More Probing
When I woke up, I found that my head was resting on Ben's naked thigh, and his cock was inches from my face. His hand was in my hair, gently stroking it. I closed my eyes. Is this real? I enjoyed the warmth and softness of his bare skin on my cheek, and I breathed in the scent of his groin. It was a masculine smell. It was familiar. I've grown accustomed to this scent since I have sucked him countless times this year in college. Yet, it was strangely arousing. I could feel my cock stirring again.
"You are awake, I can tell." Ben looked down at me and smiled.
"I wasn't in this position before. What happened?"
He smiled. "I want my cock to be the first thing you see when you open your eyes."
"You mean the first thing you want me to do when I wake up is to suck your cock."
"Yeah, but it sounds better the way I said it."
I laughed. I moved my face forward and took his cock into my mouth. It was still soft. I liked to swirl it all around and lick the underside. When he's soft, I can easily take in the whole thing. I liked to feel it grow in my mouth. It's fun. I played with his balls with my hands and gradually reaching down, feeling the area between his balls and his hole. I massaged that area and he moaned. I went further down but he stopped me.
"No playing with my ass." He held my hand with his. I looked up at him.
"You only said no kissing or fucking." He looked at me and pondered on it.
"I never put anything up my ass."
"Why?"
"It's gross. It's where shit comes out."
"But it also feels good."
"You really want to play with it so much?"
"I just want you to try it. If you don't like it I'll stop."
"Ok, fine, but be gentle."
I smiled. Ben is letting me play with his ass! That's definitely a breakthrough. Fingering each other brings us closer to my ultimate goal: ass fucking! Well, really, my ultimate goal is lovemaking, but that's not going to be easy. I wanted Ben to really enjoy it, so I grabbed some lube and put some on both my finger and his hole. He looked at me apprehensively, as though I was going to rape his ass.
"Relax, I'm only putting lube so it will go in easier."
"This is so gay."
"I thought you hated labeling?"
"I do, but this is really gay."
I chuckled. I slowly inserted my finger. It was really tight, a virgin hole. I smiled at how it closed up once I touched it. It was so sensitive it definitely hasn't been touched before. I gently rubbed around his hole, making circles. I noticed the hair all around it. Ben wasn't exceptionally hairy, but there was hair all over the hole. It's now matted down by the lube. His hole looked sexy. I wonder when I can make love to it. He watched me as I played with his hole. I have forgotten about the sucking.
"Hey, can you go back to sucking and stop obsessing with my hole?"
I smiled. His hole was indeed intriguing to me, especially because he never let me play with it before. I went back to sucking, licking up and down his shaft then swallowing his cock head and descending inch by inch. Meanwhile, my finger kept probing his hole. When he got into the blowjob, his hole relaxed. I took this opportunity to shove my finger right in and he gasped.
"Ouch! I told you to be gentle!"
"Sorry! It's really tight so I got to use some force."
My finger started going in and out while I sucked him. He was squirming, clearly uncomfortable with having a finger in his ass. This must be new to him. I wiggled my finger, trying to find his prostate. When I found it, he jumped.
"No wonder you like it so much." He was a bit breathless. I kept probing it while I sucked on his cock. I gradually increased pace, both the sucking and probing. He was getting all worked up, thrashing around and grabbing my hair. He was groaning loudly and his body was shaking uncontrollably. He was clearly enjoying it. I kept it up for a few minutes and he reached his limit. He grabbed my head and pushed me onto his cock and pumped a copious amount of cum into my mouth. Meanwhile, his ass clamped down on my finger, gripping and releasing it in succession. I imagined what it would feel like on my cock. He was breathing hard, grabbing my head until he came down from his climax.
"That was... something!"
"You like it?"
"I... I do. It felt weird having something in my ass, but the orgasm was intense."
"See, I told you it's great."
"I'm still not quite used to it yet. It's weird."
"I can help you practice."
He laughed. "You are always trying to get me to do gay stuff."
"Well, I'm gay."
"And I'm... not?"
"You are probably bi, my friend."
Ben shrugged. That concluded our day of fun. We both sucked each other, and more importantly, fingered each other for the first time. After this experience, I kept fantasizing about Ben's hole and what it would be like to fuck it. I know he's adamant about not fucking, but I couldn't help thinking about it, that tight, hairy, virgin hole. I was determined to be the first one to enter it.
Ben wasn't crazy about being fingered. On most days, he wouldn't let me. Only when he was feeling exceptionally wild did he let me do it, but every time he did, he came intensely. I think he secretly loved it but thought it was too gay. He was probably still more straight than gay, till this day. But we've come a long way, from jerking off in high school to sucking each other in college, and now fingering. But the next step, fucking, would take a considerable amount of time, and as I found out later, a radical experience.
Our freshman year was almost over. A lot has happened, with Ben and Mike. Come to think of it, I didn't regret having sex with Mike. It was some of the best sex I had and he gave me a wonderful time. It didn't work out well in the end, but it shouldn't take away the good either. I learned to cherish the memories while forgetting the bad stuff. I still room with Mike. Every time I look at him I still think about the wild sex we had together. Well, the lovemaking. I'm sure he's using some of the skills he learned while he was with me on his girls, and that's why he's more popular now. Too bad he has once again turned into the homophobic jerk he once was. But, on the up side, he's getting along with his teammates better, mocking gays in the locker room as usual. Perhaps he had a point; this is what he really wanted, to be accepted, to be part of the team.
I learned a lot this year. I'm free to express my feelings with Ben now. I'm sure by now he knows I love him, but he chooses to ignore it, to play dumb. He just kept it at the sex level and didn't want more. He freaked out whenever I tried to "make love" to him or do anything that may suggest I love him. I have learned to accept that. This is as far as I can go, for now.
So, for the next two years, things pretty much stayed the same. We would jerk and suck each other, occasionally finger each other, but more often than not, we would arrange for girls to come over and have threesomes, sometimes even foursomes. I kept my love for Ben under control; I didn't want to go past his comfort zone, not too much anyway. Perhaps I would describe one of the foursome scenes; it would be a spectacular finale, an appropriate ending to my first year of college life.