Lizzi Needs Reassurance

When you are transitioning into the junior year in college, life is good. You have finished enough of your program to be confident that you will be able to complete it, and you are far enough away from graduation that worries about "the real world" have not begun to occupy all of your free time. At this point, you are not the big man on campus but you are getting close to that point and you are much more confident than those freshman and sophomore guys.

My name is Ray and I'm a premed student at the University of Florida. I just finished my sophomore year of college and I'm attending summer term so that I can take a slightly lighter load in the fall and spring and hopefully bring my GPA up a little higher.

My sister is Lizzi and she just graduated high school. I went home and attended her graduation a few months ago. I got to visit with a few of my high school teachers and I saw a few of my high school classmates who also had younger siblings graduating. I also saw my old high school girlfriend, Sarah, and I was hoping that maybe the old spark would still be there but she's moved on with some new Mr. Wonderful, so we just had dinner together and then said goodbye. I'll probably never see her again.

Lizzi has some hot friends and I wouldn't have minded banging one of them but they were all preoccupied with graduation and didn't have time to pay attention to the slightly older college guy. I've been in a dry spell since I broke up with Alice in April. Sex with her was fun but she was so possessive and demanding!

Anyway, so Lizzi is starting college here at UF and mom and dad decided that the two of us could share the two-bedroom apartment I was already renting and had shared with Ben last year. He's living with his girlfriend now so I need a roommate and they feel safer about having Lizzi live with me.

Lizzi and I have always gotten along very well. She's a smart girl, has a good sense of humor, and was always a very loyal friend to her friends. That's something that I really like about her. She's also kinda cute, as sisters go; she's petite and has a gymnast's body. There isn't much body fat and she has small boobs and a small butt. She's also got a cute face and a clear, slightly pale complexion.

The only problem Lizzi has is that she doesn't have any self-confidence. Her boyfriend in 11th grade broke up with her and told her she looked like a boy with her small tits and that really caused her to go into a shell for a while.

She finally started dating again about three months before graduation and I think she actually lost her virginity on prom night. She told me that they got "hot and heavy" but she never actually said that they fucked. The guy - Dennis - was a baseball player and he had gotten a scholarship to Georgia Tech so that relationship would probably soon be history.

So . . . Mom and Dad brought Lizzi to Gainesville, along with way too much junk to fit in one room, and they ended up taking some of that stuff back home, fortunately. They took us all out to dinner at Francesca's Trattoria, then they left and went back home. I drove Lizzi back to our apartment and sat her down for a talk about house "rules."

"Okay here's the way it is. I'm not Dad and I'm sure as hell not Mom. We're gonna have a few house rules but otherwise, you're on your own. If I see you doing something stupid, I'll talk to you about it but I'm not in charge of your life. If it's something monumentally stupid, like you might get arrested, I probably need to tell Dad, but that's it."

"For the most part, Sunday night through Thursday night is for studying and making sure you get decent grades. No loud noise or partying. This isn't high school and you won't breeze through any of this. You need to study. You cook and I'll clean up afterwards; if I cook, you clean up afterwards. Friday and Saturday nights are for fun. If you want to have a guy spend the night, please let me know so I don't have any surprises in the middle of the night. I'll try to do the same for you if I have a girl stay over."

"Mom and Dad aren't here. You've seen me in my boxers plenty of times and sometimes that's all I wear when I'm at home. Mom would fuss about it but, like I said, Mom's not here. If you have someone over, obviously I won't run around in my boxers. However you feel comfortable lounging around, that's your business. You can stay fully dressed but I've seen you in your underwear plenty of times."

Lizzi paused a minute and then responded. "All of that sounds cool with me. I probably won't have anyone staying over unless Dennis comes to visit."

I interrupted her. "Lizzi, I know that you feel special about Dennis since you lost your virginity to him - I assume - but none of those high school romances survive once people go to separate colleges. Honey, he was your first but he isn't gonna be your last and that's okay. You'll meet other guys and have sex and relationships and maybe even end up marrying one of those guys eventually. Just make sure you're on birth control pills and use condoms!"

"Thanks, Dr. Ray!" Lizzi teased me, "but I think Dennis and I will be different. You'll see!"

"I hope I'm wrong but if I'm right, I've got a shoulder you can cry on," I offered.

* * *

We had a few days before classes started and we settled in to our new routines. Lizzi is a good cook and I was happy to have her prepare every meal, even though I hated washing the dishes and cleaning the kitchen. After dinner, we sometimes had a glass of wine or a rum and coke but Lizzi never wanted to get too inebriated.

I slept in just my boxers every night and I rarely put on any more clothes in the morning until I was ready to go somewhere. Lizzi would walk around wearing just her panties and a tee shirt, and I thought it was kinda cute that she occasionally borrowed one of my tee shirts to sleep in.

Within a few days, the tee shirts became abbreviated tees that hung just a few inches below her boobs. Occasionally, Lizzi work a thong instead of panties. She was rather oblivious on those mornings when I could see a camel toe in the crotch of her panties. I'm her brother and perhaps I shouldn't be looking at her crotch but I am a man and I had not had sex in several months. Yes, there were a few nights that I jerked off thinking about my sister's camel toe. She's cute!

About a week after classes started, Lizzi told me that Dennis was coming to visit on the following Friday. She spent that Thursday night cleaning the apartment (even though I didn't think it was dirty) and changing the sheets on her bed. I guess she was excited about the prospect of seeing Dennis and getting laid again.

* * *

He had a flight that arrived at Gainesville at 9:30 pm Friday night. That night, we each had one drink to relax. Lizzi was a bit nervous about seeing Dennis and needed to stay calm. When her phone rang around 8:00 pm, she saw that it was Dennis and she ran into her room to talk in private. At that point, I was lounging in just my boxers but was preparing to get a shower, get dressed, drive Lizzi to the airport, drive them back home, and then vacate the premises for a while.

She was in her bedroom for 15 minutes before she came out and it was immediately obvious that she had been crying. I didn't say or ask anything. There was no need to ask. I simply went to her, put my arms around her, and held her tight. She burst into tears and I put my right hand on her head and patted it to console her.

"I'm such a loser!" she managed to say. "Nobody wants a girl that looks like a little boy!"

"You're not a loser and you definitely don't look like a little boy," I whispered softly. "Why don't we sit down and you can tell me what an idiot he is, and then I'll tell you what an idiot he is."

"Okay, but I wanna get something to drink first. How 'bout a rum and coke?" she asked.

"Your wish is my command!" I responded. I quickly poured each of us a drink and returned to the living room and sat down next to Lizzi so I could hold her hand while she talked.

"I guess you figured that he's not coming. I don't think he ever intended to visit me and he just procrastinated about telling me the truth."

"Yeah, some guys have a problem being direct and dealing with the truth," I offered.

"You're right. Yeah, I lost my virginity to him on prom night and I thought that meant that what we had was special. That's what he said every other time we had sex. I was happy to have him as a boyfriend and I tried to make him happy but that wasn't enough, I guess. He said that we should each date other people and I said that I don't want to date anyone else but, obviously, he does. I asked him if there was something about our relationship that was bad and he just said that he wanted to date different women. So I asked, 'what do they have that I don't' and he got mad and said 'they have boobs.'"

"Lizzi, you don't look like a little boy. Yeah, you don't have big boobs but you've got boobs. You don't look like a boy. Lots of girls have small boobs but lots of guys like smaller boobs. I dated a girl last year that had 34B boobs and they looked just perfect to me."

"Well, I'd be happy if my boobs were that big," she responded. "You remember when we used to take baths together?"

"You mean like when I was 7 years old and you were 5?"

"Yeah, well they haven't grown since then!"

"Honey, your boobs are small but now you're exaggerating."

Her self-deprecating rant continued. "He wasn't even interested in coming down here for some really hot sex, something that most guys would love to get . . . at least they seem to love it with other girls."

"What are you talking about?" I asked.

"Well, over the summer, we had sex maybe ten or twelve times. Enough that we tried a few different things. Maybe losing my virginity on my prom night made me the last virgin in high school but I wasn't totally naïve about sex and we tried different things. I gave him a hand job and I gave him oral sex. I hate the term 'blow job' but I gave him oral sex. And he went down on me. And we went down on each other at the same time. We did it in missionary position, and girl on top, and doggy style. But there was something we hadn't tried yet that he kept wanting me to do . . ." she trailed off, and then took another gulp of her quickly disappearing drink.

"Are you talking about . . . anal sex?" I asked.

"Yeah, he kept wanting to do anal and I heard some girls say that it hurt and, honestly, I can't figure how that would do anything for a girl, so I was reluctant, but . . . I finally told him that if he came to visit me, we could do anal. I was kinda scared and excited at the same time. . . . Refill?"

"Okay, but you're definitely not going out anywhere tonight and this is your last one, okay?"

"Sure, but if this is my last one, make it a double, please!"

Refreshments replenished, we continued.

"I had it all planned out. I was gonna make him wait until tomorrow night, then I was gonna bribe you to stay gone for about three hours. I was gonna fix us dinner at home and then a drink, and I was gonna start playing some music I could dance to. Then I was gonna start dancing and stripping until I was naked and I figured he'd be so horny at that point that he would just carry me into the bedroom and do it."

"Well, he's an idiot for letting that opportunity go by. Lots of guys would jump at that chance!"

"Not after they've seen my tits! Bobby said the same kind of things to me in 11th grade. It's not just one guy."

"Baby, those are stupid boys who don't deserve you," I tried to console her.

"They may be stupid boys but they don't want me," she retorted. "You're just my brother and you're supposed to say that stuff . . . and it's easy for you to say, 'cause you haven't seen my boobs since I was 5 years old. If you saw my boobs now, you'd know the problem isn't just stupid guys. I was so stupid to think that some stupid dance would make Dennis want me that bad."

"Hey, if I had a girlfriend and she cooked me a meal, then she fixed me a drink, and she started dancing and stripping and offering me sex . . . I'd be a might happy guy!"

"You just don't get it," she said angrily at me. She stood up, grabbed the TV remote, and started some music. She looked me in the eyes, without flinching, for five or ten seconds, then she kicked off her shoes and started swaying to the music.

The music was slow and seductive and I assumed this is what she would have played for Dennis on Saturday night. After a few seconds, she began unzipping her skirt and she tossed it aside as she kept dancing. At one point, she stood in front of me, looking away from me, and bent over far enough to look between her legs and back at me. Her panty-covered ass was just a few feet from my face and I thought it was a very cute, very sexy behind being presented for my consideration.

"Is this the dance you had prepared for Dennis?" I asked.

She nodded her head affirmatively and continued dancing. She began to unbutton her blouse and soon it was hanging open, exposing the pretty, lacy white bra underneath. It was a silky blouse and a few shakes of her shoulders and it was flowing down her arms and away from her body. Lizzi was still in her panties and bra and I thought that she would probably stop at this point but I was wrong.

She looked at me and mouthed the words "please don't laugh" as she reached behind her and found the clasp holding her bra in place. She carefully held the cups in place as she pulled the bra straps off of her shoulders and down her arms.

Staring directly and intently into my eyes, she looked rather pathetic but also very sexy. I was also looking into her eyes as she let the bra fall away from her chest, finally exposing herself to anticipated ridicule.

I later learned that Lizzi wears a 32A bra. Yes, her boobs are small but she is only 5'1" tall and, on her toned body, her boobs looked perfectly wonderful. They were tanned, so I guessed that she sunbathed at least topless when Mom and Dad were both at work. Her nipples were pinkish brown and looked like little pencil erasers. The pink flesh around her nipples were about the size of quarters and the overall effect of seeing her boobs was that I instantly wanted to have one in my mouth.

At that point, I realized that I had a tent in my boxers and it should have been quite obvious to Lizzi. I expected her to run into her bedroom and hide for the rest of the night but the rum and coke had apparently made a change in her plans.

She reached down with her right hand and covered her crotch, then pressed her hand into her body and slowly pulled it upwards so that her middle finger traced through the middle of her pussy. She then spread her feet a few more inches apart and repeated the move with her hand, pushing slightly inward with the tip of her middle finger as it reached where I assumed her clit would be hidden.

When she repeated this move the third time, there was no doubt that she was stroking her clit though her panties. She then walked over to the sofa, straddled my lap, facing me and leaned forward, bringing her right nipple within inches of my mouth. As much as I wanted to lean forward and lick that delight, I resisted the urge because I still thought that she would eventually think she had overstepped the boundaries and become embarrassed.

She reached down to stroke her panty covered pussy once again as she shifted to bring her left nipple to my face, and I heard her emit a little whimper as her middle finger stroked her clit. I could smell the scent of an aroused woman.

She stood up, turned around, and bent over once again. Then she reached down and put her hand inside her panties. This time, she simply left her hand in place and started rubbing in small circles around her clit.

She briefly returned to an upright position and then turned to face me.

"Should I take off my panties?" she asked rather coquettishly.

I still wasn't sure where she wanted to go, so I responded, "If that's what you want to do."

She shook her head 'no.'

"At last," I thought to myself, "this - whatever this is - is over and she's going to go to her bedroom and sleep this off."

Wrong.

"No," she said aloud. "If you wanna see my pussy, you pull down my panties." She stepped forward as closely as she could get and she was within my reach.

My resolve was exhausted and my dick was harder. than Chinese arithmetic. I reached up, grabbed the elastic waistband of her panties on both sides and slowly pulled downward. I paused when I got to the point where her pussy was about to be exposed and she gave no indication of wanting me to stop, so I continued.

When her pussy was fully exposed, I pulled the panties down past her knees and let them drop to the floor. She stepped out of her panties and kicked them aside. Lizzi had just shaved or waxed her pubes because there was not a hair in sight. Her pussy was beautiful, a perfectly formed specimen within inner lips fully concealed and just a simple slit visible externally.

Lizzi turned around and got down on her hands and knees, spread her knees apart, and then reached between her legs and placed her middle finger in her pussy. She started finger fucking herself with her right hand. She reached back with her left hand and pulled her cheeks apart. Lizzi's little asshole was pink, a tiny little star, that looked innocent and virgin.

Lizzi looked back at me. "I probably shouldn't let you fuck my pussy, but I was wanting to learn about anal sex this weekend. Would you like to show me? I bought some K-Y."

I nodded my head in agreement with her suggestion and stood up. She turned around, still on her knees, and pulled down my boxers. My dick was as hard as steel and it sprang into place.

"I guess we can take care of that," she said.

"Grab your K-Y, but my bed's bigger than yours."

She went to her bedroom, grabbed the K-Y, then walked into my bedroom. I had pulled down the cover and top sheet and was already in bed. She got in beside me.

"Okay, no dick in pussy tonight, but . . . anal sex doesn't just start out with sticking your dick in a girl's ass. Anal sex requires you being aroused and ready for it, lots of lube, and some patience. It doesn't hurt at all and some girls say it gives them really powerful orgasms, so . . . we're gonna have anal sex but I wanna make sure you are at the peak of arousal, so . . ."

I leaned over, started licking on one of her nipples, and reached down and started stroking her pussy. She was already wet and I thought it probably wouldn't be long before she was ready to orgasm.

I pulled my mouth off of her nipple and asked, "Did you enjoy receiving oral?"

"Oh, yeah," she replied.

I repositioned her so that she was across the bed sideways, with her butt at the edge of the bed. I knelt beside the bed, placed her feet on my shoulders, and started licking her pussy. She tasted so damned sweet it was incredible. Maybe all my senses were off because this was my sister but her pussy tasted wonderful! I stuck my index finger in her pussy and it felt mighty tight. It didn't take many stokes on her G-spot before I sensed her getting close to an orgasm.

I then pulled my finger out of her pussy and shifted down so that it was lightly grazing the cute little pucker that was exposed to me. I continued licking her clit and she seemed to be quite comfortable with the first anal explorations.

I moved my mouth down and started licking in circles around her asshole while I rubbed her clit with my left hand.

"Oh, gawd, that feels so fuckin' good!" she moaned.

I grabbed the K-Y and placed some on my right index finger, placed it on her pucker and pushed in just slightly as I moved my mouth back up to her clit. As she began to moan and thrust her hips, I pushed in with my finger and soon I was in up to my second knuckle.