Winning the Bet
2008, English. Directed by Ted McIntyre.
Watch Ryan, Devon and Brett use their “winnings” anyway they see fit. Whether it is Damien secured to posts, paddled, flogged, face and ass fucked or Riley put into stocks or Kyle drenched in hot wax, flogged, paddled plus face and ass fucked. Everyone wins in one way or another.
- Runtime
- 1h 11m
- Post-credits
- None listed
- Language
- English
- Rated
- Check local
Start now and it ends at ….
Too new to call
Not enough people have rated it yet for a verdict.
Seen it? Give your verdict.
Saved privately on this device.
Where to watch Winning the Bet
Winning the Bet isn’t streaming on any OTT platform in India yet; it released on 25 March 2008.
No streaming listings yet. Search JustWatch.
Cast & crew
Details
- Released
- 25 March 2008
- Country
- United States of America
Check ratings elsewhere
News & fan talk
If you liked Winning the Bet
Preaching to the Perverted
1997 · 6.1/10
Popcorn FlickRecommended by TMDB viewers
Pillion
2025 · 6.5/10
Popcorn FlickRecommended by TMDB viewers
Fifty Shades of Grey
2015 · 5.9/10
SnoozefestRecommended by TMDB viewers
My Awkward Sexual Adventure
2012 · 6.7/10
Popcorn FlickRecommended by TMDB viewers
King Cobra
2016 · 5.8/10
SnoozefestRecommended by TMDB viewers
Nymphomaniac: Vol. II
2013 · 6.7/10
Popcorn FlickRecommended by TMDB viewers
Pink Flamingos
1972 · 6.1/10
Popcorn FlickRecommended by TMDB viewers
Tongues Untied
1990 · 6.7/10
Popcorn FlickRecommended by TMDB viewers
Secretary
2002 · 6.8/10
Popcorn FlickRecommended by TMDB viewers
Mandingo
1975 · 6.6/10
Popcorn FlickRecommended by TMDB viewers
Winning the Bet: quick answers
Is Winning the Bet worth watching?
Winning the Bet doesn’t have enough ratings for a verdict yet.
How long is Winning the Bet?
Winning the Bet runs 71 minutes (1h 11m).
Does Winning the Bet have a post-credits scene?
None is listed for Winning the Bet. Viewers tag these on TMDB, so a brand-new film may not be tagged yet.
Winning the Bet parents guide: is it suitable for kids?
No age rating is listed for Winning the Bet yet.
Which OTT platform is Winning the Bet on?
Winning the Bet isn’t streaming on any OTT platform in India yet; it released on 25 March 2008. (Checked 12 November 2026.)
What movies are like Winning the Bet?
If you liked Winning the Bet, try Preaching to the Perverted, Pillion, Fifty Shades of Grey.
Who directed Winning the Bet?
Winning the Bet (2008) was directed by Ted McIntyre and stars Damien Braxton, Kyle Young, Brett Conrad.