Stanford Sex Challenge

This is the true story of the sex challenge that my sister, Jen, and I conceived one semi-drunken night a couple of years back.

I'm Sarah, a fifty-year-old mother of two grown kids, both of whom are presently at college in Texas. Jen is a couple of years older but it's easy to tell that we are sisters; we're both tall, around five feet eight, and blessed with blonde hair and bright blue eyes, thanks to our Scandinavian heritage. In addition, we've both worked hard to maintain our figures; me by working out in the gym every day and Jen, through a combination of long-distance running and cycling. As a result, it's probably fair to say that we are both lucky enough to have figures that your average fifty-year-old woman (and man) would die for. I'm a little larger than Jen up top, 34c rather than 32b, but other than that we could probably be mistaken for twins. We've always been very close and even when Jen went off to college we'd talk for hours on the phone and spend our weekends together, going on double dates and having fun with boys.

While we have both been blessed with wonderful children, life and careers have unfortunately taken their toll on our personal relationships. I've been divorced for seven years while Jen and her husband, Geoff, though still together, pretty much stopped having an intimate relationship about five years ago. According to Jen, Geoff just seemed to lose interest in sex and she's never found a way to rekindle that part of their relationship. Consequently, each of us is often to be found complaining to the other about the lack of sex in our life.

In large part, I attribute the failure of our personal relationships to the emphasis that we placed on building our careers and our business. In retrospect, if we'd lavished as much care and attention on our marriages as we did to climbing the corporate ladder we'd both still be happily married. However, our genetic heritage seems to have endowed us with a drive to succeed above all else. Right from the time that we entered high school we were both laser-focused on being at the top of the class and excelling at everything we did.

Jen graduated with a Masters in Chemical Engineering from MIT, joined ExxonMobil, and worked overseas for fifteen years before returning to the US to settle down with her family when Geoff accepted the position of James T. Scott Professor of Chemical Engineering at Stanford University. Strangely enough, I had received my PhD. in Computer Engineering from the same institution twelve years earlier and had built a successful career in the tech industry, eventually ending up as a VP of development for Google.

Jen and I had always dreamed of forming a startup tech business together and that's exactly what we did when she quit Exxon and settled in Stanford. Our company, Alexon, designs and manufactures smart process control devices for refineries and chemical plants. Thanks to Jen and Geoff's chemical engineering expertise and my own background in computer engineering, Alexon grew quickly and within a few years, we found ourselves running a very successful company that had a multi-million dollar order book from all over the world. Three years ago Alexon was acquired by a global manufacturing conglomerate, an event that made both Jen and I extremely wealthy. Though we both still work at Alexon, we now enjoy the luxury of being able to decide on how we strike an appropriate work/life balance.

Ever since our kids were in high school, we've both been deeply involved in the Parent Teacher Organization, initially as volunteers and eventually as board members. Even though all of our kids have graduated and moved on, we've remained involved in organizing fundraisers, building and funding specialist programs and leading a mentoring project for Seniors interested in a career within the tech industry.

One evening, not too long after we had concluded the sale of Alexon, Jen and I were enjoying a bottle (or two) of wine on my deck. As I mentioned earlier we have always been best friends as well as sisters and it was no surprise that our conversation eventually found it's way to the sad state of our sex lives.

"I Just don't know what else to try! I've arranged date nights, bought sexy lingerie, tried to spice things up with porn and still I can't seem to get Geoff's attention. I'm lucky if he fucks me more than once a month!" bemoaned Jen with a loud sigh.

"At least you're getting some," I replied, giggling a little. "I haven't had a good lay since Jim and I divorced. Sure there's a long line of guys ready to date but either they turn out to be douche bags or, if they do manage to get inside my pants, they can't perform or have no clue whatsoever about what we women want in bed! I've all but given up hope that there is any man of our age out there that can satisfy me."

"Well, all I know is that I need to have a cock inside me soon!" Jen said, slurring her words slightly. "I'm only fifty-two and there's no way I'm ready to give up on sex! We need to come up with something, Sarah!"

"I know, ... I know," I said. "I'm just like you, almost going crazy having to use a vibrator to get myself off." I laughed, "You know that David Eaton kid from the school? You know, the one who plays Point Guard on the basketball team and wants to go to Vanderbilt?"

"Oh, yes...I know who you mean. What about him?"

"I've taken him on as a pool boy and was watching him skimming the pool the other day. My God, he is fit! He was out by the pool in just a pair of shorts and flip-flops and it was all I could do to hold myself back from going out there and dragging him back to my bedroom! I bet he is hung like a horse!"

Jen stared at me in amusement "Not that you or I are ever likely to be in a position to confirm that fact! I could probably walk past him naked without so much as a turn of his head."

"Not true at all! Haven't you noticed how the boys look at you when you are at the school? I'm sure there is a long list of them that are eager to get in your pants!"

"Seriously, Sarah! I'm fifty-two and while I think I've aged pretty well, I doubt that any eighteen-year-old boy is likely to have the hots for me."

"Think about it Jen, ... think about it," I said, my mind turning slowly as a result of the alcohol we had consumed. "You are beautiful, have a bank account that affords you the finer things in life and, to boot, have the sexual experience of a fifty-two year old woman! Isn't the MILF and cougar role meant to be the 'it' thing that young men salivate over these days?"

"It is! However, I'm not sure that I qualify for either of those tags!" she said with a giggle. "Though it would be nice to have an eighteen-year-old toy boy to look after me in the bedroom!"

"Wait! Maybe that's the solution! We both need to find ourselves a young guy that we can mentor and train to satisfy us in bed! It's a win-win for both parties; we get well fucked by an insatiable eighteen-year-old and he gets to learn the secrets of what keeps a woman happy in the bedroom! Not to mention the benefit of unlimited blowjobs and fucking a beautiful woman on a regular basis!"

Jen laughed. "Sarah, you can't be serious! How would we find guys like that? And, even if we did, think what would happen when it got out that we were screwing seniors from the school!"

"Granted that we'd need to pick carefully and be ultra discreet in how we go about it, however I'm sure that there must be a way. I'll give it some thought and see what I can come up with!"

That drunken conversation was, my dear readers, the genesis of the Stanford Sex Challenge which Jen, I, and two of our friends, Mary and Crystal, have been running for the last two years. The essence of the challenge is this; at the start of the summer break we each pick a male Senior that we intend to seduce and fuck over the course of the coming school year. We use our PTA connections to carefully screen the incoming senior class; first to ensure that each of our targets are over eighteen and secondly, to ensure that we are choosing the brightest and the best, both academically and physically. Call us elitist if you like, however none of us are willing to give ourselves to just anyone!

Fast forward to mid-July last year and you would have found the four of us once again sharing wine and conversation on the deck.

"OK, ladies...we've discussed the potential candidates and narrowed it down to Bob Stillwell, David Grant, Ryan Anderson and Mark Hood. All of them are over eighteen and exceedingly hot, so it doesn't really matter who we draw."

Crystal laughed. "Speak for yourself, Sarah! I'm definitely hoping to get Ryan...he does my yard work on a regular basis so I know just what a hot body that boy sports!"

I handed the bag with the four names to Jen who smiled, closed her eyes, and dipped her elegant fingers into the bag. Her smile widened and she blushed as she read the name of her target.

"Mark! Oh my God...I've known him and his family since he was ten! I'm not sure I can go through with this."

Jen quickly looked to her left, handing the bag to Mary as if it were a hot potato.

"Your turn," she muttered quietly.

Mary hesitated for a moment, looking at each of us in turn, before reaching in and extracting a name.

"Bob! Yum...he's on the swim team. Have you seen his body? Hot doesn't begin to describe it!"

With that singular rating of Bob, she passed the bag to Crystal.

"You have a fifty-fifty chance of picking Ryan," I said with a giggle. "Good Luck!"

She drew a name from the bag with a flourish. Her smile dropped a little as she read out her selection.

"Damm...David! Not to say that he isn't handsome and hot but I did really want Ryan!"

"Don't worry," I responded with a giggle. "If you are good, I might just be persuaded to share him at some point. Wouldn't that be so hot - I'm sure he'll have the stamina to satisfy us both in one session!"

This drew whoops of laughter from all of the ladies and it took us a few minutes to settle back down.

"OK, here are the rules. One; you are required to seduce your target before the end of the first semester. Failure to do so will eliminate you from the challenge. Two; Each boy will be required to complete a questionnaire at the end of the school year rating each of us with regard to our behavior in the bedroom. Three; You are at liberty to share your target, either individually or as a couple, with any one of us. Doing so will improve your year end rating. The individual with the highest rating will be named Stanford's Sexiest Mom! May the best woman win!"

"Wait," said Mary. "How will we know that each of us really did sleep with our target?"

"We are working on the honor system. It's just like playing golf at the Country Club," Jen responded. "If you say that you fucked them then we will believe that you did."

"Oh...well, can I suggest that we have a monthly lunch together to check in on progress and share the juicy details of what has happened in the previous few weeks?" Crystal asked.

September 28th

We met for lunch at Gennaro's which, if any of you know Stanford, is a divine Italian restaurant on Emerson.

"Ladies, ladies..."I said, breaking in to the animated conversation going on around the table. It's time to give your progress report for the past two months. Who'd like to start?"

"I will," Jen replied, immediately. "I've got quite a bit to report actually."

This drew audible gasps from the rest of us seated at the table.

"You haven't...have you?...Really?" Crystal said in a flustered fashion. "Surely not!"

Jenifer giggled and turned red.

"Well...actually, yes!" she said, with a distinct note of triumph in her voice.

"So quickly! How did you manage it?" Mary queried.

"I told you when we were drawing names that I have known Mark and his family for ages. From talking with Karen, his mother, I know that he wants to study Math at Stanford so I asked her whether he might benefit from some extra tutoring. She was only too grateful to accept on his behalf and I've been tutoring him twice a week for the past eight weeks!"

"Ha...in more than Math, I suspect!" Mary exclaimed. "I can't believe you managed it so quickly. We need details!"

Jen blushed a deeper shade of red. "Well, he's been coming over in the afternoon once he finishes class and I've been sure to dress sexily and flirt with him when I have a chance. A couple of weeks ago I pretended that I had forgotten he was coming over and answered the door in just a towel. He was a gentleman but his eyes were all over me. I took the initiative, kissed him and pretty soon large, fat cock cumming in my mouth." She grinned wickedly, "Let's just say that in the last couple of weeks I've been coaching him in subjects other than Math."

We all began shrieking and shouting more or less at the same instant in response to the bombshell that Jen had just dropped

"Shhhhhhhhhh...keep it down, ladies! We don't want the entire neighborhood to find out about our little challenge!" she responded in a hushed voice.

I leant forward, looking in amazement at what I thought was my goody, goody sister, as she went on to explain, in a low, muted voice, just how she had maneuvered the eighteen year old son of a good friend into her bed.

"Oh my God, you wouldn't believe just how sexy it felt to be on my knees in front of his hard body and slowly draw his boxers down to reveal his cock. I'm telling you...I was dripping like never before."

Mary gasped! "What did it look like!"

"He's long and thick...much thicker than Geoff. The head is shaped like a mushroom and has a deep purple color. There was a spot of pre-cum on the tip that I just couldn't resist licking off!" she replied, her face coloring a deep red.

It was my turn to gasp! "Jenny, did you allow him cum in your mouth!"

"Of course I did, little sister! You would too if you were able to experience the gorgeous cock he has. You won't believe just how much he produced when I eventually allowed him to cum. It was truly amazing...he just seemed to shoot string after string of the stuff into my throat."

I grinned, "I always knew that you were a little tart at heart, Sis!"

She responded simply, sticking her tongue out at me and laughing.

"Your're just jealous that you aren't the one that got fucked first ...and oh my God, did he ever fuck me! He may only be eighteen but honestly, he knows how to pleasure a woman with his cock! I haven't asked how many girls he has had but I imagine quite a few."

I glanced over at Mary and Crystal who, like me, seemed to be blushing furiously. And, while I can't speak for the others, I have to admit that my pussy was wet and tingling as a result of imagining my sister being taken by Mark.

"Just how many times has he had you?" I asked in a somewhat bitchy tone.

"Let's see," she said, thinking for a moment. "He fucked me twice that first day in addition to cumming in my mouth...can you imagine any of our husbands having the stamina to cum three times in one session! Then there was the following Wednesday...mmmmmm, ...ten times so far! And everyone of them was just perfect!"

Crystal laughed, "Well that does it, I guess It's time to make my move on David. I've employed him to look after our yard and have purposefully been sunning myself by the pool whenever he's around. I've caught him watching me more than once so far. I'm pretty certain that I'll be able to report that I've completed the challenge by the time our next meeting comes around."

"Your turn," I said, looking pointedly at Mary. "Any progress to report with Bob?"

"Well I suggested to Claire that she might like to invite him over to study as she has a number of classes with him."

Claire is Mary's gorgeous seventeen-year-old daughter, who is also happens to be a senior at the school. Given how pretty she is I could well understand why Bob would be more than happy to 'study' with her.

"They've actually been hanging out together quite a bit since the start of school. I'm pretty sure that he has the hot's for her, though she seems to be playing it cool at the moment. I've made sure to be around whenever he comes over. I've seen him looking me over and he seems a little nervous when I flirt with him so I'm sure he is attracted to me as well as Claire. Claire is still a virgin so I know that he isn't getting any from her so Phase 2 of my plan is about to be initiated!"

"That leaves me," I said.

"Knowing that Ryan is into computers almost as much as he is to swimming I've found him a job at Alexon doing some networking and computer support. He's a friendly and respectful boy; always willing to bring me a coffee or do the odd task for me. I know by the way that he looks at me that he's interested so it's just a case of reeling him in at the appropriate time."

The girls laughed. Crystal was first to respond.

"Knowing you for so many years I'm aware that you always get what you want eventually, Sarah. Just remember that you only have until the end of the semester to do the deed though."

I laughed and banged the table twice, while smiling at my good friends around the table.

"I declare this inaugural meeting of the Stanford Sex Challenge Club to be over. I'd like to congratulate Jennifer for being the first ever member to meet the challenge. Good luck to the rest of you in the coming month. Our next meeting will take place on Halloween."

To be continued...