A Wager on Chastity and Romance

The other evening my wife and I had a wonderful time together. She kept me tied up and blindfolded, then delivered what she calls the “Triple Whammy.” (This involves her putting ginger up my backside, inserting another piece down my urethra, and coating my penis with toothpaste before edging me several times). It is an incredibly intense teasing routine. Once she finished her work on me, it was time for her to reach her own climax. I lubricated my hand and began gently massaging her crotch area. As she approached the peak, I slipped two fingers inside while rubbing her clit with my palm. She went completely limp under my touch, clearly nearing her release point. She instructed me to insert my penis to finish her off. I complied, and she quickly climaxed in strong waves. Unable to hold back any longer, I joined her a few thrusts later with my own orgasm. We basked in the afterglow together, enjoying ourselves immensely. She wasn’t angry at all; instead, she laughed as I was playfully labeled the “bad boy”. Yesterday while discussing our ongoing dynamic, she mentioned wanting to keep me chaste for 30 days leading up to our wedding anniversary in August. I told her she would need to stay sharp to make that happen. We then struck a friendly wager. If she succeeds in keeping my chastity intact for those 30 days, I must take her out for dinner at a Bed & Breakfast. If she fails, the roles reverse, and she has to go on a fishing trip with me. This adds a fresh twist to our routine. Interestingly, I will be eagerly waiting for her guard to drop so I can win this bet. It is worth noting that she definitely has the power to enforce my chastity if she takes certain precautions. She can secure the Jailbird escape-proof using our tamper-evident ribbon method. Additionally, she keeps me restrained even when the cage itself comes off. Numbing cream is another tool at her disposal whenever PIV becomes permissible.

I hope you both have a wonderful time at the B&B!;)

Really? I was about to suggest he catch something big.

She wasn't mad; she actually laughed at me being the "bad boy". Not mad, eh?!:o Just so everyone knows, I'm already packing my suitcase - not my tackle box!:lol::lol::lol: mellykh

I find the wager exciting no matter who wins. If the stakes are valued highly enough, kh will prevail. I would happily make a similar deal with my own kh even though I know she could win if she is determined to be careful at all times. By the way, the longest I have gone without an orgasm is 3 weeks, so for my kh to win under our potential wager, it would mean setting a new personal record.:o

The bet begins this Friday. I am very conscious that my last few orgasms are slipping away. If she sticks to her game plan strictly, I don't stand a chance. However, 30 days is quite a duration. She only needs one slip-up.

> member_0169c7b244 wrote:...but, 30 days is a long time. She only has to slip up one time. ...we shall see about that!;) mellykh (packing suitcase for the B&B):lol::lol:

:o the heat is on! mellykh (alias: WINNER!;)

LOL, would love to see an update on this.

We are having fun! This is day 10, with 20 days remaining. The urge for orgasm is building steadily, and she feels no pity for me at all. She did slip up a few days ago by leaving me uncaged while taking her shower. I could have won the bet then, but I took the high road and restrained myself. She has been much more careful since. This morning, she brought me close to climax several times (I was blindfolded and restrained), then announced that the pleasure session was over. Before I knew it, she started rubbing something on my cock. Within seconds, my penis felt like it was on fire; she had massaged it with icy hot. Wow!!!!!! She showed mercy by cleaning me up with a soapy washcloth after only about a minute. It is easy to see how icy hot could serve as punishment.

I would not have passed up the chance for a fishing trip:D

We have a winner! Last night was amazing. After we showered together, she removed the jail bird and allowed me some edging. Then, she requested that I provide her with PIV. My instruction was not to climax. After just 3 or 4 thrusts, it happened. I couldn't believe how fast it occurred. It wasn't planned; once it started, I simply could not stop it. Boy, what a gusher too. She still wanted her own pleasure and insisted that I go down on her. I obliged, figuring she deserved it. She wasted no time getting me back into the cage. I suspect it will be quite some time before it gets unlocked again. I reminded her we have 19 days left until our anniversary in August, which would still constitute a nice release. She started whispering the lyrics to "see you in September". As a consolation prize, even though I won the bet, we are still heading out for dinner at a Bed & Breakfast.

> member_0169c7b244 wrote:...even though I won the bet we are still going to a Bed & Breakfast. I knew it!:lol: Before you leave, don't forget to hitch up the boat. 8-)

> member_0169c7b244 wrote:We have a winner! > .... even though I won the bet we are still going to a Bed & Breakfast. Remember, cheaters NEVER win!;) I guess we keep this routine until I slip up again:roll: (13 days and counting down)

Wow, my wife must have me well trained. I only get about 12 real Os per year (roughly one per month). Most of the others are completely ruined PIV orgasms where we both stop moving entirely and I release inside her with little to no pleasure at all. She likes those because I stay hard and continue pleasuring her. Does anyone else mostly stick to ruined Os while inside? My wife is very strict about this! She strongly demands that I be ruined, or she will not allow me back inside for a long time. I figure it is better to enjoy being inside her even if I don't get a real O. She has trained me well because just one real O per month satisfies little more than an hour or two of relief. She developed this system because she says I behave much better now compared to when I had higher frequency orgasms. She used to hate it when I climaxed often and was less behaved, but now she is happy with the system that works for us. By the way, she is on track to experience over 300 Os this year while I stick to my 12 real ones. Does anyone else have a similar setup? Rob