My First Older Woman_(0) free porn video

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Well as the years past a lot of things changed. I moved out of town to go to college and she wound up divorced from her husband. Anytime I would go back home I would call to see what she was up to and she was usually out clubbing or something. I was only 19 and couldnt get into most of the clubs she was going to. Well one wednesday afternoon I got a call from her asking if I would be willing to come to town to watch her kids while she hosted a party at a hotel for her boss and his company. She was his secretary so she was charged with setting up the entire party. Her exhusband was being a bit of a jerk and wouldnt take the kids for the weekend so she just decided she had to get a room at the same hotel and have someone watch the kids. I agreed to do it, if anything at least I would get to see her!

Well that Friday I drove back home and the party would be Saturday evening. I spent time with my family in my old neighborhood friday night and saturday during the day. But Saturday afternoon with a bag packed I headed to Annie's house. She explained the situation and that I would be able to be paid Sunday morning after her boss paid her. So we packed up the three kids and off we went to the hotel. She had to set up for the party in the ballroom. I spent time with the kids in the pool, as well as an arcade that they had on the first floor of the hotel. We all went to dinner at McDonalds so the kids could play before we were stuck in a hotel room for the rest of the night.

The evening rolled around and Annie had to prepare for the party. She came out of the bathroom looking sexy as hell. A form fitting black dress that plunged to show an amazing cleavage line and her curves. The dress stopped about mid thigh showing her amazingly firm legs. She kissed the kids, gave me a hug while saying thank you and went on her way.

Not even an hour had gone by when there was a knock at the door. It was Annie and a coworker who had snuck up to tell me that Annie's oldest daugher Hillary was going a few rooms over to play with her coworkers daughter, and that her exhusband had called and was wanting his other two kids. So the oldest daughter went up the hall to another room where her friend was and I was going to wait for the father. When he got there I handed off the kids and just hung around the room I had ridden with Annie so I really didnt have anything else to do, and hadnt brought anything that I could really wear to a party.

I was standing out on the balcony that over looked the pool when I saw two young people come out poolside late at night. They looked like they were either at the party hosted by Annie or another one in the building. The scurried along looking all over the place until all at once they both stipped naked and jumped in the pool. The girl was amazingly sexy with red hair and a great body. I cant give too good of stats because of the position I was at, but I can say her body was amazing. Watching her swim back and forth my cock began to stiffen immediately. After a while the couple swan towards each other and embraced in a kiss. The kiss began to heat up and after a few minutes she was riding his cock at the side of the pool. I watched intently as I reached into my shorts and started stroking my rod. This was better than watching porn because it was real and it was right there.

As I wa stroking slowly and getting near my peak I heard a rather drunk voice next to me "what are you watching down there?" Annie said, luckily enough not noticing my hand in my pants.
I was startled and jumped..."Oh nothing much....just getting some air." I kept my back to her so she didnt see how tight my shorts were from the hard on.
She looked over my shoulder and saw the couple screwing in the pool "Oh wow...well that is quite a show isnt it! Bet that is better than television!" she giggled.
"Yeah I guess so," I said sheepishly.
Annie continued looking over my shoulder and snuck a peak downward "Well it looks like you are REALLY enjoying the show arent you Scott?" I was getting a mischevious grin from her now..
I was embarassed and didnt know what to say....so I said nothing. She grabbed my shoulders and turned me around, reached down and felt my cock through my shorts.
She leaned in next to my ear and moaned, making my dic twitch with excitement. "Why dont we go inside?" She said as she grabbed my hand and lead me inside.

As soon as the sliding glass door shut she was kissing my neck and sliding my shorts down until they fell to the floor with my member springing out toward her. "There has always been something about the way you watched me that turned me on Scott."

"You have been turning me on since highschool Annie." I said in return as my hands cupped her breasts from outside her dress. She slowly slid to her knees and began to lick my rock hard piece and all I could do was stare. She slowly took the tip in her mouth and began to cover every inch of me until my entire piece disapeared into her mouth. Slowly stroking my cock with her warm mouth while her free hand played with my sack I could already feel my young self getting close to cumming so I pulled my cock away from her and stood her up. I began kissing her deeply as I reached behind her and unzipped the little black dress and slid it to the floor. There she stood in a matching red and black lace bra and panty set with those huge tits just aching to be set free. It was the best sight I had ever seen, and can still picture it like it was yesterday.

I walked up to her, reached around and undid the bra letting it fall next to her. Her nipples were standing at attention as her beautiful breasts still sat up really nicely for her age. I began licking, biting and sucking her nipples while we inched closer to the bed. We got to the bed and she slowly sat down as I slid her panties off to reveal a nice looking pussy with a small trimmed patch of black hair above it. I began to salivate at the thought of tasting that sexy pussy that I had tried my hardest not to fantasize about for so long. I dove in like a swimmer in the olympics. Licking her pussy, which was already wet and sweet, while I used my thumb to play with her clit. She was moaning and writhing with pleasure and saying words I dont know that I had ever hear her say, which only drove me wilder. I moved onto the bed and got her to straddle my face so she could grind her pussy on my face as much as she wanted. We wound up in a 69 position rather quickly where we were both just frantically sucking and licking each other. I felt her pussy contract as juices flowed over my chin as she groaned in pleasure.

After she climaxed on my face she slid my cock deep into her in the reverse cowgirl position....I had held out for a long time without cumming and didnt know how long I would last. She hopped up and down agressively as her warm wet twat hugged my rod. I was thrusting up at her as she rode and could feel the build up in begin. As if she knew what was about to happen she said "Cum inside me Scott, do it."

With her words of approval I began spewing into her as I humped viciously up into her ad she began to grind herself on me as she had another small orgasm herself. She laid down next to me both of us sweaty and out of breath as we fell asleep.

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I thought I'd tell you all about the first time I was with an older woman, It was my friends 21st birthday party. His mother threw a bit of a do for him at the house and invited a few of his friends and some neighbours over, we were drinking for most of the night and having a laugh. As the party was ending people started to leave and I began to help clean up when his mother asked me if I would walk mrs carroll home as it was dark and she lived about 3/4 mins walk up the road. It was about 1am...

4 years ago
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Eye of the Beholder Part 2

The following is the 2nd part of Eye of the Beholder. I have had some very positive feedback on part 1. I hope you enjoy this as much. Please let me know by leaving a review or email me at [email protected] Part 3 will follow shortly. Eye of the Beholder - Part 2 - by: Tanya Grant Consequences: I woke a few hours later, the smell of coffee wafted into the room, as well as toast and eggs. I realised I was starving hungry. I looked around for something to wear, and saw...

3 years ago
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Eye of the Beholder Part 3

Eye of the Beholder Part 3 ? by: Tanya Grant This is the continuation of Alex Wards undercover operation. Please read parts 1 & 2 first if you are unfamiliar with the story. This story and it's constituent parts are copyright Tanya Grant and no reproduction or use outside of those sites given permission to carry is implied or allowed. Please contact [email protected] if you want to talk to the author. Part 4, the final episode is being written and should be...

2 years ago
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My experience with a much older woman

When I was 30, and the internet was a much newer concept that it is now, I got chatting to an older woman via an online chatroom. We got on pretty well and there was a bit of flirting - it turned out she was only out of a very long and not very happy marriage. Well, out of as in separated, not yet divorced.After a bit of persuading, she agreed to meet me, and we met at a motorway roundabout one day which seemed like a handy neutral venue and was easy to get to for both of us. After a chat in...

4 years ago
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The Saleswoman

The Saleswoman Belladonna [Author's Note: Based on a cap by Commentator] The sound of a phone ringing turned Portia Dawn's head. She reached for the phone and picked it up as she saw her secretary's name appear on the caller identification panel. "Yes, Maria," Portia answered. The woman on the other end hesitated before she replied, "Jeff just stepped into his office." "Thank you, Maria," Portia replied while she felt a sinking feeling in her stomach as she hung up...

1 year ago
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Babysitter gets educated by an older woman

Jade had been asked to do an evening of babysitting for a friend of her mothers, Alison. Alison had a 5 year old daughter but the father had never stuck around to be of any use. At 18 Jade was desparate to earn a little money to let her go out at the weekend.Alison was not without means and lived in an old barn conversion in a nearby village. Being 5 miles out of town Alison had invited her to stay the night after she had returned from her night out. What exactly the night out was...

2 years ago
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Catwoman

Nacht in Gotham City. Doch friedlich ist es nicht. Während in den Straßen Gangs randalieren und die Polizei alle Hände voll zu tun hat, die Ausschreitungen in Grenzen zu halten. Im riesigen Büroturm des MyersElectronics war es ebenfalls nicht ruhig, auch wenn es von außen den Anschein hatte. Im Treppenhaus des Wolkenkratzers rannte Catwoman so schnell sie konnte die Stufen hoch. Schweiß lief unter ihrer Maske herunter und tropfte auf ihren schwarzen, hautengen Catsuit, der ihren kurvenreichen...

2 years ago
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Student keyholder

And there he was, buckling over, gritting his teeth and trying to hide the pain. I had it confirmed. Dr. Oswalt had been glancing at his female students more and more over the past few weeks. I wasn't the first to notice. I remember Leanne pointing it out to me way back in October. But after that, it seemed obvious. He was constantly taking looks at my tits, and everybody else's. I remember the theories … he wasn't banging his wife anymore, he was just becoming a creepy old man, etc. I...

BDSM
3 years ago
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Chastity with Ex as Keyholder Part 8

Chastity with Ex as Keyholder Ch. 08bychastity_sissy©"So, that is what you fantasize about? Having my hot boyfriend and me making you our little sissy bitch? Pathetic," my Ex said flipping through the pages of the story I had submitted to her, while I worshipped her sweaty pantyhosed feet per our already established agreement.I still couldn't believe an Ex of mine was actually a hot Hooters girl. Being one with a small, tiny, thing for uniforms, I couldn't believe I had let this one slip...

2 years ago
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Chastity with Ex as Keyholder Part 6

Chastity with Ex as Keyholder Ch. 06bychastity_sissy©My Ex knew me. She knew me better than I knew myself. She knew it had been a deep, disregarded fantasy of mine to be a helpless maid amongst a variety of men and women, all dressed up in pretty outfits demanding drinks and snacks from the maids passing by.She had, without a doubt, put "the guy" in his place. My cock was completely locked away in full metal, and it would require an ER visit to physically remove the device without a key. I...

3 years ago
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Chastity with Ex as Keyholder Part 2

Chastity with Ex as Keyholder Ch. 02bychastity_sissy©From what I could remember the following morning, I had definitely done something stupid. My memory became fuzzy after she had left. Just as she had predicted, I surfed the web and looked at my saved cache of porn. Unable to get off on it, I drank more and stayed up later than usual until everything became a blur and I woke up on the couch, still dressed in the corset and nylons.Good thing I had the day off.Work! How could I deal with wearing...

4 years ago
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Chastity with Ex as Keyholder Part 1

Chastity with Ex as Keyholderbychastity_sissy©Several days off. I was looking forward to it. The days off had been meant for something else, but those plans fell through. Now, I had the weekend plus several extra days. I could barely contain myself as I was excited to try out the new toy I had recently purchased.As soon as I got to my apartment, I checked with the management building and sure enough, the package was there. Before I could do anything else, I had the package opened on my table...

2 years ago
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My First Older Woman

About 10 years ago I was out at a pub for a workmates going away party, not really my scene but the workmate was a good bloke and I really needed some times away from my girlfriend, who I’d being seeing a for 2 about and a half years. But to be honest, it felt like the last few months were just out of routine. Things were on the downturn and weren’t getting any better. It was well and truly beyond its use by date, but I guess both of us were too afraid to move on.Anyway, back to the story.I...

3 years ago
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Relationship with an older Pakistani woman

Hope you guys out there enjoy reading as much as I am enjoying my time with this woman.So, I recently graduated from university and came home to visit family before starting my new job later in the year.Sex at university was always temporary and being Pakistani, I have always chosen white girls throughout school, college and university as they seem to have a more open lifestyle. Dating Pakistani girls was always put of as I never seemed to connect until recently, with a woman 10 years my age. ...

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