Kelly Ann's Starring Role Ch. 02

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She's blackmailed into sex before her wedding.
4.2k words
4.5
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Part 2 of the 4 part series

Updated 10/24/2022
Created 10/03/2005
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JRob
JRob
1,626 Followers

(Note: Reading Chapter I of this story will add some perspective for the reader)

*

Women are strange, aren't they? I mean, men are too, but women, well, who can figure out what they are thinking at any particular point in time.

I mean, I guess there is no etiquette for what happened in my basement that special night.

The vision of prim, proper, virginal Kelly Ann Peters sucking off my friends Tom, Dan and I in rapid succession was burnt into our memory. It was an exciting, erotic night, but while the guys were uncomfortable around the girl, Kelly Ann acted as if nothing happened. You would have thought she'd be embarrassed, humiliated, something, anything.

It could have been a dream or a he said, she said argument, except for the fact that I had much of the rendezvous on video tape.

In the weeks following Kelly Ann's fellatio experience each of us asked for a date in hopes of a repeat performance. Kelly Ann turned us town, saying she wasn't looking for a boyfriend, but never even remotely mentioned that special evening.

She didn't say a word to my sister Tara about her orally pleasing us, nor did she miss our weekly billiards session for the next several weeks. On those nights she didn't mention a thing, never intimated anything had happened nor did she treat us any different than she had before the episode. It was almost as if she had been totally inebriated that night.

Each of us was afraid to bring up the subject, wondering what kind of wrath would follow if Kelly Ann didn't remember anything, or worse. I will admit I didn't forget a single detail of that Saturday night when prim and proper Kelly Ann became a blowjob queen. I replayed that scene nightly, working my dick while thinking of her.

As time went on we all began dating...others.

Kelly Ann was seeing a couple guys and gradually had little time for her former pool partners. She and my sister Tara went on double dates, and Tara told me her friend was very happy with the guys she was seeing.

I often wondered if she remembered anything of THAT night, but soon moved on to other endeavors, like real dating. Still, I couldn't help thinking of the stunning redhead polishing and milking our youthful knobs before swallowing our seed. And knowing it had been caught on tape, available whenever I wanted, was quite exciting.

Over the next two years I infrequently ran into Kelly Ann, and the longer time went on the more distant she became. I heard she was bad-mouthing me with a couple classmates, which really stuck in my craw.

When she began dating the rich guy, James B. Jackson, she became not only distant but also condescending. It was almost as if she was too good for me now that she was seeing a rich boy. Her new beau was anything but a one-girl man.

Yes, he was seeing Kelly Ann, but he was still seeing several former girlfriends on the sly even after he and Kelly Ann announced their intention of marriage. Worse, he treated the gang of three --- Tom, Dan and I --- like dirt. That wasn't unusual; he treated nearly everyone like dirt. That's what rich people can do. Some suggest they are graduates of the High School of Being an Asshole.

It was summer, hot as all blazes, and I was working at a book store with faulty air conditioning when James entered in a hurry. He needed a certain book, and somehow we were out of stock. Well, the guy gave me a whale of crap, and then told the manager I had treated him poorly when all I had done was attempt to help him. I nearly got fired for that escapade and I made a vow to return the favor to the rich boy if I ever had the chance.

That chance didn't occur until I saw that marriage notice in the local paper. When I got home that night I locked my door and slipped my video tape of James' fiancée and watched Kelly Ann perform her exemplary oral talents of the Gang of Three.

Somewhere in the middle of the tape the idea struck, and the decision was made.

I might not be able to get back at James Jackson directly, but I would be able to take something of his without his knowledge...Kelly Ann Peters.

The plan was simple and took shape in minutes. In retrospect, it was probably not all that thought out, but, well, thinking of Kelly Ann and James at one time had a negative effect on my brain.

One, James B. Jackson was a jerk who needed to be taken down a peg or two or three. Two, Kelly Ann Peters was a beautiful virgin (or at least I surmised) with a blemish on her record. I had the video tape to ensure number three, I surmised, by taking care of one and two. All I had to do was find a way to make it happen.

Over the next couple days I thought of plan after plan, but honestly all sounded lame.

Then, my chance, I ran into Kelly Ann at Starbucks late one morning.

We traded cordial talk, and I congratulated her on her engagement. Then I leaned over and dropped the bombshell. "Uh, Kelly, does James know of your night with us?"

Kelly Ann blanched, her mind flashing back to the fateful evening.

"Oh, I didn't suppose he did," I murmured, answering my own question.

Kelly Ann stared at me for a few seconds, blood rushing to her pretty face.

"Jon, that was our little secret, and I expect it to stay that way. James would ruin your life if he found out about it. No matter what you say, I'll deny, and it will only mean bad things for you and your little friends. Let's face it, you aren't in my league," said the condescending girl.

I smiled at the lovely girl. I gazed at her lovely body, with my sight centering on her moist, sensual lips. I reached into a nearby envelope and pulled out a couple photos taken from the video tape. I showed the girl a couple shots of her sucking on a cock, photos that caused her to gasp.

"Uh, Kelly, I think you might better channel your concerns at his finding out about your involvement that night, not mine. And while he might not believe anything I said about your little escapade, I believe, I really do believe, that watching the video of your award-winning performance that night just might convince him that you are, well, not exactly the perfect, virginal, untouchable, chaste girl of his dreams. These photos are grainy, but the video is, well, much clearer."

Kelly Ann stammered some response, and then started to rise.

I put a hand on hers, smiled, and quietly whispered in her ear, "He doesn't need to know."

The girl looked relieved, then, seeing my smile, showed concern. "What do you want? Money? How much?"

I savored the moment, looking her directly in the eyes.

"No, Kelly, I want a little something money can't buy." She stared at me, shaking her head. She again stood, slapped my face, and stormed out of the coffee shop.

Opps, I scared her off. Maybe I had misread the situation. If she mentioned anything to Jackson I most likely would be on the receiving end of a whipping, no matter what the tape showed. The boy was a powder keg, and if he got something into his mind, well, nothing good would come of it.

I finished my coffee and sauntered out to my car, wondering if Kelly would seek help from her beau. Lost in my thoughts I didn't hear her car pull up beside mind. She rolled down her window, I mine, and the girl stared for a bit before startling me. "We can work something out. I know what you want, and it's possible, but I want the tape...no copies, nothing."

I had her! I thought for a few seconds, and then replied. "You need to know what I want. You can have the tape, but I have some specific needs, Kelly Ann."

"What do you want?"

I stared into her beautiful eyes. "I get a night in a hotel...we'll make love."

Kelly Ann digested the request, then countered. "I'm a virgin, so I will blow you, but that's it."

"That won't work, Kelly, sorry."

"You bastard," she spat.

"Yes I am, a bastard with concrete evidence. So we will do it my way or you get the highway from Jimmyboy. I can just see his parents faces when they see the tape."

Like two Army tanks facing each other, it appeared to be a stalemate. But after examining her options, Kelly Ann gave in to my demands. "Okay, but you have to be gentle. I'll do you, but it will be in my bed on my terms. Deal?"

"Deal, except for one other thing."

"What."

"We'll make love, and yes, Kelly, I will be gentle. But there's one more thing...I want a blow job on your wedding day. That's all. You get the tape, no copies will exist. I get what I want. No harm done. Deal?"

Again, she stared daggers at me. I could tell her mind was whirling.

"I am so disappointed in you, Jon, you are a real bastard," spat the girl. I couldn't tell what she was thinking, but I knew it was about me and it was not good.

"I'll call you."

Hum, it's great to be the King.

Over the next few weeks our paths rarely crossed, and when they did Kelly Ann would have a friend, friends or she was in the company of that bastard James around her. Throughout we never said a word. As the wedding date approached I began to have second thoughts about the arrangement. I imagined the young girl had enlisted help him obtaining the tape, or maybe having me meet someone's fist. I worried about arriving at her house only to be flogged by a trio of angry friends of Jackson and so forth and so on.

Maybe she called the cops. Maybe

Then, a week before the wedding, I received her call. No hello, no friendly greeting, the girl was all business.

"Here's the deal, my parents will be at the theater next Wednesday, and I will expect you to drop by at 8 sharp. Do not park near the house, and bring the tape and every single copy. You'll get your nut off, and we will be even."

I wasn't born yesterday.

"Whoa, just a minute, that sounds like a set-up to me. And I have no idea what tape you are talking about. Bye." Something told me she was recording the call, and I wasn't about to get caught in that trap.

Kelly Ann called back but I refused to answer until the third try.

"Yes?"

It was a more subdued Kelly Ann. "Please Jon..."

"Can't talk. I'm heading to the mall. Gotta be outside Nordstrom in 15 minutes to meet some friends for a movie." I hoped she took the bait.

She did, as I saw her walk from her car toward the main entrance. Nobody seemed to be following her, so I slipped in a side door and walked around front, spotting her. "Want some coffee?"

Kelly Ann followed along to Dunkin Donuts. I gentlemanly bought her a latte then spent the next 5 minutes or so staring at her.

"Jon, I want the tape. Hand it over and nothing bad will happen to you."

"Are you threatening me?"

"James has connections..."

I didn't say a word. My eyes darted around, and, seeing nobody staring at us I leaned over and whispered, "I have a tape. I think I will send it over to some friends. Actually, one has a copy, in a sealed envelop, to be send to James' dad in case something happens to me."

Kelly rambled for a minute, before a look of resignation came over her. "I'll do what is needed, but I'm not happy about it."

"Okay, now you're talking, Kelly Ann. You will get the tape and lead a wonderful rich girl life after the wedding. Uh huh, I can see you and James living happily ever after."

Allowing that thought to sink in, I set up the enchanted evening. "Okay, Wednesday it is. I will meet you right here as a matter of fact. Just hop in the car and I will wisk you away into someplace more private."

* * *

The rest of the week and days leading up to our rendezvous went past briskly. I made preparations for the night with a smile never leaving my face. It was agony not being able to jerk off, because I wanted Kelly Ann to get a full blast of baby batter.

Wednesday came and I watched as Kelly Ann pulled into the parking lot at the pre-arranged time. A prompt, perfect girl. I drove up, stopped to let her in, then sped off keeping a keen eye on the rearview mirror. I changed lanes, got off the Interstate and back on, ultimately driving to our destination...a cheap, no-tell motel I had checked into earlier in the evening.

We entered the room and I pulled her tight, kissing her neck.

"Let's get this over with," spat the girl.

"Um, no, Kelly, that's not the right attitude. We're friends, let's be friendly. Here's an outfit, try it on."

The girl looked at the bag, then inside. "You want me to wear this?"

Smart girl, that Kelly Ann.

The flimsy silk bra and even flimsier thong were very sexy, but the schoolgirl skirt and blouse would have given a blind man a hard-on. I got hard watching her handle the outfit, and waited in anticipation when she went into the bathroom to change.

Emerging, my dick grew harder. She was beautiful, and although I could tell she wasn't totally into it I saw from her face she would do what she had to do to make sure she would soon be Mrs. James B. Jackson.

"I'm not happy with you Jon. Not happy whatsoever."

I told the pretty girl that all would be fine, that she was very special to me and that given the situation she had a lot to lose. My advice was simple; she could either be with or not with the program.

Kelly Ann nodded, and said she had to be home by 11. I smiled and told her that was plenty of time for what I had in mind.

She looked adorable in the sexy little outfit, which showed off her long legs and pleasing breasts. I could have gazed at her pretty outfit for hours, but I knew time was a premium. The girl was here, with me, and I didn't want

The magnitude of the situation --- her upcoming wedding to James Jackson and resultant riches --- must have sparked something in her brain to be somewhat more compliant. She lowered her head, slowly shaking it, before looking up at me with a sly smile. "You aren't taping any of this, are you?"

I shook my head no.

She moved over next to me on the bed, put her arm around me, and kissed my neck. "This will be our little secret, right?" She whispered. "Tonight, my wedding day, and then I get the tape and we have this in our memory forever, right? Nothing more. Nothing else down the road. Agreed?"

Assuring her that was the deal, she planted a kiss on my lips, gently opening her mouth and forcing her tongue into mine.

That kiss sealed the deal.

We made out for a bit, and my hand wandered around her leg as I slowly stroked her milky why thigh. My hand meandered higher as the girl began moaning her assent. My fingers found the outside of her frilly red panties, and I stroked her mound as our kisses became more intense.

"Oh Jon," she moaned as my fingers made their way under the elastic of her panties. "Ummmm" was the sound as I gently ran my finger along her pussy lips. They were damp, and got even more wet as I continued my gentle massage.

My mind couldn't believe the luck my fingers were having at the girl's core. I though she might fight me off, but Kelly Ann was clearly getting into the sensual act we were completing. I slipped down onto the floor and gently reached under the schoolgirl skirt to remove her panties.

Slowing rolling them down her thighs I gazed at her pussy. She kept it slightly trimmed, still thick but obviously manicured. I lowered my head and began kissing her thighs and ultimately licking up and down and then in her soaking wet hole.

"Don't stop, that's incredible," said the girl, leaning back onto the bed. Her hands went around my head and she guided it up, down and against her pussy. It didn't take long, maybe 3 or 4 minutes, but soon her moans became more intense. I felt her thighs sort of shake, and soon Kelly Ann was moaning that she was cumming.

I continued to savor her pussy as she came down from her high. "That was wonderful, Jon, simply wonderful. Nobody has every made me feel that way."

"You mean..."

"Uh huh, that was my first orgasm."

The girl may not have arrived wanting an orgasm, but now that she had one she was a stick of dynamite. She began kissing me before sitting me on the side of the bed and going down on her knees, a picture of compliancy in front of me. She looked up into my eyes and then lowered her head to my cock.

Kelly Ann began sucking my dick with passion, moaning as she blew me. Her head bobbed up and down, lips encasing my dick, and I have to admit I had to slow her down before I quickly blew my load. My mind started thinking of sharp objects moving toward my eyes, nails on chalkboards and snakes in an effort to delay busting my nut in her sucking mouth.

The girl was ripe for more action, and I slowly pushed her head away and moved her up on the bed. I opened the demure white blouse and began nibbling her pert little breasts before moving up to her lips again. All the while I was fingering her slit, bringing her higher and higher once more.

It was time and I moved on top of the prone girl.

"Wait! Put a condom on," cried the girl.

I reach into the nightstand and pulled out a Lifestyles and showed it to the girl. Opening the wrapper, I held it in my hand. "Kelly, I'm going to get inside you bare back, but as soon as I do I will put this on," I assured her. "I don't want a baby any more than you do."

My speech must have calmed her, as she spread her legs wide and told me to be gentle.

I was, sliding my dick up and down her wet pussy. I couldn't believe my luck, the girl of my dreams was legs akimbo and waiting for my cock onslaught.

It wasn't an easy task. The girl was tight, and I had difficulty gaining access to her virginal hole. I prodded and pushed to no avail.

Reaching over, I grabbed two pillows and slipped them under her ass, lifting her a bit. Again I placed my cock against her tight opening and kissed the girl. I kept my dick against her hole for a few seconds before rearing back and thrusting at her hole.

I swore I heard her hymen snap but I know that was merely a thought, but whatever I was inside her gooey hole, moving in and out of her pussy. It was an incredible feeling, as her tight moist hole blanketed my throbbing cock.

Moving fast, I savored the feeling of her pussy before being sparked back to earth by Kelly Ann. "I'd enjoy this more with a rubber on you," said the girl. "I'm terrified about getting pregnant."

My mind thought she'd look good with a baby in her belly on her wedding day, but the gentleman in me, at least what was left of him, nodded assent. I pulled out, slipped on the rubber, and then dove right back into the willing girl. Thrusting in and out, I grabbed hold of Kelly Ann's ass and banged the girl with gusto. After a bit I held her tight, then rolled her over on top of me.

"What do I do," said the girl

Instructing her to move up and down my dick, the girl quickly got the idea. She began sliding up and down my cock like an experienced mink.

"Oh, this feels good, Jon. So damn good."

What started as a struggle had developed into a love fest. The girl and I moved in unison and I couldn't believe my luck. I had thought she'd fight, but whatever her motivation it translated into one hell of a fuck. Her moans became quicker and soon she was cumming for the second time that night. Soon, I reared back and followed, spewing my cum in fast spurts.

We held each other tightly for several minutes before she rose off my shriveling cock. I held the base, ensuring the rubber stayed secure, a fact not lost on the girl.

"Thanks for using a rubber, Jon, I'd die if I got pregnant," said the girl.

I kissed her, and then told her to turn over.

"What? You aren't thinking...."

"No, Kelly Ann, we didn't agree on your ass, but turn over."

She looked wonderful lying on the bed. She smoothed down the pleated skirt, but still showed a lot of leg. I told her to relax, that I just wanted to look at her, which I did. But I also wanted to snap a shot from my camera for posterity.

Mission accomplished, I slipped off my rubber and emptied its contents onto her now creamy white ass.

JRob
JRob
1,626 Followers
12