A Holiday Pleasure

I had been invited by my friend's mother to accompany her on holiday. She was supposed to be going with her husband but work meant he couldn't make it. Jan was celebrating her 45th birthday as well and I was coming up to my 21st so we decided to make it a double celebration.

Jan was 6ft tall with a body to match her height. She had long black hair which she usually had tied back. I was slightly shorter at 5"7 with shoulder length brown hair and a size 10 body. She always we reminded me of the actress Linda Carter who played Wonder Woman.

Finally, we reached our holiday destination on a warm Sunday evening. We had flown to Gran Canaria and got to our accommodation at around 7pm. We were staying in a villa on a complex which seemed to have everything. Our villa was towards the rear of the complex.

It was nicely furnished with a sofa in the main room, there was a bathroom and one bedroom. The bedroom had two single beds which were separated by a chest of drawers. There was also a couple of small wardrobes as well in what was an average sized room.

We unpacked and got changed to go and have a look around. I got changed in the bathroom as I was a little shy. I had never been away with just another female before. I put on a t shirt and jeans while Jan went with a blue skirt and white top. We went out on to the complex and found the bar in the main building.

There was a disco on and there were quite a few people in there. We stayed for a couple of drinks before moving on and having a walk around the area. There were a few bars on the main road and we visited a couple of them before heading back to the villa.

We were both feeling a little tired so once we got back I headed to the bedroom. Jan sat down on the sofa. I stripped off my t shirt and jeans and undid my bra to reveal my 34B breasts. I then slipped off my panties and put on my bed t shirt. I went back into the living area where Jan was sat reading.

"I'm off to bed now," I said.

"Ok goodnight I won't be long, just going to read for a bit." Answered Jan.

I went back into the bedroom and closed the door so the light didn't shine into the room. The beds were typical beds you find in holiday accommodation. The mattress was not that thick and every move on the bed was met with a squeak from the springs. I tried different positions until I got comfortable lying on my right side. I felt myself nodding off to sleep and I was half asleep when I heard the bedroom door creak and Jan come into the room. I watched as she stripped off. I could make out the silhouette of her body as an outside light shone through the thin curtains.

She didn't seem to put anything on so she liked to sleep naked. I closed my eyes and began to drop off again. A noise disturbed my light sleep. I could hear the slight creaking off Jan's bed and then I was surprised what I heard next. There was a slight moan from her and I opened my eyes. I could only see the lower half of her body. The chest of draws obscuring part of my view. What I could see though was Jan's legs open and her knees slightly bent. I could also make out one of her hands between her open legs.

I couldn't believe what was happening, this was something I hadn't seen before. I was no innocent and had pleasured myself many times but always on my own. I could not stop watching as Jan continued her pleasure with her moans getting louder. Her hand worked between her legs until she reached her goal with an intense climax. Her breath was heavy and she got off her bed and went to the bathroom.

I could feel my own excitement building inside as I lay in bed. My hand slid down to between my legs. I could feel the evidence of my arousal and I tried to suppress it as Jan came back into the room. I closed my eyes and eventually dropped off to sleep.

I awoke next morning at around 10am, I noticed Jan was already up and about. I got out of bed and I decided to put on my bikini and catch some sun. I took off my bed shirt and put on my black bikini bottoms and matching strapless top. I made myself some breakfast before I went out into the back garden. Jan was sat on one of the chairs reading her book.

"Morning Kate, you have a good sleep?" Jan asked.

"Yes, it wasn't too bad." I answered.

"You're just going to get some sun then today then? I'm going for a look around the shops." Jan said as she looked at me.

"Yes, just a chill day today." I replied.

Jan headed into the villa while I set up one of the sun loungers. I positioned it in the sunshine and put my towel down on it. I had brought out some sun cream and started applying it to my arms. I continued applying it to my stomach and legs. I had just finished as Jan come back out.

"Do you want me to put some cream on your back before I go?" She asked

"Yes, if you could thanks."

I turned over onto my front and Jan came over and picked up the cream and put some on her hand. I jump slightly as I felt the cold cream against my skin. I flinched again as I felt Jan unhook my bikini top.

"You don't want any strap marks do you." Said Jan as she continued rubbing cream onto my skin.

Her fingers felt nice as they glided over my skin, she rubbed over my shoulders and down my back. Her fingers then slid down my side and I felt her brush against the side of my right breast. She did the same on the other side, again I felt her fingers glide over the side of my breast. She then moved herself down and I felt her hand on my right leg.

"I have already done my legs." I said.

"You can't be too careful." She replied.

Her hand rubbed the cream into my calf and she continued moving up my leg till she reached the top. My legs were slightly open as her fingers moved over my inner thigh. I then felt her finger brush the crotch of my bikini bottoms. Her hand then moved to my left leg and she repeated what she had done with my right leg.

She finished again with her finger brushing my crotch. I wasn't sure what to make of that, was it an accident or was she purposely doing it.

Jan got up and went inside to wash her hands and I stayed laid on my front. I heard her shout goodbye and I then heard the door close. I closed my eyes and I must have drifted off. I woke up and Jan still hadn't come back, I got up to go inside and have a look to see what time it was. As I got up I realized that I was topless as I hadn't put my bikini top back on.

I went into the villa and seen it was just after 12. I got a summer dress from the wardrobe and went back outside. I put my bikini top back on and put my dress on. I was a little hungry so I headed into the main building where the bar was as they did meals. I left a note for Jan and headed off to get some lunch.

After lunch, I went back to the villa, I opened the door and Jan was back. I couldn't see her but there were a couple of shopping bags on the sofa. I could see the back door was open so I walked into the garden. Jan was led on a lounger. She was wearing a pale blue bikini.

"Can you put some cream on my back?" She asked.

"Yes sure." I replied.

Jan turned onto her front and I knelt alongside the lounger. I put some cream on my hand and started to rub the cream into her back.

"Can you untie my bikini top please?" Jan asked.

I untied it and she pulled it off and threw it to the ground. I rubbed the cream into her shoulders and down her back. As she did with me I rubbed cream down each of her sides. I could feel the side of each breast as I did this. For some reason it felt nice feeling the side of her breast's I thought I had finished until Jan requested more.

"Can you do my legs as well please?" She asked.

I moved down a little and started on her right leg. I started on her calf and as she did with me worked my way up her leg. Once I had reached the top I pushed my fingers to the material of her bikini bottoms. I then started on her left leg again starting at the bottom and working up. As I reached her inner thigh she slightly parted her legs. My fingers went up to her bikini bottoms although this time I did just touch the crotch of her bottoms. I got up and got on my lounger after taking off my dress. For the rest of the afternoon we just lazed in the sun.

It got around 5pm when we decided to have something to eat. We both put on summer dresses over our bikini's and headed to the main pool area which had a bar that also served food. We had a couple of drinks after our meal and then headed back to the villa to get ready for the evening.

I went into the bathroom and got myself in the shower. After I dried off I put on my underwear. Nothing sexy though just a blue and white bra with matching cotton panties.

I went into the bedroom and Jan was going through her clothes in the wardrobe. She had already stripped down to just her bikini bottoms and I could just see the side of her breast. She took something from the wardrobe and picked up her underwear from the bed and went into the bathroom. I continued getting ready and I put on a light blue blouse with a blue skirt. Once I was dressed I went into the lounge area to wait for Jan.

I got myself a glass of wine while I waited. It was about 30 minutes later when Jan appeared all dressed up. She was wearing a white strapless dress which came down to just above her knees.

Jan went to the kitchen area and got herself a glass of wine and came and sat down on the sofa next to me. As she sat down we heard a noise outside. I went to have a look out of the window. The noise was rain and lots of it, it just had just started pouring down. I told Jan what was happening.

"Well, I'm not going out in that then," she said.

I went and sat back down on the sofa and took another drink from my glass.

"So, what we going to do now?" I asked.

"We will have to wait till it stops, how much wine have we got?" Jan asked as she laughed.

"Enough for now." I answered knowing there were two more bottle in the fridge.

I wasn't sure what we were going to talk about as we sat there drinking. We couldn't even watch the television as it was all Spanish channels. Then Jan suggested playing a game.

"What we going to play exactly? I enquired.

"I don't know, a game of cards or a game of dare, something like that." She suggested.

I wasn't sure about a game of dare, cards seemed the best of the options. I had brought a deck of cards as we played for a while on the plane till we got bored. I got up and went in the bedroom. After a brief search, I found them and returned to the lounge and sat back down on the sofa next to Jan.

We decided to play Blackjack, and to make it slightly interesting we had some loose change that we were going to play for.

We played for about 15 minutes and by then I had won all the loose change we were playing for.

"Are we carrying on?" I asked.

Jan looked a bit bored already so I was expecting the answer of no.

"Let's make it more interesting shall we," said Jan.

I looked at her blankly as I wondered how it you could make it more interesting.

"Let's play strip Blackjack, that will make it more fun." Added Jan.

I really wasn't sure about this, I was no prude but stripping off in front of Jan. I hesitated before answering.

"I have never played it with a woman before." I answered with a slight stumbling of my words.

"Same rules as if you were playing it with a guy, just get the other person naked." Jan answered.

Jan picked up the cards and shuffled them before dealing them out. I had 17 and decided to stick with it. Jan twisted and got 19. This was not a good start for me.

"Do I have to?" I asked in the hope she would drop the idea.

"Come on get something off," was her answer.

I slowly unbuttoned my blouse as Jan watched and I then slid it over my shoulders and off.

Jan shuffled the deck again and dealt the cards. I twisted and ended on 17, Jan bust as she tried to beat me. She put her cards down and stood up, she unzipped her dress and let it fall to the floor before picking it up. She folded it and put on the back of the sofa. I gazed at her body even though I had seen her in a bikini. Her body seemed to standout more in her white lacy underwear.

Jan dealt the cards and I went for the win and busted. I stood up and unzipped my skirt and let it drop done. I picked it up and put it on the sofa. We were both down to our underwear and this is where it got a bit nervy. I dealt out the cards again and Jan hit lucky with a 21 and that meant I was about to lose an item of underwear. As I went to un clip my bra Jan decided to change the rules a little.

"If you do a dare then you can keep your bra on for now," she suggested.

"What kind of dare?" I asked.

"That would be telling, so which is it strip or dare?" she asked with a smile.

I wasn't sure which was going to be worse, I decided to gamble and go for dare.

"Ok, I dare you to French kiss me." Said Jan.

I didn't know what to say, I wasn't expecting her to suggest that. She could see I was a little shocked at her dare.

"It's just a kiss and nobody will ever know, it's just a bit of fun."

I thought for a few seconds and for some reason decided to do it.

"Ok, let's do it then." I replied.

Jan moved closer to me and put her arm around me, she smiled as she leaned into me. The next thing I knew was I felt her lips press against mine. I responded and our tongues pushed against each other. I felt her hand on my side as we continued to kiss.

Eventually when we broke the kiss I just looked at her. For some reason, it just felt right and so sensuous. My stomach was tingling with excitement as I thought about what I had just done.

Jan moved slightly away from me and then dealt the cards out. This time she was on the losing side.

"Would you like a dare instead?" I asked in the hope that I was going to kiss her again.

"No, it's ok, I'll take it off." She answered.

She reached around and unclipped her bra, she let it fall forward and exposed her breast's.

I couldn't stop looking at her D cup breast's and her large pink nipples. My gaze was broken as Jan dealt the cards again. This time it was my turn to lose and there was no dare option this time. I unclipped my bra and pulled it away from my chest.

My B cup breast's now on show. I was a little more relaxed but that was more to do with the wine I think. I certainly wouldn't have thought I would go through with this game. I wasn't sure how much further I would go though.

The cards were dealt again and my losing streak continued. I really didn't want to take off my panties. I felt that I had shown as much as I wanted too. Jan suggested another dare to keep me from losing my panties. I took the dare option not knowing what I was letting myself in for.

"Being as you can't seem to take your eyes off them, you can kiss and fondle my breast's." Jan suggested.

Again, I was surprised at her dare, I didn't know I had stared so much at them. I moved closer to her lowered my head and started to kiss her breast.

"You have to feel them as well," Jan reminded me.

I moved my hand and began to feel her right breast as I kissed her left one. My mouth was now close to her erect nipple, I took it into my mouth and gently sucked it. Jan gave out a noise which I think was a reaction to my sucking.

I moved across to her right breast and did the same which ended in me sucking on her nipple. I don't know why I did it, it just felt like the thing to do.

I sat back up to see a very smiling Jan as she dealt another hand. I lost again and I was beginning to think this was fixed somehow.

"You can have one more dare." Jan said.

I really didn't want to take off my panties. I waited for what she was going to think of next.

"You have to kiss every part of my body that I touch." Jan dared me.

She put her finger to her mouth, I moved up to her and kissed her. Like the first time it felt nice as I felt her tongue against mine. She broke the kiss and put her finger on her neck. My lips pressed against her soft skin and I kissed her neck.

I pulled back and waited to see where she pointed next. Her finger rubbed on her nipple, I lowered my head and kissed and sucked on her nipple. Next it was her other nipple and I repeated my kiss and gentle suck.

Her finger moved down and she put it on her stomach just above her panties. I moved lower down and gave it a kiss. I thought maybe that was it but she then placed her finger on her right inner thigh.

I dropped down to the floor and was now knelt in between her open legs. I kissed the part of her inner thigh that she indicated. The next was her left inner thigh which I kissed. I looked up at her and thought this was the end of the dare.

Jan put her finger on her right inner thigh again, this time though it was right next to her panties. I obliged and kissed the spot she pointed too. Next was the same on her left thigh. As I did this I kept thinking how close I was to her pussy. Jan then indicated that that was enough and I sat myself back on the sofa.

The cards were dealt and I won and I waited for Jan to ask for a dare but she didn't. Instead she stood up and slipped her panties down to the floor. All I could do was look at what was now on show. Her pussy was trimmed and I tried to stop looking but it wasn't easy.

Jan sat back down and I wondered what happens next as I assumed I had won.

"Congratulations I'd better give you a winning kiss." Said Jan as she moved up to me on the sofa

She put one arm around me and we started to kiss, somehow it felt nice as we kissed. I felt her hand on my side as we continued to kiss. Her hand then moved up and cupped my left breast, her thumb started to rub over my erect nipple. I was surprised what she was doing but it felt nice and it had been a while since I had been touched like this.

Jan broke the kiss and moved her mouth to my neck, she kissed and slightly nibbled on it. She continued to caress my breast and nipple. Her head moved down again until she reached my left breast. Her hand was now replaced by her mouth as she kissed my breast and flicked her tongue over my hard nipple.

She sucked on it gently while her hand moved down my stomach and caressed the top of my legs. There was a mixture of excitement and nervousness as I was breaking new ground. Jan moved across to my right breast and carried on with her kissing and sucking.

Jan sat up and just smiled at me as she moved onto the floor and knelt between my slightly opened legs. Her hands ran up and down the tops of my legs before she started to kiss my inner thighs. Her mouth was now up against the edge of my panties. My excitement was growing as I started to imagine what was going to happen next.

I then felt Jan's mouth press against the crotch of my panties. I gave out a quiet moan as I felt her tongue run along the material. She then rubbed her finger over the crotch and again I gave out another moan.

I was waiting for her to remove my panties but she just carried on teasing me. I lifted my bum off the sofa as a sign I wanted her to take my panties off. She did oblige and pulled them off me.

I was now sat there with Jan looking at my trimmed wet pussy. She wasted no time and lowered her head between my legs. I felt her tongue run along my lips and I moaned yet again. This new experience felt so good as Jan flicked her tongue over my clit.

I felt her fingers playing with my wet hole, I then felt her fingers push inside me.

"Oh yes." I shouted as she started to finger fuck me.

My hands were caressing my breast's as she continued to pleasure me. I could feel myself getting closer until I eventually let loose. I let out a scream as I felt the orgasm travel through me. Jan knelt up and we just looked at each other as I got my breath back.

"How was that then or do I really need to ask?" Jan said.

She didn't need to ask as my orgasm probably said it all.