My boring office job is driving my crazy. So is my sexless marriage. My
wife is beautiful and my best pal, but somehow the sex drive seems to have
dropped off the page of our life together.
Several years back I indulged in sex with a guy. I indulge in this
infrequently, but as of late the urge has been returning with a vengeance.
I think it's due to a state of boredom mixed with urgent horniness.
In San Francisco there is an Internet bulletin board called Craigslist. I
often scan the listings when I am bored at work. This site has classified
for real estate, housing, jobs, cars, and all sorts of other stuff
including personal ads. Needless to say, I spend a lot of time browsing
the "man for man" personals. The neat thing is that these ads can be
filtered which makes it real easy to narrow the focus of a search by
location, age, or sexual inclination.
Recently, I have been having fantasies about connecting with a mature older
man. Someone in his 50's or 60's who lives alone: maybe a widower or a
divorced bi guy, with a hunger for younger men. Something within me
yearned to please an older guy and to be treated as a son. Perhaps I was
dwelling on some sort of "incest with Dad fantasy," I `m not really sure?
But something about older bi and gay men made me feel as if they were more
sincere, honest and real than the jerks that normally populate this
bulletin board wanting to eat poop or have fast anonymous sex. In reality,
I want relatively anonymous no-strings sex, but I want it with a clean,
caring, mature, hygienic person with a good head on his shoulders. I don't
want to connect with idiots or assholes.
So, I started scanning the classifieds in hopes of finding an ad that
suggested whoever posted it was sincere, as opposed to the vulgar desperate
angle that most of these posts seem to have. I filtered for someone
between 55 and 75 and started scanning the results. Ultimately I found a
post that really intrigued me. It read as follows:
Mature guy looking for younger hot, fit, sexy guy to have some play and
fun!! Me: 5'7", 205 lbs., lightly hairy body, healthy, d/d free, negative
(UB2), 6.5" cut, thick, large head, nice balls, super
clean...safe, sane, and strong sex drive...YOU: fit/average/muscular body,
super clean, like long sessions with cuddling/kissing/lots of oral...more
with the right guy...TONIGHT if possible! Please send pic with your
response and I will return the same...My place--safe, discreet,
comfortable...let's play, have fun, and enjoy being two men together for
total pleasure...ongoing would be great!!...
I thought to myself, "bingo," but the chances of hooking up for real are
slim in this nutty Craigslist world. My past experiences dictated that
most guys are flakes who don't follow through. Nonetheless I replied with
a face pic and a brief description of myself:
I am 39, bi, married, closeted, sincere, passionate and very friendly.
I am 6', 210, extremely discrete, safe, hiv neg, clean and careful.
I have been bi about 5 years and only play on occasion with safe sane people.
I have enjoyed one or two connections I've made in the past with genuine,
nice older men.
I'd be interested in possibly connecting with you after we have had a
chance to exchange some info with each other.
I look forward to hearing back from you, but if you are already connected
with another, please play safely.
My work day passed uneventfully and I commuted home as usual. The next
morning I received a reply and photo from "Jim." He was good looking with
a dignified face and shocking white hair -- a strong fatherly type. His
reply read as follows:
Thanks for the response.
I like the "sound" of your email and your underlying enthusiasm.
Tonight may work. Will you have a cell phone with you?
His reply was notably vague but at the same time sincere, but I wrote back.
I'll spare the details but he invited me over that night. I gave my wife
the line that I was going to a rehearsal. (In my spare time I am a working
musician) and nothing more was said. I hopped in the car around 7 and
calmly drove south from the city with my heart pounding in my chest and my
cock dripping in anticipation.
When I got to his freeway exit I dialed him on my cell phone: "Hi, Jim.
It's me, Terry."
"Hey buddy, it's good to hear your voice," he said. I thought to myself,
He sounds so nice and real, I think we're going to have a great connection.
"So I'm nearby Jim. Is it ok to come right up to your front door?" Jim
replied with, "I live alone Terry. Feel free to knock."
Moment's later I was at his door, trying to keep my cool, but jittery with
anxiety. I nervously knocked. He opened and invited me in. He was
dressed in slacks, a white cotton button down dress shirt and loafers. His
white hair combed back neatly complimented his tanned skin. He smelled of
soap and looked delicious to me. His place was clean and well appointed
with modern furniture and had the aura of a man's home. I sensed the vague
aroma of single malt scotch co-mingled with deodorant as we sat side by
side on his plush leather sofa.
"Thanks so much for having me over Jim." "No worries Terry. I'm so glad
you could make it... So you are married Terry?" "Yes," I said in reply.
"My wife is a great gal, but we just don't have much sex as of late and my
mind has been turning towards thoughts of men." "I know how that can be
Terry. My wife died two years ago but the latter part of our long
connection was sexually inactive. I started connecting with men about 10
years ago, and now, I am fully comfortable with my gayness. It certainly
has been more erotic." As he said this, he reached out and stroked my
leg.and my cock twitched with arousal.
"So have you had any long-term relationships with younger guys Terry?" He
replied, "Well, I just got passed a recent connection with a young fellow
who wound up moving back east with his family. We had a nice thing going
but I guess you could say I am on the rebound now." "Understood," I said
with a wink. "I must say, you are a very handsome guy Jim. You kind of
match all the expectations I have had about connecting with a warm,
friendly and sincere older man." "Well I can honestly say the same about
you Terry. You have a great smile and a hot body."
By this time, we were intently touching each other, rubbing and caressing.
In fact, he was rubbing my erection through my slacks as I caressed his
torso. Then he leaned over gently and pressed his lips against mine, his
warm tongue found its way to mine, and we kissed deeply. It felt
incredible to be with him, on his sofa, in the safety and comfort of his
home. Not much more was said as we French kissed and cuddled there in the
dim twilight of an early spring evening. After a few moments he stood,
holding my right hand in his. He pulled me up, and romantically undressed
me. I reciprocated, taking time to kiss and squeeze his nipples as I
unbuttoned his shirt and unzipped his slacks.
When we were both naked we pressed our chests together in a warm embrace,
kissing deeply once again. His cock was a stiff 6.5 inches, lined with
turgid blue veins and a smooth bulbous head. Mine was similar and standing
stiffly upright with arousal. He took my hand and led me up the stairs to
He had a large king-size bed with a cherry frame that was elegantly made up
with tan sheets that matched the hue of the bedroom walls. He pulled back
the covers and we lay down together side by side and continued our intimate
snuggling. By this time I was in a state of blissful escape from my
workaday world there in Jim's bed. I was his lover, his young devotee,
catering to his sexual needs; filling the void in his world, the receptacle
of his loving attention. He laid me out on my back, wrapped his strong
arms around my torso and pressed his chest against mine. Then he jammed
his tongue deep in the back of my throat telling me through his body
language that he would be assuming a dominant sexual roll in our
connection. Then he relaxed and held onto the headboard, raising his
thick, stiff cock to my lips. I complied and his shaft eased gently
through my lips and deep into the back of my throat. I hungrily accepted
his advances, sucking and slurping his smooth cock with gleeful abandon and
loving the sensation of him inside my mouth. At the same time Jim reached
back behind himself and stroked me to full erection. I was losing control
but striving to keep my cool in this incredibly arousing situation. I was
overwhelmed with lust for this older man as his cock slammed my velvety
throat and his hand stroked me to the point of leaking. Then, just as he
was reaching his own state of climax, I shot a huge load upon his back and
all over and the bed sheets. At the same time his cum slammed the back of
my throat and with an insecure sense of trust; I devoured every drop,
savoring the warm, salty essence of his cum. He whispered, "Terry, have no
worries. I am safe and negative." Through my cum guzzling state I
replied... "Good Jim, I need to know that."
The next ten minutes we lay in a pile of man sweat and cum, cuddling and
caressing; speaking gently of our experiences and fantasies. Moments
passed and soon we were aroused again, stroking each other's stiff arousal
and moving towards something deeper.
After a few more moments Jim said, "Terry, I want you. I want to have you.
Is this something you want to?" I smiled and nodded, knowing what he had
in mind. I rolled up on the bed with my head resting on soft pillows and
placed my legs upon his shoulders. He reached over to the night table,
opened a drawer, removed a tube of lubricant and some condoms and set to
work easing well-greased fingers into my love hole. My back arched with
his touch and as he stuffed three lubed fingers deep within me and began to
nudge my prostate gland, driving me wild with desire for his cock. "Oh,
Jim... please, please fuck me now," I said. He replied, "Only too happy to
oblige, son," With the operative word, "Son," I knew our connection was
meant to be.
Without indulging in any bizarre role-play, we were, for all intents and
purposes making real my personally held fantasy to engage in a father-son
sexual connection and his way with me was extremely effective. A moment or
two later he was nudging the thick bulbous head of his condom covered cock
into and past my tight rosebud. The friction in my rear and the pressure
upon my prostate was incredible and I squeezed and milked his cock with my
ass muscles, reciprocating with my own body language letting him know
without words, how much pleasure he was bringing me.
He began to pump and buck and ride my ass, plowing me with long powerful
strokes of his cock; my rear receiving his turgid thickness and widening to
adapt to the depth of his pumping motions. After 10 minutes of this, our
bodies glistened with a thin film of sweat which served to lubricate our
motions and caused me to revel in the intensity of our lust for each other.
Finally, with the last of his hugely powerful lunges he leaned over, gazed
deeply into my eyes and pressed his tongue deeply in my mouth, swirling it
around in my cum-glazed orifice. He hugged me tightly and as his back
arched he exploded in my rear. At the same time I shot wads of spunk all
over his chest as he stroked and milked my cock to finality.
The intensity of our connection was beyond words; two lustful men
experiencing the height of erotic man to man sexual arousal. His dignified
essence showed me the way; my bi-sexual naivety was taken to a higher place
by this experienced and loving mature father-like figure of a man.
We spent the balance of the night in his bed, like spoons in a drawer. I
was his lover and the future was ours to experience...
Following my initial experience my newfound, mature fatherly lover, Jim,;
the one I'd met online via Craigslist.org, I found myself deeply smitten
with him. Of course, after our initial connection I was forced to create a
psychological firewall for myself in order to separate this new compulsion
from the very true and sincere love and friendship I have had with my wife,
but after five years of discrete bisexual experimentation I felt I was now
ready for a deeper connection with a man, albeit with all the same caution
and care I'd taken in my occasional indulgences.
>From the moment I'd connected with Jim, ours was a passionate affiliation.
We'd kissed and snuggled, had intense contact and made love in the deepest
way with Jim asserting himself kindly but authoritatively as the dominant
Father figure in the initial moments of our tryst. I was more than happy to
serve as a submissive son to this dominant but fatherly man and the pleasure
of our love making solidified the roles we'd assume. I was still not sure
why my heart was telling me that I desired a fatherly lover, but I was
slowly finding out why. We also engaged in lengthy clandestine phone calls
and exchanged many heartfelt emails that contained both fantasy and urgently
expressed emotions that drew us closer as friends, lovers and confidants.
We kept in touch via email and lengthy but discrete phone call on a near
daily basis, but the separation was causing us both a case of intense,
nearly obsessive desire for each other. When my wife announced she'd be
spending a week in the East coast at her father's house and would be taking
our son along with her, the opportunity to physically reconvene my
connection with Jim was made clear. Three weeks later on a Friday evening,
I dropped my family off at SFO and instead of heading back to my home in San
Francisco I veered south to Jim's house content with the notion that I'd
probably be spending a large part of the next week with him at his home
south of the city.
The 30 minute drive south provided me an opportunity to think about the
feelings that were welling up in my psyche about my connection with Jim.
And at the same time, I began to analyze that anxiety these occasional
man-to-man experiences instilled in me. Thinking of that first night with
Jim made my heart thump with this anxiety. And in a way it was addictive.
It was the anxiety of risk, deception and fear mixed with arousal and erotic
possibility. Images rolled through my mind of kissing Jim, his assertive
manor and rigid cock; the smell of his skin and the taste of his cum; but
also the warmth and pleasure of his presence in my life; his friendship,
adoration and tender but authoritative way with me. The more I reflected on
these thoughts the more my heart beat and my own cock stiffened. By the
time I got to Jim's door I was thoroughly aroused at the potential of what
would transpire next between us.
I knocked and Jim opened. He was beaming with happiness and wearing only
bathrobe at the door. "Terry! Thank God you're here. It's been too darn
long and based on what you've told me it seems we may have a week together?
Is this true?"
I gulped and nodded positively, "I just drove the family to the airport and
didn't even bother heading back home Jim. I felt I needed to be near you.
More to the point, I need to be with you, in your bed, by your side... as your
um, ..., well, as your son sir."
Jim smiled acknowledging my statement. He approached me, wrapped his strong
mature arms around me and pressed his lips urgently to mine. Our tongues
swirled with shared delight at the freedom of our arousal and the bliss of
this manly connection. I sensed a familiar and urgent feeling as Jim's cock
stiffened and popped through the fabric of his bathrobe poking me in crotch.
I reached down to caress and stroke him as we continued our languorous
Finally, Jim pulled back from our kiss and said, "You're probably wondering
why I'm in a bathrobe Terry?"
"Well the thought did come to mind Jim, but I wasn't obsessed with why," I
He replied, "Our first night together was so loving and so incredible that I
didn't really get a chance to show you around my place Terry. Just through
the back door I have a wonderful private garden complete with a hot tub
spa. Care to get naked and join me for a nice hot soak lover?"
"Wow, Jim... nothing would please me more," I said. Then he led me to a
sliding glass door at the rear of his house and I followed him out to a
redwood deck nestled in a lovely garden complete with a bouquet of fragrant
aromatic plants, semi-tropical palms and ornamental orchids. In one corner,
adding the idyllic atmosphere was a moss covered natural rock fountain that
trickled with the pleasant din of a mountain stream relocated in a suburban
backyard. The whole thing was an oasis of calm with the hot tub completely
concealed from the prying eyes of neighbors and my mind reflected upon the
love and care that Jim had put into this space and his own pleasure at
sharing it with me. And once again, I felt totally safe and secure with him
at his home. Any fears of being indiscrete were totally shelved in his
The hot tub itself was mounted in a hole in the redwood deck with a changing
bench and bunch of hooks for towels and clothing mounted above it. I
undressed quickly, taking time to neatly hang my clothing on the hooks and
then I slipped into the water beside Jim who was still smiling a great big
grin as he we immersed ourselves in the heated water and began to kiss and
The force of Jim's kisses and the aggressiveness of his caresses made it
clear that he was elated with my presence. His cock was as stiff and thick
as a large cucumber under the surface of the water and I took care to gently
stroke his thick turgid love-stick as we continued to swirl our tongues in
each other's mouths. Then Jim whispered in my ear, "Terri..., `son...," I was
tested for HIV last week and I am totally negative. I trust that you as a
married man are the same?"
I nodded in agreement. "I've always wanted to make love to a man in this
hot tub and have never had the chance. Will you submit to me and be the
first, here and now?"
I replied, "Jim, I'm honored and flattered but at the same time I'm not sure
if you are sincere about my being the first.., though it makes little
difference. I'd love to be your lover here and now." He smiled knowingly
and as I straddled his glistening frame and wiggled my rear end over his
rigid erection. The thought of being taken raw, without protection
frightened me, but our connection had been one based on honesty and
sincerity so I had little reason to doubt him. I also had longed for the
day when a mature, trustworthy lover would take me in this way and I longed
to feel the surging, urgent release of warm creamy cum flooding my insides.
I especially craved the loving, lustful climax of this beautiful man.
I wiggled my rear some more over his thick cock and the natural slickness of
the chlorinated hot tube water seemed to be enough lubricant to allow Jim to
enter my tight anal hole. The friction was incredibly arousing as his 8
inch cock stretched me and I quickly passed through the initial state of
discomfort I'd normally undergone when bottoming. Soon Jim was in me to the
hilt and the feelings we were both experience were of an intensely blissful
nature. My ass ring squeezed and gripped his rock hard shaft in response to
the turgid pressure of his cock so deeply buried within me. I had never
felt so aroused and my own cock surged with pleasure at his masterful
control of my body. My thighs were literally burning with the intensity of
our connection and my own cock was stiff with delight. We kissed deeply
again and then began to shift and gyrate in the bubbling water, our bodies
co-mingling with squeaky satisfaction. Ultimately, the heat and sweat got
the best of us and Jim literally stood up with my legs wrapped around his
body and his cock still deeply embedded in my rear. He carefully leaned
back and laid himself out on the deck with me straddling him, fully mounted
and drilled from below.
"God, Jim – you make me feel so damn alive with lust. I love being your
lover, your son, your boy." These words were imbued with sincerity and
meaning, but were also trigger words of our complimentary fantasy and we
both neared the edge of control, wanting to explode but backing away so as
to prolong the powerful pleasure. After a few moments it was clear that the
deck was not the best place to continue our heated sexual gyrations. I got
to my knees and pulled off of Jim's cock with audible pppppfffffftttttt.
Then I helped him to his feet and strode a few feet away to a plastic
chaise-lounge chair where I simply laid down prostrate on my tummy, Jim
gently lowered himself upon me and re-inserted his thickness in me. The
feeling of his wet, sweaty stomach against my back was a blissful reminder
of our "father-son" connection and he started to pound and buck inside me.
He nibbled at my ears and the back of my neck and then after 5 minutes of
building intensity arched his back and slammed his cock to the hilt within
me. We came simultaneously and for the first time I felt the intense, warm,
creamy discharge of a man's seed within my bowels. It spurted in excess
from the gasket of my sphincter and my own cock blasted a huge wad of semen
through the plastic mesh of the lounger and onto the redwood deck. We lay
there together, entangled in a state of after-glow and ecstasy, his
unsheathed cock slowly softening within me and my rear filled with his
enormous warm cum-load.
After a few moments Jim pulled out and said, "Terry, please don't move a
muscle. I'll get a towel for you and I have a special request which I can't
explain, but you'll understand when I return. I'll just be a minute."
"Okay Jim, whatever you say, I trust you..."
A moment or two later he returned carrying a big fluffy white beach towel.
He was wearing his robe and he leaned over to towel me off. I started to
roll over to see what all the fuss was about but he pressed my shoulders
down and said, "Terry, please don't move. I need you to remain down on your
tummy." Then I felt the tip of a thick rubber butt plug being nudged into
my dripping, cum-filled ass. My anal ring stretched wide and then with an
audible pffftttt, similar to when I backed off Jim's turgid cock, the plug
nestled itself home – the flanged base snugly filling my rear. It felt
unexplainably wonderful to have this within me. I could tell my prostate
was being pressed and stimulated and I could still sense the warmth of Jim's
cum squishing around inside me.
"Terry, can I assume you are going to spend the night with here with me?"
I replied, "Is that okay with you Jim?"
He smiled reassuringly and said, "Nothing would make me happier son."
I beamed and then got to my feet. I felt a warm trickle escape from my rear
and roll down my leg. Jim reached out again and kissed me – this time with
a romantic embrace.
"Terry, that was so wonderful. You better watch out, I am starting to fall
in love with you."
Then he winked with an understanding that told me he knew of my internal
conflict. I felt he would not insinuate himself physically between me and
my marriage, but this experience would surely give me pause to question that
relationship in favor of this one. Nothing more was said about the subject.
We sat down together, side-by-side on the lounge chair, the ethereal din
of a trickle of falling water filling the space between us as he held me in
his arms and once again, we deeply kissed.
Moments later we were in his bed. We were utterly relaxed from our hot tub
lovemaking and lay in bed fondling. This intimacy was less erotic, but
every bit as memorable and pleasant as our sex in that we could explore and
touch and pleasure each other without the pressure of performance and for
me, as a married man, opportunities to simply be loving with another guy are
rare. I savored these moments. I realized I still had the latex plug in my
rear but it caused no pain and symbolized a kind of submission to Jim. But
I found myself so calm, so serene and relaxed that I literally passed into a
Hours must have passed and light was streaming through the curtains when I
came to consciousness. Before I'd summoned my wits I realized that Jim's
arms were wrapped around me and his cock was once again deeply embedded in
"Hmmm... good morning lover," Jim whispered in my ear. "How does it feel to
wake up in my bed? Are you pleasantly surprised by my intrusion? I figured
since you are here, you are mine to have."
All I could do was purr like a kitten and tighten my sphincter to let him
know of my blissful pleasure at this early morning surprise. I guess I must
have really been exhausted because I hadn't even noticed that he'd removed
the plug he'd inserted after our hot tub session. He also did a thorough
job of cleaning me with a wet washcloth and had lubed me up liberally before
having me for breakfast in bed. He had his arms wrapped around me and at
one point he rolled over on his back, clinging tightly to my torso and
leaning his head on a pillow as he stroked and fondled my cock. I was in
heaven with his thick cock buried in my hole, his masculine arms enfolding
me and his hands massaging my stiffening dick. My body rocked and gyrated
nestled in the warmth of his and I turned my head to kiss him deeply. I
wiggled, and pumped and bucked while speared on his shaft, like the olive on
his toothpick and after some intensely blissful moments my cock shot like a
fountain spraying more cum all over my belly. He blasted raw, in my rear
once again and we simply lay in a sweaty satisfied pile as the morning
turned to day...
...After an intense night of powerful sex and an equally mind-blowing morning
of me being "breakfast-in-bed," for Jim we simply lazed around his house on
Saturday morning. My wife and child were out of town and Jim was for all
intents and purposes a divorced man who had found himself free to explore
the fascinating proclivities of his ever-growing attraction to younger men.
At 63, he was strikingly handsome with a shock of neatly trimmed white hair,
smooth, supple tanned skin for his age, plenty of muscle tone, especially in
his upper body, with a thick, lengthy cock riddled with powerful veins. What
made his crotch extra delicious was that he regularly shaved himself of any
excess crotch hair leaving his plumbing incredibly edible and extremely
enticing. His face was dignified with a strong aquiline nose and high cheek
bones and his countenance gave off an air of authority without hiding the
twinkle in his eye and the warmth of his personality.
After our morning fuck-fest I decided to cook us breakfast; eggs, bacon,
toast, juice, strong coffee and some quality time chatting about each
other's background, sexual maturity and explorations in the arousing world
of man to man sex. As we sat there toe-toe, smiling into each other's eyes
I asked Jim a pointed question and his reply turned into an extensive
recounting of his inroads into man-toman passion.
"So Jim, were you into men when you were married?" I said.
"Oh my; for sure, Terry. To tell you the truth, I've been fantasizing
about cocks and hot times with men since I was a teenager. Actually my
first experience with a guy was when I was about 16." Jim proceeded to tell
me the following tale:
"I had an older brother who had always wrestled in middle and high school
and he taught me some of what he knew, so I wound up getting involved with a
school wrestling program in the 9th grade. I had a wrestling coach, Coach
Wilson who was very fatherly and sort of took me under his wing. To tell
the truth, I didn't really have any thoughts or notions of being sexually
attracted to men at that age as I had barely hit puberty. Long story short,
I became sort of a son to Coach Wilson and would hang around after practice
and help him straighten up the gym, put the wrestling mats and gear away and
do simple errands for him."
"One winter evening, after training all afternoon, Coach Wilson noticed me
working on some defensive techniques and decided to show me a few useful
escape moves. After we'd worked up a pretty good sweat he had me down on my
all fours. Of course I was in one of those tight wrestling outfits with
head gear and wrestling shoes and he was in the top position with one hand
on my elbow and the other wrapped under me, ready to advise me on how to
escape. But it was late, and we'd already gone through a bunch of positions
when all of a sudden I felt Coach Wilson fondling my privates through my
tight outfit. He was basically massaging and fondling my balls and cock and
it felt so natural and good that I didn't react in shock or disgust. I
remember clearly moaning with pleasure at his touch and the next thing I
knew I was flat on my back in this empty gymnasium with my coach jamming his
tongue in my mouth, fondling my body and caressing my stiff little cock
through the fabric of my wrestling outfit."
"That sounds hot Jim, but also sort of frightening at that age." I said.
"Well, Terry, Coach Wilson was a handsome man, I'd say about 45 years old
with a muscle-bound, taught body and as time passed I was really growing
closer to him. When he kissed me, instead of finding it revolting, I found
myself urgently kissing back. After a while he took me into his office,
locked the door and opened up a locked closet he'd converted into a
"nap-room," complete with a lamp, recliner and small metal cot.
I was very nervous, but his way with me was very confident and capable. I
remember him sitting on the cot, with his pants off, just taking in the
image of my sweaty body, his cock stiff with erection as he touched and
fondled my dick through the fabric of the outfit and rubbed my balls and
that space between them and my ass. Then he basically tore off the rest of
his clothes and mine as well and then he pulled me on top of him and pressed
our chests and cocks, lips and tongues together. He whispered in my ear
that he would never harm me and then he grabbed a tube of lubricant he had
stashed under the cot and began to massage and widen my rear with it.
I had never felt anything like that before and it made my own cock drip
with arousal. After he worked on my hole for a good 10 minutes he whispered
in my ear again, `Jim, I am going to put my penis in you. You may feel some
initial discomfort, but I promise you it will subside, and after a few
moments you are going to feel a sense of pleasure you have never felt
before. Trust me. You will enjoy it.' Then he raised my legs up and onto
his shoulders and slowly nudged his girth into me. Sure enough, when he was
fully within I thought I was going to pee and poop right then and there. I
remember my eyes got teary from the discomfort, but after a few moments,
just as Coach Wilson had promised, the pain turned to an intense feeling of
pleasure and I was soon put in a state of ecstasy with his cock pumping and
stretching my ass. No one would ever find us in this room within a locked
room late after practice and we got even sweatier as he continued to pump
and pound my young, muscular body. Finally, he grasped me tightly and
released hot cum deep within me and when I felt the warm, wet rush of him
inside me I was pushed over the edge and my cock exploded too.
Needless to say, I spent many after-practice hours on that cot as Coach
Wilson's young boy lover. He taught me so much about man to man lust and
thank goodness no one ever found out, though our connection lasted through
four years of High School. And all the while I had a girlfriend and even
won 4 state wrestling tournaments. I figure if I hadn't been so close to
Coach Wilson I would never have become such a good wrestler, and I certainly
wouldn't have been so intimate with men, though it's difficult to say for
sure?" Ultimately I went to college. I still wrestled and on occasion had
some interesting man-to-man trysts, but nothing was quite like the
connection I'd had with Coach Wilson. After college I met Mary and figured
I was better off with a regular marriage and family in the eyes of the
world, though my mind still reeled with lustful thoughts of men.
"I'm amazed at your story Jim! Not only that, but it sounds incredibly
erotic to know that you were attracted to older men the same way that I am
to you. I only wish I were that young when I started down this road – but I
guess that's no big deal." I said. Jim smiled across the table and then I
felt his foot between my legs, rubbing my crotch. I was in boxer shorts and
a t-shirt but his touch got me hard pretty fast. This week without family
was really making me a horn-dogged guy with Jim and I was literally living
out this fantasy with gusto.
"Terry?' Jim said. "Now that we've got our wits about us, and have eaten
and had coffee, I think it's clear that neither of us is sexually sated."
He pushed his chair back from the breakfast table and held out his hand. I
rose and held out my own which he grasped and then he led me back toward the
stairs. As we mounted the stairs he had me lead and then he wrapped one arm
around my torso and whispered in my ear, "Terry, I am so glad you spent the
night here and have been my lover. The story I just told you was and served
to get me started down this road. I am wondering if you would humor me and
help me to relive it here, and now?"
I replied, "At this point I'd doing anything with you and for you Jim." I
said. You have brought me to places I'd never imagined sexually and I'd be
happy to indulge you."
He responded, "You are so great Terry. I don't know what I did to deserve
you so late in my life, but I am slowly falling for you... but have no
worries, I may ruin you for a week, but I won't ruin your life, family and
marriage. And besides, I have a pretty good notion that you've been
enjoying our connection.. wink wink?"
I said, "So what did you have in mind Jim? How do you want to relive this
fantasy of yours?"
We'd reached the top of the stairs and entered Jim's bedroom again when Jim
said, "Terry, take off your boxers and t-shirt and go in the bathroom. In
the bottom drawer of the cabinet you will find some special clothing. I'd
really like it if you would try putting them on and then come back to me
here in bed?"
I did what I was asked to do by Jim and a few moments later I returned to
him at his bedside. I was surprised that he had sort of set me up but in
the same light I was happy to share in his fantasy. When I returned to him
I was wearing a tight fitting maroon wrestling tunic with white piping,
along with calf high wrestling shoes that seemed to fit perfectly along with
matching headgear complete with ear protection and a chin strap with chin
cup. For obvious reasons my cock was turgid with arousal inside this outfit
and as weird as it seemed, I was utterly aroused to be Jim's young fuck-boy
protégé. It felt kinky and odd, but also great to be the subject of Jim's
oddly formed desire.
Moments later we were wrestling on the floor and Jim's hands were all over
me, fondling, cuddling, caressing and groping me. While we tussled Jim
stroked my cock, ass and chest. He repeatedly bit my nipples and pinned me
on my back jamming his tongue in my mouth as he forced me to the mat. I
didn't' expect him to get so physical, but I decided to let him live out his
desires since he'd been so loving and generous to me up to now.
Before I was officially pinned I decided to be playful so I arched my back
and managed to toss him off me. Moments later he was back on me with a
vengeance and had me on my tummy, pulling back the tight nylon tunic fabric
down around my ass crack.. Then I basically gave up resisting as he
aggressively forced his tongue in my rear, wriggling it about with glee and
causing my cock to stiffen with intense arousal. Sweat was building up
under my headgear and I basically just lay back and submitted to his kinky
fantasies. It felt incredible having my ass chewed and licked by Jim and I
melted with his dominant, coach-like touch.
"Terry, `Son", you are making me hot with this. Thanks for helping me
relive a formative youthful digression – albeit with the roles reversed... I
want you now to get up, remove your tunic, but keep that head gear and the
shoes on and go lay down there in my bed with a pillow wadded up under your
tummy. Will you do this for me son?"
I smiled, anxious to be the recipient of Jim's lovemaking once again.
"You're a kinky old man Jim, and I love it when you call me `son.' Of
course I will, "Daddy." I immediately got to my feet, removed the no damp
tunic from my glistening sweaty body and lay down in his big king sized bed
with a pillow wadded up under me and my saliva lubed rear raised and ready
for his attention. We were both panting with lust and our skin was damp
from the intensity of our contact. My rear was slick with his oral probing
and I had clearly grown a bit more accustomed to the girth of his beautiful
cock after the several sessions of last night and this morning.
He slipped in fairly easily and once again I clenched and squeezed his
shaft with my anal ring, telling him of my desire for his penetration. He
fucked me hard rendering me helpless by placing my upper body in a full
nelson and grasping the ear covers of the headgear. Our sweat covered
bodies grew moister and the contact of his body against my back made me leak
with desire. He stiffened his restrictive hold on my neck, arms and
shoulders as he jerked and pumped my rear with reckless abandon. He bit my
neck and ears and whispered, "I love you son," repeating it like a mantra
until his back arched and I felt his thickness once again violently explode
within my rear; excess cum spurting out the side of my hole from the
intensity of his lust. I was in a state of erotic release and I stained the
bed sheets with a huge blast of my own. Once again we lay there in
post-coital bliss, kissing and caressing till his shaft softened and fell
from my over-worked love hole.
The pleasure of the shared after-glow with Jim was beginning to ruin me.
The terse, rapid, relatively slap-bang sexual encounters I'd been having in
the recent past with my wife paled by comparison. These experiences with
Jim were intense, robust, erotic and fully realized. I loved being able to
satisfy one of his fantasies and I hoped that perhaps he had other's that I
might have a hand in recreating for him within the next week...