The Holiday that Changed my life forever (Part 1)

By NatureLover

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Tags: gay, shemale, naturism

Added: 17 May 2012 Views: 21230 Avg Score: 4.88

A voyage of discovery
The story begins when I was on a friends’ holiday a number of years ago, there was a group of us who went to college together, ten of us all together, 6 lads and 4 girls, and we were all good friends and had been through school as well together. Anyway as we approached our final exams, we thought it would be fun to go for two weeks of sun before we all inevitably followed our different career paths.

We arranged to go to Playa del Ingles in Gran Canaria and split into two’s for room sharing, I was sharing with Mike who I known since primary school.

Off we went all in high spirits, all of us enjoying our first holiday away from parents and the first couple of days were mainly filled with late nights just having fun as friends, yes, there is some sexual attraction between the lads and girls, but we’d been friend too long to spoil the friendships, lots of alcohol and long lazy days by the pool.

Sharing with Mike wasn’t an issue for either of us; we had both seen each other naked many times before during showers at school, sleepovers and the like, what I didn’t know at that time was the Mike had thoughts outside of the usual ‘straight’ ones.

My journey of discovery began on maybe the third night, we were all out in the town enjoying some drinks when one of the girls suggested we go to a ‘drag show’, that she had seen advertised around the town, so for the laugh we all went along. It was a great night, really funny show and of course plenty to drink.

After we had returned to the apartments we were staying, Mike and myself sat on the balcony having a whisky night cap, laughing about the show we had just been to when out of the blue he said he was really turned on by the guys dressed as girls and thinking about their cocks being hidden away and what it would be like to get one of these girls back to your room and then find out they had a little more than you bargained for. We laughed about how we would react, but I have to admit it I had had the same thoughts and often wondered about what it would be like to go with a TV/TS. Clearly from the bulge I could feel in my shorts, I knew I had become turned on by the thoughts.

We decided to turn in for the night and as we removed our shorts, it was clear to both of us the effect of the evening and the chat had had on us, both of us stood there with hard cocks, without trying to hide my embarrassment in the situation, I just sat on my bed, but as I did, instead of going to his own bed, Mike came and sat beside me, both of us sat together naked with hard cocks.

Maybe it was the drink but it just felt right, Mike just sat there and confessed to his curiosity about having a sexual encounter with a male, which he said had lived within his thoughts for a number of years, so without hesitation I suggested we have a little play about and see how it went, if it wasn’t for us, we would never speak of this evening again.

With that, Mike put his hand on my upper thigh and smiled at me, I couldn’t believe what was happening, but as I have said, it just seemed right, so I leaned across to him and kissed him on the lips, within seconds we had our tongues inside each others mouths and our hands wondered touching each others erect cocks. Mike’s was maybe 7 inches and hard as a rock, mine was similar. It wasn’t long before, I felt the urge to get my lips around it, so I moved down his chest, licking all the way to his shaven cock, kissing the full length before I took it in my mouth, it was so sweet, the taste of his pre-cum, deep in my mouth. I began to move my mouth up and down on his cock, it felt wonderful, no embarrassment, just pleasure and from the noises Mike was making he was clearly enjoying it as much as I was.

After a couple of minutes of this, Mike controlled a move for us both into a sixty-nine and began to suck my hard cock, and it felt great, this first time a man had had his lips around it, wow. Sucking on his cock, deep down all the way to his swollen balls was so new to me but heavenly at the same time, moving onto his juicy balls, taking each of them in my mouth, I was being swept along on a tide of passion and release, the emotions from both of us being clear as we both came to a shuddering climax, both us of swallowing mouths full of cum.

We lay there for a few minutes as our cocks went limp, before moving to lay side by side, both of us with silly grins on our face, no feeling of embarrassment, or thoughts that we shouldn’t really have done that, we’re lifelong friends after all.

The following morning when I awoke, I could hear Mike in the shower and as the events of the previous evening came back to me, I was initially worried about how we would both feel about the change in our relationship, but as Mike came back into the bedroom, it was clear I need not have worried, he just entered the bedroom, naked and smiling.

We talked about the previous evening and our feelings and agreed that whilst we do want to continue our mutual pleasuring of each other, we both still enjoy chasing girls and really do fancy women, but at the end of the day, our extra activities would remain between us.

After some breakfast in the apartment we went down to the pool to join the others, I remember thinking that the others must be able to tell what we did the previous evening by the way we were, but they couldn’t of course and we just relaxed with the others, laughing about the ‘drag’ show from the previous evening.

As the day progressed, I couldn’t stop thinking about the previous evening and as gradually most of the others went back to their rooms for an afternoon nap, I suggested to Mike that we maybe take a walk down to the beach and have a drink in a beach front bar.

Its wasn’t far to the front and we decided to walk a little way along the beach, just to stretch our legs but as we did, we noticed we were entering a naturist area, but many others were walking along in shorts and bikinis so we just carried on, enjoying the scenery without staring.

I know I shouldn’t have but seeing all the naked couples began to turn me on and could feel a stirring in my groin which whilst trying to control became a little harder went I realised we were into what seemed to be predominately gay couples, relaxing naked on their towels.

Almost out of embarrassment I needed to lie down on my front on the beach to hide my increasing erection so I suggested we make our way up the beach and within some of the small dunes that litter the area. We found an unoccupied area, which was reasonably private and I lay down, but as I did Mike just dropped his shorts and lay down beside me, commenting along the lines of, well this is a naturist area, so why not, are you not joining me?. How could I refuse, off came my short, but I had to continue to lay on my front to hide my by now very erect penis.

Out came the sun cream, each of us oiling the others back, bum and legs, which didn’t help calm my erection, the feel of his hands across my back and the cheeks of my bum, bringing the previous evenings events clearly to my thoughts.

This was my introduction to naturism and it felt good, we lay for an hour or two just relaxing not really taking any notice of others or the time. As the sun got lower in the sky, most of the people we could see from our vantage point had left, we could just see or be seen by one couple maybe a hundred metres or so away and they seemed to be touching each other intimately so I thought, well if they can, they wont mind if we do, so I leaned over to Mike and started to run my finger tips up and down his legs, and onto his beautifully shaped buttocks. He turned his head to me and smiled, so I needed no further encouragement and grabbed the sun oil and poured a little between his cheeks and began to rub my fingers within them, gradually pushing my finger down towards his little bud. I little more oil and my finger slipped into his anus, the groan from Mike told me his was enjoying it and certainly didn’t want me to pull back.

I worked his hole until I could push another finger in, two oily fingers working in and out, pleasure groans coming from Mike.

I checked around to see if the other couple were watching, but they seemed to be too engrossed in their own pleasures, from the distance I was looking, it seemed that the girl was sucking on her partners’ cock, so I thought it seemed a shame not to move our relationship on to the next level. I moved my body on top of Mike and gently slid my erect cock in between his buttocks, entering his deep passage very slowly so as not to cause too much pain. The oil seemed to have done its job and before long my full length was inside, my balls touching his smooth buttocks.

Gradually, rocking back and forth using my full length to give pleasure, and in no time, I could feel my juices building up before I had the most amazing orgasm, shooting my load deep inside my new lover.

I moved back to the side of Mike and gave him a sensual kiss on the lips, both of us smiling uncontrollably, ‘’wow that was fantastic said Mike, but what are we going to do with this?’’, he turned over to reveal his erection, which somehow seemed bigger than the previous evening. Without hesitation I moved my mouth down onto it and began sucking for all I was worth, I needed to taste his cum, and it wasn’t long before he welled up and released his juices deep into my throat.

After a little while we dressed and walked back along the beach towards one of the bars. We sat watching the sun go down, relaxing in a warm glow of our newly found joys as well as the early evening sun. After a little while a guy and a girl sat down at the table next to us and they sat chatting and then the guy said to us, ‘didn’t we see you the other evening at the drag show?’ We confirmed we had been the previous evening with a group of eight others, but don’t recognise them, it was then that they said they were made up differently that night as they were part of the show. When they explained the characters they had played it made us realise they were in fact a large part of the show. They introduced themselves as Colin & Emma and after chatting for a while, they said they had to go and get ready for tonight’s show and would be on late, but they had the following night off and if we fancied meeting them the next evening for a meal and drinks they would like that. We made arrangements to meet and off we went back to our apartment.

Mike and I continued to chat on the way back to the apartment saying how good Colin had look as a woman and that no offence intended we thought that Emma had actually been a guy dressed as a woman with it being a drag show however convincing she may have been, but from her cleavage that we could see in her bikini top, she clearly wasn’t, but both were very attractive when dressed ‘normally’.

We spent that evening with the others in our group, lots of drink and laughs and when we returned to our room, I said I needed another shower as it had been particularly warm that evening so I stripped and got into the shower. I squeezed some gel and began to soap my body, paying particular attention to my crotch and my bum, I have always enjoyed soaping between my buttocks and rubbing my fingers around my ass, pushing them in as deep as they will go, as I continued to feel myself and become aroused I realised that I was being watched, Mike had followed me into the bathroom and was stood watching me touching his rapidly rising cock. I of course invited him to join me in the shower which for a holiday apartment was reasonably roomy.

He didn’t need asking twice and quickly joined me. We added more gel into the mix and began soaping each other, water cascading over us, it felt very erotic and we were both as hard as we could possibly be, Mike went down on my cock, sucking its full length, the water falling over his tanned back. He moved his fingers through my spread legs and began to finger my already soapy hole, I could feel more fingers entering me, maybe three in there, but with the lubrication of the gel it was just pure pleasure. Withdrawing his fingers his strong hands then turned me around and pushed my upper body downwards away from him, to reveal and open up access to my ass. He then entered me gently with his swollen member and the pleasure swept me along in cries of ecstasy, he moved in and out slowly at first ensuring his motion was smooth and regular, progressing to more vigorous movements as I felt his juices explode inside of me, bringing me to the most amazing climax seconds later with his hand pulled around me. We collapsed against each other under the water as it continued to flow over our naked bodies.

After we had cleaned ourselves up we stepped out of the shower and towelled each other down and returned to the bedroom. We chatted about our experienced of the last 24 hours and the immense relief we felt and being able to enjoy each others bodies after so many years of glancing and not being able to touch. After the excesses of the day, we soon fell asleep.

The following day we decided to spend by the pool relaxing and told the others that we had made arrangements to meet a couple that evening for a meal and drinks so would most likely not see the others that evening, I noticed a couple of the girls glance at each other but didn’t say anything.

In the early evening we went back to our room to get ready for the evening, and walked into the town in plenty of time to meet Colin and Emma. We found a bar near to the restaurant we had agreed on and relaxed with a couple of drinks. We chatted about the evening and we both agreed we liked the look of them and wondered if they were a couple or just friends.

We moved to the restaurant ten minutes or so before the time we had agreed and got a table for four and sat down to look at the menu, Colin and Emma arrived shortly after, Colin dressed in knee length shorts and T shirt, Emma in a light summer dress, both with lovely tans.

We ordered our meals and began chatting, we all seemed to get along well, they confirmed they were just friends who had met through the drag show they were in and had agreed to rent an apartment between them for a few months whilst working in the show. After a while Emma asked about Mike and myself as to our relationship, was it time to admit our situation, Mike first of all explained we were with a group and we had been childhood friends enjoying our first holiday away from the confines of parents. Emma pushed the point and directly asked if we were a couple, so I admitted that although we weren’t we had pushed the boundaries and had had some sexual contact in the last few days, just a journey of exploration for us both. Admitting this to them, relaxed us further and allow us to talk a little more openly, Colin confirming our thoughts that he was gay, but did say that occasionally he likes to spend time with girls, Emma saying she was equally comfortable with either sex, I noticed a slight grin on Colin’s face as she said it which had me wondering about their relationship.

As the drink flowed Emma mentioned that they had been on the beach most days and always went for the dunes so they could relax in the naturist area which they found very liberating and we admitted that the day we met in the beach bar, we had been on the dunes for the first time and found it very natural to relax under the blue sky completely as nature intended. I then admitted that we had got a bit carried away and had a little ‘fun’ in the dunes, Emma smiled and told us that she had also on occasions had some sexual fun in the dunes.

It was getting late and the restaurant was closing when Emma suggested we go back to their apartment for a few more drinks and if we liked we could spend the night, they have two bedrooms and they could always share for the evening if we didn’t mind. It sounded like and plan and could be fun so we agreed. The apartment was a little out of town so we all got in a taxi and off we went.

Upon arrival at their apartment, we went inside; it was spacious with a lounge, kitchen diner bathroom and two bedrooms. Colin sorted out the drinks and we went and all sat on their balcony, it was large and not overlooked as far as I could see.

Very quickly the conversation turned sexual asking about our best every experience, Colin told us of the time he had a threesome with two other guys, describing in detail how he was taken up the ass whilst he was inside the other guy. Mike and I both told of times we had with girls in the past but also said how the events on the beach the previous day were right up there with the best. Emma blushed when we asked for hers and simply said that she was still learning and has some fantasies that she would love to play out sometime, but refused to elaborate.

After a couple more of drinks, Emma said to me, you know, I wouldn’t mind trying out one of my fantasies on you, if the others don’t mind sharing for the evening; you can join me in my room, just give me five minutes and come in.

Mike and Colin seemed up for the swap so I left them to go to one bedroom and I went to the other. As I entered, I notice that laid out on the bed was some lingerie, wig and high heels. Not sure what to make of the situation, I went in and closed the door. Emma simply smiled at me and said, I have always wanted to make love to a man who was dressed in lingerie, do you want to make my dream come true.

Well, this has been a holiday of new experiences and the drink had relaxed me, so I said I was up for it if she was, after all despite my gay experiences of the last few days, I had really enjoyed my limited experience with women and had occasionally put my sister knickers on when I was growing up.

I undressed and Emma helped me into the lingerie, it turned out to be a full crotchless and backless body stocking in black with some gold trimmings. It felt good and in the situation it didn’t take long for my penis to become erect and pop out through the crotchless hole. On with the high heels and then as I grabbed the wig, she said, lets put a little makeup on first, so I say at the dressing table whilst she added some foundation, blusher, eyeliner and lipstick, then on with the long auburn wig. She seemed satisfied and smiled at me through the mirror. I do have to say, I looked quite good and felt really horny being dressed up and in the company of such a fantastically good looking woman.

She asked me to walk up and down the bedroom so she got the full effect and difficult as I found it to walk in high heels for the first time, it really did give me a feminine feel. Emma moved towards me and she asked me to lie back on the bed and she moved her lush lips down and licked the full length of my erect cock, paying particular attention to the tip, before moving down and taking me fully into her mouth, her technique was the best I had ever experienced in my young days, I went to heaven and back with the sensations she was giving me, all the while her eyes never left me, and I could tell she was trying to give me a wicked smile.

She asked me to turn over and keep my ass in the air and before I knew it, she was licking between my cheeks, he tongue working into my ass hole, I nearly hit the ceiling with pleasure, alternating between blowing and licking was beyond anything I thought possible, my pleasure squeals must have been heard in the next apartment, never mind by my friends in the next door bedroom.

I needed to give her some pleasure so I turned around and slipped Emma’s dress from her shoulders, to reveal the most amazing breasts, they were perfect with beautiful nipples, that were standing out towards me, I took them in my hands and gently stroked them as I began to lick her nipples, sucking on each in turn, I gently moved down her flat stomach towards her lacy French knickers but as I did I had the shock of my life, as I removed the panties with my fingers, a cock sprung out at me! I fell back on the bed in shock, looking up at Emma; I just saw a really naughty grin on her face. My mind raced back to the drag show when I first saw her, originally thinking she was a man dressed up and then the later meeting when she appeared to be a woman, the grin on her face when she said she was equally comfortable with either sex, she was not kidding.

It took a few seconds to comprehend was I was seeing, there I was dressed in lingerie, looking at a beautiful woman, fantastic figure, amazing breasts and an erect cock pointing out at me.

I simply stuttered, and said,’ I wasn’t expecting that’, I know it sounds silly now but that’s all I could say. Emma explained that she was sorry to have given me the shock but she had never intended sleeping with me, but as that evening had progressed, she has become more and more attracted to me and with the drink she felt it was best if we could get into the bedroom before I found out her secret, particularly after my confessions earlier about Mike and myself.

After this, I realised, I enjoyed sucking Mike’s cock so why not Emma’s, so I gently put my arms around her and hugged and kissed her, reassuring her that it was just a shock and I was still very turned on as she could see. I then moved down her body and took her penis in my mouth; it all seemed so surreal as I looked up at her breasts and into her beautiful naughty eyes. We moved onto the bed and into a sixty-nine position, sucking each other gently, and our fingers moved around to each others bums and we began to finger each others hole, it was the most erotic experience as we both came to a shuddering climax at the same time, I took my girls semen into my mouth, wanting to taste her sweetness, it felt so amazing as I swallowed and then licked her to ensure not a drop was wasted.

We lay there for a while; I was in heaven, looking at a beautiful naked woman, with a now relaxed penis draped against her body, me in lingerie and high heels.

So many questions to ask of her and of myself, but those could wait, no point in spoiling the moment as we breathed in unison, staring into each others eyes as we gradually drifted off to sleep.

When I awoke the next morning, it took a few seconds to bring it all back to me but I certainly had no regrets about the events of the previous evening, everything seemed just perfect, the best of both worlds if you like, a gorgeous woman any man would be proud to have on his arm, but with a special secret.

As Emma awoke, we just lay there, smiling at each other and just looking at her special body my groin began to stir again, I touched Emma’s gorgeous breasts gently, stroking her smooth feminine skin, both our penises began to grow, Emma moved down onto mine and gently licked its full length and then took my balls in her mouth before pushing me upwards so she could move her tongue towards my hole, the pleasure rushed through every nerve in my body as Emma continued to explore deep inside my, her fingers moved in and with the saliva she greased my passage. Before I knew what had happened my legs were up on her shoulders and her cock was pushing against my anus, almost with a pop, it entered me and she gently pushed further inside of me, increasing the speed of her action, there I was lay on my back with legs in the air, being taken up the ass by a beautiful young woman, I remember thinking, life doesn’t get any better than this.

She continued to increase the motion and I could feel her balls banging against me as she shot her load deep inside of me and then without hesitation she pulled out and moved her mouth back to my hole and licked her own juices as they leaked out of me.

I was incredibly hard by this time so Emma took my in her mouth and worked on my length until I could feel my juices building up and just as I came, she pulled off me and allowed the semen to shoot up in the air and down all over my crotch area and then she began licking the whole area, the sensation of having this beautiful woman’s tongue licking around my still extra sensitive swollen cock and balls took me to another level, I could hardly take the touch I was so sensitive, this girl really is the best was my next thought.

I really thought I had found the perfect woman for me.

To be continued…