Date: Mon, 21 Jan 2008 09:48:42 -0800 (PST)
From: R Ranger <bn2rumpranger (at) yahoo (dot) com>
Subject: The First Time I Was Digitally Diddled

Warning! This story is sexually explicit, so, if you are not of legal age
to read such or are offended by this type of writing do not read any
further. If you would care to read more contact the author. To contact the
author cut and paste making appropriate corrections and E-mail:
bn2rumpranger "at" yahoo "dot" com


  The First Time I Was Digitally Diddled
  By Randy Rumper


  The first time I discovered the thrill of being finger fucked up my ass
by another guy I screamed out, wailing in pure ecstasy. Oh My God, what an
incredible experience that first time was as Bobby dexterously diddled me
with his middle digit. Bobby BoDiddly had beautiful hands and feet; his
hands and feet were what made me take notice of him. The first time we met
and shook hands I was taken by the beauty of his long slender fingers with
finger nails so well manicured. I would discover months later that those
fingers were very adept at the art of digital diddling.

  Bobby and I were unlikely roommates. He was not a particularly
good-looking guy, nor was he well endowed. Bobby wasn't blessed with
bulging biceps, powerful pecs or well-defined abdominal muscles. His
physical characteristics were that of the typical gangling geek; whereas, I
was the athlete with a strong body and good looks. My nerdy roommate was a
quiet bookworm who never ventured out to participate in extracurricular
actives; whereas, I was the social butterfly. Despite our differences Bobby
and I had grown very close over the course of that first semester. We spent
many nights confiding in each other our deepest intimacies and secrets. As
the first semester was drawing to a close we decided to pool our resources
and spend the break between semesters together on the coast of Florida
instead of going home.

  For Bobby and me, two eighteen year old collegiate freshmen, living away
from home for the first time in our lives was a new and enlightening
experience. At almost nineteen I was somewhat of a naive neophyte when
it came to sex and sexuality; however, living with my roommate was fast
becoming an edifying experience. A roommate who would educate me in the
ways male-on-male lovemaking; needless to say, I was thrilled when I
discovered that my roomy was a homosexual. I was not sure who or what I was
yet, but I knew instinctively that my roomy would help me discover my niche
in life -- my own sexuality.

  My place in life and my sexual lifestyle had been in turmoil for years. I
had a girlfriend who I had dated for two years in high school; however, she
was now attending another college over a thousand miles away. I wanted to
do the nasty with her during our relationship, but all she would do was
fist fuck me. She attempted to give me blow jobs on a couple occasions, but
she just didn't understand nor could she master the mechanics of how to do
it. She gagged, spit and even hurled on one occasion. My sister's
girlfriend's cousin however had performed oral sex on me a few times the
summer between my junior and senior year in high school. She was good at it
and I couldn't get enough. That had been the extent of my sexual
involvement thus far in life. My sexual lifestyle had not yet been defined;
however, I was sure that Bobby was going to be the one who would help me
map out my future.

  I knew from that first blowjob that I was hooked on oral sex. I also knew
after the first time I'd touched another guy's dick that I wanted to
experiment sexually with other males. Mid way through our first semester
Bobby and I rented a cottage on the Gulf coast of Florida for the break
between semesters. We planned to spend our break getting more intimately
acquainted. During the first semester in college Bobby and I had discussed
sex, but had yet to do anything other than mutual masturbation on a couple
occasions.

  One night before we took off for our break between semesters, we sat
across the table from each other drinking wine and talking about sex well
into the night. After a bottle of wine I'd become a little amorous in my
inebriated state, so I reached across the table and took one of Bobby's
hands into mine. As my fingers explored his hand I stroked and admired his
fingers, telling him what great looking hands he had. I remember telling
Bobby that I would enjoy having him explore my anal cavity with his
delightful looking middle digit. He replied that he would enjoy doing me
with it. He asked me if I had ever been diddled or cornholed before. To
which I replied, no. He told me he wanted to change that very soon. I asked
him why we didn't try it that night. To which he responded only when the
time is right.

  Bobby had asked me during our conversations about my sexual experiences
thus far in my life. I told him that my sex life had been limited, but now
that I was free of parental control I wanted to expand my wings and fly. I
went on telling him how I played with my asshole a few times when I was
younger and what an exhilarating feel it produced. I told him how I would
wet my middle finger with saliva or baby oil, playing around rubbing the
entrance to my asshole of a night while I lay in bed jacking off. Also,
when I took a bath or shower I would soap up my ass and play with my
asshole. However, the few times I'd actually inserted my finger in my
rectal cavity I withdrew it finding fecal matter attached as well as nasty
stink of shit to my finger. So, by the time I was in high school I knew my
asshole was super sensitive to touch, but also came with an offensive odor.

  As we sat across from each other I told Bobby that I'd heard and read
that some guys found anything penetrating their assholes to be repugnant
and taboo. Others found anal sex play to be a very enjoyable and sensual
experience. I informed Bobby that I thought I would enjoy anal sex, and
moan out in ecstasy if he were to diddle my asshole with one of his
beautiful fingers. I also told him I thought that I was one of those who
would find cornholing to be very sensuous. Bobby interrupted telling me
that is why he wanted to wait until we were away from the dorm before doing
anything.

  My roomy told me that he wanted us to be alone and free, so we might sing
out gleefully as we sexual stimulated each other. I told Bobby that for me
to be finger fucked while receiving a blowjob would probably be the
ultimate in sexual pleasure, bringing on wanton wails of desire from me. I
told him that during recess in junior high school I'd heard stories from
the older boys about them finger fucking their girl friends. Of course,
they always wanted to pass the odoriferous digit under our novice noses for
everyone to sniff the scent of the freshly finger fucked girlfriend. I also
heard stories about guy's cornholing each other. Although curious I had
never indulged.

  Since we'd been rooming together we would go online occasionally after
classes and read stories about gay sex. We even watched gay porn on a few
occasions. We would discuss these stories and flicks along with what we
might engage in during the winter break. Bobby told me the first night we'd
start off slow, sucking each other off and then move on. Bobby also told me
that he wanted us to experiment with anal sex. He said that he had prepared
and had all the bases covered. He said that it was something he had been
planning for weeks prior. I had heard stories that anal sex could be
painful. I didn't know first hand as I wasn't experienced in finger or butt
fucking. Needless to say, I was a little apprehensive. Hell, Bobby and I
had just recently engaged in our first mutual masturbation session.

  Early one morning after pulling an all nighter, studying for finals, we
decided to take a shower together where we begin playing with each other's
stiff dicks. We spent about a half hour in the shower soaping and rubbing
our hard cocks together before we ejaculated all over each other. The
feeling of rubbing our cockheads together was totally exhilarating.

  As we ate breakfast that morning I asked Bobby where he learned about sex
with guys. He told me that his uncle who was a year older taught him. He
said that he had learned everything about sex form his uncle, and he and
his uncle had been playing around sexually for a while. Bobby told me that
his uncle's dick was much bigger than his. He said that of course this had
all been done in total secrecy. In a few days Bobby would be my sexual
mentor.

  As we drove towards the cottage we rented Bobby told me he and his uncle
had discovered that baby oil was the best lube to use at that time;
otherwise, any type anal penetration might be painful. That was my main
concern -- pain. He told me it might hurt a little when he pushed his
finger inside me. He also advised me to just tell him to stop and he'd wait
a few seconds till I got used to it. He told me that when his uncle finger
fucked him the first time he used Crisco to lube up Bobby's asshole. Bobby
said that for a week after his uncle packed his ass with Crisco he shit
biscuits and gravy, and then he laughed. I thought at the time how gross,
using Crisco. Bobby said that since that time he had learned that there
were much better lubricants on the market that were compatible with
condoms.

  We arrived at the cottage which was completely furnished in the late
afternoon. After unpacking the car and putting our things away we took a
shower together. Bobby guided me through the preparation process. He told
me that prior to any anal play that cleanliness was the rule. He said the
second rule was to use plenty of lubricant. We made sure our anal cavities
were evacuated and cleaned. Bobby had brought all the necessary items to
insure a safe and sane time. He had in his bag Fleets enemas, condoms,
lubricants of different varieties. He also had brought along a couple of
dildos and a vibrator. Bobby came well prepared.

  We lay down on the bed opposite each other where we began playing with
each other's stiffening appendages. I had never sucked a dick before, but
had been sucked. Bobby told me to take my time and follow his lead. I
played with his cock and balls before taking them into my mouth. Bobby was
circumcised and his dick was only about four and half maybe five inches in
length fully erect; it looked to be about the diameter of a "C" flashlight
battery, all in all a very nice looking cock and cockhead. Size was of no
concern to me; in fact, I was thankful for two things. The fact that Bobby
was cut and his cock wasn't a monster.

  I had read all the stories about guys swallowing cocks that were eight
and ten inches long and the thickness of a beer can. I just couldn't
understand how they could do that. I had tried on a couple of occasion to
get my mouth around a beer or soda can. There was no way that was
happening; my mouth just wasn't that big. As far as taking eight or ten
inches into my mouth and all the way down my throat, that wasn't happening
either. So, I was thankful my mentor wasn't overly well-endowed. Besides, I
didn't think I wanted a monster cock stretching my virgin asshole, at least
not as a novice.

  Bobby was kissing the head of my cock; taking only the pink glans into
his mouth, licking all around the head, especially the crimson coronal
ring. He was taking his time exploring the full six and half inches of my
manhood. His mouth and tongue were playing with my pecans inside my scrotal
sac. Already I was in heaven as my mentor lavished his full oral attention
on my fully aroused organ. After a few minutes of oral pleasuring Bobby
pushed my legs apart and ever so gently began rubbing lubricant into my
rectal area.

  The first cold dollop of lube and delicate touch from his middle digit
brought about a surprising sigh and then a pleasurable moan. The tip of
Bobby's middle finger rubbed against my awaiting asshole but ever so
delicately. He continued rubbing my pucker as he licked my cockhead. Oh My
God, I was in heaven. I had to quit sucking on Bobby's dick for fear I
might bite it off. I lay there waiting for the moment his finger would
breach my asshole. He looked up at me and asked how I was doing. To which I
had no reply, just a whimper.

  I felt Bobby's finger becoming more aggressive. His finger tip began
putting more pressure on my pucker. The tip of my dick was leaking. As my
mentor began the penetration process his tongue found the source of leakage
and was excavating precum from my piss slit. My heart was pounding and I
was moaning with wanton desire. I knew then why Bobby wanted to wait until
we were away from the dorm before engaging in sex. He knew how to make a
grown man cry. His finger tip began pushing past the entry, the first
ring. He withdrew his finger tip and applied more lubricant.

  Once Bobby squeezed another dollop of lube on my back door hinges he went
back to work. The lube was a little cold at first but warmed up quickly as
he worked it in. Bobby would stop every once in a while to pay attention to
my throbbing hard cock. Then he would move down letting his tongue
titillate my taint. I waited for the point of pain as Bobby's finger
penetrating my sphincter. Once he had cleared the threshold of pain and
breached the second ring he stopped so I might get used to the intruding
digit.

  Bobby withdrew his middle digit again and began the process of
penetrating my pucker one more time. I was near exhaustion moaning with
desire. I was growing tired of delay I wanted him to finger fuck me in
earnest -- finish me off. Without knowing it Bobby's finger was deep
inside my rectal cavity. His long middle finger found the magical button
inside and began massaging it. Oh God, I wanted to cum, scream and shit all
at the same time; it felt so fucking good as his finger tip rubbed against
my prostate.

  With his finger buried deep inside me Bobby returned to orally pleasuring
me. I didn't know how much longer I could hold out or if I wanted to. My
mentor's mouth had fully engulfed my cock and was bobbing up and down on it
as his finger continued exploring my anal cavity. I was screaming out for
him to fuck me and suck me. I yelled at the top of my lungs that I wanted
him buried deeper in me and to suck me forever. When I blew my load I
almost suffocated Bobby with the powerful amount of spooge I blew down his
throat. He started gagging and had pull off me to spit some of it out
before returning to me.

  Bobby refused to withdraw his finger from my ass or let my cock go from
the grips of his lips. He was draining every ounce of seminal fluid from my
nuts. I had just experienced the most explosive orgasm of my young life. I
was soaked in sweat and panting to the point of hyperventilating. My eyes
were flashing with lightening. I was experiencing dizziness, chest pains
and tingling in my hands and feet. My cock was numb and my balls ached.

  I collapsed in a state of total exhaustion. I had no more to offer. I
couldn't even reciprocate and finish Bobby off. My nerdy mentor turned
around on the bed and lay next to me. Smiling at me he whispered in my ear
how much he had enjoyed doing me. He told me that after we rested he wanted
me to fill him with my cock, fucking him into oblivion. We fell asleep
holding each other. From that first time we refined our sexual repertoire,
fucking and sucking each other with wanton desire; however, nothing would
ever equal that first time being digitally diddled and sucked off by my
friend Bobby.