How Jen Lost Her Anal Virginity free porn video

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And I hate to even say this, but it’s a true story. It happened a long time ago. She was in college and the man was quite a bit older. Anyway, she lost her ass to a man years before her pussy, but that’s another story. This story happened when she was 21 and if you can believe it, she waited until 27 before she gave up the pussy, again another story.
We grew up outside of Tampa Florida in a soggy little town. She was 21 and had 2 weeks until she went back to college to finish up her degree. She wanted to hook up with all the friends she was leaving before she left town. She and her friend Nat (who was a hottie in her own right) decided to see a movie on a Tuesday afternoon. They wanted to see the Shining just one more time before the summer was over. It had been a hot morning and the humidity was in the high 90’s. They didn’t wear anything special, shorts, conservative top and sandals in case you were wondering. On a Tuesday afternoon even for a new movie there were only about 10 people in the theater. Jen and Nat got their seats same as they always do, in one of the last rows. As the lights went out and the previews started they noticed a man walking straight for them, staring at them the entire time. Soon as they got a good look they noticed it was Dicky, they turned at each other and giggled as Dicky sat down two seats from my wife (Jen).
You need to know about Dicky. We guess he was about 37 the time this happened, he wasn’t a bad looking guy, average height, build, pot belly, he was always kinda dirty and always looked like he needed a shave. But good ole Dicky was our town’s biggest pervert. If Dicky liked you, he’d follow you, and smile at you and try to walk ahead of you so he could lure you somewhere. He never had a car so he’d just walk and follow and smile . . . ok the guy was a stalker. Ole Dicky liked young men and young women, he didn’t seem to have a preference at all. His main fetish was with feet and as the story goes, if he lured you somewhere, like an abandon car in a dark alley, he would suck your cock a little bit, then he would put one of your feet in his mouth while he rubbed your other foot on his cock until he came, after which he would jack you off or maybe suck you longer if he really liked you. With the girls he mainly sucked their feet and fingered their asshole, he’d keep his finger going between her ass and his mouth getting their asshole really moist with his spit. He never once played with a chic’s tits or pussy or tried to get a blow job. Anyway that’s the rumors, it’s just what I heard . . . ok I hooked up with him too, lots of times, but Jen didn’t know it at the time, in fact I told her after she told me what she did with him. And yes this is me, Jen’s husband.
Anyway, as the movie gets going and Jen notices Dicky just watching and smiling with his eyes going from her feet to her eyes. At first she felt totally creeped out but after a while my wife said she enjoyed it. There was something about his smile. Even though this guy had a reputation of being a douche bag/pervert/rumored m*****er she said she liked the attention. She said she never had a guy look at her like that before. Of course she got all hot & bothered, she said her pussy got wet & her nipples got hard. She didn’t want to have sex with him at ALL but she got VERY hot from all the attention. An hour goes by and at this time Jen is smiling back at Dicky big time!!! It’s to the point neither of them are watching the movie, just flirting with each other. Several times she looked over at Nat and she isn’t noticing a thing she’s so engrossed in the movie. Dicky & my wife make goo goo eyes at each other, the movie goes on, Jack Nicholson freezes and nothing more happens.
As movie is ending Jen turns to talk to Nat but Nat starts off about how she never noticed something in the movie before and my wife is trying to tell her about Dicky. Jen finally gets a word in and tells Nat how Dicky had been watching my wife for the entire movie. Nat is like, big deal Dicky does that to everybody. Nat brushes it off and wants to go to the snack bar and get something to drink (and flirt with the boys) before she goes to work. They turn around and Dicky is nowhere to be seen. The girls go to the snack bar and get iced tea and of course, flirt with the boys. My wife couldn’t believe Nat didn’t notice Dicky staring at her the whole time! Dicky stares at everyone Nat says! Jen is starting to think, ok she’s right, Dicky stares at everyone. They say their goodbyes as Nat runs off to work at the mall and Jen runs to pee before she heads home. By the time Jen leaves the theater Nat is long gone, Jen goes outside and starts to walk home, her eyes are still not quite used to the bright sunlight. Jen thought it was good to see the sun, she was getting tired of all the rain. It was hot out and sooo humid. Jen turns the corner to go home and there is Dicky with that big smile of his. The first thing Jen thinks is, Dicky knows where I live and I do not want to have sex with him! Then she remembered how hot Dicky made her feel and she smiled back but tried to push the feeling aside.
Remember I said Dicky liked to lure people to secluded places? As my wife got close to Dicky he starts to walk along side of her. Dicky turned to my wife and said, “come on, follow me”. Jen said it wasn’t a request and not an order or anything like that, she just says he had a friendly tone like, come here I have something I want to show you. Then Dicky really speeds up his pace, as fast has he’s walking he keeps turning around making sure Jen was still following him. Of course she’s still following him it’s on her way home. My wife “follows” Dicky for a little ways longer then Dicky abruptly turned into an alley. Now keep in mind Jen is still walking in the same direction, she was on her way home. So obviously Jen is thinking, do I turn in the alley or do I go home? She wondered what he wanted . . . probably sex but maybe not, she knew a neighbor down the alley had a pet pig, maybe he wanted to show her the pig.
My wife got to the alley and stopped, turned and looked at Dicky. Now he is really smiling. He didn’t say a word, just made a motion, an urgent motion for Jen to follow him. Ever so slowly Jen took a step, God she couldn’t believe she actually stepped into the alley towards him!!! Dicky was thrilled and ran a short ways down the alley and stopped by some bushes. Dicky motioned Jen towards him, she thought it would be ok to at least see what he wanted so she slowly went over to him. Now Dicky had turned away from Jen and was staring at the house they were behind. Jen had a sinking feeling when she realized it was Dicky’s house! She looked towards the house and sure enough it was his! Jen said, “I gotta go” and just as soon as she said this Dicky grabbed her wrist. She looked at him startled, Dicky still had a big smile, but he let go of her wrist and slipped through a door. Jen realized they had been standing behind a small building or shed that was behind Dicky’s house. My wife saw him walk inside over to a pile of magazines in front of a small window and started to watch his house again. Jen stood in the doorway for a second as Dicky silently stared at his house. Jen walked through the doorway and took a look around, the shed or whatever was barely sunlit, and hot, and filthy, and humid. It looked like it had been used as a workshop at some point. As she looked around she noticed some hot rod pictures and a few girly posters on the walls. Then she noticed the magazines Dicky was standing in front of, it looked like they were piled on boxes or something. There were a few cars mags but from what Jen could tell it was mostly porn magazines. Now At this point Jen knows exactly what Dicky wants. He turned towards her and quietly said, “come here”. Jen says she will never forget the feeling in her stomach, for some reason it felt all nice and warm, it was just wonderful. She instantly broke into a cold sweat and trembled as she felt herself step towards him. He abruptly motioned for her to close the door and grabbed her wrist, like before but firmer. Jen shut the door with her outstretched hand and walked towards him. She made sure she could see his house through the dirty little window. Dicky pulled her towards him and put his arms around her waist pulling her into his pelvis. Jen instantly felt his hard cock pressing against her. He still had that big smile but now it was a little different, wanting and more perverted than it was before. His hands were all over her firm ass, she said she thought she was going to faint as he groped, rubbed, and caressed her butt. She said he was gentle yet firm but sort of commanding at the same time. Dicky massaging her ass took her breath away. She got so lost in it she almost forgot to look towards the house to check if anyone was out there. As she stood facing Dicky, she thought it odd that his face was arched away from her face. She seemed relieved that he didn’t want to kiss, she looked at him and his eyes were closed and he looked like he was in ecstasy. Jen realized she was enjoying what was happening but at the same time not wanting to have sex with him.
Dicky grabbed Jen abruptly by the hips and pushed her back. He unbuttoned her shorts and slid them down to her ankles. Jen gasped and pushed back with her hands on his shoulders and said, “you can’t fuck me”. Jen said that that big smile of Dicky’s was now a little evil. This was the first time she noticed his smell too, she said it wasn’t pleasant at first but it made her hot, she could smell his sweat and his breath and his pants were down (which she didn’t even notice) and said she could even smell his crotch. He quickly moved behind her and made her bend over at the waist onto the magazines. He rubbed his hard cock against her ass for a few seconds then dropped to his knees and starting rimming her. This was Jen’s first rimming and she loved it, the feeling of his warm wet tongue in a place where a tongue had never been made her almost lose control. Jen felt herself relaxing into the magazines and took a good look at them. There were gangbang magazines, oral magazines, foot fetish magazines, anal sex magazines. Then Jen saw spots that looked like spit all over the place and realized that his was were Dicky jacked off. She just closed her eyes and got into the feeling of him rimming her asshole. Then she felt him back off, then she felt a finger where his tongue had been. He rubbed and gently prodded her asshole, then the finger went away and came back wetter, the finger went away and came back wetter, on and on to what seemed to be forever. Jen loved it . . . she heard a smacking noise, was he jacking off? After a few minutes of playing with her asshole Dicky backed off, Jen wondered what he was going to do and at the same time missed him playing with her wet asshole. Suddenly Jen felt something bigger, warmer, wetter and smoother touching her asshole. The same moment my wife gasped, Dicky pushed his cock into her butt. He went back and forth in her ass like crazy for about a minute then stiffened up and relaxed. Dicky pulled out of her ass as quickly as he went entered it then moved to a corner of the shed. Jen was panting as she felt Dicky’s hot cum dripping out of her butt. At first she was horrified at what she had let him do and at the same time she was sooooo glad he that he didn’t fuck her. Jen pulled up her pants as Dicky stood silent, she said they just smiled and didn’t say a word to each other. Jen silently left and started to walked home. She got just around the corner and decided to stop by a bush so she could spy on Dicky’s shed. She heard a door shutting then a moment later she saw Dicky’s Dad walking back towards the shed. Dicky came out of the shed quickly, straightening his pants as he walked. They stopped and talked to each other, she heard them talk quietly then heard a little laugh. Soon as she heard the laugh she headed for home. On the way home she realized she let a man with a perverted reputation lure (hardly not saying a word) to a place where he got her pants off and filled her ass with cum. She loved it.
Jen got home, got out of her clothes and took a shower. She still couldn’t believe she let Dicky have her butt! And she was still grateful that she didn’t let him fuck her. Over the years she hooked up with ole Dicky a few more times and they are all nothing less than smoking hot stories. I hooked up with him a few more times too. It wasn’t until years later (we moved out of Florida) and discovered we both like our “Dicky”!
I’ve had my wife tell me that story soooo many times, I love all the detail she throws in. We like to talk about getting her ass filled in Dickys jack off place, he must have loved it! We also talk about his Dad, what if he would have joined in! The fantasies are endless! If you want to know what she looks like, yes that is her in the pics on my profile (zxmph99) here on hamster. Just so you know, neither of us like the thought of someone forcing himself on another person. Perverts like Dicky can be dangerous! So any perverts out there DO NOT force yourself on another person! True, my wife was not forced and that is what makes this true story so hot! To this day, Jen says her idea of what a man is supposed to smell like is exactly what Dicky smelled like that day! And the smell of damp magazines get her HOT!

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This story takes place straight after "My Boy Nigel" The next day was warm, so I put on a dress and a pair of strappy Roman sandals, and took a stroll down into town. An hour of window-shopping left me hot and thirsty, so I walked down to the seafront and found myself an ice cream. I sat on a bench and looked out across the beach and the sea. A few minutes later, as I was catching a dribble of melted ice cream with my tongue, a woman sat down on the bench: “There’s no one sitting here is...

Exhibitionism
3 years ago
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Me Jen Lennie and her sis

While the babies were cooking, I took a shower, I already knew how to do my own makeup, shaved my legs, painted my nails, I'm ready. I still put the wheels in my ass to be more prepared for the evening and I went downstairs to see the babies. When I walked into the kitchen, Jen was already bent over the kitchen counter and Lennie was pulling her hair and thumbing her with his other hand. I had him hard in no time and started playing with him and watching the two. Jen just shook and started to...

1 year ago
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Jen Me Descent into Narcissism

It's true. Jen has converted me into a total gym rat.It's been four months since my original conquest of my hot little sister-in-law. Through various bets and incentives, we've made love five more times. She is really playful in bed, and we have a great time. After ten years, I'm finally getting to know her. It's only since she lost the bike race that we've really talked a lot.On the other hand, we're spending less and less gym time together. I'm really working at building up some mass. I've...

1 year ago
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Vince Invites his Hot Cousin Jen over

Vince was extremely nervous today. He invited his hot cousin Jen over to stay a few weeks at his place while she would be looking for a job and a place of her own. His apartment was big and clean considering that his parents had bought it for him but that wasn't his problem, ever since Vince can remember he's had a huge crush on his cousin Jen. He knew it was so wrong, considering that she was nineteen and he was twenty-three, not to mention that they were cousins, but still he couldn't help...

Incest
1 year ago
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Jenrsquos Painful Lessons

Susan called me and asked me to stop by her house after work. Susan was a real pain. She was the widow of my dead ex-partner and, as far as I was concerned, a real nut burger, to put it mildly. Jim, my old partner had been a good friend. I owed him (and his family) I guess.While Susan was ditzy, she was also very beautiful and so was her young daughter, Jennifer. Jennifer, “Jen” to her friends, had been a marriage surprise. Susan thought she was putting on a few pounds when her doctor...

1 year ago
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It was serendipity that I lost my anal virginity

Each person remembers their first time for the major events in their lives such as going to school, a date, kiss, and sexual intercourse. For the more adventurous, anal sex can be enjoyable for both the person receiving (bottom), and giving (top). On study has reported that 40% of married couples had experimented with anal sex. The report continued by saying few men has experienced the pain and pleasure of receiving anal intercourse. At the age of forty-three, I had my first bisexual meeting....

Bisexual
4 years ago
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Jenrsquos Birthday Surprise

Jen and Jim were happily married. They had a unique relationship in that they truly did enjoy each other. They were more than just lovers and husband and wife. They were friends. They liked so many things together and that included an extremely active and imaginative sex life. They had discovered early in their relationship the importance of keeping sex fresh and new. This included exploring sexually fantasies to see where they would take them. Over the years they had lived many of those...

4 years ago
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Jen and Lisa

The anxiety is about to kill me. It is 12:30 am and no Jen yet. The evening has been pretty low key. Dressed to kill, Jen swept out the door about 7. But fair is fair, I have forced her to wait so many times. How many times have I teased her, making her wait for her pleasure, knowing the anxiety only adds to the magnitude of her release? Jen is off and to where I do not know. This is part of the game. Maybe to our swinger's club as the highly desirable single woman, maybe to a bar full of...

1 year ago
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Christine and Jen The sharing expands

As for my daughter Jen, she has been my fuck toy since turning 20. Her dirty blonde hair, flat tummy, waxed pussy and pear shaped ass have given me tons of enjoyment. I have recently started fucking her ass in addition to her pussy and mouth. At home, Christine Jen and I spend many nights in bed together. Whether the ladies are tribbing or licking one another’s pussy or asshole, or whether I’m joining them, our sex life is amazing. However we end up, I always deposit my load in one of...

2 years ago
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A few days with Aunt Jen

I was staying with Aunt Jen for three days while my parents went to Scotland for the funeral of Uncle Jack. “Aunt Jen” as I had always known her was not actually my aunt but Mum’s friend Jennifer, but she had always been known as Aunt Jen for as long as I could remember. Aunt Jen was in her mid forties and worked as a nurse, quite ordinarily but nice, although I think she had struggled financially since her husband died she was always very smartly dressed and always seemed to be wearing...

2 years ago
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a weekend with Jen Part 3

Jen and I soon arrived back by my house after chatting the whole way home about the weekend we just spent together.I greeted my husband and daughter with kisses and hugs. Jen said hello to them as well and we invited her in for a drink. It was really hot and we all soon decided while sipping on our drinks to have a swim. My hubby was already in swimming shorts and didn't take him long till he was in the pool. Jen got her bag out the car and her and I went upstairs to change into our bikinis....

2 years ago
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Jen Me the Wife Gets Involved

That first weekend had been fantastic, and the sex was raw and uninhibited, but where did it go from there? We had said all along we were just doing this as friends, but there's something about screwing your sister-in-law five times in a period of less than 24 hours that changes the relationship a bit.After the scene with Marisa it was clear that we were crossing some kind of boundary, and were more than just friends. I must say however that Dr. Barton is a genius, and once the swelling and...

3 years ago
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Wheels of Fortune Jen at Jamba

Copyright© 2004 She was tall - nearly six feet. Her flat stomach, hunch-shouldered posture, and muscular limbs fairly shouted 'athlete', so I was a little surprised to see the embarrassed flush on her face. "Hi!" she chirped as I approached the register. "No I'm not!" I replied, feigning indignation. "Uh, no, I mean, 'Hello!'" she tried again. "'Hello' yourself, and see how you like it!" I seem to remember Huck Finn replying to someone (possibly Tom Sawyer) that way in...

1 year ago
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JENNYS VIRGINITY

JENNYS VIRGINITY Jenny is my sisters daughter. She is now 17 years old and is turning into a very lovely young lady. Being 18 years younger than Sis, I have been her favourite little brother and have grown up along her own kid as a brother. I am now twenty years old and have been fairly close to Jenny all my life, having spent almost more time at Siss place than at my own parents place. However, it still came to me as a big surprise: A few months ago, on the night before Jennys seventeenth...

2 years ago
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Fucking Jens Asshole

Megan and I had gone to Chicago to visit her friend Amanda. We stopped on our way back from a family reunion in Cape Cod, when I’d sort of freaked out and given up on our relationship. We’d fought a lot during that week, but were still together and going through with our plans to visit her friend. One of the nights we went out to a bar with Amanda and her roommate Jen. Both of these women were really cool, but Megan had always been put off by Jen because every time we visited, Jen would...

3 years ago
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Jen and the Gloryhole

Introduction: Jen and her husband checkout the pot store in their new town. Jen and the Gloryhole My wife and I are the types of people willing to try new things. We are each others first time, and since then, we have been willing to experiment with new things. I spent the first year of marriage in Iraq, where on a whim, she would buy porn DVDs and mags and send them to me. What really threw me off was that the movies were almost always opened. When I asked her about it, she said she had to...

2 years ago
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Jen MChapter 3 Lover

When he lay down beside her and kissed her, she hugged him. After that, he kissed her all over, her face, her throat. All of her was adorable, but most adorable were her breasts. When he got to one, he kissed it while holding the other. Then he kissed over her belly. He’d like to kiss lower, but that would require some doing. So, he started to complete her undressing. First her shoes and socks. Which revealed some quite kissable toes covered only by pantyhose. He took only a short detour to...

2 years ago
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Jen and the Gloryhole

Jen and the GloryholeMy wife and I are the types of people willing to try new things. We are each other’s first time, and since then, we have been willing to experiment with new things. I spent the first year of marriage in Iraq, where on a whim, she would buy porn DVDs and mags and send them to me. What really threw me off was that the movies were almost always opened. When I asked her about it, she said she had to make sure there wasn’t anything too freaky, and then tell me which scene I...

1 year ago
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fun with Jen part two

There they were stark naked..except Jen's mother, who still had on her white cum soaked panties...They started making out. I could barely take it. Jens mother was beautiful. she had huge plump breast, and a nearly perfect body.."So you fuck my daughter, and you think you can get away with it?!" she glared at my hard cock, that I was hiding under the blanket...she grabbed Jen by the hair.."come her you fucking slut" Jen readily complied based on her new knowledge about her mother. She...

1 year ago
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My wife Jen in the glory hole part 1

My wife and I are the types of people willing to try new things. We are each other's first time, and since then, we have been willing to experiment with new things. I spent the first year of marriage in Iraq, where on a whim, she would buy porn DVDs and mags and send them to me. What really threw me off was that the movies were almost always opened. When I asked her about it, she said she had to make sure there wasn't anything too freaky, and then tell me which scene I should watch first.Fast...

3 years ago
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Maxine Stones New LifeChapter 184 in the Box With Jen

"Helen, I'm being held at the police station and the coffee is horrid here. I know this is a terrible imposition, but do you happen to have a few cups laying around that you could get someone to bring here. Before you ask, I don't need a hacksaw blade in it." I said into the cell phone. "Of course I have coffee, how many people do I bring it for." She asked. "Just me. Oh yeah and Jen is on the way. Let the rest of these guys drink the crap they have. Well bring one more cup for the...

2 years ago
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Donnie had four good friends So did Jen

I have four good friends, we're all in our early 30's and have been tight since we were the starting five on our small-town high school basketball team. I'm a police officer, and they all work at other jobs in this town and the one next door. We’re all married, and we socialize a lot. There’s always been a lot of flirting and suggestions back and forth about being available for sex. I would have to say that my wife Jen is a lot hotter than any of their wives.My wife has shown some interest in...

4 years ago
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Jens Desire The Conclusion

School finally ended signaling the official start of Summer. Jen madeher parents happy by bringing home a final report card with straight A'son it. Now she could enjoy her Summer break without hearing themconstantly harp about her grades for the next three months.Jen's normal Summer vacation revolved around her working part time atthe ice cream stand and hanging out with her friends at the communitypool, but that was before Flint stole into her room and she gave him hercherry. Now those plans...

1 year ago
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A Few Days With Aunt Jen

I was staying with Aunt Jen for three days while my parents went to Scotland for the funeral of Uncle Jack. "Aunt Jen" as I had always known her was not actually my aunt but Mum's friend Jennifer, but she had always been known as Aunt Jen for as long as I could remember. Aunt Jen was in her mid forties and worked as a nurse, quite ordinarily but nice, although I think she had struggled financially since her husband died she was always very smartly dressed and always seemed to be wearing...

1 year ago
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  • 8
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Jen Wife in the glory hole part two

That first night Jen worked the glory hole, she swallowed five loads of cum. She loved it so much that she is on the rotation a couple nights a week. I looked forward to her coming home and telling me about how many dicks she sucked, if she fucked any of them, and where she took each load. Even if she had fucked three or four guys, I would be so horny that I would bend her over the end of the bed and give her one last fuck and blow my load deep in her used cunt. There was even a couple times at...

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