Nancy informed Alice that she would be using the bedroom to dress me, and that she should pick out an outfit consisting of no fewer than seven articles, gather her make-up and whatever else she required and then use another room to get dressed. Furthermore, Nancy informed Alice if she didn't like what she was wearing when she returned that she would be punished, and to not waste any time dressing as she would require her help in transforming me. I had the feeling that no matter what she came back wearing she was going to be punished.
"Now the fun begins," said Nancy with a snicker.
I was led back into the bedroom and for the time being tied to the corner post at the foot of the bed while Nancy went through my clothes and picked out what she wanted me to wear. Nancy started with a butt plug and harness making sure the plug completely inserted in my ass and the harness was pulled tight. Next she picked out a black 34D bra and my falsies, freed my hands from the post, put them on me and then retied my hands. She picked out my purple open bottomed 6-gartered girdle, a short purple half slip and the purple lace top stockings followed by a pair of black ankle strap pumps with 6" heels. By now my cock was throbbing so hard and Nancy was making sure to stroke and caress every inch of my body that I felt as though I would explode at any minute and having her occasionally press and wiggle that big butt plug around in my ass didn't help either. My black under bust corset would be next and with her knee in the middle of my back Nancy pulled and laced it tighter than it had ever been, leaving me gasping for air. Having completed my underpinnings it was time for my make-up and nails. Once again I was untied, my robe was put on, and I was led back into the bathroom where I was ordered to sit in a chair and my hands were tied to the armrests.
Along about this time Alice had finished dressing and returned to the bathroom, where she was instructed to do my nails, false eyelashes and apply foundation to my face, making sure to conceal any beard growth. She was instructed not to speak to me or to peek underneath my robe at what I was wearing. Nancy informed Alice that she was thirsty and to go make some drinks while she finished with my make-up and outerwear which consisted of a white blouse, black mini skirt, and a wide purple belt. Nancy was so pleased (I was too) with the way I looked that she said that we needed to take me out and show me off. Alice returned with our drinks and Nancy told her of her plans to go out but first Nancy took Alice by the hand over to the wall and told her to assume the position.
"Wider," Nancy exclaimed, referring to Alice's legs. "Now lift your skirt and let's have a look at what you have on."
Alice slowly lifted her short gray skirt revealing a matching pink garter belt and panties. Nancy proceeded to slowly pull down the panties revealing Alice's tight ass.
"Now don't move," said Nancy. Stepping over to the nightstand, Nancy picked up yet another butt plug and lube. Upon seeing what Nancy was up to Alice became very uneasy.
"I haven't ever done anything like this before," said Alice and she began to sob.
"Now now sweetie this will only hurt a lot," Nancy said with glee as she began lubing up Alice's asshole. Alice's legs were visibly shaking as Nancy began to insert the plug and Alice let out a scream which made Nancy stop what she was doing.
"If you do that again I'll gag you. Understand?" Nancy barked. Alice nodded that she understood and Nancy finished inserting the butt plug and informing her that it would be her responsibility to make sure that it did not come out until instructed otherwise. Nancy pulled up the panties and allowed Alice to stand upright and turn around and face Nancy, whereupon she pinned her to the wall, reached one hand down between her legs to fondle her pussy through her skirt, and placed her other hand on the back of Alice's neck, pulled her in close and gave her a big, long, wet kiss. The rest of Alice's outfit consisted of a white, back buttoned, high collared blouse, a tailored 3-buttoned 3/4 sleeved blazer that matched her skirt and nude stockings ending in some gray stiletto heeled pumps.
"Collars, we need collars, before we go out we need collars and leashes," said Nancy. Alice went over to the bondage trunk and got two leather collars, one red for herself the other black for me and two little matching leashes and handed them to Nancy who then instructed us to turn around and lift our hair out of the way while she buckled up our collars and leashed us up.
"There now you are both my bitches and will behave as such, now grab your purses and coats and lets go," said Nancy.
Once in the car, there was time to my swollen cock subside and to gather my composure. I began to wonder what was next on Nancy's agenda. Even though I had been dressing for years this would be the very first time I would be out in public or would have to interact with other people. Our first stop was this quiet little cocktail lounge that Nancy liked. As soon as we exited the car the whole process started over again as the cool night air blew between my legs and up my skirt and my cock began to swell and stiffen in anticipation of what we may find inside. I was somewhat relieved to see that for a Friday night there weren't too many people in the place and we were able to get a booth in a dark corner.
After we seated our selves I was instructed to do two things. First, I was to go to the bar and get the drinks and second, I was to drop something so I could then, without bending my knees, bend over and pick it up, revealing my pantyless cock and balls. Now I was shaking all over as I stood up, retrieved my wallet from my purse, and began walking towards the bar. Halfway across the floor I dropped my wallet, and as quickly as I could bent over and picked it up. Once at the bar and in my best attempt at a feminine voice I croaked out our drink order. I stood frozen waiting for the bartender to make our drinks all the while feeling as though the entire lounge was focused on me. Thank god the bartender was a woman and although she was grinning from ear to ear she maintained her composure and treated me with respect. For this I gave her a very large tip and hastily made my way back to our table. The girls were giggling wildly as I returned with the drinks and so were a few others in the place. My face was red with embarrassment. We were almost finished with our drinks and I was beginning to think we would be leaving soon when a young man approached our table.
"Hey Nancy, what's up, who are your friends?"
My heart started pounding as she began to speak. "Dan!" Nancy said with delight. "I'm so glad to see you, come sit down." Nancy motioned for me to stand up and let Dan slide in between Alice and myself.
"Dan this is Alice and..." Nancy paused for a minute.