Well... He Did Say Please Ch. 21

As they drove away, Carl picked up his suitcase and said: "I'm ready for the bong. Anyone join me?"

I said that I would. "Let me see if Alan is back, and I'll be down."

I went to go in my room, and there was Vaseline on the door. FUUUCK!

I showed up in Carl's room with my suitcase and my coat.

Michael looked at me and my suitcase. "I'm guessing that Alan is here."

"Yes. Light that bong."

Carl ran down to the bathroom and put fresh water in it, and was back in a moment.

Carl said, "I saw Dick in the bathroom. He said they've only been in there for 5 minutes, so it looks like we've got some time."

Carl loaded the bong, and we had just taken a toke each, and there was a knock on the door. Michael answered it. Dick was there with a message for me. He intercepted a guy that was about to knock on my door, and took possession of the message. He said he was told the message was important. Michael let him in, and he handed me a piece of paper. It was folded over. Didn't look like Dick read it.

It was from Jay, asking me to call him right away ... important. "I need to handle this. I'll be back."

I left and headed for the pay phone. I reached in my pocket and I had a few dimes. Good. I called his dorm, and he answered. "Hey Jack. I have a request from Ronnie."

Veronica is the MILF that he's been seeing. Mary and I had a date with them for the following Saturday. It was going to be my first foursome with females involved (Yes. I had been involved with a foursome of guys ... I think Chapter 5). Mary and I were both looking forward to this. "I'm ready. Let me hear it."

"Ronnie says that you can fuck her, if she can peg you."

"What does peg me mean?"

Jay explained.

"Oh. Is that a thing?"

Apparently it was. "Let me think about that, and I'll call you tomorrow night."

He reminded me which dorm he lived in. He said that he would be back there after 3 tomorrow, if I wanted to stop in and talk with him. I told him to look for me.

I returned to Carl's room. The door was closed. I knocked, and Carl let me in.

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While the phone call was happening, back in Carl's room, Dick had stuck around. Carl offered him the bong, and he accepted. After a second hit, he handed the bong to Michael. He exhaled.

Dick looked at Michael. "Michael. I'd like to take you up on your deal."

"Really? When?"

We had just gotten back from 4 day Thanksgiving weekend. We may have jacked off during that time (I can't speak for everyone), so it's possible there were a few horny guys. Carl may have tagged the neighbor kid, his best friend growing up.

Dick looked at Carl. "Damn. I'd like right now. I'm so fucking horny, I'm willing to do just about anything."

"Willing to blow Carl until Jack gets back? You did say just about anything."

Dick looked over at Carl's lap. He was hard under his gym shorts. It looked big. "Can I see it first?"

Carl dropped his shorts. Dick was pretty much my size (6' and about 190 lbs), but he had the thickest white cock I've seen. "Only" 7 inches, but thick as Carl. For the first time, Dick was looking at a cock as thick as his, and longer.

Dick looked at Michael. "Is there something in the water in this room?"

Dick was referring to Carl at 5'9 and 9 inches and Michael at 5'7 and 8 inches.

Dick looked at Michael. "Are you planning on fucking me while I'm sucking on Carl?"

"It depends on how long it takes Jack to return. I may still be prepping your ass."

Michael was a little concerned. He had seen Dick at full staff when I was giving him a blow job. He knew how thick Dick was, and he didn't handle thick well. But he had survived Carl fucking him ...

Dick removed his clothes. He got on his knees, and Carl stepped up to him. Dick took that black pole in his hand, and licked it. They eventually moved around, so that Michael was able to lick Dick's ass, as Dick put 3 or 4 inches of Carl's cock in his mouth. By the time, Michael had two fingers deep in Dick's ass with lube, and Carl had worked 6 inches into Dick's mouth, there was a knock at the door.

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Carl peeked around the corner of the door, and let me in. I saw what was going on, and my first thought was if Dick was going to let someone take his anal virginity, why wasn't it going to be me? Michael was ahead of me.

Michael looked at me. "Dick. You said anything?"

The feelings from his ass were overwhelming him. "Yeah. What do you want?"

"Before I fuck you, I want Jack to take your cherry."

"Do you mean that I've got to let 2 guys fuck me?"

"Jack gets a few strokes to break you in, then I can give you your "first" breeding."

Michael was still fingering Dick's ass. Dick said, "You're mighty fucking confident."

Michael smiled. "That's the deal now."

Dick looked at me. "Ok. Come on Jack."

Carl had handed the bong to me, and I was taking a couple of tokes while watching this. I was thinking, "Come on Michael. Talk him into it." I handed Carl the bong, and started to remove my clothes. Carl gave me the bong for one more hit. I stepped up behind Dick.

I looked at Michael. "He's prepped?"

"Yes, but remember he's never had a dick before. It will take a little work."

Now I figured it out, Michael's got me doing the hard work, sort of like Huckleberry Finn. I just couldn't remember if I was Huck or Tom. But I didn't care. I lubed up my cock, stepped up and started working it into Dick's ass. It took 10 or 12 strokes to breach his sphincter, and Dick let out a groan. "Are you doing ok buddy? Do you want me to hold it here?"

Dick took a deep breath. "I'm good. It was as much a surprise as anything."

I remembered that surprise feeling when Michael breeched my ass the first time. I still get that feeling everytime Carl fucks me. I think that I knew where I was headed when I finished with my job here. I started working my cock in, until I felt my balls tap Dick's balls. I'm used to it from the other side. I liked it either way. I don't think that he had agreed to me breeding him, but I'm almost ready to blow. I'm not sure that I can hold it off ... and I didn't. Once I was balls deep, it only took 5 or 6 strokes. "Oh fuck."

Dick started cumming beneath me. He had been stroking himself the whole time. Once we were done, Dick and I sat on Michael's bed.

Carl handed us the bong. Dick took a toke, then exhaled. "Is it always like that?"

Michael answered. "There is one way to find out. Are you still ready to take me?"

Dick had cum already. He was no longer as horny as he was. "Can I take a raincheck? I need to process this."

Michael didn't push. "Take as long as you like. The offer will stand."

Dick got dressed and left the room.

Michael said, "Ok Jack. I think that you owe both Carl and me, but before you pay off, what was the phone call about?"

I told them about the pegging, and how I said that I would have to give my answer tomorrow.

Michael smiled. "Well. Did she say please?"