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Holiday spying and taking advantage

I went on holiday years ago with a girl I lived with at university, she was going out with a mate of mine and I was going out with a mate of hers so no risk of anything happening. After an OK flight the transfer seemed to go on forever in the old taxi on 3rd world roads. Needless to say we were relieved to finally arrive at the hotel until checking in to find they had lost our booking and were fully occupied. After much discussion, showing e- mails and general frustration we were upgraded to the honeymoon suite on the roof.

This sounded incredible, but the hotel was pretty basic and despite explaining over and over again that we were not a couple the bell boy led the way to the room. Language barriers and fatigue got the better of us and we just followed. Despite having lived together for years with no weirdness an air of awkwardness filled the lift as we both internalised the prospect of heart shaped breakfasts in a double bed for a week rather then the the 2 connecting rooms we had booked.

We stepped out onto a terrace that we were poignantly told was communal (presumably honeymooning couples had been busted previously thinking it was their private area) with a room at the far end looking out over the sea and the beach directly below. The door opened revealing a huge double bed with flowers on the pillow and no lack of mirrors on the wall.

The bellboy proudly pointed at the bed before leading us around the corner where there was another bed and door to the bathroom. The girl and I shared a look of relief and thanked the man sincerely. This room was awesome and the voyeur in me was already excited about the prospect of a view down to the beach (close enough for proper viewing) and of the terrace.

I quickly offered to sl**p in the lesser bed with a smaller more subtle window looking out onto the terrace on one side and beach on the other. I had calculated that I could look at the beach discreetly from my area around the corner. We unpacked showered etc and headed out for the night.

The following morning I woke late with a hell of a hangover, my friend had already got up and left a note saying she was on the beach. It was a perfect opportunity to scope out the viewing opportunities. I went to the beach window first finding the area in full view occupied by men and fat women disappointingly, the sun terrace was unoccupied but our room had potential I had realised during the night. There was an air vent on the wall next to my bed which I had discovered was annoyingly loud if someone used the toilet during the night. Even in my d***ken stupor though I had made a mental note to check it out in case you could see through it. It was just below my head height, bl**d started pumping to my penis as I looked straight through at the shower with only the finest of wire gauze filters impeding the view.

If you have read my previous posts and seen my galleries you will see that I am mildly infatuated with my blonde housemate having spied on her repeatedly over the last few years. I have been lucky enough to see plenty of her full figure with massive tits round arse and either short back and sides or landing strip in dark blonde. Her vibrator and underwear featured heavily in my perverse moments and she had unknowingly been splattered with and tasted me on a number of occasions. The vent discovery suggested that I was about to have another good set of memories for the bank.

That day passed without event and we headed out for the evening. Coincidentally running into an old friend of my housemates in a bar after dinner. She was here with her boyfriend who was a good lad. When the bar shut we invited them back to our hotel to make use of the terrace where we continued drinking for hours playing a number of drinking games and generally having a good time. One of the games involved dares, we had to write dares on scraps of paper and whoever lost that round had to pick a date and do it. Naturally all of mine had a sexually devious angle but they all seemed to be at the bottom of the hat. We continued for ages with nothing of note until finally one of mine was picked by this girl.

I could see that it was my handwriting as my pulse accelerated trying to work out which one it was. She was plain facially and wearing clothes that hid her figure entirely. I had spent the majority of he night assessing what was hidden under the outfit to little avail. As she started reading the dare I did a mental high five, she had to call room service and answer the door naked. It was taken in good spirits and she retreated to our bedroom and calling reception then starting to undress. With the curtains open wecould clearly see her as she removed her clothes to reveal one hell of a hardbody in a lacy bra and uninspiring black knickers. Things were looking up!!!!

She disappears from view as the curtains fell (bollocks!). The door to the room opened and she waved the bra and panties at us while remaining hidden. I was shaking with excitement/ frustration and there was no way I could move to see her naked without it being pathetically obvious and incurring the wrath of both my housemate and the girls boyfriend. The door shut and we waited a short time before the lucky bastard room service man appeared. He was only feet away from us and after knocking there was an audible intake of air as the door opened and he remained rooted to his spot eyes wide open staring at her naked. He realised he was wide eyed, open mouthed and visibly shocked before collecting himself eyes downcast stuttering apologies at her. The tonic water was handed over and he walked away bright red looking happy with himself.

She returned and the game continued. I was horny as hell and gutted at having missed the view. After another round she said she was going to the bathroom. My mind returned to the vent and after uttering a semi plausible excuse about jumpers followed her into the bedroom. I peered through the vent hearing her frustratingly out of view. I heard flushing before a tight pair of buttocks appeared momentarily slightly bent over then retreating out of view again. I grabbed a jumper and fled before anyone clocked something out of the ordinary. She came back oblivious to her exposure and we chatted a while longer. I delighted in chatting knowing that I had seen her beautiful ass and had the image stored for future use. When they left I even managed a glancing grope of her right cheek while kissing goodbye.

I was 10/10 horny as my housemate and I decided to head to bed me rushing to clean teeth first hoping that I could exploit her d***kenness for further 'spots' that night. After I finished she closed the bathroom door and I resumed my position at the grate. She was fully clothed brushing teeth so I used the time to adjust the lights leaving only her bedside light on so that she undressed confidently without fear of being overly obvious. I hopped into bed and pretended to sl**p facing away from her bed. She quietly closed the bathroom door and walked past me discarding jumper and hat en route. I quietly rolled and was rewarded with her back as the shirt was pulled over her head. Her hands reached back unclipping a white bra before leaning forward as the bra dropped. I caught a full side boob as she bent to remove trousers showing her sizeable ass in panties leaving enough on show for my hand to be working harder under the covers. As her second trouser leg was pulled off she tripped, turning as she stumbled giving me a full side view of her tits as they hung down bouncing as she tried to recover her footing. Balance regained she sat down on the bed giving me a full frontal of those gorgeous boobs, light pink big surrounds and small nipples. They bounced upwards as she landed before lying down. I had a perfect view as they stood upwards and flopped down on either side of her body. It had been a while since I had been lucky enough for a full inspection and it looked as if the ravages of time had not been kind as they sagged down. Scanning down her body revealed a flat stomach and boring white panties pulled tightly showing the suggestion of a landing strip and pubic mound.

My heart was now going at full pace as I held my breath praying that she would pass out like that with the light on. I started counting as heavy breathing followed by the odd snore emitted from the master bed. After reaching 500 I coughed loudly praying that she continued breathing heavily. As I listened to the uninterrupted breathing pattern my excitement and gratitude at the universe having landed me in this situation were both high. Pulling back the covers I glanced down to see me fully erect sticking out of the front of my boxer shorts. Quietly I made my way to the bed asking her to turn the light off with increasing volume to no effect.

Her legs were slightly spread allowing me to inspect a slight camel toe and the darkness of her pubic hair just st visible through the fabric. I yelled her name, picked a glass of water next to the bed in case she woke up so I had some form of excuse for being there however implausible and shook the left shoulder hard. Not even a stir! Breathing continued to be even as I traced under each tit in turn before lightly pinching both nipples until they were hard. After licking them I sucked before placing my erection on her forehead then slightly open mouth. I pulled the foreskin back and placed my head against her lips pushing it just inside her mouth while squeezing the right boob. I remembered my camera and quietly moved back to find it and begin. I repeated my previous actions, immortalised in digital form before switching to video. I captured my head entering the mouth, brushing across her lips and balls placed on her forehead. Moving back to her rack I held squeezed both in one hand holding them up and filmed them sagging back to position as I released. Lifting the front of her knickers exposing her dark blonde hair recently waxed into a slim landing strip which I rubbed. Pulling them to one side I got a close up of those big lips pulling one to the side revealing her little clit and the top of her hole. Licking downwards I realised it had been ages since I last had this taste in my tongue. Slipping my finger inside I felt the familiar warmth and a little damp. She felt tight!!

Once removed the finger went into her mouth before I gently prised each leg outward in turn. Pulling the material to one side and doing the same with each lip I looked at a completely open beautiful young pussy and tightly closed asshole with such a dark taint contrasting with such pale skin. I licked it sloppily preparing for intrusion and gently pushed with increasing pressure. It had clearly been a while since the boyfriend was lucky enough to take the ass. Eventually the ring yielded and my finger slid in pushing until it was all in and doing a few gentle strokes before spreading her anus between thumb and forefinger to watch it contract as it became empty once again. I rentered and placed my thumb in that sweet pussy feeling the wall while gently pulling it outward. Now fully confident I lifted her legs upwards slipping the knickers down her legs for the moneyshot, tasting and spreading everything. I jerked off hard with a finger in each hole occasionally dipping my head into her mouth. I delayed and delayed shooting to enjoy the moment as much as possible and I couldn't decide where to finish . Face or boobs? A tough question in stressful circumstances. I finally decided on forehead, accelerated my right hand and went for it. Having been sharing a room I was seriously pent up after only one orgasm in the last 3 days (not normal for me). I released an epic load as the wave of pleasure hit me. Several big shots landing right on her forehead and dribbled down, only the first overshooting. My cock slipped into her mouth with no resistance and I wiped a finger through my cum and after pulling open her panties pushed it inside her anus, a gift from me.

I was exhausted and after cleaning up headed for sl**p. I was startled as the phone rang loudly to discover it was late morning. No movement at all from my housemate, a heavy sl**per no less. It was the couple from last night asking if they could sunbathe on our terrace because it was really windy and the beach as a no go. I muttered "help yourself" and returned to my slumber.

When I finally emerged I was alone in my room and could hear chatting outside. Evidently the three of them were having a chat and sunbathing at this end of the terrace. Without thinking I peered out of the hole under the curtain to see what was going on. Result! They were directly in front of the window my right hand returned to its normal location as I scanned the girls athletic body. She was sporting yellow bikini bottoms and a non matching black patterned top. It was certainly a skimpy bikini but nothing outlandish. My companion had headed off somewhere leaving the two of them alone. I observed them as they chatted and occasionally kissed with some lingering hands, nothing too racy but probably further than you would go in full sight of someone. I realised that having not even switched on my light yet at this end of the room they were oblivious to my presence. My mind began whirring through potential scenarios hoping for them to do the decent thing and at least show me her naked form.

Sometime later it became apparent that they we're not going to fulfil my porn film fantasies and start doing anal in front of me but I remained undetected just in case. She applied suncream teasingly running fingers inside each cup and under the band of her bottoms, bikini bridge time!! They were raised just enough to give me a view of the top half of he area covered by knickers but not the whole deal. I could see she was devoid of most of her pubic hair but couldn't see far enough to confirm if she had a Brazilian or was clean shaven. It was a memorable spot but not the holy grail moment I was hoping for.

Shortly afterwards she sat up facing the other end of the terrace and the door that other guests came through. Her back was to me so I could see when she reached behind her toward her bra strap. I moved closer in anticipation she undid the strap and turned to face me, literally 3 feet away. She turned in my direction because it shielded her from anyone coming out of the door from the stairs and as if my prayers were being answered she slid down the top revealing pert little boobs and dark pointy nipples protruding. After reaching into her bag she pulled out a bra which she slipped on before following with a t shirt. I had been lucky enough to get a good look at both of them straight on and from the side. They bounced slightly as the bikini top came off allowing me to reasonably assess their firmness. They looked like the kind that don't swing they spring maybe as far as a little bouncing when in doggystle and being drilled but generally pert as hell. The couple gathered their possessions and headed toward the door. I raced outside desperate to have one final chat now I really had something to remember her by. Catching them just in time I bid them a fond farewell kissing her on both cheeks while picturing those tits and her ass.
I have never seen her again but think of her regularly.

I occupied the remainder of the holiday by focusing on my housemate and adopting a triple pronged attack. The first objective was spying, second flashing her and finally getting my cum on/in her. I had a great time with the vent watching her shower 3 days in a row. Sadly the dream of her fingering herself but lots of good nudity and bouncing boobs bending over and drying herself. I exposed my erection one morning, pretending that I had kicked off the sheet during the night and my morning wood just happened to have escaped the confines of my boxer shorts. She had to walk past me to get to the bathroom so having positioned the sheets I waited maintaining a full hard on. Eventually she woke up and headed in my direction. She continued to walk past the bed but made a small shocked sound before giggling. As soon as I was confident that she wasn't going to come back out of the bathroom I assumed the vent position. I was tempted to get some of her underwear but was nervous of missing out. Another successful day I thought to myself as I watched her shower saving my orgasm for the towelling off post shower. I love the bending over and swinging tits as girls dry. Sure enough I was not disappointed, painting the wall as she bent double facing away from me those saggy breasts swinging. Having emptied my balls I had an idea, what would she think if I was in exactly the same position but this time with a flaccid member? I hurried to recreate the exact pose and just made it in time. She stopped briefly and looked down at me not making a sound. At breakfast she seemed a bit distant but nothing was mentioned. That afternoon I unloaded on her toothbrush.

All in all a great holiday, I hope you the have enjoyed this tale. Please comment if you think it is worth me jotting any other experiences down, I am always keen to chat about similar experiences. I have photos of the roommate naked in my galleries and a video of her. PM me and I will point out which girl it is or let me know which girl you think it is if you are familiar with my content on here. Cheers

Updated: December 17, 2016 — 1:34 am
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