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Working with a milf

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By (user no longer on site) OP     over a year ago

One of my first jobs was working in an office. I worked closely with the receptionist, who I got on well with from the first day. I was in my mid twenties and she told me that she was in her mid forties, although I maintain she looked like she was in her late thirties. I was quite naive and unsure of myself, and I think she sensed this. Looking back, I think our friendship started because of her maternal instincts to look after me. Our boss was a bit of a bully, so that probably made us more supportive of each other. Kelly and I were in a team of four, but our jobs involved us working more closely with each other than the rest of the team. We would frequently have lunch together, and discuss what our boss had done today.

Our lunchtime discussions became quite frank and open. So we eventually started talking about more personal subjects. I didn’t appreciate it at the time, but I listened more that said anything. I had led quite a sheltered life, and didn’t feel I had much to offer the conversation. I think Kelly enjoyed being able to confided in somebody.

Several moths pass of us working quite happily. In hindsight, I how realise that I was seeing Kelly in a new light. I still thought of Kelly as a really good friend, but I started appreciating the effort she put into keeping her petite figure so toned. I found myself having to keep my lunch on my lap, or find a reason to face away from Kelly during our lunchtime chats. I became more and more flirty with her over the next few months. Although we always maintained our friendship. I think she still felt protective of me, which I think suppressed any other feelings I hoped she had for me. In think if she had told me that she wanted me at that point, I probably would have run a mile.

One day during our usual lunchtime chat, Kelly confided in me that the reason she left her husband was that he was abusive. Which had the immediate effect of making me feel extremely protective of her, and wanting to give her a big hug. During that frank conversation, I discovered that Kelly wasn’t the strong person that I thought she was. Infant she was very shy and insecure.

It was the festive season, and the team went out for a Christmas meal one weekend. I made every effort to stay as close to Kelly as possible. I’m sure this made it obvious to the rest of the team that I fancied Kelly. The rest of the team was made up of ladies about Kelly’s age or older. So I’m sure they all looked at me and thought, sweet boy having a crush. I convinced myself that I shouldn’t force the subject of how I felt about Kelly, but I think I was too unsure of myself to do anything.

After the festive season we all return to work as normal. Kelly and I continue having our lunchtime chats, and I continue to think of how I could get into Kelly’s panties and do nothing about it. One of my fanatics was to expose myself to Kelly. I didn’t expect Kelly to fall to her knees and take by cock into her mouth. Just the thought of exposing myself and have Kelly look at my cock was incredible arousing.

However, after another few weeks of not acting on my feelings towards Kelly, I got offered a promotion to a branch office closer to home. I except the job, and say my good buys to my old team. I hadn’t made a serious move on Kelly, because I kept telling myself that we had a good friendship and not to ruin it. The truth was that I was too shy any insecure. So this was the perfect opportunity for me to make my move. If she said no I was leaving, so I didn’t kneed to feel embarrassed.

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By (user no longer on site)  over a year ago

Keep going this is good, very natural.

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By (user no longer on site) OP     over a year ago

Like so many times before, I missed my opportunity. During my last few days Kelly and I never seemed to be alone, and there was no way I was going to say anything with an audience. So I left and started my knew job. For some time after, I regretted my missed opportunity. Kelly and I slowly lost touch. So I did my best to put the situation out of my head and move on.

I now had my own office which looked out over the reception, so I could see when my presence might be required. So when I say Kelly walk into the reception all my feeling instantly came back, and I rush out. I never found out if Kelly’s appearance was a coincidence or weather it had been planned, but there she was innocently bringing over some paperwork.

In hindsight, Kelly didn’t seem very surprised to see me, but she did seem happy that I came out. I started talking to Kelly about anything just to spend as much time with her as possible. Kelly was giving me all the signs, but we were still in reception and I wasn’t going to do anything with an audience. So Kelly eventually turned to leave. As she turned away, I saw her ares and I had to do something, so I offered to walk Kelly to her car.

On the way back to the multi story car park she did something that even I couldn’t miss. Kelly squeezed my bicep and asked me if I had been working out. Now I hadn’t been working out, and it by no means looked like I had. This gave me a sudden rush of confidence, and I made it obvious when I paused and looked at her arse. Kelly looked at me and said ”What?” I replied, “I should have told you this a long time ago, you have a fantastic arse.” Kelly blushed slightly, and said “Thank you”, as we continued walking to the car park.

Kelly was parked on an upper level, so we had to walk through a door and up some stairs. I followed Kelly through the door and up the stairs, watching her arse the hole time. I’m sure she was putting on a bit of a show for me. As we reached the top of the first flight of stairs, Kelly turned to walk up the second flight. As she did, I pulled her back into me. We gazed into each other's eyes for what seemed like an eternity, before l lent in and kissed Kelly passionately. This for me was an explosion of years of pent up emotion.

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By (user no longer on site)  over a year ago

Please do continue.

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By (user no longer on site)  over a year ago

Nice story... I had a similar experience when I was 17...

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By (user no longer on site)  over a year ago

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By *ragsterMan  over a year ago

Blackburn

Love young men/older women stories...horny as..

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By (user no longer on site)  over a year ago

Great so far

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By *cfc1965Man  over a year ago

horsham

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By (user no longer on site)  over a year ago


"Please do continue."

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By (user no longer on site) OP     over a year ago

After several blissful minutes of passionate kissing, we strained out clothing and continued up the stairs. I was feeling on top of the world! I can only describe the feeling as being d*unk, when your inhibitions disappear. So whilst walking across the car park, all I could think about was the fantasy I had been clinging too for what seemed like a lifetime.

We got to Kelly’s car and she got in. I crouched down inside the open car door and placed my hand on her thigh. Kelly didn’t make any signs that she was uncomfortably with my hand being on her leg, so I slid my hand onto her inner thigh. At this point Kelly started to move in her seat, and a sense of dread came over me. Had I miss read the signs, had I gone too far! Kelly moved her thighs together, clamping my hand in-between her toned legs. Kelly looked down at me, and my d*unken state of ecstasy remerged.

I can’t ever imagine doing this again, but I could only think about my fantasy. I still can’t believe I said this to Kelly, “Kelly, can I show you my penus?” “What here?” Kelly replied in a shocked tone. “Nobody can see us” I replied, and I proceed to unzip my trousers. Kelly’s eyes widened as my semi erect penus flopped out. Moving her hand down and grasped my rapidly hardening penus, Kelly looked me straight it the eyes and said “Call me”. I think part of the excitement was exposing myself in public.

I walked back into the building through the back door, being carful not to bump into anybody. I headed straight for the toilet. It did’t take many strokes. It took all of my self-control not to moan in ecstasy. I have never cum so hard in my life!

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By (user no longer on site)  over a year ago

mmmmmmmmmmmmmmmmm

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By (user no longer on site) OP     over a year ago

I am glad people like my story, I wasn't sure it you would.

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By (user no longer on site) OP     over a year ago

I was imaging what I would say to Kelly on the endless drive home. This was in the days before mobile phones, so when I eventually got home I rushed to the phone to call Kelly. So much for playing it cool! Kelly answered, and I chocked. I slammed the receiver down. My immediate thought where, why would somebody like Kelly be interested in me? I once again convinced myself of that and continued with my evening.

As I was laying in bed that, I began playing with myself as young men do. I started thinking over the day, and fantasising over what could have been. I began to remember that I had shone Kelly my penus, and she had asked me to call her. I sat bolt upright and grabbed the phone!

I dialled Kelly’s number and it started to ring. This is the point where I usually bottle out and put the phone down. A rather sleepy voice answered, “Hello?” Kelly said. I couldn’t get any words out, and Kelly once again said, “Hello”. I managed to say, “Hi Kelly, it’s me.” Kelly’s voice changed from sleepy to an excited tone. I must have fed of her energy, because I had never found it so easy to have a conversation with a woman before.

After a short conversation, Kelly invited me to come round the next evening. When I hung up I continued playing with myself. I was imaging Kelly was doing the same. When I am playing with myself now, I can control myself and extend the pleasure. I hadn’t mastered self-control yet, and I exploded in seconds. Although, they were some of the most amazing seconds of my young life.

The next day at work seemed endless, but the end of the day eventually came and I went home. Before I knew it, it was time to leave. Once I arrived at Kelly’s, I pressed the number of her flat. The intercom rang, and Kelly’s sweat voice ushered me in. I made my way up to her flat, and found the door ajar.

I walked in and called out, “Hi Kelly, it’s me.” Kelly appeared at the end of the hall, and we walked towards each other. We paused for a moment, and then hugged awkwardly. Kelly ushered me into the lounge, and asked me to have a seat. I sat on the sofa and Kelly asked me, “Would you like a drink?” Kelly returned a few moments later with a glass of wine and a soft drink for me. I asked for a soft drink because I had to drive, but mostly because I wanted to saviour every minute of the evening!

Kelly sat on the sofa next to me. We both took a drink and put our glasses on the side tables. There was a momentary awkward silence before the small talk began. I’m sure what I said next had a lot to do with the adrenalin, because it was nothing like me. “Can I ask you something?”, I asked. “Of corse you can” Kelly replied. “When we were working together, it must have been obvious that I was trying to get into your panties”, I blurted out. “So why now?” I asked, immediately hoping to god that I haven’t just ruined everything. “I was worried that if slept with you, you would assume we were in a relationship” Kelly said. “So you did think about it?” I asked with great anticipation. “Oh yes, I thought about it a lot. So when I saw you again, all those feelings came back”, Kelly admitted.

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By *thwalescplCouple  over a year ago

brecon

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By *cfc1965Man  over a year ago

horsham

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By (user no longer on site)  over a year ago

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By (user no longer on site) OP     over a year ago

We turned to each other, and lent in. There was so much built up tension between us that was instantly released. I had never had such a passionate kiss! I would have been happy just kiss all night. But I really wanted so much more! I moved my hand from caressing the back of Kelly head, and started massaging her firm breast.

After several blissful minutes of grouping Kelly’s breast and felling her nipples harden into bullets, she pulled away. All my droughts instantly came back and I thought, shit what have I done! Kelly stood in-front of me and looked me straight in the eyes. I was expecting the, what kind of girl do you think I am? speech. However, to my great relief, Kelly started pulling her little top over her head. I got my first look at Kelly toned little torso. I could have blown my load there and then! It took all of my will power not to cum in my pants.

As Kelly continued to remove her top, she revealed more and more. Until finally, Kelly’s pert breasts sprang free. Kelly wasn’t even waring a bra! Kelly started rubbing her pert breasts, whilst still keeping eye contact with me. I think Kelly sensed my hesitation, because she knelt down on the soft and sat on my lap. Kelly presented her firm tits to me. I instructively moved my mouth towards Kelly’s breasts and started sucking on her bullet like nipple. As I was sucking of one breast and roughly massaging the other, Kelly started grinding on my rapidly hardening cock. In my head I was breaking myself not to cum.Kelly through her head back and started to moan, and she began to dry hump me with more urgency. After several minutes of even more intense moaning and dry humping, Kelly pulled away and stood up.

Kelly fixed me with that come hither stare, and whilst holding my gaze, put her hands on my knees, parted my legs and knelt between my thighs. Kelly slid her hand over the bulge in my jeans, and began rubbing me through the material. This was what I had been dreaming about for months. I nearly exploded even before she had got my cock out, but I wanted to fuck her so much. Kelly was soon attacking my belt buckle, like a women possessed. Kelly put her hands inside my boxer shorts and released my cock. She lowered her head and took my length into her mouth. I had been sucked off before, but this was like nothing else! Kelly then started to deep throat me, which I hadn’t experienced before. The sight of my entire shaft slowly appearing from between Kelly’s beautiful lips was more that I could take. I exploded in Kelly’s mouth. I expected Kelly to pull away followed by a few expletives. Instead Kelly allowed me to finish, looked up at me and showed me all the cum in her mouth. Kelly then proceeded to swallow and stick out her tong. I can remember this was just like all thought porn film I had wanked off too.

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By (user no longer on site)  over a year ago

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By (user no longer on site)  over a year ago

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By *af105Man  over a year ago

Newtownards

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By *ood tongue!!!Man  over a year ago

harwich

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By *ilthy gentleman 4425Man  over a year ago

Ackworth

wow more.... hope she like hes arse fuckt... x

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By (user no longer on site) OP     over a year ago

Kelly stood up and kissed me. I had never tasted myself before. Kelly whispered into my ear, “It’s your turn now.” Kelly sat down on the couch and I stood up. I stepped between her toned thighs and took hold of them. I pulled Kelly towards me and she slid down the couch. Her arse was now punched on the edge of the cough. I stared at her crouch like a hungry wild animal staring at it’s prey. I moved my hands up to the buttons of her jeans. In my haste to reveal her pussy, I fumbled her buttons. Kelly batted my hands away, and undid the buttons herself. The hole thing seemed to play out in slow motion. As Kelly’s jeans loosened I caught a tantalising glimpse of lacy red patties. I moved my hands to the her side, and took hold of her waist band. As I did this kelly lifted her pelvis, and I pulled her jeans down.

As I pulled Kelly’s jeans down, I reveal the most amazing pair of red lacy panties I had ever seen. I could just make out Kelly’s swollen lips through the lace. I put my hands on Kelly’s knees and pushed them apart. I lowered my head and started teasing Kelly’s pussy with my tong, right through her panties. Kelly through her head back and let out low guttural moan. I pulled her panties to one side to reveal her ripe little pussy, just waiting to be licked. Kelly was so well manicured. The only short hair on Kelly’s pussy was a small neatly trimmed triangle pointing the way.

This is what I had been dreaming about! I know I should have started by kissing her toned thighs and all around her wonderfully presented pussy, to teas Kelly. But I was just couldn’t stop myself from sticking my tong between Kelly’s beautifully inviting lips. Kelly tasted so good! I lapped at her like a starving wild animal. I buried my face between Kelly’s legs and I stuck my tong as far as it would go, but it still wasn’t deep enough!

By now I had realised that Kelly was throwing her head back and moaning, like a women possessed. Unbeknownst to me Kelly hand removed her shirt, and was frantically playing with her pert breasts. The sight and sound of Kelly in such ecstasy only turned me on more. I had regained a small amount of composure now, and wasn’t thinking entirely with my penius.

As Kelly realised I had stopped licking her intoxicating pussy, her body relaxed slightly. Kelly stopped thrashing around and looked down at me. Kelly’s hair was all over her face, and I don’t even think she could speak. But I wasn’t finished! I once again lowered my head. But this time I traced my mouth round Kelly’s jewel like clit. As I sucked Kelly’s clit into my mouth, she immediately clamped her legs tight round my head. I drew two fingers up to my mouth to moisten them, before placing the fingers between Kelly’s swollen lips. I could hear Kelly take a sudden breath and hold it in anticipation. I began pushing my fingers into Kelly, and she let out the breath as suddenly as she had taken it in.

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By (user no longer on site)  over a year ago

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By *oraxMan  over a year ago

Bedford

Top stuff.

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By (user no longer on site) OP     over a year ago

My god, Kelly was so tight! I had to place one finger above the other as I slowly inserted them. I could feel every ridge as I gently pushed my fingers deep into Kelly’s warm, moist pussy. At this point I paused and moved my fingers from one above the other, to side by side. This stretched Kelly, and she put a hand on my head. She ground my face into her pussy, urging me on. I curled my fingers back and began to stroke the soft ridges of Kelly’s G spot. Kelly removed her hand from my head. I would imagine Kelly moved her hank back to playing with her wonderfully pert bests, because at the same time Kelly’s breathing became deeper and laboured. Kelly’s thighs tightened there grip on my head, and her moans became louder and more urgent. I could feel Kelly’s hole body start to convulse. The walls of Kelly’s pussy began to contract on my fingers. I continued massaging Kelly’s growing G spot. It felt incredible!

Kelly erupted, as an all encompassing organum passed through Kelly’s petite frame. I kept my face buried between Kelly’s thighs as she began to with in ecstasy. I pushed my fingers insider Kelly, so that I could feel as the organum paused through her tiny frame. I assume Kelly was on the boarder between pleasure and pain, because when I attempted to continue my oral endeavours, I was pushed away.

I waited, and waited until Kelly’s organum had passed. As Kelly lay there limp and recovering, I eagerly inserted my fingers once again into Kelly and lowered my face to her clit. Kelly once again started to moan, although this time wasn’t Kelly’s moans were slightly more restrained. This time Kelly started to speak. “Please fuck me” Kelly said. I wasn’t finished eating Kelly’s pussy, so I continued. Kelly repeated her request, but this time she was pleading with me. I found her pleading was getting me off, so I continued. “I kneed to feel you cock inside me. Please fuck me” Kelly now started to beg.

I made my way up her glistening torso, positioned the head of my cock at the entrance to Kelly’s moist pussy lips, and began to kiss her passionately. I then moved my head down to her breasts and began pulling on the base of Kelly’s nipple with my teeth, whilst aggressive massaging the other one. All the time I was rubbing up and down Kelly’s body, and gently nudging her lips with the tip of my cock. Kelly kept moving her pelvis so that my cock might slip inside. I was enjoying teasing Kelly too much. “Please, I kneed to feel you inside me”, Kelly pleaded again.

I allowed my cock to slip inside Kelly’s pussy. Kelly hole body immediately tensed, and she unleashed a low guttural sigh. It sounded like the sigh had been building up inside Kelly since we met. This was all I had been fantasising about since we had starting to work together. Part of the reason I has spent so long going down on Kelly was because I didn’t know how long I could last. Now I was inside Kelly, it took all my self-control not to instantly explode.

After several minutes of thrusting, I brought Kelly’s legs together in-front of me. I pointed the soles of her feet to the ceiling, and continued thrusting into the back of her legs. This gave me a few more minutes, but the inevitable started. I could feel myself start to cum. I laid Kelly’s legs back on the bed, and speed them as wide as I could. I grabbed the head board to try and make each thrust as deep as possible.

I manned a few more thrusts, and then I exploded inside Kelly. I collapsed on top of her, and we just lay there for several minutes. I was excused, and enjoying the feeling of Kelly’s pussy contracting around my cock, as her organum rippled through her.

This is the final instalment, I hope you have enjoyed reading as much as I enjoyed writing it.

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By (user no longer on site)  over a year ago

Yes enjoyed it very much hope you do another one soon

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By (user no longer on site)  over a year ago

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By *revorAndTraceyCouple  over a year ago

Newcastle Upon Tyne

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By *cfc1965Man  over a year ago

horsham

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By *cfc1965Man  over a year ago

horsham

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By *cfc1965Man  over a year ago

horsham

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By *untimes6969Man  over a year ago

Newcastle upon Tyne

Great experience between two special friends! Where did it lead to?

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