Memorable for the Wrong Reasons

So I looked down at my cock. It was still hard, with pre cum oozing from the tip. The spanking, painful as it had been, had still been incredibly arousing. Now that she was starting to suck and fondle his massive erection, I was even more turned on.

I looked back at Tim's cock. It was halfway down Cheryl's throat. She never cared to suck me, but seemed content to give Tim a blowjob. He tousled her long blonde hair, and she periodically flipped it back, probably so it wouldn't block my view. Her other hand was either stroking the base of his cock or playing with his balls. Tim was moaning and breathing heavily. He would cum any minute now, and Cheryl knew it.

She leaned her head back and looked up at him, lightly stroking his cock, glistening with her saliva.

"I'm going to let you cum in my mouth," she told him softly. She sucked him a few more moments then turned to me.

"How many times did I let you cum in my mouth?" she demanded to know, but the question what rhetorical. "Oh, that's right. Never!" She laughed and sucked Tim some more. "It's so much different with a big penis like this," she said to me. "You'll get hard again, won't you, and make love to me?" she asked, looking up at Tim lovingly and taking him into her mouth once more.

"Yeah, babe," he said, panting. I suspected he wanted her to just shut up and suck his cock. He placed both hands on the back of her head, but it didn't look like she would stop to give me any more trash talk. Giving him a blowjob with real enthusiasm now, I saw one of her hands reach up behind his balls, apparently slipping a finger or two into his asshole, something I had always wanted to experience and never have.

That sent Tim over the edge and he grunted loudly, cumming into Cheryl's mouth. He had a handful of her hair, possibly to make sure she took it all, but there was no need for that as she kept sucking and fondling him until his moaning subsided and his breathing slowed to its normal pace.

Cheryl then turned to face me, gave me a pouting expression and stuck out her tongue. A little bit of cum had run down her chin and she playfully wiped it off with one finger and seductively licked it clean.

She stood up and they kissed passionately for a long time. Then Tim scooped her up in his arms and placed her on the bed. He started to remove her panties, but when he had them down to her knees he stopped and began to pull off one of her boots.

"No," Cheryl said, pulling her cowgirl boot back on. "He has a boot fetish," she said with a tone of distain, pointing at me. I'm sure these boots are driving him wild so I'm going to keep them on to make him suffer even more."

Tim said that was weird and continued to take off her panties.

"You like my boots, don't you?" she asked me.

"Yeah," was all I could think of to say.

"If I had these when we were together I'm sure you'd want me to wear them in bed. Too late," she taunted. "I'll be wearing them for Tim though, any time he likes. Just remember that."

I doubted she would wear those boots during sex again, as Tim could seem to care less one way or the other. Without making eye contact with me he tossed her panties towards me in a loose underhand throw. They landed with a whisper of satin and lace just in front of my chair, and it would have been possible for me to touch them with my bare feet. I knew they would be warm from Cheryl's body, and musky from her arousal, though I wouldn't be able to enjoy the scent.

Tim spread her legs. Unfortunately Cheryl was lying on the bed so that I was facing her side, and couldn't see her pussy, which I envisioned would be shaved as she often did, her lips swollen and moist. As Tim went down on her, she turned to me and said.

"He does this so much better than you. Oh... That's so... good," she moaned.

She hooked one of her legs around his body, and slowly traced the heel of her boot around on his back. Cheryl gently rubbed his head, which for some stupid reason he kept shaved even though he could grow a full head of hair. She cooed and moaned in a blatant display of overacting, though I had no doubt she was enjoying the experience.

I knew from the years that we were together, that it would take her some time to reach orgasm, and my mind started to wander as I felt a slight itch above my left eyebrow and briefly struggled with the cuffs.

Momentarily I glanced down at the pile of gifts he had presumably bought her, and took a better look at the brochures. Like Las Vegas, it was easy to get married in Gatlinburg, and it seemed as though she had collected pamphlets from all of the many wedding chapels. Not only had I lost my girlfriend to an old friend, it looks as though he planned to marry her.

My cock was still hard, oozing pre cum, some of which had dripped onto the seat of the chair. Watching the couple, I was surprised that Cheryl hadn't positioned herself at a better angle, and spread her legs widely like a porn star, so I could watch Tim pleasuring her.

She planted the heels of her boots into the mattress on either side of him, and tilted her pelvis up towards his face, breathing heavily. There was no more fake moaning. I knew from experience that Cheryl would soon have an orgasm, and one in record time.

Maybe Tim really was better at going down on a woman, but I suspect she had started to get aroused when she spanked me. Cheryl really seemed to enjoy humiliating me, and I knew it wasn't over yet.

Her muscles tightened. She gave several long deep sighs, shuddering each time. A long series of multiple orgasms. Tim stayed between her legs, and seemed to be giving a few final, long slow licks, until all of her tremors were gone.

I expected her to tell me something like, that's how it's done. Instead, Cheryl got up slowly, catching her breath. Without words she guided Tim and had him lie down on the bed. She gave his cock a few light strokes, though it was firmly erect once more.

Cheryl climbed on top of him and her back was to me now. She leaned down to kiss Tim and tilted her ass slightly in the air, probably so I could see her pussy, slick and shiny with her juices and his saliva. It would have ample lubrication to receive his enormous penis.

Her asshole was also gleaming with the juices that had run down between her legs. A puckered shiny flower. When we were together, I used to lick her asshole while fingering her pussy, as regular foreplay during her period. That had never failed to bring her to a powerful orgasm. One of my perversions that she never did complain about. I doubted that Tim would ever thrill her in that way.

As they were kissing, I could see that he was pulling down the top of her bustier to expose her small firm breasts. She slid forward on top of Tim, and though I couldn't see, I assumed he was kissing them passionately.

Cheryl twitched her ass a little bit, most likely to tease me, and then eased backwards, the head of his penis barely entering her. To my surprise, she stopped, adjusted her position on top of him, and then slowly took him about halfway in. Her pussy looked as though it was being stretched to its limit. She began to ride him slowly, exhaling loudly and taking him in a little more with each stroke.

Tim relaxed and let her do all the work for now, though he lightly caressed her sexy ass with one hand and I assume the other was cupping one of her breasts. Once she had taken him all the way in, Cheryl looked at me over her shoulder, tossing her head to flip her blonde hair out of her eyes.

"This feels so good," she said with a tone of satisfaction. "The first time he made love to me with his man sized penis, I knew that you and I were finished."

Damn it! That means she had fucked Tim while we had still been together!

"Don't look so upset. I wouldn't want you to cry," she laughed. "You were snowed in on a business trip up in Cleveland, so your good friend came over to comfort me in a way that you never could."

"Hey, babe," I heard Tim mumble and he pulled Cheryl down to kiss her, or maybe also to shut her up. After that they both seemed oblivious to me. I had thought he was my friend, but assuming what Cheryl said was true, he had sunk low enough to steal my girl while I was out of town.

I still remember that night I was in Cleveland, with I-71 closed due to a blizzard, so I had to stay another night at a budget priced motel in the Brookpark area. As I recalled I had stayed up late looking through my extensive collection of porn photos that I had saved onto a flash drive. Lying on the bed with my laptop beside me, I had played with myself for what might have been hours.

As she continued her slow ride on his massive cock, all I could do was sit there, fuming with rage, my own cock swollen and aching for relief that it wouldn't get any time soon. My scrotum had tightened up against my body to the point that my balls felt as though they were being squeezed. Not to mention that my ass was still sore from the spanking.

I tried to spread my legs, ease back in the chair a little, anything to get more comfortable. Cheryl's little black leather flat, which was lying on the floor near the foot of the bed, had stung my behind more than I'd expected. Looking more closely, there were a few drops of liquid on the floor near her shoe. Drips of saliva, cum, or both, left over from when Cheryl lovingly sucked Tim's cock. She had never given me a blowjob like that, and always finished me off with her hand. For all I knew, he was cumming in her mouth every night.

She was taking her time now, slowly yet purposefully riding his massive penis. I was really surprised that she could take it all the way in. At that moment I realized something. He wasn't wearing a condom. Cheryl was on the pill when we had been together, but she always insisted on double redundancy birth control. Not only did Tim get to cum in her mouth, but in her pussy as well.

I was at the point where I couldn't take watching anymore. If I'd been watching a porn video clip, I would have fast forwarded to the cum shot. However, I was stuck in this uncomfortable chair, my penis painfully erect and swollen, oozing pre cum into what was now a growing pool on the seat of the chair.

Trying to let my mind wander proved to be useless. Cheryl had picked up her pace, the unused garter straps of her lingerie swinging and flapping against her sexy ass, rapid breathing almost a whistling sound.

Tim was periodically making these grunting sounds, though he didn't seem to be anywhere near orgasm. I had cum twice in one night before, with an older lady I'd picked up at a bar some years before I met Cheryl. Sex the second time around had lasted a long time, and I had savored it.

Cheryl squealed in what might have been a second orgasm. It looked as though she might have been fingering herself like you see porn stars do. Then she slowed down, and gently rolled off of Tim so he could be on top.

Her face and chest were flushed, glowing with sweat and sexual satisfaction. As she spread her legs for Tim, I caught a glimpse of her pussy, wet and gaping from impaling herself on his huge penis. She laughed at me as he got into position. I suppose I was a pitiful sight.

Tim was all business, fucking her hard right from the start. I could hear Cheryl gasp lightly after every stroke as he slammed in balls deep every time. Her legs were up in the air to better accommodate him, silver boots gleaming in the bedroom light.

He was lucky to be fucking a hot girl like her, all dressed up in her lingerie and sexy boots, though it seemed he could care less about the extra frills.

The bed springs were giving occasional squeaks now as Tim plowed heavily into Cheryl, pushing her deep into the mattress with each powerful stroke. I heard a catch in his breathing, and then he threw back his head and grunted loudly several times. There was no doubt that his orgasm had been intense and satisfying.

Cheryl lowered her legs and planted her boot heels in the mattress while Tim fucked her slowly and gently. They kissed deeply and she wrapped her arms around him as he emptied every last drop of cum deep inside her.

When at last he withdrew his softening erection, Cheryl wasted no time jumping out of bed and running to the bathroom. I expected Tim to make some smartass remark to me, but he just clicked off the light on his side of the bed, lay down and pulled the covers over himself, apparently ready to go to sleep.

I heard the toilet flush behind the closed bathroom door and Cheryl came out moments later, wearing only a plain cotton robe. She walked over to me.

"I see you enjoyed watching. I'm sure you want to play with that little thing of yours," she said in a condescending tone, looking down her nose at my swollen erection, quivering above a pool of drippings. "You need to cool off first, and then I'll release you. Goodnight," Cheryl said and then she slapped my face much harder than I thought was necessary.

She walked over to her side of the bed, switched off her light, and shed her robe before snuggling up next to Tim.

"I love you," she told him.

"I love you too," he replied.

It wasn't long before I heard Tim snoring loudly. No doubt it would be easy to drift off into a deep and restful sleep after a hot romp like that, and I realized that if Cheryl fell fast asleep, I might end up cuffed to the chair all night.

Perhaps my erection was starting to soften in the darkness, because I realized I had to use the bathroom, thanks to the beers I had drank earlier that evening. It added to my frustration because I was certain that Cheryl had fallen asleep. I could hear her breathing now, deep and slow in between Tim's loud snores.

I thought that if I tried to wake them up, verbally, or by clearing my throat, or maybe squeaking the chair legs on the floor, that would piss her off and I would have to stay cuffed even longer. Unsure of what to do, I tried to adjust my position to get as comfortable as possible, though that proved to be impossible.

At one time I'd considered buying a pair of cuffs like the ones that were restraining me, and I knew they had little safety latches so the wearer could easily escape if the situation got out of hand. Making my escape at this point seemed like the best idea and I doubted they would care at this point. However, with the linking chain on the cuffs passed through a rung on the back of the chair, I had no slack to work with, and while I fumbled around quite a bit I couldn't find any release lever.

Who knows how long I sat there uncomfortably in the dark. I knew that a few times I started to nod off to sleep, only to wake up. At last I saw Cheryl move under the covers. I thought she was just rolling over, but she got out of bed and pulled on her robe. Of course she had misplaced the key and ended up turning on a light, waking Tim who rolled over and mumbled loudly. There were no parting words or swat on the ass and I just scurried out the bedroom door, which was closed swiftly behind me and locked.

Making my way down the stairs, I realized I hadn't even bothered to turn off the TV. I shut it off and picked up my clothes which were scattered on the floor. After taking a long piss, I decided to masturbate before going to sleep. My penis was somewhat achy, feeling almost clogged from that long period of arousal without having an orgasm. I wasn't horny, but felt it was best to masturbate and release that tension. Maintenance, if you will.

Taking my small tube of lotion, I sat on the toilet to jerk off. It took a surprisingly long time to get hard, and even then I never got solidly erect. Though I tried to envision past hot sexual encounters, and favorite scenes from porn videos, thoughts of my humiliating experience not long ago upstairs kept creeping into my mind, withering my cock in my hand.

I kept at it though, having to apply more lotion at times, and a little spit. It was work, I hate to say. At last I came, and the initial burst was somewhat painful. I stayed on the toilet, slowly stroking myself until I had squeezed out every drop of cum. It was the most unsatisfying time I had ever had masturbating.

I did not sleep well afterwards, and when the alarm went off it was still dark outside. Cheryl and Tim would not be up for several hours, but I left soon after I got out of bed. Didn't even bother to shower or shave, just made my treacherous drive down the winding mountain road into town, where I picked up a large coffee to go on my way to the interstate. That had been one strange vacation, certainly a memorable one, but mostly for the wrong reasons.

During my drive home I called Scotty and learned that his hasty departure was because a favorite uncle, a really old guy, had been rushed to the hospital and it didn't look like he was going to survive much longer. In the end though, the man made a full recovery.

We hung out with other friends as usual, at the usual places, though Tim never came around. Over time I learned that he and Cheryl had become engaged, but months later they split up.

One version of the story that I heard was that he broke things off after he caught her not using her birth control, trying to get knocked up so as to get a wedding date set. Another source said that she left Tim for another man who was a doctor or had some other high paying job in the medical field. I suspected the second story was true. Leaving for a man with a larger paycheck and the other guy might also have a foot long penis. I felt some sense of satisfaction when I heard that news.

My new girlfriend is a cute little chunky brunette, who has no problems with my taste for fetishes and other kinky stuff. She has her own twisted interests, such as having sex in public places, and there have been other times when she put a vibrator in my ass while giving me a blowjob, resulting in orgasms so explosive I nearly passed out. All stories for another time, perhaps.