“Uh, more prep?” he said, but it almost sounded like he was unsure.
I looked over my shoulder to see that Forest also caught the uncertainty.
“Has it been a while?” Forest asked, running his hands down Jude’s torso.
“Uh-huh,” Jude said, biting his lip.
I threw the supplies on the bed leaning over Jude and grabbing his cheek to look at me so he couldn’t hide.
“How long?” I asked.
His eyes looked away and I cursed. “Jude.”
“Have you ever bottomed?” Forest asked, confused.
“Try never had penetrative sex,” Jude mumbled.
“You said?—”
“I know, I just never got around to it and it never felt right, but can we not make it a big deal,” Jude said, quietly looking away.
Forest and I exchanged a look. It was a big deal, Jude had gone thirty years without doing this. I didn’t know how I wanted to say this, but I wanted to be the one to give this to Jude, but I didn’t know how to say it without laying all my feelings out.
“Come on, Princess,” Forest said, picking up Jude. “It’s better if we fuck you like this.”
He laid down and helped Jude straddle him.
“You heard me when I said virgin, right?” he chuckled nervously. “I don’t think I can take two cocks at the same time.”
I laughed. “That’s not what he meant, this position will be easier to take my cock.”
Jude looked over his shoulder, his eyes widening. “Oh.”
“Kiss Forest and rub your cock against him as I get his ass ready,” I said, slapping his ass.
“Come on, Princess.” Forest pulled Jude down for a kiss.
I grabbed the lube watching them trying to settle my racing heart at the weight of the situation. This was a big thing for Jude even if he tried to play it off that it wasn’t a big deal. I kissed the middle of his back as I coated my fingers in lube. He tensed when my finger found his hole and I kissed his back again, hoping to ease his nervousness. I slipped two fingers in his hole slowly feeling no resistance and I was grateful he had prepped himself.
“You don’t have to baby me,” Jude groaned.
“A cock is very different from a plug Princess,” Forest said.
“I know, but?—”
I slipped a third finger in Jude making him stop talking.
“Three fingers is not even the same as taking my cock baby,” I said, kissing his back again, letting him get used to my fingers before I moved.
“Oh shit,” Jude moaned, pushing back against my fingers. “I need your cock, Sam, fuck me please.”
Fuck, I took a deep breath, if he kept talking like that this might be over before it had started. I had waited too long to hear those words. I fucked him a little longer before putting the condom on and squirting more lube on myself.
“If you want to stop, just tell me, ok,” I said, kissing his back again.
He looked over his shoulder before leaning up, pulling me in for a kiss. I notched myself in his ass as we kissed, hoping to distract him enough to ease him though the first time. He whimpered as I tried to push past the first ring of muscle.
“I need you to relax,” I said against his lips. “Trust us.”
