The Awakening of Jennifer Pt. 03

(The reader is advised to read Parts 1 &2 first.)

Jennifer was determined to lose her virginity before the end of the summer holidays, but in the week after she spied on Henry and Peggy in the shack, no opportunities arose. Each night, vivid images of Henry brandishing his impressive cock would torment her mind, and she would slip a hand between her legs and try and make herself come. But try as hard as she might, orgasm always eluded her, and eventually, Jennifer decided that perhaps her fingers alone were inadequate for the task.

On the three occasions when she had successful masturbated to orgasm, there had been a specific event that had inflamed her, and consequently, orgasm had come easily. She had watched Henry make himself come; she had caused Toby's premature ejaculation in her hand, and of course, the pièce de résistance, she had spied on Henry giving Peggy 'a right royal seeing-to'. Jennifer suspected that her imagination needed fuel in order to ignite - perhaps she was easily jaded and needed new experiences?

One afternoon her mother asked Jennifer if she would pop down to the kitchen and give Aggie, the chief cook, some additional instructions for their dinner that night. Jennifer was a dutiful girl and readily obliged. When she got to the kitchen, she gave Aggie the orders, and was about to leave when she noticed a basket on the floor, containing several cucumbers. Something about their shape stirred memories, and an image of Henry popped into her mind. Jennifer realised that the cucumbers were of a very similar size to Henry's erect cock!

She thought she felt herself blushing, and was about to leave, when Aggie went into the pantry to get additional ingredients for the dinner. Jennifer quickly selected a fine-looking cucumber, and rapidly made a swift exit from the kitchen. She was wearing long ruffled sleeves, and once out of the kitchen Jennifer hid the cucumber up her sleeve and took it to her bedroom.

Her heart was beating wildly. She had acted on pure impulse, and had not really thought about what she intended to do with the cucumber. Jennifer took it from her sleeve and studied it. In length and width, it seemed a perfect match for Henry's manhood. She wrapped her fingers around it, and her middle finger and thumb could only just meet. Jennifer had never had the good fortune to touch Henry, but she judged it to be about right. She knew that the span of her hand was eight inches, and had estimated Henry to be of similar length - the cucumber was longer, at least ten or eleven inches. Jennifer felt quite dizzy with anticipation.

"Do I really intend to do this?" she thought. The cucumber was very smooth, with no little bumps or rough bits that might cause her injury. Jennifer moved her hand up and down it, just as she had done with Toby's diminutive member, and as she had observed Peggy working her hand on Henry. It seemed perfect - but it would have to wait. Jennifer secreted the cucumber at the back of a drawer - she would try it out that night when her parents were fast asleep.

In the evening, Jennifer and her parents sat down for their dinner. The first course was a simple chicken soup, and then they were served a small dish which made Jennifer almost laugh out loud. There were sliced rings of cucumber, covered in avocado, and topped with a small shrimp. Jennifer found it highly amusing when she thought of what she had stolen from the kitchen, and how she intended to use it!

Her parents seldom stayed up late, and Jennifer was pleased when shortly after nine pm they retired to bed. Her father kissed her on the forehead.

"Sweet dreams, Jen," he said. If only he knew what wicked things Jennifer tended to dream about...

When Jennifer went up to her room, she made sure that she locked her door. It was a huge house, and her bedroom was some distance from her parents' room. They rarely stirred after they had retired, but she did not want to take any chances.

Jennifer stripped off all her clothes and stood in front of the wardrobe mirror. She thought of Peggy's womanly curves. Peggy had a fine pair of full, round breasts - Jennifer's were much smaller. Although her breasts were exceedingly perky and needed no support, Jennifer wore an A-cup bra. She was rather concerned that Toby had not seemed particularly excited when she coaxed him into fondling her breasts - were they too small?

Jennifer turned to the side and looked at her breasts in profile. Despite their smallness, she liked what she saw. The tips were prominent, and the areolae, (a term she only learned much later), were swollen and protruded proudly from the hemispheres of her breasts. Followers of erotica on the Internet today would call them 'puffy nipples'. Jennifer's nipples were nowhere near the size of Peggy's large teats, but seemed in good proportion, approaching half an inch in length and as wide as the tip of her little finger.

Jennifer had noticed that many of the girls at her school had nipples that were barely raised over the areola, which puzzled her - how would a baby suck on those?

She touched her nipples gently, and marvelled at how sensitive they were. They hardened instantly, which served to make them even more sensitive. Jennifer wet her fingers with spit, and touched her nipples again. The slipperiness of the spit greatly enhanced the sensation, and as Jennifer watched herself in the mirror, she became aware that there seemed to be a direct link between her nipples and her pussy. Each time she elicited a delicious thrill in her nipples, she would almost immediately feel a little contraction in the muscles deep in her pelvis, the ones that came into play when she tried to start or stop peeing. After only a few minutes of nipple play, Jennifer felt that her pussy was starting to get wet.

She recalled watching Peggy in the throes of passion - Peggy had pulled and squeezed her nipples quite violently before she came? There must surely be a link?

If her spit made her nipples feel good, what would the slippery juice from her pussy be like? Jennifer reached down and wiped her finger a few times between her pussy lips. They were, as she had suspected, very wet. She transferred the moisture to her nipples and found the experiment to be a success - the slippery juice made her nipples feel wonderful, and produced a corresponding surge of tingles in her pussy.

Still watching herself in the mirror, Jennifer liberally coated a finger with pussy juice, lifted it to her mouth, and sucked. She had tried this once before and had felt shocked that she could do such a thing, but Jennifer was now much more liberated - she had decided that if anything could increase her sexual pleasure - she was prepared to give it a try.

The taste excited her - there was both sweetness and saltiness, and a hint of tangy citrus. She stood for a moment, applying pussy juice alternatively to her nipples and her mouth. The more she did it, the more liberally her juices flowed - she could feel a trickle running down her left leg.

"Dear God," she thought, "could I make myself come just by doing this?"

Jennifer remembered the object at the back of her drawer. She checked again that her door was securely locked, and retrieved the cucumber from its hiding place. She wrapped her hand around it feeling dizzy with excitement. It was thicker than her two fingers, and much thicker than the single finger that Toby had clumsily inserted into her, but it appeared to be the equal of Henry - an image of his erect cock formed in her mind.

"Yes," she thought, an excellent match."

Jennifer lay on the bed and positioned herself so she could see her reflection in the wardrobe mirror, and spread her legs. She parted her pussy lips as she had seen Peggy part hers to prepare for Henry, and nestled the tip of the phallic vegetable between them. She moved it to-and-fro, wetting the surface with her juice, and with a wildly beating heart, Jennifer pushed.

"I can't do it, it's too big!" she thought, but she persevered, took a deep breath, and pushed again. The mouth of her pussy yielded, and Jennifer felt the cucumber gaining entrance. She pushed again and added a to-and-fro twisting motion.

"Oh yes, it's going in!" Her excitement mounted as by little increments progress was made, but soon Jennifer found that she could go no further - the cucumber seemed to be stuck, and she had not yet got to its widest part. She explored with a fingertip - and decided that as slippery as her natural juices were, they were not enough to lubricate the cucumber.

Jennifer was a resourceful girl, and got off the bed, went to her dressing table, and took a jar of Dior Prestige hand lotion back to her bed. She smeared a liberal amount of the cream over the end of the cucumber and tried again.

Jennifer let out a little squeal - the cream was cold at first and a bit of a shock when it first touched her pussy. She positioned the cucumber against her entrance and tried again.

The cream proved to be an excellent idea and the tip of the cucumber slid more easily than before. After a few tentative thrusts, Jennifer grew bolder and pushed harder.

Success - she studied the image in the mirror with fascination - the cucumber was going in! Her pussy was now stretched so wide that Jennifer felt some sharp stabs of pain, but not enough to deter her. She paused and took her hand from the cucumber - it stayed where it was, and she looked in the mirror at the green shaft sticking out of her pussy. It looked like she possessed a huge green cock. The sight was quite obscene, but also very exciting!

Jennifer pulled the cucumber out and examined it - the cream had been pushed at least three inches up the cucumber and the widest part had definitely been inside her.

"I can do it!" She was delighted, and smeared some more cream further up the shaft.

Jennifer tried again and this time the vegetable dildo slid in much more easily. She lay back on the bed, and as she pushed and rotated the cucumber she touched her nipples, pinching quite hard, and twisting them. She imagined Henry between her legs, moving his huge cock in and out, and felt her pussy respond. What had initially been an uncomfortable and slightly painful insertion was slowly being replaced with pure pleasure. The novel sensation of a large object in her pussy, stretching her wide, was feeling amazingly good, and Jennifer began to thrust the cucumber in and out with short strokes of an inch or so. The cucumber slid more easily with every thrust.

Jennifer moved up the bed and propped a pillow by the headboard and leaned against it. She tilted her pelvis upwards to afford a good view of her pussy and her clitoris. As she plunged the cucumber in and out, it tugged on her lips with each withdrawal, and her lips in turn pulled on the folds over her clitoris - it felt wonderful!

Jennifer touched her clitoris with a finger, and the touch was electric - a cascade of tingles radiated outwards. She moved the dildo faster - and deeper. All discomfort was gone - there was now only pleasure, which grew and grew. What had Peggy said?

"Fuck me, Henry Parker - fuck me with your big hard cock!"

Jennifer leaned back and closed her eyes, thrusting the cucumber faster and faster. It was no longer a cucumber - it was Henry's cock!

"Fuck me," she whispered to herself, "fuck me! Oh, God!"

Saying it out loud made her pussy throb with sensation. Jennifer grew bolder.

"Fuck me!" she gasped, trembling in excitement, "fuck me, fuck my pussy, fuck me hard - make me come!"

Her fingertip vibrated faster on her clitoris as the cucumber thrust in and out, whipping the mixture of the cream she had smeared on it and her juices into a froth. Many of her masturbation attempts had been failures - orgasm almost came but then faded away. This was different - carnal images flooded her mind - Henry's huge cock stabbing into Peggy's writhing body, Toby's hard little cock in her grasp, throbbing and dribbling semen over her hand - and the ultimate glorious sight of Henry spurting endless torrents of pearly white over Peggy's stomach and her beautiful breasts.

This orgasm certainly did not frustrate her - the ecstasy grew and grew, rising to unbelievable heights. Jennifer threw her head back and let out a long trembling wail, as her pussy clamped down on the cucumber in a powerful spasm. She relinquished her grasp on the dildo and her hands went to her breasts, squeezing her nipples to the point of pain, as wave after wave surged through her loins.

The cucumber was in grave danger of being expelled by her pussy's rhythmic contractions - Jennifer closed her thighs, trapping the cucumber inside her, and toppled over onto her side, gasping for air. The intensity of the orgasm stunned her. The others had been wonderful, but this one was on another level - she felt powerless as if the orgasm was ripping her soul out of her through her convulsing pussy.

Jennifer lay still for several minutes until her mind cleared, and then she slowly sat back up and opened her legs. She reached for the cucumber and removed it, and examined the creamy froth. It had been pushed a good six inches from the tip! Jennifer was thrilled with her achievement - it may not equal the length of cock that she had seen enter Peggy, but Jennifer was now confident she could accommodate a cock considerably bigger than Toby's.

She felt her pussy. The lips were puffy and engorged, but she could detect no damage. Jennifer nervously inserted her fingers into her pussy - did the opening feel any wider? Had she stretched herself? There was no discernible change, which puzzled her. She had always believed that virgins would suffer considerable pain and bleed profusely when first penetrated, but the cucumber was a splendid specimen, and yet there was no blood at all!

"Another mystery about sex", she thought, wiping the cucumber with a tissue.

It went back in her drawer - perhaps it would be good for another time?

A few days later, Julia Edmonstone came to visit. Julia was a year older than Jennifer, and had been in the year above her at school. They had been in the hockey team together and become good friends. Jennifer was always a bit in awe of Julia because she was so sophisticated. Julia was a tall brunette, with long tresses, often worn in ringlets that cascaded over her shoulders. Her skin was very pale, and she could easily have modelled for one of the Old Masters, such as Gainsborough or Rubens. Jennifer knew that Julia was an experienced girl - she had been seen with a succession of boyfriends, and although at school Jennifer had not shown much interest in boys, she definitely did now. Jennifer was eager to ask questions.

Jennifer sat waiting in her bedroom, looking out over the driveway, and shortly before lunchtime Julia swept up the drive in her nifty little pink Karmann Ghia. That was another thing that Jennifer envied. She kept pestering her father to get her a car, but Charles Wyndham-Brent was worried that his only daughter would kill herself in a car - Jennifer was not mechanically minded, and a few attempts to teach her to drive had almost given her father a stroke.

Julia ran down excitedly to meet her friend.

"Darling!" Julia exclaimed and gave her a kiss on the cheek, "how have you been, I haven't seen you in ages?"

Julia looked as elegant as ever. She wore a pale blue two-piece dress, the first layer was sleeveless, and the second was a lacy 'over the shoulder' affair. She sported a very fine Gucci handbag and could easily have graced the cover of Vogue.

Jennifer felt rather underdressed; she just wore a simple blouse and skirt. As usual, Julia had taken the upper hand.

There was little time for the girls to catch up, because lunch was served. Jennifer's father rather fancied Julia and hogged much of the conversation. He was a bit more generous than usual with the wine and regularly topped up Julia's glass, and of course, had to do the same for his daughter.

As a result, Jennifer felt rather tipsy. She was not used to drinking, as her father had been strict - no alcohol before her eighteenth birthday. Julia on the other hand looked as if she could handle several bottles all by herself.

After lunch Jennifer's parents announced that they were going to go shopping - there was an auction they wanted to attend and had their eyes on some rather fine antique furniture.

"Sorry to be so rude and rush off, Julia," Charles said, "it was lovely seeing you again."

Jennifer and Julia took a walk around the gardens. Julia was living a fine life. She had finished her first year at university, studying medicine, and had lots to tell Jennifer, to prepare her for when she started at Oxford in a couple of months.

They sat on a bench overlooking the ornamental pond, watching the fountain and the Koi carp swimming in lazy circles.

"Jules," said, Jennifer, "university sounds very exciting, but one thing worries me."

"I am sure there is nothing to worry about," replied Julia, "but do go on, what is it?"

"Well, I am not very experienced with boys. I have never had a boyfriend, and I fear I will be rather out of my depth. Those parties you talk about seem - they sound rather wild."

"Don't be silly," Julia said, "you don't have to do anything that you don't want to. If boys try and pressure you into sex, just say no. Go at your own speed."

"That's the thing," Jennifer said, "I am actually quite keen to... get more... experienced."

Julia laughed.

"Well, you shouldn't have any problem there. You are so pretty that any boy would love to go out with you. A lot of girls will, as well - be prepared for that too!"

Jennifer was taken aback.

"Really, girls? Oh my..."

She pondered the idea for a while. Jennifer was just getting used to the idea of sex with boys - the idea of sex with girls was something she had heard about spoken only in hushed whispers.

She studied how beautiful Julia looked - girls must surely have made advances to her.

"Jules," she asked, "have girls pursued you?"

"Oh yes," Julia replied, "and I've pursued a few of them myself."

Jennifer could scarcely believe her ears.

"But, but, you have had boyfriends - we all saw you with boys, many times," she exclaimed.

Julia put a hand on Jennifer's cheek.

"You dear girl," she cooed," you have SO much to learn. You can have fun with both boys AND girls. Nobody takes any notice these days."

Jennifer thought of her time spying on Henry and Peggy. Seeing Peggy naked had indeed been very exciting, and Jennifer had wondered at the time why she had felt so aroused. Looking at Peggy's womanly breasts, and the dark hair surmounting her pussy had enthralled her, and she had definitely felt a corresponding thrill in her pussy. My goodness - maybe it was true - was there a whole other world to be explored?

"Jules," she asked, "what is it like, with a girl? What... I mean... what do you DO?"

By way of reply, Julia smiled, leaned towards her and gave her a soft kiss on the lips. Jennifer was startled but did not pull away. The touch of Julia's soft lips on hers felt lovely, and Jennifer could smell Julia's intoxicating perfume, no doubt it was a far more expensive brand than Chanel N°5!

Julia touched Jennifer's cheek again, and the touch was gentle and lingered. Julia leaned forward again and her mouth met Jennifer's and stayed there. Jennifer felt her heart beating wildly. Oh my God - what was happening!

Julia's hand slipped behind Jennifer's neck, gently stroking, but also holding the girl captive, and the kiss deepened. Julia parted her lips and Jennifer responded by doing the same. Jennifer felt the tip of Julia's tongue slide over her lips - it was warm, wet and sensual, and felt breathlessly exciting. Jennifer closed her eyes in rapture as the kiss grew more passionate.

Suddenly her eyes flew open - Julia's hands were undoing the top button of Jennifer's blouse. She broke away.