From: Woodrow Harrison <email@example.com>
Subject: The club part 4
I couldn't drive the image of those boys in the porn film fucking from my mind.
Lying in my bed that night I wondered how it would feel to stick my cock into
another guy's ass. Under the covers I took my dick in my hand and squeezed it
holding the pressure and pushing back and forth as if fucking my fist. It was
quite a pleasant sensation and made me the more curious about actually doing it
with Henry. I resolved to call him the next day and try for a private lesson.
School seemed to drag on forever. I ate lunch with Richard, Walter, and Ralph
and they commented on my reticence.
"Guess I'm just feeling moody today." I replied.
They accepted that evasive answer and respected my silence. After my last
class I went To the office and pleading illness got excused from gym. It was
all I could do to keep from speeding as I drove home. What if Henry wasn't home?
What if he already had company? Such worrying thoughts filled my mind as I drove.
Finally arriving at my house I fished his number out of my wallet and hesitatingly
dialed it. Feeling disappointed after the third ring I was about to hang up when
"Henry? This is Woody. Recall we met yesterday?"
"Sure do. How's it going?"
"Things are good."
I hesitated for a couple of seconds then blurted out that I wanted to get together
"When did you have in mind? I'm free this afternoon."
"That would be great. It'll take me about 15 minutes to get there."
"I'll be waiting."
"See ya" I rang off and hurried out to my car.
I was at his door in 10 minutes. I rang the bell and gave my name at the intercom.
"Come on in" said Henry as the buzzer unlocked the door. He greeted me at the top
of the stairs. There was no confusion as to what was about to go down, as Henry was
wearing nothing but a smile.
"No Walter today?"
"No, I wanted to be with you one on one."
"I'm flattered. I didn't think I made that big of an impression.
I followed him to the bedroom and stripped. Henry's cock was stiff and ready for action.
We got onto the bed and began 69-ing. After a few minutes of sucking each other I had him
roll over and began rimming him. He squirmed and I placed a tentative finger at his pucker.
He immediately pushed back and my finger went in.
"Hold on a second. I have some lube on the dresser. I want you to fuck me."
Henry began coating my dick with KY then told me to work some generously into his ass crack.
I complied and soon he was as slick as an eel.
Henry knelt on the bed and I squirreled up behind him. I pointed my cock at his pucker
and slowly inched into him. I pushed all the way until my pubes were tickling his cheeks.
It felt incredibly tight and hot. Slowly I pulled back until nothing but the tip remained in
him then I pushed forward again until I was fully imbedded in him.
"O yes!" he gasped, "fuck me harder! Slam it into me!"
I began to fuck in earnest, my belly making slapping sounds against his cheeks. A few minutes
of this and I could no longer control myself. I jammed in all the way and began spurting into
his bowels. As I withdrew from him I could see a spot of my cum drooling out of him.
We lay side by side thighs touching.
"That was hot."
"I'll say. You sure caught on fast."
"I've been thinking about it ever since yesterday afternoon. Was crazy to see how it felt."
"And?" Henry was propped up his hand cupped under his chin and smiling at me.
"It felt terrific!" I replied, "but doesn't it hurt?"
"It hurt the first few times but once I learned to relax the pleasure outweighed the pain.
Want to see for yourself?"
"You mean you'd fuck me?"
"Sure, I like it either way. No pressure though."
"You'll be gentle?"
"That goes without saying. We won't do anything you don't want to."
Henry grabbed the lube and coated his cock with it then worked it into my ass crack. The
pleasure of his massaging finger heightened my anticipation of what was about to happen. Then
I felt intrusion as Henry slowly slid a finger into me. I instinctively clinched and Henry told
me to relax, that I'd get used to it after a bit. To my surprise I did get somewhat more
comfortable at which point a second finger was inserted. I cried out at the pain of it, but
Henry's soothing voice kept urging me to relax. Minutes passed and a third finger joined the
two. This time I was able to relax more quickly. Henry withdrew his fingers and I felt the
blunt tip of his cockhead pushing against my pucker. He began inching into me slowly but
inexorably as I felt it touch my prostate gland. I was sweating like a pig and the pressure
of this invasion no matter how I tried to relax it hurt like hell. He pulled back as slowly as
he had entered then pushed forward again. I was about to tell him I wanted to throw in the
towel when I felt his juice spurting into me. He withdrew and a wet pop signaled that he was
We lay back on the bed.
"Well, I'm sure it hurts a bit, but you're not a virgin anymore. Believe me you'll get to
like it after a little practice." Henry was up on his elbow again.
"I'll say it hurt and still does. But I lived through it."
"That's the attitude! Can you get it up again? I'd like to suck you off."
Why don't we 69 for a bit and see what comes up?"
Henry immediately got into the position and we began sucking each others' flaccid cocks. We
kept it up for a good 15 minutes before deciding that nothing was going to come of it.
As I was leaving Henry said we'd have to do this again soon. The way my ass felt I wasn't so
sure that was a good idea, but then he had been reassuring that eventually I would come to
The next day I felt ok and again lunched with my four buddies. I was quite upbeat compared
with the prior day and Richard seemed even more friendly than usual. Ralph and Walter were
disappointed to learn that I had taken the bus today and that they would not be enjoying an
after school orgy.
Richard and I showered next to each other then dressed and walked to the bus stop. We sat on
the rear seat placing our book bags in our laps. Richard asked if I'd like to come over and
play and I readily agreed.
Once in his den we shed our clothes and embraced. Richard's hard cock pressed against my tummy
and I was lengthening quickly as our tongues jousted in their little mock duel. Once we broke
the embrace Richard put a Miles Davis album on the stereo and we sat side by side on the
"I had a new experience yesterday." I looked at Richard earnestly.
"O? What was that?"
I recounted the recruitment of Henry and then how we had fucked each other.
"You fucked each other?" Richard was incredulous.
"Yes. I cornholed him and then he did me."
"Wow! How did it feel? Didn't it hurt?"
"It didn't seem to faze him, in fact he urged me to fuck him harder. As for me, it hurt plenty
but Henry assured me that once I learned to relax I'd enjoy taking it."
"You plan on learning to relax?"
"I think I'll try it again. Fucking is hot."
"I can imagine, but the learning process isn't real attractive."
"Want to give me a lesson?" I looked into Richard's eyes.
"O hell! What do I have to lose?"
"We'll need some lubricant."
"What kind? Vaseline?"
"Henry used something called K/Y."
"We have some of that in the medicine cabinet. I'll go get it."
As I waited for Richard to return I marveled at what a week had wroth in my life. I had been
sucked, sucked my first cock, participated in an orgy, swallowed cum, fucked a man and got
fucked by one and was about to be fucked by a second. I had turned into a really avid
Richard returned with a tube of K/Y. I stooped and sucked his cock back up hard. When he
was fully engorged I coated his cock with the K/Y and asked him to coat my ass with it.
To my surprise and delight, Richard knelt behind me and rimmed me before slathering the target.
"I need to loosen up a bit, so start putting a finger in there."
As he complied I clinched again but after a moment was relaxed enough to accommodate a second
finger. When I was able to handle a third I told him to substitute his cock. I felt that
long black snake pushing into my ass. Richard is a bit thicker and longer than Henry and his
full penetration explored uncharted territory. The pain was intense but I tried to relax and
ultimately achieved some level of comfort. Richard slid all the way in and held. He began
caressing my shoulders then reached around and grabbed my hot cock. He gave me a couple of
strokes and I lost all control. I shot a huge wad onto the carpet. My body trembled in my
ecstasy which drove Richard over the edge. I felt him spurting deep into me.
We lay there beside each other on the carpet. Richard rolled over and took me into his arms.
He kissed me deeply. There was no mistaking the ardor in him and I realized this was genuine
"I hope I didn't hurt you. That was really fun."
"I'm hoping to get used to it" I replied, "but it really does hurt."
"I doubt I'll be trying it anytime soon."
"Any time you decide you want to I am at your service."
"Gee Woody you're a real pal." Richard was smiling broadly.
It was time for me to get cutting so we dressed, kissed each other goodbye and I left. Fucked
two times in as many days, it occurred to me that I was getting wild and needed to calm down.