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Confessions of a male holiday rep
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About 5 yrs ago live took a bit of a turn and I found myself heading out for a season of work in the sun, something I wanted to do 20 yrs ago so I was determined to make the most of it. Quite a bit happened in the 1st few months but that’s for other stories. I got on really well with my resort manager Jane who lived with her son on the same street as me. We’d hit it off on day 1 and she was a bit of a party animal. She was 6yrs older than me (I was 41), 5’5” very curvy size 16/18. A few times I’d been along to hers and had a bite to eat and a few drinks in the garden. 1 Sunday I was invited to join her and a few friends for 1 of their birthdays out on boat. The drinks flowed and it was a great day out. Afterwards I ended up back at here along with 3 couples for more drinks. We were all pretty tipsy and the hot tub got switched on. 1 of the couples said their goodbyes which left me, Jane and her best friends Liz and Mike. The girls were the 1st into the hot tub followed by us. As I climbed in Liz moved around next to me and Mike joked you’d better watch she’ll want you to fill her up all night and nodded to her empty glass. I laughed and topped her up and caught her winking at him. Mike was a couple yrs old than me and his wife Liz was older. 59, 5’3”, curvy size 12/14 and the loveliest woman you’d hope to meet. She gave me a cheeky smile and said don’t let him wind you up he’s off home soon. Sorry it’s a bit long, I like detail. Shall I continue? |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Definitely |
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We had a couple more drinks, lots of laughs and I’d felt Liz’s hand on my leg a few times under the water as she made herself comfortable. I’d noticed both Liz & Mike looking in my direction a few times then winking at each other but thought Nothing of it. Around 9pm Mike started saying his goodbyes as he had an early meeting and asked Jane if she was still going to pop home with him to grab the bottles of wine he’d promised her. Jane got up & dried off saying she’d be as quick as she could and Liz headed off to the loo. I heard Liz coming up behind me a few minutes later and as she held onto my shoulder climbing back in beside me I noticed she’d taken her bikini top off. Her chest was very pert not massive but had the hardest nipples I’d seen all season. You don’t mind do you? She asked. No, I replied don’t let me stop you. Good she said you won’t mind if I lose these aswell then as she untied her bottoms under the bubbles and tossed them away. I filled up her glass and as I handed it to her she brushed my hand and said with a smile on her face, I hope it’s not just my glass you’ll be filling up tonight? I wasn’t sure how to reply but she broke my chain of thought by stating it was rude to still be wearing shorts whilst she was naked. Next thing I know I’m stood up with Liz untying my shorts and slipping them off. My now rapidly hardening cock springing free right in front of her face she looked up at me as she slowly wrapped her hand around my cock |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Nice |
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By (user no longer on site)
over a year ago
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Great start please continue.... |
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By (user no longer on site)
over a year ago
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Mmmmm |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Great start more please |
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By (user no longer on site)
over a year ago
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Lucky boy |
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I was stood frozen for a second I was kinda taken aback a little thinking is really happening, didn’t her husband and my boss just leave, omg my boss she’ll be back any minute, I’ll get sacked, her husband will find out he’ll want to kill me. I came back in to the moment and took a step back Liz let go of my cock and asked if I was ok. I reassured her I was and shared my concerns about Jane catching us and Mike finding out. She laughed and let out a sigh. Thank god for that she said, I thought I’ve just grabbed hold of his cock uninvited and he doesn’t fancy me, I’ve read all the signals wrong. I sat down next to her and handed her drink over. Taking a big gulp of mine i told her she was stunning and I admitted I might have perved a few times whilst we’d been on the boat and when she’d got out the hot tub earlier. Damn she said we that’s me lost then. Confused I asked “lost what?” A little bet I had with Mike she replied. What exactly was the bet? Well as we got off the boat earlier he told me he thinks I had a new admirer. I told him he was seeing things and that your into Jane so we had a little wager. Ahh so I’m a bet I said and laughed. So how did you end up with me alone I asked? That was Mikes plan she said. I told him you’d not be interested. Remember when he warned you I’d be wanting my glass filled up all night? Yeah, I replied. Well that was code, he was telling me to go for it on 2 conditions. Ok and those are? I asked. 1. That I give him every detail should anything happen. And the 2nd? Well the 2nd was that should anything happen I was to invite you round to ours sometime and hopefully you’d like to join us both. I sat for a minute as she took a drink and just said I suppose I’d better help you win this bet. We both put down our drinks she wrapped her arms around my neck and kissed deeply, I moved her around so she was against the side of the hot tub and lifted her out sitting her arse on the side. I stood and kissed her again moving my mouth down and sucking her nipples 1 at a time making them somehow harder than they already were. She opened her legs and it was only as I kissed down her stomach my fingers found her tight, pussy. She was freshly waxed and my tongue soon joined my fingers, flicking her clit as I slid 1 then 2 fingers deep inside her slowly fucking her. She let out a moan as I carried on and within a few minutes was on the edge of cumming. So I stopped |
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By (user no longer on site)
over a year ago
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Very good story. Looking forward to seeing more |
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By (user no longer on site)
over a year ago
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Liz was panting hard trying to get her breath back as I sat on the side next to her between big deep breaths she asked why I stopped? Well I can’t have you peaking too soon I replied, think it’s my turn. Liz needed no encouragement as she climbed back into the hot tub and onto her knees in front of me slowly wanking my cock as she lowered her head looking up into my eyes as she wrapped her mouth around me taking my cock in deep and slowly pulling away it wasn’t long before she worked up a rythem giving me the best blow job I’d had in weeks feeling my cock pulsating in her mouth I was ready to cum as she pulled her mouth off my cock and frantically wanked me harder and harder pushing her gorgeous chest towards me as I rolled back and shot a massive load of cum all over her tits. As she slowed her hand making sure she’d milked every last drop from my cock mmmmm she said I hope there’s more where that came from I’m not finished with you yet. We both sat back and grabbed a drink as we recovered. She sat across from me taking a sip as I watched her free hand disappear under the water towards her pussy. I love watching a woman fingering herself I told her, she replied I love being watched but I hope your cocks going to replacing my fingers soon. I told Mike earlier I’d wished you’d been here fucking me as I sucked his cock earlier in Jane’s bathroom. So that’s why you were away for ages earlier I asked? Ohh so you noticed did you, she asked. I did, I replied tbh I thought you weren’t feeling well. We finished our drinks and climbed out the hot tub I took her hand helping her out and we dried off a bit and made our way over to the garden sofa (thank god for soft cushions). I wrapped my arms around her pulling and tweaking her nipples as I kissed her neck and whispered to her to bend over. Hang on she said, how would you feel if I filmed this? I’d love have something to show Mike later. I’d had a couple of mmf meets before but this was new to me. Are you sure I asked? He loves hearing all the details she replied he’ll love it even more if I can show him the proof afterwards since he’s not here in person. 5 minutes later her phone was set up recording as this naughty wife was bent over my bosses garden sofa begging me to fuck get hard. |
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Great story so far. Feel free to continue!  |
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She knelt on the edge of the sofa hands on the back as I knelt down behind her and traced my fingers from her clit all the way round stopping at her arse. I need that clock inside me she said almost demanded it. I ignored her for now as I replaced my fingers with my tongue as licked her clit and then ran my tongue slowly between her pussy lips and all the way to her right arse. As I reached her arse I felt her nudge backwards I placed my hands on her cheeks as I spread them a little and my tongue flicked and probed her hole. She gave out a moan as I licked her tight hole a little harder pushing the tip of my tongue just inside as she bucked backwards into me, please fuck me she gasped as I carried on her panting getting harder as I noticed 1 hand was now frantically rubbing her clit as I rimmed her arse. I slapped her cheek as I stood up and as she was rubbing her clit I pushed my cock slowly inside her tight pussy for the 1st time. She moved her hand away and gripped the back of the sofa as I started pounding her from behind her pussy gripping my cock tighter as I felt her 1st wave of orgasm rip through her and she bit into the cushion to stop herself crying out. As her orgasm slowed I pulled out and she lead me over to the sun lounger. I lay down as she climbed on top of me feet on the edges of the lounger hands on my chest as she lowered herself onto my cock. This time she was in charge. She rode my cock like a grand national jockey and I felt my balls filling up, I’m going to cum I said, she carried on and again I said I’m gonna cum she carried on riding my cock as she softly said please fill my pussy it was only then I’d remembered I wasn’t wearing a condom (I’m always safe until I know someone and only then if it feels right) ohh god I moaned I’m gonna cum this just made her ride my coco harder and faster and as I felt the 1st load I held her hips as we both came hard my cock twitching with every spurt deep inside her. We lay there for a few minutes before I remembered Jane. She should be back. Liz climbed off me and we climbed back into the hot tub after grabbing her phone, we refilled our drinks and we were just sat there smiling at each other as we heard Jane shout from the kitchen I’m back. She appeared at the side of hot tub swimsuit on as Liz put her hand up. Stop right there lady and get that off!!! If we’re both naked there you are too. Jane looked at me and said hang on who’s idea was it to get naked. Liz replied it was me, poor boy didn’t stand a chance it was a dare and he lost. Shyly Jane had me turn away as she stripped and climbed in opposite me and I felt Liz play footsy and tease my cock as we all chatted away. To be continued |
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By (user no longer on site)
over a year ago
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Really enjoying this so far. Looking forward to reading more. |
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By *erri AnneTV/TS
over a year ago
Shannon and Costa Blanca |
What was Jane and Mike doing got so long  |
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I leave you both alone as I go to get supplies and come back to find you both naked in my hot tub, what kinda dare was this Jane asked. Liz replied, it was all my fault Jane you know what I’m like. I was getting to know him asking everything and anything and he said what is this truth or dare? So I said yeah if you like. He was a little shy at 1st but I dared him to down his wine. He couldn’t, said if it had been a beer he’d be fine. He lost so the shorts had to come off. She laughed and said doesn’t explain why your naked. Well Liz replied poor guy couldn’t leave him naked whilst I was in my bikini wouldn’t be fair. She pointed to her bra at the side and then her bottoms half way across the garden. I covered my cock as I climbed out to go to the toilet and heard them both whistle as I walked inside. When I returned Liz was drying off and saying she had to head off home hadn’t realised it was nearly midnight. She leaned over and kissed Jane thanking her for a great day/night and that next time she was to go to theirs. You young man she said to me as she winked, thanks for keeping me company, Mikes txt to say you should pop over during the week for the football and a few beers but forget the swim shorts it’s naked or not at all at their pool and laughed as she kissed my cheek goodbye. I climbed back in with Jane and we both sat there for a few minutes. She’s a bit crazy but great Jane said and I laughed. We had a few more drinks and I said I’d best make a move home. Jane climbed out and grabbed a towel she watched as I climbed out and startled me a little saying that’s a shame I was hoping you’d eat my pussy the way I’d eaten Liz’s. I just looked at her open mouthed before asking nervously laughing and asking, what did Liz say? Nothing she replied. I was confused. I got home about 30 minutes before I came out here. You didn’t notice. My mind was racing, omg I’m so sorry I didn’t mean to….. she stopped me mid sentence don’t be sorry. I seen you from the kitchen and just about walked out before I realised what was happening. I crept through to my room and was going to wait but couldn’t help myself I stood at the door and watched, I’ve never watched someone before and couldn’t believe how turned on I was. I watched you both for a few minutes before I realised my pussy was soaking wet wishing it was me bent over the sofa, I was playing with myself as I watched you fucking my best friend I had to bite my lip as I came hard |
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I can’t believe I just blurted that out she said I’m so sorry it was inappropriate, I’m your boss. I put my finger to her lips and she stopped talking. Hang on I said I’m that 1 that’s just been fucking your married best friend in your garden and your sorry!! We were standing in the kitchen so close to 1 another she leant against the cupboards and looked down at me I hadn’t even noticed my cock was rock solid and twitching against her, I slipped her towel off and helped her up onto the worktop and found myself burying my head between her legs. Her trimmed pussy was soaking wet and not quite as tight as the 1 I’d had 2hours previously but was just as tasty as I lapped at her juices now dribbling down my chin. It wasn’t long before my head was clamped between her thighs and she cumming all over my face. I helped her down and she led me to her bedroom we lay on the bed and right next to her was a massive pink rampant rabbit, she went to move it and I stopped her. That might come in handy later. She reached into her bedside table and produced some condoms. I wasn’t sure these would get any use this season she said as she expertly went down and started sucking my cock. A few minutes later she was straddling my face with her pussy my hands wrapped around pulling her arse cheeks apart as she hungrily sucked my cock. She climbed off and not open the packed and slowly slid a condom on me and squatted on the edge of the bed, hands grabbing the sheets as I stepped behind her and slapped her ass as I slipped my cock inside her |
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By (user no longer on site)
over a year ago
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As I slipped inside her she started bucking her arse back into me fucking my cock, I held onto her hips as she fucked me harder I heard her say something between moans and thought I’d miss heard, she said again “fuck my tight arse” we both slowed down and my cock slipped out as she moved and rolled over grabbing a bottle of lube from under her pillow. I watched as she squeezed some out onto my cock and wanking me making sure I was covered then squeezed more onto her fingers as she covered her tight arse and popped a finger inside I nearly came right there and then. She got on all 4’s on the edge of the bed as I stepped behind and held her hips my cock resting at her tight hole. I held my cock straight as she slowly worked her way back onto me. Twice my cock popped out but 3rd time lucky she gasped as the 1st couple of inches slipped inside her ass. Slowly I started fucking her as she grabbed a pillow and buried her face her back arched as I pounded her arse it was then I felt some resistance and noticed she’d moved a hand under her and was working her rabbit into her pussy I slowed and let her fill herself up but was soon pounding my cock into her in opposite strokes to her rabbit we were both cumming hard with minutes and were shattered. We lay on the bed just panting as I heard a txt on my phone. As we recovered she asked is that Liz? I checked and it was. What’s she saying? Sorry I’m being nosey. It’s ok I said. She asking what I’m doing, she’s telling Mike how her night went. Do you really think she’s actually telling him I asked? If I know Liz she’s telling him every single detail she laughed. Jane sat up and said can I ask you something? Of course I said. Are you going to go to theirs during the week? Mike said something earlier and it didn’t make sense but it does now. I’ve never watched someone else or been watched before but omg it was horny |
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Before I could say anything Janes phone pinged, it was Liz thanking her for a great night and asking if I’d gone home. Liz didn’t know yet Jane and watched us and replied yeah he’s just left. Liz replied. Please tell me you got it on with him. Shyly she replied my lips are sealed. I’ll take that as yes Liz replied you lucky, lucky girl. Hope your going to bring him round here? Jane replied I’ll ask him but I can’t make him if he has plans. Jane lay next me laughing, I think someone has plans for you she’s told me stories when she’s been d*unk but I took them with a pinch of salt. With that she asked if your going to come can I watch you again? Slightly taken a back I replied umm yeah sure I think. To be continued |
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By (user no longer on site)
over a year ago
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Don’t think you are going to lose your job
You have been promoted
More please  |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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By *untooMan
over a year ago
manchester |
Good story, more please |
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Great story - loving it. Look forward to the next developments |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Brilliant |
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By (user no longer on site)
over a year ago
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So very horny |
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By (user no longer on site)
over a year ago
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I left Jane’s the next morning and headed home for a shower and lay by the pool contemplating everything that had just happened in the last 24hrs. My phone pinged, it was Mike. Liz told me to say thanks for keeping her entertained last night, she never had such a laugh not too mention great company. Remember we’re on for the football during the week. Couple of folks coming over so should be good see about 5ish? I waited a little while before replying, can’t wait I’ll bring some beers. The next couple of days were quite hectic at work and then I woke on the morning of the game to a txt from Liz. Sorry I’ve been quiet I hope I didn’t make a fool of myself the other night, I’m a nightmare with a couple of drinks x. I replied are you going to be drinking tonight? I’m not sure, I’ll probably stick to soda, don’t want to show myself up x that’s a shame I replied, I was so looking forward to seeing what you had in store for me tonight. Ohh is that right she asked. Hmmmm god yeah!!! Here’s me thinking you just wanted to have your fun and tease me. Did you actually show Mike the video of the other night? I got no reply |
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By (user no longer on site)
over a year ago
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I msgd Jane after work after work to see what time we were getting a taxi and replied almost immediately. “So sorry, there’s been an incident in resort I’m not sure I’m going to make it, did Liz not txt you she’s coming to pick you up” by the time I got to my apartment she was standing waiting. What time do you call this? Do you always keep a lady waiting, she laughed. I didn’t know the plans had changed I’ll be about 15mins if you want to come up I asked. She followed me up and I let us in. My flat mates were all still in their hotels working so the place was empty, make yourself at home I’m just jumping in the shower. She went and sat out on the balcony and I went to shower. I’d only just climbed in and hadn’t heard the bathroom door opening, I turned around and there was Liz standing naked watching me, don’t mind do you? She asked as she stepped in beside me. Doesn’t look like I have a choice I said. She went to kiss me as she reached for my cock which was hardening by the second. You didn’t reply to my msg I said. Which 1 she asked? About Mike and the video I replied. Ohh that she said. Mike told me not too said he’d rather tell you in person. So you did show him it then? She smirked and grabbed my cock starting to slowly wank me. It wasn’t a video, he watched you fucking his wife live. I’d hardly even stepped in the door the other night before he was telling how horny he’d gotten. I was still a little sceptical of what was about to happen if anything was going to happen. She wanted my cock faster and faster and I was soon spurting streams of sticky cum all over her belly as the water cleaned it off. We climbed out and she smacked my arse, better get you to ours them hadn’t I she said. We arrived and joined the others who had already gathered for the game. There was us along with a couple of folks I knew and some I didn’t mostly guys. Mike spotted me after a few minutes and took my beers off me follow me he said. Introducing me to everyone and grabbing a cold drink should be a good game he said. I nodded as I took a swig then he lent in and said quietly and then we can see what Liz hasn’t stopped talking about for days. He chinked my bottle and smiled I can’t wait to watch Liz being fucked right in front of me, I just about spat my drink out. Now I knew and was a little nervous. Not sure why, I’d had the pleasure of several couples over the summer already but this felt a little different |
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By (user no longer on site)
over a year ago
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The next few hours went by like days, finally the match was over and 1 by 1 people started saying their goodbyes and making for the next games. It was starting to get dark now but was still sweltering in the heat. Liz whipped off her bikini top and jumped in the pool. I quickly followed and Liz swam over, remember my rules young man, my pool no swim shorts. You’ve got your bottoms on I protested, she quietly replied not for long. The last couple of guys finished their drinks and off they went leaving me, Mike and Liz. Mike was soon stripped off naked and diving in, swimming up to Liz giving her a kiss and cuddle. I’m assuming you didn’t pass on the pool rules he said to her. I did she replied but he obviously wasn’t listening as Mike untied her bottoms and threw them onto the side of the pool. I wriggled out of my shorts and threw them next to Liz’s. I’m guessing Kanes not joining us Mike said, she never abides by the rules anyway, I’m beginning to think she doesn’t fancy me. Liz just laughed and replied well you will try to offer her your cock at every opportunity darling. Maybe 1 day she’ll want to play he said crossing his fingers, I hope. I tried again the other night and thought I was in luck but she was just teasing. Ohhh you didn’t share that when I got home Liz said even after you watched us in action looking in my direction with a grin on her face. |
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By *erri AnneTV/TS
over a year ago
Shannon and Costa Blanca |
Loving the story can’t wait to see the next episodes |
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