From Ignorance to Bliss

I was sitting in the Student Union with Melissa and her roommate. The Sir Mix A Lot song "I like big butts" came on and Melissa commented that she didn't understand the attraction. I thought this was funny because Melissa had a really nice ass which I had admired many times in her tight jeans.
"Asses are just so nasty and dirty"
"I don't know, I find a nicely shaped butt very attractive."
"Really, I can't see it" Melissa said
"Well, maybe Sir Mix A Lot is into anal sex." said Melissa's roommate.
I chuckled and the roommate giggled and Melissa said "What's anal sex?" Of course we laughed a little more but Melissa looked confused and pissed that we were laughing at her.
"Seriously?" I said.
"Yes, seriously, what are you talking about?"
"Well, its when you get fucked in the ass." said her roommate.
"Oh My God that is so gross." said Melissa
"Well it is not horrible, just different." I said.
"Have you ever done it?" she asked to both of us.
"Mel, you seriously can not ask me that!" said her roommate.
Melissa looked at me and I kind of chuckled and said "Well, I have dabbled."
At this point we were joined by a couple of more people and the conversation shifted to other topics and I forgot all about the conversation.

About two weeks later we were walking out of class and it was just Melissa and me. She said "John, you remember that conversation we had about anal sex?"
I thought a bit and replied, "Oh yeah, sure."
"Well, I have decided that I would like to try it."
"I am sure your boyfriend will be very happy."
She punched me in the arm and said "I do not have a boyfriend and you said you have experience so I just thought..."
"Shit Mel, I am a stupid shit sometimes. When were you thinking about?"
My roommate is going home this weekend so how about Friday night.
"Sounds like a date"

The week d**g until Friday night, I went over to Mel's apartment with a bottle of wine and a bottle of Astroglide lube. When she answered the door I handed her both bottles and she asked what they were for. I said "Lube, the wine is so you relax and the lube is, well lube."
we opened the wine and drank the bottle and made small talk and cuddled a bit. I had never had sex with this girl but we explored each other with our hands, and stripped each other down. Once we were naked I said to Melissa that having a couple of orgasms will help her relax for the anal sex. I laid her down and proceeded to eat her pussy. She was hairy which I usually don't like, but seeing as I knew I was getting her ass I went at her with a relish, so I got a couple of hairs in my mouth, big deal.

She came once under my tongue and I got her into the doggy position. I worked my cock into her pussy and opened the lube bottle. I fucked her pussy slowly and warmed some lube in my hand. I picked up the pace a bit and worked a single finger into her ass. She tensed and so I stopped and started over. Soon she was used to single finger and so I added another. Again she tensed, and again I stopped and worked my way up. I did this until I had three fingers all the way into her ass. I took my rock hard cock out of her pussy and added a little bit more lube. I slowly worked my cockhead into her and she gasped, but did not tighten. I withdrew and worked it in again, and went down a little father. Step by step I did this until I was balls deep in her ass.

She was really seem to like it, but I knew hoe to really get her worked up. I handed her a vibrator I had brought and said, use this on your clit, or stick it in your pussy, and then i turned it on. As soon as it hit her pussy lips she moaned and convulsed. Soon she had the vibrator worked into her pussy and had the knob at its highest position. She had her arms down and just had her ass in the air. I fucked her hard and she came repeatedly. When I came it was like the proverbial fireworks, one of the greatest orgasms of my life. I pulled out and laid down next to her. She was simply in a ball and not able to talk. 'I have never came so much or so hard in my life." she said once she was able to speak.
"Wanna watch? My roommate made me videotape it so she could watch it next week." I was a little made, but more turned on. We watched it and she got really turned on again. This time I took her ass in the missionary position and she reached for the vibrator. I lasted longer this time and she came several times again before I came for a second time in her ass.

"Well, what do you think?" I asked her.
"I fucking love it, can I borrow the vibe?"