“On with it then.”

Annais sighed.  “Piers, you know we don’t have to do this if you don’t want to.”

“Nah,” he said.  “We’re gettin’ it outta the way.  Gettin’ it outta your system.  I’m proper pissed now.  On with it before I change my mind.”

Yes, Piers was drunk now, but he wasn’t when they discussed this.  Annais had joked one too many times about pegging him, and he’d had enough. He agreed to let her fuck him.  If he enjoyed it, great, they found something new to do together.  If not, she’d see how he really felt and leave him alone.

“I don’ like anal,” he always told her.  “Not givin’, not receivin’.  It’s just bloody disgustin’.  Can’t get over the mental image.”

She guessed it made sense. He was a bit neurotic when it came to cleanliness.  He gave it a shot when he was younger as sort of a rite of passage and claimed he was on the verge of gagging the whole time.  He’d even tried it a few times with a few different guys.  He said he couldn’t remember any pleasure due to how nauseated he was.  Yet, for some reason, he gave Annais the go-ahead.  Maybe he just agreed because he loved and trusted her so much.  Or maybe he was hoping that this time would be better. Maybe he really did just want to get it out of her system.  Whatever the reason, he had decided to give it another try with her and she was going to do her best to keep his trust.

With a heavy sigh, he bent over and lowered his shorts.  He pulled them down just enough where it looked like he was ready to pull them back up at any minute.  He had such a cute, tiny little ass.  Annais was always so amused by it, thinking it was such a shame he never let her play with it outside of grabbing it.  

Piers had prepared.  Extensively.  Despite his qualms, he took it seriously.  He’d had a shower.  He waxed. He did an enema, and hadn’t eaten since before doing so.  He bought plenty of lube.  He got completely fucking hammered.

Annais squeezed a little amount of lubricant onto her palm, allowing it to warm from her body heat before generously coating her fingers.  She brought them to him and circled his rim.  He tensed at the feel of fingertips touching such a private area.

“You okay?” she paused to ask.

Piers nodded.

“Can I put them in?”

“Go ‘head.”

“I’ll start with one.”

“I’m not a bloody virgin, Ann,” he huffed.  “I’ve had cocks in there before, y’know.”

She slipped a finger inside, causing him to arc his back and squeeze the pillow.

“Yeah?” Annais laughed.   “How long ago was that?”

“… A while,” he muttered. “Go easy.”

“I will.”

She pushed the digit in, then drew it out to test the waters.  She did this a few times before adding a second finger.  She slowly pumped the two in and out of him, noticing the task was actually becoming more difficult instead of easier.

“Relax, Nez,” she instructed as she tried to scissor her fingers inside of him.

“‘M relaxed.”

“You’re clenching.”

“‘M not tryin’ to.”

“Am I hurting you?” she asked, causing him to shake his head.  “How’s it feel?”

“… Not so bad yet.”

“Did they warm you up?” she asked, trying to converse a little to make things more comfortable.  “The guys you slept with?”  He shook his head.  

“We were dumb,” he admitted. “Didn’t know these things don’ really work as well as cunts on their own.  I was guilty too.  Poor chap.”

“It happens,” said Annais. “I was lucky to get with someone who knew better.”

Her plan worked.  He seemed to be more pliant now.  With her free hand, she felt under him, paying attention to his previously neglected cock.  She frowned when she realized he wasn’t even half hard despite her probing at his inner walls.  Maybe her little fingers were too stubby to reach his g-spot.

“How you feeling?” she asked while stroking him and fingering him simultaneously.

He drew in a shaky breath, then glanced back over his shoulder at her.  

“Ready to get it over with so we can shower.  Go on…”

“Fine,” she said.  “I think you’re as prepped as you can be anyway.”

Grabbing the bottle of lube again, she squeezed another copious amount onto her palm and stroked the little silicone cock that was securely harnessed to her.  Piers insisted all of her toys were far too big, scoffing and calling her a ‘bloody size queen.’  He was also repulsed by the idea of sharing with her.  He claimed he didn’t want to ruin something that she used frequently, so she went to one of Spikemuth’s adult shops to get the smallest one they had available.  (By herself, by the way, despite the fact he usually accompanied Annais when it came to items to use on her instead.)

Once she felt sufficiently lubricated, she held Piers’s hips and teased his entrance with the tip.

“Alright, brace yourself,” she warned.  His head fell to the pillow he was clutching as she breached his hole.  She was slow and careful as she pressed into him, not wanting to startle or hurt him.  Despite her efforts, Piers shook his head.

“Tight…” he grunted.

“Yeah.  You are,” she said.  There wasn’t much length to fit inside of him, and she managed to accommodate it all.  The leather harness that was strapped to her hips was now flush with his bare cheeks. “All in, baby.  You good?”

“‘M alright,” he said.

“I’m gonna fuck you now, okay?”

“Go slow, Ann,” he told her.

“Of course.”

Annais kept her word. The pace in which she thrusted into him would make a Slowpoke look like a rocket.  He didn’t say it was too slow or too fast, so she continued leisurely rolling her hips.  She swore she heard some muffled groans, and they didn’t sound like groans of pain. Curious, she reached in front of him again.  He was just as flaccid as he had been before she started all this.  Piers must have sensed she was disappointed and offered her an excuse.

“Whiskey dick, I suppose,” he muttered.

“Oh, fuck off with that,” she laughed.  “We both know you’re always horniest when you’re drunk…  Nez, tell the truth.  Are you not enjoying this at all?  You won’t hurt my feelings.”

He shook his head.  

“Do you wanna stop?”

He let out a deep sigh, which seemed to be laced with relief.  “… I think so.”

With that, Annais slowly removed her strap from within him.

“Sorry, Ann,” he said, pulling his shorts back up and averting his eyes.  “Thought if anyone could make it work, you could.”

“It’s okay, baby.” She unfastened the harness and let it drop to the floor.  “Thanks for giving me a chance.  Sorry it wasn’t your thing.  Can I make it up?”

“How about we discuss our options in the shower, hm?”

“That works for me.”