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Roommates With Benefits: The Working Vacation

A trip to London yields a job promotion and an unexpected souvenir.
Since the blizzard last year, I’ve kept my distance from Jayson and the chicken-head that has come home to roost. I became more focused on my photography and writing at the magazine. I had to put Jayson out of my mind regardless of his sexual prowess. I tried so hard to forget my unhappy encounter with his estranged wife in favor of bigger and better things. My self-denial paid off when I eventually landed assignments to write, photograph, and blog about fun stuff for possible syndication.

At the downtown office, my boss, Nicola Campbell, came over to my office to talk to me. A statuesque blonde with sky blue eyes, athletic build, and a great tan, she knows what it takes to gain notoriety in journalism. Thanks to her, I have a weekly online radio show.

“Sharon, are you busy?” Nicola asked me.

“No I’m not. What is it?” I answered.

“I have an opportunity of a lifetime for you,” she began.

“Oh yeah? What is it, Nic?” I ask, with my interest piqued.

“How would you like to go to London and cover the Diamond Jubilee event?”

I began to do back-to-back somersaults on the inside. It has been a dream of mine to go to London on a vacation, now the opportunity presents itself in a way I’ve never expected.

“I’ll do it. What would you like for me to accomplish?”

“Aside from interviewing the various people there, I would also like you to blog and take pictures while you’re there as well. I also want you to write a full-length feature article for me, and there’s an opportunity for you to become the lead editor and chief photographer. What do you think?”

“Nicola, I’m your woman for the job.”

“Good. The celebration coincides with your vacation. Now, go home and pack your bags for England.”

I survived the twelve-hour plane ride from Chicago to London with an e-reader, diary, and a sleep mask. When I got to the hotel, I unpacked my belongings and flopped onto the giant king-sized bed. Perhaps it was the jet-lag, but I was having thoughts of Jayson and Justine splitting up. Quit thinking ill on those two, Sharon! I told myself. You’re here on the other side of the Atlantic Ocean to do a great job on this assignment and there’s a huge promotion on the horizon. Focus on the prize!

Feeling restless, I grabbed my equipment and venture out into the streets of London. Buckingham Palace was just a stone’s throw away from my hotel, so I had a great view of the parade and I could get snapshots right from my room. As I walked around, I saw barricades up, the press box for the major news organizations and channels, and people wearing replicas of the crown. I snapped a lot of pictures of the people and talk to some of the locals and tourists. I even ran into two people I didn’t think would ever leave Chicago to come here.

“Sharon! Long time, no see! How are you?” Amber Lynn, my ex-best friend and former roommate asked me. The peroxide blonde gave me a hug.

“I’m good,” I replied. “Where’s Dante?”

“Dante’s right here,” Dante announced, coming out of the coffee shop with coffee and scones. He still looks good with his caramel complexion, green eyes, and plantation hair that’s cut into a low fade. “What brings you to London?”

“Coverage of the Diamond Jubilee for work,” I answer. “What about you two?”

“We eloped, and we’re on our honeymoon,” Amber Lynn explained.


“Are you going to cover the Olympics next month?”

“Not sure. I would love to come back to watch the games, though.”

“Do you have any plans for later on this week?” Dante asked me.

“Not sure. What did you have in mind?”

“We can hang out at the end of the week before heading back to Chicago.”

“I would like that.”

The Diamond Jubilee celebration ended with a concert put on by A-list bands, groups, and singers. I hung out in the press box and took a bunch of pictures. I also got to know the other journalists and photographers during the slow moments. After the concert, I talked to more people and shot more pictures until it was time to meet Dante and Amber Lynn at the hotel bar.

I got to the hotel lobby and I stopped dead in my tracks at the sight of Jayson and Justine. Why are they here? I asked myself. I went to my room to change out of the blouse, press pass, and jeans I wore and put on something a little more suited for the bar. I chose a little red dress with matching underwear and stiletto heels. I walk in and the majority of men took notice and bought me drinks. I ordered my usual dirty martini, and sat a nearby table to survey the bar. Dante and Amber Lynn came into the bar, and began to converse with Jayson and Justine. Ignoring the two couples, I flirted with the men, had some drinks, and retired for the evening.

I woke up to someone pounding on the door. As I looked through the peephole, I saw that it was my ex-fiancé Dante and my ex-roommate/lover, Jayson. I opened the door and asked them, “What brings the two of you to my room?”

“Watching you flirt with all of those foreign men,” Jayson replied in a licentious tone.

“You wearing that little shift dress didn’t make it any easier on us,” remarked Dante.

I shook my head to get the sleepiness out. “Oh yeah, Dante? Did you like it when I made out with the Italian guy?”

“Yes I did, sugar.”

I knew both Dante and Jayson wanted to get in my panties, so I let the sexpot come out of me. After all, they both just wanted to get laid before going back to their significant others. Who cares if they’re here with their wives? I just wanted to get laid before heading back to the States, as do the men.

“Dante, please tell me more. I want to know all of your thoughts,” I cooed, feeling Dante’s growing bulge.

I opened the door and allowed the men to come inside of my room. Jayson took a seat on the bed as I stood in front of Dante. Taking me into his arms, Dante kissed me and my panties immediately got wet. Jayson stroked my stocking-encased legs, trying to get me to open them up. He opted to unzip me, allowing my flowing dress to cascade to the floor. While I made out with Dante, Jayson unhooked my strapless bra, allowing my big breasts to breathe.

Prying me away from my great love’s embrace, Jayson threw me on the bed and ripped my panties off like a madman. Holding my hands above my head, Jayson used the scraps of my panties and tied my hands together, with Dante assisting. Spreading my legs wide, Dante cups my bare pussy and fingered the opening slowly, knowing that would drive me mad. As Jayson forced my legs open, Dante found my throbbing clit and finger it hard. I writhed on the bed, trying my hardest to resist Dante’s intimate fondling and Jayson tickling my feet.

Dante and Jayson switched places, this time with Jayson manipulating my breasts as Dante ate me out. I began to buck with Dante’s tongue plunging inside of me and I started to shake. Sensing that I was about to come hard, Jayson tugged at my nipple piercings and Dante tongued my swollen clit harder and faster. I let out a wail and squirted all over his face.

Dante planted a kiss on my lips, allowing me to taste myself. For the first time in the two-year span of not seeing or sexing one another, I saw fireworks that were more explosive than the first time he kissed me. Cupping my dripping snatch, Dante asked, “Ready for the snake, Sharon?”

“She is, I want to get into that chocolate ass,” piped up Jayson.

“I have some lube in the toiletry bag,” I responded, “you’re not going in there dry.”

While Jayson searched for the bottle of lube, Dante and I concentrated on each other. Turning me so that I was on top, I slid down onto his ten-inch shaft. As I bounced up and down, Jayson lubed my asshole and inserted two fingers inside me. I felt Jayson push his shaft into my opening. Dante kissed me hard to counter the searing pain I felt from taking Jayson in my ass. I felt Jayson pull out and Dante push in, creating a rhythm to ensure I got maximum sensation from my first double penetration.

“Oh, my god!” I screeched, feeling Jayson yank on my hair as he pounded harder into my ass.

“I’m about to come in that ass, Ebony Girl!” Jayson panted as he floods my ass with his thick spunk. Right behind him, Dante shot a thick wad in my pussy.

“Damn, that’s a tight ass you have,” Jayson whispered.

“That’s because it’s the first time I’ve ever done anal,” I whispered back.

“Oh, yeah?” Jayson and Dante asked excitedly.

“Yes. I wanted it to stay virgin tight. No foreign objects were allowed in there, especially a dick.”

“I want a turn in that ass,” Dante replied.

“Let me catch my breath first.”

Twenty minutes of drinking and laughing, I quickly pounced on Jayson. I gave him a kiss that he wouldn’t forget, even while he’s married to miserable old Justine. I kissed my way down his torso, flicking his nipples with my pierced tongue. I gave him one of my famous smiles, and then gave him a sloppy blow job. My tongue bathed his penis as I manipulated his balls with my hands. Dante stood behind me and licked from my dripping snatch to my asshole, eliciting a moan from me. He ate me out, and plunged a finger inside my butt. I removed my mouth from Jayson’s boner and straddled him, with Dante’s finger still inside me. I felt Jayson slip inside me, knowing full well he’s getting sloppy seconds.

“Fuck, Ebony Girl, you’re still tight after the reaming Dante gave you,” Jayson grunted.

“I have a dirty little secret to that: I did my Kegels while riding him,” I answer.

“Was that why I came so quickly?” asked Dante.

“Yup. Less talking and more fucking the shit out of me, now!”

At that command, Dante slammed his cock inside of my ass. He clamped his hand over my mouth so I wouldn’t scream. As both men rode me hard, Dante slipped his fingers inside of my mouth. I reveled in sucking on his fingers, allowing me to fantasize about the hot guy from Greece I had blown in the press box earlier in the week.

“Mmmmmmm,” I moaned.

“What are you trying to say, Ebony Girl?” Jayson asked, sucking on my pierced nipples.

“I’m about to come and squirt hard,” I panted.

Jayson and Dante began to fuck me hard, with their sweat dripping on me and my sweat dripping onto them. With one final thrust in me, both men creamed hard, while I squirted the hardest ever in my years of having sex.

I was sandwiched between Jayson and Dante with both cocks still hard inside of me. The room smelled of sweat, sex, and other scents I couldn’t place. I wiggled my hips, signaling the men to get out of me.

“Do I have to leave this tight ass?” Dante asked.

“Yes you do, unless you want me to text Amber Lynn and tell her where you are,” I answered.

“Would you tell Justine?” Jayson asked.

“Are you crazy, Jayson?”

Reluctantly, both men left my crevices and looked at me. My hair looked as though birds were nesting in it, my nipples were hard, my body’s flushed with sweat and scratch marks, and I had cum dripping out of both holes. As they put their clothes back on and doused themselves in bathroom Polo, I sat on my bed and watched them exit my hotel room.

My final couple of hours in London was painful. I was happy, sad, and exhausted at the same time. Dante’s married, Jayson’s getting remarried in two weeks, Amber Lynn and Justine were glowing with excitement, and I’m without a fuck buddy, a fiancé, and a great friend. Why I always choose men who choose me as the other woman was completely beyond me. I wished both guys nothing but the absolute best in their lives.

I packed my belongings and got in the cab that would take me to the airport. Jayson sat in the seat next to me, and Justine climbed in the back. Like an obedient dog, Jayson left my side, followed her into the back, and gave me a look that said I’m sorry. Dante got in as well and took the seat next to me, and Amber Lynn was perched on the other side of Dante. I looked out of the window as the four of them made plans to do married folks’ activities together.

I have a career I’m married to, anyway.

The jubilee celebration article I did for the magazine landed me the promotion of lead editor and a job as a correspondent for the news station. As an added bonus, the article was syndicated across the country and into several other places around the world, giving me more notoriety than before. I’m still able to co-host a weekly radio show and continue my work as a photojournalist at the magazine. Jayson and Justine got married, much to my chagrin.

Six weeks later, I began to feel weird. Wanting to find out what’s going on with my body, I go to the doctor and found out I was expecting. Instead of expressing joy at the news, I began to plan out the mommy blog for my readers as I ponder the paternity of my unborn child.

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