This is a standalone story, although there is some background about us here in [our introduction](https://www.reddit.com/r/gonewildstories/comments/4d088e/an_introduction_and_our_first_time_mf/)
This story takes place a few months after the events in our last story.
As the summer came to a close, Jenn and I got ready to head back to school. We’d been talking online about fantasies, seeing what turned us on and what we wanted to try. I knew that she was very open to new things, but was a little bit shy and inexperienced. I would from time to time throw out an idea just to see how she would react to it, and she generally seemed willing to give them a shot.
I’d learned that she was submissive, and enjoyed being told what to do. One night we were talking and I was telling her what I wanted to do to her once we got back to school.
“I’m going to bring you into my room, rip your shirt open and suck on your tits. After I hear you moan and can see you squirming and trying to get to your clit, I’m going to grab your hair, force you to your knees and shove my cock into your mouth. You’d like being force to suck me off, wouldn’t you?”
“Mmm, you know I would,” she replied.
“Once I’m good and hard, I’m going to bend you over the bed, pull your skirt up and fuck your little pussy hard. Slap your ass, pull your hair, reach around and pinch your nipples and rub your clit. I know you’ll be so wet. I might not be able to resist reaching down and sliding my thumb into your tight little ass. Have you ever had anything in your ass before?”
“No.”
“You will,” I reply. “My fingers, then my cock. Are you playing with your pussy now?”
“Yes. I’m so wet. I’m rubbing my clit and fingering my pussy.”
“Put your finger in your ass. Just one at first. How does that feel?”
“Different. Good.”
“You like it?” I’m getting lots of ideas now.
“Yes. I’m going to put another finger in.”
“Do it. Keep rubbing your clit while you finger your pussy and ass. I want you to make yourself cum while you have your fingers in your ass. A dirty little slut who enjoys playing with her own ass. Stretching both of her holes to be ready for me to fuck.”
As this point she came, and said that it was so intense. Not the hardest she’d even cum, but it felt so good and so dirty. This pushed me over the edge as well, and I came too.
I decided to push her a little more and gave her an errand. Over the next couple of days she should go to a sex toy shop and buy a butt plug so that she’d be ready for me in a couple of weeks when school started again.
A few days later she did, and told me about the trip. She talked to the cashier at the store about what she was looking for and he showed her the toys and explained about keeping them clean and the best lube to use with them. She picked out a set of three plugs in three different sizes, along with a large vibrating dildo.
As we began talking dirty, I had her start with the smallest one. She lubed it up, and slid it into her ass. I asked her what it felt like, and if she enjoyed it.
“Yes, it feels good. I’ve never had anything this big in my ass before. It feels so dirty laying naked on my bed, with my legs spread wide and sliding sex toys in my own ass.”
We talked a little more, having her imagine it was my cock, and rubbing her clit. I had her switch to be second size, let her enjoy that feeling for a little while, then had her put the biggest one in.
“It hurt a little bit at first,” she says, “but now as I get used to it, it feels good. I feel so full.”
“You’re about to feel even fuller. Take the dildo and slide it into your pussy while you have that toy in your ass. Really feel them stretch you out.”
It took a few moments and a little more lube, but she eventually got the toy into her pussy.
“God. Feeling the toys in my ass and pussy is so intense. I can feel them rubbing against each other through my pussy wall. I feel so full and its just so amazing.”
“Good. Now fuck yourself with the dildo until you cum. Play with your clit if you want to. But you need to cum with the butt plug stretching your ass out, and the big dildo stuffing your pussy full. Now close your eyes and pretend that its two cocks fucking you. You’re taking my cock in your ass and a stranger’s cock in your pussy.”
We’d never talking about her fucking another guy before, and definitely not about a double penetration, but I was pushing her limits and fantasizing, so I wanted to see what she would say.
I didn’t hear anything back for a couple of minutes, and I was getting worried that I’d scared her off. Then:
“Oh God, that was amazing. I was so full, and it was so hot having you make me play with my ass and fuck my pussy. And then when you talked about two guys fucking me, I lost it. I came so hard.”
“You came hard thinking about two guys double penetrating you? You want to be with two guys at once? Really acting like a little slut?”
“I’ve seen it in porn, and I knew people did it. But I never thought about it being me until you told me to. It was just so dirty that I came as soon as I read it, and as I came I imagined it happening to me.”
This was a very interesting development that I knew I would have to explore further. I was looking forward to getting back with her in person, to fuck her tight little ass, and see where else these – and other – fantasies, would take us.
Source: reddit.com/r/gonewildstories/comments/4d6ktn/getting_her_into_anal_mf