The Best Double Dare

The rain poured down hard. I was drenched and hated that I had three blocks to the train. It was a crappy end to a terrible week of work. The sudden surge of light behind me and the honk of the horn caused me to jump.

I looked back and saw a hand motion for me to come over. I squinted and made my way to the window that was halfway down.

"Get in, you're going to catch pneumonia," she said.

I looked in and it was Tammy from the office. Jesus. The pushy office manager was here to save me. Well, fuck me I thought. I rolled my eyes. For the three years I had worked there she was always on my ass about something.

"Get in," she said in a tone that said resistance was futile.

I pulled the door on her Camry. She smiled a satisfactory grin. Like saying 'ok, Mr. Wise Ass who needs who now.' We had had our fights, but I was powerless at that moment.

We drove down the road for a minute and the weather report of a storm bearing down for the rest of the night filled the silence. When we came to an intersection, I asked her to make a right so I could get to the train station. She turned left.

"What are you doing? The train is the other way?"

"We aren't going to the train. We are going to my place."

"Why? What?"

"Mike, look as the radio said, it's going to be a night of heavy storms. The train will be delayed, and you are sopping wet. You need to go somewhere warm, change into warm clothes, and just chill. Especially that last part. Mike, you are way too uptight."

"I am not."

She turned her head, tilted it down and gave a gaze with her big eyes that said come on. It was the first time I saw how big and enchanting her eyes were. We drove a few more blocks to her place in silence, while the thunder rumbled on in the distance.

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

Once we got in, she disappeared and I heard, "strip."

"What?"

She came back with two white towels and said, "get out of those clothes, wrap yourself in a towel. You will take a quick warm shower."

"Uh ok. Do I need it?"

"Do you want to catch a cold."

"Turnaround. This is a peep show."

"Ok, Mr. Sensitive."

I then disrobed, wrapped myself in a towel and followed her to the bathroom where a warm shower awaited.

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

"Your clothes are in the wash. I left a robe and shorts out here for you."

I pulled in the clothes and got dressed. I was not happy.

I walked back into the room.

"Is this supposed to be funny?"

"What? You look nice in the robe."

"Funny. You know what I mean."

I opened the robe and turned around. The short black shorts had slut written across the ass in gold cursive lettering.

"What's the matter?"

I walked towards her and demanded, "I want new shorts!"

She stopped me by putting her right hand on my exposed chest and then stuck the red nail on her pointer finger into my chest.

"No. I want you in those. And tonight you're at my house. So, it's my rules."

I was furious but also kind of aroused. Who did she think she was?

I started to reply but she cut me off and said, "by the way, nice chest. Mike, you know, you have a pretty good body. Shame you hide it behind baggy clothes and acting shy. Some of the women in the office think you're a real hottie."

She turned around and started walking away. I could see a real swivel in her curvy body and firm ass.

I came up behind her. Turned her around and at that moment the lightning crashed and the power went out. We jumped into each other's arms.

"Calm down. Don't be afraid, I am in control," she said in a soothing voice.

Her soft voice and the feel of her body in the darkness were all I focused on. My heart pounded.

"Ok," I said softly.

"Stay here, I am going to light a candle."

"Ok."

A few minutes later I saw a flash of light and heard "BOO!!"

I jumped again.

"THAT is not funny!!" I yelled.

She was laughing but then stopped when she could see I was upset.

"Mike, I am sorry. I always wanted to do that. I won't do it again and I will protect you from anything that goes bump in the night."

"Great, who's going to protect me from you?"

"You don't need protection from me. You're my guest."

"You have a funny way of showing it."

"Oh, calm down. Mike, if I didn't like you I would not have stopped. You know Trent?"

"Yeah."

"He's a real asshole," Tammy said.

"Yeah," I said and nodded in agreement.

"I wouldn't stop for him."

"So, you like me? Oooh."

"Get over yourself, Mike."

We sat in silence and darkness for a few moments.

"So, what are we going to do, Tammy? You are the host."

"Does Mike want to play a game?"

"Sure."

"How about Truth or Dare?"

"No."

"Chicken?"

"No."

"Buck, buck, buwka!!"

"Real mature. It's a stupid game."

"Buck, buck..."

"Fine, I'll play the stupid game Tammy."

"Do you want to go first, Mike?"

"Sure. Truth or dare Tammy?"

"Truth."

"Have you ever stolen office supplies?" As I asked it, I instantly felt lame.

"Yes, but not as many as you. My turn. Truth or dare Mike?"

"Truth."

"Ok. Have you ever thought about me while you pleasure yourself?"

"Uh, uh. I won't answer that Tammy. It's a personal question."

"Oh, you're busted!!"

"What?"

"That's a double dare!"

"What's a double dare? Tammy?"

"Mike, if you refuse to answer as punishment the other person, me, gets to assign you two dares or you're the world's biggest chicken."

"That's crap. I've never heard of that."

"Really? Have you ever played this game before?"

"No."

"Well then how do you know? I think you are just a big chicken," Tammy said and I could feel her smile getting bigger.

I knew she was full of shit, but I thought fuck it.

"It's dark, I don't want to lose you, so take my hand, Mike."

I felt around and grabbed her hand. It felt soft and warm. I got goosebumps.

We walked for a few steps. We were in her bedroom.

"Ok. Put these on Mike."

"What are they?"

As she put them in my hand she said, "First take off my shorts. They are sheer, lace, French cut panties."

"What?"

"Double dare Mike. You have no one to blame but yourself. I think you might actually like it."

The last part she whispered into my air and I felt the tip of her tongue as she said like it. I started to get hard. I let out an exhale, turned around, and took off my shorts.

Tammy shined the candle on my ass.

"Damn, Mike, that is really fine. Definitely the best one in the office. Do you run or do a stair master?"

I pulled up my new underwear. The soft sensation felt amazing. I also felt natural. Something in me stirred. It was almost like an afterglow, but I knew I was doing something I had been told boys don't do. I liked that sense of rebellion. I was both embarrassed, excited, and erect.

"Turn around sissy boy."

I did.

"Wow!! Mike!"

"What?!"

"You look great. I wish the lights were on. But even by candle, you look cute. I think you like it too," Tammy said looking down as she said too.

I just smiled and she approached.

"I always thought you had a big dick. The quiet ones are always the type. But damn."

She put the candle down with her right hand and pulled me in closer with her left and on the small of my back, quickly sliding it down to squeeze my ass. Then Tammy put her lips inches away from mine. She could feel my hard dick.

"Now, double dare part two."

"What?" I asked nervously. Please God let this be good I thought.

"We have your ass, now it's time for those long, sexy legs," Tammy whispered as she ran her pointer finger down my thigh.

At this point, I would have done anything she wanted.

"What are you going to do Tammy?"

"Just trust me. I know this will feel good Mike. Take a step back and lay down on my bed."

For a few minutes, I saw the candlelight bob up and down. Finally, Tammy came back.

"Now, Mike you know it's a woman's prerogative to change her mind."

"Ok.."

"So those legs will have to wait. Feel this."

It felt like silk.

"What is it?"

"It's my favorite silk scarf."

Then she grabbed my right wrist and dragged me to the headboard. She tied my right wrist and then my left. I was pinned down, in the dark, my heart was pounding, and I was fully erect.

"Nice silk scarf tie-up. Just like Basic Instinct," I said.

"Good catch Mike. I love that movie. Your turn."

"What?"

"Truth or dare?"

"Oh yeah. I dare you to do what you were going to do to my legs."

"Ok. Someone's curious, aren't they?"

"Do it or it's double dare time."

She walked away and then started lighting other candles until I could see around the room.

"I want you to see this."

"Ok," I said nervously.

She sat on the bed, grabbed my left ankle, lifted it up and then slid the black satin

stocking on to leg and all the way up my thigh. My dick was throbbing. The feel of the stockings was amazing. It felt so natural and sexy. Then she did the right leg and looked up and me as she licked right above the garter belt. We were locked in an intense gaze. She then stood up. Tammy walked over and stood right over my head.

She grabbed the headboard and lowered herself down.

"Mike. You are so hot as a sissy boy."

I would smell her wet pussy and began to stick my tongue and begin licking the hair. Before I knew it my tongue hit her lips and I began moving feverishly to open them and get to her clit.

"Oh, good boy."

She began moving 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 ahead. I wanted so badly to grab her ass and wiggle my pointer finger in her hole.

Her moans drowned out the rain that began to pour intensely and her thighs squeezed tighter and tighter until she released a few minutes later.

"Yes!!" Tammy said through her heavy breath. "Now, it's your turn."

"Untie me."

"What? Not yet."

She got up and put her lips on my left nipple and began licking. She moved down.

"Oh, one more thing."

"What?" I cried.

"Calm down," she said and pulled out a condom. She then pulled down my panties and slipped it on.

Tammy then grabbed my dick and began swirling it around. Then she slid it and thrust forward and then pulled back. She moved front and then back as she worked her way down my dick. Every inch was like a wave of pure pleasure. I was fighting so hard not to cum.

She reached back and grabbed my lower thighs.

"Oh, those stockings. Fuck me sissy boy. Fuck me. Sissy!!"

I erupted, came, and let out a moan. The eyes rolled back in my head and the next minute or two was a blur.

She breathed heavily for a minute and then pulled me out. She fell to the side and untied me on the left, kissed me and then untied me on the right. I grabbed her in my arms and squeezed her tight.

"That was amazing."

"We were amazing," Tammy replied. "No man has ever gone that far with me. You really liked it, didn't you?"

"The sex? Yeah."

"No the whole thing. The stockings, panties, tie up. Letting me take control. Becoming a sissy boy."

"Yes, I did. It was my first time doing that. Oh, and to answer your question, yes I have pleasured myself to you, and always when you wear those red high heels. What about you?"

"What? Pleasured myself to you?"

"Yes."

"That dark blue pinstripe suit drives me wild."

I blushed and kissed her. After taking off the rubber I threw it out and came back to bed. Within minutes I fell asleep.

The next morning, I woke up and the power was back on and Tammy was standing in the door way with my clothes.

"All clean," she said.

I started to take off my panties.

"Stop. Wear them home and keep them for when I come over."

"Come over?"

"Yeah, Mike, did you want this to be a one-night stand?"

"God no! I am just pleasantly stunned."

"Why?" she asked as she started to approach me with a fry smile. "You're a great guy. I've wanted you for a while. You wore that pinstripe suit on your second day on the job."

I took the clothes from her and said, "Can I ask a question?"

"Sure."

"Why did you always give me a hard time?"

"Didn't you ever flirt punch with a girl?"

"No."

"I always teased the boys I like. It's my way of seeing if you can handle me."

"Did I pass?"

"Yes, Mike."

"So, about the panties and stockings, which I really liked, am I a sissy boy now?"

"You're Mike and you can be whatever you want to be but in bed you're my sexy little sissy boy."

I looked her over and smiled.

I got dressed and left. The rest of the weekend I just kept replaying that night in my head. Every time I was rock hard.

On Monday I went to work. As I was settling in the phone rang.

"Come to my office," Tammy said.

I sprinted down like a deer and was in front of her desk within seconds.

"First, for now let's keep this between us."

I nodded yes.

"There is a package that came for you," Tammy said as she handed me the manilla folder.

I opened it, looked in, and saw new panties and stockings. I gave her a smirk and turned around to leave, then I heard a knocking sound. I turned around and saw her feet in two red heels up on the desk.

"Oh Mike, nice pinstripe suit."

"Dark blue is one of my favorite colors," I said as I turned around, and walked out with a big smile on my face.