Sister's Lost Bet

Brooke looked pretty rough herself and I told her, "You look like I feel."

"Yeah, my head is pounding."

I made us both some coffee along with bacon and eggs which seemed to help. I asked Brooke about her "friend" and she told me he was only a booty call. He wasn't very good in bed but he had a decent-sized cock. I snickered and told her my date was gorgeous but kind of just laid there and couldn't suck a dick if her life depended on it.

Brooke then gave an off-the-cuff remark, "Shit, maybe we would have been better off sleeping with each other."

I could only reply, "Yeah, that would have been better for sure."

Neither one of us said anything else about sex but if she offered, I knew there was no way I could refuse. Brooke and I spent the first part of the afternoon cleaning up the mess from our party so our parents wouldn't suspect anything. They must have known we were going to have a party but we wanted to at least be respectful of their house. We were both moving a little sluggish at first but started to feel better once we began to move around. We spent the rest of the afternoon doing chores. Brooke cleaned up the kitchen while I mowed the lawn.

When we were done, I asked Brooke what plans she had for that evening. She said she was going to hang out with some friends but might cancel. I told her I planned on calling a couple of buddies over but hadn't made up my mind yet.

Brooke replied, "To be honest, I wouldn't mind just hanging out watching a movie or something."

"Yeah, that doesn't sound too bad. Maybe we could go out to dinner with some of the money mom and dad left us."

"That's a great idea, Will. We can't have any of their money left over."

Later that evening, my sister and I went to a local restaurant for a couple of burgers. Brooke looked really good in a black lace cami crop top and tight jean shorts. It was obvious she wasn't wearing a bra and was showing plenty of cleavage. We tried to buy some beer with our fake IDs but it didn't work. We figured we'd just have to wait until we got home, after all, we had plenty of leftover beer and liquor from our party that we had to get rid of before our parents came home. Brooke and I had a nice talk over dinner about school, college, our friends, and whatever subject that came up. We were both amazed at how well we were getting along while our parents were on vacation. We both realized that if we stopped competing for their attention, maybe we'd get along when they got home.

I told Brooke, "That would help but I think doing what we did also helped us get along better."

"What are you talking about, Will?"

I didn't know if she was being coy or really didn't understand what I was hinting at so I tried to explain it again, "You know, doing it."

"You mean we get along better when we fuck?"

I looked around to see if anyone heard her and replied, "Ssshhh. Not so loud. Yeah, that's exactly what I meant."

"For goodness sake, Will. It's only sex. We were both horny so we had some fun taking care of one another. It's no big deal. So what if you're my brother. You're pretty darn good at it."

"It sure was fun. You're pretty darn hot yourself."

Brooke turned things up a notch when she said, "As a matter of fact, my date kind of left me hanging last night if you know what I mean. He wasn't concerned with my needs at all. I was sort of hoping you'd help a girl out when we got home. "

"You mean, you know."

"You can be so thick, Will. Yes, that's exactly what I mean. Besides, mom and dad will be home tomorrow. We should enjoy ourselves while we can."

"Sure. I got off last night but she was nothing special."

We were in no hurry but as soon as we finished our dinner, we paid the check and went back home. This time was going to be different because it was planned and I was looking forward to spending the evening in bed with my sister. When we got home Brooke told me she wanted to relax and have a couple of beers which was fine with me. We had all night, there was no reason to hurry. I was simply happy that I was going to have a night of great sex with a very sexy young lady who happened to be my sister. I grabbed a couple of beers from the fridge and brought them into the family room to join Brooke. I thought we were going to watch TV but Brooke wanted to talk about our relationship.

"When did you first realize that you wanted to have sex with me?"

I was caught off guard by that question and I told her, "I don't know. I began to notice that your body developed shortly after you turned eighteen. Then you started wearing more revealing clothes around the house. I couldn't help but notice your tits got bigger and you were flashing your panties more often too. Were you showing off on purpose?"

"Not at first, but I thought I noticed that you and other boys were looking at me differently. No one had looked at me like that before. The more you looked the more I wanted to show off. It became kind of a game once I noticed you getting erections. To be honest, I was trying to embarrass you."

"I knew it, you bitch," I replied half-jokingly. "It fucking worked too."

We both got a good laugh out of that which led Brooke to reply, "Yeah, I know it worked that's why I kept doing it. Tell me the truth now. Did you ever jerk off thinking of me?"

I couldn't believe my sister just asked me that and I blushed profusely. It was so bad that she said, "I thought so. You guys are so easy to tease."

I figured it was time to put her on the spot so I asked, "Did you ever, you know, think about having sex with me."

"I have to confess that when I saw you getting erections around me, I had some pretty wild dreams. I wondered what your dick looked like, how big it was, and what it might taste like."

Brooke confessed to wearing more sheer tops around me in the morning when she knew our parents had already left for work or leaning over in front of me so I could get a peek at her tits. She knew I was looking at her panties when she was wearing a short skirt so she made sure to leave her legs parted when our parents weren't looking or she'd bend over at the waist knowing the back of her skirt was lifting so I could check out her ass. Her favorite was walking back and forth from the shower in just her bra and panties. I told her that was my favorite too. Brooke told me she didn't act on some of her feelings because I was her brother but once she saw my hard cock when she lost the bet, it got her thinking. Then once she started sucking my dick, her pussy needed some attention.

I told my sister that while I enjoyed looking at her exposed body, I never considered trying to get her into bed. I thought a blow job was harmless but once she told me she wanted me to eat her pussy, all bets were off.

"Where did you learn to eat pussy like that, Will? You're damn good."

"I always wanted my partner to enjoy sex too and I like eating pussy. I learned a lot from the Internet too. It's made me popular with the girls."

"I bet it has. That first time we were together, you, uh, you licked my behind. That was nice. No one's ever done that before."

"To be honest, I'd never done it before but you've been telling me to kiss your ass for so long and you've got a really nice ass, that I just had this urge. I wasn't sure how you'd take it."

"Oh, it was nice. I wasn't sure at first either but I enjoyed it. Have you ever done anal?"

"No. No girl I've dated has been willing. What about you?"

"No. Some guys have asked but it wasn't something I wanted to do with them. I'd be open to trying it though."

I got a huge grin on my face because Brooke was giving me more than a hint. When she walked out of the room to get us a couple of more beers, there was a very noticeable exaggerated twitch in her walk. Damn her ass looked good in those jean shorts. When she came back, she leaned over in front of me while placing my beer down and opening it for me. She was showing me her cleavage and I was more than happy to look at whatever she was showing.

Brooke then told me, "I'll be right back. I'm going to change."

I had no idea what Brooke had in mind, not that it mattered. I waited for several minutes for her to return but I wasn't disappointed. When my eighteen-year-old sister walked into the room, my jaw dropped wide open and I openly gawked at her. Brooke was wearing a deep blue lace demi-bra and thong set with white thigh-high stockings and white, open-toed high heels. Half of her breasts were pouring out of her bra and her perfect hourglass waist was sandwiched between her underwear. The white stocking accentuated her legs and her high heels gave her ass a distinct wiggle when she walked in addition to making her legs appear longer. I hypnotically watched as Brooke paraded around the room like a runway model. She stopped in front of me and my eyes drank in her beauty from the tips of her pedicured and painted toes to the top of her head and back again.

Brooke then asked, "Well, do you like my new underwear?"

"Like it? I love it. You look gorgeous, Brooke. You're absolutely stunning."

My little sister walked around the room a couple more times and then came to sit next to me on the sofa and crossed her long legs. She let her shoe dangle from the tip of her toe as her leg nervously bounced.

"Oh, look at you. It looks like seeing me in my underwear has caused you a big problem."

Brooke was looking at my obvious erection and I replied, "If I didn't get hard after seeing you in that outfit, I'd think I was dead."

Brooke laughed and replied, "Well, you sure aren't dead but why am I the only one sitting here in my underwear?"

She didn't have to say that twice and I quickly stripped down to my boxer briefs with my obvious erection clearly outlined by the cotton fabric. There was a little damp spot up near my waistband where precum had leaked out of my dick. Brooke's eyes quickly darted towards the lump in my briefs and began to stroke my legs. I couldn't resist running my hands up and down the silky material of her stockings and bare upper thighs. Seeing my sister wearing stockings and feeling how soft they were, planted the seeds for me to develop a nylon fetish.

Brooke and I were talking and drinking while we toyed with each other's bodies. I would fondle her breasts and she even played with my nipples which I found I liked. We were taking our time teasing one another, drinking our beers, and enjoying the sight of each other half-naked.

When I got back from getting a couple of more beers, I told Brooke, "Stand up and let me get a good look at you again."

She playfully asked, "What if I told you to kiss my ass?"

"I'd tell you I was going to do more than kiss your ass," was my response.

Brooke stood up and did a slow twirl for me and I told her, "Damn, you've got a nice body."

I took her in my arms and began to nuzzle her neck as my hands roamed over her bare flesh. Her skin felt so soft and she smelled so nice. Brooke moaned softly as I kissed and nibbled on her neck and shoulders before I unsnapped her bra and peeled it away from her body. I immediately cupped her breasts and began to alternately suck on her nipples. My hands slid down her torso and I grasped her ass cheeks, pulling her closer so I could grind my cock against her thigh and midsection. Brooke was sinking her fingers into my ass and pulling me closer in return, moving her hips so her body was rubbing against my erection.

I couldn't wait any longer to fuck my sister so I suggested, "Let's take this into the bedroom."

Brooke picked up her bra from the floor, making sure to bend over in front of me so I gave her a playful slap on the ass.

"Ouch, that hurt you asshole. Why don't you get a couple more beers and meet me in my room?"

I watched my sister's cute ass wiggling as she walked toward her room. I was dreaming of what I was going to do with that fine ass in just a few minutes. I grabbed a couple of beers and quickly went into her room where I found her sitting on the edge of her bed looking as sexy as ever. I was too damn horny by this time to even feel a twinge of guilt about fucking my sister again. My dick needed some attention and Brooke was going to give it to me.

I got down on my knees, slipped off her shoes, and began to stroke her stocking-covered legs and feet. I gave her a short foot massage and noticed her perfectly pedicured and painted toes. I ran my hands up and down her legs then ran my face along her thighs. Her stockings felt so good in my hands and face. I picked up her feet again and began to suck on her toes while stroking her calves. Brooke picked up on how much this was turning me on and began to run her feet over my chest and face. The softness of the silk stockings felt wonderful on my skin.

I stood up to strip off my boxer briefs, releasing my dick which was rock hard, and pointing up towards the ceiling. I took Brooke's feet and put my dick between them. My sister took the hint and gave me a short foot job, stroking my cock and balls with her stocking encased heels and toes. I was afraid I was going to cum too soon so I climbed up on the bed. Brooke got in the middle of the mattress and I stripped off her thong. I spread her legs wide, taking a moment to let my eyes feast on her naked body, then I dove between her legs and began to eat my sister's tasty pussy.

In no time, Brooke was squirming on the bed, moaning loudly as I tongue fucked her. She came almost immediately after I began to focus my oral efforts on her clit. I ate her juicy pussy until she came twice then spread her legs wider and began to fuck her. I placed my sister's legs over my shoulders and drove myself deep inside her. I watched as her breasts were flopping around as I plunged into her.

When we were fucking doggie style, Brooke was shouting out, "I'm a dirty little bitch. Oh shit, fuck me hard."

"You're a horny little bitch too. Take my dick, Brooke, take it deep."

Unfortunately, it didn't take me long to cum after an evening of teasing and when I pulled out Brooke said, "I, uh, thought you were going to do me, you know, back there."

"Don't worry, sis, this was just the beginning. We have all night."

Brooke smiled in acknowledgment and said she was going to take a quick shower. I watched as she walked out of the room and paid particular attention to her shapely ass. I've noticed how fine her butt has gotten and undressed her with my eyes almost every time I saw her over the last several months. The first time I became attracted to her ass was when she was wearing a pair of black leggings that look like they were painted on her.

I remember thinking, "Holy shit, my little sister has one fine ass. Why haven't I noticed it before?"

Ever since that day, she seemed to wear tighter jeans or shorts. She has several pairs of compression shorts she wears that are even better than her leggings because they show off her shapely legs as well as her ass. When she wears them with a sports bra, it drives me nuts. Tonight, I was going to get a chance to do what I dreamed of doing to her by fucking her ass. I decided to join Brooke in the shower and I startled her when I pulled the shower curtain back.

"You scared me half to death, Will."

"I wouldn't want that to happen, not when I'm about to fuck that beautiful ass of yours."

"Kiss my ass, Will."

"Umm, I will, all in good time, Brooke. I'm looking forward to it," I replied as I slapped her on the backside.

I helped Brooke spread the body wash over her taut eighteen-year-old body. My hands glided over her breasts and her torso as they made their way to her pussy. I gathered more body wash onto my hands and spread it over her butt cheeks and asshole. In turn, Brooke soaped up my cock and balls with me getting hard again.

"It doesn't take you long to recover now, does it?"

"Not when I have a hot chick that wants to have sex with me."

"So you think I'm hot."

"Oh fuck yeah."

"I think you're pretty hot too, Will."

After we rinsed ourselves, we helped dry each other off which only served as another way to sexually tease each other.

Brooke then suggested, "Why don't you grab us another beer or two and I'll meet you back in the bedroom?"

"Sounds good to me."

When I got back to her room, I almost dropped the beers as Brooke was on her hands and knees wiggling her ass. I could hardly believe I was about to take my little sister's anal virginity and lose mine at that same time. I tried to convince other dates of mine to try it with no success. Now I was in Brooke's room and she was asking to try it. It was way beyond my wildest dreams. If someone had told me last week that I'd be in her room about to do anal with my sister, I would have told them they were out of their friggin mind. But here I was and it was going to happen.

Brooke turned over and sat on the bed as we each opened a beer and spent a few minutes drinking them. It seemed so natural to be sitting there with both of us naked.

In those few minutes, Brooke told me, "I've read some stuff on the Internet on anal sex and the trick is supposed to be to take your time and make sure we are both well lubricated. There's some lube on my nightstand."

"Yeah, I've read up a little too. I don't want this to hurt you. I want you to enjoy it as much as I will"

"I don't want it to hurt either, Will," Brooke replied with a laugh.

It seemed like we were both ready so I suggested that Brooke lay face down on the bed with a couple of pillows under her hips. When she was in position I got behind her and spread her legs wide, running my hands up and down them while I savored the sight of her from behind. It all seemed like a dream but here I was naked on my sister's bed while she was offering her ultimate prize, her anal virginity.

I moved my hands up to fondle, spank and grope my sister's luscious, meaty ass. While I was playing with her cheeks, I would spread them so I could get a look at that puckered hole that was waiting for me. I followed my urges and laid down between Brooke's outstretched legs and began to nibble and playfully slap her ass. I would kiss, lightly bite and lick her butt, taking my time to enjoy myself and hopefully turn her on.

When I got close to my sister's asshole, she lifted her hips in what I took as a hint to lick her there. I swiped my tongue across it and she responded with a light moan so I did it again but longer this time drawing further moans from Brooke. I groped her cheeks, spreading them further as I continued to tongue her asshole which made Brooke squirm in pleasure. I enjoyed analingus more than I thought I would and took my time to explore my newfound pleasure.

I was also anxious to further explore anal sex so, after several minutes of tonguing her, I reached for the lube, spread Brooke's cheeks, and dripped some on her anus. I rubbed a little bit on the outside of her asshole, then gently inserted my finger.

I felt her ass tighten around my finger and thought, "If she's gripping my finger this tightly, I wonder what it will feel like on my dick."

Brooke's ass relaxed as I probed it with my index finger. I put more lube on her ass and inserted two fingers. I finger fucked her as she got used to having something going inside of her backside. I kept adding more lube to help prepare her for my dick. I asked her how she was doing and she said it felt strange but good. I figured it was time to take it a step further and put some lube on my dick. This was the moment of truth. I was a little nervous and I think Brooke was too. It was one thing to have a couple of fingers stuffed up your ass but a hard cock was something totally different.

I promised to go slow as I placed the head of my dick against my sister's asshole. I could feel her tensing up and tried to get her to relax. I started to push forward and saw her asshole begin to widen as the tip of my dick tried to enter. I was inexperienced and didn't want to hurt Brooke but my dick wasn't entering her ass as easily as I thought it would. I didn't know why it was so hard to enter her, maybe it was because she was tense and nervous. I desperately wanted to fuck her ass, my first opportunity at anal sex which was a fantasy of mine, and this was my chance. I didn't want to blow it so I pushed hard and in doing so, about a third of my dick plunged into Brooke's ass.