Kinky Secretary First Time Dressing

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.

We met again in the bar. Julie walked in with two really large shopping bags but somehow I didn't think she had been shopping that day.

"Well you two have an attractive 'freshly fucked' look about you. I trust you slept well."

"Very well, thank you Mistress."

I whispered the 'Mistress' since we were in public but Julie nodded her approval in any case.

"Glad to hear it. Why don't we go upstairs. If Linda followed my instructions, this will be a surprise. I think you'll like it. Shall we?"

I locked the door with the do not disturb sign.

"Now then, strip please. Not you Linda. You stay dressed for now."

Now I was really confused. I had thought this would be like yesterday with some kind of twist. Julie seemed to have lots of kinky ideas. No surprise for a dominatrix.

I she my clothes as Julie dug into her large shopping bags. She produced a pair of thong panties and tossed them to me.

"Put these on. That's right. We're going to dress you up. Unless I'm really wrong you'll love it, kinky as you are."

I had a big smile as I put on the panties.

"You're loving this aren't you baby? You should have told me. I thought about asking to put makeup on you. I wish I had now."

"I started to ask you but when I brought it up to others in the past the response wasn't good. I didn't want to risk spoiling what we have. But yes, I've wanted to do this forever."

The panties were followed in short order by opaque black stockings held up by a garter belt, bra stuffed with DD size breast prostheses, and a little black dress gathered at the waist by a cincher. Julie had quite a selection in all sizes to service her clients, even one as tall as me.

She led me to the chair and started on my makeup. I was painfully hard, particularly as she painted my lips with what she called 'fuck me' red lipstick. She wouldn't let me look which added to the feeling. She clipped on hoop earrings then reached into her bag and pulled out a long red wig and carefully positioned it on a wig cap. She fussed with brushing it out which added to my desperation to look in the mirror. Finally she reached into her bag and pulled out a pair of black 4 inch heeled pumps. Wonder of wonders, they fit. I think for me and for a lot of crossdressers, the shoes may be the best part. I know I felt something when that first pair of 4 inch heels went onto my feet.

"That's it then Missy but before you look, we have to name you. Any ideas?"

I didn't have to think long. My favorite internet bondage model was Darla Crane and the red hair cinched it. I was so excited I could barely speak.

"Darla. My girl name is Darla."

"Well then let's let you have a look Darla."

She led me to the full length mirror, tottering in my heels. I was stunned to see not me but a tall and not unattractive woman looking back. I turned this way and that, twirled and preened. Julie took pictures with, of all things, a polaroid. This was before cell phones had cameras. Linda posed with me then took pictures of me with Julie. I towered over her diminutive form. I still enjoy looking at those shots, faded though they are.

"Let's get you tied up so you can channel your inner bondage model. I'll do you up like yesterday, the classic damsel in distress look."

In short order I was tightly bound, then more pictures.

"I'm going to leave you two to your own devices. I'll be in the bar or maybe do a little shopping. Call me when you've finished and please, take your time. Enjoy your moment Darla."

She left us alone and Linda smiled down at me. I asked if she was sure she really liked this.

"I love it that you're not afraid to show this side of you. It gives you such an attractive vulnerability and sensitivity. I have to admit I have some bi fantasies so this is perfect. My own damsel in distress to do with as I please."

She leaned down and gave me my first lipstick on lipstick kiss, devouring me with her open mouth.

We kissed for a while, Linda obviously getting more and more turned on.

"Oh look, I've smudged your lipstick. I'll fix it for you."

She dabbed with a tissue then repainted my lips.

"Thank you."

"Thank you what. I think you should call me Mistress seeing as how you're all tied up and I'm not."

"Yes Mistress, of course."

"I think that's enough talking. Open wide."

Linda put the ball gag in my mouth and buckled it tightly. She pushed the dress up exposing my cock, now clit, straining against the thong.

"You know I've always loved thongs. You feel almost naked. But besides that, they are really easy to push to the side."

I sprang to full attention, needless to say.

"Someone's really eager but you'll just have to wait. I think I'll have a cigarette and let you enjoy the show for a while."

She pulled a Winston out of the pack and made a show of seductively lighting it and slowly exhaling the smoke. She sat in the chair facing me and pulled her skirt up then moved her thong to the side. She fingered her wet pussy then retrieved the vibrator. She brought herself to orgasm slowly, smoking seductively while she did.

Enjoy it I did except for the fact my cock/clit was about to explode it was so tight and hard.

"Look at me, I'm a mess. Be right back. Don't go anywhere."

She went into the bathroom and repainted her own lips with the same shade of red I was now wearing. She lit another Winston and leaned over my swollen member. She took me in her mouth, smoke coming out at the same time.

"I know it's bad for you but I've always wanted to smoke a cigarette during a blow job. You know what, I really like it. Bet you do too."

Did I ever. She teased me with her mouth between deep drags and long exhales till she finished her cigarette.

"I don't know about you but this whole scene has me kind of hot. What say I fuck your brains out?"

I'm surprised my head didn't fall off I nodded so hard. She pushed me back onto my bound arms and straddled me, sinking my cock/clit deep into her slick sex.

"You should see your face. I think if got up now you would chase me down even though you're tied up. Be a good girl and show me how bad you want it."

I thrust up into her as much as I could as she slid up and down my rigid pole. I don't know how I lasted as long as I did. The eroticism was overwhelming. I looked up and saw Linda close her eyes as her breathing became more frantic and ragged.

I exploded into her in what had to be the longest orgasm of my life, at least to that point.

"Oh god sweetie. That was wonderful. I hate to untie you but I think you're probably done for now."

I was. Linda untied the knots and I gratefully stretched. Linda handed me a freshly lit Winston and I had my first lipstick enhanced cigarette.

"I know you don't want to but you need to get undressed. Julie will need her clothes back for someone else to enjoy."

I really didn't want to take of my women's clothes but reluctantly did so. I hopped in the shower and cleaned my face. When I came out wrapped in a towel, Linda and Julie were chatting. I walked over and gave her a big hug.

"That's sweet. You two were great. I hope we can do it again some time. By the way, keep the rope and gag. I've got plenty."

"Absolutely! Thank you so much."

We said our goodbyes and she left. What an experience.

"What would you like to do now baby?"

"I think I'd like to rip your clothes off and use that rope to tie you up and maybe spank you for being such a bad girl."

"If bad girls get tied up and spanked I don't want to be good. Tell me, do they get gagged too?"

"I think I can arrange all of that."

And I did. As a plus, my tying was much better after watching Julie.

We lay in bed later talking about the weekend, making plans to come back soon. Alas, it never happened. We both took new jobs in different cities, far from each other and from Julie. We kept up for a while then drifted apart as often happens.

I didn't find anyone else remotely like Linda or Julie for many years till I met Mistress. Mistress encouraged me to write this. Not jealous since it occurred so long before we met. The story met her approval since she tied me up and had her sexy way with me.

As always, I drifted off to contented sleep. The luckiest girl in the world.