Allan's New College Freedom is a seven-part story, the first four parts are almost entirely true and the last three are mostly what I wish had happened. All characters were 18 years old at the time of these events. These stories are based on my own experiences and memories, but I have taken some artistic license in the telling. The names in all the "Allan's New..." stories are changed; location & unnecessary personal information has been changed or purposely omitted to protect people's identities.
My stories never mention protected sex. But in real life, Always use condoms and get tested regularly.
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Allan's New College Roommate -- (7/7)
Culmination of Aspiration
- ... I persisted, "How about it, man? You still owe me." "You'll use your lotion and stop if I tell you to?" "Yes, I will. I promise." "Then okay... under one condition." "What is it?" I said. "I get to fuck you too." -
At this point, all I could focus on was the fact that I was going to get the chance to slide my dick between his beautiful and perfect butt-cheeks. He could have made it conditional on fucking me every day for a week, and I'd still have said, "Okay!"
Then he said the magic words that almost made me cum right then and there, "So, how do you want me?"
I got up and took the quilt off my bed and spread it on the floor and got my extra blanket and put it over the quilt. I said, "For now, lay down on the blanket, on your stomach." as I got my hand lotion and put it on the floor within reach.
I knelt down beside Kevin's naked body in the dim glow of the parking lot's lights filtered through our shades. Kevin's dick, his beautiful ass, and generally, his whole body serves as my mental image of perfection to this very day. And here, this gorgeous hunk of young manhood was laid out before me offering himself to me. I just had to savor the moment. And I could think of no better way to do that than to give him a back rub... in reality, it would be more than that as I planned to rub him with different parts of my body. I said, "Just lay there. I'm going to give you a massage to help you relax." To that, I only heard a "Humm."
I pushed on the outsides of his thighs to get him to put his legs together, and I straddled them with my knees about mid-thigh. I started rubbing on what has become my third favorite area of the male anatomy, that roughly circular area between the top of the ass-crack up to the lowest part of the rib cage. This area straddles the beltline and takes in the tops of the glutes. Some guys have a patch of hair in that area, and I love it when they do. Kevin only had "peach fuzz," but everything else was perfect.
As I started to move upward, I realized that I would be leaning too much on Kevin if I leaned up much further. So, I moved up, walking my knees up to either side of his hips so I could massage higher. When I moved back down and sat down on his legs, I discovered most pleasantly that my hard dick rested right up his crack. So, I leaned my upper body forward and started thrusting a bit and squirming side to side a bit, trying to work my dick down between those wonderful globes. It felt so good I almost forgot that I was supposed to be massaging his back. So, I switched my concentration back on that for a while.
I wasn't sure if he was ready or not, but I was burning to get started. So, I reached for the lotion as I moved off Kevin and told him to roll over onto his back. I'd heard of a position that allowed a better view of the guys face and gives you access to his dick while you are fucking him. It also opened the possibility that the two of us could cum together, although I heard that it rarely happened.
"Why do you want me on my back?" he asked as he turned enough to face me. "I'm going to put your ankles on my shoulders and do it like that. I heard that a lot of guys taking it in that position because it feels better." (Among the other reasons I already mentioned.) "Oh, okay." he said as he rolled fully onto his back, raised and spread his knees.
With lotion bottle in hand, I moved and knelt between his raised knees. Seeing him like this, ready to receive me, to give himself to me, was almost TOO exciting. So exciting that I began to shake a bit from the dynamic tension. I was trying to control it, so hopefully, he didn't see it. On the other hand, I could see that while he was less nervous than before, he was still a little apprehensive about what was going to happen. The expression on his face was not the proverbial "deer in your headlights," but his nervousness showed through, not to mention that he still wasn't hard, despite the sensual back rub. But I was planning to change that. I wanted him hard when we started.
As I put a good-sized dollop of lotion in my right hand, I said, "Spread your knees as far apart as you can and try to relax, I'm going to rub this lotion into your hole which should feel real good, AND I'm going to do my best to get you hard again, so just lay back, close your eyes and enjoy it." When I reached down below his low-hung balls to trowel the lotion into his crack, he shivered briefly because the lotion was colder than he expected, but it quickly warmed up. I also reached up with my left hand and started rubbing and playing with his balls and cock. As my slick fingers found the pucker of his asshole, I started massaging it, trying to move the lotion into it. I moved my fingers in a circular pattern when massaging, and I pushed inward when trying to move the lotion further inside his hole. This, along with the dick action, was turning him on again, and his moans were increasing in number and intensity.
I leaned down and started licking that very sensitive spot on the underside where the shaft and the crown meet. Even most cut guys have a little loose skin there, and it is almost always more sensitive than the rest of his dick. I decided to use his increased pleasure to move a finger further inside his hole. As I continued licking that sweet spot and all around his crown and the underside of his shaft, I worked my long middle finger three-quarters of the way in, and he didn't even seem to notice until I stopped my oral ministrations. That's when I felt his sphincter close down, trying to crush my finger. And from the expression on his face, I could tell that closing down like that was not pleasant. But I was determined to keep my finger where it was. He said, "What are you doing?" "I'm trying to get you ready." "Well, it hurts." "When you tense up like that, it is going to hurt. If you stay relaxed and loose, it won't.
"Was it hurting before you tightened your asshole?" "Well, no." "It actually felt good, didn't it?" "Not really..." "And I suppose that what I was doing to your dick didn't feel good either?"
Kevin had a way about him that never admitted to anything readily, and him taking that attitude right now was starting to tick me off. "If you felt no pleasure in what I was doing, I can stop and just go ahead and stick my dick in there. Is that what you want?" "No." "So, what felt good and what didn't?" "Everything felt good except your finger in my ass." "Did your ass feel good before you clamped down on my finger?" "I suppose so." "Then don't think about the pains in your asshole when they happen, think about the pleasure, no matter where it is coming from, and remember when you tighten up, it will hurt. So, really try to keep it relaxed, even if you have to force it to stay relaxed." "Okay."
I started again with both of my hands, but it felt a little dry in his ass, so I worked my finger out of his ass and quickly grabbed the lotion and applied more. It was very slick this time, but I knew that if I tried to stick my finger back in, he'd react again by closing down. So I started again slowly, and when I was ready to stick my finger back in, I played a dirty trick on him, I buried his dick in my throat at the same time I smoothly pushed my middle finger in as far as it would go. He gasped and clamped down again, but this time, he couldn't deny the pleasure he was receiving and loosened back up quickly. I continued my ministrations both fore and aft and slowly worked in a second finger.
As I started pushing in a third, I could feel Kevin begin to clamp down but catch himself and loosen up again. Presently I figured he was ready and slowly withdrew my fingers, at the same time, I did a big slurpy lick up his dick beginning with his ball sack between his balls, which made him shudder. I grabbed the lotion and pushed in another glob while his hole was still open and then spread a glob all over my dick and moved into position.
I put his lower legs on my shoulders but saw that I needed a little more access to his hole, so I moved his feet and put them on my chest, making his knees move closer to his chest and raising his butt a few inches as I again got into position. I rubbed my dick across and around his hole to let him know I was about to start pushing in. Rubbing his hole with my dick seemed to feel good to him and was exciting me all the more, if that was possible. So I said, "here goes" and started pushing in very slowly. It was tighter than I expected, and with the crown of my dick barely in, he clamped down on it and winced in pain. I stopped and waited.
I also reached to put my hand on his stomach to console him and ask him to relax, but that little movement caused him to clamp down and wince again. I did try to comfort him, rubbing his stomach and feeling the treasure trail that could only be felt in this light.
While doing that, I put just a little more inward pressure on my dick, and it moved in about an inch more, and he seemed barely aware of it. I said to Kevin, "remember that you might have to force your hole to stay relaxed, at least at the start." And again, I started to push in slowly.
He started to react, but differently, he seemed to slowly build up pressure, like a boiler building up a head of steam.
Thinking he was hurting, I stopped, and so did he, and I asked him, "what's wrong?" and he replied, "I'm doing what you told me and forcing it to stay loose." "Well, if you keep that up, you are going to blow a gasket." He laughed and promptly squirted my dick right out of his ass. At that, we both laughed. As I got ready to start again, I said, "Remember, I can stop and let you adjust as many times as it takes. Just tell me when you want me to stop." I continued, "are you ready to start again?" "Go ahead."
So, I did, pushing in very slowly but keeping up the pressure because I didn't want him to squirt me out again, and he didn't tell me to stop. Eventually, I hit bottom. My pubic hair was pressing into his balls and butt as my dick seemed to lengthen a bit further into him with the pleasure I was feeling. It was glorious. And Kevin relaxed a bit but still had a look on his face that was hard to describe.
I asked him, "How does it feel?" "The pain is less now, but I feel like I need to take a shit, really bad." "You don't really need to go. It's just that you have something the size of big turd in there, that's why you feel like you need to go." And now I understood what that look on his face said, it was the expression you could see on your own face in a mirror when you are sitting on a commode and trying to pass a huge turd that just will not come out. Well, the thought of my dick being a turd was not very exciting, so I turned my attention back to what I was doing.
Here I was with my dick buried entirely in the ass of my roommate's beautiful butt. I decided not to let my mind wander off again. His dick had deflated quite a bit during my insertion, so I reached for it and started to rub and massage it, and his scrotum. As his dick started to inflate again, I started to grind my hips slowly against his butt and then began very shallow thrusts. When I got his dick fully hard again, I started pulling out a little more on each stroke. Before long, I was pulling out until only the crown of my dick was still inside him before pushing back in. Then I noticed that just after I started my inward thrust, his eyes would open a bit wider, then I'd hear a short moan of pleasure, and I noticed that his dick was getting even harder. So I knew something was giving him pleasure, but I didn't know what it was at the time.
I just thanked my lucky stars that he wasn't telling me to stop. I stepped up the speed of my thrusts and continued stroking his dick as well. I was working up a good head of steam myself, and I knew it wouldn't be long before I'd be shooting my seed deep inside him. I was jerking his dick at the same speed I was fucking him and thinking that it might make him feel like he was doing the fucking that way. It must have worked because Kevin stiffened as if he were trying to hold back a flood by an act of will alone. Then the dam burst, and he sprayed big globs of cum that went all over his chest and stomach. One even landed on his forehead.
I kept fucking him shallowly, leaving most of my dick in him and stroking his dick now as his asshole contracted, again and again, massaging my dick in a most excellent way. As his last contractions occurred, I decided that I wanted Kevin's ass the same way I'd had my first boyfriend's ass a few years before. So, while he was still in the afterglow of his climax, I gently pulled out of his asshole. Taking his legs, I turned him to my left and told him to lay on his stomach, and I guess he was still glowing enough simply to obey me because he did.
I pushed his knees together and straddled his legs. Grabbing the lotion, I squeezed a bit more into his open asshole and leaning forward lowered my dick to his asshole again. And without stopping, I smoothly sank my dick back into his ass between those beautiful globes. Kevin held his breath when he realized what was happening, but there was no protest or signs of pain.
When I was all the way in, I leaned on my elbows but put my hands under his shoulders and turned them up to hook them there. With my legs outside his and his ass filled with my dick, I began stroking in and out of him. I gave him long, luxurious strokes while the feel of those perfect globes pressed into my groin, again and again. It was wonderful. I was in heaven. So, of course, I didn't last long. My climax built very quickly with each long stroke into that beautiful butt. Then it arrived.
Like the moment at the top of a huge roller coaster when the mechanism suddenly lets you go, and you plunge headlong from a great height into a deep valley of excitement. I plunged into his valley, using the leverage of my hands on his shoulders and my weight on top of him, I thrust my dick in as far as it would go and let loose a flood of cum into the deepest reaches of his guts. With each gush of cum, it felt like I was moving even farther into him until it felt like he should be able to taste my cum in his mouth.
A couple of minutes later, I had calmed down enough to regain my sense of reality and felt my softening dick withdraw a bit inside his ass, and I gently pulled it the rest of the way out. I rolled off of him to finish coming down from my sex glow, and he rolled away from me onto his back.
After a few more minutes, I said, "WOW! That was wonderful!! Thank You!" "You're welcome." he said, then "were you serious when you said you'd let me fuck you too?" "Of course, I was. I promised, and I will keep my promise." "Okay." he seemed satisfied. "Then would you mind if I fuck you tomorrow, I am drained right now." "Sure, just let me know when." I said, happy to have another chance to have sex again with this beautiful hunk. "Then I'm going to bed. See you in the morning." "Good night." "Good night."
As he climbed into his bed, I picked up the blankets and put them in my clothes hamper and went to the bathroom to take a piss. By the time I returned to the room, Kevin was asleep and snoring softly, so I quietly climbed into my bed and drifted off to a thoroughly sated sleep, with the pleasant thought of my sperm slowly leaking out of his dick-stretched asshole as he slept.
--- Epilogue ---
The next night Kevin fucked me, but that was all he wanted to do. No foreplay, no touching me except when he was fucking me, and he was not nearly as gentle as I had been.
After he came, he climbed into his own bed and said, "Goodnight." When I protested "That's all??" He only said, "that's what you promised, and that's all I wanted." and rolled away from me clearly communicating that the conversation was over. I was pissed and we didn't exchange more than pleasantries for a few days after that.
Then one evening he did his little strip tease again, before and after his shower. And when the lights were out, he said, "Allan, I'm awfully horny, will you let me fuck you." I said, "Will you let me fuck you too?" There was silence for a few seconds, then, "No, I don't really want to do that." With that, I knew that he only wanted to get his rocks off and had no concern for me at all except as a hole into which to dump his cum. And if I gave in and let him do this, that was all I'd ever get out of him ever again. "Then I don't either." was my response.
He tried the striptease a few more times with the same results. So, we didn't have sex again for the rest of the term. After finals, we both went home for the long Christmas break.
Kevin was sexually selfish with me, only giving me what I wanted to get what he wanted, but then again, I guess I was doing the same thing. The difference was that what I gave to him I did so happily and enthusiastically wanting to pleasure him as well as myself. But, it appears he thought that after he got me going, he could stop giving and let the sight of his beautiful body be my only reward. Also, that "date-rape" situation could have messed with his head somehow. But I hold no grudges, he was young, as was I, and we all make mistakes until we learn better.
I don't know, but I suspect that Kevin had been fucking his previous roommate. That might be why the roommate so easily gave up a clearly better dorm room.
When I got back to school from Christmas break, Kevin was not in the room. It even appeared he didn't leave anything behind over the break. I wondered why, so I asked around. Even when I asked the people who knew him from his hometown who had just gotten back on campus, they didn't know. So, I asked an RA in the dorm office who told me that Kevin dropped out of school. I went back to the room feeling down a bit because I had hoped Kevin and I could come to an understanding to occasionally "help each other out." It crossed my mind that he might have gone home, got some unsuspecting girl pregnant, and planned to marry her just to hide the fact that he also liked fucking guys.
My musings were interrupted with a knock on my partially open door. A young Hispanic guy with a short-trimmed mustache pushed the door completely open and stood there with a whole bunch of stuff that he had obviously just carried up three flights of steps in one trip, and said, "Hi, I am your new roommate."
- THE END -
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Positive comments and suggestions are always welcome. Allan Allan@Grassyvalley.us
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