Day of Sailing added 2 years ago

By: gray6lover009 Age: 58 Country: United States

Currently 3.5/5 Stars.
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Rate by The Naughty Meter
Naughty level to be set later
Categories: Virgins/Young women, Anal Sex
Tags: lick pretty buttocks tears swollen pain incredible
Location: Other
Roleplay: Stranger/Stranger
Fulfillment: Share it only
Nature: Romantic

I took Jenilee out for an all day cruise on my yacht. Jenilee was laying on the chase lounge nude, I was by the bar, fixing myself a mixed drink of bourbon and cola before walking back around to join her. I took a long gulp of my drink and walked over to where Jenilee was stretched out. She smiled up at me from where she lay, and reached up alluringly with her right hand for me. I took hold of that hand and kissed it tenderly, then leaned down to kiss her passionately on the mouth.

At last, though, I pulled away, and took another deep drink of my bourbon mixer before putting it down on a nearby tabletop. When I turned back to Jenilee again, she was giving me a broad, salacious smile and had her legs spread wide apart, her pussy stretched wide open and exposed for me to see.

"Well, isn't that a sight to behold..." I breathed in honest admiration, staring hungrily at the young woman's spread-open cunt. I could see right into her pussy, as the outer lips were wide open and her pink bits were exposed. She was quite wet between her legs, and obviously so – Jenilee was turned on by the fixated attention, and couldn't stop squirming about under my intense gaze.

Jenilee reached down with her left hand to run a couple of fingers through her moist, wet flaps, and then let one of them slide deep into her throbbing cunt. She moaned softly when her clitoris was stimulated, as I just watched on now, smiling ever so slightly as she continued to play with herself for their shared pleasure.

I reached down at last to take hold of my inflating cock, and started to tug myself off as Jenilee slipped a second finger into her vagina. It was incredibly arousing to watch a young woman, like Jenilee deprave herself by masturbating, as a man she'd only just got aquainted with watching on and playing with himself as well. It made me tingle all over with desire, but it was the anticipation of what was going to come that made it all the sweeter... Jenilee had never been seduced by an older man.

"Are you ready, baby?" Jenilee whispered, taking the cum-slick fingers out of her cunt and raising them up to her lips. She took them into her mouth and sucked the sweet juices down her throat, then took them back out again and grinned broadly. I didn't need any more prompting. I raced forward to join Jenilee on her deck chair. She had to scoot up a little bit to give me enough room on the seat, but was more than happy to do so.

Moving in to kiss Jenilee again on the mouth – this time with a little more soft, thoughtful tenderness than the fiery passion that they shared previously – I took hold of both of the small, cone-shaped tits and squeezed them tightly. Roughly kneading her boobs in my grasp, I kept on kissing her on the lips, but this time the hunger and desire was back. Our tongues slid around in each other's mouths, as the burning need for each other grew stronger. I flicked Jenilee's budding nipples with the thumbs and forefingers of both my hands, and smiled in our kiss when she moaned with lust up into my mouth.

I then moved my right hand down towards her moist, dripping pussy, as she thrust her pelvis up into my right leg with the passionate, mindless hunger of a sex-crazed fiend... soon enough, my thigh was soaked with her juices. As I moved my attentions away from kissing her and began to travel further south, licking and sucking a path up over the rise of her right breast to take Jenilee's hard, budding nipple into my mouth, I stroked a couple of fingers tenderly over her throbbing clit. Jenilee let out a loud gasp" Ohhh. Ohhh. Uuhhh. Uuhhh. Uuhhh. Ohhh." as her body trembled in pleasure, then groaned in ecstacy as two fingers slid slowly inside of her.

Sucking back on Jenilee's tit with ravenous passion, I slowly thrust my two probing digits in and out of the youthful woman's tight pussy until she was bucking and thrashing about on the deck chair. Soon enough, her cunt was dripping with the juices of her arousal, and she was thrusting her pelvis up against my inquisitive fingers with violent abandon. Rivers of tasty jizz were running out of Jenilee's moist snatch, and I was trying my very hardest to lap up as much of the delicious bodily fluids as I could. At the same time, my two fingers were beginning pistoned in and out of her tight, gripping pussy, and I continued to rub at her swelling clit with desperate intensity. Soon enough, Jenilee was squirming about on her back on the deck chair, her eyes clenched shut and her mouth hanging agape. Her face was flushed with passion, and her body tensed and thrashed about while I continued to slam my fingers into her, and slide my tongue around the outer edges of her dripping smoo.

Then I moved on to the other boob, taking the budding nipple into my mouth and lightly nibbling on the erect nubbin of hard, taut flesh. Jenilee gasped in estactic rapture, and I at last pulled my slick fingers out of her vagina. I took my mouth off her breast for just a moment, to suck both of my own fingers back and taste Jenilee's sweet pussy-juices. After savouring the delicious flavours of her moist, wet snatch, I continued my travels further down over her stomach. For a few long moments, I darted my tongue quickly in and out of Jenilee's tight little belly-button, causing her to moan softly "Ohhh. Ohhh. Uuhhh. Uuhhh. Uuhhh. Ooohhhhhhh." in pleasure as I tasted her. Then I moved on again, heading south. It was quite obvious now where I was heading for, and she could hardly wait to feel my tongue and mouth working on her womanhoodPulling her pelvis up into my face now, I went to work in hungry, passion-filled earnest. I parted Jenilee's outer pussy-lips with a couple of fingers of my right hand, and then slid my tongue as far as I could into the tight, wet folds of her pussy. She moaned "OHHHH, MMMMMM, OHHHH, MMMMMM" softly in pleasure as I drank back on her cum-juices. Then, suddenly and without any forewarning, I jammed two fingers right up into Jenilee's cunt, driving the digits right up into her as far as I could get them. With my thumb, I managed to stimulate the hard, budding lump of flesh in the crevice above her open pussy, making the young woman grunt and groan "OHHH........OMG.....OHHH...... OMG OMG.....OHH...OMG AH, AH, AH, OH, OH, OHHHHH" out loud as waves of orgasmic pleasure rose up inside her tingling body.

For a few long moments, I darted my tongue quickly in and out of Jenilee's tight little belly-button, causing her to moan softly "Ohhh. Ohhh. Uuhhh. Uuhhh. Uuhhh. Ooohhhhhhh." in pleasure as I tasted her. Then I moved on again, heading south. It was quite obvious now where I was heading for, and she could hardly wait to feel my tongue and mouth working on her womanhood.I slowly began to push the bulbous plum head barely inside her as a tease, it seemed like she was a virgin. The walls of her pussy were so tight that I literally could not push further. The lips of her pussy were wet, but her pussy was so small and tight, the more pressure I applied it caused pain. I guessed that she had not been fucked for a while. The more I tried to penetrate her the harder my cock grew. I decided to lubricate my cock with gel to help open the tight walls up of her pussy. I lubricated her pussy and my cock, then thrusted the bulbous plum head aganist her pussy, the shaft sank part way into her. " STOP! STOP! Please, it hurts."

We kissed again, with our tongues fucking each other's mouth, and the fragrent aroma of her pussy getting stronger making me even hotter. I grabbed her ass with both hands causing her to spread her legs further apart. Jenilee screams " OMG! OMG! STOP! STOP! as I push the bulbous plum head further into her. Then with a hard push the baseball bat size shaft starts stretching and tearing the small tight channel, Jenilee sobbing and screaming " OMG! STOP! OMG! STOP!" YOU are hurting me. I must push all of my cock into you, I must feel your pussy around my hard cock squeezing me.

"Your pussy is so very tight Jenilee, a small tight wet velvet box wanting to wrap around my hard cock. "Oh Baby! Tighten it up again Jenilee. "I murmured." Jenilee tightened her sheath, feeling me sinking all the way into her, "OH! OH! OMG! that long thick throbbing hard cock feels incredible." she screams. My fingers find her hard stiff nipples slowly pulling, twisting the sensitive nubs.

I have found that when I grab a woman's ass pulling her towards me , I can get deeper penetration. Jenilee is curvy with a nice firm ass, I literally pulled her ass towards me thrusting hard and deep into her pussy, resting the head of my cock aganist the wall of her uterus with each thrust. I pull her ass really tight aganist my groin, then start thrusting into her like a pile driver."OOOOHHHHH it hurts," she said with tears running down her face. " Ooooohhhh." Jenilee moaning as she nuzzles into my shoulder. " Oooohhhh." Pain subsiding, then moans of escatsy. Moans of one body responding to another. Moans of acceptance. " Ohhh. Ohhh. Uuhhh. Uuhhh. Uuhhh. Ohhh." Jenilee continues responding to my gentleness. Ohhh. Ohhh. Uuhhh. Uuhhh. Uuhhh. Ooohhhhhhh." Jenilee started moving in time with my hips and thrusts, her pace increasing as I did, her pelvic area grinding against mine.

I kept sliding my hot, hard cock in and out of Jenilee’s spasming pussy. " Ohhh. Ohhh. Uuhhh. Uuhhh. Ohhh! OHHH! UUHHH! UUHHH! MMMMMMM!" Jenilee screamed. " OHHH! OHHH! UUHHH! UUHHH!" " OHHH! OHHH!! UUHHH! OHHH! UH-UH-UH-UUUHHHHHOOOOOOOOO!!!!" Jenilee groaned as her body was wracked by a series of tremendous orgasms. Her entire body trembling, pushing me over the edge as well. I erupted in her like a volcano my hot cum flowing like lava filling her. Her orgasms began to ebb as I pulled my now dripping cock from her except the head. Looking down I saw her pink ass hole winking at me. Jenilee was moaning softly and pushing her pelvis back towards me trying to keep my cock in her. I pulled all but my cock head out of her pussy. My one hand kneaded her ass cheek I casually placed my wet fingers on her puckering ass hole. As I gently pushed forward my slick finger past her sphincter muscle. Jenilee froze. What was he doing? She hated the feeling of my finger in her ass hole. "No John, that’s sick" she complained "Just fuck me, it feels so good." "Shut up" I growled "One more small tight virgin hole left to test." Jenilee’s heart skipped a beat.

She shivers as my other hand pulls her cheeks apart and hold them that way with thumb and forefinger. I run a finger over her exposed asshole, making her body tense up and then...OH GOD! Jenilee feels the pressure on her exposed asshole as my finger pushs aganist it and she bucks wildly, tensing her muscles trying to keep me out. My finger continued pressing until pushing inwards inexorably, she feels pain as my finger goes in deeper and deeper, up to my knuckle, buried in her tight virgin ass. Jenilee is trying to relax hoping the pain would go away. She relaxs a little, then I start sliding my finger in and out. Jenilee screams, "PLEASE! PLEASE! Don't." My finger pops out of her, leaving her feeling sore. Then I slowly trace a path up her crack to her clit and again she cries out "OMG! OMG!" in lustful desire. Reaching her clit, I let my tongue swirl and twirl around that hard little button again and again. I slowly lower to her wet pussy, tongue fucking her then I go back to her clit, then take long slow slides with my tongue from her ass to her clit.

I instruct Jenilee to get on her hands and knees, she leaned down on her elbows raising her beautiful small firm ass high in the air. Standing at the

end of the lounge chair, I caressed her ass cheeks sliding a finger up and down her crack. He couldn’t be thinking of that. Please god don’t let him be thinking of that! But she knew that I was. My finger was moving in and out of her puckering hole. Before she knew it I had two fingers imbedded in her small tightest of holes. Dear god how could she ever fit John’s big wide cock in her tiny little ass? I was not to be dissuaded though.

As I removed my fingers she heard and felt me spit into her ass hole. Jenilee felt the head of my cock rubbing up and down the crack. I pushed against her anus and she braced herself for the brutal pain she would be forced to endure. "No, AAAAGGGG, not there, it hurts so bad, please don't, AAAAGGGHHHH, OMG STOP! " she cried as my cock began the painful journey up her ass. It felt like a ball bat was being forced into her ass.

Instinctively she clenched her muscles. "Better relax" I laughed " Its going in, one way or the other, but it will hurt a lot less if you just relax." I pushed a little harder. " Boy, her ass is small and very tight" I thought. As I put a little more weight into it I felt the head of my cock push past her tight muscle. I paused for a moment to let her get accustomed to the feeling.

Jenilee tried to catch her breath. John’s cock felt huge in her ass. There was no way, she was sure, she could ever accept his huge cock into her ass. "OMG! AAAAGGGHHHH! OMG! STOP! AAAAAAGGGGHHH! PLEASE STOP!" the pain was unbearable. I was pushing again. First one then two inches disappeared into her ass hole. I began to pull back only to push even more into her. As her abused ass hole became accustomed to its intruder the pain began to subside only to be replaced by something that almost seemed like pleasure. "I can’t possibly be enjoying this" Jenilee thought but certainly the initial pain had eased. The friction of John’s cock thrusting in and out of her ass hole was developing heat that was indeed pleasurable. Before she knew it she felt my heavy balls WAP! WAP! WAP! slapping her wet pussy. I was in. She had accepted all of 14"!

I couldn’t believe it. Jenilee had not only taken my full 14" but her ass was pushing back at me. She was looking for more! I knew she would be a hellcat once she got started but this was beyond my wildest dreams. I began deep stroking her. Pulling all the way out until just the head of my cock was left in her tight hole then pushing all the way back in. Jenilee was actively bucking back at me now. Her moans had turned to grunts as she raced toward yet another orgasm. I felt my own orgasm building. I let out a deep groan as I erupted like a volcano in her ass, my warm cum flowing like molton lava filling her full.

I pulled out of her ass as another load was ready to shoot, moving to the front of the chair facing her, she opened her mouth as my cum shoots filling her mouth. Jenilee crying as I felt my balls rising up and the muscles in my legs turning to molton lava. The cum raced up my shaft, I let out a deep groan as my cock shot its load onto her beautiful face. I said with a smile " I want you to remember this as a pleasant experience.