Lindsey Gaps My Ass

Lindsey and I had been friends since the beginning of middle school and all through high school. We were never a couple, just good friends but that didn't mean we didn't share everything together, and I mean everything.

Now Lindsey was one of the popular kids at school, she was head cheerleader, head of the school council, and leader of the debate team, none of which I was on, but I knew why she was. Lindsey had a major domineering fetish; she always had to be in control, which was why most guys won't date her. I on the other hand didn't mind being bossed around, not to say I was weak, but it really turned me on. We both knew these things about each other which is probably why we got along so well.

We had a very open relationship, shared most everything, and tried not to judge. We had a good time together, and that was most important, there was never any feeling of I have to hang out with her, more I wanted to. Lindsey and I would usually stay in and make fun of people on TV, play video games and what not. Even after high school we both decided to rent a house together. It was a nice two story, two bedroom, in a good neighbor hood close to the college campus. She was going to college and majoring in engineering, while I worked construction for my dad, so we also had a lot in common there too.

About a week after moving in, Lindsey and I were sitting in the living room watching TV when an ad for Trojan condoms came on.

"Huh, I should really get a box of those" I blurted out of the silence.

"What would you need condoms for, you've never even had sex" Lindsey said back to me.

"Yeah, well I might some day; we're not all as experienced as you"

"That some day might be soon" She said shifting in her chair to look at me.

"Yeah, what have you heard" I replied staring blankly at her. "Does some one like me?"

"It could be some one in this room" Lindsey said starring at me. It took me a second to gather what she was saying, but once it hit, it hit hard. "I want to do everything we ever talked about, you and me. I think we have waited long enough, don't you agree?"

I was in shock, all I could do was nod my head and mutter "yes" and just stare at her. Her beauty suddenly became apparent to me. I had always known she was hot, a stone cold fox, to say, but now her long brown hair, perky boobs, and tight ass, seemed all the sweeter.

"I'm going to go get changed, I'll set your outfit out side the door." She said walking towards her room, I waited half a minuet to take it all in, and then followed her up. Hanging on her door was her old cheerleading uniform. My cock swelled with anticipation as I started to get undressed. I slipped the ping thong on, which was a very new sensation, then came the skirt and skin tight top. She also included a pair of fake breast she stole from a department store, it really rounded out the package, I thought. Then there was a knock at my door.

"Is my little bitch ready?' Lindsey said. "Come on out, I want to see my new girlfriend."

I walked out the door to see Lindsey standing in skin tight latex bra and pants, with high heeled shoes, my dream. I spun my dress around, and her eyes lit up, she grabbed me and threw me to the ground, I went willingly.

"Now follow me."

We walked/crawled down the stairs to the living room, and in front of the TV there was a blanket spread out with dildos in order from smallest to largest. Now, Lindsey was the only one I ever told it was one of my fetishes to gap my asshole, and I was to shy to buy any dildos so all I had ever used to fuck myself with was house hold objects like flash lights, and a lava lamp nothing like these.

"You like my collection of toys; I made that jerk Scott buy them for me. He though he would get to use them on me, what a tool." Lindsey said. (Scott was her old boyfriend and she found out he was sleep with the rest of the cheerleading squad, and apparently just used him to buy all the sex toys and cloths she could ever want.) "Didn't think I remembered you liked gapping your ass, did you? Well let's see just how big we can get that tight ass of yours. Now flip over and lie on your back, and let's see what we've got to work with."

I did as told. She placed a pillow under me to prop my ass into place and spread my legs a part. The thong moved aside and I felt a finger massaging my hairless ass, and then it slipped in, then another, and soon all 4. Her hand was small so my ass took them easily, but I new that would not be that case looking at the size of those dildos. The largest, was a butt plug about 3 inches around, I thought I could never take it all the way in, but I would sure try. Lindsey worked my ass, going deeper with her fingers until she reached the knuckle.

"Tell me what you want, you dirty girl." she demanded

"I want you to fuck my ass, gap me open like a whore." I moaned.

She wasted no time after that. A few drops of lube splashed my ass, and I felt the double dong begin to press against my puckered butt hole. It slipped in, and traveled straight to the back of my rectum, as deep as I had ever gone. "Now push for my like you are shiting." I did, and the dildo traveled farther in. It was the greatest feeling I ever had in my ass, just then I felt the other head of the dildo being forced in. I tried to relax and let it in, but she was to fast for me and crammed it in.

The pain was intense, my eyes closed shut and I clenched the blanket. I opened my eyes and looked up at her face; she had a smile on her face after seeing me in pain. That look, her look of power in that black latex made my cock stand straight up and my ass grab that dildo soo tight it hurt even more. The pain soon subsided and was replaced with pure ecstasy. This is what we both always dreamed of.

The dildo was pushed the rest of the way in, my ass was now pretty loose. She removed it, I felt empty, but soon a bigger, cock like dildo pushed its way in and filled me to capacity. It had to be 1 ½ inches around, and the biggest I ever got was 2 inches, and the next toy in line was a 3 inch butt plug. All I could do was relax and try to take it, because Lindsey wasn't going to stop now.

After working me for about 10 minuets, she stopped and pulled the dildo from me. "Get on your knees." I quickly spun around and kneeled in front of her. She grabbed the plug and positioned it under me. "Now lift your skirt, sit on it, take it all." She commanded. I look at her and slow sat on the massive plug. I was nearing my limit, so I began to move up and down on it to loosen my ass more. It was working, soon I was so close to slipping it in, but I just couldn't get it. Lindsey was standing behind me and saw my struggle; she got that smile on her face and pushed down on my shoulders. I collapsed on the plug and my body quivered.

"That's my girl she said massaging the fake breasts through my uniform, now you just sit here and I'll be right back." Like I was going to go anywhere with this in my ass, I was afraid to move, but slowly I got used to it. Lindsey returned a couple minuets later with a camera and a tripod. "I want you to see your slutty ass. She said hooking the camera to the TV, the screen flashed on, and she pointed it right at my ass. "Now watch as I pull this from you."

I bent over, my head facing the TV ass facing the camera, and Lindsey grabbed the end of the plug. The pull on my sore ass was excruciating but I couldn't draw my eyes from the screen. I saw it starting to stretch open, I used my hands to help hold it open, and just as I started too fully open, it popped out, and I was left with a massive gapping ass.

"Wow, you are a little whore look at that," She said as her finger slid around the edge of the hole, then it slowly closed, as I could not hold it any longer. I finally took my eyes from the screen and looked at Lindsey. "Was it every thing you expected?"

"Everything and more" I replied "What can I do for you though?"

"When ever I want you, and for what ever, I get you" She said sitting on the couch and motioning me over

"Sound good to me, we both win" I said sitting next to her. "Now about that video…"

"Don't worry about it, but I will be posting it on the net, I know people who have been want to see this for a long time."

I looked at her intrigued, she winked, got up and left the room, I quickly jerked off thinking about what was to come.