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Picking Cherries
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By *ister_E OP Man 9 weeks ago
Hayling Island |
I got a wink from a couple up in the Midlands a few weeks ago, To far away to take seriously as anything other than another fantasist / pic collecter but out of curiosity I had a quick look at their profile anyway.
Sounded pretty vanilla, new couple, looking to explore, both str8, no pics or interests, and not looking for single guys etc..
So without any expectations, I sent a quick email saying "hi" Introducing myself and asking if they were looking to chat etc.
To my surprise they messaged right back. Nice holiday pic of a good looking mid 30's couple in swimwear. He was tall, dark hair, slim waist, but decent build, nice muscular chest with a fair bit of hair like myself.
She was so pretty it hurt! About 5'4" dark hair, pale porcelain skin, green eyes and a gorgeous, mischievous smile. Gorgeous curvy hourglass figure and she filled her bikini to bursting point!
They definitely had my attention!
They introduced themselves as Danny and Sarah and explained that they were new to this and wanted to explore some shared fantasies and whilst being slightly nervous they were really excited about the idea of watching each other with other people. And were so turned on by the thought their parner being pleasured by a stranger  |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
I of course quickly replied! I responded that I loved chatting with new couples and was happy to share my experiences and any advice that I could,
I informed them that I had a little experience with first time couples and have enjoyed a few incredible meets with amazing cuckold and Stag and Vixen couples
And if it wasn't fornthe distance I'd be only to happy to use or pleasure Sarah while Danny watched and supported her. |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
It Sarah I was chatting to and not Danny, but that wasn't the surprise...
They were coming down to Hayling for a weekend and were potentially looking for a meet ....
But again that wasn't the real surprise either...
Their fantasy wasn't to cuck Danny, or for it to be Sarah's first MFM 3sum either...
Sarah had found out that Danny actually had A Bi fantasy and she wanted to surprise him with his first man on man experience and that she wanted to just watch and film the whole thing |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
I was blown away! I had not seen that coming at all! So more pics and messages were exchanged. We switched to Kik so that we could share pics and videos easier.
And a week or so later I was freshly shaved and showered and rock hard, and standing ouside their Static Caravan texting that I was there... |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
Sarah opened the door in her pink dressing gown and fluffy slippers. She invited me in with a very nervous smile and a hug.
She accepted the bottle of bubbly I had bought with me, and led me to the konge, where a very nervous looking Danny was waiting awkwardly his dressing gown and she introduced us.
He was almost visibly trembling from either nerves, or excitement, or both. So I figured that the best thing was to be confident and matterb of fact, and to try to normalise things as much as possible... |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
I took his outstretched on hand and pulled him into a quick man hug. I said "don't talk, it just gets awkward, and makes it worse." I smiled confidently to reasure him "Just take it slow and follow your gut and you don't need to do anything you don't want to. I'll stop anytime either of you ask me to. The best way to get past your nerves is to close your eyes and go with your gut! Just do what your body is telling you feels right". |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
Sarah was positively glowing with anticipation and started pouring drinks for us, I took his hands and placed one on my chest and the other I guided directly onto my bulge and leaving it there I started undoing my shirt. |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
I still remember the rush the first time I held another guys cock, and I wanted him to enjoy that same 'taboo' thrill, without any pressure or feeling hurried...
I calmly unbuttoned my shirt and looked across to where Sarah was standing mesmerised in anticipation. I think she was almost as exited as we were... she was clearly a very naughty girl 
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By *ister_E OP Man 9 weeks ago
Hayling Island |
His left hand absent mindedly stroked my chest, running his fingertips throug the coarse hair as I shrugged my shirt off and let it fall away.
But he was truly lost in what his right hand was doing he stroked and grasped my cock, with eagerness and a profound desire that only made me harder.
I moaned softly to encourage him!
I ran my right hand slowly down his chest and then down his arm and over his hand to slow him down and guide him.
Then I placed it onto his cock, so that I could gauge his response and feel his desire building. |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
Even through the thick soft fabric I could feel that he was rock hard and bigger than average.
I couldn't close my hand around his shaft through the thick fabric. But I was able to grasp him firmly and squeeze and rub and pull on his lovely big dick.
He exhaled a deep soft, moan of pleasure. And I actually felt his knees give out slightly at the overload of pleasure he was experiencing. 
He matched my actions and movements and I could feel his confidence growing as he began to let go of his inhibitions and loose himself in the moment. |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
I let go of him long enough to undo my trouser button and ease my fly down slightly... an open invitation which he quickly accepted He eagerly slid his hand down the front of my trousers and his bare hand found my naked shaft waiting for him.
His fingers encircled me, my cock twitching and throbbing in response to his touch. I could see him entering that exquisite, trans like state of erotic bliss, as he squeezed and stroked another man's bare cock for the first time in his life
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By *ister_E OP Man 9 weeks ago
Hayling Island |
Unable to resist any longer I slidbmy own hand under his gown and gripped him firmly and then began to stroke him very slowly.
Sarah was watching with rapt interest. Especialy when I dropped my trousers to stand there naked and then opened his gown so that she could see everything! |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
I had to keep slowing him down, because the way he was rubbing my exposed glans was getting a little uncomfortable. So I showed him how to properly hold a circumcised cock and explained the difference when you're stroking one. And I demonstrated different techniques with his big cock as I spoke.
He was an eager and apt pupil and
I needed to change the pace before we went to far. I led him to the sofa and invited her to sit next to him.
I let him stroke me a little more , at more of an eye level this time. She slipped her dressing gown off to reveal a gorgeous lacey black and white lingerie set that got my blood racing!
I was hoping he would automatically know what to do next, but he wasn't confident enough.. So I said "let me show you what to do next". I slowly sank to my knees in front of him grasped his cock at the base and tilted it towards me. As I looked directly up into her burning eyes |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
She was so ready for this. Biting and licking her lips in anticipation.
I touched my lips to his glans and felt the pre cum stick to them as I kissed the tip. His eyes were closed and he was thrusting his cock out to me,
Wordlessly begging me to just grasp his shaft and then suck him deep....
But I pulled away teasing him, teasing them both, and licked the trailing pre-cum from mu lips as I gazed directly into her eyes.
I kissed the tip again and opened my lips slightly this time. Each time I took him ever so slightly deeper, licking his head, shaft and slit in between. He moaned and gripped the seat cushions in frustration and pleasure as I teased him ad then he gripped my head as I took him as deep as I could.
I showed him how to swirl my tounge around the edge of his head,and lick under the rim of the glans to stimulate all of those nerve endings. I showed him how to control the depth of penetration with my hand around the base of his cock.
I showed him that I could fuck him with my mouth or let him fuck my face as hard and fast as he wanted, but that I could always maintain absolute control of how much cock I wanted.
I stroked and licked his shaft, balls and perrenium and sucked and cupped and squeezed his balls to show him so.e of the many ways to pleasure and own a man with your mouth....
She was enraptured by my mouth on his cock. She was hugging him and stroking his chest, kissing his face, neck, ears and lips. She even held him and stroked him as I sucked him and she played with me. Wiping his glans across my lips teasingly. And taking pre cum off his tip and putting it to my lips to suck her fingertips clean.
I wasn't trying to make him orgasm. I was just pleasuring him and myself too! |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
I wanted to give him a break, so I pulled away and stood up I front of him again.
Without hesitation he grasped me in his hand again and this time she did too her delicate hands on top so that she could be a part of it too.
Then slowly he brought his head forwards. To meet my aching cock,
I was so hard that it was throbbing with a life of its own by now.
He also began by kissing the tip and then followed my examples from earlier. She was holding me for him to suck though... fuck that was so gorny and unexpected
I'd genuinely thought she was just going to watch, and seing her tripping on his pleasure and desire was so erotic. Especially when she fed him my pre-cum! |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
He worked my head for a long time.... from the way he sucked it in and swirled his tounge around it was clear he had payed attention when I was sucking him and I was amazed at how deep he took me. Literally to the hilt, which amazed me  (although I later found out that they had been practicing with her steapon)
She was Golding his head with her hands and fucking me with his mouth as she told him how hot this was and how much she was loving it.
I had to stop quicker than I wanted as I didn't want to cum in his mouth as I knew he would never handle it. So, when I warned them that I was going to cum. He pulled away and she wanked me harder and faster as I blew a massive load all over his his chest, face and neck. I just kept spurting jet after jet of hot cum all over him as she guided it and milked every drop out of me!
Then he sucked me softly as I began to relax and he clearly wasn't put off by the trickle of cum escaping as my throbbing cock as I came down from my orgasm he obviously like it a lot because he swallowed every drop and watching her kissing him afterwards was hot as Fuck! |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
She was kissing him and whispering to him how hot it was for her as she cleaned all of my cum off of his naked body with a towel and then wet wipes.
It was such an intimate moment between them, that I was reminded what a privilege it is to be invited to share moments like this with a couple who love each other so deeply.
I just stood back and enjoyed the afterglow, and gave them some space for a moment.
I wasn't ready for him to cum yet . So I was not going to finish him off with my mouth straight away.
I wasn't being selfish, most 'str8' guys experience a post orgasm guilt the first few times they play with another guy. There is a strong sense of shame and embarrassment that overwhelms them and they just want to go or for you to go. It can be incredibly awkward for them.
And if you ever make a 'str8' or curious guy orgasm then it's best to wrap up the meet quickly after that and not expect to hang around drinking beer and making small talk...
There were still to many things I wanted to to do with and to him to let it end now. So I gathered up the drinks and suggested that we move to bedroom to carry on with the fun |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
I placed the lube and condoms I'd bought with me on the side table. And I could see from the toys in the room that they had been having plenty of fun getting him ready for his big night
A big tube of lube, a couple of butt plugs various dildos, a Hitachi wand, some restraints, blindfolds and a very realistic looking strap on in a harness... These two clearly knew how to have a good time
There was no way we going to use even a fraction of that lot this time, but it created a very hedonistic atmosphere and left no doubt about where this was going to end up  |
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By *ister_E OP Man 9 weeks ago
Hayling Island |
I was sitting on the bed when they came in so it was only natural that his cock ended up in my mouth again... (he had a lovely cock to suck by the way)
It was almost inch longer than mine which is something I've not often got to experience, but not nearly as girthy as mine.
It was perfecly straight, with a slight downward curve and a loose foreskin that easily and fully retracted to expose a slightly pointy head that was a only a little wider than the tapering of his shaft.
It was almost enough to tempt me to try and bottom myself. Lol never going to happen, but the point is he had a lovelycock to play with and suck on... so thats what I did!
It was enough to start my cock stirring again so I lay back and let him play with and suck my semi in return... It was clear he was enjoying feeling it responding to his touch and growing harder in his mouth.
I was a little regretful that I'd cum so quickly as I wanted to be a full mast to enter him. Anal can already be tricky when your partner is really tight and almost impossible if you're not really hard when trying to open them up.
But his hot, wet mouth and the pleasure he was taking from sucking me off was already starting to have the desired effect.
And Sarah standing next to him, guiding his head, kissing him and even having a little go herself as they sucked me together was so hot. She also kept touching him and massaging and slowly tugging on his cock.
It was really got to see that this was her fantasy too! She was loving his obvious pleasure, and her involvement was without any jealousy of any kind, her involvement was clearly about adding to his experience and pleasure and not that she was feeling left out at all.
I suggested a change of positions and for him to get up on the bed.
As he did so I changed around so that we were lying next to each other on our sides.
I took a moment to remind her that I was happy for her to take pictures or to film us if she wanted to. (It's so easy to forget in the heat of the moment and I knew that they would regret it if the didn't keep some momento's to remember the nights pleasures...
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By *ister_E OP Man 9 weeks ago
Hayling Island |
So we did some slow relaxed 69 stuff, stroking and sucking each other for her to watch and snap a few pics.
It just playful, relaxed pleasure, neither of us trying to make the other cum. Just enjoying holding and sucking a nice cock and putting on a bit of a show for her to enjoy...
Then I moved my body around so that I was kneeling in between his legs. Whilst he was clearly disappointed that I took his new toy away, he was also Intrigued and exited to see what I was going to do next
I pointed at the lube which she passed to me and put a bit on my hands and started to give him a slow, sensual, slippery lubed handjob playing with his balls and appreciating how his legs opened wider and wider, exposing his pink virgin hole. Putting more lube out my hand I stoked his perrenium. Rubbing up and down as I stroked his cock and edged him.
He let out a gasping moan and his whole body shuddered as my fingertips brushed his hole |
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By *ister_E OP Man 8 weeks ago
Hayling Island |
His puckered pink hole twitched and winked in eager response to my wet fingertips. I circled and rubbed my fingers slowly over and around it.
I was in effect rimming him with my fingertips while I edged his cock. My index fingertip slipped eaily inside him with a slight pressure. So I deliberately worked it in and out . Pushing lube into his hole.
He took the whole finger next moaning in pleasure as I touched his prostate. Two fingers was a little tighter, but no real resistance and he was now rocking himself and fucking my fingers with his ass.
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By *ister_E OP Man 8 weeks ago
Hayling Island |
Sarah was sitting on a chair with her phone in one hand and the other inside her panties. She was rubbing herself hard and ow with a fleet fingertips and her panties were pretty soaked from how wet she was. I replaced my two fingers with my thumb and put his cock to my lips to taste his precum that was oozing out in a slow steady trickle.
It tasted so good that I sucked him super slow and just let him grind himself on my thumb. He was pushing against the base of the thumb and desperately trying to get it deeper inside him.
I asked Sarah to hand me a condom and he shuddered so hard at the words that I thought he was about to cum lol...
We were lying on our backs next to each other and she came over and stroked us each in turn and together. She bent over and sucked him deepand them much to my shock did the same to me.
She held me firmly and rolled the condom down my swollen throbbing cock and cupped my heavy balls for a moment.
She took the lube and applied it liberaly to my cock and then to his ass as I got into position to penetrate him.
I chose their favourite pegging position... spoons... it wouldn't have been my first choice personaly, but it was what was most comfortable for them and would give her an incredible view of everything! He lay on his side squeezing and rubbing his lovely cock as I moved to position myself on my side behind him.
Sarah supported his raised leg and guided my cock to his nervous, waiting, fuckhole.
She held me in her lubed fist as I started to apply slow, firm,steady pressure... |
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By *ister_E OP Man 8 weeks ago
Hayling Island |
I am forced to admit that his moan of pleasure as I started started to enter him almost made me cum right there and then.
His ass was so tight, but offered almost no resistance as I slid through the first sphincter.
He drew in a huge breath and his hole clenched around my head. I'm sure I could have just pushed through and entered him to the hilt in a single thrust, but I wanted it to last and to draw the experience out!
So I just held it there for what felt for ever... not releasing any pressure but not pushing further. I couldn't see Sarah because she was videoing and I was focused on reading his body language, and enjoying the throbbing clenched of his ass squeezing me as he got used to the feeling.
He lay with his eyes closed and his moans were so erotic! He was rock hard and he was gripping and squeezing his cock in pleasure.
I felt all the resistance drain from him as his hole opened to welcome my girth. My full length slid effortlessly into him and I thrilled with his pleasure as he shuddered and moaned.
He was leaking pre cum in a constant stream. And he used it as lube to wank himself as I gently began to rock slowly back and fourth.
Sarah was wild with delight at this point. She had abandoned her camera, and was stroking him and rubbing herself as I ever so slowly began to fuck his virgin ass.
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By *ister_E OP Man 8 weeks ago
Hayling Island |
I had to fuck him so slowly it was almost painful! Not to avoid hurting him, but rather that I knew he was only a deep hard thrust or two away from orgasm
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I eased my cock back and fourth. Almost pulling out and slowly pushing into him with an accompanying gasp and moan of pleasure. Then I would just hold it there for as long as possible before doing it again.
She was licking and sucking on his massive, leaking cock now and I was rubbing and fingering her soaking wet cunt, as I stretched and filled his bum with my thick cock.
I eased out him and told him to kneel on the bed for me and I instructed Sarah to lie down and let him lick her out.
She lay hack and spread her legs. And he buried his face in her gorgeous pussy as she spread herself wide with her fingers.
I really wanted to fuck him on his back like a woman. I just love stroking a guys cock as I fuck to orgasm, and see see him shooting his hot cum all over himself as he climaxes.
But thos was their moment not min. his hole was pink and slightly puffy from stimulation a arousal and it looked so good as I spread his cheeks wide with my hands.
Then I lowered my face to it an licked it as he gasped in unexpected pleasure I teased rimmed and probed his hole with my tounge as he went into a frenzy with hi own tounge in her pussy. I Rimmed him deep and hard as they both moaned with pleasure.
Then sensing the moment had come I straightened up and lubed us both up again before pushing all the way into his ass again with one long, slow, smooth thrust. Although he didn't resist I felt he was so much tighter in this position! He was licking her like a hungry dog and she held his head there and looked directly in the eyes.
She was wild with animalistic and told me to fuck him! To "fuck him like a bitch" I couldn't HD back much longer and began with tiny, hard fast thrusts, pushing his fave into her and working his prostate.
They were both moaning and gasping and he started to shudder almost immediately. His whole body began to shake and spasm.
His anal muscles gripped me so hard that it was almost painful.
His shaking animalistic moans and shaking was unmistakable and his massive orgasm triggered my own I nside him.
Gripping his hips I roared with easure drove my cock deep into him. Long, hard, deep, fast thrusts. Pumping my cum into the condom. Jet after jet of ot cum with every thrust, timing each trust with with the spasming of his arse.
She heard and felt our climax and she had her eyes screwed up and was gripping the bedsheets and making keening noises as he licked her though her own orgasm even as my final thrusts pushed his face hard into her.
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By *ister_E OP Man 8 weeks ago
Hayling Island |
I didn't pull out straight away. We all just help each other as our orgasms slowly subsided. Every time each of us had another aftershock it would trigger the other two into a mini spasm of pleasure and all of us would shake and shudder in pleasure.
With my cock deflating I reluctantly slid out of him and moved closer to watch him slowy and gently lapping up the final juices of her orgasm.
Sarah reached out and clumsily removed the condom, splattering my cum everywhere and tossing it aside. She then drew my semi Into her mouth and sucked me clean. With soft, sensual intensity.
I was oversensitive really so it it was almost painfully intense, but also to good to stop. He just lay there touching himself and his rubbing his bumhole in a kind of dreamy extacy.
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By *ister_E OP Man 8 weeks ago
Hayling Island |
Then they began to kiss and touch each other softly and intimately as lovers do when in the afterglow.
I retreated to the small bathroom where I washed and silently got dressed. I didn't make a fuss about leaving and neither did they. We had discussed post-coital shame and depression, and had all agreed that it would be best all round if I left right afterwards with the minimum fuss.
So I reluctantly left them to enjoy thr moment, and each other. Hoping only that they will both be back soon |
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By *ister_E OP Man 8 weeks ago
Hayling Island |
There is no greater thrill than sharing a first time encounter with someone! The "first time" is something that they will always remember and I love to try and make make it something special for them.
Picking a cherry is such a privilege. And when someone trusts you enou6to gift that to you its something to treasure and respect.
So hopefully there will still be many more couples looking to share their first time swinging or first time bi experiences with me!  |
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By *ister_E OP Man 8 weeks ago
Hayling Island |
Thanks for all of the support and interest in my story To answer a few questions.
Yes, this is a true story.
No, my wife doesn't watch or play
And no I'm not going to travel hundreds of miles to come fuck your arse!
Lastly I love all the questions and support, but post your questions and comments here rather than sending me a pm. Thanks!
ET
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