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A True Story About My First Proper Girlfriend And An Unexpected Encounter

"An unexpected encounter with a much older man and my eighteen year old girlfriend"

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This is another true story about my first ever girlfriend June.

Those of you I have shared her folder of photos with will know how beautiful she was at the time, and will have seen the dress and heels that play a strong part in this story.

The events I write about here are perhaps my first tentative steps in cuckolding, even though I had never heard of the word at the time. I now feel it was what happened that lovely hot summer's day that played on my mind, and eventually led to my usual arrangement with Angela, a few years later.

It was the summer of 1980, and June and I had been dating for a few months. She had just turned eighteen and I was nineteen. At the time, I was quite inexperienced, sexually; in fact, it was she to whom I lost my virginity to a month or two before the events of this story. June was quite a lot more experienced than me, and had dated two guys before me, and lost her ‘cherry’ at a mere sixteen years old. She loved sex and loved trying new things and she was a very feminine girl. She loved to dress sexily, which attracted me to her from the start.

June loved to wear short skirts and dresses, but she also loved longer flowing dresses, usually of the wrap-over kind. She always wore very high heels, and she owned more pairs of high heels than any girl I have ever known. Her legs, of course, were perfect for shoes of this type, and she loved to make the most of that fact when we went out together or she was at work in the city of London.

She was even approached once, by a talent scout for a modelling agency, and after getting her parents' permission she did attend a professional fashion shoot in Central London for a hosiery company. Pretty Polly tights and stockings of the 1980s period did in fact feature June’s legs on the cover of the packets, as she eventually did two shoots for the company and they paid her well, despite her young age and her being an unknown model.

I remember well how nervous she was at that first casting shoot, but the people were most professional and took care of us both that day. She left with a nice glossy portfolio of prints of her legs in various heels and stockings.

Back to that summer day, in 1980.

We had driven up to Yorkshire to visit her brother and his wife in the village of Todmorden, for a long weekend. The weather that weekend was incredible, especially for the north of England, and we took summer clothes with us. June packed her favourite short summer dresses and three pairs of high heels. However, it was one particular dress she took with us that is the ‘spark’ for the events I tell here. I have attached a photo above of her in the dress, and heels she wore on the day of this event.

The dress was black chiffon, long-sleeved, with buttons down the front and a pretty collar It was of the drop-waist style, very fashionable at the time, and was very short.

The really sexy aspect of it however was the hemline, which was partially see-through. The dress was ultra-feminine, delicate, and extremely sexy. It suited June perfectly of course, and she adored wearing it.

She added a lovely pair of black suede high heels that had thin ankle straps. Under the dress, she wore a pair of silky black tanga-style knickers, but due to the weather that day she decided not to wear a bra.

We had decided, as it was our last day in Yorkshire, to visit the famous ‘Tavern Inn’ on ‘Stoodley Pike’, one of the area's highest peaks. It’s now called ‘The Top Brink Inn’, I think, but back then it was widely known as one of the highest pubs in England. The drive to the top is quite a beautiful experience, and due to the altitude, our ears ‘popped’ a little on the way up.

As I drove us along the winding lane to the top of the mountain, June sat next to me, her long smooth legs stretched out beside me. The dress had ridden up her thighs, and through the see-through hem I could just make out her tiny black silky knickers.

She looked sensational that day, with perfect makeup, and the week before our Yorkshire trip she had visited her hairdresser and had her hair cut a little shorter and restyled into this gorgeous little collar-length, wavy style that oozed sex appeal.

Eventually, we reached the crest of the mountain, so I turned my car into the car park of the pub and parked not too far from the main door.

We both got out of my car, June grabbed her handbag, and we made our way to the pub's front door. June’s high heels clicked loudly on the path, and I could see the wind playing tantalisingly with the hem of her dress. As she walked beside me, I hung back a little and watched in awe as the back of the dress was flapping up due to the wind, revealing June’s black knickers and her delicious ass. She smiled at me, cheekily, then used her hand to pat the back of the dress back in place.

We entered the pub together, walking into the main bar area. Inside were a few couples and families, enjoying meals and drinks at tables; however, I soon noticed there seemed to be far more men inside the Inn than women. Given how lovely the weather was that day the pub was by no means full, and we found ourselves a table with ease.

As we walked across the floor of the pub, and I couldn’t help noticing a few male eyes followed June as she walked in front of me. Most of the guys seemed to be a lot older than either of us and with her being so young, I assumed it was rare to see such a sexily dressed young girl inside the Inn.

As we passed one guy standing standing by the corner of the bar, he followed June with his eyes, looked her up and down as she walked, and said, ‘Oh yes baby girl, dressed to kill and looking so gorgeous.’

He was of medium height but stocky build, and appeared to me to be in his mid fifties or so. He was smiling at June, and she politely smiled back I noticed.

He then did a low whistle at her, and said, ‘Those legs baby,’ June was still blushing a little, but smiled at this man again. He then took his beer and walked away towards the right-hand side of the pub.We sat down, and soon after, the waiter approached our table. We ordered lunch and some drinks, then relaxed and enjoyed the atmosphere inside this famous English Inn.

Our lunch was lovely, and after I ordered more drinks, June got up from her seat and said she was going to the toilets. As she walked away, again I noticed several pairs of male eyes followed her every move. Her pretty little sheer dress did little to hide her long slim legs, and her high heels clicked loudly on the pub's wooden flooring.

She was gone for some time, but when she returned to our table, she had a sort of flushed look on her face, and she was almost blushing. I asked her if everything was ok.

‘Yes fine, Mark,’ she replied. ‘When I walked around the back of the bar to go to the toilets, I was whistled at by some of the men round there,’ she added.

‘That is hardly surprising babe, considering how beautiful you look today, and your outfit of course,’ I said.

’Two of them touched my bum as I passed them,’ she said.

‘Again, hardly surprising, darling,’ I replied.

We enjoyed our drinks, then I told her I too needed the toilet. So I shuffled past her legs and made my way to the toilets. June said she would buy us some coffee at the bar while I was gone.

As I rounded the bar, I noticed a small group of four men, all sitting and drinking pints. They all appeared to be in their forties and fifties and were engaged in conversation. As I drew nearer to them, I overheard some of what they were saying.

'Who the fuck was that?' asked one guy.

The man from earlier said, ‘That’s the girl I was telling you about.’

‘What a tasty little babe,’ said one of them.

‘Fucking gorgeous legs on her,’ said another, ’She looks so young, and that tight little ass on her.’

‘I could fuck that little blonde slut from here into next week,’ said another, ‘I bet her teen cunt is as sweet as honey.’

The last guy said, ‘I want her so badly, and I plan to have her, she looks perfect, would you be up for this gentlemen?’

‘Too right we are,’ they said.

‘Look how sexily she is dressed, she is begging for it surely?’ said the first guy.

I passed the group, my mind shocked at hearing them talking like this about my girlfriend; however, I found their words excited me a little, and inside I was proud to have such a pretty girl as June for my own.

I went into the male toilets, thinking about what I had just overheard from these men, any one of them more than old enough to be June’s father.

Suddenly I realised the zipper in my shorts was stuck. I tried and tried to free it, but it wouldn’t budge, so I calmed myself down a little, washed my hands and face, then applied some soap to the zipper. Slowly it began to loosen, and after some time I eventually got it fully free and I was able to pull it all the way up.

Panic over, I realised I had been ages in the toilet, and thought to myself how June must be wondering where I had got to.

I left the toilets and passed the group of guys once again. I noticed that there were now only three of them sitting at the bar. They ignored me of course, and I assumed they had no idea I was June’s boyfriend.

As I made my way around the bar, I suddenly stopped in my tracks at what I saw.

June was standing at the bar; she had bought our coffee, which was on the bar in front of her. Standing next to her, very closely, was the guy from the group, the one who had said, ‘I want her so badly.’ He was smartly dressed, and despite some grey strands in his hair, he was dark and ruggedly good-looking. I guessed his age to be around fifty or so, yet he was well built, with broad shoulders, and was very tall. Even wearing her high heels, he towered over June’s tiny frame.

They were engaged in conversation and June was smiling at him, not like she knew him but politely, however it was what he was doing with his hands that grabbed my attention.

He had one hand around her waist, and the other was holding one of her hands softly, both their arms were raised, with their elbows resting on the countertop.

I kept back, slightly hidden behind the curve of the wall I was standing against, and watched them both with interest, but also mild surprise. June seemed quite comfortable with this older man holding her hand and with his arm around her. Far from feeling any jealousy, I recall feeling excited by what I saw, and I could feel a stirring in my shorts, my cock getting slightly hard watching them both.

After a few minutes of this, he then took her delicate hand and kissed it softly; she was now blushing quite noticeably, but still appeared to be at ease. As I watched from my vantage point, his arm around her waist slowly began to slide lower down her body, and onto her ass. He caressed it gently through the thin chiffon hem of her dress; however, she then reached around with her left hand, grabbed his hand, then placed it back around her waist.

I continued watching the scene before me. They carried on talking, with this guy occasionally kissing June’s hand again. Soon he did it again, his left hand slowly slid down her body and back onto her bum. As before after a few moments, she reached around and carefully replaced his hand around her waist. This little ballet went on for around fifteen minutes, so I quickly moved out from my hiding place, walked quietly to our table, and sat down, now struggling to hide my ever-increasing hard-on inside my shorts.

As I sat back in my seat, the table conveniently hid the bulge in the front of my shorts from view. I noticed the pub was now almost empty of people. June and her new admirer were at the bar, and I could still hear his companions around the side, talking together.

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The man flirting with June had now lowered his hand once again, but this time he kissed her softly on the mouth at the same time. At first she made to pull away, but he gently pulled her head closer to him, and she relaxed as he kissed her, his other hand round the back of her head.

After a few moments, she began to respond to his kisses, kissing him back, softly at first, then more deeply, his hand still caressing her ass through her short little dress. As I watched open-mouthed, his hand slowly moved lower, under the hem of the dress, then inside and onto her satin knickers. This time, she did nothing to stop him, and they carried on kissing passionately while he felt her ass through her knickers.

I couldn’t believe this was my lovely girlfriend, June, happily letting this man old enough to be her father kiss her and feel her ass in public.

As I sat back watching this in awe, he then slowly slid his hand inside the top of her silky knickers, her dress now held up by his arm, slowly he worked his hand inside until he was feeling and caressing her bare bum right before my eyes. Their kissing was still just as passionate with him now holding her blonde hair in his hand and working his tongue inside her open mouth.

My cock was, by now, bursting through the front of my shorts, painfully so, but thankfully still hidden by the table I sat in front of. Why this turned me on so much, I did not understand at the time, but it did, massively so!

June then pulled away from him, straightened her dress, and grabbed her handbag, she spoke to him, and I could just make out her saying she was going to the toilets. He pulled her close again, then whispered something in her ear; she blushed, then smiled and whispered something back to him.

‘Good girl,’ I heard him say to her.

She then walked away from the bar, and round towards the toilets once more. She passed our table, grinned at me, then winked as she walked past.

I sat there in silence, totally dumbstruck at what was happening. My cock still threatened to rip through my shorts, at any moment!

I looked at the guy at the bar, and he was looking right back at me. He smiled, then nodded in my direction. Not really knowing what to do, I simply nodded back.

Around five minutes later, June returned from the toilets She had freshened her makeup and lipstick, and she looked as beautiful as ever. As she approached the bar again, she walked over towards me; before I could say anything, she reached inside her handbag, brought out her little satin knickers, and dropped them into my lap.

‘The man I have been with at the bar told me to take these off and give them to you, Mark,’ she said.

I looked down at her knickers in my lap, picked them up, then realised they were soaking wet; not with water, but with June’s pussy juices. I was about to say something, but June just smiled at me, then walked back towards the bar, taking her place once again next to the man.

Now without knickers on, the see-through lower section of her dress, did nothing to hide that fact and I could clearly see June’s bare ass as she walked back to the bar.

Their chatting and flirting continued, him once more, kissing her deeply, his hand soon went back down onto her ass, then under the hem of the dress, lifting it as he did so, then onto her now naked bum.

I just sat there, dumbstruck, my heart pounding in my chest, my cock straining even more inside my shorts, and I could feel myself leaking badly.

Then he slowly turned June more towards him, still kissing her and holding her close, his hand on her ass, then moved around to the front of her dress. He stroked her bare thighs, to begin with, then he move his hand between her thighs, and inside the front of the dress. June, parted her legs, just a little, and I saw his hand move deeper between her legs.

As they kissed, he was now probing deeper inside her pussy, and by the movements of his arm, I could tell he had worked his hand inside her, and his hand was going back and forth.

Occasionally, he would look over her shoulder at me, smiling, then he would carry on kissing and feeling her.

Watching this became too much for me and suddenly I climaxed, there and then, inside my shorts. Soon after, a wet patch appeared between my legs, but there was little I could do about it.

As I struggled to hide my still bulging cock and soaked shorts, I looked up to see them both walking away from the bar, round the other side, and to the back of the pub. June smiled at me as she went past our table, the man, did the same and nodded at me again. He was holding her hand as he walked her away to the far end of the pub.

I had to follow and see where he was taking her, and what was going to happen next, but first I had to deal with my wet shorts. I got up and dashed into the toilets, used the sink, then the hand dryer, which thankfully was powerful enough to dry my shorts so they looked almost as they had before.

I left the toilet, then made my way around the front of the bar and towards the back of the Inn. I noticed the man's companions were no longer sitting where they were before, and the pub was now pretty much empty apart from myself, June, and her new admirer.

As I made my way toward the far end of the pub, I noticed there was a partition wall, where I could stand but not be seen. June and the man were now sitting together in a corner booth, kissing once more, her legs now parted wide. Her flimsy little dress had been pulled up over her waist, her smooth pussy exposed. He had also unbuttoned the top of the dress and parted the two halves, exposing June’s small tits.

Also, I couldn’t help but notice, he had his erect cock out from inside his trousers, and one of June’s hands was stroking it slowly.

The man now had his hand buried between her thighs, his fingers probing and working inside her as they kissed. I heard June moaning through his kisses, and it seemed she was getting close to climaxing as well.

I stood there in silence and utter amazement as this stranger brought my young girlfriend to orgasm right there in the pub.

As her climax shattered through her young body, she bucked and writhed and jerked her long legs, the man still kissing her which stifled her cries of pleasure. Her dress was now round her waist, and she nearly slipped off the seat due to her orgasm being so intense, but the man held her firmly in place.

Suddenly, I realised someone was standing behind me. I looked around to find the man's three friends, all grinning and watching the spectacle before them.

One of them then said, ‘Is she your girlfriend, son?’

I stammered my reply. ‘Erm, Yes, she is.’

‘She is so fucking gorgeous, son,’ he replied.

‘Thank you,’ I said, not knowing what else to say.

‘How old is she?’ He asked.

‘She has just turned eighteen,’ I replied.

‘Fucking perfect, she is a prime cock-slut, and the perfect age,’ he said.

One of the others then said, ‘That's Steve with her by the way, he is going to make her an offer soon, that we all hope she accepts tonight, son.’

I said nothing to this, and just listened as he added, ‘Us four guys would love to show her just how we like to enjoy a tasty teenage girl like her, later on, tonight. If she agrees to Steve’s offer, that is.’

‘What is his offer?’ I asked.

‘Wait and see lad, I am sure he will tell you soon enough.’

I looked back towards June and the man to find he had pushed her head down deeply on his hard cock. He had a hold on the back of her head and proceeded to ‘bob’ her head up and down on his shaft.

Not long afterward he gasped once, then held her head down fully on his cock as he climaxed, pumping his load deep into her young mouth. I could hear her moaning and gurgling, no doubt she was swallowing his cum as best she could.

‘Ahhh, fuck!’ he said, ‘That’s it, baby girl, you swallow down daddy's spunk.’

Watching this, my eyes wide and my mouth open, I was suddenly jolted back to reality by one of the men behind me.

‘Come on lad, leave her with Steve, as he needs to speak to her in private about his offer.’

The three men then led me away from June and Steve. We went back to the bar, where they ordered fresh coffee for us all.

Soon afterward, June came to join me, followed by Steve. She was blushing and looked flushed and sweaty; she told me she would just be a minute, then walked towards the toilets to clean herself up.

Steve then gave me a slip of paper. ‘That’s my phone number and address, Mark, if she changes her mind, call me tonight, then bring her to my house, I live just two miles from here, and I promise you the four of us will give her a night of fucking she will never forget.’

Speechless again, I just listened as he added, ‘All holes, no condoms, no limits, and we will fill her teenage body with more cock and cum than she has ever imagined, Mark’

‘You can relax at my place and watch it all, son, if you would like that.’

‘I, I, don’t know what to say,’ I replied.

‘Would you like to watch that, lad?’ asked one of the other guys.

‘I... I don’t know, I think so,’ was all I could think of saying.

‘I am sure you would love it, Mark,’ said Steve.

He added, ‘We are all experienced enough to know just how to use and enjoy a sexy little slut like her.’

Another of the group added, ‘We all cum heavily, Mark, and we can repeat more than once, that’s a promise.’

‘Especially for a tasty little teenage girl like yours.’

He added, ‘You can’t bring a young girl like her into this pub, looking like that, wearing that dress and those fuck me heels, then not expect guys like us to all want to fuck her, son.’

The same guy added, ‘I would love to pump her tight little ass full of my cum for you, Mark.’

The others all agreed on his point, with them adding how beautiful they thought June was, and how much they hoped she would decide to accept Steve’s offer tonight.

‘Talk to her after we leave, Mark, talk her into it; neither of you will regret it, I guarantee you that,’ said Steve, adding, ‘We would love to put her through her paces together for two to three hours tonight, Mark.’

‘Has she been gang-banged before, Mark?’ asked Steve.

‘I don’t think so, I don’t know,’ I replied.

‘Well eighteen, is the perfect age for her to start,’ he said, ‘And we have gang-banged young girls like her many times before.’

The four guys said their goodbyes and made to leave the pub, just as June was returning from the toilets.

‘Hope we all see you later, darling,’ said Steve.

We left the pub soon afterward. In the car as we drove down the mountain, I asked June, ‘Did you enjoy yourself, babe?’

‘God yes,’ she replied, ‘I think you could see that, Mark.’

I then popped the question. Steve’s piece of paper was by the gear lever, ‘Do you want to call Steve tonight and accept his offer?’

June looked sheepishly at me, then said, ‘I don’t know, I said no to him in the pub as I don’t want to ruin our relationship, Mark.’

‘I don’t think it would ruin anything, June, my love, if it’s what you want to do?’ I said.

‘Wouldn’t you be eaten up with jealousy?’ she asked.

I replied, ‘I don’t think so, no, not if it’s truly what you want to experience.’

‘Remember, I am not on the pill, currently,’ she said.

‘Yes, I realise that babe, Steve said no condoms, didn’t he?’ I said.

‘Yes, he did,’ she said, ‘but I am very tempted, Mark.’

With that, we drove to the bottom of ‘Stoodley Pike’, then back to her brother's house for our last night in Yorkshire.

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Written by Lazycalm56
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