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Taking her anal virginity.

Vic's first time trying anal sex.
This is based off of a real life experience.

Casey is my girlfriends friend. She has had this fuck buddy for a while now.

Anyway, Vic texts me, "hey, gonna be late gotta go to cvs casey needs something that rhymes with smplan beee"
So about 15 minutes later, they catch up with me by the Dorm rooms.
"So casey, what happened?" I asked.

"He came in my ass and it leaked onto my pussy, I didnt want to get pregnant!" she told me.

"Wait. in your ass?" said Vic

"Yea, you guys should try it"

Now, I have put a finger or too back there, but I didn't want to hurt her.

I called Vic back at night after I drove home to say goodnight.

"Ugh, Casey keeps telling me to try it back there.

I have done anal with an ex, but I was not sure that Vic wanted to try. So jokingly I told her, "Yeah you should, some girls like it back there."

"Yea, but you're bigger than average"

Ok, I dont consider myself huge, but I am about 7 and a 1/2 inches and 4 inches around. And I have never heard any complaints. My best friend once asked for a picture to text some douchebag with a caption reading Grow one this big and maybe we'll talk.

"Yea, its ok, I don't really care, if you wanted to try I would, but I won't go anywhere if you don't babe"
______________________________________________________

Hey chris, after class want to go back to my room for a little? read the text message from Vic.Of course I was down.

We laid down, planning to nap before our next class when her roommate came back in.
She then told us she was off to the library to study. And she left. I took that as a cue to play around with my girlfriend because who doesn't love a few hours alone.

We started making out on her bed. Nothing out of the ordinary. I lifted her shirt, took it off to expose her sexy bra (which did not stay on for any longer than her shirt). And there they were, her sexy B-cup breasts. I started by kissing her left breast then switching to her right, while caressing the opposite.

She then reached down to undo my belt and button/zipper. And she had my pants at my ankles. Then I started to make my way down to her pussy. She was already soaking wet. I started slide one finger in and out of her dripping pussy while feeling her up and kissing her.
I then got a second and third finger in. Once they were wet, I started to circle her tight anus with my pinky. Then I slid it in. I continued fingering her with 3 in her pussy and one in her ass when she had her first orgasm. She was shaking, as well as sinking her fingers into my back. She then stopped me.

"Chris, do you want to fuck my ass?"

"Babe, I love you, you don't have to fall to the peer pressure haha."

"But what if it does feel good?"

"I mean it could hurt and I do not want to hurt you"

"I'll tell you to stop if it does alright?"

"You sure? Let me know if it hurts"

I then got a second finger in her ass and started to stretch it out. I could tell by her facial expression she wanted me to stop. So I did, I asked her if it hurt. She told me to keep going, it was only uncomfortable. So I spit on her ass and let my fingers get covered in the lube. I slowly continued sliding my fingers in and out of her tight ass and pussy simultaneously.
She then came again. I then got a third finger in her ass hole. She was rubbing my dick so hard and the idea of fucking her ass was pushing me close to the edge. I told her, and she laid off. I continued to finger her ass in the mean time, stretching her tight hole for my cocks anxious entry. I had three in her ass when I decided that we should try. I told her that I should put on a condom for extra lube. She does it for me, so that I can maintain the stretching of her ass hole.

She got the condom open and on. Then playfully jerked me twice "Is it on?" with a very sly smile.

"yes love, push me off if it hurts. I don't want to hurt you."
She nods and looks at me in waiting.
 
We shift so that she is on her side in a spooning position. I get on top of her and push the tip of my cock against her ass hole. I slip the head in slowly. I could tell she is not completely comfortable. She tells me to keep going. I Slide about 4 inches in and let her adjust to the feeling.

The tight feeling is amazing. She started to feel the pleasure as well. I started to finger her pussy while I was sliding in and out of her ass. She has an orgasm and squeezes my hand and dick out of her.

I continue fucking her and I feel myself getting close to cumming.
She must have been able to tell because she grabbed my ass and pulled me in to her ass all the way I came. She then pulled me out of her ass and ripped off the condom.

She then started to suck, slurp and lick off all of the cum on my dick. She brought my dick back to life and then sucked my dick until I came in her mouth. She collected it all in her mouth and then took the most erotic big gulp ever.

let me know what you think, if or where I need to improve thanks!

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Comments(6)

Gym
Posted 04 Oct 2013 16:11
An interesting story, the basics are all there but it needs some thought and fleshing out.
satisfying
Posted 12 Sep 2013 11:20
a nice story but u have kept the heat of it to yourself by not giving more details. good one mate!
Boombabong
Posted 02 Dec 2011 16:28
more development needed..
ibee
Posted 20 Oct 2011 11:34
ditto..no need to rush,a nice job.

TheDevilsWeakness
Posted 20 Oct 2011 06:30
Good story... take more time explaining things for your next one... hope to see more

Buz
Posted 20 Oct 2011 05:34
Good story dude!
 

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