Stew's Fantasy - Mie's Story

Keith and I have been together for twenty five years. I have always known that I =was gay beginning in High School in Texas, where I got caught have my face fucked by one football player while another plowed my rear end. Up until the advent of AIDS I was pretty promiscuous, but fear of the disease caused me to slow down my conquests. It was just pure luck that I had not acquired HIV when young. I probably was fucked by ½ of the guys at my college. In fact, Keith was one of the few men that did not fuck me - only, as I learned later, because he was fucking his roommate Richard in the ass every night.

After we got together, Keith and I remained in a committed monogamous relationship though we occasionally discussed doing something with another man or couple. Being bisexual, Keith had some interest in adding a woman and her husband to our scenario, but I am strictly gay. I find pussies repulsive, and the only way I ever fucked a woman (once) was to mount her from the rear, penetrate her asshole, and pretend that she was a man. Still, Keith could have fucked her while her mate fucked me.

Truthfully, we never did much more than talk about it. HIV is still a real threat to our emotional well-being, and to be truthful, anyone willing to enter into a relationship thanks to a Craiglist ad probably is the type to potentially get HIV. Still, I like to pursue the ads and share them with Keith.

So last week, I came across this add that caught my attention. Titled "Fulfill Straight Guys Gay Fantasy", the advertisement read:

"I am a 65-year-old heterosexual male. I have never had a any sort of sexual relationship with another male, nor do I really desire one. However, 35 years ago I watched a porno film in which a blond woman was fucked simultaneously by two men, one who mounted her doggy style and the other who fed her his dick in her mouth. I found that image extremely arousing, so arousing that I have since wondered what it would be like to be that woman, sandwiched between two men. This is the one and only gay fantasy that I have ever had. Now that the government is taking Craigslist Sex Ads off the web, this may be my last chance to look for two men to fulfil this fantasy of mine. I am looking for two men, disease free, preferably straight like me, to take turns fucking me once in the mouth and once in the ass while the other fucks the other orifice. I would really enjoy it is your wives/girlfriends watched. Because of diabetes and medications, I have difficulty getting and maintaining an erection, but I will gladly use my tongue, mouth, and asshole to satisfy any of you."

After showing the ad to a skeptical Keith, I contacted the man, explaining that Keith and I were a committed gay couple willing to bring him into our bed to satisfy his sexual fantasy.

A week later, he got back to us. I think we were the only people willing to fuck him, for in spite of not being straight, and not being able to provide an audience, he wanted to meet us and proceed with a sexual encounter. We set something up for the following weekend and waited for our encounter.

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His name was Stewart, and he showed up on our doorstep that Saturday at 10 AM as planned. He was, as he had warned us, an older, obese man who looked 12 months pregnant and had a bushy white beard. He was obviously very nervous, and I began to think that he might be legitimate. It was clear that he had never done such a thing before. Inviting him in, we sat down in the living room and introduced ourselves. When Stewart emphatically stated that he wanted to go thru with this, we retired to the bedroom to undress and get ready.

I am used to the fact that people would rather look at Keith than look at me. Stewart was clearly focused on Keith's attractive body. Keith still looks like the basketball player he was a CTBC. Also, he probably has the biggest dong in creation. Black men are well endowed, but Keith is better endowed than most. We have measure his dick as being 14 inches long flaccid, and when he is erect, it grows another two inches in length. The circumference of his cock is 11 inches wide, which means that when he enters my asshole, I must open it over three-and-a-half inches wide to get him inside me. By the tine Keith started fucking me, I had a lot of experience taking cocks of all sizes into my ass, but even for me it was a stretch to take him inside, and somewhat less than comfortable at first to have him move in an out of me. He told me that the first time he fucked his roommate Richard in college, it took almost 40 minutes for him to finally get his dick all the way up Richard's ass, and then he had to be content with short, vigorous thrusts in order to cum.

Anyway, it was not surprising to see Stewart staring at Keith's male member and to know that he was having second thoughts about having it in his tight virgin's ass. Personally, I was getting fairly excited myself. Although Stewart's dick was showing signs of life, mine had sprung up to half mast. Flaccid, I am a little under five inches long and five inches in diameter, but when aroused, my cock expands in girth to 6.5 inches and becomes 6.5 inches long, so I would say I have a normal, thick cock. But does anyone look at it? NO! They are too busy gaping at Keith's massive male member.

Once we were undressed, we went into the bathroom and got into the shower. For me, showering with other men is a turn on that goes back to my days at Hondo High School. By this time, I was fully erected, my prick standing at attention. Keith reached over and began to soap my dick before turning to Stewart and reaching down with his soapy hands to caress Stewart's dick. I don't think Stewart knew what to make of this, for he seemed to shrink. His prick certainly did. It pulled in to his abdomen and looked like the hairy counterpart to a small boy's penis.

I maneuvered behind Stewart and began to wash his back. Reaching around his body, I pulled him to myself and began to nip at his neck while Keith soaped up his chest, moving down across his bloated belly to his pubis. Moving his hand between Stewart's legs, Keith began to run his hands up Stewart's crack. We could tell that the shower was beginning to have its desired effect. Stewart began to relax and reciprocate, running his hands across our bodies, and grasping in them our erect cocks.

"You sure you want to do this?" I asked as we entered the bedroom. "You don't have too if you are having second thoughts.

"I have wanted to do this for four decades," Stewart replied. "My only concern is that I had no idea how big Keith was, but if you can take him up your ass, then I should be able to also," he replied.

"Yes, but I have been fucking Keith for over 20 years. You told me that no one has ever fucked you, that you do not even finger fuck yourself. It is going to be different. It is going to hurt. You sure you want to do this?"

"Yes," he replied. "Let's get on with it."

We crawled onto the bed. Keith was by the headboard; I was towards the foot of the bed where I could put my legs down if necessary. Stewart was in his desired place, his ass pointing towards me, his face gazing on Keith's erection.

"Let's do it," he said again, and he leaned forward and took Keith into his mouth. Seeing that he had begun to blow Keith, I lubed up my fingers and inserted one into his ass. Stewart moaned as he moved forward, his mouth sliding over a small portion of Keith's dick. Then he pushed back against my finger, further impaling his asshole upon it. For a few minutes he rocked back and forth on Keith's cock and my finger before I placed another finger into his asshole. Another moan escaped his throat. A longer period passed with him face fucking Keith's member while impaling himself upon my two fingers before I added a third. He seemed to have trouble accepting this finger, so I pushed it deeper into him and began to screw his shit chute with my three fingers until they were all the way in his asshole. Than I began to move them in and out, and he resumed his riding of my digits. After about ten minutes, I inserted a fourth finger. Again, it was difficult, and a moan issued from his face, not a moan of pleasure, but one of pain. Ignoring his pain, I twisted my fingers in his ass, loosening his sphincter as I contemplated how I was going to butt fuck him.

Removing my four fingers from his asshole, I stood up and pulled Stewart to the end of the bed. Keith then moved forward to replace his dick in Stewart's mouth. I had noticed that Keith was hardly moving as Steward had attended to his dick. Now I noticed a slight rhythm to Keith's hips as I prepared to enter Stewart from behind. Placing a generous amount of lube on my cock, particularly the head, I moved behind Stewart and placed the head of my dick against the hole of his loosened sphincter. Pushing against it, I encountered resistance.

"Relax, Stewart," I told him. "Bear down like you are trying to take a dump. It will make it easier."

Complying, I felt Stewart's anus pushing against my cock head, and I began to slowly insert my prick into his shit chute. In increments of about ½ an inch, I pushed my penis in before withdrawing it from his chute. After I had inserted about two to three inches of my male hood, I stopped taking it all the way out, and simply continued to push in and out, always moving a little deeper into his hole. He was whimpering in pain, but I did not let that stop me. The cunt wanted to be fucked by two men, for Pete's sake, so now he was going to get fucked. Looking across his bare back I could see that Keith had much the same idea. His pelvis was thrusting his dick in and out of Stewart's face, a steady rhythm forcing more of his member into Stewart's mouth.

Before ten minutes were up, my dick was completely in Stewart's ass, and his hole had been stretched to accommodate the two-and-a-half diameter of my dick. Instead of encountering resistance and listening to whimpers of pain, Stewart had begun to push hi hips back to receive me and was moaning with a degree of pleasure. I picked up the pace and began to fuck him faster and faster, my pendulous balls slapping against his perineum. The faster I went, the more he moaned and the louder his moans. Reaching around his body, I cupped his tiny little dick in my hand. Although not erect, it was slick with the precum driven from his prostrate gland by the head of my penis striking his p-spot. I smeared the viscous liquid around his penis and tried in vain to coax an erection. A muffled "fuck me, just fuck me" emerged from around Keith's head. So, placing my hands on his buttock, I began to thrust deeply into his rectum, pulling out my penis virtually the whole seven inches before driving it deep inside him. As my tension mounted, my body became tenser until finally, with one last driving thrust deep into his body, I spilled my semen deep inside Stewart's bowels.

It was an interesting sensation, being in Stewart's bung hole while Keith finished fucking his face. My cock was growing limp, yet the sensitive feelings were still present as I felt Stewart's anal sphincter bearing down on my dick. Like a piece of shit in his chute, the relentless compression of his sphincter pushed against my flaccid manhood, and though the length slowed down progress, eventually Stewart expelled me from his asshole. Stepping up to bed, I lay down facing the ceiling, my newly exposed cock lying limply across my left thigh.

Keith too lay down on his side facing us, while Stewart stretched out face down upon the bed. We relaxed for a few minutes, nobody speaking, each wrapped up in their own thoughts.

"Well, Stewart, how does it feel to have fulfilled a fantasy you have cherished for so many years?" Keith asked.

Pushing up onto his elbows, Stewart responded. "I feel good. It hurt a lot but I expected pain to be a part of the process of loosing my virginity to you guys. Of course, I had no idea how big you were, and I am sure it hurt more because of that, but right now I feel good. I feel like I have accomplished something important."

"Well, you are not finished yet," I reminded him. "You told us that you wanted us to switch places after we came. As soon as we have recovered, you get to suck my dick and have the pleasure of Keith's massive make member deep in your ass. Then, and only then, will you have accomplished what you set out to do."

He silently contemplated that.

While my cock was thicker than Stewart's, he was not as afraid of it. He eagerly embraced it with his mouth and began to give me a primitive blow job, a blow job which was interrupted when Keith pushed his enormous dick deep into Stewart's ass. In a way I was not surprised. Keith had told me how he essentially raped his roommate Richard when Richard offered to be used as an instrument to prepare for Keith's honeymoon. Keith has a real problem with gays who pretend their straight, which is surprising because he himself is bi, and understands that people can be attracted to both genders. Yet his savage thrust into Stewart's bowels interrupted my blow job, and it really took Stewart a while to resume his work.

Once Stewart became accustomed to Keith's massive dick inside his still tight ass, he began to suck my dick with enthusiasm. Keith had told him to suck cock as you want your cock sucked, and Stew had taken that to heart. While it was obvious that he was still a novice at cock sucking, I was enjoying his ministration, doing little to enhance the pleasure I was receiving. Instead, I just gradually slipped my dick deeper and deeper into his throat until my hanging balls felt his chin. Stroking his head, I whispered "all of me is in you now." I think he was surprised to hear that. With that, I began my own series of thrusts into his mouth, moving my cock in and out, feeling it swell slightly as Stewart pleasured it.

Having come in his ass less than an hour earlier, I was in no need, mood, or condition to come right away, so for the next ½ hour I gently fucked his face while the suction of his mouth and the warm wetness of his tongue caressing my cock satisfied my sexual needs.

Keith came with a deep thrust that impaled Stewart on my prick. I wondered if Stewart would be able to push out Keith's flaccid 14 inches from his anus that way he had mine. I kind of doubted it. I have slept with Keith in my ass many a night: such a length is not easily moved by the strictures of a sphincter.

I decided that Stew had probably had enough though, so increasing the frequency of my thrusts, I sank my dick entirely into his mouth and exploded, pouring cum into his gullet. His air supply suddenly cut off, he quickly swallowed the spray of white jism I had deposited.

I don't know if we will ever see Stewart again. We fulfilled the fantasy that had troubled him for decades. We left him with a sore and bleeding asshole and the taste of jism in his stomach. Whether he would ever accept the homosexual side of his nature or not remains to be seen. But for a moment, he got to experience what some porno slut had experienced three decades earlier- being sandwiched between two men, their cocks exploding in the bitch caught between them.