Dessert

I cannot resist the temptation to tell Millie to go make me a sandwich. She is in her French maid outfit, it is a food themed evening, and besides, I am getting hungry.

Millie returns from her kitchen with a big sandwich she has cut in half, so we share that accompanied with some red wine she has brought,

We relax for a bit, then Millie asks me if I am ready for desert and hands me the last envelope.

Millie is standing next to the bed as I open the envelope, and she seems really nervous.

I open the third envelope, and it reads:

"Your desert is to fuck me in the ass in one position of your choosing, you can cum wherever you want"

I notice Millie has changed the card, and she has crossed out "one position of your choosing" and written "missionary position" and there is some more writing as well from her on the card:

"Please be gentle Matt, I am not very used to anal and your dick is really big".

I look over at Millie where she is standing next to the bed, she looks nervous but determined. She has one hand moving around behind her ass, and I realise she is in the process of lubing up her ass and is using her finger to stretch out her ass and push the lube in.

I reach over and give Millie a kiss, and Millie gives me a nervous smile, then sits down on the edge of the bed, grabs a pillow that she puts under her ass, then lays back, holding her legs high. Millie looks at me for a while, then says:

"I want you to fuck me in the ass Matt"

I come out of the bed and stand in front of her, her ass is perfectly aligned with my dick, but I pull her a bit closer to me. I put a bit of lube on my dick, then press it gently but firmly against Millie's sphincter, but her ass does not open up. I apply a bit more pressure, and the head of my dick slides into Millie's ass. Millie moans a bit from the pain of her ass being stretched by my dick, so I hold still for a while, letting her ass adjust to the presence of my intruding dick.

After a while, I slowly start sliding my dick into Millie's ass, Millie's hand is on my thigh, guiding the pace of her anal penetration so it is not too fast. I finally get my whole dick in, then slide it about half way out, then push back in again.

Each time I slide my dick out, Millie's body relaxes, like it thinks it is about to escape the intruder into her ass, and then as I push back in, Millie's body tenses up again.

I can tell that this is a tough experience for Millie, but she is being a real trooper about it and taking it in the ass like a champ even though she is nervous and her ass must be hurting.

I don't want to fuck her ass for too long as I hope to fuck Millie's ass again in the future and that is unlikely to happen if I prolong this for too long, so I sacrifice my enjoyment of slow fucking Millie's ass and increase my pace of fucking her ass.

But then, the miracle happens, and I can feel Millie's sphincter start to dilate and open up, which means Millie is no longer in pain from the ass fucking she is taking. Millie's moans of pain change into moans of pleasure, and she is starting to meet my thrusts into her ass by moving her hips, even grabbing my ass and pulling me deeper into her ass.

Millie screams: "Oh yes, that is good Matt! Fuck me in the ass!"

"Yes! Yes! Fuck me in the ass! Yes! Yes!"

I look down, see my dick in Millie's ass, see her big tits bouncing around from the ass fucking I am giving her, and this sight of me fucking this big titted MILF in the ass brings me over the edge and I cum. Millie let's out a brief moan of disappointment when she feels me cum, she wanted to be fucked in the ass longer!

As I collapse on top of her, my dick still in her ass, she kisses me intensely, saying how wonderful that was.

Millie walks of to the bath room for a shower, and I take this opportunity to check my "to do" list which is in the pocket of my pants, have I completed it all?