The Jaylynn Chronicles : My first time with older men

My name is Jaylynn Nichole, I was 18 when this experience happened and honestly I don't know why I chose this story to be my first instalment, but it has to be the most amazing time of my life, so far.

My boyfriend an I had been together for a couple of months then and even though he was really nice, we never had sex. See he was a shy guy and he never made a move on me. If any moves were done it was by me, and once it started getting a little hot and heavy he would get nerves and we'd end up stopping. My god how I wanted someone to just take control of me and bang my brains out, like the videos I had seen on the internet.

one day I was hanging out with my boyfriend at his place and we were in the game room playing pool when a gang of men came in. It was my boyfriends dad, uncle, and three of there friends. Now I dident mention this before but I have always been attracted to older men, even at a young age it always made me wet when I would see older men checking me out and tring to be all discrete about it.

I quickly learned that the men were intoxicated and came to hangout and play pool, so my boyfriend and I moved over to the bar and allowed them to have the pool table. My boyfriends phone wrang and he turned to talk when his uncle sat down beside me with this enormous grin on his face and he said, "what would it take for a man like me to have a shot at that sweet little ass?" I have to admit I was completely shocked at the bluntness of his question, but at the same time completely turned on. I decided to play along with his little game so I responded, "when ever you're ready, just let me know daddy." The look on his face was one of shock and excitement, I was pretty shocked myself if I do say so. I've always been smaller, at 18 I was only four foot eleven, and weighed 105, so I always had this young girl attitude about me,which I realized turned men on.

my boyfriend spoke up and said his cousin called from dallas and was in jail and he had to drive up there and get him out, so we walked out to our cars, me feeling the eyes of the five men undressing me, and said our goodbyes then headed our seperate ways.
I made a couple of blocks then came back and pulled into the drive way. Looking in the mirror I decided that this is something that if I do it I can't chicken out. No matter what he wants to do to me its all or nothing.

I walked back in and my boyfriends dad approached me first. He walked up and said, "you alone babygirl?" I smiled with my most innocent smile and replied, "how could I be alone with all you guys here?" He smiled and went back to playing pool.
when I made it to the bar, the uncle approached me again and said, "so, you said something about me just letting you know when I'm ready?" "I sure did," I spoke back. "Well then I'm totally ready little momma." I told him to give me fifteen minutes then come up to Emilys room. Emily was my boyfriends ten year old little sister who was only inches shorter then me, so I know I could change into something of hers real fast.

As I entered her room I noticed the teddy bears and babydolls on her bed, and the hot pink bed spread. I looked in her dresser drawer and found some white hello kitty panties, and a Hanna Montana tee shirt. I quickly changed clothes and sat down on the bed as my boyfriends uncle walked in. He had the old biker look, long beard, lether jacket, you know the rustic look. He clothes the door behind himself, walked up and said, "my, my, my, what do we have here?" I smiled and leaned forward, inches away from him. I could smell his sent, the sent of a real man, and it made me all jittery inside.

He ran his rustic hands through my hair as I reached out and kissed the bulge that was rapidly increasing in his pants. A bulge that I could tell had already surpassed any size I've ever encountered, and I could only imagine the complete gurth underneath those pants.
As I staired at his crotch he said, "you think you're ready for this babygirl?" Before I knew how to respond my head was shaking yes and he was unleashing his snake from his pants. As the pants hit the ground a gasp escaped from inside me that I could not stop. I couldent believe the sight of his penis, never in my wildest dreams did I think there could be one this size. The grin on his face showed that he knew exactly what I was thinking.

He pushed me back on the bed and crawled on top of me. I felt his hands caress my small a cup breast and slowly move down between my legs. He stroked my pussy slowly, and I felt his finger slip under the cotton panties and slowly split the lips beneath them.
He spoke of the smoothness and warmth of my bald vagina as he tried slipping his finger in. He was able to eventually work it in, remember I hadent had much penitration in a while, but the feeling was overwhelming.

He slid my panties off and kissed the bare lips underneath. Then spreading them with his fingers he nudged inside me with the tip of his nose. His tongue then began probing the inside of my girl tunnel and I moaned, without warning. He continued this for a few minutes then slid up next to me. I watched as he smelled his finger, smiled, and covered two fingers with saliva. He rubbed them between my young pussy lips moistening the entrance that he planed to invade soon with the mammoth tree trunk he called a dick. Honestly I was a little scared, but staying true to what I promised myself I spread my legs and alowed him full access to me.

He crawled up on top of me and I could feel the weight of him engulfing me. He raised himself up on his elbows and looked deeply into my eyes as he slowly tried pushing his sausage inside of me. As the head split me open I could feel it was already wider then I had ever had. He spoke saying, "goddamn little girl you're tight." I put my hands on his chest as he moved up and down slowly inching deeper and deeper into my tiny teen hole. The deeper he moved the faster he seemed to go until his cock was completely engulfed inside of me.
I was totally in shock. Never would I believe that something would be this deep inside of my vagina. It hurt a little but the pleasure and excitement were way more overwelming then the pain. It felt as if the tip of his man cannon was touching my rib cage.

He moved up to his knees, raised up and started pounding my hole with everything he had, slamming deeper and deeper. I could hear the sound of our skin slapping together over the intense moaning escaping our mouths when he spoke saying, "im bout to cum, oh shit im gonna cum, " and with that a hard deep cock plunge drove the deepest inside of me yet and the feeling of what seemed to be a gallon of warm man juice shot deep into my vaginal cave.

Laying atop of me smelling of sweat and sex he whispered, "damn little momma I've never met. A girl as good as you." He started pulling his cock out of me but the tightness of my young tender womanhood held on, I thought for a moment that it was stuck, but as the swell of his bat subsided it eased its way out of me.

he raised up and slid his pants on and said, "baby you were awsome, why don't you come down stairs and shoot some pool?" Easing back into my panties I said, "I think I need to go home, maybe next time." A chuckle escaped from his mouth as he said, "that's cool, if your scared I understand, you're just a little girl." A little outraged by what he said I told him I wasent scared not one bit, and I would meet him in the game room.

As I slid off the bed, he left and headed down stairs. I followed moments later and headed to the game room. When I walked in only dressed in panties and a tee shirt, all focus fell on me. My boyfriends father spoke up saying, "well, what do we have here?" Shocked by the look coming from the men, like hungry lions stairing at an injured fawn I felt a bit frightened. The uncle walked in behind me and said, "gentlemen, let the games begin." I turned around facing him when I felt someone walk up behind me and run his hand across my ass. Looking back I saw one of the friends pushing up on me. With an arm around me he walked me over to the pool table, lifted me up and sat me down on it. Raising my now dangling legs he said, "let's see what u have for us little darling." Heart racing I allowed him to pull my panties off, and as the others gathered around to watch the show he planted his face between my legs tonguing my clit and pushing a finger inside of me, I started gasping from the intense ecstasy of it all. I felt someone crawl behind me and pull my legs straight up in the air spreading me wide and the fingers that were in my young hole moved lower to my asshole. He worked a finger in and I almost asked him to stop but really I thought this is what I got myself into so im gonna go with it. In and out in and out until he thought it was time to unleash his monster.

The others started pulling out there huge members and stroking them as I was pulled off the pool table, turned around and bent over, exposing my bare anal hole for everone to see. With one hand on my back holding me down I felt the tip of his cock pressing on my untapped territory. A wetness ran down my crack from a glob of spit released on my ass, as he spread my cheeks he pushed his prick inside my asshole. Honestly I expected it to hurt alot more then it did, but I guess the finger work he gave me before hand helped loosen the tightness.
Once I was completely spread apart he started ramming his cock into me harder and harder. Screams of intense pleasure started escaping from inside of me, and I think that caused him to thrust harder and harder because at this point he was ramming my young tight ass with everything he had, rocking the pool table, and making my teen body vibrate rapidly. All I expected was to have the uncle bang my brains out, but now I find myself in a situation that involves deep anal probing and domination by a room full of older men and I was loving every bit of it.
I heard a scream of ecstasy when he yelled out, "im gonna cum, im gonna cum," and he shot a load of hot cum into my gaping teen ass. Pulling out he spread my ass open and said, "look at that little thing gape open, girl I ain't ever seen anyone take it in the ass like that."
I heard my boyfriends father say, "my turn little darling, come here and sit in daddys lap." He was sitting on the couch so I straddled him working his enormous cock into my pussy. Rocking back and forth he grabbed me by the hips and started pulling me back and forth fast and hard. He was so deep I almost couldent stand it when I realized he was tring to fit the rest in. His cock was at least two inches from being completely inside of me and he was already hitting bottom. He pulled me two him grabbed both ass cheeks and forced the entire chunk of man meat into my small tunnel. Gripping my cheeks he started slamming me up and down on top of his prick. Screams escaped me from the the pounding my pussy was encouraging.

Just then I felt someone come up behind and say, "let's see how wide we can stretch this little girl," when his cock started tring to move into my ass with this other huge member deep in my pussy. There's no way this is gonna be possible ,I thought. He started stretching my asshole by inserting one then two fingers ,spitting large amounts of saliva on my brown ring until he felt sure he could get in. He started inching his cock into me slowly, then leaned over my tiny sweating body and said, "brace yourself sweetie, I like it rough." With that being said he thrust his dick into my ass with everthing he had, ripping my anal hole wide and filling me completely. I screamed but not only from the pain because it did hurt, but from the excitement of being dominated by these men. This was my fantasy coming to life. He started ramming hard brutilizing thrust so deep and strong into my asshole that the cock engulfed by my pussy dident have to work, the rhythm of the ass pounding was doing it for him. Soon I could hear him say over my screams, "here it comes bitch" and his warm jizz shot deeply into my now distroyed asshole. He eased out slowly and I could feel the hot cum ozzing out of the gaping tunnel I call my asshole.

My boy friends dad who still hadent cum told me to turn around and strattle him reverse style, and even though I was wore out and my poor little legs were shaking I did as commanded. He eased my streched out gape hole of an ass over his cock and started working me up and down on it. The other friend walked up in front of me and said, "open your little mouth." I did as told and he eased his cock in stretching my jaws wide. He grabbed me by the back of my head and started ramming his cock down my throte leaving it deep in there until I gagged then pulling out and watching the large amounts of saliva string from my chin. Then he would do the same again, fucking my little neck hole until I gasped for air.

As this was going on the ass fucking I was receiving from my boyfriends dad was almost unbearable. He was slamming into my asshole with so much intensity I knew the next day I was gonna be bruised. With one cock in my throte and one slamming my teen ass I felt the warmth of hot jizz shoot down my throte watering my eyes, and the rhythm of the ass pounded increased, almost to much to handle I heard my boyfriends dad say, "here it comes doll." He lifted me up off his cock, cum dripping from my chin and running from my ass, stood up, pushed me too my knees and shot loads of hot cum all over my young face. I tried catching it all in my mouth but it was no use I was covered with milkey white jizz. I rolled over panting, tring to clear the snowballs from my eyes, when my boyfriends dad helped me up,now wearing his boxers ,and took me to the bathroom to shower up.

My legs shook so bad I could hardly stand. Once I finished I wrapped a towel around me and found my cloths and got dressed. The guys were all dressed and back to playing pool when I walked through, tring to hide the limp I had from that pounding, and the uncle said, "come back whenever you want darling, my nephew is lucky to have a girl as beautiful as you." I shot him a little grin and walked out to my car. Before leaving I thought about what just happened and a smile crept up on my face, I did what I said I was gonna do and more without chickening out. And I loved it.

Jaylynn Nichole