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:
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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