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First Anal

Posted by: Age: 23 Posted on: 8 comments
15 likes 129 views Category: Sex Stories Anal Tags: Female-Male, Sex Stories Anal, anal masturbation, squirt,

I’ve been masturbating analy for a long time, since Jessica taught me the delights of it in Spain.  But since then I’ve been feeling a real urge to do more. 


Of course, I’ve read about it, and talked to trusted friends. Most said they’ve never done it, but I suspect that might be “nice girl” syndrome. One said she tried full on anal and it hurt like crazy. 

One of my friends was very quiet during the discussion and when I was alone with her a couple days later, she said yes, she’d done anal masturbation, been analy masurbated and gone the whole route too. “It’s the best orgasms I’ve ever had, but some guys just wont go there.”

Since I am in a long term relationship, I figured I’d talk about it. 

We were in bed, kissing, and I was enjoying his amazing fingers. He has very long fingers and boy, do they reach the right spot(s). I didn’t figure I could just say “Hey. Stick a finger up my ass.” But I could give him little hints, like when he grazed his finger across my butt hole I pressed back on it and moaned loudly. 

He got the message, and thanks to my crazy vaginal wetness, there was plenty of lubrication there already. He pressed in a little, then some more and soon his whole finger was deep in me. I felt on fire! He went down on me too but didn’t take his finger out of my butt. The orgasm was totally different. It kinda crackled, if that makes any sense.

When he got on top of me, I guided him not to my vagina, but to my butt. He pressed, I pushed, and although I felt stretched to the max, there wasn’t any pain at all. 

When he started moving though.....ho-ly FUCK! Sensations like I’ve never felt before. It felt like he was in my womb! 

I came....twice....and then he told me he was close. I just told him go for it.

When I saw Jessica next, I told her about losing my anal cherry. She chuckled that dirty laugh of hers and told me welcome to the club. 

Again, that tension. Again that feeling that we both knew we were going to do it, but each was waiting for the other to make the first move. 

Jessica cracked First. She walked to me, shedding her dress and panties in the process. By the time she got to my chair, I already had my legs wide open and her finger was running up and down my wet lips before....mmmmmm.....she slipped it in my butt. 

Now, explain this! How can a girl’s finger in there feel so much different to a guys? It did though. Maybe it’s because it’s smaller, thinner? I dunno. Anyway, I got a real good ass fingering while she licked my clit. It was heavenly, and when I got to finger her, I got the taste of her squirt full force in my mouth. 

I know anal isn’t for everyone, but if it works, hey, why not?



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