The Diary Of J. (Chapter 1;First Time)


As we sat down she took a sip of a half empty drink while smiling… She looked great. We had been in Greece for 3 days now and already she looked decisively darker. Her black curly hair looked great at shoulder length and her plunging neckline was trying desperately to grab my attention… I looked away… She was my best friends older sister and out of bounds… Although Thomas would never admit so, I felt anything happening between me and his older sister would be… well strange. However despite my reservations, the more and more I consume, the hornier I get and the hornier I get the less I care about this ‘strangeness’ that I prattle on about. ‘Where’s my mum?’ A voice said killing the my train of thought. ‘Taking Rose home’ I said, matter of factly…‘She coming back?’‘Yes. We’ve just to stay here and have a drink’ said Susie. I looked again at her face… man she was sexy. And my god was I horny!Thomas slumped down beside me and started to get stuck into a huge cocktail he had bought. He looked to be feeling the aftermath of a daylong drinking binge and was now looking like he had one or two drinks to go before he collapsed…‘I’m going to dance, d’you wanna dance?’ Is she asking me I thought…‘Sure…’ My mouth answered before my brain could tell it not to…I followed her to the dance floor and started to dance, it was a fairly slow number in relation to the others that had preceded it and I cursed my luck to get stuck with the slow song. As we danced I smelt her perfume, and it smelt really good. I was so turned on by everything. The night, the holiday, her smell… her body…As we were pressed up together I felt that maybe I should kiss her… then I decided against it, which may have been extremely smart or extremely dumb… either way it was ‘safe’. However my safety was blown apart when the slow song came to an end only to be replaced with the sexy sounds of the Neptune’s…MY MILKSHAKE BRINGS ALL THE BOYS TO THE YARD… echoes all around the dance floor…‘I love this song!!!’ Susie said extremely excited. Before I could even suggest going back to the seat for another drink, she was ‘milk shaking’ her ass into my groin and throwing her hair about much to my arousal. A million and one thoughts ran through my head at the time and not one would have got me into heaven.

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   I was skating on very thin ice… Suddenly she came up face to face…‘Meet me in the girls toilets by the door in 5 minutes. ’ She said enjoying the look of shock on my face…Before I could answer she had turned and walked away. A mixture of fear and excitement froze me. I stumbled back to the table where Thomas was still drinking ask him if he wanted a drink which he surprisingly declined. I turned and made my way to the men’s toilet to regain myself. As I entered I was happy to see there was no one in. I splashed more water on my face and twisted one of my blonde curls with my index. ‘What the fuck are you gonna do John?’ I asked myself, expecting an answer. Fuck it I decided, I was too horny and too drunk NOT to do this. I quickly regained myself and walked outside. ‘There you are!’ Said a very familiar voice. I turned around and my guess had been accurate. It was Thomas’s mum Gillian. What timing I thought. ‘Hi…’‘I need you to do me a huge favour son.

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  ’ She said. ‘Sure what is it?’‘Can you take Thomas back to your hotel?’‘Now??’ I said a little too dramatically in retrospect. ‘Yes why are you busy or something?’Yes I’m on my way to lose my virginity to your oldest daughter in a toilet I thought. ‘No, of course I’ll take him back. ’‘Thanks, you’re a sweetheart. ’ She said leaning over and giving me a peck on the cheek. As I carried him back to the hotel I pondered what I had sacrificed to do so. It depressed me, although part of me thought there was still a chance of sex as I had been told to go back to the club once he was in his bed. As I put him on his bed I noticed that sex in here was a no-no. The room was a one bedroom room with 2 single beds. So for me to try and get his sister here we’d have to have sex in front of him… fuck that. That left either his mum’s room to the left of ours, (which I dismissed immediately) or her room to the right of ours, which she shared with her aunt. Suddenly the thought of losing my virginity in a toilet was looking more and more appealing. I again checked myself in the mirror before exiting the hotel, however as I walked out the main foyer doors I was shocked to see Gillian and Susie on their way towards the hotel. And both didn’t look happy.

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   For a brief moment I got extremely paranoid. I approached them smiling. ‘What’s happening?’ I ask hoping its got nothing to do with me. ‘Her. Shes has been in a bad mood since I came back. God knows why, just been a little bitch who cant handle her drink. ’ Gillian says. ‘Shut up mum. I’m going to my room… alone. ’ Susie said in a very pissed of manner. We both watched as she stormed away. A silence hung heavy…‘So, did Thomas go straight to sleep?’‘Yeah…’‘Are you going to bed?’‘Guess so… Unless you’re wanting to back to Mancudo. ’ I said wishfully. ‘No, I don’t. But you’re welcome to come in to my room for a few drinks, if you get drunk you’re only next door so that’s no a problem.

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  ’‘Sure ok, although getting drunk shouldn’t be a problem as I am already more than halfway there!’ She giggled as we started to make our way to the room. Once we were in her room it hit me on what I was doing. I was in my best friends mums hotel room. Having a drink. The irony of me thinking his sister was crossing the line was not lost on me. An hour or 2 past as the drinks flowed. We talked about stupid stuff like, why I broke up with my girlfriend 2 weeks prior to the holiday. Why she was single now. ‘I need to go get out of this skirt etc, I’ll be 5 minutes. ’ She said as she walked away. ‘Ok…’I sat there, becoming more and more aware of where I was yet not caring as much as maybe I should. I guess I can thank the drink for that. As she returned I noticed for the first time how sexy she was. I always knew she was attractive and fairly young for a mother but now that she was wearing a nighty I seen her body, or at least the shape of it for the first time. I was awestruck.

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   She sat down to continue our drinks and conversation as if what she was wearing meant nothing. ‘So what do you think Thomas would say about us getting drunk together?’‘Em he’d slag me. No offence. ’ I said wanting to die. ‘Haha, why’s that?’ She asked. ‘Because… I can’t believe I’m saying this to you of all people. But he thinks I fancy you. ’ I said… regretting each word as it left my mouth. ‘Me?!? Why would he think that?’‘Because I said to him you were nice looking for a mum. ’ I said semi embarrassed. ‘In a cute way or a sexy way’ She asked inquisitively. I shift uncomfortably in my seat. ‘Well it was in a cute way but seeing you dressed in that, it would be a sexy way. I never knew you were so…’‘So what?’ She says moving closer to me…‘So…’‘So what?’ She says as she’s a breath away. ‘So sexy.

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  ’ I say as I think about kissing her…Suddenly she makes the decision for me and kisses me hard, I feel a huge flush of blood soaring to my groin as I kiss her back. We passionately kiss on the couch as her legs inadvertently kick drinks over. We both start to giggle as we stop. ‘D’you want to go into the room?’ She asks…I nod, speechless. She takes my hand and leads me into the room. As I walk in I realise the reality of what is happening. I dismiss it almost immediately. We both sit on the side of her bed and begin to kiss again, this time its faster and more reckless. She pulls the my top over my head and discards it as I unbutton my trousers. We are in the middle of the bed now, kissing still as our hands wonder…I begin to explore her curves as she runs her hands up my back and back down to my ass, and in a sweeping motion begins to pull my trousers down. I’m sensing that its time for me to make a move, run my hands up her soft milky thighs and gently pull her pants down. She aids me in this and kicks them off, then almost simultaneously pulls her nighty over her head exposing her breasts. I start to kiss her neck as she moans lightly while my right hand starts to explore her wet lips. Back and forth I run my index finger along her lips until they seem to suck me in…She lets out another moan and I begin to kiss her on the mouth again. She then pushes me over onto my back and pulls my trousers off completely.

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   Then she does the same for my underwear… I suddenly get a jolt of paranoia about penis size seeing as I had never went this far with anyone let alone someone of her experience… Her look is a diplomatic… ‘I’ve seen worse sorta look’ which to me is a mile away from what’s that!!! So I was happy. She took my dick in her right hand and placed her left hand by my right hip…Slowly she started to massage it and it felt so good. I lay there not wanting it to end… I closed my eyes while murmuring…‘God Gillian that feels so good…’‘Just relax John… lets make this last…’Suddenly I felt a wet sensation on my cock. I opened my eyes and seen this older sexy woman sucking my dick. MY DICK. I could barely contain myself as she continued. I didn’t even know what to say that wouldn’t be abundantly obvious. I just lay there and enjoyed it. ‘This tastes so good…’ Gillian said as she slobbered over my hard cock. ‘God Gillian don’t stop… please don’t stop…’ She continued to suck on it as I lay back in dreamland… The sound of her sucking made it harder for me to control myself… then she stopped and pulled me to her and kissed me as her hand continued where her mouth left off. We kissed hard as my hands went through her hair, down her back and slowly up her sides till each one had a breast in it. I slowly began to tweak the nipples. As I did this she pushed me fully onto my back and whispered in my ear…‘Have you got protection?’‘Ye. . yess’ I spluttered as I reached for my trousers, trying desperately to pull out my wallet without having to change position.

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   Suddenly I had my wallet and removed the condom before throwing the wallet away. I handed it to her. She smiled and stared me straight in the eye as she ripped it with her mouth… ffffffft… the she grabbed my dick and began to kiss me again as she slipped the condom on my hard cock. ‘Gillian…’‘What is it?’‘I’ve… never… I mean this is my… I’m not… This is my first time…’ I said feeling slightly embarrassed. ‘Don’t worry hunnie… just relax…’ She said pushing me back to the bed. She then sat aside me gently masturbating me…‘Are you sure you want to do this?’‘Yes’‘Ok… this is gonna be the best, most wonderful, unforgettable night of your life…’She hiked a leg over me while still holding my cock and slowly sat down on it.
    She moaned lightly as it enclosed me. I groaned…‘Awwww’Slowly she placed her hands on my chest and began to rock back and forth into me… ‘Hows that? You like that?’‘Awww yes… It feels so good…’Gillian then began to pick up the pace as I lay there… almost instinctively I began to grind back into her as I placed my hands lightly on her ass. I could feel the moisture from her soaking wet pussy as we continued to fuck. We got faster and faster and the noise of flesh clapping together was no longer subtle. ‘That’s it… fuck me… oh yeah fuck me…’‘Gillian this feels so good… oh yeah faster. She started to grind heavy as she let out heavy breaths when suddenly I felt a huge burst of heat coming from my cock…‘Aggggggghhhhhhhh I’m coming…’ I gasped as I filled the condom and her pussy. She slowed down while I was still in her and came to kiss me…‘I’m sorry Gillian… I’m really sorry…’ I said apologetically…‘Don’t worry… Lets find something fun for you to do to me…She climbed of me and removed the condom from my cock, before throwing it on the floor. She then grabbed my hand and pushed it towards her pussy. I inserted 2 fingers almost instantly and I felt her started to grind into them.

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       She then used her hand to guide my head down…I start to kiss her thighs just around her pussy as I continue to finger her, this time with a single finger. As I kiss around her groin I smell her. I begin to be hugely aroused by this as I withdraw my finger start to kiss her pussy. Slowly I part her lips and insert my tongue, making careful sensual strokes, but making sure they vary. I may not have been an expert at sex… but this was something I had done… and I had done well…As I continued to eat her out her breathing increased tenfold… to the point I actually became paranoid about being caught. ‘Huh… hu… huh… god that’s it… up a bit… oh fuck yeah…’I keep at it and soon my face is soaked in her… As I continue I insert a finger again and move my mouth to her clit… Soon Im working it and she is delirious, her body is shaking violently as I get faster and the more she likes it the more I am getting turned on. Suddenly she pulls me up to face her and kissed me hard…‘I want you inside me again. ’Quickly I rummaged about the floor for my wallet and took out another condom before climbing onto the bed, she lay on her back as I put it on. We start to kiss again as she pulls me into her and after a few misjudgements she grabbed my now rock hard cock and put the tip into her. ‘Now fuck me. ’I thrust hard and send it deep into her feeling a huge rush of pleasure. I place my hand under her right leg and lift it up to my shoulder and start to push in and out. ‘That’s it… deeper… deeper…’‘Awww yeah…’We both begin breathing very heavily as I pound away at her soaking wet pussy. As I lift her leg higher I seem to hit a good spot…‘MY GOD… There… keep it there… oh Fuck me… oh my god it feels so good… don’t stop…’I keep at it. I can barely speak as my hips grind into hers.

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       I feel her hands on my ass pulling me deeper with every stroke. I sense I’m close but keep on at her. ‘Its good’… she murmurs as she has now lost the ability to speak…I keep going feeling it building up when I hear the words Ive been waiting for…‘Im close John… I so close…’With that I get faster… I fuck her faster than I had done… knowing each stroke has the potential to be my last… when suddenly…‘AWWWWWWWW yes… Im coming… aw yes… oh god…’As she screams I feel her vagina tensing up and I come almost instantly and I feel like Im never gonna stop coming…Both of us continue to grind as we slow down… then to a complete stop…‘That felt… you sure that was your first time?’ She says as she lies breathless covered in sweat…‘No… That was my second time…’ I say as I begin to laugh… breathless also…We lie in a mess of sweat-drenched bodies on her bed, with the smell of sex firmly in the air. I kiss her once again and turn over when she brings me back down to reality…‘You better get dressed and get into your own before someone catches us…’‘Yeah I guess so…’ I say as I quickly pull on my boxers, now slightly embarrassed to be seen naked. ‘Its probably best if we don’t mention this to anyone. It’ll be our secret. But it must be a one off. ’ She says rather coldly. ‘Of course. ’ I say as I go towards the door. As I’m about to open the door she pushes it shut and kisses me. ‘I really enjoyed tonight. But they wouldn’t understand. ’She kissed me again and ushered me out. As I stood outside my room I realised I wasn’t a virgin anymore… And with that thought in my head I knew I was gonna have a great nights sleep.


      (First time story so be gentle so to speak!).