Terris Awakening

By Brenda Chaplin

Published on May 9, 2012

Transgender

Terri awoke early the next morning from a restless sleep. The anticipation of today's events kept her awake most of the night. She wrapped her silk robe on over her lace nightie and head to the kitchen for breakfast and coffee. After a light breakfast of egg and toast she call Denise for some advice.

Denise was very excited that Terri would soon be a full woman with the pending loss of her t-girl virginity. She told Terri to just relax and accept his cock when the time came and also to give herself a good enema to make sure her pussy was nice and clean.

She then hit the shower and gave herself a full body shave. When she was clean and smooth she dried herself off and wearing just her robe made another coffee. The door rang and she answered it. A UPS deliveryman handed her another package, which she signed for. The delivery guy gave a strange unsure look as he walked away.

In the box was a single red rose and a traditional school satchel. The bag was filled with the every day equipment a schoolgirl would need including trashy pop music mags. There was another note from Kevin instructing her that she had to be ready and dressed by 2.30, and pack an over night bag. She looked up at the clock and saw it was a little after 9am. She would have to get a move on to get all she had planed to do for today.

Terri got dressed in some skinny jeans and a t-shirt. Pulled her hair into a pony tail and added some light make up. She was amazed how well she could pass for a real woman. She grabbed her hand back putting some cash; phone and spare make up and head out to her car. Her nosey neighbour was out in her garden and Terri smiled and gave her a wink. The old woman just looked away embarrassed.

Terri got into her little Ford Ka and drove to the local parade of shops. Parking up and locking her car she headed to the chemist for some supplies.

She chooses some Durex love lube and a self-enema kit as well as some mail polish. Usually buying such items made her nervous and embarrassed but after the last few days Terri was out to the world and she could not careless what people thought. She popped in to the supermarket and got the latest hello magazine and a couple of bottles of wine. She headed back to her car noticed a middle aged man staring at her with I want to fuck you eyes she giggled to herself an deliberately dropped her car keys and turn and bent over giving the guy a perfect view of her arse in cased in the skin tight denim. So tight the out line of her thong could be seen. She stood back up and opened the car door just before she go in she turned and made eye contact with the guy and winked at him. With a smile on her face she drove home.

She spent the next 4 hours doing her work. She had to remember to lower the tone of her voice when she called colleagues back in her office. After she had completed enough work she glanced up at the clock it was 1pm. She sent her work to the office and logged off. One and half hours to the big date with Kevin.

She headed to her room pulled out a small suitcase and filled in with her nightie, toiletries and well as clean underwear and outfit.

She took the box he sent yesterday and. Laid out the items in it. Short grey pleated skirt, white button collared blouse, grey pullover, blue girls blazer with the schools breast patch and navy blue tie with silver stripes. She took some hangers and hung the uniform up. She laid a towel over her bed and went to the kitchen to boil the kettle. She took a jug and put the enema kit in it. When the Kettle boiled she made herself a coffee and poured the rest into the jug to warm the enema. She took both back to her room. She stripped naked and sat on the bed She sipped the coffee as she knelt on the bed. Taken the warmed enema she bent over sticking the lubed tip up her pussy squeezing the warm liquid deep inside her. A satisfied smile spread across her face as the warm liquid ran into her bowels. With the bottle empty she pulled it out and clenched her pussy lips tight together.

Gingerly she got of the bed and head in to the bathroom. She started to run a bath and sat in the loo waiting for the 10 minutes the enema needed to work to be over. Preoccupying herself with running to bath to quash the desire to push the liquid out. All to soon the 10 minutes was up and she relaxed her arse and evacuated the enema liquid and all the shit up there. She giggled as she was making some very unladylike noise. Satisfied her bowls were clean she sank herself into the warm bath and soak for a while breathing on the aroma of the bath products she put in to soften her skin. She grabbed her razor and removed any signs of hair. She washed and conditioned her hair to give it volume and bounce.

She stepped from the bath wrapping a towel around her midriff and head to her room to get ready for her third date with Kevin. She turned on her hit rollers and popped to the kitchen for a large glass of red wine.

Back in her room she drew the curtains to block late afternoon summer sunshine. Lit a couple of candles put on her soppy love song CD and pulled her box of toys out from under her bed. She picked a 6-inch butt plug with rotating tip. Applied a modest amount of lobe to her finger pulled off the towel and started to work the finger into her pussy. Her cock instantly grew but she willed herself not to touch it. A minute or two later with 3 fingers burred to the hand on her pussy she pulled them out added some lube to the plugs tip and easily accepted the whole length into her pussy she wiped her hands with the towel and using the wired control to her anal invader turn on the plug setting it to a random cycle. She felt the tip start up and turn and pulse sending shivers up her spine. She ached her back closing her eyes as her prostate was stimulated. She sipped her wine as the plug prepared her for the real organic invader that would flood her pussy with hot man seed later.

She turned the plug to its minimum setting in order to allow her to get off the bed. Placed her wine on her dresser and slipped on her silk robe. She sat down and started to brush her hair out and started to take her hot roller and started to put them into her hair. With the last one in place she took a face wipe and cleaned her face. She stopped briefly as the butt plug sent a shiver through her. Re composing herself she took her foundation make up and applied it. She applied her eye make up like Eva Green giving her blue eyes dark frames. A light blush to enhance her cheek bones and some light lipstick to add some gloss to them.

With her make up complete she took off her robe and stuck her breast forms in place and took the white lacy bra Kevin had sent on. She took the crisp new school blouse of its hanger and put it on. She buttoned it up from the bottom leaving the top 3 buttons open. She took one of her gold necklaces with a little love heart pendant and put it around her neck fastening the clasp. She put a gold stud into each ear, couple of rings on her fingers.

She pulled up her cuffs exposing her wrists and sprayed a little Tommy Hillfinger's Tommy girl perfume on them and rubbed them together. She followed this up with a little spray around her neck and breasts though the opening in the blouse. Taking another sip of wine she walked back to her bed and knelt with her legs apart, she reluctantly pulled the plug from her pussy and gave her hole a quick wipe to capture any loose lube that ran out of her hole. Wiping the butt plug she put it back in her toy box and pushed it back under her bed. She took the knee-high socks that was sent with her outfit and put them on, followed by the virgin white panties. Next she stepped in and pulled the grey box pleat skirt up to her waist and tugged the blouse under the waistband. She took the 2" black leather pumps and slipped them on her feet. Sitting back down she took the hot rollers out and clipped the back of her hair in the middle letting cascade down her neck leaving the two curly bangs framing her face. Picking up her gold DKNY watch and fixed it to her left wrist and a gold bracelet to her right wrist.

She lifted the collar and pulled the blue and silver striped tie around her neck. Buttoning the remaining buttons to her collar as well as the two cuffs. She evened out the tie and tied it with a full Windsor knot. She pulled the knot into a perfect centre position under the collar covering all the buttons, falling just on the waistband of the skirt. She pulled the collar down and straightened it out. Taking grey v necked pull she pulled it on pulling her blouse cuffs down so they popped out below the cuffs of her pullover. Checking the mirror the pullover had pulled her tie down showing her top button. She quickly pulled the knot tighter and was happy it was perfect again. Last she put on her blue blazer and checked herself in the full-length mirror. Perfect she thought.

She picked up the make she had used and put inside her satchel as well as her phone and a small purse with some cash in. Just in case things go sour she said and I need to get myself home.

Checking her watch it was 2pm, 30 minutes to go. She took her back and wine and headed to living room sat down and finished off her wine, reading her new magazines.

At 6 sharp there was a knock on the door. A final check in the mirror by the front door, this is it she thought and struck a sexy as she could muster pose and opened the door. To her surprise and embarrassment it was not Kevin standing there. A tall man in a black suit and peak cap stood there. Looking past his shoulder she saw a stretched limo. The chauffeur introduced himself as Greg and would be her driver this evening.

She was surprised that he did not seem surprised to see a woman dressed a schoolgirl.

She asked for a minute fished her lipstick out and freshened it up in the hall mirror. Grabbed her keys and locked the door. Taking Greg's arm she was led to the car where he opened the rear door open for her as she slipped into the back seat. Greg closed the door and got into the driver seat, started the engine and pulled away from Terri's house. On the seat next to her were a dozen red roses and an open bottle of champagne on ice with a glass pre-poured for her. Greg said Mr Harris would be waiting for her at the school disco. Nice cover Terri thought, that would explain the lack of surprise about her outfit. He also said that they had a couple of hours drive ahead of them and to make full use of the cars facilities.

Terri wandered where she was going and Greg had instructions not to tell her.

The trip took a little over 3hours to get to west London from Chorlton. Terri had finished the champagne an hour into the trip and had fallen asleep on the wide leather seat. As the M40 turned into the A40 Greg opened the privacy shield and gentle called to wake Terri up. Terri awoke and looked out the window, the buildings that went by were all familiar. This is where she had grown up, it all seemed like a lifetime ago.

The limo turned off at the Greenford turn and headed towards the high street. Terri now knew that her destination must be her old school. She slipped her blazer back on rechecked her make up and hair. The Car passed the high street junction and she saw the familiar buildings coming up on the left.

The limo pulled into the school grounds, drove through the car pack to a side access gate behind the main building and pulled up next to an access door leading to the playground. Greg stepped out of the car and opened the door and held a hand out for Terri. Terri stepped from the limo and looked around the playground she spent 5 years of her life playing on.

Gregg opened the side door leading on to the corridor and told Terri that he would take her bag on to the hotel and that she was to head for room 17.

Terri thanked him and throw her satchel over her shoulder and walked down the corridor. There were plenty of butterflies in her belly as she traced the steps of her youth. All too soon she was standing outside classroom 17. Taking a deep breath she reached out and opened the door. Blowing the breath out she stepped through the door.

The sight that greeted her instantly transported her back to being 16 years old. Sat at a front desk Kevin sat dressed in his school uniform. Unlike Terri's Kevin's was not regulation. He wore trainers instead of black shoes, he had no pullover, his blazer sleeves were rolled up and his collar was open and his tie was loose around his neck.

She closed the door and smiled at him. She said she was impressed that he managed to set all this up. Kevin winked and said money talks.

Terri stood there for a monument as Kevin rose from his seat soon they were face to face an Kevin leaned in and kissed her he whispered in her ear that he is looking forward to for filling her fantasy. He took a step back and to all of Terri in. God if you dressed like this back then you would have been the most beautiful girl in school. Terri closed the gap and whispered in his ear that he deserved a reward for making all this come true. Her right hand slipped over the front of the crouch of Kevin's grey school trousers. His cock was already semi hard as her lips meet his. Their tongues danced together as she massaged his rock hard cock. Slowly she eased away and pushed Kevin to sit on the edge of his desk. She soon had his belt and trousers open and pulled his cock out. Dropping down on one knee she licked the head of his member gentle nibbled down it length sucking each hairy ball sack into her mouth. Kevin closed his eyes as she worked back up shaft and took all 8 inches into her throat. She swallowed him whole for a few seconds before pulling out to the head again holding him there before another quick deep thrust in to her moist mouth. Kevin started to pant and call her a uniformed cock sucking goddess who will soon have her pussy pounded. Terri picked up her pace and massaged his balls whilst the other hand found his ass hole. She soon had her index finger deep within him. The head if his cock was start to grow in her mouth and she new her reward was coming soon. Kevin heaved the sides of her head and thrust his cock down her throat as he screamed and let loose 6 hot streak of spunk down her eager throat. She swirled her tongue around the shaft and head as he slowly pulled his spent organ from her mouth.

Licking her lips she stood and grabs Kevin's head and pulls him into a kiss there she snowballs some of his seed. Breaking the kiss Kevin turns Terri around making her spread her hands on the desk. He eases her legs apart and lifts her short school skirt revealing her panties. Terri felt the warmth of his mouth through the thin lace of her panties as he kissed her pussy. With his hands he cupped and stroked her arse cheek as he licked her panty cover hole.

As he assaulted her womanhood. She took in the surroundings. The class where she had her English classes not so different in the years that had past. Her outfit the look of a prim schoolgirl with her tight collar, perfectly knotted tie. She lowered her head and felt the tie cares her chin. Looking over her shoulder she saw her dream boy from all those years ago on his knees eating her pussy. Kevin pulled her panty to the side and stuck his tongue into her. She immediately lost all train of thought as ecstasy overtook her. Kevin work a couple of fingers in her. Soon he felt she was ready. He stood up and slid her panties down. Leaning over her kissed her neck and collar. He whispered if she was ready to become a really women. She simple said take me. His recovered cock was oozing pre cum. He rubbed it up and down her slit then he started to push in. Soon the head had past her entrance and she purred as he pushed the whole way into her. He continued to kiss her neck and telling how good she feels and how sexy a schoolgirl she made. He started to pull out and push in with small strokes taking his time to build up his rhythm. Terri felt as if his cock was like a train leaving station and knew he would be up to full speed.

Kevin's pace soon quickened and could only be described as a good hard fucking. Kevin reached around and found Terri's throbbing cock, his gentle touch turned Terri into a quivering moan mass as he pump her cock in time to his own thrusts. Terri urged him to fucker her hard and fill her up with his love seed. Kevin did not need any further encouragement he was already feeling his own orgasm building and put in one last spurt of speed. Terri panted then gave out an almighty cry as her cock exploded over Kevin's hand and the classroom floor. This caused her arse to tighten and thus sent Kevin over the edge firing his load into her hot arse. Terri felt the warmth spread through her bowel. Kevin brought his hand to her lips as she licked them clean. He turned her around and they kissed as lovers. The kissed and rub each other for a while before Terri again took his cock into her mouth. Soon it was back to attention. She stood up lead Kevin to a chair and positioned herself over his pole. Slowly she lowered herself onto him. When she was sat in his lap she started to bounce up and down his shaft in this position they faced each other. Kevin unbuttoned her blazer and found her breast cupping them as she rode him. As the feeling grew so did her pace. Kevin grunted and dumped another load in her as she fired her juice over Kevin's shirt and tie without any of them touching her cock.

They sat there for a moment to get their breaths back. What a sight they made should someone walk by. Two school kids fucking in a classroom.

Kevin looked up at the clock and told Terri they had to out in 10 minutes. Terri slid off Kevin's spent shaft and retrieved her panties. Kevin pulled up his trousers and wiped Terri's cum off the floor. He buttoned his blazer to hide the stains and took Terri's hand and led her back down the corridor to the side entrance. Greg was waiting with the limo. Kevin asked him take them to hotel. The car pulled around the front of the school and stopped briefly for Kevin's to lower his tinted window and passed a white envelop with new £20 notes stuffed in it to the school caretaker. The car pulled back out on to main road heading back to the A40. Kevin cuddled Terri and asked does this mean we are boyfriend girlfriend now. Terri purred that she would not want it another way. And nestled close to him.

By Brenda Chaplin

Want more, then let me know.

Brendachaplin2000@yahoo.co.uk

Next: Chapter 5


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