A Day Out Goes Wrong

Hi, my name is Matt and am 25 years old. Early on in my relationship with Lynn I had found out that she enjoyed being a bit more dominant. Not taking control of simple life decisions, but she liked to partially take control of my life. I found out how much control on a sunny but cold autumnal day out.

We had decided to go to a picturesque town at the seaside with a small harbour. Much of the town is hundreds of years old with stories of smuggling, secret tunnels, murder and intrigue. Lynn's friend Donna came along as well, so I thought Lynn wouldn't do anything stupid, surely.

We had been there about an hour in our big coats, visiting a few nice shops and had found a nice place to have lunch, when we went down a side street. It was steep and cobbled. I didn't know what happened, was I pushed or did I just slip? Somehow though, I found myself sliding off the side of the path, down a muddy bank and into a pond. I was muddy and soaked from head to foot.

After Lynn's and Donna's laughter subsided, they helped me out and we carried on down the steep path to the bottom. I was starting to shiver as it was definitely a chilly day.

Looking around us at what shops were about, Lynn spotted a small charity shop tucked away in a little corner next to a ladies clothes shop. It was so dark inside, we didn't even know if it was open until we were right outside. Thankfully it was open, just didn't have any customers until we rocked up.

Lynn went inside to speak to a staff member, a lady in her 70s if it was ok for me to come in, all dripping wet. Quickly I was ushered in and was directed to the small cubical at the back with a curtain for privacy.

Inside, Lynn passed me a large carrier bag and told me to put my clothes in it to see if they were worth rescuing. I had to peel of my clothes off, piece by piece.

Standing in the cubical wearing just my underpants, Lynn poked her head in and said "Are those wet as well?" I nodded that they were.

"Right put them in the bag as well. We are having a look round to find something for you to wear but its a small shop, so not many options." And she was off looking at the limited number of rails.

Donna, kindly and carefully not looking, handed me a towel to dry myself. I was still shivering, but at least the towel was dry and warm.

Lynn knew my sizes off by heart, so she scanned quickly.

I heard her say from across the shop, "Nothing in men's that are even close to your size." My heart sank at that news.

I asked "Isn't there a men's clothes shop nearby?"

The lady behind the counter said, "Sorry, no. The only shops selling ranges of clothes are this charity shop and the posh ladies shop next door. You will have to go to the big town for men's items."

As I dried, I heard Donna ask the lady if they had any underwear?

Lynn called out that just in case I was still wet, anything I tried on, I would have to buy.

Donna came over to the cubical and told me "Sorry, they do not have any underwear at the moment, but this may help." Her hand came round the side of the curtain holding a bikini bottoms. Ordinarily this would have been a good suggestion, but in her hand were bright pink bikini bottoms. My head dropped.

Just then I heard Lynn pipe up "I think we are in luck."

I took ages just getting the bikini bottoms on as they were a funny old style that didn't stretch like modern swimwear. Eventually though I got them right and the little piece of pink material at the front covered my cock....just.

Lynn's hand came round the side of the curtain and she handed me a pair of jeans. Oh thank god I thought to myself. I held them up and something was wrong. There was no zip at the front. There were no pockets either. The zip I found at the side and the material wasn't your normal denim, but quite stretchy.

I asked Lynn "Surely my clothes will have dried a bit, I could put those back on."

Lynn replied "Sorry. Donna had a look and they were disgusting. So she has taken them down the road to bin them!"

I carried on "I cannot wear this, surely it wont fit anyway." Although they were a bit stretchy, I couldn't get the zip to go up. As my bottom half was now covered, I came out of the cubical to show Lynn the problem. Lynn looked at my now only half naked body and laughed at the bulge in the jeans.

"You stupid fool." She said and unzipped me, thrust her hand down the front and forced my dick back between my legs. Without any thought for me, she then yanked the jeans up so the waist was a good few inches higher and then zipped them up properly. My cock and balls were wedged underneath and the front of the jeans were perfectly flat and tight.

Without a second to lose, Lynn grabbed one of my arms and started to put a shirt on me. It was a dark red long sleeve shirt. Once on though, I noticed the material felt very light and the buttons were on the wrong side.

Lynn saw me role my eyes, "It is all they have that will fit you and looks remotely masculine." She said as she did the buttons up. I looked in the mirror and to be honest, I just looked like a guy wearing a red shirt and a pair of jeans. The bottom of the shirt was just long enough to cover the side zip. Lynn looked at my bear feet and was off again.

Soon I was sporting a pair of short pink socks, well hidden though by a pair of Chelsea boots with front laces. To finish off, I was handed a black, leather look, zip jacket. I slipped it on noticing that it didn't have any pockets inside or out.

Lynn looked at me and wasn't happy, the hem of the red shirt was below the jacket. So she tucked the shirt into the jeans waistband and now she was all smiles.

As I had no pockets in either the jacket or jeans, Lynn offered to hold onto my wallet and phone. Before we left Lynn used my debit card to pay the lady, who had quite a smile on her face!

No chance to reconsider, we were off down the road and back to the main shops. As we walked I found the back of the jeans, cutting into my butt crack, working its way deeper and deeper. Waiting in one shop, I felt the back and the vertical seam of the jeans was deep between my bum cheeks. Finding a mirror, I had a look and the jacket hid nothing, my skin tight jeans were clear for all to see. So I wondered how long before I got a funny comment.

Lunchtime came and we went to the place we had found earlier. We just wanted a light lunch as there was a decent restaurant we wanted to try in the evening.

After eating, Donna and I needed the toilet before hitting some more shops. Being the gentleman, I let Donna go first as there was only one bathroom. Once I had relieved myself and got dressed again in the stupid clothes, I went to wash my hands. I literally just touched the tap, the head came flying off and water gushed everywhere, especially on me. I couldn't believe it, I was soaked.....AGAIN!

Lynn and Donna laughed even longer than before as a staff member came running past and stopped the water spurting out. With the jacket unzipped, even the red shirt was sodden. Jeans and shoes were soaked as well.

After Lynn paid for our meal, with my debit card again, I soon found myself back in the small charity shop, peeling off the wet clothes. I put them in another large carrier bag and was again handed a towel to dry myself.

I was seriously miffed, but Lynn, Donna and the lady in the shop were giggling, laughing and all excited.

For a second time I was in the charity shop, naked in the cubical, at the mercy of Lynn to find me something appropriate to wear. Could I trust her? I found out the answer was resounding no.

All I could hear was, "I warned him there wasn't much choice here!" and "He will have to just go with it or go naked!"

I then started to think, 'Did Donna sabotage the tap? And if she did, maybe Lynn had pushed me into the pond.' I snapped out of this thought process as a pair of knickers were passed into me. Donna had been to the ladies clothes shop next doors and purchased, I guessed with my debit card, some underwear.

There dangling before my eyes was a bright yellowy green, almost fluorescent coloured knickers. The front and back were of lace with thin straps to the sides.

"Couldn't you buy men's clothes?" I asked.

Donna replied "You know there isn't a single men's clothes shop in this town."

Still the knickers dangled there on Donnas finger. Trouble was I was painfully aware of my nakedness.

Then Lynn spoke quite loudly "Look, just put them on or go naked, we do not care!"

I dejectedly took them and slipped them up my legs. Annoyingly, being blond, I had hardly a hair to show on my body, arms, and legs. So when I followed Lynn's trick from the morning, folding my cock back between my legs, it looked weird. It looked almost feminine.

Once Lynn was sure I had them on, she whipped the curtain open and pulled me out into the middle of the shop. Her, Donna and the shop lady, all had a good look at me and it seemed like they were having a silent conversation. At the end of it they all were in agreement. Agreement in what, I did not know.

Lynn stepped towards me, "Look, you are ruining this day with all YOUR accidents. We are spending all the time dressing you, rather than shopping for fun and nice things." She lifted one of my arms and started to fit a bra on me. Her expression was the one where you do not argue with her. It matched the knickers in colour and material, with lace cups and thins straps. Clipping it in place, I found it to be comfortable. Oddly it actually felt OK, well more than OK, erm, quite nice in reality.

As my mind was adjusting to the feeling of wearing a bra, Lynn lifted something over my head and directed my arms into sleeves. When she let go of the dress, DRESS!! the hem slid down to between my knees and hips. The material felt amazing.

Lynn could see I was mesmerized. "Its 100% silk and with this tunic style, will hide your body shape."

With the silk dress not being lined, I could see the lumps of my nipples through both the bra and dress. While the lady of the shop was busy with something else, Lynn grabbed my nipples through the material and pinched them hard.

Lynn came close and whispered "No more messing about! OK!" I still thought Lynn and Donna had possibly caused the accidents, but I was not going to start arguing now. So I meekly did nothing nor said anything as Lynn fitted a pair of heeled strappy silver shoes on me. The heels were a good three odd inches and buckled around the ankle. This was followed by a wig from one of the mannequins. It was a blond shoulder length bob.

With me not arguing, Lynn took the signal to carry on. Before we left, I sported a silver neckless and bracelets. Plus a ring that had an adjustable size, so Lynn took great fun squeezing it quite tightly onto one of my fingers.

I quietly asked Lynn "Why are you doing this?"

Lynn replied "Because I can and you would be naked if we didn't, so get with the program!"

There was no talk of a coat, cardigan or jumper. Lynn used my card yet again to pay for what I was wearing and I was pretty much dragged out into the street. The lady of the shop was laughing quite heartily as the door closed behind us.

It was only now that I realised how little protection silk gave against the elements. The cold air whisked around my bare legs and feet. A breeze would send cold up the dress and I could even feel the cold air on my nipples. Either the torture by Lynn or the cold were the cause, but my nipples were like bullets.

The material of the dress swayed as we walked and just didn't hide my nipples that seemed to jiggle as well. I just waited for someone to point and laugh, but no one did.

Lynn and Donna were definitely in the mood for trouble, as we entered a little department store that had a beauty counter. Before we left Lynn had tried a new lipstick on me and had covered me in the latest expensive perfume.

For a good three hours we went from tourist shop to antique shop, from bits and bobs shops to art shops. It was really difficult in the heels keeping my balance on the cobble streets and didn't take long before my ankles ached from keeping me upright. All the while at every opportunity Lynn or Donna would grab one of my nipples hard, squeeze and twist it to make sure it stayed hard.

In our last shop Lynn came up behind me, thrust her hand between my legs and said "So I can tell you like wearing silk. I think we need to make this a regular thing." And with that she pinched my bum through the thin material, so hard, I had to hold back a loud scream.

After a most embarrassing dinner we headed home. All afternoon I had been freezing in the skimpy outfit and only now was warming up from the heat of the cars blowers.

At home Donna left us as Lynn was busy unpacking the bags of purchases. I was too tired to get out of the silly clothes immediately, but enjoyed a cup of tea before

heading to bed. Lynn sat down next to me.

In all seriousness Lynn looked at me and said "You definitely had the most fun today."

I looked at her perplexed that she actually thought that. In the bedroom, I looked for some pyjamas. Normally I have a fresh pair ready on the bed but they were not there so I went to my drawer. I opened it and was shocked with what I saw. Before me were about six nighties, all in satin material and of various colours and styles.

Lynn entered the bedroom "I knew you were enjoying it today, so I decided you needed to try something new."

Dejectedly I took out a black nightie, stripped and put it on. Within minutes we were in Lynn's favourite sexual position. Me on my back, with Lynn's vagina over my mouth and my tongue doing the business on her. Lynn allowed me to pleasure myself while she tortured my sore pained nipples further.

The next day I was in for another shock, to find that all my underpants had been taken and there in the drawer were knickers of many different colours, materials and styles awaiting my use.

I asked Lynn why she had done what she had this weekend?

She looked me in the eye and said "Because I can, and I know you love it! If you are lucky we may do this nearly every weekend."