Office Perks

The look on Jessica's face morphed from surprised to sinister after a brief moment of silence. "Sure!" she said, appearing eager to please me as she pulled her shirt back on. "If you've done it before, then why not? That sounds like a lot of fun!"

It was just like Tommy had said it would be and almost too easy.

* * *

Unlike with Abigail, I was proactive this time with suggesting double penetration, which really was a deal-breaker for me. Instead of letting Jessica do her own research on the subject and risk her becoming unnerved, I looked some things up myself to see the plausibility of such a dastardly act that had always turned me on but that I had never actually done. I was discouraged at first by the lack of real and positive information on DP, not so much because I was concerned for Jessica's well being but because I wanted to have something to show her that would convince her to willingly go through with it. I was also starting to grow worried that DP was just something that looked hot in porn but didn't really work in real life for anyone but pornstars.

At last, I came across a website wherein a girl laid out tips for a male-female-male sandwich, promising, if followed, intense enjoyment for not just the men but the woman as well. I printed out the webpage and brought it to work the very next day. Around lunchtime, I strolled over to the other side of the office to where Jessica was hard at work. I'd noticed that having such little respect for this woman actually made it easier to trap her into Tommy and my plan. In this instance, I had no real trouble making the proposition to her. I can't imagine even suggesting such a thing with a girl I actually respected.

"I've been doing a little research into the activity we have planned for this weekend," I said to Jessica, who was just finishing up some paperwork before she dug into the salad that was on her desk. "I came across some interesting ideas. What do you think of this?"

Jessica took the paper from my hand and began to read it. She was silent at first, an inquisitive expression on her face. She didn't seem surprised or startled by what she was reading, though; rather, it appeared that she was taking it very seriously, reading the page and considering her options.

"Is this something you'd be comfortable doing?" she asked, at this point communicating some incredulity.

"Definitely," I said confidently. "I think it would be a lot of fun, if we did it right."

"You'd be comfortable being that close to . . . you know . . .," she then whispered just in case anyone could hear us, "Tom?"

"I've considered all the pros and cons," I responded. "And, trust me, he's on board if you are."

"Let me think about it," Jessica said. "I've done, you know," she whispered the next word as well "anal." That fact was a new tidbit for me that excited me because it made my proposition more likely, even if only slightly. "But I've never done it like this," Jessica finally finished.

"Take all the time you need," I said, "but just let one of us know by the end of tomorrow." I left Jessica to her salad and made my way back to my office. By the time I had grabbed my own lunch, I was gripped by anxiety that I was making it too easy for Jessica to refuse something on which I had set my heart. Before I finished my sandwich, I decided to text Jessica, which allowed me to be less discreet. "Honestly," I texted, "after reading into it, I see no reason to not give it a try. I think DP is really hot. Wouldn't you like being the center-of-attention like that? I think you'd be really sexy." I felt bad for pressuring her, but all I needed to do was remind myself of what a bitch Jessica had been to me, and I was OK with myself.

Not even a minute later, my phone buzzed. My hand shook with excitement as I grabbed the device, almost knocking over my bottle of water as I reached. "What the hell," the text read. "If you think it will be fun, then why not?" My heart leaped in my chest from excitement before another message came through: "I agree with you, actually - it sounds really, really hot!"

"Let me go tell Tommy the good news," I texted back, glad that she couldn't see my excessive excitement or the boner in my pants. Then, almost as soon as my text was delivered, another response came through.

"Do you want to hang out tonight? I have something in mind."

* * *

We were both panting heavily. Jessica was positioned in front of me on her hands and knees with her ass facing me. She twitched her neck to fling her long, brown hair over her shoulder and out of her face so she could watch me as I tried something that was new for me but not for Jessica. With those brown eyes intently looking at my erect cock, which was hanging free, I used both of my hands to spread Jessica's ass as wide as I could.

"Just do it," Jessica said between breaths. "Just do it, baby. I want you to." I leaned forward, my sprung cock poking at the dark, unfamiliar hole of my ex-girlfriend. Once I had steadied my tip between Jessica's ass cheeks, I took one hand off Jess's butt and held my cock instead. As soon as I had leverage, I very slowly pushed forward, sinking just the head of my penis into the girl's asshole.

Letting out short, forced breaths, Jessica became rigid and continued to watch me over her shoulder as I entered her through the back door. All of my instincts told me to be gentle, since I can only imagine how rough anal sex can be. However, after I had inserted another inch or so of my prick into Jessica's tight, tight hole, I remembered my lack of concern for this particular girl.

Jessica screamed and tensed even more once I suddenly and selfishly shoved the rest of my length into her shitter. She didn't scold me or complain - we both knew she was in no position to complain. Now with both hands on Jessica's ass again, I ground my hips up against her, bottoming out in her lubricated ass, pressing my balls against her taint, just above the hole with which I was much more acquainted.

From there, I held on firmly to Jessica's ass and began to thrust back and forth, in and out of her ass. How constricted it was dominated my thinking as I fucked it. I had screwed my fair share of tight cunts, but nothing like this asshole. I moaned without filter and shamelessly pounded that bitch's was without mercy, taking only a moment to adjust to the sensations of Jessica's raw anal walls before just going to town on it.

Jessica managed to put a lid on her cursing and crying after a minute or two and then just took the ass-fucking like the whore she is. She straightened her back and looked forward, holding herself up on her hands and knees and appearing more comfortable as she adjusted to the situation to which she had willingly submitted. I railed her in the ass to my heart's content until, at last I felt my cock begin to swell. Undeterred, I relentless thrust in and out of her until I nutted in my ex's ass.

Jessica cried out with what sounded like a mix of surprise and amusement as I unleashed my entire load in her rectum. When I finally pulled my cock out of Jessica's butt, a trail of cum dribbled out as well. As I caught my breath, I asked her if she wanted to taste her ass. I gave her the options since I figured a little mercy might go a long way. She declined, which was OK. She wouldn't have the luxury of declining anything once Tommy and I had our way with her in a few nights.

* * *

Jessica had tested and proved her ass and now was ready for the main event. Even after the rough ride I'd given her, she still appeared eager to go ahead with Tommy and my depraved plan. It was even her suggestion that we not have sex again until the big night so that I could save up my load for her. For that reason, I was happy to abstain from any sexual action for the next few days and advised Tommy to do the same.

Since it was so late in December by the time we were ready to go, we intentionally set the date of the threesome for December 31, New Year's Eve. None of us had any obligations that evening, so we all planned to ring in the new year together in the hottest way possible. If it went according to plan, Tommy and I would be plugging up my ex-girlfriend right at the turn of 2016.

For the first time, Tommy and I closed the office on New Year's Eve. The day off would give Jessica the day to rest up and mentally prepare, while Tommy and I would have been too distracted to get any work done anyway. Our other employees, of course, were just happy to have the day off, so there was no questioning the somewhat unusual closing.

Tommy met me at the office around 10:30 pm. I had been there for half an hour already. I was too excited thinking about the threesome to do anything else leading up to it, so I had shown up early and made sure everything was straightened out and in order. By the time Tommy arrived, his help wasn't even needed. He was greeted by a fully cleaned and prepared conference room, complete with wine, some light snacks and a big clock that would let us know when it was the new year.

Once Tommy was there, we both sat in the conference room and waited for Jessica's call to let us know she was in the parking lot. We were both pretty excited to be teaming up on a girl for the first time in a long time and really eager to try our first double penetration. For me, it was an especially satisfying evening as I would be fully venting my remaining frustration and bitterness toward my ex-girlfriend. Honestly, after tonight, everything she had done to me would be all worth it.

True to form for most females, Jessica was about 15 minutes late. It felt more like an hour to us horny guys who were agonizing over finally getting things started. My heart was beginning to sink as I thought that she wouldn't show, which wouldn't have totally surprised me. Finally, my phone vibrated to indicate that my co-worker had arrived.

"Let me in!" was all she said when I answered, and she hung up. I immediately made my way to the front door, where I could see through the glass that Jessica was waiting in a long, heavy coat that covered almost all of her body. What I could see was that her hair hung straight down and that she was wearing black high heels, even though it was snowing and a little icy outside.

I opened the door, greeted by a blast of cold air and a hot brunette. In that moment as we anticipated the raunchy fun we had planned, I almost forgot my disdain for this girl, and it actually kind of warmed my heart to see her. Also, while I'd always thought she was beautiful even though I hated her for most of the time I'd known her, Jessica seemed to be getting prettier and prettier lately. I couldn't wait to see what was beneath that long jacket.

Jessica did her usual small talk, acting as if she were oblivious to what was going on, kind of like how after a month since reconnecting with me, she'd yet to indicate any awareness at all of our past relationship. It didn't matter anymore, though. Tonight would be a night I would remember for the rest of my life. Once Jessica let me fulfill this fantasy, I could consider us even.

I led the young woman into the conference room where Tommy was, and Jess was delighted by the setup in there. Tommy had a glass of wine ready for her before she even began to take off her jacket. I realized, as much as I wanted what was about to transpire, it was a little depraved even for me and that a drink or two might not be a bad idea to help take that edge off.

The first glass of wine I poured ended up spilling mostly on the floor because of my shaking hand due to the fact that right then Jessica took her coat off. I didn't expect her to catch me very much off guard, since I had already seen her naked and nailed her a bunch of times, not to mention fucked her ass even. However, out of those several times we'd been intimate, Jessica had never dressed up for me - until tonight.

As Jessica hung her coat on the back of one of the chairs by the table, I hardly paid notice to the alcohol I had wasted on the floor while I took in the arousing specimen before me. Jessica stood erect and threw her hair back as if to subtly display what she was offering tonight, which was her thin, curved frame that she had draped in a sexy blue dress. The garment hung from her shoulders by two thin straps. It was very low cut, showing off Jessica's boobs, which were pressed together and practically falling out. From there, the dress clung to her hips and tapered off about halfway down her thighs. To accentuate the outfit, Jessica sported four-inch black heels, a pearl necklace and two silver bracelets on her right wrist.

"Damn, girl," I said. "You never dressed up like this for me before."

"I've never had to please two men at once before," she answered as she had her first drink.

"And one of them is your boss, remember," Tommy chimed in, taking a drink himself. Then, wasting no time, he stepped behind the girl, running one arm down her side to her thigh. Looking at me he said, "How about we get this lady a seat and some more to drink?"

Grabbing the wine and first finally pouring myself a glass without spilling it, I made my way toward Jessica and Tommy. I quickly imbibed my first drink and then poured myself another, setting it down on the table along with the wine bottle before pulling a chair out from the table for Jessica. The chair didn't have wheels on it or anything, so it would work for what we had planned. Once the chair was positioned against the wall, I took Jessica's empty wine glass and filled it up again, handing it back to her. I, too, took another drink, which would be just the right amount to eliminate my inhibitions while not getting silly.

The clock showed us it that there were only 20 minutes left in 2015, so we had to move on with our plan if we were going to both be inside Jessica at the turn of the year. Tommy and I, of course, were already sporting large bulges in our pants, so without further delay, we started to undress. We had dressed up as well, wearing office attire, including dress pants, button-down shirts and ties, but those pants were coming off now, along with our boxers. Jessica squealed with delight as these two boners approached her. As soon as I was close enough, Jessica grabbed my tie first and looked up at me with those pretty brown eyes. For a moment, I began to feel my fondness for my ex-girlfriend return.

Jessica didn't say a word, and I caught myself no longer looking into her eyes with fondness but now down her dress with lust. Meanwhile, Tommy stepped up on Jessica's right and grabbed her wrist, pulling her hand up to his cock. Jessica tore her gaze away from me and grabbed her supervisor's cock, looking up at him and saying, "Is this what you want, boss?" Tommy just sighed with pleasure as his employee began to stroke his stiff erection. She then looked back at me. "How about you, lover?"

The feeling of Jessica's soft hand sliding up and down my shaft made me not even care that she had referred to me as her lover. I just sighed and watched on as Jessica beat us both off at once. I first ran my hand through her soft, golden brown hair and then decided to pull the strap of her dress past her shoulder, which revealed a little more of her left boob. Tommy saw what I did and followed suit, only he didn't just push the strap down but used two hands to follow up by pushing the dress down past Jessica's large tits so that they both fell out and were exposed.

"No bra," Tommy commented.

Jessica looked at him, smiled and shook her head. Then she leaned forward, putting her head level with Tommy's prick as she stuck her tongue out and began to lick the tip.

Tommy cursed putting both hands on Jessica's head and forcing her to suck him off after just a few seconds of her licking his dong. Meanwhile, she continued to stroke my cock on her other side. For the next couple minutes, Jessica alternated between Tommy and me, sucking our cocks and gently rubbing our balls. Having slept with Jessica many times in the past, I had seen her in her fair share of hot situations. However, none of my past experiences were quite as hot as watching this topless babe go back and forth between sucking two cocks - and we were just warming up.

While I would have loved to have allowed Jessica to continue with the blowjobs, Tommy and I pulled away after just a couple minutes. We were running out of time if we wanted the main course by midnight, and it was more important that we preheat Jessica for what was in store than that she pleasure us. Without hesitation, Jessica briefly stood up to push her dress down the rest of the way, revealing a cute black thong, which also ended up around her ankles with no delay. As Jessica stepped out of the clothing, she quickly unclasped her necklace, at which point I advised her to leave the remaining jewelry on as well as the heels. To my request, Jessica simply smiled, dropped the necklace on top of her dress, and kicked all the discarded clothing aside.

Now nude, save for her shoes and a couple bracelets, Jessica was seated again. The clock read 11:48 pm, so we had really no more than 10 minutes of foreplay with Jessica before we needed to get her into position. At this point, Tommy and I took off the rest of our clothes but stayed on our respective sides of our female employee, who suggestively spread her legs for us as she remained in the chair. Tommy leaned right in and kissed her, squeezing her left boob. I, meanwhile, squatted down and picked up Jessica's heel, bringing the shoe to my face. I started my foreplay by licking the top of Jessica's foot and travelling all the way to her knee. Jessica moaned and quivered a bit while still making out with Tommy as he fondled her breasts.

Next, I lifted Jessica's leg over my head and drew closer to her exposed twat. First, though, I slid my free hand underneath her, searching for her asshole while I rested her leg on my shoulder. I had never fingered a girl's ass before and didn't really want to this time either, but I knew our best shot of getting right to double-fucking Jessica was to work her ass in a bit before putting a dick in there. Jessica gasped when she felt my finger poke her stink but she allowed me to proceed without complaint. As my finger slid inside her, still not really my thing, Jessica put one hand on Tommy's head, which was now sucking her tits, and the other on my head. Her fingers combed through my hair as I began to thrust my finger in and out of her tight butthole.

One finger became two, and then I was ready to lean forward and eat my ex's pussy. Jessica really cried out now as her ass, pussy and tits were all stimulated at the same time. As I licked Jessica's pussy and sucked on her clit, I knew as well as anyone in the room that she was nice and wet, ready to fuck.

With only a few minutes to go until the new year, it was time for the main event. Tommy and I pulled away from Jessica's body and lifted her up from her seat, leading her over to the conference room table. It was wooden but solid and sturdy. Remember that we had been fucking girls in this room for a while now, so all the furniture was purchased with that purpose in mind, even for the most extreme scenarios. This table would be more than capable of supporting all three of us if it needed to do so.

I got up on the table first and lay down, followed by Jessica who hovered over me on her hands and knees. I put one hand on her lower back while holding my cock with the other and aligning it with that wet pussy. Jessica briefly used one hand to help me find her hole and then went back to supporting herself with her hands as she sank down on my cock. We both moaned in unison as Jessica lowered herself until she was on the very base of my cock.

It was almost midnight, so there was no time to work Jessica up to Tommy's entrance. Instead, Jessica's boss stood right up behind her, in between my and her legs as he spread her ass with one hand and steadied his prick with the other. Jessica looked intently over her shoulder while I held her in place and Tommy put one hand on her lower back, pressing his cock against Jessica's alternate entrance. Then I felt it, the head of the other man's cock pushing into the hole adjacent to the one I was filling. It was a weird feeling, but hot more than anything else. While Tommy and I were straight guys who had never had our parts this close, it wasn't our first time sharing a girl either, so neither one of us felt very awkward.