Sarah's Story

by Rob Henson

 

Chapter 2 – Sarah and Ben

It was coming up to Easter when one evening in the coffee bar the group sometimes used, Ben turned to Simon and put a proposition to him. They had become good friends over the months going out together on occasion and visiting each others houses to listen to music or just chill out. They shared the same taste in music and video games which they played late into the night. The affinity was strong but never questioned or analysed. Both were mature enough to recognise that many allegiances were made and broken during teenage years and they were happy to simply enjoy each others company for a while sometimes with others and also on their own.

"My Sister is going away for the weekend with her husband and she asked me if I would stay there for a few days to look after the dogs. Fancy coming? We can relax for a day or two and have some fun," said Ben.

"Yes all right," replied Simon, "where does she live?"

"In Stratford, we can go across by train it's not far. They leave Friday morning and return on Monday night, so I though we could pack a few things and go over Friday afternoon and come back after lunch on Monday. Stratford's a great place with lots of good clubs if you know where to look."

Ben arrived at one o'clock the following Friday and they walked to the station. Each had packed a games machine, lots of games, CD's and videos as well as a few clothes. The journey took about twenty minutes and it was only a short walk to the house from the station. It was a large, nineteen thirties, detached house with its own drive and high hedges in a small close just off one of the many main roads into town near to the Stratford and Avon canal.

"Wow this looks grand" said Simon gazing up at the ivy covered walls looming high above him.

"Yea, Geoff's got a really good job, running some sort of computer agency in town. They are planning to start a family soon and they got this cheap when it came on the market for a quick sale."

Ben had a spare key and they went in. The dogs were in the conservatory where the door was shut. Ben liked the two terriers and they seemed to know him too especially when he made a fuss of them and gave them chocolate biscuits.

"We'll need to take them out for a walk a least twice a day but it's a nice town and not very big so we can go together," said Ben.

"Sounds good to me, where's the bedroom?"

"It's upstairs I'll show you," said Ben. He shut the conservatory door and the dogs settled down again.

"Here we are. Linda said we could use the spare rooms. You can have this one and I'll have the bigger of the two, the one with the double bed, since she is my sister." Ben smiled and went to his room to unpack his things. He returned a few minutes later and saw that Simon had just tipped everything on the bed and was about to put his clothes away.

"How about we rent a video tonight and get a pizza?" asked Ben, "what's the matter?"

Simon had opened one of the draws to put his clothes away and found it was full of Linda's underwear – panties, bras, tights and slips. He opened another draw and found that it was also full of her clothes.

"Look, am I in the right room, these seem to be full Linda's things?" Simon asked slightly alarmed.

"Yea, this is right, their room's is down the hall. She was always magpie at home, never threw anything away."

Ben went to the built in wardrobe and opened it. It was full of her older dresses, skirts coats and shoes as well as out of season outfits.

"I remember some of these things from when she was at home, she hasn't worn them for ages."

He pushed the hangers to one side holding out the dresses so Simon could see them. Simon eventually found an empty draw at the bottom of the chest and put his things away.

"Mmmm, that does give me an idea though," said Ben his eyes sparkling.

"What do you mean?" asked Simon nervously, curious to know what he might have planned.

"Don't worry. I'll tell you later, it will be fun you'll see," and they went downstairs to feed the dogs.

That evening they stayed up late playing computer games and watching TV. The next day was Saturday so they both slept in late. As the morning drew on they took the dogs out to the nearby common to give them their exercise.

"So what are we going to do tonight," said Simon as they sat down on the sofa with some coffee. Ben had prepared lunch and used the last of the food since Linda had almost emptied the fridge before she left. Ben sat down close to Simon so that there shoulders were touching.

"Well, I have an idea which I think you might like," said Ben, "How about we take the dogs about for a walk this evening only this time I take someone else?"

"I don't understand, what do you mean? Who are you going to take?" asked Simon puzzled.

"Well, my young friend, we could have some fun. How about if you got dressed up in Linda's clothes and we went out with you as my girlfriend. I have a feeling that you might like that, mmm?"

Simon turned to Ben alarmed.

"Dress in Linda's things? I don't know. What would she think and what if someone saw us? I'm not sure. If we got caught we'd be in real trouble," said Simon nervously.

"That's interesting, I notice you haven't objected to doing it though, am I right?"

Simon lowered his eyes and nodded. "Yes I think I would like to be your girlfriend," he said quietly after a long pause, "but I don't know if it would work."

Ben gently lifted his chin until their eyes met.

"Simon, I have had boyfriends as well as girlfriends but you have always been different. When I have been with you it always seemed like I was with a girl, or rather it feels like something in between. It's odd but its not like being gay at all. You could easily pass for a girl especially with your long hair. Why don't you get ready and we'll see how you look. Believe me I do not want to walk around town and feel embarrassed either so if I don't think it's going to work I'll tell you, in which case we can just stay in and have some fun here instead. What do you think?

"I suppose so, but do you think Linda will mind?" asked Simon.

"She won't ever know. I just told her I would be bringing a friend and I think she assumed it would be girl in any case. Besides everything you need will be in your room I'm sure. Like I said Linda never throws anything away. You won't need to go into her bedroom or use her things at all."

"Go on, you get ready while I go to the shops to get us some food for the week-end and I'll see you when I get back. I think this won't be your first time dressed either so I'm sure you'll look great. We'll decide what to do then."

Ben got up to check what was needed in the kitchen and Simon went upstairs to get ready. As he entered his bedroom the full realisation of their decision begun to dawn on him and his stomach turned over. He was thrilled at the opportunity that had arisen but extremely nervous at the same time. After all this would be the first time he had ever been out fully dressed including wearing make-up which he hoped he would find in the wardrobe.

First he ran the bath using more perfume salts than he should have but he really wanted to look and smell his best for Ben tonight. If he was going to do this it had to be perfect. He quickly got undressed and slipped in to the hot, steamy water thinking about what he might wear. Linda certainly has wonderful choice of clothes and they're just the ones she no longer wore he thought. He washed his body with the creamy soap and checked his legs which were smooth. He still had little body hair which seemed to be a family trait and certainly made life easier for him. He climbed out and wandered back to his bedroom and started to gather all the things he would need. In the draws he found a matching set of underwear but then had to decide between tights or stockings. He chose the tights in the end since he wanted to wear one of Linda's short dresses which he knew would show off his nice legs. He pulled up the pink, shinny nylon panties and tucked his cock into the gusset. He was very excited now and his breaths were coming quickly but his cock stayed soft which was good because he did not want to ruin the line of the dress.

He had noticed recently that he never played with himself as much as he used to in the early days when he got dressed. It still excited him sexually but he much preferred the feeling of tranquillity and comfort of 'being a girl' sometimes without masturbating at all. He began to wonder if this more than just a fetish and whether there were deeper changes occurring.

He found a pair of dark tan tights and pulled them over his arm like he had done hundreds of times before. He loved the feeling of pulling the soft smooth nylon up one leg and then the other. He pulled the waistband over his hips and checked himself in the large wall-mirror next to the wardrobe. He turned a few times and saw how shapely his legs looked and noticed how much better they would be in high heels. He put on the bra and used some of the stockings from the draw to give him a nice feminine shape. It wasn't perfect but good enough to pass he thought. He then went to explore the depths of the wardrobe and found an assortment of things he would love to wear. It then occurred to him that if this was successful and especially if Ben really liked what he had done, he might be able to stay as a girl the whole week-end since no one around here knew him in any case.

He also found a small case of make-up in the bottom of the cupboard and a box with some jewellery. It wasn't expensive but just simple things to go with the different costumes. This room was turning out to be a real treasure trove for him.

He found a short dress in pink with long sleeves and white cuffs which looked simple but sexy at the same time. He stepped in to it and pulled it up his legs feeling the nylon lining on his tights. He leaned back and pulled up the zipper and attached the clip. It was good the way the dress pulled in tight giving him a feminine shape. Perhaps he'll try one of those basques in the lower draw while he was staying at the house. That would certainly pull his figure in he thought. He slipped on a pair of black medium heels and set to work on the make-up.

He used a very light cream which hardly showed when it dried but gave his face a lovely smooth texture. He applied the eyeliner and shadow choosing a light-blue to go with the dress. Then the mascara for his eye lashes. He put it on thick which really made the difference to his appearance and finally a deep red lipstick. He checked in the mirror and was pleased, not overdone but very effective, he was getting good at this he thought. He heard the door slam and Ben shouted up that he was back.

"Don't come up, I'll be down in a minute," Simon called down.

He found some clip on earrings, two rings, a slim necklace and bracelet, with some perfume from the bathroom completing the task. He was now ready to tidy up his hair. Once dry it had gone thick again so he simply parted it in the middle and backcombed the front section. This gave him the very femme appearance he wanted. He stood up once again and turned a few times checking in the mirror all the which for the slightest discrepancy or possible problem. He could find none and was very pleased with his appearance, more to the point though he hoped Ben would appreciate his efforts. He found a short coat that went with the dress and went downstairs to the kitchen where Ben was putting the last of the groceries away.

"Well, what do you think?" asked Simon standing in the doorway in a deliberately softened voice. Ben turned and his jaw dropped.

"My god, is it really you, I can't believe it." Ben went quite and just looked Simon up and down.

"You look…. well…. beautiful, fantastic but how ….?" He stopped again, running out of words and just stood there looking some more. Simon lowered his eyes.

"I do look nice then?" Simon asked sheepishly misreading Ben silence.

Ben walked over, held Simon by the arm and kissed him on the forehead.

"You look absolutely stunning, I just can't believe it's the same person I left and hour ago, you look older and I can see it is still Simon but your different, you're beautiful," Ben smiled, "but we can't keep calling you Simon, do you have a girls name?"

There was hint in his voice that he knew Simon would have given himself a name when he had dressed previously.

"I was thinking about it while I was getting ready and I think I like the name Sarah." Simon had remembered his time with Sally all those years ago.

"That's a nice name and it suits you very well. Come on then my gorgeous Sarah, do you feel like going out now?"

"Do you really think we should?" Sarah was nervous again.

"Of course, the only problem you're going to have to face is fighting off the boys. Here let me help you with your coat and then I'll go and get the dogs."

They left the house, crossing the road into the industrial estate and walked up the hill. Halfway up was a gap in the hedge that led down to the canal path. The canal had been built in the early nineteenth century by a contingent of Irish immigrants desperate for any work they could get. The water was murky and had probably never known a time when visibility was more than a few centimetres. The path by the side of the canal was narrow and the dogs were enjoying themselves exploring the hedge rows and long grass. Ben had let them have a long rein which they took every advantage of. The sky was cloudy but bright with few other people using the path even though it was the week-end.

Sarah made little conscious effort to assume her new role, it just seemed to come quite naturally. Her steps were short and her feet were more in line when she walked than a boys would be with her wrist turned slightly out. She enjoyed the feeling of the nylon on her legs and the slight chill on her thighs and calves. She also noticed the sound of her high heels as they tapped along the path. She sighed audibly which Ben immediately noticed.

"Are you OK?" he asked also sensing the tension in her arm as she held on to him while they walked.

"Yes I'm fine," she said, "I was just thinking how nice this feels and how natural," said Sarah. "I am beginning to think that I don't want to stop."

"Well, you don't have to, for a while anyway."

"What do you mean?"

"Look, I can see this wasn't the first time you have dressed as Sarah but you have never been out like this, right?" Sarah nodded. "So, we are here until Monday and you can stay as Sarah until then if you want to. I have to warn you though, if you carry on looking like that I will not be responsible for what I might do," they both laughed. Sarah fell silent for a few minutes and then spoke softly.

"I think I should like to stay as Sarah for while so long as you don't mind. In fact I was rather hoping you might do something rather irresponsible at some point," she said quietly. They stopped walking and Ben turned towards her. He smiled and their lips met, fleetingly at first but then deeper as they shared their first kiss together.

They walked slowly on with her arm resting in his as they stopped at the lock to watch the boats negotiating the artificial water steps. They passed a quay where there were a number of old looking narrow-boats tied up, some with their owners drinking early evening aperitifs at the back. Although they looked similar they were nothing like the original haulers of the industrial age. They were the long boats, not of the Viking hoards but of a more recent warrior, the builders of a modern industrial empire. The genuine boats would have been filled to the brim, not with the amenities one would need for a comfortable holiday on the water, but with coal. The owner's family would have lived at the end of the boat, near the rudder in just a few square meters of very cramped space. And their horse would have spent its life on the river bank hardly ever having the time to frolic in the fields even though they would pass many during the day. They watched one of the narrow-boats enter the single gated lock which was designed and built with space for just for one boat, no yachts or cabin cruisers were welcome here. They passed under the narrow bridges and followed the path round and doubled back on themselves to cross a small bridge.

"Why did it do that?" asked Sarah looking back at the strange monument.

"It's a clever way of getting the horses onto the other side of the canal without unhitching them," explained Ben who seemed to know everything. Eventually they arrived at Bancroft basin which was the last morning point before joining the languid River Avon. Sarah noticed the Shakespeare Theatre on the other side of the gardens and smiled to herself thinking of the many plays that had performed on its famous stage with their over abundance of girls pretending to be boys at various times. Perhaps she was redressing the balance just a little bit. They bought some cold drinks and sat by the river watching the robotic skullers pumping their way up over the smooth water to the consternation of the swans and coots who weren't at all impressed at having to frantically move out of the way. Sarah moved closer to Ban and rested her head on his shoulder. He slipped his hand onto her leg gently rubbing her nyloned thigh and sensually playing with her knee.

"Come on," said Ben, "I think its time we went back and had a cuddle."

"I hope we do more than that," said Sarah holding on to Ben even tighter.

It was dark by the time they got back to the house and Ben settled the dogs down for the night. Sarah had removed her shoes and was sitting on the sofa. Ben sat down and put his arm around her shoulder and she snuggled into him.

"You really look amazing," he said again still not really believing what he saw. Sarah smiled and their lips met once again. They wrapped their arms around each other and held each other close. Ben ran his finger through her hair and kissed her neck. She closed her eyes and lay back as he caressed her nylon covered thighs. She loved the feel of his hands running up and down her leg.

She slowly undid the buttons of his shirt and slid her hands over his strong chest pinching his nipples as she went. She heard him groan and he writhed in the seat. Very slowly she moved her hand down and undid the clip on his jeans pulling the zip open very slowly. She could feel how big he was by now and slipped her fingers inside his pants and took his solid cock in her hands, squeezing it gently. He lay back and groaned again. She knew what he wanted, it was what all men wanted, to feel the lips of a beautiful lady around the head of their cock. She moved down and kissed the large head that was showing between her fingers and then took it fully into her mouth rocking he head from side to side.

"Oh Sarah, don't stop, don't stop." She loved to hear these words at last after so many years of exploring her identity. She was now convinced what the future, near future at least, would be like. She sucked harder and harder until she felt him push the head deep into her mouth as he started to pump his thick cum into her throat. She took it all and carried on sucking until he was dry and spent. She lifted her head and they kissed again.

"God that was wonderful," Ben said quietly.

"Good, because we have a few days left yet," she said with a big sparkle in her eyes, "and I think Simon should disappear completely for a while."

The next morning Sarah was up early. She looked into Ben's room but he was still sleeping. Although it was late when they went to bed they had gone to their own rooms which seemed the natural thing to do.

Good, she thought, this will give me time to get ready. She had decided to spend the rest of their time together as Sarah and had packed Simon clothes back in the holdall, she wouldn't need them again until Monday morning. She had another look through the wardrobes and draws in her room and couldn't believe the amount of clothes Bens sister owned and these weren't even her current ones.

She decided to really go to town and look her best for Ben this time. She set the bath running and then prepared everything she needed. She had found a whole range of nail varnishes in the bathroom and set to work shaping her nails. Since she never chewed and rarely cut them they were quite long so she was able to shape them into something quite feminine. The bath was ready and she had a long soak in the oil and perfume rich lather. She washed her hair again and trimmed her eyebrows into a thin line. Although she was dark her hair was not prominent and didn't require much trimming. She dried off and used some of Linda's talc, quite liberally and wallowed in the rich perfume smell.

She went to the dressing table and opened the top draw where she had found Linda's underwear. Suddenly she began to feel exited again and her cock swelled in anticipation. She would have some fun this time she thought while Ben was still asleep. She found a pink set which consisted of matching bra, panties and suspender belt. Surprisingly perhaps, she had never worn stockings in all the time she had been dressing. She had seen them in Clair's room but much preferred the look of tights especially when she wore short skirts. She fingered the plastic buttons and became aware of what she might be missing. Yes perhaps she would wear stockings tonight but not now, during the day she wanted to show off her sexy legs again.

She pulled on the panties and clipped up the bra padding it with Linda's tights and then chose the colour she wanted for her nails. She was really enjoying the moment taking her time and savouring every second as she transformed into the girl that she was beginning to realise was slowly, day by day, taking over her personality. She found a bright red bottle and varnished her toes and while they were drying did the same with her finger nails. When she had finished she held them up to dry and admired the look. Her finger were slim and lady–like to begin with, now though no one would take them for a boys.

She found a light pair of tights in the draw and pulled one leg over her fingers. She noticed that the toes weren't reinforced and remembered how her mum liked that type to wear with sandals especially if your toes were varnished. She would remember that for later. She pulled them over her freshly painted toes and then up her foot and around the heel. She then work it slowly up her leg until just above her knee. Next came the other leg in the same way, this time pulling the nylon al the way up to her thigh before returning to the first leg again. Carefully she played the nylon out through her fingers until the tights were snugly in place. Her toes looked very sexy and she caught a glimpse of her legs in the full length mirror. Her legs were definitely her best feature she thought.

Now, what type of shoes? She loved high heels and had becoming quite adept at walking in them but they were not too practical for the house. She found a pair of dark green medium heels and slipped them on. She would save the blue high heels she had found for when they went out. She had also noticed a number of slips hanging in the wardrobe. She had never worn these before. She felt the smooth satin run through her fingers and selected a medium length light green slip with a lace hem. The feeling as she pulled it over her head was incredible and she delighted in smoothing it out with her palms and feeling the silkiness like eclectic running through her. She looked in the mirror again and felt the flowing slip on her legs as she moved. Her cock was so hard now it was straining inside her tights. She pulled up the slip and eased her tights and panties down just enough for her cock to spring free. She pulled the chair over to the mirror and sat down stroking herself for the next ten minutes, sometimes fast and then slower until she shot into her hand. After a moment she wiped herself clean and became decent again. Her cock had diminished in size and she was able to tuck it well away so that it left no bulge. Now for her hair and make-up.

She wanted to look good for Ben and make sure he never felt uncomfortable when they went out. He seemed OK with her the night before but she would do her best just the same. She brushed out her hair and parted it to one side as she had the previous night. Her hair was brown, shoulder length and fairly thick. When she had finished she studied the image in the mirror carefully and was pleased with the feminine appearance. She took her time over her makeup ensuring every bit was in place and correct. First the light green eye blush to go with the dress she had chosen for that day and then the mascara. This was more tricky and took time but she was happy with the result. This alone changed her appearance the most to that of a young woman rather than a girl. Next some blusher for her cheeks and finally lipstick, pink this time.

She didn't bother with jewellery during the day but decided she would tonight after she had changed. Now for the green sleeved dress she had found in the back of the wardrobe. It seemed quite old but had been dry cleaned recently and still looked good. It was quite short and she had selected it to give the maximum effect to her legs. She pulled it slowly over her knees and placed her arm in the sleeves. The zip and clip were a bit awkward but she finally managed. She straightened the dress with her palms and looked in the full length mirror. She was ready and looked great; not only good looking but sexy too. She walked around the room a few times and then went downstairs. She could hear Ben having a shower and guessed he would be down in a few minute so she prepared a light breakfast for them both.

"Good morning, I thought I could hear….." Ben stopped as he enter the kitchen, "Oh, you've done it again. You look fabulous. I really can't believe it's you again."

"Why, thank you kind sir," said Sarah blushing.

"No really, you look great. We need to walk the dogs again this morning, are you coming with me again?"

"Yes if you think I will pass OK in daylight," Sarah said hesitantly.

"If you were standing here you wouldn't ask that," Ben went over to her and they kissed as they had the night before, long and deep.

"Wow, I can honestly say I have never had a sexier girlfriend," said Ben. Sarah blushed again. She loved to hear all his nice comments about her femininity.

They returned a couple of hours later and Ben went to feed the dogs. Sarah made them both a long, cold drink and went to the lounge. When Ben came he took her hands and pulled her up off the sofa.

"Come here you sex-pot, I don't know how I kept my hands off you while we were out," Ben held her close and the kissed long and hard. Sarah felt so good. She felt sexy and totally a girl in the hands of this handsome boy.

Ben slid his hands down her waist and kissed her neck. She threw her head back and he kissed her throat. This was so wonderful she thought, treated as a woman like this. Ben slid down kissing her body until he was sitting on the sofa and nuzzled his head into her groin, running his hands up and down her smooth nyloned legs. She held his head in her hands and moaned. She loved the feel of her own legs in tights but someone else touching her was almost unbearable. Both were very excited now. Sarah moaned again. Ben pushed his head deeper into her and lifted his hands pulling her dress up as he reached her smooth rounded bum.

"God, you have a gorgeous body." He said his hands revealing her waist. He could see the single brown seam of her tights disappear between her legs, her panties only just hiding the bulge now growing inside. He kissed her tights and she moaned once more.

"Oh Ben, that feels so wonderful."

He slipped his fingers into the waistband of her tights and slid them down just enough to reveal her panties. He kissed her again and then slipped her panties down, just an inch or so, to lie in the folds of her tights. Her cock sprang free and stood out fully erect by now. It wasn't big, under five inches and not thick either but it was very solid; a feminine and elegant ladycock, almost a large clitoris really. Her balls were small and tight and with her hard cock stretching the skin all around her groin, they had all but disappeared giving Sarah the appearance of a feminine crutch but without a pussy slit of course. She was completely smooth apart from a little thatch she had left above her cock. He kissed the tip gently and it twitched with pleasure. He kissed her again flicking his tongue across the end and then, with his finger and thumb slowly pulled back her foreskin to reveal a small, glistening red head. He licked her bud once more and then slipped his lips over the head and down her shaft, pushing her cock into his mouth. He pulled back and then pushed in again twisting his head and sucking at the same time. Sarah was groaning continuously now and pulling his head on to her as far it would go with her hands. He continued rub his hands up and down her legs and around her pert little arse and sucked harder. Pushing in and out, in and out until he took her whole length inside of him using his tongue under her cock with each thrust.

"Please, please, harder," she moaned. He sucked hard as ordered until he could feel every muscle in young smooth body tighten, just for a second and then relax as she pumped his mouth full of cum. It seemed as if she would never stop until eventually she relaxed and collapsed on the sofa.

Ben pulled up he panties and tights and set her dress again.

"There, we don't want you looking like a slut do we," he smiled.

"Oh Ben I have never cum like that before, ever, it was wonderful."

"The pleasure was all mine I can assure you," he said feeling the wet patch in his trousers, "Come on lets watch a film."

The train rattled back towards Warwick on Monday morning while Simon gazed through the window distractedly.

"What the matter, you look miserable? Didn't we have a good time this week-end," asked Ben.

Simon turned and smiled "Of course we did, I am just sorry its over, that's all."

"Well, it makes a change to see Simon again I must say, quite strange really. Listen, I thought you looked fantastic as Sarah and if I had to compare the two Sarah seemed to be the more natural. You need to think about her future since I know she is not going to go away, if anything I expect she will grow stronger. That wasn't just dressing up you were doing, its obvious she is a big part of you and I think you are going to have some big decisions to make at some time or other."

"I hadn't really thought about the future in that way," said Simon quietly.

  

  

  

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