You Dare

Story Info
Sylvia pushes him to the limit.
3k words
3.99
139k
9
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It all began innocently enough, a little flirtation now and then, nothing too serious. I guess you could say I always knew Sylvia had a dark side, but it was nothing to be alarmed with. Her husband was a nice enough guy, but they just didn't seem to go together. She was a green-eyed, red headed beauty and he was...well in a word plain. She was outgoing, friendly, and genuinely fun to be around; he was backward, shy and reserved.

Sylvia knew I missed home and would occasionally make a little goody for me. My absolute favorite was "Buckeyes" chocolate covered peanut butter balls. Our office had a little anniversary party and we all went to the bar to celebrate. All week long Sylvia complained that Doug was away for business and she was horny as hell! Jokingly, I suggested that she go to the local smut-hut and pick out a toy to help pass the time. To my pleasure, she informed me that she had all she needed at home.

Slowly our coworkers left one after another, but Sylvia and I continued to party. Shortly after the departure of the last of our cohorts, she excused herself to "powder her nose." When she returned, she had a cookie tin with a ribbon on it and a card. All the card said was "open if you dare..." She slid it across the table, with a look so sly that I just had to open it. The tin was filled with Buckeyes, layered nicely on wax paper; row on top of row.

"You dare," she asked.

"Of course I dare," I responded popping one in my mouth.

"You better be careful, I may have something extra in there," she warned with that smile again.

As the evening progressed we drank more, talked, laughed, and danced. Now instead of sitting on opposite sides of the table, she moved next to me, and fed me the Buckeyes. Each time she would hold it up, and ask "You dare?" With a drunken boldness, I would open my mouth and she would pop it in. Slowly the tin disappeared layer by layer. By now it was getting late, the bartender had made last call and folks were pairing up for the door. We both knew it was time to go, but neither of us were in any condition to drive so we hailed a taxi. It was at this point that I discovered that I was out of cash, but Sylvia came to my rescue.

"I'll loan you the cash, but we have to go to my house first, if you dare" she said mockingly.

"If you dare," I repeated warningly. By this time I was hornier than hell from our dancing and feeling that awesome body of hers. Up until now, I only fantasized about this woman, but now I wanted her for real!

We fell into the cab arm in arm, more for support we each kidded ourselves. All during the ride to her house she kept feeding me the Buckeyes with the same line "You dare?" When we arrived at her house she said she had to run in to get the money. She started to get out and stammered, "I-I need help walking. I'm more wasted than I knew!" Feeling chivalrous I got out and walked her to the door, opened it and went inside leaving the door open. We stumbled down the hall to the kitchen. She opened a jar full of dollar bills and handed me a handful, "Go pay for the cab, then come back in here, I'll make sure you get home."

YES! I thought to myself...you ol' dog you're in there for sure tonight. Hurriedly I walked out and paid the cab driver and strutted back in. As soon as I closed the door, she asked, "You dare?" There was a different tone now. As my eyes searched the unfamiliar surroundings for I nearly tripped on her shoes. They weren't there when I left, I thought. Slowly I walked down the hall peering into every corner looking for this Siren.

I found her lying on a huge bed. Leaning back on her elbows, dress nearly falling off her shoulder and a Buckeye resting on her inner thigh. I think for the first time, I truly wanted this woman and come hell or high water I was going to have her!

At 6' 4" I have yet to encounter a bed that couldn't easily climb into, but this one was high. The satin sheets and comforter only served to enhance my intoxicated induced awkward ascent. She laughed and again asked, "You dare?" Starting at her ankle, I licked a trail up her leg to, then past the Buckeye. Quickly she grabbed my head, "No, no. You're gonna eat it."

"That was my intent," I said coyly.

"No I mean this," and she put the Buckeye in my mouth.

Being so close, smelling her perfumed body, only served to further my drunken state. My head was spinning, and my ears were ringing. After what seemed an eternity, she pulled me on top of her and wrapped her arms around me and kissed me passionately. Her tongue darting in my mouth, as her fingers ran through my hair. Eagerly I returned her hungry kisses and thrust my tongue into her mouth. With each moment our passion grew, as did my cock. It was now becoming uncomfortable since my pants kept it pointing to my feet. I managed to break from her kiss and began to lick down her neck and behind her ear, while unbuttoning her dress front. Laying back she allowed me to work my way to the very last button.

I stood up on my knees and looked down at this fiery beauty, her dress splayed open exposing her sexy body, as she had nothing on underneath. Her breasts were large and firm, and her nipples jutted up proudly. Her mound was nearly shaved, except for a small row that seemed to point to her swollen lips. With my mouth watering I descended to her slightly parted legs. Gently I kissed all the way up her thigh across her flat tummy and down the little patch of lightly colored hair. I could easily smell her muskiness now and gently kissed those soft lips. She let out a little moan and spread her legs wider, giving me even greater access to her soft folds. I have eaten my fair share of pussy, but to this day it is the one I so often recall. It seemed that with every lick and kiss, she would squirm and grab my hair pulling me to her. As I kissed and swirled her clit with my tongue, I slipped two fingers into her steamy cunt. I began to slowly work them in and out of her and could feel her tensing. I knew her orgasm was building and soon would release, and I wanted to eat her even more.

With a near scream, "Ohhhhhh god...I'mmmm cumming" and she began to cum harder than I had ever witnessed. Convulsing, twisting, seemingly in agony but holding my head and grinding her pussy into my face. I began to realize I was no longer was in control; she was, and no one could deny her orgasm. I distinctly remember feeling as though I was being used--but who cares?

Like a woman possessed she sat up and flipped over on top of me, and began to ride my face making sure to use my nose to my chin. She straddled me and had my arms pinned under her legs, cutting off the blood supply to my hands. I could not lick fast enough or long enough to keep up with her juices. It was incredible, she was cumming again and again...and I didn't even have my belt loosened.

Afterwards she rolled off of me and eagerly began to undress me. Nearly ripping my belt loop off trying to get my pants off. She slid my pants off and said, "You're wet too," referring to a huge amount of precum that had soaked through my briefs.

"Isn't that uncomfortable? Having your cock restrained like that," she asked. Hardly waiting for an answer she bent down and began to suck the precum through my shorts! Never before had anyone given me head like this woman did. She eased my shorts off and my cock flapped up onto my belly.

"Oh my, I have missed a large cock for so long," was all she said as she eagerly engulfed my whole cock. Eagerly sucking and pumping it all the while playing with my balls. She again straddled my face in an incredible 69. I could tell she was ready to cum again, so I drove my tongue deep into her pussy, fucking her with my tongue. Moaning while sucking my cock, she started to cum which drove me over the edge. I shot my load down her throat and she never lost a drop. We were both spent, but lazily she reached over to the tin and lifted it to show me, the last layer had a note on top of it. It read, "Continue, only if you dare..." Reaching in I pulled it out, took a Buckeye and defiantly popped it into my mouth. She snuggled up against me and we both fell asleep.

"You dare," she whispered in my ear, not a question but rather a statement. Still groggy, the previous night was a blur, I struggled to wake myself up and recall the previous night. I remember reaching into the tin but thats about it. "You dare," she again whispered.

Have you ever had a moment when you realized all is not right? Mine was then. In an instant I realized several factors of this strange environment. The least of which was the fact I was blind folded, and my arms and legs were securely stretched to two of the corners of the bed. But all of the blood was rushing to my head as I realized I was on my stomach and there was a large pillow that had my ass propped up in the air. I felt as though I was still drunk, but not really the same. I have never taken any illegal drugs, hell I hate to even take cold medicine, but this was a different feeling...I was awake but I just couldn't work up the strength to care about anything--much less do anything about it. It was sort of like being in a dream.

I heard her again repeat, "You dare?" I raised my head and opened my mouth expecting another treat. What I got was a cock shoved into my mouth! Surprised, I instinctively pulled back only to feel a burning sensation rip apart my asshole and a weight bearing down on my back. I could feel her tits on my back as she leaned forward and said, "You dared."

"If you don't like the feel of this strap on dildo in your ass, then you'll suck that cock. Otherwise, I will fucking rape your ass while he watches. It's not that big, so it won't choke you."

I had never had anything shoved into my ass, and could not imagine enduring the pain. Slowly I inched my way forward easing my ass off of it's violating object. Two hands guided my head to a waiting cock. As it lightly touched my upper lip, I opened my mouth and I could taste the precum. I never sucked cock before nor since, but I oddly I found it exciting in some strange way. At first I just locked my lips around the head and swirled my tongue around it, which he enjoyed immensely.

"Thats not how you suck cock, here let me show you," she said almost playfully. She hoped down off the bed and pulled the blindfold off.

"Watch and learn." As my eyes adjusted to the morning light, I watched as she held his balls in one hand and sucked his cock like she had done to me just the night before.

"There now, you do it," she commanded. The look on my face must have made her realize I could not use my hands, because she just said "Oh yeah," and chuckled. "I'll help you," she said guiding his cock back to my mouth. Then grabbed my hair and began bobbing my head up and down on his cock, while she played with his balls. In the position that I was in, I could not see anything but his pubes and balls but I knew instinctively it was Doug. She was right; he did not have a big cock at all. After what seemed an eternity, his excitement grew. Holding both sides of my head he began to pump his cock in and out of my mouth and I knew he was going to come soon.

There was no way I was going to swallow this man's cum, no way at all. But soon he was slamming his cock deep into my mouth and held it there while he came. I could feel his cum on the back of my throat and tried to pull away, but couldn't. Sylvia was watching me intently and seemed to know I would spit it out. "You better swallow it all," she warned.

As he pulled out a string of spunk dripped from his cock onto the carpet. You would have thought he killed her cat. She was so pissed; she pushed him to the floor and for the first time I got a good look at her torture stake of a strap on. It seemed to be every bit of 12 inches long and as thick as a child's arm.

"What have I told you about keeping the floors clean," she screamed at him. "You are going to pay for that!" And with those words she rolled him over, pulled him to his knees and slid that monstrosity up his ass. She unmercifully ravaged his ass, slamming up against his ass cheeks repeatedly. I began to feel sorry for him as he whined and whimpered, soon he was crying "I'm sorry, I'm sorry, please forgive me!"

At this point I was beginning to really come out of my stupor and regain all of my senses--shit, she said swallow it all! A chill overcame me and I started to worry that my ass was next. In my awkward position, all I could really do was slide back and forth. My movements caught her attention.

"What are you trying to do? Leave? I don't think so." And with that she walked up to the bed, her "cock" swaying with every step. She stopped at the foot of the bed and I could see and smell his shit and blood on her sword. She knelt down until her face was in mine and sweetly said, "I told you to swallow all of it."

"You don't like the taste of Doug's come? It's not good enough for you? Well we will just see about that." And with that she slipped a noose over my head and around my throat. Pulling me to the very edge of the foot of the bed and fastened it. I now couldn't move any way without straggling myself.

She stood up and unfastened the straps, taking the strap on off. Placing it on the dresser. She walked over to Doug and lay down next to him and commanded, "Fuck me." I could tell, he was sore but he stood up and to my surprise was hard as a rock. He then mounted her and began to hump her in earnest. "I said fuck me! I can't feel it you needle dick bastard. You are gay aren't you Doug, you would rather fuck some guys mouth than your wife's pussy." After a long while, and a string of verbal abuse he came inside of her pussy.

"Get off me, get up on the bed and give me some room." He quickly jumped up and came over to the bed, untied the fastened end of my noose and climbed behind me, pulling me backwards. Sylvia then got up walked up to the foot of the bed climbed up and said, "now eat me like you did last night." I looked down at her pussy and could see his cum running out of her and looked back up at her.

"You saw what I did to his ass, do want the same?" HELL NO, I thought to myself and began to lick her clean. I was determined to make her cum to save my ass no matter what. It wasn't long before she started to moan loudly and grabbed my head to better control my tongue. Soon she was cumming like the previous night. My cock now was hard as a rock and aching for attention. In the heat of the moment I forgot Doug was behind me, but his cock too was turned on. I could feel the head of his cock sliding between my butt cheeks. And without warning he slid his narrow member up my ass. It was better than hers, I told myself and kept licking her to another orgasm.

"Doug, how is his ass, better than mine?"

"No dear, but it is tight."

"Do you want to cum in it?"

"Yes dear, very badly."

"Well go ahead then." With that, Doug was cumming again, in my ass. Sylvia was cumming again, too. But I was not so lucky. My cock was so hard it ached. Not even a reach around, those words went through my head as they both began to relax.

"Doug, since he sucked your cock, I want to see you suck his. After all, he has played nicely with us."

He slipped from my ass, and slid underneath me and began to devour my cock like a pro. She hopped down off the bed and walked behind me and began to play with my balls, licking and tugging on them. When she easily slipped a finger up my ass I began to cum like I had never before. Doug swallowed every bit of it.

"Doug, you can leave now, your flight is in two hours."

I heard her grab the tin and asked "You dare?" I lifted my head and opened my mouth for the last Buckeye, and before long I drifted off to sleep.

Please rate this story
The author would appreciate your feedback.
Share this Story

Similar Stories

Wife's Cocksucker Domme wife feeds bound husband her toes, and more...in Fetish
Angie's Slut I have a visitor while I sleep.in NonConsent/Reluctance
Nikki Cuckolds Me and Forces Bi Sex Wife cuckolds and abuses husband, and he...enjoys it?in Loving Wives
Truth or Dare with Beth They play Truth or Dare and Beth decides to take control.in Anal
His First Taste of the Real Thing She watches her boyfriend suck another man's cock.in Fetish
More Stories