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Published : 13 April 2022

   

Already seen Paul's first time, click here to read Awakening, or here to read June's First Time, or here to read after June's deflowering

Awakening – Paul's first time
by Isabella

Story Code: m/F, M/m, MM/m, F/F, Voyeurism, Exhibitionism, Incest, Mum/Son, Prostitution

Our holiday was turning out to be not only an eye opener for me about my wife's past sexual history...after so many years of her refusing to tell me anything about her past sex life before she met me but it also changed me in a massive way, from wanting sex once a month or less, to wanting to fuck my wife every time she added a little more about her sexual history as a part of the Wellingborough 'Game of Life!' group. I would have put it down to misremembered acts from her preteen years or fantasy daydreams made real by a nine year old girl's imagination but, there seemed to be a small cadre of players of the same game in our holiday village and June managed to spot every one of those men, just from the way that they acted around children and young people on the beach but also, because June was able to spot a secret message that players used to identify each other.

We were on the beach early on the third morning of our holiday, June pointed out a man wearing blue trunks, "Remember him, he took two girls behind the bar that first morning that we were here on the beach, he's paying a lot of attention to the man in the red Speedo trunks, he's so white, he must have arrived here on last night's flight from England...if you watch his hands, he'll make two fists and tap his right fist down on top of his left hand, little finger of his right hand on top of the index finger of his left hand...oh!"

I looked at her, "Oh...what?"

"Ok, it's the man in the red Speedos that's making the opening sign, if you look at his hands, you'll see that the shape makes up a printer's lowercase 'G'! If the man in the blue trunks is a member of the game, he will respond by touching the tip of his right index finger against the third finger of his left hand...see...see, he's making the response. Now, the man in the red speedos will place his index finger across the palm of his left hand, roughly around the heart line!"

I looked back to the man in the red Speedos, his hands were in the exact positions that June had said that they would be.

"So darling...what did all that messaging mean?"

"It is very simple Paul darling, the three hand signals spell out 'GOL', for Game of Life!"

"How did you know exactly how the players identified each other?"

She grinned at me, "From years of watching new players coming into the area and identifying each other, when I realised that they were using sign language, I asked a deaf friend what each hand gesture meant and as soon as she said that it was 'G', 'O' and 'L', I realised what it was all about."

We watched the two men starting to get to know each other, they exchanged contacts and swapped files across their mobile devices and then they went off on the hunt together, one man cutting a child out of a group and passing that child on to the other before returning, back as close to the parents as possible to throw suspicion off of him and a little later, the other man would encourage a child away from its family for his friend to try to win over. Because they were both players of the game, they were always gentle with the kids and never hurt them more than was needed to have their fun before sending the child back to its parents before they were missed.

June reached for the sun lotion, accidentally stroked her hand over the front of my trunks, finding my cock hard from watching yet another young girl slip into the shadows behind the bar with one of the two men, their fifth success between them that morning.

June smiled at me and whispered, "Shall we pop up to our room and see what we can do about this?"

I nodded my head with a stupid schoolboy grin on my face, "I'll grab us a couple of cocktails of the day from the bar and follow you up!"

Today's cocktail was a Brandy Alexander, it looked more like a milkshake than an alcoholic drink, not so appealing to me but as they were free, I took them anyway, I was sure that June would happily drink them both if I didn't like the taste.

When I got up to the room June was naked and waiting for me on our bed, I handed her one of the two drinks, she sipped at it and said, "Mmmm...lovely!"

Page 1

I sipped mine and said, "I'm glad you like it, you can drink mine as well!"

June took a gulp of her cocktail and then popped it on the bedside table and said, "Why don't you tell me about your earliest memory of sex darling...while I suck your cock for you!"

I lay on my back while June sucked my cock and I remembered back to my first memory of having sex...

When I was eleven years old, my mother's best friend at the time was Ann Smith, her son Jimmy was my best friend and we hung out together almost every day...that was, until Ann caught her husband in bed with another woman and she left him, not just moving away but emigrating to the Socialist Republic of Leicester and I totally lost touch with Jimmy but my mother did keep in touch with her friend Ann.

I'd actually forgotten all about Ann and Jimmy Smith over the years but just after my sixteenth birthday and quite out of the blue, my mother told me that she was going to visit Ann Smith in Leicester, it had taken five long years but Ann had finally got her 'Decree Nisi' from the court and was now a free woman and wanted to go out and celebrate and my mother was planning on taking the train to Leicester, going out for a drink with Ann and stopping overnight at Ann's house.

I wasn't really included in my mother's plan at the outset but my father made plans for himself that also didn't include me so I ended up having to go on the train to Leicester with my mother, I would keep my once best friend company while my mother and his were out on the tiles and I'd sleep in Jimmy's bed with him overnight while my mother slept in Ann's bed with her.

Meeting Jimmy for the first time in five years was a shock, he'd changed a lot, I still considered myself a sixteen year old boy, Jimmy considered himself a sixteen year old man. He followed my mother around the house as she was getting ready to go out, I spotted Jimmy peeping at my mother while she was wearing just her bra and knickers...I have to say that over the years, my mother had often been careless in that way around me, I usually just looked away until she was properly dressed or left the room. The door closed behind our mother's back as they left for the local pub and Jimmy almost jumped in with, "Are you still a virgin Paul?"

I was really shocked, "Of course I am!"

"I thought so...the way you blushed when your mother walked past us in just her bra and knickers and couldn't even look at her...well, I'll tell you this, if I get the opportunity when they get back, I'll have a go at fucking your mother if she's drunk enough."

"Are you telling me that you're not a virgin?"

Jimmy laughed, "I lost that within weeks of us moving to Leicester!"

He'd moved to Leicester when he was only eleven years old, so if he did lose his virginity within a few days of moving to Leicester he must have only been eleven when he lost his virginity.

"So...how did that happen when you were only eleven years old?"

The first Saturday that we were in Leicester, I went exploring in the city centre while my mother was doing her shopping, I found an amusement arcade called 'Playland' on Humberstone Gate right next to the Grammar School, it had a few boys around my age and a lot of older men playing the machines...I met a man called John, he asked me if I liked girls...naturally, I said that I did and even though I knew that it might not be safe to get in a car with a stranger, I did for the chance to meet a girl.

He asked me if I'd like to go home with him to meet his daughter, she was a little older than me and really liked boys but there weren't many young boys where they lived.

John's daughter, Samantha, was the first girl that I ever fucked, John watched us and while I was screwing Samantha, John undressed himself and joined us on the bed, after I finished screwing Sam, I had to let John play with me...that bit was painful but it was worth it to be able to return to see Samantha again. Over the past five years, I've screwed six different girls but Samantha was always the best.

Page 2

Jimmy had a pile of dirty books in his bedroom and we spent the evening reading through those books, Jimmy had a passion for younger men having sex with older women, in all of his books, the pages with those stories on them were the most thumbed as well as the most 'Stained'. Jimmy encouraged me to read all of his most favourite stories, some were mothers and their sons having sex, a few were aunties and nephews and fewer still were grandmothers and their grandsons having sex but the biggest number by far were of older neighbours seducing young boys in their neighbourhood.

During the course of the evening, I realised that from the staining on the pages, I could work out which stories turned Jimmy on the most and the one that had the most stains of all was a story about a boy seducing his best friend's mother.

At ten thirty, Jimmy suggested that we change into our pyjamas and wait in the living room for our mothers to get home. There was a program on Channel Four at ten thirty about young American girls that took part in Beauty Pageants and the lengths that they, and their mothers, would go to just to win a stupid pageant, including offering sexual favours to the judges, that Jimmy wanted to watch.

I stripped down to my vest and underpants and was about to pull my pyjama bottoms on but Jimmy stopped me, he shook his head and said, "Just your Pyjamas Paul, nothing under them, pants and vests just get in the way of having fun!"

I complied with Jimmy's instruction but I have to say that I was suspicious that he had plans to fiddle with me, as Jimmy told me about his early sexual experiences, men often came into the story, men having sex with Jimmy after letting him screw a girl or woman that the man had control over.

Jimmy's living room was very tidy but Jimmy changed that, he piled old newspapers and magazines on one of the single comfortable chairs, he made me sit on the other single chair while he sat on the two seat sofa on his own. We watched TV for an hour before the front door banged open, my mum shushing Ann, "Shhhh! You'll wake the boys Ann!"

Ann giggled, "My Jimmy won't be in bed yet...he'll be watching something dirty on the TV at this time of night."

The living room door crashed open in a similar way to the front door, my mother stumbled through the door first, Ann was encouraging her to come deeper into the room and guided her to sit on the sofa next to Jimmy, Ann said, "You sit there while I go and make us some coffee!"

Ann didn't leave the room, she stood behind the seat that I was sitting on, she was stroking my shoulders and neck for a few seconds, just long enough to watch Jimmy moving in on my mother, he stretched his left arm over my mother's shoulders, behind her neck, he was stroking the left side of her neck as he whispered, "Did you get lucky tonight Elizabeth?"

My mother looked into Jimmy's face and she giggled, "No, there were no suitable men out in the pub tonight!"

Jimmy's right hand had moved, he had turned slightly towards my mother and he had placed his hand on her stomach.

Ann moved to the side of my chair, "Come and help me in the kitchen Paul!"

I didn't get the chance to say no, Ann grabbed my arm and pulled me out of the chair.

I heard my mother giggle again but as I reached the doorway, her giggle was cut short, I looked over my shoulder, Jimmy's lips were covering my mother's lips and his left hand had stopped stroking her neck and shoulder, it was now pulling the zipper down the back of her dress open.

I went to go towards the kitchen but Ann pulled me towards the stairs, "Your mother won't thank me for a coffee for a few hours, we need to find something to do until she's ready to sober up!"

I was pulled into Ann's bedroom, her hand slipped inside the fly of my pyjama bottoms and she rubbed my cock...I was shocked, not only at her attack on my cock but the way it responded to her touch, it jumped from totally sleeping to fully hard in a fraction of a second. As Ann rubbed over my cock, she kissed me and then she whispered, "Unzip my dress for me please", between a barrage of kisses.

Page 3

I was still a total virgin...not just a technical virgin, before today, I hadn't had a sexual thought in my head...or should that be in my body? But it was strange how, without even thinking about it, I reacted to Ann's requests, I stripped her totally naked in her bedroom as she stripped me out of my pyjamas.

I jumped on her body on the bed and fucked her, my first ever fuck and as the feeling of intense pleasure flooded through my body, I realised just what I'd been missing, even though the whole thing was over in fifteen seconds.

Ann was a little disappointed at how fast I'd climaxed but she wriggled out from under my panting body and she sucked my cock until it was hard again and we repeated the fuck, the second time, I lasted two and a half minutes, rather than fifteen seconds. We went through several more iterations of Ann sucking me hard after I had climaxed into her and me fucking her all over again and lasting several minutes longer before climaxing each time.

After an hour of fucking, Ann called it a night and she went down stairs to make my mother her cup of coffee, leaving me in her bed. Ann was still totally naked as she went down to the kitchen, I waited for a few seconds and then remembered that my mother had planned on sleeping in Ann's bed with her so I grabbed my pyjamas and ran for Jimmy's bedroom but in the hall, I heard 'Huh...huh...huh...huh!' from the living room and that stopped me in my tracks.

I'd seen the opening salvo between Jimmy and my mother as Ann dragged me through the doorway, I didn't know quite how far my mother would have let Jimmy go, I knew that she'd been happy for Jimmy to look at her wearing just her bra and knickers earlier but my mother wasn't like Ann, my mother wasn't divorced, she was still married to my father, I wouldn't say happily married, they didn't really seem to even like each other very much but they still slept together every night...well, every night that my father was home.

I dumped my pyjamas on Jimmy's bed and crept down the stairs, Ann was in the kitchen, the kettle was close to boiling, creating a noise that was covering my approach to the living room, I looked around the corner, mum was on the sofa, her bum was right on the edge of the seat cushion, Jimmy was kneeling on the floor in front of her, her knees were over his elbows and they were both totally naked and Jimmy was fucking her.

Jimmy whispered, "Does Alan fuck you like this Liz?"

Mum shook her head, "We hardly ever have sex these days."

"Is it safe for me to cum in you or do I have to pull out before I climax?"

Wow, that surprised me, Jimmy must have been fucking my mother for close to an hour and he still hadn't climaxed yet.

Mum shook her head again, then she groaned with pleasure, "No, I'm safe, I've gone through the menopause, I can't get pregnant."

Jimmy pushed himself up, folding my mother a little more and he doubled his fucking speed into her and he whispered, "Can you feel it, can you feel my spunk filling your cunt darling?"

"Oh God yesssssssss!"

I felt heat at the side of my cheek, Ann had my mother's cup of coffee in her hand and her left arm had just snaked over my shoulder, "My Jimmy is a very experienced lover, do you like watching your mother getting a damned good fucking Paul?"

Mum's eyes suddenly shot open and she looked over at the open doorway, she was pushing at Jimmy, trying to get his cock out of her cunt and complaining to Ann that she had promised to keep me out of the way for at least an hour.

Ann tapped her wrist watch with her right index finger, her right arm in front of my face, "I've kept him busy for ninety minutes...you should have kept a better eye on the time if you didn't want Paul catching you out like this...anyway, the damage is done now, Paul has seen you fucking Jimmy, so just make the most of it!"

Ann guided me with her arm still over my shoulder, "What do you think of that position Paul, would you like to fuck like Jimmy?"

Page 4

I shrugged my shoulder.

Ann handed my mother her cup of coffee and Ann sat at my mother's side in the same position, "Come on Paul, try it like this, see if you like it as much as my Jimmy does.

I must have been a little reluctant or slow in moving, probably because my mother was right there, watching and I was worried about her seeing me having sex. Either way, Jimmy seized his opportunity and he jumped from between my mother's legs to his mother's side of the sofa, my mother watched as Jimmy lifted his mother's knees over his arms and he slipped his cock into her pussy and started banging her.

Ann seemed to climax a lot quicker with her son's cock in her than she had with me but that didn't surprise me because Jimmy had so much more experience than I had but then I saw a different reason for Ann's speedy and deeper orgasm, she was looking over at my mother, mum had stopped looking in my direction, she'd taken a sip from her cup of coffee and decided that it was too hot and placed it on the table at the side of the sofa until it cooled down a little. Once my mother's back touched the seat of the sofa again, Ann twisted herself a little towards my mum, mum was staring straight at Ann's cunt, watching Jimmy's cock sliding in and out of it.

Ann stroked her hand over my mother's breast and up to her chin, turning mum's face to hers and Ann leaned across the gap and as she gasped through her orgasm, she covered my mother's lips with her own and they had a deep kiss. Ann let go of my mother's chin and she gestured to me to come further into the room, she kept pointing at my mother's cunt and she was basically telling me to copy Jimmy but on my own mother.

I was reluctant at first but then, well, it was such a turn on watching Jimmy fucking his mother while she kissed my mother and played with her tits, I eventually stepped in and started fucking my mother at the side of Jimmy., copying him thrust for thrust. Mum rocketed to her own orgasm, she was bouncing about under me so much that I almost climaxed several time but Ann's earlier tutoring had given me a few tips for delaying my own orgasm as long as possible, that and I'd already climaxed several times in the evening with Ann.

I knew that it was wrong to fuck my own mother but the reaction of her body under my cock spurred me on to fuck her harder and faster until I let my cream fly in her...

June's mouth left my cock just as I was about to cum, I groaned in disappointment, "I never knew that you fucked your own mother...you never mentioned that before, and you said that the first time that you had sex was with an older woman but you never mentioned that it was one of your mother's old school friends."

I agreed with her, "No, I never mentioned that my mother was bisexual either..."

After I filled my mother's cunt, she forgot all about her coffee and she dragged Ann up to the master bedroom and the two of them dropped on the bed together, I think that Ann and my mother had expected me and Jimmy to go to bed in his bedroom but he pulled me into his mother's room and we stood and watched my mother and Ann fucking each other. I had no idea that two girls could actually have sex together, I'd never heard of lesbianism in my life before but watching my mum and Ann fucking had turned me on all over again.

Jimmy started rubbing my cock as we watched our mothers fucking, I went to an all boys school so I was no stranger to boys having sex with other boys and the alpha males in my school didn't care if anyone else saw them raping weaker boys, so, unlike a girl with a girl, I knew just what boys could do to each other and Jimmy wanted to get something going with me while we watched our mothers but I'd always fought boys off at school and I wasn't about to let Jimmy seduce me, he even tried to get behind me so that he could bum me...

June interrupted me again to ask me what I meant by bumming. "It just means anal sex but boys at school don't know the word anal so we all just called it bumming when we saw it."

"You mean that you often saw boys having anal sex with other boys when you were at school?"

Page 5

I nodded my head, "The alpha boys only needed a few seconds and a place where the teachers couldn't see them, they didn't care if other boys saw them because they knew no one would tell on them or they would get beaten up if they did, they either got the weaker boy to wank them off or suck their cocks and in the end, they fucked them up their bums."

...anyway, I stopped him trying to bum me and in the end, all four of us ended up in bed together, Jimmy fucking my mother while fucked Ann again.

In the morning Jimmy asked me if I wanted to go to Play Land with him, Ann talked my mother into putting pressure on me to go with Jimmy to Play Land while she met a few of Ann's new friends from the local area.

It was only a short walk into the centre of Leicester, the area around Humberstone Gate was very old fashioned, standing at the front door of Play Land, we could see the thousands of people milling around the shopping centre, just the other side of Charles Street but none of them came close to the part of town where Play Land was...unless they were actually coming to Play Land.

Jimmy was welcomed by several of the older men, I watched the greetings from a safe distance, each man stroked Jimmy's head, stroking their hands down the back of Jimmy's neck and giving his head a little shake in a friendly way, each man asked who I was because I'd been seen entering the amusement arcade with Jimmy, he told them that I was a friend of his from his old area.

I watched a whispered conversation between Jimmy and a man called Winston, a large West Indian man who seemed to be spending more time stroking Jimmy's neck than any of the white men had done so far. I watched as Jimmy nodded his head in agreement to something that Winston had said to him, Jimmy walked over to me and he gave me a few coins, "You play on the Cyclone for a few minutes while I go and have a chat with Winston, I'll see you back here in ten to fifteen minutes."

I popped a ten pence coin into the Cyclone machine, it was a cross between a pinball ,machine and a one-armed bandit, reaching a high score on the pinball won you spins on the one armed bandit and if you won there, you could get your initial stake back or even double your initial outlay.

I had my head down, fighting hard to keep my ball alive in the pinball section of the game and a hand suddenly rested on the small of my back, "Morning Jimmy, you're in early today!"

I jumped away from the machine as well as away from the man, he looked at my face and then he gave me a half smile, "I'm sorry love, I thought that you were my friend, Jimmy, this is his favourite machine!"

I looked in the direction that I'd seen Jimmy and Winston walking as the steel ball of the Cyclone machine disappear in the 'You Lose' hole, I scowled at the man for making me lose my ball, and I said, "Jimmy went in that direction with a black guy called Winston!"

His smile widened and he held out his right hand, "Hi, I'm John, I'm Jimmy's best friend, I've known him ever since he moved into Leicester!"

I relaxed a little, I remembered Jimmy telling me about the man who had taken him home to meet his daughter, 'Now...what did Jimmy say John's daughter's name was?'

"Hi, you must be Samantha's dad!"

His smile turned into a belly laugh, "I have a son called Samuel but no daughter I'm afraid!"

I looked down the passage that I'd seen Jimmy and Winston go down as I started playing on the Cyclone and it stole all of my attention.

"Where did Jimmy tell you that he was going?"

"He said that he was just going for a chat with that bloke...Winston!"

There was another laugh, "Well, I'm sure that Jimmy wouldn't be so rude as to talk with his mouth full...want to see what he's up to?"

Page 6

I nodded my head, John gestured with his head for me to follow him across the main room towards the little passageway. At some point in the walk across the room, John had moved from in front of me to just behind, when we reached the passage, it was so tight that John put his arm over my shoulder so that we could walk along the tight passageway side by side.

John opened the door into the men's toilet and I spotted Jimmy and two men, Winston the black man was behind Jimmy, I didn't need a close up look to know that Winston was bumming Jimmy while Jimmy was sucking the cock of the second man. John was standing right behind me now, whispering in my ear, "Jimmy takes a cock up his arse really well doesn't he...when I first tried him, I couldn't get in so I had to take him home so that my son could start him off and I could use Sam's spunk to slip my cock up his bum!"

John pushed me in closer to Jimmy and his two friends, something else that I didn't miss were three five pound notes in Jimmy's right hand...the men had paid Jimmy to have sex with them. When I was about three feet away from the trio, John shuffled across my back, his right hand slipped around my side and he put the flat of his hand on my belly, nowhere close to my cock so I didn't worry about it, then his left hand pressed on my left shoulder, he was pushing me forward with his left hand and he pulled back with his right hand.

I staggered a little, trying to keep on my feet and suddenly, my right ear was touching Jimmy's left ear and the man fucking Jimmy's face started stroking my head with his right hand, pulling my head in closer to Jimmy's head before pulling his cock out of Jimmy's mouth and pushing it against my lips. I tried to fight him off when I suddenly felt pain from my bum and I couldn't hold my mouth closed any longer.

John must have been very well versed at getting what he wanted from boys because I hadn't even felt him pulling my trousers and underpants down and getting his cock against my bum hole. I jumped out of the gap between the three men, pulled my trousers back up and made a run for it while the four of them laughed at me. I hadn't actually been sodomised, John's cock was far too big to get up me and the other man had only managed to tickle my tonsils once.

I ran all the way back to Jimmy's house, leaving him in the toilet with three men to look after. I ran into the house through the back door and searched around for my mother and Ann, the downstairs area was empty so I ran up to the bedroom and found Ann in her bedroom with two black men and my mother in Jimmy's bedroom with another two black men...

June pulled her mouth off of my cock once again and she whispered, "Once you've had black, there's no way back!" and after getting that off of her chest, she went back to sucking my cock for me again.

June started sucking my cock hard and fast now, her left hand fondling my balls, she'd done that before and she knew that I liked it a lot but then something new, she slipped her right hand under my bottom and started massaging my tight anal muscle with the tip of her middle finger as she tried to get me off as fast as she could.

I just stood there watching my mum being double teamed by two black men, when they started out, she had one man in her cunt and the other in her mouth but things transitioned and the man that was in her cunt moved a little further back and slipped his cock up her bum and the man that had been in her mouth moved onto her cunt then mum did something strange, I had no idea that she even knew that I was standing there watching but she beckoned to me to go over and she took me in her mouth as she was being fucked by the other two men.

Ann called an end to our three-way fuck-fest, she stood in the doorway and told my mum that we only had forty minutes before our train back home. The man fucking my mum's arse turned out to be our taxi driver and my mother was letting him fuck her in lieu of the money for the taxi trip to the railway station.

We dropped into our seats on the train and mum leaned in to my side and she whispered in my ear, "We must never do anything like we did this weekend ever again and please don't tell your father about me and Ann...and especially don't tell him that I've had sex with two black men...he'd never speak to me again. Things are strained enough between us for the last few years as it is, if he thinks that I've been a black man's meat, that will be the end between us!

June got me off at that point and as I started to convulse through my orgasm, she rammed her finger deep into my anus without pain.

Page 7

June wiped her lips clean, she said again, "Once you've had black, there's no way back..."

"Why do you think that is darling?"

"Most white men can't handle the thought that their wife or girlfriend have been had by a black man...you know all that crap about black men have bigger cocks than white men...I think that the reason that things were strained between your mother and father back then was because your father actually has a thing for little boys...I'm surprised that your dad never had a go at you!"

"How do you know that my dad had a thing for little boys back then?"

"Remember my telling you the other day about a boy from Irthlingborough Village that I sucked off when I was nine years old..."

I nodded my head.

"...your dad was the man that brought him into the game!"

I was a little shocked at that, "How come no one ever said anything...I mean, like when I took you home to meet my mum and dad for the first time, how come neither of you said that you'd already met before?"

"Well, you know how I've been, I've never been comfortable talking about that period in my life and if I'm honest with you, I think that Alan was so into young boys and men that I don't think that he even saw me when I sucked William's cock for him...I'll tell you something...it's a pity that you turned Jimmy down when he wanted to bum you on Friday night, if you had let Jimmy do you, it might have been less painful when John tried to do you that way on the Saturday and you might have had a lot more fun on your two day trip away."

I laughed at June's comment, "You think that I should have tried anal sex with a man then do you?"

June nodded her head enthusiastically, "Of course...and I'd love to watch you when it happens!"

I just shook my head, "I can't see myself going down that road darling."

"Not even to please me?"

Well, that gave me food for thought, when I asked June to do things for me, even if she didn't like doing them, she still did if I asked her too, so, perhaps I should consider doing it if she wanted to watch me!

5,900 Words.

Already seen Paul's first time, click here to read Awakening, or here to read June's First Time, or here to read after June's deflowering

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