The Waitress, the Biker and the Cuckold

By smallerDdesire.


I could see her quite plainly through one of the restaurant’s big plate glass windows facing the parking lot. She laughed a bit as she poured the hot black coffee into a customer’s cup. She was good at her job, always knowing just how much or how little to flirt with a man to get the best tip. I couldn’t hear what was being said, but I saw the truck driver-type customer smile and chuckle. Tammy would get a good tip out of him. However, it wasn’t the trucker I was interested in. It was the big biker with the long ponytail and tattoos at the coffee counter I was there to observe.

Tammy and I’d been together for years, but it wasn’t until the last 2 years things got bad enough between us that she’d cut me off sexually. Still, every night after her shower, she’d walk through the living room naked, crossing right in front of the television, so there was no way I could miss seeing her go by on her way to the laundry room to get her pajamas. Tammy loved to work out and to keep her rocking body tight and in shape, so despite our problems, I couldn’t help it when my mouth watered. My dick stirred when she made her nightly ‘catwalk.’ She’d toss her long wavy brown highlighted hair as she went by, the light from the TV reflecting off her D-cup tits and shaved ‘V’ between her legs.

Even though we weren’t talking or touching every night, I would wait for that catwalk. Then on the way back to the bedroom, she’d be covered up in her pajamas, and I knew I wouldn’t see her naked flesh again until the routine was repeated the next night. So no, it wouldn’t be me that would be touching Tammy’s bare flesh. It would be him, the biker at the counter.

I knew Tammy well enough to know that even though she was punishing me by withholding sex, she’d be getting her needs met somehow from someone. Waitresses get hit on all day, and I’d found the coffee cup full of names and phone numbers she kept in the console between the seats of her car. So about a month ago, I had begun to discreetly park outside the restaurant where she worked about an hour before her shift ended to see if she had someone meeting her needs. Sure enough, it wasn’t long before I began to see the biker come in and sit at the coffee counter where they would flirt a bit. Then Tammy would put down her dish towel, give him a look, and head to the back to clock out.

She’d leave first and wait in her car. Then, he’d finish his coffee, leave a couple of bucks on the counter, and leave out the front. The first time I saw this, I began boiling with anger as I followed them to a nearby motel. I watched from my truck as they climbed the second-story stairs up to a room and disappeared inside. Thoughts and feelings swirled inside me as I contemplated what I would do and what I would say when I confronted them. Why wasn’t I good enough for her? I’d always known I’m on the smaller side down there, but Tammy seemed to love it. Before things got so distant between us, she used to ride me and cum over and over, or so I thought anyway.

All this and more was going through my mind the first time I walked across the motel parking lot and up the stairs. Then, as I raised my fist to beat on their door, I heard something that stayed my hand in mid-air. It was Tammy. Moaning in a way I’d never heard before, low and guttural, then louder and faster.

“OH. OH. OH,” I could hear her cry in time with the bed springs squeaking as if they were being pressed flat and then rebounding. I could hear the headboard hitting the wall too. The moans and squeaking and the knocking of the headboard held me transfixed for a long moment as I thought to myself, ‘We’ve never fucked like that. And I’ve never heard her (or made her) moan that way.’ Then, as I stood outside the room listening, I noticed too that my cock was straining against the fabric of my jeans.

All four inches of me was rock hard as I listened to another man fuck my girlfriend! I dropped my hand as the cries got louder, and the squeaking and knocking of the bed got faster and faster. As I stood transfixed outside the door, it was as if someone else was in control of my body. I wanted to beat on the door and make them stop. Confront her for cheating and lying. I wanted to leave and not listen anymore, but I couldn’t move. My rock-hard cock was aching as I listened to Tammy’s cries come faster and faster and louder and louder.

Suddenly she let out a series of short, sharp cries and then one long moan of ecstasy as the biker cried out, “Oh, Fuck, Yes, Baby! Take my cum, Bitch! Take all my cum!”

As it grew quiet inside the room, I found I could move once more, and as I walked quietly away, my heart was racing, and my thoughts were swirling. All I could do was just drive away. I did nothing to stop her. Soon she’d be home from being freshly fucked, and what would I do? The whole drive home, my dick had remained rock hard. As soon as I shut the truck off in the driveway, I ran to the front door and fast as I could. With trembling hands, I unlocked the door and practically ran inside, slamming the door behind me. I couldn’t get my pants unzipped fast enough as my dick had been aching and throbbing for the last 45 minutes. I ripped down my pants right in the foyer, and as soon as my underwear came down, it happened.

The sperm came flowing out of my four inches like a fountain! Jesus! What was happening to me? I dropped to my knees from the intense orgasm and realized the sounds of my cheating girlfriend getting her brains fucked out just made me shoot cum halfway across the room, and my knees buckle! I knelt there with my confused thoughts for a few moments and then slowly got to my feet. As if almost in a trance, I wiped off my cock and zipped up my pants. I got a paper towel and wiped my cum off the floor of the foyer. In a semi-daze, I made it to the couch and just sat there, my mind a cloud of confusion.


It wasn’t long before the sound of Tammy’s keys, hitting the counter, startled me from my fog. “It smells like cum in here. Have you been jacking off again you bastard?” she shouted.

Not hello, how was your day? She’s not even pretending to play it cool because she might feel guilty for having come from getting her pussy pounded and brains fucked out. Not Tammy. She just went right on the offensive.

“You better have cleaned it up, you cocksucker.”

She hardly glanced at me as she breezed by on her way to the bathroom. I listened to the sound of running water coming from the bathroom as I contemplated what to do next. I’m going to confront that bitch. I’m going to tell her I know everything. What she did where and with whom, but as I heard the sound of the shower running, my resolve began to slip as my cock stirred in my pants. Holy shit, I was getting turned on as I thought about the way she moaned.

When she came parading by with just a towel wrapped around her head, all I said was, “How was your day, baby?”

“Fine…” was her curt answer. “Did you get us something to eat because you know I’m not cooking after being on my feet all day?”

That’s how it all began.


Now for the third time, I found myself outside a motel room door listening to Tammy’s moans as she was once again getting her brains fucked out by her biker buddy. I was so engrossed I didn’t take note of it when the sounds inside grew still. Suddenly the door comes flying open, and a naked Mr. Biker sprang out. Grabbing me by the throat, he dragged me inside and held me against the wall. Jesus, this guy was big! He must have had 65 pounds on me.

“What the fuck are you doing here, fuck face? Listening to us? Were you going to do something, pervert?” he said as his grip tightened on my throat.

I could only shake my head a little bit as his big hand on my throat was cutting off my air.

“Don’t hurt him!” I hear Tammy cry. “That’s my boyfriend.”

“What the fuck, Tammy! This guy is a pussy! Look at him. His dick is hard,” the biker growled.

It was true. My dick got hard as a rock as I stood outside listening, and even all the aggression had not changed that.

“You actually fuck that?” he continued. His grip slowly relaxed as he pushed me into a nearby chair. “Sit down, fucker. What were you doing, spying on us? You think you’re going to be some Billy badass and come in here and do something about it?”

I could see a small smirk across Tammy’s face as I shook my head no.

“I don’t think you can do shit, you pussy. Especially with that…” the biker said as he pointed to my crotch.

Still standing there in the nude, this guy’s cock must have been 4 inches soft! He grasped his dick in his hand and held it in front of me.

“Now, do you understand why I’m fucking YOUR girlfriend, and YOU aren’t?” the biker demanded.

Tammy’s smirk got much bigger as again. Again, all I could do was shake my head. “By the way, this is ‘Skulls,’” as she pointed over to him.

Skulls turned to me. “I’ve heard of you. Now I gotta see this. Drop your drawers, Bitch,” he said as he grabbed the front of my shirt and shook me like a rag doll.

Real fear began to grow in the pit of my stomach, and I knew my hard-on was no more.

“Do it! Hurry up, fucker!”

I looked over at Tammy. “Better do it,” she said. “He’s been to prison and doesn’t care.”

I looked at her as I unbuckled my belt, his grip still on my shirt. I unzipped my pants and pulled them down just above my hips.

“All the way down, fuck face,” he shouted.

I pushed my pants and underwear down to my knees, exposing my now fear shrunken button dick and tight ball sack that looked like I just got out of a cold shower. He smirked as he looked over at Tammy.

“I can’t believe you see anything in this pussy,” Skulls said.

“I quit fucking him two years ago. So now you understand why?” Tammy replied as she looked at me.

Turning back to me, he said, “Now you’re going to see how to really fuck. Not that you’re ever going to be able to, your too much of a pussy. This is as close as you’ll ever get to her pussy again.” He grabbed Tammy’s panties and shoved them in my mouth. “Don’t move; I’m going to show you how it’s done.”

As I sat frozen in the chair with my pants down to my knees, exposing my shrunken dick and balls with Tammy’s soiled panties in my mouth, he moved to the bed and grabbed a handful of her hair. Then, as his cock moved towards her, he steered her head right down to his crotch.

“Start by licking my balls, bitch.”

Tammy’s face disappeared into his pubic hair, and I could hear her tongue moving back and forth over his nut sack.

“Yeah, lick those balls, good!”

I could only stare as it crossed my mind that she had never licked my nuts at all.

“That’s enough, now suck on this dick.”

Incredibly, his cock had grown to at least twice its size soft, at least 8 inches long and thick. Still holding Tammy by her hair, he put his cock to her lips, pulled her head down on his dick, and began moving her head up and down. Slowly sliding his member from top to bottom, as it slides in and out of her mouth, grabbing either side of her face, he rocked his hips back and forth, fucking her mouth faster and faster.

“Take that dick, bitch! Don’t stop.”

I marveled at Tammy’s ability to swallow a cock like that. I had no idea, but how could I have known? Having my dick in her mouth must have been like licking a Dum-Dum compared to Skull’s member. Water began to form in the corner of her eyes, and drool trickles down her chin as the fat dick pumped her face.

“That’s my girl. Suck that dick,” he said, and then to me, “See how it’s done, pussy boy? Watch, because you’ll never match this!”

As if I could take my eyes off the scene taking place in front of me. Skulls pulled his dick from Tammy’s mouth with a pop and pointed at me. “Look, baby, little dick must like what he sees. His little boner is leaking!” At which point, they both burst out laughing. I looked down, and it was true. Precum had leaked out and started to run down my dick. Tammy reached over, pinched a big drop between her thumb and finger, and wiped it on my lips.

“Don’t let it go to waste. Have a taste,” she said and laughed loudly.

It was then that Skull’s reached over a flipped Tammy over on her stomach like a rag doll. Then, looking at me, he said, “Now this is how to fuck. Watch and learn.”

With her feet on the floor and her ass in the air, Skulls took her from behind doggy style. First, the thrusting started slow and short until gradually, his dick was bottoming out against her ass while her moans grew louder. Soon all that could be heard was the sound of his heavy balls slapping Tammy’s pussy over and over and the sound of her moaning. With her back arched and the sheets bunched tightly in her fists, the first of her orgasms hit.

“Oh, fuck yes. I’m cumming! Don’t stop! Don’t stop!” Tammy moaned.

Wave after wave of pleasure seemed to flow over her as she pushed back against his cock in rhythm with his thrusts. While still ramming her pussy, Skulls looked over at me.

“I know you never saw her like this before because ain’t no way your little pecker could pull it off. Stroke that little stick, fag, cause you ain’t getting your little pecker in this pussy again.”

As I began two-finger stroking my four inches, Skulls let out a big groan as he blasted his seed deep in Tammy’s hot hole.

“Yeah! Oh, fuck Yeah! Now that’s how it’s done, boy,” Skulls said as he pulled out of Tammy and roughly flipped her on her back and spread her legs wide.

“C’mere, pin dick. Taste your girlfriend’s pussy after it’s had a real man’s dick in it.”

Skulls pulled Tammy’s now soaking panties out of my mouth. As my pants were still bunched up around my ankles, I could shuffle my way over to the bed, where Skulls pushed my face down between Tammy’s legs with my face into her sopping wet pussy. As my tongue probed her cum covered pussy, Skulls began to spank my bare ass hard.

It almost took my breath away as he yelled, “That’s for sneaking around while I fucked your girlfriend!” Again and again, he rained down blows on one ass cheek and then the other. “Are you going to do that again, pin dick?”

I could only get out a muffled, “No,” as my face was deep in Tammy’s pussy.


“No, what?” Skulls bellows.

“No, Sir!” I cried.

The beating stopped as I continue to lick Tammy’s cum leaking hole. “That’s better. You call me ‘Sir’ from now on.”

“Yes, Sir!”

My ass felt like it was on fire as I continue licking Tammy’s clit and probing her hot hole with my tongue.

“Get something straight pussy boy, from now on, no more motels. When ‘your’ girlfriend and I get together, it’ll be at your place from now on, and you will like it, right?”

“Yes, Sir!”

“Good. Now get the fuck out of here.”

Skulls pulled me from between Tammy’s legs by the back of my shirt and shoved me out the door with my pants still around my ankles, my little boner sticking out, and my ass cheeks throbbing in pain. I hurriedly pulled up my pants and hobbled towards the truck. I drove home carefully, as I could barely sit. My ass hurt so bad from the beating Skulls gave it.


I was sitting on ice packs when Tammy got home hours later. What could I really say? I had been totally humiliated and beaten while she fucked another guy. However, she was just as sweet as sugar as she handed me a small box.

“I stopped on the way home and got you a gift. Luckily, they had one in extra small.” She said.

Wondering what it could be after all that had happened, I thought to myself. Maybe she does love me after all until I unwrapped the box to find a chastity device with a tiny padlock!

With a big grin on her face as I held it in my hands, she said, “Go lock it on…NOW!”

After that day, Skulls was true to his word. A couple of times a week, he would come by, he and Tammy would fuck on our bed while I was either in the other room listening or tied to a chair in the bedroom where I could only watch and do clean up duty when Tammy or Skulls wanted me to, which was most of the time. After the first day, the chastity device stayed on almost all the time; Skull’s friend at the health clinic gave him a nice supply of Testosterone blockers and Depo shots that I got every two weeks from then on.

Even when the Chastity cage did come off, there was nothing I could do with a little dick rendered limp and useless from the drugs. My life had become one of sexual frustration and that of a cuckold voyeur. Tammy eventually left me and moved away. The drugs wore off, and things worked again. There was just one problem. She had taken the key!

The End.


*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.

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