Playtime Chicago

What was your first time like ?

By Playtime Chicago, July 23, 2020 in Cuckold Dating

• firsttime
• cuckold
• (and 2 more)

  Tagged with:

  • firsttime
  • cuckold
  • watching
  • shame

Any cuck regret stories?

By Playtime Chicago, August 23, 2019 in Cuckold Talks

• reluctant wife

Cuck or hot wife themed movies ?

By Playtime Chicago, January 13, 2020 in Cuckold Talks

Away from home for a month and hope she gets some seed

By Playtime Chicago, May 26, 2020 in Cuckold Dating

• cuckold

Where is the most sexually adventurous place in the USA?

By Playtime Chicago, June 12, 2020 in Cuckold Talks

• cuckolds
• hotwife cuckold
• (and 2 more)

  Tagged with:

  • cuckolds
  • hotwife cuckold
  • vixen
  • stags

My friends quandary

By Playtime Chicago, May 27, 2020 in Cuckold Talks

Do I ask her again as my birthday present?

By Playtime Chicago, January 11, 2020 in Cuckold Talks

• cuckold;
• stags
• (and 1 more)

  Tagged with:

  • cuckold;
  • stags
  • hotwife

How do I get my wife to do this for the first time.

By Playtime Chicago, December 6, 2016 in Cuckold Talks