Helping Hand

He rolled his head on the head rest to face me with his hand full of napkins he had yet to use.

"Ill do the party if you make sure I look nice."

I blinked, this was a lot for him I could tell. He began to clean himself as we sat in silence for a moment.

"I will make you beautiful."

Our date ended and I kissed him for the first time, I had to point out I kissed his dick before I kissed his lips and we both had a decent laugh at that. I wasn't even out of the parking lot before he was texting me looking for another date. I loved his eagerness. I considered his idea of driving to our town's shop for sexual accessories.

My own shop, how would I even begin?

I ended up making a purchase of a harness and a six inch cock, thinking it would make the most sense for his first time and mine. I was eager to try it on my whole drive home telling Jason I had a surprise for him. I stood in my living room wearing the harness humping the air feeling silly. I took it off and put on my own lingerie before putting it back on, I looked at myself in the mirror and that's the moment I felt like a sexy dominant. I took a quick picture and sent it to him.

I waited longer than I thought I would have too before he responded by sending me a picture of himself in his burgundy with a hard cock. I smiled like a teenager, I replied with comments on how he owed me one. Playtime was nearing its end as I still had to go to work. I rebuffed his request to come over and give me what he owed, as much as I wanted it, today had been a day and I needed a night's rest.

I woke up to a good morning text, it started my day with a smile. At work we text back and forth like love struck teens. I picked out a few items and paid for them to go with the halloween costume. I settled on the classic playboy bunny look, a bikini corset, nylons, and the head of a separate bunny costume. So he could feel sexy and be hidden. He was still nervous about the idea but agreed so went with it. The party was in just a few days and we didn't have long to prepare.

The end of my day took to long to reach me, I packed up shop wondering how things would go if I owned my own store, the things I would change. One thing I did know, I was keeping my size chart!

We agreed to meet the following day giving me more time to sew a bunny tail on the back of the corset but once I had the entire outfit laid on the bed I couldn't wait. I picked up my phone and called.

"Hey! Didn't think I would hear from you today. I am excited about tomorrow."

"Yeah that's what I am calling about I can't wait, I am sending you my address, shave everything from your ankles to your eyebrows and meet me at my house!"

I had to wait a whole hour and a half before my doorbell rang. I sprung to get the door wearing the same lingerie from the night prior under my robe. I opened the door and jumped into his arms planting a long kiss on his lips. I felt his unease melt in my mouth as I broke the kiss and led him in.

"How did shaving go?"

"It was more difficult to reach certain areas than I thought it would be."

I laughed, it sure is. "Maybe next time I can help." I led him to my bedroom, smiling back at him already seeing the bulge in his khakis.

"Yeah I would like that."

"Good now, close your eyes!"

His hands went to his face and I led him the final few feet and closed the door behind him. I led him to the foot of the bed and told him to open his eyes. I watched as he excitedly ran his fingers over everything.

"You like?"

"I love it!"

"Well put it on! I will grab us a few drinks and let you get acquainted."

I landed a playful pat on his backside and walked out the room grabbing some glasses pouring some tequila. I walked into the living room and placed the glasses down pulling out the strap on and putting it on, opening the robe posturing myself so that as soon as he walked out he would see me lounging wearing the fake cock and lingerie.

I nervously took a sip and adjusted my bra, ran my finger through my hair and tried to put on my most seductive face. I waited a moment, re adjusted, went for my glass again and finished it to calm my nerves.

"Almost done there?" I called out.

"Uhm yes, I am coming."

I grabbed his drink and took it down in two gulps. I felt like I was about to start sweating. I got my pose just right once more when the doorknob turned and he opened the door. We both froze, our eyes wide taking each other in. I was the first to move curling my finger at him and he followed wordlessly his outfit betraying his arousal.

I waited until he stood right in front of me, I reached out running my hand over his smooth nylon covered thigh.

"You look great."

"Y-You look amazing."

I stood, rising to my tip toes. I kissed him. We let our tongues dance for a moment as my fake cock poked his real one.

"On my bed."

He obeyed without hesitation and was on his back on my bed in moments. I undid his corset but left the nylons on him.

"Have you played with your ass before Jason?"

I pulled the vial of lube I got with the cock out and began lubricating the cock.

"Yes, I have a dildo I practice with...mistress."

I arched an eyebrow at this new word he was trying, I liked it and wanted to explore it late but now I wanted to try this.

"Good so this shouldn't be an issue, but let me know if you are uncomfortable."

He hooked his hands behind his knees and pulled his legs back.

"Yes Mistress."

I was nervous, yet excited as I walked up to the edge of the bed and ripped a hole in the crotch of the nylons. I lined up and slowly pushed. He didn't flinch and moaned for me as I sunk it in. I was more shocked than he was.

"You like that?"

"Yes! Mistress please fuck me!"

I wished I would have practiced more, I began to thrust slowly unsure of how rough I could be. It took me a minute to catch my rhythm but when I got the stroke we were both comfortable with it was beyond apparent. His moans echoed in my room and his cock strained under the nylons. I reached out and stroked him through the fabric allowing him to feel it.

"That's a good girl." I whispered to him.

Again it didn't take long until he finished all over himself. I leaned forward and licked the head of his cock through the nylons making him jump as he was still sensitive. I kissed his shrinking shaft as I pulled out of him forcing him to moan more. I sucked his balls while I unstrapped myself and then let the cock hit the floor.

I stood watching him look up at me. "Come take these off sweetheart."

He quickly scooted to the edge of the bed and to his knees taking his hands and slowly peeling my panties off of me revealing my wet mound. I pointed to the bed and he climbed back on, staying on his back. Climbing on top of him I stopped to kiss his cock and then his lips before putting my thighs on either side of his head.

"Eat me slowly."

He mumbled what I assume was yes mistress while his tongue danced in my pussy. I moaned and rode his face. It had been so long a man had tasted me I felt the wave grow quickly before coming crashing down on my body leaving me a quivering mess. I laid down next to him kissing him, tasting myself on his lips and feeling his wet nylons in my leg.

"You are an amazing mistress." He moaned into my mouth.

"No you are amazing." I giggled in return.

We spent the rest of the night rolling in bed kissing and giving me one more orgasm before drifting off and making me late for the first time in a year, it was worth it.

Having Jason distract me I had gotten behind on my messages from people on the internet. I spent most of my day replying to people and taking photos seriously considering the idea of opening my own shop. I began to google how to start my own business and saw how much I needed. I had about half, so I started a savings goal and smiled. I was going to do this. The next day was all planning as I worked out a business plan and talked to the bank about my options. I needed to find a location but otherwise the bank was willing to lend me the money.

I took Jason with me every step of the way, we spent the entire day together and were both just as excited about "Cassandras'' as we were excited about his first outing as a woman. Hours before we got him dressed again having to buy new nylons so we didn't have him out in ones we ripped and came in. I felt his nerves coming back walking him out the house with the mask on. It was obnoxious in the car but I knew it made him feel comfortable. I placed my hand on his thigh as we drove talking about ways to design the shop to take his mind off what we were about to do.

When we pulled up we saw several anonymous people funneling into this nightclub Halloween party. Scandalous was not even the word to describe today's "costumes" they were down right slutty and my witch costume made me look like a hag.

"Are you ready for this?"

"No I am not."

"Do you want to stay here?" I asked, squeezing his thigh watching the head tilt down.

"No, let's do this, mistress."

That night Jason and I had an amazing time and it was truly the day my business partner and wife came into the world. That was five years ago and today Jordyn and I fell in love on a dance floor with a bunny head piece between us. We still have that very head in our store, just to be able to tell the story. If you ever need a helping hand feeling pretty and getting your sizing right feel free to call on us at "The right touch" lingerie.

xx

Belle