The Fourth Time's the Charm

by Matt Moreau

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

Desc: Humor Sex Story: Man in love just refuses to trust his whorish girlfriend though he remains her best friend through the worst of times.



I'd met Lana at State College. I was gradding in the M.A. program in June, but she had a year to go on her B.A. I'd majored in Psychology and she in Liberal Studies. The circumstances of our meeting were her taking a Psyche II class that I was student-teaching under the watchful oversight of Professor Duncan.

Lana Albright was pretty, slight of build, possessed of a winsome personality, intelligent, and she was the campus whore. It was common knowledge, and it was common knowledge that she relished. Seeing her sitting in the second row of the theater-style classroom shook me. Okay, yes I did want some of that. Gawd! what an incredible cunt, I thought. As I stood, there were twenty-seven bodies staring at me like I was an idiot, but I didn't care an iota; I knew I had to figure a way into her pants.

"Mr. Colson? Are you all right," said Mary Gilford: a student who had taken two other courses student-taught by me. Her words brought me out of my temporary coma.

"Oh—yes—Mary. I had my mind somewhere else, I guess." I said.

There was a low pitched gaggle of giggles and guffaws. I ignored them; I had no choice.

Somehow I got through the class without completely making a fool of myself.

Class ended, Mary came up to me and asked me a question relating to a theory of Carl Jung's. I gave her the reference and started packing my brief case to leave.

As I turned to go, I literally slammed into Lana. "Geezsus! I said as I caught her just in time to keep her head from hitting the floor. "Ms. Albright, I am so sorry. I didn't see you..."

"Shush, Mr. Colson. No harm no foul. I have a question if you don't mind," she said.

"Oh, no, that's fine. What can I do for you?" I said, still struggling to get some sense of control back. I combed back my hair with my hand, straightened my glasses on my nose, and waited for her to tell me what she wanted. She had to be able to tell how shaken I was by her presence, but thankfully she didn't show any sign that she did.

"Well," she said, "I would really like you to fuck me. I have time right now if you aren't in a hurry to go somewhere," she said.

The tent in my pants was sinfully obvious. "I don't—"

"Mr. Colson. I know you want to. It is soooo obvious. And, I'm in heat and needing a little TLC. Whaddya say," she said, smiling the smile of a cat with its paw in the fish bowl.

"My name is Jess Colson," I said. "Jess to you." I wasn't passing this up. I walked up the ten steps to the classroom door and threw the deadbolt. I walked back down and motioned her to follow me into the small office off to the side of the room. Entering I locked it too. She smiled at me and began disrobing. "Take a seat," she said. I did, and I watched her enthralled. Damn, she was pretty! And now she was naked.


She moved toward me and just stood there for several moments. Her pubis was baby-bare. I gazed at her slit, which was almost at eye level and wondered if the female form wasn't the most perfect thing in the entire universe.

She stepped back, turned around, ad bent over. Her butt was less than eighteen inches from my face. The rear view of her lips was mesmerizing, and her anus was as pink and beautiful as anything I had ever seen. I was overcome with a desire to kiss it and lick it and to try and penetrate it with my tongue—something I had never contemplated before.

Had anyone asked me at that moment; I would have said that this woman could have been the "face, and the body, that launched a thousand ships and laid low the topless towers of Illion." She was that spectacular. The only bad part, as I suspected, was that she absolutely knew it and understood her power. And in Lana's case, power did corrupt and that absolutely.

As she stood there bent over, I got out of my chair, stripped naked in no more than eleven seconds, knelt behind her, grasped her hips and pulled her buttocks to my face and its waiting tongue. I made love to this woman's most private place and adored her as the ancients would have a fertility goddess.

She straightened up, tossed her hair and turned to face me. Still on my knees I licked her slit and kissed her lower belly for what seemed a thousand times. I felt her hands on the back of my head pulling me tightly to her.

"That's right baby, make me feel good. Be a good boy and make me cum." And I did. At that moment, I would have agreed to be her slave forever more. Talk about pussywhipped.

She shivered, and I knew she had orgasmed. Weak in the knees, she knelt down and faced me. We kissed in that position for some moments before she collapsed onto her back on the floor and spread her legs in surrender to me.

I loomed over her and lowered myself to spear her womanly form. She smiled.

"Ugh!" she moaned as I mastered her. I began punishing her loins as I thrust again and again inside of her. Soon she was jerking in paroxysms of sexual completion ohohohohohohhoh! She stiffened and collapsed in on herself life a dying star. "My gawd that was good," she said.

I came three seconds after her, washing her insides with my blazing hot semen. I lay on top of her for a few seconds before rolling off of her and onto the floor beside her.

She rolled on top of me and began kissing and licking my face. The smell of her was overpowering and I gloried in it.

Tiring, she lay back beside me and relaxed. For a long time both of us just lay there in the afterglow.

"That was the most wonderful fuck I have ever had," I said.

"You might be the one," she said.

"What one?" I said.

"The one I will marry," she said. "I will let you know."

I wasn't sure if she were kidding or serious. But at that moment, I would have agreed to do anything she wanted any time she wanted to do it.


We began dating immediately after that first time. We were a monogamous item for a whole three weeks; then she broke a date with me for the first time. I wasn't an idiot; I knew what she was doing, and I was not about to let it get to me. I broke off with her.

"Why are you breaking up with me?" she asked, the next day seeming to really want to know. I had actually pouted at first, and then gotten a little bit angry at having been stood up.

"Why! Am I dreaming or did you ask me why?" I said too loud for normal conversation.

"Yes, why?" she said. "You knew before we met that I liked to date more than one guy. I never made it a secret. I know what they say about me around campus. Mostly it's true. I do not, however, pull trains, no matter what they say."

I just stood there with my mouth hanging open wondering if I should say something or just walk. I decided to just walk. If I'd been smart I would have walked clean out of the state.


A couple of weeks later I was sitting in the cafeteria going over some notes for my thesis. I was having trouble relating some of the evidence that I had gathered directly to my project: too much of it was anecdotal; I needed more cross references for support.

I took a sip of the cold coffee I'd been nursing for three hours.

"Hi," I heard from behind me.

I turned. "Lana? What?"

"May I sit?" she said. Not waiting for me to say okay, she sat. "How have you been, Jess?" she said.

"Okay. Lana, this is not..."

"Shush, young man," she said looking directly into my eyes. "I miss you. I want you back. So, tonight pick me up at my dorm at 7:00, okay."

"No, Lana, it's not okay. I don't share my girl with other men. I just don't, and I know..."

"I've turned over a new leaf, Jess. I'm yours if you want me. I know I disappointed you before, but it won't happen again; I promise. No more standing you up; really, I promise."

I stared at her for a long moment. "Lana, I don't know if you can change. You love the chase too much. I'm not into heartache and mental distress," I said.

"Jess, you're not hearing me. You have to give me a chance to prove to you that I love you and that I will be good. You simply must," she said. She was beginning to cry. That stopped me. Call me a fool, Call me pussywhipped, I just can't let a woman cry when I can do something to stop it.

"Okay, Lana, I guess a date won't be all that big a deal. I'll pick you up at 7:00." And I did.

The date was good. No sex though. I wasn't going for any of that until I was sure that she really had turned over a new leaf.

Two months later I graduated. Lana and I and my parents and some of our friends had a wonderful time at my folks' country club.

Lana and I continued to date. I remained at the college as an adjunct instructor in Psychology and Philosophy; at least now I was getting paid as I worked toward my Ph.D.

It was at a faculty party in the spring semester of that first year that I proposed to the girl of my dreams. She sprang into my arms and the sex for the next three days was nothing if not historic! Gawd! I loved that girl, and she loved me. She loved me so much that she stood me up again and fucked my best friend the night after we'd set the date for our wedding.

I hurt so bad that I cried for two hours straight that night. When she showed up the next morning, she begged me to understand, to forgive her, to start over.

I loved her, but I knew this wasn't anything that I needed. I walked away. She couldn't help herself. I left her sobbing bitterly and swearing that she didn't mean to do it; that it just happened.

Outside I shook myself and let myself feel good. I was free! I had almost made a bad mistake. Well, one lives and one learns.

The semesters progressed. It was June and Lana graduated. I received an invitation to attend her grad party; she'd asked for an RSVP; I didn't respond. Her parents were evidently footing the bill for the hotel. Lana was nothing if not tenacious.

I got a late night call the night before the party. "Hi, Jess, it's me," she said so softly I barely recognized her voice. "Are you coming?"

It had been six months since I'd even seen her let alone talked to her. I later suspected that she had made sure that I'd had plenty of time to get over my mad before she laid siege to me again. I hadn't gotten over it.

"Coming to what?" I asked. I really had forgotten about her grad party.

"My party at the Hilton tomorrow night. I've gotten my B.A." she said, a little louder.

"Oh, no I can't, Lana. I am very busy working on the proposal for my dissertation. You understand."

"Jess, this is a very big day for me. I've told everyone that you'd escort me. Just for old times' sake," she said.

Now, I am not the village idiot. I have an IQ of 172. And, unlike Einstein, I actually do tie my shoes, comb my hair, and dress well. So, with all of my more than impressive qualifications, I should have been able to repel her assault on my Psyche; I had an M.A. in Psychology for Chrissakes!

"Okay, Lana, for old times' sake." Her glee was almost too much, over the top, suspicious in its intensity. I knew I was in for it, and I wanted to punch myself in the nose for being—well, the village idiot.

We talked a little longer, and I agreed to pick her up at 6:00PM; she had to be there early, she said, to make sure everything was managed right.


The grad party was a good one. Everyone ate and danced and talked and danced some more.

Lana doted on me. "Honey, do you love me?" she had the brass cojones to ask. I answered her truthfully.

"With all my heart," I said.

We happened to be dancing, and she melded her body to mine. Now, from a scientific point of view there are few things in the wide world that feel as wonderful as the female body pressed against that of a man. The feel of it, the smell of it, the heat of it: there is nothing like it anywhere. And, if any female on the third planet from the sun was an expert at using her body to enslave a man, Lana was that female.

During the evening Lana made sure that my senses, my mind, my very soul were under almost irresistible pressure to knuckle under to her skills. I very nearly succumbed.

"Honey, you know I've kept the engagement ring you gave me before—before I flubbed everything up," she said. She sounded like a helpless kitten in need of a fireman.

I looked at her. I had actually forgotten about it. And it had cost me $1,400. But, I wanted her to have it. I wasn't interested in marrying her anymore, but I did still adore her, love her; that wasn't going to change; she owned my heart—but not my good sense. "You keep it, dearheart. It's memento of what might have been," I said, as gently as I could.

"Jess, couldn't we try again. I've learned my lesson," she said.

Gawd! how I was tempted. "Honey, Lana, I do love you. I think you know that, and I think you know how much. But, I can't trust you. I don't know what it is for you, but you simply cannot help yourself, and I need a woman that is there for me and me alone. I want a woman to share my life with, and to grow old and crotchety with. I don't want other men sharing my bed with you. I just can't get around that, and you can't either; I wish that you could."

We danced and talked and she begged and I begged off, and finally the evening was over. I took her home. Kissed her goodnight and wished her well.

A month later, she married my former best friend, Dave. I wasn't even invited to the wedding. I considered that a lucky break.


The couple were doing well by all accounts. I heard bits and pieces of what was going on with them from time to time. Dave considered her his trophy wife, and adored her; hell, all of the men I ever met adored her; she was adorable, a slut, but an adorable slut. Going on two years after their marriage Dave caught her doing that which she had vehemently protested she never would. He caught her pulling a train. It was the entire basketball team at the college, all fourteen of them. I remember thinking at the time; there were seventy-one members on the football team; I guess she knew her limits.

Dave actually showed up on my doorstep begging forgiveness for poking her that first time and ruining my life, or so he imagined, asking my help in getting a divorce. He said he just couldn't bring himself to do it without somebody holding his hand. I told him to get some backbone and do his own dirty work; he literally howled in despair.

Their divorce was final eight months later. Dave was a physical wreck. He still couldn't believe that she would cheat on him. There was a rumor later on that he had tried to slit his wrists when he found out that she had gotten engaged to someone else soon after their divorce. But it was just a rumor; I didn't think he was capable of doing anything to himself. He just doesn't have the balls for something that dramatic.

But I digress. Before she got engaged to Gerd, I got a visit from her.

I was just finishing up a class in the same theater where we had first met. She had to have planned it that way. Talk about drama queens.

"Hi, Jess," she said. "Got time to buy a girl a cup of coffee?"

My eyes narrowed involuntarily. "Uh—sure, okay," I said.

It was pleasant talking to her. She really got into her persona. Everything that had happened during the past two and a half years was fair game. She looked a little weary to me, but her energy level remained undiminished.

"Jess, I'm available if you want me," she said.

"Huh?"

"For the night or for a lifetime your choice," she said. "I'm still the most talented slut in town, you know."

And I did know. And I did want to fuck her. "My place or yours," I said.

"Yours, I don't want to run into Dave. He's been stalking me since the divorce. I don't know why; it was his idea to get the divorce; I didn't want it. We could have worked through it."

The sex wasn't good; it was Olympian. Geezsus that girl could fuck and suck; she really did have no equal in the arts of love. In the morning we said our goodbyes. I had the feeling that I had not heard the last of her. But, in point of fact I had; well, for the next five years at any rate.

The night after our one night stand, she had gotten engaged to a History professor twenty years her senior, Gerd Trotska. I think she made an effort to be faithful to him. I saw her a lot: she attended all of the faculty functions. I even escorted her to two or three of them over the years at Gerd's request. And then it happened again.

Gerd had come home for lunch unexpectedly. He caught her in bed—with his sister! He went insane with rage throwing things, screaming at her—at both of them "queer-assed bitch, pig, whore, asshole—the list of epithets was long. Finally, someone, a neighbor, called the cops. No one was hurt. But, the cops hauled Gerd downtown to let him cool off. He was out the next day when Lana came down to bail him out. His gratitude was limited however; he divorced her less than two weeks after the fiasco with his sister.

After the divorce was final, Lana laid low for a while. As far as I could tell she wasn't banging anybody and kinda disappeared from the local social scene. It was something less than a year after her latest divorce that I got another visit from her. She was broke.

"Jess, can you help me? I'm at a loss. I can't even buy food. I lost my job. Gerd flips me off every time I've gone over to ask him for a little help, you know, just to tide me over. Geezsus, Jess, I need help!"

I thought to myself that she sure did, but not the financial kind, but the fact was that I still loved her, so I let her shack up with me for a while and gave her a little assist financially. She was grateful: she damn near wore my penis off, and I loved every fucking minute of it, no pun intended.

She cooked for me, cleaned the place, even did some of the yard work. I knew what was coming: I tie my shoes and comb my hair, remember.

"Wanna try again," she said as we sat sipping wine one evening in the fall.

"Do you want to marry me?" she said. "I do windows."

"Tempting," I said. "But you know I'm a one woman guy, Lana, and you are not t a one man woman. If you ever really do become one, I'll consider it."

"I'll hold you to that," she said. What I didn't say was that I wouldn't be holding my breath.


It was just before Christmas that she disappeared for almost a week. I knew what was up. And, I'm sure she knew I knew. I just wondered who he was this time.

Well, it turned out that she wasn't going out with anyone initially. No, she was in jail: a drunk driving offense. Why she didn't call me to bail her out was kind of a mystery. She later told me that she was too ashamed to tell me. I never knew, but I think that the reason she was ashamed was because she'd been fucking some guy or other and just couldn't face me. Nevertheless...

She did get bailed out, by none other than the cop who had busted her: one Herbert Gillis. He'd evidently brought her in and then spent some effort using his resources—read the resources of the PD—and figured out who and what she was. That she was the village slut seemed to intrigue him.

After he bailed her out, they dated a few times, and seemed to become close. She'd told me about him. One night a couple of months later she was waiting for me when I got home from work.

"Hi, hon," she said. "I've got something I need to talk to you about." I figured I could guess what it might be. One thing about Lana, she wasn't a mystery.

"Okay," I said, "shoot."

"It's about Herbert," she said. I motioned her to go on. I was smiling to myself, such a drama queen. "Well, he has asked me to be his wife," she said.

"That's wonderful," I said. "He's a lucky guy. When are you two planning to tie the knot?"

"You're not mad," she said.

"Heavens no," I said. "Am I invited to the wedding?"

"Well—sure—I mean of course," she said. "I mean if you want." She clearly had expected me to be upset. We had cohabited for quite a while, in point of fact, and I guess she figured that I would want to keep her around.

"I want," I said. "You know I love you, and I want you to be happy. I hope you don't, well, you know," I said.

"No, I've given all of that up," she said. "I'm a one man woman now, as you used to say."

"Well, then you will make that fella one very happy guy," I said. "I felt like I needed to say one more thing to her. I did love her, I just didn't trust her a whit; and I worried about her more than I was willing to admit.

"Lana, he's a cop. He has resources you have no idea of. If you mess around, he will find out, and you will be in deep shit," I said.

"Jess, I told you, I'm a changed woman. I intend to be totally faithful to my new man," she said. I smiled sympathetically and kissed her. "Good," I said.

I think it was David Hume, the great skeptic of the 1700s, who said that nothing is for certain, not even that the sun will continue to rise in the east. As short as the odds were that Lana would remain faithful to her new husband, I knew I could be wrong. And, I was, for a long time.


It was some fifteen years, before I heard a rumbling in the east. Lana was forty-five and at that stage in life when many women begin to get hot pants related to the physical changes in their biological clocks. Of course Lana had never had cold pants. But in her midlife crisis, her pants were extra hot. She messed up with another cop: a close friend of her husband's. Herbert heard about it and he was not happy. I got a call from St. John's Memorial Hospital; it was from a nurse.

I picked up the phone on the third ring. "Yes, this is he ... what! ... where ... I'll be there in fifteen minutes." I slammed down the receiver and was out the door, in the car, and on the road in less than sixty seconds.

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Story tagged with:
Ma/Fa / Romantic / Humor / Cheating / Cuckold /