The Homeless Shelter ch. 20

I had been volunteering at the homeless shelter since my retirement from work for a couple of months, and things had been going great. Quite a few of the guys who had been using the shelter when I’d last volunteered, practically a year ago, knew me and, more importantly, my fetish for servicing the homeless, so I was getting lots and lots of extramarital cock. Additionally, I had been seeing my black lover Todd quite often, especially when my husband Ted had been away on business for lengthy periods. Despite the fact I had Ted’s blessing to let Todd fuck me and the fact it seemed to only have enhanced our personal sex life when Ted was home, I still felt guilty and a little ashamed at the fact I was having other sex. Despite that, I knew I couldn’t give it up.

What the fuck is wrong with me? I thought to myself one evening as I made my way to the loading dock behind a furniture shop, close to my lover Todd’s liquor store, having just let Todd fuck me. Todd had fucked my pussycat hard with his big cock, and then, thankfully, he had taken me anally and spurted his hot cum into my anus, so my pants hadn’t yet filled with cum as I walked. As per usual, I had collected a bottle of Irish whiskey to take to Gil, a homeless guy who slept on the dock, with my mouth already drooling at the thought of sucking his big cock and that of anyone else who was there. Although I’d let Gil and a few other guys fuck me, a couple of times, on a grubby mattress they had up on the dock, I told them that the weather was getting far too cold for me to be naked and they would have to make do with me sucking them off.

To my surprise, when I got there, Gil was alone, but his eyes still lit up when he saw me and the bottle of Irish whiskey I was carrying. For a minute or two, I began to wonder what he liked the thought of more, me or the whiskey, until I saw him begin to rub his crotch as he called out to me, "Hey, posh lady! You’re a sight for sore eyes and a throbbing cock. Gil was sitting in a wooden chair, and he stood up, went to a shopping cart next to him, and pulled out a couple of plastic cups and a blanket. As I leveled with him, he dropped the blanket on the floor in front of the chair, and as I handed him the bottle of whiskey, he handed me the two cups. Gil cracked the bottle and poured some whiskey into each cup before he took one, tapped it against mine, and said, “Here’s to you, sweet lady.”

We both downed the whiskey in our cups in one go, and as I felt the harsh fluid burn my throat and stomach, Gil refilled his cup, took a seat on the chair, and said, "Oh, sweet lady. Do your stuff, honey! Make old Gil a happy man!” Like the slut I had become, I immediately dropped to my knees on the blanket Gill had dropped on the floor, kneeling between Gil’s legs. I could already see the outline of his mammoth cock pressing against the tight material of the sweatpants he was wearing. I rubbed his throbbing cock through the material a few times as I stared at him, and then I hooked my fingers into the waistband of his sweat pants and tugged them down as Gil briefly lifted his buttocks off the chair.

Gil’s sweat pants and boxers slid down to his knees, and his massive cock flopped free, still only half-erect but already at its full ten inches in length. I gripped it, still staring up at him as I began to stroke it, feeling the blood pumping into it and making it swell. Gil gulped down his second shot of whisky, then grinned at me as he refilled the cup again. I leaned forward and began to lick the tip of his cock. Little beads of pre-cum oozed out of his piss hole, and I greedily lapped them up with the tip of my tongue. Gil’s cock continued to swell, and I took the big plum-colored head into my mouth, sucking hard on it and probing my tongue into his piss hole. I heard Gil let out a groan, and I sensed his body relax.

Once he was fully hard, I continued to suck his cock head, allowing the saliva that was building up to dribble out the sides of my mouth and stroking it up and down his thick throbbing shaft, making it slick, all the while going lower with my head, easing the length of his cock into my mouth until the head of it pressed against my throat. I could feel Gil’s cock pulsing as I kept it wedged deep in my mouth, and I had to fight my gag reflex. I was determined to give Gil a treat, so I took a deep breath through my nose, braced myself, relaxed my throat, and forced my head down. Gil groaned loudly as the head of his cock passed my tonsils and entered my throat, and I felt his hand on the back of my head, forcing it even lower and forcing his cock into me right to the hilt. He held my head there as I gagged, my nose buried in his wiry pubic hair, and the smell of him stinging my nostrils made my eyes water even more.

I put a hand on the back of my head, finding Gil's hand and scrunching his fingers around my hair, before giving it a couple of thrusts up and down, encouraging him to be rough with me. Gil took the hint; he gripped my hair so tightly that, in his boney fingers, my scalp burned with pain. He then began pulling and pushing my head, using my mouth as a fuck hole. Gil got a little carried away with his thrusting, and I felt like his cock was going to burst out of my throat as he kept holding my head down, his cock throbbing and filling my throat. Spittle was spurting through my lips, my eyes were watering, and my nose was burning as I kept breathing hard, and the stale smell of sweat and grime rushed up my nose, making my head dizzy.

As this continued, I was mindful that it usually takes Gil a long time to cum, and I was beginning to feel dizzy and sick with the smell and the lack of oxygen getting to my brain. I pushed hard against the chair with my hands, forcing my head up, and as Gil’s saliva-soaked cock was ejected from my mouth, I sucked in the air, gasping for breath and clearing my head. "Oh, fuck Gil. I can’t do that for too long, sweetie.” I softly murmured.

Gil looked down at me, looking almost sad but certainly disappointed. “C’mon, baby, make old Gil happy one last time.” He groaned. I looked at him and asked him what he meant. Gil told me the weather was getting cold and he had been given a place in a hostel, way over the other side of town, so he had taken it. “This may be the last time you see me here, posh lady,” he said with a smile. My heart thumped a little in my chest, and I felt strangely sad at the thought of maybe not seeing Gil again. I made a choice, going back on the promise I’d made to myself about only blowing jobs from now on.

Despite the fact I’d been fucked hard by my black lover Todd just an hour earlier and my pussy was sore, I knew my pussy was clean of cum, so I stood up and smiled at Gil as I peeled off my pants. I then peeled off my pants, noticing they were wet with my love juice, which I threw at Gil, and unfastened my coat. I hadn’t bothered wearing a bra when I went to see Todd, and as soon as I unfastened my coat, my nipples turned bullet-hard, poking through the fabric of my zip-up top. "Well, if it’s the last time, I’d best send you off with a bang, then hadn’t I?” I said this to Gil before I picked up my cup and asked him to fill me up. Gil reached for the bottle of whiskey and poured some into my cup, over half filling it. I took a deep breath and slugged the whole lot down in three big gulps. My throat and stomach burned as the liquid hit them, and seconds later I felt a fuzzy rush to my head.

I stepped forward and straddled Gil before reaching down between my legs and gripping his mammoth tool. “You know I’m married, right?” I asked him. He nodded and smiled. “I want your big cock in my posh married cunt!” I groaned at him before I guided the head of his big, hard cock between my pussy lips. I rubbed it back and forth a little, but there wasn’t much need for lubrication as his cock was already wet and sticky with my saliva. “Oooooooooohhhhhhhhhhhhh!! Fffffuuuuuuccccckkkk! Yeeessssss!” I groaned as I slowly lowered my hips, impaling myself on Gil’s massive throbbing tool. As my buttocks landed on Gil’s thighs, I felt his big cock head push through my cervix and nestle in the entrance to my womb. I panted away, breathing hard, as my throbbing pussy stretched around the invader, getting used to its size.

After a minute or two, I began to feel comfortable, and the feeling of pain was now just a feeling of sheer sexual fullness. I began to lift myself up and then lower myself down, slowly at first. Each time I lowered myself, it felt like Gil’s cock was penetrating me again. After a couple of minutes, his cock was soaked with my juice, which was flooding from my pussycat, and I began to bounce up and down on Gil’s cock, my hands gripping onto his shoulders. As I bounced up and down, my D-cup breasts bounced under my zip-up top. My nipples were so sensitive that they tingled and stung as the fabric of my top rasped over them. I paused for a second and pulled down the zip, exposing my breasts to Gil. Within seconds, his boney fingers were squeezing them and pinching my hard nipples.

I carried on bouncing on Gil’s cock for several more minutes. The feel of it was amazing—so big and so deep inside me—but something inside me made me want more. I stopped bouncing and started grinding my clitoral bone against Gil’s pubic bone. “Oooooooohh! Uuuuuughh! Nnnnngggghhh! I groaned as sexual shock waves shot through my body. Again, I stopped. I wanted to feel headier. “Pass me the bottle, Gil.” I moaned. Gil reached down to his side and passed me the bottle of whisky. He took a slug and then passed me the bottle. I wrapped my lips around it, tasting his saliva, before I tipped my head back and drank several gulps. My mouth, throat, and stomach burned. I kept the last gulp in my mouth as I handed Gil the bottle back.

I waited for Gil to put the bottle down, and then I grasped his face with both hands before I let some of my mouthfuls of whiskey dribble out of my mouth and onto my breasts. When it was nearly all gone, I leaned forward and pressed my lips hard against Gil’s mouth. As we kissed, I forced my tongue into his mouth and let the last trickle of whiskey flow into it. I swirled my tongue around Gil’s mouth, flicking it across his rough teeth, and Gil forced his tongue into my mouth. It felt so long and thick as it filled my mouth. I bounced up and down on his cock faster, and I felt my insides throbbing and shaking as tremors rumbled through me.

“Oh god, Gil. I fucking love your cock!” I shrieked as I bounced even quicker. Gil lowered his lead and started licking my whiskey-soaked breasts. “Yessss! Suck my nipples. Fucking bite them!” I wailed. Gil went to work on my breasts and nipples with his mouth, sucking and biting me, his rough, unshaven face rasping across my soft flesh. “oooooooohhh! Oooooowwww! Less! I failed as he got rougher and rougher with me. I bounced on his cock harder and faster, grinding my clitoral against him. “Ooooooooooh Gil. Fuck me. Make me cum on your big cock!” I squealed. Gil sucked hard on my nipples—so hard it felt like they were bleeding. His hands grasped my buttocks, his boney fingers with long nails digging into my flesh, almost tearing it.

Gil pulled my pelvis hard against him as I bounced up and down. As the pressure on my clitoral area increased, it felt like it was going to burst. My pussycat was on fire, and every inch of my body tingled, from my toes to my bullet-hard nipples. Gil was busy sucking and biting as I rode his monster cock. I felt my insides begin to rumble, and tremors rushed through my body. “Oooooooooohhhhhh! Fuck! Yessssss! Oh, Shit Gil! I’m going to fucking cum.” I wailed. “Oooohhhh! Ohhhhhhh! Oooooh. Aaaaaaaa! Aaaaaaaah! Mmmmmmmmmmpppppphhhhh! Yessssssssss!” I squealed as my back arched, and a hot flush came over me as my orgasm hit me so hard that I almost crushed Gil as I clamped my arms around his body.

We remained locked together, my whole body shuddering as my orgasm sent wave after wave of sexual pleasure through me. I could feel Gil’s rock-hard cock wedged and throbbing deep inside me as my pussycat spasmed around it, almost trying to suck the cum from his balls. Finally, my orgasm began to ebb, and the feel of Gil’s hard cock deep inside me told me he hadn’t cum yet. I breathed deeply, letting out a huge post-orgasmic sigh as my body went limp and I slumped forward, my head resting on Gil’s shoulder. For a couple of minutes, we remained still as my mind raced, and thoughts I never believed I’d ever have entered my head. I leaned back and looked Gill in the eyes. Then I lifted myself off his cock, and once I was standing, I took his hand and led him to the grubby mattress, where I had been fucked before.

I lay down and urged Gil to kneel between my legs, then pulled him towards me. Gil lowered his body, and our eyes locked together. I paused and took a deep breath, not believing what I was about to say. I already hated myself, but I knew I couldn’t resist. I wanted it so much. “Gil!” I said softly, as tears almost welled up in my eyes. “Make love to me!” Gil smiled, probably not believing what he had just heard, and paused for a few seconds. Then he lowered his head and kissed me gently on the lips. After a few seconds, Gil pushed his tongue between my lips, and I willingly opened my mouth to accept it. Gil’s tongue filled my mouth, swirling around my tongue. It still tasted of whiskey, and my taste buds felt warm and tingly.

Gil continued to kiss me for another minute as his hands wandered over my body, my skin tingled, and his bony fingers traced over my breasts and stomach. And then he began to work his way down my body, his big tongue flickering over my breasts. He sucked my nipples before he continued to work down, circling my navel, and eventually, his mouth hovered over my pussycat. I was wet and trembling with sexual anticipation as I felt his hot breath on my pussy lips, and then it happened. I almost jumped as his tongue probed between my pussy lips, slithering up and down my slit, circling my sensitive clitoral area before he probed his tongue deeper. Gil’s tongue had felt big in my mouth, but it felt even bigger now as he forced it into me, snaking its way deep into my love tunnel. The rough hair of his unshaven face rasped over my soft pussy lips as I squirmed beneath him, heightening my arousal and the burning inside my pussy.

As Gil continued to fuck my pussycat with his huge tongue, his boney fingers went walkabout on my sensual areas. I felt a bony finger beginning to probe into my butthole, and another finger found my clitoral area. A full-on assault then commenced on all my private parts. The boney finger in my butthole went deeper, and the other boney finger on my clitoral area was replaced by Gil’s mouth. He clamped his lips around my clitoral area and sucked hard, occasionally stopping to flick it with his tongue. I could feel my whole body starting to tingle, and my pre-orgasmic tremors began. I cupped my breasts and squeezed my hardened nipples, pulling them hard as Gil drove me to the edge. Seconds later, my back involuntarily arched and my orgasm exploded.

I panted and shrieked my way through my orgasm, for what felt like an age, my whole body shuddering, my insides throbbing and burning as Gill forced his tongue deep into my pussy, lapping at my cum. Eventually, with a huge sigh, I began to relax, and my body went a little limp. “Oh fuck me, Gil, that was amazing.” I softly moaned as I continued to breathe heavily.

“I ain't done with you yet, posh lady!” Gil responded with a slight chuckle, sounding like a man who was very pleased with himself. As he spoke, he moved his head towards my face, and as he got closer, I could feel his hard cock prodding against the lips of my pussycat. Gil was leaning on his hands, on either side of my shoulders, his arms taking his weight. “Stick my big cock in your posh cunt for me!” He demanded. I obeyed, gripping his massive throbbing tool and guiding the head of it past my pussy lips into my pulsing love tunnel. It felt tight, but it didn’t deter Gil, and he pushed his hips forward, sliding his full length into me.

“Ooooooommmmmpppppphhhh! Ooooowwww! Oooooh, fucking hell!” I groaned as his cock filled me to the bursting point. Then he started fucking me. He rammed his huge cock into me slowly at first, getting a little quicker as the minutes went on. My pussycat was so sore and stretched, but I loved it and urged Gil to fuck me harder and faster. “Come on, Gil, baby! Fuck me. Fuck my posh married cunt hard. Hurt me!” I shrieked as Gil increased his speed and how hard he rammed into me. I knew it was only a matter of minutes before I was going to cough again; my pussycat was on fire, the heat radiating through my body. I wrapped my legs around Gil, my heels digging into his buttocks, and gripped his shoulders. I pulled his face toward me, staring into his eyes. "Oh, fuck me, baby! Seed my cunt!” I cried out. Gill planted his lips on mine and forced his tongue into my mouth. The taste of my orgasm juice on his lips and tongue took me over the edge, and I came hard, my hips bucking upwards to meet his thrusts.

Gil broke off the kiss, and his head went onto my shoulder, his body pressing against me and his pubic bone grinding my clitoral area as he continued to fuck me through my orgasm. My head went fuzzy, and I suddenly had an almost out-of-body experience. Images flashed through my mind of me looking down at the scene. A blonde, middle-class, former career woman, now housewife, prim and proper pillar of the community, legs spread on a grimy, piss-stained mattress, and an unkempt homeless black guy buttocks clenched as he fucked the shit out of her orgasming, shrieking body. Tears suddenly welled up in my eyes and rolled down my face as I heard Gil grunt and cry, "Oh yessss! Here it fuckin comes, posh lady!” Then, with a final deep thrust, he pumped his cum deep into my womb. It felt sticky and hot as it spurted into me for what felt like ages.

Finally Gil stopped thrusting and panting. He let out a sigh and propped himself up, pulling his cock away from me. He stood and walked away, towards the chair, picked up the whisky bottle, and drained the last of the contents. He pulled up his pants and grabbed a coat, putting it on. He stood staring at me. “You’re one fine fuck posh lady. I’m going to miss you. I gotta go get me some food and drink.” He said this before he walked away, leaving me exposed and lying on my back. Tears streaming from my eyes and cum flowing from my stretched and throbbing pussycat.