The Actuary Couldn't Figure Pt. 02byJRob©
(Part one of this story gave the background of my helping the Head Actuary who handled our business account out of a career wrecking jam. As payment for the miracle I worked to save her ass, she was going to repay me by giving me her virgin ass. Please read the first installment for all the details. Enjoy.)
Once Stephanie reluctantly agreed to seal our deal, I had to figure out a way to get my payment for saving her job and career while not drawing suspicions from co-workers and her inquisitive husband. It was not an easy task.
I schemed for the 48 hours, trying to find the perfect spot for our romp. Her house was too dangerous, too many spying eyes, and there was no way my roomy would be quiet if I brought her to my place. Then it dawned on me.
There was a swanky resort about 40 miles away, the one complete with a full spa, and didn't Stephanie deserve a little rest and relaxation after having worked so hard in recent weeks? And it catered to, shall I say, an older crowd. Don't think there would be a lot of family friends of either of us happening to head there for a spa vacation.
Make a few calls, got the special off-season rate for Friday and Saturday nights, heck, it would be worth it.
Called Stephanie and outlined the details. We'd meet after work at the resort at 7. I would have already checked in, and she'd merely meeting me in the lobby. We'd have dinner, a couple drinks, and then travel to a more erotic place.
The week went by in a flash. On several occasions Stephanie attempted to talk be out of it, but, well, a deal is a deal, right? She wasn't happy, but, by the same token I had gotten her off the hook, saved her job, helped her get a big raise all while putting my ass on the line.
How appropriate she had to put her ass on the line.
I know that over the months since fixing the problem I'd had a special affection for her ass. It had always bedazzled me, but given the situation I found myself sneaking peaks at her when she walked the hallways. I'd fantasize about that ass, knowing that there was a great chance I not only would be seeing it bare but also banging it bareback.
Still, I thought she might back out of the deal. So when I noticed from the bar that she was walking through the front doors of the resort I couldn't help but smile. She looked wonderful. She glanced around, not seeing me, and walked around the lobby. That gave me a good view of her swaying ass.
After a bit I sauntered over to her. She was sitting awkwardly in the lobby, attempting to make busy with her phone, but I could see her eyes darting to a fro as she looked for me. When she saw me, our eyes met, and I swear she shivered a little at the sight of my presence.
"Good evening, Rob."
"Hello, Mrs. McCann, how are you tonight?"
She looked around, and, seeing nobody within hearing distance, spat her answer. "How do you think I am, you bastard? I don't want to be here."
"But you are, Mrs. McCann, you came here of your own free will," I said with a smile. "Come on, it's not that bad. This is a wonderful place! Lots of cherry and mahogany. And speaking of cherry, how's that ass of yours?"
The woman started to smack me, but thought better of it. She clenched her fist, screwed up her face, and saw back into the large stuffed arm chair with the realization of our little deal was going to be satisfied.
"Let's get it over with," said the woman. "This is not, as you say, by my own free will. You are forcing me."
Smiling, I handed her a heavy metal room key.
"We are in suite 309. Why don't you change into something for dinner? I will be up in a bit, but our reservation is for 8:15 so don't dally."
I think she thought I'd take her right to the room and bang her, so the dinner and lack of pawing through her off her game. Resigned, she mentioned there was an overnight bag in her car. Taking her car key, I said I'd get it.
A few minutes later I entered the suite and head the water running in the expansive bathroom. It was a bathroom for a queen, complete with a large bathtub, shower, bidet, two sinks and make up table. It overlooked the fields behind the hotel, and since we were in a high room one could prance around undressed and not be seen from outside.
Knocking on the door, I said I had her bag. She demurely opened it, hiding behind and reaching out, and I gentlemanly looked away as I held out the bag.
She said she'd only be a few minutes, but 15 minutes elapsed before the door opened. The wait was worth it. She wore a light blue dress with black stockings. The top was cut low, accentuating her breasts, and a large golden necklace graced her neck. She looked adorable and sexy.
Complimenting her on her taste, we escaped the wonderful suite to the grand ballroom where dinner awaited. I won't bore you with the details, but let it be known that her plunging neckline was noticed by both men (who stared) and women (who growled at their husbands). Being in love with Stephanie's ass I hadn't really paid a lot of attention to her breasts, but they were on display like fine diamonds at a museum.
After dinner we strolled the grounds of the resort under a near full moon, pausing at a gazebo adjacent to a lake to sit for a spell. As she had numerous times before, Stephanie attempted to get me to let her off the hook. She pleaded, throwing out her husband's honor, her kids' move and you name it.
I halted conversation with a reminder that a deal was a deal, and that she wasn't little miss innocent. She screwed up royally at work, and then sucked on my dick on several occasions over the last months. Not exactly a perfect wife and mother, now, was she?
We headed back to the suite, entering about 11.
She wasn't going to hear the executioner's song, but it appeared as if she thought it was the same thing.
Into the bathroom she went, and when she came out she looked adorable: A red baby doll nightie, with red panties underneath, and nothing else.
I had changed into pajamas, dark red if you must know, and led her to the expansive bed. Shutting off the lights, I slipped inside the covers and slid over to her.
"I had a great night, Stephanie, thanks for the good time."
"Are we going to...uh...you know?"
"Patience, Stephanie, patience. We've had a long day. Let's get a good night's sleep, why don't we."
You could sense the reprieve hitting her. I swear she exhaled a deep breath.
"You know, Stephanie, I sleep better when I'm, uh, not horny. And right now, with you in that wonderful nightie, I am very, very horny."
"I should have known," said the girl, reaching over to caress my dick. "Men!"
Stephanie slipped under the covers and played with my cock for a while, slowly stroking it to full attention. I couldn't see her, but that was okay, the sensations were intense as I could only tell by feel what she was doing.
She got me hot as a firecracker and nearly brought me off with her hands. When she finally locked her lips to the tip of my dick it took every bit of control I had not to immediately cum in her mouth.
Still, I couldn't have lasted more than a minute before she stroked and sucked the cum sauce from my cock into her wet, willing mouth.
"That was incredible, Stephanie," I cooed as she moved out from under the covers.
She didn't say anything, just moved up, fluffed her pillow, and then turned away from me. If she did this move to let me know she wasn't happy, her attempt failed. Because when she turned away her ass was right next to me. That perfect ass.
Sliding over behind her, I settled my spent cock into a wedge of her ass, then moved an around her. I had held her all night long.
The following morning I woke her at 7, ordering her up.
"What, what?" she questioned, rubbing her eyes...
"You have a spa appointment at 8, and breakfast will be here in 10 minutes. So, unless you want to let the delivery boy see you in your sexy undies I suggest you get up and get ready."
Knowing full well I'd open the door to food whether she was partially clothed or worse, she escaped to the bathroom. Inside, she called out. "Spa?"
"Yes, you have an appointment for the works. You deserve it."
"You never cease to amaze me," was all she said before the shower started in the marble bathroom.
Little did she know, as I was setting her up for a fall from my perspective. I just thought that if she was in a decent frame of mind she'd be more compliant. I know, I had the goods on her. Why else would a happily married woman be in the hotel suite of a co-worker? Still, I wanted a perfect weekend for me, of course, but wanted no repercussions down the road either.
As she showered out breakfast came and I opened our curtains. The view of the gardens and distant hills (okay, we call them mountains, but anyone from the West would call the molehills) and the wonderful morning. Opening the sliding door brought in a bouquet of smells from the garden that was more than pleasant.
Stephanie hadn't lost any of her modesty, re-entering the room dressed in sweats, looking wonderful in them. Not a bit sexy, more motherly, but that's okay. I'd get to see all I wanted in time. We shared coffee and assorted rolls before she whisked her way to the spa for her treatment while I prepared for my own treatment of her upon her return.
Thinking of that wonderful ass, I wondered how hard it would be to conquer. I mean, she had agreed to give me her ass, but that didn't mean it would be easy and I wasn't an expert as fucking an ass.
Still, she was going to do what I told her, so my preparation was merely to have lube ready to help the task. It didn't hurt that I'd received a handful of blow jobs from the woman over the last few months. They went a long way toward settling the ledger of me helping her out of the numbers jam at work.
The nice thing about small digital cameras is they can easily hide between books and knick knacks on the wall shelves. I pointed the camera at the table where we had breakfast and smiled. What a perfect scene!
Monique called from the spa just after noon. "You're, uh, wife just left. Have fun."
I had told the spa staffer than Stephanie had needed a break, and that we had needed some quality time together. I let her know that Stephanie would be, uh, spending the afternoon in bed. Stephanie had received a massage, seaweed bath and facial before a bikini way and a second massage. Three full hours of pampering before I ravished her.
I flipped on the camera when I heard her key in the door.
"Oh, that was marvelous," said the naughty Actuary. "I think I will change and head down to the pool if that's okay with you."
"In a couple minutes, Stephanie, I had a something else in mind..."
She nodded, mentioning she figured I'd want a little afternoon delight. Like the perfect woman, she walked over and dropped to her knees and began to unbuckle my pants. Reaching into my boxers, she pulled out my cock. "Maybe this will get you in the mood to join me at the pool."
Hum, that was a good thought. I watched as the woman licked my dick hard, and then began sucking the tip. She worked her tongue over and around the tip of my cock before tightening her lips and slowly working my cock into her mouth. It was as if her lips were locked to my dick, and the sensations were mind blowing.
Stephanie worked my dick for several minutes before I pulled her to her feet. "I want to see you ass and touch it before I finish in your mouth."
She looked questioningly at me but moved to my prods toward the breakfast table. Turning her toward it, I pushed her over it and slowly lowered her sweatpants making sure I held the cheeks of her ass as I pulled down the cotton covering. I left the sweats around her ankles, and then began lowering the flimsy red bikini panties.
Dropping to my knees I began playing with her ass as my head bobbed toward it with kisses. I kissed each square inch of that perfect ass, spending some time in the cleft.
"Be careful back there, it's sensitive," said the woman as my finger slid up and down between her ass cheeks.
Licking that perfect ass was very erotic. My dick throbbed and I knew what I wanted.
I heard her say she'd finish me off before she went to the pool, but it wasn't a blow job I wanted. I rose while keeping a hand on her back. "Gonna rub against you and cum," was all I said. I think that lowered her guard, because she didn't argue when I held open and played between her ass cheeks with my cock.
"You have such a great ass, Stephanie, I love looking at it and feeling it," I said as I worked my fingers around front of her and then up and down her wet slit.
"No pussy, Rob, remember?"
She wasn't emphatic, but I said of course I wasn't going to fuck her precious pussy. I wanted to play with it, which I did, bringing out a moan when I slid my fingers around her clit.
"Oh, that's hot," cooed the girl. "We shouldn't be doing this. Oh."
Of course we shouldn't be doing this. She was married, but she was also in Dutch to me because of her mistakes at work. She was here because she had to be, and while it was totally wrong I think she actually thought I was a nice guy.
While bringing out the soft moans from the girl I maneuvered behind her. I rubbed my dick all over her backside, pushing under to get some of the wetness from her pussy on my dick. I told her I wouldn't be fucking her ass, at least not now, and that gave her some relief.
And then I pushed my cock against her ass hole. I pushed a little, and then stabbed at it, pushing with all my weight.
"Ah, you bastard," screamed the woman, "Stop it! Don't!"
I pushed down on her back while continuing my push at her ass hole, hearing a distinctive "pop" as I got past the sphincter before pausing.
The girl started to scream but I grabbed a napkin and held it over her mouth. She attempted to push back and push me away but I was like a boulder. My cock was wedged inside her ass and I pushed harder.
The groan that came from her came from deep inside. It was like a caged animal, growling to scare me away but I wasn't budging. I remembered I hadn't lubed up my cock, but, well, the opportunity presented itself and what could I do? Really, what could I have done but push into her asshole?
Glancing down I saw her trying to kick out her legs but the sweat pants around her ankles kept her secure. She attempted to slap back at me but with my full weight on her there wasn't room to make a swat with any power. And with the napkin cloaking her screams she couldn't cry out.
All that was left was for me to push further inside her ass, which I slowly did.
Inch by inch I pushed inside her ass. With each inch came more of a groan from the girl. It was more than erotic, it was fantastic. Her ass hole was perfect, and I loved moving into it. When I was in several inches I moved back a little then pushed more inside.
Soon I was fucking her right up her pretty ass.
I had no experience in ass fucking. Heck, I hadn't had all that much experience in fucking in general. But the sensations as I moved in and out of her ass were awesome. I moved my hand away from her mouth so I could get a little more leverage to push inside and she didn't scream.
"You're a bastard, you fuck," said the breathless girl. "You promised you wouldn't."
I just kept fucking her. In and out I went, and after a bit I swear Stephanie began to move with my motion. That was a ruse, though, as when she thought my defenses would be down she pushed back with her all in an attempt to get away. Luckily, I was able to repel the move and I thrust her back down on the table and pushed with my all into her ass.
Balls deep, I skewered the woman on my cock and held still inside her. Every inch of my dick was in her bowels and I remained still as the girl tried to push away from me. Her actions brought sensations to my dick never felt before. Oh, I was fucking her in the ass, but it was she who was doing the fucking.
The woman growled all kinds of curse words, curses I would never have thought she would have known. Curses which, if they could have been magically granted, would have left me ball-less with a chopped off dick.
I just smiled and fucked her up the ass, making sure the camera was catching the action and giving it a big thumbs up.
"Oh, you are killing me, you are killing me," cried out the girl as I wedged my cock into her ass.
I started thinking of her husband and it brought be down from shooting my load. I guess I could have thought of snakes or something, but instead I thought of her husband. I was getting something he never had gotten, Stephanie's perfect ass. Still, the thought of the guy finding out quickly brought me a little down from a high.
That only lasted a few seconds, because then I thought of how hot it would be for him to find out that his little lovely wife was being fucked in the ass. Would he beat me up or her? I smiled as I knew our little secret would be safe. Stephanie would never tell anyone about this act. Heck, then she'd have to admit to screwing up the company books, blowing me at will and getting her as fucked to boot. No, our secret would be safe.
Fucking the girl harder I couldn't help but drive myself over the edge. I truly wanted to make this moment last forever, but Stephanie's ass was just a master of my dick. I may have wanted to hold back, but her ass had a completely different idea. If I hadn't known better I would have thought her ass was milking my cock.
No thought or action could stop me from cumming. As I fucked her ass I felt the cum boil from deep in my balls. My dick began to erupt its sauce deep in her bowels in quick, firm spurts. I emptied my balls in her ass and continued to fuck her now moist ass hole for a minute or so before my dick began to come off its assfucking high.
Holding still inside her for as long as I could, I began stroking her back and up toward her head. I played with her hair and told her how wonderful the fuck was. I reminded her a deal was a deal, and that it was well worth the wait.
With a pop my cock moved out of her ass and I stood. Stephanie stayed bent over the table for a minute, gaining her composure I guess, as I stroked her perfect ass.
Soon she pushed her way to her feet and she reached back and calmly stroked her backside. "That hurt, Rob, that was awful. You are a real bastard."
"A deal was a deal, Stephanie,"
She turned and smacked my face.
Okay, maybe I deserved that. But I smiled.
"You are a bastard," said the girl, watching me smile at her while gliding backward away from any further Smack.
"I could make you blow me now,"
She looked aghast at the thought of putting her mouth anywhere near the dick that had fucked her up the ass.
Instead I reached out and took her to the bathroom. I drew a warm bath while holding her to me. "It's okay, it's over," was all I said as she cried on my shoulder.
I slipped off her clothing and helped her into the bath. She kept looking at my cock, a look that I thought was one of hate.
Leaving her to her own, I walked to the bidet and sat. I didn't want my back to the pissed off woman, but I did want to clean up. Fumbling around, I had never seen a bidet before, I figured out the faucets and began cleaning my cock. Lots of soap, I make it squeaky clean.
Then I walked over to the bath and got into the massive tub with the woman I had just fucked up the ass. It was quite a feeling. Sure, it was without her true consent, but by the same token, she was going to get it up the ass sometime that weekend so it wasn't totally unexpected.
All I knew was that it had felt tremendous. As I rubbed Stephanie's back I only hoped that the woman would make a mistake with the books once again in the future.