The MD and IT guy

Working in a bar

So here I am due to some financial miscalculations during my university years having to work 2 jobs, during the day I work in the IT department of a large financial services company in Colchester, 3 evenings a week I work in a local bar to make ends meet.

My name is Steve and I am 24 years old, I am 6ft tall with dark brown hair and an average body though I do get a workout most days normally by lifting and changing beer barrels. I am quite popular with the ladies at both my work places as I have a winning smile and a sunny disposition.

I flirt with the ladies where I work but it always seem to be older ones that really catch my attention, there is something about that slightly wrinkled faces and sensible but classier dress sense that draws me in, or it could be the fact that I lost my virginity aged 18 to my mate's mum.

"How I lost my virginity 6 years earlier"

Chris Armstrong was my best mate through school and 6th form and we were always close. We used to spend nights around each other's houses and play video games or watch DVD's.

Chris' mum was called Sharon, she was a mumsie type mum if you know what I mean, always dressed respectably and impeccably nearly always in a blouse and cardigan with slacks, with her short blonde hair styled neatly, there was never a hint of cleavage or inappropriate flashes of skin, that's not to say she wasn't attractive, she had a beautiful face and from what I could tell a slim body. She would always fuss over us and make sure we had enough to eat or drink, she was always smiley and was very touchy feely with me, she would always hug me when I arrived and left and would insist that I called her Sharon.

One day I popped round on the off chance to see Chris, Sharon answered the door but looked like she had been crying, she was all smiles as usual but her mascara was smudged and her eyes were puffy. I hugged and just said "What's wrong Sharon?"

That set her off again and she buried her head into my chest, "Chris' dad has been cheating on me and he told me last night that he is going leave me, he has taken Chris on a last minute father/son bonding trip and to tell him, he told me I was fat, old and ugly and that he was upgrading to a newer and younger model."

I didn't have much experience of dealing with crying women so just held her and stroked her back. She just held me close and I just said "Excuse my French Sharon but he's a bastard and will come crawling back when his younger bit of fluff gets bored with him and he realises that he has left the perfect woman behind."

She looked at me through her puffy eyes and stroked my face, "Thank you for trying to make me feel better" she said. I stayed the evening being with her on the sofa and made sure she had enough food and joined her in a bottle of wine, she got changed into her pyjamas half way through the evening. Her pyjamas were pink and silky; she laid her head on my lap and I stroked her back and side whilst watching TV. I soon realised that the feel of her silky pyjamas and the fact I could no longer feel a bra as I stroked her back was giving me a rampant stiffy. She felt it when she moved her head and looked at my face and then my groin; she smiled and said "How sweet," and sat up and laid her head on my shoulder.

She fell asleep and I carried her upstairs and lay her gently on her bed and covered her with the duvet, at this point I twigged that Mr Armstrong always slept in another room. I had been told that it was because he snored but was it something else? I grabbed a blanket from the hall cupboard and fell asleep on the sofa. I woke at 7 in the morning to the smell of toast being wafted under my nose.

"Wake up" said Sharon, she was up showered and dressed. "Thank you for being there last night, I really appreciated it."

"No problem, sorry for the Errr thing," I said

She smiled and said "No problem, I'm just pleased that I can get that reaction from a young man."

"You always have done from me," I said before shutting myself up by biting into the toast.

She looked at me and said "Thank you, you are the just the ego boost a newly single lady needs, now can you come round tonight? I'll cook you lasagne."

She knew lasagne was my favourite meal, "Ok, I need to let my mum know what's going on and I can stay as long as would like me to."

"Bring a few days worth of clothes, I don't want to be alone in the house." she said.

Chris rang and told his mum that was going to be away with his father until the following week, he wanted to spend time with him before he left the house.

I returned to the Sharon's that evening after 6th form and was greeted by the smell of lasagne and home made garlic bread; she seemed in a cheerful mood. "I've been to see a solicitor and am going to take him to the cleaners, for some reason that and having you here makes me feel a whole lot better about myself," she said.

I kissed her on the cheek and watched as she bent down to the oven, she did in fact have a lovely arse, it wasn't fat and looked good in her slacks, "Nice arse," I said as she put the lasagne dish down on the hob.

"If I didn't know any better I'd say you were hitting on me," she said.

"Would it matter if I did?" I asked,

She smiled and just said "Dinner is ready."

We ate in silence at the table in the kitchen until she said "Do you really think I'm attractive?"

I just thought I was massaging her ego when I said "I've always thought so and if your fuckwit of a husband can't see that then he is a knob." She looked at me and said "Will you hug me again on the sofa whilst we watch TV again like last night?"

"Of course, I'll try and think of grass or something to stop little Steve misbehaving," I replied smiling,

She patted my cheek and said "You have always been a nice young man, why couldn't I be 25 years younger, we could really get along."

"We do get along," I started to say and then realised what she meant and blushed.

We finished eating and then at her behest put on my nightwear, which is a pair of sweat shorts and t shirt, .whilst I was getting changed she went upstairs and come down in a different pair of pyjamas, these had short arms and the bottoms were shorts, they were also silky but black in colour, the top button on the top was missing so it showed more cleavage than the designers had in mind.

I was lying on the sofa and she said "Don't get up, just move back."

She lay in front but with her back to me and lifted her head so I could feed my arm under her, I placed my other arm over the top of her and she held onto my hand and clasped it to her body as my arm passed over her, she then wiggled her bum back which rubbed against my by now rapidly hardening cock. I kissed her on the cheek and she sighed and she then moved my hand that she was holding up so that it was rubbing against her breasts, she turned around in my arms so she was facing me and my hands were stroking her back and said "You can't tell anyone," and then she gently kissed me on the lips. It was like kissing the softest warmest thing she could imagine, I kissed her back softly as she wrapped her arms around me neck and then we were snogging, full on French kissing, I was in heaven.

After a minute Sharon said "Let's get more comfortable and go upstairs."

I let her go and she stood up, as I stood up she took my hand and led me upstairs to her room, "Have you ever seen a naked woman before?" she asked as she started to unbutton her pyjama top, I just shook my head, "Would you like to?" I nodded my head, she unbuttoned the top but left it on, "Now you can't tell anyone," I nodded my head, "Good, now love me," and then she removed the top, her breast were wonderful, they were soft and warm and she had nipples that were already half an inch long as she said "Your turn," and walked over to me as I removed my t-shirt, we then engaged in some seriously heavy petting as I tweaked her nipples. She grabbed the waist bound of my shorts and pulled them down; she looked shocked as my cock nearly hit her in the face. "Fuck me, that's could split me open," as she looked at my 10 inch long and 2 inch wide cock and stroked it. She then kissed the end and opened her mouth and sucked the end into her mouth, with that I came into her mouth, she sucked it all in.

"Good now you've come, you can see to me properly, but first it's my turn." she said after swallowing it all.

She fell back onto the bed and pulled her shorts down, she was now naked and the most beautiful thing I had ever seen. I walked over to the bed and tried to mount her, "No, you have to get me warmed up first," she said "Lick me down there please."

I looked confused and she said "I really am going to be your first, I'm going to teach you everything about sex, now for lesson one," and guided my head between her thighs. Soon she was issuing instructions like "lick there, kiss me there, softer, harder, suck that" and then she came, I had never been so proud of anything in all my life, I had made this beautiful mature woman come, "Yes, you wonderful man, you've done it and I'm cccccooooooooooommmmmmmmmmmiiiiiiiinnnnnnnngggggggg."

She grabbed my head and pulled me back up to her face and kissed me hard, as I leaned into her my cock with the homing instincts of a cruise missile pierced her lower lips. Her mouth opened and her head rolled back as my cock slowly entered her, her mouth was brilliant but this was something totally different, as my cock slowly slid inside her it felt like warm jelly was encompassing it on its journey.

When my balls were resting on her arse she just said "Make love to me, slowly and considerately," started to flex her inside muscles, soon we were in a rhythm and she wanted me to change her angle of penetration so that my cock rubbed her clit on the way in, this triggered another orgasm in her and she wrapped her arms and legs around me and I warned her I was going to come, "In me, do it in me please," she said in my ear as my cock erupted my seed deep inside her. When I came it was like 1000 fireworks went off in my brain and she held me tighter and tighter until she relaxed, I later learnt she had come so hard when I came inside her she thought she was going to pass out.

We kissed for the next couple of minutes until she said she had to go to the toilet and we uncoupled, a copious amount of our juices landed on top the throw on her bed, she scooped it up and placed it between her legs to catch anything else that may drip out of her. Sharon returned a few minutes later and put on a thin dressing gown, "We need to talk," she said with a serious face, "As good as that was we cannot let anyone know it happened, Chris will be hurt and it could jeopardise my divorce case, I'm sorry but we cannot see each other."

"So what does this mean?" I asked.

"I cannot be your girlfriend, we can still see each other but when other people are around we must be seen to be as normal, when no one is around you can fuck me as often as you like, in fact I insist on it, I have never come that hard and I need you again." she said.

"So am I your fuck buddy?" I asked.

"I guess so, In return I will show you everything I know about sex and you will be on to a good start with any girl you meet in the future, now hug me and then we can have lesson number 2. " she said.

For the next 6 months we fucked whenever Chris was seeing his dad, she even managed to get me on a dirty weekend away to a cottage but then she met a man more her own age that she could start a relationship with and I moved away to university.

Every now and then we still hook up for old time's sake and she still reckons I'm the best shag she ever had but we can never be together.

"Back to now."

I was single and living in flat above the bar where I worked part time, I didn't want a full on relationship so just went from one fling to another. One night working in the bar a lady from the office walked in with a group of ladies, her name is Muriel and she is 50 years old was celebrating her 50th birthday with a pub crawl with the girls, her husband was away working and wouldn't be home until tomorrow.

Muriel was normally the shy retiring type but tonight she had had a few drinks and was quite loud. "Hi Steve darling," she called out when she saw me and turned to the rest of the ladies and said "this is my favourite IT support man."

"Hi Muriel, I've told you before to stop looking so gorgeous or I'll forget you are married." I replied. She was wearing a blue dress that hugged her UK size 14 figure like a glove , the dress was knee length and showed off her assets to perfection, the dress sparkled as I realised it had had sequins all over it.

Muriel giggled and asked me to get a bottle of fizz and 5 glasses, "who's the other one for?" I asked counting Muriel and 3 other ladies.

"You silly," she replied.

I asked my boss if he minded and said "go for it, you can get them to buy a few bottles whilst they are here."

An hour later and the 3rd bottle had been nearly drained, the other 3 ladies had all decided to go home as they had husband's waiting but one called Liz who I had my eye on slipped her phone number on a piece of paper into my back pocket and patted my bum when the others weren't looking.

I asked Muriel to stay and told her I would make sure she got home ok, "I need a coffee and I understand you live upstairs, would you make me one?" she asked.

I took her hand and her though the bar and to the stairs, I let her walk in front and to the side as I followed her up the stairs, she stumbled and feel slightly backwards, I grabbed her to make sure she didn't fall on me and my hand grabbed one of her breasts, I could feel her nipple through the dress and realised she was bra less, "Cheeky," she said and we walked upstairs with me cupping her breast and an arse cheek, as soon as the door to the flat was closed she turned around and kissed me quickly on the lips.

I said "I deserve more than that," and pulled her close to me, her arms went around my neck and she kissed me open mouthed on the lips, soon we were swapping tongues as I felt for the zip at the back of her dress, I located it and started to pull it down until it reached her waist, she kissed me harder as she felt my hand move inside her dress and stroke her now naked back.

"We can't, I'm married," she started to protest as I peeled the dress of her shoulders so that it bunched at her waist, she started to pull away so I kissed her again and placed a hand on her bare breast, there was some sag but it was still appealing.

She kissed me back harder and then she pulled back and started to undo the buttons on my shirt, "You can't tell anyone," she said as she pushed my shirt off me and then really started to kiss me as started to undo my trousers and push them down, As we stood there I detached from her lips and led her into the bedroom where I pulled her dress down off her hips so she was standing there in just a pair of sensible white cotton knickers. I pushed her onto the bed and she giggled as she landed and I started to kiss her feet, moved up her calves and inside her thighs. I pulled her knickers waistband down and she lifted her hips to help, and then I kissed her lower lips whilst reaching up and playing with her nipples, "Oh my that's nice," she said as I went to work, soon she was moaning and running her fingers through my hair and then she came, she went stiff and a silent scream left her wide open mouth as she clamped her thighs to my ears. Her nipples were now like mini torpedoes in my fingers as she held my hands to her breasts.

She released her grip on me and I kissed up her body and pulled my boxers down, we were kissing as she felt my cock bump against her mound, she grabbed it and placed it at her entrance and then grabbed both of my arse cheeks and pulled me in, she was so hot she pulled me in all the way in one movement and then grabbed my head, "Wish me a happy birthday properly," she said as I started to move in and out of her. She came once as my cock was sawing in and out of her hole, this time it wasn't silent, it was a full on screaming orgasm. As she calmed down she asked, "Can I go on top? So you can play with my nipples."

I rolled us so we were still connected and she ground herself against me and then leant over and dangled her breasts over my face, I sucked a nipple in which caused her to gasp and then she started to hump me, there is no other way to describe it, she moved my cock for her own pleasure until I told her my sap was rising which made her sit down as low as she could get on my cock so that it exploded as deep within her as it could get and caused her to come again. "Happy birthday Muriel," I said.

She kissed me deeply and said "I might have to have you as my birthday treat every year from now on."

"What about your husband?" I asked.

"I think we should keep this just between you and I." she replied.

I rolled us back over and started to move in and out of her again as she realised I was still hard, this time it was just a hot sex, no caring about the other party, just good dirty sex and she came a few times before I emptied myself into her, this time she needed to go to toilet and we cuddled up until we both went to sleep.

I woke up at 3 in the morning to find the bed empty and a note saying "thanks for my birthday present, see you here next year. M xx."

The next morning my mobile rang on my way into work, it was Liz, I remembered her because she was about 45 with an average figure but a really beautiful face, it was classical English rose beautiful and she had a sexy deep voice. "Hi Steve, I couldn't wait for your call and got your number from Muriel, I told her I need something sorting out at my house, can you come round this evening and look at my home PC? It's doing strange things."

"Of course, anything for a friend of Muriel, give your address and I'll be there at 7 if ok with you?" I replied.

"Wonderful," she said and gave me the address.

I arrived 10 minutes early and she opened the door wearing a dressing gown, "You are early, I've just got out of the shower, the PC is in the lounge, I'll go and get dressed and then I'm all yours."

"In that case don't bother getting dressed," I offered with a cheeky smile.

She smiled and showed me the lounge and just said "Be back in a minute."

She came down 10 minutes later wearing a red blouse with the top 3 buttons undone, the blouse was see through and she had a red bra on underneath. She had on a pair of black jeggings. She looked absolutely gorgeous and I told her so, "Your husband is a very lucky man," I said looking directly at the point where her buttons were undone on her blouse.

"I'm gay," she said.

"Oh well lucky girlfriend then." I replied.

"She's out of town at the moment, but I got you over here on false pretences," she said. "I know that you have already screwed Muriel but I was wondering if you would screw me, I want to know what it feels like to fuck a real cock rather than a strap on or dildo before I marry my girlfriend. This is for one night only and will never be repeated. "

"You are beautiful and I would gladly be your first man if you would like, my challenge will be to see if you want a repeat." I replied.

"Excellent, come upstairs in 5 minutes, it will be the door that is open," she replied.

I waited 5 minutes and walked upstairs, the only door open was into a bedroom, as there were very few personal items I guessed it was a spare room, Liz was lying on the bed wearing nothing but a smile and the red blouse only done up with 2 buttons in the middle and a red thong, her breasts looked firm and welcoming under the sheer material of the blouse.

"Well would you?" she asked,

"All the fucking time, you are sex on legs and it's a shame you are gay because we could make a lot of sweet music together," I replied.