My first anal experience

By | 17 October 2019

My first anal experience with my older Bisexual Neighbour

My First anal experience was with Steve and I had been playing around for
about a month now. I was the kid who did some yard work for him. He was in
his 30s, I had just turned 18 and was young, naive, and horny.

My first time was when I walked into his house while doing some work for him.
I walked in unannounced, and caught him in the livingroom on the couch,
stroking his dick. I was the typical wide-eyed kid. But also damn horny. He
must have been able to tell, because instead of stopping his stroking, he
continued as I watched, the bulge in my crotch filling out the cut-offs
I wore. He apologized for being in such a “condition”, but he also said he
could tell I liked what I saw. I couldn’t tell then how he had known. He was
a married guy with a cute wife. Why would he want me? I knew I liked cock.
In school, I was always checking out my class mates’ equipment in gym class.
And a three of us had circle jerked the past summer. I loved seeing a hard
cock spurt cum. Now I was watching this grown man play with his dick.

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We ended up jerking off together then. I can still remember his hand as it
explored my crotch and unbuttoned my shorts. When my cock popped out into
his hand, the sensation of his touch almost made me cum. In not too many
strokes, I did cum, filling his warm hand with my boy spunk. He held
me close and kissed me, rubbing my body with my cum, his tongue gently
pushing into my mouth. Our tongues played and I reached for his penis,
stroking it and making it harder and harder until he came with lots of
shouting and spurting.

We collapsed together and talked for nearly an hour. He told me about his
bisexuality and how, even though he loved his wife a lot, he needed sex with
a guy. He praised my youthful body and told me how much he wanted to show
me how good sex could be with a man. He told me that I should accept
my sexual feelings as OK and good, and that sex between men is OK and
not something to be ashamed of.

Over the next few weeks, every opportunity I had, I spent with Steve.
Education at school was never like this. I loved Steve’s strong arms and
large cock. He savored my foreskin, which he loved to play with and suck.

But all our encounters were fairly short, and we both longed to be together
a full day, or better, a full day and night. That chance came when Steve asked
if I’d like to go for a weekend trip to Lake Tahoe. He had a friend who
had a cabin up there, where we could play without interruptions. Steve
talked to my parents, and they approved of the trip. Steve and his wife,
Angela, were beyond reproach. All the neighbors liked them and trusted
them. So for my parents to send me off for a weekend with Steve was not
unusual.

We left early Saturday morning for the cabin at South Lake Tahoe. I could tell
Steve was anxious to get moving, horny for play time. I could see his thick
dick meat pushing against the front of his shorts as he sat behind the wheel.
I dressed in my cutoffs, as usual, except this time I left off underwear so I
could pop the buttons open and treat Steve to a Cock Treat if the opportunity
presented itself.

We stopped for breakfast at the Coffee Tree in Vacaville, and we made
a quick retreat to the john, where we drained our bladders, side by side.
I stole glances at my friend’s thick man meat, and he stole a kiss, his lips
meeting mine and his tongue pushing into my mouth. My cock jumped to
attention. Steve continued the kiss, and his hands wandered to my ass cheeks,
which he rubbed sensuously. We broke the kiss — for fear of being caught in
the act — and went to our table.

While we ate, I felt Steve’s hand under the table massaging my knee. I guess
we could have fucked on the spot. But there were still several hours of
driving left.

As we rode to the cabin, I put my hand on Steve’s leg and sometimes rubbed
his crotch. He felt so big and hard. I knew I wanted him. And when he
put his hand on my leg and felt my crotch, I knew I wanted him, too.
Once I slid down on the seat and rested my head on his leg. I wanted to
unzip his pants and slip his dick into my mouth, but I worried about the
curvy Highway 50 and how unpleasant it would be if we ended up at the
bottom of some steep canyon. But I knew how good Steve’s cock felt in my
mouth and I wanted it. I knew how turned on he was by me. My first time
I showed him my man/boy penis, I think he almost came just from looking.
It hadn’t grown to it’s full 7 inches, and the hair was sparser, but my
uncut prick pleased Steve.

When we arrived at the cabin, the first thing we did was open all the windows,
because the summer heat made the small house very warm. As soon as we
emptied the car of our supplies, Steve took me in his arms and held me close.

His mouth gently touched my lips and gradually his tongue parted my lips,
seeking the warmth of my throat. His hands roamed under my t-shirt and
rubbed my back, his fingers running under the waist of my cut-offs and
traveling over my behind.

His touch made me shiver, and I knew then — as his fingers toyed with
my butt — that I wanted I wanted his cock for my first anal experience.
But I’d always rubbed myself under my balls and back to my
butt hole when I was jacking off. I was determined Steve would fuck me.

Quick as a flash, Steve raised mt t-short from my body, then knelt before
me and quickly unbuttoned my worn shorts. My extremely hard penis poked
him in the face as he admired my form. I watched as his head bobbed down
to engulf my manhood. My body shook with sexual energy as his talented
mouth sucked me and his fingers gripped my boyish buns.

I watched in ecstasy as Steve swallowed my prick, at the edge of cumming,
but trying to hold off just a bit longer. Then I felt it. A finger poking
into my ass. Oh, God. I lost it and spewed squirt after squirt into
Steve’s waiting mouth. Cum dripped down his cheeks as I held his head
on my cock, waiting for the spasms to end.

My knees felt weak, and I dropped to the floor. Our lips met again
and we kissed passionately. I tasted my cum and clung to my friend.
My first orgasm of a long weekend.

I offered to suck Steve’s painfully erect cock, but he wanted to wait.
He was almost ready to shoot without my mouth on his cock, and he wanted
to cool down before he did more.

So we talked. And hugged. And talked some more.

Steve explained how unusual and special our love for each other was. Yes, I
knew what we were doing was considered wrong by many people: an older man
“seducing” a teenager. But Steve wasn’t doing anything I didn’t want
done. There was no force involved. If I hadn’t walked in on him that day,
I probably would not have known about his desires or he mine.

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Steve told me his wife, Angela, knew about his bisexuality and that while
she didn’t really approve of him fooling around, she didn’t forbid it,
either. They were both sexually liberated, and he would not get mad
if she had an affair with a man or a woman.

I had played a bit with girls, going as far as feeling the very wet
cunt lips of a sexy little blonde girl in my math class. I hadn’t
gone all the way, and I asked Steve to tell me about it. He described
what it was like to make love to Angela, how he liked to suck her,
and then slowly piston his cock in her pussy. His description made me
hard again, and Steve laughingly suggested that maybe someday I could
fuck her someday.

The warmth of the cabin had made us both sweaty, and Steve suggested
a shower. Naive as I was, I thought he meant a shower alone. We ended up
sharing the small stall shower, enjoying the cooling water and exploring
each other’s bodies, working up a lather in more ways than one.

Steve soaped me from head to toe, paying special attention to my
genitals and my butt. His fingers played up and down my crack, and I felt
him push one into my hole. The invader in my ass had a direct line to my
sudsy cock — an instant erection sprouted. If there was any doubt about
my fuckability, none existed now.

I told Steve I wanted his cock up my ass so I could experience my first
anal experience, which I wanted to have with Steve. I wanted to be fucked just
like Angela. Steve smiled and hugged me. Our cocks tangled and pushed
against each other. We were both eager for the next step.

We rinsed and stepped out of the shower. As I started to get out, I felt
Steve’s hands pulling my butt cheeks apart. Then a new sensation — a warm
tongue dipped into my crack and licked my hole. Oh holy jesus god. Fuck me
Steve.

I pretty much knew what fucking meant. But I wasn’t prepared for Steve’s
next move. He lead me to the bed and had me lie on my side, knees drawn up
to my chest. Soon I felt something pushing into my ass, something hard
but not a cock.

I peered behind me and saw Steve hooking up the tubing and bag. An
enema? Good God! Steve calmed me and told me he liked fucking clean
asses, not butts filled with shit. He told me that he and his wife
butt fucked, too, and that he always gave Angela a couple of small
cleansing enemas before his fucked her.

I had to admit it felt good as he slowly let the water run into my
butt. And he made it feel even better by slowly stroking my cock
as the water entered me. It wasn’t a large amount of water, just
enough to do the job. He pulled the nozzle from my behind and
helped me to the john, even watching as I sat there and pumped the
water from my bowels.

One more time he filled the bag and one more time I took the water and
emptied it. Then it was time. The virgin boy’s butt was gonna be fucked.

Steve was in no hurry, however.

After he wiped my ass with a washcloth, he took a tube of lube from his
satchel and applied some to my butt crack. I’m on my stomach and my ass
is lifted slightly. Then his finger pushes into me. Slowly then a real
fucking, in-and-out motion. Then two fingers.

We lie side by side, embracing and kissing. Steve’s hands all over my
cock and balls, stroking, rubbing, squeezing, pulling.

His mouth travels down my neck, biting and sucking his way to my
smooth chest. He bites down on my nipple and I shudder. It feels good
to have him playing with my body.

I reach for his cock and hold on to it. It is still very hard. I wonder how
long he can hold out after being aroused for so long.

He rolls me on my back and straddles my chest. His fat penis sits invitingly
in front of my face. I open my mouth wide and he thrusts forward.

Steve’s penis is beautiful. The full mushroom-like head crowns about 7-8
inches of heavily veined shaft. Surrounding his meat and balls is a thick
coat of black pubic hair. In fact, his whole body is very hairy. His chest,
legs, arms and ass all swirled with dark hair.

I want to take him all in my throat, like he did me, but I can’t yet. I
taste his pre-orgasmic juices and wish I could taste his cum. At almost
the same instant, Steve’s body shakes, and a loud moan catapults from
his lips. I’m taking his cum in my mouth. Spurt after spurt of warm, creamy
cum. It fills my throat and makes it hard to swallow. He pulls his penis
from my mouth and we both smile.

More hugs and kisses. Steve promises me it won’t be long before I get
my first fucking. I kid him about old men needing a long time to “recover”. He
laughs and swats my ass, telling me I’ll get it soon enough!

We embrace like two spoons in a drawer, both on our sides, his chest
against my back. I can feel his now-soft dick resting against my buns.
We sleep.

For about an hour we rested. I awoke feeling Steve’s hardness between
me ass cheeks. “Fuck me,” I whisper.

Steve pushes me onto my tummy and gently covers my body with his. I feel his
man-cock pressing into my hole.

He pushed forward and I yelp.

He stops and kisses the back of my neck and reaches under me to play
with my still-hard dick.

Again a forward push. Ohhhhhhh. More and more of him is in me. Little by
little, he moves forward into my butt. His cock fills me with erotic
passion. My cock is dripping and my ass feels stretched as it never
has before.

Once he’s all the way in, he pulls out.

“Don’t leave,” I say. Then I feel him moving back in. Fuck me, man.

And he does. Steve moves in and out of my ass, slowly then fast. Slow, then
fast. Finally I am experiencing my first anal fucking and he plays with my
cock as he fucks, and I cum. Like never before. Cum all over.

Steve’s fucking continues. Steve’s fucking his neighbor boy. Neighbor
boy is in heaven. Faster and faster he plunges into my hole.

I wonder if this is how his wife must feel as my man’s penis invades
my body. What a lucky woman to have this man to fuck her.

I feel his body tense up and another load moan and a series of quick jerks
tells me he’s found heaven, too. He collapses on top of me and
let’s his prick grow soft in my hole.

He slips his spent penis from my rectum and again we taste a deep and
prolonged kiss.

It’s just Saturday afternoon. The whole night remains. Steve is
teaching me well.

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