A Holiday to Remember

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Double Penetration

I was on holiday with three of my friends Dave, Eddie and Paul. We were all completely contrasting personalities with different appreciations and distastes but, in the fathomless miracles of friendship, we for some reason identified as equals in a group.

Paul is the tallest of the group towering at six feet. He was incredibly well-built as a result of years of cross country running and being in the services. He took such pride in how he looked so always dressed smartly and was clean shaven. We had been friends through school so I didn’t see him as a service man, more the kid I grew up playing out and getting in trouble with. His main downfall whilst on holiday with us was that he got drunk very easily and this got him in some crazy situations.

Eddie stood, compared to Paul, a runty five feet six inches but was tougher, honed, and exercised until no evidence of softness lingered in his muscled physique. He was the newest member of the group having met Dave in college. The first night out he came on we quickly realised he had the same sense of humour and fit in well. Within 3 months of meeting him, he was booked on our next holiday and has been with us since.

Dave was just inches shorter than me with jet black hair. He wasn’t toned but there was no fat on him anywhere. He was just an average looking guy all around. He liked to be the life of the party. He was having a run of bad luck with the loss of his father and splitting from his girlfriend all in the past couple of months which had quietened him down a lot. Then there is me, five feet, ten inches with brown hair, played sports and worked for myself in the building industry so just naturally had muscles but not overly toned.

We were all of equal standing in the group really but if we were going out it would be up to me organise it, if someone had a problem they came to me to sort it. I guess I was in charge of the group. As for our taste in women, Paul and I were always into similar women. The only difference would be he looks for a girlfriend for a long term relationship and falls in love very easily, where as I had no plans of settling down anytime soon. Eddie was a legs man, which we gave him stick for because with him being short, girl’s legs were at his eye level. Not really but it’s still fun to tease him. As for Dave, he is all about the boobs. If a girl had big boobs he more than likely couldn’t tell you what colour her hair was.

We all needed the break from reality as we all were working really hard at our jobs. So we decided to go back to the Canary Islands because we knew the night life was amazing out there. When we arrived the weather was incredible, not a cloud in the sky. Even at this early morning stage the heat was amazing. We had booked two suites at a hotel that was just off the main strip of clubs and only a 5 minute walk from the beach.

I shared a room with Dave as we had on all our previous holidays. Walking into our room we thought we had hit the jackpot. The two single beds where split by a small bedside table in the middle. Dave took the bed closest to the balcony which was fine by me as the air conditioning was closer to my bed. There was a small kitchen area in the corner of the room, with a mini bar. The bathroom off to the side had a big double walk in shower. A pretty simple room but after some of the previous places we stayed in, it was a palace.

I walked out onto the balcony and we were two floors up overlooking the pool that occupied the majority of the first floor. It was the perfect place to catch the sun. It had a table and chairs out there so we could have a drink out there and relax without being overlooked by people. Paul and Eddie where two doors down but there didn’t seem to be anyone in the rooms between us.

After settling in our rooms we all took showers to wash the flight off us and refresh. As usual after his shower Dave walked round the apartment naked. He was well hung even when he was soft. I knew it grew a lot as I had watched the sex videos he had made with his ex. But he had shaved everywhere which made it look bigger. I could see why he showed such confidence with the girls. I was used to him being naked and after the initial look because there is a naked person in your room I just carried on getting ready as normal. I was thinking that it would be easy to get him a girl tonight after seeing him like that.

Our plan was to chill out and have a drink before heading out for the night so we started on the mini bar while getting ready. I was hoping he would meet someone to change his luck and quiet mood.

The first night went as expected, we all got drunk on a bar crawl. There were plenty of girls there and we ended up drinking with a group of beauties. Even though we were not the most attractive group of lads we seem to attract the girls because we’re always having a laugh and we will speak to anyone. I guess that helps them feel comfortable around us. Plus we were all on holiday and kurtköy sınırsız escort the sun and drink gets everyone horny as hell. As the night went on the group of people with us grew bigger.

Standing with Paul and Dave we realised Eddie wasn’t round. He was at the bar with one of the girls. She was only a bit taller than him even though she had heels on. She had dark brown hair and had caught a nice tan. But we saw what actually caught his eye, she was wearing little red hot pants. All of her legs where on show. They were pretty impressive. We just looked at each other knowing what the other was thinking.

Paul started talking to a tall blonde that had joined the group. She was stunning. Hardly any make up on and still looked like a model. Her figure hugging dress showed off her trim body. I was tempted to join them and mess with his head a bit, but she seemed to like him and as usual he was quickly falling in love. Again. So I left them too it. Dave and I were still in the group talking to all different people. Well I was, Dave just seemed to be drinking and nodding along with the conversations.

Paul came over with the girl who I found out was called Nikki and another girl called Sarah. Sarah was only about 5 feet tall. She looked tiny in comparison to her friend and Paul. Her flame red hair ran all the way down to the base of her back. She was wearing a little crop top that barley covered her tits which looked huge on her little fame and a skirt that flicked out over a beautiful shaped arse. My first thought was this girl was beautiful. After chatting to her for a bit I thought she would be good for Dave.

You could tell Paul was hoping one of us would get with her so he could be with Nikki. But he got no response out of Dave at first who would have normally been all over Sarah. He just excused himself and went to the bar to apparently talk to Eddie. But once it was obvious he wasn’t going to be any help. I started talking to her more. She wasn’t someone I would normally go for, but she seemed up for a hook up. Plus I was a sucker for a great arse, so I had no problem playing the wingman tonight. Fickle I know but we were on holiday and I was here to have a good time. A sexy little red head will do just fine for tonight.

The music was blasting, drinks flowing and the warmth of the night was keeping spirits high. It was such a good atmosphere in the club that even Dave had to loosen up a bit. He and Eddie where still out on the dance floor when Paul and I left with the girls. I just thought the Eddie and Dave would go back to our rooms with the girls they were dancing with when we left.

We walked back to our hotel in the morning and were quite happy with ourselves. Paul was telling me how much he liked Nikki and that they were going to keep in touch when they got home. I had a great time with Sarah and the sex was intense. It was fun having someone so small to throw round the bedroom. I just tossed her into the positions I wanted with ease and I got no complaints from her so I guess she was enjoying being dominated. We both knew we were just here for the sex not a relationship. That just added to the occasion.

When we got back Eddie had that smug smile on his face that we all knew meant he got laid but Dave was quiet and didn’t really join in with the usual morning after chats. Apparently he had just walked home alone and gone to bed. He hadn’t wanted a girl since his break up but thought maybe the holiday would change his mood and get him out his funk. We spent the day out on the beach recovering and enjoying this paradise away from home. Warm sand cool sea’s and hoards of beautiful women. I couldn’t help think that this had to improve Dave’s mood.

The next night we met up with the same group and went to get some food. The alcohol was flowing and everyone was well on their way to being drunk. We were joking round when one of the girls choked on her drink. The lads being dirty as usual said guess you can’t deep throat with a gag reflex like that, unlike Alex. This comes from a drunken party at college when everyone was seeing how deep into their mouths they could get a banana. So this was a running joke now that I could deep throat.

As the night moved on it was going the same way as the night before until Dave said he was heading home. You could tell there was something up, so I said I would go back with him. He refused the gesture and said he would be fine. Now anyone that has had a long term best friend be it male or female knows it’s heart-breaking when your friend is hurting and there is absolutely nothing you can do to help except be there if they need you.

I stayed out with the others but couldn’t get my mind off Dave. At this point I figured Paul slept with Nikki the night before so didn’t need me to play wingman. Sarah was happily dancing with some other bloke so I had an out there without it being awkward and Eddie was about to disappear maltepe otele gelen escort with the same girl from the previous night. I decided to head back to the apartment to see how he was doing.

On the short walk back to the room I was playing over in my head ways to try and help Dave. The problem was everything I was trying wasn’t working. We had a perfect day in an amazingly beautiful location with no stress of home life. But if he makes no effort to enjoy his surroundings I didn’t know what to do. I know he wants to be on his own but it’s been a few months and he has shown no signs that the old Dave is still in there. I know it’s selfish after what he has been through but I missed my best friend and wanted him back. I had booked this holiday to help him and planned on doing whatever it took to break the funk.

When I got back he was on his bed in his boxers with his headphones in listening to music. He smiled once he realised I was there and took his headphones. We started to chat, both pretty drunk and he started to open up about things. He spoke about his dad which I thought was the major reason behind his moods. I could not have been more wrong. He seemed ok about that as it was a drawn out illness so he knew his dad was finally at peace and got to say his goodbyes before the end. What surprised me was when he told me it didn’t work out with his girlfriend because he was in love with someone else. Then the shock of all shocks when he told me it was me. We had been friends for over ten years and at no point had this occurred to me.

Now I had asked him to open up but I wasn’t ready for this. Once over the initial shock we spoke more in depth and he explained he didn’t think he was gay but after everything we had been through and how close we had grown these feelings got stronger. He didn’t know how to deal with these feelings so was trying to distance himself hoping they would pass. I burst out laughing which broke the tension.

“Here you are trying to distance yourself from me and I book us a holiday so we a stuck sharing room for a week.”

“Yeh, some help you are.” Was his reply. He realised at this point I wasn’t mad with him or anything.

We were only there for about half an hour talking but it seemed like we had covered a lifetime of conversation. It was the most comfortable and relaxed I had seen him in months. It was now obvious that this was the burden that was constricting his behaviour. The weight had been lifted now he had shared it with me. Then he threw the next curveball, he had fantasies about us sleeping together. Now I love him because we were so close but hadn’t considered this. Even after being told he loved me, I still hadn’t got to the point in my head that made me realise he wanted to have sex with me. I was wondering if I was willing to go that far if it meant I got my partner in crime back. Was I going to fuck him to make him feel better? I wasn’t convinced. It didn’t even occur to me that he may want to be the one to fuck me.

The fact he was lying there in only his boxers and saying these things made me look him up and down. He noticed and chuckled to himself. The one day of sun had worked wonders on him. His tan looked great. He just lay letting me survey the situation. The heat was intense as he hadn’t put the ac on when he got in. The balcony doors where shut so there was no breeze through the room. The sweat started to drip down his hairless chest down onto his flat stomach and beyond. My eyes just followed the drops all the way. I was obviously staring at the bulge in his boxers. My thoughts raced back to the sex tapes he had shown me of him and his ex. I was honestly terrified. My mind was racing in a thousand different directions. Less than an hour ago I was in a position to get with Sarah again. Now here I was contemplating sleeping with Dave. We were best friends, what would that do to us if it all went wrong. If this would help he get back to normal am I willing to do this? I trusted him with my life so I know it would stay between the two of us. Would I be able to fuck him? I had never been with a man before. Whatever it takes. That comment just kept coming to the front of my mind.

“I want to be with you even if it is just the once.” He said not totally believing once would be enough for him.

I hadn’t realised he had taken his cock out and was rubbing it freely whilst talking to me about his fantasies. After listening to him for a few minutes it became abundantly clear that all his fantasies where about him being the one doing the fucking and me on the receiving end. My naivety was like a punch to the stomach. I couldn’t seem to catch my breath. It was suddenly a totally different prospect. At that moment my fear went from, am I going to do this? To, can I do this? It was like him getting naked had me resign to the fact we were going to do something. I was already losing control.

My anxiety was apparent kartal rus escort as the realisation of what saying yes to this actually involved. Dave’s confidence seemed to grow as I was squirming more and more by the second. He was sat there his tanned body naked as the day he was born, glistening with sweat. His tan lines just seem to emphasise how big his cock was. He was just oozing that confidence I had seen so many times with women. He was leaning against the top of his bed. I was opposite to him on my bed watching him move his hand. He was just watching me waiting for me to make a move. But I wasn’t going anywhere. My arms felt like they were made of lead. There was no way I was going to make the first move.

“Go on, touch it.”

It sounded totally different to anything I had heard from him before. I had never been spoken down to by him. It was like he was becoming inpatient with my indecision. His mind was made up that this was happening now and there was no going back.

I would blame the drink for what I did next but that wouldn’t be true. I reached across the gap between us and replaced his hand with mine. My hand was trembling as it wrapped around his dick for the first time. My heart was racing. I guess him telling me to do it made it slightly easier than me just reaching out for his cock. It was a thrilling feeling doing this to him and it was totally turning me on.

After a few minutes of this he was rock hard. His dirty talk had stopped and turned into moans. My eyes didn’t leave his cock once I had hold of it. He had me. I was totally engrossed in what was happening when he suddenly shifted his weight. I thought he was going to cum but he was just changing position. It occurred to me that maybe I could just get him off with my hands and that would be enough to please him. He turned and stood up, I didn’t want to let go. He told me to stand up to and then he started undressing me. He was this totally dominant person, instructing me on what to do and where to go. So unlike the friendship we have had for years. Once naked he grabbed my cock and I was rock hard.

“You are enjoying being a slut aren’t you” he said.

Wow here I was naked with my best friend in a hotel room with him wanking me calling me a slut. It was true I was totally turned on. The lights at the top of the beds lit the room enough that we could see every detail of each other. As I looked over the body that I had earlier called regular I was finding it sexier and sexier as I got more and more turned on. No matter what happened from here the power in our friendship had shifted. I knew it and he knew it.

“Get on your knees slut,”

As he sat on the side of the bed he opened his legs. There it was again, like a slap to the face. I wasn’t used to being spoken too like this by anyone, Dave loved every minute of it and so was I. I felt like I had no control over my body because next thing I know I was on my knees between his legs with his cock just inches from my face. As I said I have seen his videos with his ex and him walking round naked so his cock wasn’t a new sight for me but from this view it was totally different. His rock hard 9″ long dick was thick as well. I was examining every vein, ridge and contour of it, totally back in a trance. Dave noticed this

“Stop admiring it and get to work.”

Grabbing my head he pushed me down onto him. I opened my mouth without thinking and he shoved it in. I put my hand at the base of his cock to stop him pushing it all the way in. So he worked the rest of it in and out for a while then he was ready for more.

“Move your hand slut we all know you can handle more and I plan forcing every inch down your throat.”

He moved my hand then placed both of his on the back of my head forcing me down further. Once he was all the way in he started to pull back out but not all the way and slammed it back down my throat. He was just using my mouth at this point he had total control. He finally let me up for air. I asked if we could change positions as my knees where hurting. I could not believe it, here I was asking permission to move so I could suck him easier and it just seemed so natural. My world has truly changed quickly.

Once he was lying back on the bed I climbed back between his legs and got back to work as he called it. I had more control in this position so this was more of me sucking him than him fucking the hell out of my face. In my mind were all the things I liked having done to me when getting a blowjob. Plus what he had told me he like when we spoke about these things in the past. I licked from the base to the tip before putting it back into my mouth, all the time massaging his balls with my hand. Working away like this his moans where increasing, I suddenly had a moment of panic with the thought of him cumming in my mouth. For some reason I just didn’t feel ready to let him do that. Dave wasn’t ready for that either but for different reasons.

“Stay right there and don’t move”

I was told and like the good slut I had become I obeyed. He pulled himself up and out from underneath me and went to get something from his case. He had a huge smile on his face that just told me he was in total control and was going to do what he wanted to me when he wanted to do it.

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