Turning The Tables Ch. 03


The story so far: Phillip is on holiday with his wife, Jacqui and her best friend Hilary. Following on from a pleasant evenings cross-dressing with Jacqui and Hilary at home, He has been encouraged to spend the week as Pippa and so far the experience has been an enjoyable one.


We awoke the next morning quite late after the exploits of the previous night, the three of us still on the double bed. I woke first and headed for the loo. I looked a right state with smeared make-up wearing the short red silky nightdress Jacqui had given me to wear. I was about to relieve myself when the door, which I hadn’t locked, opened to reveal Hilary.

“I hope you’re not gonna pee standing up like a guy!” she said with a small smile that made it clear she wasn’t joking. She stood there and watched as I sat and made no move to leave. “Don’t mind me Pippa, all girls together, you go ahead and pee.”

I was too desperate to argue, but felt strangely vulnerable as I did. She carried on and gave me my ‘orders’, which I then followed. I was to shower, using depilatory cream on my legs, arms and chest; shave my face twice, then dress in my undies. I did so carefully, knowing that if I annoyed her, she might make my life a misery by putting me in unpleasant situations during the rest of the day.

Soon I was wearing my corset-like waist clincher, a clean pair of silky panties over which I wore a cream-coloured pair of tight Lycra panties to disguise any male bulges. When I first wore them they had seemed uncomfortably tight, but now I found their tightness comforting. Even the restrictive waist clincher helped me act in a feminine way as well as giving me a really thin waist.

Today I put on a pair of sheer tights that gave the effect of tanned legs. Then Jacqui helped me stick my false boobs in place, and I put on a matching cream bra. Jacqui and Hilary indicated which make–up I was to use and then they disappeared in the bathroom together where, judging by the noise, they shared an enjoyable shower. I was quite jealous, but I couldn’t mope as I wanted to be ready when they came out. Soon I had applied my make-up, put on my wig and was wearing a short black skirt, with a small slit on the front of the left thigh, a simple white blouse, a pastel blue sweater and a flat pair of black shoes. The others came out of the bathroom to find me admiring myself in the mirror. I must confess I was very taken by my feminine appearance on this holiday and I liked the outfit they had chosen for me.

The shoes were the only disappointment, reminding me a bit of the black plimsoles you had to wear for gym at school when you were a five year old. My disappointment must have shown because both Jacqui and Hilary teased me about it, suggesting that I would rather have a pair with six-inch heels.

“Well, maybe not six inches!” I protested.

“Pippa doesn’t think she can manage six inches!” squealed Jacqui making the double meaning of her comment very clear.

“Maybe Pippa will find six inches a pain in the butt!” retorted Hilary picking up the theme. “Don’t worry, Pippa dear, our first stop today is the shopping centre to get you some new shoes and some other clothes. Anything else will have to wait.”

The final addition to my outfit was a handbag. Hilary told me to wear it with the strap running diagonally across my body, strap on my left shoulder, bag resting on my right hip. This meant the strap went between my boobs, serving to emphasize them. Together we looked just like three twenty-something young women as we walked through the hotel reception and out to our car.

The centre was a few minutes drive away from our hotel, so I didn’t have time to get very nervous. Although the hotel had been quite busy on the first evening, the shopping centre could be very busy and there would be no hotel room where I could run and hide. However, in spite of the risks I was actually looking forward to the trip. We parked near to an entrance and made our way in. At first I found myself scanning the faces of the other shoppers, looking for signs that I had been detected, but as I saw no adverse reaction at all I stopped and began to relax. I still kept an eye on the other shoppers. Disconcertingly I noticed that men, even when they were with a female partner, were taking the opportunity to check out all three of us. This gave me slightly mixed feelings. Obviously I was pleased not to be discovered, but some of the looks we got made it quite clear what the guys were thinking. I had never been looked at in such a way. It was a weird feeling to know that guys were looking at me and thinking I was pretty or fit or, worse still, an object of their lust!

I mentioned this quietly to Jacqui and Hilary.

“You should get used to it Pip.” Jacqui replied. “You look like an attractive woman, not a man in a dress. Like all guys you look at the image and react. You’ve done it enough times when we’ve been out shopping, you just didn’t know I could tell. Well now the tables are turned bomonti escort and you’re getting looked at. You should enjoy the fact that all these guys think you’re as hot as the two of us.”

“Any way what harm is there in them looking? You don’t have to let a guy fuck you just cos he likes the look of you!” Hilary added. That was twice she had made a reference to me having sex with a guy. I didn’t say anything but I was starting to worry what she had planned.

We began by looking in some clothes stores, taking it in turns to pull items off the rack and as the opinion of the others. I watched what the others did closely and tried to copy them as much as possible. I choose a nice red dress, rather short and clingy, but stylish nevertheless. Unthinkably Hilary then said that we were going to the changing room to try on our selections!

There was no escaping for me, and I followed the others obediently, taking my one item disc from the young girl attendant. She paid me no more attention than any other customer, continuing to chew on her gum, like a bored cow in a field chewing the cud. (Not that she bore any other resemblance to a cow, being quite slim and pretty!). To my relief there were separate cubicles, with lockable doors, so I felt safe as I tried on the dress. My biggest problem was getting my sweater off without messing up my make-up or dislodging my wig. .

“Are you ready yet Pippa?” said Jacqui, knocking on the door.

“Nearly, but I need help with the zipper” I hissed back.

“Open up then silly!”

I did and Jacqui zipped me all the way up. The mirrors were outside on the walls at the end of the room so out I came. There were two other women in front of us at the mirror, but they soon disappeared back into their cubicles. We admired the dress Hilary had picked, a wraparound style dress in a highly patterned material. It suited her very well. Jacqui had chosen a classic little black dress, but I was a bit shocked to see how much cleavage the low cut front displayed.

“I love it!” she announced.

Finally it was my turn in front of the mirror. I had caught only a few glimpses of myself, but knowing that Hilary in particular was taking great delight in any discomfort I showed, I had tried not to seem too anxious.

The dress had a high round chocker-neck and long sleeves. The body of the dress was tight fitting but it flared out below the waist, with the hemline at mid-thigh. It fitted perfectly and made me look very feminine and glamorous. I did a few practice twirls in front of the mirror and the dress moved delightfully. I wanted to own it so badly, but I tried to act cool.

“It looks ok, do you think?” I tried to sound matter of fact.

“It looks great and you know it you smug bitch!” said Jacqui using harsh words but an affectionate tone, accompanied by a quick hug, that conveyed her true feelings. “I guess you want to buy it?”

I nodded and the seeing that a bit of a queue was developing, hurried back to change out of it, first getting Jacqui to lower the zipper, before I could disappear into the cubicle. The lack of a mirror concerned me a bit, but when I was sure my wig was ok, I rejoined the others who were waiting for me in the queue for the tills, where Hilary told me that to check that there was enough in my purse to pay for it.

“Otherwise you’ll have to find some way to raise the cash” she sniggered.

Next on the agenda were shoes. As we browsed in the shoe shops I realized that I was enjoying shopping much more as Pippa, than I had before. I was enjoying the different feeling of shopping as a woman. I was even coping better with any admiring looks that came my way. If any guy wanted to lust after me that was up to him, I’d just take it as a compliment and move on. With my new confident attitude my fears about Hilary’s plans receded.

The others helped me pick out two pairs to try on. First was a pair of black, knee-length boots with a spiky 3 inch stiletto heel. The others were red, strappy wedges with a four-inch heel. Luckily I had smallish feet, so I could ask for my size without arousing suspicion. The only free assistant was a young man, still a teenager. Eagerly he took the shoes I handed him and set off in search of some in my size from the stockroom, while I slipped of my shoes and sat waiting.

John (he was wearing a name-tag) was very attentive. He knelt at my feet and insisted on helping me on with the boots, even zipping them up for me. He invited me to try them out. Gingerly I walked a few steps around the shop. I could manage to walk in the heels ok and I liked how the boots looked when I looked in the mirrors. I sat back down.

“Were they ok?” asked John.

“Yes, John they were fine, I’ll be taking them. Let me try the others on now.”

As he helped me take off the boots I finally realized two things. John was touching my feet and legs rather more than was strictly necessary and that his eyes kept cihangir escort straying up my legs, but never as high as my face. I guessed that he was checking out my legs or perhaps trying to sneak a glimpse of my panties as I was wearing a short skirt. Earlier in the day I might have been freaked out by this, but now I took it as a compliment, just something I had to deal with if I wanted to dress and act like this. I decided to be a tease.

I crossed my legs, very slowly, sliding my right leg upwards against my left leg, so the silky material of my tights made a delightful swishing sound, over the knee and then swiftly down. It was a bit like that scene in that thriller, where the woman suspected of murder is being interviewed by the cops. During her interview she crosses her legs to distract them. Only in this recreation there was a shop assistant instead of cops and tights and panties instead of nothing! However from the way John blushed and stammered he had enjoyed it as much as I had; maybe he had caught a quick view of my panties!

I maintained my cross legged pose, with my leg pointed out, twisting and turning my foot to admire the strappy red shoes, all the while keeping an eye on John. He obviously enjoyed the view too, because I am sure I saw him have to adjust his cock to make himself more comfortable. Just to make sure he was thoroughly teased, I allowed my bare foot to brush against him, stroking his crotch, accidentally of course.

In the end I bought both pairs, giving John two good sales in addition to the teasing, so I felt it was ok. After we left my antics got a mixed reception from my companions. Hilary was thrilled that I had been, to use her phrase, ‘such a prick teasing bitch’ and I got a hug from her. Jacqui was more muted in her praise and she seemed a bit surprised that I had been able to be so comfortable with my behaviour. During the drive back to the hotel her displeasure showed in the crunching of gears and erratic braking.

Back in the room she took me completely by surprise, grabbing me by the arm as I passed her and pulling me, face down onto her lap.

“You’ve been a naughty girl Pippa and naughty girls get spanked!” she said, tugging my skirt up to expose my bum. Hilary assisted her by holding my arms out in front of me. The first few slaps were delivered and they stung, but Jacqui clearly wasn’t satisfied that I was suffering enough. She dragged my tights and both pairs of panties down to expose my bum, but not far enough for my stiffening cock to free itself. The first few slaps to my bare bum stung like mad, but the Jacqui was handed a hairbrush by Hilary. She was really giving me a good spanking and the hairbrush made each blow much more painful. Worse still, as I squirmed on Jacqui’s lap, the rubbing of my cock made it harder still. The spanking continues and the pain no longer receded between blows, my bum cheeks felt on fire. Jacqui finally stopped and I was hauled to my feet. A tear trickled wetly down my face and I realized I was crying, but my punishment wasn’t over yet.

“Hands on your head!” ordered Jacqui, much more dominating that she had ever been. I obeyed meekly. My skirt was hitched up, hemline tucked in the waist to keep it there and my knickers and tights were tugged down to mid thigh. My erect cock bobbed up and got slapped by her, very firmly. Then she began to wank me, rather roughly, in a business like way and totally without passion. It was obvious to me this was punishment and not pleasure.

“Warn me when you are about to cum.”

I did warn her in time and my cum spurted into a plastic cup, held by a grinning Hilary. Jacqui took the cup and held it to my lips. “Drink a sip and then swallow” she ordered, tipping the cup. Obediently I sipped the sticky liquid and swallowed, resisting the urge to spit it out.

She moved behind me. “Bend over” she said, and I leant forward resting my hands on the bed. I felt her pour the remainder of the sticky liquid on my still stinging bum. I felt it trickle down my sore bum cheeks and down my bum crack. She then began to massage it all over my bum, rubbing it well in and using it to tease my bum hole with her sticky finger.

“Get used to the feeling, cos if you carry on like you did today in the shoe shop, one day some guy won’t be pleased and you might find yourself in a worse position than this.” Jacqui explained. “I did this for your own good Pippa, so say thank you.”

“Thank you Jacqui, I’m sorry I was a bad girl.” I mumbled, still sniffing back the tears.

She then embraced me, kissed me and whispered “All over now”. She led me to the bed and hugged me until I had stopped crying.

“Get in that shower and clean yourself up Pippa” she said giving me a playful slap on the bum.

I stood up, bobbed a small curtsy, saying “Yes Mistress” and headed for the bathroom.

That evening we went out for a meal and then onto a pub for what I thought was to be a quiet drink. kurtuluş escort The pub however was very busy and after a few minutes at the bar it seemed to be a bit of a pick up place for singles. The others reassured me that it would be fine. The others hadn’t changed and, apart from my shoes, which I had replaced with my new boots, I was wearing the same outfit as before. In addition to showering I had also shaved my face again and reapplied my make-up.

A quiet drink was out of the question. In spite of my excellent ladylike behaviour soon we attracted the attention of three guys. The others assured me that if I behave myself they would look after me. The guys looked a little younger than us, but I didn’t catch their ages or what they did, although I think they might have all belonged to the same rugby club. They bought us drinks and we were soon sat round a table. Although I was being very careful after Jacqui’s warnings, my successful days shopping meant that I was still enjoying the attention and confident I could handle the situation. However quite soon, rather than being six people round a table, the conversations and body language made it clear that we had become three couples.

I was receiving the full attention of Mark. I tried to concentrate on what he was telling me about himself, but he was actually quite boring and I was more concerned with his wandering hands. He maneuvered his arm around me quite subtly and I was taken by surprise as he pulled me gently towards him. He was quite a bit bigger than me so I couldn’t resist without making a fuss, so I allowed myself to be hugged. I kept telling myself ‘he’s hugging Pippa; he’s not really hugging me and I’ve done nothing to encourage him’ while I tried to act naturally. His other hand kept resting on my thigh, which I could cope with, but every now and again it would try to slide up, under my skirt, which meant I had to find excuses to move and move his hand back down. I was also trying to keep an eye on my wife, Jacqui, who was getting very close to her partner for the evening.

A trip to the loo, while the guys brought another round of drinks gave me the chance to regain my equilibrium.

“Can we go soon?” I asked hopefully.

“Nope” said Hilary flatly. “We’re all having a good time and you were happy enough to tease that shop assistant. Now the tables are turned and you’re the one feeling uncomfortable, tough, you’ll just have to put up with the attention.”

Jacqui didn’t back me up either. “Dealing with guys comes with the territory as a woman. You were happy enough to be the one in control earlier, now deal with being the hunted.” More reassuringly she added, “Just remember what happened at the hotel and try not to lead him on.”

We returned to our table. One of the chairs had been taken and rather than make a fuss, we were going to squeeze up. Then Mark had an idea.

“Come on Pippa, there’s plenty of room here” he said patting his lap. The others said nothing. If I had refused it would have spoiled the atmosphere. Maybe they were right; perhaps I had to take what my chances. I sat on Mark’s lap where he held me with his arm round my waist and my arm round his shoulders. I felt so helpless perched on his lap. I wasn’t even too heavy for him. I shifted around, trying to get comfortable.

“Oh I like that Pippa, you little tease!” he whispered in my ear. Damn, he thought I was wiggling my bum for his enjoyment. I didn’t know what to say, so I said nothing, smiled, and took a sip of my white wine.

When he wasn’t drinking his beer, Mark’s free hand resumed its exploration of my thigh, a task made easier by the fact that I was on his lap and that my skirt was riding up all the time. I had to tug on my hemline almost every ten seconds. It was then I began to feel confused. I was wishing he’d stop, but at the same time, enjoying the feeling of having my smooth legs stroked through the silky material of my tights.

I looked towards Jacqui, hoping to catch her eye and then she’d know I wanted to leave. She was staring intently at her new admirer, just about to share a passionate kiss. I was on my own. Mark hugged me a little tighter and his had stroked my thigh again. I move about on his lap again. He groaned. Then I realized. Pressing hard against my bum was a distinct bulge between his legs. He had an erection and was rubbing it against my bum!

Perhaps it was the wine, perhaps it was the heat of the room and the tightness of my tight, constricting underwear or perhaps it my latest discovery, but I began to feel faint.

“I’m sorry Mark, I don’t feel well, and I need to go outside.” I said in a voice that sounded weak and feeble, even to me.

“OK Pippa, your wish is my command” he said. Instead of letting me go, he stood up sweeping me into his arms and proceeded to carry me outside, putting me down gently on a bench and then sitting beside me. I felt so helpless, my head resting on his shoulder, tears welling in my eyes. He was being so nice, I thought.

Then turned and kissed me, full on the lips, firmly and intently. I was powerless to stop him. He must have thought I was making an excuse to be alone with him, I thought, perhaps I had been sending out too many of the wrong signals. Our lips parted and he took my hand and held it on his crotch.