tagGroup SexDare You Dare Debby?

Dare You Dare Debby?

byimhapless©

I'm Debby Wright, but most of my friends call me "Debby Dare." I'm a buxom lass, with big beautiful tits, a big round killer ass, a three pack (half a six pack), sculptured thighs, naturally blond hair, blue eyes, and a usually moist hairless pussy; and extremely humble (ha, ha).

I must have the gene that craves excitement because - to re-state the obvious - I crave excitement. I've never intentionally done anything life-threatening [I'm not an Evil Kenevil], but I sure have done some bizarre things, many of them just plain sexual, or with sexual overtones, most as a result of goading by my friends.

As examples: While in high school, in the 4th of July parade in my home town, ala Lady Godiva I rode on a white horse with just my bikini bottom on, only my long blond hair barely covering my big tits. In college, I fucked the librarian in the stacks at high noon. At work, after a co-worker "pennied" my male boss in his office so he couldn't get out the door, I pressed my bare ass against a transparent panel of his office wall.

So a few weeks ago, I was having a beer with some of my co-workers, Brad, Simon, Tina and Louise, after work at the bar in a local restaurant. We were reminiscing about the pressed ham incident (the boss never figured out who it was, and he was fired by the home office soon thereafter for unrelated reasons), when Louise asked if I'd ever gone completely naked in public.

"Sure," I said, "many times."

"Bullshit," Simon, Tina and Brad blurted out, virtually simultaneously.

"It'll cost you $20 each if you want me to prove it," I retorted.

After the three skeptics each laid a Jackson down on the table, I gave the money to Louise to hold, pointed out the window to a newspaper vending machine across the street, got 50¢ out of my purse, and said "Let me get a paper for you."

Since it was summer, I had little on -- just a sundress, bra and panties. I walked outside, quickly removed them, held them under my arm as I ran across the street in my birthday suit and got a newspaper from the vending machine. I then ran back, holding the paper over my head in triumph.

As I was running to-and-fro, my mammoth tits were bouncing up and down so much they almost bruised my stomach and poked out my eye (ha, ha). No wonder I wear a jog bra when exercising!

It was still very light outside, so there were lots of stunned looks by passers-by. Of course all of the guys who saw me were hooting and hollering, with many cell phone cameras pointed my way (maybe I'll be a You-Tube star). I didn't have to worry about traffic, though; all cars came to a halt as I ran across the street and back; lots of horn honking, but not out of anger, more joyful than hateful sounds. I don't think I caused any auto accidents -- I hope not!

I had a big smile on my face the whole time. I enjoy being naked no matter what the circumstances, so it was great fun for me. I would have done it just as a dare with no money involved -- the $60 just made it that much sweeter.

When I triumphantly returned, I put my dress back on outside the restaurant, not bothering with my bra or panties, and returned to the table with a self-satisfied grin. While Tina was pissed, Brad and Simon each has saucers for eyes, and said the show was well worth the $20. "Next time I'll make it $100," I replied.

Over the next few weeks, my co-workers schemed to find ways to win their money back with various dares, taunts, and challenges involving escalating levels of exhibitionism, public nudity, and voyeurism. But contrary to their expectations, I was getting a lot more spending money, and they were crying in their beers. It culminated when I shocked them by accepting a dare to crawl under the table at the restaurant and suck off Simon. He ended up embarrassed, first because he had a really ugly dick, and he knew it, and second because I didn't swallow but rather made him cum all over his pants. I thought that might put an end to their dares, but not so.

Perhaps I was getting too cocky. But I couldn't help myself; damn I was good! Then one Friday I arrived at our normal watering hole after the other four were already ensconced in our conventional seats. I didn't realize they were playing me when they offered to buy my libations, telling me I was too classy for beer and purchasing mixed drinks for me instead. They continued to flatter me, lauding my bravery and appearance, as I got more and more high.

Eventually Brad pulled a $100 bill out of his wallet, ostensibly to use to pay our tab. Before doing that, though, he started laughing. When Tina asked what was so funny he said "I wonder if I dared Debby to fuck anyone in the restaurant named Ben Franklin," (whose visage appears on the front of the $100) "if she would?"

"Why would I?" I asked.

"I guess you have become too complacent in view of your past winnings," Simon teased, "The Debby we knew and loved would take that dare in a heartbeat. Let me sweeten it. I'll add a Franklin of my own."

"What if there is no Ben Franklin in the joint?" I queried, knowing it was very unlikely there would be someone named Ben Franklin in a place having a maximum capacity of 100 with a good number of them women.

"Then you get $200 bucks without having to do anything," was Brad's retort.

"I'm in too," Tina and Louise said almost in unison, each pulling a hundred out of their purses.

I was a combination of too brash and too high to realize I was being set up so I agreed.

"Come with me, Debby, and let's see if we can find a Ben Franklin," Brad entreated.

So off we went, followed by the other three, questioning everyone in the bar section, and at every table. No Franklins at all! The only section left was the private dining room. When we went in there my mouth dropped. There were about ten guys, ominously each wearing bifocals and a wig shaped like a bald top of the head surrounded by shoulder length gray hair.

With a big shit eating grin on his face, Brad called out "Anyone named Ben Franklin in here?" At the same time he asked his question he laughed as he pointed out a sign on the marquee near the door "Welcome Local Ben Franklin Society." All ten guys raised their hands.

I was flabbergasted. My first reaction was to run, but Tina, Simon and Louise put a stop to that, saying "A deal is a deal," and such shit. Then I asked to see IDs. All of them produced a driver's license with the name "Benjamin Franklin" on it, with different middle initials. Holy shit!

Brad asked "Does any Ben Franklin want a good fuck with this lovely buxom lady?" putting his hand on my shoulder. "I know the original Ben would never pass up an opportunity like this."

"Thanks, asshole," I murmured under my breath in Brad's direction.

Brad invited all the Bens, Tina, Simon, and Louise back to his apartment. Six of the Bens took him up on the offer. I tried escaping, but Brad, Simon, Tina and Louise all sat with me in the cab on the way to Brad's apartment and made sure I wouldn't slip away. I was conflicted. I was scared, excited, turned on, apprehensive, pissed, and resigned all at the same time.

When we got to Brad's apartment and the Bens arrived, without their wigs and glasses four of the Bens were actually really cute; one was OK; the other one looked like the original Ben - after being buried in a coffin for 200 years. All looked as excited as kids waiting to see Santa.

Now it was fish or cut bait time. My decision was made when the cutest of the Bens came over to me and started chatting me up. I could see a really large bulge in his pants, and he was totally charming. "OK," I said, "This Ben is in for a treat." I grabbed the charmer by his arm and lead him into Brad's bedroom. My co-workers tried to follow us in, "To confirm," Brad said. I shut the door in their faces and said "Get fucked, that's not part of the deal."

When I closed the door, Ben #1 acted fast. He had quick hands, a long thick dick, and an active tongue. Before I knew it, he had all my clothes off, I was laying on my back on Brad's bed with my legs spread apart, his tongue probing my slit, and his hands all over my DDs massaging and twisting the nipples. Hey, this dare might just turn out OK!

Ben #1 was doing a really nice job bringing me to a climax without even having touched my clit. Then he found it! My clit is big enough to be a tiny dick, and seems to grow just like a dick when stimulated -- and holy crap did he stimulate it. He worked one side of my clitoris with his tongue, and the other side with a finger, occasionally sucking it completely into his mouth and gently rubbing his teeth over it. He was finger fucking me at the same time. It didn't take long before I was screaming loud enough to wake the dead, and I'm sure get everyone who could muscle a place at the door to put their ear at the bedroom entrance to hear what was going on.

Ben #1 brought me through two orgasms and then lifted me off the bed. He sat down on the foot of the mattress with his pants off, then lifted me up with my back to his chest and literally impaled my cunt with his chubby. It was as big as any dick I ever had the pleasure of being reamed out with, and he knew how to use it. He bobbed up and down, lifting me up by the hips every time he bobbed down, and pushing me down every time he bobbed up. He pace was methodical. He grunted with each reciprocation, and when not grunting was licking or biting the back of my neck or an earlobe.

After about five minutes of this over-the-top pleasure, he shivered, grabbed both of my now fully hard nipples, and unloaded a fire-hose-like stream of seminal fluid into me. Not only did it literally lambaste the interior of my cunt, it was sufficient in volume to have enough sperm to re-populate Chicago! I was moaning and writhing around like it was my first climax ever, it felt so good.

Once Ben #1 stopped moving and was just sitting there moaning, I gyrated around to try and get every ounce (it seemed more like every gallon) of that hot cream into my pussy. Not satisfied with that, I popped off his fuck tool, got down on my knees, and licked every part of his maleness until he was clean as a whistle, looking up at him with appreciative eyes the whole time, and taking great solace in the expression of pure ecstasy on his face.

I was reluctant to let Ben #1 leave. But he apparently had compassion for his fellow Franklins, and put his pants back on and left, but not before I got his card, he got my phone number, and he promised that we would have a sequel if I was willing. (IF I was willing? Does the Pope poop in the woods? Is a bear Catholic?)

I went outside the room, completely naked with a "fully fucked" look, and grabbed two of the other cute Bens and escorted them into Brad's bedroom. I sucked Ben #2 off as he sat on the bed, and presented my pussy to Ben #3 to enter me doggy style. Unfortunately, this experience was as disappointing as the first encounter had been exhilarating.

Ben #2 sat without touching me and giving little chipmunk yelps while I sucked him -- real irritating. Ben #3 had a nice sized dick, but didn't know how to use it and also made wimpy sounds. Both acted like they never had a decent blowjob or fuck before, and came in about 90 seconds flat. The only good thing was that I could get rid of them quickly.

After the disappointment of Ben #s 2 and 3, I almost called a halt to the proceedings. But my co-workers still had excited looks on their faces, so I dragged the last cute Ben, and the OK one, into Brad's room. I repeated the positions from the last episode, sucking the last cute Ben, #4, while the OK Ben, #5, entered me from the rear.

Fortunately, #s 4 and 5 were MUCH better than the last two. Ben #4 had an average size really nice looking dick, and a heavy set of testicles. He grabbed my hair, stroked my tits, and talked dirty to me while I was sucking him, encouraging me to swallow him completely and massage his balls while I did. He was really fun to blow.

Meanwhile, Ben #5 -- though not particularly good looking -- obviously had had lots of intense sexual experiences, and came with his own lube. While he was pounding my little cunt with his good sized dick he apparently lubed up his fingers, and started inserting one, then two, then three, into my tight little anus as he was fucking my cunt. My screams were muffled by #4's dick, but the fucking excited me so much I really was working on the dick and balls in my mouth and hands.

Ben #s 4 and 5 also had apparently talked about coordination while waiting their turn, and had good control; they came within seconds of each other. As he was cumming, Ben #5 also twisted his fingers in my anus. Holy shit did their ejaculates and the finger twisting feel great! I actually got weak in the knees and let Ben #4's dick spring out of my mouth before I got every last drop so that some cream flipped onto Brad's bedspread (serves him right for tricking me).

It took me about ten minutes to recover from the work-over I had received from Ben #s 4 and 5, but they were real gentlemen and helped me up and gently massaged my tits, back, neck, pussy and ass until I recovered. I finally re-gained my composure, we exchanged mutual thanks, and I asked them to let me be for a minute before I got Ben #6.

As I earlier described, Ben #6 looked like death, and I sure as hell didn't want to fuck him. But I didn't want my co-workers to have any reason not to pay up, so I came up with a plan. I got some lipstick out of my purse and painted red spots near my genitals, buttocks, and lips, and turned on all the lights in the room.

When I exited the room to get Ben #6 he was literally slobbering in anticipation. I'm sure he had never fucked a beautiful woman before -- in fact if he ever got anyone to fuck him I would be surprised. When I led him into the bedroom he pulled down his pants, exposing the ugliest most misshapen dick you have ever seen in your life, and started to try and kiss me while at the same time getting a good look at my crotch. He obviously saw the red blotches and hesitated.

"What are those?" he asked, his false teeth almost falling out.

"Oh, those are genital herpes sores," I said matter-of-factly. "I'm having a bit of a flair-up right now."

"You mean those other guys fucked you when you had herpes?" stammered Ben #6.

"Oh, the lights were off, so I don't think they noticed," I replied, "They must have been too excited. But you don't mind getting herpes for a good fuck, do you?" I teased.

"Uh, suh-suh-suh-sorry," Ben #6 stuttered as he pulled up his pants. "I gotta go," he continued as he quickly exited Brad's bedroom.

I got dressed, went out of the bedroom, and held out my hand for the $400. "What's with that last guy?" Simon asked.

"Oh, he couldn't get it up so he left," I chirped, "now pay-up assholes."

Unfortunately, my co-workers weren't as unobservant as I had hoped, since I had forgotten to remove the lipstick "sores" from my mouth (and crotch).

After I got the money and was getting ready to leave Louise asked "What are those red blotches by your mouth, Debby?"

"Oh I didn't have a mirror so I didn't put my lipstick on properly, I guess," I replied, trying to hurry out the door.

"Bullshit," exclaimed Tina. "Let me see your crotch."

"No way," I said; but now all four were suspicious, so Simon and Brad held my arms while Louise lifted up my dress and Tina inspected my crotch, running her finger over the red blotches there and inspecting what came off closely. "You painted yourself up with lipstick, didn't you?"

While I was trying to deny it, a light bulb went on in Louise's head.

"Why you dirty little cunt, you faked having herpes so that dead-looking guy wouldn't want to fuck you, didn't you?"

I couldn't help myself. I started laughing heartily. While the others started laughing too, their laughs were diabolical, not funny like mine was.

First they wanted their money back. When I refused pointing out that there was no agreement that I wouldn't try and dissuade any Ben Franklin from fucking me, they had to admit I was right. But, they said, that didn't mean that they had to just take my subterfuge.

Brad, who always liked looking at my killer ass any chance he got, came up with the idea of a spanking. Despite my half-hearted protests, Brad and Simon bent me over the back of a padded chair while Louise lifted up my dress and pulled down my panties. She and Tina took turns swatting my bare ass, encouraged by Brad and Simon. Then, as I knew he would, Brad demanded a turn -- the pervert. So Tina and Louise held the arm Brad had been holding, and he spanked me bright red.

They only stopped with the spanking when they thought I might actually be enjoying it -- in truth, I was. We all laughed merrily, and then as I left I flippantly remarked to my smirking co-workers, "Nice doing business with you," and went and got a cab home.

I learned four things that night:

1) Don't get too smug, or drunk, before accepting a dare.

2) I was going to get with Ben #1 again and fuck his brains out.

3) It always pays to carry red lipstick in your purse.

4) You should also bring a wet-nap with you in case you need to wipe the lipstick (or something else) off.

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