The Paperboy Delivers Pt. 03

Then, Lisa moved around and sat at the head of the bed with her legs on either side of my head. She slid her pussy under my head and encouraged me to lick her. As my tongue made contact with her pussy, Roy's tongue rimmed my hole. I eagerly tried to spread my ass, but it was difficult laying on my stomach as I was. Lisa saw this and had me lift my hips so Roy could shove two pillows under them. I settled down onto the pillows and could feel at once how they let me spread my ass without really having to try. I felt both relaxed and vulnerable at the same time.

As Roy went back to licking my hole, Lisa rotated her hips so that I was looking at her brown pucker. I noticed for the first time that her ring was nearly as dark as her nipples, making an inviting target for my tongue. She whispered to me, "Come on you ass licking slut. Make my tight little hole feel good."

As I eagerly swirled my tongue around her dirty hole, Roy was painting my hole with KY Jelly. That was soon followed by first one, and then two fingers gently fucking my ass. I wasn't much different from when he and Lisa had fingered my ass before, but the thought of what would be following had me flushed and breathing hard.

When he tried to put a third finger in my ass for the first time, I clenched up and had to tell myself to breathe and relax. After a few seconds I could feel them slip in, but my ass ring was definitely being stretched.

As Roy's finger banging became deeper and faster, the burning tightness never went away, but it was transformed into a hotwire signal to my cock. Even though I'd come for the third time that day just a short time earlier, I could feel my almost fully erect shaft throbbing under my belly.

I'd been lazily eating Lisa's ass and pussy that whole time. Suddenly she shifted to kneel in front of me as she reached for something on the nightstand. As she sat down on her feet, she held a dildo in front of my face saying, "This is going in next," before she held it to my mouth indicating I should suck it.

As she fed me the fake dong, I could tell it was just a little smaller than Roy in both length and thickness, but it had the same kind of fat bell end that I knew I was going to feel. As she worked to dildo deeper and deeper into my sucking mouth she said, "I love the way the fat head on this one stretches my hole going in and out. I'm going to get a picture of your ass trying to keep it in."

That's when I saw her Polaroid camera on the nightstand with some pictures of Roy and I sucking and fucking strewn around it.

She pulled the dildo out of my mouth and held it in front of my face as she slathered it with lube before handing it to Roy. As Roy accepted the toy from Lisa, he had three fingers in my ass which he withdrew and quickly replaced with the dildo. As Lisa had predicted, that was my biggest stretch yet, but I found myself actively helping Roy to bury it in my hungry hole. Roy obviously knew what it felt like, because he spent a lot of time using it to tug at my ring or pulling it out completely and then reinserting it.

I was moaning into Lisa's pussy and alternately grinding my cock against the bed and trying to fuck my ass onto the dildo. I maneuvered Lisa back into a position where I could eat her from her ass to her clit a few moments before Roy pulled the dildo completely out of my ass and handed it to Lisa.

As Roy lubed his cock and socketed his head in my ring, Lisa said, "I hope you enjoy losing your anal cherry. Now you'll be a full-fledged bisexual slut."

Roy leaned forward, bracing himself with his hands next to my body as I felt his cock split my ass ring. There was another burn, but that had my pulse pounding as I moaned and pushed back to meet his thrust telling him, "All the way. Put it all the way in. NOW!"

I could barely breath with everything I was feeling. Roy had settled on my back, supporting his weight on his hands as his hips and chest touched me. He was kissing my neck and Lisa was stroking my hair as I continued to nuzzle her mound. I was focused on the feeling of Roy's hot cock filling my ass. I could tell that it was my friend's living, pulsing cock sending waves of pleasure radiating from my ass. I would have been content to stay like that, but instinct told me that having that meaty shaft pound my hole would feel even better. So I said, "Roy, fuck me please. Fuck me hard and make it last."

Roy made a few long, slow thrusts into my ass before I felt him pounding me hard and fast. Each time he slammed his cock into my ass he hit my prostate, which soon had me moaning and whimpering.

I didn't know there was such a thing as an anal orgasm, but I could feel the familiar buildup in my balls. What was different was the sensation of having my ass filled. My ass was trying to clench the way it always does when I cum, but the cock filling my hole was stopping that. The effect was to make my ass ring pulse in an attempt to squeeze shut around the intruder. That amplified the burning and stretching in my ring until it reached a crescendo.

My orgasm started at the point where Roy's cock was hammering my prostate. I could feel that gland quiver and clench as I drenched the bed underneath me with precum. The good feeling from my prostate made my ass and balls clench and the next thing I knew, I was lying in a huge puddle of cum. Unlike a regular orgasm, this one kept coming in waves until Roy said, "Cumming for you Ian. Cumming," and buried his cock deep in my bowels.

Roy wrapped his arms tight around me as he kept instinctively pumping his cock into my hole. I could feel him kissing me between my shoulder blades as he rode out his orgasm. I was disappointed when he stopped, but as he lay on me catching his breath, I was able to enjoy the tiny movements of his softening cock in my ass. We both groaned in disappointment when he finally went soft and popped out.

We snuggled and kissed for a bit after that, but it was getting late, and I knew my mother would be curious if I didn't get home pretty soon. Lisa and I showered together before I dressed and left.

They both gave me a kiss right before I walked out the door. As I stepped out, Lisa said, "We hope you're up for more afternoons like this. And if you ever want a morning quicky, try the door when you drop off the paper. We'll leave it unlocked if one of both of us have time to play."

That was the start of a fun and educational year for me.