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Introduction:

Jia learns the pleasures of anal sex
Jia's Awakening Ch 5 - Anal exploration

It had been a couple days since the girls had come over, and I relived that experience of taking Jia's cherry over and over. It was keeping me quite keyed up and wanting more, but I hadn't heard from either of the girls.

Then on the third day, I was relaxing at home watching some movies when I heard a light knocking. I went to see who was there and there stood Jia wish a sheepish look on her face, wearing a denim skirt and button up blouse. I invited her in of course and we sat down. I was nervous as she seemed uncomfortable. I hoped she wasn't regretting our fun a few days ago, or had told anyone.

We started with the usual "How are you doing" small talk for a few minutes before she finally took a deep breath and said she had something to ask me. "Go for it Jia, how can I help?"

"Erica told me that you have a big collection of movies, and I've never really seen much, but I'm curious. I was wondering if you wouldn't mind showing me some this afternoon"

I was a little unsure what she was asking, and didn't want to assume and get myself into some trouble, so I decided to see if I draw out of her exactly what she wanted. "What kind of movies are you talking about? I have my whole DVD collection here with sci-fi, action, romance, comedy, drama, etc etc"

"No, you know what I'm talking about" She replied back and giggled.

"You mean 'adult' movies Jia?"

"Yes, Erica says you like to watch them and play with yourself and sometimes you play together. I want to see some. And watch you. And maybe play a bit myself" she said with a shy smile.

"Ah, ok. Let's go back to my office where the computer is, as that is where they are all kept." I smiled and so did she.

Once we got back there and I found a second chair for her, I pulled up my external drive where I stored all my downloaded porn. "What are you in the mood for?" I asked her.

"I dunno....you pick"

I thought about it for a few moments. I didn't want to pick a lesbian flick, as she had done that in real life, and regular fuck flicks can get boring. So I decided on a scene of one of my favourite porn actresses, Melissa Ashley, gets fucked by a cowboy in an old fashioned bar, and he ends up fucking her ass good too.

As it began, I decided that she'd seen me naked, so I just dropped my pants and sat there in my underwear. She looked over and smiled. As we watched, I was rubbing my cock, and she put her one hand between her legs under her skirt. Before long, I had my cock out, and Jia had unbuttoned her blouse and lifted her skirt. She was breathing deeply and moaning as she had a hand in her panties. I reached over with my free hand and began playing with her nipples, which elicited even more pleasurable moans. Soon I was licking her nipple and I reached down and removed her panties, and then began fingering her as she continued to watch the action on screen.

I pulled Jia into my lap, removed her blouse and skirt so that she was totally naked, and continued to suck on her nipple. As the action on screen turned towards anal play, I also took my very wet finger from her pussy and began teasing her tiny ass. It was like she was given an electric shock, and she was crying out more as I fingered her teenage ass as she watched this young looking girl on screen getting her ass fucked deeply.

I went from thrusting my finger in and out of her back door to just moving it back and forth quickly, almost like a vibration, and I sucked hard on her small breast in my mouth. Less than a minute later she was letting out cries as her first orgasm coursed through her slim body. The incredible thing was that neither of us were touching her pussy or clit. Her body tensed up and her back arched, and I never let up on the stimulation on her nipples and ass. And just as she collapsed against me, we enjoyed seeing the cumshot on screen.

"Wow, that was incredible! I've never cummed before without touching my pussy. I didn't know I even could cum like that." Jia said to me.

"I have known a few women that have anal orgasms, and after seeing Erica working you over that first time and seeing your reaction to her finger in you back door, I thought you might be capable of it." I explained.

Jia smiled and replied "I've never seen such a small woman take a cock up the ass like that before, it really excited me. And she's so tiny, just like me!"

I smiled and confessed "Well I do have a bit of a fetish for slim, petite women"

"Do you have any others?"

"Well, this actress did quite a few, but only a couple other anal scenes. How about another favourite of mine who is a total anal slut but who is also very petite?"

"Sure" she replied.

So I pulled up my collection of Kat videos and picked one where she gets double penetrated. Just as it began, it showed Kat using some toys on her ass before the guys showed up, and I had an idea, so I paused the video and told Jia that I'd be right back.

I went and got one of my toys, a vibrating egg, and showed it to Jia. "You ever used one of these before?" I inquired.

"Nope, but I'm more than happy to try! In fact, why don't you use it one me as we watch this one?"

"Now how could I refuse that offer!"

So I sat in the chair and Jia climbed back into my lap. I was rock hard, but I told her not to play with me for now, as I had an idea for later that I wanted to save my load for. I began the video again and Jia watched it intently as I began to tease her entire body.

I turned on the egg and as it buzzed in my fingers, I began by caressing her nipples with it. She jumped from the sensation and let out a little squeal. I kept that up, alternating from one nipple to the other. As the action on the screen turned to the guys playing with Kat and fingering her holes, I in turn moved the egg down her tummy until I was between her legs, exciting her bare tiny teen pussy. Her hips were moving unconsciously in time with my hand playing with her and rubbing her with the buzzing toy. Soon I had it inside her tight hole and I rubbed her clit, and I began sucking her nipples. Very quickly Jia reached another orgasm, but was much louder this time, and after she came down from it, she showed no signs of wanting a break, so I just kept going.

Then as Kat was taking one of the guys cocks deep in her ass, I could see that Jia was hypnotized by the action on screen. I had an idea. As I continued to finger her clit, I pulled the buzzing egg out of her pussy, and I dropped it lower until it was right on her tiny butt hole. She nearly jumped out of my lap, but her eyes never left the action on the screen. So I rubbed the toy all around her ass and then finally I put it right at her hole and pushed. It popped in nicely, and Jia nearly exploded with a powerful third orgasm as I finished pushing it into her ass. She started whimpering and spasming non-stop as the egg buzzed away inside her back door. I sucked on her tits and played with her pussy and clit. I was rubbing at her clit pretty fast and hard, and I put some fierce suction and flicked her nipples with my tongue. Then just as the action on the screen climaxed with the two guys cumming inside the little slut pornstar, Jia let out another howl and her body tensed up again as she had her fourth orgasm in less than an hour.

"More, oh my god I want some more!" Jia breathlessly begged while trying to catch her breath.

So I had another idea and went for a couple more toys. I hid them from Jia's sight as I came back into the room, and I began another Kat video for her to watch as I worked her body over. The vibrating egg was still inside her ass and she was idly playing with her pussy, which was swollen and very wet, and her tiny nipples were almost as hard as my naked cock.

I grabbed the first toy, which was a basic vibrator and without turning it on yet, I placed it at her pussy and began to rub it around. Jia really liked that and began thrusting her hips against the toy, Soon I was pushing it into her little teenage pussy. After a couple minutes of stroking it in and out of her, I turned it on too. Jia just loved that and took over control of the vibrator, She began ramming it hard and deep over and over as it buzzed inside of her.

Once she was mesmerized by all the stimulation and the video, I decided to pull out the final toy and really driver her wild. So I pulled the small buttplug out and without warning, I pushed it into her ass, driving the vibrating egg even deeper into her. This finally drover her over the edge, and Jia began having one powerful orgasm after another, to the point where her body was convulsing and she was letting out primal grunts as her pleasure sensors were overloaded. Then she seized up really tight in one last mighty explosion of ecstasy and lasted like that for nearly 30 seconds.

After her body let go, she was shaking in my lap and quietly begging me to pull all the toys out of her. As I did, she went totally limp and passed out. I was surprised at that, and I picked her up and took her to my bed and laid her down, where she quickly began to rouse.

"Oh my god, I've never felt anything that powerful before" Jia smiled as she spoke.

"It was one hell of a show to watch I have to admit." I told her. "I think that was called a multiple orgasm"

"Whatever it was, I'm going to be feeling it for a few days! I loved seeing how those big cocks were going deep into every one of her holes in the video, especially her ass!" Jia exclaimed.

I decided that I'd see how far I could get her to go, so I asked "Would you like to try to take me up your ass?"

Jia just stared at me for a few moments. "Do you think it would fit?" she asked nervously.

"I think with some patience, a lot of lubrication, and some play beforehand with toys, it just might."

"OK good. I thought you might just spread my legs and try to shove it in like in the videos!"

I laughed and explained "I'm pretty sure they do some off-camera preparation with toys and lubrication themselves. Don't worry, I'll take it easy on you. I don't want to hurt you at all. In fact, I really want you to enjoy it alot. That way you'll let me do it again and again!" And I laughed a bit more.

"So, how do we begin?" Jia asked me innocently.

"Like this" I replied, and I leaned in and began kissing her softly on the lips. One hand went to her small breasts and cupped one and teased her nipple. Her own small hand reached down and grasped my rigid cock and stroked it slowly. My hand fell from her breast and worked down to her pussy, where I rubbed her clit and then inserted a finger into her still wet pussy. I gently fucked her with my finger for several minutes. Jia was getting very worked up again, and I could feel her hips rocking in rhythm with my finger as it went in and out. Then I pulled my lubricated finger out of her and I moved it to her anus. She gasped into my mouth as we continued to kiss, and I pushed gently at her entrance. Because of the toys before, my finger went in fairly easily, but her ass was very tight and I wondered at that point if I could actually get my cock in there. I pushed in the first two knuckles of my finger and then gently eased it back out. Then I pushed it back up inside her again as I moved my head down and licked one of her nipples. I continued this gentle finger fucking as I sucked on her small tits for some time. Eventually I had my entire finger inside of her butt.

Jia was thoroughly enjoying this and had forgotten about stroking my cock, which I didn't mind so much, as I didn't want to cum before I got to try to get my raging hardon up her teenage ass.

I decided that her ass needed some more preparation, so I withdrew my finger, grabbed the small buttplug, and began to ease it into her. I also let go of her nipple from my mouth and moved down between her legs and began to lick her bare pussy. She really enjoyed this of course, and was soon oohing and aahing and squirming around as I toyed her ass and ate her out. Several times I pulled the buttplug out and gave it a liberal dose of lubrication and then put it back in. I wanted my cock to glide in easily when the time came, and the toy was a good way to get lots of lube into her. After about 10 minutes of the combination of oral and anal play, Jia had another orgasm, though it was not as intense as her previous one.

After her orgasm, I decided the time had come to take her anal cherry. I pulled the buttplug out and spread her cheeks and gave her a good licking which she really enjoyed. Keeping her legs spread wide, I sat up on the bed and looked down at her slim, gleaming body that was writhing in sexual desire.

"Are you ready Jia?"

"Fuck yes, I want to feel you in me, just please be gentle."

I didn't need any more encouragement than that! I grabbed the lube and coated my cock, then I scooted forward and placed the head of my rock hard cock at her ass. "OK, here I go." I told her.

With that, I began to push my cock against her little opening, which was gaping ever so slightly. It took several tries before her ass would open enough for me to begin to enter her. When it did, the head of my cock slipped right in, but that was all that was going in at that time. Jia's eyes bulged wide at the feeling of her ass being violated by something so big the first time. My hands stroked her breasts and body as I soothed her and helped her get used to the feeling of the tip of my cock in her back door. After several minutes, she finally began to move her hips again saying "Oh my god it feels so big in me. But I want more. I want all of you inside of me. I want to feel you exploding inside me"

Damn but she was eager! I started to push again, then pulling back, gently fucking her ass. At first nothing really moved because she was so tight, but slowly my cock started to push deeper inside of her. Her ass was the tightest thing I'd ever put my cock into, and I was really fighting the urge to cum so early. Every time I pushed a bit deeper, it caused Jia to gasp in shock and pleasure. I asked her several times if it hurt, but she always reassured me that it didn't and that she was just getting used to the feeling but urged me to keep going. A few times we had to slow down and give her some additional time to adjust.

After about 15 minutes of us working things slowly, I asked Jia how she was, and she smiled and answered "Amazing".

I told her then "Guess what? I have my entire cock inside you ass baby"

"Really? I'm glad, cause I'm feeling sooo stuffed I wasn't sure I could take much more" Jia replied

"Oh, if it's too much for you, I can take care of that" and I pulled back fairly fast all they way out.

"Noooo! Put it back in!" Jia begged

Laughing, I stuck my cock back into her tiny tight teenage asshole, and this time I pushed hard and drove the entire length of my cock, just 7" long but I am about 50% thicker than most guys. She hissed through her teeth as her head flung back. Then I began to slowly fuck her, nearly pulling out each time I pulled back, and then pushing it all the way back in a bit faster.

Then I had a naughty idea (like what I was doing wasn't naughty enough!) and I asked Jia "Do you want to see what you look like with my cock buried up your ass?"

"Sure" she exclaimed.

So I reached over and grabbed my digital camera and looking down on her I started taking pics of her naked body, covered in a light sweat, her legs spread wide and bare swollen wet pussy shining, and my cock poking up her ass. Most of them I didn't get her face in, but a few I did get the look of pleasure and joy that was exuding from her.

Then I grabbed her and picked her up, my cock still in her ass, and held her in mid air. She laughed as I turned us around, and then I laid down on the bed with her on top. She took the hint and started riding my cock like no tomorrow. It was really hard not to lose my load deep in her ass as I watched her little frame bouncing on my dick. I reached up at one point and played with her nipples, pinching them, which drew little yelps from her. After we fucked like this for awhile, I told her to turn around and face away from me. She rode me for a few minutes like then. Then I decided I wanted to finish this with me fucking her from behind, so I held onto her waist and got up again, keeping her ass tight against me with my cock still impaling her. I spun us around again and placed her on the bed kneeling. Then I took a few more pictures as she looked back at me, enjoying the feeling of her first ass fuck.

I then began to really pound away. I started to tell her how good she was and how she was just like the porn star we'd watched on the computer. Jia really liked this and began to push her ass back against my every thrust.

"Oh fuck, I'm going to cum again" Jia announced.

"Go for it baby, I'll cum too" I told her.

And with that she let out a shout and her body tensed up again for her 5th orgasm of the day. And as she began her own orgasm, her ass clamped down so hard on my cock I thought she might break it off. And that just led to my own long-awaited release. I let out my own howl as I pumped even harder and began to shoot my cum deep in her bowels. Feeling me shooting deep in her drove Jia into an even more intense orgasmic state and she began to spasm violently as I continued to pump away at her tight teenage ass.

When I finally finished, I fell down on the bed beside her quivering body, my cock still lodged in her back door. I just held her as we both caught our breath.

Jia finally began to come back to reality and spoke "I've never cum like that before. Feeling your cock fucking my ass, it's just the most amazing feeling and I came without touching my clit or pussy. I just can't believe it"

"All I can say is that I loved it, and I'm glad you enjoyed it too" I told her.

After I finally softened and my cock slipped out of her ass, we actually slept for while like that. When we awoke we got up and went to the shower to get cleaned up. I got totally hard again watching her body in the shower, but she laughed and declined for another round, saying that she could barely stand up anymore, but she did suck me off and swallowed the load to relieve my aching. I asked her if she'd like to try anal again someday, and she told me that it was all she wanted to do from now on, which surprised me.

Before she left, I gave her the small buttplug as a gift so she could have fun at home. She kissed me and headed home.

I had totally forgot about the pictures we had taken before that, so after she was gone, I pulled then down onto my computer and enjoyed looking through them. I called Jia to tell her how great they looked I actually ended up jacking off to them while I talked to her and looked at the pics. She begged me to email her some, but I teased her and refused, telling her she'd have to come over to see them, and that I might share them around if she didn't take care of me properly! We laughed and talked a bit more and then said good night.

And so continued Jia's awakening to her sexual pleasures.
1 comments

Virtual_TouristReport

2009-04-10 23:30:02
That has to be the best build up to anal sex that I have read on this site.

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