2 comments/ 30420 views/ 3 favorites The Seduction Of Simon By: sack Miss Prim smiled. The buxom 28 year old had finally decided it was time to implement her plan....to seduce Simon, her very handsome 19 year old voice student. She hurried to the music school where she worked, anxious to get out of the 90 degree heat. Fortunately, there was no air conditioning on the second floor which was going to make her seduction even easier. As she mounted the staircase to her studio, she fantasized making love to the six foot four Simon. She had been mentally undressing him since their first lesson, and was pleased to discover he seemed very well endowed under his loose chinos. Simon consistently wore colorful jerseys with no undershirt, cute short white socks and either boxer shorts or no underwear. Miss Prim decided early on that he probably wore boxers, since he was nerdy and a goody two shoes type...she couldn't picture him going "commando". Well, today she would finally get to see his underwear and hopefully so much more. Miss Prim had purposefully worn the most provocative outfit she could think of, a VERY short dress which was cut quite low in front. Her tight powder blue bra could barely contain her huge breasts and underneath her dress were matching powder blue panties. She opened up the door to her studio slowly and could see Simon warming up inside. He seemed shocked to see her dressed the way she was, but said nothing. During the first part of the lesson, Simon was taking great pains not to look at her, but would occasionally steal a glance down the front of her dress. She sat at the piano as low as she could as he sang, giving him a perfect view of her powder blue bra. As the lesson progressed, Simon's pants began to bulge out in the front. Miss Prim decided it was time to make her move. Stopping in mid-phrase, she suddenly got up from the piano and faced Simon. He immediately stepped back away from her. "Simon! What were you looking at?" "Uh...err....nothing,nothing!" "You were looking down my dress weren't you?" "Uhhh..nooooo...I wasn't, I really wasn't!" Simon began sweating profusely. "You were trying to see if I was wearing a bra, weren't you??" Simon started to turn crimson. "no, I wasn't". Miss Prim smiled. "well, I am wearing a bra, would you like to see it?" Simon squirmed and looked down at the floor. "uhhhhhh noooo, nooo" "That's OK, it's a bit hot in here anyway" With that, Miss Prim let the top of her dress fall over the loosely belted waist. Her ample tits bulged out of the tiny blue bra. Simon gasped "oh my God!" Miss Prim just grinned. The front of Simon's pants were really bulging now. He quickly put his hands in front of his crotch to hide his burgeoning erection. "What's the matter Simon, haven't you ever seen a woman in a bra before?" Miss prim stared at him wickedly. "Uhh...sure...course I have" Simon was talking very quickly, slurring his words. "You look very hot. why don't you take your shirt off? It's OK with me if you get more comfortable" "My shirt!" Simon looked incredulous. "Oh no, I'm OK, it's not that hot in here" "Oh, but it is, here let me help you". Miss Prim walked over to Simon and quickly grabbed the top of his striped jersey. She pulled the garment over his head with some difficulty, as he kept moving his arms back and forth, muttering under his breath. Finally, the jersey was completely off and Simon turned beet red. As usual, he wore no t-shirt and Miss Prim took in his slightly hairy chest for the first time. She went down his chest slowly, noticing his cute belly button and two inches of blue plaid boxer shorts that were peering out from his trousers. Miss Prim grinned, happy that she was right about his choice of undershorts. Miss Prim loved young men in boxer shorts and short white socks, and Simon was clearly wearing both today. "There, that's better" Miss Prim smiled her best evil smile as she put Simon's jersey on a chair. "Now, what do we have here?" pointing to the enormous tent in the front of Simon's slacks. "n-o-o-ot-t-h-h-i-n--g-" Simon stuttered. "n-o-o-t-h-i-n-g" "Oh, but there is something" Miss Prim gently pushed Simon's hands away from his crotch and put the flat part of her palm over the bulge in the slacks. Simon immediately let out a loud moan. She rotated her hand slowly, until she found his prickhead under his pants and boxers. She then took her thumb and two fingers and lightly masturbated Simon's swelling prickhead through his pants. After about 10 seconds of this treatment, Simon's moans suddenly became louder and higher pitched. Miss Prim realized what was happening in an instant...Simon's engorged member was gradually pushing out of the fly slit of his boxers under his pants! Excited about this, Miss Prim vigorously jacked off Simon through his slacks until she thought the full length of his ample endowment was poking throgh the flyhole of his boxer shorts. Then, she got up and once more faced Simon. "I think it's time for us to get more comfortable" With that, Miss Prim stepped out of her high heels, undid the belt to her dress and stepped out of the garment. There she was, clad only in her powder blue bra, brief matching panties and sexy dark blue pantyhose. Simon went into complete shock. "ohhhhh JEEEESSSUSSS". "Now it's your turn Simon, take off your pants!" "MY PANTS! Simon bellowed..."I can't....I just can't"...he seemed close to tears. Miss Prim was persistent "Simon, I've seen men in their boxer shorts before, what's the big deal?" "yeah....b--b-b-b-b-b-b-u--t-t-t-t-t" Simon was stuttering worse than before. "SIMON" Miss Prim stared at him fiercely "Do you have a boner sticking out of your boxers?" "I d-d-d-ooo-n't t-t-think s-s-s-oo" Simon could barely talk at this point. "Then we are going to have to find out..now you take off your pants, or I will!" Miss Prim spoke like she really meant it. "I -I-I c-c-c-ca-an't" Simon was really close to tears now." "Suit yourself" Miss Prim got on her knees and removed Simon's sneakers. He looked down and his jaw dropped as Miss Prim unbuckled his belt and slowly maneuvered his zipper down, not wanting to get his hard prick caught in the teeth. When the zipper was finally all the way down, Miss Prim pulled Simon's pants down slowly. As they cleared his crotch, Simon's fat eight inch prick bounced out of the fly of his boxer shorts and hit his stomach with a loud THWACK! "Oh my GOD, Simon" Miss Prim reached into his full cut blue plaid boxers and hauled out his wide meatballs. The sight of her fantasy man, naked except for his nice boxers and short white socks was simply too much for her to take. She leaned forward and slowly took Simon's fat cock in her mouth. He immediately let out a loud shriek and began to spurt buckets. "ARRRRRR RRGGGGGGGGGGGGGHHH HHH" Simon almost fainted from the feel of his intense orgasm. At that point, Miss Prim was suddenly aware of a loud ringing sound. She awoke slowly, barely able to press the bar on her alarm clock down. It had all been a wonderful dream! Miss Prim looked down at her powder blue panties. They were completely wet, and she obviously had experienced multiple orgasms during her erotic reverie. Miss Prim forced herself to concentrate on the clock. Good heavens! She was running a bit late! It was time to get ready for Simon's singing lesson.... The Seduction of Simon: Aftermath Miss Prim was constantly horny since her intense wet dream about Simon. She decided to rent some porno movies after work one day to see if there were any really good scenes she could frig herself to. Her patience was rewarded...the last flic she chose had a 20 minute scene which involved 4 men and a stripper at a wedding. The men were fully dressed except for their pants, and they all wore full cut white boxer shorts. The stripper all gave them long, hot blow jobs with their dorks and balls poking out of their boxers, then sat on their dicks one by one until they blew their hot wads in her butt. Miss Prim came 4 times while watching the hot scene. She enjoyed men in boxer shorts and was determined to recreate the same scene at the music school where she worked. The next day, Miss Prim carried out her plan. She decided on 4 men that were not married and very cute: Scott, 22, 5'10", 185 lbs., Dave, 26, 5' 8", 140 lbs., Hank, 30, 6' 3', 200 lbs., and Mike, 25, 6'0", 180 lbs. In each of their mailboxes, she placed a polaroid picture of a pair of crotchless panties and scribbled a brief note: "Let's meet in janitor's closet at 6 PM tomorrow for some sexy fun. He'll be at dinner for an hour and we'll have the place all to ourselves. Oh, and don't forget to wear clean boxers!" Miss Prim snuck the messages into their mailboxes in the staff room when no one was looking. Needless to say, the next morning was a very perplexing one for the 4 horny and hunky men. They had gotten the messages the night before, and had no idea what was in store for them. As it worked out, they all wore boxers anyway except for David, who chose white jockey briefs. However, David had recently started to wear white baggy boxer shorts to bed, since they were so comfortable. He decided to wear the white boxers under his pants instead of his usual briefs. The day passed by excruciatingly slowly for the four men. Finally, at six o'clock, they all snuck in one by one into the roomy closet. Miss Prim decided to be a little late on purpose, figuring that would add to their horniness. As she entered the room, she could see her calculation was correct: all 4 men had slight, but definite bulges in their slacks. "Good evening gentlemen" Miss Prim tried to sound formal "I suppose you wonder why you are here. Well, here's the deal. I've been real horny lately and yesterday I rented this super hot porno flic. There's one scene that was so hot I want to recreate it with you four guys." There was a sharp intake of breath among the four men. Finally, Hank spoke. "What did they do in the scene?" As Miss prim described the wedding scene in detail she delighted in seeing the mens'eyes pop and jaws drop. When she had finished, you could have heard a pin drop. David finally whispered "you mean you'd...give us head?" "That's right, Miss Prim smiled "with your cock and balls sticking out of your boxers" The men gasped and muttered under their breath. They had never seen each other in their undershorts, nevermind with their hard dicks sticking out of them. But each young stud was so horny and hard, their pants bulged way out in front, a sight which was not missed by Miss Prim. "I think I'm going to get more comfortable". With that, Miss Prim lifted her lightweight dress over her head. The 4 men gasped audibly...she was completely naked underneath!! "Oh my God" David and Mike exclaimed at once. "OK, guys, your turn. Step out of your shoes and pants." Miss Prim grinned with glee. The men grunted and groaned but kicked off their shoes and slowly lowered their slacks. Miss Prim was in heaven as their hairy legs and tented boxer shorts were revealed. David's were pure white, Hank's were baby blue, Mike's were green plaid, and Scott's had thin red stripes on white. "Not bad" Miss Prim nodded. "Now at the count of 3 I want you to pull your cocks and balls out of the boxer flies...ready, 1...2...3...!!! More grunting and groaning as the men pulled their equipment out of their boxer flies. Miss Prim practically fainted. All of the men were very well hung and their balls were enormous! She guessed David's dick to be about 7 inches, Scott and Mikes' were closer to 8, and Hank's was the monster in the penis department with a fat 9 incher. Miss Prim got on her knees and faced David. "Time for the fun to begin!" She stuck out her tongue and made contact with his slightly hairy balls. The next 2 minutes were pure ecstasy for David as she tenderly sucked his ample ball sacs. Then, Miss Prim opened her mouth wide and swallowed about 4 inches of David's dick in one gulp. He let out a loud moan that could have been heard down the hall. When Miss Prim felt David leaking precum, she knew it was time to move on. She faced Hank's monster cock next and gave him a similar deep ball suck followed by tuneful skin flute. Hank's breath came in shallow gasps and his eyes were tightly closed. Miss Prim then did the same deep throat treatment to the other men, who were in an extreme state of contentment. Although all had jacked off frequently with their cocks and balls poking out of their boxer slits, they had never been blown in them. This was definitely the most erotic thing they had done sexually so far. When Miss Prim had brought all 4 men to the brink of orgasm, she had them sit down on 4 folding chairs that she had hastily set up earlier. Then she positioned herself on top of David's lap. She loved the way his cute cock looked sticking out of his sexy white boxers and had to feel it in her bum. David took in a deep breath as she lowered her ass on his dick, one delicious inch at a time. She let out a loud moan when all 7 inches of David's love pole were deep in her rectum. Then she rode his cock like a bronco bull, loving the feeling of cotton against her buns on each downstroke. "Sweet Jesus!" David yelled. He had never felt sensations like this in all his young life. The other 3 men masturbated furiously as they watched Miss Prim bounce up and down on David's cock. In a matter of minutes, David couldn't hold his load back any longer. "I'm going-g-g- to POP!!!" Miss Prim experienced the incredible sensation of her own intense orgasm as David's cock exploded in her butt. Her cumming set the other 3 men off, and they squirted huge volleys of cum all over Miss Prim's naked body. After 30 seconds of frantic orgasming, the four men and Miss Prim collapsed on the floor. She reluctantly got up after a minute or so of recovery and put back on her dress, still enjoying the sight of the mens' limp dicks and balls sticking out of their boxer shorts. "I assume I will see you next week, gentlemen?" Miss Prim grinned as she opened the door. All they could do was nod they were so spent, each silently plotting a way of getting their girlfriends to do what Miss Prim had performed with David! As to Miss Prim, she went home and masturbated 4 times thinking about her sexy experience with her hunky co-workers...she was content, for the moment!! PS- If this story encourages you to have some fun with your husband/boyfriend in his boxers, write a story about it! The Seduction of Simon Ch. 03 After her intense session with the four young faculty members at her school, Miss Prim had gained enough confidence to plot her seduction of Simon, along with two of his buddies, Ray and Isaac. As it worked out, she had volunteered to coach a small chamber group...as Simon sang, Ray played piano and Isaac played clarinet. She hurriedly mounted the steps to her second floor studio. It was a beastly hot day, and she could hear the three young men rehearsing inside. Isaac and Ray were only 18 and very handsome. Ray was about as tall as Simon and very skinny, while Isaac was short and compact, about 5' 6" and 135 pounds. Miss Prim opened the door and greeted the young men. They seemed surprised to see her in just a lightweight short dress which revealed part of her aqua bra. She quickly noticed they were all dressed in nice fairly loose trousers, sneakers with white socks, and button down shirts. "Hi guys" Miss Prim smiled her widest evil smile. "Hot enough for you?" They groaned in unison, wishing the 2nd floor had air conditioning. "We'll just have to do the best we can" Miss Prim stood in the center of the room and started to coach the boys. As the rehearsal progressed she frequently bent down to give each man a nice view of her aqua bra. After about 10 minutes, there were unmistakable bulges in the three mens' chinos. Miss Prim decided it was time to make her move. "I don't know about you guys, but I can't take the heat in here. Let's have the rest of the rehearsal in just our underwear" You could have heard a pin drop as the three mens' jaws dropped and their eyeballs popped out "Our UNDERWEAR??" Simon was incredulous. "Yeah, what's the big deal, you've been in your underwear in front of your girlfriends, haven't you?" Very reluctantly, the three men shook their heads. Miss Prim grinned..."there's always a first time for everything...I 'll go first" With that, she lifted her thin dress over her head. The boys gasped as her matching blue panties and bra became visible. Miss Prim kicked off her shoes and sat down in a low chair, giving the men a great of view of her huge titties poking out of her bra. The bulges in their pants were becoming much more pronounced. "Ok, guys, your turn" They shook their heads in unison. "w-w-wee can't" Simon said. "what's the matter boys, aren't you wearing t-shirts? Once again, the three young men shook their heads...it had been too hot to wear them. "well, then how about undershorts?" This time they nodded yes...none of them had ever thought of going commando! "What kind?" she turned to Ray first. He turned beet red as he stammered "b-b-oxer shorts" and you Isaac? Isaac thought he was going to faint "b-b-oxers" "and how about you, Simon?" Miss Prim was persistent. Simon looked at the ground and wanted to die "b-b-oxers too" "Looks like I'm going to have to sweeten the pot" Miss Prim smiled. "I'm going to undress each of you down to your boxers and socks. Whoever has the nicest boxers....she paused triumphantly...will get a blow job with his cock and balls poking out of his boxers" "A BLOW JOB??" Simon croaked. "Yep, a blow job" Miss Prim was going to have to act fast. She walked over to Ray first and unbuttoned his shirt. He muttered and swore under his breath the whole time, but let her do it. She then repeated the same procedure to Isaac and a very reluctant Simon, who fought her the whole way. But Miss Prim persisted, quickly taking each boy's sneakers off. Now all three were bare chested and their short white socks were turning Miss Prim on. Only Simon's boxers were visible above his slacks, about 2 inches of baby blue fabric. "Now it's time for the unveiling" Miss Prim kneeled in front of Ray, who was practically hyperventilating at this point. He made a loud grunting sound as Miss Prim quickly undid his belt and zipper. His slacks immediately fell in a heap to the floor, exposing his lightly hairy very thin legs and cute blue plaid full cut boxer shorts. The right leg of his boxers was tented fully with his ample endowment. Then, Miss Prim moved to Isaac, who was sweating profusely. She unbuckled his belt with tantalizing slowness, drawing his zipper down and slowly pushing his trousers to his feet. Isaac sported red plaid tapered boxers, with adorable little slits in the side. His legs were moderately covered with dark brown hair and Miss Prim couldn't help but rub her hands up and down them. Finally, she turned to Simon, who was practically crying at this point. "p-p-p-please don't take off my pants" "Sorry Simon, it wouldn't be fair to the other guys" With that, she undid his zipper and belt quickly, and excitedly shoved his pants down. Simon had very hairy legs covered with curly black hair, and his baby blue boxers really turned her on. Miss Prim took in the gorgeous sight of the three young studs clad in only their boxers and white socks. "This is a close call...but lucky for Simon, light blue is my favorite color" "Oh my GGGGOOOODDD!!!" Simon screeched. He couldn't believe that in a matter of seconds Miss Prim's lips would be wrapped around his aching cock which was trapped in the left leg of his boxers. "I want Simon in the middle with Ray and Isaac on either side" The men quickly took their positions. Miss Prim ran her fingers over the bulge in the left leg of Simon's boxers. With exquisite slowness, she pushed his cock toward the center fly slit. Simon moaned loudly watching the inevitable progress of his dick toward the opening. Finally, Miss Prim gave his wang one strong push and all eight inches of his endowment sprang out of the fly of his boxer shorts. She reached in the wide opening and fumbled out his enormous meatballs. Then she lowered her mouth to his appealing organ and took down 4 inches in one gulp. Simon let out a wail that probably could have been heard down the hall. Miss Prim continued stuffing more and more of his prick down her mouth until all eight inches were inside. Then, she deep throated Simon vigorously as he let forth every swear word in the book. At the same time, she reached into Ray's boxers on her left and Isaac's boxers on her right. She jacked on the two long and thin prongs furiously, causing both boys to groan and grunt loudly with pleasure. After giving Simon a prick tongue bath for two torturous minutes in which his whole body shook, Miss Prim turned her attention to his meatballs. She licked one ball sac at a time, forcing her tongue to go way back almost to Simon's buttcheeks. He howled in pleasure and tried to keep from holding back. But after another 2 minutes of heaven, he knew it was time to blow. "I'm going to PPPPPPPoppppppp!!!" Simon wailed as the Load of Loads blasted out of his prick and into Miss Prim's mouth. She swallowed all eight healthy spurts, enjoying the taste of Simon's seed. His orgasm was so intense, it was enough to bring both his buddies off at the same time. With moans of lust, Ray and Isaacs pricks shot huge loads all over Miss Prim, running down to her bra and panties. The force of the three mens' orgasms was so intense, they collapsed in a heap on the floor, along with Miss Prim, who had experienced at least 5 intense orgasms as she was blowing Simon. After a few minutes of heavy breathing, Miss Prim was finally able to get up. She spoke in a hoarse voice. "Guess our session is over for today....next week we will have another boxer shorts contest and the winner....she took a long pause...will get to screw me" The men uttered a sharp intake of breath, nodding as well as they could in their absolutely spent condition. Each immediately tried to think of the sexiest boxers they owned....it was going to be a long week!! The Seduction of Simon Ch. 04 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!! The Seduction of Simon Ch. 05 After the sizzling encounter with Simon, Isaac, and Ray, Miss Prim was so horny she knew she would never be able to wait a whole week for more sex. Remembering how good it had been to screw David, her hunky coworker, she decided to leave a note in his mailbox to meet her at 6 o'clock in the janitor's closet the following evening. When David read the note he was thrilled. He had jacked off furiously at least two times per day since his tryst with Miss Prim and had a perpetual semi hard-on in his pants as he walked down the halls of the music school. As he got ready for their hot encounter, David chose his clothes carefully...a dark blue jersey, navy blue pleated pants, white socks and sneakers. Underneath, he wore a plain white crew neck t-shirt and white full cut Hanes boxer shorts. Since it was obvious that Miss Prim was turned on by the white boxers he wore last time, he had experimented by wearing them under his dress slacks for about a week instead of his usual white jockey briefs. To his surprise, he adjusted to the extra fabric of the boxers rather quickly. They were especially comfortable under the pleated trousers he sometimes wore. Ultimately, David decided to switch to boxers completely. He threw away his worn out briefs and bought a couple of 3-packs of full cut plaid boxers, one 3-pack of baby blue full cut boxers, and 3 pairs of plaid trim boxers to wear under shorts or tighter pants. David hurried to the janitor's closet at 6 o'clock on the nose. As he opened the door, he saw Miss Prim arriving from the other end of the hall. They went in together, since no one else was around. Miss Prim shut the door and locked it from the inside. Then she passionately embraced David, kissing him deeply. "Hmmmmm, I've looked forward to this" Miss Prim cooed. "s-s-oo h-h-ave I" David was stuttering in his extreme excitement. "Let's strip to our underwear" Miss Prim quickly got out of her dress. Underneath she wore a baby pink bra and matching pink crotchless panties. David pulled his jersey over his head as Miss Prim sunk to her knees and quickly divested him of his sneakers. Then she moved up to his crotch, fondling the enormous lump in his slacks until David begged her to stop. Smiling, Miss Prim unbuckled David's pants and slowly lowered the zipper. He helped her by stepping out of his pleated slacks completely. Miss Prim groaned. David looked like a white angel in his white crew neck t-shirt, white full cut boxers, and white ankle socks. She patted the firm bulge in the right leg of his boxer shorts, pushing his full erection agonizingly slowly toward the center fly opening. After what seemed like an eternity, Miss Prim was treated to the amazing sight of David's rock hard 7 incher and prodigious ball sacs protruding from the front of his boxers. She started with his balls, sticking her tongue out as far as it would go as David writhed and groaned in pleasure. At the same time, her hands went up the back of his boxers and she inserted a couple of fingers into his butt. Miss Prim frigged David's buttcheeks unmercifully as he howled loudly with delight. She then moved to his prickhead, swirling her tongue all around the large ridge. David shrieked as she opened her mouth completely and swallowed about half of the length of his fuckstick in one gulp. Miss Prim then deep throated David with abandon as he made loud guttural moans. When David started to spew copious precum into her mouth, Miss Prim let his penis slip from between her lips. Breathing heavily, she tipped him back in his chair and slowly lowered herself on his love muscle. David let out a loud groan and tried to hold back as Miss Prim started to give him the ride of his life. She did all the work, sliding up and down on his prick with abandon. On each downstroke, David was inside her so deeply she could feel the cotton fabric of his boxer shorts against her crotch. After about 2 minutes of extreme bliss David knew he was at the brink. "Here it commmmmeeeeeesssssssss....... AUUUUUUUUGGGGGGGGGHHHHHHHHHHHHHH!!!!!!!!! Miss Prim felt David's cock explode in her pussy. At the same time she experienced her own sweet orgasm. "OOOOOOOOOHHHHHHHHHHHHH" Miss Prim moaned so loudly she wondered if either of them could be heard. David shot off eight huge spurts in Miss Prim's twat, then fell to the floor, panting heavily. As for Miss Prim, she was so aroused she easily frigged herself to another orgasm while David watched. The exhausted couple lay on top of each other for two full minutes. Finally, Miss Prim reluctantly got up and started to put her dress back on. "Thanks David, I really needed that" Miss Prim gently took his limp penis and put it back in his boxers. "Anytime...and I do mean anytime" David winked back at her. Miss Prim opened the door, waved goodbye to David and cautiously went out in the hallway. She immediately started to plan her next encounter...an underwear party at her home, with just her and the seven males she had fooled around with so far!! The Seduction of Simon Ch. 06 Miss Prim's intense erotic session with David was enough to keep her fulfilled...for a few days!! Fortunately, her last coaching session with Simon, Ray, and Isaac was about to take place and Miss Prim could hardly wait! She wore no bra and her skimpiest thong for the occasion, humming and bouncing along as she climbed the steps to her 2nd floor studio. Inside Miss Prim's room, the three young men had gathered early to practice. Even more than the previous week, they had been in a perpetual state of arousal, trying to imagine what it would feel like as their rigid pricks explored Miss Prim's tight buttcheeks. Ray bought a huge bottle of lube which he generously shared with his buddies. Using lube, they had all had jacked off several times per day, recreating the whole seduction scene in their minds as their hands danced on their rock hard boners. Even though Miss Prim hadn't even entered the room yet, each man was already partially erect under his trousers... The door opened suddenly and Miss Prim waltzed into the room. "well, hello guys, ready for our last session?" "Yes, mam," they all replied in unison...were they ever!! "Then let's practice first and see if we can make beautiful music together" she winked at the men seductively. The first 15 minutes of the coaching proceeded without incident. Miss Prim gave the men a view of her ample titties whenever possible, delighted in seeing the front of their slacks spontaneously tent out to the maximum. After she felt they were ready for the performance next week, she stopped conducting and walked over to Isaac, who was sweating profusely. "Ready for the contest, men?" Miss Prim smiled as she started to unbutton Isaac's shirt. "S-s-su-u-r-e," they uttered in unison, too excited to speak properly. Miss Prim continued undoing Isaac's shirt until it dropped to the floor. Then, she quickly took off his sneakers as Ray and Simon shed their own shirts, t-shirts, and footwear. "Time to get more comfortable" Miss Prim opened her blouse and slid out of her short skirt. There was a loud gasp from all three men as her enormous breasts flopped out and her brilliant blue thong was revealed. "That's better" Miss Prim walked over to Isaac and knelt in front of him. He moaned and muttered under his breath as Miss Prim slowly and sensuously lowered his trousers to his ankles. Isaac sported blue silk boxers that were cut shorter than usual. Miss Prim tickled his prick through the right leg of his boxers and blew hot breath through the opening. "Oh my FRIGGIN LORD" Isaac thought he had died and went to heaven. Miss Prim played with Isaac's prick through his boxer shorts for one wonderful minute, then moved over to Ray. She quickly opened his brown chinos and pushed them down eagerly. Ray wore teal silk boxers that were short, tight, and mouth watering. The head and part of the shaft of his prick already poked out of the fly opening. Miss Prim tenderly jacked him off until he was fully hard, enjoying his facial grimacing and loud grunts and groans. Then she opened her mouth and took Ray's mushroom head inside. He let out a loud moan and started to buck his hips back and forth. Miss Prim took more and more of Ray's love muscle inside her warm mouth until she reached his balls. Then she deep throated him vigorously as he howled with lust. After a minute of intense cocksucking, Miss Prim let Ray's wang slip out of her mouth and turned her attention to Simon whose whole body was shaking. She smiled as she unbuckled his belt and let his loose chinos fall to the floor. Simon was wearing white satin boxer shorts what were trim cut. His 8 incher was trapped in the right leg, as usual. Miss Prim pushed it toward the fly opening until she was greeted with the beautiful sight of Simon's quivering cement hard dick. Without missing a beat, Miss Prim ran her tongue over his hefty balls, enjoying his screams of pleasure as she stuck her long tongue back into places Simon had never been explored. He started hyperventilating as she spontaneously deep throated him like there was no tomorrow. When Miss Prim felt Simon's copious precum on her tongue, she knew it was time to stop. Getting up off her knees, she faced the young men and offered her best wicked smile. "Well, looks like we have a three way tie...silk and satin really turn me on!!" "A t-t-t-ie," Simon couldn't believe it. "Yes Simon...a tie....and that means you all get to take my bum" General pandemonium erupted as the men jumped up and down, giving each other high-fives and shouting with excitement. The men settled down as Miss Prim faced them to lower her thong. Then, she walked over to Isaac, turned so that her butt faced him, and slowly lowered her cheeks on his torpedo shaped shaft. Isaac uttered a deep groan and shut his eyes tightly. Miss Prim let out a long moan of contentment as she continued to force more of Isaac's prick into her butt. Finally, she reached rock bottom, enjoying the feel of Isaac's silk boxers against her asscheeks. Then, she bounced on his cock, screaming with lust in a mixture of pain and intense pleasure. Isaac let forth with a torrent of swear words as the incredible feeling of Miss Prim's tight buttcheeks around his prick caused him to nearly faint with lust. After two minutes of intense bliss, in which Miss Prim and Isaac came close to orgasm several times, it was time to move on. Miss Prim reluctantly got off of Isaac and turned her attention to Ray. He had been masturbating furiously watching Isaac's first ass-fuck and was more then ready to have his own turn. Miss Prim spat on Ray's dick, then slowly impaled herself on the fat seven incher. "G-G-G-O-D-D-D!!" Ray shrieked. The sensations were incredible, even better than when he had screwed Miss Prim the week before. Miss Prim screamed with delight as she rode Ray like a bucking bronco, slamming down on his balls so hard with each downstroke she could feel his silk boxers against her asscheeks. After 3 minutes of blissful screwing, Miss Prim got off Ray's cock and faced Simon. He had been jacking himself so quickly, he almost came twice in his excitement. Miss Prim lowered herself on Simon's penis exquisitely slowly, enjoying his long guttural moan as she impaled more and more of his fuckstick until finally she had reached his balls. Then, she bounced up and down slowly as Simon howled with lust. Miss Prim gradually quickened her tempo, giving Simon the ride of his life as his balls slapped against her bum. Simon was too excited to hold back. After about a minute of frantic screwing he knew he needed a release. "THIS IS ITTTTTTTTTTTTT.... AUUUUUUUUGGGGGGGGGHHHHHH." Simon's prick exploded in Miss Prim's butt just as Isaac and Ray started to squirt their seed all over the screwing couple. The three mens' orgasms were enough to bring Miss Prim over the edge. "AHHHHHHHHHHHHHH...EEEEEEEE." Miss Prim let out a high pitched wail as she had the best orgasm of her entire life. Simon continued to cum in her butt a solid nine spurts before withdrawing his prick from her ass with a loud popping sound. The exhausted quartet collapsed on the floor, still not believing what had just taken place. After what seemed an eternity. Miss Prim put her thong back on and turned to the catatonic men. "This will be our last rehearsal...but I want you all to come to an underwear party I'm having at my house next week. My sister, Miss Proper is visiting and I want her to share in all the fun I'm having" The men were incredulous....Miss Proper? Would she be Proper? How about her tits? Would they be as full as Miss Prims'? Two buxom women were going to be beyond their wildest fantasies! Isaac and Simon turned to Ray and grinned. "Can we borrow more of your lube?" Ray just laughed...they were all going to need it!! The Seduction of Simon Ch. 07 At last, Miss Prim's twin sister, Miss Proper had arrived for the week. They were both looking forward to the underwear party which was slated for Friday night at 7:00. Invitations had been sent, requesting that the gentlemen wear full business attire. All seven had accepted and masturbated furiously three times a day in anticipation for the event, with their cocks and balls poking out of their boxers. Finally, Friday night came. Miss Prim was dressed in a turquoise blue dress in contrast to her sister's baby pink gown with white stenciling. They greeted the men as they came in one by one....Scott, Simon, Isaac, David, Mike, Hank, and Ray. All the men were dressed to the nines with expensive suits and ties. The women couldn't believe how sexy they looked in them....but the best was yet to come! As for the men, they couldn't take their eyes off Miss Proper's ample bosum, shapely figure, and sparkling blue eyes. Seven sleeping penises began to wake in their boxers. When everyone had assembled and downed a few drinks, Miss Prim took a spinner out of a box on the table. "I think we are all a bit overdressed, and there is a lot to come off. I found this spinner in an old party game I had. Whereever it stops, everyone will have to take that particular piece of clothing off, no exceptions." The men whistled and cheered....they really wanted to see what kind of underwear Miss Prim and her sister had chosen for the party. "You go first, Simon" Miss Prim thrust the spinner in his face. Simon spun the spinner meekly, which is pretty much what Miss Prim had expected. It stopped on the drawing of a shirt. "Shirts" Miss Prim yelled. And that means jackets and ties too! Miss Prim and Proper let the front of their gowns down to reveal matching powder blue bras. Their swollen nipples pressed out the fabric and were clearly visible. The men threw their jackets and ties on the floor and hastily removed their white shirts. Simon, Ray, and David wore wife beaters, while the other four men sported white crew neck undershirts. The fronts of their trousers were beginning to bulge promisingly. Miss Prim then gave the spinner to her sister, who twirled it rapidly. Miss Proper grinned as she eyed the next item..."socks, and that means shoes, too!!" The men easily slipped off their dress shoes and dark dress socks. Miss Prim and Miss Proper took off their pumps and pantyhose. Everybody was breathing rather heavily now, in anticipation of the next item. David got to spin next. He watched the rapidly twirling spinner gradually slow down until it stopped on the line between shirts and pants. Miss Prim walked over "Looks like shirts are already gone...pants next!!!" She instructed her sister to take care of Scott, David, Hank, and Mike, while she turned her attention to Ray, Isaac, and Simon. The three men watched incredulously as Miss Prim knelt by Ray and fondled the huge bulge in his pants. Then, she undid his belt and lowered the zipper. Ray's expensive slacks fell to the floor, revealing full cut green plaid boxer shorts tented obscenely by his big prick. She quickly took off Isaac's pants as well, showing the group his pure white tapered boxers. Simon's eyes were tightly shut as Miss Prim worked on undoing his trousers. She pushed them down slowly, smiling at his baby blue trim boxers which barely contained his rigid eight incher. "I see you men are all ready for me." Without saying anything further she reached into Simon's shorts and pulled out his throbbing prick. Miss Prim gulped it down as if her life depended on it. Simon moaned so loudly the neighbors probably heard it. He had never been deep throated this expertly, and was soon at the brink of letting go of an enormous load. When Miss Prim felt Simon's precum on her tongue, she moved over to Isaac, blowing hot breath on his prick encased in his boxers. With her hand and mouth, she gradually worked his cock over to the fly slit, letting it bounce out lewdly before taking the head between her lips. Isaac grunted in appreciation as Miss Prim gave him the blowjob of the century in his underwear. After a minute of frantic thrusting, Isaac was disappointed to see Miss Prim let his penis out of her mouth and turn her attention to Ray. "Last but not least", she pulled Ray's prick and balls out of his roomy plaid boxers and slid her tongue all over the beautiful mushroom head of his endowment. Ray swore under his breath and then let out high pitched shrieks as Miss Prim suddenly started to deep throat him. She brought Ray to the brink of an explosion before letting his rock hard prick out of her mouth. Then, she took off her dress and stood before the men in crotchless panties and a blue bra. "I want all three of you in me at once..let's go by the stairs" The men followed her transfixed, eagerly watching her titties, (only partially covered by the tight bra), go up and down. When they reached the stairs, Miss Prim embraced Simon and helped him position his cock at the entrance to her wet pussy. At the same time, Ray lowered her panties in the back and rubbed his penis against her tight bum. Isaac climbed a couple of stairs and thrust his cock through the slats of the bannister. That gave him easy access to the cleft between her tits. "Ok, men at the count of three, I want all of you to push forward....1, 2, THREE!!!" Miss Prim let out a loud scream as Simon and Rays' cocks slowly invaded her willing holes. Isaac, not wanting to be left out, thrust his cock sideways across Miss Prim's breast as she kneaded the rock hard organ with her fingers. After a few tentative shoves, Simon and Ray got a strong rhythm going and thrust the full length of their organs into Miss Prim's quivering body. She began to howl in a mixture of pleasure and pain. As for Simon and Ray, they could feel their cocks rubbing together inside Miss Prim which just added further to their excitement. As the three students enjoyed their teacher, Miss Proper was having just as much fun with David and his friends. She had stripped to a pair of pink crotchless panties and first knelt in front of David. Undoing his belt and zipper, she savored the sight of his full cut white boxers, her favorite color and length of underwear. Miss Proper then quickly got the other men out of their pants and enjoyed the view. Hank wore full cut boxers with thick red stripes, Mike's were blue plaid and trim cut, and Scott's were solid baby blue. She fished four rock hard cocks and their accompanying meatballs out of the men's boxers and started to suck David and Hank alternately, much to the delight of the two men. Miss Proper had a very wide mouth and quickly decided to put it to best use. She pushed David and Hanks' cocks together and took in both their turgid heads in at the same time. "J-j-j-j-e-e-s-s-u-u-s-s-" David was in such ecstasy he could barely talk. "s-s-s-h-h-i-i-i-t-t-t-" Hank couldn't believe the sensations Miss Proper was causing him to have as she played the best skin flute in the world. Miss Proper got about half of David and Hanks' cocks in her mouth before she let them out excruciatingly slowly. She then turned her attention to Scott and Mike, giving them a double deep throat as they shrieked and moaned lustily. After a minute or so of intense sucking, Miss Proper let Scott and Mike's penises slip out of her mouth. She turned to face David and Hank, letting Scott and Mike have a nice view of her butt. "Ok, I want David and Hank to take turns screwing me while Scott and Mike take my bottom" The men got into position eagerly. David positioned his piston into place as Scott pressed his rock hard flesh into her bum. Then, Miss Proper screamed "NOW" and at that moment David and Scott pressed forward. "AAAAAAARRRRRGGGGGGGGHHHHHHHHHHH," Miss Proper couldn't believe how good it felt to be screwed by two handsome men at once. The sight of her sister being taken by her three students in their cute t-shirts and sexy boxers just added to her excitement. The two groups of sex craved men and women kept at it for a good 10 minutes, the men's grunts and groans getting louder and louder as they came close to dumping their loads. Miss Proper had several orgasms as David and Scott plowed her into oblivion, then enjoyed the change of Hank and Mikes' equally rigid tools in her hot orifices. Simon was the first to go over the brink. "I-I-I-I-I-I-I-I'm going to POP!! He began exploding in Miss Prim's twat a good nine full spurts. Watching Simon cum easily brought Ray to orgasm. "AAAAAAAAAAAHHHHHHHHHHHHH," he howled as his prick erupted in Miss Prim's ass. Isaac shot off between Miss Prim's tits just as Hank and Mike blasted 15 spurts of white cream into Miss Proper between them. Finally, David and Mike orgasmed, shooting volleys of cum all over Miss Proper. As their ample orgasms finally subsided, the seven men and two women were so spent they collapsed completely on the floor, in a delightful state of A.F.O. (All Fucked Out). After about 5 minutes of heavy breathing, Miss Prim smiled to the group..."Does everybody like my sister?" The men used all their strength to nod in approval. "Good, because she's going to be on the faculty of our school....a new flute teacher" The men couldn't believe their good fortune...now, what were they going to do until the next semester? As if she was reading their minds, Miss Prim continued..."and we are going to have at least 3 underwear parties over the summer, anyone have a problem with that?" Ray piped up "only three??." The group laughed...it was going to be a summer to remember!!