Summer Holiday

by Shelley

  

For any of you that have considered replying to a personal ad, it's not always a fairy tale.

 

I replied to an 18 yr old TV who said she liked older guys to fuck. Claiming breasts but still with a penis that was described to me as substantial. Just what I was looking for though 18 was a little young so I am sure some of you will think I got everything I deserve. I forgot how cruel youth can be.

After exchanging some e-mails and I thought established a basis for a friendship and maybe some ground rules, we met in a small tourist town near her city of Rio.

She met me at the airport and to my delight she was truly lovely, slim, beautiful legs and yes, breasts. She was wearing a short blue and yellow dress that showed off her lovely shape, hard to believe that there was anything concealed underneath, I found out later that she had not exaggerated.

I made my first mistake when I greeted her. "Good morning Senhora"

She kissed me on the cheek, smiled and told me that she liked me calling her Senhora and that would be her name for the time I was with her, but I should say it 'A Senhora' This pretty much means Mistress but is always a term of respect. You don't think this is so bad? Well think about referring to the woman you are with as Mistress at all times, in restaurants, "Would Mistress like a drink?" "Mistress would like extra towels for the room" "Yes Mistress, thank you", every situation told the people around us that she was my Mistress and that I was her???????

When we got to the hotel, I filled in the check in form. When I was about to hand it to the receptionist, she very politely asked me if she could sign in. "Yes Mistress of course" In my innocence I thought she was thinking of my privacy…. Boy was I wrong.

She pocketed my card and filled in the new form, When the receptionist asked for her ID card, she smiled brightly and handed the card to the girl, Paulo ___ and a photo of what looked like a 17 year old boy to match the name. The poor receptionists face burned red with embarrassment. I won't tell you about mine. Was this all planned? You bet, they always ask the locals to provide ID if they are checking in.

We went to the bedroom, lovely, great view and a veranda opening directly to the pool.

We unpacked without saying a word to each other and I was just starting to lose my tomato red face.

I finished first and watched as she carefully placed her underwear in the drawers and hung up her dresses. Her huge suitcase was on the bed where I had put it. Can you take those bags and put them on that table.

There were 4 wash bags, all the same, plain black leather. I did as she said. I had thought of asking could I use her girls name instead of 'A Senhora' but I was sure that if I did she would make it worse and probably ask me to call her Senhora Paula.

I put away her shoes and some other boxes and bags that remained unopened.

She kissed me on the cheek again and suggested we go for a walk in the town, then we could come back and play a little before dinner.

I was relieved to be just going for a walk, and despite my fears was aroused at the thought of coming back to play with what I believed by now to be a mischievous minx, no more than that.

She took her little backpack, bright pink plastic like material and off we went but not before she asked me to change to shorts and beach shoes. The shorts she chose were the ones I used for swimming, light material and to me, too short for a walk in town, but, she insisted sweetly with a kiss and a hand brushing across my groin.

The town was a lovely, old and full of character, interesting houses and shops selling gifts and clothes. I knew she was looking for something in particular, her eyes searching in every store that sold t-shirts.

With my arm around her shoulders and hers around my waist, it was easy to forget about the hotel and just enjoy this sensational 18 year old girl that held on tightly and occasionally and discretely brushed her hand against my ass or groin.

As we passed a t-shirt store near the pier, she asked me to wait outside, that she wanted to buy me a present. I was delighted, I had brought her some presents but hadn't given them to her yet, and here she was going to such trouble to buy me one, I was humbled.

After a few minutes she came back out and told me we have to come back in 20 minutes to get it.

I suggested a coffee and I realized again how much attention you can bring to yourself calling someone Mistress. I asked for a coffee and a fruit juice, innocent enough I thought, but she insisted that I inform the waiter who the coffee was for and who would be drinking the juice.

When the waiter arrived "Thank you, the coffee is for me and the Juice is for A Senhora" I think I would like some ice, she said to me. "A Senhora would like some ice please". The look on the boys face….

We went back at the shop, my present was ready, wrapped up as a present, even with a ribbon. I kissed her and said "Thank you A Senhora" and went to open it. No, keep your eyes closed, I'll help you put it on, so right there in the shop, I took off my polo shirt and put on the t-shirt.

When I opened my eyes the shop girl was unable to hide her laughter. I went to a mirror to see myself wearing a bright pink cap sleeved t-shirt with sparkles around the word bitch, also printed in sparkles.

We had talked about me being her bitch, that she would fuck like a bitch and I would like it, so…. Here I was middle of town, wearing my 'Bitch' t-shirt.

She cuddled up beside me and looked anxiously at my face and asked me if I liked.

What could I say so I said "Yes A Senhora"

She kissed me full on the lips, with her hands everywhere that they could go without the shop girl calling the police. I was very aroused and she could see it. She told me we would have to do something about that, and winked at me. I was delirious, I couldn't wait to go back to the hotel. So I made the mistake of asking.

A cloud appeared on her face and I was left to apologize, not knowing exactly why but eventually my pleading for forgiveness got through and she said okay, we could go back to the hotel but that I would have to do something for her. Okay I said anything.

She asked me to close my eyes, I could hear her bag open and something being taken from it. I felt her arms around my waist as she pulled something around, I heard what sounded like the click of a lock and a zip.

I opened my eyes but before I could see she hugged me and told me she wasn't finished. I closed my eyes again and felt her reach up and pull my shorts off. Why I didn't move and then stepped out of my shorts, I can't tell you, I was just so aroused and blinded by her beauty.

I opened my eyes with permission. I was wearing a knee length denim skirt. It was a wrap around and had a leather belt as part of it which was now locked with a small but strong padlock. It was quite flared too long to be mistaken for a pair of denim shorts.

She asked the shop girl who was not even trying to conceal her amusement what she thought. " His hairy legs spoil it" laughing hard. "He needs a pedicure"

A Senhora thanked her for such good advice. The two of them laughing as we left the shop.

It took me a few steps to realize that in my urgency to get away from the laughing shop girl that I was now in the open, wearing a pink t-shirt and a denim skirt. I stopped.

She walked over to the side where there was a step and called me to her. I went over and she put her arms around my neck, this gave me some comfort because I couldn't see the people staring.

She spoke softly in my ear. We were now going back to the hotel and she was going to fuck me, because now I was really her bitch. After listening to her detail the humiliations I was about to suffer, I was again so aroused that I could live with if not forget and ignore this public humiliation.

She took from her bag a pink collar and a small chain. She told me that if I didn't walk proudly beside her and show her how happy I was to be with her and wearing the clothes that she had chosen for me then I would wear the collar and she would lead me back to the hotel where I could pack my bags and go.

I didn't want that to happen, especially the part of leaving. I smiled my bravest smile and said I was sorry and that it was a lovely gift and that she was right, that I should be proud to be her bitch.

We passed though the streets, people stopped to stare, calling friends from the shops (some more discretely than others). I pretended at first that I wasn't bothered, that it wasn't really happening but Senhora wanted me to smile back at them. So I did so and greeted them. It got easier.

I had to go to reception and get the key, a man this time, the owner, he was not impressed that he had a male guest strolling through his hotel in a skirt, he wouldn't have known what the English word bitch meant, but he would see a bright pink t-shirt. I forgot to mention, I was by now carrying the bag, while she held the collar in chain in her hand as a reminder for me.

Back in the room I sat on the bed while she had a shower. I couldn't take the skirt off and saw little point in taking the t-shirt off.

She came out still wet and handed me the towel she had wrapped around her. My mouth opened in surprise and delight. What a body, truly gorgeous, beautiful breasts and to my utter amazement a fully erect 8 inch penis.

She told me that I would like to be on my knees, it wasn't an order, it was an observation.

I was on my knees and staring fixedly at her.

I remembered the towel and started to dry her feet. I worked my way up til I got to her penis and moved the towel towards it. No, with your mouth. I knew there was no way I could take all that so I licked it all over, drinking the water from the shower, sucking in the water in her pubic hair. She asked me to show her how much I could take, and then told me she would teach me to take it all.

She turned around and I locked her ass dry as well. She handed me another dry towel (that I had asked for at reception, for my Mistress) and I finished drying her. I has hoped she would let me lick her breasts, but not this time.

I got her a robe and she unlocked me so I could have a shower. I shaved my legs, arms and armpits as instructed. She came in as I nearly finished to check my work and took the razor to trip my pubic hair, a neat bush, not unlike her own. Just my penis was no where near as big.

When I came out, dried, I was surprised to see the variety of leather straps laid out on the tables, on the floor and a couple on the bed.

She had a massive butt plug in her hand. Can you take this she asked me. I had to say no and thought she would be disappointed. Pick one of these and pointed at 6 butt plugs of different sizes. I picked the second smallest. She smiled and told me that she was going to enjoy opening me up.

She picked up a bottle of oil and started to massage it into my chest, it was heavily scented. After my back and arms I lay on the bed and she massaged the oil into my legs and feet.

She said we would get a proper manicure and pedicure tomorrow but for now I would have to do with a quick dab of polish on my toenails.

I lay back and watched her efficiently apply two layers of deep red polish to my toenails.

As they dried she took from a bag some more clothes, not her style or size I thought. She didn't even look at me while she hung them up, was she so confident that I wouldn't leave?

When she was finished she told me that she had borrowed some clothes from her mamma, she was my age. She smiled as she told me that her mamma was looking forward to meeting me. This was news for me and if I was to meet her mamma it certainly wasn't going to be while wearing her clothes.

She looked so sweet when she turned around, no make up, her long dark hair still damp and loose around her face. Her breasts gleaming with the same scented oil I was wearing.

She walked to me and as I lay on the bed kissed my toes, each one in turn, watching my reaction. She attached a white leather strap to my right leg, with practiced ease that should not be with an 18 year old. As she kissed me along my legs to my hips, I went red as she described my penis as cute, she kissed and said it should have a ribbon.

When a pink ribbon was tied around the base of my balls and penis, with a small bow at the top, laced through my pubic hair to secure it, she commenced kissing my chest. All the while she was talking to me, telling me how she loved seeing me like this, that I tasted salty in some places and very sweet in others, her gentle kisses were hypnotizing me.

I was far too into this to object to the straps placed on each of my wrists and then as she reached my ankle on the left side, a strap was attached there

Where the spreader bar had been I can only guess but now it was keeping my legs apart and securing my hands. I was trussed up like a turkey.

The butt plug I had chosen was now in her hand, she pushed it slowly into my ass watching my eyes, seeing how much it hurt, it did. You should have prepared better she told me, but went on to say that she was glad that I was a virgin. I hadn't said that, but it was true.

I admitted that I was, so she told me she would make my first time very memorable.

She told me to pay attention as she took my penis in her mouth, that I have to learn to take all of hers.

She used the butt plug to massage my prostate and applied a pressure above my penis.

She told me to tell her when I was about to come.

She massaged and explained more about how to suck her cock and it wasn't long before I was breathing rather than speaking when I said I was about to come.

The sharp smack on my balls took what wind was left in me and any idea that I might have an orgasm was gone.

She continued to massage me and suck me until I could feel a small trickle of liquid from my penis, she licked it all and kept massaging until again I needed an even sharper smack on the balls to stop from coming. She said from now on I should just ask her to smack my balls whenever I think I might come. If I don't think one is enough, I should ask for two, and that she would be happier with me if I asked for two, even I thought one would do.

Over the next half hour, though it could easily have been just 10 minutes, I asked to have my balls smacked 9 times. After the last set of two, she asked me if I was sure two was enough, I said no, so she hit me harder than anytime before and stopped everything. I was left gasping for breath and she held my head and kissed me gently. We're going to do that every time before I fuck you, she said and that she wanted me to ask for it and that I should also ask her in advance that if during what she called milking me, that I should ask for my balls to be smacked.

I could tell that she was content, she had enjoyed milking me.

On her instructions I closed my eyes and she removed the butt plug. It was quickly replaced by something else, it was just in a few seconds and it too was replaced.

She was in me, I was being fucked, she talked to me and I talked back, it was hurting I told her, she knew it would but she was happy about that, and she pumped at me and pumped into me as hard as she could. She called me her bitch and I called her Senhora.

She stopped, but hadn't come, I was relieved of the pain but she was still in side me, the sweat on her face, her hair damp from the shower and exertion.

She was going to turn me over, but would have to let my hands be free. I asked could she tie them to the legs of the bed.

With my legs still in the spreader bar and my hands instead of the legs of the bed, they were attached to a collar on my neck, it was uncomfortable and my movements restricted.

Before the collar was locked on, she told me the key was in Rio, and was I sure I wanted it on. I breathed yes Senhora and it clicked into place. I wanted more, at any price.

She was in me again and I was rocking back to meet her thrusts. I thought I would come so I asked her to smack my balls a hundred times, but she just laughed and pushed deeper inside me. I thought I came, but then it happened again. When I had sensations of coming a third time I was confused but ecstatic.

At last I could feel her orgasm inside me, I tried to absorb it into me, holding her.

She slowly withdrew and stepped to the side of the bed to look at me and allow me to look at her. She was smiling so much that I could only imagine that the feelings I had for her were love. Maybe she knew this, because quickly she picked up a riding crop and lashed at my bare ass as hard as she could. I was devastated.

I was left there with my ass stinging as she took a shower.

She look off the spreader bar and released my hands from the collar. We curled up together in the bed and she kissed me, she was smiling and kissed me, I returned her kisses hungrily.

She told me that she will always beat me after fucking me and that I should ask her to. She said she used the crop because it was my first time but that she prefers a braided whip. It hurts a lot more and I should think carefully before asking for it.

I asked her would she like to use it now, she was so happy with my response that she kissed me again. She said no, it could wait til we got back from dinner. She said it as if it was something for me to look forward to.

I had a shower and returned to see her already dressed in a blue dress and matching sandals, no bra. Her hair tied up and a flower over one ear. She was breathtakingly beautiful.

She had been joking about the collar on my neck and it now lay on the bed with the lock beside it.

She put the ankle straps back on and the spreader bar, my mind was racing, we were going to play for longer, I was hungry from the activities of the day but not so much that I would refuse more time with her.

She told me that the denim skirt wasn't suitable for dinner and that I could wear either a dress or skirt and blouse.

I said I would rather not.

She looked so disappointed that I quickly offered to wear a panties and stocking underneath.

She smiled at me and told me I was sweet.

She went to a box and took out a dark blue bikini top and matching panties, I was about to object but thought it best to stay quiet, maybe nobody would notice it under my jacket.

I realized to late that he top was padded and it was already being clipped on when I saw that even with a jacket, it would look like I had breasts.

She was already helping me step into the panties, unclipping one side then the other to get past the spreader bar.

The collar was put back on my neck and a chain attached, she asked me to hold the chain while she put some color on my lips and eyes. I tried to object but I was met with a defiant demand for what did I want, first I refused the clothes she chose for me and now I was refusing to wear a light pink lipstick that nobody would see and would come off when I had my first drink. The eye shadow she insisted that would only serve to highlight the color of my eyes. When she tried the second time to apply the lipstick, I didn't resist. The eye color was applied and mascara and as she said a little blusher to show I had cheeks.

She seemed so happy with her work and by extension with me, that I was sorry I had been so mean.

Her smile was positively beatific as she applied her perfume, I couldn't help but lean a little forward to smell it. I shouldn't have bothered for immediately I was using the same perfume. She told me she wanted me to smell nice always.

With that she opened the door, it was only by chance that nobody was passing, with the light on in the room and the darkness outside, anyone passing would have no choice but to see me wearing a bikini while she held me on a collar and chain.. She hadn't looked to see if anyone was passing, to her it didn't matter at all who saw me.

I begged her to shut the door, but she just smiled and asked why. It was my idea not to wear a dress, she had thought I was being obstructive until I suggested I wear panties. Since she had every intention that I would be wearing panties and a bra, it seemed to her that she was being kind by allowing me to wear her mammas bikini instead. She didn't want me wearing stockings cos that would hide my toe nails

All through this, the door was open and I was in a panic.

So what do you want to do she asked me, do you want the dress I pick for you or not?

"Yes A Senhora"

She told me I was lovely and kissed me passionately before closing the door. She was back to smiling and enthusiasm immediately.

She buttoned up my dress and told me I looked lovely. She had a pair of matching flat sandals in her hands and she started towards the door, it was the drag of my weight against the chain that stopped her.

She jerked the chain fiercely and I moved forwards out the door. Once outside, I anxiously glanced every direction, hoping nobody would see me, she put my sandals on for me and removed the spreader bar.

She asked me if she would need the chain and I replied quietly "no A Senhora."

Her enthusiasm was back in a flash of smiles and she kissed me.

She opened the door and threw the chain and spreader bar back inside. I pointed out that the collar didn't match the dress, she laughed and asked me was I getting concerned about how I looked?

When I replied that a bitch should look her best at all times, she laughed and said I was way too new to referring to myself as her. She returned from the room with a scarf that she wrapped around my neck and I guess to show me that I shouldn't try to manipulate her, she told me that my lipstick didn't match either and proceeded to apply a dark red color that would certainly not come off with the first drink.

We didn't meet anyone as we left the hotel until we were actually walking out the door.

They looked at me anxiously as well they might, I know that it would take more than lipstick to make me look like a woman, nobody we met would even for a moment think I was anything but a man wearing a dress.

It suddenly occurred to me to wonder why she was not embarrassed to be seen with me, so I asked.

I think you look lovely, why shouldn't men wear dresses? Maybe you can start something in the town. She said all this with a big smile but she turned serious and added quietly. In your e-mails you said a lot of things about what you like, what you are afraid of but secretly desire, well, during the next week you are going to experience a lot of the things you desire and some things that are just for my pleasure. When the week is up, you will come with me to my home, meet my family and be able to look back on this week as a fantasy realized.

With that she kissed me and her smile returned.

The evening was lovely, yes lots of people saw me in my dress, all knew I was a man, calling my Lady A Senhora was no longer a problem, paint on my toenails was not a problem, I reapplied my lipstick during the night when she did hers and turned down a couple of proposals though Senhora turned down a lot more. At one point I was in a panic when it looked like she would accept a proposal on my behalf, she enjoyed my reaction so much that she had tears in her eyes.

The rest of the week was just as… eventful as the first day, but I doubt if anyone wants to hear about it.

  

  

  

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