The Evolution of a Bet

"What now?" she asked in a husky voice once we had finished kissing.

"I think you need an orgasm or two, to make sure you are fully relaxed," I told her.

"Oh, goody," she suddenly squealed, "can we try a sixty nine?" Be still my beating heart...

I removed Julie's underwear, only because I didn't want to damage it in the throes of passion later, and I lay down on the lounge positioning her on top so she could choose the depth that she wanted my cock in her mouth. She looked and smelled very clean as she positioned her pussy over my mouth and I realised then that she must have given herself an enema while she was inside the house preparing. This gave me a plan for later. I found her clit quickly, but started with light strokes of my tongue to get her used to the contact. Her tongue found my cock head and she started licking too.

I knew that Julie had to cum first because if I was trying for a second orgasm when I was in her ass it was going to take a long time and I knew this was going to hurt her, no matter how much preparation she had made. The problem was that she had learned a lot the last time and she was now putting it into practice. She was licking and nibbling under the head of my cock and her hand was active too, usually gently squeezing my balls. I tried to put those sensations out of my mind and I concentrated on her. I licked her clit and her pussy, one after the other, and even used my tongue to push into her tight little hole. Each time I did it amazed me that I had managed to get my cock in there, it just didn't seem to have enough room.

Eventually I slipped a finger into Julie's sopping wet pussy, and she moaned in pleasure as I did. A second finger followed for a little while and then I steeled myself, removed my fingers and licked across Julie's puckered little asshole. She jumped, but I held her firmly in position as I did something I had never done before and I kissed an ass. I once had a girlfriend who insisted on washing me thoroughly and who then rimmed me. I would call it a pleasant experience, but it was a bit uncomfortable to start with so I could sort of understand what Julie was feeling as I did it to her.

"Relax," I whispered gently and then blew air where she was wet, making her writhe again.

"I don't know..." she started saying, but I pinched her clit and squeezed gently, making her moan.

"Just go with it," I told her, and she did.

I was still stroking her clit as my tongue gently probed her ass. She still tasted clean, so my greatest worry about this act was not realised. Eventually I wet a finger and gently pushed it into her ass. She trembled as I did, but my tongue returned to her clit and this relaxed her enough for me to continue. I slipped another finger into Julie's pussy and began to pump both fingers in and out. I could feel Julie shudder in time with my stroking and I knew she was getting very close. She realised this too and desperately sucked my cock as deep as possible into her mouth, but I was able to hold off as she moaned and I felt both holes spasm around my fingers. I hadn't realised that happened, I thought it was just the pussy.

Julie collapsed onto me and my cock slipped out of her mouth. I gently manoeuvred her until she was kneeling on the side of the lounge and her beautiful ass was there for me to plunder.

"Lube," Julie murmured, pointing at her clutch bag, and I was impressed with her forethought. I went and got the lube and squeezed a good amount into my hand. Using two fingers now I worked it into her ass and Julie groaned with what I assumed was a combination of pain, pleasure and nervous anticipation. Without wasting time I coated my cock with the greasy stuff and then I guided the tip to her virgin asshole. I was going to ask if she was ready, but I didn't want to make her any more nervous, so I gently applied some pressure. Julie tensed up.

"Relax," I advised softly, and she laughed.

"Easier said..." she gasped and then I pushed a bit harder and saw her ass open slightly around the head of my cock.

"Oh fuck," she groaned.

"Exactly," I agreed, trying to distract her. I stopped applying pressure; trying to wait for her to adjust to the intrusion.

"Keep going," she said, "you're making the worst bit last longer." She must have had some advice to have said that.

I pushed again and slowly the head of my cock penetrated her. She gasped and moaned, but I continued until the head finally popped through her incredibly tight little ring.

"Wait now," she said, panting, and I waited as she puffed like a woman practicing her breathing in preparation for child birth.

"OK?" I asked, worried, and she just nodded.

"Now," she finally said, "fuck my ass Darren, but please do it gently."

I can tell you right now that it would have been damn near impossible to do if Julie hadn't been doing her preparation. Her ass still gave tight a new meaning. Even though my cock was now as hard as it could be, when I was pushing in so much blood was squeezed down to the base it felt like it was twice as thick as normal. On the out stroke it squeezed the blood up to the head and I had horrifying visions of a balloon popping as it was grossly over inflated. Now this all sounds incredibly bad but it managed to feel incredibly good. I would have enjoyed it more if Julie wasn't struggling so much to keep her composure.

For the first few minutes I slowly worked in and out until I could finally get my full length inside. For this entire time Julie had her head buried in a cushion, and she was whimpering softly. I suggested we should stop, but she told me to keep going. Apparently it would get better. I kept adding lube to the equation, and this did seem to help as eventually fucking Julie's ass stopped feeling like somebody was trying to skin my cock using just pressure. If there is no slip it is amazing how far the skin on a penis will stretch.

"Damn it Darren," Julie moaned into the cushion, "what are using back there? That feels twice as big as it was yesterday."

"It's the same," I assured her as I kept working back and forth.

After a while I was just fucking her gently and Julie finally lifted her head and looked at me. I could see she had been crying.

"It is getting a bit better," she said, half hopefully, and I nodded.

"Is it good for you?" she asked.

"It is amazing," I told her, and she nodded.

"Speed it up a bit Darren," she managed to say through partially gritted teeth, "I want to feel you cum inside my ass." I nodded.

I'd like to tell you that Julie got right into it and came four times from her first ass fuck, but that isn't what really happened. I did get up a good pace, and she did start moving with me, and she definitely did stop crying, but that was about all there was to it. I was sweating profusely as I fucked that tight little ass and I could feel my orgasm approaching.

"Ready?" I gasped.

"And waiting," she said sounding rather keen for it all to be over.

The last thing a man usually does when he is about to cum is bury his cock as deep as possible inside whatever it is that he has that appendage in. You can call it biology, you can call it instinct, or in Julie's place you can call it torture. She shrieked as I pushed my cock full length into her and then sighed with relief as she felt it pulsing as it unleashed a torrent of cum. I eventually fell forward, exhausted, but managed to use my elbows to keep most of my weight off her.

"Are you OK?" I finally asked, and she nodded.

"I think I'm going to need more practice with that," she said, and I was relieved that wasn't saying something like 'never again'. At least I hadn't made her initiation that bad.

We waited until my cock shrank down, but she still groaned when I pulled it out.

"Pool?" I asked and she shook her head.

"Today you come in and have a shower," she told me, and I could understand why. No Matter how clean she had made her ass there would always be some concern about hygiene.

"When can you change the last screens?" Julie asked, reminding me of the reason for all of this.

"Now," I told her, and I clicked my fingers theatrically. "Done," I said smugly and she stared carefully at the final wall.

"You already..."

"I told you I was ready to let you off that one," I said seriously.

"Are you glad we did it?" she asked and I gave her a huge satisfied grin. She nodded and said "Me too."

"What now?" I asked her as we both seemed to have recovered.

"What do you suggest?" she countered.

"If you can put up with my work clothes when you are dressed up so well we could go out for dinner," I suggested, and then I realised what I had said.

"Are you asking me out on a date?" Julie asked, looking at me seriously.

"It doesn't have to be," I said back peddling madly, "I know I'm way to old and ugly for a beautiful woman like you."

"Really?" she asked.

"Look it was the bet that led is to do this, so I won't over estimate my place in your life but I..."

"Ssssh Darren," Julie said, placing a finger on my lips. "None of this was actually about the bet at all."

"It wasn't?" I was confused.

"I've really got enough put aside to do the whole job over again," she said, and she giggled.

"Really?" My head was spinning.

"What this was all about was me trying to finally find a way to show you how attracted to you I am."

"You are?" This was totally out of control.

"I want us to go inside and have a shower together. I want us to go out on a romantic date together. I then want to come back here and have you take me to bed. If we are both up to it I want you to fuck me to sleep and then fuck me awake tomorrow." I was staring at Julie, my mouth wide open in astonishment.

"I love you Darren," she said, "I love who you are and I love what you do to me. I don't care about age and I think you are the most handsome man I have ever met. I want to learn about things from you. I want to learn about sex, I want to learn about music, I want to learn about movies, I want to learn about landscaping. I want it all. So," she demanded, looking straight at me, "what do you say?"

"I say yes Julie," I said sincerely, "and I think I am the luckiest man alive. I love you too."

We kissed then, and this time I was able to put all my passion into it. This wasn't a onetime thing anymore, this was my new life. Julie finally turned and gingerly walked toward her clothes.

"Let me start by telling you," I said grinning, "about Roy Rodgers."