Embarrassing dare?

[crystal]

mine is having toanswer the door for delievery food guy naked then ask if i gave him a blowjob i could get food for free

[crystal]

masterbaiting on a bridge filled with cars

[fork]

Never really had any that were that embarassing.
I guess it would have to be acting like a dog.. but I was alone, so it just felt kinda weird.

[batman]

Originally Posted by crystal

mine is having toanswer the door for delievery food guy naked then ask if i gave him a blowjob i could get food for free

did you get the food for free?

soz should have PMed that

[legbarer]

Mine was when my wife and were on a clothing optional beach with another couple. We wore swim suits but joked about getting naked. The other woman had great breasts, but said she would not go naked, unless I agreed to stay naked for our entire week at this beach, shave my pubic hair in front of the group back at the hotel, paint my toenails red, and wear strappy high heels to dinner each night that week. The woman's husband assured me that I would not be disappointed when she removed her top. He was right. The week turned out pretty good, after I got over my embarrassment. I got a lot of compliments on my red nails and black strappy high heels.

[naked40]

walk naked through an area frequented by gays who were also naked

[Memories for Life]

I'm guessing it was only your girlfriends who got to you do this! Were they supposed to give your clothes back after a few minutes but tricked you instead and ran off with your stuff? How far did you have to go to get something to put on?

[Memories for Life]

Originally Posted by the nuge

Well it was a dare from my friends and they helped him the whole time. He didnt actually do that much cuz my friends were having fun mocking and humiliating me.

Did you get your bare ass spanked alot with hands and/or belts? Were you penetrated in every possible opening?

[redneckman]

i had too get naked and go lick to a hot girl and "accidently" fall into her boobs

[Memories for Life]

This wasn't embarrassing for me but it was for the girl that had to endure it!

She had recently lost her job and had to make a $400 car payment. Her new job wouldn't pay her for 2 weeks so she came to me begging for help because she knew I had a great job and was generous with my money! She didn't know about my kinky side but she would find out!

I told her that I'd give her the $400 on one condition -- she would have to pay an exchange rate. This girl was only 19 and she was (is) smoking hot and worked as a shooter girl at a strip club (she could never do the stripping in public thing). She said what kind of exchange -- I told her for each $1 I would spank her butt as she laid over my lap! When she realized it would be 400 spanks, she wanted to reduce it by some! I offered half off on spanks if she was half off in clothes -- I'd give her 200 spanks wearing bra and panties! She still didn't think she could take 200 spanks so she offered to be completely nude for only 100 spanks but she needed to have the money in hand up front before she took anything off! I agreed and we would meet the next morning in the middle of the parking lot near my bank.

I suspected she might try to pull a fast one by getting the money and then driving off! I couldn't try to get it back in public because I'd look like a bad guy for trying to solicit prostitution. She had to do this willingly. I went my bank early and withdrew the $400 all in single $1 bills. I then put 200 $1 bills each, rolled lengthwise and rubberbanded tight inside (2) resealable plastic snack baggies! This produced (2) 6inch long x 2inch thick packages!

When she met me in her car at the parking lot, I noticed her windows had very dark tint so I knew she might agree to my special conditions. She said where's the money and I told her we both wanted our side of the deal to be completed so here was how the exchange would happen. She desperately needed the money that day or the car company would take her car! I showed her the money packages and told her, to ensure she had to allow the spankings, she had to give me all her clothes AND I would insert one money roll in her pussy and one in her asshole AND she had to keep them there while she drove naked across town to a place where she would be spanked. Her eyes got huge and she couldn't believe I was such a freak! She knew it was crazy but she had to have the money so she agreed. After taking off all her clothes, she easily pushed one money roll up her pussy like she did it every day. However, I had to liberally lube the other one and force it up her formally virgin asshole! She turned bright red with embarrassment! I took her clothes and anything else she could use to cover herself with and told her to follow me in her car. Make sure you keep both rolls all the way in!

I drove across town to a deserted restaurant parking lot I knew, calling her along the way to bug her about having enough gas to make it! She couldn't take out the cash -- she had to make some other deal to buy gas! Her reply wasn't very cordial. When we arrived at the destination, I climbed into her backseat of her 4-door sedan. I told she could get out of her driver door and walk around the car completely naked or she could climb over the seat back and onto my lap. Her clothes remained locked in my car until the spanks were all done. Even though the parking lot was deserted and it was off a minor street, she didn't want to be naked in public so she chose to climb over the seats and onto my lap -- I told if either money roll fell out, I'd add 100 spanks per roll to the total. Fortunately, she was able to keep both orifices clenched tight! Once she was in position on my lap, I started raining hand spanks on her bare ass cheeks. After a few minutes, she says please stop, how many more is there??? I told I wasn't counting, she was supposed to count after each spank. I guess we'll have to start over. She groaned "Oh No!" but what could she do?

Her ass was already bright pink and my hand was hurting so I used one of her sandals to "formally" spank her. She counted each strike as I did 10 on each cheek before switching to the other cheeks. In the "end", her butt was a dark red color but she wasn't crying from the humiliation. She told me she orgasmed as least twice during the entire ordeal. The front of my pants showed the proof of both our "enjoyment". I gave her back her clothes and told her if she needed any more "help" she could cum to me anytime! She gave me a kiss on the cheek and a hug while whispering in my ear "next time I'll need more money!"

[Embers]

Probably one of the first 'dares' I gave myself, my family were all out so I decided to try some self bondage and got caught by my older sis was bad times lol

[The Laughing Fish]

Back in my teenage years, one game ended up with me having to kiss the bare ass of a male friend, in front of other male friends. Which meant I was pretty much owned by him from that point onwards.

I was generally smarter and witter than him and could usually outargue him, but every time I got the upper hand could be nullified by "Well, you kissed my ass."

[thedaring1]

Mine was probably 1 year ago, I was playing t or d with a gf and she dared me to wear her little sisters My Little Ponie panties for 3 hours. It was very humiliating but turned me on a bit :-/

[Liz]

My dare was really embarrassing! I was 17 and I have pretty big boobs. All the guys at my school were always joking about them, etc, etc. So, at a party we were playing truth and dare and one of the guys dared me to strip naked and do a dance for them. I accepted, just because I'm a sucker for dares! I stripped naked as they cheered and began a quick dance. As I was dancing, they were all laughing and cheering me on. I was bright red and feeling really foolish though! Finally I finished but they had pictures of it and still tease me!

[sambora123]

me and my gf play a game where the person giving the dare tells you what you basically have to do, and nothing else no details or anything, so i could say "all you have to do is walk through that door" but that could mean the door is locked so you have to get the key to go through it but the key is taped to the doorbell of next doors and you have to go naked for example. then when she tells you the basics you have to say yes or no to whether you'll do it or not. can be a lot of fun especially if you have a selection of two and you have to do 1 so choose your fate lol.

anyway we had to get home from her parents house it was late and we lived like 60-75 miles from there, so we decided to play the game, a few dares were completed when we pulled over with bout 30 miles to go, i gave her a dare said she had to trust me she said yes so she had to handcuff herself topless to a lampost and leave me the key and after 5 mins i'd free her. and she did it lol, but she was angry in a playfull way saying its payback time.

so she said all i had to do is sit there and think of the one thing i wanted the most, sounds easy right, so i accepted. big mistake. she smiled went got the tow rope from the boot(trunk), took my top off and thoroughly tied my hands behind my back around the seat. pulls everything off leaving me naked then she said "now think of what you want most in the world, you have till we get home or if you can escape b4 then, which i doubt, you can get what you want most in the world meaning your clothes back a little earlier than expected. then she drove home, now it wouldnt be that bad but she is really into bondage and knows how to tie someone so i was squirming immediatley
knowing i was in trouble we went through towns and villages i noticed she avoided motorways and took local routes being seen would be more likely.

got her back though but very embarrassing