“I’m afraid it will hurt.”

“Well it will if you aren’t relaxed, but trust me, if you are horny enough and prepared by someone who knows what he is doing, it will only be slightly uncomfortable for a couple of minutes. Then it will be pleasure beyond your wildest dreams. It’s something you can’t possibly imagine until you actually experience it yourself.”

My best friend Amy lay in front of me, her long legs hanging off the edge of the platform built into the wall that our college liked to call a bed. “Yeah, therein lies the problem. I don’t have a boyfriend, so I don’t have someone who knows what he’s doing.”

“Sure you do…” I looked at her like she’d suddenly lost her mind. “Don’t look at me like that. I’ll let you borrow Jeff; he definitely knows what he’s doing.”

“I realize we share everything Amy, but don’t you think that might be going a bit far even for us?”

“Well, the way I see it Gabby, you have three choices: Use him, do without…”

“And the third choice?” I prompted as she hesitated slightly. “Me with a strap-on.”

“Damn,” I muttered softly. “How am I supposed to choose between the two of you?”

Amy and I were not only best friends, but we also shared each other’s beds from time to time. Like I said, we shared everything. “He’d be a better choice… at least until you got used to it,” she assured as her hand lightly traced along my calf muscle. “He’s long but not too thick… and he feels much better than a piece of plastic or silicone.”

She sat up and tilted my head so our eyes would meet. “But don’t worry baby, once he gets your ass used to cock, I’ll fuck you anytime you want it.” A shiver raced through me as she leaned close and brushed her lips across mine. I opened my mouth, wanting to feel her tongue sweeping against my own, but the slamming of the front door to our dorm room alerted us that one of our other room mates was home. We quickly separated before Anna blew into the room.

“Hey guys,” she said as she plopped into the desk chair. “Boy, I am so bushed. Matt gave me quite a work out last night.” Amy and I looked at each other, both of us mentally rolling our eyes as Anna regaled us with unwanted details of her boring sexual escapades with her boyfriend.

“Man, I thought she’d never shut up,” said Amy as Anna bopped from the room to take a shower. “You think she’d have figured out by now that we aren’t interested in her stories considering the blank stares we give her.”

“Maybe next time we should just tell her to shut the hell up and get out.”

“Good idea,” I replied. “Now where were we?”

“I was about to call Jeff and tell him his expertness is needed tonight for your ass.”

“That’s not exactly the where I was thinking of,” I responded with a pout. She giggled softly as she reached for the phone.

“Later baby, I promise.” Amy spoke for a few moments and then placed the handset back on the base. “It’s all set. He’ll pick you up in the commons at seven and take you back to his apartment.”

I wanted to ask her again if she was sure she wanted to lend me her boyfriend for the night, but once Amy had made her mind up about something, there was no shaking her.

***

“You don’t have to do this you know,” I told Jeff as he opened the apartment door. “What? And turn down the chance to introduce a beautiful woman to the joys of anal sex? Seriously babe, there was no talking me into it; I was chomping at the bit.”

I followed him down the hall and into the bedroom. My stomach did a flip-flop as he turned on the lamp on the bedside table and killed the overhead light. I knew I was in good hands, but my heart still raced a tad. I wanted this but it was a little weird being with Amy’s boyfriend. However, when his lips touched mine, and his arms circled around my waist and pulled me into the warmth of his hard body, I completely forgot about any misgivings I had about the situation and simply melted into his embrace. He certainly lived up to everything Amy had said about him. He wouldn’t let me do anything for him.

“Tonight is all about you,” he stated as he laid me on the bed and planted hot kisses down my skin as he removed my clothing piece by piece. His joined the pile of mine on the floor and he lay on top of me, his skin feeling delicious as it pressed against mine. I arched beneath him as his lips trailed down my skin once more, this time stopping to feast upon my stiffening nipples before continuing downwards. The hard pebbles jutting from large brown areolas throbbed with want, his teasing licks and sucks doing nothing but igniting a burning desire within me.

I wanted his mouth back on my breasts, but I also didn’t want him to stop the descent to my pussy. His tongue reached my mound and I bucked upwards, my ass rising off the bed. My fingers grasped the sheet as his tongue delved between my puffy outer lips and flicked against my clit. He attacked it with such frenzy that I flooded his face with cum in no time. My body was still trembling with after shocks when his fingers spread my cheeks apart and the touch of his tongue in my most intimate place had me gasping in surprise at the rush of pleasure it brought. Using fingers and tongue, Jeff brought me to another explosion of spasms as he stretched my tight anus open.

As I came down from release, he flipped me over onto my stomach and pulled my shaky knees up underneath me. I felt something cold and slippery dripping down my cheeks and worked inside me as he slid a finger into my tight virgin passage to push the lubricant inside and ease the way for his cock.

I breathed deeply as the tip of his cock rubbed against my pucker and pressed forward. A slight burn filled my ass as he slowly opened me up with the head of his dick. Sharp pain shot through me when it popped past the constricting rings of my sphincter. He held still for a moment, and I sucked in a few ragged breaths as the pain dulled to a mild discomfort. Inch by inch, he pushed on, feeding his cock into my tightness, stopping each time he moved forward to let me adjust. As he slid all the way into me, I reached between my legs and delved between the sticky folds of my pussy. Rubbing my clit, I moaned as tingles of pleasure shot through my body.

Seized by the sudden urge to feel him moving inside me, I rocked back on his cock. He took the hint I was ready and started to thrust, slowly at first until I was begging him to go faster. His fingers gripped my ass cheeks as he plunged into me, sending waves of ecstasy rolling through me with each forceful stroke. I stroked my clit hard and fast as pulses of pleasure throbbed through my body. A loud wail ripped from me as my hand clawed at the sheet. I bucked against him, driving him deep as spasms wracked me. His guttural cries joined my own and warmth filled my ass as he came inside me.

After I’d recovered enough to think that my trembling legs might actually hold my weight, I rolled to the edge of the bed and started to get up.

“Where’re you going?” he asked as he reached out and grabbed my arm, pulling me back to lay beside him. “We’re not done yet.” I wasn’t sure if my ass could take a second fucking so close to the first, but the delicious warm tingling made me think I would at least give it a try. Amy had been right about Jeff’s expertise. The initial discomfort had been driven from my mind so quickly, it was difficult to even remember what it had felt like. I had a feeling there would be other nights spent in his bed before all was said and done… and more than likely, Amy would be present for some of them.