Jenna's Fantasy

by Paris Waterman

Copyright© 2012 by Paris Waterman

Sex Story: Jenna confides her secret fantasy to her boyfriend who endeavors to make it come true

Caution: This Sex Story contains strong sexual content, including Ma/Fa   Mult   Consensual   Rape   Rough   Humiliation   Group Sex   Size   .

We had been drinking wine and beer; had even done a couple lines of coke that fateful night while fooling around on my couch. As I recall, I had a hand under her bra toying with her nipples when Jenna asked if I'd like to hear about her fantasy.

"Of course I would, Jen," I replied. And why not, any insight into her deviously feminine mind might prove helpful in our relationship.

Jen gave my dick a friendly squeeze, giggled nervously and said, "All right. I've been wanting to tell someone about it."

"Maybe I can make it come true," I volunteered.

She laughed outright at that then said, "Jeez, wouldn't that be something!"

"So, go on, lay it out for me, Jen."

"I lay in bed at night thinking about being raped."

"Do I know this rapist?" I asked, thinking it was me she had in mind.

"To be honest, sometimes it's you, but more often of late it's somebody else. Someone I've never met. You know, a complete stranger."

"And it makes you hot," I added.

"Does it ever; I have to jill off afterward. I have the most tingling sensations for hours afterward."

She climbed onto my lap and, keeping her eyes coyly averted, caressed my shoulders. I must have derailed her train of thought when I started kissing the hollow of her throat. I felt a shiver run down her spine, and a soft sigh escaped her lips. I worked my way up her neck, becoming more adventurous with every kiss.

Jenna pressed herself into my lap, wrapping her legs around my waist, her skirt hiked up above her thighs. My hands drifted down along her ribcage to the curve of her waist, caressing all the way then skimmed along the silky smooth texture of her thighs.

Her palms shimmied their way over my chest, her fingers toying with the taut nipples, obviously enjoying the firm muscle beneath her hands. Jen had told me her old boyfriend had been skinny, and she couldn't get used to the difference between us. I had hopes of making her forget him completely.

Her body was responding with an enthusiasm that was almost embarrassing. The wine, coke and touching my body along with my strategic kisses had her giddy enough to confess that she found my mouth ever so sensual as it moved over hers.

"Like what I'm doing?" I asked, teasing her into responding by ending my kisses for the moment.

"Um ... you're kisses ... they're sooo hot ... I love the way you suck on my lips and all the teasing and pressures and the starting and stopping..."

Jenna paused to take a deep breath. I continued caressing her, moving my hands up the backs of her thighs and under her skirt to squeeze the cheeks of her fine ass. I heard her encouraging me with murmurs of excited pleasure. My fingers seemed to float over the crotch of Jen's panties. They were almost soaked through. On feeling them make contact with her genital area, she parted her legs, inviting me to do more.

We entered a hungry, wanton kiss, that lasted until I rolled her over on her back, laid on top of her and began moving her body up and down the length of my cock; then I renewed the kissing.

From then on all Jenna wanted to do was have me fuck her.

"Wanna suck my dick for a while, Jenna?"

"Sure, lemmie take it out."

She straddled my legs and extracted my cock. I moaned as her hand moved over the swollen, sensitive flesh of my erection.

Then with one hand holding the base, she lowered her lips to the circumcised head, circled it with the flat of her tongue and absorbed it into the wet warmth of her mouth.

I found my hands curled in her hair, whispering encouragement to her actions.

Jen sat herself on my abdomen, making sure I could feel how wet she still was against my skin, and leaned in to kiss me on the mouth. Blindly, I reached around her and released the clasps on her bra and attacked her lush breasts while she kissed my neck at the point where it met my jaw and sucked softly, leaving a very noticeable love bite.

"Mmm, Jenna, c'mon finish me off," I pleaded, my voice sounding husky even to me.

"Kay," she said, and drew the head of my cock into her mouth and held its penetration at about two inches. After a minute or two, she discovered her mouth was producing a great deal of saliva, and found my cock easier to manage.

Actually I had thought Jenna had had more experience in oral sex. I would learn that mine was only the third cock she'd had in her mouth. The first had been a furtive experience, over to quickly for her to realize what she'd done right or wrong. The second was with a guy who'd cum quickly after a long make-out session, and when he came in her mouth he'd almost choked her with his semen.

Still, Jenna hadn't been reluctant to accept me when I asked and I took that as a positive. Actually, her technique, such as it was, improved minute by minute. Having satisfied her that I wasn't going to come for some time, Jenna began experimenting; wrapping her tongue around my cock and making me feel pretty damn good.

"Good job, baby," I cooed to her. Jenna responded by sucking hard and her tiny hand circled that part of my dick not in her mouth and began jerking me off. It was instinctual on her part, and more importantly, Jenna was enjoying it.

I called her name out. Jenna removed me from her mouth. "What? Am I doing it wrong?"

"No, but keep it out for a minute. I want to see you licking it."

Jenna began licking the head as if it were an ice cream cone.

"That's great," I told her. "Now, just run your tongue up and down it, all the way. Then take it into your mouth and suck hard. Do it a couple times, okay?"

Eager to please, and anxious to learn, Jenna said, "Oh, yeah, for sure."

Her pink tongue darted out to flicker over the sides of my dick from the base to the crown, and she seemed to revel in the sound of my groans. Her tongue was moving like a snake, coating every inch of my velvety soft, yet hard as steel cock with a fine patina of sweet, warm saliva.

"I ... I can actually feel the blood rushing through your ... um, cockie.

"Do my balls," I croaked, no longer trying to control my voice. "Lick them, just like my cock."

Without the slightest hesitation Jenna moved to my testicles, holding the soft globes in the palm of her hand and examining them carefully before applying her tongue to them, licking softly, knowing they were delicate beings, and feeling the joy of having me trust her to handle my 'crown jewels.'

She became a little more adventurous with my love sacs, opening her mouth wide, and taking both balls into her mouth. And when I couldn't stand it anymore, I whispered feverishly, "Suck my cock again ... hurry!"

Reluctantly, Jen relinquished my balls, and after brushing the hair from her eyes, took me into her mouth. She also made sure she kept my balls in her hand, teasing them with the tips of her fingers as she increased the velocity of her suction.

"Jenna! I'm almost there!" I called out in warning.

She renewed the intensity of her sucking.

"No! Please stop!"

"What?" she said, plopping me from her mouth.

"I ... I want to try something. That is if you don't mind."

"What is it, baby?"

"A tit fuck; I want to fuck your tits."

Jenna didn't understand and blurted out, "There's no fucking hole there. How are you gonna fuck them?"

I managed a weak laugh, and Jenna gave me a questionable grin.

"Rub it between your tits," I told her. "Go on, squeeze it between them."

"Oh," she said, beginning to understand. She took my dick and pressed it against her chest, using her other hand to press her breasts together. Glancing down, Jenna saw for herself how her breasts formed a nearly perfect channel for my slimy cock to ride.

I began moving. Every now and then my prick would protrude all the way to her mouth, allowing Jenna to make further use of her talented lips and tongue.

"Take it into your mouth again," I croaked a few seconds later. "I'm ready to cum now. Don't be scared. I'm going to shoot off in your mouth."

"I don't want that," she said.

"Don't worry; it won't choke you, Jen."



Moments later her tongue was dancing over the head of my cock again; I held off as long as possible, prolonging that feeling of pure rapture that comes with the orgasm.

I came. With the first spurt, Jenna whipped me out of her mouth, and then not knowing what to do with it, held my cock scant inches from her face and I emptied my balls all over her face.

Evidently Jenna found this funny and more pleasant than having to choke on the load that would have filled her mouth had I remained in it while ejaculating.

Jenna got up from the couch as quickly as possible, and ran into the bathroom for a towel. She wiped the sperm from her eye, and then tried to clean it from the rest of her face. I have no doubt but that she was extremely embarrassed at letting me witness her lack of composure.

"I ... I guess another woman would have handled the situation differently," she said, revealing her mortification to me. I quickly reassured her that what she had experienced was fairly common, especially when not all that experienced at giving head.

"Why didn't you have better aim?" she asked petulantly.

"Um, how do I say this tactfully?"


"Jenna, you were holding the weapon that discharged in your face. Um, you were aiming it, not me."

She started laughing. "I was wasn't I?"

"Yeah, you was," I added, joining her in the laughter.

We had some more beer and wine, and then thinking I'd never find her more receptive to the question I wanted to ask, put the question to her.

"Jenna, don't fuck me over..."

"I'm not fucking you over!"

"Yeah, you are. You told me earlier about your fantasy; said you dreamed of being raped."

"I do!"

"Maybe so, but that's not really your secret fantasy, is it?"

"How ... how do you ... I mean, what makes you say that?"

"The rape thing was a kind of test, wasn't it?"

"Where did you get that idea?"

"Women tend to lie about their fantasies."

"And you know this how?"

"I ask them. They tell me the lie or lies, and I ask them again. When they realize I know they're bullshitting me I get as serious as possible. Now you and I are about as intimate as we can get at the moment. It's the perfect opportunity to share that fantasy without fear of my making it anything but a common thread between us."

This was pure bullshit, but it sounded sincere as hell, I waited for her reaction. A minute went by. Two minutes went by, and then she started to cry.

"I was bullshitting you. I mean, I wasn't lying, not exactly. I think all girls dream about being raped, you know. It ... it removes the stigma of giving in to someone by having the male take what he wants without permission. Society ... hell, parents, teachers, friends all warn you about giving it up too easily. So being raped takes all those barriers and tosses them aside. You aren't giving it up to the rapist."

"So what is your real fantasy, Jenna?'

"Okay ... I have this ... fantasy about finding myself with my boyfriend in an alley next to a club. We're making out, maybe a minute or so before he's gonna do me when these two big guys come out of nowhere. I never even see them. One of them holds my boy friend; the other covers my head with a bag of some kind. After slapping me a couple times I stop struggling. He yanks my top up, I'm not wearing a bra, and he smacks my boobs around, I'm crying and begging him not to hurt me anymore.

He has me face the wall and enters me from behind. A little bit later I realize it's the other guy fucking me and that I've got the first guys cock in my mouth. I've never been hotter in my life. And as I start to cum I wonder what my boyfriend is doing. I mean, no one's holding him. I'm thinking they killed him and I'm next; and that brings on the greatest cum I've ever had.

After they finish with me, they're gone as suddenly as they arrived. I pull the bag from my face and see my boyfriend standing there with his cock in hand jerking off.

Instead of feeling outraged that he allowed them to violate me, I'm boiling over with lust. I tell him to put it in my ass. He pins me to the alley wall and fucks my virgin ass. Then he helped me put myself together and takes me home, where we go at each other like the animals we are.

"And that's about it," Jenna says softly.

"That's a great fantasy, Jen."

"You think?"

"What would you say if I told you I could make it come true?"

"Oh, no!"

"Why not?"

"It's a fantasy. I don't ... I never thought about it as actually happening."

"I want you to think about it. I want you to refine the details. Take a couple days, mull it over. We'll talk about it again; maybe change a detail here and there, you know, like tweaking a script. Add something here, take away something there. But always with what you want to happen because it's your fantasy."

"I don't..." changing tact she tried to turn it around on me. "You haven't told me your fantasy."

"I've lived mine already. That's why I want to help you live yours. It's really fantastic. It's something you'll relish the rest of your life. Think about it. None of your girlfriends will have done this. You can tell them if you want to see their faces fall."

I paused for a minute, and then repeated what I'd said earlier. "Just think about it, Jenna. Live out your fantasy." I got up and dressed.

"I'll call you Friday. We'll go out for drinks, catch the late show. No pressure, I promise. Then when we're back at your place you can give me your answer. Is that fair enough?"

It took Jenna a while before she answered me.

"Okay, sounds fair. See you Friday then."

We kissed for a while and then I left, counting the minutes until Friday.

"Okay ... I have this ... fantasy about finding myself with my boyfriend in an alley next to a club. We're making out, when these two big guys come out of nowhere. One of them holds my boyfriend; the other covers my head with a bag of some kind, and they rape me repeatedly."

I couldn't get Jenna's fantasy out of my mind. If I tried to make it come through would she go for it? I had told her to think about it, but couldn't resist calling her the following morning.

"So, Jen ... did you think about having your fantasy a reality?"

"I did. I couldn't sleep a wink last night. That's all I could think about. Tell me more about what you have in mind," she said. The excitement in her voice told me more than her words had, which was plenty.

Since I had no actual plan to relay to her, I winged it, and told her that the alley was out of the question, as a passerby might call the police and there would be no end to our explanation. Jenna accepted this at face value, only asking, "So where then?"

"How about your apartment?"

"My place? You want me to let strangers into my place?"

"They won't have a key, Jen. We'd leave the door ajar, they'd come in, surprise us and overpower me and have their way with you."

"I don't know," she said, obviously reconsidering the factors involved in making her fantasy come true.

"Look, Jen, let's talk about it over dinner, okay?"

"Okay, Dino's on 4th?"

"Dino's it is, say an hour?"

I made three calls; my plan was underway.

Jenna walked into Dino's sixty-two minutes later, pony tail bobbing as she walked. The short pink sundress rode up her shapely legs, and she had to constantly pull the straps back onto her shoulders as they slipped down. She looked gorgeous, even if the pigtails did make her look five years younger, at twenty-one-years of age that five years made quite a difference.

She glanced at my crotch, saw the tell tale bulge and smirked. Her outfit had done its work.

"I'm glad to see you too, sweetie," she chirped, full of confidence ... for the moment.

But I knew that she was probably game for whatever I had in mind, and after we were seated in a secluded booth and placed our drink orders I pointed to her nipples poking through the thin material of her sundress and said, "You seem kinda horny Jen, or is it just me?"

Actually she looked adorable, even with the pouty lower lip that I knew was more for effect than anything else.

"Come closer, Jenna."

She edged closer. "Don't panic at what I do next."

"What are you... ?"

I slipped the straps of her sundress off her shoulders and turned her so that her front was facing the bar where one solitary man sat. It didn't appear that he was looking in our direction, but I knew better.

Having bared her breasts in the dimly lit restaurant, I reached around her and cupped them, stroking the nipples with my thumbs.

"Christ, I'm not getting arrested for exhibitionism, put them back!"

"He's watching us, you know," I whispered in her ear.


"They guy at the bar."

She shuddered then froze. "Are you fucking with me?" Her eyes widened as she looked over at the bar and saw him slowly stroke a tell tale bulge in his slacks, drawing the motion out to make certain she understood what he was doing.

"My God, how did you..."

"I have friends in low places, Jenna."

"You certainly do, but what has this got to do with..." she was fumbling her tits back into the cups in the sundress.

"Your fantasy? Everything and nothing. After we eat, and we are going to eat, we'll head back to your place. The gentleman at the bar will follow."

"You can't be serious!"

"Of course I am. Just let things play out and you'll have lived your fantasy."

"You seem to have forgotten there were two guys in my so called fantasy."

"I haven't forgotten a thing," I said as I gave the man at the bar a lazy, high-five kind of wave.

Jenna could eat no more than a tablespoon of her pasta. I cleaned my plate, chuckling when the man at the bar paid his tab and got up to leave.

"But ... he's leaving!" Jenna gasped.

"He knows where you live. He'll be waiting for us." I didn't mention that he wouldn't be alone. I kept my eyes on her face, wondering just how far I could push her boundaries. I decided to push as hard and as far as I could without Jenna screaming for the police.

In the ride back to Jenna's, I had her dress up over her hips and fingered her as she drove, avoiding careening into other vehicles by the proverbial cunt-hair. The fact that she kept her legs spread and never told me to stop while my fingers made sloppy squishing sounds told me she would go along with my plan without protest.

I let her pull into her garage and park before pistoning my hand into her and getting her to cum hard. We walked to her apartment on shaky legs; hers from the orgasm still rippling through her; me from the excitement that lay ahead for the two of us.

Once inside Jenna's apartment, I left the door ajar and steered her into her bedroom and flipped her onto the bed. The slickness in her pussy signified her definite arousal. I had her lick my fingers clean of her juices and concentrated on her breasts. She loved having them played with, and the rougher I treated them the more she liked it. I had shared that information with those about to join us.

Wondering where the others were, I finished toying with her tits and pushed my face between her legs. I wanted her hotter than a two-dollar pistol when the others made their appearance.

Jenna moaned and tried to sit up, knowing that someone was coming, but not when. "They'll be here later," I told her, although my voice was muffled by her twat.

She whimpered and seized my head with both hands. "Eat me, baby, please make me cum again!"

What could I do? I gave her a savage tongue lashing that had her moaning and then squirting (yes, Jenna was a squirter.) into my mouth and face while she squeezed her nipples and told me she was cumming.

I heard Dominick (the guy from the restaurant) and the others enter when they closed the door to the apartment. I kept my face buried in Jenna's snatch; she helped by humping my mouth frenziedly as she came again. I think she heard them when they walked in on us in the bedroom for she called my name out twice, even as I sucked her clit into my mouth and rolled the little bud from side to side with my serpentine tongue.

"SOMEBODY"S..." she screamed, just as Dominic hauled me off of her, a bit more vigorously that I had planned. I fell to the floor and moaned in real pain.

"HELP!" Jenna screamed, before Dom got a hand on her mouth and snarled at her to: "Shut up or else!"

"Don't hurt me!" she cried, but in a lower tone. Freddie slapped her across the face. Jenna stopped protesting, but continued to cry.

I lay on the floor waiting for them to cover her head with the hood before getting to my feet. Let her think it was real for a while, I thought.

I stood at the base of the bed and watched as Freddie flipped Jenna over and positioned her so that her ass was raised up. I had to lick my lips on seeing her inner thighs glistening with her juices and my saliva. Freddie ran his finger up Jenna's thigh and then stuck it in his mouth, sucking it clean. Jenna was sobbing, and I knew that at the moment she had forgotten about her fantasy and thought she was being raped, or had completely given herself over to it. In either event, the 'uninvited' trio went to town on her.

Freddie spread her pinkish pussy lips which were fully engorged. He sent two fingers into her and swirled them around. She moaned and moved her hips. Pulling the finger out, he positioned it at her ass, Jenna suddenly balked.

"Don't do that!"

Both Freddie and Dominic were taken aback, and paused long enough for Jenna to say, "It's dirty," in a shaky voice. "Things aren't supposed to go in there."

Dominic moved into action and slapped Jenna hard on the ass. SLAP!

"Ow!" Jenna yelped, seemingly confused at the direction of the blow.

Slap! Slap! Slap! Jenna's ass now had distinctly red handprints on it.

I noticed that Jenna hadn't called out my name since they'd entered the room. I knew that she had to realize this was part of the plan to fulfill her fantasy and was going along with it.

Slap! "OH! Please no! Stop it, I'll be good!"

"You're going to do as I say, aren't you?" Freddie snarled.

"Yes, yes, anything you say, yes!"

Freddie's voice brooked no argument, "I want to put something in your ass, and I damn well will put something in your ass. You hear me?"

"Yes, yes I hear you!"

"Now spread those red cheeks for me!"

With her face buried in a pillow, Jenna reached back and pried her ass cheeks apart. Freddie shoved two fingers into her pussy, wet them thoroughly and then with no hesitation pushed both into her supple asshole.

"OOOOH!" Jenna screamed, "It's killing me!"

Dominic slapped her ass harder than he had before and roared, "Shut the fuck up, bitch!"

Jenna choked on a sob as her asshole was stretched even more as Freddie's fingers began moving in and out of it, making her even more uncomfortable. There seemed to be no lower debasement for her to go, with her ass impaled on his fingers while her ass was hunched up for him. In full acceptance of her fate, Jenna gritted her teeth and prepared for the worst.

There was the unmistakable sound of a zipper, and then he was pushing his dick into her pussy from behind, making her realize that she had stayed wet the entire time he'd been playing with her ass. He held her hands at her wrists, pressed above her head against the headboard. One cheek and her breasts were flattened against the sheets; and as he began to move in and out of her, Jenna realized the others were watching everything.

Freddie grunted and she felt him spurting his seed into her. Thank god I'm on the pill! She thought as he emptied himself in her vagina.

He didn't ass fuck me! She told herself and felt a huge wave of relief sweep over her.

As Freddie dismounted he gave her sore ass another slap. Jenna saw this as an opportunity to rid herself of the hood over her head, and did so. Quickly glancing around, she saw Freddie and then Dominic; turning the other way, she saw me standing there playing with my dick as I watched her being abused.

"Jesus Christ!" she barked in my direction. "How many... ?"

Dominic sprang at her, cutting her words off in mid-sentence while brandishing a long serrated knife. I hadn't counted on anyone using a weapon of any kind. They knew she wasn't going to fight them off. What the hell was he doing?

"I won't hurt you unless you make things difficult," he snarled.

He was wearing a t-shirt and gym shorts, and the erection in his shorts was obvious. Jenna started babbling that she would be good. She would do anything if they promised not to harm her or me.

There is more of this story...
The source of this story is Storiesonline

To read the complete story you need to be logged in:
Log In or
Register for a Free account (Why register?)

Get No-Registration Temporary Access*

* Allows you 3 stories to read in 24 hours.