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.
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