Tiebreaer

About a dozen years ago I started working at an international company at one of their offices in the US Midwest. The team of ten people worked closely and grew to know each other through hours sitting together. In situations like that solid, long-time friendships can develop. Other relationships can develop, too.

Jenny began at the company when I did. She was engaged to some guy. I swear the only time I saw him was in a really neat picture of Jenny riding on his shoulders at some sports event, a picture she kept in her cube area. Those two really appeared to be a fun couple, but Jenny was most often reserved and serious. In the picture she was smiling and goofing around. I wanted to find out more.

Jenny aspired to be successful professionally, and that seemed to guide her interactions. Over time she opened up and her business-like demeanor loosened up. She even became a bit flirtatious. After two years it became apparent she came across as prim and proper but there was more going on. I just knew it. Beneath that demeanor was a WILD woman, I was positive.

Unfortunately, Jenny followed a dream to move to California. Her engagement had fallen apart – hell, I didn’t think he was deserving anyway! Once out there she and I kept in touch for a couple of years in which she shared tales of dating or fending off guys. She continued to flirt openly. Yes, we were different in a few key ways and never got beyond the talk even though it seemed like the potential was there.

As luck would have it Jenny eventually returned to our company only this time working in another city. But she WAS back and in the same division of the company as me. Hmmm...good, I thought. But damned if she didn’t get engaged AGAIN though. Yes, busy gal. She could attract the guys; they’d fall for her every time. However, after just a few months, this engagement fell through, too. Jenny was always full of surprises.

In our jobs we now attended the same meetings at various locations. We also took time helping each other’s careers, plus held late-night discussions wherever we were. I did try to put the move on to her a couple of times but was rebuffed in a nice, consistent way. I never pressed the issue, but she kept teasing me along and, being a normal horny guy just ate it all up!

We shared stories at every opportunity with no one in the company any wiser. She was serious about being successful, and I wasn’t going to fuck that up. We continued to talk about relationships, family, and frankly, things of a sexual nature. I gave up hope of something happening but it was still fun as Jenny had a smart mind but more importantly dirty and very naughty. I could learn some things from a woman’s perspective. Cool, I thought.

Timing again worked on my side when we were promoted to a similar level and scheduled to attend the same three-day training/celebration. The celebration session was the kind where money did not matter and the company spent freely - first class all the way AND the perfect setting for something to change in my admitted lust for Jen. This was now six years after we first met. So we both flew into the same city to join hundreds of other new executives. I was at my most business-like behaviour, of course. But Jenny seemed to be much friendlier with me than before. Or maybe it was just my male ego?

The first two nights of the session there was plenty of drinking, networking and bullshitting going on. Late at night she and I gathered in her room to talk: I did my usual pop-psychology about her dates, boyfriends, and fiancés. And she did her usual tease that drove me a bit crazy. She innocently made sexy remarks and seemed to shed clothes while we spoke, “Oh, I’m hot do you mind if I take this sweater off?” or “I’m going to put on my jammies but you know I only wear a t-shirt, is that ok if I get dressed for bed now?” Not fair!

Finally, the anticipated blowout party night arrived. The company rented a sports dome and had a half-dozen open bars, games, and fun going along with a live band. It was a carnival atmostphere and I was feeling no pain after a few trips to the bar or grabbing drinks off countless trays being carried around. I challenged Jenny to a few games – she being very competitive – and we ended up tied in total wins. Jenny said she would figure out a tiebreaker later. I didn’t know what she meant at the time.

We left the party during the night for a short bus ride to take a tour. On the bus we had a few more toddies until reaching the destination. On the way everyone toasted our success and, at the right moment, I kissed her cheek. She just smiled.

Once at the location we took a series of three escalators up to the private tour’s start. On the second of three escalators I was a step below her and Jenny started rubbing her body, her ass, all over my chest. Her TIGHT JEANS felt good. She bent her neck and head backward to whisper in my ear, "Tonight is the night." I was a bit stunned. “What does she mean?” I thought. It was so damned noisy I wasn’t sure – but my mouth went dry anyway. I said nothing but stared up at her. She watched my reaction grinning.

Next we were part of a same small tour group and, as the tour progressed, Jenny pulled me to the back at each stop, stood in front of me, and rubbed very deliberately backwards. I couldn’t react (though I was having a hard time, so to speak). She gyrated her NICE ASS on me, grabbed my crotch casually, and whispered in my ear and such. I just pretended to listen intently to the tour host. But my COCK was HARD most of the tour!

The tour ended, we got back to the bus, and Jenny led me to the very last seat on it. As the bus roared back to the party she started messing with my belt and zipper. I still wasn't convinced she wasn’t teasing me more, her most devious flirt. I had been rebuffed before. I played along.

Once inside back at the main party we walked around a minute or so when she told me to grab some wine and MEET HER BACK IN HER ROOM a little later. Then she took off. I still couldn’t believe it, but I was sure those were my instructions. Fuck, this was the night!

I made it back to the hotel about a half hour after she had left the party. I was still not sure this was really happening but my cock was pretty positive and had been twitching for a long time. I hustled through the crowded lobby and entered the elevator with drinks in hand. As the doors opened onto her floor I walked down a couple hallways to her door, casually double-checking both ways in the hall for observers. No one there. Good. I kick-tapped the door’s bottom and it opened, an arm extended out, a hand pulling my sleeve and me inward. The door closed quickly behind.

The room was barely lit. Jenny was behind me, telling me in a soft voice to set the cups down somewhere. I did so without even turning around. I did finally turned and there she was in a robe. I had seen her in her robe many times - she had tantalized me in it a few times – but this time I might be able to see the inside of the robe.

Jenny asked me to dance, something we neglected at the party since we were too busy competing against each other at those games. She said the dance was the tiebreaker, a slow dance contest. I nodded. We embraced gently and started to move slowly, with no music except the beating of my heart; well, I could feel it beating at least. My palms were damp. Damn, this was nice.

After a minute or so my hands moved up to her hair, down her back, along her butt. She didn’t push my hand away. She wasn't teasing this time.

Finally, I made a bolder move and put my hands on the robe, helping it drop off her shoulders to the floor. I could hear a puff of air escape from her lips, the sound of anticipation.

We kissed, our lips meeting tenderly, our tongues intertwined. My hands were roaming her body as I had imagined many times.

I pulled the vixen over towards the bed; its sheets already pulled back as she had prepared the room before my arrival. Jenny moved onto the bed. I was still fully clothed. I removed my shirt as she just lay back, luxuriating on the soft mattress. Her hands moved over her own body, watching me as I unbuttoned my shirt. She looked super sexy.

I bent to kiss her again, my hands finding her breasts this time. I had wanted to touch them for so long and I was in no hurry now that my opportunity had arrived! I started to kiss her neck, nuzzle it, and lick it. Now I teased her body a bit. We weren't talking much. We had talked for hours as friends and colleagues. This was NO TIME FOR TALK!

My lips found her titties. I knew what to do from here. She was starting to moan. I started to WORK ON HER NIPPLES, paying attention to both and teasing between her breasts with my tongue. I was sucking, chewing, and nibbling on them with my mouth. Her hips were slowly bucking up and down, barely, but noticeably.

My right hand slid down her legs, moving around touching her, my nails lightly touching her skin. Finally I moved my hand near her soft patch of dark hair, my middle finger and index finger alternately touching the lips of her pussy. She was VERY WET and she lifted up her hips to meet my fingers.

While I continue to do my best on her knobs I slid a finger knuckle deep into her slit. I moved the tip of that finger around. Jenny gulped, her breath caught. Her left hand pressed on top of my hand showing she wanted more. I moved more of my finger into her MOIST SLIT. There was a squishy sound I could hear as my mouth still worked on her chest and neck. I moved that finger in-and-out of her cunt only to the second knuckle-depth, my palm lying on her mound steadying my hand.

My hand was going nowhere as she increased pressure on the back of it. Jenny had one hand on my head and the other on my hand, getting what she wanted in her now SOAKING PUSSY. I inserted the entire middle finger inside her and pulled my hand up to begin a long, slow finger-fuck. I also felt around her folds watching her reaction where it felt best. She was breathing faster.

I stopped licking her nipples, tugging on them, and playing as I slid my torso backwards, my knees landing on the floor. I removed my fingers from her tunnel and used both hands to pull her hips toward the edge of the bed, her legs bent at the knees over the side. Jenny still didn't say anything. There were no noises outside in the hall – the only sounds were us!

I moved my head between her legs, my LIPS FINDING HER CUNT, my fingers spreading her and I began licking her clit, alternately using my tongue as a cock. I attached my lips to her pussy and she moaned loudly, yelping a bit. Her hands were either on the top of my head or grabbing the sheets of the bed, gripping hard. She bucked her hips like she wanted to HUMP MY FACE. Fuck yeah!

I continued to lick and use my fingers in her wetness. Damn, Jenny, the PRIM AND PROPER WHORE, was now soaked. She said, for the first time in quite a while, "Yes, yeah. That's it." Words like that. Words of lust. "Faster. Move your fingers faster...yes....!". Her hands pulled up on her nipples as far as they could go. She also held onto the sheets to steady her body as it convulsed.

Jenny continued to lift her hips upward, meeting my quick, deep finger movements. I could feel her PUSSY TIGHTENING around my drenched fingers. A couple of minutes later she sort of froze with her hips up off the bed, her head lifted off the mattress, her body convulsing in quick, jerky motions. Her voice pitched higher as she moaned and sucked in air. Jenny was CUMMING SO HARD I stopped to watch my fingers continuing to do their thing. Damn, she looked so fucking hot and so fuckable.

Jenny finally stopped and I pulled my fingers out slowly, gently. She laid in silence. I could hear her breath slowly. Her body was motionless. I had been on my knees for a while so I stood up and sat back down on the edge of the room's other bed.

It was quiet for a couple of minutes. I walked over to grab the wine, taking a sip of the now warmed content.

Jenny asked me to come back over. She sat up, no longer caring that she was naked and that we were together at this time and place. The sheets were a mess, a couple of pillows on the floor. She looked so pleased like a cat laying in the sunlight. A perfect setting.

I had been rock hard, but retaining that erection for too long inside my pants was not possible. We kissed and she reached for my belt, a belt she had teased and toyed with only hours before on the bus. She removed my belt while I felt her shoulders, neck and played with her hair. Her body was still all new to me.

Finally, she RELEASED MY PENT UP COCK, which rose quickly to hardness. I was half-sitting up using the pillows behind me for a backrest. She played with my tool, with the head, the underside. She tickled my balls. Jenny whispered into my ear hat she was going to, "...make you very hard and then feel your hard dick deep inside." Seemed like a good idea to me!

She started to SUCK COCK and, as Jen had told me a few times, she loved sucking dick, and she was proving her credentials. She was really good, totally SLUTTY like I knew she would be. I didn't say too much but admired her passion and technique. Jenny bobbed, sucked on the mushroom head, and took it deeply several times. Beautiful cocksucker Jenny just kept doing her thing.

I could have CUM RIGHT THEN AND THERE – maybe I should have? - but I maintained control. The sucking ended as Jenny moved up and got in position to straddle my now super-hard shaft. She lifted her leg and mounted me like a jockey getting on a horse. I was ready for this race. She was so wet my cock slid smoothly inside. It felt fucking great to finally be in that pussy she had bragged and teased me about.

She was in silhouette as I watched her ride me. That’s such a great sight to see a woman mounted on a cock. She moved up-and-down on my rod, my hands on her sides helping her body use the stiff pleasure toy. I played with her breasts, too, SQUEEZING and KNEADING them. We built a good thumping rhythm. She talked nastily and seemed to revel in telling me how much she liked fucking and being filled with my cock. Jenny’s cunt was like her mouth – and that was good. It was difficult not to just PUMP HER FULL OF SPUNK but I wanted it to last all night. Or at least for a while longer!

After a few more minutes Jenny wanted me on top of her, driving into her and fucking her as hard as possible. She wanted to be FUCKED, THUMPED and POUNDED. This wanton fuckslut would get her wish. I wasn’t going to debate that point. We shifted positions with my COCKSHAFT somehow staying inside her tightness. It was like we had practiced fucking over the years during our verbal foreplay.

I obliged Jenny with a hard, relentless banging. Maybe some of what I did was REVENGE for years of verbal torment. It was just after midnight at that point, and I knew this would take all the energy I had left. She lifted her legs back and held onto her knees spreading as much as possible. I steadied myself over her body and my hips thrust my engorged MANMEAT into her SLOPPY WETNESS. I loved watching her tits bounce around as I gave her tunnel a thrashing.

Jenny’s face looked so great below me as my fuckstick worked her TIGHT CUNT. I knew she could feel the cock’s veins pressing her walls and the thick head deep in her snatch. And she seemed to love it all.

I lasted longer than I anticipated considering my load had been building up all night long. I grunted pushing my body forward as I finally spewed the jizm deep into her body. Fuck yeah, I just LAID DOWN THE PIPE and kept going like a madman! She was screaming at me to, “Shoot hard! Fill me with cum! Give it to ME! GIVE IT TO ME!” I figured the whole fucking hotel could hear her wail and cry out, but frankly I didn’t give a rat’s ass – I needed to spew deep into Jenny’s snatch and loved the sound of her urging me on. I drove into her like I was trying to shoot a wad of THICK CUM into the center of the mattress.

I finally spurted so much jizz into Jenny I figured she would be leaking it for a week! She deserved every fucking ounce, too. Next time, I vowed, the white mess would be on her ass, her chest, her tummy, her hand, or her face. Maybe everywhere!

I was drained and spent so I lay on top of her. She held my head in her arms. It was a cool moment. I was breathing hard but not out of breath. Damn I felt good – and I knew she did, too.

After a few moments we decoupled. It's always an odd sensation to do so, ain’t it? But my cock pulled out of her with an audible plop. She said she wanted to clean herself up as the cumjuice started pouring back out of her pussy. She also wanted to see the sizeable load, which I thought, was a nice touch on her part. Damn, she was still being a naughty young lady.

We were in no hurry nor were we feeling weird about this culmination of years of flirting. It was a bit awkward in the room but we were also comfortable, having known each other for so long and having established a solid foundation of trust.

I was still a bit surprised by her change of heart that we hadn’t discussed to that point. We would eventually. We had crossed the line we had teetered on before but crossed it we did. She came back to the bed and we lay next to each other talking. Everything was cool.

We both had early flights out. I left her room knowing that things had changed but really not too much. We were cool.

We have our own lives but once in a while we gotta break that tie again!