Whatever It Takes?


It was a classic 'eyes meeting across a crowed room' moment when I met Penny. It was a Thursday night and I was at a corporate function where the firm I worked for were trying to drum up new business. Penny represented one of the companies that had received an invite. I had noticed her as soon as she walked in; elegantly dressed she looked beautiful, with her dress giving the occasional hint of a stunning figure, but without being too obvious. Someone like her was way out of my league. I did my best not to stare, but I couldn't help myself and sure enough she caught my eye. When she smiled back I felt myself blushing deeply, then I gave a small look over my shoulder, just to check that Penny hadn't been smiling at someone else!

I was flustered. Gorgeous women like Penny didn't normally smile across crowded rooms at me. As she made her way towards me, I began to panic slightly and to pray that I didn't make a complete fool of myself.

Let me introduce myself; I'm Daniel and I'm the antithesis of the traditional tall, dark and handsome. I am, in fact, short, say 5'6", which is about the same height as Penny I realized as she stood next to me, slightly taller than me because of her high heels. To complete the image I have mousey, light brown hair, worn quite long, and my features are embarrassingly delicate, rather than handsome or rugged.

She spoke. She had a very sexy voice.

"Hi I'm Penny."

The small talk was excruciatingly painful at first. When confronted by a beautiful woman like Penny, I find it hard to say anything witty or amusing. In fact I find it hard to say anything at all sometimes! However Penny made me feel almost at ease and to my amazement, after about half an hour of small talk, she suggested that we left the function. Soon we were in a cab, heading for Penny's apartment.

What happened next was so far beyond my wildest dreams as to leave me in a daze. Once in the flat we began kissing and it seemed to me as if Penny couldn't wait to get me undressed. As her hands roamed across my body I had to use all my willpower not to shoot my cum too soon. Swiftly moving into her bedroom we stripped. Penny gave me a look like a lioness about to pounce on an antelope and then pushed me on the bed and sat astride me. She proceeded to give me the ride of my life and it was only a few moments before I climaxed. Penny hadn't, but this didn't bother her. She simply moved up my body and lowered her pussy, dripping wet from the mixture of her juices and my cum, onto my face.

This was another first for me. I had never licked a pussy dripping my own cum before. Well to be strictly honest, although I didn't admit this to Penny, I had never licked anything more exciting than an ice cream. I did my best despite the strange taste. Eventually with a lot of assistance from Penny in the form of gentle guidance and her using a small vibrator on her clit, she climaxed noisily. Tired from our exertions we soon fell soundly asleep.

I awoke the next day, Friday, and, hearing Penny moving about, realized that it hadn't all been a dream. I peered round bleary-eyed, aware my need for a wash, to get dressed and go to work. Penny was standing by the bed, giggling and wearing my boxer shorts.

"Hey! What am I gonna wear?" I protested sleepily.

"These!" Penny replied chucking me her own silky knickers.

I looked at the knickers. They were made of a silky red material, with panels of lace. Penny had looked stunning in them and the thought of wearing them sent unexpected butterflies loose in my tummy. I didn't want to seem unsophisticated or naïve so I got out of bed and put them on. The silky material snugly caressed my bottom and my cock; Penny rewarded my bravery with a stroke of my bum.

'There's just one snag, Penny,' I stammered, 'I haven't got time to go home to change before work...' my sentence tailed off.

'So you're going to have to wear my silk knickers all day.' Penny finished off my sentence for me. 'And when I meet you for a drink after work, you'd better still be wearing them!'

I set off for work, wearing the knickers under my trousers. No-one commented on my slightly scruffy appearance or the fact that I was wearing the same shirt and tie as the day before. Also my departure from the function with Penny had gone unnoticed. To my relief there didn't seem to be any sign of my unusual attire, such as a visible panty line, and I began to enjoy the whole experience. I was so pleased to have met someone as beautiful as Penny, who clearly liked me, I would have agreed to almost anything to please her. Wearing her knickers was a reminder of her reality. Also, I found her request intriguing, giving her an air of mystery that I wanted to explore. Slightly disturbingly, I also found wearing the silky knickers to be a most enjoyable experience.

During the morning I got this text message from Penny:

"Send me a pic of u in my knickers ;-)"

Blushing I went to the toilets and in one of the cubicles took and sent a picture of my lower half, trousers down, knickers clearly visible, which I sent to her.

I was rewarded by this reply:

"Cute! Wet just looking at u. xxx"

Blushing I tried to concentrate on my work.

In the afternoon I got a picture message from Penny. I was of two pairs of knickers laid out on her bed. One pair was black, with a lacy front and silky back, the other a cream-coloured silky pair. The text said: "u choose 1 4 me & 1 4 u"

Flustered I went to the loo again. My cock was straining in the knickers I was wearing – the thought of being asked to choose a pair to wear tonight was nearly too much! My hands shook slightly as I typed my reply: "black 4 me, cream 4 u xxx"

In return I got a picture of her wearing the cream knickers!!!

We met after work at a pub just round the corner from work. I was slightly surprised by the hug she gave me, but more surprised when she slid her hand down the waistband of my trousers to stroke my bum.

'Just checking Danny' she whispered in my ear.

We had a quick drink and then headed back to my flat, so I could change. I quickly showered and came into the bedroom to find that Penny had been through my wardrobe and chosen my clothes for me. They were laid out on the bed along with the black knickers. I dressed quickly and we went out.

Penny seemed pleased that I made no complaints and went along with her instructions. In fact, although I still didn't admit it to her, I so enjoyed the silky feel of her knickers under my jeans, that by the time we returned home I was very definitely aroused, a fact that Penny must have noticed as we kissed goodnight. I invited her in, but she declined sadly, telling me she had a business meeting on Saturday morning and that she hoped I'd meet me at her flat tomorrow evening. She laughed when I said her boss was a slave driver. It was only once she had left that I remembered I was still wearing the black knickers. I texted her asking if she wanted me to wash them before returning them. Her reply was clear: "wash them? If u like, but u'd better be wearing them 2morrow ;-) xxx"

I did wash them, before putting them straight back on as soon as they came out of the drier. They felt so nice as I slid them up my legs and over my bottom. They felt both physically and mentally good to wear; physically because of the silky material against my skin and mentally because they were a constant reminder of Penny's arrival in my life. We had a great evening, a nice romantic meal followed by dancing in a club. I don't dance very well, but Penny didn't seem to mind. We ended up back at her flat and soon we were almost naked and entwined in each others grasp. I say 'almost naked' because Penny was most insistent that I kept her knickers on. I moaned with pleasure as she stroked my cock and balls through the silky material. Finally she slipped my cock out of the leg of the knickers, leaving my balls encased in the smooth silky material. Again she went on top, lowering her moist, open pussy lips onto my cock. This time she went to work on her clit with a small vibrator while she slid up and down my cock and soon she was on the point of her own orgasm. The gripping movements this caused inside her pussy pushed me over the edge too and we climaxed almost together and then lay holding each other in bed, till sleep overtook us.

The next morning as we lay in bed together we read an article in a Sunday newspaper about a new fad in male grooming. Apparently there was a trend towards body hair removal, a fact the paper illustrated with photos of the undoubtedly hair-free bodies of some top professional sportsmen. Penny was completely taken by the idea. She said I would look stunning. I tried to sound doubtful, but the endorsement by such athletic male role models made the suggestion an appealing one and anyway I found it impossible to say no to her.

I am not a naturally hairy person, but I do have a few hairs on my arms, my legs and an embarrassingly small number on my chest. A quick trip to a local chemist shop and Penny had bought what we needed. Back at home she took control. First I undressed and we went into her bathroom. I was feeling excited by the prospect and was looking forward to it. Using the sponge provided, I rubbed the cream all over my arms and chest, all the way down to just above my pubic hair or 'bikini-line' as Penny insisted on calling it. Then Penny worked on my shoulders, back and finally my legs, covering them all from front to back and all of the way up to my bum. After a couple of minutes I got into the shower. To my delight Penny joined me and we started to scrape off the cream using the other side of the sponge. I was surprised at how easy the hairs came away. Once we were finished I was almost completely stripped of body hair.

Penny rubbed her hands up my now silky smooth legs and the feeling as her carefully manicure nails traced a winding pattern along my legs was amazing. The water from the shower was running in rivers down between us. Penny reached for a moisturizing shower gel, took a handful and started to rub it all over my chest and groin, also massaging my hard cock and balls. I took a handful of shower gel and started to massage it into her boobs and down to her crotch and bum. She had the loveliest firm bum which I massaged with my fingers. She looked straight into my eyes before reaching round behind me and returning the favour. With one hand she squeezed my bum; with the other she stroked my cock. The shower water was now cascading all over us. We kissed passionately as our bodies glided against each other, while we enjoyed out intimate massage. I was nearly ready to cum, and Penny sensed this and pulled away, saying 'later'.

Out of the shower she looked at her handiwork.

"Perfect" she said, picking off a couple of loose hairs. "Just two more things. First we need to shave your underarm hairs," she said, picking up a razor. I raised my arms in the air and then she applied a little foam. She carefully shaved away all of my underarm hairs, until I was smooth. She then rubbed on a little moisturising cream, saying; "This might sting a little". It did but I couldn't complain too much: I was enjoying the attention. Then she made me stand on a towel. Very carefully, using a small pair of nail scissors, Penny proceeded to give my pubes a trim! My cock twitched every time she snipped. The effect was certainly much neater. Penny certainly seemed to approve!

It was only when I got home that I got cold feet. I caught a glimpse of myself in the mirror. With my long, nearly shoulder length hair, slim hair-free body, wearing only the silky black knickers, I looked just like a slim, flat-chested girl! I was pleased that Penny liked my appearance, but I had a nagging feeling that I had to do something to reassert my masculinity. Then I had an idea. I decided it was time for a hair-cut!

When I told Penny she nearly exploded! 'You even think of getting your hair cut and you're dumped' was how she phrased it. I hurried to reassure her it was only an idea. Then I voiced my concern about my slightly feminine appearance and she assured me that she knew I was all man, she just like the way I looked in her knickers and that she liked me with long hair. She was quite frosty that evening and I sensed her displeasure. The following week she was still rather distant, brief on the phone and there were no flirty text messages. I began to wonder if I'd lost her. Perhaps that's why the following Monday morning I didn't make a fuss when I discovered what she had done the day before while we were at my flat.

Picture the scene. It's a Monday morning and I'm late for work. I'm not seeing Penny that day so I can wear my dull, but appropriate, boxers. I open the drawer. There are no boxers. The drawer is full of pairs of knickers of all descriptions. I'm late so I have no choice but to pick a pair, pale blue cotton with contrasting white lace trim since you ask, and get dressed. On the train it dawns on me that on Sunday, Penny had a large bag with her, saying she'd got her gym gear. She must have swapped a bag full of knickers for my boxers! I send a text to Penny to check and to ask what she has done with my boxers. The reply confirmed my suspicions.

"Binned them! You'll have 2 wear knickers all the time now 2 keep me happy ;-) send me a pic when u get 2 work. Luv u xxx!"

I thought of the consequences of not sending her the picture and of buying new boxers – no more Penny. It was a no-brainer. I sent her the picture and began to wear knickers every day. I knew it was odd, kinky or even weird; I decided I didn't care! Wearing knickers everyday was no hardship to keep Penny in my life.

Next weekend, one chilly November evening, the weekend of bonfire night as it happened, I arrived at Penny's apartment, dressed for an evening in; shirt, jumper and a thin pair of black trousers. I was a bit put out when Penny announced that she wanted to go to a firework display in a local park.

"I'll freeze!" he complained.

Penny was not to be deterred. "I'm not going to let your clothes stop us going! I'll sort you something out to wear. Strip down to your pants, I mean knickers!"

My cock gave an involuntary twitch as I wondered what Penny had in mind. Following her instructions I undressed. Dismissing my trousers as too thin, she went on "Wear these tights, they'll keep you warmer and you'll love the feel on your legs."

With Penny's help, I pulled on a pair of black tights over my black knickers, noting with some pleasure that Penny was right: the tights did feel wonderful. Penny noticed me smiling.

"Enjoying yourself?"

Blushing I stammered "They're alright, not as uncomfortable has I thought they might be." I had become a master of understatement. They felt wonderful! She handed me a pair of her jeans. I stepped into them and quickly realised they were the faded blue, skin-tight pair she owned. I struggled into them. Oddly I found the process of placing my-self fully in Penny hands quite exciting. Fastening the zip my enjoyment was all too obvious in the distinct bulge. "Let me help you with that" said Penny. She unzipped the jeans and reached inside my knickers. I prepared myself for a brisk wank. However with a swift push and a tug on my knickers, I found my cock tucked between my legs and held in place by the knickers and tights. Now when I zipped up the jeans they fitted just fine. The boots Penny produced were brown mid-calf boots, worn with the skinny jeans tucked into them. They also fitted fine, but, although I would be warm enough, with their obviously feminine style my bottom half looked like I was a woman; my top didn't. I pointed this out.

Penny just smiled. "You're right, but I've had a brilliant idea" she announced. She frowned and paused. "But after last month I'm not sure you love me enough to try it." Eager to win some brownie points I assured her I loved her enough to do anything she wanted. She smiled.

"Anything?" she questioned.

"Anything" I confirmed, wondering what I was letting myself in for.

First she made me put on a plain, purely functional sports bra, which she proceeded to stuff with cotton wool balls and scrunched up tissue. For me to wear over my newly formed bust, Penny gave me a snug fitted, white t-shirt, and a fluffy pink v-necked sweater. I was about to look in the mirror when Penny stopped me.

"Make-up first, my pretty one!" she said.

Make up? I suppose it made sense; I might as well let her do the job properly. She applied a quick layer of foundation, a dab of eye shadow, a quick flick of mascara and some lipstick. Finally she used heated curling tongs to get some shape into my hair.

"Now you can look!" she announced with a hint of triumph. "If you don't admit you make a beautiful young woman, then you're a liar!"

I looked. Startled, I looked again, more carefully this time. She was nearly right. I'd use the words 'plain but convincing' instead of beautiful, but took care not to say so. Penny appeared having dressed quickly. When I saw what she was wearing I could see I'd been set up good and proper. A baggy rugby shirt, loose fitting boot-cut jeans and a pair of timberlands. I needn't have been dressed up as a woman if she'd let me wear her stuff!

I was about to point this out, but something stopped me. It was a 'light bulb' moment, like in the cartoons when someone has an idea. It was all so clear. Right from the party where we met she had been 'grooming' me for this. The knickers-wearing, the body-hair removal, the insistence that I didn't cut my hair; this was just the next step along the path. I could speak up now and risk losing Penny or keep quiet and prepare myself for more of the same, to travel further along the path which Penny was leading me.

"Every thing all right?" she asked.

Would I, should I, could I do whatever it took to keep Penny happy?

What should I do?

What would you do in my place?

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