Dory and the… 26 in Dick

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Dory and the Man Who Claimed to Have a 26 Inch Dick.

Leaving the bookstore I impulsively grabbed a copy of a swingers mag. At home I paged through it but found nothing worth pursuing until this:

“Twenty-six inch cock needs sword-swallower. First time deep-throaters need not apply.”

Obviously, that was hyperbole, meant to indicate he had a very big cock. And, well, I’ve always wanted to deepthroat a really big cock.

I answered the ad asking how big it really was, what he wanted to do to me, where we could do it, and whether or not he was married.

I got a reply two days later: he said he was twenty-six inches long, but I questioned his sincerety, he wanted to fuck my throat slowly, we could do it at his house because he was single. He also asked how long I could hold my breath.

I would have ignored his email as ridiculous but that part about me holding my breath intrigued me. I told him I needed to see a pic. I also answered that I had timed myself and could hold my breath for seventy seconds.

Again, another two days went by: his reply was curt and unsatisfying. He said he wanted me to call him ‘Sir’, that if I wanted to see it I had to come over, and that I wouldn’t be invited until I got my time up to two minutes.

What an arrogant son of a bitch! While I liked the idea of calling him Sir, I wouldn’t make a trip out unless I knew it was big. I told him as much. Taunting him I added that after some practice I could hold my breath for two minutes and that it was his loss.

In the next email Sir said he liked my surly attitude and would enjoy putting me in my place. He asked what the biggest cock I ever sucked was. He ended with, “Master is proud of you for getting up to two minutes. Few cocksuckers have the perseverance to learn. I’m willing to take a chance on you.”

It felt like an accomplishment to have been accepted, even if I did lie about holding my breath for two minutes. I told him the biggest I had sucked was nine inches and asked again for his real measurements.

It was a week before Sir sent another email. Nothing like being in a hurry. This one included a picture of him from the waist up; he wanted a similar pic from me. He told me if I could do nine, I could do fourteen, or twenty-six. He ended with a bet and a challenge. He said that when I came over we would both put $500 in a hat. Then, “If mine isn’t the biggest you’ve ever swallowed you can have all the money. But if it’s bigger than the largest you’ve done I keep it all.

The chance to have a record-breaker slowly reaming me would be worth five hundred should I lose. But if he were smaller then I would suck his cock and walk out with the cash. I agreed to his terms as long as I could bring a witness. This was just too strange to be believed – or safe.

But now I needed to learn to hold my breath longer. I started practicing and by the end of that day my time was up to eighty seconds.

I was excited to see the red flag on my email account a few days later. Opening it, I saw that he told me that the witness needed to be someone small so that the two of us wouldn’t overpower him and steal the cash.

I tried to think of someone who would fit the bill and the only person I could think of was the new girl I was dating. Only she didn’t know that I sucked cock. How would she take it?

First I sent back an email, “OK, I’ll bring my girl. When I suck you, would you like me to kneel, or 69, or what? Does next Friday work?”

I could now hold my breath for ninety seconds.

Eight days before the “big event” and I had yet to talk to Dory. She might stop seeing me when she heard how fucked up this all was. It wouldn’t be the biggest loss in the world, but I did enjoy her company. There was definitely something different and refreshing about her. Should I throw away a chance at what might be a really good thing with her for what might be a chance at a really bad hook up?

I would miss her body too. She was average height with a slim waist, and smallish tits. Classic blue-eyed, platinum blonde curls, eye candy. She always dressed ultra girly, dresses, hose, heels, etc.

We came back to my place after dinner and I broached the subject, “So, we’ve been dating for a few weeks now…” I could tell by the look on her face that she knew this wasn’t a casual conversation. She smiled weakly and nodded. I asked, “Have you ever dated a guy who was into a kink?”

The smile left her face. Then she looked worried. Then, slyly, she smiled again. “I’m open minded. Would you like me to dress up like something? Or put my finger up your bum when I blow you?” She held up one painted finger while she said this, then tilted her head sideways waiting for me to go on.

I felt some hope that she really would be open. If we were still dating by the end of the night I had dreams of really finding out how open minded she could be. I swallowed what felt like a walnut in my throat, “Did you ever date a guy who was curious about the other side?” almanbahis She looked confused, so I gave her more, “Playing for the other team.”

I saw the realization come over her face. She answered coyly, “Not yet.” She drew out the word ‘yet’ holding the syllable really long. Then dropped her own bombshell, “Did you know I experimented in college…?”

I didn’t know I had been holding my breath until I let it out. I guess I interrupted her. Ignoring her revelation I asked, “So, you’re OK with it?”

“Oh, Honey, I’m sooo OK! In fact, if you want, I know a guy who wants to dress like a girl and suck a dick. I could set it up for him to blow you…unless…Is it something else you want to try?” She leaned closer as she was saying this and patted her ass provocatively. “You could have mine, you know”

I had no idea Dory was so wild. Up until now all our sex had been very vanilla: a handful of blowjobs really was all. This was going to be a great thing. And I was starting to think if it didn’t cross any lines, she would be willing to be my witness.

“Dory, I’ve done it before you know. Before we started dating. More than once…” I felt like I needed to clarify, “I’ve…I like to suck.” There! I said it.

A wicked smile spread from ear to ear, “Oh, you naughty boy! If you like we can go looking. I’ll be your wingman.”

So far nothing shocked or surprised her. Would my next news? “I’ve already found the guy. Well, we’ve emailed. I just need a few things to make it work.”

She seemed dejected but hid it, “And you’re asking for my permission? How cute. I didn’t think we were exclusive. But you’ve got it.” Dory touched my hand comfortingly, “Will you tell me all about it? I mean…after?”

I went on as if she didn’t just initiate the question about our relationship definition, “I’m interested in big ones. This guy is big. Well, he says he is. I’ll know when I get there. He even promised that if he’s not the biggest that, er, you see, we made a bet, that he’ll pay me. He’s that confident.

But with money on the table he wants a witness.” (A little white lie) This is where I got nervous again. “Would you, I mean, be willing to watch?”

Dory laughed in my face. At first, I thought she was refusing me. “It sounds like a hoot. I’ve never seen that.

I took her face and I kissed her. Really passionately. Her hands roamed to my cock and, in turn, I squeezed her boobs through her tight push up bra. Still massaging my growing penis she asked, “So how big is this man anyway?”

“That’s the thing! I don’t know. He bet he’ll be bigger than any I’ve ever had, but he says he’s twenty six inches long, that’s like eight inches bigger than the world’s record. So I guess we’ll find out when we get there.”

Her eyes were like saucers, “Do you really want to do it if he’s that big? I, for one, wouldn’t want to. It’s bound to hurt.”

I was staring at her cleavage. I guess I couldn’t look her in the eye. I answered softly, with trepidation, “I do. Especially if he’s big. The bigger the better. If he’s bigger than nine I lose the bet but it’ll be a personal best for me, and if he’s smaller than nine I’ll walk out with $500.

“Shit Jim! you’d pay five hundred just to suck one bigger than nine? There’s gotta be easier ways. Besides maybe size isn’t that important. What else is nice about a dick?”

She had me on the defensive here. She was right that there would be easier ways. “It’s not just that he’s big. His scenario sounds hot too. And if by some odd chance it’s really twenty six inches, well, don’t you want to see that? Just to see it would be something else.”

She dismissed my thought, “We could find pics like that on the internet. But what really has me curious is that whatever quirky situation he’s got going on, it has you all hot and bothered. I can see it on your face, and your cock is harder than ever, I can practically feel your pulse quicken.

Soooo, out with it. What’s your dark little secret? Tell me and I’ll share mine…”

She made it sound like whatever my secret was I just had to tell her and it would all be alright. But would it? She had this view of me as a strong protector. She had even assumed I wanted to top and I had had to admit I saw myself as more of a bottom cocksucker.

I was being a size obsessed broken man. And now she wants me to admit that I want to be dominated, to call him ‘Sir’, to have him abuse me so much that he’s going to choke me on his big cock. It was all too twisted. She wanted me to confess that that’s the reason I would pay $500. I just couldn’t do it.

I think she sensed my reluctance saying, “When we get there we’ll see how big it is. In the meantime, I have a little fantasy too. Do you think you might help a girl out?”

I agreed not knowing what it was. But it was good to change the subject. I saw her weigh her options in her mind then she spilled the beans, she just wanted to play doctor. She was so horned up by the idea that we even went to the sex almanbahis yeni giriş store to buy props. And we had fun. Not cocksucking fun – but fun. She was the sexy doctor and she put me through her dirty exams. Naturally, it ended with a sperm count.

The next morning I checked my email right away. I kinda felt like a giddy newbie, and sure enough there was a note from the guy. “You’re gonna come in and take off all your clothes. Every time you open your mouth you and your girl will use the word ‘Sir.’ I have a chair for you. I’ll show you my cock, and when both you and your girl agree it’s the biggest, I’ll feed it to you. All the way down. No going back. Two minutes at a time!”

I had a sense of foreboding. Dory would see firsthand what I couldn’t bring myself to tell her. Furthermore, she would see me be thrilled to be abused.

But also – two minutes!” Something about that thrilled me.

With more practice my time got longer each day. I watched videos on deep sea diving and learned to hyperventilate. By Thursday I was up to a minute forty-five before I would explode in a gasping fury of expelled breath and painful lungs. Every additional second felt like an impossible eternity.

I picked up Dory at eight. She said she’d been doing her make-up all afternoon. Then we did a joint to relax and drove over. Twenty minutes of conversation talking about anything but. It should have been awkward but nothing ever was with Dory. My hand was frigid as I grasped hers. Hers was too. But why would she be nervous? I was the one who would have to tell her that we were both expected to call him Sir, a scary hint explaining what the scenario would be like.

My finger paused before the bell. We could just turn around. Dory even said we could just look for a smaller dick. But she also spurred me on, “I’ll still love you after.” She had never said that before and in that moment I realized I loved her too. I turned to tell her but the door opened before I could push the doorbell.

Sir wasn’t particularly impressive. He wasn’t not impressive either. I looked for a line running down his leg and didn’t see one.

His attitude was bossy, “Sir is here to be serviced and you are here to do it. Come in if you accept, both of you.” Did he expect sex from Dory? I couldn’t let him do that. I felt her hand on the small of my back directing me in. In my consciousness, all I heard was the clicking of her heels while we crossed the momentous threshold.

Sir commanded me to put my clothes on a chair by the front door. He was super rude which is something I would not put up with except in the sub/dom context. Also, I didn’t really know if he was talking to just me or both of us. I didn’t want Dory to expose herself to him but, reading my mind, Sir offered, “No. just you.”

That concession gave me the courage I needed. I stripped and we followed him to what he called the ‘playroom.’ Sir led, Dory followed me: the only nude one. I can’t say I’ve ever felt more naked. My penis felt shrivelled and small, whereas at its best it’s normally a good seven and a half.

In the playroom were the normal pieces of furniture one would find in a living room, chairs, lamps, clock, except for the presence of one of those sitting massage chairs that had the hole for your face. Sir motioned for me to sit in it. I spoke for the first time since entering, simply saying, “Yes, Sir.” My girl heard me calling him ‘Sir’ and my face burned hot with shame.

He made a show of putting five hundred dollars into a big Ringmaster’s hat and Dory deposited mine as well.

Next he started a long monologue, “My Father was consumed by the thought that a large dick made the man. I caught the sickness too. As a young man I found a doctor who offered to make me huge. He had a treatment that tricked one’s body into thinking it was prepubescent. The result being that my cock kept growing as long as I took it: just like anyone’s cock grows in early puberty.

My sclong grew to a big size. But I always wanted just a little more. I devoted all my resources to that end, and it worked. By the time I was done, I was tremendous. And out ten grand.

But my fantasy turned into a nightmare. No woman would have me. The prostitutes mostly ran and the one’s that stayed could only take a fourth of it. Can you imagine only fucking with the first fourth of your cock?

Anal sex is out of the question. Masturbation is, uh, problematic, too. Only the human esophagus is long enough. By now he had taken off his shirt.

The fags and bi-curious are sometimes willing to try. Then again, mostly they give up, if given the choice.” He looked to Dory, “You can appreciate their fear?”

She nodded then added, “Oh yes Sir. I’m sure they do. Choices can be so hard.” Somehow, her calling him ‘Sir’ too, put us on a level plane.

Then he went on, “So you’ll both understand why I have to get a commitment before you see it? There’s no turning back,then?”

We agreed with head nods, but almanbahis giriş that wasn’t enough. He barked, “Say it!”

“Yes Sir.” I said.

“Yes Sir, what?”

Cowered, I affirmed what he wanted to hear. “Yes Sir! I’ll suck it. And I won’t back out.”

He pressed for more, “Do you both agree you won’t back out. I’ll fuck his throat and neither of you will try to stop me? It’ll go all the way to his stomach. You won’t complain, Dory?” She seemed lost in thought. “Dory?!”

She agreed but that too wasn’t good enough. He gave her a stern look and she responded, “Oh Yes Sir. You can do it. I won’t stop you – Sir.”

He probed for more, “And…” He took off his shoes and socks.

She gave her full consent much too readily, “Right, Sir. I won’t even complain, Sir. In fact, I want to see it. Push it to the hilt.” However, she didn’t know what I knew. She didn’t know about the two minutes.

“When your boyfriend wants to quit, or even if you just want him to quit, you need to have restraint. But you will be impulsive. You will want to help. It’s a woman’s nature. We can’t have you rushing in.” With that he handed her some handcuffs. “Try them out first. There’s a combination lock. It will only take a minute to unlock them. You can take them off yourself. But it will take a minute to enter the code. One, six, seven, nine. In that minute you will get control over yourself.”

She locked and unlocked them, then she put them on and sat in a chair, crossing her ankles, to watch from the sidelines.

Sir faced me, “I’m about to show you. But you have to promise not to leave when you see it.” He held up some straps. “Do you submit?”

“Yes Sir. I promise I won’t leave.” Sir started to strap my head into the padded face-hole. “I promise you can fuck my throat.” Sir strapped my hands down too. “You can go all the way. You can choke me for minutes.” Sir fastened my ankles as well.

I glanced to Dory, afraid to see how she would react now that she fully knew why I was here. She blew me a kiss. Hell if I knew what it meant, but it seemed…accepting.

Sir removed his pants. I could see something lurking inside his boxers.

He placed his thumbs inside the elastic. “When you see how big it is, you’ll pay up?” Within the confines of the contraption which imprisoned me I assented.

Sir lowered his underwear enough for us to see his great bushy mass of hair. It was thick and black and dense.

Next he dropped them to his ankles. There! I saw it. Soft it was over ten inches. Sir was asking,”Do you surrender the cash?”

Neither one of us could speak. He wasn’t even nearly hard and he’d already won. Could it really get to be twenty-six inches? Surely he was a shower rather than a grower. It would probably only grow a few inches. Yet, I had both butterflies and a pit in my stomach.

Sir was still talking. “And do you surrender your mouth?”

I wasn’t at all sure. I pulled on the restraints and they barely budged. I struggled against each one: I was committed, like it or not. I worked up the courage to answer but before I could say anything Dory answered for me.

Her amazed voice was breathless and barely audible “He does Sir. He surrenders his cash and his mouth to your cock and cum. He needs it. And we’ll be back for you to do him again.”

At my house she had seemed so unmoved by the concept of a huge cock and here she was under its spell so soon.

He asked her, “Do you want to make it wet for him?” Mesmerized, she shook her head slowly, in disbelief. Not willing to take the risk herself but totally willing to volunteer me.

She regained full control of her voice so, louder now, she asserted with husky gusto, “He…I need you to spear him. At this moment it’s all I want. Do it!” Her cuffed hands dropped to her lap. I couldn’t turn my head much but I’m pretty sure I saw her fingers snake under the bunched up hem of her dress. “Do it! Sir”

I wasn’t sure how well I knew this woman who minutes before announced her love for me. Who moments before I felt the need to return that love to. Sir had said she would feel a need to help me, but I saw zero evidence that she was on my side as opposed to his.

Sir stepped forward but was still a foot away. With his left hand he petted the back of my head and with his right he lifted the massive hefty salami that arched downward under its own weight. He hoisted it up higher than my mouth letting the hanging end flop down toward me.

On my right Dory was saying anxiously, “Open up, Jimmy.”

Sir slapped the head onto my tongue and left it there. I closed my lips over the end, sucking hard and fast, needing to bring it to life. And boy did it ever. As it grew Sir left just the tip in me, sliding his feet back as it expanded.

It must have taken three or four minutes for it to grow. Sir was two feet away from me now but the long bridge still arched across the channel connecting us. Dory whistled in awe, what else was there to say?

Sir was first to say anything. He was talking to Dory, “You’ll let him take it?”

With cuffed hands and two extended fingers she pointed to my mid-section, “It’s gonna reach to there.” I could hear the disbelief in her voice. “Is it gonna, will it hurt?”

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