Glenn is a friend and fuck buddy with a desire to be a cuckold husband or boyfriend. Frequently when he and I get together, we role play his fetish. Sometimes he wants me to arrive at his home full of cum, and tell him about how other guys fucked and filed my holes. Other times he likes to watch me being used by other guys, and even being told to clean out my holes or even being made to clean and suck cocks occasionally.
Last summer he and I decided to go to a private swimming hole for our role playing. The swimming hole is on private property, posted against trespassers and is in the middle of a wood lot so it is completely hidden. Many of us use it as a place for skinny dipping and sex. It has a grassy area around 3 sides of it as well as a strip of sand.
In preparation for our date I contacted a couple other fuck buddies and asked them to meet us there and described their roles in the game to them. I also told them to make it as realistic as they could and to be sure to take complete control. They did not disappoint me or Glenn as they took their parts to heart.
Glenn had prepared sandwiches for a picnic lunch. When we arrived just before 11 AM we spread out a blanket in the grass at the edge of the sand. My other fuck buddies, Gordon and Steve, were already there and in the water. Once the blanket was spread out, I stripped out of my clothes. Glenn removed his shirt and sandals, but not his shorts. There were a few other people around but not many.
I laid on my stomach so Glenn could rub sunscreen onto my back. When he finished there, I rolled over. I was not surprised to see Gordon and Steve a few feet away, watching as Glenn squeezed more sunscreen onto my upper chest. He set the bottle down, but before his hands reached me, the 2 stepped closer. Gordon called me sexy and asked if I needed any help. Glenn turned to look their direction and remarked ‘no, that he had it.' Gordon responded with a dismissive, "I was not talking to you."
Naturally I knew what their cocks looked like, but I made it obvious that I was checking out their big, stiff dicks. "Mmm, why yes, I think I could use a bit of assistance," I said, before running my tongue along my upper lip.
Within seconds Glenn was shoved aside and the 2 men were on either side of me, both with hands beginning to spread the sunscreen over my chest and tits. They were definitely doing more fondling than rubbing and quickly had my nipples up and hard. Glenn moved a few feet away, sat cross legged and just watched. He had an almost pouting expression on his face, but his eyes were sparkling. After a while, their hands moved to my stomach and inched closer and closer to my wet pussy.
Just as I expected fingers to begin exploring between my legs, Steve, who was at my right side, moved to beside my head. He pulled my left shoulder and rolled me onto my side. His cock inches from my mouth. I obediently parted my lips, without him saying a word. He slipped the head of his cock between them. At the same time, Gordon's hands began rubbing my butt cheeks. Glenn started to say something, but Gordon told him to shut up until spoken to, and added they would show him what real men could do with a woman.
I licked and sucked the head of Steve's dick while Gordon's hands explored my buttocks and butt crack. After a couple of minutes, Gordon lifted my left leg and his other hand slipped between my legs. A finger found my slit and pushed inside. He wiggled for a moment before declaring that I was already very wet. Almost before I knew what was happening, I found myself on my knees with Steve's cock farther into my mouth and my legs spread. The head of Gordon's cock pushed into my slit and rubbed up and down in it a few times.
From the corner of my eye I saw Glenn move and sit where he had a view of both cocks. As Gordon began easing his cock into my pussy, Glenn shimmied out of his shorts. While Glenn fantasizes about being cuckold, and maybe being a bit of a sissy, he is no slouch when it comes to his dick. It is easily 8 inches long and a bit fat, and it jumped out, fully erect, as his shorts slid down his legs. With the shorts at his knees, he began stroking his cock.
Gordon carries a monster between his legs. It is 11 inches long and about 7 inches in circumference. He had pushed about half of it into me when he grabbed my hips and drove the rest, balls deep, in my pussy. The force of his thrust propelled me forward so all of Steve's 9 inch dick slipped down my throat. Steve tangled his fingers in my hair and the 2 men began pushing and pulling me so each of their cocks rammed into me in turn.
It was not long before I began to moan softly. Gordon's cock plunging into me, stretching my pussy, was exquisite. Minutes later I knew the guys would not be cumming soon, but my first orgasm was starting to build. Tingling fingers were running up my spine, exciting my brain. Suddenly, Steve pulled my mouth completely away from his cock and called out "Switch."
Gordon's dick instantly abandoned my pussy. I moaned, but from disappointment, not pleasure. Steve laid on the blanket and Gordon, still holding my hips, guided me to straddle Steve. He lowered me onto the tip of Steve's cock. As I settled, letting that dick slide in, Gordon laid beside Steve with his hip next to Steve's right shoulder. Gordon's big right hand grabbed a fistful of my hair. He pulled my head to his throbbing cock. I opened my mouth wide to let it in.
His hand continued pushing my head down. The angle was not good for taking such a monster balls deep. However, 9 inches, maybe a little more, had slipped into my throat before it started to bind and cause me to choke. Gordon was not deterred. With one powerful thrust of his hips, his pelvis slammed against my chin and my nose pushed into his balls sack. I gagged and began to retch. He did not let up, holding me down on his monster for a few moments. I struggled for control and to breathe. Just before I actually puked, he pulled my head up so my mouth engulfed his cock's head. I took a breath before my head was forced back down as his hips drove upwards.
While Gordon forced his cock deep into my throat over and over, Steve's cock was ramming up into my pussy repeatedly. As he fucked me, he yelled to Glenn. "Get over here wimp! Rim and lick the slut's ass. Get it ready to take a real cock. Move it!"
A moment later Glenn's hands spread my butt cheeks and his tongue began licking my asshole. It only took a couple of minutes for that interrupted orgasm to resume building. The tip of Glenn's tongue squeezed into my sphincter as my body began to quiver. His fingers clutched at my butt cheeks, attempting to hold them still while pushing his tongue deeper. Gordon raised my head just in time for me to scream, but the scream was cut short when his cock rammed into my throat again.
My ass was getting quite sloppy. I could feel Glenn's saliva running towards my pussy and around my labia. I am sure some was running onto Steve's balls. My second orgasm was stronger. All my muscles twitched. My spine seemed to ripple as a wave of pleasure washed over me. Gordon prevented my scream by holding my head down and his monster balls deep in my throat. I gagged and choked. Saliva and phlegm oozed out of my nose and from around his cock, slowly coating his scrotum.
Over my gags and choked off scream I heard Steve tell Glenn to stick some fingers up my ass. "Get some fingers in there, wimp. Gape the slut's ass good ‘cause it is going to take a big cock."
It seemed like no time at all passed before Glenn was adding a third finger to those he was already pumping in and out of my ass. My sphincter was stretching. God! It felt wonderful! I was wiggling and rocking my hips, driving both Steve's cock and Glenn's fingers faster. My third orgasm was taking forever to build, while fingers of pleasure raced up and down my spine. Gordon's deep, rough fucking of my throat only added to my pleasures.
"Hurry it up, little man! Fist the bitch!" I heard Steve, however the words never actually registered. My mind was drifting on a sea of ecstasy. I never noticed Glenn's fourth finger, or the fifth, slip up my ass, but when he doubled up his fist and rammed it deep, my orgasm exploded. Despite Gordon's grip on my head, I rose up and screamed. I shook violently. My scream was still echoing around the swimming hole when Gordon's cock forced its way down my throat again.
Glenn's fist was fucking my ass at nearly double the speed of Steve's cock pumping in and out of my pussy. The fist and cock, rubbing against each other with my sensitive inner walls squeezed between them soon had me in the throes of another orgasm. This time my cunt spewed juices and I squirted. Being pressed against Steve made my fluids spray out in every direction. Gordon purposely held his monster deep in my throat, using both hands to guarantee my screams could not escape.
The orgasm barely passed when Gordon declared he wanted my pussy again. Steve immediately barked at "Little man" to get out of the way of "the real men," and warned that I "the slut" better be gaped enough. Glenn's hand yanked from my ass and he moved away quicker than the words came from Steve's mouth.
My muscles were quivering and not being very cooperative, but the guys quickly had me turned around and mounted on Gordon's dick. He wasted no time thrusting upwards, impaling me with its full length. He grabbed my hips and pulled me down as he resettled his ass on the blanket. Steve moved behind me. He began pushing against my back, laying me onto Gordon. I was not completely laying down when his cock pushed through my sphincter. He hesitated a moment while I adjusted myself, then drove deep. I squealed.
Gordon's strokes were not very long, but his monster had my pussy tingling almost from the first thrust. Steve's dick was soon rapidly pounding my ass deep, with long strokes. The 2 dicks pressing the thin linings between them pushed me to another orgasm almost instantly. I could not resist pushing my ass back to greet Steve's thrusts, making them harder and quicker. As they fucked me and waves of pleasure sped through me, seeing Glenn stroking his cock, with lust written all over his face only fed my own pleasure.
My moans were replaced with shrieks and screams as my juices gushed and my head was nearly overwhelmed with ecstasy. Keeping my eyes glued on Glenn was probably the only thing keeping me from being lost in that pleasure. However, by keeping my face turned to Glenn prevented me from realizing what was happening on the other side of me.
I heard voices, but they did not register. Completely oblivious of the guys who had come over to watch, I was surprised when my hair was grabbed and my head turned to find a cock waiting to push into my mouth. Before I could look to see who the cock belonged to, it rammed through my lips and into my throat. It began throat fucking me without a second's hesitation. The screams and shrieks ended as I could hardly catch my breath.
Steve's first thick wad of cum erupted into me. My whole body shook violently even though all 3 men held me. My mind fogged as a huge orgasm exploded in my head. I am not sure how my own fluids kept gushing. I would have thought I would have been dehydrated. After dumping only a few wads up my ass Steve pulled out. As I heard him tell the "wimp" to suck his dick, another cock slammed up my ass.
Gordon's monster was next to explode in me. I had no choice. The ecstasy overwhelmed me. I know a short time later I choked and coughed as cum shot into my throat, but I still had little idea of what was going on around me. I have only a slight idea of how much time passed, but when the fog began to clear I was sprawled out on the blanket, with cum in my face, coating my tits and stomach. Glenn was licking at it while Steve and Gordon were rinsing some of it off with their streams of warm piss.
Later, as Glenn and I headed for his place he told me how amazing it was to watch 5 guys have their way with me, and then to suck the last of their loads from their cocks. My plan to make his fantasy come true had gone better than I expected, for him and for me.
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