An Itch that Needs Scratching

This is a story of anal sex and cheating. If this is not of interest to you, please search the Literotica files. I'm certain there is something there that will interest you. All the people in this story are over 18 years old. No animals or humans were harmed in the publishing of this story. As always, constructive comments are welcome but there is enough negativity in the world to add any here. I have self-edited so any mistakes are mine alone.

An Itch That Needs Scratching

I pushed the flashing button on the intercom. "Sara, could please come to my office. I have something I need help your with."

"Sure Mr. Wilson, I'll be right there. But you do realize it's Friday and almost time for me to go home, right?" I couldn't help but smile a knowing smile.

"Yea, I know Sara but this is important."

"Ok, let me lock up and I'll be right there." I logged off my computer and locked the front door. I opened the door to my boss's office to find him sitting behind his desk without a shirt. His bare chest was broad and muscular. For a man in his 60's, he was still in very good shape. I knew it wasn't just his chest that was bare. I knew that before I saw the pile of clothes beside his desk that he was naked.

I began disrobing as I neared his desk. I added my blouse and skirt to the pile as I stopped next to him, now equally naked. There was no need to remove my panties and bra. They were in a drawer at home. You see, this was a game we played every Friday after everyone else left for the day. "So, Mr. Wilson, what is it that you need help with?"

Pushing back from his desk, he showed me. "I need help with this."

"THIS" was a large 8" uncut penis. I know it's length because we measured it one day after I teasingly told him I wasn't sure it was big enough for me. He swiveled his chair around to face me as I kneeled. "Sure boss, I think I know just how to fix this" I quipped as I took it in my hands.

I love uncut cocks. The soft smooth flesh of the skin that covers the firmness of the cock itself. How the skin slides down the shaft to expose the head when it peeks out of its cover. I willingly leaned forward and took the tip in my mouth. I love the taste, slightly salty with a hint of his man odor. I pulled the skin all the way down his shaft and sucked it into my mouth. The swirling of my tongue around it brought the expected moan from my boss. He loves it when I suck his cock.

And I love sucking it. I love cocks in general. I have sucked more than a few in my time. The way they fill my mouth. The satisfaction in the man's voice when he moans and groans. The way it swells in my throat just before it explodes. And the cum...OMG...I love the taste of cum. The more the merrier. When it fills my mouth to overflowing and spills down my body, soaking my tits I'm in heaven. I have had an orgasm myself just from sucking a big cock.

After slathering the shaft with licks and kisses I moved back up to the head. I slipped the skin back up the shaft until it formed a bit of a cup around the head. Then I ran my tongue thru the cavity I created, lapping up his pre-cum. This always drives my boss wild. I accepted the non-stop mummering as a compliment as the hands on the back of my head held me in place. "Oh my god, Sara. You know that drives me wild. Please stop before I blow my load. I have another place in mind for this load of cum."

I knew exactly where that place was and couldn't have agreed more. But first, another favorite of mine. I leaned back and motioned for him to bend over the desk. My boss has a nice ass. I separated his ass cheeks and licked him from his nut sack to the top of his butt crack. Then I curled my tongue to a point and pressed it against the opening. This brought a groan of pleasure from above.

I love eating his ass. His ass is just as firm and muscular as the rest of his body. My tongue worked on and around his asshole while massaging his ass cheeks. Alternately slurping and licking his asshole and probing with the tip of my tongue, I attacked with a vengeance. After a time, I reached between his legs and pulled his cock back to me. I slowly stroked it as I ate his ass. Then I added sucking his cock to the kissing, slurping, and tongue probing. "Damn it, Sara. You know that pushes me over the edge. If you don't stop, this load is not going to make it to its pre-determined destination."

But then, I knew that already. His cum tastes delicious and I had every intention of enjoying another offering. I stroked him and focused my tongue on breaching his sphincter muscle. I licked and probed until I felt my tongue slip inside. I knew he was close. Just before it was too late, I took his cock in my mouth and forced the middle finger of my right hand into his ass to the hilt. "Ahhh...damn you...I'm cummm...Aggggg..."

And then I got what I needed. His cock erupted and flooded my mouth with his delicious cum. I gulped and sucked, trying to keep from losing a single drop. And I almost succeeded. Only a couple of drops escaped and ran down my chin. I held the last mouth full and savored the taste before allowing it to slip down my throat. I held him in my mouth until if softened. Only then did I release it. My boss slumped against the desk to recover.

After he recovered, he stood and smiled down at me. "That qualifies as cruel and unjust punishment, young lady. Now get up here and lean over my desk so I can punish you properly," He joked. It was punishment I had been waiting for all week. I eagerly stood and bent over the desk, anxious for what was to come. What was to come was my boss's massive cock buried balls-deep in my needy ass.

You see, my boss is an insatiable ass man. Which works at great for me because there is nothing, I love more than having my ass stuffed with a big, hard cock. My boss, unlike my husband, is glad to fill that need. My husband thinks anal sex is disgusting. I knew that going into the marriage but was certain I could change his mind. I mean, what man wouldn't jump at the chance to fuck his wife in the ass. Especially a wife who begs him to do it. Well, I know one.

I reached behind me and spread my ass cheeks to provide easy access. Expecting his cock, I jumped in surprise when I felt his tongue press against my anal opening. As his tongue worked its way around my asshole, the fingers of his hand toyed with my pussy. A very wet pussy. First one then two fingers slid effortlessly inside me as he tongue-fucked my ass.

I was in heaven. My boss didn't eat my ass every time but when he did, he drove me crazy. He is good at his art. He apparently has had lots of practice over the years. It didn't take long for my first orgasm to hit. I pushed my ass back against his tongue as my body shuddered thru it. It was just a nice gentle release that warmed my body.

After another equally satisfying orgasm, it was time for the main event. "Please, John. I need you to fuck my ass." And he did.

Standing behind me, his now hard cock replaced his fingers in my dripping pussy. His cock felt good in me. He had, of course, fucked my pussy before. But most days, it was just used to lubricate his cock to aid in its journey to the depths of my bowels. That was the case today. We were past the need for preliminaries.

He held my hips as his cock pressed against my opening. A little more pressure and I felt it breach my anal opening and slip in. No matter how many times I feel a cock slip into my ass, that moment when it first enters is a favorite of mine. He knows it and paused briefly to let me enjoy the sensation.

Then, it's back to business. Inch by inch, stroke by stroke, my boss drives his flesh spike deeper, nailing me to his desk. And then, I feel his hips and know he has bottomed out in my ass. That's another sensation I love. Once again, John paused and allowed me to bask in the feeling of my ass being stretched around his huge cock. Then, pulling back, he reversed direction until just the head remained in me. Then it's back down my anal canal until I felt him once again bottom out. Then it becomes a repetition, in and out, in and out, each time becoming faster and more aggressive. I can feel an orgasm building way down inside the depths of my being.

The desk cut into my thighs with each thrust. My boss didn't care. Neither did I. The feel of his big cock in my ass more than compensated for whatever pain there might be. A brief thought about how I would explain the bruises to my husband was cut short when my boss roughly yanked me back against him, held me tight against him and filled my ass with his hot cum. I was close to cumming myself so that last slap of his balls on my pussy pushed me over the edge. My scream mingled with his moans as I joined him in release. His load filled me, then flooded out of my ass and spilled out on the floor next to his desk.

My boss finally pulled his softening dick out of my ass. It flopped, long and wet between his legs, cum still dripping from the tip. He stepped back as I turned and kneeled, taking him in my mouth to lap up the cum dripping from his flaccid cock. Once it was clean, he began dressing while I rounded up my skirt and blouse and did the same.

I gave him a quick kiss of thanks and turned to leave his office. "Same time next week?" he joked as I approached his office door. You see, since we had discovered our mutual need, Friday had become our weekly "scratch the itch" day. My boss, John Wilson, owns a small law firm. He has two other lawyers on staff in addition to him and I was the office manager / secretary / janitor in our little office. The office was usually empty by Friday afternoon, which worked out well for us.

Smiling back over my shoulder, I quipped, "You bet, unless something 'pops up' that you need some help with before then." He smiled a knowing smile. There had been times when Friday was too far away and we had to make different arrangements at one of the local motels, if you know what I mean.

I was pulling the door shut when he said, "tell my son to try and be on time tomorrow morning. Our tee time is 8:00 a.m. sharp." Yep, you guessed it, the man who fills my need and fills my ass weekly is my father-in-law.

_______________

My name is Sara Wilson. My husband, Sean, is two years older than me at 35. Having no interest in the field of law, Sean is a sales manager for software company. We have two young boys that keep us busy most days. Sean works from home when not on the road and I work at the afore mentioned law office. Sean is a big, viral, handsome man with the size and talent to keep a woman very satisfied in the bedroom. Except, of course, his refusal to fuck me in the ass. For some reason foreign to me, he has zero interest to the point of refusing to even consider it.

By the time we met in college I had been introduced to anal sex via a strap-on used by my roommate Liz and a couple of willing guys. She and I are from different parts of the country but hit it off immediately as roommates. Unlike me, she had previous experience with sex with other girls. Inexperienced but a willing student, she slowly and gently introduced me to that world. The final step being the strap-on up my ass.

We were in bed together one night was in the middle of a rather heated session. Liz had pulled out the strap-on that we had taken turns using it on each other over time. She fucked me to a few satisfying orgasms and we were cuddling when she said, "Get on your knees. I want to show you something one of my ex-boyfriends showed me."

Always up for an adventure, I readily complied. I was expecting a little doggie style action although that would not have been new. What Liz did next, caught me totally off guard. Kneeling between my legs, she spread my ass cheeks and buried her face between them. Her tongue zeroed in on my asshole. I jumped in surprise when she licked and kissed around the opening. That was a new one for me. No one had ever licked my asshole.

The closest I had ever come to anal sex was an occasional finger as Liz was eating my pussy but had never even thought about anything more in my ass. By morning my ass had been both eaten and fucked. I became an instant fan of both. It became a regular part of our fuck sessions.

I continued my training with a couple of willing boyfriends before falling for Sean. While both of them had good sized cocks they were more than willing to shove up my ass, that was about their only redeeming value.

Sean swept me off my feet and into his bed on the first date. Apparently, cock size runs in the family, as I would eventually discover. So does uncircumcised dicks. In fact, it was my husband's cock that introduced me to the world of uncut cocks and I became an instant fan.

We settled into suburban life and had the boys. Sean traveled a lot with work and I took care of the boys until they started school. Then I got bored and wanted something to do. And, no. Before you ask, I never cheated on Sean until...well, ya know...Unless you consider cheating using a couple of dildoes to keep my ass somewhat satisfied. Ok...ok...there was that one-time Liz stopped by on her way thru town while Sean was out of town. We had a passionate night of reminiscing, if you know what I mean.

_______________

About a year ago, John's previous secretary moved away and he offered the position to me. Things started out like any other law office job. Copying, filing, blah, blah, blah...the usual routine. John mostly hung around the office and let the other attorneys do the work.

My father-in-law was a good boss and easy to work for. The other lawyers, Raymond and Steve, liked him and everyone got along just fine. A weekly extended lunch at a local watering hole with the four of us became a routine when work permitted.

I had been there a few months when, just as we were leaving for one of those lunches one Thursday, one of John's clients showed up and said she needed to talk with John immediately. Cheryl Lawson was a prominent local business woman embroiled in a bitter divorce. Seems her husband, the local city manager was on his way to prison for embezzlement and Mrs. Lawson wanted to sever all ties with him before he went away. He, of course, didn't want the divorce so it had gotten ugly.

John stayed while the rest of us headed to lunch. After a quick lunch, I left Raymond and Steve with their normal "liquid desserts" and headed back to the office. I knew they would be there a while and I had some work I needed to finish.

Seeing Mrs. Lawson's car still in the parking lot I eased back into the office thru the side door so not to disturb their meeting. As it turns out, what I would have disturbed was not your normal lawyer / client discussion. The noises coming from my father-in-law's office had nothing to do with court strategy.

His office door was cracked open slightly. What I saw thru that opening made my heart jump. Mrs. Lawson was probably in her early 50's. The upper body I saw stretched across my boss's desk looked several years younger. She obviously took good care of herself. I had a flash back to my time with Liz and, for a brief moment, wished I was laying across that desk with her. I felt a wetness in my panties as I watched, unable to pull away from what should have been a private moment for them.

I should have quietly turned and snuck back out the door and left them to their "meeting". But you know I didn't. I was mesmerized, and turned on. The wetness in my panties was growing. Seeing my father-in-law naked for the first time was both disturbing and exciting. Disturbing because, well...he's my father-in-law and my boss. Exciting because I realized for the first time that he was a hunk. I had, of course, known he was a handsome man. But...damn.

It was apparent that they had no idea I was there. My boss had his client by the hips as she lay across his desk. Her and the desk shook each time he slammed into her. I had just gotten my hand under my skirt and into my panties when she had an orgasm. The shriek could probably have been heard on the street as her body convulsed. I felt my knees weaken slightly as I silently came with her. Holy shit that was hot.

Thinking the "meeting" was over, I was trying to gather myself. I had decided that I would go hide in the conference room to allow them their privacy until she left. I had just turned away when I heard Mrs. Lawson speak. "Oh god, John. That was great. I needed that. But you know what I really need. You know Charles is too much of a prude to do it. So...please John. Please stuff that big cock in my ass."

I suddenly felt faint. What?? A distinguished business woman and the wife of a city official likes being fucked in the ass? And, she was asking my father-in-law to do it for her? And she has a husband, or soon to be ex-husband, that wouldn't do it? I had found a soul mate, even though she didn't know it and most likely never would, we shared a common bond.

I almost tripped over myself turning back to the door. I got there just in time to see his client turn and kneel in front of him. I got a quick glimpse of his dick before she took it in her mouth. And what a nice dick it was. I guess size runs in the family. It did in this family for sure.

I was leaking again when Mrs. Lawson stood and once again draped herself over the desk. "Oh John, I need you in my ass. Please fuck me like you did before." And he did. My boss and father-in-law buried his cock in her ass to the hilt and pounded her unmercifully. He drove both of us to orgasm, me a couple of times, before he howled like a wild animal and emptied his balls deep in his client's bowels.

I was light-headed with lust. I hoped in an instant that their noise drowned out whatever noise I might have made. I staggered to the conference room and quietly closed the door. As I was trying to calm down and analyze what I had just seen and heard I realized she had said, 'like you did before'. This wasn't the first time my boss / father-in-law had fucked her.

I suddenly felt jealous. Yes, I realize my boss is also family. Yes, I know it could seriously jeopardize my marriage. Yes, I realize it is wrong to even think the thoughts racing thru my head at this moment. But...why not me? I like anal sex as much as any woman. Actually, probably more than most. Why can't it be me bent over that desk?

Those were the insane thoughts I was struggling with when I heard my father-in-law escort his client into the main office and out the door. Now I had to figure out how to get out of the office without being discovered. I couldn't let him know I had witnessed what took place in his office. I eased open the conference room door to find my boss leaning against my desk waiting for me. This was going to be a little uncomfortable.

"Hello Sara, you are back from lunch early." My boss / father-in-law stated the obvious. He seemed as uncomfortable as I felt.

"Yes sir, I had some work I wanted to finish and I figured the boys were gonna be there a while." I hesitantly looked at him as I spoke, not sure what his reaction would be.

"The Lawsons are long-time friends and Mrs. Lawson is going thru a rough time, what with her husband headed to prison. As you know, I'm handling her divorce. What you heard, and possibly saw, in my office was just two friends helping each other. Scratching an itch that doesn't get scratched at home, so to speak."

"Yes sir, I understand." What I really wanted to tell him was that his daughter-in-law has the same itch and I desperately need someone to scratch it since his son won't do it.

His next question took me by surprise. "You did watch, didn't you?" The knowing smile told me he already knew.

I wanted desperately to deny it but I knew it was useless. I couldn't look at him. "Yes sir."

"Ok, cut the Sir crap. And I thought I heard you at the door. By the way, you are kinda vocal when you orgasm." A huge smile covered his face as I lowered mine in embarrassment. "So...are you ok? You seem a little uneasy."