My First Older Woman_(1) free porn video

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My First Older Woman


I was sixteen years old at the time and I lived right next door to two wonderful women. The first one was an adorable thirteen-year-old that worshiped the ground that I walked on. She would do anything that I asked of her and she did. She even gave me her virginity when I asked for it.

Gretchen was looking very good the day that I asked her. She was in an orange bikini top and a pair of white short shorts that looked like they were painted on. She had on open toed shoes and her fingernails and toenails were painted bright red. She had on a light shade of pink lipstick too. I loved the way her shorts were tucked up into the crack of her ass and the way they formed a snug “V” around her pussy. That was when I told her that I would like to make love to her. I wanted sex of course but Gretchen was the girl that I loved, not just a fuck buddy, so making love was what I wanted to do to her.

I was a virgin too so it would be something that we would both remember for the rest of our lives. She took me up to her bedroom and undressed for me. I liked what I saw and when I got undressed she seemed to like what she saw too. I had fondled her breasts and her pussy on several occasions, I had reached into her panties, and I had sucked on her nipples too, but that was the first time that I had ever seen her naked.

We kissed and fell onto her bed and then we kissed some more. I played with her pussy like I had before when I gave her an orgasm with my finger, she had enjoyed it before, and she enjoyed it then. I felt that I couldn’t wait any longed and so Gretchen opened her legs for me, I got between them, and I thrust down into her. She gasped and I started to cum right away as I thrust into her. The whole thing lasted less than a minute but it was the most exciting minute of my life. I kissed her and got dressed to go home to dinner.

I was in seventh heaven all evening, I jerked off to thoughts of Gretchen that night, and I just smiled at school the next day. I never told anyone what I had done with Gretchen. I was truly in love with the girl next door.

The next day after school, I rushed over to her house hoping to do it again. Gretchen was willing but that time she wanted to be in charge. Okay!

I got undressed and lay on the bed while Gretchen stayed dressed and sucked on my cock. In a minute I was cumming in her mouth. She had a strange look on her face. She swallowed my cum and then ran into her bathroom to throw up. She brushed her teeth and came back out naked. She then straddled my hips and slipped my cock into her pussy as she squatted down on it. She moved about for a couple of minutes while I played with her tits and she played with her clit. Then I cum again. She told me to keep playing with her breasts and especially her nipples until she had an orgasm. That took a couple of minutes more but she really enjoyed it. Once again I got dressed and left.

I could not believe how great sex was and that I had pleased my woman like that. In my mind I was the best lover in the whole world…but apparently not in Gretchen’s mind.

The following day when I went over to Gretchen’s house for sex she was not there but her mother was. She then sat me down and told me the truth…I was a terrible lover and that I only took care of my own needs. She told me that she could teach me how to please her daughter or I could go back to jerking off. I didn’t want to jerk off anymore. I liked putting my cock in Gretchen and I wanted to keep doing it, so I gave in.

For the next several hours Gretchen’s mother taught me everything that I need to know to please her daughter. It was simple things at first like how to kiss better, how to use my tongue, and even how to unhook a bra gracefully. She taught me how to fondle her breasts, roll her nipples between my fingers, and how to suck on her nipples so as to give her the most pleasure. She taught me how to give her a massage from the back of her neck and down over her butt to her feet. Then she taught me how to do the same to her front. Part of my training was oral sex so I had to learn to like the taste of her pussy, to lavish up the moisture, and to swirl it around in my mouth before swallowing it. I even gave Gretchen’s mother three orgasm orally without using my fingers or my cock. Of course finger manipulation was a part of my training too on her nipples and her pussy but also on her asshole. I finger fucked her asshole until she begged my to put my cock in it. I came instantly and she made me do it again, and then again until I could last a couple of minutes. My final test was to fuck her pussy with her legs up and splayed way out to the side opening up her pussy wide. I had very little friction that way and besides it was my forth time to cum so it took a lot longer. Almost ten minutes later I cum in her and she congratulated me.

She taught me how to undress a girl, how to do it in a sexy manor, and how to pull her panties down with my teeth. I also learned that I was to please Gretchen before I got pleased.

It turned out that my mother was in on it too. She had taken Gretchen to a movie and then out to eat before bringing her home. My father and Gretchen’s father had gone away for the weekend. That way I could spend the night in Gretchen’s bed with her.

Of course we went to bed early and I showed her what her mother had taught me about undressing her, giving her an all over body massage, and then oral stimulation that ended with me giving her four orgasms with my mouth and tongue. When I did slip my cock into her I had secretly cum twice while giving her oral sex so I was fully ready to rock her world, and rock her world I did. I fucked into her missionary style, then doggy style, and finally with her ankles up around her ears as I filled her with my cum. I had looked at the clock and was very proud that twelve minutes had gone by and basically in slow motion. It was my best attempt yet and it was with the woman that I loved.

It was only about eleven o’clock at night but we were hungry again. I put on my pants and Gretchen put on a light robe. On the way past her mother’s bedroom we heard some strange noises so of course being curious Gretchen opened the door to peek in. What we saw shocked both of us. There were our mothers on top of the bed locked in a sixty-nine, each engulfed in their own orgasms and continuing to give their partner more pleasure too. We watched for a while then quietly closed the door before we were observed.

In the kitchen we fixed two peanut butter and jelly sandwiches, got glasses of milk, and were sitting at the kitchen table when our mothers walked in. Surprisingly they were both fully naked.

Gretchen’s mother looked at me and then removed her hand from my mother’s pussy before putting her fingers into my mouth. I had the honor of tasting my third pussy and possibly the best tasting one too.

Gretchen removed her clothes and the three women sat at the table and discussed sex while I was told to crawl under the table and start licking their pussies. I started with my mother first because she tasted so good. I decided that Gretchen’s mother was next on the list and finally Gretchen herself. As I licked I listened to the women talk about washing their pussies, giving themselves douches, and even inserting cherry flavored LifeSavers into their pussies to add flavor. Apparently that was what Mom had done before letting Gretchen’s mother eat her. Gretchen’s mother had douched with a vinegar solution. Gretchen on the other hand had my cum mixed in there and she had a well-fucked taste. I realized that Mom and Gretchen’s mother had only their own secretions in their pussies for me to taste. As I listened I found out that our mothers had been lovers since before Gretchen and I were even born. I also found out that Gretchen often joined them in the last few months. It was also their idea for Gretchen to have sex with me. At that moment I was giving Gretchen an orgasm and she told them all about it too.

That night I slept with Gretchen and Mom slept with her mother. On Saturday I got to fuck Mom with Gretchen’s permission. She had wanted to see what I had learned and also to see if there was anything that she could add. Mom gave me a very nice blowjob and told me that I tasted better than my Dad did or Gretchen’s Dad did. That was when I found out that our parents wife-swap from time to time just to spice up their sex lives. I thought it was cool that they did it openly and that it didn’t hurt their marriage. Then since I had fucked both of them she asked me if it would be all right if the men fucked Gretchen. I felt a pang of jealousy but then I remembered that I had fucked two other women so it was only fair to let her fuck our fathers.

Gretchen thanked me for giving her permission and then reminded me that she did not belong to me yet and that she could fuck anyone that she wanted too. She then said that she would sleep with each of our fathers once just to see what it was all about. Then she gave me permission to screw our two mothers all that they would allow, but no other women if I wished to screw her. I quickly agreed. Gretchen was all the woman that I needed but I couldn’t pass up the opportunity to screw our mothers again.

With everyone’s permission Gretchen and I slept together every night after that. We took turns sleeping in her bed and sleeping in my bed. On occasion Gretchen would sleep with her father and with my father as well as with her mother and my mother. Gretchen was very popular among the five of us.

Gretchen stayed in the Grade School for two more years before coming over into the High School with me. It was no big deal when she did though because she knew practically everybody that I knew. We had gone to all of the High School dances, basketball and football games, as well as to the plays and concerts that were being put on. Gretchen outgrew her Grade School the day that she lost her virginity and became a woman…my woman.

We both finished High School and went on to college. I graduated from a four-year school and Gretchen graduated from a two-year school before we were married.

Life just kept getting better and better. Then one day we had a daughter and became parents ourselves. All to soon Gretchen will be teaching our daughter and her boyfriend about sex.


The End
My First Older Woman
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party with an older woman

party with an older womanAbout six years ago I went to a party at a friends neighbors house. While I was there i noticed several attractive older women whom I'm guessing were in their 40's. My buddies neighbors house was pretty big and had a lot of rooms. The owner was an older male who lived there alone, after speaking with him and introducing my self he asked me to go to the basement where the extra drinks were kept. Once in the basement I noticed a bathroom, I was drinking beer and I had to...

2 years ago
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SRU The Womanizer

Yeah, it's a predictable little story from me. So sue me :-) Spells R' Us: The Womanizer by Stephanie Josh saw the slap coming, but could do nothing to avoid it. "You're scum!" said the girl he had been talking to. She turned on her heel and stormed out of the bar. Josh shrugged and turned back to his drink. It had been a long shot, but it had been worth a try. He checked his watch. It was nearly quarter past five. He had left work early so he and his wife could go...

2 years ago
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Noblewoman

Yes, my dream would have been more satisfying if it had gone along the lines of…a voluptuous red-headed noblewoman who lusted after one of her servants. She frequently sent him subtle hints of her desire, brushing up against him as she passed by, bending forward to show off her cleavage, and complimenting him on his strong build (when what she meant was his powerful legs and tight ass). She was sure that he felt the same way about her, as evidenced by his obvious erection during her latest...

3 years ago
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The twin sisters of the cross dresser policewoman

(This post is a fictional story on a bondage forum in China, and I am the prototype of the story. I just translated it into English. The copyright belongs to the original author, and the portrait right of the photos in the original link belongs to the original author and me)In the middle of a gloomy and horrible room stood a woman with a shawl. She was wearing a sexy red cheongsam, a pair of sparkling flesh-colored stockings like cicada wings wrapped around the beautiful woman's slender legs....

3 years ago
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How I lost my virginity an older woman

It was a hot July and I was working at my father’s restaurant. Since it was seasonal the staff only worked there from May until September. I started working there when I was ten years old, but now that I was older and I was promoted to a more responsible position. The restaurant had a cellar where we stored all the foodstuffs, a main floor that could accommodate 180 people, and an upstairs that could hold 80 people. I was in charge of the cellar. My father employed waitresses and chefs from...

2 years ago
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My First Older Woman

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
4 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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