Unfortunately, tonight hadn't gone any better. Well, from one point of view one could say we were more successful, but from another point of view one could say the whole thing was a disaster.

It started off well enough. Belle had been a Lot more determined to see this through and seemed to be mentally prepared. She wanted to try her anal insertion flat on her back while holding her own knees to draw her legs up and out of the way. I made sure she and I were both plenty lubed up. I ate her to a screaming orgasm to ensure she was as relaxed as she could get, pulled the butt plug, and swiftly replaced it with my cock.

I actually got through her anus and pushed about two or three inches of cock inside before she clamped up Like crazy and started shaking her head rather violently, grimacing in agony and = yelping,

“Nope-nope-nope-nope-nope!"

You bet I pulled out of her fast and held her while she sobbed in my arms whimpering about how much it hurt. Two minutes later, she was crying while apologizing to me as if the whole thing were her fault. I shushed her and kissed her and reassured her that I was perfectly fine whether or not she was ever able to have anal sex with me. By the time she stopped crying, the determined and stubborn Belle attitude was back as she declared she simply needed to train with the biggest butt plug for a while.

We got into the shower to clean up and rinse away all the regular Lube while applying the oil-based Lube to her pussy. I picked her up, parked her against the wall, slid smoothly inside, and started pumping. I pounded her to a squealing orgasm before she had me turn off the shower, hump her Little body until I was ready to blow, and then park her on her knees so I could cover her face with my creamy Load. Matty's

Little Cumslut licked up what she could, we turned the shower back on to clean up again, and we finally dried off to change into our pajamas.

We were downstairs cuddling on the big couch browsing cable channels when Mother came home. She and Belle had a quick conversation before

Mother excused herself. After finishing a random episode of some TV show I can't remember anymore, we returned to my bedroom, peeled back out of our pajamas, and made love. Ten minutes Later, I asked her, "In or out?"

My Annabelle sighed, kissed me sweetly, and murmured, “In.”

On Saturday, Alice showed up in a cute skirt and spaghetti-strap tank top that showed off her tits quite well. Her hair had been freshly brushed and pulled back with a pink headband. She had a smattering of makeup on, nothing heavy but definitely more than usual. It transformed her face from “pretty" to “eye-catching”, and I had no idea how to react except gape at her with my jaw dropped.

Had she asked me, “What do you think?" or “Do you like it?" or anything remotely like that, I would have complimented her and probably tried to start something sexual. But she made absolutely no mention of her attire and walked past me as if nothing were out of the ordinary, which made me do my best to act as if everything were normal. I couldn't tell if she was waiting for me to compliment her on my own or prove I could treat her as the same old "buddy Alice” she'd always been. The noble part of me wanted her to understand a change in clothing wouldn't change our friendship. Like, I didn't want to treat her as a sex object or in any way make her believe my valuation of her was somehow dependent on how feminine her clothing.

The end result was that I kept sneaking glances at her tits while she stared forward at the TV screen, all her attention on playing the game.

The distraction proved quite effective as she pretty much wiped the floor with me for over an hour.

Finally, Alice switched off the console after her latest dominating victory, gently took the controller out of my hand, and climbed into my lap. Wrapping her arms around my neck, she wordlessly started a makeout session, which I was quite happy to return. Having stared at the cleavage of her D-cup melons in that tank top all afternoon, my boner was quick to make itself quite apparent in my gym shorts. When she discovered it pressing against her mound, she shifted slightly so that she could grind herself against the bulge, started kissing me a little harder, and moaned into my mouth.

Finally, she broke the kiss, panted at me from inches away, and had a rather impish grin on her face.

“Like the outfit?" she asked coquettishly.

"I'd Like to see you take it off, actually," I replied breathlessly.

Alice grinned, the light blue eyeshadow and purplish lipstick giving her an otherworldly quality that made her Look both undeniably familiar and yet exotically sexy. "Good answer.”

I'd later discover that Naimh had taken her shopping during the week, with a few more new outfits still to be revealed. This outfit, despite my reply, she didn't actually take off. Instead, she pulled the front of the tank top down below her nipples along with the cups of her bra, so that the material squished her big tits together and elevated them up beneath my chin. Alice sat up straighter to give me access, and I was quick to duck my head and devour her nipples. At the same time, she helped me yank my gym shorts down to my ankles while I hopped on the couch cushion to create a little room. And rather than remove the skirt, she flipped up the front, pulled the strap of her panties to the side, and started dry humping her soaking wet pussy against my upright erection where it was trapped between our two bellies.

I wondered if today would be the day she finally let me inside, and that electric anticipation (fear?) of the unknown had me on edge the entire time we were together.

Spoiler Alert: She didn't. By all outward appearances, she seemed ready. She was certainly horny enough, and it would only have taken a shift of a couple of inches to bury my entire throbbing dick deep inside her. But for whatever reasons, she held back.

Instead, Alice dry-humped her pussy against my cock until she squealed and climaxed. You know, the term "dry humping" is a complete misnomer when her pussy gets so wet that it feels Like there's a puddle smeared against your midsection and trickling into your lap. Not that I was complaining, of course. When she was done, Alice dismounted, knelt in front of me, and sucked my dick pretty powerfully for two minutes until

I started jetting thick wads of sperm straight into her mouth.

I still didn't know when, or even if, Alice would eventually want me to take her virginity. But for now I was perfectly content to let her set her own pace.