Rate by The Naughty Meter
Naughty level to be set later
Categories: Anal Sex, Virgins/Young women
Tags: outside scream college Vaginal
Location: The beach
Roleplay: Sugar Daddy/Baby
Fulfillment: Share it only
Candice ran ad on an internet dating site; Looking for Sugar Daddy to pay off my student loans will provide personal services. A business associate seen the ad and emailed her on my behalf, telling her I was very interested in being her sugar daddy. That the personal services would involve descrete sexual encounters. These encounters would be in various locations around the country and she would be provided a private jet, limo, expense account, and high class accomendations. I would pay her student loans off and possibly provide employment opportunity.
Candice is 24yr old college student heavly in debt with student loans. She is 5' 5'' tall with a curvy body, angel face, 34C breasts with prominent nipples and long brunette hair.
Candice immediately accepted my offer, I flew to meet her. Candice was waiting in the lobby of a 5 star hotel. I pulled up in my red jaguar convertible, the doorman signaled for Candice. I opened the passenger door for her and she jumped in wrapping me in a hug. As we pulled away I said " Wow... you are a beautiful young woman." Then my eyes traveled from her bare throat and stopping for a second on her breasts then down further until I stopped at her bare thighs where her skirt ended.
Driving down the quiet street, blaring my radio, we didn't talk much. I drove to my favorite spot near the beach. We sat in that parked car for a few minutes but the silence made it seem so much longer. She was about to say something when I stopped her. "You're so beautiful, and young..." My voice was but a whisper; She didn't understand what I was trying to say so she thought she had done something wrong. "John? What's the matter? Are you o..."? Again I stopped her, this time by firmly placing my lips on hers.
I tried to pull away but she placed her hand on the back of my neck and pulled me back to her mouth. Her lips parted and my fingers wound in her hair as our tongues intertwined. Gently sucking, biting, moaning... I pushed her back, forcing her into the back seat. She became shockingly aware of how short her skirt was. "John...John please..." She placed a hand on my chest as we continued kissing, fumbling with the buttons on my shirt then finally rubbing my toned arms and abs with her small soft hand.
She heard me breath out deeply. She pulled away long enough to lift her shirt over her head before forcing my tongue into her mouth again. My rough hands found the clasp of her bra and with one quick movement it was thrown into the front seat. I kissed her lips, gently sucked on her lower lip before kissing my way down her neck. I kissed her collarbone, sending a wave of electricity through her. Her breath quickened as I kissed down her breasts before taking one into my mouth, flicking and sucking the nipple.
The electricity came back, She moaned my name as I massaged and sucked her breasts. She felt my free hand travel down her side and down her leg, bending her knee up. My fingers barely touched her skin as I moved them up her thigh, brushing them slightly across her panty-covered slit. I moved my hand farther up and soon her thong was up in the front seat with her bra. My fingers danced across her mound, She knew I could feel how wet she was. She was sure I felt how badly she wanted me, needed me. Before she knew it I had two fingers in her wet pussy, pushing them in and pulling them out. My head was between her legs, licking up and down her slit as I fingered her.
Candice was 24 yr old virgin, looking up at me with apprehensive eyes. I smiled down at her with a barely concealed contempt that made her both revolt against me... and desire me. I told her, without ceremony, to lie face down on the backseat, with a pillow under her tits and her ass in the air. Candice feels my hairy legs pushing her legs apart, I begin to stroke down her back to her buttocks, my finger traces up and down her ass crack. She jerks, as my hands bein roaming over her slender thighs then under her grabbing her firm ass exploring her.
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! Candice 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 continues pressing until pushing inwards inexorably, she feels the pain as my finger goes in deeper and deeper, up to my knuckle, buried in her small tight virgin ass.
Candice is trying to relax hoping the pain will go away. She relaxs a little, then I start sliding my finger in and out. Candice screams, NO! PLEASE NO! My finger pops out of her, leaving her feeling sore. She feels my rock hard 10 inch cock pressing aganist the lips of her pussy, she jerks as my hand runs up and down her pussy, stroking her clit, then back down and now one finger begins to enter her pussy. Candice whimpers and moans opening her legs more, giving me access to her pussy."Please, don't do this, it hurts," as one finger becomes two and then they begin to move in and out of her pussy.
With a hard jolt, I push two fingers deep inside her and stop. Candice feels my fingers beginning to spread her open. " It hurts, please stop" she cries, but the fingers continue to spread open her pussy. The two fingers retreat, but three enter into her pussy. Kneeling between her legs, I slowly rub both hands up and down Candice's inner thighs, enjoying the feel of the nylons she wore. I always been a leg man, and Candice has beautiful legs. I rub my hands over her inner thighs, up to her stomach and over the satin of her garter belt, up to her breasts. I gently, softly fondle her breasts, small moan escapes Candice's throat.
"Uuuoooohhhhhh." Candice moans as I gently push sliding my big hard cock into her wet pussy, lightly kissing her neck and shoulders as I did. Candice looks back at me as I began to slowly, thrust easily into her. As I lean down to kiss her neck again, Candice closes her eyes.
" Ooooohhhh." Candice moans as my balls slap aganist her. " Oooohhhh." These were not the moans of pain. They were moans of one body responding to another. Moans of acceptance. " Ohhh. Ohhh. Uuhhh. Uuhhh. Uuhhh. Ohhh." Candice continued responding to my gentleness. " Ohhh. Ohhh. Uuhhh. Uuhhh. Uuhhh. Ooohhhhhhh." Candice was moving in time with me, her pace increasing as mine did, her ass pushing back against me. Candice felt the stirrings deep inside her. Slowly, she was becoming aroused. I was kissing and fondling Candice, moving in cadence with her as I felt my own excitement grow. I drove deeper into her like a pile driver and she responded, moving with me, driving her hips back to meet my thrusts.
" Ohhh. Ohhh. Uuhhh. Uuhhh. Ohhh! OHHH! UUHHH! UUHHH! MMMMMMM!" Candice moaned loudly. " OHHH! OHHH! UUHHH! UUHHH!" Candice moaned as she pulleded me tighter against her. She felt the feeling of arousal growing inside her, felt her body responding more and more to my attentions. "OMG! OMG! OHHH! OHHH!! UUHHH! OHHH! UH-UH-UH-UUUHHHHHOOOOOOOOO" Candice screamed as I thrusted hard into her popping her cherry.
" OHHH! OHHH!! UUHHH! OHHH! UH-UH-UH-UUUHHHHHOOOOOOOOO!!!!" Deborah groaned as her body was wracked by a tremendous orgasms. Her entire body trembled, pushing me over the edge as well.
" Oh God!!" I moaned as I began shooting my load into Candice. Candice was still in the throes of her own orgasms as she felt the heat of my sperm filling her insides. The throbbing of my cock inside her caused her to groan as her orgasms began abating.
" Mmmmmm." Candice sighed, as the trembling of her body slowly ceased. I collapsed aganist her with a sigh of contentment. I raised up off her, sliding my hands up and down her long slender thighs and rested them on her ass. "You have such a beautiful ass and I bet it is hot, virgin and tight. I parted her legs, tears began to fall from Candice's eyes. Her legs were now spread obscenely, opening her pussy and her ass to me. "That's too far, it hurts", she cried.
I looked at this beauty spread naked before me, her ass open, her anus peaking out. I again eased between Candice's thighs. "What are doing" she yelled. "Quiet down and do as you are instructed. My hands began fondling her ass. My hands slipped between her cheeks moving toward her anus."Please not there, that will hurt." My finger reached her anus and Candice cringed in fear as it began to enter her."Relax your ass and let me have my way."
My finger was dry and it hurt as it entered her. I pushed deeper into her rectum,"OOOWWW, that hurts, you're pushing too hard." I pushed hard and my finger plunged deep into her rectum until my knuckles hit her ass."Tighten your ass on my finger. Candice grasped my finger, "Again, you are very tight." Candice grasped my finger again. My finger pulled from her anus with a pop.
"First time to be fucked in the ass, Candice. "Yes, I would never do that, it would hurt."
You look so good spread out and your ass is so hot and tight. I am going to fuck you in the ass. As you know I have a large cock, so it will tear your ass as I fuck you, but the blood will aid as a lubricant. I can go about 20 minutes so by the time I come up your ass, you will be very sore.
As I pull my cock out of your ass, I want you to squeeze my cock with your ass muscles. Candice felt me press my naked body aganist her. She could feel my big hard cock push between her cheeks of her ass, resting on her anus. My 10 inch long and 3 inch diameter hard cock rested on her anus. She began to sweat in fear.
I stroked her sides squeezing her breasts, "OOOWW, that hurts." That's nothing, wait untill my cock forces its way into your asshole." Candice could feel me push up from her body and fist my cock placing it on her anus. "Your lesson is about to begin" and I began to push the bulbous head of my cock into her anus. My cock was dry so at the beginning, all it did was try to push into her anus. I lubricated my cock with KY gel and again pushed into her anus. It felt like a baseball bat was driving up her ass as I continued to push and pull back and push again, each time gaining a millimeter at a time."OOOOOWWW, it's too big, don't stick it into my ass," she wailed.
I pushed harder and Candice's anus gave up to the assualt and opened to the head of cock. "AAAAAAAAAHHH, OWWWWWW, its tearing me, take it out, don't push it in," she yelled. You only got the head, wait until you get all 10 inches fucked up your ass. I am going to stretch you open, You better fuck back. I pushed another inch in, than out. The next thrust gained two inches, than back out. Candice's asshole was bleeding from the assualt, adding lubrication to my cock for me to continue.
"Here comes all of it baby" and I pushed with all my might into her asshole. Ten inches of hard cock forced her asshole to open bigger then it ever did. Her asshole was stretched and torn to accept the fucking of her ass. I pulled my cock out to the head and than began the painful journey back up her ass. My cock was gripped tightly by her ass.I began to fuck her ass hard and fast, riding her. My cock thrusted into her deeper each time, causing her to cramp as it was forced to accept my hard cock. Each stroke of my cock brought a fresh batch of pain to her ass.
Candice felt my cock swell as I thrusted into her, I groaned as I exploded in her. My hot cum flowing like lava in her. I collapsed on top of her breathing hard in her ear. Deborah was shivering and crying as I pulled my cock out. Every time we meet be prepared to be fucked in the ass.