The Lost Bet - Consequences Pt. 05

Anal tonight, anyone?

I told Jodie to be ready for her anal payment the following Saturday. I think she practiced pushing various things up there all week. I know I found some pretty messed up unpeeled little bananas in the trash. And a very small cucumber, unpeeled, but looking sticky on the outside.

Saturday night, we met in the master bedroom. She had on a new pair of panties that covered everything, except they had a fairly large prominent round hole in the back, directly lined up with her asshole. I could see the dark brown winker looking at me when she bent over. I told her she should probably take them off, given all the places the lube ended up last time. She agreed and wriggled out of them, kicking them to the corner. I was fully naked already, so we started on our warm-up sex stuff. Since we both knew what needed to be done, no explanations were needed. She had a bowel movement earlier and also decided on a warm enema. She said the warm water had felt kinda good up there (until she had to push it all out, which is kinda messy for the toilet). I planned to wear a condom, not to keep cum out of her ass, but to keep bacteria out of my pee-hole. I didn't want an infection of any kind. I didn't like the idea of the rubber taking sensation away from my cock, but I needed some of that anyway, since great sensations on my cock have caused premature ejaculation for me at times. And Jodie's very tight asshole compared to any typically looser pussy would surely make my cock want to explode early.

To change things up, Jodie did all the warm-up work. I laid on my back with my erect dick pointing at the sky, bobbing with each heartbeat. Jodie moved up and sat on my face, while sucked and lapped with my tongue on her pussy, pussyhole and clit. She never liked this at all before, but the bet payment session had made her want to try it again, even without the satisfaction of making me lick my own cum out of her fucked pussy.

After a few minutes of this, with me kneading her ass-cheeks from behind, she dropped down and slid my hard cock up into her hot pussyhole. She pushed back and down, driving it all the way in and gasping "Unnnnhhhh" when she knew it could go in no further. She paused only for an instant, then started rotating her hips while rocking her mons against my pelvic bone. I had planned to go only 1/2 way to climax, but I couldn't stop her from speeding up her gyrations and panting to a sudden ending for her.

I fought to keep from cumming and was JUST able to prevent that. I REALLY wanted to cum inside her asshole because I thought it would be worth the wait, but it was very difficult time to come inside her hot slippery pussy, especially with her going through a full orgasm on top of me. All of her different cumming sounds usually set me off.

I let her chill out on top of me, her pussy juice oozing out onto my cock and balls. I figured it might make good lube for the butt sex coming up soon. Then, I rolled her off of me and moved her into a Magic Mountain position. She now loved this for pussy sex, but this wasn't going to be that.

I moved around behind her and slid my cock into her pussy bareback. She arched her back as I slid in and moan with pleasure, not expecting me to slide in there at this point. She ground back on me some. After a bit, I poured lube on her ass and my fuckfinger and pushed it into her ass. She pushed back a little and gave a small grunt, but it was small enough not to cause her any pain at all. I pushed it in and out a few times, then took the smallest dildo, lubed it and pushed the head into her. This one was a bit larger, but smaller than my cock, so a good one to push in. I waited a minute, then pushed it slowly into her, a little at a time. I asked her now and then if she was ok and she always responded yes. When the entire 5" was in her ass, I started pulling it out and pushing it in.

I still had my cock in her pussy, so at this point, she was getting some normal sex feelings from that action. I pushed it in and out along with the ass dildo. She gyrated her ass a fair amount so it seemed she was enjoying at least the pussy action so far.

I withdrew both the dildo and my cock at the same time. Her body settled down and seemed to miss having them inside her. I unrolled the rubber onto my cock, doused it with lube, dribbled some inside her open asshole and put the head against the opening. It was only a little smaller than my cock size so I expected this to go pretty well. I pushed the head into her sphincter easily, then asked if she was ok. She said "I'm good. It hurts a tiny bit but actually less than when you poke me in my pussy when I'm not quite expanded and ready for you. Go ahead. Don't leave my pussy out of the action though. I need a little something to make this worth the trip." Her pussy reminder was helpful. In all the excitement of buttfucking her for the first time, I could easily forget to twiddle her twat some.

I added still more lube to my shaft, then began to slide it in. It slid in quite easily, since the head had expanded her sphincter, so the shaft could just slide right in. I still went slowly, only entering an inch at a time, pausing with each further entry move. When I was fully inside her, I again confirmed she was ok. She said "Yes, but my pussy is hungry!"

I reached underneath my balls, found her pussy, and stroked it from slit to pussyhole. After a bit of this, I slid two fingers into her while thumbing her clit, she started bouncing forward and back against my hand, moaning with each thrust. My cock was also sliding out and in, stopping when the head hit the sphincter. I wanted to experience everything she had available, so I asked her to tighten her sphincter and release it around my sliding cock. She started that action and it sent me over the orgasm edge immediately. The feeling of being gripped tightly then being released as my cock slid in and out was just too amazing and different to resist.

I grabbed both her ass cheeks and pushed in and out, blowing load after load inside the rubber. She wanted to feel the cum splash against her intestine, but that wasn't possible for us.

I rolled from behind her and she pulled the rubber off of my cock. It looked perfectly clean; the enema seemed to really help. She grabbed a washcloth, wiped my meat down, then climbed on top of me to finish her fuck. I didn't have much erection to offer her, but she ground her wet slippery pussy against my pelvis for a while then she moved up, spread her legs and pressed her pussy against my erect nipple. They weren't big like hers, but I guess she could feel them pushing against her pussy and clit as she ground down.

She ground for a full minute, then I felt her breathe in and hold it, then slowly let out a groan as her whole body shuddered through her orgasm. Some pussy juice flowed out onto my chest and she ground a little more on me. We both collapsed in a heap on the bed. I slipped my thumb up into her still-open asshole and a finger into her loose pussy hole. She felt it enter and bore down with her sphincter around me. She said she liked that feeling of something big sliding in and out of her sphincter. Alone, it wasn't as good as pussy sex, but with the pussy fingering, it was almost better, having both holes filled at the same time.

The usual question was then asked: "What do you think? Do you want a re-run sometime?" Her retort? "We'll see." Which usually means No, not ever again. But, in this case, the way things went for her, I wasn't sure about that.

We'll see.