View Full Version : Diary Dares.

05-29-2007, 08:59 AM
This was written by a very special friend; she asked me to edit it and gave permission to post it here.

Diary Dares
by Victoria Day
Dare was to dress sexily and go to an XXX video store
Dear Diary
The video store was easy... and that's what they thought of me, I'm sure. But to make it more daring I chose "Cum on Her face 2 " for my rental and a pair of black lace panties.
The guys in the store ( four men... no other women ) were mostly averting their eyes when I was looking and I can only guess they were peeking at the most revealing moments. I was wearing a pleated skirt and halter top with runners but no socks, bra or panties. Movements up ( arms ) and bending down ( bum ) must have made for a sexy display. I bent down to inspect the bottom shelf videos a total of seven times!
No whistles or pick-up lines, but I noticed the clerk was smiling when I left.

Dear Diary
Dare was to go to a pet store and buy a dog collar and put it on in the store
I am typing this out with a new toy in my ' toy box '. and the smile on my face is nothing like the grin I gave that pet store clerk...
I wonder if giggles count as keeping a straight face on the dare? Because I sure giggled a lot. But that was part of my game... I dressed sexy 'little girl 'fashion with cut off jeans, halter top, runners ( no underwear at all ) and my hair done up in a single plait in back.
I changed a few plans... this turned out even better... I saw they had rubber dog bones near the leather dog and cart collars; so I picked out the collar ( giggle ) and chose the largest ( 9 inch ) rubber bone and took it to the counter... I was the only customer in the store.
I paid for the items and had the clerk cut the tag off the collar... ( guy in his mid thirties, I'd say ) ( giggle, in fact at this point I turned red and had a hard time controlling myself ) then I put it around my neck fumbling with it ( giggle ) so my arms and bare armpit stayed up and sexy and said, " Is that the biggest bone you have? "
I figured that was the line to make the guy blush but I was wrong; he said completely straight faced, "that's the biggest they make I'm sure your dog will like it. "... ( giggle )
What a chance... I just had to say it. Picking up the rubber bone I leaned over the counter and said with a giggle and a 'little girl voice, "Oh, I don't have a doggie, sir; this is for my pussy... ( giggle )"
I watched for a count of three and he went red... I smiled and winked and turned around and walked out of the store wiggling my bum seductively. He was behind the counter so I don't know if the blood rushing to his face was the only on-rush taking place in his body.
I am sure he will enjoy this episode for a long time to come ( no pun intended ) but the pun on dog, bone and pussy will put a smile on his face more than if I had streaked though the mall naked. Well, maybe that would please him too.

The dare was to make a bet I was bound to lose and, when lost, would be humiliating.
Dear Diary
It wasn't raining and that's a good thing because as we watched the last ten minutes of the game, Hal teased me into adding one more thing to the dare: the loser had to strip naked before getting on his / her knees and paying off the bet. In fact, the loser would have to be naked the whole time while sucking the winner's toes as well as his cock ( her cunt ). His point was that the loser would have to be buck naked, outside behind the dumpster for a good 15 minutes ( at least ). This would make it more likely some bar staff would catch us in a rather embarrassing position.
Even if it didn't happen, the risk that it would happen would make it all the more thrilling... for both of us, I think. We were pretty giddy and a little drunk too.
But that wasn't all, Hal was so sure of himself ( or such a Montréal fan )... he insisted the loser would have to shout between sucks... " The T-Cats ( Allouettes ) suck and so do I! " I have always been a Ti-Cat fan and I was drunk. That was my excuse as I took the bet.
A local band was playing in the main part of the pub but we managed to get a booth near one of the three TV screens and got them to tune in to TSN... volume down. We sat and watched. I admit I was playing with myself under the table ( remember, I wore my pleated skirt with no panties. ) I don't think Hal noticed.
The game was over by 10:30... And, without a word, we shook hands, finished our drinks and made our way out the door. Okay, we were both smiling as we left O'Connor's Irish Pub. The Guinness was good and we were about to find out if we'd go ahead with it.
You know what? We didn't even look at each other once we got out the door. We walked around the corner and straight over to the dumpster, turned facing each other and the loser just nodded and stripped naked leaving their clothes in a pile on the cement.
The winner obliged by removing shoes and socks. The winner leaned against the side of the dumpster and lifted one foot at a time for the loser to kiss and then suck. The toe sucking began and after each toe was sucked for ten seconds ( we worked the details out in the bar... shit, we were quite tipsy by then ) the loser had to admit ( out loud ) that their team sucked and so did they! Ten toes sucked clean and no one caught us.
Then the loser looked up and, at the approving nod of the winner, proceeded to dine on tastier meat. As agreed, the loser would give head until the winner was satisfied... this ended up taking, I reckoned, another 15 minutes. at one point we distinctly heard the sound of a door opening and a match being struck ( Ottawa is totally non-smoking in public places like bars and restaurants ) likely a waiter or waitress having a smoke break. But we couldn't see... they couldn't either as we were behind the dumpster.
But the loser dutifully said ( not quite so loud this time ) that their team sucked and so did they. Whoever was out having a smoke must have heard but if they did, they didn't let on.
The door closed and we continued for another ten minutes or so. Then it was over and the bet was paid in full! The Montréal Allouettes maintained their unbeaten streak. Hamilton lost. The Ti-Cats sucked and so did I.

The dare was to 'accidentally' stroke guys where it counts on a crowded bus
Dear Diary
It took two transfers this morning from 7:30 until 8:40 am to get just the right situation... but it paid off... I brushed by a few men ( no one in suits... they usually avoid public transit anyway ) with my thighs or back of my hand making fleeting contact with their manhood... some squeezed together type of thigh/cunt jostling into their asses... I was dressed early summer casual with no panties under my cut offs... tank top gave everyone a good view of my armpits as I hand from the bar above with one hand and pressed the flesh with the other...
On the last transfer i saw a guy, tall, cute and wearing tight jeans... I zeroed in on him ( he had a wedding ring so I felt safe... ) I jammed up against him and lightly toughed same as with the others before, but when the bus lurched I ' accidentally ' bumped into him with my ( no bra on) breasts and I let the palm of my hand ( not back of my hand ) bump into his crotch which started to grow... I LEFT MY HAND THERE... AND SWAYED BACK AND FORTH letting my boobs brush his arm back and forth and this brought my nipples erect... my hand jostled too and i pretended to be pushed from behind and... 'accidentally ' pushed my hand harder against his... well, hard on... I gave a gentle squeeze before pulling away and demurely mumbling... 'sorry... '' then got jostled back a few seconds later and pressed the flesh some more and YES I squeezed a second time... to break my fall... tee hee... I repeated this two more times and then I looked up at him... he was turning slightly red but he wasn't trying to move away from me...
I let put a few grunts which were half moans each time the bus 'forced' me to push against him... he was still acting as if nothing was happening but I can tell you... his cock knew something was happening.
I decided to make a joke of it and ease his embarrassment... "ooppps", I said... and smiled up at him as I gave his crotch-bulge a parting TWO taps... like patting a dog... 'down, boy'... and made my way to an aisle seat that just became free...
He inched his was over to my seat and stood beside me, his front to my side... What could i do, i couldn't pass up the opportunity... I raised my left are and grabbed the bar on the seat in front of me which meant my arm was raised and I leaned toward the aisle so that my left shoulder came into contact with his still bulging crotch... I moved gently back and forth and for the rest of the ride that guy got a ' shoulder-job'.
He got off first... off the bus I mean. but I'm sure the front of his shorts was as wet as my pussy was.

Dare to have an erotic jogging experience
Dear Diary
I bumped into two nice looking guys on me mine this morning. As you suggested I took a different route, the jogging and bike paths that run along the shore of Lake Ontario past Parkdale. I did as you demanded and nearly knocked the first guy over. I slapped at his bum with my right palm and grabbed his crotch with my left. I collided into him all the time laughing until I looked up at his face and mine turned to mock horror, I very nearly screamed and then blushed deeply. I sputtered my apologies but broke into giggles as I spoke, covering my mouth with my hand and looking, for all the world, like the most embarrassed girl on the planet. I did this twice, same routine, same effect... they both took it in stride.

Donut Shop Dare
Dear Diary
I had to do this right away or else i figured i would chicken out. I was dressed in runners, pleated skirt and blouse ( no socks, no bra and no panties ) I went to Tim Horton's for a coffee and a Danish... The donut shop was crowded as it always is on weekday mornings... I waited until I saw a guy across the way glancing... then i just adjusted my body to face him, with one swivel of my bum, then lifted my right foot on to the seat, bent down to re-tie my shoe lace, and let my skirt ' accidentally ' slip up my thigh... he got a fair view... but I spread my legs out a bit more to make sure he could see my shaven pussy... I took about 15 seconds to tie the shoe... caught his look... and gave him a shake of the head in disapproval... No one else must have seen... or at least didn't seem to notice... his face was red though...

Dear Diary
The dare was to get spanked by a stranger, on the bare or in the nude.
That went well! It only took a few minutes to do once i found my stranger. I found a lad on campus; he was in the main building which is open 24/7, he was in the student laundry room sorting his clothes. And guess what. He wanted me to be most daring but just watched as I took all my clothes off ( I was only wearing sweat pants and top and socks and runners ).
The problem of where was solved.right then and there in the laundry room. Well it was early, around 6:20, and no one else as there, so we went to it. Problem 2: He wanted to know how many spanks, it wasn't in the dare. So I said, " Oh, that depends on how naughty you think I've been." I was trying to be cute and play the dumb blonde.
So he says I have been very, VERY naughty and should get 100 spanks. Shit! I wasn't expecting that many but had to go along.
He took his time too. With me naked over his lap, he paused a good 3 - 4 seconds after each slap ( not really too hard, but hard enough after the 20th or so. AND he was a gentleman about it; spanking no hanky-panky ( although I couldn't help but notice his cock get hard under me. )
My bum was red when this girl comes in with a load of laundry. He just kept spanking me ( but harder now ) and said to the girl who was beside herself laughing, that I was pledging and had another 25 smacks to go. She just laughed and kept watching us. I played along and when it was over I thanked him and got dressed.

Dear Diary
The dare was to get strange men to hug me in public
This is the survey I've devised for the dare... I will play a third year RPI student doing field assignment for a sociology class. This has taken all morning to work out. This is what will be on my clip board
( Title ) Level three Human Social Behaviour Survey:
( sub-title ) Male response to hugging a pretty girl whom he has just met
( Script: Read each line and engage in field response with male participant )
Excuse me sir, do you have three minutes to help with a survey. It's an assignment for my Human Social Behaviour Class at Ryerson Poly-technical Institute? Yes? Thank you.
( if "no", say " thank you for your time anyway; have a nice day" )
Our premise is that Canadian males are friendly and feel comfortable with public displays of affection. Our enquiry is designed to discover ( a ) degree of comfort levels under a variety of circumstances, and ( b ) degree of positive or negative response from friendly interaction under a variety of circumstances.
I am going to ask you to give me a hug, given five different theoretical circumstances each of which are in a public setting. After the hug I will ask questions related to the survey parameters. Okay?
First situation: You have just been introduced to me by someone you know casually ( say at a conference ) and I reach out to you with open arms. Okay, ready?
( Student and Participant hug as per situation described )
Now in that situation, when hugging me did you feel: (1) very comfortable, (2) somewhat comfortable, (3) no feelings, (4) somewhat uncomfortable, (5) very uncomfortable
The second situation calls for your second meeting ( in public ) with someone you are used to greeting with a hug. You reach out with open arms. Okay, ready?
( Student and Participant hug as per situation described )
Now in that situation, when hugging me did you feel: 1 very comfortable, (2) somewhat comfortable, (3) no feelings, (4) somewhat uncomfortable, (5) very uncomfortable
The third situation calls for your meeting ( in public ) with someone you know very well and are, in fact are used to close physical contact in private settings. We both reach out with open arms. Okay, ready?
( Student and Participant hug as per situation described )
Now in that situation, when hugging me did you feel: 1 very comfortable, (2) somewhat comfortable, (3) no feelings, (4) somewhat uncomfortable, (5) very uncomfortable
The fourth situation calls for long-time intimates meeting in public in a situation where you want to express pleasure at seeing each other. We embrace for a long and intimate hug. ( wandering hands above clothing only ) Okay, Ready?
( Student and Participant hug as per situation described )
Now in that situation, when hugging me did you feel: 1 very comfortable, (2) somewhat comfortable, (3) no feelings, (4) somewhat uncomfortable, (5) very uncomfortable
The fifth and last situation calls for two strangers in a public situation, but each feels a strong sexual attraction to the other; their hugging is more like groping with hands wandering beneath clothing, intimate touch at comfort level. Intimate embrace to continue until one participant pulls away. Okay... Ready?
( Student and Participant hug as per situation described )
Now in that situation, when hugging me did you feel: 1 very hot, (2) somewhat horny, (3) no feelings, (4) somewhat embarrassed, (5) very naughty and in need of a spanking?
Thank you for participating in this survey. Have a good day.
Right... so that's the set up. I will be wearing the following: runners but no socks, mid-riff tank top and no bra, tan flannel running shorts ( baggy with elastic waistline so the guys can easily slip their hands down my pants to grope me in front or behind ) and NO PANTIES... pussy, as always, smooth shaven and, no doubt, wet. The men making it to situation five will have a pleasant surprise.
I hope to carry this out around noon hour later this week when I have a late shift at the store. My dare target: Ten men taking it to at least level four and at least two guys going all the way to level five.

Hugs survey dare!!!!
Dear Diary
GOD, I NEED A SHOWER... But I have to jot this down first... My sticky, sweaty clothes are in a heap in the bathroom, my pussy is so wet I could smell myself though my clothes this morning.
What a dare this turned out to be... I wore a Blue Jays baseball cap to better look the part ( yes, I wore pig-tails tied off with elastics to look cute ). Now, as to who I picked to survey: I was discriminating only in as much as I picked good-looking guys only. But married or not, all races, tall and short: they were approached for the RPI Sociology survey ( I like to think of myself as an equal-opportunity slut ).
The results... I wouldn't have believed it... of those who took the survey 14 ( about 1 in 4 that I stopped ), ALL of them got to question number 3 and gave close physical contact hugs ( some squeezed and I squeezed back ) but some stopped after hearing the next step was groping in public.
Only six of them went further after hearing question number four... Only one guy stopped after feeling me up ABOVE my shirt and grabbing my ass... he chickened out? Or wised up and wouldn't slip his hands down my pants. In fairness, he was wearing a wedding band.
The other five were not so shy... I have to say, the guys who went all the way could tell this was a college prank or dare... and they said as much afterwards... Still, I kept a straight face and insisted it was just my homework... But by then they could probably tell I was hot in more ways than one... Like I said, I could smell myself getting horny.
The five-fingered five who completed the survey took at least 30 seconds each on their final hugs and let their hands wander in back and in front... I kept a straight face but I couldn't stop myself from moaning as they touched me. One guy tried to kiss me and I acted very offended and said, "Sorry sir, hands only. " Two tried to get my phone number and I really acted offended but as I was breathing heavily at that point, I don't think they took my protestations seriously.
Honestly, the fab five must have clued in early on and just had fun... anyway, I did... but I must take my shower now...

Try before you buy dare
Dear Diary
On my way to work I pass by a shop with a sign that reads. 'Marital Aids". When I first saw it I thought, " Oh, I guess they sell karate sticks." Then I saw the XXX Videos sign. I felt like I was having a "Blonde Moment". I was confusing 'martial' with 'marital. "
The Sensations Store carries aids, lubricants, cards, mags and videos; I knew because I had visited one outlet a few weeks ago on a dare. Dare WAS to buy a vibrator while sexily dressed, but it went a bit further than that.
So here's how this latest dare turned out last night.
I wore runners, wrap-around skirt over cotton, brief but not thong, panties, white tube-top ( showing bare shoulders and tummy ); I wore my hair down.
I went straight to the 'toys' display ( noticing there were four male customers and the clerk ) and perused the dildos. After a couple of minutes ( the men were all giving occasional glances by now ) I took one realistic dildo to the counter and in as 'dumb blonde' a tone I could manage, I asked, " Sir, these marital aids; do they work if you're single, or do you have to be married? " I had to rephrase and repeat my question. He assured me they work... but I then asked how do you know if it's the right size... By now everyone was in on the conversation and I could hear sniggering which I ignored.
I asked if they had a bathroom I could use. Reluctantly the clerk indicated a small toilet in the back by his office. I went in and took five minutes. What they heard in the store was me 'trying out' the merchandise. I took off my panties and put them in my purse, then fucked myself for a few minutes letting out moans and appreciative gasps.
I went back to the front of the store and ignored their looks and said, " Too big, but I'll take it anyway." Then I opened my purse to get money and "accidentally' my panties fell out on to the floor. "OOPPS! " I said and, spreading my feet wide apart, I bent from the waist to pick them up; naturally my short wrap-around rose to expose my bare bum and pussy. I paid and left with my newest toy.

Head Tax Dare
Dear Diary
Sigma Girls Rock!
It cost me ten bucks but it was worth it! After work I went home and got changed. I stripped and then put on... First, jeans cut offs ( the ones with the slit on the right side ) runners ( no socks ) loose fitting white shirt ( men's Large with button-down collar ( don't ask how I acquired that )... then on TOP went my bikini panties over my shorts and over my short went my black lace bra.
In my back pocket I stuck my ping pong paddle, but first I scribbled Sigma Theta Chi on the face of it in black marker. I stuffed two five dollar bills ten into my shirt pocket ( under my right cup ) and marched over to the Carleton campus.
The Student Union building ( where the laundromat is ) was busy with students watching the Olympics on CBC. There's a cash bar there. I walked in as bold as can be... got lots of looks and more laughs and I just bowed low to everyone ( as if that were part of my ( all too obvious ) sorority pledge.
First I went up to a girl who was giggling with her friends at my appearance. I smiled and asked if she would help with my initiation. She said... sure
And I handed her my paddle, turned my back on her, bent low and said, " 12, please." And sure enough, she gave it to me. I turned back and thanked her. Took the paddle over to another girl. Same thing.
Then I went up to a guy who was hooting at my antics. He smiled and put his hand out for my ping pong paddle.
" No, sir." I whispered to him. " But I'll give you five dollars if you let me give you a blow job in the men's room. " I didn't have to ask twice. We went down the hall into the gents, locked the door and I got on my knees, took a fiver out of my pocket and held on to it while I pulled his zipper down, yanked down his shorts and took his cock and balls out. Then with the fiver still in my hand, I gave him a very satisfying blow job; he took his reward and gave me mine. It took 10 minutes at least. He was about to come.
I was not finished. I stayed on my knees and pulled the other five dollar bill out. With his cock in my hand I said, " One more pledge test... I'll give you five more if you finish off and cum on to my face." I held his cock and placed the head on my out-stretched tongue. And then I lifted my head back and let my hands free; his cock resting and throbbing on my face.
Just a few seconds pause, then he took the second five from my hand, grabbed his cock and started stroking himself right in front of my face. It didn't take long. He came all over my face.
I got up, bowed low and handed him my paddle. I figured it had to look like a sorority gig and this was the best way.
" Thank you, sir. Now, Six on each cheek. " I said. He obliged They were hard swats too. Now the real ballsy thing. I took the paddle back, thanked him and marched out of the washroom ( with him triumphantly trailing behind ) without wiping any of the cum off me. I walked briskly up to the bar where the girls were who had paddled me before; I thanked them, turned and walked out and down the steps, out into the parking lot and into my car.
It's amazing what supposedly smart college students will think a girl would do to get into a sorority.

Dared to play 'sex slave'
Dear Diary
I must write down my non-cyber discipline experiences. I really have only two. One was great, the other too nasty to remember. But my weekend with ' Sir Stephen " ( his real name was Ken ) was wonderful. It was from Friday night to Sunday afternoon. About six months ago, in the early fall. I had answered a posting from a Sir Stephen... he said I was the only one to respond, seeing the allusion to the Story of O.
So, after one encounter, when we learned to trust one another, we set a date for a weekend of fun and games in his cottage. We arrived late, I driving while he played with me under my skirt. I wore no panties, as per the book, but carried them in my bag along with a 'toy' i was told to purchase.
Inside the cottage his demeanour changed to strict and authoritative:
" I'm going out for a pee, when I get back I expect to see you naked, kneeling and with you hands clasped behind your head. " He returned in under a minute and I had obeyed.
20 strokes with his belt on my bare buttocks. Up I rose on command and lay on a table top which was under a cross beam; he fastened my ankles with strips of cloth and tied them to the cross beam, legs spread fully. He used my panties to tie my wrists together and fasted the joined hands to a leg of the table. I was bound and open.
Next he inserted an English cucumber into my gapping pussy. and worked it for a while. When I started to cum, he used the soft leather flail I had brought ( it was my favourite ) on my thighs, bum and open pussy. Every so often he would stop, stand over me and masturbate next to my face but stop short of cumming.
After some time he released me and placed me in a variety of positions and used belt, paddles and bare hands to give me the discipline I craved. And, after much begging on my part, he let me suck him off. I kept his load in my mouth as I drifted off to sleep. In the morning, I said I could still taste him.
The next day he took me to an isolated spot ( up a logging road ) He stripped me, bound me to a low-hanging tree limb, and gave me a whipping with a switch. Then he untied me and told me to close my eyes for 5 minutes while he left ( with my clothes ) he said I could find them somewhere beside the trail, but I would have to go naked through the bush to find them.
It took me half an hour to get back; he told me later that he had returned in just ten minutes.
Evenings in candle light and candle wax games were the order of the day. I am / was a smooth shaven girl and he said my cunt lips invited drips of hot wax. My breasts, while not too large, have very pronounced nipples when stimulated. He introduced me to paper clips as a way of adjusting the pleasure/pain level. i still use them.
Sunday we went visiting and I acted totally normal... until we returned and he ordered me to play with myself with the dildo I had been ordered to buy. He sat and watched. Then back home. He tried to get me to join in a foursome a few weeks later. But Ii said "no"; I had enjoyed our weekend but thought it too risky.

05-30-2007, 02:17 AM
long story, but good, thanks!

05-30-2007, 02:19 AM
Amazing stuff thanks