Date: Tue, 24 Jan 2012 00:05:29 -0500 (EST)
From: whitewold999@icqmail.com
Subject: Rick's College Outing 2 (gay/authoritarian, fetsh, oral, anal, M/MMM)
DISCLAIMER:
This story is a work of fiction and contains descriptions of explicit sexual
acts of boys and men discovering their sexuality. It contains graphic
scenes of sex between consenting adult males. If this type of content
offends you or you are under the age of 18 do not read it.
Author's Note:
This story is the property of the author. It can be downloaded for
personal reading pleasure or sending to a friend, but if you wish to re-
post them at your own site, please contact the author for permission.
If it is illegal to read such material where you live or if you find the topic
distasteful the please leave now. If you enjoy the story or if it evokes
memories of your own, please let me know. I am happy to write stories
from outlines.
Copyright 2012 Wolf, All rights reserved.
You may contact me at whitewold999@icqmail.com if you like. All
flames will be ignored.
Rick's College Outing 2
First Job
By
Wolf
As soon as I graduated from college I was fortunate enough to
land a job working for an Atlanta, Georgia advertizing firm down town.
I found an apartment in a complex not too far from work. The office
building was occupied by a variety of business, retail and restaurants on
the ground floor. In some cases multiple businesses occupied a single
floor. The advertizing business was located on the north side of the fifth
floor. There was a Human Resources Department located across the hall
and occupied the southern part of the floor.
I had not been working there long before I worked up the nerve
to ask out one of the young women working for the Human Resources
Department. We would see each other while waiting for the elevator or
going to lunch in one of the restaurants in the area. I thought she was
way out of my class.
She was a very tall and slender woman. She was five-feet nine
without heels, and no more than 110 pounds. She looked like she was all
legs. She had small perky breasts, and her hair was slightly longer than
shoulder length. Her naturally blonde hair looked like it was
professionally styled and streaked. She didn't have an ounce of body fat
on her. I learned eventually that she worked out every day at a fitness
club near her apartment, and learned that her apartment was about 10
miles from mine. Her job required that she travel up and down the east
coast for a couple of days at a time.
I consider myself an average guy, blond hair, only five-feet nine
and 150 pounds. If anything I look almost feminine. I did my best to
stay in shape, by working out regularly in the gym, and played tennis at
the local racket club on weekends. I manage to play a pretty good game
of tennis, as a result of three years of collegiate compaction. I don't have
an over powering serve, but I can hold my own placing shots where my
opponent has a hard time getting to them. My game is to keep them
running, so they can't set up for a power shot. At least the exercise
keeps me trim. I am reasonably hug, even if tend to round up the actual
size.
It took me some time to work up the nerve to approach Barbra for
a date. I was as nervous as a school boy for the first couple of dates. I
dreaded the first kiss, but she was very sweet about it. I don't even
remember how many dates we had before I made a pass at her. She was
very gracious about it and even helped me complete my first penetration.
After several times in bed I felt like I was not getting her off. Oh...she
was very good about faking it really well.
Barbra was not a big fan of oral sex, but she would at least suck
my cock long enough to get me hard enough to get it in her. When I
realized that I was not getting her off, I started going down on her. I
didn't enjoy sucking her cunt right after I had cum in her pussy, but I got
used to it. After a couple of times I could do it without gagging. I can
proudly say that I did a pretty good job of it. I think Barbra preferred
me going down on her over fucking her. After a time she rarely went
down on me. So that became our sex life, we enjoy each other's
company, and went out almost every weekend when we were both in
town. We managed to have lunch with each other two or three times a
week. We attended parties together, and were known as a couple, by our
friends. I thought we were doing well, and was planning on asking for
her hand in marriage in about six months. Then it happened.
There was a Halloween costume party planned at her apartment
complex with a 500 dollar prize for the best costumed couple. We sure
could use the money, so we racked our brains about what would be a
winning costume for the two of us. We discussed going as Jack and Jull,
Snow While and Prince Charming, Dick and Jane the list was long, but
none suited us. Every idea we came up with was discarded just as
quickly.
One day while we were having lunch with Gilbert, a black guy
that worked with Barbra, and lived in the same apartment complex. He
was planning on going to the same party. While we were explaining our
dilemma about appropriate costumes, he sat back studying the two of us
for a time. After a long pause he said, "You have it, go as a Pimp and his
hooker!"
I was thinking that Barbra would look great dressed up like a
hooker. I could see her in a short skirt and a short top tied under her tits.
I figured that putting together something that looked like a pimp
wouldn't be a problem. I figured that would be great fun. Gilbert and I
would be the pimps.
Gilbert said, "The two of you kind 'a look alike, with wigs and
makeup you could even pass as sisters."
Barbra jumped on that idea. I didn't see myself getting rigged up
like a woman, but Barbra assured me that with her help I would look
great. She assured me that the 500 dollars was in our hands. The two of
them kept pushing me until I agreed. For the next two weeks Barbra
went about gathering the clothes she figured would be appropriate for
our costumes. When the day arrived we took the day off from work.
Barbra spent the day getting me ready. She made me shower and shave
particularly close, then shave my under arms and legs. When I called her
to check me out, she said that was not going to work. She retrieved a jar
on Nair. She applied the stuff all over my body. When she rinsed it off
there was no hair on my arms, back, legs and shoulders. She even
removed the pubic hair from around my cock and balls. She only left
one of those landing strips above my cock like the one on her pussy. I
was shocked by the sight of my naked body in the mirror.
Barbra led me to her bedroom and sat me down before her
vanity, so she could apply makeup. First she covered my hair with a
nylon skull cap that pulled my temples back, making my eyes and eye
brows rounder and wider open. Then she started applying a makeup base
that evened out my skin tone. Then she applied fake eyelashes and
lipstick. She even plucked my eyebrows, talk about some pain, to give
them a more feminine look. I couldn't believe how full she made my lips
look. She handed me some self supporting nylons that were very
flattering when I pulled them up my legs. I had to struggle, with her
help, to get into a garter belt. She helped attach the garters to the nylons.
Then she glued latex foam rubber breasts on my chest with some type of
contact cement before helping me get me into my bra to hold them in
place. She put me in black pumps with four inch heels. When she helped
me to my feet, I felt like I was going to break my ankles. I told her that I
couldn't figure out how women can walk in these damned things. She
simply said, "Practice!"
She walked around me inspecting her work to that point. After a
couple of touch ups she seemed to be pleased with her work. When I
saw myself in a mirror I hardly recognized myself. All I needed was a
wig and I would look like a mid twenty-year-old girl. She handed me a
small thong to put on. When I stepped into it, it was a struggle to pull it
up. I complained about it being too tight. She said that it had to be, to
hold my cock against my body. But my cock was fully engorged, and
stuck out over the top of the thong.
Barbra said, "That is not going to work. I suggest you do
something about it while I get myself ready!"
I asked, "What should I do?"
She said, "You know what to do. Jack off, so we can finish your
outfit!"
While she was bathing I jacked off furiously until I squirted cum
into a hand full of tissue paper. When my cock got soft I tried putting it
in the thong. When Barbra returned she suggested that I stuff it back
between my legs. She used the same contact cement to secure my cock
between my legs. It was hard to tell that there was anything down there
besides what looked like a pussy under a thong. It even had the camel
toe look.
I watched Barbra putting on an outfit very similar to the one I
had on. She also put on a nylon skull cap. She had two identical blonde
wigs. She helped me put on mine, before she dawned her own. We
finished our outfits with miniskirts and short jersey tops with the
message emblazoned across the front, "SEE ANYTHING YOU LIKE"
The final touch was a couple of transfer tattoos that was the Omega
symbol that she put on our shoulders and small of our backs.
She insisted that I practice walking in the heels. She also
instructed me to relax the hip not supporting my weight and allow it to
drop. That would accentuate the swing of my hips. After a little
practice and her instruction I was managing to swing it like a pro. Barbra
suggested that I place each foot in front of the other as if I was walking
on a balance beam.
Gilbert made his appearance before the party time all decked out
like a pimp or a rap star. He had enough bling on to reflect enough light
to serve as a disco ball. He was favorable impressed with our look. I
have to admit that I made a pretty good looking woman, but Barbra was
stunning. We made our way to the nearby hall called Scott's, where the
party was being staged.
The party was in full swing by the time we arrived. We
socialized and danced with friends for about an hour. I was getting felt
up and my ass pinched by a number of guys. I have no idea if they
recognized me or actually thought I was a girl. All in all we played the
part well, I thought. We received nothing but compliments during the
evening. After consuming several drinks, my feet were killing me, and I
needed to piss in the worst way.
I made my way to the bathroom. The men's room had a line five
and six deep behind each urinal. I did get some strange looks though. A
guy that was behind me, told me to follow him, and he led me upstairs.
There were no lines. He let me go first. Because of the way I was clued
up I could not use the urinal, so I used the toilet, and had to sit down to
pee. When I looked up the man was standing in front of me watching
me pee. He was standing there fishing out his cock out of the fly of his
pants.
I thought he was going to use the urinal, but felt uncomfortable
about him pulling it out in front of me. I was in mid peeing and couldn't
stop if I wanted to stop. His cock started to get hard and he stepped
forward towards me, holding his cock. He said, "You know that you
look good dressed up like a girl. No real guy would ever dress like that
unless he had some repressed female feelings! I know that your sweet
lips want to be wrapped around a cock like mine, and live out the fantasy
your living. Go on have some fun!" He pushed his hips forward,
pressing the head of his cock against my lips, while grabbing the back of
my head and pulling my head against his crotch.
I refused to open my mouth, so he grabbed my ears and twisted
until I opened my mouth, so he could shove his cock in. He actually
fucked my mouth for five or six minutes, before I realized he had let go
of my ears. At one point he told me to look up, but don't let my cock
fall out of your mouth. When I looked up he had a cell phone in his
hand, taking pictures. I continued sucking his cock until he filled my
mouth with warm cum. When he was finished snapping pictures, he
said, "Do you know who I am?"
He did look familiar, but I couldn't place the face, due to the
makeup completing his costume. He said, "I work in the same building
as you on the fourth floor. I see you and your girlfriend on the elevator
and going to lunch. I also live in the same apartment complex as her. I
see her exercising sometimes. I could have died when I realized that he
could expose me as a cock sucker to everyone that knew me. He put his
cock back in his pants, and as he headed for the door he said, "I will be
in touch! Don't let me down!"
I felt so dirty. I rinsed my mouth out from the faucet on the sink.
I checked my makeup in the mirror. Except for a little less lipstick I
looked okay. After getting my clothes back in order I made my way
back downstairs. They were calling for everyone to line up for the
judging. Barbra saw my face and insisted on applying fresh lipstick. As
the master of ceremonies held his hand over each couple the applause
was measured on a meter, that was hooked up to a large screen plasma
television. When it got down to just three couples left, I was thrilled
when we won the contest until I saw the guy I had sucked off taking
additional pictures with his cell phone.
The three of us made our way back to her apartment and had a
party of our own. I got so damned drunk I passed out. Barbra and
Gilbert argued about the split of the prize money. She insisted that he
deserved halve, because it had been his idea. Gilbert insisted that he
only deserved a third. She was resolute and prevailed.
I had a pounding head ach the next morning. I scrubbed my
body raw in the tub. I felt little comfort putting on my own clothes. I
worried about what that guy was planning on doing.
A day or two passed without any incident. I even was on the
elevator with him a few times, but there were also other people on the
elevator with us. I was beginning to think he was going to let it pass,
until one afternoon my phone rang. When he identified himself his
suggestion was more like a command that I come down to the fourth
floor. I complied with his request. He led me into the men's room on
the fourth floor. He pushed me into a stall and closed and locked the
door behind us. He made me sit on the toilet, while he pulled out his
cock. He stuffed it into my mouth and fucked my mouth until he filed it
with cum.
He insisted that I visit him after work. I felt so dirty, as I made
my way back up to the fifth floor. I could hardly work the rest of the
day. I was struggling with how I was going to avoid Barbra while
coming and going to the guy's apartment. At least his was on the other
side and facing another street.
When I knocked on his door he greeted me with a sardonic smile
on his face. When he closed the door he offered me a beer before he
showed me a collection of famine lingerie that would only be selected by
a cheap woman. They looked like they were right out of a Fredrick's
catalog. He forced me to strip right there in front of him and put on the
fishnet stockings, platform heels that were at least six inches tall. The
crotch-less panties were black see through things with feathery things
around the crotch opening. My cock and balls were dangling out of the
opening. He had realistic falsies for me to glue to my chest with Skin
Bond breast form adhesive. The bra he made me put on was so lewd.
My body hair was starting to grow back and was starting to itch. He
demanded that from now on that I keep my body shaved. He made me
parade around his apartment while he sat in his recliner. Then he made
me knee in front of him and remove his shoes and socks, before pulling
down his pants and underwear. He made me suck his cock for awhile
before he insisted that I jack him off in such a way that his cum splashed
all over my face.
He made me visit him two or three times a week. Barbra was
beginning to think was regretting our relationship or I was seeing some
other woman. I tried to pass it off as work pressure. It was making me a
nervous wreck, and losing sleep. The stress was making me lose weight.
The strangest thing was I was beginning to enjoy sucking his cock. The
more he degraded me the more it was turning me on. I was soon licking
his asshole on demand. Just when I thought it could get any stranger he
insisted on fucking my asshole. One day he even made me go up to the
roof top of the building where he fucked my ass on the roof.
One evening when Barbra was out of town he made me come
over. When I entered his apartment there was another man there. This
man was a hulk. He was well over six-feet four, and looked like he
weighed over 300 pounds. He had a scruffy beard and was smoking a
cigar. His heavy southern accent revealed utter contempt for faggots,
but that didn't stop him from whipping out a thick dark cock surrounded
by dark hairs. He made me suck his cock. When I got on my knees and
put my head in his lap it smelled like he hadn't washed in days. I
thought I was going to hurl, but I managed to suck him off. The man got
a laugh watching the host fucking me in the ass at the same time. After
it was over I was ashamed of myself because as degrading as it was it
was also the most thrilling thing I had ever done. I must have jacked off
a dozen times when I got home.
He was inviting a number of different men from his office to
have sex with me. There was a lot of beer drinking while I was getting
fucked in the ass two or three times a week. He had me even visit cross
dressed completely, including wigs. I was getting adapted at putting on
makeup. Then one night when I entered his apartment I could have died.
The other man was someone from my office. They made me blow them
both, tongue fuck their assholes and they took turns fucking me, while
the other one pissed in my face.
At work I couldn't look the guy in the eye. He would tease me
by doing things like sticking his tongue against the side of his mouth like
a cock was in it. He even grew bold enough to get me in an empty
office, lock the door and either made me suck him off or fuck my ass.
He teased me about Barbra getting suspicious. He said, "I bet
she thinks you're fucking some other bitch! Should we alleviate her
fears, by allowing her to witnessing you servicing my friends?"
I pleaded with him not to destroy my relationship with Barbra.
He was amused with my discomfort. I was willing to do anything he
wanted to insure he wouldn't out me. He even made me dress up and go
to a transvestite bar and pick up an older man. When I brought the man
to his apartment, from all appearances we had the place to ourselves. I
let the man fuck me after I sucked his cock until he was hard.
The guy was really getting into fucking my ass when the door
opened and Barbra was standing there with the guy that had brought me
out. I was crushed. I pleaded with Barbra to let me explain, but she left.
I couldn't leave because the man was clinging to my hips, while he was
still fucking me in the ass.
If you enjoyed the story and have a story you want me to write about
your introduction to the world of male sexuality, please send your outline
to whitewold999@icqmail.com