Doin' the Boss: Babysitting

This is the third installment of my on and off affair with my now former boss. We worked together for two years before I ended my affair with the man 12 years my elder, only to rekindle our relationship over the Christmas holiday. For those of you who have written nice feedback, THANKS! For those who insist that I am a loose morals slut, you are entitled to your opinion. At your request this story is about a babysitting assignment I had about a year into our relationship.

I’m not proud I was involved with a married man. It wasn’t something I had planned, but the fact is I did seduce my boss, K. Lawrence Little, the Vice President of a bank Credit Department. I am not proud about it, but I do admit to having this relationship with then man who is 12 years older than me.

It wasn’t planned, but while we were in the throws of our relationship, it was surely red-hot.

In the last two installments of my chronicling of this affair I’ve described how we met, how I seduced him, how he later led me on and how I dumped the married man with a family. I also described how we had gotten back together for some raunchy sex on Christmas Eve, 2002. Along the way I’ve discussed how I continued to date other guys while secretly meeting my boss in a variety of locations for sexual escapades. My other boyfriends had no idea of my relationship with my boss, nor did his wife have any inkling of his infidelities.

I mentioned a few of our, uh, activities, and how we’d have escapades in various locations. One such adventure that drew several requests from readers for me to reveal was my night of babysitting.

Now, on the surface it was innocent enough. Mr. Little and I had been meeting, first in his office, then, after his concerns of being caught in a compromising situation at work with his administrative assistant, we moved most of our liaisons to his car or various external locations. I have to admit the baseball dugout at lunchtime on a workday was quiet exciting given the number of people who were in the vicinity. But the babysitting assignment and resulting activities that evening were superbly erotic and supplied some of my hottest memories of our affair.

Mr. Little and his wife Mary had long been scheduled for an evening charity event at the Philadelphia Art Museum. It was always strange for me, working for the man and dealing with many of his personal issues while at the same time having an intimate relationship with him.

On this particular day all seemed well until I answered his telephone at about 4 p.m. on the day of the Art event. “Mr. Little’s office, may I help you?”

“Robyn, it’s Mary,” said a frantic sounding woman. Mrs. Little had been married to my boss for 15 years. She regularly called him at the office, and knew her voice by heart. The woman was about 5-6, just a bit taller than me, with auburn hair and a never-ending bright smile. I may have outweighed her by a smidge, but then, my 34c top was definitely bigger than hers.

“Oh hi Mrs. Little, how are you?”

“Not too good, Robyn” she despairingly replied. “Tonight’s the charity event and my babysitter just cancelled. I’ve been frantically trying to find a replacement but I haven’t had much luck. Lin is going to be so upset, he was so much looking forward to our evening. He likes rubbing arms with all those dignitaries and celebrities.”

I’m not sure why, but after a little more talk I mentioned to Mrs. Little that I was available that evening for emergency duty if she needed me to watch the kids. While she first said no, I eventually convinced her that it would be fine.

When I told Mr. Little that’s I’d be watching his kids that evening, and that maybe he and I could get a little time together for some special payment he laughed and called me incorrigible. There was just something very hot about being inside “her” house taking care of “their” kids!

I arrived on schedule at 6:45 and was greeted first by Mr. Little and then his lovely wife. Mary Little was wearing a slinky black cocktail dress that accentuated her modest curves. Her makeup and nails were immaculate. Around her neck was an exquisite diamond pendent necklace. She looked every bit the perfect wife.

After leaving me with detailed instructions, as well as $25 for the pizza delivery person, the couple left for the charity event. As they left Mr. Little told me to “be good” and I told him to have a great time. He winked at me and mouthed the word “later” as he exited his house.

I hadn’t babysat for years, but any worries I had about the kids being misbehaved soon dissipated. They were perfect angels and even went to bed right on schedule, leaving me to watch a romantic comedy on HBO. Oh, I did look over their videos to see if there were any nasty ones around, but most were of the PG variety.

I couldn’t help visiting their bedroom, where I found Mrs. Mary Little, the perfect suburban spouse, had a nice lingerie collection, which surprised me because my boss had mentioned on several occasions how plain Jane his wife was. I guess the man was entitled to a few “secrets”.

At about 11:30 I heard the front door open and Mrs. Little ask if I was “decent”, of which I laughed and said “of course.”

“Just didn’t want to walk in on you and Luke,” she said, mentioning the name of my current beau. “I can remember babysitting assignments of my own! Remember Lin?”

My boss chuckled as he hung up their coats. I mentioned the kids were adorable and perfect all night, and the couple each thanked me for filling in at such late notice. After some small talk Mr. Little said he’d walk me to my car. “Okay, honey,” said his wife, “I’ll be upstairs getting ready for bed. It’s been a long night. Thank you so much Robyn for helping us out in a pinch.”

On the walk to the car Mr. Little stunned me when he asked if I wanted to meet him for a quickie. Before I could protest, he added that he’d like to meet in his basement! I was intrigued and suddenly excited with the thought, to say the least. “How are we going to manage that?” I quizzed. “There’s the little matter of your wife!”

A big smile came to my boss’ face. “Where there is a will, there’s a way,” he said.

He looked up at the house, then back at me as I entered my car.

“Mary will be heading off to bed soon, she kept saying how tired she was at the affair,” said my conniving boss with the dirty mind. “ I’ll meet you at the basement door. To be on the safe side wait out back…there are a couple chairs there. Just drive up the street and park there for 15 minutes or so, then walk down the alley to the back gate. Come up to the house and wait for me near the basement door. I will join you when the coast is clear.”

I hesitated, thinking only of the dangers. But it was the basement, two stories away from where his wife would hopefully be fitfully sleeping. The thought of blowing my boss in his own house while his wife was in residence had a certain titillating aura to it, and after a small bit of deliberation I finally agreed after telling him to make sure she was down for the night before even thinking about coming to meet me.

Doing precisely as he advised, I drove up the street, found a parking spot and waited a bit before slinking back down the back drive, staying in the shadows, and making my way toward his two story, quaint, suburban house. I quietly opened the rear gate after ascertaining the upstairs was dark. The moon lit my walk toward the back door, which, sure enough, was slightly open when I arrived. I didn’t dare go in, choosing instead to be safe and wait where I could quickly make a getaway if need be. Mr. Little wasn’t around, but soon I heard him open the door and whisper that the coast was clear.

Mr. Little said Mary was soaking in the tub, and if past practice were followed would head directly to bed from there. The man smiled, then drew me into his arms and passionately kissed me. We held the kiss for a bit as he began fondling my body. First he caressed by breasts, and then began gently rubbing his hands on my ass. “I’ve been thinking about this all night,” said my boss, stroking my hair away from my face. “I want you so much. I got a hard on thinking of you when we were sitting with some folks eating hors d’ouvers.”

After a few minutes or foreplay and small talk, we broke our embrace and slipped over to the fluffy basement couch. We kissed some more as Mr. Little’s hands roamed my body. As he began fondling my breasts I unleashed his manhood from his bulging pants.

“Um, what have we here?” I wantonly cooed, stroking his dick. “Is this for me?”

“Oh, Robyn, your hand feels so good, I love it,” said my boss as I continued playing with his cock. I caressed his dick for a while as we continued to kiss, then slipped onto the floor, planting my knees on the hard surface and moving around to face his midsection. I looked up at the man and smiled.

“Do you want me to suck this?” I questioned, knowing the answer in advance.

My boss groaned out a “yes” as I began licking his dick all over, bathing it with my tongue. Once it was good and moist, I lowered my lips and began sucking it to its full hardness. I remember thinking how much I enjoyed hearing Mr. Little’s enjoyment of my oral sex technique. The man absolutely loved blowjobs, and I was happy giving them. The fact that we were in his basement while his wife slept upstairs made the act even more exciting.

There was always a challenge in sucking his dick. Oh, he loved me performing for him, it was just a question of whether I’d slowly tease and bring him off slowly, or work double time and cause him to explode fast. I think that’s why he loved it so much, because each time I would try to do something little different. A little twist here, a little pull there.

To this day I receive a great deal of enjoyment in sucking the man’s dick, but on this night I was tingling. It was so hot kneeling between his legs, fingering myself over my jeans as he writhed and groaned above me. His midsection bucked against me as I blew him, and I knew he was close to cumming. Mr. Little was lost in the joy of having his dick sucked, but a creak from above pulled my mouth quickly off his dick.

“What was that?” I shockingly quizzed, pulling back from his pulsating cock.

“It’s nothing,” he replied, attempting to pull my head back onto his knob.

“No, really Mr. Little, I hear something!”

This time he heard it too, a walking sound. It was a good think he had hardwood floors above, because a cushioned carpet would surely have spelled disaster. He quickly pointed to the storage room steps away and told me to get inside, my exit out the basement door blocked by the possibility of the intruder coming down the steps. “Quickly!” he motioned, putting his finger over his mouth to ensure I was quiet. No kidding, I thought, as I slipped into the dingy room and sat on the floor after closing the door.

I heard Mr. Little start up the steps, where his wife apparently met him. “Hi honey, I thought you were sleeping,” he said.

“I was waiting for you, mister. Where have you been?”

“Uh, just watching some television. But I’m ready for bed now. Let’s go upstairs.”

There were some hushed tones that I couldn’t hear, but I did get the gist of it. The little woman wanted a little lovin’, and had been waiting patiently for her husband to give it to her.

“Well, sailor, want a show a girl a good time?” teased my boss’ wife. “How about here in the basement? I hear you guys on leave like it any way you can get it. Fifty bucks and you can have me any way you’d like!”

There was a bit of uncomfortable laughter as Mr. Little mentioned that the bedroom would be more comfortable, but Mrs. Little had other ideas. I couldn’t see what was happening, but I could imagine. After a couple minutes, and after my boss thought ahead and turned on a romantic CD, I became brave enough to peer through a crack in the wall at the basement. In the dim light I spotted the married couple in a lip lock on the same couch I was sitting on minutes before.

Mrs. Little was wearing a bright red teddy with matching lace-topped stockings. There was no doubt she had been waiting for her husband before taking matters into her own hands. I sat, quietly, in envy of the woman. She had pushed the man’s head down between her legs and he was licking her pussy while reaching behind and fondling her ass. “Oh honey,” she cooed. “I was so hot for you all night! You looked so handsome.”

My bossed laved his wife’s wetness for several minutes before moving up to her mouth to kiss her once again. She reached down and unzipped his pants, slipping them down his legs as he continued the kiss. Mrs. Little then lay on her back and told the man to go down on her…and he complied. He sucked her for a few minutes before she reached down and pulled his cock up toward her mouth. My boss kicked off his pants then moved over her face. Soon the couple was locked in a passionately wet 69.

I watched as the married twosome licked and kissed each other’s genitals, and I have to admit I was both excited and jealous at their sexual display. Mr. Little continually told me how his wife didn’t like sex, but this woman was nowhere near the cold fish he had portrayed. She was sucking his dick like a pro, while enjoying his tongue on her pulsating pussy.

“Fuck me,” commanded the wife, breaking their coupling. “Now.”

Mr. Little moved around and began rubbing his dick up and down his wife’s crack. He teased her before inserting his cock into her soaking wet pussy, bringing forth a satisfying, throaty groan. My boss began rocking in and out of his wife as I watched the coupling from barely 20 feet away. I couldn’t spy nor hear everything that went on, as they slid around the couch and later slid down to the hardwood floor. But suffice it to say I probably could have made all the noise in the world and neither would have known so lost were they in their coupling.

Needless to say I kept as quiet as a mouse as I played a backroom role in a voyeuristic play. He pumped into his wife hard, as his white ass recoiled then thrust in tandem to her pushing. Every now and again I’d twinge when the woman would slap her husband’s ass or he’d instruct her to move faster or slower. Soon their work paid off, as Mrs. Little informed her pumping lover that she was about to cum.

“Cum in me, Linny, give it all to me!” the woman demanded. I heard her moan as my boss pumped a load of sticky sauce into her wifely pussy.

The two held each other for a bit, kissing and cuddling before Mrs. Little broke the embrace. “That was incredible,” said the woman, who was still short of breath. “I hope we didn’t wake the children.”

My boss mumbled something as the two stood. “Head up to bed honey, I will make sure everything is locked up,” said my boss as they rose the stairs. I waited for a bit, not wanting to get caught in an unexplainable act. After all was quiet for a bit I heard the upstairs door open and I cringed. But it was Mr. Little, who looked embarrassed by the entire situation.

“I couldn’t help it,” he said, head hung low. “I’m so sorry.”

“Don’t worry about it, Mr. Little, she is your wife, it’s allowable,” I responded. I truly think he was afraid I might scream or worse. I just wanted to exit the premises while I was still in one piece. I kissed the man and quietly said good night before striding toward the basement door.

“Wait a sec,” said my boss, willing me over toward him. “Come here, I want another kiss.”

I think he had already overdosed in the kissing department, but I complied. We kissed for a couple minutes before coming up for air. Once again I was tingly, and I mentioned to Mr. Little how hot it was watching another couple having sex. While I would have rather watched someone other than my lover banging his wife, I had to admit to him it was hot watching him in hot action with the woman.

We kissed once more and I was stunned by the firmness in Mr. Little’s pants. His dick was getting hard again!

“Please, Robyn?” was all he said.

I couldn’t help myself. Thinking back, I can’t imagine how he got me to do it. For the second time that night I slipped down to my knees and unleashed my bosses six-inch dick from his pants. I began sucking his cock as it expanded into my slurping mouth like it had dozens of times before. I tasted his wife’s cunt on his dick, a sort of tangy mixture of pussy juice and cum sauce. I swirled my tongue around and cleaned his dick of the sticky stuff and then began bobbing my head on his expanding dick.

My boss wasn’t super hard, but he obviously loved the oral attention I was giving him. It was quite odd, sucking on a semi-hard cock that had been satisfied minutes before by another woman’s pussy. At first I felt a little humiliated, but then I realized how much of an effect I was having on this man. How his dick was growing in my mouth so soon after having shot its sauce in her sex.

Mr. Little whispered how much he loved my mouth, how he loved me to blow him. I told him his dick was wonderful, and rubbed it along my cheeks to emphasize the point. He patiently watched, then held my head firmly in his hands as he rocked in and out of my sucking mouth. His dick soon began pulsing to the movement of my lips and I realized that while his wife and fucked him he wasn’t completely drained. I backed off his cock and began licking below, savoring each of his balls and the sack that surrounded them. I kissed the underside of his dick, then slowly licked from the bottom to the tip of his cock several sensuous times. Then I began to suck his dick with fervor.

“Oh Robyn you are such a great cocksucker,” he whispered. “ Don’t stop.”

I’m not sure I had a choice, for if I wanted to remove my lips from his dick I would have needed help. The man was gingerly fucking my face like a man who hadn’t had sex in months. Knowing his wife had fucked him just minutes before incented me to work hard and satisfy his beastly urges.

Soon I was rewarded for my efforts as Mr. Little began rocking faster in my mouth. He muttered and groaned as I blew just the top half of his dick, stroking the lower half with my hand. As one might imagine, he soon reared back and began firing shots of cum into my sucking mouth. It wasn’t a copious load, and the tangy spurts were quick to subside. He remained in my mouth as I sucked him clean, then he helped me to my feet.

He hugged me, and then told me he’d see me Monday morning. “That was incredible,” he quietly said as I kissed him on the cheek. “You are a sweetheart. I’d like to hold you for a while but we better not chance it any more.”

Uh huh, Mary might wonder where you are, I thought. Then I smiled to myself, wondering what she’d get if she wanted seconds. That thought stayed with me all the way home, and I got myself off while thinking of her trying to get his dick hard again.

Monday morning there was a fresh bouquet of roses on my desk.

“Did your wife have a good time Friday night,” I asked.

Mr. Little smiled. “Uh huh, she had a great time. And I had a wonderful time too.”

I smiled back at my boss. “Me too!”

Later that morning Mrs. Little confirmed that she had a great evening, and couldn’t thank me enough for filling in as a replacement babysitter. “You are a doll,” said my boss’ wife. “We had a great night at the affair, and the evening got better as it went along…” Her voice trailed off, saying nothing but implying, girl-to-girl, that she had had some bedroom excitement upon their return home.

If only she knew!