Date: Wed, 20 Jun 2018 08:53:22 -0700
From: wrsjrm@gmail.com
Subject: SEDUCING THE MIDDLE AGE GUY

SEDUCING THE OLDER GUY

Support Nifty, please.

I would love to correspond with anybody who has been through the type of
experience like the one I had, whether you were the younger or older of
the two.  Contact me at wrsjrm@gmail.com.  I would like to add your story
of "intergenerational" sex to this and maybe make this a series, if there
is interest.

This is sexual encounter between a middle age man, John, and me. I had
just graduated form a local suburban high school to the northeast of
Seattle and it was my first real gay experience.  I admit I loved looking
at gay porn, as a teenager, and my curiosity in seeing another man naked
and in person became an obsession.   My dad had died of cancer a few
years earlier and I was the youngest and only male in a house with two
older sisters and my still single mother.  I really missed my father and
longed to meet a guy around my dad's age. I remember how I was amazed at
seeing my dad's penis when I was able to catch him naked after his
morning showers as a grade school boy. He was never shy about his nudity
in front of me and would answer most questions asked by a curious kid,
like I was, about my own and his genitals; mostly concerning the
difference in sizes, his pubic hair and my lack of, etc. And, at the
time, I wondered if his penis got hard like mine did to which he assured
me it did.

I initiated the encounter with John and, from the start, he showed a
cautious interest in me, probably due to my age, of which I had turned 18
in late May of 1999. He was in his early 40s, the same age my dad would
have been which made this encounter perfect.

John had posted an ad on a well-known personals web site seeking a mutual
masturbation encounter with anybody who might find it erotic to do this
with him.  I started to write responses to John's ad several times, but
would ultimately chicken out.  It wasn't until late June I got brave
enough and took a chance that would change my life.

I was fairly athletic; I ran track and cross-country teams for my high
school and played soccer as a mid-fielder; a position that assured I
would be running quite a bit as one of the `work-horses' of the team.  I
graduated in the top 10% of my class and I had plans to join the Air
Force. I had sandy blond, crew cut hair and my body was slim and I had a
good looking six pack going for myself. I loved how I looked naked and
posed often in front of the mirror on the inside of my bedroom door;
admiring my physique and, more importantly, a nice hard erection I got
when posing naked.

I finally got up enough courage to hit the send button on a response to
John, "Hey, I really like your ad.  I'm not the same age guy you're
looking for, rather an 18-year-old-guy that is also looking for a guy to
masturbate with, because the look of a penis and parts are a major turn
on to me."

John was surprised, a little hesitant and expressed some doubt that I
was for real. I guess most 40-something guys find it hard to believe a
young guy like me would be willing to get naked with them. John responded
and asked if I was really interested in masturbating with him.

I replied, "Yes, I would really like to see the masturbation technique of a
40-year-old guy.  I've never done this before with my friends and none
really showed any desire so I haven't been persistent about asking
them.  I think a mutual show-off would be a major learning experience and
something worth doing. My desires, well, I'm definitely straight, I like
girls too much to be gay."

Did I really write that? `Yeah, right,' you, as the horny Nifty reader,
are thinking. But I really did write that.

At 18, I was much into self-denial that I had any major sexual interest
in other guys.  It is obvious now I was going through what many boys and
young men experience while trying to figure out ultimate sexualities.

I continued, "But I'm certainly bi-curious.  I like to jack off to gay
porn I see on the internet and have always wanted to jack off with
another guy.  I guess what I'm expecting out of this meeting is to see
how it is, how other people perform this type of sexual expression.  I
would love to watch you then show off myself.  I want to see what men are
like, I mean really up close, not just in the YMCA shower or whatever.  I
want to play with your penis, compare your boner to mine and see you
jacking your cock and watch your techniques.  Sounds like you have
similar desires."

Since it was summer, I was home alone during the day while my mother and
sisters had jobs.  I bravely suggested John come over to my house.  This
was immediately rejected by John who reminded me that neighbors could
notice him "visiting" and it would not go well if neighbors saw a
stranger enter my house during the day.  John suggested he would rent a
room at a local Motel 6 and I could meet him there.  And, thus, an
encounter was set.

John took a short vacation over the July 4th holiday weekend.  When he
got back, he emailed me and asked if he was still interested.  Boy, was
I!  My interest had grown and the fantasy of meeting up with a guy like
John made me horny with anticipation. Every email from John made my penis
jump and my balls tighten with excitement.  I put urgency in my reply.  I
was going leave for Air Force basic training in August and in coming
weeks, I would become increasingly busy.  A date was agreed upon, in mid-
July, on a Tuesday. John suggested a Friday, but I had been "saving" my
sperm up for the meeting and I really needed to jack off soon.  John
quickly agreed.  I was seducing the middle age guy!

It was then that I went further with my requests, "Is masturbation all
that you want to do?" I asked.

John wanted to masturbate me and he thought I only wanted to return the
favor.

I continued, "I'm also curious about trying some oral."

John agreed that everything was on the table as long as it was safe and
pain free.  He set things up and emailed instructions as to the hotel and
time. He gave me his cell number and asked me to give him a discrete text
of my agreement.

Despite my being nervous, there was going to be no turning back, now. I
indicated my willingness to keep our date with just six numbers:
"696969!"

It takes about 15 minutes to drive to the motel, off I-405, about 15
minutes from my house. My cock was semi-hard and emitting pre-cum with my
obvious excitement as I drove.  He had told me what he was going to wear
and he would be waiting by the pool, reading a newspaper.  Nervously, I
walked past the front desk with little notice and to the gate to the
pool. John was there and set his paper down.

He was a typical "dad" type guy and he looked and dressed nice, like a
businessman.

He came to the gate and, with a firm handshake, introduced himself. He
spoke gently which kind of sounded sexy to me. Just the same, I nervously
followed him to his room.

He appeared to be very eager to do this. We shut the door to the room and
it was John and I, alone.

After some small talk, we stripped down to our briefs.  We were both
hard.  I continued my seduction of John.  I invited him over and dared
him to start feeling me up.  He slipped his fingers through my waistband
then around the openings in his crotch. I had a serious case of blue-
balls and my very erect manhood screamed for its freedom.  I made sure I
was feeling him up the same way.

After a few minutes of fondling each other through our briefs, John got
brazen and teased, "Let's see what you've got."

With this, he pulled down my briefs and found a little surprise.  I was
wearing my sister's bright red bikini thong that was barely able to
contain what was still hidden from view.  John quickly pulled this down
revealing my nice late teen cock at its ultimate 6-1/2" long.  I returned
the favor and pulled his briefs down and out sprang his cute 6" erection.
His boner was thinner than mine, and a little shorter, also.  His penis
tip had a luscious mushroom look that was drooling with pre-cum.

In comparison, I had a thicker cock, much wider at mid shaft than at the
tip. My piss slit always went agape when I got erections but John's slit
stayed tightly closed. I was getting what I wanted: comparing my manhood
with that of another guy. I loved the differences in our cocks. Both of
our cocks were drooling with pre-cum.

"I really want to look at your cock up close," I said.

He agreed, so we laid on the bed, 69, and started to go to work on touching,
stroking, working our nuts over and placing fingers on those sensitive
erogenous areas between our nut sacks and assholes.  Next thing I knew, I
was gently licking the pre-cum off his cockhead.  I took it into my mouth
and I bravely was giving my first blow job to another guy!  John appeared
to be in heaven.  One good turn deserves another, so he took his tongue
to my slit and tasted my pre-cum.

"Please play with my balls," I remember whispering.

I was really enjoying having my 18-year-old erection and nuts worked over
by someone over twice my age.  After a while, John mentioned he would
show me something that he liked to do to himself.  It's extremely
stimulating but he promised it wasn't enough to bring about an
orgasm.  Besides, I had said I wanted to have a "major learning
experience."

He put some lube the palm of his hand and started to gently massage my
cockhead.  First the slit, mixing the lube with my flowing pre-
cum.  Making small circular motions with his palm, John started to work
my cockhead over.  He varied the speed and direction.  Soon I was
squirming and he probably noticed how delightful I thought this was.

"Oh yes, that really feels awesome!"  I probably said.

John then let me work him over; he definitely wanted to experience an
orgasm at the hands of an 18-year-old. I stroked him with my best
masturbation skills up to this point.  I paid close attention to John's
nuts as I stroked away. He closed his eyes and was obviously enjoying the
ride I was giving him.  His nuts started to tighten and then came his
first delightful pump of cum.  I stopped stroking and just held his
penis, which kept him on edge for a few short seconds.  The next pump
came, then a third. He was spewing his load right in front of my face.

John then turned his attention to my cock. He had brought lube and he
applied it and then started in His masturbation technique was different.
He did my cock with slow but consistent strokes. Always moving, never
stopping. As his hand glided over my cockhead, he would give it a little
twist. The best way I can describe this was that I, no, my boner was
being tortured, slowly, but what a beautiful erotic torture! John was not
in a hurry to see me cum. I pleaded with him to speed up.  He was having
a great deal of fun seeing how a young man was responding to the
techniques he had developed over his 30 some years of masturbation
experiences.

"Hold my balls," I pleaded.

I could feel them tightening as I was now very close to cumming. John
asked if I wanted to be relieved of my exquisite sexual agony. I felt my
cum pooling behind my balls as my cockhead swelled in anticipation of its
much deserved reward.  My first shot flew over my shoulder and landed on
the bed.  It was quickly followed by several more that shot out of my
exploding cock like water bubbling out of a drinking fountain. John then
went about cleaning my stomach and pubic area with his tongue. My own
cum's taste was always a sexy turn on, to me, and I hope John enjoyed it,
also.

I never saw John again but I really would like to. He was gentle. His
kindness and patience with me assured me that my own budding homosexuality
was real, although I had a lot more to figure out.

Again, I would love to correspond with anybody who has been through this
type of experience, whether you were the younger or older of the two.
Contact me at wrsjrm@gmail.com.  I would like to add your true story of an
`intergenerational encounter with a stranger' type sex to this.  It should
be a `first time' encounter (as far as one knows) for the younger guy and
I'm NOT looking for an encounter between an adult and a child under the age
of consent.

Maybe I will make this a series, if there is interest and interesting
stories.

Comments, feedback and questions about this writing are also welcome.