tagAnalJill Ch. 05

Jill Ch. 05

by5425TVR©

Chapter 5: Graduation Day

The day finally arrived; my ACT score was delivered in the mail. It was only three weeks before Jill and I were to graduate so there wasn't any time to retake the test if I didn't have that magic number 19. I took the letter from the kitchen table and went into my room.

I sat on my bed, took a deep breathe and opened the letter. There were four scores but the composite, 'COMP,' was the important one to me. They read: English 17, Math 22, Social Studies 18, Natural Sciences 19, and Composite 19.

I jumped up screaming in elation and ran as fast as I could to Jill's. My mother looked at me, smiled and laughed as I ran out the door. Jill was outside weeding the flower garden and heard me 'Whooping it up' the whole way.

She started running in my direction and we met in Mrs. Ackerman's front yard. She was knitting on her front porch watching our commotion. I was breathless as I just held up my scores for Jill to see.

She took the letter and read it. She was crying by the time it finally sank in. I had achieved the minimum score to gain entry to her college. We hugged and kissed and by this time all the neighbors had gathered in Mrs. Ackerman's front yard to congratulate me.

After the hand shakes, high fives and the crowd cleared, Jill and I went back to my house and called the Admissions Office to see what my 'status for admissions' was now that I had a better ACT score. After being on hold for nearly 20 minutes, we talked with Daren and he said that this year's scores were higher than last year's. At this point, I was number 79 on the waiting list for admissions. I was supposed to check back weekly as students finalized their plans. Daren was confident I would be sent an acceptance letter soon.

We were cautiously optimistic about my chances of acceptance to Jill's college and life progressed as normal. We planned our graduation parties so we each could attend the others. We prepared for our final exams with the occasional study break of sweet hot sex.

Finally, it was the eve of our high school graduation. Jill and I were making out on her bed. I was feeling a little frisky and she was nervous about her big speech. Apparently her performance on the Debate Team rewarded her with opportunity to give a speech at the commencement ceremony.

I was extremely proud of her for this honor. But as the time got closer to her giving the speech, she became more distant. Maybe distracted is more accurate. Nonetheless, I felt she was pushing me way.

When I asked her, "What's wrong?"

She promptly said, "Oh I'm just nervous about tomorrow morning. Would you mind if we cut it short tonight so I can practice?"

This was weird. Jill never asked me to leave; not even when we had a fight. I guessed anything was possible, but she had spoken to larger groups than the few hundred that would be in attendance at the ceremony. I was confused.

I said, "Sure, I'll see myself out so you can make it perfect. I love you."

"Love ya," she piped back as we kissed.

On the way out, I asked Jean, Jill's mom, if she knew what was up with Jill. I said, "She's acting a little strange."

Jean said it was probably just nerves. I wished her a good night and left.

Early in the morning, I dressed and quickly made my way over to Jill's house. I was supposed to give her a ride for her dress rehearsal. We were going to grab a light breakfast and then march down the aisle (so to speak).

When I arrived, Jean met me at the door in her white transparent silk robe that left nothing to the imagination. She said Jill left a few minutes ago with her father. Then, she asked if I wanted to come in for breakfast. I went in, not so much to eat, but to talk.

I was confused. Jill and I had been together for over five years. I was now number 3 on the waiting list for admission to her college. Now, that our lives were finally on track to be able to spend them together for the rest of our lives, Jill's attitude towards me grew more distant every day.

Jean made pancakes while I discussed my concerns. Jean had always been frank with me so I knew if there was something going on, she would tell me. As I talked, Jean sashayed around shaking her ample ass and bodacious boobs. Slowly, I became more interested in Jean than the problems I was having with her daughter.

My cock rose and I decided if she was going to tease me like that, I was going to fuck her senseless. I quickly took my clothes off and threw them on a nearby chair. My hard seven inch cock bobbed as I made my way to this sexy MILF.

I reached around her waist as my arm slid across her 38DD boobs and turned off the burned to the stove. She turned to find me naked as her robe fell open. It had been about a month since we last fucked and I was ready for another marathon session before the graduation ceremony.

Jean knelt in front of me and started sucking my hard cock. When she had it nice and wet, she spit in her cleavage and sandwiched my cock between her great mounds. The soft warm skin of her bosom felt great as my hard rod slid easily between them.

I knew Jean, like her daughter, had sensitive nipples that when tweaked properly would send electric sensations right to her pussy. So as Jean had those big beautiful breasts encompassing my cock, I pinched each nipple slightly jiggling them. This allowed the massive weight of each boob to create the sensations she loved.

Within minutes, Jean begged me to bend her over the kitchen table and fuck her. I could see she was dripping wet but I wanted to wait. I knew the longer I waited there was more of a chance her husband, Jake, would return.

Jake loved to watch me fuck his wife. Then, he would fuck her and show me how I could improve. I loved the two of them more than they could ever know.

Finally, Jean couldn't take any more; she stood, strutted over to the table and assumed the position. She bent at the waste with her boobs smashed into the table. Her arms spread her meaty ass cheeks and she swayed her ass seductively. "Get over here and fuck me, NOW!" Jean hissed as I spent a little too much time admiring her sexy body.

I casually strode over and in one quick stroke sunk balls deep into this vixen's silky hot cunt. Jean moaned with extreme pleasure at the sudden assault on her pussy. Jean was used to her husband's cock. It was two inches longer, had more girth and could pound the deep recesses of her channel.

So to please this woman, I gave it to her hard and furious. Jean did not have the incredibly tight pussy Jill had, but she knew how to use her pelvic muscles and when she contracted them, seemingly at will, she rocked my world. Jean sensed that I was daydreaming or loosing focus as she clamped down on my manhood to snap me back to reality and the task at hand: to get her off.

When she contracted her muscles, I was on a downward thrust. The sensation I felt changed from a sloppy blow job to a firm hand job. With this increased friction, my hard fast thrusts caused me to feel the first twinge of my impending apex. I wanted to last more than a couple minutes so I suggested we change positions.

Jean knew my favorite was sitting on the couch and having her ride my dick as her big mama tits bounced or smashed into my chest. She loved it when we lined up perfectly and she would grind the back of her cervix against my cock head. This is still one of my favorite positions and reflecting on these memories always brings a smile to my face.

Jean and I quickly moved to the couch. I sat and Jean slowly strattled my waste and sunk her sweet lips around my throbbing cock. She bounced and I countered with thrusts of my own. Her lovely boobs swayed and jiggled as they bounced against my chest and I was in heaven.

"Honey, I'm back," Jake announced as he walked through the front door.

"We're in the living room," Jean quickly shouted.

As Jake entered the living room, he saw his sexy wife of eighteen years riding the boyfriend of his daughter's cock. He smiled and said, "I see Jean is giving you your graduation present early. Care if I join?"

Jean squealed with delight at the idea. A threesome was something we had never done before and I was excited by the whole idea. "You bet, let's do it."

Jake quickly undressed. While removing his clothes he asked me, "Do you want the ass or pussy son?"

I hadn't really thought about it until Jake said something. I truly loved Jean's pussy. The warm, wet, tight gripping snatch was heavenly. I wondered what fucking her ass would be like; but, I was not to keen on the whole 'shit dick' thing. "Jake, what do you suggest?" I asked deferring my decision to the man who had fucked both holes repeatedly over the years.

Jake smiled sensing my aversion to anal fucking. Jake said, "Son, some day you are going to have to 'man up'. Right now, sex is new and wonderful and exciting. Some day, I know it seems impossible now, the same positions will get boring and sex can turn into just another chore that you have to do. Keep an open mind and explore your partner's body. There are so many possibilities; don't limit yourself. You may not enjoy everything you try; but at least you tried something new and that will show your lover you cared enough to try."

This speech seemed a little out of place: all of that over an ass or pussy. I was confused but thanks to Jean, I was still balls deep in a grinding pussy and oh so close to blowing my load. I knew I was close, so rather than just stay in Jean's pussy and cum, I said, "I'll try the ass."

Jean immediately corrected me, "Jean's wonderfully tight ass, if you please."

"To go without saying, my dear," I quipped.

Jake sat next to me on the couch while Jean shifted over and strattled Jake. I was surprised Jake was rock hard already. Usually, Jean had to work on him a little but not this time. I wondered if our little show earlier got his juices flowing.

Jean grabbed Jake's thick stick and gave it a quick couple of strokes. She brought her hand to her mouth and licked it, leaving a trail of dripping saliva as she returned to his pole. Satisfied there was enough lube, Jean slowly sank down on Jake's massive beast.

Next, Jean leaned into Jake. Jake told me, "Lube that sweet little asshole, boy. Stick your tongue in as far as it will go and enjoy the sweet taste."

The thought of sticking my tongue in anyone's ass made me want to puke. I wasn't sure if Jake was some how messing with my head or if I was really supposed to do it. Jake had always been a straight shooter and never gave me any bullshit, so I figured he wouldn't start now.

As a result of this reflection, I leaned towards Jean's luscious ass with my tongue flicking. The first thing I noticed was the strong pungent aroma of Jean's sweet pussy juices and the distinct smell of sweat and shit. Surprisingly, the combination of the smells was not gross; NO, it was intoxicating.

I couldn't wait to dive my tongue deep in Jean's tight crinkled star. As I neared this taboo area, my flicking tongue touched Jean's asshole and she flinched and giggled. My taste buds exploded with delightful new flavors I had never experienced. I hungrily began to stab my prodding tongue into Jean's ass.

"Take it easy tiger!" Jean squealed as I tried desperately to taste every glorious inch of her long dark tunnel. After a few short moments, Jean said, "I think I'm ready...give it to me baby."

I really didn't want to end my all-out anal assault with my tongue; but I really wanted to try this double penetration thing. I had seen it in porno movies and it had always turned me on. Now, it was my turn to try it.

I grabbed my throbbing cock which was oozing pre-cum like crazy and placed the head directly on Jean's now winking crinkle. I just watched in amazement as she literally winked with her asshole. Again, I lost focus until Jean's subtle, "OK, I'm ready."

I slowly sank my cock into her anus as she grunted and flexed that mighty chute. I thought to myself, "It looks like she is trying to take a crap." This thought quickly disappeared as I experienced the tight grip of her ass milking my hard rod. As I slowly bottomed out with my balls dangling on her cheeks, I felt Jake move his big cock.

The thin membrane between Jean's ass and pussy seemed as thin as a condom. I could feel Jake's bulbous head as Jean moved to fine a good rhythm that we could all follow. Jake's head moved along the bottom of my shaft. It felt weird at first; like another finger running along under my dick.

Jean's ass was tight and when she flexed her muscles, the grip was extraordinary. She actually squeezed my cock; not so tight that I couldn't move, but tight enough that I had to concentrate to keep my steady rhythm. Jake's cock went in when my cock went out.

The clutching of Jean's ass combined with the added pressure from Jake's cock created the ultimate sensation. I grunted, "I am so close."

Jean gasped, "Baby, I am too; clench your ass cheeks until we can all cum together."

I clenched my cheeks so tight; I feared I wouldn't shit for a week. The overwhelming sensations eased a bit. Then, Jean's deep tunnel started to twitch and contract in ways she hadn't before. These new movements were making it to difficult for me to concentrate on my clenching and still maintain the strokes in rhythm. The extreme pleasure I felt had me dizzy and my balls reached the boiling point. My toes curled and my knees wobbled. I had to CUMMMM.

Jean screamed, "OH MY GOD!" Her anal contractions went into over drive and I rammed hard into her ass as I shot a powerful blast of cum deep in the recesses of her tunnel. I lost balance and I collapsed on her back.

Jean flailed around grinding her pussy on Jake's monster cock as he pumped his seed deep in her pussy. I felt the powerful jets of Jake's cum bounce off Jean's thin wall and against my cock. This made my cock twitch and expand its girth. Jean smiled as she turned her head and kissed me and then Jake.

We all lay there in a massive heap panting for air with sweat dripping from our bodies. Our position became uncomfortable and our cocks slowly deflated. When my withered cock popped from Jean's ass, I slowly stood and then lay on the floor at their feet.

Jean quickly followed my lead. She rose off Jake's cock and immediately cupped her pussy and then her ass. I wondered what she was doing as she ran out of the room. Then, it dawned on me as I saw the cum leak between her fingers. We had filled her pussy and ass with two huge loads of cum. She didn't want to have cum stains on the couch when the guests arrived for Jill's graduation party.

Jake looked at me and said, "Use Jill's bathroom and clean up. It's about time for you to leave for the ceremony, isn't it?"

I had twenty-two minutes to take a quick shower, get dressed and drive to the high school. Thankfully, it was close. I hurried out of the room gathering my clothes and showered.

I arrived just as my classmates were lining up. Jill led the procession since she had a part in the presentation, I was near the back. As we walked in, I tried to catch her attention but she seemed distracted.

The ceremony was fine. There were the traditional boring speeches and scholarship presentations. It ended with Jill's speech. I patiently waited for this because I knew all the hard work she put into it. As she opened the folder to read the contents, she looked at me for the first time. She stared for an uncomfortable amount of time as tears welled in her eyes. Then, she began to read her speech.

As I watched my beautiful girlfriend, she seemed distant. Her speech titled "Live Your Dreams" was a roaring success. Applause erupted throughout the rousing parts. Sobs were heard from mothers and students during the touching pieces. Then, the last few lines of the speech hit me like a freight train.

What I say to you now is 'live your dreams'. Do not sacrifice your dreams for the sake of the ones you love. Go into this new chapter of your life with your head held high knowing that you will make a difference. Do what you know you must; don't sacrifice your happiness to live another's dream: 'LIVE YOUR DREAMS!'

Tears trailed down my face. I knew this was Jill's way of breaking up with me. She knew I was going to her college to follow her dream. She knew I didn't have the feeling she had for art but I was willing to follow her anywhere.

I also knew that we would have a face to face break up. We had been a couple for over five years. We were each other's 'firsts' in so many ways. Now, my world was collapsing around me.

As we walked out of the gym, I tried to compose myself. As we filed out of the building, we had to stand in line for nearly an hour as everyone in attendance shook our hands. This was hell. I just wanted to run over to Jill, hug her and tell her she was my 'dream'.

After the dog and pony show ended, I searched for Jill. She was nowhere to be found. So, I jumped into my car and raced to her house. Driving along Main Street, I looked at the familiar stores. All the memories Jill and I made in them streamed through my mind.

Then, I passed the Army Recruiting Station. Staff Sergeant Jones sat at his desk as I rolled to a stop (still in the middle of the road). Old Man Jenkins honked his horn at me to knock me out of my trance and I pulled into an empty parking spot.

Old Man Jenkins pulled next to me and said, "Gonna follow in the old man's foot steps, ehh?"

I looked at him and said, "Yes sir!"

He nodded and smiled, "Good for you," with his yellow brown teeth gleaming in the sun. He got out of his rusty truck and headed to the café. As he walked away, I glanced at his faded "Death From Above" tattoo and vowed not to get one for myself.

I went into the recruiting office and 30 minutes later I was the newest Army private. Staff Sergeant Jones and I had talked on several occasions and he had the paperwork ready for me to sign (just in case I ever changed my mind). He knew my family's history and we talked at length about what specialty would best suit my skills and future needs.

Because the skill I selected was so specialized, I only had two dates for the year to choose for my training. The first date was Monday morning. That meant I would have to leave tomorrow. The second was November 15th. I chose Monday because the thought of being around Jill if we weren't together tore me up inside.

When I arrived home, my parents wondered why I was so late. I told them I talked with friends. I was brief and they assumed I wanted to get to Jill's party.

I changed clothes, farted around and eventually went to Jill's party. By the time I arrived, most of the guests had already left. There were just a few relatives left helping Jean clean up.

As I entered, Jean and Jake quickly announced my presence and the relatives all came rushing over to greet and congratulate me. Finally, I saw Jill. She was the last to hug me.

She whispered, "Let's go to my room, we need to talk." I thought to myself, "Here it comes. Be cool." I nodded and we held hands until we were sitting on her bed facing each other.

She leaned in and gave me a sweet kiss and said, "Congratulations, graduate."

"You too," I waited for her to continue.

"What did you think of my speech?" She questioned.

"It was powerful and moving. The audience was both touched and inspired," I truthfully said.

"No, what did YOU think?" Jill pressed.

"I know the last paragraph was wholly devoted to me. To tell you the truth, I was pissed, hurt and embarrassed that you chose that moment to break up with me," I quivered as my emotions were getting the best of me.

She quickly said, "It was the only way I could tell you how I felt without backing down. We have so much history together, but ultimately, I can't be the one to ruin your life. We just don't have the same visions for our futures. I want to travel the world and see all the major art pieces ever created. You are happy to run the family business and stay here your entire life."

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by5425TVR© 2 comments/ 28377 views/ 4 favorites

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