Friends, Roommates, and Lovers

Author's note:

This story ended up being much longer than I intended. For those of you who like the quick thrill stories, feel free to skim the first two sections before getting to the juicy stuff in section three. For those you who like longer stories, I think you'll find this very enjoyable.

New Friends

My name is Jamie Morgan. It was mid-January 2012, and I had just graduated college in December with a boring old accounting degree. After spending my college years attending a small school a few miles from my parent's house I had a real urge to prove to myself that I could live own my and be a responsible adult. In order to do that, I decided to only seek out job interviews in places as far away from home as possible.

It turns out that in the technology age many employers are okay with giving interviews over the internet to qualified applicants who live far away. Because of this, I was able to have several interviews with the Human Resources departments of many accounting firms, any of which I would have taken. After two weeks of interviews I finally received three job offers from firms, each of which would take me far away from home.

It was up to me to choose which offer to accept. They all were located in lively and entertaining cities, so that was a toss-up. They all offered starting salaries of just over $38,000 per year, so there was no clear winner there either. The deciding factor came down to the HR reps who interviewed me. Two of the three had very generic and boring HR reps, however the HR rep from the firm in Seattle was not generic and boring.

She was gorgeous. I was surprised she offered me the job because of how nervous she made me in the interview. I couldn't help but worry that she would notice how sweaty and uneasy she was making me. Her name was Sarah Wallace. She was a blue eyed blonde and would have easily been the hottest woman in my hometown. If there was a chance to catch a glimpse of that beauty on a regular basis, I had to take it.

Before I knew it I was saying good bye to my parents and leaving little Midland, Ohio and flying over 2000 miles to my new home in Seattle, Washington. I arrived at the airport on a Friday evening and was promptly greeted by Sarah Wallace, who was far more stunning in person. I had a hard time speaking to her, but eventually managed to introduced myself and follow her into a cab. She dropped me off at a hotel near the firm that would serve as my temporary living quarters until I found more suitable housing. Sarah also informed me that there would be a staff party tomorrow at the firm where I would get acquainted with my new workmates. After I was settle in, she headed home and said she'd see me tomorrow.

It didn't take me long to realize that Saturday would be February, 10th and this was likely going to be a Valentine's Day themed party. The thought of hooking up with Sarah at the party sent trills through my body. It was unlikely to happen because she surely would act professional at work function and more than likely a beauty like her would have some type of scumbag boyfriend. However, the improbability of it did not keep me from dreaming dirty thoughts about it.

I arrived at my new place of work ready to party wearing my best work suit. I had spent nearly all of my graduation money on that suit and just maybe it would come in handy in my new life. Not only did I want to look professional to my new bosses, but I really wanted to impress Sarah.

It was Sarah who greeted me at the door. She was wearing a strapless white dress with pink hearts that came midway down her thigh. The dress showed off just enough of her ample cleavage and sexy legs. She also wore a stunning smile that was accentuated by her perfectly done makeup. I would do anything this woman wanted. She introduced me to many of my new coworkers and my new bosses.

Everyone seemed nice enough, though many were surely your stereotypical boring accountants. There were a few attractive women in the crowd, but only two of the employees I saw could come close to Sarah's beauty. But by coming close to her beauty they were also true beauties. It was becoming clear that tour with Sarah was nearing its end when she introduced me to one last person.

"Hey Pete," Sarah said as we approached a rather good looking man who I assumed would be a fellow accountant. "Pete, this is Jamie Morgan, our newest accountant. Jamie, this is Peter Halpert. Well I've got to meet up with my boss, you two be friendly, alright," said Sarah just before heading back to the main group of people.

Pete was appeared to be very athletic and handsome. I'd say he was about 6'1" and probably weighed a muscular 190 pounds. I'm sure he had been an athlete before being an accountant. He had dark black hair and a neatly trimmed, but full beard. Compared to my slender 5'7" frame, Pete was the picture of masculinity. Not to say that I was completely feminine. I'd always been told that I was pretty good looking and never had any trouble hooking up with girls throughout my college days. However, just by looking at Pete, I would guess that he was far more popular with the ladies than I had ever been and I could see that he would have much better odds at getting with Sarah. Yes, I believe they would make a sexy couple. Did I just refer to him as sexy? No, sure he's handsome but she's the one who would make that couple sexy.

"Sounds like she's trying to set us up," said Pete, shaking me out of my thoughts.

"Set us up? What? But, I'm not gay," I replied, clearly missing something. "Are you gay?"

"No, HA. It was supposed to be a joke dude," replied Pete laughingly. "That Sarah Wallace sure is a fine piece of woman, huh Jamie?"

"Yeah I noticed, she's probably the hottest girl I've ever met. Pretty much the only reason I took this job was because she did my interview. Have you ever made a move at her Pete?"

"No. I've only been working here for a couple of weeks, and I usually like to ease my way in with ladies like her," said Pete coyly. "I do plan on asking her out soon though."

"Well good luck man, I don't think I have a chance with her if you're after her.''

"Hey don't sell yourself short, anyone has a chance if they're confident enough. So Jamie, what do you think of that chick over by the water cooler?" Pete pointed at a very attractive black girl with curly brown hair who was wearing a short and cute purple dress. "That's Claire Thomas, the new front desk lady at the firm," he said. "And I hear she's into dudes and chicks."

"She is sexy, and I have always had a thing for bi-girls, maybe she'll be my fall back if you take Sarah out from under me," I replied somewhat jokingly, but mostly seriously.

"For some reason I've never been into black girls. I mean I can tell she's obviously very good looking, but for some reason she's not my type," said Pete. "I hope that doesn't make me sound racist."

"No dude, I don't think that makes you seem racist," I said. "I wouldn't tell her that you don't think she's hot because she's black or anything like that because I'm sure that would could across as racist. I just think that everyone has their own type. I had a friend in college who was only attracted to chicks from India and I don't think that made him racist against all other races. And let me tell you, college was not fun for him because there were not many Indian girls to choose from at our school."

"That's pretty funny, Jamie. Say, what do you think of the hotel? I've been working here for two weeks now and I'm still living there. I can't stand it."

"It doesn't seem too bad after one night, but I'm sure it will get old," I said.

"Well I do have a nice townhouse in my sights," said Pete. "You interested in being roommates?"

Before I could answer we were interrupted by a commotion coming from the center of the party. Pete and I made our way through crowd in an attempt to get a better look. Sarah was standing in the middle trying to get everyone to calm down and back away as quickly as possible. It appeared that she was standing over someone who had a bit too much to drink, vomited on her feet, and then passed out right beside her feet. It also appeared that the party was over.

New Roommates

Just a week after moving to Seattle and beginning my new job, I moved in to the nicest townhouse I could afford. Pete and I decided to go through with being roommates so we had a much better setup than either of us would have been able to have rented alone. The house had a common area and kitchen on the second floor, my room was on the third floor, and Pete took the ground floor. I think he did this because he didn't trust me to protect the house from invaders, but that left me with the better room. The common second floor had a beautiful balcony that had an amazing view of Lake Washington. It was nice being that close to the lake, though we didn't exactly have waterfront access.

Being roommates with someone you only knew for a week was awkward at first, but luckily each floor had its own bathroom so we each had enough privacy. Things became much more comfortable when we settled into a routine. Pete did almost all the driving because I didn't have a car. I did almost all the cooking. I was more than happy to do so since I had flirted with majoring in the culinary arts before settling on accounting.

Things at work were going fantastically for both of us and we were both quickly becoming well liked employees. However, the job itself is mostly just numbers, graphs, and tax figures so it's not really exciting to talk about. But it paid pretty well for two guys fresh out of college and we we're not shy about spending our money like dumb college kids.

Our first purchase was made after we discovered a mutual love for movies and video gaming. We put our money together and bought a 55" Samsung HDTV that fit in nicely in our common living room. This came in handy during long movie and gaming marathons that took place in the early days of our living arrangement. Our second major purchase was made after we discovered a mutual love for baseball. My assumption of Pete being an athlete was correct as apparently he had played four years of Division II baseball in college. I was very impressed. We both agreed to buy Seattle Mariners season tickets because we figured that during the summer we'd be spending a lot of our time after work at the ballpark. For two guys who looked like an odd pairing, one very masculine and one more than slightly feminine, we had a great deal in common.

Neither one of us did much dating during March because we were too busy getting used to the new house, but it was getting clear that both of us needed some action soon. It was in the middle of April when Pete begged me to let him have my ticket for the Mariners game on the 21st because the White Sox were in town and he said the girl he was talking to was originally from Chicago. I agreed as I figured it would be good for at least one of us to get some. I found out later that the girl he took was Sarah Wallace. Pete had discovered that she was from Chicago and was a casual White Sox fan. I was disappointed at first, but I had to admit it was a very smooth move on his part. And it couldn't have worked out any better for him because the game she went to just so happened to end up being a perfect game for White Sox starting pitcher Phil Humber. Pete was a lucky bastard. He and Sarah were officially boyfriend and girlfriend by morning.

I couldn't have been more jealous during the first few weeks of their relationship, not only because she was my dream girl, but because they had sex all the time. She was pretty loud too. Pete must have been very skilled. I thought the townhouse was very spacious when we moved in, but I guess it takes hearing your roommate fuck his girlfriend a couple dozen times to make you realize it's not as big as you thought. The worst part was that I now spent most of my nights alone instead of hanging with Pete in the common room.

It wasn't until the middle of May that I stopped pitying myself and decided to get back in the game. It turned out to be pretty easy to hook up with women in the city when you had a stable job and the money to buy girls drinks at bars. So, many nights when Pete would stay in with Sarah I would borrow his car to head out on the town. I must have hooked up with as many girls that summer as I did during all four years of college, which was about nine or ten lucky ladies. None of them looked as good as Sarah, but there wasn't much I could do about that.

Once I started having fun again, life in the house turned out to be more enjoyable than ever. However, now that Sarah was spending a lot of time at our place during the summer I realized I was glad that I never hooked up with her because our personalities just didn't mesh. It turned out that she was a bit too much of a bitch quite simply. I was happy enough being with a different girl every other week and was glad I wasn't the one tied down to her. Pete seemed to be happy enough being a one woman man, but I couldn't tell if it was because he was a romantic or if he really liked being with Sarah. I hoped it was him being a romantic and that hadn't completely fallen for that shrew. Maybe she was just a shrew to me because she could sense my jealousy when they first started dating.

As summer was nearing its end I could tell that Pete and I were becoming the best of friends. I don't think I've ever had a friend I could talk to like Pete or one who could make me laugh like Pete. Any time we spent together was guaranteed to be a great time. Our firm had a company softball team that summer and Pete was the star. I may not have been a great athlete, being only a cross country runner in school, but Pete stuck up for me and made sure I had a spot the team. I was the right fielder, which in slowpitch softball is reserved for the worst player, but I at least was on the team. I greatly wished that he was single and that the two of us could go out on the town to pick up chicks together. But it was still a great time nonetheless.

It was mid-October when I decided I wanted to find a real girlfriend for a change. This was probably because Pete was spending more time with Sarah now that our summer activities had come to an end. I set my sights on Claire, the gorgeous African American front desk worker. She and I had been friendly since I started working there and had just ended things with her last girlfriend a few weeks prior. I wanted to think of something smooth to win her over like Pete did with Sarah. Halloween was coming up and I decided my plan would revolve around the firm's Halloween party.

I decided I would to the party dressed as the hottest brunette I could possibly make myself because I knew that Claire had a thing for brunettes. I had my doubts I could pull this off because I had zero crossdressing experience, but I knew I would give it my full effort. And I figured that even if I couldn't pass as a sexy brunette then at least Claire would see that I was an outgoing liberal guy and give me a chance anyway just for trying. It probably wasn't as good a plan as Pete's, but it was best I could think of. Pete only laughed and said good luck when I told him, but Sarah was surprisingly giddy about the idea and said she would do her best to transform me into a knockout.

A week before the party Sarah said that we would spend as much time as necessary to make me as feminine as possible. It turned out that Sarah and I could pretty much wear the same sizes since we were almost exactly the same height and had similar waists and leg measurements. She was a bit more well-endowed when it came to breasts though, being a large C cup. But she thought that with the right breasts forms, her bras would be perfect for my body type. She had me try on nearly every piece of clothing she owned including dresses, blouses, camisoles, tights, skirts, bras, regular panties, thongs, g-strings, bikinis, lingerie sets, garter sets, baby dolls, high heels, and the sexiest high heel boots. I couldn't believe how much wearing these things turned me on, but I did my best to hide it because I didn't want Sarah telling Pete. She spent most of her time teaching me how to do my own makeup and teaching how to act more feminine. Walking, sitting, and talking were the hard parts, but after a few hours each day I had it down pretty well. Pete had a good time watching all this. He always had a good laugh each time I walked by him in heels. All I could do was smile, flip him my middle finger and walk to another room.

New Lovers

The day of the party arrived and I couldn't have been more excited. Sarah came over that afternoon to help me pick out my outfit and to make sure I did my makeup as well as possible. She also came over to coordinate costumes with Pete. She was going as probably the sexiest Catwoman you'd ever see and he was going as probably the hunkiest Batman you'd ever see.

My first step was to take a bubble bath and shave off every inch of my body except my hair of course. I wanted to be as feminine and realistic as possible for Claire. Sarah, or I should Catwoman, came in to help with my outfit. We decided to go for a more casual feminine look. This started with the sexiest black g-string that Sarah had. It barely covered my penis in the front and in the back looked so sexy stuck in between my ass cheeks. Next we picked a pair of skin tight blue jeans that hugged my hips perfectly and made my ass absolutely pop. Did I mention I was a cross country runner in college? It paid off. My ass and legs were easily as sexy as Sarah's would have been in those jeans.

We then applied the breast forms with adhesive and covered them with a very sexy black lace bra that matched the black g-string. Then we picked out a very cute and sparkly light blue camisole top that slid on perfectly. Sarah decided not to take any chances and did my makeup for me, which I thought was unnecessary because I'd been practicing all week for this. But I couldn't complain because I thought it was stunning. She kept the cover-up subtle but managed to make it look like I'd never once grown any facial hair. She applied a light touch of dark mascara and the hottest pink lipstick I could imagine. Next she added some acrylic nails to my fingers and painted my toenails hot pink, both of which couldn't have been sexier. She fitted me with the perfect brunette wig that we picked out at the costume shop and added a cute matching heart earring and necklace set to complete the look. I then stepped into a pair of three inch black strappy heels that I could die for.

When we were finished Sarah I looked in the mirror and both were shocked. She then sprayed me with the most delicious perfume I had ever smelled. Sarah said that she would take me home herself if she was into girls, which made me laugh because I'm not a girl, right? I certainly looked the part, and was really starting to feel the part. I then took the black purse she gave me and filled it with the essentials for the night. These included my cell phone, wallet, keys, perfume, lipstick, mascara, and some condoms in case I got lucky with Claire that night.

Sarah stayed in my room to work on her outfit, which was a rental and was more worn-out then she expected, while I headed down to the kitchen to get a much needed nerve calming beer. As I came down the stairs I noticed Pete, or should I say unmasked Batman, was sitting on the living room couch watching a college football game. I decided to ask for his approval.

I walked as silently as I could on the carpet so he wouldn't notice me. I stood right beside the TV and did sexiest pose I could think of. In my most sexy feminine voice I said, "Hey Peter, so am I a hottie?"

No answer. He just stared at me with a look that was hard to read, but he was definitely bewildered. The longer he looked at me the more I began to blush.