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You're never too late - Age 43, Canada
My wife and I were one month shy of our 20th anniversary. I had thought about it for years. Anal stimulation was always part of our foreplay. One "the night" I grabbed some lubricant off the night table and began working it into her. Then I asked her to get on hands and knees. I got behind her and rubbed my cock up and down her backside. Finally, I just pushed in the head and stopped, waiting for her to relax. I wasn't sure how she would react, but after laying very still for several minutes she began to rock back onto me. It was wonderful, now part of our regular lovemaking. better late than never.

 

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The first time I fucked a girl in the ass was in high school. It was a nice early afternoon session of love in the sunshine and nobody to bug us. She didn't take all that much coaxing. I just rubbed the redeye while the other stuff was going on, licking the finger and slid it in. Gently at first rubbing in a circular motion around the rim to get the hole nice and big and willing; that drives 'em wild until they're begging for it. Then slide it up in slowly if it's her first time. Then getting deeper and faster you know the drill. 

She lived with her family in a condo, and she was on all fours in the living room  facing towards the front door about 3 in the afternoon. I'm straddled behind like a true cowboy and she's howling in either pleasure or pain. My cock sliding in and out of her fresh juicy ass and... bam, in walks someone!!! Door was supposed to be locked but in our frenzy to get down and dirty someone must have forgot. It was only her brother so I was lucky. If it was her father walking in on some horndog banging his only daughter's virgin ass then I woulda been sailing over the balcony with a smile on my face and my final load shooting out my cock. So here's my tip: lock the front door

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After the video finished, my girlfriend and I sat on the couch making out. I rubbed her breasts through her shirt, pinching and flicking her nipples. She lifted up my shirt and sucked on my nipples, her tongue dancing quickly across them. Then she stopped and said "Take your shirt off and lie down on the couch. Close you eyes. I've got a surprise for you." I did so and she went into the other room to collect some stuff. When she came back with massage oil, she gave me a wonderful backrub, both sensual and therapeutic.

I then returned the favor, rubbing oil on her shoulder and neck. I told her to lie down, and I put oil on my hands and massaged her breasts and belly. She was very excited by this, so I began stroking her now-moist mound. She was going crazy with desire and I was greatly enjoying watching her twist and moan. We were both incredibly turned on. Her moans suddenly stopped, as an orgasm swept over her. She turned over on her hands and knees, saying "Take me in the back. Fuck my ass." This kind of surprised me, since we had only fingered each other before this. I grabbed the bottle of massage oil and poured some on my hands. I rubbed the oil all around her tight rosebud, and then slowly inserted a finger in to help open it up. I then put oil on my hard cock and got into position behind her.

Ever so slowly, I gently pushed my cockhead into her tight ass, as I didn't want to hurt her. She screamed, "Yes! Give me your dick! Fuck my ass!" I slowly pushed my cock into her, spreading her cheeks wide with my hands. She pushed her ass back against me, and I began stroking in and out of her. She was going wild, moaning and pushing into me. I grabbed her shoulders to help thrust deep within her. Her asshole was so tight and gripping that after only ten or fifteen strokes I came hard inside her, while I kept thrusting. I must have cum for 40 seconds at least. It was one of the most intense orgasms I've ever had. And it was the first time for both of us.

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One time, my boyfriend and I were having sex and he told me that he wanted to put his dick in my ass but I told him that I had never done it and I didn't want to try it at the moment. He said he understood where I was coming from and he didn't pressure me.

The next day, when I was home alone I started thinking about how painful anal sex could be. so i decided that if I wanted to please him, i would have to try. So I ran to the bedroom and took out the K-Y Jelly and lubed up my middle finger. I gently  massaged my asshole, once it was relaxed I slowly inserted my finger into my ass. It felt a little uncomfortable but i did like it. After a few minutes of doing it a decided to try two fingers. After a while 2 fingers wasn't enough. I had to try something bigger. I don't have any dildos so i went to the kitchen and got a banana. I put a condom on it and started fucking my ass with it.

When my boyfriend came home, I was eagerly waiting for him. We started fooling around. I gave him a blow job, and after that I lubed up his cock and  laid him flat on the bed. Then I took his hard dick and guided it towards my asshole. When he felt the tip of his dick around my asshole, he said "what are you doing". I did not reply   continue to stick his dick into my ass. I rode his dick for about 20 minutes until I made him cum inside my ass. I loved he feeling of warm cum in my ass. since then I have become an anal freak



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