Lucky This Isn't Real

“I have something to ask you,” Maggie said, pulling me from my thoughts.

“Of course, darlin’.”

“Do you think— I mean, do you think it would be possible to, uh, try anal?”

My cock instantly hardened.

“We can try. Though it might—”

“Hurt?”

“Aye. Are you sure?”

“I’m sure.” She stroked her fingertips up and down my chest. “I would like to try. If it hurts too much, we can always stop. I want to do something different to celebrate. It’s not every day a girl gets engaged.”

“If it gets to be too much, tell me. The last thing I want to do is hurt you.”

Confusion furrowed her forehead.

“What should I do? Get onto all fours? Go over onto my back?”

“I think it’ll be best on your side, love.”

“Okay,” Maggie said, positioning herself onto her side.

I gently bent her legs so that they were up against her chest and started massaging and squeezing her ass with one hand while working her pussy with the other. Before long, she came, shaking gently with a low-level orgasm.

While she was still relaxed, I moved my hand down to her asshole, bringing her wetness with me, and massaged gently in small circles. Maggie moaned as I stimulated her puckered nerve endings, moving my hand from her pussy to her hip as I kept stroking, helping her to relax.

Once she was completely relaxed, I leaned down and used my tongue like I did on her pussy, getting her as wet as I could.

When Maggie was as ready as she was going to be without the help of a butt plug or lube, I lightly pressed the head of my cock against the rosette of her ass. She moaned slightly but didn’t pull away.

I eased the head all the way in before she made another sound. This time it was a bit of a cry.

“You okay, sweetheart?”

She let out a long breath.

“Yeah, I’m okay. It’s a new experience, but it feels good.”

I reached down and stroked her pussy as I gave her a moment to get used to the feeling of my intrusion. When she relaxed enough, and her breathing evened, I started to move again, easing my cock about halfway into her tight asshole.

Leaning down to kiss her on her precious, flushed cheek, I began to move inside her, pumping my cock in and out of her ass, slow and gentle at first, but then gaining in speed until I built up to a steady, moderate rhythm.

There was no objection coming from Maggie. She moaned and sighed in time with my movements.

I played with her clit and moved my fingers down to her opening, and slid two in. She reared back and sobbed in ecstasy.

Her inner muscles clamped down on my fingers. She was close. Gently, I moved my fingers in and out of her while flicking my thumb over her distended clit.

A few seconds later, she lost it. Her ass clamped down on my cock, and her pussy clamped down on my fingers.

She cried out my name over and over again, and my eyes rolled to the back of my head.

She was so wonderfully, beautifully tight and warm that it didn’t take long for me to cum, filling her asshole with my huge, thick, hot load. When I’d given her all I had, I eased my cock out and kissed her on the lips before carrying her into the bathroom and running a warm bath for her.

“Thank you,” she whispered and pressed kisses to my chest. “I never imagined it could feel so intimate and loving.”

“No, thank you, darlin’. Thank you for giving me every part of you.”

When she was finished bathing, I dried her off all over. We got dressed and then took a cab to the sober living facility my dad had been in since finishing rehab.

He still wasn’t doing great, trying to get over decades of heroin addiction. The withdrawal had been brutal when he was first getting clean, and he was already weakened from the infection.

I took Maggie’s hand and kissed her on the cheek as we walked into the reception area.

“Well, look who’s here,” Noel said with a laugh. “The happy couple.”

“He finally made an honest woman out of you?” Liam asked Maggie.

Maggie lifted her left hand, showing off the sparkling diamond.

Jim took her hand and lifted it to the light.

“Granny’s ring looks beautiful on you.”

Out of nowhere, my brothers took me into a back-slapping group hug, only dispersing when a nurse appeared.

“You can go in now,” she said. “He’s waiting.”

Leaving my brothers behind, Maggie and I went into dad’s room, where he sat in a big chair reading one of his damned Trocchi novels. He’d put on weight, and there was a hint of color in his usually yellow complexion.

He lowered his book and looked at us from beneath his reading glasses.

“Well, look who it is.”