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"Crete" - Chapter 14:- “Pirates, Advice And Experimentation”

"Don gives David some advice while Sarah enjoys some experimentation..."

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Author's Notes

"Set in 1987, David and Sarah, are on a sexual exploration journey with their older neighbours, Don and Ashley. In this chapter, we find ourselves in a pirate kingdom where Don offers some advice and Sarah starts to give in to her inner slut. <p> [ADVERT] </p>She wants those experiences before the holiday ends and before she has to return to her quiet home life..."

We paid to go into the nude pool area. It was down a twisty path, which was flanked by a few trees and lots of flowering bushes, and within a minute we came to a high green fence; it surrounded the nude pool. Once in. We were told to put everything into a locker, clothes, our towels, literally everything apart from our books, sunglasses and our sun cream. We were left there, standing completely naked other than our flip-flops with two clean pool towels in our hands.

It was with a smile that the attendant then showed us through to the nude pool area itself. It was like walking into a different world.

It was a world of nude people and pirates.

The first thing that struck me was the size of the pool area. Now inside, you could hardly see the high green fence that surrounded us. It gave us privacy and went right back to the cliff face. To break up the fence, there were high palms, other colourful tropical trees and bushes, many in full flower. Their presence made it feel like we were at the edge of a jungle.

To our left, we spotted a small bar in the shape of the rear end of a galleon ship. A couple were sitting there on their towels. Like us, they were completely naked as they tucked into a late breakfast. It was only the staff who wore clothes; they were all dressed as pirates.

I looked at Sarah. She was grinning at what she was seeing and I joined her as the nude pool just seemed so unreal, but it was certainly a place I was going to enjoy exploring.

Considering it was still quite early, it was busy. We walked around, looking for two sunbeds and getting to know our bearings. As Ashley had mentioned to us; they had themed the entire area, just like a pirate’s kingdom. There was a fake waterfall, its water splashing into the cool pool. A diving board made to look like you were walking the plank, and in the pool itself, a small treasure island with three real palm trees growing on it.

The island came complete with a fake opened treasure chest. Its plastic jewels and gold for all to see, and topped off with a large plastic cutlass sticking out of the treasure. It was very well done.  

It was only as we completed our circuit that we saw Don and Ashley; they were waving to us. We walked across and took the two sun loungers next to them.

Sarah and Ashley sat next to one another while Don and I said, “Good morning,” before I took my position on the other end of the four sun loungers, Don and me being the bookends. It wasn’t long before the girls went into conversation mode and as I lay out; I let my mind drift and relax. I was enjoying the ambience of this hidden nude oasis.

After a while, the two girl’s conversation turned into occasional whispers, and Don and I just picked up our books and read. Though I remained very intrigued as to what the two women were now saying privately to each other, especially as every other sentence seemed to end in a quiet giggle. 

Like every day so far, it was another hot one, and we made frequent trips to the pool where we spent some time larking around as we cooled off. It was all good fun, and we had started to really bond with the older couple as it became more like we had known each other for years rather than just for the few days since we arrived here.

I also noticed that Sarah and my all-over suntans were starting to come along nicely as our white areas had now started to disappear, in fact, Sarah’s breasts were already a very nice shade of golden brown and I told her how much I preferred them like that. She smiled before telling me that it would be good for her new modelling career. I thought she was playing with me, teasing me; but with this new emerging Sarah, I was never quite so sure.

I chose the easy option; I just smiled back at her and kept quiet.

At lunch, we went to the pool’s galleon bar where we all had something to eat and our first alcoholic drink of the day, three cold lagers and a cocktail for Sarah. We sat there chatting and eating like old friends, and the fact that we were all nude was unnoticed. It just felt like the norm.

It was after we finished eating lunch that Ashley announced in a low voice that she and Sarah were going back to their apartment for some private girl time.

I looked at Don and he grinned before saying, “Okay, we come by in an hour.”

I also smiled, but at that time I was concentrating more on not getting another erection caused by the idea of Sarah being with another woman.

“We see you later,” I eventually mumbled.

“Make it an hour and a half,” Ashley announced as she looked at a smiling Sarah. That remark turned Sarah’s smile into a grin and it did nothing to help me stop getting an erection. I pulled my chair closer to the table and managed to survive.

With a big grin, Sarah kissed me, and the two girls left. After we finished our lagers, Don and I returned to our sun loungers, with me taking the now vacant one next to him, as I wanted to have a private word.

“Does Ashley normally play with other girls?” I asked. I knew the answer was yes, as it was what she had previously told me. But I was interested in understanding their dynamic, thinking this could apply to me and Sarah in the future; especially if today’s experimentation was a success.

“As you know, David, we have been swinging for many years and as our children got older, we had more of a chance to experiment. So to answer your question, yes, Ashley has always gone with other girls and it has become the norm in the last few years. So you were lucky to have her. I would say Ashley is now very bisexual.”

Don stopped and looked at me; then chuckled. “Don’t worry; Ashley will show Sarah what to do.”

It was a comment that made me start to softly chuckle, as I knew Sarah had been thinking about this for years. So I replied, “Oh, I am not too worried about Sarah; it is more Ashley I thinking about.”

Don looked at me, maybe a little concerned.

“Last night, Sarah told me in confidence that her top sexual fantasy was being with another woman. So I am thinking that Ashley is going to have a very willing pupil in her hands,” I quickly added.

Our neighbour smiled. I didn’t like the fact that I had mentioned this to Don; as it was Sarah’s secret to explore, but I thought this case was an exception. It was all going to come out over the next day and, because of that, Sarah wouldn’t mind.  

“As we have some time, I tell you how we started swinging. It might help you understand us and maybe also with your future.”  

I was not expecting Don to tell me this, but I was ready to listen. After all, wasn’t that what Sarah and I were currently doing?

Swinging with our neighbours.

“It was Ashley who got us started by placing an advert in an adult contact magazine. We were just looking for another local couple to swap with occasionally. It was all Ashley’s idea. As you already know, we were struggling as a couple, mainly because of the affair, but there were other unspoken issues; I know we should have talked before.”

Don went quiet. I was not expecting him to go through it all again, but he was telling it from his perspective, and also from his heart. I was eager to listen, as my greatest fear was that one day I might lose my girls to another man. I felt it was important to learn and understand from someone with experience like Don.

“Even back then, Ashley would look for couples with bisexual wives. So I guess you could say she has always had the desire to be with another woman; though she never had been with one before we started meeting other couples.”

“About ten years ago, when our children were older and could be left at home overnight, we started to go to lifestyle clubs. I should say that up until that point, we only had played with a few other couples, some regularly, who we had met through contact magazines. The lifestyle clubs really upped the number of new partners we met and we started to experiment.”

“I guess you could say that is when we got into swinging and until very recently; it was a big part of our social lives. We were even members of a local swinging group. But, for personal reasons, we just cut back a little on our swinging activities and now it is no more than an occasional bi-monthly visit.”

I nodded in recognition.

“As you know, my wife was the driving force to start with, but now it is more than fifty-fifty, with Ashley now leaning much more towards watching than joining in; and when she does participate, it is now almost exclusively with another woman.”

Don stopped and took a deep breath, his eyes looking at me carefully.

“That is something I prefer, as I never really liked sharing her with other males; but the truth is, I have now shared her many times with other men.”  

That got me reflecting. I was thinking of Sarah, as I felt it was quite likely that she would want to experience another man in the future; even though at that very moment she was exploring sex with another woman.

“I hope you do not mind me asking this,” I stated, and as I did so, I tried to gauge Don’s reaction. It was neutral.

“I have a feeling think Sarah will want to carry on experimenting sexually in the future, and if that is true, it is probably more likely going to be with men than other women. It is with that in mind I ask, has your life together been better since you started swinging?”

Don laughed, “It has been different, and that’s for sure.”

He paused as he collected his thoughts before carrying on.

“You have to remember we only started to save our marriage, and it did help me. It gave me new confidence and new sexual energy after Ashley cheated.”

“Ashley also told me that she needed swinging too; as she liked the variety and our sex life went through the roof. So yes, it did help; and there was something else… I did start to see that sex is just sex and love is something much more important; though I don’t need to tell you, David, that everyone is different.”

I nodded, though I was not sure I really got what Don was saying. I needed a little time to analyse and reflect.

“I tell you one thing,” Don then said. “It is something that has not completely stopped, and that is jealousy; I still get jealous when Ashley is with another man, especially a new man. Yes, it has gotten better than it used to be. I can control it but it did please me when her thing became watching me. That I have encouraged but jealousy, or maybe it is just hurt, is something which is still there. I think it is because there is a small part of me which still has trouble separating love from sex.” 

Don looked over at me and said, “Does that help answer your question?”

“Maybe,” I replied. “Though, at the moment, I am not sure.”

I then added after a little thought.

“I am looking for answers to the way our relationships move forward. But I only just realised having a long-term relationship with two very attractive independent ladies is not easy; especially when I want to keep them both for myself.”

Don chuckled.

I glanced at him. “Maybe I should explain.”

Don laughed again and said, “I look forward to hearing this. I go and get us two lagers and then please do tell me your story.”

A couple of minutes later, Don came back with two cool pints of lager and passed me one. I then drank a quarter of it before I started on what I wanted to stay…

“So with me, as you know, I have two hot girlfriends and you need to trust me when I say they are both equally hot; you have seen the photo of Clare.”

Don nodded as he took a sip of his cold lager.

“I am trying my hardest to pick a path in life to keep both as my girlfriends; until we are all old and wrinkly.”

Don laughed, then apologised, before saying. “Good luck with that. As you know, I only had one, and I nearly lost her!”

“Sorry.” I quickly replied. “I didn’t mean to bring that up!”

Don just waved his hand as he sipped his cold lager. I joined him before pushing on with my story.

“I am trying my hardest to keep them both and in doing so, I am really looking for some good general advice. I just need to talk to someone, someone like you, Don; with experience.”

Don laughed again… “You mean old!”

I smiled. He was partly right.

“Okay, I am listening.”

I went back over the story of how I met Clare in Majorca and this time as Sarah wasn’t there; I didn’t hold anything back, which included our messy and somewhat kinky sex; how I was so instantly attracted to Clare. How we just connected, how I just immediately fell in love with her and how I thought she was the one for me. 

“You love her?” Don both remarked and questioned.

“Yes, but it is more complicated than just that,” I need to explain further.

“Clare is a stunning-looking girl, just like Sarah. I have to say when I met her again, four years later, it surprised me just how attracted we were to each other. I had never experienced that before, even with Sarah, and I am not just talking about lust and sex. I am talking about true love for another, even soul-mates.”

I caught my breath and then carried on, trying my best to explain how I felt.  

“There I was in Majorca, already in love with a girl who I spent only two nights with. I was a little shocked and, importantly, I thought I didn’t have that with Sarah, but I was wrong.”

Don cut me off; then remarked. “That is not so different to me and Ashley, David. We fell in love very quickly too; so I would suggest that your instant attraction and love for Clare is not unique.”

Then Don asked, “Does she feel the same way about you?” 

“Now, yes. However, Clare is more complicated and stronger-willed than Sarah. Before me, she regularly cheated on her long-term boyfriend to sleep with other men, and that includes when she slept with me in Majorca. Clare won’t mind me saying this as she says it herself, but she is a bit of a slut. She has cheated many times on her previous long-term boyfriend; I was not even the first man she slept with on her short holiday!”

“Anyway, since we got back home and are together, she has told me many times that she does love me and, importantly, I not only believe her; I can feel it is true.”

I paused and sipped my lager. “Don, I get to my point about Clare in a minute, but I need to go back to Sarah.”

Don nodded as he drank more of his lager.

“Sarah is slightly different to Clare, and I not talking about looks or personality or even sex. I am talking about her upbringing and her inner beliefs. In a way, Clare has become battle-hardened. She found it tough growing up, moving around the country; her father was in the army and therefore she regularly changed schools, homes and, most importantly friends.” 

“For Sarah, growing up was almost the polar opposite. She always lived in the same home, the same village, with the same school and friends. She is yet to experience the wider world and the temptations it has to offer, yet at the same time it seems that her sexual identity is very much like Clare’s, and I like that!”

“But it also worries me. She needs life experiences to not become jealous of Clare and that is part of the reason why I gave Sarah her sexual freedom; though at the moment we agreed to keep it that way just for this holiday.”

I checked, Don was still sipping his lager but, importantly; he was also listening to every one of my words. I was just getting to the crux of why I was giving him all this information and I needed to make my point. It was important to me, and us, as a future three.

“Don, I didn’t want to give Sarah her sexual freedom, and I didn’t want to share Clare, either. But I had no choice. Clare told me she didn’t want a long-term relationship with me unless she could have sex with others; mainly other women. I had to say yes if I wanted to keep Clare as my girlfriend.”

Don stared at me as if he didn’t fully understand.

“Clare has promised me that she will be honest with me. Tell me everything that sexually happens when she is with other partners. That appealed to me. Also, Clare has found a lesbian partner. An older lady called Brenda. She has become her steady girlfriend. Sarah and I have met her and, importantly, we both like and trust her; so Clare is in expert hands.”

Don smiled and nodded.

“But I felt like I was being put over a barrel when it came to Sarah, as I had to treat both girls equally. So, I found myself giving Sarah her sexual freedom, too. This is part of what this holiday is about, Sarah and me bonding and finding our sexual boundaries; even reconnecting as a couple.”  

“Sarah and Clare are already good friends, and now with both their recent revelations about their sexuality, it has made me realise there is hope that they could be soon lovers. I would like that!

“That’s why I said Ashley may have a very willing pupil today and that’s why I am hoping Sarah and Clare will start having regular sex together. That way, our three-way relationship triangle might become more equal and balanced.”  

“It is a hope I have for the future; a three-way harmony…” I smiled and then added a rather salient point. “I am also not sure in the future if I can keep up with the urges of two very sexual girls.”

Don chuckled. Then took a large gulp of his beer before stating an unfortunate fact. One I tried not to think about. “You have to choose between them one day, as you cannot marry them both!”

I smiled. Maybe I was in denial as I wanted to marry them both, and that wasn’t going to change.

“I know,” I quietly replied, though I wanted to say something different.

“But my first hurdle is keeping them both as my girlfriends, and it’s why I am asking for some advice. With Clare, I not worried about her as much as I am Sarah.”

I paused, and I looked down and it appeared that our lagers had both evaporated in the early afternoon sun. I needed a drink before I continued as the next part of what I was going to say I was still wrestling with in my mind.

I went and bought two more cold ones. The fact that both Don and I were completely naked had long since been an issue. It now felt perfectly normal.

After a long sip, I carried on. “Sarah and I had a long chat last night when we got a little drunk, and then this morning we repeated most of it, sober. Our discussion covered many sexual desires, including Sarah wanting to be with Ashley. But that was not the only thing.”

I hesitated, as I wanted to get the next words right.

“Don, while we are here, Sarah and I want to push our sexual boundaries as a couple.”

I looked at Don. I felt certain, and yet also unsure, but I knew it was time to explain what was on my mind. I gulped my lager and its coolness brought clarity.

“Apart from Sarah being with Ashley, there are four things that sexually, from now on, we want to do with you and Ashley.”

“Go on,” Don said, his lager now not so interesting.

“This came up this morning. It was Sarah’s suggestion, but I have agreed with her. From now on, if you fuck Sarah, you don’t need to wear a condom. Sarah doesn’t like them, and I don’t like wearing them either. As she is on the pill and you had a vasectomy, there seems little point.”

Don smiled. “I like that idea, but you still need to wear one with Ashley. That is, unless you had the snip, David, and that is something I find very unlikely.”

I laughed and confirmed I was still very fertile.

“The second is, I won’t be playing with Ashley from now on; that is, unless you want me to.”

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“Why the change?” Don quietly questioned. I noticed a smile had crept over his face. 

“From now on, I want it to be all about Sarah. She didn’t directly request this, but she did express the wish to be the centre of all sexual attention. I think it is because of Clare that Sarah sees this as the chance to explore those sexual fantasies that Clare has already experienced. They are sexual fantasies that she could never do back at home.”

“So the third thing is, as I just mentioned, Sarah wants to be the centre of attention in the bedroom; maybe treated like a slut… but only in the bedroom and by only the three of us. So no Kurt’s and normal rules, no means no; Sarah is in charge and there will not be any overnight stays.”

Don’s smile was now a grin. He picked up his glass of cold lager and then said. “So I can fuck Sarah without a condom whenever I want to.”

“Yes Don, but only at the apartment and most importantly ONLY if Sarah wants sex with you, though after having that conversation last night and again this morning; I am pretty sure she was going to say yes.”

“There is one more thing and this one I have added and Sarah doesn’t yet know about it. It is something Sarah, and I have been talking about, and I will talk to her again later tonight.”

“Go on,” Don slowly said.

The lager he was drinking reminded me of just how dry my mouth was. I took a quick swig of my drink.

“Sarah told me that you wanted to have anal sex with her, but she was not ready; mainly because she has never had anyone back there.”

Don nodded, “Sorry, I should have asked you first.”

“It’s all right Don, Sarah told me and has since asked me to take her anal virginity this holiday, but the more I think about it; the more I like it to be you first.”

As I said those words, I felt my cock come alive; it rapidly started rising, and I had no choice but to turn over onto my front. Don noticed, but I did not think anyone else did.

“This turns you on, doesn’t it, David?” Don joined me as he turned and laid on his front; he obviously had just gained an erection just like me. He was probably thinking of fucking Sarah’s ass.

“I am not sure why, but it is just such a naughty thought; you taking Sarah’s anally first.”

Don chuckled. “Don’t tell me about it; that’s why my ass is now facing the sun too.”

We lay there; each with our own temporary boner, and it gave me the chance to ask Don another question.

“When we get home, Sarah and I have agreed that we will revert to our normal monogamous relationship with Clare as our friend and my second secret girlfriend; though I am hoping if Ashley is successful in persuading Sarah to enjoy lesbian sex, then she can have Clare as a girlfriend, too.”

“She can be very persuasive,” Don chuckled.

I chuckled too. “I hope so; if my girlfriends are more into each other, it just might help me in my quest to keep both of my girls, as my girlfriends.”

“My question is, have you any suggestions to help me in the future?”

“That’s a big question with no straightforward answer,” Don quickly replied.

It didn’t surprise me that he was not going to give me an instant answer; no one could, but little bits of information might help me on my journey. To find the solution to the puzzle of how to make our three-way relationship work.

“For us, swinging has worked, but everyone is different. So I say this with that proviso,” Don said, then added. “If you want to share Sarah with another man, then first you need to talk with her and understand if this is something she really wants. She might not, and this could just be a holiday thing.”

I was pretty sure it wasn’t a holiday thing, but Don might be right!  

“If Sarah does want to continue swinging, then set some rules that cannot get broken or putting it another way, some boundary lines that cannot get crossed.”

“I would suggest that you do not involve friends, families and work colleagues. Keep it to people you just met and maybe set a limit on repeat visits. This will help stop any emotional involvement.”  

I nodded that I understood.

“If you are both still in agreement, then may I suggest you start how we did, through a personal contact magazine. Put an advert describing your requirements, maybe even an anonymous photo.”

“But, be warned!

“If you do that with Sarah, you will get hundreds of men and couples enquiring. You will need to go through those inquiries and sort out two or three that are of interest. Make sure they are not fakes and then go from there. That is a safe and private way.”

“As for controlling Sarah, well if find out the secret of how to control a woman, then please let me know. All I can suggest is to set the rules out carefully and perhaps one of them should be, at least to start with, that you play together and not as individuals.”

I knew that it would be a little difficult to get Sarah to accept, as she had already mentioned that she didn’t enjoy watching me have sex with other women other than Clare.  

“Whatever you do, you need to both be comfortable and, above all, talk to one another. You should have talked with one another before you ever started; as communication will be the key to it working.”

Don paused, then stated. “I think that’s all the advice I can give really, as I said at the start, we’re all different.”

Don was right. Sarah and I needed to talk and to keep talking. I wasn’t sure what would happen after the holiday. I hoped that both Clare and Sarah would just want me and each other, and any swinging notions would just simply fade away. But I knew that was also very unlikely.

I thanked Don and made a note to write this all down in my ever-growing orange 1987 journal.

 

*****

 

When we got back to the villa apartment, both girls were sitting topless together in our small pool. There was a drink waiting for us. Don and I climbed in and sat next door to one another, opposite our two girls. Sarah looked across and smiled at me. She looked flushed.

“Did you both have fun?” I questioned.

They both said, “Oh yes,” and then kissed each other as we both watched. That got both Don and me asking questions, but it soon became obvious that they were not going to give us any more information, other than to carry on teasing us…

In the end, I retorted. “Well, we had fun too,” which caused Don to spill his drink before we all started laughing.

“So that’s why you brought the anal lube,” Sarah giggled.

It set the tone for the rest of the afternoon, where we just talked, fooled around a little and drank quite a few beers and cocktails… either in or around our small, private apartment pool.

 

*****

 

Don and Ashley retired to their apartment at around five-thirty, as they were going into town. We also had the feeling that, like us, they both needed their own time, but one thing both girls told Don and me was that when possible, every afternoon they wanted at least one hour of private girl time.

Don and I looked at one another, which brought out the comment from both girls…

“You can both have your private time, too!”

Later, when Sarah and I were alone in our apartment, I asked how had gone with Ashley. I assumed it went very well by the amount of kissing and touching the two girls had done with each other in the pool, of course, all done to entertain their two men.

Sarah smiled, “She is an excellent teacher,” but chose to say no more.

So I asked again and got a different reply. “She also had a very understanding pupil,” then Sarah giggled, and I thought I would hear no more, but I was wrong.

“I tell you after we have eaten,” and with that, Sarah disappeared to shower and change… alone.

It had become our normal routine.

It was later as we sat on our own in the terrace bar, Sarah wearing her short yellow dress and frequently proving to me, nothing else, that she started to tell me about what her first full-on lesbian experience had been like with Ashley.

“I enjoyed it,” she said. “Remember, it is something I have thought about since I discovered masturbation.”

“What age was that?” I asked as I pulled Sarah close, expecting a nudge, but that never happened.

“Probably about the same age as you,” Sarah quickly replied. She had no intention of telling me.

What six?”

That remark did earn me a nudge, but Sarah laughed too. That was always a good thing.

Sarah then told me very graphically how Ashley and she had sex with one another until they were both completely spent. She went on to tell me that Ashley was very experienced with girls, and because of that, she was a good choice and a wonderful teacher.

“Today, I learned a lot.” Sarah giggled. “I made Ashley cum by just using my tongue, and of course, I came to. You could say it was a very enjoyable experience.” Sarah grinned. “As you well know, we are planning to get together at least once a day for the rest of the holiday.”

That comment made me smile. I was pleased for my girlfriend, that she was now letting herself relax and let go. That she was now experiencing something she had desired, yet suppressed, all her adult life.

After Sarah had finished recounting the girl-on-girl adventure, we started to talk. It was something we both needed to do and perhaps should have done more often during this sexual adventure holiday.

“I guess Clare going to be pleased that you decided that you are now into girls too,” I suggested.

Sarah laughed. “I would not say I am into girls, that Clare’s area of expertise, but I will say this. Now I have had some experiences of being with another woman. It would be something that I am happy to repeat in the future, and maybe quite often. It is just the case of finding the right partner.”  

My cock was fully erect, and Sarah smiled as she saw my discomfort. She leaned over and whispered in my ear, “I guess you will be getting your full girl-on-girl sex show with me and Clare sometime in the future.” 

Sarah then squeezed my cock. “We better get back to our apartment, as I have another hole I want you to fill.” On seeing my reaction, Sarah giggled, “Unless you want Don to go first?”

I hesitated. I suddenly felt sheepish.

Why had I promised Don could take Sarah’s anal virginity?

I wasn’t sure what to say. I started to mumble, and Sarah saw my concern.

She smiled. “You want Don to go first?”

I went quiet, I was thinking. Sarah squeezed my erect cock once again.

“You do?”

“No, I don’t know…” I mumbled, the alpha man now completely deserting me.

“It came up again, this afternoon, with Don. I said he could be first. I don’t know why, it just came out that way.”

Sarah’s hand was still on my cock. She was reading my thoughts.

“It came out that way because you thinking with this.” She squeezed my cock once again and giggled. “Despite my teasing, I want you to be first, David… not Don!”

I looked at Sarah and smiled… She then read my mind.

“I won’t be the first girl to lose their anal cherry… twice!

I laughed and then grinned as we returned to our apartment. I knew Sarah was giving me a gentle reminder to think more often with my head, or something might happen that I might regret. But the truth was, while happy to be the first, a small part of me still wanted Don to have that honour.

 

*****

 

On our arrival, we stripped and rolled around on the bed. Giggling, and laughing as we kissed each other, with me going one step further by giving little kisses all over Sarah’s ticklish body.

“Stop it,” she cried. We were both in a playful mood. We were riding this wave of lust and fun, but more importantly, we were deeply in love, this holiday together being exactly what we needed.

Today we had taken another step on our sexual exploration road. Sarah then went to my bedside cabinet, where she produced the bottle of lube.

Sarah remarked, “I saw it early and I will need it when you take my anal virginity, which I hope will be in about five minutes.”

I smiled and took the bottle.

It pleased me that I was doing this with Sarah before I had a chance to do it with my second girlfriend, Clare, as she was no anal virgin. She had hinted that she had done it with several of her partners, maybe most, though never with her long-term ex-boyfriend, Alan.

Sarah rolled onto her front and pushed her bottom up. “Ashley said you need to lube me first and slightly loosen up my anus before you grease up yourself. Then you need to go slowly, very slowly.”

I grinned. “You have been doing your research.”

“Absolutely; I want to enjoy this and remember it, and let’s put it this way. If I get pleasure, then you can have my ass as many times as you want.”

My grin got wider and my cock nodded its approval, though my twisted mind went straight to Clare. I suspected that I could have her ass as many times as I wanted; as she had told me she loved anal sex. That information I very sensibly chose to keep to myself, even with my ego.

I squirted a generous amount of lube straight onto Sarah’s asshole and she winced before saying…

“That’s cold!”

“Sorry,” was all I could say before adding some more and sliding my index finger easily into her now well-lubricated rear hole. I was eager.

I slowly worked one finger in and out of her, in circular motions, slowly stretching her open. I added a second finger and another dollop of lube and I continued to slowly massage her rosebud, her asshole now starting to gape a little open.

“That feels good,” Sarah purred, her fingers now busily working her clitoris.

I inwardly grinned. I had to get this right, as I wanted to have Sarah’s ass regularly. Anal sex was my thing. So, I added another generous amount of lube, all the time slightly stretching her anus with a finger; every rotation, just a little more, and make her rear opening a little larger.

My cock, now also lubed, was hard, waiting; ready to take the plunge and take my girlfriend’s anal virginity. I placed it at her rear entrance and slowly pushed forward. It was bliss.

Sarah groaned, “Go slowly.” My cockhead probed her rear opening, my brain feeling the euphoria of that sexual feeling as I slowly slid forward, and then a pop. I was inside her. It was ecstasy.

I stopped; waiting for Sarah to relax, my cock now in her, stretching her, wanting to do more.

“Go slowly,” Sarah said. I daren’t move; I was so close to paradise.

I applied more lube and waited to make sure Sarah was okay. Her fingers were still busy rubbing away as she brought herself off for the first time.

“Okay,” she moaned, and I slowly pushed forward. She was tight, very tight. It felt fucking fantastic as inch by inch my cock slid inside Sarah’s ass. To me, it felt like heaven.

I was halfway in. I eased out, as I needed to get this right. So I added another generous dollop of lube, just to be sure. I eased myself in again, slowly, and thought, why had I ever suggested Don to be the first?

Sarah groaned. Had she cum again?

My eyes were now closed, my entire mind now inside my cock, enjoying every little fresh sensation that Sarah’s rectum produced. I pushed. I was three-quarters of the way in, and then I pulled almost out, then in again, right to the hilt, all seven and a half inches.

My girlfriend moaned again. I was now truly fucking her ass. She was no longer an anal virgin, as I moved slowly back and forth; and then, being the pervert I am, I picked up my waiting camera and took several photos of Sarah’s brown hole, gripping me tightly.

Another moan filled the room. She was cumming once again from both her fingers and the new sensations she was feeling in her ass. I carefully fuck her with slow, long thrusts. It felt so good. Her anus was around my cock. It was the best feeling, taboo, but also divine; it was something I could certainly get used to.   

In my head, I asked why we had not done this before, though I knew the answer. We were only doing this now because of Sarah’s new attitude to sex, to try new things, to do things that were deep within her psyche, things that Clare had already experienced.

I felt my girlfriend cum a third time.

Sarah’s tight ass gripping me was having its effect. I needed to hold back from cumming. I let my mind think of different non-sexual things. I thrust in and out, trying my best to keep an even pace, trying my best to delay that moment of climax and keep my well-lubed cock in paradise. My mind was now busy recounting the alphabet backwards, but it was all too much and the blissful sensations won. My nether regions let me know my climax was fast approaching.

My cock twitched. I wanted to shoot my load deep into my girlfriend’s bowels, but I needed to get this right, so I asked, “Where do you want me to cum?”

“On my face,” Sarah moaned. She was in her newfound full slut mode.

And with that, I gave Sarah four or five fast anal pumps before withdrawing completely. She spun around, and I unleashed my seed all over her face as she masturbated, and then she came in a gush, soaking the bed as my jism hit her.

It was my first cum of the night, and squirt after squirt plastered Sarah. She became painted with my semen as she smeared it over her tits. I took another photo, knowing that these pictures like all my others would have to be developed by Brenda, but Sarah didn’t seem to care about the photos and who would see them… she was currently enjoying her sexual bliss.

She was no longer an anal virgin.

Sarah may have looked a mess, but she was happy, especially as she had cum several times before my completion. Sarah licked it off herself and then looked at my cock, then up at me and grinned, her deep blue eyes once again smiling at me.

She took my dick into her mouth and cleaned it, well aware that it had just been in her ass. I was both surprised and turned on. It was so slutty, Sarah knew that, and my cock responded as she carried on working it with her sweet mouth, trying to keep it hard.

This was the new Sarah; a slutty Sarah, pushing her holiday sexual boundaries. Showing me that she could be a slut if she chose to be and at the same time reminding me, she was special.

Sarah worked me with her mouth; I took more photos, and her eyes looked up at me… CLICK… It was an erotic photo, but definitely not one for the family album.

It took her a good ten minutes to get me to cum again. She took the first blast down her throat, but the rest she directed over her. I knew this was what she wanted, and it was then that she told me she was a bit of a cum-queen. I didn’t even know she knew that term, but she then reminded me that this was something she had done quite often in the last couple of months she had been with her previous boyfriend, Jerry.     

As she rubbed in the last of my sperm, Sarah said, “Let’s shower.” We climbed in and washed all evidence of our sexual performance off our now exhausted bodies.

A few minutes later we lay in bed, and Sarah sleepily whispered that today she had set a record for the number of times she had a climax in a single day, but not had a single cock in her pussy since with me this morning.

That got me thinking, as I waited for the number, but it never came.

So I asked, “How many times?”

I did not get an answer, just a mumble. Sarah was sound asleep beside me, and I pulled myself up behind her naked form. We spooned and then I joined her as I drifted off to sleep.

I was happy, contented, and had one of the women I loved in my arms… Sarah.

It had been another fun day… a day of advice and experimentation.

Authors Note:- All characters engaged in sexual acts are 18+  ©2023 wxt55uk. This story may not be reproduced in any manner, without the express permission of the author.

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