Carree Loves Billy: Holiday Weekend - Cover

Carree Loves Billy: Holiday Weekend

Copyright© 2002 by Carree Wilson

Chapter 2

Erotica Sex Story: Chapter 2 - Bill meets me on a ski trip with my girlfriend who agrees to give us a day alone to experiment and get to know each other on a more intimate basis. I give Bill a special surprise that he never expected to prove my love for him. The story entails our first time sleeping and waking together. We experience tenderness and passion as young lovers as we experiment with our bodies and sexual freedom.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Teenagers   Romantic   True Story   First   Oral Sex   Anal Sex   Sex Toys  

With that, they were off. I hurried to clear the table and load the dishwasher. I turned off all the downstairs lights and went to my room after locking the outside door. No one could get in unless they knocked. I needed that privacy.

I went up to my bed and fished the butt plug from my pillowcase.

I lowered my shades, much as I do when I do my homework, so no questions need be asked if they came home early. I opened the package and inspected the rubber gel sex piece. I didn't feel very sexy. I decided that if I gave myself the little shave I needed around my vagina, I might feel a little frisky. I went to the bathroom and grabbed a towel and ran hot water for a washcloth. I stripped off my jeans and panties, spread the towel on my bed, grabbed a razor and sat on the towel. I used the hot wet washcloth to help soften the week old peach fuzz I had going.

Then, I used some baby lotion as a shaving aid. I had been shaving myself for about a year now and this was the routine, once a week. Shaving gels and creams seemed to irritate me, as they all had fragrance and other stuff in them. Shaving my entire bush off made Bill happy, and kept me a little giggly myself. It was something that made me feel so feminine. My Mom hadn't discovered it yet, and at this point I really didn't care.

Usually I shaved just before I was going to see Bill, because it always made me feel so sexy. Tonight was a different story.

After the shaving and manipulating my private parts to get a bare, smooth look and feel, I retrieved the KY jelly and the Little Blue Devil (my butt plug had a name!) I wasn't really sure how to do this. I had only touched myself there a few times and Bill has used his tongue on me a few times. Neither he nor I had tried to penetrate me there.

I kept my shaving towel on the bed and sat on it laying back to expose my little ring. I saw no genteel way to introduce the lubricant other than to rub it in with my fingers. I played with my pussy a little to engorge myself. Feeling blood rushing to those parts generally felt good, and made me more sensitive.

After a few minutes of rubbing while trying to avoid my clit, so as not to get too hot, I was ready to try some experimenting. I opened the tube of KY gel and put a dab on my finger and placed it right on my anus. COLD!, for sure. I put the tube underneath my arm to try and warm it a little. I rubbed my finger around over my little hole for a couple minutes and felt it opening a little, as it did the couple times Bill used his tongue on it. I got the KY tube again and put a little more on my finger and repeated the same massage. I had stalled long enough and brought my finger to the tube for a good coating of the gel. I placed it right on my anus and pushed. Surprisingly it went right in, not far, but right in. I didn't have the best angle and then remembered the anal girl in Kim's video and how she reached it from under rather than over her pussy. A switch of angles and I was able to reach a lot deeper, if I wanted to, this way. I held my finger there for a minute trying to decide if it felt good, or just different. I worried that the stimulation was going to make me want to "go", but I had my regular morning visit and felt that I should be OK. I didn't want to bother with an enema for this experimenting. I decided that a finger in my butt hurt a little at first, but eventually felt good and I continued to piston it in and out, if only to the second knuckle. I wasn't sure how much time I had to be alone, so I removed my finger and got the Blue Devil out. I coated it liberally with the KY jelly. The thin end was decidedly a lot thinner than my finger, and that gave me a little courage. It was also a little softer than my finger, so I noticed as I placed the tip to my butthole. I was apprehensive at first, but the tip slid right in. I worked that first inch or two with no trouble and began to think how easy this was, even though it was making me catch my breath because of the new feelings it was bringing. I began to pump the couple inches of the plug in and out of my butt. I began to get braver and let more in to myself when, I came to a stop! There was a decided muscle that was saying no. I shortened the stroke and just got the tip past that muscle and moved it in and out an ever so slight bit past it (my sphincter, I assumed).

Then on one of the in-strokes on the assault of that muscle it just slipped past the stop point. All of a sudden I was stroking about 3 inches back and forth in my butt. It felt strange, but good, and it was making me grunt in a pleasure pant. There was no time like the present, I thought and gave the plug a good push, and plunged into sharp pain. I must have been overconfident with my little strokes and felt this was going to be "that" easy. It wasn't enough to make me turn around and forget it, but I wanted to re-lube myself. I placed a dollop on my finger and brought it to my butthole and discovered it was not the impenetrable closed hole it had been a few minutes ago. It was dilated, ever so slightly, like the size of a Lifesaver candy hole. I pushed that dollop in and got one more and pushed that in too. I brought the plug back and slid it in, with one motion it went further than it had before and I was beginning to feel the bulb spread my butthole. That was causing me the most discomfort, the stretching of my anus. Without removing the progress I had made I wanted to get more lube on the bulb and around my stretching butthole. When I relieved the hand pressure on the plug, my body sent it flying out past the towel to my bedspread. But something wonderful happened there. The feeling of the withdrawal was delicious, and I craved to be filled again. I grabbed the Blue Devil and re- inserted it. It was a little painful as I got it past any previous point of penetration, but nothing that was going to discourage me now. I was giving short little strokes, swallowing about half the bulb when I went for broke and pushed it past the bulb so only the round flat base remained outside my body. In plain English, my asshole hurt like hell for a moment from the assault. I began to writhe from the pain and was about to clutch my stomach and roll over when that pain ebbed and I felt myself flush. It was definitely something I felt whenever I masturbated, the flush, but it had a different tenor to it. It felt nice. I touched my clit to relieve myself a little. As I did I ground my butt into the bed causing the butt plug in my ass to move from the friction of the base against the bed. I began to hump my ass down on the plug as I rubbed my clit.

"Oh, Bill I wish you were here right now", I shouted out in a high-pitched voice.

I was being double stimulated by my finger, and the device in my butt. There was definitely something here to like. A little perversion?... for sure, by doing the forbidden... and a physical reaction to anal stimulation. I flushed once again and suddenly, faster than I ever remembered, I was in the caught breath,

turning red as a beet,

raising my butt off the bed,

all muscles tensed mode of... DEEP ORGASM.

I felt my eyes roll back into darkness and felt my pussy flex in ejaculation. I looked in time to see a stream shoot from my pussy over my fingers causing it to splay to both of my legs. It was a good squirt and felt incredible. It was definitely the best and biggest quantity of ejaculate fluid I had passed since the first time Bill licked my butthole and massaged my G-spot on the slouch couch in his writing room almost a year ago. The passing of whatever that is may be the most pleasant feeling a female can have by herself. I shuttered quick again, lost my breath and let one more stream go. I was bouncing on the bed when this one geysered and it landed on my belly in a pool near my navel. Not a lot, but enough to fill that dimple. Instinctively, I put my finger in it to taste the fluid that resembled watered down milk.

It was decidedly sweet and not urine. I had really ejaculated!!

I had ejaculated on at least 3 other occasions, but with only one of them was I 100 percent sure of the passing of fluid that was not urine. I was sure, now, that I was a squirter. A female ejaculator. It's something that a little more than 6 of 10 are capable of, and only 2 in 10 actually do. I wondered if it was a blessing or a curse. I might have stains to explain.

I rested and caught my breath. I needed a drink to irrigate my mouth from all that heavy breathing I had done. I got up to go get a drink when I realized I was still impaled with the butt plug.

Ooooo, it felt good having this invader in my butt as I moved around. Instead of just going into the upstairs bathroom to get a cup of water, I decided to go downstairs to the fridge and get a can of Coke. I went 3 steps down the stairs when I realized I was wearing only a smile and the butt plug. I went back to my room and got my robe, just in case my parents came home while I was downstairs. Wouldn't THAT be a shock!! (Oh Carree, are you aware there is something stuck up your butt?) Going up the stairs gave me as much a thrill as going down did with the butt plug in me. I threw on the robe and went back to the refrigerator and found that can of Coke I longed for.

I guzzled half the can in one long tug on the can. As I tipped my head back to get the second half down I arched my back a little causing even more good feelings from between my butt cheeks.

I set the can down and went to go back upstairs. As I padded through the darkened house, I stopped to look out the window.

No one was in sight.

I was back up the stairs in a flash with that constant pleasure goose hitting me in my core.

I shucked myself from the robe and plopped down on the bed, being careful not to impact the base of the plug in my butt. I turned on my side and began to pull and extract the Blue Devil from me.

As soon as the bulb got halfway out, the whole plug glided gently from me. What a feeling! Quickly I pushed the clear blue pleasure shaft back into me. Wow, what great vibes this had. It slid right in, swallowing the bulb to rest on the base. I grabbed the base and began to work it in and out of me. The feeling of being full, relieved, and refilled by the plug was,... was sheer ecstasy!

I was lying on my hip, on my bed, fucking myself with an anal dildo!! In one way I felt like I was cheating on Bill, because he should have been here for this, but on the other, I remembered HE was going to be doing this to me in a couple days with his beautiful hard cock!! A cock I was going to suck until it begged to put into my warm body. My thoughts turned into orgasms as I grunted against the butt plug, over and over and over.

My hand finally grew weary of holding the base of the plug and thrusting into me, plus I needed to catch my breath again. I pulled the plug totally from my ass. WOW, what a feeling! I was so surprised at the pleasure this toy had brought me. I only hoped Bill's penis would be as pleasurable. I then thought of the rubber penis I had hidden in my doll trunk. Could I take that as easily? That was about as big as Bill, should I try it?

Oh,... why not?

I went to the window and peaked from behind the shade to be sure their car was not coming up the drive. I opened the closet and layed the trunk down and undid the brass clasps. Pinching the center clasp and pushing the right bottom released the false door and I grabbed the white rubber penis. It looked like the real thing, except the veins were exaggerated a little. I went back to the bed and squeezed about 3 fingers of KY onto my hand and stroked the white gel-like cock with it. I tried to figure the best way to position the cock to get it into me, I decided to squat over the towel that was protecting my bed from my workings.

I put the white cock right under me as I lifted my hips a little.

I was going to impale my butt on it! The first pressure I put on my butt with the dildo sent it sliding away from my anus and it went about 4 inches right into my pussy. I panicked that I would break my cherry and bleed right there and ruin a rite I was saving for Bill. I fell back onto my spine and pulled the phallus from me. If I bled, surely it would have shown on the white surface of the dildo. It was clean! WHEW!!!, I thought. But I still wanted to be filled. I knelt back up and rocked to a squat and positioned the white sex toy to my butt hole again. I placed my fingers protectively over my vagina slit as I teetered over the white dildo. My balance on the bed in this squatting position was not too good and I began to lose it. I was just going to use my hands to make a 3 point stance on the bed, when the white cock slid right up my ass. Wider than the plug, the hurt and pain was intensive for a second and I panicked that I may have hurt myself, but as I settled involuntarily on it and it filled me and the pain soon ebbed into a long slow groan.

"Oohhhhh, Ahhhhhhhh, Arrghhht", I exclaimed in guttural reports from my throat. I was full and I couldn't wait to move this cock in and out of my ass. I gave up trying to squat and move on it.

Once again I fell to my hip and reached for the rubber cock within me. I began to slowly move it in and out of me. Where with the plug I as able to quick-slide it in rapid fire, this full sized rubber cock would have split me if I tried that. I had to move it nice and slow, in and out, and the feeling was beyond words. I was loving anal sex. I worked up to one good orgasm, not quite a grunting, squirting one like before, but a long satisfying one. I was about to switch sides to my other hip, when I heard the growl of an engine outside. Quickly I bounded to my feet and went to the window and peeled back the shade. It was Mom and Dad. Just as that thought hit me, the white dildo dropped from my body leaving me to feel a void, an emptiness.

Quickly I scooped up the white rubber cock from the floor, noticing a couple very small, but telltale, brown streaks on it.

I put that together with the butt plug, and the KY jelly tube and rolled them in the towel I had spread on the bed. I took the whole mess and put it into the open doll trunk, closed it with a click, put on my robe and quickly went downstairs to unlock the outside door and let Mom and Dad in. They were just on the porch, all lit up from the sodium light their motion had set off, when I got to the door.

"Hi Mom, Hi Dad, did you get me that white convertible?" I asked.

"White? I thought you wanted a red convertible. Well, either way, no convertible, but a nice two tone, tan and bronze, Crown Victoria. You will love it when you see it. If you're a good girl, I'll let you drive it", my Dad kidded.

"Oh, Daddy, you know I'm always a good girl. I waited to get in the shower so I could let you in didn't I?... plus I loaded the dishwasher and cleared the table and... " I said before he interrupted me.

"OK, OK. You were a good girl while we were gone. When I get it next week, I'll let you drive it." Dad said and he hugged me.

"Carree, you hurry and finish your shower. I need you to help prepare some of tomorrows pies and polish the good silverware for your grandparents", my Mom added.

"Okie, Dokie, Mom", I said. "I'll just be few minutes", and I went running to the bathroom to start the water. Once inside I reveled in the empty feeling I had up my butt.

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