The Seduction of Simon Ch. 04

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Another boxer shorts contest.
1.5k words
4.44
25.4k
2

Part 3 of the 6 part series

Updated 11/02/2022
Created 08/05/2003
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Miss Prim was in an upbeat mood as she mounted the steps to her studio. Today was the day that either Simon, Isaac, or Ray was going to plow her sweet twat. Miss Prim wore nothing under her lightweight dress and her ample tits bounced as she bounded up the steps. Inside her studio, Simon and his two buddies were warming up. They had been so horny for the whole week they had jerked off 2 to 3 times per day with their hard cocks and balls poking out of their boxers, fantasizing about Miss Prim slowly lowering her wet pussy lips on their firm endowments. Each wanted to win the contest really badly, as they were all virgins and couldn't get their girlfriends to put out.

Miss Prim opened the door quickly and sashayed into the room, wiggling her bosum back and forth. The men caught their breath as they spontaneously all realized Miss Prim wasn't wearing a bra. Under their pants, 3 semi hard dicks began pressing against their boxers.

"Hi guys, what's up!"

Miss Prim giggled....certainly at least three objects were!!

"Good morning, Miss Prim" the three men exclaimed in unison.

"Let's get right to work, business before pleasure" Miss Prim began coaching the men as if nothing had happened the week before. She noticed that all three had replaced their button down shirts with pocket T-shirts; Ray's was black, Isaac's was blue, and Simon's was light purple. As she instructed them, she made sure to kneel occasionally to give each man a nice view of her oversized tits. After 15 minutes of this exquisite torture, Simon couldn't stand it any longer.

"Miss Prim, aren't we going to have the..." he stuttered and stopped.

"Oh, you mean the boxer shorts contest...oh yeah, I almost forgot"

She smiled wickedly and quickly undressed, tossing her dress on the floor.

The men let out a collective loud gasp. With the exception of a few porno tapes, they had never seen a naked woman. Their firm pricks felt like battering rams in their loose trousers.

Miss Prim quickly walked over to Ray and patted the huge bulge in his slacks.

"Are you ready for me?" she looked at him pleadingly

"yes-s-s madam" Ray hissed.

Miss Prim unbuckled Ray's trousers with exquisite slowness. She then undid his zipper and let his loose pants fall on top of his sneakers. Ray was wearing baby blue full cut satin boxer shorts. Miss Prim loved the fabric, making Ray wince as she ran her palm over the bulge in the right leg of the boxers. She then turned to Isaac who was muttering and swearing under his breath in anticipation of what might happen to him. Miss Prim unbuckled Isaac's belt, took down his zipper and pushed down his pants in all one deft movement. Isaac sported light blue trim boxers with white piping on the side. Miss Prim ran her hands into the cute little slits on the side of his shorts, relishing his lightly hairy legs. Then, she turned to Simon, whose eyes were tightly shut. Miss Prim rubbed the bulge in Simon's pants as she opened the belt, causing him to moan and groan with pleasure. Then she hastily lowered his pants to his ankles. Simon wore full cut boxer shorts with thin pale blue stripes on them. Miss Prim removed Simon's sneakers, as well as the other mens' footwear. Then, she stood back, admiring the three young studs in their sexy pocket t-shirts, hot boxers and cute white ankle socks.

"I can't make up my mind men" Miss Prim shook her head "appears to be a three way tie".

"You mean no one wins?" Isaac looked like a dejected puppy.

"Oh no, we just need a tie breaker" Miss Prim nodded knowingly.

"A t-t-tiieee b-b-b-reak-k-ker" Simon could barely get any words out.

"yes, a tie breaker. I'm going to give each of you guys a little head. Whomevers' cock tastes the best...will get to screw me!

The three men shivered in anticipation....a blow job! This was beyond what any of them had expected! Their pricks were as hard as blocks of cement in anticipation of the lewd act.

Miss Prim kneeled in front of Ray first. She tenderly nudged the bulge in the right leg of his boxer shorts toward the center fly opening. Ray's jaw dropped as he watched the fat head and large shaft of his dick slowly protrude out of the opening. Miss Prim deftly reached into his boxers for his large balls and blew hot breath on Ray's equipment, making him moan in ecstasy. Then she opened her mouth and took in his fat prickhead. Ray shuddered and let out a loud groan. In response, Miss Prim deep throated him passionately, gulping down his endowment like a skilled professional. Ray let out stentorian shrieks as his dick pistoned in and out of Miss Prim's mouth. After one minute of extreme bliss, Miss Prim let Ray's dick out of her mouth as he gasped for air.

"Delicious Ray, absolutely delicious."

Ray grinned widely as Miss Prim turned her attention to Isaac. He swore under his breath as she skillfully fished his dick and balls out of his tapered boxers. Miss Prim couldn't wait to have Isaac's cock in her mouth. It was a marvelous torpedo shape with a nice mushroom head. She got the cockhead into her mouth easily and immediately started to bob her head up and down on Isaac's penis as her fingers massaged his meatballs.

"OH MY FRIGGIN' LORD..... JJJJEEEEESSSUUUUSSSS!"

Isaac just about lost a huge load as Miss Prim gave him a first class blow job. When she was certain he was about to cum, she quickly took her mouth off his dick. Isaac's organ was a bit more pungent than Ray's but still tasted just fine. Miss Prim then faced Simon, who was shaking with excitement.

"Ready, big boy?" she lighted traced Simon's rock hard prick in the left leg of his boxer shorts.

"R-r-r-eeaadddyyy" Simon stammered, still not believing he was going to get two tube jobs in the space of a week.

Miss Prim very slowly pushed Simon's prick toward the wide center fly slit. She opened her mouth as his organ bounced out of the opening, swallowing about 3 inches of turgid flesh.

"ARRRRRRRGGGGGGGHHHHHH" Simon screamed in erotic pleasure. Miss Prim gradually stuffed more and more of Simon's prick in her mouth until she had swallowed all 8 inches. She then bobbed her head up and down on the salty tasting prick, causing Simon to howl with delight. After 2 minutes of extraordinary bliss for Simon, who was close to hyperventilating, Miss Prim reluctantly took his rock hard member out of her mouth. She then got up and faced the young men.

"Well, it was close guys, but the winner is....Ray!!

"YEEEEEESSSSSSSS!!!!!!" Ray was so excited he started to jump up and down like a little kid. Miss Prim giggled at the sight of his rigid prick bouncing up and down, as it still poked out of his boxers. She walked over to Ray, and gently pushed him back on his chair toward the wall, putting a large pillow behind him to cushion their lovemaking. Miss Prim then got on top of Ray and slowly guided his rigid prick into her gaping pussy lips. The look on his face as he slowly entered her was precious, a mixture of wonder and sheer delight. When she felt the base of Ray's prick inside her vagina, she slowly let his organ slide out before quickly impaling him again. Ray made so much noise Miss Prim was glad each studio was soundproofed. She rode him like a bucking bronco, doing all the work. Isaac and Simon masturbated their dicks furiously at the incredibly erotic sight of their teacher fucking their best buddy. After about 3 minutes of extreme bliss, Ray couldn't hold back any longer.

"AAAAAAAAHHHHHHHHGGGGGGGGHHHHHHH"

He erupted in Miss Prim's twat with such force she had her own spontaneous orgasm.

"OHHHHHHHHHHHHHHHHHHHHH" Miss Prim let out a wail that could be heard for a city block. At the same time, Isaac and Simon came together, blasting out 15 spurts of cum between them. Their seed dribbled all over Miss Prim's tits, twat, and legs, and a large glob even landed on Ray's boxers. After 10 seconds of intense orgasms, the quartet fell in a heap to the floor. Nothing could be heard but heavy breathing and panting until Miss Prim finally spoke.

"We'll have another boxer shorts contest next week...and the winner will get to plow my butt".

The men groaned loudly, each wondering what it would feel like to drive their rigid shafts in and out of Miss Prim's tight buttcheeks. Even in their absolutely exhausted state, they managed to smile at Miss Prim as she quickly got dressed and opened the door.

"See you next week, gentlemen, and don't forget to practice your instruments...she glanced at their limp members... and I do mean ALL of them!!"

By the time the men could respond, Miss Prim was gone, sexually satisfied and very content....until next week!!

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JoeehartleyJoeehartleyabout 15 years ago
Finally

The build up in the first two was great, and I've been wating for this one.

-Joe-

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