Probably best if we move on to the rest of the holiday of exploration.

Mike and I left Colin and Emma’s apartment and continued to meet up with them during the rest of the holiday for some more fun, but this story is about how things developed between Mike and myself as well as a couple of the girls we had gone on holiday with.

It was another hot sunny day when we woke in our apartment, Mike and myself both naked in our own beds, I looked over to see Mike looking at me.

‘It’s been quite a few days hasn’t it’, he said, ‘It sure has’ I replied,’ coming on our first holiday as a group of eight young friends, I never really expected to spend my evenings, learning about gay sex and even more strangely spending time with a transsexual and cross dressing into the bargain’, it had been a steep learning curve, but very enjoyable and liberating, but confusing at the same time, I had gone away as a ‘straight’ lad, looking to see if I could get off with a girl and ended up with my best male friend as well as Colin and Emma with her special body.

We decided we should join the others by the pool for the day, so we put our shorts on and grabbed towels and headed off to meet the others. When we got to the pool, there were only two of the girls there, Laura and Janine, so we settled down on the sun beds next to them, Laura is very slim with tight pert breasts, and spiky hair dyed with a tinge of purple, Janine has shoulder length dark hair, and a fantastic slim figure with legs that go on for ever.

They told us how the others had gone off to a bar on the front for an all day session, but they didn’t fancy it, still recovering from the night before, telling us they didn’t get to sleep until about 6am.

I went and got us all a soft drink from the bar and we settled down for the day.

As it got hotter, we all jumped into the pool to cool off and were messing about as you do, but I noticed that Laura and Janine seemed to take every opportunity to touch each other, not intimately, but just a bit more than they needed to. After throwing a ball about for a while, we swam up to the bar and order some more drinks and began chatting.

Laura asked about who we had been spending time with, so I told them we had met a couple, Emma and Colin who we had got very friendly with and apologised for not seeing more of them, but they said they had been fine and had really enjoyed being together, just to the two of them.

As the drinks flowed and the conversation turned sexual Janine confessed that they had been exploring their sexuality and had enjoyed each others bodies on more than one occasion over the last few days; I smiled and said I had noticed the gentle touches in the pool and had wondered if there was anything between them.

As Janine pushed Mike on what we had been up to with Colin and Emma, he confessed that we had all slept together and that Emma was a transsexual, which really got the conversation racing. Laura seemed particularly intrigued about her, but Janine seemed to guess that Mike and I had been intimate and it seemed fair after their confession that we come clean, and I told them that we had in fact got it on together.

As we had a little more to drink, we relaxed and the conversation got a bit flirtier and after a while, Janine said why don’t we all go up to their room, they had some wine in their fridge and we could share that. We quickly agreed, hoping that we would get more than a glass of wine out of the visit.

When we got into their apartment, Laura and Janine got the wine and glasses and we started to make room on the balcony for the four of us when Janine shouted to us, they were planning on relaxing on their beds with us, so no hesitation from us, we were back in the room in a flash, to find that the girls lay down on the one bed, they gestured to us to lay on the other bed next to it, so we did.

As we drank the wine, Janine, began to run her fingers around Laura’s bikini top. Laura pushed out her pert, firm breasts and allowed Janine to reach behind her and unclip her top, pulling the straps over her shoulders to reveal her fantastic smooth breasts, her nipples stood erect. I looked at Mike and he was as engrossed as me, we had known these girls for a number of years and with being such close friends, we never really expected to see them in a sexual act, let alone with each other.

They both smiled at us, before Janine moved and began licking at Laura’s breasts, taking each one in turn, using her tongue to flick around the erect nipples, before moving down Laura’s toned and tanned body towards her tiny bikini bottoms, which she quickly pulled at the tassels on each side to allow them to fall from around Laura, As Janine’s tongue reached her pussy lips, Laura gave out a low moan of pleasure, we were being treated to quite a show and we were getting horny, I could see Mike’s bulge under his shorts, and he began to touch himself, I was in the same situation.

As the girls swapped positions, they noticed Mike and I touching each other, whilst watching them. Laura undressed Janine, revealing the rest of her sumptuous figure as they moved into a sixty-nine position, each licking each others juices. Laura, looked over at us and gestured us to move over and join them, how could we refuse.

Off with our shorts and we quickly joined the girls on their bed, I lightly ran my fingers over Laura’s petite torso, concentrating on bum which was looking stunning, really tight and toned, white against her tanned body. I moved down and began to lick her buttocks before taking them in my hands and separating them to allow my tongue to move in between and lick at her sweet little hole, I herd groans of pleasure coming from her, she was being licked by Janine and me at the same time. I was in heaven so I could only imagine the pleasure that Laura was feeling. Janine moved her finger and pushed against Laura’s anus, whilst I licked around it, giving the moisture to allow the finger to enter and it wasn’t long before one finger was its full length inside. I continued to lick and put my finger against Janine’s and gently pushed in, two fingers from two different people exploring her most intimate area.

Mike who was hard by this time from Laura’s touching, moved around behind me and began fingering my ass; there I was being fingered by my best male friend whilst fingering one of our lifelong girlfriends.

I could feel Mike increase his efforts on my ass, pushing more and more fingers into me, I could feel four, exploring me and opening my hole for the pounding I knew he was going to give me.

As he removed his fingers, I knew what was coming next and sure enough I felt his cock push against me and in it slid, his balls right up against mine as he took me in the most passionate and hard way he had ever done, clearly being encouraged by the girls who were both watching us by this time, whilst touching themselves, they were clearly as turned on by our show as we had been by theirs.

I felt Mike’s cock swell inside of me before shooting his load deep inside of me as I cried out with pleasure. As Mike collapsed against me, the Janine said, I need some of that.

I was thinking that I was going to take her anally, but it quickly became apparent that it was me who was going to be taken again, as Janine grabbed a strap on from the bedside draw, saying, look what we bought yesterday, why do you think we were up until 6am last night, we truly were up, up each other, it was wild.

With this, she strapped it on pushing a shorter section inside of herself, leaving a long hard cock to service me, She moved behind me and quickly entered me, it was longer than Mike and I felt it go deep, deep inside of me, hitting areas that I had never experienced in my short sex life.

She pounded away, whilst Mike lay at the side watching and recovering, as Laura encouraged her to go deeper and deeper, harder and harder, saying to me that I had better get ready as she was next, I was being used by men and women as their anal fuck buddy and it felt great.

Janine cried out in pleasure as the internal section of the dildo clearly brought her to orgasm and she collapsed onto me, shaking with emotion.

After a short recovery time, she withdrew and undid the buckles on the harness and passed it onto Laura who quickly strapped up and was ready to go, so in she went, I must have been wide open by this time, as it slid easily in, the full length, I could feel Laura against me, as she pounded my ass for all she was worth.

I began to get a sensation that I had never experienced before as the dildo rubbed against what must have been my G spot and brought me howling to what I can only describe as an anal orgasm, as she rode me harder and harder, encouraged by the others.

Janine grabbed hold of my hard cock and worked it and it wasn’t long before I was having the most amazing orgasm as I shot my load all over her hand.

As I, totally out of breath, relaxed, Laura withdrew from me and licked up my cum from Janine’s hand, before they both moved to kiss Mike, my cum was being shared orally between my three friends.

It really was turning out to be quite a holiday and my life really was changing.

To be continued……