into her puckered asshole. The asshole itself was a little rough, though it was a little better after I was in.

"Oh... GOD!" She moaned as her ass swallowed my head. "Give me a second... Okay, go for it."

I'd love to say that her ass was amazing and I went in smoothly, but that would be a lie. Her ass started gripping and grinding my cock and I only got in about an inch before we both looked at each other and knew it was a bust.

"Shall I add some lube and see if it goes better?" I asked.

"Yeah, that really doesn't feel good." She admitted sadly.

I reached over to my lube and dribbled some on her asshole, gently pulling my cock almost completely out, then pistoning it to drag the lube in. The results were immediate, and in a matter of seconds, I had my cock in her ass up to my hilt.

"Oh, Fuck! That's so much better!" She moaned as my dick pressed into her depths.

Now properly lubricated, her ass was one of the best feelings in the harem. It was tight and smooth enough to make the fucking feel great and textured and gripping enough to stimulate my cock.

"God! I fucking love your dick in my Ass!" Berkley moaned.

I got into a solid rhythm, driving hard and deep into her making her moan and grab the sheets with one hand as her other rubbed her clit. Her moans rose in pitch each time my cock bottomed out in her ass until she screamed as she orgasmed.

The only good part about the unpleasant verification that we needed lube was that it had left me with a lot of fucking to do before I was gonna come. I kept plowing her sexy tight asshole for at least 20 minutes and lost track of how many times she orgasmed with my dick buried in her puckered asshole.

Finally, my climax would not be put off any longer and I pushed as deep into her ass as possible and dumped my cum up her poop shoot.

"Fuuuuuuuuck....!" She groaned happily as my cock spat six pulses of cum into her butt.

I pulled out and admired the shrinking asshole in front of me. I couldn't help it, I grabbed my phone and took a picture of the cum leaking from her ass while there was still cum, a little blood, and lots of pussy juices leaking from her pussy. To make it even better, Berkley looked back at me and smiled.

I flopped down next to her and we cuddled.

"I'm so happy right now." Berkley cooed as we cuddled. "I was worried that I was committing myself to an... interesting... alternative lifestyle before experiencing anything else, and the fear that maybe I'd be happier with another man, all to myself, has crossed my mind. But... if you can make me feel like this... I'm satisfied."

I smiled and we cuddled until Berkley left to take care of some of her duties.