The Lost Bet - Consequences Pt. 04

Pegging 101

The day after we "climbed the mountain", Jodie said she wanted to get my pegging done.  I was thinking we would do her anal sex first, then she could get payback by pegging me, but I guess she wanted ME to experience back-door sex before her, so I might be more empathetic to what it all feels like and go easier on her.  It was a good strategy actually.

I told her we had to first choose and order the equipment.  We had almost nothing for sex toys, so we basically needed everything:  a leather harness for her, a dildo to put in it and plenty of good lube. We searched online and found a discreet site that carried many different options that we could choose from.  I told Jodie she could pick out whatever she liked, to get her involved in the whole process and get her interest up.  She kept it all a surprise so I wasn't able to see it until she was actually ready to peg me.

The packages came and she opened them, cleaned each item properly, and charged the batteries.  Once all that was done, we decided to use it the following Saturday.

Saturday arrived and both of us were nervous.  Jodie wasn't sure she wanted to poke me (although, she often talked about me poking her in the pussy).  Over the years, she had said on more than one occasion "I'd like to be able to poke you so you can see how it feels, when you're not feeling well or you have a real headache or you have cramps or you... just... don't ...feel like having sex that night but he's horny and hasn't had it for a week so I guess I have to let him poke me.  Turnaround might feel good, if not physically, then mentally.  So, there was that.

She came into the bedroom naked but carrying a buttload of stuff (pun intended).  She dropped them all on the bed, then separated them into individual items.  First, there was a nice leather harness that fit around her upper thighs and her waist.  There was a large hole where the leather made an X in the front, to slip the dildo in that would do the actual penetrating.of my ass.  Beside that were 4 dildos of varying sizes, each a different color.  They were all made of pure medical grade silicone.  Most looked much like an actual penis, with a head, veins, etc.  The first was smaller than my dick.  It was about 1" across and 5" long.  The next was 1.5" across and 6" long.  The third was 2" across and 7" long.  The last was huge: 2 1/2" across and 9" long. When I saw it, I said "Why did you buy that one?  You won't be using it tonight, will you?".  "It depends on my mood later.  Be nice to me." she said, arousing my concern.

"So, how do we go about this?" I asked with some naïveté. "Well, in my research, you use LOTS of lube, start on the small side to spread your sphincter muscle out gradually, then move up the sizes.  It's actually pretty remarkable how large a dildo can get shoved up there" she said with confidence.  "The two critical items are: lots of lube and start small and work your way up." she added.

I already had my clothes off. And, I had not only gone number 2 earlier in the day, but I did an enema also, just to be sure, as a newbie to all this.  I should be as clean as a whistle in there.

We had placed large old bath towels over the bed, in case anything nasty showed up.  We positioned several bottles of sex lube around the room, on and near the bed.  Jodie placed the dildos in order by the middle of the bed within easy reach. The harness we found had an easy in/easy out setup to swap out dildos quickly. Hopefully easy in/easy out applied to my asshole also.

We decided to mess around some before we started the main event.  My cock wouldn't be involved in the packing process at all; and Jodie's pussy wouldn't get a workout either.  Consequently, we decided regular sex might be sort of a warm up, or at least 1/2 way to a climax, to get us in a hot sexual frame of mind.

Jodie got on her back and I started sucking her perfect nipples.  When erect (like, now) they were 5.16" tall and 5/16" across.  The areola's were dark brown (when she was very excited) or pinkish when not (they were pinkish at this point.  I had some work to do, I guess.) As she got excited, several bumps would protrude from her areolas on both tits.  I loved every facet of her breasts, areolas and nipples.  In my mind, for my tastes, they could not be beat. 

As I moved from one breast to the other, I spread her legs wide and slid the head of my cock against the top of her pussy slot, mostly against her clit and clit hood.  I was always leaking pre-cum fluid everywhere, so this made the head very slippery and it slid easily along her pussy crack, through her dark bush.

After a bit of this, I asked if she would flip to lay on her stomach.  I rubbed and scratched her back for a bit, then spread her legs just a bit, to slide my cock along her ass-crack.  At one point, I went a bit too low and the head caught on her puckered butt-hole. "HEY!" she shouted. "You're not allowed in there tonight!   You'll get your turn, just cool your jets big fella!"  I put a little sex lube on my cock, spread her legs further still and slid up into her pussyhole.  She was so wet down there by this time, it just slid all the way in.  You can't actually get in too far when the woman lies flat on her stomach and you enter from behind.  Her ass cheeks keep you from diving deep, no matter what size her butt is.  Of course, a tiny ass will get you deeper, but Jodie's is perfectly average, so I only get in 3-4".  But, I wasn't planning for either of us to climax, I just wanted both of us in a hot, sexy, "we'll try anything" horny state of mind. 

And, we were soon there.  We were both breathing fast and heavy when I pulled out to get to the main event.  Jodie REALLY didn't want me to stop, but I wanted her lusty, not satisfied and sleepy. To set up a bit, Jody poured herself a big glass of wine, then downed most of it in one big hit.

I moved to the middle of the bed while she put the harness on and strapped it tight, with the smallest dildo installed in it.  I crouched on the bed with my butt in the air towards her and waited.  She was a little unsure of herself, but she followed the instructions, coating the dildo with sex lube, then my asshole.  She used her thumb to push into my sphincter to get lube inside. Her thumb was smaller than most any poop I've ever had, so it actually felt good.  

Then, she leaned forward, placing the dildo head directly in the middle of my winker and pressed forward a little.  It immediately popped in just past the head, due to its small size.  She waited a bit, then pushed in again.  it was past the 1" sphincter muscle so it went in up to the harness in one quick move. "Ooops, did that hurt?  I didn't mean for it to go in that far.  It just got away from me." she asked with some concern.  "No, this one feels fine.  It's the others I'm concerned about" I cautioned her. 

Since this dildo was so small, we didn't see much use in thrusting much with it, so after a minute, she pulled out and replaced it.  I couldn't see which one she put in; I assumed it was the next size up.  She lubed both the dildo and my butthole again, pressed the head against the now slightly open butthole and gave a firm push.  The head popped in, but not without some noticeable resistance. "HEY!  THAT is NOT the next sized dildo, I'm pretty sure." I cried.  "I decided to skip a size, since the first one was so small.  You'll be fine.  I just need to get your sphincter opened up. Just relax your ass for a bit, like trying to get a big shit out.  I've seen the results of that, so I KNOW you can do it!"  She cackled.

After a full minute of relaxing, she lubed a bit more and shoved.  Nothing happened, but it certainly hurt on my end.  Another shove.  Another nothing. Then, a BIG shove.  My ass felt like it was split wide and she pushed in past my now VERY tender stretched out sphincter.  "You good?" she queried. "I'm sorry, did you feel a little poke there?  That's what I feel like when you push into me before I'm warmed up!"  She seemed a little hot.  I was now worried.

She pushed against me until the 7" was fully in my ass then paused for just 10 seconds, before starting to thrust the big meat in and out of my ass.  Now that the sphincter was stretched for this dildo, it didn't hurt.  I'm not sure it felt GOOD, but it didn't hurt at least.  

She drank another 1/2 glass of wine, then yelled "Ride 'em cowboy!" and began pounding my backside with the dildo.  It's hard to describe the feelings you get while this is going on.  It's NOTHING like sex, but it feels kind of good.  It's different for a man than a woman.  Men have a prostate back there, which can feel very good when rubbed against.  Women don't have that, but sometimes their G-spot can become involved, greatly increasing the pleasure feeling.

She poured another glass, drank most of it, then I heard her slur "Let's get this party started.  Where is that big, bad motherF***er!"  She somehow quickly exchanged the 3rd sized dildo for the 4th, lubed it up and pushed it against my asshole.  "Don't! It won't fit!" I pleaded.  

She was too far into it and gave a mighty shove.  The entire cockhead disappeared up my ass. It hurt like hell for a few seconds, then it subsided some. She placed a leather strap across the front of my legs to pull against while she pushed with all her might with her pelvis against the gigantic dildo sticking out of my ass.  She applied the rest of the lube bottle, getting it everywhere.  Then, with a great deal of grunting, she slowly pushed it further and further into my ass.  I could feel the enormous shape filling my insides, moving further and further into me until it seemed like there was no more room in me. 

She stopped pushing and said "Well, it's almost in all the way, but I don't think it will go any further.  Can you push back against it to start to push it out, like a big poop, so I can stroke it in and out?" she asked.  I did as instructed and squeezed my sphincter and pushed.  It slid 1/2 way out, then Jodie pushed it back in.  We did this several times.  On the last few, Jodie reached around me, lubed up my cock and started stroking it.  I started getting very aroused as she pushed the huge dick into me and jerked my meat with her warm slippery fingers  She put her other hand inside the harness, found her pussy and started fingering herself.  There was no shortage of lube anywhere.  It was on her belly, on her ass, all over her pussy hair, all over my ass and now my balls and dick too.  I think she came about the same time I did, shooting wads all over the towels.  I was glad we placed them there.  She pulled out of me and collapsed backward on the bed, the enormous dick sticking straight up in the air.  No loss of erection after sex for him... EVER!

After we both caught our breath, she asked too loudly "What do you think cowboy?  You want to go again?  My cock is ready for it!  And, I know your ass is spread wide right now to take it!"  She was right about my asshole. I put my fingers into my butthole and 4 of them easily slid in!  "NO, I don't want to be ass-fucked again, not now, not ever!  You know, you still have the buttfuck payment due.  We'll see how you like THAT!" I threw at her.  She had already passed out of all the wine, so my retort went unheard.

I peeled the harness and lubed dick off of her naked little body.  Before I went to bed though, I lubed and slid the smallest dildo into her slippery pussy hole, already enlarged from all her fingering and her orgasm. I figured she could wonder what happened when she woke up tomorrow.  She's lucky I didn't push it up her ass.  That would be pretty mean though, I thought.  Payback is a bitch, baby!