Allison's Endeavors to enter Womanhood

by Aeralyndal

Caution: This Sex Story contains strong sexual content, including Teenagers, Romantic, Humor, Petting, School, .

Desc: Sex Story: A late bloomer who has now entered Swanhood. These are the trials and tribulations of her endeavors to enter WOMANHOOD!


Author's note:

If you are expecting Wham, Bam sex every other page then THIS is not the story for you. IF our heroine ever has sex then the whole purpose of the story is ruined!

This story is a TEASE from start to finish. There will be a LOT of titillation, a lot of NEARLY doing what they both want but... Think of the old 'Perils of Pauline' cliffhangers with sex and you have a good idea of what I am after. I HOPE I can bring it off. I have asked several other authors who's work I respect to suggest additional scenarios for the couple. If YOU have something different that you would like to suggest let me know. As I said, I am open to a good suggestion. Like the Greek Tragedies, these will be called EPISODES, not chapters!

Allison McCleary was a very lovely young female. She was brown of hair, green of eye, long of limb, very shapely and a virgin! This was something that she was hoping to remedy in the very near future and had been making plans towards that goal. Allison was a late bloomer. An ugly duckling until she finally started to blossom mid way of her senior year in High School. She was still turning into a Swan when she graduated. She had been very active in many of the school activities but had never caught the eye of anyone she was interested in dating. Sure, she had been asked out by every nerd, wooze and loser in school but she was interested in someone who was closer to her ideal. Studdly, handsome, rugged, manly, tall! (You can see now one of her favorite pastimes, reading romance novels.) He would have to be tall for her to look up to him as she was 5-10 herself.

While working at the local florist Allison had met a young man who was spending the summer at home between his freshman and sophomore years at the same college that she would be attending in the fall. Charles Ashworth Pennington! Charles' Mother (an Ashworth of course!) made sure his WHOLE name was always used. The Ashworths were an old and respected family in that area of the state, the Penningtons had money. Charles' Father had taken over the old Ashworth Manor house by the simple method of purchasing all the mortgages, liens and outstanding debts against the property and then foreclosing. An arranged marriage soon took place and Charles was the results.

She saw right away that he was tall and handsome. As they spoke she found out that he played football which should make him rugged and manly. She had also seen him in a bathing suit as some of the girls around the pool teased him and knew he was also Studdly! If Charlie had a problem it was that he wasn't the brightest bulb in the pack. To make up for that deficiency however he was generous, funny, very open and extremely likeable. Oh, well, a girl can't have everything but Allison DID plan on having him in her bed before much longer.

Charlie's Mother was giving one of her special 'Teas' that week end and Charlie had invited her to attend so he could show her off. The fact that she would also be the only person there anywhere near his age had nothing to do with it!

Episode One

"Oh, Chaarlie. I'm so thrilled to be going to one of your Mother's famous 'Teas'. Only the 'best' people are invited to any of her functions," said Allison as she batted her eyelashes up at him.

"I still say they have to dust most of them off before they allow them out of the mausoleum! I think the youngest one there must be 90! I HATE these things yet Mother Dearest requires me to attend so that I can meet, be seen by and associate with my social peers. She's really hung up on this society crap as if the social scene in a town this size really meant something! We'll just walk around a bit, smile a lot and then beat feet out of there to have some FUN!"

Allison already had HER idea of what would be fun and hoped they coincided with his. TODAY! She would join the ranks of womanhood and LOSE her virginity!

When Charlie introduced her to his Mother he made the mistake of introducing her only as Mildred Pennington.

"It is Mildred ASHWORTH Pennington, Charles I have told you before that I am very proud to be an Ashworth," retorted Mrs. Pennington, excuse me, Mrs. ASHWORTH Pennington!

As expected Mrs. Pennington looked down her nose at Allison even if she had to tilt her head back to do it. Mrs. Pennington did not consider the McClearys to be social equals even if Mr. McCleary owned his own successful business. To hear her speak, they were simply 'in trade'. Allison didn't help matters when she reminded Mrs. ASHWORTH Pennington that the McClearys owned three of the mortgages on Ashworth Manor before Mr. Pennington bought them up.

The two young people circulated around the gathering, meeting, speaking with and socializing with all the others who had been invited. After more than an hour of this they slipped off to be alone, to be away from all the others. Charlie had been showing her through one of his father's prizes and the reason for the 'Tea', his greenhouse when they decided to slip away. One of his special hybrids, an African Violet was about to bloom. It was rare for this particular breed to blossom and they were making an occasion of it.

Cutting through one of the extensions Charlie had just warned her to be careful when she pulled him to her and kissed him deeply. The prim and proper white sundress she was wearing was low cut in the back and it was obvious that she was not wearing a bra. This was another thing that turned up the nose of Mrs. Pennington, Allison going braless and having a bosom to flaunt while she herself, even as an adult female who had given birth, was barely out of the training bra stage!

Charlie returned her kiss with just as much fervor and enthusiasm. In fact he went a little overboard as they moved closer and closer to the shelves of plants housed in this section of the greenhouse. One of his hands was groping her shapely ass while he moved the other up to fondle and gently squeeze one of her lovely melons. Her only response was to move closer to him and to assist him as much as she could.

His hands were feeling so good and they were having the desired effect and she just KNEW before long she would be joining the ranks of WOMANHOOD when suddenly Allison's back was drenched in cold water! The automatic sprinklers for this section of the greenhouse had come on.

When hit by the cold wetness against the heated skin of her back she, of course, bowed her back and moved forward to escape the torrent of falling water. This action on her part unfortunately knocked Charlie into the trays of plants just where two trays came together. His weight caused the other ends to fly into the air and hit the long trays above them knocking them down as well. There he was, sitting on the floor with pot after pot of plants cascading down on top of him.

Being hit repeatedly by the falling tile pots was bad enough however the plants inside the pots were a species of African Violet to which Charlie was highly allergic! Responding to her high pitched scream as a results of the sudden cold shower Charlie's parents came upon her trying to shield him from the falling plants, get those that had fallen on him off and to move him out of the way. As happens most times when you attempt to do two things at once, much less three you end up doing NONE of them and that was the situation that those responding to the screams saw. Allison was missing the falling pots, catching them on the first bounce as they ricocheted off Charlie and moving them aside. Again unfortunately she was placing them in such a position that they impeded her attempts to move Charlie out of the way of more damage. Luckily they were hitting him in the head which, as we mentioned earlier, was rather thick therefore not causing any real damage.

Turning off the sprinklers Mr. Pennington then moved to assist Charlie. So did his Mother who only succeeded in getting in the way even more until such time as the falling pots had stopped due to no more pots being on the tilted shelf to fall!

After having all the pots fall on him, the plants rub all over him and being exposed to their pollen (?) Charlie's allergies went into overtime and his breathing passages were closing up. To make matters worse, the prize African Violet that was the cause of the celebration had broken off and the Just-about-to-open bud was now lodged behind Charlie's left ear reminiscent of the South Seas Island girls!

Quickly moving to the first aid kit Mr. Pennington removed a syringe with an antidote and injected Charlie. Knowing the Pennington's had a greenhouse and Charlie's allergy the Doctor has provided a sealed container with the proper dosage for an emergency treatment until proper medical attention could be received. He then used him cel phone and called for an ambulance. That done he turned back to see about helping Charlie's young lady and couldn't believe his eyes. The affects of the water on the white sundress, against a nicely tanned body had turned the dress translucent! Her beautiful breasts were being displayed as only those of a healthy young female's can be. The darker brown of the nipple seemed ever darker and stood out more against the small white area of the bikini she had worn while tanning. The breasts themselves stood up proudly from her chest and swayed wonderfully with each of her movements. Charlie unfortunately was so groggy from the affects of the allergy, the medication and from repeatedly being hit on the head that he was unable to appreciate this most fetching sight. His father, ever the gentleman, removed his own jacket and offered it to the seemingly bare-to-the-chest young lady. Filling his eyes and his memory with the glorious sight before she covered it up with the offered jacket.

It was only as the ambulance drove rapidly away that Allison realized that she now had no way home. Mr. Pennington gallantly offered to give her a ride home as he was going in that direction now anyway. He needed to go to the hospital if only to pick up his wife.

It took nearly a week for Charlie to recover from the reaction to the violets AND the crashing pots. Each time that Allison visited him his Mother was present and her only reaction to seeing the female who had endangered her precious son was a loud sniff! She wouldn't even leave the room so they could talk quietly together. She listened and made comments to anything that Allison tried to say to Charlie.

So ended the sweet young lady's FIRST real attempt to enter the ranks of WOMANHOOD! Her fertile imagination however was already coming up with other ways that this could be accomplished!

Episode 2

Allison McCleary's first date with Charles Ashworth Pennington had not ended as either of them had anticipated nor desired! Charlie had ended up in the hospital where he had to remain for nearly a week before he could be released. Mildred Ashworth Pennington (again insisting that HER family name be mentioned also) did not look fondly on the association of her only son with this, this PERSON, who was obviously below his station. She did NOT however place very many obstacles in the path of the two knowing full well that the fastest way to drive them together was to forbid her son from dating the creature.

Allison for her part was a very nice and attractive female. She was well educated so far even if it had been only a PUBLIC school and was enrolled at the same university that Charles was attending. Allison however was going on an academic scholarship, something she had herself earned, not something provided by her parents however willing and more than able they were to send her there. Mildred Ashworth Pennington made sure she did NOT make any despairing remarks about her attending the same university as Charles. She did play down the scholarship as being more charity than something earned as her darling Charles was dumb as a post and had only earned a partial athletic scholarship due to his prowess in the sport of football.

When finally even his doting Mother could find no excuse to keep him at home they were going on a picnic, a picnic alone, away from prying eyes so that they could indulge in an activity that they BOTH wished to partake.

They first went to the lake where unfortunately they were immediately spotted by some of their friends and couldn't get away. They swam, roughhoused and played with the others, laughing along with them at the good sport even if this wasn't the sport that the two wished to play. It had finally sunk into his dense head that Allison was as eager to have sex with him as he was with her. The only obstacles being where and when! They weren't even able to play in the water. As soon as one or the other of them began a little touchy, feely someone else would blunder in to interrupt.

Getting hungry they decided to go to one of the local hangouts and get something to eat. One, there wasn't enough for all the others in what they had packed and Two, possibly they could escape the crowd and be alone. However nothing would do but all the others decided to go also and even when Charlie tried to lose them to go someplace else they were followed. Finally the two of them accepted the fact that their friends were determined that they would not consummate their desires that day so they gave up trying.

That night after taking her home Charlie called her and in very explicit detail he told her what he wanted to do to her. If nothing else they could have phone sex!

The next two days they couldn't get together due to schedule conflicts. Allison had to work and Mother dearest had things planned for Charlie. Finally on Thursday they were both free and decided to go on the interrupted picnic. THIS time however they wouldn't go to the lake. Allison knew of a nice quiet place not too far away where they could go, that would be private and they could BOTH fulfill their heart's desires.

An hour after he was supposed to be there to pick her up Charlie finally called to let her know that the date would have to be cancelled as someone had stolen his car while he was stopped for some ice and drinks. His wallet and clothes had been in the car, all he had with him was his credit card and it had taken a while before he could get the money to call the police and then her.

It was as if some higher power did NOT want her to lose her virginity! All her plans had come to nought.

Saturday she had to work mornings at the florist but was only scheduled until two pm. Charlie would meet her at the shop and they would leave from there on their date. THIS time things would be different.

Friday night she spent in the kitchen. She boiled eggs for deviled eggs, boiled potatoes to make into a potato salad, she cut up all the other ingredients for the salad, she battered and fried chicken and made biscuits. She had it all done, wrapped and in the fridge when she went upstairs and took a long leisurely bath with lots of bubbles and bath oils.

Coming back downstairs for a coke she was aghast! Her inconsiderate brother and three of his asshole buddies were sitting at the table eating her picnic! Taking a pan of cold water she upended it on his head and then began to whale away at the others with the pan.

"That was for my picnic tomorrow, you insensitive, unthinking louts! GET OUT! If I see you again tonight I'll probably kill each one of you. I just spent all evening fixing that for ME and you ass holes come in and just help yourselves," she screamed.

Knowing better than to stay all four of them fled the house. Slamming the door behind them while she sat down at the table and bawled. She was still there when her parents came in a few minutes later. Her Mother came inside highly incensed and demanded to know what she had done to her brother. When Allison saw him back in the house she hit him with the pan and chased him back outside.

Grabbing her arm and stopping her from chasing her brother even farther Mr. McCleary told her, "Your Mother is talking to her. Now answer her!"

"You want to know? I'll tell you what's wrong, that asshole you call a son is what's wrong. He's too fucking busy to come home for supper and too goddamn cheap to buy something to eat. He and those cocksuckers he runs around with descended on this place like a swarm of locust and ate the picnic I spend all evening fixing for me and my date tomorrow. And now the son-of-a-bitch is complaining? I'll kill him if he comes back in here!"

"Clean up your mouth young lady, THIS INSTANT! Ted, get in here. Did you eat her picnic?"

"How was I supposed to know? We were hungry," he whined.

"It was in the fridge, wrapped in foil you imbecilic bastard. Even as dumb as YOU are you know better than that!" screamed Allison.

"Allison, that's enough! Ted, Twenty dollars! NOW! You will PAY your sister for the food that you and your friends ate."

"Dad, I only have twenty dollars and I need it for a date tomorrow."

"Your sister needed all that food you and your friends ate for a date also. You didn't care about what SHE wanted or needed so PAY HER NOW!"

"I know it's not the same Punkin but you can stop at KFC and get what you need. Ted is paying for it," he said, handing her the twenty her brother had just given him.

The next day she and Charlie stopped at the KFC near the Florist shop where she worked. They got the chicken and all the fixings as she bemoaned the doings of her younger brother and his idiot friends. As they started out of town for their picnic they picked up a tail. Her brother and his three idiot friends.

Every time they tried to lose them the annoying foursome followed. Turn after turn, time after time until finally they drove back into town and had a picnic on Allison's front lawn. Her smirking brother and his asshole friends thought that was very funny and from time to time they still tried to pester them. having enough Allison excused herself from Charlie. She told him to NOT let any of them touch anything there. Some time later she returned and sat with Charlie to continue their picnic. The boys only left when the McClearys returned from shopping.

That evening the three of them were finishing off the left over chicken when Ted returned from where ever he had been. As he approached the table and began to look over what was left Allison pulled a large butcher knife from her lap and smiled at him.

"Go ahead and reach for something you son-of-a-bitch. You will never use that hand again!"

"Allison, what is the meaning of this!" shouted Mr. McCleary.

"Asshole here is oh too busy to work, he has to scrounge off you but he and those hoodlums he runs with aren't too busy to spoil my date. When Charlie picked me up at work they followed us everywhere we went. Finally we had our picnic on the front lawn while these inconsiderate, illiterate rejects stood around and carped at us. And NOW he wants some of the chicken. BULLSHIT! I'll cut his fucking hand off before I'll let him do more than smell it!"

"Allison, I TOLD you to clean up your mouth. Ted, give me your car keys. If you can't be responsible with that car then you can't drive it."

"Hey, SHE ruined my date, it was only turn about!"

"NO, YOU ruined your date when you ate the picnic you KNEW she had fixed special for today. Now GIVE me those keys!"

Slamming the keys down he stormed off to his room.

"This will stop, do you hear me, STOP!"

"Dad, I haven't done anything. I fixed the picnic and HE and those retards he runs with ruined it. We bought KFC like YOU said with money YOU gave me and HE and his retards ruined that as well on top of pestering us when we came back here and we tried to have a quiet picnic on our own front lawn. I paid for this food and I'll say who eats it and HE won't!"

"Maybe when you leave for school next month we can get some peace in this house. Four hundred miles should be enough distance to quiet things down."

Later that night Allison called Charlie and reported what had happened. "Ted's been grounded for a while. He lost his car and none of his friends have one. Can we POSSIBLY get away for a while tomorrow? We could go SOMEwhere."

Early afternoon Sunday Charlie pulled into the driveway in one of the family cars. Allison was waiting for him on the front porch when he pulled in. Before he could even get out of the car she had the passenger door open and was getting.

"Let's go Lover, we need to get out of here."

"Take us somewhere private," she continued as he pulled out of the yard. "Someplace we can be alone and away from everyone." Charlie's only response was a very large grin.

A few turns later they were on a secondary road leading into the countryside. Too excited to wait Allison slid across the seat closer to him and began to rub her hand up and down his leg. Charlie was getting excited also which became very evident from the large tent he had in the front of his trousers. With a mischievous grin on her face she slowly unzipped his pants and slowly moved her hand inside to free his rampart manhood. Finally free of any obstacle she leaned closer and gently blew her warm breath across the head.

Not able to take anymore Charlie placed one hand on the back of her head and gently pressed downward. Paying more attention to what she was doing than to his driving he didn't notice that the road slowly turned to the left. Just as her lips were passing the head of his cock the vehicle ran into a large washed out place on the side of the road.

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Story tagged with:
Teenagers / Romantic / Humor / Petting / School /