A Sissy Shopping Trip Ch. 01

My wife, Cindy, and I were in the bedroom getting dressed for a party at Tim and Karen's place. They were good friends that we had known for even before our marriage four years earlier, with whom we had shared a lot of good times, including many a camping trip and tipsy card game, always with plenty of hot talk rife with innuendo.

Well, technically, Cindy was getting dressed and I was lounging on the bed, clad only in my panties, watching. I always enjoyed watching Cindy get ready to go out. I love her body, with its perfect, curvaceous ass, full breasts and long legs, all perfectly matched with pouty full lips, beautiful green eyes and perfectly arched brows. Always, though, I felt an undercurrent of envy. If anything, this time I felt it more than ever.

She had bought new things for the party and they were the hottest I had ever seen. I wanted them for myself. I wanted to wear the short skirt, the low-cut top with no bra and the stiletto's and to show off a perfectly formed ass, breasts and legs. I would never have the shape but I loved to dream. I felt my cock stir and begin to tent my panties.

Cindy, seeing me staring intently laughed a bit and asked, "What do you think, dear? Is it working for you?" With a knowing look at my crotch, "Looks like it might be."

It seemed like I was in a trance and came out slowly, stuttering, "Uh, I love your new clothes. When did you get them? They're so sexy."

"Sorry Sweetheart, I know you love shopping with me but I wanted to surprise you. I got new makeup too. How do you like my eyes?" she asked, fluttering them at me.

They were outlined darkly, with long mascaraed lashes and, with the hazel and golden eye shadow, they exuded sexiness. With feelings in a jumble of pride, lust and envy I whispered, "I love them. I love you. You are so sexy. I just wish ..."

"What's that, my little sissy? You wish you could go to the party all dressed and made up sexy too?"she interrupted.

"Uh..." I muttered. "I guess so."

"Sorry my sweet, I don't think Tim and Karen are ready for that yet, do you? Much less all the other people that'll be there. Sorry, you'll just have to go in your man clothes and try to look the part."

I could see the clips from her garter hanging down. She always leaves her stockings till last so they won't get snagged as she gets ready. This was no exception but, as she turned to open her top drawer, my breath caught and it came back to me with a lurch, what I had forgotten to do. I had been home alone while she worked the late shift for the past couple of weeks and had dressed up as sexily as I could, in my own lingerie, mini skirts, tops and high heels. I loved to take pictures and dream about going out all dressed up. Unfortunately I had run out of stockings and borrowed a few of hers. In fact, all of hers. She had nothing left except her backup pantyhose.

I felt my face grow hot as I watched her rummage around. When she turned to express her frustration guilt was written all over my face. "Ahh," she exclaimed as understanding came, "So what happened to them?" As she made a beeline for my lingerie drawer I tried to intercept her but she had the drawer open in a flash. They couldn't be missed. The well-worn stockings in all of the colors she likes to wear, including the bright red ones she wears out for our hottest dates. All were noticeably well-worn.

She turned slowly to me with hands full of stockings and a scowl on her face. "What is this?" she demanded. "I know you like to dress up but we agreed that you wouldn't wear my stuff! Didn't we? Well, didn't we? So, you spent that last couple of weeks wearing out my stockings? Couldn't you just go get some of your own?"

"I,m really sorry, Sweetheart," I whined. "I was all dressed up and I didn't feel like getting changed."

"Well," she scowled, "That's a bad excuse for the first time but what about after that? You've obviously been at it a lot! Couldn't you have bought more after that? You just thought I'd let it go, didn't you! You selfish pig. Even while you're dressing up like a sissy you still act like a selfish man don't you!"

"I'm sorry, Sweetie. I... Well, I... I just forgot and they were... Well, they were just there." I finally blurted out. Embarrassment overwhelmed me. I always taken a kind of of smug pride in the thought that I was more sensitive and thoughtful than a typical man. My feminine side. It was how Cindy and I had explained my desire to dress up in sweet and sexy women's clothes. She clearly doubted that now.

She looked daggers at me. "Well," she hissed, "That's not going to help me now is it?" I cringed as she continued, "I think my little sissy is going to have to be taught a lesson about borrowing without permission." Then, with an evil smirk, "I have just the thing. We're going shopping tomorrow. Don't make any plans."

I always enjoyed shopping for sexy things with my wife so I breathed a sigh of relief. I loved the feel of the sexy things and, as I helped her find just the right sizes and styles. As I watched her try them on, I would imagine them on myself. She always ordered me to join her in the change room in the stores that would allow it and gave me an extra thrill by ordering to to find her different sizes and styles to try on. Somehow she never seemed to get just the right size in anything and found many excuses to send me searching. Did the sales people have any idea why I went with such enthusiasm and looked through every rack for just the right thing? Always, so far, I had been too afraid of being caught to actually put anything on myself but usually managed to get some things in my size out of the deal.

I thought no more of it as she picked through the used stockings to find the least worn pair.

To me she looked as sexy as ever but she complained bitterly about having to wear dirty, worn-out clothes and about how they were baggy and no longer fit her properly. "I have to pull them up to may waist to keep them from looking like sacks," she complained.

I felt bad and could hardly wait for the night to end. It was, as I would find out, only the beginning.

At the party my wife looked radiant and, as she drew stares from every man there, I was totally proud and thrilled to be with her. She, on the other hand, threw me dirty looks at every opportunity. Finally, Karen, our hostess, caught up with us during one of the few dances when Cindy wasn't out on the dance floor being fondled by yet another guy. "Are you guys all right?" she asked. To my wife, "You seem really upset."

It seems that Cindy was dying for the opportunity to talk about her frustrations and proceeded into a litany about how she was forced to wear old baggy stockings and how they were so gross. Then, to my horror, she explained, in detail, why she had no fresh stockings to wear, "My little boy, here, sometimes likes to play at being a little girl. You should see him. All dressed up with his heels, his panties, corset, sexy skirt and stockings. Even makeup, believe it or not. Five pairs of stockings worn out in this past couple of weeks. Maybe, someday, I'll have to show you his pictures."

Karen was almost speechless. She turned red and giggled. She blurted out something to Cindy that sounded like, "You poor thing," and made a quick escape. Minutes later I saw her laughing quietly while talking to her husband, Tim. Tim, big, burly Tim, was looking over at me and smiling. I wished I could sink into the floor. He winked and turned back to Karen. He was saying something and shaking his head. I only hoped he was trying to persuade her not to tell everyone at the party.

Tim came over later and, smirking, spouted some clever innuendo about having a girls night out sometime. I felt myself turn beet red and blustered about how it was just something I did for fun once in a while. He just winked and left it at that.

The rest of the party was uneventful except that I couldn't string two words together and everyone, I'm sure, thought I was stoned or something.

Thinking that the storm had passed I thought I might get a good night's sleep but found myself lying awake with fantasies running through my mind all night. Dreams of shopping, parading around in my new purchases, trying on everything in sight with salespeople helping find just the right thing and Cindy encouraging them the whole time. Other dreams of dressing up in my sexiest things and doing my best impression of a slut for Tim. Again, with my wife offering encouragement and giving advice on how to perform just right. Always, though, the specter of my upcoming punishment loomed, adding a touch of fear, as an extra spice, to the tension I was feeling from head to toe.

In the morning I dragged myself out of bed and sat down with a pot of coffee to clear my head. When Cindy hadn't yet gotten up I went out to do some chores in the yard, not wanting to incur more wrath by leaving them any longer. About an hour later she stuck her head out the door and I waited with a bit of pride at a job well done for her to exclaim how pleased she was and was shocked when she yelled, making sure the neighbors could hear, "Come on Sweetie. Time to get cleaned up so we can go shopping. We need to buy you your own sexy things." I felt my face get hot and raced into the house before she had a chance to repeat it.

I started to complain but she hushed me, saying, "Get ready to go my sweet little sissy. This is your punishment and you had better take it and do what you're told or there'll be no more dressing up in this house. You are either a sissy or you aren't!" I hesitated for a second but I could see that she was dead serious so I headed for the bathroom.

After I had shaved and showered Cindy followed me into the bedroom. I started to get my clothes out. Panties as usual but with typical man socks, baggy jeans and t-shirt. I had always wished I could dress up in more feminine clothes but was horribly afraid of what people would think. I always wore typically male clothing outside of the house, even staying away from anything that fit too well for fear that it would give away my inner desires. Today was different.

As I started to put the clothes on she stopped me, "You can't wear that horrible stuff to shop for sexy things. What'll the sales people think?" She proceeded to get out my sexiest lacy panties, one of her stretchy scoop-neck tops and the least worn pair of white stockings she could find in my lingerie drawer. After I had put on those things she pulled out a pair of her jeans from a couple of years ago, before she had lost ten pounds, and said, "I think these might fit, Sweetie. Try them." A bit stretchy, they fit perfectly, framing a nicely rounded ass and showing of my panty lines perfectly. A shiver of excitement went through me and my cock hardened perceptively. I started to complain about going out that way but, again, she hushed me, saying "That's enough Sissy. Do as you're told."

She pondered having me wear my 5 inch stiletto's but decided that, for now, I would just have to wear my best loafers. "You just won't be able to walk around enough in those. Maybe we'll see what we can find while we're out. You need something new anyway."

Just before we left, Cindy said there was one more thing to do. She had me close my eyes and I heard a phhht sound. She came around behind me and reached into the front of my jeans and down my panties, gently caressing my cock and balls. The aroma of her favorite perfume wafted up. Another phhht and I felt a light spray on my neck. "Now," she said, "You're ready." I felt another shiver from head to toe and had to admit to myself that this was a dream coming true.

"OK, Sweetie, lets go!" she exclaimed and I started toward the garage door, carefully walking on my toes, one foot carefully placed in front of the other and with an exaggerated wiggle. "Nice," she said, "But you're going the wrong way." At my look of confusion she pointed out that Tim and Karen had borrowed our car for party preparations while their was in the shop. "Remember, Sweetie? We have to pick it up from their place."

"No," I thought, in a panic. Fear, humiliation and pure excitement took over and, as my knees threatened to collapse, I almost fell. I turned to my wife pleading, "Not Tim. Please, Baby. I can't do it."

"Oh yes you can," she snarled. "Its not like Tim doesn't know anyway. Besides, I heard you last night. Tim, Tim, Tim, over and over again. Oh, I think you can all right!" With that she gave me a push toward the door. "And lets see that sexy walk again." Even as I resisted I was thrilled and proceeded to the door. Just as I stepped out she stopped and said, "You head over there. I said we'd call first so I'll give them a quick call and catch up with you." With that she closed the door in my face and all my hopes of sneaking up unnoticed by Tim evaporated.

As I walked down the driveway I saw the curtains pulled back in our front widow and Cindy watching, phone in hand. She did a little upright wave with her hand to signal that she wanted to see me wiggle while I walked. I grimaced but proceeded down the street with my behind swaying, secretly hoping our neighbors were watching. Excitement at being out in these even slightly sexy clothes was winning out over the humiliation. I wanted them all to see.

As I expected, I sashayed up Tim and Karen's sidewalk alone and I saw them standing behind the window, watching me every step of the way. They waited for me to ring the doorbell and made me stand there for minutes, drawing out my humiliation. Then, as the door finally opened, I saw Tim standing there alone and in his underwear, with a hardon pushing them halfway up his hairy belly. "Sorry," he said, "Didn't have time to get dressed. Hope you don't mind." He chuckled, "Mind you, from what I hear, you probably don't mind at all."

I felt myself blush brightly and could only mutter a muffled, "Uhmmm," while I stared at the ground.

"That's a really cute outfit," he said, grinning. "Turn around, lets see all of it." I turned and just as I was facing the street he dropped the keys on the ground in front of me. "Sorry," he said. I bent to pick them up and felt his hand on my ass lightly rubbing back and forth, "Looks like sexy panties you're wearing. What color?" Startled, I turned and straightened quickly, rubbing my face up his protruding cock in the process. "Oh," he exclaimed, "What's this. Is there something you want besides keys?"

Suddenly the smug grin disappeared from his face and he looked embarrassed. I heard Cindy's voice behind me, "Mmmm, Tim. Looking good! Maybe we can both try some of that some day." Tim turned bright red as I felt the same familiar flush myself. "Not today, though. My little sissy and I have some things to do." With that, she grabbed the key from me and headed for the car beckoning me to come along.