Hi, my name is Don and this is a story based on events that happened last summer. It took me nearly a year to be able to write about it, but I had to share it with someone, so thanks for reading this. The events that happened that summer afternoon were based on events that had been building up for several years. My wife Jill has an odd friendship with a woman named Lisa. Their “friendship” started in high school and it seemed that no matter what they were involved in, they took it as an opportunity to try to “one up” the other.
Both women are now in their early 30’s, but act as competitive as they did as teenagers. Lisa and Jill have retained their “friendship” in spite of their intense competitive relationship that they have. Any outsider observing their behaviour towards one another would think that they were life long enemies, instead of friends. Jill lives to top Lisa and this drive has influenced most of the decisions that Jill has ever made, including marrying me.
I work as a chemical engineer at a global pharmaceutical firm that has a research facility in our town. Jill found me her freshman year, while I was a senior and we dated and got married when Jill graduated with her teaching degree. Jill knew early on that she wanted to marry a guy that would give her the lifestyle that she had grown accustomed to, since her dad was a successful small businessman that enjoyed spoiling his daughter. Since Jill was so involved in cheerleading and studying in high school to compete against Lisa, she rarely dated and she had remained a virgin until our wedding night.
Lisa played the field in high school and in college and Jill would tease her for her “looseness”, but Lisa wanted to make sure she sampled all of life’s pleasures before settling down. Lisa was not stupid and managed to graduate with a 3.5, a few notches below Jill. However, both women ended up teaching at the same high school. Jill taught mathematics, while Lisa taught English. Jill would often make remarks on how Math was so much more important than English and how she should be paid more. Jill’s opinions became even more vocal when Lisa married John, the new P.E. instructor.
Because of Jill’s desire to one up Lisa, she constantly pushed me into taking on new projects and to climb the corporate ladder, so that I could provide her with more of the “finer things” in life. I loved Jill and wanted to please her, so in being so passive I created a spoiled brat. I never felt that I was in control of the relationship. In fact, I was always surprised when I saw a guy do what he wanted and how it did not matter to his wife, since she would do whatever he said. I just figured some guys had found women that were more “wired” to please their man. Lisa and John’s relationship was like this. Lisa would do anything to please him, like he was her drug dealer and she was a crack addict. While I on the other hand would work like a dog at work and around the house and rarely got an “I appreciate you” sex session from my wife.
In spite of my wife’s opinions of him, John and I had always gotten along pretty well together. In fact, last spring when John heard that we were going to put in an in ground pool, John offered to teach me to swim, since I had never learned how. I work a lot of hours, but John said that he often works out before school and that I could come over to the school gym and get my lesson before work. Jill insisted that we get a pool, since she hated the idea of being seen by her students in her bathing suit at the local beach. A side benefit of the pool was that it allowed Jill to rub it into Lisa that she had a pool and that Lisa would never be able to afford one on her and John’s salary.
When I arrived for my first lesson, John pointed to the locker room and told me where to change and that he would be in the pool, where a couple of the freshman swim team guys were doing laps. This was the first time that I saw John without his shirt on and I was impressed with his chiseled physique. Since I work so many hours I have become a bit soft and I was hoping that with the pool I could at least start to swim a few laps and firm up a bit. Turned out that John was pretty patient with me and the initial lesson went well.
I agreed to come each morning for the next month, and we discussed my training program as we headed into the locker room. As I was soaping up I saw John walk in with the freshman boys and my jaw nearly hit the floor. Besides being so buffed, John happened to have one of the largest cocks that I have ever seen. When soft, mine barely hangs 2″ and is just shy of 5″ when fully erect. Shoot, the boys that walked in easily had more hanging than I did. Easily, I had the smallest pecker in the locker room that day. John easily hung down over 6″ and was quite thick. I felt a bit intimidated standing there with my “wee willy” next to a man that could easily be a porn star. John must have noticed my staring as he smiled, but he never said anything to add to my embarrassment.
That night in bed, Jill asked how the lesson went and she was pleased that I was going to stick to the program since she has always loved the water and it eased her guilt in making me buy her the pool in our backyard. Jill was surprised to hear that I showered at the school, but I told her that with my project I did not have time to drive home.
Jill asked if the guys showers were separate stalls, like the women’s shower rooms and I told her how it was just a big room with several nozzles sticking out of the wall. Jill mentioned how she would have hated the lack of privacy, but I told her that every gym that I was ever in was designed the same way. What happened next really surprised me. Jill reached over to me and said, “So how did “little Don” fair today? ” “Little Don” is what Jill calls my cock when she is feeling playful. Jill calls it Little Don, not cause she thinks it is small, but that she thinks it has a mind and personality all of its own. Until our honeymoon, Jill had never seen another man naked. Jill is quite petite and with her small 5’2 inch frame she is nice and snug for me, so she has always assumed that I must be “quite endowed”.
Besides having very limited dating experiences, Jill lives a very sheltered and conservative lifestyle. We have never seen an adult movie or purchased sex toys or anything else on that level. So, as Jill was prying on how I was next to John I knew it would kill her to know that she would be getting something less than her rival Lisa. So, I did what any other normal guy would do that wanted to keep his wife happy, I lied to her. I did not just lie, I told Jill a “whopper” telling her how John was even smaller than the freshman boys that were in there with his little “button” between his legs.
I told Jill that I was easily twice John’s size and Jill squealed with delight as she jumped on top of me. As she was riding me, she said, “No wonder Lisa can be so bitchy sometimes, probably the lack of meat in her diet.” Jill was riding me so hard, that I slipped out a couple of times before she had orgasmed. I think when it slips out it teases her clit even more causing her to climax so quickly. Afterwards, Jill told me on how she was so glad that she did not have to settle with a guy like John.
As Jill smiled and giggled to herself thinking how she had another thing that Lisa didn’t I lay there thinking about what I had just said. As I thought about it I realized that there was no way that Jill would ever become the wiser about my lying to her. Jill and I would never discuss sexual things with another couple or friend, but Jill just liked knowing that she had something over Lisa. As I thought about this I realized that I had nothing to fear about Jill finding out, so I went to sleep feeling happy that I was able to once again provide my wife with another victory over her nemesis.
The weekend before July 4th, Georgia was sweltering and I was glad that we had the pool to cool off in. Jill wanted to show off our new kitchen and her latest love, her new Lexus GX 470, which cost me most of my bonus. I have often felt that if she had to choose between me and the new Lexus, that it would be the Lexus.
Jill could not wait to rub in our new toys with Lisa. Jill called Lisa and invited her and John over for a pool party. Lisa asked Jill if they could invite Beth and Tom over, since Beth was new to the area and taught History at their school. Beth and Lisa socialized a lot after school, but Jill hardly knew her. However, Jill thought the idea of rubbing it in Lisa’s face with an audience was great and readily agreed. Jill told Lisa that we would pick them up at 2:00 PM, so that she could show Lisa how nice her new car rode. Jill added, “I doubt that you and John would ever get a chance to ride in something so nice, again.” Jill giggled as she hung up and let me know that we would be picking the other couples up next weekend in her new car.
When we woke up Saturday, I reached over to Jill hoping for a little “play time” before the party, but Jill jumped out of bed and told me that we did not have time. I had been working a ton of hours that month and it had been weeks since Jill had made love to me. Being the type that does not like confrontation I got up and helped Jill prepare for our afternoon pool party.
Jill and I drove up to Lisa and John’s modest home and I cringed as Jill commented to Lisa on how she would probably feel pretty frustrated with her car after being in the Lexus. Jill added, “Once you have experienced a ride like this, all other cars will just frustrate you.” Lisa, just nodded politely, but did not comment, but smiled as she rubbed John’s leg. As I looked in the mirror, Lisa seemed very cool, like she had something up her sleeve.
We picked up Beth and Tom at their apartment. You could tell that they were newlyweds as they giggled and kissed in the back of the car. I thought they were a nice couple and I was looking forward to getting to know them better.
Jill had quite the spread laid out and I blushed several times as Jill rubbed into Lisa’s face on the things that we had in our home. Jill spared no expense and even stocked our new bar, so that our guest would be so impressed. This was uncharacteristic of Jill, since she rarely drank. Jill showed the couples where to change and told them to meet us on the patio when they had their suits on.
As Jill and I were changing, I kept looking over at her admiring how she looked. Her blonde hair and nice tan seemed to go so well together. I felt it was a shame that she kept her figure hidden behind such a modest bathing suit. Jill wore a navy one piece that was modestly cut. Since Jill had always felt so self conscious of her very small bust, she picked the suits with a built in padded bra that made her look much bigger and prevented her nipples from poking through when she was cold. I often told Jill that if she was an AA or a DD cup, I would love her just the same, but she told me that she would never wear a bikini around people that she worked with. Jill said, “Perhaps, when you get that next promotion I will let you buy me a bikini for me to wear for you around the house.” I smiled at the thought of seeing her 34A bust enhanced by one of those Wonder bra bathing suits that I have seen at Victoria’s Secret.
As Jill and I were getting things ready, our guest walked outside and my eyes must have looked like they were coming out of my head. I have always thought that Lisa was a pretty woman, since I had a thing for brunettes. Lisa has long brown hair and looks like an Amazon next to Jill, towering her by at least 6″. What was most shocking was the swimsuit that Lisa chose for today, a thong bikini that made her bust look like they could have provided shade for a small boy. I thought that they would easily be a D-cup or larger. Her bottoms were so snug; I could have sworn I could see her “camel toe” which seemed so prominent and sassy.
I quickly excused myself, worrying that my erection would be seen and made up an excuse to go in the house to get something. While inside, my curiosity got the best of me and I went into the bedroom that Lisa and John used to change and I reached into her changing bag to pull out her bra. I nearly came in my pants as I read the 36DD tag and was going to jerk off in our bathroom when I heard Jill yelling for me. The fear of Jill or someone else catching me quickly made my erection go away. I knew I could not let “little Don” get carried away today, since out of all of life’s forbidden fruit, the rival of your wife’ is the most forbidden of all.
When I went to the grill, I was happy to see Beth come outside in her bikini, too. Beth is an attractive blonde, but her bikini was nowhere near as provocative as Lisa’s. Also, Beth appeared quite a bit bustier than I would have guessed. I had never noticed this before since I had always seen her in “teacher’s clothes before. Beth’s breast looked so firm and full, but she was easily a cup smaller than Lisa. However, with the scare I got earlier I was not going to verify it like I did Lisa’s since it would be a disaster if I got caught. I never realized how much Beth and Jill resembled each other, until I saw them both together. Beth looked a little blonder, a little younger, and a lot bustier than Jill, but their smile and facial expressions seemed identical to me. I thought to myself as I looked over my patio, a man can have worse days than staring at 3 pretty women half naked in his backyard.
Fortunately for me, all the guys wore loose fitting trunks, so it was not obvious if a guy was packing 4″ or 14”. Jill pulled me aside a few times complaining about how Lisa and Beth were dressed. I had to act like I was just as offended, while deep inside I wanted to see both their tops ripped off, so that I could see even more of them exposed.
As the afternoon wore on and as more drinks got consumed the atmosphere became more relaxed. As our guests finished a game of water volleyball, each woman climbed on her husband’s shoulders getting ready for a game of “chicken fights”. If you have never heard this game, basically you have your girl on your shoulders trying to pull the other girl off and become the winner. The guy tries to manoeuvre the two of them to give his girl more of an advantage over the other players.
Lisa yelled over to Jill, “Hey Jill quit working on the house and grab that husband of yours and climb on top of his shoulders, so that we can play a game of chicken fights. Unless, of course, you are too afraid to lose?”
Jill responded, “Lose? To who, you and John? Just because you’re taller does not mean you have any advantage over me. In fact, your height and your choice of swimwear will work against you!”
Lisa yelled back, “Well, bring it on bitch!” and everyone laughed at her challenge.
So, Jill threw off her wrap and took my hand and led me to the pool. Jill then climbed on my shoulders and adjusted herself to make sure she was on good. Lisa announced that the last couple left standing with his wife on his shoulders is the winner. The women then yelled, “Go!” and we all tried to get in position to knock off another couple. Knowing how Jill would want to save Lisa for last I went for Beth and Tom, but both couples must have made some plans in advance, since they both surrounded Jill. Soon, Beth and Lisa grabbed a shoulder strap of Jill’s and did a quick yank almost causing one of Jill’s pink nipples to be exposed in front of Tom. Jill was so busy trying to conceal herself that she lost track of Lisa as she grabbed her from behind and pulled her off of my shoulders. In my attempt to stand up, I bumped into Tom’s legs, causing Beth to lose her balance, so that only Lisa and John were upright.
Lisa screamed, “We won, we won!” Jill angrily got up to the surface, trying to get her hair out of her eyes. Jill then said, “You cheated, no one said that another couple could do such a dirty trick as to pull down one’s swimsuit! We were setup!” Lisa just laughed and told Jill, “All is fair in love, war, and chicken fights!”, and everyone but Jill and I laughed at Lisa’s remark. Jill was angry and was about to let her temper get the best of her. I tried to calm her down when Lisa said, “Do not worry, the guys did not see anything they have not seen before, except only smaller, a lot smaller!” Lisa and John were laughing as Lisa added, “Do you think John and Tom are going to be all flustered after seeing your mosquito bites exposed, when they can see ours anytime they want?” I assured Jill that I doubt if they saw anything, but just the thought of it made Jill stew. Especially, seeing John grin and enjoy Jill’s predicament, someone that she saw at work on a regular basis.
Jill just replied, “Any more than a mouthful is wasted, fortunately for me I have more of everything else that you could possibly want!”
Lisa said, “What do you mean by that? Care to make a wager? Second thought, no sense betting with you, you would just back out anyhow!”
This made Jill even angrier. Jill said, “I will put my new Lexus up as collateral, if I welch any bet that I lose with you! What do you say to that?”
Lisa just said, “Bring it on! You have always been all talk and no action! To show that I mean business, I will hand Beth my Jeep keys to give to you if I welch!”
I wanted to try and calm Jill down, but before I could do anything Jill marched inside the house because she was formulating a plan and she needed the other couples inside to get things rolling. Jill had her cover-up on and yelled for everyone to come inside for a glass of wine. As everyone was sitting at the table, Jill showed them her Lexus key chain. Jill then tossed her Lexus keys to Beth saying, “If I lose and welch out on my bet with Lisa, you have my permission to give her my car! Since the value is not equal, my only request is that I get to choose what we bet on!”
John said, “Man, I would love to have that car without paying a dime!” Lisa told John that Jill has rarely beat her at anything, so be prepared to drive it home tonight. Jill interrupted her, “Even if I did lose, I can only lose my car if I refuse to pay up, so do not be counting on anything yet, John! Besides, I have beaten Lisa many times in the past. If you do not believe me, just look around this house to see who the real winner in life is!”
Beth asked Jill if she could get in on the action, too, since she has always been a bit competitive herself. Out of pride, Jill readily agreed as Beth tossed the keys to her Camry on the pile. The addition of Beth was an unexpected wrinkle to Jill’s plans, however she knew most of all that she would be able to beat Lisa, so that was all she was focused on for now.
Jill stated, if you lose to just one couple, you just have to do one task that the winning couple gets to choose. If you are the one couple that loses to both couples, then you have to do three tasks that the winning couple chooses. Jill could not wait to have Beth and Lisa wash her car and clean her house while their husbands mow their lawn. Jill could not wait for this to start.
Jill pulled out her tape recorder from her pocket and says, to make sure no one backs out I want to hear everyone agree to the terms and to agree to do the tasks that the winner says or they will forfeit their vehicle. Jill added the caveat that since she has the most expensive car to risk, she gets to decide what is being betted on. Lisa added that it can not be some weird math problem or something mental, and Jill smiled and quickly agreed. Jill said, “If the losing couple makes any attempt to not to readily participate in the tasks, then they automatically lose their car!” Jill could hardly contain herself thinking about humiliating Lisa and John.
Beth added, “The task has to be something that can be done in an hour or less. I do not want to be someone’s personal slave for the day.” Jill agreed and said that when she asks them to clean her house or cook her meal that an hour will be fine. Lisa said, “What makes you so sure you are not going to clean my house, huh?” Jill just smiled, and said, “Are you in or not?”
When everyone agreed to the terms I wondered what Jill had in mind to make such a bold bet. Did she think she was going to out run or arm wrestle Lisa for the title?
Lisa then looked at Jill and said, “So, what is it? What is the bet? We are all in and let’s get this thing started!” Jill got up from the table and walked to the head of the table where we were all looking at her. Jill pulled out a tape measure from her cover-up pocket and announced, “I bet that my husband has the largest penis of the three husbands!”
Both Lisa and Beth gasped at such a wild statement made from their prissy friend. This was totally uncharacteristic of Jill. Being the bolder of the two Lisa said, “Penis? What is this, high school biology? It is called a cock, Jill.” Jill added, “Is a cock what you call something that is 3″ long? I am going to enjoy seeing you and John lowered a notch tonight!” Beth looked at Jill like how would she know John’s cock size? However, with the amount of wine that everyone had and the threat of losing one’s car, no one objected to the bet since they all had agreed to participate.
I could not believe my ears, how could my Jill do this? Jill was now going to see at the worst time how I had lied to her earlier this year. My only hope was that Tom’s dick was smaller than mine. That way, I would not have the total humiliation of being the least endowed of Jill’s friends.
Jill wanted to cause Lisa to squirm and announced that we would go first, followed by Beth and Tom, with Lisa and John going last. All the couples left the table and went into our living room. Jill smiled and grabbed me by the hand, so that I was in the centre of our U-shaped couch while the other couples were gathered around. It was kind of surreal seeing Jill kneel down to me with her tape measure in her hands. I was so nervous that when she lowered my trunks, I was shrivelled to just an inch. I could sense that Beth and Lisa wanted to point and laugh, but to their credit, they kept up their “poker faces” and watched Jill try to stroke me.
I was humiliated as she started off with her thumb and index finger stroking my soft cock. Jill’s back was to them and she did not see that Lisa lowered her bikini top a little giving me a glimpse of her pink nipples causing my cock to grow to maximum hardness. Jill yelled, “I know one woman who is getting a real surprise right now, knowing that she has lost to at least one couple.” No one said a word, they just watched Jill now use her one hand to stroke me and she proudly put the tape next to my dick and said, “5 inches, beat that, girls!” While she was still stroking me, Lisa pulled aside her swimsuit bottom revealing her strip of dark pussy hair that ran up from her bare slit. Seeing this and not having sex in so long, I came immediately in Jill’s hand. Beth laughed and said, “You should have bet who can cum the quickest. You have been married for how long and he comes that quickly?” Jill was now a little less confident that she was going to sweep the event since she thought Beth’s remarks were so bold. Jill “knew” she had Lisa beat, so that is all that mattered to her. I never let on to Jill what Lisa did to me or she would have been real mad at me for getting off from Lisa’s exposed body. Instead, Jill beamed with pride thinking she had a well hung stud for a husband and that her sexual techniques were so good that she could make a grown man cum so quickly.
I cleaned up and sat next to Jill as Beth and Tom got up next. I knew this was the make or break couple for us and was never so anxious to see another man nude. I felt sick to my stomach when Beth lowered Tom’s trunks to reveal a 4″ soft cock. Being naïve, Jill wrongly assumed that it would not grow any bigger and she was mentally preparing her tasks for Beth and Lisa. Beth then surprised everyone there when she took Tom’s soft cock and started to lick it as she caressed his balls gently in her hands. Beth did not approach oral sex in the “If I have to do it” mindset, no, she approached it like a starving man would a steak dinner, she eagerly started to devour it. I have never seen a woman approach oral sex with so much enthusiasm and energy. Tom proudly told us, “Fellas, you are about to see why I always walk around with a big grin on my face, I am married to the best cock sucker in the world!”
With that, Beth slowly let Tom’s now hard cock slowly release from her mouth.Jill nearly gasped as she quickly realized that Tom was easily bigger than me. Beth placed the tape next to his hard cock and showed everyone that it measured a proud 7 ½ inches. Beth said, “A whole inch and a half over average, and I appreciate every bit of that, too!” With that, Beth went back down on Tom and made him cum violently into her mouth. Being the good wife, she caught every drop and cleaned him up nicely. Jill just whispered in my ear, “Did you ever hear that the average penis is 6 inches?” I shook my head no like it was the oddest thing I had ever heard. Jill never knew how many times I would stroke “little Don” as a teen hoping I could reach that milestone of 6 inches. Women do not know how that number haunts us guys that are below 6 inches. I was thankful that Lisa did not make a big deal about authenticating Jill’s measurement of me, since truth be known, I am exactly 4 ¾ inches. Being the mathematician that Jill is, the 6 inch rule would drive her nutty with the fact that the majority of the women out there were getting 25% more in bed than she was.
Jill has now mentally accepted that fact that she may have to do a task for Beth, but she is anxious to see John and Lisa humiliated. Jill is surprised that they are not more anxious about this as they calmly walk into the center of the room. Jill can not let things lie and says, “Now we are about to see why Lisa is such a bitch and so frustrated in life!” Jill is surprised that she is the only one laughing. Lisa asks Beth for the tape and drops to her knees, like the other women did. Slowly, Lisa would start to lower John’s trunks, like she thought she had the losing hand. Jill was on the edge of her seat, waiting for John’s three inches being exposed. She could not wait to see this jock lowered a notch cause of how he laughed at the thought of Jill’s breast being exposed earlier.
When Jill saw his pubic hair she started to lean closer to get a better view. Lisa lowered slowly and his shaft was now beginning to get exposed. Jill was surprised that for being so short that his penis appeared so thick. Jill was expecting John’s head to be exposed as Lisa lowered the trunks even further. Instead of seeing the head of his cock pop out, we just kept seeing more and more of his shaft. For the first time it became real to Jill that she may be the big loser today. Jill gave me a look that could kill as she now realized that I had lied to her. I just hanged my head, knowing that I had failed my wife. Before long, the trunks were pulled to the floor and John’s soft cock was now exposed. Lisa said, “I will now measure it soft, 6 ½ inches.” Lisa looked at Jill and said, “Even soft he is far bigger than what you have to settle with.”
Jill wanted to hang her head in defeat, but her curiosity got the best of her as she stared at John’s cock. Instead of giving John oral sex or a hand job, she stood up, and slowly untied her top, letting it fall to the ground. With her breast now exposed to everyone, Jill turned her head aside in shame, knowing that Lisa’s areola alone would more than fill her small bra. Jill then looked over to John and almost gasped out loud as she saw John’s erect cock pointing towards the ceiling. Lisa placed the measuring tape over it and showed everyone how it measured to 10 inches. Lisa pointed out that her man was nearly twice the size as Jill’s husband.
As Jill sat dumbfounded she was surprised that Lisa did not bring her husband to climax like the rest of the wives. Instead, Lisa said, “I was just going to let you sit there in your humiliation and come up with some things for you to do around my house. However, with the way you taunted and showed off when you thought you had me, it got me a bit ticked, so now I am going to make this a bit nastier. Perhaps, teaching you a bit of a lesson.”
Lisa then pointed to the pile of car keys and said, “Will Beth and Jill please stand in the center, so that they can receive their first task?” Tom teased at Beth, “You better get on up there if you do not want to have to walk to work this next year or so.” Beth teasingly punched her husband in the arm and started to walk towards the middle of the room. I told Jill, “You got us in this mess, unless you want to lose your Lexus, you better get up there, too. I will be damned if I am going to buy you another car like that!” Jill replied, “No, you got us in this mess, if you did not lie to me earlier about John’s penis size we would not have been in this position!” The other couples laughed and I hung my head in shame knowing that she was right. However, Jill was not going to lose her car and add insult to injury and resigned to the fact that she had to do each of Lisa’s tasks, so she did not have her car to rub it in each day.
Lisa then stated, “John and I have had a disagreement for the last few months that the two of you are going to help us finally settle. John and I just agreed that which ever one of us is right, gets to have the third task as that person sees fit without any consequences from the other spouse. John and I have agreed on the first two tasks, since the first one will settle our debate.”
John said, “I have always thought that Jill was not a true blonde, but that Beth was definitely one. Lisa always stated that she has known Jill since she was a kid and knew her to always be a blonde and had no doubt that Beth was a true blonde, too. However, when guys state the words ‘true blonde’, they mean, do the curtains and carpets match. We do not mean do they use a hair dye”
Tom started laughing and said, “A scientific task, how noble of you John. I never knew you were such a man of science.” John and Tom continued laughing while Jill just stared like she did not understand.
Lisa could see Jill’s confusion and blatantly told Jill, “John does not have any doubts that the hair on your head is blonde, but he doubts that your pussy is blonde!” Jill blushed at her comments and intuitively dropped her hands in front of her crotch as if John had x- ray vision or something.
Lisa said, “So, ladies we are going to answer this great mystery by letting me undress you in front of everyone. Of course, you can back out now, but it will cost you your car.” With that, Lisa nodded to the pile of car keys.
Lisa walked up to Beth and said, “Ready and willing?” Knowing that the tape player was still running and would be used as proof, if anyone balked.
Beth said, “Strip away, my busty friend!” Beth giggled as Lisa started to unhook the back of her bikini top and whipped it away, revealing her light brown nipples. I could not stop staring at them. Beth’s tits may have been smaller than Lisa’s, but they were so sexy and firm. Lisa’s were a little rounder and fuller, but Beth’s seemed to defy gravity as they stood up proud and firm. Both sets were definitely keepers, but I liked the contrast to the pink nipples that I was used to.
Next, Lisa asked Tom and John to begin the drum role as she got to her knees and placed her thumbs under the waist band of Beth’s bikini bottoms. As the guys began drumming, Lisa slowly started to lower Beth’s panties, when all of a sudden the first hint of hair started to show and it was indeed, blonde! Lisa lowered them to the floor revealing to all of us her pretty blonde V. Beth’s bush was not white blonde, but a nice soft gold color. As Beth stood with her legs slightly separated, I could see that she shaved her slit area keeping the V shape on top of the slit. Unlike Lisa whose bush was in a one inch landing strip that extended further than Beth’s and Jill’s pussies did. I was getting hard seeing Beth totally naked. Beth was quite comfortable naked, bowing to the clapping of Tom and John. Beth then walked next to Tom and snuggled up close and said, “Did I make you proud?” Tom said, “Yes, I have always been proud of that pussy of yours!” Beth squealed and kissed Tom and told me and John to enjoy the show since after this hour was up, she doubted if we would ever get a chance to see her naked again and laughed as she sat back to see what Jill would do.
Jill said, “You know I have no choice bitch, so let’s get this over with!”
Lisa said, “First, remove your cover up and slip your arms from your shoulder straps. Your hour does not start until you are accessible to me.” Jill removed her cover up and slipped her arms from her straps and stared at the clock in the living room. Jill could not make eye contact with anyone as she stood in the center of the living room waiting to be stripped.
Lisa said, “Gentleman, if I can trouble you with another drum role?” Tom and John started to drum and Beth joined in making her breast flop with each slap on her thighs. Lisa said, “First, let’s see what Jill has been hiding up here!” Lisa tapped over her breast to show that her swimsuit was padded with a thick covering. Lisa said, “Here is what you should have seen in the pool!” Lisa slowly lowered the top until each of Jill’s very small breasts popped into view. Jill’s whole body blushed crimson as the cool air conditioned air caused her small, bright pink nipples swell outside of her control. Tom said, “Looks like a small girl trying to hide two eggs under her chest!”
All four of them laughed and as I studied my wife’s small breasts I had to admit that his analogy was right. Jill’s breasts looked so miniature compared to Lisa and Beth’s. They barely protruded from her body with not enough weight to cause them to drop down. Lisa commented that Jill could use two nickels at the tanning booth to shield her areola since they were so small. What was worse is that Jill knew she could not stop them unless she wanted to give up her car. Jill just stood there as Lisa commented on Jill’s tiny breasts. Finally, Lisa yelled to John, “Care to bet that my areola is bigger than Jill’s whole tit?” John said, “No thank you, I know a sucker bet when I hear it. Your nipples alone would more than fill her small bra. What do you think she is, a double A?”
I tried to defend my wife and without thinking I yelled, “Try 34A, John.”
Jill looked at me, like how could I divulge such personal information and looked at me as I betrayed her. Lisa laughed loudly and said, “No wonder you hid them so well in gym class, I have not seen an A-cup since 6th grade.” John added, “That is the cockiest you have been all night, Don.” After stating that, he held his fingers 2″ apart and the four of them laughed at his comparison.
Lisa said, “Now to settle this argument I have had with my husband. Jill, you better not let me down, or I will make the next task more humiliating for you!” Jill was motionless, she knew this was going to be a long hour; she could not wait to get her clothes back on!
Lisa nodded to the others, “Drum role, please.” Lisa started to slowly unroll Jill’s one piece bathing suit. Soon her stomach was revealed and Lisa continued to lower her swimsuit without mercy. As they went down further, Tom blurted, “Shouldn’t we see some pussy hair by now? John, do you think Jill shaves it all off?” Lisa giggled and told them to be patient and that got the three of them chanting, “bush, bush, bush, bush” over and over again, building in volume with each tug of Jill’s bathing suit.
Finally, about a 1 1/2″ from the top of her slit the first of her pussy hair was now seen by the room. Lisa yelled, “Shit, it is as black as coal! No wonder you never spread those legs for anyone, you knew that after seeing your tiny boobies they were sure to be disappointed not to see any blonde pussy fur.”
With that Lisa yanked the bottoms off revealing Jill’s small dark unshaved bush. Jill’s bush was in a natural V shape that covered her slit and went up an inch and a half. Unlike Lisa’s that seemed to be twice as prominent as Jill’s. Beth stood up next to Jill and said to Tom, “Are you thankful to be married to a real blonde?” Tom yelled, “Hell yes, that is one sparse, dark pussy. The only place it is thick is along the slit. Shoot, you can barely make out where her slit is with how thick it is there. I have never seen a pussy like that, especially on a blonde.” John nodded in agreement as Jill continued to stare at the clock in total humiliation.
Lisa announced, “I think that I have had a change in plans for my 2nd task. Jill has always been a little spoiled brat and her bush looks so odd contrasting the rest of her that I have decided that the 2nd task is to have Jill submit to Tom’s razor!” I choose Tom because he has the most experience with blondes and he did beat Don in the contest tonight. I think each day that Jill looks down at her bare pussy it will remind her on what a little brat she is. If she wants to act like a kid that is OK cause now she will look like one with her small boobies and bare pussy!”
Jill’s eyes widened. Jill looked at me and I looked over at her car keys and shrugged my shoulders. I wanted to tell her I was sorry, but before anything could be said, Lisa picked up the tape recorder and asked Jill, “Can Tom shave your pussy right now?”
Jill swallowed, looked at her car keys and quietly said yes. Lisa told her to speak up, and Jill said, “Yes, Tom can shave me, Lisa.”
Lisa and John were surprised that Jill was going to go this far. Lisa looked at the clock and told Tom to hurry and go find a razor because you have 20 minutes to shave her, so that John can have Jill totally naked for a half hour for her last task.”
Tom and Beth got up and ran to our bathroom to look for the supplies. Lisa giggled and yelled up stairs, “If you can not find a razor, just grab a pair of tweezers, because there just is not that much to remove.”
Before long Beth and Tom were heading downstairs. Tom had the shaving cream and a new razor. Beth went through Jill’s stuff and found one of her 34 nearly A heavily padded bras and had it stretched over her large titties. Lisa laughed and said, “You can not cover up until your hour is up Beth.”
Tom said, “Don lied again, the back of this tag says nearly A, so she is not far from needing a trainer.” John pointed to Beth’s brown areola spilling out from the cups of Jill’s small bra and said, “Good thing I did not make that bet with you, Lisa. Beth’s nips are easily smaller than yours and look how they more than fill Jill’s small bra!”
Beth laughed, “Are you sure mine are smaller? Care to make a bet?” Beth laughed again, and said, “You know that I am kidding, right? I know that Lisa’s are bigger than mine!”
Lisa thanked Beth and said jokingly, “I was about your size after high school, so cheer up you may surpass me someday.” Lisa then playfully swatted Beth’s bare bottom as she went next to her husband.
Beth helped Tom lay a sheet over our leather chair and asked for Jill to sit there, so that each leg is over an arm on the chair. With Jill in this position it would allow them a good angle to do a good job. Jill complied and very slowly separated her legs. Jill intuitively had her hand over her slit and Lisa came by with the Lexus keys and shook them making Jill lifting her hand exposing her pussy to the room.
Beth said, “I bet someday, you will thank us for this beauty treatment.” Beth began to apply the shaving cream over her entire pussy. Tom then started at the top and with one stroke he had all the hair above her slit removed. Tom rinsed the razor and started to shave the left side of her slit, revealing her lips for the first time since she entered puberty. When Tom shaved the right side, he asked Beth to hold the lips a bit taught, so that he could get the last tuft of dark hairs over the top of her slit covering her clit.
Tom took a warm wash cloth and washed the cream off and said, “I have more time left, I think I will oil her up, so it will not be irritating later on.” When he removed the wet wash cloth from her bare slit, everyone whistled and said, “Nice work, Tom, not a hair in site! Now, when she walks down a nude beach, no one will know that she is not a true blonde anymore!” Lisa added, “Problem is, people will wonder if she is either a sexually active 12 year old girl or an underdeveloped 30 year old!” I had to admit that Jill’s slit looked so fragile and tiny void of hair. Even with her legs spread wide, there was no way to see inside since her lips did not gap open. Tom had Beth sit next to Jill with her legs spread and pointed out to John and I how small Jill’s slit is compared to her.
John studied it and said, “No wonder she never knew how small Don was with a pussy that tight. When you oil her up, let me know how snug she really feels, OK?”
Tom, said, “You must be reading my mind!”
With that, Tom started to massage the oil over Jill’s bare slit. I could tell that his warm hands were having an effect on my wife since now, instead of staring at the clock, she was biting her lip and watching as Tom was teasing her freshly bared pussy. Tom used three fingers and started to go up and down her pussy hoping to get his middle finger to sink into Jill’s slit.
The last thing that Jill wanted to happen to her happened. Beth yelled, “Look, I think I see her clitty swelling up!” Jill tried in vain to not respond, but with her slit void of hair and the warm oil being massaged all over her she could not help but to respond. On the rare occasions that Jill allowed me to kiss her pussy I always noticed how her clit swelled when she was real aroused.
I could tell that Jill’s mind was a storm of thoughts: betrayal, humiliation, jealousy, greed, and now arousal. Nothing that happened to Jill today was planned. Tom looked at the clock and saw that he still had 10 minutes. He went over to Beth and whispered in her ear and she blushed and told him, “You better enjoy this, because I doubt that this will ever be repeated, but because I love you I will do this for you.” With that, Beth oiled up her hands and started to manipulate Jill’s small pink nips. I thought Jill would scream or bite her lower lip off as she was fighting in vain with her body. Beth just said, “Relax Jill, I just want to give you and Tom some pleasure.” With Lisa and John watching, the last thing Jill wanted to happen was for her to orgasm in such a humiliating setting. Jill kept trying to keep her body from responding, but was failing miserably.
Beth continued, “I recently read in Cosmo that all women’s breasts had the same amount of nerve endings. The article mentioned that smaller breasted women are much more likely to experience an orgasm from just nipple stimulation than larger breasted women like Lisa and I. Further into the article it stated that the smaller the male penis is, the more sensitive it is, too. The article noted that the man with a smaller penis has a harder time with controlling his ability to not cum prematurely and that they rarely can last more than 5 minutes of penetration. How sad for the poor women that marry men with small cocks, huh? Besides being unable to penetrate as deeply as their endowed counterparts can, they cum much faster, too. Have you found this to be true Jill? We already saw today that Don came within just a few strokes where Tom took a lot more foreplay. Now, as I tease your little nipples I can see your slit moisten and you are at the brink of orgasm.
Jill just laid there and watched Beth playing with her small pink buds some more making them more erect that I had ever seen them. Jill tried to fight moving her ass, but everyone could tell that she was being played by a master and wanted to release herself from fighting this, but she was determined to not give Lisa the satisfaction.
Beth surprised all of us next as her oily hands continued to tease Jill’s nipples, she knelt between Jill’s open knees and started to use her tongue on her pussy. Jill’s eyes widened even more as she was not sure if she should be shocked or turned on. Beth’s tongue found Jill’s exposed clit and teased and sucked on it bringing her close. Lisa told her to just bring her close, but not all the way, so Beth continued her playfulness. I saw the sweat falling from Jill’s forehead as she lay there panting like a horse that just completed the Kentucky derby.
Lisa smiled over to John and said, “I know what your task is going to be, go get it Tiger! Show her how a ride with you will make all other cocks frustrate her, especially ones as small as Don’s.”
Lisa use of Jill’s line to her about her car came back to haunt her. Jill was now shaken back a bit into reality as she now realized that John’s final task was to enter her pussy. Jill looked scared and for the first time this evening I think Jill gave the thought of losing her car some serious thought. If I knew what I do now, I would have easily made the trade of her car for her pussy being left untouched by John’s large cock.
Jill looked over at me and said, “I just have to last 30 more minutes and this nightmare will be over, you make good money, but not enough to throw away 55 grand. Ok, Lisa, you won this battle, let your husband stick his big dick in me.”
John was now standing next to Jill with his cock rubbing on Jill’s oiled up nipples, so that it was getting nice and slick. Jill’s eyes kept getting bigger and bigger as she stared at his monster between his legs.
John said, “I am really looking forward to this, being the first man to find your ‘button’. Up to now, you have experienced a clitoral orgasm or two, but tonight you will experience an orgasm like none other you have felt before. When I am Done, you will not be satisfied by a small cock again. You will be frustrated every time you see Lisa because you know she is getting this pleasure any time she wants. Sure, you have your car, but Lisa has true riding pleasure every day.”
Jill tried to turn her head from him, but she wanted to try to stay in control, so she watched as he kissed her nipples and sucked on them making her squirm once again. His mouth would alternate between each nipple as his finger would trace her slit. John told her to open her mouth and accept his cock and Jill had no choice but to comply. Jill could not open up enough, but seeing this high and mighty math teacher trying to get his head in her mouth was worth it all. He knew she could not get the rest in her mouth and did not want to waste any time because with her tight pussy it was going to take some work to ease it all the way in.
John worked his way up her body giving her pussy one final kiss. His mouth easily covered her whole slit and she screamed out loud trying to fight his touch. She hated her clit for responding since John just look at her and smiled as his tongue flicked her exposed clit knowing she was his for the taking.
John kneeled between Jill’s legs and lifted her legs over his shoulders, so that her pussy was in front of his cock. John took his cock and rubbed it up and down slowly on her slit making her squirm. John then told Jill to grab his cock and rub herself with it. Jill’s hands trembled as she tried to control the monster from over taking her.
John took her hands into his and raised them over her head, so that her breasts appeared nonexistent. He smiled as he looked down her body with the head of his cock at her opening. Jill knew what was about to happen next, she still had 15 minutes left. John was a gentleman and eased the head into her opening. Being oiled up he was able to get that first inch or two, but he yelled, “Man, Don, you have left me with the tightest pussy I have felt in years, thank you!” He went in a little further and Jill grimaced a bit, but it was not as bad as she had feared.
In fact, with him being so thick it was feeling very good, even though she wished it didn’t. With each move her slit was tightly stretched around his cock and when he pulled out you could hear a suction sound followed by a pop. Very similar to the sound of your foot stuck in mud as you pull out.
Jill looked down and could see that her juices had only reached a third of his cock and that he would not be happy until it was all the way in. Problem was her clit wanted it more and more. With John being so thick, each stroke he made caused his shaft to rub on her clit, something she had never experienced before.
John then started to suck on her stretched titties as he went inside again, this time going 5″ with the first push, He stopped sucking to tell Jill, “You are about to experience your first real cock, remember this feeling well, for you probably will not feel it again.” With that John eased more of his cock breaking her 5″ barrier. Jill has never had penetration last so long; if this was Don he would have came 2 strokes ago. John pushed in a few more inches and Jill let out the loudest deepest sounding moan I had ever heard her utter.
Lisa looked at me and said, “Jill just felt her ‘button’ get pushed for the first time in her life. Hard to say how this will change her Don. After John did this to me, I knew I was captive to him for life because I knew I had never had it found by any other man. I will do anything for John as long as he will fuck me with that large cock of his.
I then realized that perhaps the reason that some men seemed to have more control of their women was because they were able to be the first to discover this button on their woman.
John asked Jill, “Want to feel it all in, baby? Want to feel what it feels like to come with 10 inches of hard meat inside of you?” Jill did not say a word at first, but wrapped her legs around his back and said, “Fuck me hard, you big stud, show me what I have been missing my whole life.”
John backed up a bit until only a couple of inches were left inside, then he pushed all 10 inside as Jill started panting and crying with her first vaginal orgasm of her life. John was getting close, but he wanted to drive her harder and grabbed her ass as he drove violently into her. John yelled out, “I am cumming!” Jill just yelled, “Ah, ah , ah, ah over and over again until she yelled a final scream as she said she could feel his cock squirting so deep and hard inside her and she nearly passed out before John could pull his cock out of her.
When John finally pulled out we all gasped as we saw her small slit gape open for the first time. Being overcome with lust I went down on her and pumped my small cock inside amazed how her once snug pussy hardly had any contact on my small cock. Seeing her nipples so hard I came within three strokes.
Being the smart ass, Beth announced, “See, Cosmo never lies. Even after orgasming nearly an hour ago he still prematurely ejaculates.” Our friends laugh at Beth’s comments as my shrinking cock easily slips out of my wife.
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