The No Strings Challenge - Cover

The No Strings Challenge

Copyright© 2007 by lametoad

Part 19: Wow, just wow!

Erotica Sex Story: Part 19: Wow, just wow! - Regular guy puts out a challenge on the internet to have the best sexual experience possible. Things work out pretty well.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Group Sex   Harem   Oral Sex   Anal Sex   Slow  

To my subscribers:

This year taught me that every woman brings special qualities to any emotional or sexual encounter. Having to rank them does a huge disservice to that truth. Because there are too many variables, It's not even really possible to rank a particular activity like a woman's oral sex skills. I had the time of my life trying and finding out though :} Yes, some women are better at it than others, but beyond a certain level - mood, preference, emotional connection in the moment all play too big a role. While I can't imagine any man, even the Pope, being less than ecstatic to get fellated by Stefani, she's not a perfect fit for just anyone :}.

All the women I met through this experience were winners in every sense. That said, this is America (we rank everything) and many of you helped pay for this site because you expected/demanded a final ranking for the No Strings Challenge. I get that. I repeat that I'm really reluctant to do this. Many of these ladies aren't just friends now, they're much more than that to me. I know that ranking their sexual talents is going to hurt feelings. Ladies, please believe me when I say that doing this hurts me. I foolishly made this promise or at least implied it at the beginning of the Challenge, but I have to keep my word.

Again: I am rating my first sexual encounter with each of these ladies, nothing else. I am also rating it as a sexual not a personal experience, the original terms of the Challenge.

12. There were supposed to be 12, but I know that one of my 12 didn't really know she was part of the Challenge. It's not fair to rate her in anyway. It also means that no one finished 12th or last because none of these incredible women could ever be said to be last.

I did also have the pleasure of meeting with Kayden Kross just before I checked out of the Bellagio. I had a wonderful time with her, but we had an equally wonderful time just talking about books. We grew up in the same town, so it was fun sharing that as well. She would definitely not have been twelfth.

11. Ginger Lee - Before this started, if anyone told me that Ginger Lee would finish 11th in this thing I would have sworn that person was on crack. She was my fantasy girl for a long time and when we did our scene together she did nothing to disappoint me on that count. She was everything I imagined she'd be both physically and sexually. It was really the fact that our meeting was limited to shooting what was supposed to be a POV blowjob scene for a porn movie that affected her ranking. Ginger is sweet, Southern, and she says "simple", but she's one of the brightest women I've met. She's a great kisser and if you've seen her movies all I can say is that she's even more incredible in person. I still can't believe that Ginger Lee swallowed for me and that I have the proof on video.

Here's the bottom line. I still fantasize about her from time to time. If meeting Ginger had been the only thing that happened during this challenge, it would be one of these secret-treasured memories that I'd be savoring on my death bed. I can't even say that it won't be anyway. Fwiw, I loved the off-camera Ginger as much if not more than the on-camera version of her. She easily would have been my trifecta. I just wish that she had better taste in sexting partners though I understand that he was the one doing the sexting.

10. Vicki Mitchell- By any standard, Vicky was and is a natural wonder (two of them actually). I'm still jealous of Frank Mitchell and that's a big part of the reason her ranking was affected. Whatever happened between Vicky and me, she did for Frank in some sense. As wonderful as it was, I was always aware that I literally and figuratively don't measure up to him. Vicky's also more of a fucker than a sucker and as you're well aware, I'm the opposite. However, after what happened with Tabby and Frank that apparently may have changed some. In any case, Frank's going to be the only one to be the judge of that. I just hope that I can someday have the sort of love in my life that Vicky and Frank share.

My experience with Tabby and Vicky in the strip club changed my understanding of what was possible sexually. She was an equal partner in my first threesome and even though I supposedly have a one woman heart, I'm not sure I'm going to give up being with two women at once. Unfortunately, I can't count it for the challenge. fwiw More people read about that encounter than any of my adventures. Vicky, Tabby's lucky to have best friends like Frank and you.

9. Dani–This is no reflection on this woman's incredible skills or her beauty. I had never thought of fellatio as an art form before my dessert with Dani. Obviously, the limitations of our meeting are the impediment here. We only had oral sex. It was exquisite and memorable. I still count her lessons for Alix the greatest present I've ever gotten. Whenever Alix goes down on me, I'm always reminded (don't tell Alix) that Dani was responsible for some of the extra pleasure she gives me.

I may have said that Stefani, Tabby, and Darcy were the three best cocksuckers in the world, but the one thing they have in common is that they all took lessons from Dani at some point.

8. Audrey- People have asked why so many of my encounters were with sex workers. One simple reason is that women who escort or do movies are far more likely to be willing to do it with a stranger, especially a stranger who was also going to post about it on the internet. Not too many wives or girlfriends in regular relationships were going to try this. That said, there is something to Malcolm Gladwell's 10,000 hour rule that says that practice matters. With a couple notable civilian exceptions, I believe that call girls and pornstars do tend to be better at the physical side of sex because they get more practice with partners they don't know well. I also learned that a lot more women have had sex or at least have been sexual for money than people think. Often they do it for a bit, then just blend back into the supposedly normal world.

I did eventually have a threesome with Samantha Sierra, but I was with Audrey first. I didn't have sex with Audrey; I made love with her and I treasure that memory. In fact, this ranking is amazingly high given the fact that Audrey and I didn't have oral sex that night and that's my favorite activity. This was the beginning of my discovery that the best sex included feelings. We did nothing exotic. I only came once, but once can be completely satisfying.

Audrey, you are my special friend in all of this. We shared very intense personal feelings, but much like Vicky it's clear to me that you were in love for the long haul with someone else and that simply made things different. If I could count our morning together with Nikki, you would be much higher in the rankings. Btw thanks for helping me live out my pornstar fantasies in every sense possible.

7. Alix- My first reaction was that this had to be higher, but I promised to be objective. Alix was amazing that night and has been even more amazing each time we've been together since. We already felt like best friends before our encounter and that may have taken some of the edge off of it. I knew that I'd be seeing Alix again no matter how things turned out that night. If I had to rank on total experience together, Alix would be on the top of this list.

6. Darcy - If I regret not spending more time with anyone, it's Darcy. There were several beautiful women in the Challenge. Darcy is a match for any of them, but she also happens to be the woman who is exactly my physical type. Darcy had a set of sexual skills that were particularly attuned to older men. I like to think of myself as middle-aged, but relative to Darcy I probably am an old guy. She was so good orally that I suspect that with a couple years of practice, she might go from being close to Tabby and Stefani in this area to being well beyond them. She had the most amazing sense of rhythm and grace in bed. It was like she was making sure everything looked, felt, and happened just right. She won the 3 minute challenge and that story she told about how she loved to slowly get a man hard with her mouth and tongue so much so that the longer it took to get there the better got me both completely turned on and relaxed at the same time.

Darcy is almost a perfect combination of the best sexual qualities of Tabby and Alix. Our match personally was different though and that has nothing to do with the Challenge. Darcy's courtesanship skills are so good, I still don't know if she was sincere or putting on a show. Tabby says that she doesn't think it was an act, but I guess I'm still wondering.

5. Dr. Tarah- Not that she isn't gorgeous, but voluptuous women weren't really my thing until I saw Dr. Tarah belly dance. I also wasn't that interested in anal sex until I met up with Dr. Tarah's ass (though that wasn't part of our first meeting). What man wouldn't want to hear from an expert that he has a magic cock? Sometimes, I think any one of my top seven could have been my top one. I don't know that I've had a more exciting moment than getting to the hotel room with Dr. Tarah after she'd finished her act in that secret strip club. Imagine a day that begins with going to a doctor to deal with your impotence and ends with coming in a beautiful woman's mouth.

4. Stefani –I had no idea that there were woman out there who loved sucking cock more than I loved having my cock sucked. Tabby and Alix were the first to persuade me that it was possible, but Stefani is the woman who erased any remaining doubt. There are women who actually prefer sucking to fucking, but Stefani is the only woman I've met who seems to prefer sucking cock to breathing. It helps that Stefani is seriously hot too. She remains my perfect fit and the best cocksucker I've ever been with. In the heat of the moment, I told Tabby once that Stefani was the "best cocksucker" and Tabby gave the best "blow job". I had no idea what that meant when I said it, but I think I understand the distinction now. Cocksucking is the purely physical aspect of the act. The blow job is that but also includes the mental and emotional which often depend on the chemistry between the blower and the blowee.

During the challenge, my sexual tastes also shifted. I started out as a guy who was all about the blow job. Because I was meeting such talented and sexy women, my palate shifted some and other aspects of sex became more important. I'm still primarily oral, but that first time even Stef admits that we weren't very good together at regular intercourse. She learned pretty quickly from Nikki, but once again our threesome doesn't count. One discovery I didn't mention was that kissing and touching were much more important than I thought they were. Fwiw, Stefani's a terrific kisser, thoughI have to confess that it was a little odd kissing a woman who had recently done a blow bang with seventeen men then hunted down the camera guy afterwards.

This is the bottom line though. Stefani got me, a middle-aged guy, to come nine times in a single night. I'm actually surprised that she didn't finish higher just for that alone.

3. Nikki –The first time I saw Nikki, I was stunned just to be in the presence of a woman who was that beautiful. When she suddenly took off her dress and propositioned me, I forgot to be self-conscious or nervous in the way I often am around beautiful women. We fit together both sexually and personally. There was no learning curve with one another's bodies. I also trusted Nikki in every imaginable sense immediately. For some reason, I never doubted that the trust and comfort was mutual. There's no more exciting feeling than to look down at my penis and see Nikki's exquisite face instead. As amazing as her body and face are, if you asked me what the sexiest part of Nikki is, I'd say without hesitation that it's her smile. She's also, along with Dr. Tarah, the best partner I've ever had for conventional sex.

Maybe this comfort level explains why Nikki's so amazing in a threesome. It's just that I can't count those meetings in this ranking.

2. Tabby – I've masturbated to my fantasies/memories of Tabby more than any woman I've ever known. From the beginning, Little Miss Hoover has known how to press every one of my sexual buttons. I've never been the same since. Not only did she introduce me to physical tricks that I never dreamt existed, she opened up the whole matter of just how mental really great sex is. What I thought were my limits, simply weren't. On top of that, I fell in love with her. I suspect that my body knew that before my heart and mind did. No woman combines the physical with the mental and emotional skills more completely than Tabby. I'm always mesmerized in her presence. The hardest thing about the Challenge was meeting Tabby then thinking that I might never see her again. I know I'm different, but the whole call girl thing turns me on. Tabby is the dirtiest girl that I've ever known and that might be the highest compliment I can give as long as she's my dirty girl.

1. Gina – It wasn't fair. Gina came into the challenge with something of a joker in her hand. I had unresolved issues about my long ago relationship with her Aunt Lisa. Gina gave me closure with those issues in spectacular fashion. In addition, what guy wouldn't want to learn from so beautiful and sexy a woman that he's been her crush for years?

Throw in the fact that Gina's physical beauty rivals Nikki (I confess, some of that is because I'm into blondes and Gina's a brunette) and her physical, mental, emotional skill set in bed is a very close match to Tabby's. I didn't get to have as many adventures with Gina as I did with Tabby or Dr. Tarah, but we're only grading that first meeting. Even without the prior connection, Gina would probably have finished close to the top of the Challenge. I know it's cliché, but the poolside- suntan-lotion routine got me very wound up. It's an old trick but Gina and that particular bathing suit brought it to a completely different level. I also can't discount the role of BBW Dom in the build up to our encounter. Before the challenge, I didn't realize how much I love being teased. Tabby, Gina, and Alix are all artists of the slow build and surprise. In the end, I thought Gina did it best.

I didn't expect the Uncle Charley thing to get to me. That had never been one of my fantasies, but it is now, at least with Gina. Call it nepotism, but my favorite niece is the winner of the No Strings Challenge.

I've had so many incredible memories in this challenge. There was Tabby betting me that I couldn't last three minutes in her mouth, Alix having me fill Gina's shot glass while teasing me about doing a threesome with Gina, the shock of Tabby coming to the door of Vicky's hotel room then turning up as the surprise star at the strip club, Vicky confessing that I got her off in a way that her superstar athlete husband hadn't, Audrey's orgasm when we made love, waking up to Samantha Sierra and Nikki sucking my cock together, my whole first night with Stefani, having Darcy and Tabby duel over my cock, Dr. Tarah's dance, and I'm sure I'm leaving several out. There is, however, one moment that stands out. It's Gina on her knees in front of the bathtub and begging me to come in her face for BBW Dom. It wasn't exactly romantic. It was actually funny, well as funny as giving a beautiful woman a cum facial can be. Still, how could someone this beautiful have ever had a crush on someone like me and how could she really be anticipating every one of my sexual fantasies like that? It's one of many moments where I was sure that I was the luckiest man in the world.

<hr>

I took several days to post the final rankings and comments to my website. I don't know if Alix or Tabby is the most sexually competitive woman I've ever met, but Tabby had the satisfaction of arguably winning the challenge since Gina had unique advantages that weren't fair, but they were within the rules. On the other hand, Alix finished behind both her stepsister and her best friend in her boyfriend's own rankings. I'm scared that she's going to make me pay. At the same time, the prospect of that is oddly exciting. Here's what happened in between that night at the Bellagio and now.

<hr>

After being with all four women in the night before, I slept. For one, Alix and Nikki's ages added together was less than my own. All three ladies were in superb cardio-sexual condition and I felt it was my duty to satisfy each of them. I didn't wake up until my cell phone rang at 12:30 in the afternoon. It was Dr. Tarah.

"Charley, I had a minute off before my presentation on the new restorative tonic. I wanted to make sure you survived last night."

I rubbed my eyes and looked down at my penis.

"The only thing that would have made it better was to have you there too."

"Charley, you know I had a date."

I didn't say anything.

"Tarah, thank you."

"For what, Charley? I've told you that swallowing your cum is as much fun for me as it is for you."

"I hope it is, I've never had a guy cum in my mouth."

"Funny, Charley. You know what I meant. And, I've never had a man cum as much you do or taste as good. Come to think of it, are you free for drinks this afternoon? I could show you the real meaning of 'Happy Hour'." I laughed.

"Seriously Tarah, I appreciate how you set things up with Frank and Tabby."

"Well, I worried that you might not be happy about Tabby kissing him and playing with his dick."

"It wasn't any more than what happens in a lot of lap dances."

"As someone who knows about these things, I have to tell you that some lap dances go further than that."

"I'm surprised that some of your customers even made it to the lap dance."

"Seriously, I hope you know now how much Tabby cares about you. She's not hanging around only because she loves your cock. I just did what any medical professional would do."

"Tarah, can I ask one more question."

"Of course."

"How do you really feel about me?"

There was a pause.

"Charley, I uh really have to start my conference session. Can we talk some other time about this?"

"Sure. But I was wondering if you knew how I feel about you?"

"Charley, dammit, you said just one question. I'll say this - you were probably hoping for one thing to happen with Frank and Tabby and the woman in me was rooting for the other."

The phone went dead. After all this, I was reminded that I didn't fully understand women. I don't know that guys are supposed to, but I regretted missing Dr. Tarah's signals. She'd been trying to see if I'd fight harder. Was it now too late? Was that something I wanted to do?

<hr>

I'd actually spent more time with Doctor Tarah than any other woman in the No Strings Challenge. She was also the only woman who was close to my age. It was kind of nice not to have to explain references, though Tabby was very used to being with men my age so she had absorbed a lot of things she'd never lived through. A few minutes later, my cellphone rang again. This time it was Nikki.

"Charley, I'll make this quick. I was wondering if you and I could spend time alone this evening."

"Of course. My only worry is about whether it'll be fair to the other girls."

"Charley, trust me. Being fair to Alix and Tabby is why I need to see you alone."

"Nikki, is this about Audrey?"

"Well, it is and it isn't."

<hr>

Nikki said she wouldn't be able to come up for another hour. For the next thirty minutes I waited for her in the suite. That's when Tabby texted, "Charley, we really need to talk before tonight."

My head was going a million miles a second. If I had no idea what might be up, it likely would have been easier on me. Instead, Nikki had any number of reasons to want to talk to me alone. She was living with Audrey, Alix was her stepsister, and somehow there'd never been anything completely casual about our sexual encounters.

I texted back,"Tab, I'm supposed to meet with someone else for a bit."

"I can't believe how horny you are. You should be resting not rutting."

"I don't think it's a sexual thing. Nikki said she really needed to talk to me alone."

"Oh God Charley, trust me I need to talk to you first."

"She said her thing was urgent."

"Charley, I'm asking you for this."

"Is Sierra okay?"

"She's fine. I miss her though. This isn't about her. Can you postpone your meeting with Nikki?"

I couldn't say no to Tabby. I texted Nikki, "Could we maybe meet a couple hours later? I have something I really have to do."

Nikki texted back, "???"

"I can't talk about it."

"Sure, hope you have fun with Kayden, but haven't you figured out by now that you can pretty much get laid anytime you want this week and you can talk to me abou t it too?"

"I'm not seeing Kayden."

"Oh."

"I'm pretty sure that it's not sexual."

"Didn't mean to sound jealous."

"I was thinking. I've gotten to live my fantasy. What would yours be?"

"Sexually?"

"Well in general too?"

"That's what I wanted to talk to you about."

"Maybe I could see if Tabby can postpone."

"You're seeing Tabby?"

"Shit, I probably shouldn't have said."

"It's fine Charley. I'm not like that. I just think that with Miss Hoover it always winds up being sexual."

"I guess it has so far. I promise, I won't do anything with her before I see you."

"You don't have to make that promise, Charley."

"I want to. Nikki, I know that you and I have big stuff to talk about. After Stefani left the other night, something was different between us. I'm not sure the whole fuck buddy thing worked."

"I felt the same thing, Charley."

"Oh God!"

"Exactly. C U in a couple hours."

"You sure?"

"Suck your cock and hope to die," Nikki texted.

"CYA then."

"Can't wait. BTW, I promise to have sex with you regardless."

"I can't wait either."

My head spun and my stomach churned. Once again, too much was happening. I needed to get out of the suite and maybe eat something. I got my card key then went in search of the vending machines. I went up a few corridors before I found one. Mostly, the Bellagio was about room service.

I expected to be the only one buying snacks and sodas, but that wasn't the case. A woman about my own age was already fiddling with the buttons on the snack machine. The red tin of Altoids she'd chosen had fallen on to the ledge instead of into the bin below. She hit the glass on the front of the machine, but not very hard.

"Dammit!" she groaned.

I stayed near the door of the vending area. The woman pushed more random buttons. She was dressed casually but elegantly. Her sandals and matching top and shorts were clearly not from Walmart. She was petite with reddish brown hair that came to her shoulders. No freckles, but a girlish face and a body that made me think string bikini. Her only body parts that appeared to be oversized were her breasts, butt, and eyes. Had she appeared before the No Strings Challenge, I would have been thinking about her for days. I also wouldn't have had the nerve to talk to her.

"Can I maybe help you?" I said softly.

She turned and smiled, "It's not that big a deal. I can buy another box downstairs probably."

"But it looks to me like you want those Altoids now."

Our eyes met and hers brightened.

"As a matter of fact, yes. You know that feeling."

"Of wanting something that can blast your mouth clean?"

She blushed. I hadn't intended or caught my own double meaning, but it was pretty clear that she did.

"Well, something like that. I missed breakfast and have been at this conference most of the day."

"So what conference are you here for?"

She looked at me again, "I'd rather not say. I don't mean to seem rude, I'm just not at liberty."

I nodded, then helped her tilt the snack machine forward. Before I did that, I had her step to the side, just in case it fell on her.

"Once I get it leaning, can you smack it on the side? That should get the Altoids over the lip."

My auburn-haired friend slapped the side of the machine with a solid thwack. The tin of Altoids plopped into the space behind the metal flap. She slipped her forearm in, got her Altoids, then winked at me.

"You sir are a true gentleman."

"Glad to be of service to a lovely lady."

She pulled off the plastic with a red-painted fingernail. "The least I can do is to offer you an Altoid."

She ran her tongue across her lips, then slowly popped three Altoids into her own mouth.

"Those are some very lucky Altoids."

My first thought was that I'd gone too far. I half-expected to get slapped and fully expected her to walk off. Instead, she smiled.

"Here, I took you for the shy type."

"Well, I used to be."

She took another Altoid from the tin between her fingers and placed it seductively in my open mouth letting me taste her fingers. In doing so, she brushed against my chest. I put my hands just above the flair of her hips. Her top exposed a tantalizing glimpse of flat stomach. She kissed me.

"Mmm, you know what would really go great in my mouth with these Altoids?"

She slid her hand over my bulging zipper.

"Does it melt in your mouth and not in your hand?"

"We'll have to find out. That is, if it's okay with you?"

She dropped to her knees, then motioned for me to close the door to the vending area and to keep an eye out through the half glass for anyone coming down the corridor.

"Let me guess. You're here for the Bella Luna Convention?"

"How do you know about us?"

"I was lucky enough to meet a member."

My Altoid friend had gotten my penis out and already had about a quarter of my shaft in her mouth. As soon as her tongue touched my cock, I felt a cool jolt, the peppermint from the Altoids. The skin on my penis tingled.

"Curiously refreshing," I said in my best British accent.

"I spent most of the morning licking my girlfriend's pussy. She's great, but I really really needed some cock."

"Glad I could help."

I stroked her hair as she went back to work. This was clearly no beginner. She combined suction, with a snaking tongue movement on the underside of my shaft, and a steady unhurried rhythm. The only sound in the room other than her gentle slurps and my sighs was the whirr of the ice maker in the corner.

"God, that feels good. This is the best Altoid, I 've ever had."

She started to laugh, but wisely pulled me out of her mouth.

"You really shouldn't make a girl laugh with her mouth full. You could get bitten."

"Am I going to get to return this favor?"

"I don't have time, have to get back to the conference. If you want to join my girlfriend and me tonight, I'd love it. You don't mind being shared do you? We used to get together with her husband. He definitely didn't mind."

"Is your friend as hot as you are?"

"Probably hotter, especially if you're into blondes."

"Well, right now I'm totally into redheads."

"Good answer, let's show the studio audience what you've won."

She swallowed my cock again. The prospect of another threesome momentarily made me forget my complex and possibly scary commitments for the evening. I pushed into her mouth and she gagged.

"Sorry!"

"Why sorry? I love rough oral with the right guy."

She slipped me back in her mouth as I began to thrust towards her throat. For whatever reason my big head re-gained control for a moment, "Oh God, I never thought I'd get an invite like yours and find myself saying this, but I have to take a rain check. I have to be somewhere and there's no way I can cancel."

"Well, bring her along."

I thought about how sleazy what I'd just said sounded. It wasn't like I was some congressman from New York or the Governor of California. I softened ever so slightly and hoped that she didn't notice. She did. She kissed the tip of my penis.

"Don't worry about it sweetie. It's not like we're going steady. Let's not get ahead of ourselves. I'm perfectly happy just having this chance to suck a friendly stranger's gorgeous cock. Shall we get back to business?"

I sighed.

"Of course, it just felt really awkward. I'd love to meet your girlfriend. I'd love to spend some time with you alone too."

"She must be pretty hot, for you not to ditch her for what I just offered you."

"She, I mean they are."

"Oh my! I've caught myself a serious player here."

The tin of Altoids was now on the floor next to where she was kneeling. She reached in for another and dropped it on her tongue, then took her cocksucking to yet another level. Between the tingle from the Altoids and the softness of her tongue, I wasn't going to last much longer.

"I'm going to come any second."

Her only response was to point her index finger at her own mouth, nod her head, and stare playfully into my eyes. Keep in mind that I'd had five orgasms the night before, but my balls didn't seem to know it. I started to spurt. After the third or fourth spurt, her eyes widened. I'd clearly caught her by surprise, but she managed to keep my in her mouth until it stopped spasming.

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