“Where?”
“Kiss my feet,” I whispered. “Kiss the backs of my legs?”
“Yes.”
Would Bobby come looking for me if I stayed away too long?
“Are you thinking about it?” he said.
I moaned a little into the phone. I was fingering myself like crazy. “Then you’d put it inside me?” I said.
“Yes.”
“Would you let me get used to it first, before I called him?”
“If you want.”
“When?”
“Tomorrow,” he said.
“I thought you were busy?”
“I want you now.” He said it, plain as day.
“Bobby’s still home.”
“Are you seeing him tomorrow?”
“At night,” I whispered. “He has to go see his family tomorrow.”
“I’ll come over then.”
Of course that’s what I wanted him to say. He was coming over tomorrow to take my anal virginity.
Suddenly Bobby knocked on the door. I froze with my finger against my clit and the phone digging into my shoulder. “Hey, honey?” Bobby called. “Katie, you okay?”
“Yes, baby,” I called through the door. “Allison called to tell me something.”
“Alright.” I heard him shuffle back down the hall.
“I should go,” Tom said.
“Wait,” I said.
“I have a lot to-”
“No,” I said. No meant no. Tom stopped talking, didn’t protest. I could here him breathing over there. How badly did I want him here? I continued to stimulate my clit, alternating back and forth between rubbing the clear juices into my labial lips and rubbing myself.
“Are you going to cum?” Tom said.
“I think so,” I whispered.
“Will you let me hear it?”
“Yes,” I gasped.
“Are you thinking about me in your ass?”
“I’m thinking about you in my pussy.”
“Think about me in your ass.”
“Ah,” I said.
“Pushing the whole thing inside.”
“Ah.”
“Inch by inch.”
“Yes-”
“Call daddy.”
“Yes, daddy.”
“Tell him you’ve got a friend over.”
I growled as my finger sped furiously over my clitoris.
“You’re perfect, Cat.”
“Don’t call me Cat.”
“You’re perfect.”
“Awnh.”
“I want to cum all over your back.”
“Pull it out and cum on my back.” I arched my neck; briefly I saw myself in the mirror. I’d thrust my chest out and my breasts were hanging away from my chest. “You should see me now,” I said. I could hear him breathe. My right hand was deep inside my bush. “Make a great picture,” I gasped. I was going to cum. “Rub it into my skin,” I whispered. “Fuck me,” I said. “Fuck me.”
“Tomorrow, say it.”
“Tomorrow,” I said.
“Tell me what you’ll let me do.”
“Tomorrow I’ll let you fuck me up the ass!” That did it. I felt my pussy open and I came for him, came over the phone, the floodgates were released and I felt myself warm and wet. “Ahn,” I said. “Oh God, I will…” He hung up. He stayed exactly as long as he told me he would. What would I tell Bobby I was doing tomorrow? He wanted me to come see his family.
* * *
He kissed the soles of my feet. He’d let me shower and then he’d toweled me off.
He didn’t say anything when he arrived. He just put the money on the table and I led him upstairs.
I was wearing a cotton t-shirt and nothing else.
He rubbed the cheeks of my ass with care, got deep into the skin. Before I knew it he was giving me a full on massage, carefully working into the knots and tensions in my back. Unconsciously I’d begun to drag my foot up and down his leg. He still had his pants on.
He bent down and kissed the back of my head, breathed in my smell. I sunk my head down into the mattress and let him work the muscles in my shoulders, massage my shoulder blades, work out the kinks in the vertebrae of my spine. I opened my eyes and looked at my dressing table, at the five hundred that was there in the sunny daylight. Tom squirted more oil into his hands and worked it down my sides. Then he slid his fingers up my buttocks and separated my ass cheeks.
“Mm,” I grumbled.
“Relax,” he said. He bent low and blew against my asshole.
My sphincter went tight. I turned over my shoulder. “Don’t do that!” I said, and laughed. He’d actually made me laugh. Our eyes met when he slipped a slick thumb up into my bottom. “Ah,” I said. I kept my gaze locked with his and he pushed the thumb deeper into my asshole, pulled it out, worked it gently against the walls of my anus.
“Relax,” he said. “Let go.”
“I’m trying.” I looked down to see the bulge in his pants. “Take your pants off,” I demanded.
He pulled his thumb out of my ass and undid his belt. With no underwear in the way his dick sprang up to meet me.
“Put the condom on now,” I said.
“Alright.” He went over to his gym bag. “Put a pillow under your stomach,” he said. I watched him bend down and watched the muscles ripple over his back and side. I reached over and took one of my pillows and set it under my belly. I watched him wrap the condom over his penis and come back to the bed. He got up behind me and the bed sank so that my ass lowered to meet him. He squirted some more KY into his palm and worked it into my asshole.
“Oh!” I said. He slid his ring finger in, then his middle. I realized I’d have to call my father soon.
It was strange having Tom’s fingers up there. It was weird, not what I’d call pleasurable yet, just weird. I felt violated, which always made me hate whoever was asking me to do this and why I’d never gone all the way. I wondered if that strangeness would go away or if it would feel better or if it would just hurt the whole time. If it hurt maybe I could do this without letting my dad know. If it felt good I’d be in trouble.
But this time, unlike any other time, there was an understanding between us. This wasn’t meant to be beautiful, open up any doors or ascend the relationship to a higher plane of existence. It was sex, down and dirty, slightly demeaning, but balanced as well as it could be. Maybe.
The minutes flew by and I finally relaxed enough back there for Tom to be satisfied. I heard him squirt more KY but he didn’t rub it into me. I heard him rubbing it up and down his shaft. The slick sound of it coating his dick, and his hand slipping up and down the head, down the latex to the base, aroused me. I contemplated asking him just to fuck me, to leave my ass alone, but that wasn’t what he’d paid for.
Then his cockhead was between my ass cheeks.
Tom spread my buttocks far apart.
“Do you have the phone, Catherine?”
I pulled my cell phone from under my breasts and showed it to him.
“We’ll go slow.”
And he did. Tom grabbed hold of his dick at the very top and worked it against my anus. I was so lubed up back there and he himself was so wet that it had no problem sliding into the tip of my sphincter.
“Ahn!” I sighed.
“Easy,” he said. “Relax.”
“Yeah…” I tried to relax. I couldn’t all the way but the KY took care of most of that. He was filling me, I realized. He was sliding in. He was pushing in. It was so weird being filled without feeling him in my pussy. I felt suddenly like I had to take a shit. But that was him, that was him taking up the empty place in my ass. “Ahhhh,” I hissed.
“Alright?” he asked.
“Mm,” was all I could say. Now it started to hurt. He was in more than the first few inches and my sphincter was trying to accommodate the full length of his prick. “I don’t…” I started. “I don’t think I can… take you all the way…” I was blowing air through my cheeks.
“You’re doing good,” he said. “I can stop here.” He pulled out a little and pushed back in.
“Ohh.” This might be a problem. How could I talk to my father with a dick up my ass?
As if reading my mind, Tom said, “Call him.”
I’d planned this out. I tried to focus on anything but Tom back there. He pulled out a little, pushed in a little. If he kept it up like that I’d do okay. I pressed the speed dial on my phone and called my dad up. He was in the city today working in the office. This was the hour he usually took for lunch, but he seldom ate a full lunch, and spent most of the time planning out the rest of his day. I heard the first ring.
“How long do you want me to do it?”