Well... He Did Say Please Ch. 15

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Jack keeps expanding his repertoire.
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Part 15 of the 21 part series

Updated 02/05/2024
Created 11/08/2018
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pdiddyd55
pdiddyd55
255 Followers

It was Friday morning. I had 2 big tests this week, but they were over. I didn't have a class until 11, so I was hoping to sleep in a little. I was shaken awake by my roommate, Alan. "I'm sorry Jack, but I still haven't found a release, and I could really use a blow job. Could you help me out, please?"

Well ... You know how I am when someone says please.

I looked at that 7 inch cock with its large helmet. I was still half asleep when I reached for his balls and started caressing them.

"Thanks Jack. I'm sorry, but I haven't got much time. I need to get to a class."

I sat up, and took his dick in my mouth. The first thing I notice is that he was already leaking pre-cum. I have mentioned before that I've enjoyed the taste of his pre-cum above all others. It's been more than a week since I've had him in my mouth, and I'm savoring the taste. I took him all the way down, feeling it slip into my throat. I reflexively swallow as it enters the throat.

"Oh fuck. That feels great Jack."

He grabs my head and starts fucking my mouth. He's insistent, without being overbearing. After a few minutes, his balls are no longer slapping my chin. I know that he's getting ready to cum, and he does. I clamp down with my lips and push him back a little, so that his cum fills my mouth. He finishes and removes his dick. He walks over to his closet and wipes his dick on a dirty tee shirt, then starts to get dressed.

"Sorry Jack. I sort of promised that I wouldn't do that to you. I just needed that."

"That's ok. I'm glad that I could help you out this morning."

I looked at the clock on my desk. Fuck. 8:45. I had a class at 11, so I was planning on getting up in 15 minutes anyway. I slipped on a pair of shorts, and grabbed my toiletry bag, and headed to the restroom. First order of business was to get morning ablutions out of the way. After a visit to a toilet stall, I went to wash my face and brush my teeth. I noticed some stubble on my chest.

Bill had helped me shave my chest, groin and ass almost a week ago. It was time to clean it up. I returned to my room, replaced my shorts with a towel, and headed for the showers. I saw Michael in there, said hello and took my new Trac II razor and headed into the shower. Shaving my chest and around my groin was not difficult. I was hesitant about shaving my balls, but gave it a try. Playing with my balls, and moving my cock around to shave around it, got me hard. I contemplated rubbin out a quick one, but decided I would enjoy my time tonight more if I didn't.

I determined that shaving my ass wasn't going to be possible, at least at this time, so decided to ask Michael to help with that. I remembered that I promised to help Pete shave tomorrow. I started daydreaming about maybe tapping that ass. That did nothing to help my boner go down. I decided to finish up with my shower, then stepped out to grab my towel. Carl was there now, along with several other guys. Seeing Carl's limp dick hanging down wasn't helping my hardon situation. I tossed the razor in my bag, then started drying off, making sure that my ass was facing Carl when I bent over to dry my legs. Why should I be the only one with a hardon problem this morning?

I wrapped my towel around my waist, and turned to ask Carl if he was headed down to breakfast. I saw that my plan had worked. He wasn't hard, but he was headed in that direction.

"Have you had breakfast yet?"

"No. No I haven't. Michael is waiting for me. Did you want to join us?"

"Sure. I'll head down to your room once I get dressed."

Which is what I did. Michael was dressed when I got to his room. We were just waiting for Carl.

I asked Michael, "What time are we heading to John's place tonight?"

"I figure we'll leave here about 7. Does that sound good?"

"That should work for me."

Carl entered the room, threw his towel in his basket and got dressed. We grabbed our books and our coats and headed downstairs.

I saw Mary when PoliSci finished. She came up to me, and said that she wouldn't have time for lunch today, but was looking forward to our date tomorrow. So was I. I gathered my stuff, put on my coat and left the room. I was free the rest of the day. I decided to grab an early lunch. There was a McDonald's not far from campus, so I headed there. I hadn't had a Big Mac in a long time. As I was leaving the building, I saw Mary walking with a guy. I saw him put his hand around her waist, and they turned, heading in the direction of her dorm. Maybe explaining to her that I didn't want to be exclusive, if the subject should come up, wouldn't be that difficult. McDonald's was in the other direction, so I turned and headed that way.

I hit the UGLI (Undergraduate Library) in the afternoon. I had no tests for the next couple of weeks, so just made sure I was up to date reviewing my class notes, and looking up salient points in my textbooks. I was back in my room by 2:30. I decided to take a nap and woke up when Alan returned to the room.

"Sorry Jack. I didn't mean to wake you."

I was yawning. "No problem. I just wanted a quick nap anyway."

I looked at the desk clock, and noticed it was 4:00. "Were you going to have dinner soon? I could join you."

"Yeah. Then I was heading out to the GRAD for a couple of hours. Look. I'm sorry again about this morning. It was not cool waking you up like that."

"Don't worry about it. If you do something that I don't care for, I'll let you know. I'm going to check with Carl and Michael and see if they want to join us for dinner. Meet me down there?"

"Sure thing."

Michael was in the room. He offered me a joint, so we took a couple of tokes each, when Alan knocked on the door. Michael got up and let him in.

Michael offered the joint to Alan.

"No, but thank you. I'm headed to the library after dinner, and I'm not good with studying while I'm high."

We headed down to eat, then Alan left for the library and Michael and I returned to his room. Carl had just returned. When we entered, he offered to fill the bong. How could we refuse? He hadn't eaten yet, so he headed downstairs after a few tokes.

I looked at Michael. "Can I ask a favor?"

"Sure thing. What do you have in mind?"

"I was able to shave my chest and groin in the shower this morning, but couldn't figure how to get to my ass. Do you mind shaving me?"

"6 months ago, I never thought I would hear a request like that. Now, it doesn't seem strange at all. I'll get some hot water, while you strip down."

I found a towel, and spread it on the floor. Michael returned with a bowl of water. We figured the best way to do this would be to have me on all fours, with legs spread apart. I felt Michael feeling up and down my crack. "I don't think this should take long."

He wiped my ass with the washcloth, then applied some shaving cream. A few swipes of the razor, and another couple of swipes with the washcloth, and he declared that I was good to go.

Michael slapped my ass. "It's a little early, but why don't we head over to the house and see if John is there yet."

"That works for me. Let's go."

Michael grabbed his coat. We stopped by my room and grabbed mine, and off we went.

Michael asked me, "Are you and Mary still going out tomorrow night?"

"Yeah, and I spoke with Alan about having the room later in the evening. We worked out a signal so that he would know whether it was safe to come in or not."

"Oh? What's the signal?"

I explained that we didn't want anything that was obvious, or could be fucked with. "We decided the most discreet thing would be to just wipe the doorknob with some Vaseline. No-one walking by would notice it, and I wouldn't have to worry about someone removing a note, or whatever from the door just to fuck with me."

"That might work. I'll have to run that by Carl. It might work for us as well."

We arrived at the KOK house. We were well enough known there that we felt comfortable walking in without ringing the bell. Jay, one of the pledges that I had met at the party last week, was just exiting Ken's room. "Hey Jack. Are you here with Carl?"

"No. I'm here to see John, his brother. Have you met Michael? He is Carl's roommate."

"No. I haven't."

He held out his hand to shake Michael's. Jay, of course was black. He was my height, 6 feet, but slimmer. The pledges, and I, had worn grass skirts at the party last week. I remember that Jay was smooth on his chest, without much muscle mass. I was guessing he was about 150 pounds.

Michael shook his hand. "Nice to meet you Jay. Do you live here?"

"Not yet. I'm pledging. I was just speaking with Ken about that."

The way he made this statement, I wondered if he was having a hard time finding someone to help him with his requirements. I had already helped Carl, and I had promised to help Rufus. How was I helping? Each pledge had to provide a white person to be fucked by 3 of the house members. My ass was my way of helping my friends. "Have you found someone to help you with the pledge requirement?"

"That is what I was just talking to Ken about. I found a woman, but she is not a student. She's in her upper 30s and loves to be fucked. She came on to me in a bar last night and took me to her house where she fucked my lights out. I asked her, and she jumped at the chance. I just wanted to make sure there were no requirements about age that would prevent this."

Michael looked him up and down. "I assume that she's good looking. I can't see you settling for a skank."

"Thank you for that Michael, and yes ... she's a fucking MILF. I actually hate to share her, but I want to get into the fraternity."

They had to explain to me what a MILF was.

John entered the front door. "Hey guys. Come on up. I want to take a shower, and you guys can have a joint while you wait if you like."

Michael added, "How about if we all have a joint, then we can join you in the shower?"

I saw Jay's eyebrows raise. I'm sure he was aware that some of the brothers liked to fuck asses. Carl had told me that not everyone in the house was into fucking guys, but the ones that were not, did not say anything about the activities of those that did, and the house DID have a resident white kid, Adam, that was there solely to relieve the blue ball syndrome of those members that had not gotten any recently.

John nodded. "Ok. Sounds like a plan. Jay, do you want to join us?"

"No, but thanks for asking. I have a date tonight."

Michael looked at him. I think he was jealous. "With your MILF?"

"As a matter of fact, yes."

That got John's attention. "A MILF? Really? Way to go Jay. Come on guys."

He headed up the stairs. Michael and I said goodbye to Jay and followed John up the stairs. Once in his room, John lit up a joint and we started to pass it around. He said this was some Mexican. Not the best, but it got the job done.

After Michael took a toke, he filled John in. "Jay is lining up this MILF as his pledge requirement."

John was just taking his shirt off. "Really? Wait here a minute. I want to see if he's still downstairs."

John ran from the room.

I laughed. "I'm guessing John wants to get his name on the top of the list."

Michael explained something to me. "I'm betting that Ken is already at the top of the list. John has told me that Ken doesn't fuck guys, but he likes to take advantage of all of the female volunteers that he can, and since he's the president this year, he has the ability to put his name at the top of the list. Not even Ty can do that. It's the biggest perk of his office."

John returned to the room. "Damn. I missed him, but I ran into Ty and explained the situation to him. He said that he would call Jay at his dorm and try to get our names on the list. The fucker's going to get his name above mine, but nothing I can do about that. I don't know where Jay lives. There is nothing like a MILF to get the blood rushing to your dick. Well, that and a twink (looking at Michael)."

John grabbed the hemostats, and we took care of the roach. We undressed and headed across the hall to the bathroom. Carl and I had been in this shower together before, but this was the first time that I was in there with 2 other guys. It was a little cramped. We scrubbed each other down, and headed back to John's room, dripping water all the way. Forgot to bring towels.

We were already nude, and hard, so the foreplay was out of the way. John's room was set up so that there was space on each side of his bed, as opposed to having a side of the bed against the wall. John had me lay down on his bed with my legs off one side, and head off the other. With the size of these cocks, it was much easier to get into my throat in this position. John started rubbing his balls across my face, eventually settling them into my mouth. As I was licking and sucking on his balls, Michael lifted my legs, handed them off to John, and proceeded to eat my ass, getting my ass ready. Michael got the jar of Vaseline and started lubing me up, and his cock.

John slapped his cock on my face. "Are you ready Jack? We're going in from both ends."

He presented his cock to my mouth and Michael placed the tip of his cock on my ass. They each pressed forward. Within a few minutes, they were each balls deep. Michael was 8 inches of white cock with a moderate girth. Michael was only 5'6 or 7", so the cock seemed disproportionate to his height.

John was 6'2" and had an 11 inch cock. His girth was similar to Michael's. At times, I had 11 inches coming in from the top, and 8 inches coming in from the bottom. If I were a shorter guy, I wondered if they would meet in the middle. God, I love getting fucked when I'm high. The random thoughts just keep on coming. And speaking of cumming ...

Michael was stroking my cock as he was pumping in and out of my ass. His 8 inches was just managing to rub my prostate, while his hand was stimulating the nerves on my cock. I came first, which cause my ass to clench around Michael's cock. He increased his pace and proceeded to fill my ass with his seed.

John didn't want to be left out. "Ok Jack. I've been wanting to breed your throat since we last fucked. I'm going to start long dicking your throat. Let me know if it's too much for you."

He proceeded to withdraw his dick until just the helmet was in my mouth, and he steadily moved it all the way back down balls deep. A few of these strokes, and he held it in. "Try swallowing Jack. I want to feel those throat muscles on my cock. Oh yeah. That's it. You're about to get your reward."

Another couple of pumps and he started cumming while his balls were resting on my forehead. I felt the dick spasm a few times, and I had to push him back so I could catch my breath. The rest of his cum filled my mouth. I swallowed as quickly as I could. John withdrew his cock and wiped it across my face. Michael still had his cock in my ass, and he leaned forward and licked the stray cum off my face. "That was so hot Jack. I can't take his cock all the way down. I'm amazed that you seem to have no problem with it."

Michael stood up, removed his cock from my ass and found a clean washcloth on John's dresser. He ran across the hall, leaving the door open. There had been no attempt to keep our activities quiet. The house members were used to these sounds coming from various rooms. Bill was standing outside when Michael ran across the hall. He stuck his head in.

Bill was one of the guys that fucked me for Carl. He was about my height, with a 10 inch cock, thick like Carl. To this time in my life, it was the only cock that I had seen with a downward curve.

BILL: "Do you mind if I come in?"

John looked up. "Not at all. Come on in. We'll light up another joint."

Michael returned with the washcloth. I think that he had washed his cock while he was across the hall, and he came over and washed my ass for me. An all around nice guy.

John was just getting ready to light a joint. "Michael, do you know Bill?"

"I only know of him, I think. You're one of the guys that helped Carl out with his requirement?"

"Yes. I saw Jack was in the house again, and I wanted to talk with him before he left."

I was recovering still. After Michael washed my ass, he grabbed a towel and suggested that I sit up and sit down on the towel.

I looked up at Bill. "Do you want to talk here, or down in your room?"

"Here is just fine. I just wanted to see if we could get together again. I'd love to shoot a load down your throat and have another chance to breed that ass."

John held up the joint. "Join us in this joint. Maybe you can join us for round 2."

Bill looked at Michael and me with a look on his face to see if we had any objections. I didn't.

I smiled. "I'm game, but you're a little overdressed for this party, Bill."

Bill grabbed the joint, took a toke, then a second one. "I'll grab a shower and be back if that's ok. It'll give you guys a little time to recover."

Being 18 and 20 years old, it didn't take much time. It didn't take much time for Bill to shower either. In a little while, Michael and I were in a 69 with me on top. John had to stoop a little bit to get lined up, but he was entering Michael's ass. Bill was behind me and entering my ass at the same time. John and Bill started thrusting in and out of our asses. Bill was able to bottom out quicker, not because he was smaller than John, but I believe because Michael had already opened me up, and my activities of the past few weeks has had my ass more receptive.

John eventually went balls deep into Michael and started long dicking him. I had a front row seat, watching that cock come all the way out, a momentary rest on Michael's ass, and then re-enter all the way. Michael started moaning around my cock.

In the meantime, Bill was stroking his cock along my prostate. This got me moaning. Neither Michael nor I could really do much to help stroke the other's cock. We were just holding on with our mouths. I know the moaning coming from Michael was causing a vibration clear through to my balls. It didn't take long, and I was cumming, filling Michael's mouth with my spunk. Bill was still rubbing his dick across my prostate, causing me to moan some more.

Bill increased his speed. "Man, I love how your ass takes cock. Here it comes Jack."

And I felt Bill's cock spasming in my ass, and as he did so, Michael started cumming, filling my mouth. John wasn't finished, and Bill wasn't letting me up. In fact, he just kept pumping. I think his dick never went down. He just started pumping faster.

John's long dicking was picking up the tempo. I felt Michael reach up for my nipples and start twisting them. I was going to cum again, and soon. My dick slipped out of Michael's mouth, and when it did, I sprayed what cum I had left in me across his chest. I took my mouth off of Michael's cock and just went with the feeling of having Bill pummel my ass. I was watching John's dick go in and out of Michael's ass and on an out stroke, I managed to lean forward and lick the top of his cock. On the next out stroke, I did the same thing.

"Oh fuck Jack. That does it."

I saw him jerk inwards, slamming his balls into Michael's ass and I knew he was breeding my friend. Then I felt Bill give a couple of more thrusts, and for the second time in this fuck, I felt his cock start to spasm. He pulled out and the last couple of spurts landed on Michael's face.

"Fuck. Sorry Michael. I didn't mean that."

I think Michael was too tired to speak. He just gave Bill the OK sign. Bill went over, grabbed the washcloth and ran across the hall ... once again leaving the door open. What is it with these guys leaving the doors open? Again, I assumed that he had washed his cock off, and returned to the room. I was rolling over to start to unwind. Bill handed the washcloth to Michael so that he could wipe the cum from his face and chest.

Michael thanked him. After wiping his face clean, he handed the washcloth back, suggesting to Bill that he clean up my ass, which he did. John withdrew from Michael, and grabbed the washcloth. He ran across the hall, to clean himself up, then returned and took care of Michael's ass. When he returned, he never closed the door. There was a knock at the door, and when we looked up, Jay was standing there. "Mind if I come in?"

pdiddyd55
pdiddyd55
255 Followers