My First Time With An Older Man... free porn video

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When I was growing up, I would do pretty much anything for a bit of cash in my pocket. I worked in a sweet shop/newsagent every weekend from age 14 through until I had just turned 17. Our customer base was pretty much older men who would pop in during the day and spend as much time as was reasonably possible in the shop buying their sweets and papers, and chatting to the shop owner and me. It was during these years that I learnt how to deal with and appreciate the older man.

My boobs had started to grow before I had started work in the shop, and by the time I left I was sporting a rather nice pair of 38H and was a size 18 in clothing. I started going out to clubs with my friends and found that I got a lot of attention and I had a lot of fun... however my fun times were not sustainable without an income and my parents were refusing to continue to fund my nights out.

Now, fast forward to a few months after I left the shop. A new family moved on to our street. The adults were an attractive couple. The female, Jill, was 38, around 5'5" with long bleach blonde hair, a very slim build with tiny tits. The male, Steve, was 44, about 6'2", dark hair, and was an average build. They had a couple of rugrats in tow. They were unpacking their van as I was walking down the street and I stopped to say hello and asked if they needed any help. I mean, I had nothing else to do.

They politely declined my offer but mentioned they would be looking for a regular babysitter due to the nature of their jobs. Now I have never been a maternal being and looking after brats was the last thing I would have considered at that time so I just said I'd put the word round for them. A few days later there was a knock at my door and it was Jill. She said they were desperate for a babysitter and she was willing to pay me £50 for the emergency help. I thought for a second about which one of my friends would help out. It wasn't long until my stupid brain kicked in that she'd offered £50. £50! So I told her I'd do it.

I walked down to her house with her as she explained the rules she expected me to adhere to. She told me Josh & Lucas were already in bed and I had the run of the house until her or Steve got home. I spent the night just sat on their sofa watching TV hoping that the k**s stayed asleep.

At around 10:30pm Steve got home. He was shocked to find me sat there so I explained what had happened. He paid me the £50 his wife had promised and we sat chatting for a while. I found out that he was a solicitor and spent a lot of time dealing with clients outside of normal office hours. He could be called away at any time. He told me Jill was a personal assistant for a very needy business who just called on her at any time.

After chatting for an hour or so I made my excuses and left with my £50 - got taxi to town and boozed it away. The next day I battled through my hangover and popped down to my new neighbours to offer my babysitting services more regular, much to their delight. They offered me £30 an hour and wanted me to be available 24/7.

Over the next few months I'd be called upon most nights, and most nights Steve would come home and we'd chat away for a while before I left or Jill got home.

One day Jill told me she was going away with her boss on a business trip for a few days and asked if I'd be able to stay over at their house for the first night as Steve was going to a party and would likely be very drunk when he got home. I didn't see any issue with that and said "Of course I will! No problem!"

This was the point it all changed.

I had my blankets and pillow setup on their couch and had just fallen asleep when I heard Steve stumbling at the door. I had already changed into my PJs which were a silk & lace vest top and short shorts. I didn't have a bra on and my boobs were just hanging free under my vest. However, Steve was not finding his way through the door and I knew I was going to have to let him in. I figured he'd be too drunk to even notice what I was dressed like anyway. So I got up and opened the door. He stumbled into the house, looked at me and said "Helllllo baby! When did you get so... attractive?" Then he reached out and grabbed me by the waist. I pushed him away saying he was drunk and he should behave. Being honest though, I kinda liked the attention. He sat on my made up bed and beckoned me to sit next to him. I sheepishly walked over and sat down. He put an arm around me and gave me some drunken conversation before getting up and going to his bed. I realised I was quite attracted to him and he'd got me horny. It was too late now though as I'd let the moment pass and he'd wake up tomorrow not remembering. So, as I lay in his perfect house, on his perfect couch, I fingered my sopping wet pussy imagining it was Steve ramming in to me... I came hard for the very first time from masturbation that night.

In the morning I went upstairs for a quick check on the k**s and figured I'd have a shower if they were all still asleep. They were still all sound so I took that shower. I had popped my head into Steve & Jill's room before to check he was ok. He was asleep but had some serious morning wood going on. I could pretty much tell how big his cock was through his blanket. This has turned me on again so I decided I would get myself off in the shower.

I was still relatively new to masturbation, even at 17/18, so the only way I could hit the right spot was to sit down in the shower... I began rubbing my clit slowly with one hand and grabbing my tits with the other. As I got more into it, I couldn't stop my moans. I could practically feel Steve's big old cock pushing inside my tiny tight pussy. Just as I was about to cum there was a knock at the door and Steve asked if I was ok. I shouted back saying I was fine.

"How long do you think you'll be?" he whispered back, "I'm dying to piss! Could you just cover up with a towel will I go quickly?"

I quickly grabbed a towel and shouted "Yeh sure" back to him.

He ran into the bathroom, whipped out his cock and pissed for England as I stood there naked in his shower, except from a towel, watching him. I couldn't take my eyes off his cock. My pussy was throbbing already, and my nipples were rock hard and rubbing against my towel.

"Hey, stop looking at my dick!" Steve turned to me and winked.

I went bright red and apologised. I was so embarrassed and realised he was never going to use that cock on me anyway.

"Nice shower?" He asked.

Oh my gosh. He's making conversation with me in the bathroom?! "Errr, yeh, lovely. I didn't think you'd mind..."

"Nope, I don't mind at all," he replied as he walked towards the door. I closed my eyes for a second to thank the lord that he was leaving the bathroom. I heard the door click closed, I flung my towel off, turned around and switched the shower back on. As I moved back around to face away from the wall I noticed Steve hadn't left the bathroom. He was stood at the door watching me with cock in hand. I had no idea how to react to this. He locked the bathroom door and moved towards me. Without saying a single word, he shook his ankles free from his boxers and climbed into the shower with me.

He picked up a sponge, covered it with shower gel, and began to wash my body. It felt so good. My legs were turning to jelly and I had to grab him to stay upright. His cock rubbed against me and it was hard as a rock. As he continued to soap my body up, I grabbed on to his cock and began to slowly wank him. He moaned gently and started to suckle on my nipples. No one had ever done that to me before and I almost came just from that. It was so erotic. He dropped the sponge and began to rub at my clit as I was stroking his cock. I came within seconds, and he quickly followed. He smiled and climbed out the shower, slipped his boxers back on and left the bathroom.

I was left shuddering and wondering what had just happened. I showered off properly, got out, dried and changed and made my way back downstairs.

Steve was in the kitchen making breakfast for the k**s, who were in the living room watching TV. I told him I'd get going home now. "I'll ring you later if I need you," he said with a wink.

I walked out of the door and went home. I'd only been home for 40 minutes and was lying on my bed masturbating again, (He had really turned me on) when he rang me saying he was going to need me tonight for sure... "Perhaps you could stay over again?"



To be continued....



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Older Weman

As some people of Ukex know, i adore the more mature lady. I have a great sex life with my wife , but have to say that even though she was happy to do most things, she isn't a patch on some of the older ladies I have had sex with in the past few years.One of my lovers is a divorcee named Jean who is 64, and is a work colleague. Jean worked in the office, (still does in fact).We first had sex when I had been dropping her off home for a few weeks, and as a thank you she said that, if i didnt...

2 years ago
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My Pleasure Moments With Suman

By : Delhibiz Hi, this is Gautam from Delhi. I like the most the stories of ISS and reading them from long time. I am 28 years now and this story is 3 years back with one of my exclusive friend. However, she is not with me now and married to someone. Her name is Suman (name changed). We are of same age and worked in different firms in Delhi. During my official tour to Mumbai, we met each other and the story begun. Let me describe her about her physique.She is quite fair with some extra pounds...

2 years ago
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first time was with an older man

i was only new into the cruising scene and very inexprienced as well but i had urges to feel what it was like to have a hard cock in my mouth so i jumped on line.i wasnt to sure what to expect on these sites but from the first moment i saw how many guys were floating about i knew i was hooked for life, i viewed alot of profiles not exactly sure what i was looking for but i knew one thing i like older men, maybe because they know what they are doing or maybe just because i like to please....

1 year ago
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Seducing a telephone repairman

I’ve had fantasies about the cable guy that I had once seduced. Jimmy and I unfortunately didn’t have video of it but he was able to take pictures of me taking his big black cock. I’ve recently had to go back to that picture set and loudly reminisce about it as Jimmy fucked me in bed one night. Ironically, a day came when we had trouble with our phone line and finally Jimmy placed a repair request order to fix the problem. When we were finally told what day the telephone repairman was coming to...

Erotic
2 years ago
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The Amazing Mr Mortimer

THE AMAZING MR. MORTIMER My girlfriend Rachel and I had decided to take a two week vacation to PuertoRico. I had first come across the girl on the streets of San Juan. She cameup to me and begged me for some money. At first I was going to say no. ThenI noticed how beautiful this young girl was and I was intrigued. I startedto reach into my purse to get her something, and she smiled at me. She hada very beautiful smile. It was in fact an entrancing smile. I kept her close to me with small bribes...

1 year ago
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Robin and the Catwoman

“Oh my head.” Robin whispered as he stirred awake. It took a few moments for him to fully regain consciousness. His last memory was of chasing someone across the Gotham rooftops, now he was in someone’s apartment. “I’ve been captured!” He screamed in his mind as he suddenly realized he was under restraints. Taking a deep breath, he willed himself to think calmly, just as Batman as taught him. Take stock of the situation, then form a plan of action. The room was in semi-darkness, illuminated...

3 years ago
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In Praise of Older Women Part 5 Emancipation

Meg’s Tale      Both my lovers, Jack and Kate, had returned to their normal lives. My decisions now were made. I had decided to sell my house in the suburbs and move downtown into a condo.This would be another life change for me. Meg the suburbanite had resolved to become Meg the follower of new lifestyles which could not occur in the suburbs. I had spent my marriage in this house and the years where I had rebuilt myself into a new woman here. I was now ready to face the world and new...

MILF
4 years ago
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Ek Main Aur Ek Manu

Hello ma crazy reader my name z Siraz, siraz sidaqi. I was also a reader of ISS lyk you. Actually still I am while reading ol d stories on ISS. I used to thought about se fun in ma like and humesa hi mauke ki talash me rhta tha bt aisa lgta tha ki jaise upper wale ne ek mere hi liye koi mauka banaya hi nahin, isi tadap me aur us parwar digar se narajgi me meri jindagi bit rahi thi bt wo khte hai na, ki dhundho to khuda v mil Jata hai to baki ki kya majal bs usi tarz pe wakai wo din aa hi gaya...

4 years ago
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The Keyholder Pt 2

What was she doing playing chastity games with a twenty something guy? She knew it was crazy, yet Amy was smiling to herself as she stepped off the bus and walked quickly to the address that Ben had given her, a two bedroom apartment in an upmarket development. She hadn’t seen Ben since they’d made love at the hotel a week ago, but she could still remember the feel of his body and his freshly unlocked cock. She hadn’t belted him when they parted the next morning. This wasn’t because Ben didn’t...

BDSM
2 years ago
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The Keyholder

“Just that please,” Ben mumbled as he nervously placed the steel chastity cage and padlock on the counter. He was on his way back from drinks with the football team and the elation of winning combined with the alcohol had given him the courage to finally indulge one of his fantasies. Careful not to make too much eye contact, he glanced briefly at the woman behind the counter, who smiled kindly as she wrapped the cage for him and took the cash. He was now really starting to feel embarrassed,...

BDSM
3 years ago
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The Airman

The Airman?.. It?s strange how the mind can recall certain events with such clarity yet blot out others. It was as if my life began during the years of World War Two. I don?t recall much of anything prior. Of course, being raised and educated in an orphanage doesn?t highlight much. I do remember enlisting into the military at the earliest possible age, to be on my own. As a young airman in the Army Air Corp, I remember my last bombing mission and the ensuing events...

4 years ago
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How Do You Solve A Problem LikeMiss Manson

After her meeting with Ms. Storey that lunchtime and on hearing that the strict young deputy headmistress was going to allow Rebecca Mulligan to carry out her plan to deal with Miss Manson, the head of Music at St Katherine’s School did not hang around for long after the end of the school day. Once she had taken the full school orchestra for their after-school practice she returned to the Music office, packed her bag and hurried to her car. She arrived home just after 5 pm and decided that she...

Spanking
2 years ago
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Crazy Sexperience In Manali

I am Niki and I am back with my second sex story. This was my first one – https://www.indiansexstories2.net/couple/kritis-crazy-sex-story/ This happened a few years back when my four friends and I were on our way to Manali from Delhi. We were thrilled to take a few days off to enjoy the lovely spring in Manali. It was three girls including me and two guys. One of the guys had taken his brother’s Innova car for the trip to drive down. Basically, amongst the 5 of us, we had a couple, two single...

3 years ago
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TV Repairman

TV REPAIRMAN by kimmie oh The doorbell rang, and Billy padded barefoot over the hardwood floor of his apartment. He quickly checked his reflection in the mirror one last time. Then he took a deep breath, smiled, and opened the door. He felt a blast of January cold on his rather scantily clad body. In the vestibule stood a tall, good-looking older man in worn work clothes. The man gave Billy a quick once-over and Billy held his breath. He wondered if he had gone too far: the...

4 years ago
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The Horseman

Once upon a time there was a princess. She was feeling very trapped in her kingdom so she wanted to take a ride. She summoned her horseman to take her on this ride. He was a loyal man and was willing to do anything her royalness asked of him. Because deep down inside he had serious feelings for her, But was afraid to show this because he was afraid that she did not feel the same way about him considering their positions in the social order as they were. He brought the horse around and helped...

4 years ago
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The Legend of the Dickless Horseman

 It was a dark and stormy night. I was reminded of that fact by a beagle glaring down at me, hunched over like a vulture, perched on the porch of my destination. I pulled my raspberry beret down snugly for protection from the bitter New York wind.I glanced at the decaying house before me. The years had not been kind. Whereas it once stood majestically on a hill radiating beauty now it was an eyesore; the real estate equivalent of Kathleen Turner. Still, it was precious to me. Full of wonderful...

Fantasy & Sci-Fi
4 years ago
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My First Time with an Older Man

I was working at a factory in my hometown over the summer. I was a19-year-old college student at the time and I needed the money. The workwasn't hard, just boring. Worse yet, my hometown was a fairly small andun-interesting place as well. My mind wandered a lot during the day and italways ended up wandering to the same thing. Ever since I had discoveredpornography on the internet, I have been obsessed.I didn't have my own computer in college so I always had to use someoneelse's. During...

1 year ago
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My Friend Suman

Hi friends mai bhaut dino se iss ko padathe arahu to maine socha ki maine bhi apni ek real stori post karu. kya malum apko pasand aye or na ahe thik hai. ok my name is joy and i from mumbai.any girl or any woman want relationship with me to contact my email id.. ok maine abhi meri stori pe aata hu. aap ise fake samse ya true its on you but its my true story in my life. ok. Main Mumbai me ek chawl me rahata hu. me us time 12 stands me tha main dikhane itna handsome nahi hu. esiliye main...

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