Anyone for Tennis?

By Alison Barlow

 

Let me tell you about the weekend I discovered a whole new side to myself......

Sarah and I had been seeing each other for six weeks and things had started to get a bit more serious between us. We had a mutual friend Carole who had nagged us both about meeting up, as we were perfect for each other. Despite a healthy fear of blind dates I had finally agreed and was relieved to meet a normal human being. Actually Sarah was rather more than just normal, she was in fact gorgeous, I was amazed when she suggested at the end of the date we should meet up again and even more so when I realised she meant it!

Sarah had to dog sit for her parents and invited me along to keep her company and have some fun. Now I knew Sarah's parents were not poor and the opportunity to spend the weekend at their house was certainly not one I was going to turn down especially as Sarah and I would have the place to ourselves!

We decided to take the Friday off and drive down in the morning to beat the inevitable traffic jams. The house was stunning set in over an acre land on the edge of the Cotswolds it was a mansion to me who had grown up in a small semi in the suburbs. We pulled up the gravel path in my battered old ford which looked all the worse in the opulent surroundings.

Sarah let us in and she was immediately leapt upon by Cassie the golden retriever, my welcome was not so enthusiastic.

"Don't worry its nothing personal its just that she doesn't really like men" Sarah informed me, "Dad is the only one who can go near her".

Cassie kept close behind Sarah and gave a low growl.

Sarah showed me round the house, all seventeen rooms including a swimming pool and Jacuzzi! I never knew her parents were quite that well off, her Dad was something in the city but the place must have been worth a small fortune.

Sarah looked a little embarrassed at size of her home, she certainly wasn't a spoilt rich kid and I hadn't know or even suspected her background until Carole had told me. We sat in the kitchen where her Mum had left some soup for us along with a list of instructions of what where how and when.

"Do you fancy a game of tennis after lunch?" Sarah asked, "according to Mum's note Dad has just had the court repaired"

"Erm yeah but I haven't brought any stuff, I didn't even know you had a court!" I replied, "I only have these trainers, no shorts or anything"

I hadn't expected to play any sports and had only really brought smart clothes in case we met any of Sarah's friends.

Sarah giggled "Well don't you worry about that I will sort something out for you, we have a few spare rackets."

She seemed to be planning something, not unusual, even in the few weeks I had known her she had displayed a wicked sense fun.

We ate the soup quite quickly but the washing up was delayed by a bout of tickling and play fighting, we both ended up on the floor out of breath from laughing so much. Cassie stood by obviously caught in two minds, wanting to join in and play but still very wary of me.

With the dishes eventually washed and dried Sarah lead me to her bedroom, it had obviously not been redecorated since she was young as it had flowery pink walls and the bed was piled high with teddy bears etc., a shrine to her younger days.

"It used to be so embarrassing coming back here," Sarah said in the mocking style of a teenager, " but now I find it reassuring and comforting my little safe haven"

She rummaged in her wardrobe and pulled out a hanger with a white skirt and matching sleeveless top draped over it. I sat on the bed as she rummaged through her drawers to find a pair of white gym knickers and tiny pair of ankle socks with a fluffy ball at the heel.

"Isn't this a little OTT?" I asked, "after all you will be playing the bloke in the trousers and T-shirt"

"Oh no my dear, " Sarah put on her plumiest accent" Daddy only allows whites on the court, one can't play unless one is appropriately attired"

Sarah dressed whilst I watched, seeing her slip into the white knickers gave me a great thrill, Sarah had a lean athletic body with long tanned legs.

She wrapped the skirt around her waist "OK OK you can stop perving now" She teased catching me staring at her as she checked her self in the mirror " Lets get you sorted"

In her parent's room Sarah stood in front of me holding up the most enormous pair of shorts, "I didn't think you would be a size 38 waist!"

"38 inch waist, I think I am only just a 38 inch chest!" I replied.

"Then I think we shall have to be a bit more imaginative" She took me by the hand and led me through to a smaller bedroom at the back of the house. Inside the wardrobe there was a jumble of boxes, shoes, blankets and all kinds of junk all crammed in. Sarah searched through the mess clearly looking for something specific, "I do hope they haven't thrown it away, no no here it is" She pulled out a white box embossed with a gold pattern, Sarah peeked inside and smiled. "This will be great, come on, come back to my room."

I shut the cupboard door and followed.

 

In her room Sarah smiled "These should fit you, but they are a bit dated, you don't mind do you?"

"No I don't mind" I was suspicious though, she was up to something, but the way she looked butter wouldn't melt in her mouth.

"Good, don't worry no one will see anyway" Sarah took the lid off the box and laid it on the bed.

At first I couldn't tell what it was, all I saw was some very pale pink material delicately embroidered with a pattern of small pink flowers.

"Here let me," she said, and reaching inside the box she pulled the material out to reveal a little tennis dress straight out of the early 70's. It had capped sleeves, a dainty v-neck and a fitted top-half that flared slightly below the waist. The edges were trimmed with a thin border of dainty white lace it must have been very expensive in its time.

"It's beautiful baby but just what do you propose to do with it?" I asked.

"Its not what I am going to do with it, its what you are sexy!" Sarah replied "You're going to wear it for me"

"No way! I can't wear that"

"Well unless you want to sleep in the spare room you'll do as I say" she replied sternly.

I wasn't sure if she was joking or being serious.

"Come on it will be fun, get your clothes off, there's no way I am going to let you perve at me with out me getting a chance to perve at you in return" She had done her hair up in pigtails and as she spoke she pulled them around her face and stuck out her bottom lip, she knew exactly the way to make me melt and get her own way!

I stripped to my boxers whilst Sarah went through her drawers again, I watched her bend over and could see the flash of her gym knickers as her little tennis skirt rode up, I felt myself stir.

"Don't think I can't see what your doing" Sarah turned quickly and my hand shot to my side in a very guilty manner.

"Now put your arms out straight in front of you" She was holding a white bra that she placed over my hands and slid down the length of my arms. She fastened the clasp at the back and stuffed a pair of rolled up socks into each cup moulding them into the shape of breasts. Next she slipped the dress over my head gently pulling it into place she zipped up the back and smoothed it over my body.

"Not bad, not bad at all, how does that feel?"

I was mesmerized, I had worn women's clothing before, once in a charity pub crawl but that couldn't compare to this. The whole sensation of being dressed by Sarah, and the feel of the stunning dress, so sleek and feminine, I was in heaven.

"Well it seems I have shut you up at last, now for the final touch"

In the bottom of the box was a pair of white knickers, covered with pink edged frills. Sarah removed my boxers and held open each leg of the panties for me to step through. She pulled them up my legs very slowly so that I quivered uncontrollably in response to their silky touch. I looked in the bedroom mirror and saw how the slinky dress clung to my newly padded chest, the frills of the panties pushed the dress out over my hips to give me a set of womanly curves. I ran my hands over the soft fabric following the profile of my breasts down to my hips. As I passed over the panties I could feel the sensual spring of the frills beneath. I felt incredible so girly and feminine, coy and yet very very sexy.

Sarah gave me a hug "Baby you look so beautiful, I could just eat you"

We kissed and petted for a while until I felt so heady and drunk I thought I was going to faint.

As if sensing my state Sarah broke off and skipped over to the door, "Come on lets get some fresh air."

"Wait a sec, I need to put some shoes on first"

"Get some socks from the drawer and hurry up"

I delved into her knicker drawer and found a pair of ankle socks similar to the ones she was wearing, the array of sexy underwear gave me a new thrill as I sorted through it. I was not imagining Sarah wearing them any more, now I was imagining how they would feel on me!

In the hallway I encountered Cassie, remarkably she did not bark this time and she showed no signs of backing away. Instead she simply cocked her head to one side and looked at me.

"I don't think she knows what to make of you" Sarah said from the doorway, "come on lets go play."

I felt awkward about going outside dressed as I was, I felt very vulnerable and as though the eyes of the world were staring at me. I took my time putting on my trainers slowly tying the laces convinced someone was watching.

"Is my little girl having trouble with her bows?" Sarah was mocking me, she grabbed my arm and dragged me outside.

I felt a breeze around the full extent of my legs and ruffling the frills on my panties. I had to admit it was a fantastic sensation, I wanted to skip to the court but thought I had better run to catch up with Sarah who had already disappeared around the corner. I looked around secretly hoping someone was watching, the thrill it gave me was overpowering.

Once we had started playing tennis I lost myself in the game and hardly noticed my new attire. The only differences were that the dress gave me much greater freedom in my movements and I had to tuck the balls into the panties as I had no pockets. After a while my outfit seemed the most natural thing in the world, Sarah occasionally gave a joking wolf whistle or a 'phwoar' from the other side of the net. Even though I blushed her comments made me feel very sexy, I even started playing for compliments by bending over to flash my panties to her when I picked up a ball or by seductively adjusting my dress when I knew she was watching.

At the end of the game she had thoroughly beaten me though I did claim some degree of distraction! We met at the net and instead of the traditional handshake she grabbed me and pulled me close for a kiss. As we embraced she slid her had under the hem of my skirt and into my panties.

"I am not that sort of girl!" I joked as I pushed her away.

"Well I am, so you had better watch out"

With that she chased me back to the house, both of us giggling like schoolgirls.

"We had better take Cassie for a walk, Why don't you grab a quick shower. Use the one in my room, I'll use my parents'."

I felt a tinge of disappointment having to take off my pretty pink dress but I couldn't wear it all day. I washed off the exertions of the tennis game and put my own drab clothes back on. Sarah was already downstairs playing happily with Cassie but as I bounced down the stairs Cassie immediately stopped and retreated behind Sarah as she had done when I first arrived.

"What's the matter you not like the big horrid boy!" Sarah said to Cassie.

"I thought she was OK with me after earlier."

"Hmm, I wonder if it was the tennis dress?" Sarah was thinking, "Lets do an experiment, come with me." Sarah bounded back up the stairs

"My Mum has an old wig somewhere, I used to play dressing up in it when I was young." Sarah was back in the small bedroom rummaging around the wardrobe again.

She pulled out a blonde wig cut in a sixties style bob.

"It needs a bit of combing but I think it will look great on you, lets dress you up properly this time and see if Cassie likes you then"

Now I understood what Sarah's experiment was going to be, and I had to say after the tennis game I was actually looking forward to it.

Sarah selected a pair of racy red panties with a matching bra.

"These are supposed to give you the ultimate body by lifting your buttocks and slimming your tummy, lets see if they can control you!" Sarah was loving this almost as much as me.

I stripped off and hurriedly slipped the panties on desperate to cover my ever excited self. They were tight around me I couldn't tell if my buttocks were lifted but I certainly felt under control. Sarah padded the bra out with some tights and started flicking through her clothes to select something for me to wear.

"I think we should start with something simple, I don't want you looking like a drag queen now do I."

She um'd and ah'd for a while before selecting a full length black skirt with a gentle flair and a light blue roll neck mohair jumper.

"Lets get you some tights and as you have the same size as Mum we could dig you out some boots as well."

I was baffled by the tights and could not work out how to get them on, Sarah laughed at my struggles and eventually showed me how to gather them around the toe before sliding them up my legs. Feeling the luscious sensation of the tights on my legs and Sarah's gentle hands guiding them up my leg caused my panties to get even tighter, I was feeling very heady.

With the tights on Sarah helped me into the skirt and zipped me in, as the material swished around I could feel the satin lining brushing against my legs, it felt great so smooth and silky. Just as I settled to the sensations the skirt and tights were giving me I encountered the angora jumper. Wow, it was unbelievable so soft next to my skin, I ran my hands over my new pert breasts letting the soft wool caress my fingers. How come none of my male clothes felt this good, why on earth did women wear jeans and t-shirts when they could have this! I felt astounding all my senses were heightened my skin felt like it was crackling with electricity.

Looking in the mirror my short hair and masculine features still belied my true gender but from the neck down I looked totally feminine. I was desperate to complete the outfit and perfect the beautiful illusion the clothes were making. Sarah sat me at her dressing table and set about my face with her make-up kit, a base layer of foundation smoothed out my skin colour and hid the traces of my beard. She gave me a soft blend of eyeshadow and filled my eyelashes out with mascara making them look long and luscious. A hint of blusher highlighted my cheekbones and finally a touch of lipstick made my lips red, full and eminently kissable! Sarah brushed out the wig taking out the knots and restoring its style, she then put it on me and fussed with the hair until she was satisfied. She had selected a pair of black knee high boots with a modest heel from her mother's wardrobe and after a bit of work we got them on.

"OK you can stand up and look in the mirror now, my beautiful little girl."

I looked in the mirror and was amazed, the masculine features were gone and before me stood, a woman, her blonde hair bobbed around her face and her eyelashes fluttered seductively, it was me, but I was transformed.

"A little bit of perfume I think and then lets see what Cassie thinks!"

My first few steps in the boots were tentative but I soon found by adding a little wiggle to my walk they were very comfortable, they also felt very sexy hugging my calves and forcing me to stand properly.

I carefully negotiated the stairs and caught up with Sarah at the bottom, she straightened my clothes and stood back to admire her work.

"Well let's see if you can fool your first and probably toughest inquisitor."

Sarah called Cassie in from the lounge and the dog immediately bounded through, Tail wagging she leapt up at Sarah and attempted to lick her face.

"Ok ok, steady girl" Sarah pushed her back to the floor "I want you to meet my new girlfriend."

Cassie clearly quite an intelligent animal turned to face where Sarah was pointing, directly at me. I felt very nervous, which seemed stupid it was after all only a dog, but somehow it seemed important that Cassie accepted my new feminine role, I desperately wanted to pass as a girl. It was clear Cassie was hesitant but slowly she padded over to me. She was just a foot from me when she clearly decided I was OK, her tail started wagging and she gave out an excited bark. I was relieved and very happy, I could have kissed Cassie but a combination of her dog food breath and not wanting to smudge my makeup fortunately stopped me, instead I settled for a hug and pat.

"It seems she has accepted you my sweet, and I am not surprised you look amazing! Shall we celebrate by taking her for a walk?"

I did not really get chance to think about the implications of this statement as Sarah picked up the lead and Cassie immediately sensing what was about to happen started to bark and run around in a very excited mood. Sarah passed me a coat, it was long and black with a fake fur collar. Instinctively I put it on and we were out of the door being dragged by a manic dog.

I hadn't even twigged the consequences of us turning into the lane outside the house when I was confronted by them. Walking towards us was a middle aged lady accompanied by an overweight and out of breath cocker-spaniel.

"Afternoon," she hailed, looking straight at me and smiling.

I smiled back and mumbled something in a neutral a tone as possible. Fortunately Sarah was alert and beamed a loud and confident hello back. Once the adrenalin had died down I realised I was delighted. The woman had looked straight at me and had not even blinked, I was sure there had been no doubt in her mind that she had just met a couple of young girls walking their dog.

Sarah was chuckling to herself, "You certainly fooled her!" she said excitedly, "Well aren't you the beautiful young lady!"

We did not meet anyone else on the walk but I was floating on air. I got really into the part trying to walk like her and watching her mannerisms a lot more closely.

I had a few accidents with my heeled boots but with all the walking practise they felt more and more natural if not a little sore. Cassie had totally accepted me and trotted happily by my side.

Upon our return I removed my coat and boots but nothing else. Sarah showed no signs of wanting me to change and I certainly did not want to let go of my new look. We ate and drank a couple of bottles of wine between us watching television snuggled up together on the sofa. I had loved my day and it felt entirely natural to ask Sarah for a pretty nightie to wear in bed. So we slept embracing each other her in a pair of silky blue pjamas and me in a long cream silky nightdress.

The next morning Sarah suggested a swim and to my delight she offered me a daisy patterned speedo swimming costume that had an integral skirt to hide my manhood. Wow it was amazing, a snug fit but it hugged my skin all over and defined my body. I took great delight in hooking my fingers under the elastic around my bottom to snap it firmly in place. I had seen girls do this as a lad it had fascinated me, now wearing a girl's costume it was brilliant to actually experience. Sarah donned her pink swimsuit and armed with fluffy white towels we made our way to their pool. I sharn't tell you everything that we got up to but it was a fantastic morning. Suffice to say we swam, jacuzzi'd and whiled away the hours eating, reading and of course playing!

 

 

 

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© 2002 by Alison Barlow. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.