It All Started With Kelly

[Deleted Member]

A not so short erotica for your enjoyment . I hope. 

 

Back in 2010 I started a new job as relatively lowly office junior on a degree programme. It was probably by week two that I had started to hear about Kelly. She had built up quite a bit of a reputation over the office. Kelly was in her mid thirties so a few years older than me. She was quite curvaceous but her Hazel eyes are what struck me the most and I still remember to this day. Over time I get to know her quite well. In the office Kelly was quite shy, kept her self to her self. But a couple of drinks after work in the right company she was fantastically charming. Quite a bit of a flirt too match. I could see how she could get a reputation but I tended not to listen to the office gossip. For me it seemed mostly like harmless fun and was quite happy to flirt back a little. It was only a bit of banter after all. She would always joke if is she was 10 years younger, she'd be over me like a rash. Again, something I always thought of nothing more as a harmless quip. And I must admit I was attracted to her. Then it happened. All the joking and laughing around; well maybe we had teased each other a bit too much it was bound to happen. 

You know those horrible team building events. Yep, raft building, trust events and getting to know eachother exercises in the lake district. We all stayed up playing cards in the hotel bar until last orders. I had not got to speak to Kelly much over the weekend and she suggested grabbing a bottle of wine and going up to her room to keep playing. Well I thought like usual it would just be a session of moaning about the bosses and bitching about colleges. So we grab a wine bucket and head up to her room. 

I open then wine and start to shuffle the pack. Kelly execuses herself to the bathroom. As she comes out the bathroom I ask her if she wants to start. 'Okay Mark' she replies. Then I feel her behind me. Her bosom softly pushing against me a soft silky texture on the back of my head. Her hand reaching around to slowly unbutton my shirt and caressing my chest. As she kisses my neck, I need to speak up albeit I am enjoying the moment. 

'Stop Kelly. We can't. Everyone will know and gossip about us in the office.' She continues to unbutton my shirt until she reaches the top button of my trousers. 

'Well stop me then Mark' She explains as reaching into my trousers. 'I see the way you look at me. Don't deny that you don't want this too.' She squeezes my cock whilst saying that feeling it grow bigger in her hands. 'And don't worry no one will find. I'll make sure of it'. 

'But people talk. This could be bad for both of us. And the age difference its not that I don't find you attractive but it's not like it will work in the long run.'  Kelly moves around. Displaying the silk negligée she has put and straddles me facing towards me. Those Hazel eyes piercing me. Melting away any thought I had of stopping this from happening. 

'Bless a relationship. God no you know I've always said your too young for me. But a Fuck'. With that last breath she kissed me. It was that kiss that sealed it. 

The sex was electric. It was everything I had always secretly masturbated about and still do to this day. God she was insatiable. She did things and asked me to do things that I still use to this day and still never fail. It was the best sex I ever had and one of those times you will never forget. Kelly was the one who introduced me to my kinky side who made me want to be more experimental. 

Half way through whilst kissing her neck I told Kelly how I had secretly dreamed of this moment. 'Oh you naughty Boy. At least it makes two of us who have been thinking about it. Don't worry I will make sure you won't forget it. I can work wonders with a guy'. She kissed my lips softly and asked me too lay down. 

Those Hazel eyes as her lips enveloped my cock, an image burnt into my memory. Alongside what was about too happen next. I could tell her enthusiasm and her enjoyment as she sucked me. This was not for my pleasure also. She reached for my balls grasping them gently at first and then a little firmer. 'Oh do you like that Mark. Move your legs up a little bit so I can get a better grip'. Of course I obliged she could work wonders indeed. She started to stroke me so gently but so firm. Just keeping me on the edge. 

She took me in one hand whilst caressing my balls. Then her finger started to stray southward. She started to slowly circle it around my ass. I did not stop her. As she stroked my cock it felt kind of nice. I could then feel a little bit of pressure building. I started to clench a bit but was still fixated on her stroking. After a while I notice that I had stopped clenching and so did she. 'Do you like that Mark?' 

'Sort of I don't know. Why' 

'Do you trust me?' 

'Well maybe a bit late to ask that question but yes.' 

'Good boy. Now wait there' what the hell was going on? Kelly went to grab her bag and bring it down to the end of the bed. She climbed back on and started stroking me again. This time however as she circled my ass I could tell her fingers were a bit more well lubricated. 

'What are you doing?' 

'Don't worry trust me'. Maybe it was the wine or just how good the sex had been but as she stroked my cock she comforted me again and that clenching had once again stopped rather quickly and the pressure of her finger grew. My mind was also a hundred miles an hour. What am I doing. Then without resistance at all I could feel her finger slip in at which point I did start to clench again. But with small swirling motions and massaging I was relaxed. 

'So do you enjoy that she asked?' 

'Hmmm yes' is all I could muster. And as I did I could feel her second finger starting too explore. Gently again both of them swirling around my ass. Slowly but surely from a tip, to the first knuckle too both of her fingers she was in and massaging me. The pleasure so intense I had forgot that she had stopped stroking my cock but just lost in the massaging sensations. It was a pleasure I had not felt before. Like I needed to cum but quite couldn’t. Surreal but an overpowering pleasure in relaxation being kept on the edge. 

'Well I am glad you enjoyed it. Wait there I need to clean up.' A few minutes passed I was exacerbated lost for words on what had just happened, bound to the bed in bemusement and fulfilment. I shut my eyes. I then feel the bottom of the bed move her lips kiss from my cock up my body around my neck and too my lips. 

'Thank you for trusting me.' 

'No thank you Kelly.' We kiss but I feel something I wonder what it is. 

'Lift your knees up again' 

'What' 

'Just trust me' I don't know why but I do I lift my knees up again. And again I feel that that pressure. 

'What are you ..' no chance to finish my words Kelly kisses me deeply and firmly. 

'Shhhh' the pressure builds again and I open for her. 

'What are you doing' 

'Fucking you' 

'What' 

'Relax' She kisses me again her Hazel eyes staring into mine. And with that kiss I do and I feel that pressure inside me. I can do not resist. There is something pleasurable as we kiss just feeling something inside me again. Slowly she thrusts her hips up and down. A little bit at a time giving getting deeper. I can not help but groan. I am enjoying it. She kisses me softly calling me a good boy. I can't help but let Kelly have her way with me. Our embrace eases me as she fills me the pressure and gripping has gone now just like before that massage again mesmerised by her gaze. I grow harder as she starts to thrust a little harder. She move up to hold one knee under her arm. 

"Good boy" I can not stop her the pleasure is too much. Too new. I start to tense in my stomach. Not an orgasm but the need to cum and I do a little. She takes her finger swirls it around in what I have just ejaculated and precedes to lick her finger. Wow the naughty girl. 

'Hmmm' so you do enjoy it I seem to be hitting the right spot. As she takes my other knee under her arm we are fixated on each other. Me staring at her as she stares at me glancing also to watch what she is doing. Her moans get stronger. Perplexed as to why she continues to moan. I have heard these before like she is going to cum also. Is she really enjoying this too. And as her moans grown stronger so do her thrusts. She's getting close. 

'Fuck me!.' Where did that come from but I can't help but to encourage her. 

'Fuck me, fucke me, fuck me' 

'Yes, yes, yes' 

She get harder and deeper and I can feel my stomach muscles tension my whole lower body lifting and shifting in the need of something. 

'Cum for me Mark. Cum for me. That's it Cum for me' 

'Yes Fuck me. Make me cum for you!'  ... 

'I'm cumming for you Mark' 

A joint  'Arhhhhh'. Wow did I. I narrowly missed my own face! But she continues with a half dozen deep hard thrusts. Each time I twitch a little more cum still appearing from somewhere. 

Kelly collapses she is also spent. Her sliding out is as much of a relief as her kiss afterwards. We lay there foreheads together. Closed eyes recovering. Until she says. 

'See no need to worry no one will need to find out we had sex as if they do i will tell them exactly what just happened my boy.'

And this is where my kink journey began. 
 

[Vi****]

I enjoyed this alot, I think Kelly is my kind of gal' 😀 also I have to know is this how it really all began, if it is wow you must have really been relaxed and trusted her to peg you, or just sweptnup in the moment. Either way this was super hot 🔥 and enjoyable

[Deleted Member]

Thank you glad you found it! Certainly my type of gal' 😝 there is some fiction involved with the story line to build up a setting. But some of it is not too far off how it all began. I did trust her and was swept up in the moment but well was something had always wanted to try before. Super hot indeed and very enjoyable 🔥 I'm very glad you enjoyed the read 🤍