The Tangled Web
Chapter 1

Copyright© 2017 by harry lime

Coming of Age Sex Story: Chapter 1 - Julie is ready for the prom, ready for college and definitely not ready to lose her virginity just yet. Now she has this silly problem with the scholarship committee thinking she is a he and she has to choose between four years of lying and deceit or give up her scholarship and probably her chance at getting a college education. It was a certainty that her family would not be able to pay her way without some help from her athletic scholarship.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/ft   Mult   Teenagers   Coercion   Consensual   Reluctant   BiSexual   Heterosexual   CrossDressing   TransGender   Fiction   School   Sports   Spanking   Group Sex   Anal Sex   Exhibitionism   First   Masturbation   Oral Sex   Pegging   Petting   Safe Sex   Voyeurism   Big Breasts   Size   Small Breasts   Teacher/Student  

“Julie!”

That single loud shout that echoed up the well-worn steps of the carpeted stairway was almost immediately followed by a longer and even louder yell that penetrated Julie Costello’s tender ears like some noisy police drama on the wide-screen television in the basement recreation room.

“Julie Costello, get your teenaged butt out of bed and get down here for breakfast because mom needs to go to work right now.”

The young and extremely attractive brunette with the slender body of a cross-country runner turned over in the narrow twin bed and peeked with one eye squinted open at the small digital clock on the cluttered night stand.

At that very instant the dial flicked from 7:00 to 7:01 and the pretty young senior student bolted out of the sheets to reveal all she had worn in the nocturnal hours was a skimpy pair of pink and black pussy-cat panties and an almost invisible 14 karat gold anklet chain given to her by Josh Randell on her seventeenth birthday as a memento of his supposedly adoring friendship. It bothered young Julie to think of Josh so early in the morning because he was becoming desperate to taste more of her hot but totally disinterested teenaged body. She knew her almost eighteen year old runner’s body was in peak condition had no intention of gifting Josh with its use in a way that she was not quite ready for as yet.

In fact, the thought of carnal pleasures was distressing to her because it interfered with her studiously assembled program of muscle enhancement and stamina building that she needed for the grueling cross-county meets.

In fact, the hidden guilty truth was that she was a lot more interested in his older brother Mark with his college football player’s physique that had all the girls on Elm Street gaga with feminine daydreams of intertwined limbs and searching lips.

Still, it was nice to have a decent-looking guy like Josh willing to let his fingers and his tongue do all his wooing and knew enough to keep his nasty boy equipment inside his bulging trousers. She had absolutely no curiosity to investigate his masculine equipment because she was certain it was just the same as all the other so-called dates that pestered her to fondle their package well out of sight of any on-lookers. She had generally agreed to their request if they were well-behaved because she had a natural curiosity to compare the equipment lengths and sizes to see which ones interested her the most. In fact, she had become quite adept at bringing most masculine shafts to spurting release with a few tricks she had learned from her elder sister that had already joined the Army and was assigned overseas.


Julie ran into the bathroom and brushed her teeth whilst sitting on the unpadded throne like some queen in a pink and white realm of porcelain and tile in every direction. She smiled as the sound of her emptying bladder filled the small room with the unmistakable sound of a healthy urological system. Some nasty thoughts flitted though her mind. She pushed them from her consciousness like an unwelcome stranger. Julie wanted desperately to retain her perfect four point zero grade point average and win the cross-country contest on the coming Saturday morning. She was certain it would give her all the ammunition she needed to be accepted into State college the coming year.

Quickly, she whipped off the pussycat panties and washed her sensitive parts with the warm washcloth. Momentarily, she considered her status as a virgin and wondered if that helped her or hindered her in her finishing kick across the finishing line of the school district competitions. Whenever any of her friends asked her,

“Are you still a virgin?”

She would just look at them and smile a little mysterious smile to make them think she knew all she needed to know about boys and the things they could do with their business in the back seat of their parent’s car. Julie let them make up their own minds about that and most just believed what they wanted to believe and she could not be accused of actually lying about anything. She used that same process for most questions that she didn’t want to answer for fear of giving up too much information about herself that she would rather keep hidden.

Today was the day they were taking the photos for the yearbook and she took her limited stash of make-up with her to make her face pop with some added color. She seldom used cosmetics because they had ingredients that she didn’t quite trust and she was happy with the way she looked with just a hint of color on her lips from her mother’s favorite lipstick.

As she was running out the door to jump into the family car, she saw the mail on the porch table. Right on top of the heap was the letter she was expecting from the State College advising her if she had been accepted or rejected. She stuffed it into her back-back and decided not to look at it until after the photos were all taken. It would be a no-no for the photo op session to have her face look all teary-eyed if she didn’t make the cut.

The morning classes were all a bit boring because she had so many other things on her mind. Her best friend forever Elizabeth was sending her eye signals that caused her to join her in the ladies room to discuss the fact that neither of them had lost their virginity over the weekend. Sometimes, she just wanted to shake Elizabeth and tell her that it was no big thing and that whatever would be, would be and there was nothing either of them could do about it that would change the outcome.

To top things off, silly Josh was giving her an ultimatum about her putting out for him before the clock struck midnight on prom night. It was so ridiculous that she almost told him to find another date if that was his attitude. Fortunately, she calmed down enough to consider the fact that it would mean her missing the all-important prom that was only two nights away.

She gave him one of her best Julie the bitch smile’s and whispered,

“We will have to see what happens, sweetie. Just be sure to bring some protection because I plan to go to college after the summer.”


The photos were a big success and she was certain the lipstick and the eyeshadow made her face look a lot more interesting than when she went without any make-up at all.

She had missed the bus and decided to walk home because she needed the exercise anyway.

It was the perfect time to open the letter from State College and she skipped over everything just to read the last paragraph that welcomed her to the new class and wished her the best of luck in her studies. The entire day had been just perfect except for the silly position taken by Josh about giving up her cherry on prom night. She was well aware that a lot of other girls were already planning to do the exact same thing and had bragged about it in the gym class to the other girls to make them jealous of the exciting evening happening in the near future.

Julie almost skipped down the sidewalk knowing it made her look positively juvenile, but she didn’t care what people thought about her childish appearance. She planned to change into her running togs as soon as she got home and do the cross-country run that she loved more than life itself.

Her running helped her to forget all thoughts about boys and their need for sex.

When she reached a certain distance, it never failed to bring her to a peak of satisfaction from the friction of her inner legs and the way her shapely buttocks slapped together each time her foot hit the ground. Julie instinctively knew it was in effect a replica of sex and whole lot less complicated because she was the only one involved. The only regret she had about the whole running routine was that her breasts had not developed like the other girls and she had only bee-stings to display when she took off her shirt in gym class.

It was almost dusk when she finished the demanding warm-up run.

After dinner, she spent a little more than two hours stretched out on her pink and white bed dressed again only in her favorite panties. She did her homework religiously and was conditioned to focus on the subjects in front of her with absolute diligence. Before she brushed her teeth again and did her other bathroom duties, she read the letter from the State College once more to make certain she understood her requirements exactly.

Then, she saw the sentence in the middle of the next to last paragraph that read,

“Subsidy for room and board is contingent on satisfactory participation on the men’s varsity track and field team at all times. It is imperative to maintain adequate grades in all assigned courses of study and not be found in violation of any published rules or regulations to receive this athletic scholarship.”

Julie nervously went over that paragraph several times because it was the first time she had noticed the word “men’s”. She was tempted to giggle imagining herself as a man and she found it impossible to believe they could possible think her to be a male with a name like Julie.

Then, she noticed the envelope was addressed to Jules Costello.

She rechecked her original application and saw the typo that stated her name was Jules Costello and that she had not specified her gender in the block that asked for a block to be checked. In fact, nowhere in her application had she mentioned her female characteristics. Her flat-chested photo taken after a cross-country race had her sweaty face looking quite androgynous under her close-cropped hair that she liked best of all because it helped reduce the drag on the upward slopes.

There was no doubt in her mind that they thought her to be a boy and that the scholarship slot was for a male student on the men’s cross country team.

She tucked the letter away in her backpack and decided she would straighten the whole mess out after she arrived at the school.

The night of the prom was coincidentally a night of a full moon and Julie looked up at the bright circle in the darkened sky wondering how she was going to break the news to Josh that he was definitely not getting lucky in the midnight hours. In a way, she kind of felt sorry for him because she was certain he was as much a virgin as she and he had been planning this coming of age ceremony for the entire year.

Her study hall partner Louise Honeyhopper called her right before Josh was due to turn up and told her in a shaky voice,

“I don’t know what to do, Julie. My date fell off his motor bike this afternoon and can’t go because of a broken leg. I am all dressed up and my parents are fit to be tied because they spent so much money on my dress.”

Julie was immediately moved to offer to take Louise with Josh and her to the gym hall for the dance and they could mingle once inside with no embarrassment to the distraught young girl.

Louise was not her best friend forever by any stretch of the imagination but she was a steady study partner and Julie didn’t want to see her evening ruined.

It was certain that a number of single males would be at the dance because the rumor mill was filled with stories of young girls losing their cherries in dark corners and outside the hall in the back seats of the four door sedans. It seemed reasonable that some of those bewildered young girls might be interested in a little comparison shopping whilst having fun at the dance.

Of course, Louise was a bit overweight but that was compensated by the fact she was endowed with a set of boobs that filled most of the male student body with an urge to investigate their flexibility and taste. Julie had helped her pick out a nice control top semi-girdle that made her lower half look a bit more appealing from behind even if it did make her look a little stiff on the dancefloor. There was no reason why she shouldn’t attract some young lad to give her a nice tumble before the night was out.

Julie knew that Louise was not a virgin because she had given her graphic descriptions of how her boyfriend Donald had taken her standing up against a tree in the woods behind the school. Julie had to run home and bounce on her teddy bear for almost a half hour just to get her female parts back into normal condition of passive rest.

After that candid confession, Louise constantly had given her reports of the many disgusting things that Donald had made her do in order to continue being her steady boyfriend. Deep down inside, she knew it was all perfectly normal for young people to do such things, but Julie still believed in the fairytale of true love and finding a soul-mate to take care of all such nonsense.

She ran out to Josh’s car waving goodbye to her parents over her shoulder.

It was easy to convince him that just had to help out Louise in her time of need. He was not too enthusiastic at first but changed his mind when she leaned over to kiss him flush on the lip using lots of tongue to help him decide. The fact that her hand accidently fell down to rest innocently on top of his rising erection closed the deal with nothing else needing to be said by either of them.

The evening promised to be exciting and it seemed like the addition of Louise to her date was the icing on the cake because now she had another girl to exchange thoughts with before, during and after the night of adventure and intimate exchanges. She began to see a way to get out of her sort of semi-promise to Josh about ending his limbo of virginity providing Louise was in a mood to be a life-saver and stand-in for her when push came to shove.

The wheels started to whir and click in her devious female brain as she pushed the whole virginity thing out of the limelight and started to sort out her plans for switching her college future from a male student scholarship to a female one because she would be hard-pressed to play the role of silly boy chasing after a bunch of even sillier young things away from home and on their own for the first time ever.

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