A Little Friendly Advice

Every guy thinks he's God's gift to women.

We're raised to brag about our conquests, play off our mistakes and tell tall tales of our talents in the bed room.

It's really just part of our ego.

And that's what made my life on this particular fall day quite miserable.

See, my name is Tom. I'm a 25-year old male who has never been in a serious relationship and while I've had my share of sexual experiences, they're really nothing worth bragging about.

In fact, it would probably be the opposite.

Every single time I've had sex, it's been with the intention of developing things into something more serious. Only problem is, that's not what the other person wanted and, in the end, I was left pondering what went wrong.

It's not that I'm a bad looking dude. I'm 5' 10'', 180 pounds, lean and somewhat muscular. It's just that things never quite seem to go my way in this department.

There was Tammi, the drunk 19-year old I lost my virginity to on a college-sponsored spring break trip four years ago. She was my first and I spent the entire week flirting with her. Sure, it was fun, but something about a girl leaving to throw up moments after climax was a tad disheartening.

Safe to say things didn't really blossom after that.

Then came Sheila. Oh, lovely Sheila.

Sheila and I met in an advanced math class my junior year and fooled around for a little over two weeks. She was the first person I ever went down on, the first person who ever went down on me and everything was going well...until she told me she found someone else and wanted to "just stay friends".

Lastly, there was Ashley.

Ashley was my most recent real conquest (the occasional blowjob by a one-night stand notwithstanding) and we met through mutual friends at a birthday party.

I never really thought she was that into me until the night we were hanging out at a local bar and started flirting. Flirting led to hugging. Hugging led to kissing. Kissing led to ... well, you get the drift.

The only snag was, no matter how hard I tried, no matter how long I went down on her or changed positions, I couldn't make her cum.

I just couldn't do it.

She never told me what was wrong, and I thought she was having a good time, but we could never get her past that obstacle.

Needless to say this hurt my self confidence.

Which bring me back to my original point.

As guys, we're trained to think we're God's gift to women. When something throws a chink into that plan, it's hard to know where to go from there.

Luckily for me, I wasn't alone in my journey to reclaim my confidence.

==========

No matter how bad I think I've had it, my friend Amber always finds a way to one-up me.

When I told her the story of Tammi, she told me about how when she lost her virginity, it hurt so much she cried the entire time.

I told her how much it hurt when Sheila ended things and she came back three weeks later having just caught her boyfriend Mark having sex with some other girl.

Over the past two years, Amber and I have had our share of bad luck in the relationship department and I knew that I could turn to her for advice on how to gain my confidence back after the Ashley fiasco.

I never expected it to turn out the way it did, though.

It all started with a text message.

"Hey, you free tomorrow night?," I asked. "I really need some advice and am feeling like shit right now,"

Amber said she had to work until six, but after that, she'd come over and we'd rent a movie, veg out and get my mind off things.

True to form, she was at my door with ten minutes to spare and as I took her coat, I could tell she had something on her mind as well.

"So, what's going on?" I asked.

"Oh, nothing much," she replied. "It's just the same ol' shit. Met this guy named Ken on EHarmony, went out for some drinks and he said he just didn't feel a connection. What the hell is that? First off, this guy was like 20 pounds overweight and then he says HE doesn't feel a connection? I swear, if my mother wouldn't kill me, I'd give up men altogether."

"Hey, don't lump us all together. There are still some of us out there that are good," I said.

"Yeah, but they're all gay or married or both," she chuckled.

We went on like this for about an hour. I told her about Ashley, she shook her head and did her best "Come on, you're better than that" speech.

It really wasn't having an effect.

"Well, you want to drink your troubles away?" she asked.

"Sure, why the hell not?" I replied and got up to head to the fridge. "The usual?"

"You know it,"

Back from the fridge I came with a hard lemonade for her and a mix of Jack and Coke for me.

The booze made the movie we were half-watching a tad more enjoyable, but I still to this day couldn't tell you what it was about. Something about a guy trying to avenge his family's loss or some crap.

It was right around 9 p.m. when I really started feeling a little bit buzzed, and then Amber asked me a question I really didn't know how to answer.

"Tom, do you think I'm pretty?"

"Well, um, yeah. You know you're good looking, I mean, people stare at you all the time."

In truth, I wasn't lying. At 5' 5'', 125 or so pounds, Amber had a body most 23 year olds would kill for. She was fit but not muscular, strong but not masculine. And as far as T&A, well, let's just say that I've taken my fair share of glances.

I never asked her directly, but I had to believe she was on the small side of a C cup, with wavy brown hair that flowed down to her enviously round ass. Just picturing it now brings a smile to my face. The curves caused her jeans to roll around, nearly forming a perfect half-circle. I always wondered what it would be like to see her naked, but chalked it up to my genes and the fact that as a man, I'm inclined to wonder that about just about everyone.

"So what's wrong with me that I can't find someone?" she asked.

"Eh, nothing. I mean, you know it will happen when it happens. These things take time." I answered back, trying to sound polite while spewing those lines for the 10,000th time.

"I just don't get it," she responded with a slight sigh. "I see these women everywhere with boyfriends ten times as hot as them. What do they know that I don't?"

"Maybe they're sluts," I joked, causing her to hit me with one of the pillows on her side of the couch we were sharing.

"You make it sound like I'm a prude," she smirked. "Trust me, I'm far from it."

"Oh yeah, here it comes. Is this you're 'I'll do things with the right guy' moment?" I asked.

"Shut up," she barked kiddingly. "It's true. I'm not gonna fuck some guy on the first date, but it's not like I'm waiting for marriage either."

"So what are you waiting for?" I asked.

"Someone to say they like my tits," she responded.

We both immediately fell to the couch laughing. I hadn't expected such a blunt answer from her, and while I was sure she was joking, I couldn't pass up such a window.

"Well, I like your tits," I said.

"Do you now?" she laughed while cupping them in her hands. "I really am quite proud of them. I don't know though, maybe , guys are intimidated by them."

"I doubt it," I said.

"Well, then, asshole, what is it?," she smiled. "If it's not my tits, what is it? Why won't anyone flirt with me?"

"Maybe it's your charming personality that scares them off," I said and moments later regretted as another pillow came flying at me.

"Like you can talk...Mr "I want someone to love". What kind of bull is that? You're 25, you need to go out and get some," she said.

"Hey, let's not change the subject," I said. "Back to your tits."

"What about them?"

"I don't know. You brought them up," I said.

"Yeah I did," she laughed, going back to her juggling routine. Before I could ask her what the hell she was doing, she reached under her white shirt, grasped the fabric and lifted her shit and bra, revealing to me two of the best breasts I have ever seen.

Not too big, not too small, the size was just perfect. Her pink nipples equidistant, shining, radiant.

The sight of her breasts made me speechless. Here I was, wanting to have a talk about my lack of self confidence and here she was flashing me.

How the hell did this happen?

"See," she said, readjusting her shirt back to where it was earlier. "I told you: intimidating. What, you got nothing to say?"

"What the hell do you expect me to say to that?," I asked after snapping back to reality. "I mean, who does that?"

"Ah, they're just tits," she said carefree. "So, what did you think?"

"Um...."

With that, she lifted her shirt again, this time resting it above the top of her breasts. She grabbed each one with a hand, as if showing off a piece of art for exhibition.

"Do you think they're too small? Too big?," she asked.

"No, um, they're a good size," I said.

"Well I like them," she replied.

"Good?," I asked, still bewildered that I was staring at one of my best friend's breasts.

"Don't be afraid. They're not gonna bite," she said.

"Yeah, I know that, but I don't know what you expect me to say here,"

"Don't say anything. We're just joking around. Come here, feel them," she said.

"Are you kidding?" I asked, feeling the blood starting to work its way below my belt. "What is this, show and tell?"

"No, it's nothing like that," she replied. "I just want a little advice from you. As a man, what do you think of my body? Should I work out more? Is it sexy"

With that her words drifted off. With a smaller tone I heard her ask "Would you do me?"

"Yeah, if we weren't friends," I said. "I'd be lucky to mess around with someone as hot as you."

"Good. Now come over here and give me your friggin' opinion." She said.

I don't know why I did it, but I got out of my seat and walked over to her. I took a seat on the loveseat next to the couch we were sharing and said "Um, ok".

As I reached my arms outward, all I could think was 'this isn't really happening' and something about the taboo of messing around with a friend really turned me on. I could feel myself bulging and was doing my best to hide what would probably have been a fairly obvious erection.

But, nevertheless, she asked nicely so here I was, inches away from touching her breasts.

My first thought as I felt the warm flesh fill my hands was that this was going to be something I was going to jerk off to the moment she left. I don't know why I thought about that, but it just was in there, circling my mind.

I reached and gently cupped her breasts, first the right one. Softly, I caressed it, holding its full weight in my palm and gently brushing across the nipple. As I didn't want this situation to get out of control, I did my best to keep it as medical-like as possible.

I didn't want her getting the wrong idea, of course, and lord knows what she would have done if she could have read my mind that instance.

I pictured kissing each of her breasts, gently flicking my tongue across her nipple as I slowly circled my index finger and thumb around the outer edge. I pictured taking both in my hands, sucking on them as she moaned passionately in my ear.

Her voice brought me out of my daydream and, from the looks of it, it wasn't a moment too soon.

"See, I like them because they're soft enough to the touch but also nice and firm and they don't move," she said.

With that, I went back to the loveseat and did my best to think of anything else.

"Yeah, I can see that," I said matter-of-factly. "They're definitely nice and they have a really nice glow about them."

"You're like the third guy that's said that to me," she said. "But most of them don't know what they're doing anyway. Mark thought they were like doorknobs, twisting, turning. It got to the point that I usually left my shirt on when we were messing around."

"That sucks," I replied. "I know what you mean though. I used to be like that until Ashley told me she didn't like it when I did that. She was pretty sensitive and she showed me how she liked to be touched."

I demonstrated my technique for her, slowly circling both my hands in motion, allowing them to meet in the middle. Just for the fun of it, I even acted out kissing them. That got quite the chuckle out of Amber.

"Good job Lover-Boy," she said.

"Yeah, well, I guess it was nice to get one thing right," I said.

"What do you mean?" she asked.

I got into more detail about Ashley. I told her about how when we had sex, I tried a bunch of different positions and still couldn't get her to climax.

"So what do you care," she asked.

"It messed with my mind," I replied. "When I can't get her off, I start thinking something's wrong with me. Then I can't focus and I can't climax either. It's not fun."

"Oh, come on, it's a little fun right?" she giggled.

"Well, yeah, but then it ends awkwardly and I swear I'm swearing off sex forever."

"Maybe she just doesn't cum during sex," Amber said blazingly. "I'm like that sometimes. Hell, even when Mark was at his best, it was still 50-50 if I got to cum or not."

"I'd take those odds," I said.

"Alright, spit it out," she said. "What do you think you're doing wrong?"

I tried to change the topic, and said "Nothing", but Amber wasn't going to take that for an answer.

"Come on, I told you what I thought was messing me up. Now spit it out." She said.

"If I tell you, I swear to God, you better not tell anyone else," I said.

Amber agreed, but I still couldn't bring myself to say it.

"Well I....I.." I stammered.

"I....I.. nothing. Stop stuttering and say what's on your mind," she answered.

"Fine, to hell with it," I snapped back. "I don't know about my size."

"Oh, come on, you're not even close to 200 pounds, you're far from fat."

"That's not what I mean," I said.

As if a light bulb just went on in her head, Amber replied. "Ohhhhhhh."

"Yeah," I said. "I know I'm not small or anything, but it's got to be something, right?"

"Well, let me see," she said.

"Excuse me?"

"Yeah, let me see."

"No way,"

"Oh, come on, I let you see me naked."

"Yeah, but that was different. You flashed me and asked me to feel you up to give you an opinion of your tits. We're talking about me whipping out my dick like it's nothing."

"Eh, so what?" she replied. "It's just the two of us here, it's not like we're going to break some kind of rule. You said you felt like shit right? Well, maybe if you had someone neutral to give you an opinion, you'd feel better."

Showing Amber my penis wasn't that big a deal. The problem was, her asking to see it caused me to get even more turned on than I was when I felt her up.

I couldn't stop thinking about what it would be like to show her it and then take her right on the couch. Plus, it wasn't like I could hide the fact that I had an erection if I took it out.

"You know, this isn't exactly what I had in mind," I said. "And frankly, all this talk is getting me a bit hard and I don't want that to make things weird."

"Please," she said. "Man, I've been wet for like 20 minutes."

"So what the heck does that mean?" I asked. "Isn't this a little strange? We're friends. We shouldn't be doing this."

"We're not doing anything," she said. "I showed you my tits, you felt them, I got wet. I asked to see your dick, you got hard. It's just natural things the body does. It's not like I'm going to start banging you on the floor. We're still just friends. We're just trying to help each other out."

Maybe it was her calm approach, maybe it was the fact that I wanted to see where this was going, but either way, the next thing I knew I was sitting there on the loveseat getting ready to take my shorts off.

Since I didn't want to just stand up like a Roman statue or anything, I continued to sit on the cushions and reached my hands to the waistband, clutching my shorts and briefs with one motion.

"You can't laugh or snicker or anything," I said.

She nodded her head and I lifted my legs, took both the shorts and briefs off and kicked them aside.

I adjusted myself so she could see a little better and there in all his glory was my erection, pre-cum glistening off the tip.

"Hmm, not bad," she said.

"What do you mean 'not bad'," I asked.

"Well, it's hard for me to tell from here," she said, scooting to the floor.

In a slow-motion moment I'll likely never forget, Amber dropped to her knees and crawled over to me, positioning herself in between my legs.

"Do you mind," she asked, motioning that she was going to touch it.

"Uh...no," I stammered out.

She grasped my dick in her hands and carefully moved it from side to side, examining it much in the way I had done her breasts earlier.

"It's a good size," she said. "I'd say probably five-six inches, which is average. You've got a decent width too, and that's really the important thing."

Without noticing it, or at least I don't think she knew she was doing it, Amber's hands started moving up and down. Her grasps on my penis was soft, her touch causing me to swell even further.

"No, make that seven inches," she giggled. "It's really nice, Tom. I mean it."

"Oh, um, thanks," I said.

"Listen, can I ask you a favor?" she said, gently continuing to stroke me. At that moment, I would have agreed to anything.

"Yeah, sure,"

"Just don't freak out, ok?" she asked.

Before I even had a chance to respond, Amber flicked her tongue across the tip of my penis. She moved her face closer, opening her lips and stretching them out to the top of my crown. I felt her lips part and work their way down to the middle of my shaft and felt an immense heat engulf me.

"OH, god, what are you doing?" I asked.

"I just want to try something on you," she said. "Just let me know if it feels good."

"But you're sucking my dick!" I exclaimed. "We can't do this, we're supposed to be friends!"

"Listen, I asked you for advice, you gave it," she said. "You asked for advice, I gave it. Now it's my turn again. So, does this feel good?"

She moved her head back down, this time grasping my shaft with her right hand and as she moved her lips just over the crown, I felt her tongue swirling across the head. She went down as far as she could and as she came back up, make a loud sucking sound that drove me crazy.

Without being able to control myself, I put my hands on the back of her head and did my best to enjoy it.

"Ummm, you like that?" she asked. "You like the way I suck that big, hard cock of yours?"

Her dirty talk nearly pushed me to the breaking point.

"Oh god, don't stop." I said.

"I'm not going to," she said.

Amber began to softly stroke my dick with her right hand and moved her left to softly caress my balls. Meanwhile, her lips moved faster and faster down my shaft, only every so often would I see the tip.

"This feels so good," I said.

With that, Amber's eyes looked up and we stared right at each other. Gone were the words. All that remained was the feeling of her lips giving me one of the best blowjobs I had ever received, her mouth heating me up to the point where I wanted to explode.

"Oh, god, I think I'm going to cum," I said.

"Go ahead baby," she said. "Shoot that hot load into my mouth. Yeah, you like that?"

She sucked faster, her tongue bouncing and circling around my member.

"MMMM, come on baby, let me feel it," she said.

Her hands cranked faster, up, down, back, forth.

"Let me feel that hot load," she said.

As if almost on cue, I felt it building inside me. I didn't know how much longer I could hold out. Her eyes started right at me, almost begging me to cum inside of her. I moved both of my hands to the top of her head.

"Oh, god, here it comes," I said, trying to warn her. "I can feel it.....OOOOOOOHHHhhhhhhh."

I felt the first blast explode out of me, no doubt hitting her in the back of the throat. She slowed her rhythm down now, still pumping, still sucking.