Sorrento Pt. 03

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A romantic holiday that changes a woman's attitude to sex.
3k words
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Part 3 of the 4 part series

Updated 10/28/2022
Created 11/29/2014
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'I have no idea what to call you,' Anna said. Her voice, soft and gentle, washed over me like a warm breeze. 'Mrs. De Carlo seems a bit formal now ...'

'Now that you came on my face?' I suggested.

Anna laughed. 'I was going to say now that we are lovers, but ok, now that I came on your beautiful face.'

I blushed. 'It's Katherine,' I said, 'but my good friends call me Kat.'

'And do you consider me a good friend?'

'I am beginning to think of you as a lot more than just a good friend.'

There was a long pause while Anna studied me, her beautiful dark eyes somehow reaching deep into my soul. There was an almost insane smile on her face that screamed happiness.

'Okay, my lovely Kat, but now I have to go back to work.' She kissed me, deeply and passionately on the lips, the sensations lingering long after she got up.

I lay on the bed for a while listening to the sound of the shower, then joined her in the bathroom. I apologised that I needed to pee. Peeing was something that I had only done in private since I was a small child, yet having known this woman for less than two hours, it felt natural to sit there while she looked on. Anna was not fazed in the slightest.

I sat and watched while she stepped from the shower and dried herself. She really did have the most beautiful body. I couldn't help but stare at those pert breasts, fascinated how those large brown nipples responded to being rubbed with the towel. When she bent over I had a delightful view of her perfectly formed rounded bum cheeks, and that sweet puckered hole.

'Have you ever had anal sex?' I asked.

Anna looked at me. 'Yes, and no,' she hesitated. 'Apart from some experimenting when I was a teenager, I have not had sex with men, but I do occasionally get the urge to feel something inside me, so I have invested in some toys.'

I sensed some nervousness in the way she was speaking, as if this was something she had never discussed. The fact she was now freely telling me gave me a warm fuzzy feeling. 'Does it hurt as much as they say?'

She crouched down in front of me, resting her hands on my shoulders to keep her balance. There was tenderness in her eyes. 'Have you never tried?'

'I have never done anything. Sex with my husband is the only thing I have experienced, and I now think that has been very ordinary.'

'Sex should never ever be ordinary, my sweet Kat. What is it that you want to experience?'

'That's the trouble, I don't know.' I hesitated, trying to make sense of the thoughts that were racing through my head. 'You have made me realise that there are possibilities that I can't even imagine. I want to experience more, but I don't know enough to tell you what that means.'

She wrapped both arms around me and held me tight. I suddenly felt so vulnerable and exposed that I thought I might cry; something else I had not done, other than in private, since I was a small child.

'I will help you if I can, and I am sorry that I have to rush back to work.' She stood and passed me a bag from the shelf. 'Those are my toys. Please play and enjoy them as much as you wish.'

I unzipped the bag, and pulled out a ten inch replica rubber penis, realistic right down to the pulled back foreskin and veins.

'Perhaps don't start with that,' Anna laughed. She vanished into the bedroom.

I emptied the bag, lining the contents up on the floor next to me. When Anna returned, now fully dressed, she found me studying a six inch piece of black rubber shaped something like a miniature Christmas tree. I think I had worked out what it was for.

'Anal can be painful at first. The muscles down there never get stretched, so the first few times can hurt, but when you get used to being stretched, it can be very enjoyable. If you are able to leave that inside you, it will help.'

I watched while she checked her clothes and hair in the mirror, then stood and kissed her. I wanted to say thank you. I wanted to say that I loved her, but somehow standing there with a dildo in my hand, nothing seemed appropriate. I just kissed her and smiled.

'Ciao,' she called as she slipped out of the door.

I ran myself a bath, and sunk down into its warmth. The combination of alcohol, sex, and hot water should have made me feel sleepy, but I was just excited by all that was going on. A different life seemed to be opening up before me, and it both scared and thrilled me.

I reached over the edge of the bath and picked up the anal toy. With the bar of soap, I gently massaged the entrance to my bum, and then slowly positioned the dildo. The feeling reminded me of Anna probing me with her tongue, which excited me even more.

I pushed slowly. At first it seemed easy. I pushed a little more, suddenly reaching the point where the muscle screamed NO. It hurt. It seemed that less than a quarter of the thing was inside me. I lay there, tried hard to relax, then pushed a little further. Again it hurt, but I held still.

I continued in easy stages. The worst pain came as I reached the widest part, and I honestly thought the muscle would tear. I remembered pain of childbirth, but then there were people standing by with drugs and all manner of surgical equipment. This was all down to me; I had to deal with it alone.

Finally it slipped in, leaving just a circle of black rubber pushing into my cheeks on the outside. It is difficult to say whether the sensation was pleasant or not; I just felt full. That in itself was nice, but I quickly realised making the wrong associations with how it felt would not make it seem sexy.

I stayed in the bath until the water began to feel cold. Bed seemed the most practical place to get warm again, so that is where I headed, grateful that the room was a twin, and I had the option of a bed that was clean and undisturbed. I had drifted off to sleep when phone Rang. It was Anna.

'I am in the back office,' she whispered. 'I'm afraid I cannot talk for long. Someone may come in. Your husband just phoned. I told him that I could not locate you. I hope that was okay.'

'Of course.' I did have a flush of guilt, but I knew that Tom would not have expected me to stay at the hotel all day just waiting for him to call. I was being irrational.

'He left a message,' she continued, 'He said that he was staying over, and would call at 8.00.'

I wanted to scream with delight. Not only did I have the day, but now I had a whole night. A whole night to explore what ever I wanted. The only reason I did not shout, I did not wish to break the magic that seemed to be surrounding me. I could almost hear the smile on Anna's face.

'Will you have dinner with me tonight,' she asked.

Of course I would have dinner with her. I could not think of anything more perfect. The time it would take to speak with Tom would give her a chance to change out of her uniform, and we would meet outside, away from prying eyes. The only difficulty I foresaw was the having to wait three hours.

'Did you try what I suggested?' she asked.

'Oh yes,' I laughed.

'Oh boy. Give me ten minutes and call me at reception. I have to go. Ciao.'

Anna answered on the third ring. 'Buon Giorno. Parlando Anna.'

'Anna, it's me, Kat.'

Good afternoon Madam, and how can I help you?'

I was at first confused, but soon realised that Anna was at the reception desk and giving nothing away. 'You wanted me to call.'

'Certainly Madam, we can help you with that. Do you have the recommendations with you?'

Recommendations. What were recommendations. 'Do you mean the toys?' I asked, 'they are back in the bag in the bathroom.'

'No problem at all Madam, I can wait while you fetch them.'

I jumped off bed and ran. I had no idea what was going on, but I could feel my heartbeat starting to quicken. I was getting excited. 'Okay,' I said, 'but I have no idea what to do.'

'My personal preference is to take several short breaks during the year, rather than one long one, but I am sure we can help you either way.'

I took out the small vibrator. 'Anna,' I asked, 'are we about to have phone sex?'

'Certainly madam. We are always happy to help you with reservations, whether it is in person, or by phone.'

I sighed involuntarily, and felt that now familiar warmth flooding my groin. 'You want me to fuck myself with a vibrator?'

'Of course, madam. A good choice if I may say so. If you would like to give me all your details, I will make sure we have everything properly noted.'

I turned the vibrator on and slid it between my legs. I was already wet and had no problem at all getting the cold buzzing plastic between my lips. I started to tell Anna exactly what I was doing, and how I was feeling, though I am sure that my now laboured breathing was far more expressive than any words.

'Please madam, take your time. There is no need to rush. We want to make sure that everything is perfect for you.'

I could hear a slight hesitation in Anna's voice, and sensed that she was aroused. It made my heart ache knowing she would be stood there, in public, and unable to find any sort of relief, but equally, it made me all the more excited. She was doing this for me.

I pushed the vibrator into my now dripping vagina, upwards so it pressed into my bladder. The vibrations seemed to echo right through my body. It took a few minutes but suddenly I could feel myself getting close.

'Anna, I am going to ...' I couldn't finish the sentence. With the base of my hand pressed hard against my clit, and the tip of the dildo rubbing against my cervix, I came. Every muscle in my body tensed. I shook over and over. I screamed obscenities. I felt warm fluid escaping from me and running into the crease of my bum. I felt wonderful.

'Anna...' The words that were in my head were, Anna, I love you, but I had no idea how to say them.

'Yes Madam, we have all that. Is there anything else we can help you with,'

'Yes,' I stuttered between gasps, 'but you would have to be here in person for that.'

'Then we will look forward to seeing you very soon.'

'Yes, and thank you Anna.'

'You are very welcome Madam, Ciao.'

Anna told me later that she had been so wet she thought it was going to be visible though her trousers, and had to beg another girl to cover her while she ran to the toilet. She confessed that she had to play with herself and had cum, and had to leave the now soaked panties in the waste bin.

We met at the appointed time and walked through the town, arm in arm, talking of inconsequential things as though we had known each other our whole lives. I don't think I could have felt happier. The bar come restaurant that Anna took me to seemed to be owned and run by Anna's uncles, aunts and cousins. Everyone seemed to be related to Anna and to each other, which meant a lot of introductions, hugs and kisses to go through when we arrived.

Unlike a lot of Italian families, they were content to just accept that I was Kat, a friend, and ask nothing more. It actually made me feel very much at home, as if I were eating with family. I immediately relaxed and started to enjoy. Perhaps because the atmosphere was so endearing, the pasta had to be the best that I had ever eaten, and having married into a large Italian family, I had a lot to compare it to.

While we enjoyed our food, and consumed far too much red wine, Anna suggested a game. Pick an ideal lover. The only restriction, it had to be someone we could see in the bar. The contenders were numerous.

Two older gentlemen sat in the corner playing chess and drinking brandy; I argued that their joint tally on years experience outstripped everyone else; Anna rallied that the pot belly's might be a barrier to full and satisfying penetration. Our next, Aunt violet; we were at least able to agree that it would be a delight to get lost and never be found between her enormous breasts, or better still, her thighs. Roberto, the chef, had to be high on the list, because of the sensual way he wiped his face whenever he opened the ovens. We even considered the middle aged businessman, having dinner with what appeared to be a young female secretary, because he looked suave and sophisticated in his designer suit, and hungry for a lot more than pasta.

My favourite though, had to be the young waiter that looked after our table; he had a deliciously tight bum, which showed in his equally tight trousers. 'A perfect choice,' remarked Anna, 'he is my cousin, and he claims that he has never had any luck with women. You could be his first.'

I did not know whether she was being serious or playful, so I asked her for her choice.

'That is very easy. I would choose you, even in a room filled with a million people.'

I immediately wrapped my arms around her neck and kissed her. The sound of mock applause and cheers arose from the surrounding tables and staff. I blushed. There had been several moments in the past eight hours, that had melted my heart, but this had to be the worst. Or best.

I really did not have the right words to express how I felt at that moment. What came out of my mouth was a slightly slurred 'thank you.' I was more than a little drunk. We both were. We sat in silence and held hands discreetly below the table. I felt like a teenager again going through the angst of my very first crush

Anna finally ordered coffee for us. 'I am very glad that you like games.'

'I do, especially ones that I can share with you.'

'That's good, because I had organised a little game for you back at the hotel,' she confided quietly, 'well, more of a party really.'

My mind hung onto the first word. Had. Past tense. It was not hard to know what was going on in her mind; it mirrored mine perfectly.

I thought about the afternoon spent with the stallion. 'When you say party, do you mean that I was going to be fucked?'

Anna giggled and smiled. 'Yes.'

I sat and thought for a few moments. 'If I am going to get laid, then you have to promise me two things. And I mean, absolute, cross your heart, hope to die, promise.' I was definitely drunk.

She looked at me. Those big dark eyes again searching deep into my soul. 'I will give you an honest answer to whatever you ask, but before I can promise anything, I need to know what the question is.'

'Okay,' I said, trying to process the long sentence. 'If I am going to be fucked by anyone, anyone other than you, I need to know that you are okay with it. Because, if you are not, then neither am I.'

She sat, considering what I had said. 'I want to show you and let you experience the true joys of sex. I want to do that while I can watch you and be with you. I want you to know what it is like to be had by men, because that is what you have craved. If you do not do it now, you will continue to crave it, and then you will do it without me being there to watch you and help you.'

'I want you there. I know I will feel safe and protected with you there, but more than that, I want to share that joy with you. If this has become too difficult to share that joy, then I will not do it. I cannot do it.'

Anna swallowed hard. I sensed she was fighting back some strong emotions. I know that I was. 'I promise you that I am okay with it. This is for you my dearest, sweet Kat.

'Then you have to make me a second promise. One doesn't work without the other.'

'Ask.'

'You have to promise that you will stay with me all night. You will not leave my side.'

'What if I have to get up and pee? I am not sure I can go all night without peeing.' She was smiling.

'Especially if you have to get up to pee,' I said laughing, 'that's the most important bit.'

'Then you have my solemn and absolute promise.'

I held my pinkie out to seal the deal. I was not sure that it meant anything in Italian culture, but Anna clearly understood the gesture, and wrapped her little finger into mine. Then she pulled me close and kissed me.

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READ MORE OF THIS SERIES

Sorrento Pt. 02 Previous Part
Sorrento Series Info

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