Sissy: That Time of Year Again

by Dapper Dan

Copyright© 2009 by Dapper Dan

Romantic Sex Story: Betrayed in love, Sissy becomes embittered and builds defensive walls against any kind of emotional involvement with men. But eventually, there came this... You'll just have to read the story to see what transpired.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Cheating   .


Sissy ... lead female character, twenty-nine, business exectutive
Sue ... female assistant to Sissy, twenty-two
Kamp ... boyfriend of Sissy, thirty, gave Sissy a diamond
Kari ... female assistant to Sissy, twenty-two and unknown rival
Curt ... lead male character, thirty-four, business executive in same company as Sissy

Damn, Christmas, again. Bah, humbug!

I remember three years ago at this time. Actually, it was the weekend before Christmas. Kamp and I were in bed in our apartment. His cock was buried to his balls in my pussy and he had just dumped a load of cum into me.


"What?" I managed to mumble out in my post-coital haze.

"I have something for you."

"I thought you just gave it to me--in my pussy."

"No, this is for your finger."

I opened my eyes--and there was a ring. A ring with a rock big enough to rival the Rock of Gibraltar, or so it seemed.

"Damn! Does this mean you're proposing after three years?"

"Yes, that's exactly what it means. I thought that since you can't be here over Christmas weekend, I'd give you your present now."

"Oh, My God!" I cried as he slid the ring on my finger.

Still coupled, I moved my hips into Kamp. His cock grew again and we pumped away on another go 'round. I grabbed Kamp around the back and pulled him down unto me, crushing my boobs into his chest and holding him still.

"I just want to enjoy your full cock stretching me to the limit. Lie still and hold me."

The next Friday saw me in a cab on the way to the airport. Although I would be paid extremely well for it, my job required me to be out of town over Christmas weekend this time. The job was far too good to turn down the assignment. Refusing would have been a very bad career move.

I flew out Friday night of Christmas weekend, expecting to return home Monday, the day after Christmas. The plane was an hour from my destination when I got the word that the meeting was canceled. God Damn! What a fucking waste of time. But, I was lucky. I got a return flight back home an hour after landing. That was normally impossible during the Christmas weekend holiday with all the travelers, but I did have my connections and clout.

The flight back seemed twice as long. I was seated in an aisle seat. A nice looking stud across the aisle was giving me the once over and a definite invitation. I just grinned and rested my rock covered left hand on my right thigh where it must of blinded him. He grinned and left me alone for the rest of the flight.

About midpoint on the flight back, I decided to surprise Kamp, so I didn't phone him of my impending return. The time was two-thirty a.m. when my cab pulled away from the cab stand outside the terminal An hour later, the cabbie let me out a block away from my apartment at my request.

Carrying my overnighter, I trudged the block in slushy snow. My excitement level went up along with the elevator, as did my pussy moisture, in anticipation of getting Kamp's cock back where I most liked to have it--buried deeply in my pussy.

My entrance into the apartment was as silent as I could make it. So was the apartment--silent, that is. Well, at this wee hour of the morning, he should be fast asleep. What a surprise he's about to get. Ha! That's how much I knew about it all. Listening intently, I finally heard it, muffled sounds from down the hallway, towards the bedroom.

Whaaat? Damn, that better not be what it sounds like!

I slipped out of my pumps and padded softly down the carpeted hall. The sounds grew louder. A moan. Of pain. A groan. Of pleasure. The bedroom door was open just a crack. I eased it open some more and looked in.

Talk about surprises. But it was I who got the damned surprise, a double barrelled surprise at that.

There, both butt ass naked, lay Kamp on top, his cock embedded to his balls in the pussy of my best girlfriend and colleague from the office. Kari orgasmed as I watched and I could see, from experience, that Kamp was very near.

For some dumb reason, I still had my digital, single lens reflex camera hanging from my neck. I reached for it, aimed, and fired off a shot, moving in and taking several more rapid fire shots just as Kamp dumped his load into Kari's box. Perfect timing. I got his head thrown back, the deep arch of his back, and the facial grimace as he climaxed. That's not to mention her deeply arched back and her upthrust pelvis as she rose into his final, deep thrust of ecstasy.

The bright flash of the camera strobe finally broke through their sexual frenzy and they momentarily froze in place, both looking directly into the camera. I got that picture too.

As I backed out the bedroom door, I slid off the engagement ring and flipped it his way. On the way down, my hand snagged the camera shutter button and the camera went off, accidentally catching the ring in a mid air picture just before Kamp's hand enclosed it.

"You slimy bastard, you stinking asshole two-faced bastard! There aren't words enough to express what I think of you. But there's your ring back. Maybe Kari will wear it."

I turned and fled for the outside door, but not before I heard the unmistakable squelch and pop of his cock popping free of Kari's wet pussy as he disengaged and clambered off the bed to stumble after me.

"Sissy, wait. I can explain! Please."

"Sure you can! Tell it to Kari. you two-timing asshole. It was her cunt your cock was punching like a jackhammer,"

I said as I slammed the apartment door in his face. If he'd still been sporting a hardon, he would've blunt-nosed it straight into the closing door. I sorely wished he'd had a stiff boner bashed. It'd serve the bastard right.

The weekend passed in excruciating slowness as I cried the whole time in my downtown motel room. No one knew where I was, and I'd instructed the desk, no phone calls, no visitors just in case. I left my cell phone turned off. I tuned in a country music channel on the television and just bawled away the weekend, all three days of it.

Tuesday, it was "business as usual," back at the office. Kari had called in sick. I called her a colleague, but she was one of my two assistants and I think she knew what would be coming down on her. Sue, my other assistant, stepped into my office with two cups of coffee and closed the door.

"I'm so sorry, Sissy."

How did you know, Sue?"

"Kari called me to call in sick and told me you walked in on them."

"Oh. How long have you known?"

"For some time. I wanted to tell you, but didn't know how. If you want to know the whole truth, the bastard was triple timing you. He was fucking two other women in addition to Kari."

"Oh fucking shit! Shit!"

"That's not all, Sissy. He even hit on me two or three times before he got the message I wanted nothing to do with him."

"God, Sue, I was so blind. I had no idea."

I was already a workaholic. That got even worse as the current new year grew old. My social life dropped to just company functions where attendance was not required in writing, but was still expected if one valued his job. Men and in particular, sex, was no longer part of my twenty-nine year old life.

Now, Christmas has rolled around once more. Like I said,

"Bah, fucking humbug!"

The company Christmas party was combined with New Year's for one big, combined party New Year's Eve. Like all the other office meetings, this one wasn't directly required, but just the same, one had better put in an appearance. One's job did definitely depend on it. The party was three hours old and I was seriously looking for an excuse to leave.

I had to be careful if I left the main party room as most crannies and/or offices were likely places of sexual encounters of the fucking nature and one could never predict who would be doing whom. In this age of political correctness and company liability to sexual harassment charges, I was quite surprised that so much of this kind of behavior was still in fashion on company property.

Still looking for my excuse, I was standing at the hors d oeuvres table, placing several delectables on a small plate. I turned left to leave the table just as the man to my left turned right to also leave the table. We collided.

His plate of hors d oeuvres went into my cleavage, generously exposed by my low cut gown. Mine went all down his front, his shoes, and the floor.

My pent up emotions surfaced as I lashed out with a snarl, "Why don't you watch where you're going, you fucking pig! You fucking clumsy pig, I should say. Damn it all, look at the mess you've made of me."

"Ditto," he said with a big grin, as he picked up another hor d oeuvre and smashed it into my forehead.

"OH yeah?" I snarled out again, as I picked up an hors d oeuvre in each hand. I smashed one into each side of his face.

"Yesss," was his grinning reply as he picked up another and mashed it into my lips, forcing my mouth open in surprise. He pushed the hors d oeuvre on into my oral cavity. I nearly choked before I spit it out into his face.

He was still wearing that shit-faced grin. That infuriated me even more. I don't suppose my face looked too pretty as I glared at him, boiling mad.

By then, we were attracting a great deal of attention. People stopped to stare rather fearfully. I picked up a full drink and pitched it into his face. He reciprocated by pouring a full drink on top of my head and watching it course down both my front onto my tits and down my bare back.

I grabbed his belt and pulled his pants out just far enough to dump a full martini glass down into the space. He grabbed my low neck line, exposing my braless boobs to his view and reached over with another full plate of creamy oeuvres which he emptied into the void.

While I momentarily stood speechless, the man pressed his hand against my pastry filled cleavage and massaged the goo all over both boobs. He looked to be thoroughly enjoying his copping a great feel of those twin globes.

My reaction was automatic. I delivered a stinging, open handed slap to his face. Just as quickly, he turned my head with a wringing slap of his own.

I leaned forward, hands on hips and glared at him. He reciprocated. We stood then, literally, nose-to-nose with our hands on our hips, glaring red faced and angry at each other. Well, I was angry. He just mocked me but kept breaking into that silly grin.

A crowd now stood around us, frozen into poses of fright and horror and just staring dumbly at us. There was a long, pregnant pause. Would the volcano blow?

Simultaneously, we began to crack little smiles. Then big grins. Finally, we broke into guffaws of laughter, side splitting laugher that brought tears coursing down both our goo laden faces and cheering laughter from the relieved crowd. God, what a mess we'd made of each other.

"We're really into the Christmas spirit, aren't we," he finally said when he could speak again. "My name's Curt. What's yours?"

"People just call me Sissy," I responded. "It's just simpler than trying to use my Christian name."

"Well then, Sissy, shall we get out of here?"

"By all means. I was still scrambling to find an excuse to leave. At least you've now provided me with that."

Then, impulsively and incongruously, I blurted out, "Let's go to my place and clean up."

"Better mine, I can more easily replace my outfit at home than at your place and you can wear something of mine, a big shirt, maybe."


In the car, I finally thought to ask, "Since you were at the party, you must work for the company, but I've never seen you before. What do you do there? And, did you have your wife at the party? Where's she?"

"Slow down, Sissy and I'll tell you. First, I'm a thirty-four year old bachelor. Second, I do work for the company. I'm Director of Overseas Operations and work out of an office on the fiftieth floor. What about you?"

"Oh. I'm single and a bit younger than you. I'm Director of Domestic Sales and work out of an office on the thirtieth floor. I guess that's why I haven't seen you before."

"That and the fact that I spend a great deal of my time checking on things outside the country," said Curt.

We chatted about the party and the goings on there while we drove. God, for thirty-four, he's still a hunk, was all I could think about as we drove and chatted. Rugged good looks with brown, grayless hair accompanied his broad shoulders and drum tight abs. At least they must be drum tight if that elegantly fitted tux was any indication. Long torso and long legs added to the look. I wondered what else was big and long.

God, why are those kind of thoughts suddenly surfacing after so long?

My wandering mind was brought back to reality as we walked in the front door of his spacious town house and Curt said, "Why don't you go first. Strip out of those dirty things and take a shower. You don't appear to be wearing a bra and I don't have one to lend you, but I think we can get you one of my long sleeve shirts to cover your generous endowments pretty well."

Generous endowments, indeed! But I liked that he was obviously aware of me. "Show me the shower."

The main bathroom amenities were located in a first floor, huge room. A large double sink vanity and wall mirror occupied one side and a smaller room off to the other side with the pot. Further in through another door, was the shower. Holy Cow, what a shower. It was huge. Two shower heads occupied opposite end walls and four were spaced across the back wall. The entire front wall was clear glass which faced a full, mirrored wall across the room. A dressing bench was on the floor in front of the mirrored wall.

Curt left and I stripped. Standing naked in front of the mirror, I couldn't help turning and admiring my voluptuous curves. Late twenties peak of ripeness, I thought as my hands found my more than ample boobs and explored their fullness. As my tits responded, one hand dropped to my snatch, my bald, clean shaven snatch. I groaned aloud as my middle finger worked into my crevice and over my clit.

Over the past three years, since I'd given up men, I did the masturbation thing a lot and I couldn't help myself now. The anticipation of what was likely ahead tonight added to my sexual tension as my finger found the opening to my pleasure center and plunged into the depths. The copious presence of pussy juice sped my finger along, not to mention my desire.

My boobs tingled with fire enhanced with the actions of my right hand. My pussy tingled with even more fire with the action of my left hand. The tingling fire met inside my core and I climaxed hard. The water of the shower was anticlimatical, but it felt like heaven anyway.

After forty minutes in the shower, including another climax, I stepped back into the dressing area and dried myself. The hairdryer was a Godsend. I also found the long sleeve, white dress shirt Curt left for me. The shirt was long enough to more than cover my ass and pussy. Well, we'll see about that!

I left the neck button and three more down undone as well as three up from the bottom, stepped into flip-flops left for me, and walked out into the hall.


"I'm in the study."

I walked to the doorway and struck a sexy pose.

"My, my, that shirt certainly looks better on you than it does on me, Sissy. I'll go and shower and then rejoin you in here. I fixed you a drink. Just took a chance on what you might like."

My rum and coke was just what I needed while I waited--and contemplated the meaning of those sparks of sexual electricity that both of us had obviously felt in front of that hors d oeuvres table. Those sparks were still crackling between us. In fact, I think I glowed more than the Christmas tree across the room.

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