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The Holiday that changed my life forever (Part 2)

The continuation of my holiday of exploration
After we had cleaned ourselves up a little Emma and I decided to go and shower together, so grabbed a couple of towels and walked to the bathroom, the door was open and we could hear the shower running, we popped our heads around the door to see, Mike and Colin in the shower together, Colin seemed to be licking at Mike’s ass, with the water cascading over them both, quite a turn on but we needed to give them their privacy so we moved into the kitchen area and made some coffee.

Shortly after Colin & Mike came out of the bathroom, still naked, sorry they said in unison, we didn’t realise you were up. Don’t worry I said, totally distracted by Colin’s body, so toned, not a hair on his body with a huge cock dangling down between his muscular legs. They went into their bedroom and put on some shorts returning to join us for a coffee.

Mike looked a little sheepish, so I said to him, I am glad you have had fun, whilst we have been lovers doesn’t mean we are an exclusive couple so if you and Colin become an item, that fine by me, but if you need me I’m here for you, besides I was hardly in a position to comment after the night I had just had.

Colin told me they had lots of fun the previous evening, but couldn’t help but hear us so whilst he already knew Emma’s secret it was fair to say you maybe had a little shock at some point. Your not kidding I responded, with this Mike looked at me, he was the only one of us that didn’t know, Colin said he felt it wasn’t his place to say anything. A puzzled look came across Mike’s face, and Emma obviously thought it right to fill in the gap for him, so she just stood up and removed her towel, letting it drop to the floor. There she was naked, long auburn hair, beautiful breasts, fantastic figure, long legs and a flaccid cock dangling down between them. The look on Mike’s face was a picture as he almost split his coffee, wow, was the only thing that he was able to say. It’s real said Emma, swivelling her hips to make it move about. Mike looked at me and said no wonder we could hear you last night I bet that was a bit of a shock. It certainly was I replied but it turned out to be a most pleasant one.

We finished our coffee and went to shower, Emma stepped in and I followed. As we soaped each other, we both quickly became aroused, I was back into heaven, naked, showering with a she-male, one of the most beautiful girls I had ever seen and her cock was sticking out and against my hard member.

We began to work the soap into each others holes using our fingers, gradually increasing the depth, I could feel myself welling up and almost without warning, I shot my semen all over Emma’s cock. As the water pored down, I licked at her cock, tasting what was left of my juices as Emma suddenly groaned and released her own into my mouth; I swallowed all of her sweetness with a passion that I had never experienced before.

When we had finished showering, we towelled each other down and moved into the bedroom to get dressed.

I only had the clothes I had arrived in the previous night, so Emma suggested that we go via our apartment to get changed but she would like me to wear a pair of her black lacy knickers on below the shorts. After last night dressing I was more than happy to do so.

We chatted with the others and Emma insisted that we go to see her and Colin perform that evening, but in the meantime it would be nice to spend the day on the beach. So we agreed that we would get a taxi back into town and Emma and Colin would wait in a bar whilst we went to our apartment get changed.

When we arrived at our apartments, the others were by the pool so we said hello and explained we had spent the night with our new friends and that we would most likely be away that night as well, they didn’t seem to mind as most of them had paired off we new found friends.

We quickly changed; I made no attempt to hide the lacy knickers from Mike who gave me an admiring glance and said they looked particularly sexy, I’m sure if we had had time, another session with Mike would have developed but we had friends waiting, so off we went, taking extra clothing for that evening.

We met the others and walked down towards the naturist area, a new openness had developed in us, Mike was holding Colin’s hand, chatting as they went, Emma and myself were following on behind, I took the opportunity to ask Emma about her past. She confirmed that she had been born male, but always felt she should have been a girl, taking to wearing dresses at a young age. When she was in her late teens, she consulted a doctor and started taking the hormones with a view to having a full sex change but after her body had changed into the vision I now saw, she became content to stay as she was with the secret in her panties. It was at this time she had moved to Gran Canaria and met Colin in the show and become friends and had stayed for the last couple of years, occasionally working in bars as well as the drag show. I kissed her as we walked along, it was just to say, thank you for being so open with me and the fact she had opened up a whole new world to me.

We arrived at the naturist area and walked back into the dunes to find a secluded spot for us, it was an area hidden from the main view and someone had added a ring of stones built up which gave us additional privacy. Mike and Colin stripped off and lay back on their towels, as I dropped my shorts to reveal the lace panties, Colin noticed and smiled and winked, off they came and I began laying two towels out, Emma then stripped revealing her truly magnificent body, I couldn’t help but notice Mike staring at her body but in particular her male part.

Out came the sun oil and we helped each other with the parts you cant reach, erotic as is was, we all managed to control ourselves and began our relaxing day in the sun, reading, listening to some music and the like.

It was a lovely hot day, cloudless blue sky and just a great feeling to be lying down in the sun, totally naked, no moving of shorts to ensure maximum tan, all of us just relaxing as nature intended, chatting openly about anything and everything. Although we were lovers, in this environment you quickly forget you are naked and just talk to each other as if you were clothed, not really taking any notice of the fact you are naked, it really was a special feeling, and a lifestyle I have continued to follow whenever possible to this day.

We got a light lunch of sandwiches and cold drinks at one of the beach kiosks situated along the area, no need to dress to go and get them, Mike and I simply walked up to the kiosk, everyone was the same.

As the afternoon progressed, the Emma and Colin talked to us about the show and how much they enjoyed the camaraderie of running the show with four others; it turned out to be three guys and one girl, who was a girl. We agreed that we would come along that evening, but it was then that Emma suggested that we should both ‘dress up’ for the evening, between them they said they had plenty clothing that should be suitable back at their apartment and they would find it fun and a real turn on if we would come to the show dressed as girls.

Mike looked at me nervously, so I explained that I had dressed up the previous evening for Emma and found it fun, although to go out fully dressed as a woman was a whole new area, but then this holiday had been about exploring my sexuality so my new phrase became, if you haven’t tried it, how do you know if you don’t like it’ so I was up for it if Mike was. Colin looked at Mike and gave him a little smile and stroked his leg, encouraging him to go for it. It was clearly visible to us all that the thought was turning Mike on, so when he agreed it was hardly a surprise.

As my thoughts turned to dressing up, I could feel myself becoming aroused and Emma and Mike pushed things by discussing the type of stockings and panties they thought would be suitable and the outfits they had, the sexual tension grew in all of us and before we knew it we were all sat there with hard cocks.

We began to touch each others, hands moving amongst us, Mike seemed particularly intrigued with Emma’s so I moved onto Colin’s, it felt good, it was the longest of all of us, it looked fantastic the oil glistening on it, I grabbed some more oil and worked his length with my hand as his did similar with mine, looking across, Mike was moving down to suck on his first girls penis, whilst Emma worked her hand up and down his shaft. What an erotic scene, all of us naked, sat in the sun, working each others cocks and it wasn’t long before we all exploded, semen spurting everywhere including Mike’s mouth as he lapped up Emma’s juices.

As I went for the bag to get a tissue, Mike leaned over and began cleaning me up with his tongue, before moving onto Colin, so it seemed rude of us not to clean him up, so in unison we moved down on him to lick what remained of his cum.

After relaxing for a further hour or so, we decided we had better head back as Emma and Colin had to pick up some outfits for themselves and head off to prepare for the show that evening. We agreed to come along and shower before taking a look through their wardrobe to choose our clothing for the evening.

After coming off the beach, we got a taxi back to their apartment.

Emma and Colin grabbed their outfits and said they would see us about 10pm for the show, but we mustn’t let them down as it would really make the show special to them if they knew we were dressed and in the audience and we must not worry as we wont be the only ones, many dress up to attend these shows, so there will be no embarrassment.

After they had gone, we relaxed on the balcony for a while, having a couple of drinks to conquer the nerves. We chatted about the evening ahead of us and agreed that although we shaved down below, we needed to ensure we had no body hair at all if we were going to be convincing women, so we nipped out to the local store we had seen and purchased some shaving gel and razors as well as picking up some pizza to take back.

Upon return we ate although I must admit my stomach was churning, I was going out that evening dressed as a woman, what if I met one of the gang we came with, would they recognise me, would someone abuse me, all these questions, but talking to Mike, he had the same concerns, but we had both seen many sights around town in the evening so we hoped that our concerns were unfounded and after all we were both keen on a further new experience to our already fantastic holiday.

Anyway it was time for a shower and shave, so we stripped, grabbed the shaving gel and razors and headed for the shower. We helped each other soap up first of all to ensure our skin softened and the pores open and each began applying the gel and shaving our legs, arms and chest, before helping each other the backs and checking we hadn’t missed any areas, I then got Mike to bend over whilst I shaved his anus area and perineum, before turning him around to complete the job on his sac and penis, which was growing as I shaving it. I soaped him all over again and his skin felt so smooth and looked great with his all over tan against his hairless body, the water glistened against his skin. His turn to now finish the first stage of our feminisation for the evening, so he worked his away around any areas I had missed and then opened my ass cheeks and applied the gel and gently shaved the area and then turned my around to complete my balls and cock, I was already hard by the time with the sensations I was experiencing, the tingling as he ensured all my intimate areas were completely hairless and smooth.

We could control ourselves no longer and Mike turned me around and used some shower gel to lubricate my ass and then gently inserted his hard cock into me until his smooth balls hit my newly shaved ass, the sensation was even better than the previous day and as he increased the speed of his action, I was in heaven, masturbating my cock with another one deep inside me and it wasn’t long before he came to a shuddering climax inside of me which sent me of the edge and I shot my juices in the most amazing explosion of pleasure.

We turned to each other and kissed gently, the most sensual of experiences, before we cleaned ourselves and dried ourselves off. We found some moisturizer that Emma had in the bathroom and feeling sure she wouldn’t mind, we massaged it into each others skin, it felt wonderful.

We then moved into one of the bedrooms to look through their wardrobe of female clothing. After searching through, Mike chose some skin tight shiny blue leggings and a pale blue blouse. I went for a light orange summer dress with thin shoulder straps. We then had a look through the wigs and we chose similar collar length light brown wigs.

Moving onto underwear, we found a couple of white corsets that tied at the back, which we agreed would help our figures become more feminine and convincing. I picked out a pair of peach coloured silk panties and matching bra whilst Mike chose something similar in pale blue. As we searched we came across some false breasts that Colin must use to give him cleavage, as we touched them they felt very realistic although we were hardly experts in those days. Further searches of the underwear drawer revealed what I now know to be a ‘cache=sex’ which is worn like a pair of knickers but has control to hold the penis in place between the legs restricting any bulge,

We helped each other into our corsets, pulling them really tight in an attempt to womanise our figures and then each put our cache-sex on and then our chosen lingerie, it was too warm for any stockings plus I wanted to feel any breeze there was against my feminised skin.

It was time for applying some make-up and I have to admit that whilst I had seen my sister applying hers on occasions, I really didn’t have much idea, but fortunately Mike said he had helped his sister from time to time, so he said he would supervise this stage, making me up before taking care of his own needs. Within what seemed a matter of minutes, Mike seemed happy with his efforts and it was time to finish dressing and inserting our artificial boobs into our bra’s before fitting our wigs.

Though I say so myself, we really did look pretty good for two guys, the corsets ensuring we had a more womanly shape with the boobs enhancing our figures so I felt sure that nobody would recognise us. On with our shoes, with a short heel and open back and we were almost ready.

We decided we needed to a bit of a practice walk before we set foot outside so we walked up and down the apartment a few times, watching each other and attempting to give helpful advice on posture as well as looking in the full length mirror in the lounge area.. After a few attempts we felt confident enough that we would be able to walk pass someone without them realising the truth. We then picked out a matching handbag each before leaving the apartment to go down to the street to get a taxi.

As we walked out into the street, I was so nervous, however much we had convinced ourselves we looked good, it is only when someone else sees you that you really know.

We hailed a taxi and told him where we wanted to go and off we went arriving just outside the complex where the club was situated. We paid the fair and walked up the steps and found a bar to get a drink, I think we both needed one, so we ordered drinks in the best female voice we could muster and went to sit down. We got a couple of looks from both sexes but we certainly didn’t see anyone laughing or pointing which helped relax us. Looking around the bar, I noticed a guy and a girl sat down and suspected that maybe she was a he dressed up but they looked good.

After a couple of drinks we moved towards the drag club to ensure we got good seats and as we arrived at the club we were met by two of the act whom we recognised from the previous visit, they obviously didn’t recognise us but greeted us with a smile and showed us to a table near the front which would give us an excellent view of the stage. We ordered a jug of sangria and settled down, trying to sit in a feminine posture. We chatted for a while as others arrived a nice friendly male/female couple arrived and sat on the next table to us. They broke the ice asking us if we had been to this type of show before so we explained we had been to this one earlier in the week and had become friends with a couple of the artists. I think they guessed we were males but took us at face value and continued to chat.

The show was about to start when I saw Emma peep through the curtain from the side of the stage, clearly looking for us, before her eyes met mine, she clearly recognised the clothing and smiled and gave me the thumbs up.

The show commenced and seemed to fly by, the acts were really good and light hearted, Colin and Emma winking at us when circumstances allowed.

After the show was over we were finishing our drinks when Colin & Emma came from back stage still dressed and sat down with us and ordered more drinks. Emma was in a short skirt with a low cut top, showing off her cleavage, Colin was in tight bright pink leggings and what looked to me like a basque type top, both looked really good.

They both seemed really pleased with our efforts and congratulated on us being able to come out dressed up, but as we said this week had been crazy already so it just felt right to go to the next level.

We agreed to go back and spend the evening with them so went outside and got a taxi back to their apartment.

Upon arrival we went out onto their balcony for some more drinks and a chat, Emma again saying how impressed she had been with us having the confidence in ourselves to carry off the cross-dressing. Mike said, whilst it was his first time, it has been a real eye opener and enjoyed the feeling.

I said whilst it had been fun to be dressed up, I thought it was time to free ourselves of our clothing, so we all stripped off and as the balcony wasn’t over looked we had no issue with continuing our evening naked. This obviously led so some arousal which was clearly visible to on all of us, so it wasn’t long before hands started to wander, I was sat between Emma and Colin, so I was touching both, whilst Mike was touching them as well, they were in turn touching us and I then raised my foot under the table to press against Mike’s inner thighs.

Colin moved down onto me and took my cock deep into his mouth before Emma moved down on Mike. After a few minutes of mutual sucking we moved inside into one of the bedrooms and spread ourselves across the bed, mutually pleasuring each other, Colin moved to lick my ass whilst I was sucking at Emma, whilst still licking Colin inserted his finger into my ass, lubricating it with his saliva, I pushed Emma’s legs high over my shoulders as I began to pleasure her beautiful ass, Mike meanwhile was licking at her breasts, it really was the most amazingly erotic scene and my view was of a beautiful young girl, my tongue and finger working her ass as her erect penis stood before my eyes, before I knew what was happening, I could feel a cock pushing against my hole and with the wetness I already had, it slid in quite easily, I moved up and continued to lick and pleasure Emma’s body, her shaven cock, her beautiful flat, toned stomach leading to the most fantastic natural breasts and above them the prettiest face I had ever seen. As Colin continued to pound my ass, I could feel him welling up inside of me, before he shot his warm juices deep inside of me. As he withdrew, Mike took his place and slid inside me with Colin’s juices lubricating his member. There I was, enjoying a most romantic time with Emma, seductive kisses and gentle, intimate and erotic touches, whilst my ass was pounded by the second man in a matter of minutes, it was almost a contradiction in feeling, seductive gentle romantic pleasure at one end whilst wild uncontrolled pleasure at the other. Again I felt swelling inside of me as Mike shot his load.

As he pulled out, Emma quickly moved to my ass to lick the mixture of the guys semen as it dribbled from my open hole. She turned my over onto my back and gave me the naughtiest smile I have ever seen as she inserted herself into me. After the power and lust of the guys, Emma’s love making was different, more controlled and sensual, befitting of a beautiful young girl and as she lay on top of me, she seductively kissed and licked at my chest, lost in the moment I could have easily forgotten about the two guys lay at the side of us, kissing and mutually pleasuring each other as they recovered from their orgasms. I could tell from Emma’s face as she was approaching her climax, her wicked grin, her beautiful eyes seemed to sparkle before I felt her juices explode inside of me.

As she moved off me, the guys began to lick at my still swollen cock and then Emma moved into position, and they took turns in taking me deep into their mouths, I was on the verge of orgasm very quickly and as I released, they all licked ravenously at my juices, ensuring none was wasted.

What an evening I’d had, I’d cross dressed in public, been taken anally by three people and then had my cock sucked by the same three; it was quite an introduction to my fast developing life.

To be continued……..

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com with this note attached, it has been posted without my permission.


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