Sally and the Entertainer
written by:
Carole

Sally part 1: The Entertainer

9 months ago, my bloody husband ran off with a younger, brasher model. This had been very difficult to deal with, and I had rattled around at home on my own. However 3 months later my daughter gave birth to my first granddaughter, Sophie, which was just incredible. Of course I doted on little Sophie, and helped looking after her as much as I was allowed!

My daughter, Sam, and her husband, John, invited me on holiday with them to help look after Sophie and give them some time off ... and to look after me as well. I jumped at the chance and it seemed no time at all until we were in the air on the way to Turkey. We landed and settled into the holiday. It was an activity holiday so Sam and John were off playing tennis and cycling during the morning, and I looked after Sophie all morning. At lunchtime, I handed Sophie back and in the afternoon I lazed by the pool, read my book, and occasionally either Sam or John would take me out sailing on a catamaran in the bay.

The meals were included and after eating we would go to the bar and have coffee, drinks and listen to the entertainment. This was provided by an Entertainer who sang songs with a guitar, or ran quizzes, and so on: not very serious, but good fun. The Entertainer was quite good looking, light brown hair, quite tall, and a dozen or so years younger than me.

After settling into the routine for a few days, I was now completely relaxed and loving the holiday: time with Sophie and relaxing in the sun. I had looked after Sophie all morning and then we had lunch together. Sam and John went off with Sophie and I went to the bar for my treat; a real Italian coffee, strong and black. But this time, on a whim, I decided to walk into the village and have one in a café on the seafront. I wandered slowly into the town wearing a simple blouse, long sun skirt, sun hat and shades. My shoulder length grey-blonde hair in a simple pony tail

Half way there the Entertainer caught me up and started chatting. He introduced himself as Andy and asked if I was having a good time. "Wonderful and relaxing," I said. We chatted some more and I invited him for a coffee at the café overlooking the sea. It was a wonderful afternoon, the sun was strong, sky was blue, I could see the sailing boats in the distance and we were in the shade cooled by a breeze off the sea. We drank our coffee and chatted, and I enjoyed the attention of a gorgeous, uncomplicated, younger man. Bliss.

As we left, Andy asked if I wanted to hear a new song he was learning, and so we walked up to his house. He rented a house along with half a dozen other staff from the hotel, and we went into his room at the back of the house, which just big enough for a large bed, wardrobe and a sofa. Typical man on his own, his clothes were strewn all over the room, and he quickly bundled them up and shoved them into the wardrobe. He had 3 different guitars and he chose one and started to play a soft love song.

As he was singing I watched him concentrating on reading the music, with his hair just down over the collar of his polo shirt and a frown on his face, and decided then and there that he was mine for the afternoon. When he finished, I applauded, then got up, stood over him and holding his upturned face in my hands, kissed him. He looked surprised, especially when I opened my mouth for a lovers' kiss, and he responded with enthusiasm.

I took the guitar out of his hands, placed it on the sofa and then sat on his knee. Andy held me tightly around the waist and kissed me hard, his tongue exploring me deliciously. I had one hand around his neck playing with his hair and then dropped my other hand into his lap and felt for his cock which I found already hardening. He jumped slightly and then carried on kissing me, perhaps more urgently.

My body was responding to more attention than it had had for months, and I could feel the warmth in my pussy. My breasts are fairly small, but my nipples can get very long and they needed some attention: on cue, Andy reached up, cupped my breasts, and then tweaked and pinched my nipples. "Arrghh, mmmm" I gasped and buried my face in his neck; "don't stop ..." I was getting seriously turned on, and remembering how horny I'd been through lack of attention these past months.

Andy carried on kissing and nibbling my neck, while massaging my breasts, bringing my nipples up to full hardness. This was too much and I could smell the aroma of my pussy as my knickers were getting wet.

Now I needed some fun, so I stood up, pulled Andy's polo shirt off, pushed him back on the bed, unzipped his shorts, pulled them and his pants down, and his gorgeous hard erection sprang out. Savouring the sight of his large, purple headed, cock for a moment before I licked up from his balls to the head, and then lowered my mouth over it. My tongue swirled around the top of his cock and then I slid my lips slowly up and down his shaft. I couldn't get all his cock in my mouth, which boded well for later! It had been a very long time since I'd had a nice cock to suck on. Andy lay back on his elbows watching me and luxuriating in my ministrations.

Eventually he grunted as a sign he was getting close. I wanted him inside me, not cumming in my mouth, so I stopped and Andy shucked up to the middle of the bed. He watched as I stripped, and then I crawled up the bed, knelt either side of his thighs, lifted his cock up, rose up, located the head in the open, wet, entrance to my pussy and then sank down uttering a primeval deep contented sigh. God it had been a long time since I had a nice hard cock inside me - especially belonging to man I liked! And a big cock too!

I sat straight upright with my hands on his chest, playing with his sparse chest hair; I wanted a long slow delicious fuck, so I rocked my hips on his cock. It moved inside me, pulling on my clit and just fast enough to slowly move me towards my orgasm.

Keeping up the rocking, I leant forward to kiss him and nibbled on his nipples, before returning to upright. Andy played with my nipples, tweaking and pulling them in time with my rocking. My breath was starting to become ragged, and I couldn't help sighing in time with my motion.

"Oh fuck, I'm getting close ... I must ... need to ... go faster ..." I got faster and faster, still rocking back and forwards and then round and around. I fell forward onto his chest, and started lifting off his cock and slamming back down again. "God, this is too much ..."

Suddenly my orgasm rushed over me, and my pussy clenched hard on its prize again and again. I couldn't help screaming a little with my face buried in his neck. It had been so long. My orgasm seemed to go on and on, as my legs were now straight out behind me and my body was rigid, bouncing on his cock.

Suddenly I relaxed as my orgasm flowed away into the distance, and I went limp on top of Andy; still impaled on his cock, and whimpering softly. As I came to, I was aware of a very hard cock still inside me. I got up, turned around, kneeling on the bed and presented my arse to Andy. He quickly located his cock inside my pussy entrance and pushed hard, lifting me off the bed. He started fucking me hard and fast. "Come inside me," I ordered.

He kept thrusting until he grasped my hips harder, thrust sharper, lifting me off the bed as his first jet of cum squirted inside me; followed by more thrusts until he slowed down and he collapsed pulling me down onto the bed, holding me tight to him as his cock softened. He was breathing hard into the back of my neck, "God that was awesome, thank you. It's been a long time." "Yes, it has for me too," I said. We lay in sweet contentment and what seemed like an awful lot of cum dribbled out of me.

Eventually I needed to go, so I got up, grabbed a handful of tissues to make myself decent, and dressed as he lay and watched. He got up to kiss me as I was leaving, still nude with his cock now hanging down. I turned, "Can I come back tomorrow?" Now I'd found a man, I needed him regularly. "God, I hope so," he said, holding my head and kissing me. "Until tomorrow ..."

I walked slowly back to the hotel, savouring the feeling of having just made love. Swinging my hips slightly more than normal because of the sex, and with deliciously damp panties and a permanent smile! I got back to the hotel, and sneaked up to my room for a shower, washing the smell of our love-making off me, before going back down to take over babysitting duties.

We had a nice meal and a lovely relaxed evening. Andy played his guitar, including his new song which he dedicated to "all the lovers in the audience," looking straight at me! I wandered upstairs early and had a long refreshing night's sleep.

The next day was similar: I looked after Sophie all morning and then we all had lunch together. Once Sam and John had gone, I walked back into town and up to Andy's house. Luckily all the other staff were out of the house so I got into his room unseen. I rushed up to Andy and pushed him down on to the bed, kissing him hard. We rolled on the bed enjoying kissing each other and the feel of each other's bodies. I rolled on top of him, locating his hard cock against my pussy through my skirt, and enjoyed gently rubbing my pussy on him. I was feeling very horny again and my pussy was already wet and ready to go further.

I undressed and lay on the bed, I wanted to feel Andy and his weight on top of me for a real fucking. Andy undressed and his lovely cock sprang in to view. He knelt down, and pushed my legs apart, pulling me down towards him.

He gently opened my lips with his fingers and then licked up from the bottom up to my clit, swirling his tongue around it. "Arghhh," I grunted pushing up to get more pressure, "fuck that feels good." He set to eating me out. First licking up and down my lips, then teasing them apart and thrusting his tongue inside me, then sucking on my whole pussy, then rolling my clit around with his tongue. He never kept up one thing for long before moving on. He pushed his fingers inside, rotated them and started massaging my g-spot, then used them to push down against my whole pussy.

"Oh god, yes ... don't stop ... fuck that feels good ... mmmm," I was blathering as he worked on me, not too fast and not too slow. The warm feelings in my pussy were growing, and I could feel my orgasm starting to grow deep inside me.

I was now thrusting up in time with my feelings, as he fingered my g-spot and licked my clit. "Yes, yes ... for god's sake don't stop ... I'm cumming ... ngghh ... fuck," then I screamed as he tipped me over the edge and my pussy clenched on him as my orgasm washed over me. He kept on fingering me and kept my orgasm going until I had to push him away - too sensitive.

"Now, fuck me, please," I begged. Andy pushed me up the bed, held his cock down to the open entrance of my pussy and pushed straight in up to the hilt. We both grunted as he hit home. I grabbed his arse and pulled him close, my thighs up in the air on either side of him. Andy took his weight on his elbows and started fucking me hard, pulling almost all the way out and then slamming in again to the hilt.

He kept going until his thrusts got a little more urgent, grunted and then suddenly thrust sharply, jetting his cum deep inside me. This was just enough for me to have another mini-orgasm as he filled me up. He collapsed to the side holding me close and breathing hard. I could feel his cock still jerking slightly as he relaxed down and we cuddled close, not needing to say anything.

There's nothing like holding a man close, his cock softening in your pussy, with the warm glow of an orgasm fading inside you. I relaxed in his arms, contented, as Andy dozed for a few minutes and his cock softened and slipped out of my pussy.

All good things come to an end, eventually I pulled myself up, and dressed while Andy slept. I knelt on the bed and kissed him goodbye, "same time tomorrow?" "Yes please, you angel," he murmured. I walked back to the hotel, with the warm comfortable, slightly sore, feeling you get after good sex; and then slipped back to my room for a shower.

At the airport, I'd gone into Boots and on a whim, bought a small bullet vibrator for my holidays. As I soaped myself in the shower, I thought, well I won't be needing that any more!

For the next ten days, I went to see Andy for an afternoon of love making every day. On our last day, Andy asked me to ride him like on the first day. I enjoy that position and I had a deliciously long slow ride ending in me cumming hard on him. Then as on the first day, he fucked me from behind and then held me close on the bed as we relaxed again.

"Thank you, you've been a life saver. I've not had a good time since my separation and I really needed to be appreciated and loved." Andy chuckled, "and you've done me a world of good too. It's been a long time since I've had an angel in my bed. I'll miss you." "And I'll miss you." "When you get home, you need to find a good man. You're too sexy to stay single." "Thank you" and I kissed him deeply. We dressed and parted slowly, with joy for a wonderful time and sadness that it was ending. We held hands, tight against each other, and then I slipped out of the door.

That evening, Andy sang the love song again, and dedicated it to "all the lovers in the audience," looking straight at me.

The next morning was a rush getting Sophie ready for an early flight and heading off to the airport. Finally as we waited for our flight I sat down for a coffee with Sam, while John walked Sophie up and down to settle her. "So did you have a good holiday? Lots of sun, sea, sand ... and sex?" I asked Sam. She laughed, "well plenty of the first three anyway; Sophie's a good contraceptive!" "And how about you?" "Well I had a great time. I enjoyed babysitting, and of course the sun sea sand," and then added in a low voice "... and the sex." It took a second for Sam to register, "What? You didn't?" "Might have done ... every afternoon as it happens." Sam looked shocked, "Good for you. Who with?" "That, my dear, is for me to know and you to wonder about!" I said patting her arm, as our flight was called.