Date: Wed, 30 May 2012 16:02:57 +0800
From: Ben Ng <ng.ben9@gmail.com>
Subject: Rick's Diary Part 23 - More Probing

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.