The Finest Double Dare


The rain poured down exhausting. I used to be drenched and hated that I had three blocks to the practice. It was a crappy finish to a horrible week of labor. The sudden surge of sunshine behind me and the honk of the horn brought on me to leap.

I regarded again and noticed a hand movement for me to return over. I squinted and made my method to the window that was midway down.

“Get in, you are going to catch pneumonia,” she stated.

I regarded in and it was Tammy from the workplace. Jesus. The pushy workplace supervisor was right here to avoid wasting me. Effectively, fuck me I assumed. I rolled my eyes. For the three years I had labored there she was all the time on my ass about one thing.

“Get in,” she stated in a tone that stated resistance was futile.

I pulled the door on her Camry. She smiled a passable grin. Like saying ‘okay, Mr. Sensible Ass who wants who now.’ We had had our fights, however I used to be powerless at that second.

We drove down the highway for a minute and the climate report of a storm bearing down for the remainder of the night time crammed the silence. Once we got here to an intersection, I requested her to make a proper so I might get to the practice station. She turned left.

“What are you doing? The practice is the opposite manner?”

“We aren’t going to the practice. We’re going to my place.”

“Why? What?”

“Mike, look because the radio stated, it may be an evening of heavy storms. The practice will likely be delayed, and you’re soaking wet. It’s essential go someplace heat, turn into heat garments, and simply chill. Particularly that final half. Mike, you’re manner too uptight.”

“I’m not.”

She turned her head, tilted it down and gave a gaze together with her huge eyes that stated come on. It was the primary time I noticed how huge and enchanting her eyes had been. We drove a couple of extra blocks to her place in silence, whereas the thunder rumbled on within the distance.

We sprinted to the door, and I huddled subsequent to her as she opened it.

As soon as we acquired in, she disappeared and I heard, “strip.”

“What?”

She got here again with two white towels and stated, “get out of these garments, wrap your self in a towel. You’ll take a fast heat bathe.”

“Uh okay. Do I would like it?”

“Do you need to catch a chilly.”

“Turnaround. This can be a peep present.”

“Okay, Mr. Delicate.”

I then disrobed, wrapped myself in a towel and adopted her to the toilet the place a heat bathe awaited.

A couple of minutes later, as I dried myself off, I heard a knock on the door.

“Your garments are within the wash. I left a gown and shorts out right here for you.”

I pulled within the garments and acquired dressed. I used to be not completely happy.

I walked again into the room.

“Is that this speculated to be humorous?”

“What? You look good within the gown.”

“Humorous. You understand what I imply.”

I opened the gown and rotated. The brief black shorts had slut written throughout the ass in gold cursive lettering.

“What is the matter?”

I walked in the direction of her and demanded, “I need new shorts!”

She stopped me by placing her proper hand on my uncovered chest after which caught the pink nail on her pointer finger into my chest.

“No. I need you in these. And tonight you are at my home. So, it is my guidelines.”

I used to be livid but additionally type of aroused. Who did she suppose she was?

I began to answer however she reduce me off and stated, “by the way in which, good chest. Mike, you understand, you will have a fairly good physique. Disgrace you disguise it behind saggy garments and performing shy. A number of the ladies within the workplace suppose you are an actual hottie.”

She rotated and began strolling away. I might see an actual swivel in her curvy physique and agency ass.

I got here up behind her. Turned her round and at that second the lightning crashed and the ability went out. We jumped into one another’s arms.

“Relax. Do not be afraid, I’m in management,” she stated in a soothing voice.

Her mushy voice and the texture of her physique within the darkness had been all I centered on. My coronary heart pounded.

“Okay,” I stated softly.

“Keep right here, I’m going to gentle a candle.”

“Okay.”

A couple of minutes later I noticed a flash of sunshine and heard “BOO!!”

I jumped once more.

“THAT just isn’t humorous!!” I yelled.

She was laughing however then stopped when she might see I used to be upset.

“Mike, I’m sorry. I all the time wished to do this. I will not do it once more and I’ll shield you from something that goes bump within the night time.”

“Nice, who’s going to guard me from you?”

“You do not want safety from me. You are my visitor.”

“You may have a humorous manner of displaying it.”

“Oh, relax. Mike, if I did not such as you I might not have stopped. You understand Trent?”

“Yeah.”

“He is an actual asshole,” Tammy stated.

“Yeah,” I stated and nodded in settlement.

“I would not cease for him.”

“So, you want me? Oooh.”

“Recover from your self, Mike.”

We sat in silence and darkness for a couple of moments.

“So, what are we going to do, Tammy? You’re the host.”

“Does Mike need to play a sport?”

“Certain.”

“How about Fact or Dare?”

“No.”

“Hen?”

“No.”

“Buck, buck, buwka!!”

“Actual mature. It is a silly sport.”

“Buck, buck…”

“Positive, I am going to play the silly sport Tammy.”

“Do you need to go first, Mike?”

“Certain. Fact or dare Tammy?”

“Fact.”

“Have you ever ever stolen workplace provides?” As I requested it, I immediately felt lame.

“Sure, however not as many as you. My flip. Fact or dare Mike?”

“Fact.”

“Okay. Have you ever ever thought of me whilst you pleasure your self?”

“Uh, uh. I will not reply that Tammy. It is a private query.”

“Oh, you are busted!!”

“What?”

“That is a double dare!”

“What’s a double dare? Tammy?”

“Mike, when you refuse to reply as punishment the opposite particular person, me, will get to assign you two dares otherwise you’re the world’s greatest hen.”

“That is crap. I’ve by no means heard of that.”

“Actually? Have you ever ever performed this sport earlier than?”

“No.”

“Effectively then how have you learnt? I believe you’re only a huge hen,” Tammy stated and I might really feel her smile getting larger.

I knew she was stuffed with shit, however I assumed fuck it.

“It is darkish, I do not need to lose you, so take my hand, Mike.”

I felt round and grabbed her hand. It felt mushy and heat. I acquired goosebumps.

We walked for a couple of steps. We had been in her bed room.

“Okay. Put these on Mike.”

“What are they?”

As she put them in my hand she stated, “First take off my shorts. They’re sheer, lace, French reduce panties.”

“What?”

“Double dare Mike. You haven’t any one accountable however your self. I believe you would possibly really prefer it.”

The final half she whispered into my air and I felt the tip of her tongue as she stated prefer it. I began to get exhausting. I let loose an exhale, rotated, and took off my shorts.

Tammy shined the candle on my ass.

“Rattling, Mike, that’s actually tremendous. Positively the most effective one within the workplace. Do you run or do a stair grasp?”

I pulled up my new underwear. The mushy sensation felt superb. I additionally felt pure. One thing in me stirred. It was virtually like an afterglow, however I knew I used to be doing one thing I had been informed boys do not do. I preferred that sense of rise up. I used to be each embarrassed, excited, and erect.

“Flip round sissy boy.”

I did.

“Wow!! Mike!”

“What?!”

“You look nice. I want the lights had been on. However even by candle, you look cute. I believe you prefer it too,” Tammy stated trying down as she stated too.

I simply smiled and he or she approached.

“I all the time thought you had a giant dick. The quiet ones are all the time the sort. However rattling.”

She put the candle down together with her proper hand and pulled me in nearer together with her left and on the small of my again, rapidly sliding it all the way down to squeeze my ass. Then Tammy put her lips inches away from mine. She might really feel my exhausting dick.

“Now, double dare half two.”

“What?” I requested nervously. Please God let this be good I assumed.

“We’ve got your ass, now it is time for these lengthy, attractive legs,” Tammy whispered as she ran her pointer finger down my thigh.

At this level, I might have completed something she wished.

“What are you going to do Tammy?”

“Simply belief me. I do know this may really feel good Mike. Take a step again and lay down on my mattress.”

For a couple of minutes, I noticed the candlelight bob up and down. Lastly, Tammy got here again.

“Now, Mike you understand it is a girl’s prerogative to vary her thoughts.”

“Okay..”

“So these legs should wait. Really feel this.”

It felt like silk.

“What’s it?”

“It is my favourite silk scarf.”

Then she grabbed my proper wrist and dragged me to the headboard. She tied my proper wrist after which my left. I used to be pinned down, at nighttime, my coronary heart was pounding, and I used to be totally erect.

“Good silk scarf tie-up. Similar to Fundamental Intuition,” I stated.

“Good catch Mike. I really like that film. Your flip.”

“What?”

“Fact or dare?”

“Oh yeah. I dare you to do what you had been going to do to my legs.”

“Okay. Somebody’s curious, aren’t they?”

“Do it or it is double dare time.”

She walked away after which began lighting different candles till I might see across the room.

“I need you to see this.”

“Okay,” I stated nervously.

She sat on the mattress, grabbed my left ankle, lifted it up after which slid the black satin

stocking on to leg and all the way in which up my thigh. My dick was throbbing. The texture of the stockings was superb. It felt so pure and attractive. Then she did the suitable leg and regarded up and me as she licked proper above the garter belt. We had been locked in an intense gaze. She then stood up. Tammy walked over and stood proper over my head.

She grabbed the headboard and lowered herself down.

“Mike. You’re so scorching as a sissy boy.”

I might odor her moist pussy and commenced to stay my tongue and start licking the hair. Earlier than I knew it my tongue hit her lips and I started shifting feverishly to open them and get to her clit.

“Oh, good boy.”

She started shifting her hips and pussy up and down my face. I moved my tongue in a circle then she grabbed my head and drove it straight forward. I wished so badly to seize her ass and wiggle my pointer finger in her gap.

Her moans drowned out the rain that started to pour intensely and her thighs squeezed tighter and tighter till she launched a couple of minutes later.

“Sure!!” Tammy stated by her heavy breath. “Now, it is your flip.”

“Untie me.”

“What? Not but.”

She acquired up and put her lips on my left nipple and commenced licking. She moved down.

“Oh, yet one more factor.”

“What?” I cried.

“Relax,” she stated and pulled out a condom. She then pulled down my panties and slipped it on.

Tammy then grabbed my dick and commenced swirling it round. Then she slid it and thrust ahead after which pulled again. She moved entrance after which again as she labored her manner down my dick. Each inch was like a wave of pure pleasure. I used to be preventing so exhausting to not cum.

She reached again and grabbed my decrease thighs.

“Oh, these stockings. Fuck me sissy boy. Fuck me. Sissy!!”

I erupted, got here, and let loose a moan. The eyes rolled again in my head and the subsequent minute or two was a blur.

She breathed closely for a minute after which pulled me out. She fell to the aspect and untied me on the left, kissed me after which untied me on the suitable. I grabbed her in my arms and squeezed her tight.

“That was superb.”

“We had been superb,” Tammy replied. “No man has ever gone that far with me. You actually preferred it, did not you?”

“The intercourse? Yeah.”

“No the entire thing. The stockings, panties, tie up. Letting me take management. Changing into a sissy boy.”

“Sure, I did. It was my first time doing that. Oh, and to reply your query, sure I’ve pleasured myself to you, and all the time once you put on these pink excessive heels. What about you?”

“What? Pleasured myself to you?”

“Sure.”

“That darkish blue pinstripe go well with drives me wild.”

I blushed and kissed her. After taking off the rubber I threw it out and got here again to mattress. Inside minutes I fell asleep.

The following morning, I awakened and the ability was again on and Tammy was standing within the door manner with my garments.

“All clear,” she stated.

I began to take off my panties.

“Cease. Put on them dwelling and preserve them for after I come over.”

“Come over?”

“Yeah, Mike, did you need this to be a one-night stand?”

“God no! I’m simply pleasantly shocked.”

“Why?” she requested as she began to strategy me with a fry smile. “You are an awesome man. I’ve wished you for some time. You wore that pinstripe go well with in your second day on the job.”

I took the garments from her and stated, “Can I ask a query?”

“Certain.”

“Why did you all the time give me a tough time?”

“Did not you ever flirt punch with a lady?”

“No.”

“I all the time teased the boys I like. It is my manner of seeing when you can deal with me.”

“Did I go?”

“Sure, Mike.”

“So, in regards to the panties and stockings, which I actually preferred, am I a sissy boy now?”

“You are Mike and you may be no matter you need to be however in mattress you are my attractive little sissy boy.”

I regarded her over and smiled.

I acquired dressed and left. The remainder of the weekend I simply stored replaying that night time in my head. Each time I used to be rock exhausting.

On Monday I went to work. As I used to be settling within the cellphone rang.

“Come to my workplace,” Tammy stated.

I sprinted down like a deer and was in entrance of her desk inside seconds.

“First, for now let’s preserve this between us.”

I nodded sure.

“There’s a bundle that got here for you,” Tammy stated as she handed me the manilla folder.

I opened it, regarded in, and noticed new panties and stockings. I gave her a smirk and rotated to go away, then I heard a knocking sound. I rotated and noticed her ft in two pink heels up on the desk.

“Oh Mike, good pinstripe go well with.”

“Darkish blue is one in all my favourite colours,” I stated as I rotated, and walked out with a giant smile on my face.