Catching Up with an Old Friend Ch. 02

I woke up about three in the morning, we were both lying there naked, legs intertwined. I slipped from the bed to take a leak, as I walked back in, the moonlight lit the room and I could see Scott's firm, white ass, open and inviting. I began to stroke my cock until it became stiff, then I took the lube from the bedside table and drizzled it up and down the crack of his sleeping ass. I then coated my own cock and climbed onto the bed.

I eased the head of my cock into his crack, smearing the lube around and then pushed into is anus. He woke up instantly and moaned, then pushed upwards with his ass as I pushed downward. I slid easily into him and pumped harder and faster, as he raised up onto his knees, his head buried in his pillow.

I fucked his tight hole for twenty minutes straight before I felt my load building. Just before cumming, I pulled out and flipped him onto his back, he instinctively opened his mouth and I jerked my load onto his waiting tongue. I filled his mouth and wiped my cock onto his cheeks, smearing the remaining drops of cum across his face. He swallowed the load and smiled.

"That was fucking awesome!" He said, "I don't think I've ever been woken up by a cock in my ass."

I smiled back, "Sorry, I couldn't resist when I saw your legs spread and you tight white ass just waiting on me."

"Can I cum now?" He asked, slowly stroking his own fully erect cock.

I moved his hand and started stroking him off, squeezing his cock tightly as I pumped faster and faster.

"OHHHHH SHITTTTT" he said, "I'm almost there...oh..oh..." he breathed.

I bent down and took his cock into my mouth, which he then filled with his creamy cum. I held it all in my mouth and let it finish before moving up and placing my mouth above his. He opened his mouth and I opened mine, letting his cum drain into his waiting mouth. He swallowed it all, then we kissed, letting his tongue scrape the rest of his cum from my mouth. We then kissed deeply.

I rolled off of him and we again drifted off to sleep.

The sun woke me up early Thursday morning. Scott was not in the bed, nor did I hear the shower running. I looked around and his clothes were gone. I assumed he'd had left because he needed to go to work.

I was wrong, he came back into the room about about 20 minutes later with coffee and donuts.

"I hope I didn't wake you, I wanted to get us breakfast and I had to call in sick to work," he said smiling and handing me a cup of coffee.

"Nope, woke up and was surprised you weren't here. Glad you were able to take off today."

"Me too, I told them I'd probably be off tomorrow too, I hope that was okay," he added.

I smiled, "Yep, that works for me." I took a donut from him, and sat at the table in the room, he sat his coffee down, stripped out of clothes and joined me.

My cock was already semi erect and was getting harder as we chatted about the fucking we had done the night before and the loads of cum he had swallowed.

"I've not been fucked this much in like ten years," he said, adding, "and I know I've swallowed more cum in the last twelve hours than in at least that long! Well, other than my own loads."

"Well, I haven't fucked that many times in a single night in a long time myself!" My cock was now fully erect again.

"What do you want to do today?" He asked.

"Well, I want to fuck you like a girl, legs up on my shoulders, you on your back, taking my cock into your tight butthole." I said.

He smiled, and said, "I love that idea, wanna fuck me now?"

I shook my head, "No, I want you to," I took a donut from the sack and slid it onto my cock, widening the hole and letting the chocolate glaze slide up and down, "eat this donut off of my cock first."

He dropped to my knees and began to eat the donut, licking the glaze off my head and sides of my cock. He ate the entire donut, licking and sucking my cock as he went.

He looked up at me, donut glaze on his lips and asked, "Will you fuck me now?"

I got up and pulled him up from the floor and had him lay back on the bed. I grabbed the lube, squirting it onto his crack and my cock. I then lifted his legs and slid the head into his hole. I could tell he was getting more used to my size as I slid in much easier than before.

I began fucking him like a girl, holding his legs against my shoulders, running my hands up and down his legs as I pumped him harder and harder.

He moaned louder and louder as I fucked him harder and harder. His own cock bounced up and down with each stroke, leaking precum as I pumped. As we fucked, I pictured him in stockings, his legs silky and smooth and said, "I think we will go shopping for stockings and panties for you later," I moaned, picking up my pace.

"Oh shit, I love that idea!" he groaned, "Haven't worn those since college," he added.

"You want to be my bitch, my girl?" I asked, my breathing picking up and my balls filling with cum.

"Yes, Yes, Yes," he moaned, "I'll be your bitch! Dress me like a whore, I'll be your whore." He groaned, pumping his fist faster and faster on his own cock.

"OH FUCK! I'M CUMMING SLUT!" I yelled.

He groaned as cum flew from his cock, his ass tightened with each spurt of his cum, "FUCK YEAH! FILL MY ASS! FILL MY ASS!"

I pumped harder and faster and came hard, pumping a heavy load of cum into his tightened hole. I kept pumping until I was completely emptied inside him.

I kept my cock in him as it slowly deflated and slipped from his hole, my cum running out behind it. I kept his legs on my shoulders and kissed them, sliding my hands up and down them. I looked down and he was smearing his own load all over his stomach and chest.

"Fuck!" he said, "That was amazing!"

"No shit!" I replied, "You should see the river of cum leaking out of your ass."

He smiled and asked, "Are we really going shopping for stockings?"

I nodded, "Yes, I want you dressed sexy tonight. I might even have you shave your legs," I said, smiling at him.

He looked up, "I would, I would shave everything off if you want me to. I want to be your bitch, your slut, I want you to fuck me like a whore."

"Maybe we should find another guy to join us, so you can have two cocks at once." I said, rubbing his legs that were still on my shoulders.

"Anything you want, anything," he said, then added, "I haven't been used like this since college. I want to be used, I want to be a total cum whore today."

We took another shower together and then dressed to head out. I went to an adult bookstore first, where we purchased a silver metallic buttplug that had a pink jewel in the end of it. We went into the bathroom where I had Scott insert it into his ass.

We then headed to a clothing store that specializes in tranny clothes, basically girls clothes in men's sizes. We purchased two pairs of stockings, one black and one white. We also purchased matching thong panties. I also purchased a full body stocking that was neutral in color, that had the crotch - front and back - removed for easy access.

It was lunch time so we grabbed a quick bite to eat and then I had Scott call the friend he was supposed to have met last night. I had him ask the guy if he would like to play in a threesome with Scott in the middle, Scott explained to him that we would both be fucking him and he would be sucking both of us. Though I could not hear the other side of the conversation, I could tell he was skeptical. Scott continued to describe how he would be letting us both do whatever we wanted. The guy wasn't buying it and in the end said no.

"Well, I guess we could try CL and see if we can find a guy that want's to come play," I said.

"Yeah, I guess, that works," he said, adding, "I know we can get a guy interested if we post a couple of shots of me in my stockings and this buttplug."

I grinned, "How is the buttplug?"

"Heavy, and making me want more in there," he replied, smiling.

We went back to the hotel, where Scott slipped on the black thigh-high stockings and got on the bed on all fours, the pink jewel of the buttplug shining as I took several photos of him. I had him stay that way while I then posted an ad on CL seeking a third who had to be under 40, clean, discreet and a top, as he would be fucking and getting sucked repeatedly.

After posting the ad, I walked over to the bed, stripped and eased the buttplug from his ass. I then climbed on the bed and slid my hard cock into him. I slid in much easier, though he was still very tight. I grabbed his hips and began to slowly, very slowly slide my cock in and out of his butthole. I went slowly on purpose, simply enjoying the tightness of the fuck. I fucked my friend's asshole for almost a half an hour before I could feel my cum building. I then picked up the pace and began to ram my cock hard into him. My balls slapping against his as I plunged the full length of my cock into him.

I began to cum, pumping shot after shot into him.

"Put your face all the way down," I said and he moved his hands down and slid his face onto the bed, I slipped out of his hole, it staying open about the size of a quarter and slid the buttplug back into him. Sealing my cum in him.

He rolled over and I grabbed his cock, pumping it up and down a few times he blew his load, covering his stomach and chest again. I smeared the cum all over him.

"You like that, don't you? Having my cum sealed in your ass and your cum covering you?"

He smiled, nodded, then said, "I love it. Man, I'm such a cum whore!" He laughed.

I left him lying there while I checked email. We had almost twenty, of course in typical CL fashion more than half were fake and several were just pic hunters. But, there were three that seemed like a match.

I emailed all three and waited. Two were in their twenties and were available after work, one was in his mid forties and was available between three and six only. He sent a pic of himself and he looked to be build like both of us. His cock was short and very big around, probably five inches long and as wide as a beer can. I sent him the hotel info and explained that we would be ready by four, it was already three.

We jumped in the shower again, and I removed the buttplug from Scott's ass. We also removed the small amount of crotch hair he had trimmed closely and I then shaved his ass too. I decided on our next trip out I would get Nair for his legs.

I had Scott slip on the white stockings, I slid the buttplug back into his butt and told him to pose for me. I took dozens of photos of him, his cock was fully erect as he paraded around the room in his stockings and the buttplug.

There was a knock on the door and I instructed Scott to let our guest in...