Kinky Secretary First Time Dressing by cdDarla

I mentioned in my story of meeting Mistress for the first time that my luck with partners who liked bondage was limited. My experience finding someone who liked the idea of me dressing was practically nonexistent. There was one brief exception and I’ll tell you about it.

I briefly dated a girl named Linda. She was open minded about sexual issues and we were great together in bed. In fact, there was little she hadn’t tried and less she wouldn’t.

I brought up the subject of bondage and she thought that sounded really fun. We traded off tying each other up for sex though neither of us were terribly good at it. It was still such fun for both of us.

I used to read Variations and read a story where the man and woman were both tied up tightly. Hands behind and legs together but she pulled her legs up toward her chest and he was able to penetrate from behind. I never knew if any of those stories were true but it sounded like something I would love to try. I brought it up to Linda one time as we lay in bed smoking a post coital cigarette and enjoying a glass of wine. Predictably she was all in even though it would involve a third person.

Now how to make it happen. I thought of friends who might be open minded enough to tie us both up but came up empty. Besides, the bondage would likely be sloppy.

I asked Linda if we could look for a dominatrix in the closest big city. She thought that was a cool idea. The bondage would be tight, better than we had been able to do, and confidential.

I took to the internet and there were several who looked interesting. I emailed a lady named Julie who was a petite dark haired woman. How do you choose these things? I just thought she looked great in her posted pictures and tight bondage was listed number one under services provided.

I told her what we were interested in and she responded that she loved working with couples. She was available for the coming weekend also. I booked a suite in a nice hotel and off we went.

Julie suggested we meet in the bar and get to know each other first. Linda and I arrived first and ordered a glass of wine and nervously smoked cigarettes. It was before indoor smoking bans were so ubiquitous. I saw Julie walk in, easily recognizable from her pictures. She was so petite! I have to admit I wondered how good she would be given her size.

I waved to her across the room and she joined us. I asked if she wanted wine but she said she never drank while working. She asked for a glass of water and lit a cigarette.

“So tell me exactly what you two have in mind.”

I explained in more detail than in my email. We really wanted the bondage to be expert. Really tight! I didn’t know it it would even be possible to do what I had read about.

“Sounds a bit ambitious but who knows. If you can’t manage it exactly the way you plan I can always untie Linda’s legs and you can do it that way.”

She asked about gags. We had used stockings with panties in the middle but Linda said she had brought ball gags if we wanted to try them.

“Trust me, you’ll love them.”

We chatted a while longer. Julie excused herself to use the restroom and give us a chance to talk.

Linda spoke up right away. “I love her. Let’s absolutely do this!”

Julie walked back to the table and we both nodded we wanted to go ahead.

“Let’s go upstairs then.”

She picked up her shoulder bag and we headed to the elevator.

I locked the door and put out the do not disturb sign.

“Let’s have you both strip. And by the way, from now on call me Mistress. You two get moving.”

We both responded, “Yes Mistress.”

Julie smiled at that. She sat back in the chair and lit a cigarette as we disrobed. I was rock hard already and Linda was already wet.

“Well let’s have some fun then kids. Hands behind, both of you.”

She dug a mountain of rope out of her bag. She started with me and I felt her wrap then cinch the rope. Any questions I had as to her level of expertise were long gone. No way I was getting loose. I watched as she tied Linda’s hands and realized how much better this was than our meager efforts.

She tied our ankles, above the knees and pinned our arms with a tight chest harness.

“What do you think? Tight enough for you?”

We just laughed. More than tight enough.

The bondage was sexy enough but having it done by someone so small seemed even more erotic. Both of us at the mercy of this petite thing who couldn’t have been more than 5 feet tall.

“Some of my clients get a kick out of smoking while they’re tied. Do you want one?”

We both said yes and Julie put Winstons in both of our mouths and lit them. We smoked them hands free with Julie’s help. She stubbed them out and smiled.

“Let’s see if you can make this happen. I’ll admit, I’m going to enjoy watching. I’ll leave your mouths free for now. I suspect you’ll find a way to use them.”

I turned toward Linda. Her lips were already parted. We kissed frantically. What a sensation! Tightly bound so we couldn’t wrap our arms around each other. We took turns sucking and gently biting each other’s nipples.

“Let’s make this a bit more fun for you two. Look what I found in my bag.”

She had tweezer nipple clamps and quickly applied them to both of us. I had never experienced this. It was incredibly erotic.

“Just one more thing you’ll enjoy.’

She pulled out a length of thin cord and wrapped it around the base of my cock several times. I didn’t think of it as a clit yet. Then she twisted the twine and separated my balls into two tight packages.

We wriggled up onto the bed, laughing at our helplessness but finally managed to get into a 69 position. She took me in her mouth and I licked at her pussy though it was difficult with her legs tied together.

I knew if we kept this up I would explode into Linda’s mouth. Certainly not a bad thing but I really wanted to be inside her.

I wriggled behind her and asked her to pull her legs close to her chest when Julie spoke up again.

“I see it’s time for the main event. Let’s get you both gagged. If you do happen to manage this, the orgasms will be even better gagged. Trust me!”

She buckled bright red ball gags into both of our mouths then sat back into the chair to watch. I realized then if I didn’t know it already that I was without doubt an exhibitionist. Naked, tied up, gagged and trying my best to fuck my girlfriend while a fully clothed woman watched with a smile on her face.

I thrust my hard cock toward her pussy and she managed to use her bound hands to guide me. I know it sounds impossible or at least improbable but I was really hard and she was really wet.

She got me to the right place and I pushed forward. It was so tight but she was literally drenched. As if I weren’t hard enough, Julie’s cock and ball bondage added another level.

I pushed again and again as Linda squealed with pleasure into her gag. I finally buried my cock into her and what a feeling. Amazingly tight but I was able to thrust at least somewhat. I’d like to say it lasted a while but neither could hold back. We came explosively and slumped exhaustedly. My cock softened and slid out of her pussy and I struggled to a seated position.

“Bravo! Well done. I’m going to put this in my next blog. Maybe it will generate more couples business. I suppose you want me to untie you.”

I nodded yes. Julie made a show of looking at the cash I had left on the dresser.

“Hmmm. There’s enough to cover tying you both up but only enough to untie one of you. Ladies first so you stay tied and gagged. I’ll let Linda decide what to do with you.”

She untied Linda and handed her a glass of water. Linda put a robe on and lit a Winston, exhausted. Julie gathered the rope she used on Linda along with her gag and nipple clamps.

“I guess I’ll have to come back tomorrow for the rest of the rope. That is, if you two want me to.”

“Absolutely Julie. You were incredible.”

I would have agreed if I hadn’t been gagged.

Linda walked Julie to the door and they chatted a minute but I couldn’t tell what was said. She walked back to me slowly and dropped the robe to the floor.

“What am I going to do with you? Answer, anything I want. I will take the gag out though it does look kind of cute.”

Linda took out my gag and put a lit Winston in my mouth.

“See how sweet I am. Enjoy your cigarette while you recover.”

It didn’t take me long. I was a lot younger then. With a few caresses and licks from Linda I was hard again.

“Now I want you to wriggle your butt off of the bed onto your knees.”

She put a pillow down and I did as she asked. She sat on the edge of the bed and brought my head down to her still wet pussy. I needed no encouragement to bring her to orgasm.

“Ooooh, really nice baby. Now if you can manage to get up onto the bed I’ll return the favor.”

With minimal help from Linda I got onto the bed and lay on my bound hands. She took me in her mouth, sliding up and down my shaft. She paused every now and then to flick her tongue against the tip of my cock. She smiled down at me and straddled my cock. I lasted a little bit longer this time but the eroticism was still intense. Linda threw her head back as she climaxed at the same time.

She rolled off eventually, kissed me on the cheek and went into the bathroom.

She walked back into the bedroom and looked down at me.

“You know, I could just leave you tied up as my sex slave.”

I shook my head. I was really ready to be untied by this time. It seems like nothing now but I wasn’t nearly as used to being tied up for long periods.

“Oh, ok. Spoilsport!”

She untied me and I wrapped her in my arms and kissed her. We showered together and ordered room service. As we lay in bed, I asked Linda what she and Julie had talked about. She absolutely refused to tell me.

“You’ll see tomorrow. It’s a surprise.”

I didn’t see how it could top today but I knew it would be great. I drifted off into a contented sleep.

As you can probably guess, I was about to get dressed though I didn’t know it at the time.

We both slept late and had brunch. Julie was due back in the afternoon. I kept pumping Linda about what they had planned but she just laughed and told me to be patient.