The Long and Winding Road

“Dave Jensen called this morning.”

“Dave Jensen? From work? What did that jerk want?” I managed around a mouthful of gluten free, heart healthy Cheerios.

“He wants to fuck me senseless,” revealed Sherry. “He said he’d bring Nancy Murphy along for you. He said Nancy agreed to your new rule of three times with the woman. He said she was probably disappointed it wasn’t five or six.”

“Shit! That asshole wants to sleep with you? I’ll have to nix this one. You will not be sleeping with that miserable fucker!” I stated emphatically.

“As I recall from seeing him at your Christmas party, he’s a dreamboat. You’re not ruling him out because he’s so good looking, are you? He used to play quarterback in college, didn’t he?”

“Yeah, for a Division II backwater school,” I quickly pointed out. “It’s all he ever talks about. Well, that and all the women he’s bedded over the years. He’s off limits.”

“You promised you wouldn’t rule out men just because they’re hunks!” protested Sherry. “You’ll be getting that Nancy from your work three times, so I think it’s a fair trade.”

“Nancy is the boss’s tight-ass personal assistant!”I protested. “She’s probably all dried up and dusty. I’ve never even seen her smile! Besides, I have to top off Brooke the next two nights.”

“Well I’m sure you’ll put a smile on Nancy’s face, at least three times,” replied Sherry. “I told Dave you had two more nights with a sexy coed before we would be free. He seemed impressed with that information and agreed to come over next Tuesday to stretch out my pussy.”

“Goddamn him!” I exploded. “He’s always bragging about all the women he’s fucked. He’ll tell everyone at work that he fucked you senseless.”

“And Nancy will be singing your praises. It seems like we both win,” responded Sherry, oblivious to my concerns.

I dreaded Tuesday more than I had ever dreaded anything, including the time I had to tell my dad I had smashed his sports car into a cement truck on Main Street.

“Jim! It’s good to see you. Sherry, you look fantastic. Your tits look even bigger than last time I saw you,” was Jensen’s opening gambit.

“Thanks, Dave. It’s probably the push up bra I’m wearing,” replied Sherry with a giggle.

At least Nancy had the grace to be embarrassed by Jensen’s coarse language and rude behavior. She blushed and shook her head in disapproval as Sherry grabbed Jensen’s hand to lead him to her lair.

I gently pulled Nancy toward the master bedroom. She seemed reluctant and I certainly wasn’t going to push her into anything she didn’t want to do, especially since I seriously doubted I wanted to do it.

We talked about our big project and the people we worked with. Nancy was a surprisingly good judge of character and pretty much had figured out everyone at work.

“I agreed to this for a couple reasons,” admitted Nancy.”The first is the one you probably guessed. I don’t get many dates and haven’t had sex in a few years, and it wasn’t very good for me when I did. Jensen told me about how you were trading turns with your beautiful wife for chances to bed other women. He dared me to be his partner in this, pretty much telling me it would be a real hoot if he traded my skinny ass for your wife’s amazing one. He seems to feel that Sherry is everything I’m not, and sleeping with your wife appeals to his warped sense of humor. Plus the fact he’s jealous of you.”

“I don’t think he’s jealous of me. He’s got the boss eating out of his hand,” was my reply. “He gets all the pussy he could possibly want, including my wife’s.”

“The boss may act like Jensen’s in the catbird seat, but you’re the one he relies on. Mr. Blake has often mentioned how well you carry out your objectives without constantly going back to him for guidance. Dave Jensen’s bluster hasn’t fooled Mr. Blake.

“You must know that Jensen’s going to do his best to humiliate and embarrass you at work,” added Nancy. “He’s not a friend or a gentleman. Everyone there will hear that he fucked Sherry and you went along with it. He’ll probably complain that she’s a lousy lay just to embarrass you even more.”

“Then why did you volunteer to go along with him?” I demanded. “You knew he’d use fucking Sherry to humiliate me. Why would you be willing to go along with the asshole? If he couldn’t find a woman to cooperate with this damn scheme, he wouldn’t be buried ten inches in my wife at this very moment.”

“Don’t blame me for your dumbass scheme! The truth is two other women at work wanted to be his partner for the swap. I just used the fact that I’m Mr. Blake’s personal assistant to influence that ass kisser to choose me,” revealed Nancy.

“Now I’m confused. Two other women were willing to climb into bed with me, but you used your position to get to the head of the list? That begs the question why. You’ll be humiliated at work, the same as I will. What could you have to gain from this weird agreement?”

“Jim, I know what everyone at work thinks of me. I’m the dried up spinster who never dates, dresses like it’s still 1950, and is either gay or asexual. My reputation can only shoot way up when they hear I’ve been sleeping with you. Being known as a seductress is a little farfetched, but I can at least shake the gay and dried up parts of my reputation.”

“You’re not unattractive and I would guess still under forty, so why don’t you go on some dates with single guys instead of getting involved in this cluster fuck?” I asked.

“Jim, no one has asked me on a date in four years and the last guy was creepy as hell. I’ve had a little crush on you since I was hired as Mr. Blake’s PA. This is my chance to finally experience a fantasy or two of my own. I’ll have some nice memories to keep me warm at night. I’ll be thirty-six in March, and people think I’m forty or older. I’ve got nothing to lose and some fun to gain.

“I’ve noticed that you aren’t exactly ripping my clothes from my body. Would you rather I went home. I know I’m in the same class as your wife. Hell, I’m not even in the same game,” added Nancy. “I had hoped for a mercy fuck, but I’ll understand if you simply don’t want me. It’s okay.”

Once again I was confronted with the insecurity of a woman. I never realized how many wanted and needed some sort of approval from the male of the species. I always thought Nancy didn’t care for male companionship, but apparently, that was not the case. It wouldn’t take much to totally destroy her confidence.

“Why are you still dressed? I thought we’d be having this conversation naked,” I replied as I began to undress while she watched.

“I’m not nearly as curvy as Sherry. Are you sure you want to see me naked?” asked Nancy. “Can I suck your beautiful cock before I get undressed? I may not be able to get you hard after you see me nude.”

That was the start of a really great evening. Nancy was smart and sensitive. Between her few sexual experiences and her vast collection of romance novels, she was a lot of fun. I not only got hard for her, but she got me off three times. She cuddled up to me and fell asleep after our lovemaking finally came to an end.

I was always a pretty early riser, but once again I found my bed partner had already departed the bedroom when I awoke. I found Sherry and Nancy chatting at the kitchen table.

“Where’s the miserable fucker you slept with last night?” was my first question to Sherry.

“He said he had to get to work early. Mr. Blake likes that he’s always on time or early for work,” responded a subdued Sherry. “He probably wants to be sure everyone hears about how his big cock stretched out my little kitty.”

I felt pain and despair at Sherry’s words. She seemed to be aware of the kind of guy Jensen was and how uncomfortable he’d make my life in the office, yet she had no problem banging the bastard.

“Will you be coming back tonight?” Sherry asked Nancy. “You still owe Jim two nights of pleasure.”

“Would that be okay? Don’t get me wrong, I’d love to come back tonight, but I don’t want to ruin your evening or interfere in your marriage,” replied Nancy with genuine concern.

“I don’t think you’ll be the cause of any problems in our marriage,” replied Sherry softly. “I think I can handle that on my own. Please come back tonight. I can tell Jim had a good time and you earned the pleasure of two more nights with him.”

Nancy had a quick breakfast with us and then left to go home and change her clothes for work. Sherry was quiet as I chomped on my Raisin Bran and read the paper.

Nancy spent the next two nights in my bed. She did her level best to convince me the people at work really weren’t calling me a fag cuck behind my back, but I knew better. The dynamics of the office had subtly changed.

For her part, Nancy admitted that some of the other women were asking her how she enjoyed sleeping with me and if I was as good as they thought I’d be. She had a great way of making me feel a little better, but I knew she was laying it on pretty thick since she knew I was fighting my depression.

I stopped at the grocery store Friday night to pick up some things for dinner. Sherry had promised her mother she would take her shopping for her birthday, so she’d be a little late getting home. I had learned to grill pretty well, so I was planning on steak and salad for dinner.

I pushed the cart around a corner and someone pushed their cart into mine. I thought some guy was jerking my chain a little until I saw the person with the cart. She was young and very attractive. Her blouse was just low enough to make you want to see more of her amazing globes.

“Jim? Is that you? I’m Glenda. I work with Sherry. We met at last year at the Christmas party, remember?”

“Of course I remember. No red blooded male could ever forget your lovely face, or other attractions,” I replied suavely.

“I’m so glad I ran into you,” Glenda admitted with a big smile. “Sherry and I work with a guy named Bill. He’s single and thinks he’s a real stud. He’s been trying to get into Sherry’s pants for the past year. Has she told you about him?”

“No, I don’t think she has,” I answered as my mind kicked this information around. Was this stud the reason Sherry decided she wanted some strange cock?

“Somehow, Bill found out about your famous Ponzi Pussy Scheme and asked me if I’d help him finally get into Sherry’s pants. I wasn’t too keen on it at first, but then I remembered how nice you looked at the Christmas party and thought it might be fun. Can we make an appointment, or whatever people do to get in on your famous scheme?”

“You’d need health papers and can’t be in a relationship with anyone, with the exception of Bill. You’d owe me three nights to his one and I have installed a new rule today. You will owe me three nights, but I retain the right to assign a person of my choosing to stand in for me. That means you may be sleeping with a total stranger and he could be an older guy, or barely legal. You wouldn’t be able to refuse if I told you to sleep with the guy,” I stated flatly.

I had come up with that idea after Brooke had used Sherry to help the fat kid score some pussy. It was really unlikely that there are many women like Sherry who would be willing to jump into bed with some old codger. That proviso would quite likely be the deal breaker and extricate me from the Ponzi Scheme. It seemed like a great idea the time, but I knew I’d be much happier if Sherry had loved me enough to actually forsake all others so I never had a reason to dream up the damn scheme.

“You’d expect me to sleep with whomever? I’d have no say in the matter?” repeated the bombshell next to me.

“That’s right and I have a fat kid and a lecherous old bastard in mind for you if you become part of my pussy parade,” I responded forcefully, believing it would frighten the little minx.

“Wow! That’s kinky as hell! You’d own my pussy for three night of unbridled passion, or even three nights of obese, geriatric, tantric sex? I’m in!” declared the sexy, but obviously perverted woman. “Bill and I knew about the health report so we took the liberty of getting them earlier in the week. My running into you was no accident. I followed you from your work. Let’s boogie!”

To say Sherry looked surprised when she came into the living room around seven o’clock and saw Glenda sitting on my lap on my recliner while Bill waited on the couch.

“What the fuck?” were her exact words. “Glenda? Bill? What are you guys doing here?”

“We’re you’re newest clients!” declared Glenda with a dazzling smile.”Bill’s finally going to get some of your once precious pussy while I rock your husband’s world.”

“But… you need health papers and condoms and an appointment,” began Sherry before Bill cut her off.

“All taken care. Our appointment is right now and here we are. I told you I’d find a way to enjoy some of that pussy, and now’s my chance. Glenda has sacrificed a lot to make this possible and I don’t want to waste another second.”

“I haven’t had any dinner yet,” whined Sherry. “Maybe we should reschedule.”

“A large pizza was just delivered. Half of it is in the bedroom. We’ll eat it in bed,” insisted Bill. “You’ll love the special topping I have in mind!”

I really felt like pasting the smug bastard, but if Sherry wanted the fucker, she could have him. It was hard to believe she was so willing to kill our marriage just to sleep with the slimy prick.

Sherry’s surprise was so complete; she couldn’t think of anything to say as Bill scooped her up and headed for the bedroom I had shown him. She’d get the cock of her fantasies, and I’d get some of Glenda before I began executing my exit plan.

With Glenda in tow, we strolled into the kitchen the next morning to find Bill eating my Cap’n Crunch. I asked where Sherry was. For the first time in a long time, she had already left for work before me.

“She said she had to get into work early,” answered Bill as little Cap’ns flew from his mouth and over the table, some landing on the chair across from him. “She’s probably in a hurry to tell her girl friends what a great time she had last night.”

Glenda chuckled quietly at Bill as she shook her head. “I really doubt that, for more reasons than I care to mention. I owe you a couple of nights of passion, Jim. When do you want to cash in?”

“I have your number, so I’ll call when I firm up my plans,” I replied to the beautiful blonde woman. “You’re like money in the bank for me.”

Bill and Glenda left, so I got ready and went into work. Jensen was walking around the office grinning from ear to ear, but I ignored the miserable bastard. Nancy winked at me when I passed by her desk. I noticed she was dressed a bit more fashionably and nodded my approval. That brought a really cute blush to her face.

When I walked in the door that night, Sherry met me with two suitcases. “Sis called. She’s having trouble carrying her baby. The doctors want her on total bed rest. Mom and I are driving down to help her and Brent with the other two kids. This is all very sudden. Mom called me this afternoon with the news.”

“How long will you be gone?” I asked.

“I really don’t know. I doubt you’ll even notice I’m gone unless your pathetic pussy parade peters out. I had the worst morning of work in my life today. That damn Bill was telling everyone that would listen how he finally tagged my ass, as he put it. I could have lived with that, but Glenda made me feel even worse. She was bragging about how great you were in the sack and how she’s going to make that trade as often as possible.”

“So it’s my fault I gave her a jolly rogering?”I snarled. “You’re the one that wanted to sleep with that slimy bastard, Bill. You had to experience some strange cock. It seems like you’d be happy as hell.”

“I work with those people! How can I show my face there when everyone knows I sport fuck losers while my husband takes beautiful women to nirvana?” demanded Sherry.

“The same way I manage!” I snapped. “You agreed to fuck the single most annoying prick in my entire company. Everyone at work knows I swapped your ass for Nancy’s.”

“I wonder why you did that. Most husbands would have just refused to let me have a lover. Not you! You twisted it into a fuck fest for yourself. That was pretty damn selfish!”

“Like deciding to sleep with other men when you’re married isn’t the epitome of a selfish, degrading action. You got what you wanted, so why are you so upset? Look at all of the dicks you’ve had.”

“I’m upset because my husband wasn’t man enough to stop me from being so damn foolish! That’s why I’m pissed. Sure I had some new cocks and a few orgasms, but look what I lost! I’m a laughing stock at work and with our friends. My husband is fucking everything and anything with a damn twat! I can’t even keep my husband satisfied. That’s what they’re all saying,” cried Sherry.

“You were fine with it when it was only going to be me that couldn’t keep my spouse satisfied. You were awfully eager to hang the horns on me and make me into the town cuckold. Sauce for the gander and all of that. What did you expect to happen when you started fucking other men? Did you honestly think no one would ever find out and we’d go back to being a loving couple after a few romps? Get real!”

“I’m taking a leave of absence from work and going to my sister’s. Don’t call me for a week, at least. I need time to decide what I want. I don’t know if this marriage is worth saving, you miserable bastard! Have fun fucking Glenda and her big tits. I’m sure she’s hoping we’ll divorce so she can scoop you up. Maybe she’ll get her wish.”

“That won’t happen!” I yelled. “I’m done with marrying beautiful cheating sluts!”

“Fuck you!” were Sherry’s last words as she grabbed her luggage and headed for her car.

To say I was pissed would be a huge understatement. I like to think it was a combination of Sherry being so unwilling to accept responsibility for her actions and the opportunity handed to me on a silver platter, but I went a little berserk.

Over a period of three hours, I fielded calls from Brooke, Marla, Gladys, and Nancy. They all wanted to arrange another night of sex. To my utter amazement, each woman readily agreed to my new terms. They would give me three nights when their male companion had one night with Sherry, or an acceptable replacement.

I worked up a spread sheet in order to keep track of my banked pussy. Since Glenda already owed me two nights, I set her up with Brooke’s latest loser friend. That gave me three nights with Brooke, so I assigned her one night with Stewart Santori, and another with Jensen. Glenda sleeping with Jensen gave me three nights with Nancy, so I arranged for her to sleep with Marla’s brother, Glenn. That left Gladys with Bill, which also gave me another three nights with Glenda. The pussy was piling up faster than I’d ever be able to satisfy it!

We had a four bedroom house and all four bedrooms were in use most nights. When I wasn’t sleeping with one of the ladies, I would sleep on the couch so the pussy interest could compound. After five nights, my banked pussy was up to fifteen nights owed by the ladies my service literally serviced.

I was relaxing in my recliner and watching a football game when my doorbell rang. I couldn’t conceal my surprise when I opened the door to find Dorothy Grant and her husband, Ben. I ushered them in while looking around the room for something I could use for self-defense. I needn’t have worried.

“Ben has been after me to give him a night with Sherry. It seems you were right about her appeal to the average man,” stated Dorothy rather bluntly. “I’m willing to spend two nights satisfying your sexual perversions if Ben can have one night with Sherry. Do we have a deal?”

My befuddled mind gradually began to function. Dorothy hadn’t come to chew me out about whoring out her mother and daughter for my personal pleasure! She wanted to join her mother and daughter as a member of my team! I wondered if she knew that her Gladys and Brooke were in my ‘stable’, as I now thought of my ladies.