A Sissy Shopping Trip Ch. 02

At the car, I headed for the driver's side as Cindy opened the passenger door. Before I could take more than the first step her almost shouted exclamation, "Excuse me!" stopped me in my tracks. I looking warily at her, wondering what was wrong. "Come on," she smiled tightly, "girls ride over here. I'll take care of the driving today." My macho pride rebelled at first and I tried to stare her down. It wasn't to be and I finally slunk over and got into the passenger seat. As I did I knew that this was submission and a wave of deep satisfaction went through me. While I was lost in the sensation Cindy went to the driver's side, lowered the top and, in her best imitation of a macho man, squealed into traffic.

As we headed out of town, Cindy explained that we would be going to the mall on the outskirts of the nearby city, pointing out that it might not be good for her career to be caught hanging out with an obvious girly man. I mumbled a grateful acknowledgment, at the same time realizing that she had not, in fact, said anything about my own career. She went on to warn me, "Sweetheart, I realize that you might feel a bit uncomfortable today but I really want you to accept what happens and do as I tell you. Are you willing to do that?" I looked at her, a bit shocked that she was giving me this warning now, after all that I had already been through. It gradually dawned on me that this might be only the beginning.

"I don't know. Could it be any worse than humiliating me in front of Tim?" I whined.

"Oh, my little sissy baby, I probably will get more interesting but you can handle it. In fact," she said, leering at the lump in the form-fitting jeans, "I suspect that she doth protest too much." As I turned bright red, she continued sternly, "Now how about if you just admit that you are a sissy and that you get off on being treated like a sexy little lady. How about if you just stop with playing at the protests and resistance and we just have some fun with this."

I was shocked to hear her sum up my innermost feelings so bluntly. I still wasn't ready to acknowledge them and sat stone-faced for miles, trying to get my feelings sorted out. Whether to give in and find out where this roller coaster of sensations and thrills would take me or to hold onto what dignity I could. I realized that once I crossed the line there might be no going back. The control was Cindy's now and once I said yes it would most certainly never come back to me. It seemed like a dozen times that I almost said yes but each time pride or fear won out and I said nothing. Finally, Cindy grew impatient and, slamming on the brakes, swung the car into a screeching U-turn, saying, tensely, "OK, babe, I get it. Lets call it off."

It was an immediate and terrible sense of loss. It came to me abruptly that it was now or never and I whispered, "Yes." Then, at her questioning look, louder, "Yes, I would love to do whatever you want." I tried to smile but just managed a grimace.

"OK, Sweetie," she said. "Are you sure? If you are, you'd better smile like you believe it right now and beg me to turn around. Is this something you really want?"

Pushing my fears aside I managed a winning smile and said, "Yes, Sweetheart, it is absolutely what I want. I want you to take me in hand as your little sissy and I will do whatever you tell me. This is a dream come true for me. Please turn around."

She slowed and pulled over. After carefully scanning my face she abruptly swung the car into another U-turn. As we traveled I tried to wheedle out her her plans for the day but she would have none of it. "You'll find out when we get there," was all she would say.

As we pulled up in front of the doors to the department store at one end of the mall I felt a rush of adrenaline as the fear and excitement welled up. Looking curiously at Cindy, I wondered why she had pulled up here instead of just parking the car like we usually would. She looked back at me, speculatively. "I think you can manage it. Girls do every day," she said thoughtfully. "OK, I'm going to find parking," she said, looking out over the packed parking lot. "I might be a while. While I'm gone I want you to go to the lingerie section and get a bra. Not just any bra but a pretty one that fits. Pink would be nice."

"How do I pick the right size?" I stuttered, "I don't know what size I am."

"You are such a naive little sissy, aren't you. You have to get it fitted. You find a salesperson and ask her to help you. Now go!"

I felt my face turn beet red but got out of the car. As she drove away, I stood on the sidewalk trying to ignore the stares from the people going by but still noticing the mixture of leers, scowls and furtive smiles. Wondering how I could do this and knowing I had to. I needed to keep going. This was what I wanted and I was dying to know what the day would bring. I forced myself to walk through the doors.

As I walked into the lingerie department I looked desperately for a salesperson who might be willing to help me and not throw me out on my ear. Try as I might I couldn't tell. Finally I simply resorted to browsing through the bra's. Taking a couple from their hangers and holding them against myself. One salesgirl cruised by. I looked up hopefully but she quickly looked down and walked on, ignoring me. I saw her go back to the counter and talk to a couple of others hovering there. I could see her giggling and pointing in my direction and I felt my face grow hot. As I watched, though, the oldest of the group, curvaceous and perhaps in her late twenties, left the group and headed my way.

I was terrified. She would throw me out. Have security take me away. Report me to the police. And then, she was in front of me and smiling, "Can I help you? I see that you've found our prettiest bra's. Do yo need help getting the right size?"

"Uhhh," I mumbled.

She chuckled lightly, "It's OK. I see that you're checking them out on yourself. Is it for you?"

Her gorgeous smile was infectious and I found myself smiling hesitantly. "Uhhh, yea," I muttered.

"OK, lets get you measured up so we can find some for you to try on," and off she went to get the tape measure. As she did, I saw her say something to the other girls and they hesitantly joined her as she returned. She measured around my chest, under my breasts and announced "38! Now tell me, do you want something to fit your breasts as they are or do you plan to wear something to make them bigger?"

"Uhhh, I'm not sure."

"Well, I think we could try for a B cup with a bit of padding or, we have these cute little breast forms that we sell to some of our less endowed customers. Would you like to try those?" As I hesitated she asked one of the other girls to get the forms, "The larger ones. I think those would fit his... oops," giggling, "Or should I say, her, chest best."

To the other girl she said, "Hey Jill, how about finding some 38C's." To me, "Do you have a color in mind? A nice baby blue would look sweet or dark red would be so sexy. Maybe pink for a really cute look? Or, do you want cream to match your top?" I hesitated, caught between pink as Cindy had suggested and all of the other wonderfully sweet, or cute or sexy colors. Finally, after what seemed like ages, she broke in with, "I tell you what, why don't we just try a bunch of them and you can see what you like best." As she nodded at Jill to carry on, she grabbed a couple of bras from a nearby rack and, with the forms in hand, led me across the store to the mens changing rooms, pointing out as she went that men weren't allowed in the womens' and they would be fired immediately if they allowed it. "Sorry dear but we just can't risk it."

My face grew hot as she walked up to the young man attending the change rooms, saying, "Can we borrow one of your rooms? He, uh, she isn't allowed in ours but she wants to try some things on."

He chuckled a bit, "Sure, why not?" and opened a door just out of sight of the sales floor but near enough to his station that he could easily see it. I saw him watching closely as I entered. The girl passed me a bright orange bra and told me to put it on and come out so she could see how it fit.

I took off my top and put the bra on as I'd seen my wife do many a time, snapping it together in front then turning it around and pulling the straps up over my shoulders. I opened the door and came face to face with the young man. He grinned, "She had to go away for a minute. She asked me to give you these and tell you to put them in. She said to look for the L and R on the back." We looked together and he stood and watched as I slid them into the cups. "Hmm," he noted after I had them positioned in what looked like more or less the right place, with some amusement and obvious interest, "That would be almost sexy if it weren't for the hairy chest. Are you going to shave or something?"

A familiar voice came from around the corner, "Of course. She can't run around all hairy like that, now can she." Cindy and the sales girl came around the corner, both wearing big smiles. "But first lets pick out the right things for her." Jill came around the corner just then with an armload of bras and, I noticed, quite a few matching panties.

What followed was like a dream, me trying on bra after bra with the ladies all looking on, offering opinions, adjusting here and there, chatting amongst themselves and discussing the merits of each bra. I was thoroughly enjoying myself, getting lost in the look and feel of the silk and lace in an amazing range of colors and styles. Spinning around to show off and to see them from every possible angle. Every once in a while blushing brightly when I caught the young man's eye as he watched closely throughout the process.

As each bra was removed the girls decided together, with frequent comments from the young man, whether it was a keeper or not. Finally there were none left to try and there remained only five bras in the keeper pile. Three panties were also on the pile, having been added when the matching bra hit the pile.

"OK," Cindy smiled, "Good job, Sweetie. Now we just have to go through these few again and make your choice. You might as well try the panties on too. Matching panties are so cute so I really want to see you in them."

I felt myself turn red yet again but took the first of the sets. Closing the door, I undressed, leaving on only my garter belt and stockings, and put on lacy pink panties and the matching bra. After a moment to catch my breath and work up my courage I took a deep breath and swung the door open. All were watching, including the man.

Through a haze of excitement and humiliation, I heard the comments, "He's so cute."

"So sexy."

"Look at the stockings and garter. What a sissy."

From him, "Wow, looking hot but the hair has to go."

I looked at him and blushed as I saw him staring at my rock-hard cock, plainly visible and tenting out the lacy panties. I scanned downward and saw a hard lump in his pants and the tiniest bit of wetness at the top. I smiled, feeling a thrill at the thought of having that effect on a man.

"OK, you two," Cindy took control again, "Save it for later." To me, "Go! Try this one now," handing me a deep red set."

Finally, after trying on and modeling my way through the second stack and after more chattering among the group we settled on two sets, lacy pink and cute baby blue with pink flower embroidery. Thinking that the task was done I started toward the exit carrying the two panty and bra sets and breast forms but was stopped mid-step. "Hold it!" Cindy commanded. "You might as well put the pink ones back on while we're in the changing rooms. You'll be wearing them for the rest of the day."

I turned to her, shocked, realizing that the bra would be obvious under my cream top. She was adamant "Do it, Sweetie. You know you want to. In fact, why don't you thank these nice people who have helped you so much and tell them how much you want to wear the clothes and be a girlie."

Hanging my head in shame, I mumbled, "I do love to wear girlie clothes and I really want to be a sexy girl. Thank you for your help."

"Hold your head up, Sweetie, and say it so they can hear you."

I put on my best smile, held my head high, looking straight into the young man's eyes and said it again. He winked and leered.

I changed quickly, putting on the lingerie and adding the breast forms, giving myself relatively small but distinct breasts. I glimpsed myself in the mirror and was thrilled at the girlish figure I saw.

As we left the changing rooms, my wife grabbed a piece of paper and pen from a nearby counter and I watched her write my cell number on it. She handed it to the young man and said, "Call her some time. She'd really like to help you with that." As she did so, she grabbed my hand with her free one and pulled it down to stroke the lump in his crotch. It was huge and I couldn't help myself as I continued to fondle it and stroke it. Finally, my wife pulled me away, "Le's go my little sissy, lots more to do and you have an appointment to get to."

Expecting to head to the checkout counter, I was surprised when we headed in the opposite direction. Just as I started to ask why we entered the cosmetics area and I found myself being pulled toward a couple of expectant looking people behind one of the counters. One was a lady in her 30's and the other was a young man in his early 20's, wearing unisex clothing and heavily made up. He greeted us, "Hi, I'm Matt and this is Julie." I went to shake his hand but he pulled me close to give me a quick peck on the mouth. "Hi, darling, no need for formalities here. I assume you're the one your dear wife told us about."

I was at a loss for words but Cindy jumped in, "Yes, this is her. You can see that we have a bit of a challenge."

Cindy had me sit on a stool in front of the counter, "OK dear, I'm going to leave you with Matt and Julie. They promised to take good care of you. I think I'll wander around the store for a bit. Maybe see if I can help that young lad in menswear out with that little problem he had." She winked and grinned lasciviously.

For the next forty-five minutes Matt and Julie took charge. They held different types and shades of makeup to my face, argued about the best colors and products, applied huge samples of all sorts and finally came up with a selection of products. They next proceeded to apply them, explaining as they went, "...concealer under your eyes to hid the puffiness..."

"This is foundation. You use it to make your skin tone even. This is a special one that'll help hide your beard."

"...darker beside your nose to make it look narrower..."

"...blush just below the corner of your eye and back..."

On and on it went, through eyeshadow, eyeliner, mascara, lip liner and lipstick. A number of customers came by and gawked. I heard many manly snickers, ladylike snorts of disgust and a few oohs and ahs. I tried to see the source of some of these but after having my head pulled back around non too gently and getting scolded several times I gave up and just absorbed it. The snickers and disgust just as thrilling for me as the oohs and ahs, driving home the humiliation that I craved.

I drew back briefly when Matt picked up some tweezers and approached my eyebrows. I knew that there would be no hiding them later. He was determined, though. "You just can't go out with those big caterpillars on your face. I won't let you and your wife won't let you. Now, sit still," and again my head was pulled around. As Julie held my head still from behind Matt proceeded to pluck and trim. I forced myself to relax and, finding that I could ignore the pain I gradually began to look forward to the end result.

Finally, it was done and they brought a small mirror over. I couldn't believe it. I looked like a different person. I exuded sexuality. I turned this way and that to get the full effect. There was no way I would pass but I was clearly a sexy looking ... something. I looked at Matt and Julie and whispered, "It's wonderful. Thank you so much."

Julie gave me a quick hug. Matt, though, seemed to be almost in tears as he said, "Oh, Baby, you look so sweet." He gave me a hug and another kiss on the lips this time pushing his tongue into my mouth. I hesitated momentarily then started to suck hungrily on it and then pushed my own tongue through. I couldn't get enough and attacked his mouth with my own. Pushing deeper, sucking him into me and playing with his tongue with my own.

Distantly, I heard my wife chuckle, "If you girls are just about finished."

I pulled away and turned to see my wife standing there, her hair disheveled and her lipstick smeared. "Oh, my little sissy, you look so lovely," she cooed. "It looks like we both need our lipstick fixed but before we take care of that come here, I've got something for you." With that, she pulled me in and kissed me deeply, pushing her tongue halfway down my throat. I tasted cum and knew that she had been back to mens wear.

Finally, she asked Matt to help us with our lipstick. After he was done she again wrote my cell number on a piece of paper and stage whispered to Matt, "Call her. She would love to finish what you started." I heard snickers from the onlookers behind me and was overwhelmed with embarrassment and with love for my wonderful wife.

And then, abruptly, Cindy was off and running, dragging me along to the checkout, "C'mon, Sissy girl, we have to get moving if we're gonna get to our next appointment on time."