Daring To Leave The Friend Zone

My friend Kelly had broken up with her boyfriend of two years about a month ago, and she wasn't having much luck with men since then. After a series of "rebound" dates that ended up showing just how much of an asshole her dates were she was extremely frustrated. Since the moment I met her eight years ago I've been extremely attracted to her. However, timing is everything, and it's never quite worked out for us. You know the drill, she's in a relationship, I'm not, I'm in one, she's not, and it's been quite frustrating.

That's why, when timing finally chose to help me instead of screw me as usual, I jumped at the chance and offered to take her out. However, remembering her string of bad dinner and a movie dates, she asked if we could stay in, so I offered to make her dinner. Now, I'm no Emeril in the kitchen, but I'm no slouch either. By the time she showed up on Friday, I was halfway through making our dinner: wine chilling in the fridge, etc. She let herself in and I turned around to see her standing there in a pair of faded low rise jeans, a skimpy tank top, and an unbuttoned collared shirt. Not the sexiest thing ever, but on her it just looked incredible! Her streaked blonde brown hair pulled up left her gorgeous neck and collarbones showing, and her amazing green eyes twinkled at me. I drank in the sight of her for a good few seconds until I noticed the look she was giving me.

"What's wrong with you? Haven't you ever seen a girl before?"

"S-s-sorry," I stammered, "Do you want a glass of wine?"

"Sure, I'd love one," she replied.

After she took her glass, she sat down at the bar next to the kitchen to talk to me as I cooked. The small talk was great between us as usual, we had a rare ease in our interactions, it was one of the reasons we were so close. Once the dinner was over we adjourned to the living room.

"That was a great dinner Steve," she said, "I really glad that we've gotten to spend some time together lately, we always have so much fun together."

"Yeah, me too," I said, "it's been too long since we've had a chance to get together. I think the last time we hung out just the two of us was that time in college when we played truth or dare after everyone else left my party and your boyfriend passed out on the floor next to my girlfriend on the couch."

"Really?! Has it been that long?" She said.

"yeah, I think so," I replied. "I mean just the two of us hanging out."

"Wow," she said. "That was a really fun time, I couldn't believe the stuff you told me, you were definitely drunk that night! Oooh, we should play that now, might as well keep with form for our nights alone!"

"Hmm, well, I'm not sure I'm drunk enough to say all the stuff I don't remember saying last time, but I'm game if you are."

"Okay," she started out, "Truth or Dare?"

"Oh, my turn huh? I guess I'll start out with truth."

"Hmm, do you think I'm pretty?" She asked.

"Do I? I think you're absolutely gorgeous! I have a confession to make, I was totally checking you out when you came in, and you look perfect in that outfit. In fact, I've had a thing for you for quite awhile, but one or the other of us was always in a relationship and I've never been sure if you were into me that way."

"Really?" she asked in disbelief. "Wow, I never knew you felt that way. Do you think I would look better with bigger boobs? I've always wanted them."

"You with bigger boobs, hell no, I think you're perfect looking right now. Your small breasts suit your body frame and, well, at least in a bikini anyway, since I've never seen them, they make you look really really toned with that killer stomach and belly ring. Truth or Dare?"

"Hmmm, I'll go with truth. . ." she replied.

"Okay, how would you feel if I asked you out on a date instead of a 'friend date'?"

"Haha, well, I don't know are you asking me on a date? I would definitely be interested. I mean you're such a great guy, and pretty hot to boot, so yeah, I'd have to say I think that's something I'd be willing to explore with you. Truth or Dare?"

"hmm, well, yes I think I am asking you out, and I'll take Dare," I answered.

"Well, I dare you to kiss me!"

With that, I stood up and moved over to the couch and lifted her hand until she stood up. Then I leaned in, wrapped my arms around her and gave her the best kiss I had. It was amazing, everything I had ever thought it would be, as I always knew it would be with her. We kissed for a couple of minutes and my hands started to roam up and down her back; going farther down with each pass.

"Wait," she said, "it's my turn, I want to keep playing! I've still got to get some good stuff out of you!"

"Okay," I said as we sat back down on either end of the couch, "Truth or Dare?"

"Dare."

"I dare you to. . . show me those breasts of yours, since I've never seen them."

She stood up with a devilish look in her eye and slipped off the button up shirt to reveal only a tanktop. It was one of those tank tops with the built in bra and it looked like she wasn't wearing a bra, since, well, she didn't need it with those perky little A's. She winked at me as she stood up and in one smooth motion, she pulled her tanktop off over her head.

I sat in awe of the sight before me. I've always been attracted to athletic girls, especially a nice toned stomach, but she was amazing. Her large A cups looked to be about the same size as if you cut a softball in half and were just as perky. She had small nickel sized dark pink nipples that stood out almost a half inch like pencil erasers. She let me look for a minute or two and even gave them a quick fondle before she grabbed the button up shirt and put it back on, but instead of buttoning it up, she just tied it in the front so her wonderful cleavage and stomach were showing.

"What do you think?" she asked.

"Oh my god, you're absolutely perfect!" I groaned. "At least what I've seen so far. . ."

"Thanks, you sure know how to make a girl feel good. Truth or Dare?"

"Dare."

"Hmm, well, you did get to see me, and I want to know how turned on you are. I dare you to show me your cock."

"Okay, no problems there, he's at his best after your . . . display!" I said as I sat up and began to unbuckle my pants.

I took off my pants and stood up, my large erection supporting a tent in my boxers. Thinking that it would look kind of stupid to have no pants on and my t-shirt, I pulled that off over my head too, showing off all the work I did in the gym. I've worked hard to keep my college basketball body after my college career was over. I'm 6'6" and about 230lbs of lean solid muscle. So when I took off my shirt, my toned stomach, arms and chest came into view. I looked back up at her because I wanted to see her face I as I completed my dare and she was already blushing. I hooked my thumbs under the waistband of my boxers and gave a little tug causing my cock to pop free. Now, I'm not going to lie and say I've got a giant 14" pulsing pornstar cock; but I do have a solid 8 ½" with a good solid girth (not too thick or too thin). I mean bottom line, I'm not huge, but I'm definitely not small. Since I spend so much time in the gym trying to keep my body toned and in shape, I also keep myself well groomed and shaved.

At the sight of my cock, Kelly gasped slightly and her hand went unconsciously to her crotch as she took it all in. After a few seconds she caught herself and removed her hand from her clit and sat back up.

"What do you think?" I asked.

"It's beautiful. It looks like the perfect size, not too big to hurt, but plenty big enough to please," she said; not able to make eye contact and still staring at my cock.

As I pulled my boxers up and sat down, I asked "Okay, your turn, Truth or Dare?"

"Definitely Dare," she exclaimed.

After a moment's thought I said, "Okay, I dare you to masturbate to an orgasm. But if you're uncomfortable in front of me, then you can go in my bedroom. But I'll need some kind of confirmation that you came."

"Okay, I'll go in your bedroom she said and giddily hopped up and ran and jumped on my bed, closing the door after her.

After a few minutes she called out, "Steve, can you come in here a minute . . .?"

"Sure," I said as I got up. I walked over to my bedroom door and opened it, expecting to see her done, instead I almost fainted from the sight before me. She was laying on my bed on her back, totally naked. Her hands were busily stroking her clit and rubbing all over her completely shaved pussy.

"I need some help," she said and motioned me to come sit in a chair she had pulled next to the bottom of the bed. "Will you help me get off? Can you finger me so I'll cum, I just can't seem to finish on my own tonight?"

I didn't need any further encouragement. I sat in the chair up against the edge of the bed and she scooted down so her pussy was right on the edge of the bed and her legs were on either side of me. I gave her a questioning look and she nodded as I stuck my middle finger inside her. I quickly found her G-spot and began a gentle massage on it that made her eyes roll back in her head as she started to moan and wiggle her hips.

"Ohhh. Myyyyyy. Goooooddddd," she screamed as her climax began to envelop her.

She began to chant my name as I slowly massaged her g-spot. As her orgasm began, she gyrated her hips and lifted her ass off the bed. Her left hand was subtly pinching and twisting her left nipple as her right hand frigged her clit with increasing intensity. When she finally plopped back down spent on the bed I finally got a look at her in full. Her nude body was breathtakingly beautiful. Everything was perfect, well toned, and beautiful. Her legs were long and well toned, her stomach had the shadow of a six pack under the flatness of her skin. Her breasts capped her heaving chest and her collarbones, neck, and face were flushed from the intensity of her orgasm. Her clit was fully swollen and a wonderful dark pink color and since she was completely shaven, I could see every fold and crease on her lovely pussy.

She looked up at me finally and gasped "oh my god, you have no idea how bad I needed that orgasm. I've been so stressed with work and my stupid ex-boyfriend couldn't last more than 2 minutes with sex and was completely grossed out by getting me off any other means, which means that orgasm has been building for about 4 months."

"Well, I guess I'll let you slide on the dare, since I said to masturbate yourself, but I'm not going to complain. I'm just glad I got to watch, that was really hot."

"Okay, truth or dare stud?"

"Well, as much as I love a good truth, I'm liking the way these dares have turned out, so I'll have to go with dare."

"Okay, I dare you to masturbate, right here, in front of me. I want to see a real cock in action, I've sorely missed it."

With that she got up and we switched places. She sat down in the chair and I sat on the edge of the bed. I leaned back and quickly yanked off my boxers exposing probably the largest hard-on I've ever had in my life.

"You realize, after what I just saw, I'm probably not going to last very long with this right now, right?"

"Yeah, I know, but I've never seen a guy jerk off, and you've got a magnificent cock, and well, you've seen me do it, so it's only fair."

With that I licked my hand and got a nice motion going, trying to last as long as possible. The fact that she was sitting naked in front of me didn't help my staying power. What helped even less was when she slouched down in the chair and moved right over so her legs were on the edge of the bed and her pussy was within inches of my hard cock.

"I want to get a good view you know . . ." she reasoned when I gave her a questioning look. "Can I touch it?"

"Sure" I said. She reached down, without moving and wiped her hand in her pussy juices and slowly wrapped her hand around my throbbing member.

"My god this thing is perfect," she said as she gave it a couple of quick jerks that nearly sent me over the edge. "I want you to jerk off, right here, right now, and I want to see you cum!"

At that I started stroking in earnest, not worrying about how long it would take. This girl wanted to see a load of my cum and I was damned if I was going to keep her from it. I started to stroke faster and as I felt my orgasm approach I asked her, "I'm going to cum soon, where do you want it?"

"All over me. I love the feel of cum on my skin, and I love the taste!"

As soon as I heard that, I went over the edge. Looking down at her naked toned body that I've been fantasizing about for years combined with hearing her say those words was more than I could take. I felt like I was going to explode; and explode I did. I heard myself grunt loudly as I shot a wad of cum all the way up her body to her chin and neck leaving a long trail of cum a foot long across her tits. As the wave of my orgasm hit me, I shot rope after rope of my thick cum all over her body, completely covering her in it. When I finally finished, I looked down at her and saw her with her eyes closed, her tongue licking at the cum on her chin, her right hand rubbing it around her stomach and her left hand frigging her clit. As I watched, she had another orgasm and her body spasmed so hard I thought she was going to break her own back.

When she finally came back down to earth, she looked up at me and said, "fuck that was good. Do you normally cum that much, or was that just for me."

"Well, normally I do come a lot and shoot it pretty far, but I think there was a little extra in there for you because you got me so hot."

"Damn," she said, "then I can't wait until our 'date' . . ."

To Be Continued...