Side Bet Bluff Ch. 02

"Please," begged Jaycee.

"Please what?" I asked, as I slowly moved my right hand down.

"Eek!," squeaked Jaycee as she jumped away from me, and fell off my lap to the floor.

"You may have a fear of having your cute little butt touched, but I swear to you, Jaycee, you'll be over it by the end of our week," I predicted.

"I don't know that a week is long enough, Will," Jaycee said solemnly.

"Well you can have your butt touched lovingly with my caresses, or harshly with my spanks. The choice is yours," I said while helping her up to her feet.

"Your little fear there must make doggy-style particularly difficult," I added.

"I ...," she hesitated. "I've only ever had sex in missionary and cowgirl."

"Really? Well, we'll definitely have to fix that."

"Will," a very nervous Jaycee said, "I don't think I can do this."

"Jaycee," I said in as calm yet commanding a tone as I could muster, "you don't have any say in the matter." I half expected Jaycee to show some defiance or protest, but she just looked nervously down.

"Now, I think one of us is wearing too many clothes, don't you?" I asked.

Jaycee looked back up at me and smiled. She then proceeded to strip me of my clothes, and she was as careful in folding each item as she had been when she had taken off her own clothes back at Aaron's place. After removing my sweater and shirt, Jaycee looked at my chest appreciably.

"I don't remember you looking this firm over the summer," she said.

"I don't like to expose myself too much at the beach," I replied. "I'm pretty paranoid about sun damage and so I usually cover up."

"Too bad," she lamented. "Maybe I would have considered you datable material if I had known how well built you were."

"That's a little shallow, don't you think?" I asked.

"Weren't you the one who told me I could get any guy I wanted? After that I started setting pretty high standards."

"Touché," I replied.

Jaycee then knelt down and undid my belt and snap to my jeans.

"Shoes and socks first," I ordered. There's nothing more ridiculous looking than a man naked except for socks, except for maybe socks and shoes. Jaycee nodded and took care of my footwear.

"In retrospect," Jaycee said, "I think I haven't had much dating success because of that."

"How so?" I asked.

"The guys I started going out with were the types who could get any girl they wanted," she said as she kneeled at my feet. "Good looking, confident, rich. They didn't have the patience to deal with my crap. And I've never been very good at letting guys get close, and have a big problem with guys who don't respect the boundaries I set."

"Until this week," I reminded her.

She looked back up at me, gulped, and then returned to my pants. She moved my zipper down while gently grazing her fingers against the bulge underneath. Jaycee then grabbed the sides of my pants and pulled them down. I lifted up from the edge of the bed to help, and soon she was folding my pants to put with my other clothes.

When she turned back to look at me in my boxer briefs, she smiled. I looked down to see the very large stain of pre-cum right in the middle of my shorts. Jaycee knelt back down in front of me and slowly slid her hands up my legs about halfway. She then stopped, moved them down, then back up a little further. I idly wondered if this was one of her masseuse techniques. It certainly felt good, but at the same time I thought she might be teasing me a bit to try to exert some control, to make me react to her. Instead I just leaned back slightly and enjoyed it.

Eventually she had her hands at the top of my underwear and she grabbed and pulled down. When they were about halfway down she froze, and just sat staring at my cock.

I know in these stories every guy has a huge cock that he uses to ravage women left and right. So I guess it will seem cliché when I say I've got eight inches when I'm fully engorged. Maybe eight and a half, I haven't actually gotten out the freaking ruler, and besides it's got a bit of a curve, to make it harder to measure. But I estimate eight inches.

Still, I'm here to tell you that having a big cock can be a curse. This is a big part of the reason why I demanded a full week instead of just the weekend. I've never successfully concluded sex on my first attempt with any woman. It takes a while to stretch out a woman to accommodate me. Or, at least, it takes a while to stretch out the few women I've been with. Maybe I've just been unlucky. But this has meant that when I finally was able to have sex with a woman where it was enjoyable for both of us I had invested a good amount of time and energy (and sweat and frustration) and was loathe to go looking for someone new. Since breaking up with Hannah I'd had a few one night stands, and came close in my last one to having good sex, but got a little too aggressive when I got excited and started hurting her. So the next couple days would prove interesting to say the least.

"I've never seen one that wasn't circumcised," Jaycee said, still staring.

Oh. Well, so much for why I thought she was staring.

She then resumed lowering my underwear, set them aside, and returned to staring at my cock.

"Suck it," I ordered.

Jaycee gulped, then nodded and leaned in. She gently grabbed my dick with both hands to steady it, and softly, almost reverently, kissed the tip. She then started stroking with one hand while scraping my upper thighs with the nails of the other. She soon added her tongue, slowly licking up the underside. Pretty soon Jaycee was sucking on the head while pumping me with her fist.

Jaycee came up for air and said breathily, "are you going to cum all over my face?"

"Don't," I ordered. Jaycee froze and looked at me questioningly. "No sex talk. It doesn't turn me on. Quite the opposite in fact. At least, that's the case when it sounds contrived. Just concentrate on making me feel good. Everything will flow naturally from that."

Jaycee nodded, gave me a little understanding smile, and then resumed my blow job. After a minute she took me out of her mouth and smacked my penis on the side of her face. I had never experienced this before and it was unexpectedly exciting. Going from a moist, warm environment out to the open air with sudden staccato bursts of sensation sent shivers up my back, especially when she immediately plunged my cock back into the heat of her mouth.

After the third time she did that I was so excited that I grabbed big handfuls of hair at the back of her head to control and guide her and started fucking her mouth. I was careful not to go too deep, but I definitely wanted to set the pace and penetrate just a little further than she had taken me to that point.

"I want you to swallow," I told her.

"Mrmph," said Jaycee as she tried to pull back. I increased my grip on her and resumed my pace.

"Yes," I said, "you will swallow."

Jaycee looked up at me as my cock sawed in and out of her mouth. Her hands now held me at my waist and I picked up the pace slightly while trying not to go deeper. Finally I reached my peak and gripped her hair tightly as I held her in place and started coming into the back of her mouth.

Jaycee didn't move a muscle at first, letting my cum gather in her mouth, but after a few seconds I felt her neck muscles move, contract and release. After she swallowed, I laid back on the bed to recover. Jaycee stayed in her position, lightly kissing my cock and lightly stroking my legs and upper torso with her fingertips. I thought I could occasionally feel her stiff nipples touching my inner thighs, too.

Now for stage two. I wanted to return the favor. Eating pussy was one of my favorite things to do. I loved the taste, and loved being able to focus such pleasure on a woman I was with. I'd made sure to eat all of my one-night flings to an orgasm so that they left with something to remember fondly of me. However, I needed to maintain my dominance over Jaycee, and having my face stuck in her crotch was hardly a power position. I thought about it a bit as I recovered.

Finally I got up and turned to Jaycee. "Lie face up on the bed with your head here," I said, pointing to a spot about a foot below the top right corner.

I made my way to my closet without looking to see if she was following my instructions. I grabbed an old necktie I hadn't worn in months and returned to the bed. Jaycee lay where directed but over to the far side, looking expectantly at me.

I got up on the bed, grabbed her far hip and dragged her back to the center of the bed so that she was now at a diagonal angle, then threw my right leg over her so that I sat lightly on her stomach.

"Put your arms straight up, placing your hands past and on opposite sides of the bedpost," I ordered. Jaycee stared at me for several moments then got a bit of a panicked look in her eyes.

"No. I can't do this. Will, I don't think this is a good ...," she began when I grabbed her, rolled her over quickly and [SMACK!] delivered a strong, open-palmed slap to her exposed butt. It wasn't just a casual swing of the arm either. I really put some strength behind it.

"Ow!," screamed Jaycee. She tried to move out from under me, bracing her hand and knee on the mattress to spring upwards. "That hurt you prick..." [SMACK!] "Ow!" [SMACK!] "OW!"

I rolled her back over, quickly sat on her stomach again trapping her, and pressed my hands down on her shoulders immobilizing her torso. "Place your hands on opposite sides of the bedpost," I calmly ordered.

Jaycee's eyes looked a little watery and she half-raised her arms to the top corner of the bed and stopped. I slightly raised my eyebrows at her and she slowly and with small jerks raised her arms the rest of the way. I lifted my weight off her, took the necktie and tied it to her right wrist tightly, then wrapped it several times around the post, tied it to her left wrist, and lastly tied together the ends of the necktie that dangled off of each wrist. Halfway through the procedure I realized, somewhat embarrassingly, that my semi-flaccid cock and nutsack must have been dangling right above her face.

I then scooted down, putting my weight on her thighs, and looked Jaycee straight in the eyes. She was looking hurt, and scared.

"Jaycee, I have two purposes here that are sometimes going to be at cross purposes. Firstly, and primarily, I want us to both give each other pleasure. Ideally, we will give each other more pleasure than we've ever experienced before. I doubt we'll actually accomplish this, but I believe in setting high goals." Jaycee's eyes softened a bit. I took that as an opportunity and gave her a soft kiss on the lips. She even returned it, albeit half-heartedly. I decided to give her more kisses, working my way slowly down her body.

"Secondly," I continued. [kiss] "I want you [kiss] to obey my orders. If we [kiss] were involved in a relationship, [kiss] then I wouldn't have this as a goal. [kiss] Instead [kiss] we'd be engaged in constant negotiations [kiss] and bartering, [kiss] trying to seek advantage [kiss] in some endless power struggle [kiss] even while we should [kiss] be going about the simple task of giving each other pleasure."

I decided to concentrate on her breasts, slowly working my way in towards her nipples and frequently alternating between them.

"But here tonight, [kiss] and for the next week, [kiss] there is to be no negotiating, [kiss] no bartering, [kiss] no power struggle. [kiss] I have the power." I gave her a little nip, with teeth, and could hear (and feel) her suck in her breath. "You have no power. [nip] I know this, [kiss] because you gave me all the power [kiss] when you agreed to be my sex [nip] slave. [nip]."

I stopped and raised my head up to look her in the eye. "I've told you how I will deal with your attempts to not do as I order, and now you've experienced it not once but twice. The third time will be as bad as those two put together. I don't want that to happen. I assume you don't want that to happen. Especially when we could single-mindedly be pursuing that first purpose of giving each other extraordinarily amazing pleasure."

"Now, will you be a good girl?" I asked. "Will you follow my orders not only because you gave me your word that you would, but because you trust me to act for our mutual pleasure?" Jaycee was trembling slightly. And her long nipples looked like they were about to start firing bullets like Austin Powers' Fembots. She nodded her head in the affirmative. "Good," I said.

"Will," she said, "you told me to tell you what turns me on and what doesn't. Being tied up really doesn't turn me on."

"See?," I started. "Wasn't that a much better way of getting your point across without directly telling me 'no', calling me a 'prick', and getting your fanny spanked?"

"So you'll untie me?" she asked hopefully.

"No," I said quickly. "I want to tie you up, and so I will. My wants trump yours."

"Also, you're lying," I added. And I moved back up to kiss her lips.

"Lying?" she protested. "About what?"

From mere inches from her face, I said quietly, "about being tied up not turning you on." I kissed her hard. Jaycee quickly opened her mouth and accepted my tongue. I stroked her arms up and down as I kissed her, then grabbed them and tugged downward slightly to feel the resistance from being tied. Jaycee groaned in mid-kiss and then aggressively thrust her tongue back into my mouth.

I once again moved down her body, kissing along the way.

"I'm turned on by other things that you're doing," she took the break to explain. "Having my arms tied has nothing to do with it."

"Still lying, though maybe you're lying to yourself."

As my hands moved down her arms and across her armpits, Jaycee squirmed a bit. So she was ticklish. That's good to know. I concentrated on her breasts again, this time suckling on her nipples. This was a little different, as I'd never experienced being with a woman with such unique protrusions before. They appeared to be very sensitive as well, considering Jaycee started squirming a bit and was audibly groaning.

After a good five minutes of working over her breasts, when I was sure that she wasn't going to cum just from tit suckling (for a while it seemed like she might, and I wanted to make sure), I started moving further down her torso. As I did so, Jaycee flung her legs apart. She was obviously looking forward to my continued travels.

I briefly slipped my tongue into her belly button, and felt her body twitch and her stomach muscles writhe from the ticklish sensations. Then I continued my downward trek before she would be overcome enough to complain. I really didn't want to interrupt right now for her third spanking.

I skipped over the most sensitive, and obviously aromatic, area and placed small kisses and licks on her inner thighs. Jaycee was now rhythmically pulsing her butt slightly off the mattress as if I was already fucking her.

"Oh Will, please," pleaded Jaycee. I continued the slow build-up, now kissing an orbit all around her pussy. Finally, when I was out of my own patience, I hooked my arms under her upper legs, took hold of her hips, and gave her one long, slow, strong lick from the bottom of her opening lips to the top. "Ooooh-oh-oh-oh," Jaycee moaned. She tasted wonderful. A bit strong, but sweet. I never understood when people said this was gross. This was the elixir of the gods, sweet ambrosia, the potion of love and the fountain of youth.

I licked, I lapped, I nibbled, and I nipped. I experimented to see what she liked the best and then repeated those, while still giving her some variety. But I stayed away from her clit, and I didn't penetrate her with my fingers, only my tongue. Jaycee placed her heels on my back, slowly pushing me with them to set a rhythmic pace.

"Oh God!", she moaned. I immediately stopped and pulled my head up, looking at her.

At first her hips still bucked up at the same pace, but now with a bit of urgency looking for her lost lover. Finally she looked down. "Wha? What?" she groggily asked.

"That's not one of the names I told you to call me," I answered.

"What?" she repeated.

"God is not one of your approved names for me. You may only call me Will, William, or Sir."

She giggled. "Yes, sir."

"Good girl," I approved. "I'd hate to have to spank you for such a small transgression as that." And then I plugged back in to her pussy.

She ground back at me. "Oh, Will!!!!"

After a few more minutes, I pulled my left arm out from under her, and snaked it around so that it was poised just below my chin. Then I edged up slightly, planted my mouth directly over her clit, and went to town on it while pushing two fingers up her surprisingly tight pussy.

Jaycee came unhinged. She bucked wildly, with her ankles now slapping my back.

"OOOHHH-AHAHAH-ARUMPHAH-AG-G-G-G-GOOO-RRRR-AIIIEEE!!!" Or, at least, that's my best approximation of the noises she made. She came. And came. And came.

Damn, I was good. Her pussy clenched my fingers again and again. Her back arched off the bed. Her ankles slid off my back and she used her feet as leverage to shove her pussy even more into my mouth.

Finally she collapsed. Her back flopped back down onto the bed. Her legs splayed out to the sides. And she gasped and heaved for breath. I pulled my fingers out, with a giant spasm coming from Jaycee and a squeaked "Oh!" from her mouth. And I rested my head on her right inner thigh. After thirty seconds or so when I had caught my own breath, I pushed my left arm back under her leg and re-positioned myself for another round.

With my first new lick, Jaycee clenched her thighs against the side of my head. "No, don't! I'm too sensitive!"

She was squeezing me tight. I tried to pry her legs apart with my hands. "Jaycee ..." I warned.

"No, Will, you can't."

I move backwards to extricate myself, moved to her right side, then rolled her over.

"Oh, no, Will!" [SMACK! SMACK! SMACK!]

I rolled her back over.

"Spread your legs," I ordered.

Jaycee spread her legs. "I'm sorry, Will. But I'm really sensitive after coming. It won't be pleasurable for me."

I had my own theory about that. We'd find out who was right. But I definitely liked it that Jaycee was apologizing to me for making me spank her. And I was obviously still keeping a dominant position over Jaycee even while eating her out. It looked like my plan was working nicely.

I returned to my position and once again started with soft kisses on her thighs. But only a few, and then I went right back to her glistening pussy.

"Oh! Er! Oh! Rmph!" went Jaycee. Then I grabbed her tightly and went right back to her clit.

"NNNOOOOOO-EEERRRRR-AAAA!!!"

Back to long licks up and down her pussy lips as her bucking slowly lessened. Jaycee was still whining, and crying, but as soon as she was almost back under control I went back to her clit.

"IIIEE-EEK" and then silence. But her body started vibrating and her back was once again arched up. Before she blew a blood vessel I went back to licks.

"[GASP!] OH! [GASP!] What [GASP!] are you [GASP!] doing to me?" Jaycee managed to get out. "OH!" I continued to alternate between her pussy and her clit with each length of time getting shorter. Finally I thought the time was right. I pulled both hands out from under her legs and placed my hands on either side of her stomach above me. Then I gave her clit once last lick and suck and pulled myself up above her. I grabbed my dick, placed it right at her opening and plunged in so that my head was captured by her soaking pussy.

Jaycee's eyes snapped open and seeing me hovering above her she shouted "YES!" and brought her legs up, rotating her hips upwards, and then placed her ankles across my ass. Even though my face was drenched in her juices I forced myself down on her. Jaycee didn't even hesitate. She opened her mouth wide and tried to suck my tongue down her throat.