The Homeless Shelter ch. 13
In the few weeks since I’d stopped volunteering at the homeless shelter, my infidelity had gotten right out of control. When I’d worked at the shelter, my extra marital sex was pretty much restricted to weekend days. When I volunteered there, I was kind of able to justify my infidelity, using the theory that I was providing a service to the homeless, especially military veterans who were homeless. However, now I've gone wild. I couldn’t get through a week without going to the sex shop and using the video booths, sucking cocks at the glory holes, and even letting some guys fuck me. I knew that on some days the homeless were allowed inside the booths free of charge, but I didn’t really know that the people I’d sucked off were homeless; in fact, I knew only a small percentage were.
In addition, I’d also succumbed at work and used to get Rick, one of the security guards, who was a friend of Ben, the first homeless military veteran I’d let fuck me, to come to my office after office hours and, on one occasion, during work hours, which was super scary but also super exciting. Rick didn’t mind; he loved fucking me, especially up my butt, and I loved having sex with my husband, Ted, in the evenings after Rick had fucked me, knowing that Rick’s cum was sloshing around in my bowels. But it had to change, as I was beginning to feel guilty. I wondered how I could; I knew for sure I couldn’t give it up, as I loved it.
I decided that the best way to make me feel better about it was to try and ensure that in the main, my extra marital sex was just to do something nice for the homeless, but how? I didn’t really want to go back to the shelter, as I didn’t know the new owners, although Maxine told me they were very nice. I thought about asking Gemma in the sex shop if there was a way I could arrange to service only the homeless in the video booths, but as we discussed it, I knew it wasn’t going to be practical. I had to do something, so I set about racking my brains.
Things all fell into place, purely by accident, one evening after work. I’d had a long, tough day and wanted a drink, but I knew we had no wine at home as I was due to go to the supermarket before the weekend to stock up. Ted was away, so I couldn’t ask him to get some, and the supermarket was in the opposite direction of work from home, so it would have meant a long journey just for a bottle or two of wine. Then I remembered that when I’d walked to the sex shop several times, there was a liquor store on the way. I decided I’d be OK to go to the shop and buy a bottle, although I knew that probably meant I’d end up in the sex shop, as just the fact I was going near it had my pussycat throbbing and my mouth drooling, to satisfy my craving for cock and cum, although I had kind of made a pledge to myself that I’d try and stick to helping the homeless.
The liquor store was less than a ten-minute walk from my work building, and when I got there, I saw an old black guy, maybe in his sixties, although with the homeless, it’s hard to tell until they are cleaned up, standing outside next to a shopping cart. As I passed him, I could see the shopping cart was full of shopping bags, bottles of water, a couple of blankets, and three sleeping bags. As I passed him to enter the store, he very politely asked me if I could spare some change. Although my heart went out to him, I didn’t carry any cash when walking around that part of town, so I had to tell him I had none. "OK, ma'am, well, you have a nice evening anyway,” he said.
I went inside the store, and the store owner was talking to a couple of Hispanic guys, who also looked like they were homeless. The store owner handed one of the guys a six-pack of beer and told him to stay safe. As they backed away from the counter, one of them accidentally banged into me. “Oh jeez, I’m very sorry, ma’am. Are you okay? I just didn’t see you. I told him I was fine and that I appreciated the apology. “Thank you, ma’am. You have a nice evening now.” He said as they both wandered off out of the door. As I watched them, I saw them talking to the black guy, and the three of them wandered off down the street together.
The store owner broke my gaze, asking me if I was OK, and I told him I was. He nodded in the direction of the door and told me they were a bunch of homeless guys. I commented that they were very polite. He then told me they were all ex-military; the black guy was a veteran, and the two Hispanic guys had been discharged after going off the rails a bit following some overseas deployment. He told me they were very nice guys, just homeless, and as he was an ex-military himself, he used to help them out. “They do a little humping and dumping for me, and I give them some free beer every now and then. It keeps them near the store, away from the worst part of town, and they sleep out back in the loading dock of the furniture shop next door,” he told me before asking me what he could get me.
I was a little touched by the plight of the three, and if I was honest with myself, I was a little horny knowing they were military veterans and I had after all pledged to help them. I looked at the bottles of wine behind the counter; there wasn’t much choice, but they had a reasonable-looking Merlot, so I asked for two bottles. As he wrapped and bagged them, I had a thought. “I’ll also take a bottle of that Irish whiskey,” I said, pointing at some pretty cheap-looking bottles. He wrapped and bagged the whiskey separately, and I paid on my card, wished him a good evening, which he reciprocated, and I left.
I walked down the street a little in the direction the three homeless guys had gone, and after only about twenty yards, there was a small passage. It was dimly lit, so I walked down it slowly, and after about thirty to forty yards, it opened out into a kind of courtyard. I looked around and could see several dumpsters and one edge of a loading dock attached to the back of the building I’d just walked past on the street. I walked towards the dock, my heart thumping, and I could hear voices.
I walked around the back of the dumpsters and saw the three guys sitting on the dock. The old black guy was sitting in a chair, and the two Hispanic guys were sitting on a mattress on the floor, leaning with their backs against the wall. The three of them were drinking the beer the store owner had given them. The black guy saw me and said, “We ain’t doing any harm, lady; the owner lets us sleep here because it's dry and out of sight, so we feel safe.”
“Oh no, it’s fine.” I said. I saw you outside the store asking for change, and I told you I had no cash, which is true, so I bought you a bottle of whiskey on my card.” I said, holding out the bag with the whiskey in it.
“Mighty kind, ma'am." He said this before asking me to step up onto the dock with it, pointing at some steps to the side. As I got to the top of the steps, the black guy stood up and said to the two Hispanic guys, Hey boys, where’s your manners?”
With that, the two Hispanic guys jumped to their feet and, almost in unison, said, "Sorry, ma’am. It’s much appreciated.” I handed the bottle to the black guy, who said, “We really appreciate it, ma’am. My name is Gil, and these two are Bobby and Vinnie. Please sit with us for a spell and have a drink,” he said, pointing to the chair he had just been sitting in. I told them my name and took a seat, and he dug around in his shopping cart, found some paper cups, and poured some of the whiskey into them before handing them out to me, Bobby, and Vinnie.
Although I hated whiskey, I took a sip. It was raw and rough, and it felt hot as it went to my stomach, but the three guys drained their cups and Gil refilled them. I asked them how they were homeless, and Gil told me he’d split from his wife ten years ago and just kind of went downhill; he’d now been homeless for about five years. Vinnie then told me that he and Bobby had served together, gotten in trouble with drugs after being overseas, and been kicked out of the Army. They had ended up sleeping rough; in between their casual jobs, they still did now and then. They had met Gil a few months ago, who had shown them the best places to get free food and sleep. They have kind of stuck together since.
I was touched by their stories, and as they had been speaking to me, I realized I’d emptied my cup. Gil noticed and refilled it. I drank the whiskey, and now it doesn’t taste too bad. I then asked them if they knew there was a homeless shelter down the street that they could use to get cleaned up during the day and get hot food. Gil looked at me and suddenly said, “Wait a minute, are you the Sarah who works at the shelter?” I told him I used to but didn’t anymore.” Gil told me he had used the shelter a few times and that he knew Ben.
My heart almost thumped out of my chest, and my insides fluttered. Ben had been the first homeless man I had let fuck me; he had been a regular at the shelter but had managed to find a full-time hostel and work in another city months ago. I kind of missed him too. As I thought about what Ben Gil said, "Oh, Ben told me all about you, Miss Sarah, and how you were very kind to the homeless.” As he spoke, he stared at me and had a look of lust in his eyes, which kind of made my insides flutter even more.
“I’m sure Bobby and Vinnie here would love a little of your kindness, Miss Sarah. Wouldn’t you, boys? Gil said with a wry smile on his bearded face. I looked at the faces of the two Hispanic guys, their eyes full of hope.
My heart melted. “Well err! I suppose I could sit with them a while,” I said, knowing fine well that there was going to be a lot more than just sitting involved. Gil jumped up and motioned for me to sit on the mattress in between Bobby and Vinnie.
As I sat down, Gil took my place on the chair before he said, “Come on, boys. Manners, tell Miss Sarah how hot and sexy she looks this evening.” Vinnie and Bobby looked at each other, then looked at me and told me I was a really sexy woman. I asked them why they thought I was sexy, and there was no reply. They both looked a little dazed.
“Don’t be shy, boys.” Gil said. “Miss Sarah loves to be complimented.”
“Well, you sure have really nice-looking big tits, ma’am.” Vinnie said.
“Why thank you.” I said. “Wouldn’t you like to get a better look? You can feel them too if you like.” I said, not really believing how slutty I had become in recent months. I was about to let two homeless strangers fuck me on a grubby mattress on a loading dock behind a shop. My heart gushed at the thought. Vinnie and Bobby couldn’t wait. Within seconds, they had my blouse undone and were groping my tits through the fabric of my bra. I have to laugh while writing this, as I used to call my tits my breasts and so forth, but now my choice of language regarding sex has gotten as dirty as my mind and my actions.
As they groped me, Vinnie tried to kiss me. I pulled my head away and said, “No kissing lover, boy. I’m married. Why don’t I undo my bra and you two get your nice cocks out for me?” The two of them followed my request, quickly getting their cocks out while I stood up and decided to slowly strip for them as they stroked their cocks to hardness. I looked down at their cocks; they were so alike they could have been twins, both about seven inches long and of nice thickness. I couldn’t wait to suck on them, so I dropped to my knees between them and took hold of them, stroking them and feeling them throbbing while Vinnie and Bobby groped my tits and pulled on my nipples.
“Stand up for me.” I said. Vinnie and Bob stood up and offered their hard cocks to me, which I began sucking, alternating between them both. I guessed they hadn’t had sex for a while, as they were both leaking pre-cum like crazy. I lapped up the sweet-tasting fluid, teasing their piss holes with my tongue as they groaned. I could feel their cocks throbbing, and I guessed they wouldn’t last long.
I heard Gil say, “Come on, boys. Enough of that. Give the pretty Miss Sarah what she wants.” With all that was going on, I’d almost forgotten about Gil behind me. I turned around, and he was sitting on the chair. a whiskey bottle in one hand and a cock in the other. His cock was long, thick, and flaccid, and his balls were huge, hanging down between his legs, almost touching the chair. I thought perhaps he couldn't get erect anymore; he just enjoyed watching sex these days.
As I was looking at Gil, the two other guys maneuvered me around so I was on all fours, side by side with Gil, meaning he was going to get a really good view as Bob and Vinnie spit toasted me, which I was certain was their intent. I wasn’t wrong; seconds later, I felt Vinnie rubbing his cock up and down the slit of my soaking wet cunt, and then I groaned as he slid his cock into me.
Vinnie wasn’t gentle; although I don’t think he was intentionally rough, he seemed more frantic than anything, as he fucked me with the urgency of someone who hadn’t had a woman for a while and was worried he was going to be told to stop. As Vinnie went at me, Bob thrust his cock into my mouth. He had a similar kind of urgency to Vinnie and wasn’t at all gentle. I frequently gagged as his cock rammed against the back of my throat.
I heard Gil call out for the boys to change, telling them they should have even gone and not to cum too quickly. The two guys followed Gil’s lead and immediately swapped over, and my cunt was soon being pounded by Bob’s cock. He had a slightly different technique from Vinnie and seemed to rub his cock against my G spot a little more. I could feel the throbbing in my cunt radiating through my body; my nipples were tingling as my tits swayed back and forth beneath me. Vinnie rammed his cock into my mouth and began face-fucking me. His cock was soaked in my cum juice, and it turned me on even more, and the throbbing in my cunt intensified.
“Don’t go shooting off in her pussy, boys.” I heard Gil call out, and I looked across at him. He was still in the chair, plating with his cock, but it had grown considerably and was now semi-hard. Maybe he could get it up after all, I thought, as my two younger lovers fucked me from both ends, regularly swapping and giving me a freshly cumin-covered cock to enjoy. My cunt was throbbing from the constant hard pounding Bob and Vinnie were giving me, and I wondered where they were going to cum if they followed Gil’s instructions.
I didn’t have to wait long; out of the corner of my eye, I saw Gil approaching; his huge cock was now fully hard, and my eyes widened at the sight of it. "OK, Bobby, move on over and let old Gil have some fun.” He said this to Bob, who was fucking my cunt at the time. Bob duly obliged and pulled his cock out of me. I felt Gil kneeling down behind me, and then he was rubbing his huge cock against my slit. He pushed his cock head into me, and even though I was well juiced up, it felt tight as it stretched my lips. Slowly and gently, Gil began working his cock into my soaking cunt until he was all the way inside me and I could feel his bony hips digging into my buttocks.
I felt Gil’s boney hands grip my hips, and then he began fucking me with long, deep, steady thrusts, each one making me gasp and my cunt throb as his cock stretched my vaginal passage. Gil was fucking me deep, and Vinnie increased the pace with which he was fucking my mouth. He had a hold of my head, and suddenly he tightened his grip on it. Seconds later, he started to tremble, and then, as he said, "Oh, fuck, yeah!" His cock erupted in my mouth. He pumped five or six spurts of cum into my mouth, making me swallow it all.
Vinnie pulled his softening cock from my mouth, and I just about managed to take a couple of deep breaths before it was replaced by Bob’s cock. It was still all sticky from being up my cunt, and I savored the taste of myself. He began to shove it deep, his balls banging against my chin, making me gag. Every time he pulled back, saliva spilled from my mouth, running off my chin. Gil had increased the pace of his thrusts a little, and now he and Bob were in sync, both thrusting into me at the same time. I could hardly breathe, and just when I thought I’d pass out, Bob grunted and came hard. His first spurt went right down my throat, almost reaching my stomach, which was followed by another half dozen big spurts.
Finally, Bob pulled his cock out of my mouth, and I breathed heavily, gulping in the air. I braced myself, expecting Gil to start fucking me harder now that Vinnie and Bob had finished with me. I was wrong! Gil pulled his cock from my throbbing cunt, my pussy walls clinging on to it as he withdrew, not wanting to release it. He dug his boney hands deeper into my flesh and lifted my hips slightly, flipping me over so I was now lying on my back. He then shuffled down, laying between my legs with his head hovering above my pubic mound.
I could feel his breath on my gaping love hole as he lowered his head even more, then sank his tongue into me, licking, slurping, and sucking my juices as I squirmed with delight. His bristly beard was course against my soft lips, and his moustache rubbed over my clitoral area. As he went to town on my cunt, Vinnie and Bob both lowered their heads and began sucking on my nipples, so hard they started to sting, while their hands squeezed my fleshy D cup tits hard. My whole body was tingling, and I thought I was going to explode as the three of them used their mouths on me for several minutes. Every time I was about to go over the edge, Gil paused and kept me hanging on.
Vinnie and Bob finally gave my stinging nipples some relief and stopped sucking on them, only for them to launch a full-scale assault on my mouth as they both began shoving their cocks, which were now hard again, into my mouth, alternating between sticking them in my mouth and slapping my face with them. I closed my eyes and pictured the scene. A middle-class professional career woman is lying on her back on a grubby mattress with three homeless men abusing her body. I groaned with bliss at the thought and only wished there were people watching me.
Gil stopped licking my cunt again, and I felt him shuffle upwards on the mattress. He parted my legs a little more and guided his hard cock right into my hole, sinking it deep. It was almost as if they knew what was about to happen. Vinnie and Bob stopped what they were doing and moved back a little, still both kneeling on either side of me. Gil lowered his body so his torso was pressing against me, his grubby clothes rough against my already stinging nipples, as he humped me with his huge cock.
Gil thrust his cock deep, and it hurt—his rough pubic hair rubbing against my sensitive clitoral area—so much so that I thought it was going to burst. Then he slid a hand underneath my head, holding it before he looked into my eyes and leant forward, pressing his lips against mine. The smell and the taste repulsed me—stale breath, stinking whiskey, and stale food. It got even worse when his rough tongue snaked its way into my mouth, so deep it almost touched my tonsils. I wanted to be sick; I was almost retching beneath him.
Then it suddenly changed. I once again saw myself from above, as a spectator to this bizarre event. I heard Bob and Vinnie cheering him on, “Go on, Gil! Give it to her. Fill her up!” I realized he was going to cum inside me, and my out-of-body self joined in with Vinnie and Bob. I screamed in my head, “Yes! Yes! Yes! Go on. Fill those white sluts with cum!” My arms wrapped around Gil’s shoulders, and my legs gripped his hips, pulling him deeper and deeper into me. My body was shuddering; he pulled his mouth off mine, and I sucked in the air and screamed, "Oh, Fuck Yessssss! I’m going to cum! Fuck me.”
Gil rammed his big cock into me at a furious pace. I felt like my cunt was going to burst into flames, the heat radiating through my whole body. He pushed himself up so he was almost kneeling, his thigh under mine, the shaft of his cock rubbed my G spot, and his thumb pressed on my clitoral area. Gil grunted and started to shake. A new feeling of heat gushed into my chest; his seed was flooding me; fireworks went off in my body, and I came hard. As I shook, I felt more heat on my face and tits. Vinnie and Bob were showering me with their second load. Hot cum is spurting all over me. I was in sexual heaven.
After a couple of minutes of all four of us being a mass of grunting, gasping, and shuddering orgasms, we all began to relax. Gil pulled his cock out of me, stood up, and walked away to his shopping cart. Bob and Vinnie joined him, and as they spoke, I lay there on the grubby mattress, cum all over my face and tits, Gil’s cum flowing like a stream from my throbbing cunt. I breathed hard for a couple of minutes, trying to slow my heart rate and staring at the three homeless guys who had just used me, standing there laughing, their spent cocks hanging down.
After another minute, Gil pulled some wipes from his cart, brought them over to me, and began to clean me up. Bob and Vinnie joined him, and between them, they gently cleaned my body, mopping up all the cum. I eventually felt able to stand. The three guys watched me as I dressed. I was a little lost for words. I picked up my bag with the two bottles of wine in it, took one out, and handed it to Gil. “I’ll need the other one when I get home.” I said, almost laughing.
I asked Gil if he slept on the loading dock every evening. He looked at me and smiled. “There is always someone here,” he said. I walked away, back to the street, and headed back to my car. Despite the clean-up the guys had done, I still felt cum running into my pants. I smiled as I recalled Gil’s last words. “Every Night! Hey?” I thought to myself.
In addition, I’d also succumbed at work and used to get Rick, one of the security guards, who was a friend of Ben, the first homeless military veteran I’d let fuck me, to come to my office after office hours and, on one occasion, during work hours, which was super scary but also super exciting. Rick didn’t mind; he loved fucking me, especially up my butt, and I loved having sex with my husband, Ted, in the evenings after Rick had fucked me, knowing that Rick’s cum was sloshing around in my bowels. But it had to change, as I was beginning to feel guilty. I wondered how I could; I knew for sure I couldn’t give it up, as I loved it.
I decided that the best way to make me feel better about it was to try and ensure that in the main, my extra marital sex was just to do something nice for the homeless, but how? I didn’t really want to go back to the shelter, as I didn’t know the new owners, although Maxine told me they were very nice. I thought about asking Gemma in the sex shop if there was a way I could arrange to service only the homeless in the video booths, but as we discussed it, I knew it wasn’t going to be practical. I had to do something, so I set about racking my brains.
Things all fell into place, purely by accident, one evening after work. I’d had a long, tough day and wanted a drink, but I knew we had no wine at home as I was due to go to the supermarket before the weekend to stock up. Ted was away, so I couldn’t ask him to get some, and the supermarket was in the opposite direction of work from home, so it would have meant a long journey just for a bottle or two of wine. Then I remembered that when I’d walked to the sex shop several times, there was a liquor store on the way. I decided I’d be OK to go to the shop and buy a bottle, although I knew that probably meant I’d end up in the sex shop, as just the fact I was going near it had my pussycat throbbing and my mouth drooling, to satisfy my craving for cock and cum, although I had kind of made a pledge to myself that I’d try and stick to helping the homeless.
The liquor store was less than a ten-minute walk from my work building, and when I got there, I saw an old black guy, maybe in his sixties, although with the homeless, it’s hard to tell until they are cleaned up, standing outside next to a shopping cart. As I passed him, I could see the shopping cart was full of shopping bags, bottles of water, a couple of blankets, and three sleeping bags. As I passed him to enter the store, he very politely asked me if I could spare some change. Although my heart went out to him, I didn’t carry any cash when walking around that part of town, so I had to tell him I had none. "OK, ma'am, well, you have a nice evening anyway,” he said.
I went inside the store, and the store owner was talking to a couple of Hispanic guys, who also looked like they were homeless. The store owner handed one of the guys a six-pack of beer and told him to stay safe. As they backed away from the counter, one of them accidentally banged into me. “Oh jeez, I’m very sorry, ma’am. Are you okay? I just didn’t see you. I told him I was fine and that I appreciated the apology. “Thank you, ma’am. You have a nice evening now.” He said as they both wandered off out of the door. As I watched them, I saw them talking to the black guy, and the three of them wandered off down the street together.
The store owner broke my gaze, asking me if I was OK, and I told him I was. He nodded in the direction of the door and told me they were a bunch of homeless guys. I commented that they were very polite. He then told me they were all ex-military; the black guy was a veteran, and the two Hispanic guys had been discharged after going off the rails a bit following some overseas deployment. He told me they were very nice guys, just homeless, and as he was an ex-military himself, he used to help them out. “They do a little humping and dumping for me, and I give them some free beer every now and then. It keeps them near the store, away from the worst part of town, and they sleep out back in the loading dock of the furniture shop next door,” he told me before asking me what he could get me.
I was a little touched by the plight of the three, and if I was honest with myself, I was a little horny knowing they were military veterans and I had after all pledged to help them. I looked at the bottles of wine behind the counter; there wasn’t much choice, but they had a reasonable-looking Merlot, so I asked for two bottles. As he wrapped and bagged them, I had a thought. “I’ll also take a bottle of that Irish whiskey,” I said, pointing at some pretty cheap-looking bottles. He wrapped and bagged the whiskey separately, and I paid on my card, wished him a good evening, which he reciprocated, and I left.
I walked down the street a little in the direction the three homeless guys had gone, and after only about twenty yards, there was a small passage. It was dimly lit, so I walked down it slowly, and after about thirty to forty yards, it opened out into a kind of courtyard. I looked around and could see several dumpsters and one edge of a loading dock attached to the back of the building I’d just walked past on the street. I walked towards the dock, my heart thumping, and I could hear voices.
I walked around the back of the dumpsters and saw the three guys sitting on the dock. The old black guy was sitting in a chair, and the two Hispanic guys were sitting on a mattress on the floor, leaning with their backs against the wall. The three of them were drinking the beer the store owner had given them. The black guy saw me and said, “We ain’t doing any harm, lady; the owner lets us sleep here because it's dry and out of sight, so we feel safe.”
“Oh no, it’s fine.” I said. I saw you outside the store asking for change, and I told you I had no cash, which is true, so I bought you a bottle of whiskey on my card.” I said, holding out the bag with the whiskey in it.
“Mighty kind, ma'am." He said this before asking me to step up onto the dock with it, pointing at some steps to the side. As I got to the top of the steps, the black guy stood up and said to the two Hispanic guys, Hey boys, where’s your manners?”
With that, the two Hispanic guys jumped to their feet and, almost in unison, said, "Sorry, ma’am. It’s much appreciated.” I handed the bottle to the black guy, who said, “We really appreciate it, ma’am. My name is Gil, and these two are Bobby and Vinnie. Please sit with us for a spell and have a drink,” he said, pointing to the chair he had just been sitting in. I told them my name and took a seat, and he dug around in his shopping cart, found some paper cups, and poured some of the whiskey into them before handing them out to me, Bobby, and Vinnie.
Although I hated whiskey, I took a sip. It was raw and rough, and it felt hot as it went to my stomach, but the three guys drained their cups and Gil refilled them. I asked them how they were homeless, and Gil told me he’d split from his wife ten years ago and just kind of went downhill; he’d now been homeless for about five years. Vinnie then told me that he and Bobby had served together, gotten in trouble with drugs after being overseas, and been kicked out of the Army. They had ended up sleeping rough; in between their casual jobs, they still did now and then. They had met Gil a few months ago, who had shown them the best places to get free food and sleep. They have kind of stuck together since.
I was touched by their stories, and as they had been speaking to me, I realized I’d emptied my cup. Gil noticed and refilled it. I drank the whiskey, and now it doesn’t taste too bad. I then asked them if they knew there was a homeless shelter down the street that they could use to get cleaned up during the day and get hot food. Gil looked at me and suddenly said, “Wait a minute, are you the Sarah who works at the shelter?” I told him I used to but didn’t anymore.” Gil told me he had used the shelter a few times and that he knew Ben.
My heart almost thumped out of my chest, and my insides fluttered. Ben had been the first homeless man I had let fuck me; he had been a regular at the shelter but had managed to find a full-time hostel and work in another city months ago. I kind of missed him too. As I thought about what Ben Gil said, "Oh, Ben told me all about you, Miss Sarah, and how you were very kind to the homeless.” As he spoke, he stared at me and had a look of lust in his eyes, which kind of made my insides flutter even more.
“I’m sure Bobby and Vinnie here would love a little of your kindness, Miss Sarah. Wouldn’t you, boys? Gil said with a wry smile on his bearded face. I looked at the faces of the two Hispanic guys, their eyes full of hope.
My heart melted. “Well err! I suppose I could sit with them a while,” I said, knowing fine well that there was going to be a lot more than just sitting involved. Gil jumped up and motioned for me to sit on the mattress in between Bobby and Vinnie.
As I sat down, Gil took my place on the chair before he said, “Come on, boys. Manners, tell Miss Sarah how hot and sexy she looks this evening.” Vinnie and Bobby looked at each other, then looked at me and told me I was a really sexy woman. I asked them why they thought I was sexy, and there was no reply. They both looked a little dazed.
“Don’t be shy, boys.” Gil said. “Miss Sarah loves to be complimented.”
“Well, you sure have really nice-looking big tits, ma’am.” Vinnie said.
“Why thank you.” I said. “Wouldn’t you like to get a better look? You can feel them too if you like.” I said, not really believing how slutty I had become in recent months. I was about to let two homeless strangers fuck me on a grubby mattress on a loading dock behind a shop. My heart gushed at the thought. Vinnie and Bobby couldn’t wait. Within seconds, they had my blouse undone and were groping my tits through the fabric of my bra. I have to laugh while writing this, as I used to call my tits my breasts and so forth, but now my choice of language regarding sex has gotten as dirty as my mind and my actions.
As they groped me, Vinnie tried to kiss me. I pulled my head away and said, “No kissing lover, boy. I’m married. Why don’t I undo my bra and you two get your nice cocks out for me?” The two of them followed my request, quickly getting their cocks out while I stood up and decided to slowly strip for them as they stroked their cocks to hardness. I looked down at their cocks; they were so alike they could have been twins, both about seven inches long and of nice thickness. I couldn’t wait to suck on them, so I dropped to my knees between them and took hold of them, stroking them and feeling them throbbing while Vinnie and Bobby groped my tits and pulled on my nipples.
“Stand up for me.” I said. Vinnie and Bob stood up and offered their hard cocks to me, which I began sucking, alternating between them both. I guessed they hadn’t had sex for a while, as they were both leaking pre-cum like crazy. I lapped up the sweet-tasting fluid, teasing their piss holes with my tongue as they groaned. I could feel their cocks throbbing, and I guessed they wouldn’t last long.
I heard Gil say, “Come on, boys. Enough of that. Give the pretty Miss Sarah what she wants.” With all that was going on, I’d almost forgotten about Gil behind me. I turned around, and he was sitting on the chair. a whiskey bottle in one hand and a cock in the other. His cock was long, thick, and flaccid, and his balls were huge, hanging down between his legs, almost touching the chair. I thought perhaps he couldn't get erect anymore; he just enjoyed watching sex these days.
As I was looking at Gil, the two other guys maneuvered me around so I was on all fours, side by side with Gil, meaning he was going to get a really good view as Bob and Vinnie spit toasted me, which I was certain was their intent. I wasn’t wrong; seconds later, I felt Vinnie rubbing his cock up and down the slit of my soaking wet cunt, and then I groaned as he slid his cock into me.
Vinnie wasn’t gentle; although I don’t think he was intentionally rough, he seemed more frantic than anything, as he fucked me with the urgency of someone who hadn’t had a woman for a while and was worried he was going to be told to stop. As Vinnie went at me, Bob thrust his cock into my mouth. He had a similar kind of urgency to Vinnie and wasn’t at all gentle. I frequently gagged as his cock rammed against the back of my throat.
I heard Gil call out for the boys to change, telling them they should have even gone and not to cum too quickly. The two guys followed Gil’s lead and immediately swapped over, and my cunt was soon being pounded by Bob’s cock. He had a slightly different technique from Vinnie and seemed to rub his cock against my G spot a little more. I could feel the throbbing in my cunt radiating through my body; my nipples were tingling as my tits swayed back and forth beneath me. Vinnie rammed his cock into my mouth and began face-fucking me. His cock was soaked in my cum juice, and it turned me on even more, and the throbbing in my cunt intensified.
“Don’t go shooting off in her pussy, boys.” I heard Gil call out, and I looked across at him. He was still in the chair, plating with his cock, but it had grown considerably and was now semi-hard. Maybe he could get it up after all, I thought, as my two younger lovers fucked me from both ends, regularly swapping and giving me a freshly cumin-covered cock to enjoy. My cunt was throbbing from the constant hard pounding Bob and Vinnie were giving me, and I wondered where they were going to cum if they followed Gil’s instructions.
I didn’t have to wait long; out of the corner of my eye, I saw Gil approaching; his huge cock was now fully hard, and my eyes widened at the sight of it. "OK, Bobby, move on over and let old Gil have some fun.” He said this to Bob, who was fucking my cunt at the time. Bob duly obliged and pulled his cock out of me. I felt Gil kneeling down behind me, and then he was rubbing his huge cock against my slit. He pushed his cock head into me, and even though I was well juiced up, it felt tight as it stretched my lips. Slowly and gently, Gil began working his cock into my soaking cunt until he was all the way inside me and I could feel his bony hips digging into my buttocks.
I felt Gil’s boney hands grip my hips, and then he began fucking me with long, deep, steady thrusts, each one making me gasp and my cunt throb as his cock stretched my vaginal passage. Gil was fucking me deep, and Vinnie increased the pace with which he was fucking my mouth. He had a hold of my head, and suddenly he tightened his grip on it. Seconds later, he started to tremble, and then, as he said, "Oh, fuck, yeah!" His cock erupted in my mouth. He pumped five or six spurts of cum into my mouth, making me swallow it all.
Vinnie pulled his softening cock from my mouth, and I just about managed to take a couple of deep breaths before it was replaced by Bob’s cock. It was still all sticky from being up my cunt, and I savored the taste of myself. He began to shove it deep, his balls banging against my chin, making me gag. Every time he pulled back, saliva spilled from my mouth, running off my chin. Gil had increased the pace of his thrusts a little, and now he and Bob were in sync, both thrusting into me at the same time. I could hardly breathe, and just when I thought I’d pass out, Bob grunted and came hard. His first spurt went right down my throat, almost reaching my stomach, which was followed by another half dozen big spurts.
Finally, Bob pulled his cock out of my mouth, and I breathed heavily, gulping in the air. I braced myself, expecting Gil to start fucking me harder now that Vinnie and Bob had finished with me. I was wrong! Gil pulled his cock from my throbbing cunt, my pussy walls clinging on to it as he withdrew, not wanting to release it. He dug his boney hands deeper into my flesh and lifted my hips slightly, flipping me over so I was now lying on my back. He then shuffled down, laying between my legs with his head hovering above my pubic mound.
I could feel his breath on my gaping love hole as he lowered his head even more, then sank his tongue into me, licking, slurping, and sucking my juices as I squirmed with delight. His bristly beard was course against my soft lips, and his moustache rubbed over my clitoral area. As he went to town on my cunt, Vinnie and Bob both lowered their heads and began sucking on my nipples, so hard they started to sting, while their hands squeezed my fleshy D cup tits hard. My whole body was tingling, and I thought I was going to explode as the three of them used their mouths on me for several minutes. Every time I was about to go over the edge, Gil paused and kept me hanging on.
Vinnie and Bob finally gave my stinging nipples some relief and stopped sucking on them, only for them to launch a full-scale assault on my mouth as they both began shoving their cocks, which were now hard again, into my mouth, alternating between sticking them in my mouth and slapping my face with them. I closed my eyes and pictured the scene. A middle-class professional career woman is lying on her back on a grubby mattress with three homeless men abusing her body. I groaned with bliss at the thought and only wished there were people watching me.
Gil stopped licking my cunt again, and I felt him shuffle upwards on the mattress. He parted my legs a little more and guided his hard cock right into my hole, sinking it deep. It was almost as if they knew what was about to happen. Vinnie and Bob stopped what they were doing and moved back a little, still both kneeling on either side of me. Gil lowered his body so his torso was pressing against me, his grubby clothes rough against my already stinging nipples, as he humped me with his huge cock.
Gil thrust his cock deep, and it hurt—his rough pubic hair rubbing against my sensitive clitoral area—so much so that I thought it was going to burst. Then he slid a hand underneath my head, holding it before he looked into my eyes and leant forward, pressing his lips against mine. The smell and the taste repulsed me—stale breath, stinking whiskey, and stale food. It got even worse when his rough tongue snaked its way into my mouth, so deep it almost touched my tonsils. I wanted to be sick; I was almost retching beneath him.
Then it suddenly changed. I once again saw myself from above, as a spectator to this bizarre event. I heard Bob and Vinnie cheering him on, “Go on, Gil! Give it to her. Fill her up!” I realized he was going to cum inside me, and my out-of-body self joined in with Vinnie and Bob. I screamed in my head, “Yes! Yes! Yes! Go on. Fill those white sluts with cum!” My arms wrapped around Gil’s shoulders, and my legs gripped his hips, pulling him deeper and deeper into me. My body was shuddering; he pulled his mouth off mine, and I sucked in the air and screamed, "Oh, Fuck Yessssss! I’m going to cum! Fuck me.”
Gil rammed his big cock into me at a furious pace. I felt like my cunt was going to burst into flames, the heat radiating through my whole body. He pushed himself up so he was almost kneeling, his thigh under mine, the shaft of his cock rubbed my G spot, and his thumb pressed on my clitoral area. Gil grunted and started to shake. A new feeling of heat gushed into my chest; his seed was flooding me; fireworks went off in my body, and I came hard. As I shook, I felt more heat on my face and tits. Vinnie and Bob were showering me with their second load. Hot cum is spurting all over me. I was in sexual heaven.
After a couple of minutes of all four of us being a mass of grunting, gasping, and shuddering orgasms, we all began to relax. Gil pulled his cock out of me, stood up, and walked away to his shopping cart. Bob and Vinnie joined him, and as they spoke, I lay there on the grubby mattress, cum all over my face and tits, Gil’s cum flowing like a stream from my throbbing cunt. I breathed hard for a couple of minutes, trying to slow my heart rate and staring at the three homeless guys who had just used me, standing there laughing, their spent cocks hanging down.
After another minute, Gil pulled some wipes from his cart, brought them over to me, and began to clean me up. Bob and Vinnie joined him, and between them, they gently cleaned my body, mopping up all the cum. I eventually felt able to stand. The three guys watched me as I dressed. I was a little lost for words. I picked up my bag with the two bottles of wine in it, took one out, and handed it to Gil. “I’ll need the other one when I get home.” I said, almost laughing.
I asked Gil if he slept on the loading dock every evening. He looked at me and smiled. “There is always someone here,” he said. I walked away, back to the street, and headed back to my car. Despite the clean-up the guys had done, I still felt cum running into my pants. I smiled as I recalled Gil’s last words. “Every Night! Hey?” I thought to myself.
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