The Evolution of a Bet

"I didn't know that you were married," she said, "you never told me."

"You never asked," I responded, but it was with a kind smile, and she grinned.

"That's true," she said quietly, "I didn't want you to be married."

"What?" I asked, confused, but Julie just looked at me and then grinned wider.

"You've seen this," she announced, and pulled her shirt straight up over her head and off without undoing the buttons. I smiled.

"And these," she said reaching behind to unclip her bra, and then dropping it off her spectacular tits. I smiled wider and nodded.

"And this," she said, slipping her skirt down over her hips revealing a cute pair of pink panties.

"And beautiful they all are," I finally responded.

"But not this," she said finally as her underwear met the pavers.

I just moaned my appreciation. Her pussy was trimmed around the edges, but most of it still had a healthy but quite light covering of black pubic hair. For a while I went through a phase where I preferred women who shave entirely, but I was now back to wanting some hair down there. Let's just say I don't like a barren landscape and I don't like a massive jungle, I like a nice neat and tidy garden. Julie's was exactly what I liked.

"Perfect," I said, echoing my thoughts.

"Really?" Julie asked dubiously.

"Really," I confirmed.

"You don't think I should shave? Toni shaves..." Julie said, and then stopped as if she had said something wrong. Neither of us had mentioned Toni since my blow job, and I sensed there might have been a story there somewhere.

"I prefer exactly what you have right there," I said sincerely, looking straight into Julie's eyes.

"Good," Julie said, "now fuck me Darren, I'm horny and I want it now."

I looked carefully at Julie. She had said what I wanted to hear, but there was something wrong in the way she said it.

"What's the matter?" I asked.

"Nothing," she replied, even less convincing with that line.

"You're scared," I said, fairly sure I was on the right track.

"No I'm not." Her denial was too quick and too forced. I stared at her for a moment.

"How many times in your life have you had sex?" I asked her, thinking I might know what the issue was.

"I, uh... er... three," she stammered.

"Uh huh," I said, "did you enjoy it?" Julie hung her head.

"No," she admitted, "it hurt like... er..." Her head dropped further as she realised what she was saying. I shouldn't have laughed, but I did.

"Like fuck," I said eventually. She looked up at me and she had tears running down her face.

"It was awful," she said.

"So why are you doing this?" I asked.

"The bet... the screens.." her voice trailed off again. I knew then that I was on the verge of doing something that was much closer to rape than I ever wanted to be involved in. I decided on humour as my approach, and I put my hands under her chin and lifted her face to mine.

"I'll bet you the rest of our bet that this North Melbourne supporter can make you enjoy what those nasty Collingwood supporters made you hate," I said, grinning.

"Huh?"

"If my making love to you hurts enough at any time to make you ask me to stop, I will stop," I explained, "and then I'll change the rest of the screens back and we are square." Julie looked into my eyes.

"What do you get from this bet if you win?" she asked.

"I get to have sex with you," I replied, "an astoundingly beautiful young woman."

"You already get that and more. You have to get something new," she said stubbornly. "What else do you want?" I had to think quickly.

"OK, if I am right and you actually enjoy this then I get a bonus extra blowjob, just from you, and an extra fuck as well after this bet is completed." I suggested.

"I can't really lose can I?" she said, nodding her agreement, "but I know it's going to..." I kissed her before she could get the words out. It was a very long and very passionate kiss, and she tensed up at first and then she relaxed and kissed me back.

"No," I finally said after pulling my mouth off hers, "you can't lose, but neither can I."

With that I picked Julie up and laid her gently on the sunbathing lounge.

"Just close your eyes and don't say a thing," I whispered, and her eyes flicked shut.

I kissed her face then, starting on her closed eyelids and working my way around everything I could reach. I nibbled her ears, making her giggle, and I finally kissed my way down her throat and worked down to her tits. I already knew they were very sensitive, so I licked and sucked them until she had an orgasm, and then I gently placed a hand on her pussy and kept sucking those incredible tits.

Her tenseness that I had felt when I put my hand on her pussy seemed to fade as I got her going again, and I gently sought out her little pleasure button with a finger. She groaned when I found it, and her eyes opened.

"You like?" I asked, taking a short break from sucking a very erect nipple.

"Ooh yeah." She replied, and her eyes flickered and then closed again as she surrendered to her feelings.

I brought her to orgasm again, this time stimulating her breasts and her clit at the same time, and then she moaned softly when my mouth moved down to her belly. I was still rubbing her clit and I don't think she realised what I was going to do until my mouth replaced my fingers.

"What the...?" she said, opening her eyes and lifting her head.

"Ssssh," I whispered, "you are really going to like this."

"But I..."

"Ssssh," I repeated, and then sucked her clit into my mouth. She tasted musky and a bit stale, which was not surprising after a day at work, but I knew I was going to lick that away pretty quickly and get down to her real taste.

Julie's head was thrashing around as she came again, and I slipped a finger into her slick pussy. She was very tight, but I had made her extremely wet and totally relaxed, and I wondered for a moment if she had even noticed.

"Feels good," she said, "not sore."

"I know," I said and returned to my task.

I had managed to work three fingers into her tiny pussy and I was pumping them in and out when she came again. I knew it was time for the real thing, and I'm sure she did too. Julie watched me intently as I slipped out of my clothes and crawled up between her open legs.

Julie's pussy had already been every bit as good as I had hoped it would be. It looked exceptional, it tasted fantastic, it was hot inside and it was incredibly tight. Now it was going to be exactly where I wanted it to be, and that was wrapped around my throbbing cock.

"You will be gentle?" she asked, looking nervous again.

"It's OK," I said reassuringly, "you will love this."

Julie nodded her head and watched intently as I rubbed my cock head up and down her slit until it was thoroughly soaked in her juices.

"Tell me if it hurts too much," I said and I gently pushed my cock against her tight entrance, which resisted for some time, but then finally relaxed enough to allow some movement. I spent some time just pushing my cock head in a tiny way and then backing out again and when she was fully relaxed with that I pushed in a bit further. At the same time I was gently stroking her clit with a finger, just to try and make her feel a bit better and less nervous.

Julie flinched a bit as my head finally penetrated her opening, and I stopped to let her pussy adjust. I looked into her trusting eyes for a while and then she nodded.

It would have been at least five minutes before I finally worked my cock all the way in. I was being as gentle as I could, using only very light pressure and very small movements, but finally that moment arrived.

"Is it OK?" I asked, and she smiled nervously.

"I think so," she replied.

"Did it hurt?"

"Only a little."

"Do you want me to stop?"

"Fuck me Darren," she said, and this time she really meant it.

It started as a slow and gentle fuck. I was using long strokes and just stopping short of pulling my cock out completely before pushing in again. At first Julie just lay there, tentatively feeling the sensations, but after a while she started pushing her hips up to meet my thrusts and I increased the speed.

"Never.. thought... it... could... be.. this... good," she grunted as I started to fuck her in earnest. The build-up had taken a long time, and that long stimulation, combined with the exquisitely tight grip of her pussy meant that this was not going to be a marathon effort.

To try and last longer I eventually pulled out of her and changed to doggy style on the side of the lounge. This worked well for a while, but then a couple walking their dog down the footpath outside stopped as they heard our moans, peering at the screens for a moment before shrugging and walking away. This distracted Julie so I changed again, this time to cowgirl, a position where Julie could not see the street and be distracted.

Julie rode me like a champion, and I struggled to decide what to watch. The motion of her massive tits as she bounced up and down was sensational, but looking down and watching those delicate pussy lips stretch as my cock entered her on every stroke was pretty special too.

"I'm going to..." she moaned, still a bit too shy to complete the sentence.

"Me too," I replied, and moments later my cum finally sprayed deep inside Julie's pussy. I beat her by a couple of seconds, but I was still squirting when she shuddered and her pussy clamped around my cock as she joined me in that final orgasmic moment.

Julie had collapsed on me as she orgasmed, and we lay there panting for a while. My cock slowly shrank inside her, but didn't pop out. It was still too deep to do that. I hugged her and she clung to me as her breathing returned to normal.

"Darren?"

"Mmmm?"

"Thank you so much that was just the best." I squeezed her against my chest.

"I'm looking forward to repaying the new bet," she said.

"Me too," I replied, as Julie, a beautiful girl about half my age, told me she really wanted to fuck me again.

Damn, I thought, I am just so lucky.

PART FIVE

I changed the other long side the next morning, even though we hadn't discussed which side was next. I spent some more time finishing off the paving Job, and I reflected on how long this particular project had taken to complete. I always took my time when I did a job, to make sure it was the best it could be, but this one had already taken a week longer than it should have. That was partly due to putting up the screens, taking them down and replacing them and then gradually swapping them back again. The rest of the reason was that I had worked more slowly than usual to give Julie time to fulfil her side of the bet. But it was time to move on now and start on the next job which I had been delaying.

I also thought long and hard about the last part of the bet. If Julie had struggled so much with a straight fuck how could she cope with anal sex? My cock is quite long, I know that, but it is also very thick and that is the dimension that can cause major problems with such a tight little hole. Anal sex is a bit of a double edged sword to me. It can be great, with a tightness and intensity that is incomparable, but it can also cause a lot of pain, and I don't like inflicting pain. I really wanted to 'complete the set' by taking Julie in every hole, but deep down I knew I couldn't. I would tell her that the anal was not going to happen and move straight to the extra blow job and fuck, something that I was anticipating greatly anyway.

I changed the last screens. As far as I was concerned the original agreement was now complete, and with that I felt a huge sense of relief. We could complete our agreement and then I could move on, and that was good because I was becoming far too attached to Julie. She was a young kid with her whole life in front of her and she didn't need an old letch like me hanging around trying to take advantage of her.

"Darren?" Julie called as she entered the pool area.

"Yeah?"

"How do they know?"

"How do who know what?" I asked, confused.

"The girls at work," she replied, "almost all of them have said something to me today about my 'big night' or my 'good time', and one even said I look like I was royally fucked!" Julie's face glowed with embarrassment as she said this, and I grinned.

"It could be that wonderful aura of satisfaction that surrounds you," I suggested, and I could see that, "it could also be that huge smile on your face," I continued, and yes she was wearing a grin as wide as the Yarra River was long, "but it might also be the fact that you are walking like Roy Rodgers," I said, laughing a bit at the same time. Julie ran to me and she kissed me and hugged me tightly.

"Who is Roy Rodgers?" she eventually asked, but I never got around to answering that question. The kisses got priority.

"Julie," I said sometime later as we lay together on the lounge hugging, "I've been thinking about the anal sex thing and I really don't think we should..."

"Stop right there," she demanded, and I stopped, looking at her curiously.

"You have been so nice to me Darren," Julie continued, and then she took a deep breath. "You have made me feel good about things that I hated."

"I..."

"No, let me say this," she interrupted again, and I smiled my acceptance.

"For all my life Toni and I have been best friends and also the best rivals too. We competed for highest marks at school while we helped each other study, we gave each other alibis when we were out when we shouldn't have been, and that sort of thing. Almost everything was great, but then when it came to boys somehow Toni always got the good ones and I got the bad ones. "

"Uh huh," I said and waited to see what the point was.

"I was jealous of her Darren. Toni was sexually active early, but when I tried it was awful. Toni was great and she tried very hard to help me, but as soon as my boyfriend's met her they just lost interest in me." I looked at Julie in disbelief, wondering how anyone could not see she was the more attractive of the two sisters. "I was too much work," she explained, "I was too hard..."

"And she was too easy," I said grinning. Julie slapped me lightly.

"I didn't mean that," she said, and I nodded. "But now I've found you, and you are different. You took the time to make it good for me. You made me enjoy sex and for that I will always be grateful." Julie looked at me, and the sincerity of what she was saying was obvious. "You didn't run to Toni after you met her Darren, you wanted to stay with me instead," she said and I nodded again. "I didn't bring her as a test, I really needed her help to get that right, but it also showed me that you cared about me more than you cared about her, even after she got your whole cock into her mouth. Even after all she did you still didn't talk about her until I did. You made me feel important."

"You are important," I told Julie sincerely and she smiled.

"I know, and that's why I want to complete our bet."

"How does that work?" I asked, confused,

"If this is ever going to happen to me I want it to be from someone who I know is gentle, someone I trust totally and some I... uh... care for," she said. She was going to say 'love' I thought, and my heart jumped. I was very attracted to Julie, but did I love her? I had been so hung up with the older man younger woman thing that I hadn't really considered that.

"But I can't stop this from hurting you," I finally said, "and hurting you is the last thing I want to do."

"I can stop it hurting, at least a bit," Julie said. "I told Toni about the bet and our agreement as soon as it happened and she said most of it should be all right but I needed to prepare for the last part, the... um... anal," she explained. "Toni got me some... um... things to make me bigger down there," Julie said, turning scarlet again, "and I have been using them every night and most days."

"Uh huh..." I said, my head spinning. She'd been using butt plugs for days on end just so that I could fuck her ass? Now that's dedication.

"So don't you dare back out on me now, because I don't want to have gone through all of that for nothing, right?"

"Errr, right," I agreed.

"So I'm going into the house now to prepare, and when I come out you'd better be ready to pick the last cherry left on this tree." I smiled at her wording, as she grabbed my cock and gave it a squeeze.

"Aye, aye Sir," I responded saluting both above and below.

"That's Ma'am to you," Julie said and she got up and walked away, leaving me there with a bemused expression on my face and a hard on in my pants.

I stripped off and plunged into the pool, wondering at how quickly my well laid plans had been completely overturned. I had only mentioned anal in the first place because I wanted to give Julie a way out that kept her pride intact, and I had never expected any of this to actually happen. I still couldn't understand how it had happened, but I knew that I was falling for her and walking away after our deal was complete was going to be one of the hardest things I had ever done in my life.

It would have been about an hour later, and I was back in the pool, when Julie came back. She was dressed to kill in a tiny black dress that clung to her every gorgeous curve, a subtle matching diamond pendant and earring set and shiny matching black clutch bag and stilettos. The shoes had thin straps that wound their way up around her calves. She had even done her hair and was wearing it up, exposing the graceful curve of her neck. I was stunned.

"Wow," I gasped as she spun to show me the full effect.

"You like?" she asked, with a mischievous grin.

"I love," I replied, and she reached around for the zipper on her dress.

"Wait," I said quickly, and she paused. "This is one gift that I want to unwrap myself."

She waited.

It was interesting swimming from the far side of the pool to the steps. I had my own version of the famous 'winged keel' that was instrumental when Australia won the America's Cup all those years ago. Unfortunately mine was an encumbrance, not an advantage, but I got there eventually. Julie smiled as I came out of the water and waited patiently while I dried myself hurriedly. I then walked to her and took her into my arms, hugging her passionately as a lover does. This wasn't just about the sex anymore; this was all about the beautiful woman who was willingly offering me her most personal prize.

I kissed Julie's exposed neck as I slowly lowered her zip and she leaned her head back to make my access easier. I reverently peeled of the black dress and found the most amazing lingerie under it. Usually when a woman is very big in the chest department her bras are quite large and more about load bearing than about being sexy. Julie's was the exception to that rule. While still quite large in size it showed a lot of her spectacular cleavage and it was made of some sort of mesh that was very see through at the top and it gradually darked as it went further down so you just couldn't quite see her nipples. This wasn't just a couple of bits of material sewn together, it was one single piece. At the bottom of the bra it looked like a smooth and solid black satin material. The straps were thin, almost a shoestring style, as they went up, but they did widen out around the shoulder.

"Oh wow," I exclaimed as the bra was revealed.

"You like?" Julie asked again and I grinned.

"I love," I replied again.

I am one of those men who thinks that a woman in sexy underwear can be more of a turn on than one who is naked, and Julie standing there in her heels and underwear was the absolute proof that I needed in that regard. I had peeled off her dress and that had revealed the matching bikini briefs that she wore.

"You are stunning," I told her.

"You...?"

"Love," I said and I pulled her to me and kissed her deeply.