"Because we will take ye here, we will fuck yer arse and yer pussy at the same time."
"Now?" she asked turning her head and looking up at Connor.
"Nay, lass. We have to train yer arse to take us."
"She's tight, Connor," I affirmed.
Rebecca moaned as I slowly worked the plug into her. It was quite small, perhaps the thickness of my smallest finger, but to her it must feel quite massive. 'Twould take time to stretch her open for both of us to claim her, but based on her responses to little hints of pain with her pleasure, I had a feeling that arse play would be something she'd enjoy.
Continuing to circle her hard clit, she relaxed even more and the plug slid in all the way, the narrowed valley allowing her body to close most of the way around it with a flange that remained outside of her so it could be pulled free.
"Good girl," I said. "Ye took yer first plug so well."
"I want to see," Connor said.
I stood and moved out of his way.
"Ah, lass ye're dripping wet again." Connor focused directly between her legs, then lowered himself heavily into the chair I'd vacated. She tried to bring her legs together and sit up, but Connor would have none of it. He tugged once on the end of the plug and she gasped, her eyes flaring wide. "Did ye like having yer arse filled?"
She shook her head but said nothing. "Ah, lass, yer body never lies." He stroked a finger over her inner thigh, slippery from her arousal, and then slid a finger into her tight channel.
"So greedy, lass. Ye're squeezing my finger. Do ye need to come again? Dash's mouth wasn't enough for ye?"
"I...I—"
"Shh, it's all right, lass. We know what ye need." Connor stood and undid the front of his pants, his erect cock falling into his palm. "A big cock."
Stepping forward, he lined himself up with her very eager opening. Slowly, as she had a plug in her arse, he slid in all the way to the hilt. Rebecca cried out and Connor groaned. Leaning forward, he placed a hand once again beside her head, leaned down and kissed her, his hips beginning to slowly move.
"So tight, lass, with the plug in yer arse," he whispered. "Imagine what it will be like when it's me in yer pussy and Dash fucking yer arse."
She moaned and arched her back.
"That's it, lass. Take it. Take what I give ye, what Dash gives ye."
She did. It was beautiful to see her surrender, to watch as she lifted her knees to squeeze them against Connor's hips, to hear her breathy cries of pleasure, to watch her body stiffen as she gasped through her pleasure. Connor came quickly, for she must have been unbelievably tight. Kissing her forehead, he slowly slipped from her body, stood and exhaled loudly. "Fuck," he muttered as he put his pants to rights. "She's insatiable."
Rebecca lowered her legs so they dangled off the edge of the table, then hissed out a breath as the plug nudged into her, brought her hands up to her face and began to cry. All of her emotions, the excess arousal, had to bleed off somehow and her orgasms weren't enough, or perhaps they were too much. Connor pulled her up and into his arms, sat down in a chair and held her, letting her cry. It was a short jag, lasting only a minute or so.
"Shh, we are so pleased with ye. Ye are fine. Dash, however, isna doing so well. Look, lass, look."
He pointed to the cock stand that was uncomfortably pressing against the front of my pants.
"Look what ye do to me, sweetheart." I undid the front of my pants and pulled my cock out, gripping it at the base. "The taste of yer pussy made me hard. Filling yer arse made me harder. Watching Connor fuck ye has me all but coming in my pants. Since yer pussy's most likely sore and ye've been through enough for now, ye can watch me come."
I began to stroke my cock, finding a rhythm familiar, a pace I knew would be pulling the seed from my balls readily enough.
"You can...come without being inside me?" She sniffled and leaned her head against Connor's chest. She wasna sitting upright any longer, which was a good sign.
"We can, sure enough, but the feel of yer sweet pussy milking the seed from my cock is like nothing else," Connor told her. "Or your mouth. As Dash made ye come with his mouth, ye can take a cock in yer mouth and make a man come."
Connor was instructing her all the while I worked and rubbed my cock.
"Ye can also grip a cock in yer hand and do it."
"Why does he look like it hurts?" Rebecca asked. My hips started to buck into my thrusts, the orgasm building at the base of my spine and into my balls. They drew up against my body.
"It feels good, a painful pleasure."