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About ChicagoLady

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  1. Hi PaintsRed - It is good to know that there are HOHs and ERs on this site like yourself who are respectful, fair, and know how to lead a spanking relationship. Your announcement and ritual are perfect for putting EEs in the right state of mind for punishment. Chicago Lady
  2. Although we can ALL agree that it would feel great at the time!!!
  3. Now that I ponder on this a little more SassyLittle, you may have a point that disconnecting his brakes and setting his house on fire could have jail cell and spanking consequences! Perhaps I was a tad rash and vicious there...🤔 Sorry SissyMissy - Checklist Item #4 may not be the most legal or mentally healthy solution for getting over a spanking break-up.
  4. Isn’t that what those tiny portable gas cans are for?! 😉 Oh no...this could get REALLY dark REALLY fast!
  5. Thanks for your kind words! Things weren’t perfect between us, but he will be a tough one to forget and replace, but always one to respect and treasure. Spanking relationships are so lovely, special, and deep. So glad that you have found your perfect spanking companion!! My we all be blessed with that as well!
  6. SassyMissy Checklist: 1. Block this guy so he doesn’t bother you again and your not tempted to contact him. Take control where you can! 2. Dive into SassyMissy Super Self-Care! Whatever that is for you! For me a bubble salt bath, with candles, soft jazz and a glass of champagne. 3. Reclaim your holidays! The holidays associated with pain have to be redefined. Maybe with just friends next time or traveling someplace new! 4. If you know where he lives and parks his car 🚗, disconnect his brakes. Just Kidding! Here I go with my bossy self!
  7. So sorry to hear that you had this experience. Strange, unnecessary comments. She obviously was struggling with some serious issues. Sounds like you handled it with kindness and dignity - great ER traits! Glad that you shared this so we could provide support!
  8. My longest punishment spankings were 30 minutes with brief breaks to get in a new position for a different implement. He always determined how long in each position. 1. I would go bare bottom OTK for his hand and hairbrush. 2. Then positioned bending over with my hands on the bed and bottom out for his paddle. If using the school paddle I am over his desk. My bottom always had to be pushed out to meet his paddle. If not, that swat didn’t count and was repeated. 3. Then positioned over the spanking pillows on the bed so my bottom was raised for his strap / belt. Always
  9. In my last TiH relationship, I received Sunday night maintenance spankings at bedtime with his hand and hairbrush. If I had already received a punishment spanking that week it would be harder and longer. He would also increase maintenance spankings per week if necessary. This was done through scolding to increase my embarrassment and submission. “How many punishment spankings did you receive this week young lady? Do you think that’s acceptable? Do you think we should have a harder spanking tonight? Would that improve our behavior this week young lady? Perhaps more maintenance is c
  10. And I am limp over his lap, with a very sore spanked bottom, crying tenderly, grateful for his discipline, and awaiting his sweet aftercare...Perfection!
  11. And of course my whimpers at every spank, holding back tears, and trying my best to take my spanking like a good girl!
  12. So well stated! Yes it would definitely add to the embarrassment!
  13. Please, please be gentle with yourself! Please don’t feel stupid and foolish for loving so deeply! My break-up with my TiH partner was devastating also. Even though we had some serious problems and it needed to happen, it still blew me apart. Sometimes I don’t think of him for weeks, other times I can’t get him out of my head for days. I think these break-ups are hard for us because we spend so much time communicating and building trust with our spanking partners. Our bond with them is so unique and beyond words. But thank God we had that bond! He may be out of your
  14. Scolding with questions while being spanked with the hairbrush was so embarrassing for me and extremely effective. He easily picked up on this so it happened during repeated punishment spankings. “So I guess we are still struggling with talking back?” ”Apparently the last time I spanked you for talking back didn’t make an impression, did it young lady?” “I guess I didn’t spank you hard or long enough with the hairbrush did I?” “Should we follow it with the paddle and belt young lady?” Amazing that talking back was no longer an issue afterwards! 😉
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