Solving My Little Problem

My first few sexual experiences weren't very pleasant, mostly because I have a deep, dark secret. The truth is, I have a fairly small penis and I'm really embarrassed to let anyone know it. Growing up, I was as horny as any boy my age, but having a small cock kept me from being sexually active until I was out of high school.

To add to my misery, I have an older sister who was always very popular. Throughout high-school, I had a dozen chances to score with her hot friends, but I was too embarrassed to even try. Any time one of them showed the least bit of interest in me, I'd push her away.

The summer after I graduated from high school, my sister, Linda, came home for vacation from college and brought a few of her college friends with her. These girls were all smoking hot, too.

My sister, Linda, didn't waste any time making herself at home after being gone all semester. She and her friends hadn't been there half an hour before they all changed into their bathing suits and started laying out by the pool.

Of course, with all that eye-candy around, small dick or not, I wasn't going to be left out. I changed into some swim shorts and made my presence known by the pool. I even tried being polite by asking the girls if they needed anything and offered drinks and snacks, all the while, giving myself the opportunity to check them out in their tiny suits.

My eyes were constantly drawn to Angie. She's a brunette of average height with largish breasts and a cute face. She was wearing a two-piece suit with a little sarong skirt on over the bottoms, which appeared to be thongs. The top did a good jobs of accentuating her tits together and giving her some ample cleavage.

Erin's physique contrasted Angie's. She was tall and slender, and she had much smaller breasts. She had long, beautiful, brown hair that she wore draped over one shoulder and a beautiful face to match her body. Despite her sexy appearance, she still had an innocent, inviting smile. She was wearing a two-piece suit also, which was much skimpier than Angie's, and she was definitely wearing a thong. I was trying to look at her without making it obvious that I was checking her out, but she was pretty obvious about looking to see if I was looking, so finally after I looked away when she caught me looking a few times, she just looked at me and smiled, then turned to face away from me to bend over and pick something up off the deck. That gave me a great view of her ass crack and the thin patch of material that covered her snatch. Her actions were so obvious, my sister let out a wailing, "Oh, my God, you tramp!" Erin giggled and said, "Shush. I'm just having fun."

Linda's other two friends didn't have a whole lot to say. Cheryl was a red-head. She had a shapely body and probably the nicest ass out of all of them, but she also had the smallest tits of all the girls. She was wearing a one-piece suit and seemed to be very shy about showing off her body. She kept her eyes on me any time I was around her as if she was trying to force me not to check her out. Really, even though she didn't have very big tits, she was still attractive, especially the way her hard nipples pressed against the thin material of her suit. In the front, she had a major camel toe. I don't know why she was wearing a one-piece. It accentuated more of her sexuality than the other girls' two-piece suits did. When she wasn't glaring at me, the few rare times I saw her smile, she had a decent smile, one that I'm sure would melt the hearts of most guys.

Rachel was the tallest of the girls, with boobs I guessed to be a C cup. She was wearing a two-piece and she looked like she had dozed off in the sun.

My sister, Linda, didn't seem to mind that I was there at all. She sat back in the pool chair in her little two-piece outfit and just grinned watching me check out her friends.

After sitting by the pool and trying to interject something meaningful into the girls' conversation, I decided to go inside and watch some TV in the family room. The room faced the pool, and from the sliding glass door, I could still see everything that went on out there, just in case something interesting happened. With the sun still up and no lights on in the family room, I could sit there without the girls realizing I was there.

When I got inside, I could barely hear what the girls were saying with the TV going, so I turned the volume way down. After I muted the sound, I could distinctly hear Angie say, "Your brother is kind of cute."

"He's not so bad," Linda said, "For a brother anyway. I just feel sorry for him sometimes."

"Really?" Erin asked. "Why is that?" I was also curious. Why did she have to feel bad for me? She couldn't have known my secret, could she? There's no way she could know about my little dick.

"I think he's still a virgin," Linda said.

I was immediately embarrassed. She might not know my darkest secret, but knowing I was still a virgin and talking about it to her friends was almost as bad as knowing I have a small cock. The worst of it was that she was right, I was still a virgin, but how did she know that? Not only that, but why did she have to tell the other girls and why were they talking about it? I could hear them giggling.

"Really?" Erin asked. "Why? He's not ugly and seems to be able to hold a conversation. He must have had at least one opportunity in his life to do something with a girl. And you know he's not a fag. I saw the way he was looking at my ass."

"Who could miss that? You were practically shoving it in his face! I don't know why he's still a virgin," Linda said. "I think he's just shy. You know how some guys are."

"Yeah, like Mark." Erin shook her head. "Remember him? I swear, he never even touched me. He was a nice guy, too."

"I would have fucked Mark, too," Rachel said. "He was cute."

"Yeah, I would have fucked him, too, "Erin agreed, "But he never made a move on me. I made a few on him, but I think it scared him away."

"Yeah, guys don't like strong women, they think you're pushy if you take some initiative," Cheryl said, joining the conversation.

"That's bullshit," Angie said. "I bet if you made a move on any guy, he'd be all over it unless he's gay or something."

"I disagree," Cheryl folded her arms over her petite chest. "You'll scare him away."

"Wanna bet?" Angie asked. "If I came onto Linda's brother, he'd be all over it."

"Are you saying you're going to try to take my little brother's virginity?" Linda asked.

Angie was quiet for a few seconds, then responded, "Would that bother you?"

"No," Linda grinned. "If you want to fuck my brother, knock yourself out."

Fuck. My crazy sister was out there talking to her friends about whether one of them should fuck me or not. I couldn't believe what I was hearing. If I hit on one of these girls in public, they wouldn't give me the time of day, but because they were with my sister, they acted like it was no big deal to fuck me.

"I hope you like rejection," Cheryl added. "How would you plan on doing it?"

"I don't know," Angie looked thoughtful. "Maybe I could say something like, 'Nice shoes, wanna fuck?'" The girls laughed. "Yeah, with my luck, he won't be wearing shoes." Angie stood.

"You're going to do it now?" Linda sounded surprised.

"Yeah, why not?" Angie said.

"With all of us here?" Linda asked.

"What kind of a whore do you think I am? I'm not going to bring him out here and fuck him in front of you bitches. I'll do it inside."

Angie started walking toward the back door. I panicked a little, then fumbled for the remote control to turn the volume back up.

"Hey," Angie said, entering the family room.

"Hey," I replied.

"Weren't you wearing shoes earlier?" She asked.

"What?" I asked. "Shoes?"

"Nothing. I was going to make a joke. Forget it. Hey, do you have any more of that lemonade you had before?"

"Lemonade?" Now, I was starting to sound like an idiot. I was nervous and I was hoping it didn't show.

Angie grinned. "Yeah, you know, yellow liquid. Kids sell it on hot days."

"Sorry," I acted like I didn't get the sarcasm. "Would you like a glass." I stood from the chair and walked toward the kitchen.

"Please," she smiled, following me, "Unless you want to just pour it in my mouth for me." Apparently, she had a sarcastic sense of humor.

In the kitchen, I poured her a glass while she stood there in that hot bikini of hers, twisting her hair around a single finger as she leaned on the counter.

"Are you into music?" she asked.

"What do you mean?" I asked in return.

"Music. What do you listen to?"

"All kinds of stuff, I guess. Probably nothing you'd like."

"How do you know what I like," Angie smiled taking the glass of lemonade from me. "Got a big collection?"

"Yeah, a couple hundred CDs," I said.

"Where are they?" She asked.

"Upstairs. In my... They're in my bedroom," Geez, I was stuttering at simple questions. It wouldn't have been so bad, but she'd just been outside talking about how she was going to come in the house and fuck me. I was far too nervous for this. To make matters worse, my sister and three of her other friends knew what was going on.

"Can I look?" She asked.

"Sure, just go up the stairs and turn left," I know. I'm a fucking idiot. She was throwing herself at me and creating the perfect opportunity and I was so stupid I was going to blow a sure thing, too.

"You're not going to show me?" Angie sounded disappointed.

"Oh, sorry. I'll take you up there. Follow me." The prospect of fucking a hot girl like Angie had me so excited, I had to force myself not to take the stairs two at a time. I looked over my shoulder a couple of times to make sure she was still behind me.

"I'm right behind you," Angie said. "Don't worry, I won't get lost."

When I got to my room, I sat back on the bed and pointed to my CD collection. Angie followed me in, closing the bedroom door and locking it behind her. My heartbeat quickened. My brain was on overload.

Angie stood with her back to me, then bent over in front of the stereo. It only took her a second to find the power button. She turned the stereo on and hit the play button, starting up the CD that was already in the player.

When she stood and turned, she caught me looking right at her ass.

"Were you just checking me out?" She sounded serious, but not angry.

"No," I lied. "I was..."

"You were looking at my ass, weren't you?"

"Well, I was just... It's just that..." Damn, I was tongue-tied again.

"Hey, it's okay, really. Actually, now that we're on the subject, would you mind giving me your honest opinion?"

"About what?" I asked. What could I possibly have an opinion that would matter to her?

"Well, you're obviously a guy, right?"

"Yeah," I answered.

"Okay, then do you mind if I ask you a few questions?" She stood with her hands on her hips.

"I guess so. Like what?"

"Well, I don't want to embarrass you, but I'd just like the opinion of a guy on a few things. You're my best friend's brother, so I feel more comfortable asking you some things than I would a guy I'm dating. Know what I mean?"

"I guess so," I had no idea what she was getting at.

"Okay, cool. First question: Do you think this bathing suit looks okay on me?" She untied the sarong skirt and held it loosely in one hand as she turned to show me her near naked ass. "Be honest."

I swallowed hard, "Yeah, I'd say it looks good on you. You must know that already."

"Thanks. You don't think it looks slutty? My ex-boyfriend thought it did."

"No, no, I would have to describe it as sexy, not slutty."

"Really? You think it's sexy?" She continued to change poses in front of me.

"Yeah, very sexy." I could feel my cock growing in my shorts. I was hoping it wasn't too obvious to her and for once, I was feeling fortunate about the small size of my cock. Maybe it wasn't sticking out too far in my shorts and she wouldn't notice it.

"That's sweet of you. Thanks. Do you think it could be sexier?" She asked.

"Sexier? What do you mean?"

"Like, if I wore it differently, like this..." Angie raised the waist bands of the bikini bottoms so they were higher on her hips, narrowing the patch of material in the front in the process.

"Oh, I see what you mean. Uh, yeah, I guess that's sexier."

"You think so? Why?" I know she knew why, but I felt like she was trying to get me to say it out loud.

"Well, when you raise it up like that, the material in the front gets a little more narrow and it shows more of your uh, well pubic region."

"You think so?" She glanced down at herself, then slid the material in a little more, causing the patch to narrow to about two inches. "How about that?"

"Yeah, yeah, that's even sexier," My voice cracked as I spoke.

"What about my ass in this thong?" Angie asked, turning slightly to show it to me. "Do you think it's okay in this?"

"Yeah, definitely," I said. My cock was as hard as it was going to get. I couldn't believe it. She was in my room and modeling her body for me.

"You don't think my ass is too big?"

"No, definitely not. I think it's perfect."

"I'm glad I can ask you these things," She smiled, then turned to face me again. As she did, she slid her hands up and down her waist, drawing my attention to her flat stomach. "Can you tell I do a lot of aerobics?" She patted herself on the belly.

"Yeah, it looks like you do," I agreed. "You're in great shape.

"Want to feel how hard my tummy is?" She took a few steps toward me until her legs straddled one of mine.

"I guess," I stuck out my index finger and poked at her stomach gently.

"Not like that, silly, like this..." She grabbed my hand and flattened it out on her stomach, then ran my hand up and down her tummy from the top of her bikini bottoms to the bottom of the bikini tops. "How is that?" She let go of my hand, but I continued to move it around on her stomach.

"Wow," I said. "You have a really tight stomach."

"Thanks. I also work on my butt almost every day," she turned to face away from me. "Check it out."

With her back to me, I reached out both hands and gripped those beautiful ass cheeks. Giving them a good squeeze, I took both thumbs and parted her ass cheeks enough that I could view the thin material of the thong that ran the length of her ass and barely covered her asshole. I let go of her ass as she started to turn around to face me again.

"Do you work out?" She asked.

"Some," I said.

"It looks like you do," Angie reached forward and placed both hands on my shoulders, "Especially here on your shoulders. Do you mind if I touch you here?"

"No," I gulped.

"Linda never told me she had a brother with such a hot body," Her hands worked their way down from my shoulders onto my chest, then toward my stomach.

"I doubt she would have described me that way to her friends," Now, Angie's hands were on my stomach. I just sat there, waiting for what she might do next.

"You have a hard stomach, too," she kneeled in front of me, rubbing her hands up and down my stomach. As her hands massaged my stomach, her forearms brushed across the head of my cock, which was pressing at the material of my swimsuit. I know it was on purpose because she kept doing it again and again until finally, she was obviously moving her arm around to rub against my cock on purpose. "It looks like you have another strong muscle," Her hand slid from my stomach and onto my thighs. Her thumbs rested dangerously close to the crotch of my swimsuit. The pressure of her thumbs tightened the material down on the swimsuit, accentuating the shape of my short cock.

I looked down at Angie as she appeared to have her eyes locked on the small bulge in my shorts. I suddenly became aware of several possible outcomes in this situation. Angie didn't seem to be alarmed at the small size of my cock, at least not yet, but if she touched it or pulled my shorts down, I know she would notice. And if she did that, she might tell her friends about it, and worst of all, she might even mention it to my sister. There was also the possibility that she might just laugh right in my face. I couldn't face that kind of embarrassment, so I sat up a little and reached for Angie's hands. I was going to pull her hands away from my swimsuit, but before I could grab her hands, she reached up and stopped me, grasping my hands in hers.

"What's wrong?" She asked.

"I just... It's just that... Well, I'm not sure this is the right thing," I stammered.

"What do you mean?" Angie looked genuinely concerned. "I didn't embarrass you, did I?"

"No," I was trying to find a way out of this before she exposed my secret.

"Are you okay with me touching you?" She asked.

"Yes, it's not that. It's just that..." I couldn't finish the sentence.

"Have you ever done anything with a girl before?" Angie asked. "Is that it?"

I didn't answer. I just looked at her.

"Hey, that's okay," She rubbed my hands gently. "There's nothing to be ashamed of. We all had our first time some time, right?"

I nodded my head.

"If you don't want to do anything, that's okay. I didn't mean to take advantage of you or anything. I just thought you and I might have some fun. That's all." Her voice was calm and soothing, like she genuinely cared how I felt.

I know my face was burning red with embarrassment at what I couldn't say. I didn't want to admit to her that I was ashamed of my small cock.

"I think I know why you're so shy," She said softly.

"Really?"

"Have you ever had a girl touch you before?" She asked.

I shook my head.

"That's okay. I understand. We'll just take it nice and slow," Angie pushed my hands down to my sides, then let them go. She reached for the waist of my shorts and started to pull them down, but I quickly gripped her hands, stopping her from exposing my little dick.

"Don't you want to do this?" Angie looked up at me.

I nodded.

"It's not just because it's your first time, is it? I think you're embarrassed because you have a small dick," She said. My secret fear was realized. She came right out and said it. "I don't mean to be mean, but I can see already by the little bulge you're making in your shorts that it's not very big." She paused for a long time, looking at me. I could have died from embarrassment. "That's okay, though," she smiled. "I bet we can still have some fun with it."

"I, I don't know," I stuttered.

"Are you worried I'll say something to the other girls about it?"

I nodded my head.

"You don't think I'd pull your pants down so I could look at your little dick, then go and tell the other girls about how small your little dick is, do you? That would just be mean. Why don't you let me get these shorts off of you and show you some thing that feel good and we can just keep it our little secret, okay?" She smiled. I couldn't believe how many times she referenced the size of my cock and I was further embarrassed that she'd chosen to call it a 'little' secret, but I figured the worst of it was over.

"Okay," I released my grip on her hands and placed my palms down on the bed, gripping the top sheet firmly with my fingers.

Angie tugged my shorts down to my ankles and let me kick out of them, leaving me completely naked and exposed in front of her. I was really nervous. No one had ever seen me naked before, especially a girl as hot as Angie. Now, I was lying on my own bed with my erect little cock pointed at her.

Angie's eyes fixed on my little dick. She grinned as she made eye contact with it. I guess it amused her to see a cock as small as mine struggling to be as erect as it was. She slid her hands up my legs, then with the index finger of one hand, she traced the outline of my cock, gently running her finger up one side, then down the other.