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"You know, you can never go wrong with a black cotton Hanes Her Way panty brief." Karen stood behind me as I sat at my desk typing. "Excuse me?" I stuttered. "Except if she was wearing white slacks and you'd possible see the dark panty material through the slacks, but you're wearing appropriate slacks, so those panties are perfect with your outfit." "I'm not sure what you are talking about." I turned my chair and faced her while talking. "You're wearing Hanes Her Way black high cut briefs. I can tell. I have those exact same panties and I know what the waistband looks like. They're perfect for when a woman is in her period time, their sexy because their black, and they're much more comfortable than those lacy nylon bikini or thong style panties, wouldn't you agree, James?" I was trying to determine if this was some kind of sexual harassment situation or what kind of response I could give that wouldn't make me out as some kind of deviant. "I've always thought of you as a bit of a panty-waist, James. I'm not saying that's a bad thing, but really, you should be a little more careful about tucking your shirttail in. People will talk if they know you are wearing women's panties. I'm not making any judgments, dear. I think it's cute. I'm just saying; cover up a little, girlfriend, and do be little more careful before you flash those sexy panties in front of someone who gives a damn. I wouldn't want you to lose your job." "Thank you, Karen. I'll be more careful from now on." I turned my chair around, fixed my shirt a bit to make sure it was tucked in the back and then started working again. I didn't think I could ever be so embarrassed. Karen and I had been working together for a few months and this was by far the most embarrassing thing I'd done in front of her. She left the area, a sweet innocent little smile on her face. I received an email a few minutes later; Karen was inviting me out to lunch. I really didn't have the money, but she said it was her treat. Okay, I figured, why not? If she was going to pay, and I knew what she'd want to talk about. She came by my desk at noon. I slipped on my jacket as it was supposed to rain later and didn't want to get caught in the rain. We walked to her car where she opened the passenger door for me. "Kind of makes you feel like a 'lady,' doesn't it?" she asked me. I climbed in, and she closed my door. I did reach over to open her door but she corrected me when she got in. "I'll take care of opening my door, thank you!" she said this but not in a condescending tone. It kind of felt like she wanted to be in charge and I overstepped my bounds a bit. "Sorry," I mumbled. We drove to the mall, and she directed me to stay seated so she could open the door for me. Okay, this was strange. But I liked that authoritative persona - She was buying me lunch. After she opened my door and I started getting out, she noticed she had a run in her pantyhose. "Damn!" she pointed out the run and looked at me like it was my entire fault. "I'm not blaming you, dear, but do be a honey and run into JC Penney, get the same brand you buy for yourself, in a color that matches my skirt, please - we probably wear the same size, so just buy a couple pairs, and I'll get us a table at Ruby Tuesday's. You don't mind, do you, dear?" She looked at me as if she were daring me to question her authority. "Not a problem, Karen. I'll meet you in Ruby Tuesday in 15 minutes. I'll take iced tea if you get a table right away, please." How did she know I wore pantyhose? Or what brand? This was getting a little scary. I mean, she did catch me in the panties so she could have made a logical assumption that I probably wore pantyhose as well. And we do look like we're both about the same size. I wasn't sure if I should be angry about this. I wasn't sure if she was trying to embarrass me by making me purchase her pantyhose, but like I said, she was buying lunch, so a few pairs of stocking wouldn't be too much to ask in return. I bought a couple pairs of control top pantyhose in a grey tone. Karen was wearing a gray skirt and jacket, and like she said about wearing black panties, I don't think anyone can go wrong in a gray skirt and top. I hoped I wasn't making a bad judgment about control top pantyhose, but she did say to purchase the brand I prefer, and I'm embarrassed about admitting I have a little pudge in my tummy. I even own some spanx and am not afraid to admit that (privately.) The woman at the sales counter informed me that there was a terrific bra sale going on, and she handed me a brochure with my sales receipt. I found Karen quickly in the restaurant. She stood, walked to my side of the table, helped me take off my jacket, and pulled my chair out for me. She'd already ordered lunch for us both. I handed her the package but she just handed it back to me. "You take care of this for a bit, would you?" she asked. She did notice the bra pamphlet though and pulled it out as she pushed the bag back to me. "Oh, a bra sale!" She sat across from me, facing the restaurant, and I was sitting facing her and the wall. I couldn't see if anyone was behind me but there were people to our right and left. "Their bra sales are very popular," she stated as she was thumbing through the catalog. When I've taken women out for dinner, I usually sit facing the restaurant so I can gain the attention of the waitress. I felt a little funny not facing that way now. The ladies on our right were an older woman and what I'm assuming was her daughter out for a mother/daughter lunch. On my left was a mother with two young girls, both too young to be in school. The mother looked a little stressed. She was having a hard time getting her daughters to eat their lunch. So here I was surrounded by a bunch of girls and women, and Karen was treating me like I was her date. And she now wanted to talk about the JC Penney semi-annual bra sale. This was getting a little more embarrassing. I didn't notice the waitress behind me when she reached over and placed a couple of glasses of water on table. She put an alcoholic beverage in front of Karen, and I just got the water. When the waitress pulled away, her bracelet pulled the package of pantyhose off the table and the packages slid out of the Penney's bag. The waitress bent over to pick them up, and said, "Oh, I'm sorry, but I'm glad that happened. I've got to get some new hose and their semi-annual bra sale starts today." Karen just agreed and told her that I was just there to pick up some pantyhose and brought back a pamphlet. She handed the pamphlet to the waitress and they chatted for a few minutes about the bra sale. Apparently the JC Penney semi-annual bra sale is quit the women's event because the older woman and her daughter joined in on the conversation. "Oh! We're going there next," the older woman stated. "Were there a lot of women in the lingerie department?" she asked me as I tried to hide behind my glass of water. I guess Karen thought I must be concerned with my weight as she didn't order me an iced tea or an alcoholic beverage. "No, it was pretty quiet when I was there, I mean, I just went right in and out," I responded to her question. The older woman noticed I'd purchased the control-top pantyhose. "Are their pantyhose on sale as well?" she asked me. This was embarrassing. All the ladies were looking at me like I was the experienced JC Penney lingerie expert as I'd just come from that department. I responded to her questions as Karen just sat there smiling at me. Things settled down a little after the waitress placed my pantyhose back in the back and placed it next to me on the table. I put the bag next to the table leg after she'd left. Lunch went by without a hitch. I mean, Karen did talk about the last semi-annual bra sale and all the people who attended. She told me I was lucky to be in and out with the pantyhose purchase. It sure seemed we talked a lot about women's clothing during lunch but I let Karen do all the talking. I'm not an expert on women's fashions. I think this surprised Karen because she knew I was wearing the panties. We ate a light lunch and Karen paid the bill. I'm surprised I wasn't that embarrassed as women seem to be doing this more and more. As Karen had made all the decisions anyways, the waitress handed her the bill. I think the waitress probably noticed Karen had stood when I arrived, helped me with my jacket, and pulled my chair out for me, so it would have been logical to give the bill to Karen. We were out the door and walking toward the mall exit when the waitress yelled out to me, "Sir," she said. "You forgot your pantyhose." She ran toward me with the JC Penney bag and she also had the brochure in her hand as well. She handed them both to me. Karen just laughed a little. I'm not sure how many people noticed that she said the pantyhose were mine, but I sure noticed. Karen didn't even try to take the bag, just allowed the waitress to hand the package to me. "This brochure has some coupons that I'm sure you can use at the bra sale," she advised me as she handed me the catalog. Karen held the door and we walked out. She placed her arm into mine and we walked toward her car like a couple. "That was nice of her to return that brochure to you. Those coupons are great." I told Karen that I really was a guy and had no reason to wear a bra, but she told me not to be silly. "One can't wear pretty panties without wearing a cute bra to go with it." She once again opened the car door for me, took the package as I got in, and then handed it back to me before closing the car door behind me. This time I didn't reach over and open her door. She walked around, unlocked and opened her own door and slipped right in. It was like she didn't even worry about that run in her stockings any more as she didn't mention anything about it after lunch. I was looking at her legs and noticed that she'd actually removed her pantyhose. She must have done that while I was at JC Penney. I asked her if she was just going to put on the new pantyhose when we got back to the office, but she told me no. "Why, don't you think I have nice legs, James?" she asked me. Why did she ask me to get the pantyhose if she wasn't going to wear them anyways? She pretty much opened the doors for me all the way to our office. She made me carry the package, though I thought I bought them for her. She didn't even take the package when I offered it to her when I got to my desk. "No," she said, "those are for you! Why don't you go and put on a pair? They'll make you feel sexy!" She didn't look like she was going to take 'No' for an answer so I took one of the pairs out of the bag and walked toward the men's room. There are not a lot of guys in our office, so I wasn't too concerned about there being anyone in the restroom. I went into one of the stalls, removed my trousers, and carefully rolled the pantyhose up over my panties. Karen was right. I did feel kind of sexy. I don't normally wear pantyhose, but sometimes, during the winter, I might put on some cable tights under my slacks. That always makes me feel kind of young girlish. I remember looking at girls in my middle school in their short skirts and cable tights. I always liked that look. Karen was still at my desk when I returned and she did something she's never done before. She hugged me really close and rubbed my bottom. "I love the feeling of the nylons rubbing against a panty. Don't you, James?" she asked me. I didn't want to offend her by pushing her away, and I did like the feeling of her rubbing my slacks against the panties and hose. I did suggest that we really shouldn't be hugging each other in a work environment, but she just blew that statement off. "Don't get your big girl panties all in a bunch," she laughed as she broke away from the hug and started walking back to her desk. As it was Friday afternoon, the office environment was a little more relaxed and I was getting a lot of work done. I was totally comfortable in my new pantyhose, and wasn't worried that Karen now knew I was a bit of a panty-waist. Hell, she was encouraging it. I got another email about closing time, again from Karen, inviting me to attend the semi-annual bra sale with her the next day. "We'll go early for the best selections," she informed me. "I'll pick you up at 8:30." I didn't even know she knew where I lived but apparently, she knows all about me. "Don't forget the brochure, James. It's got the coupons!" I think the most embarrassing thing any man can do is to compliment a woman on some item of clothing and ask her where she got it. Before Karen and I went shopping, she handed me her organizer. Not a masculine looking item, I can assure you. Not a bright pink, but definitely a woman's organizer. She directed me to talk with at least five women in the mall and compliment them on some item of clothing that I found attractive, shoes, a skirt, a dress, those types of things. Then I was to write the information in the organizer, just so they knew I really was interested in the location of the discussed item. She requested that I talk with each for at least a minute, so might ask about price or color or something. She didn't care if I was embarrassed about it. When we walked into the mall, I heard the clicking of a woman's high heels on the tile and turned to look. Karen told me that was 'interview number one,' since it got my attention. I walked over to the woman and the conversation went like this: I love your shoes! Would you mind telling me where you got them? No, of course not! Aren't they cute. Taylor's, and they were on sale! How high are the heels? Three inches, but I'm sure they have different heights, if you're concerned! So they were on sale. Would you mind totally if I asked the price? I really need a pair like that! $45.00, if I remember correctly. And thank you so much for asking. I love getting a compliment about my clothing selections. You'd do great at shopping at Taylor's. They have a wonderful assortment of sizes! I really must be going. Enjoy your shopping. I walked back to Karen as quickly as possible. I don't think I could have been more embarrassed. I know I was as red as a beet. It took me a moment to find her. She wasn't going to let this woman know I was with anyone. I'm sure she wanted that woman to assume I was writing the information down in my own organizer. I'm sure she thought the information was for me. One down, four to go. The second was a woman who'd sewn a pair of blue jeans into a skirt. Karen knows I like women with a bit of modesty, and a long skirt always captures my attention. The woman was walking in front of us. "Interview number two!" Karen directed me as she walked into one of the stores near us. I love your skirt! Did you sew it yourself? Thank you! Yes I did. I don't sew much, was it difficult? Oh, gosh no! And you can get the pattern at Michaels. It was a breeze. And you might as well use those old jeans that don't fit any more, wouldn't you agree. (She was looking at me funny, but I don't think she was too uncomfortable). I know what you mean - I started writing the information about Michael's down in the organizer. I think it's wonderful that you kept the length. So many women like to wear the short jeans skirts these days. I prefer a little modesty in skirt lengths. Well, that way I don't have to shave my legs as often, you understand. It makes a woman's life so much easier. And I don't have to wear pantyhose or tights. And this skirt is warmer in the winter. It really is more comfortable than our tight jeans. But hey, I'm sorry I really must be going. Thank you so much for the compliment. Interview # two out of the way. Karen walked out of the store as I finished writing my notes in the organizer. "That really is a cute skirt, didn't you think," she asked me. Of course I said yes, as she knew I'd like to wear it. We were getting closer to JC Penney and wouldn't you know it but there is a wig shop in the mall. "Have fun, Jamie" - she pushed me in the door. There was a woman trying on a wig that I really liked, a pageboy, dark, but not black. I walked around the wig store for a few moments as the woman and the sales girl were working with fitting, care and maintenance of the wig. While she was standing in front of the mirror, I gathered my wits and started talking to her. That style is perfect on you! It frames your face wonderfully! Why, thank you! I'm not used to hearing compliments like that from a young gentleman. My husband probably won't even notice. May I ask you, what is the name of that wig? I mean, what is the brand and all that? Oh, you should ask the sales girl. She is so helpful. Oh, but she went to the back room for the proper size. I'm sure she'll be right back and she can give you all the details. Oh, that's okay. I just think you have wonderful taste. Like I said, that wig defines your face. It's such a classic look. I'll be you think it makes you look younger? I don't mean to be impolite, but you look so young in that pageboy style. Definitely go with that wig! She took the wig off and I started writing the information down in the organizer about the style and the price. When the sales girl came out, she started talking with us both about the wig and I just continued writing the information down. The sales girl gave me her card, telling me she could definitely fit me in that style if I was interested. I left the store, searching again for my missing Karen. I didn't have to look long. She was standing near the Taylor's store. A women's swimsuit was on the model. A conservative two-piece, skirted bottom. Karen was talking with another woman as they looked at the bathing suit. Karen pointed the woman at me and then walked away. The woman walked up to me and introduced herself to me. She and Karen were friends and Karen asked her if she wouldn't mind helping me to get some additional information about that 'adorable' swimsuit. Her name was Alice and she put her arm into mine and told me we'd go get that information about the swimsuit that Karen was looking for. She noticed the organizer and asked me if I were Karen's secretary or something. "Something like that." "That is an adorable swimsuit, don't you think?" She pulled at the bra top and pulled out the information card. "And it comes in sizes up to 18! Perfect! And look at this cute bottom! Retro and skirted, any woman would be comfortable wearing something this adorable at the poolside, don't you think?" I wonder if that is the only color it comes in? Black seems a little provocative, don't you agree, Alice? Wouldn't you want to be, wearing such an adorable two-piece? Women wear black to be a bit sensual. And that suit screams 'provocative!' You'd definitely turn a few heads wearing that swimsuit. But I'm sure it comes in different colors if you're interested in asking. Let's find a sales girl. We spent a few minutes walking around until we found the swimsuit section of Taylor's. Taylors is a woman's store. You shouldn't expect to find young girls swimsuits here. Most are the one-piece tummy control type of suits. We looked around for a few minutes. The sales girls were pretty busy this morning. "Karen told me you were looking for some shoes here. Let's go take a look while we're waiting." We went to the shoe department where I opened the organizer and found the information about the heels I'd complimented on earlier in the mall. We found the pair and Alice asked me about size. Don't mess with me, Jamie. Karen told me everything. What is your shoe size. 11 ? - Women's size. Kind of large, but Taylor's caters to full-size women. It took only a moment to find the shoes I was looking for. Alice didn't even have me try them on. A sales girl came to our aid and we walked straight to the swimsuits. Jamie here likes this two-piece but was looking for something besides black. Would you have something like this in a floral or possibly a pinkish color? The sales girl looked at me and smiled. I'm sure we can find Jamie the perfect little bikini any woman would love to wear by the pool. And what size are you looking for? Jamie? 18 please, and black is fine if you don't have a floral or pink. I really don't want to be a bother. Oh, it's no bother at all. We want all of our customers to be happy. Oh, I see you've found some heels to go with your new suit. I'll try and find the perfect little two-piece that'll make the boys jaws drop, Jamie. I'll make sure there is a dressing room available, you'll want to try it on before purchase. Thank you! I noticed Karen had entered the store. Probably wondering what was taking so long, but when she saw that the sales girl was checking on a dressing room and looking at the swimsuits for sizes, you could tell she knew what was going on. Karen and Alice started talking as I just stood waiting. The sales girl called out 'Jamie' and directed me toward the dressing rooms. I found a floral skirted retro style that is just adorable. Won't you come this way? I walked into the dressing room as she handed me the swimsuit. Karen and Alice walked up and stood by the door. We'll want to see you in your new suit and heels, please. I knew that was coming. Needless to say, I wished I'd shaved my legs. I stood at the door in the two-piece, in high heels. I wasn't wearing the wig, but Karen informed me that we'd make that purchase on the way out. It only took a few minutes and nobody else saw me except Karen, Alice, and the sales girl. I don't know why they didn't laugh at me as I'm sure I looked foolish, but they all agreed that that suit and those heels were perfect. I went back in and changed, made my purchases and thanked Alice for her help. One last interview to go and we hadn't even started shopping for bras at JC Penney's. Karen told me I could do my last interview in the lingerie department of Penney's. I was carrying a Taylor's bag and Karen's feminine organizer as she and Alice walked ahead of me. JC Penney's was pretty busy this morning. A lot of women attend the semi-annual bra sale. We walked straight to the lingerie department. I noticed a woman looking at one of the more lacy, risqu? black bras when Karen held her hand up and held all fingers out. # five. "Don't you think that lace would be kind of uncomfortable? It is pretty though, but I think I'd just die wearing such an itchy bra. "I don't know, it is pretty though." She looked at me for a moment, then saw the organizer and Taylor's bag. "Are you shopping for your wife?" No, I'm not married. I just can't resist a sale. And you're looking for bras? Well, not really. I was just walking through. I was just wondering how women can stand wearing lacy lingerie. I'd think it would itch and be uncomfortable all day. Well, a woman wouldn't be wearing a sexy bra like this all day. This is the kind of bra a woman plans on getting out of quickly. And look, it comes with matching panties. Do you think a man would let a woman wear something like this for very long? I don't think so. "What is the price?" I asked her. We spent a few minutes looking at the bra and the tag. She held up the panties and well and I started writing the information in Karen's organizer. Karen walked up at this moment. "That bra is like totally you! James. What are you doing in this department? And who is your friend?" She asked like I was with the woman who was interested in the lacy black bra. "Oh, we're not together. He was just asking me if this type of bra itched. I was explaining that this was the type of bra a woman doesn't wear for very long. I mean, look at these panties." She held out the thong style panties and I took them. "Certainly not like those briefs you wear, are they, James?" Karen took the panties and put them down. She took me by the arm and asked that I write about the last interview in her organizer. "Let's find Alice and do some real bra shopping, shall we?" Alice was standing next to a large round table. Karen directed me to stand next to her and help her to find whatever she asked me to look for. Karen took the organizer and the Taylor's bag and pushed me toward the large round bra table. "James! Thank you so much for helping me. I'm looking for any 36 C cup with a lace band, hook and eye, with underwire, wide straps, and hidden seams." "Okay!" I looked at her like she was crazy. She directed me toward the opposite side of the table. I really didn't know that much about bras so I asked the lady next to me if she wouldn't mind helping me to understand exactly what Alice was talking about. We spent a few moments as this woman found different types of bras and pointed out the specifications that Alice asked for. A sales woman walked up and started explaining some of the complexities of the bra style as well. A few other women listened in, like we were all part of a bra class. I didn't have time to be embarrassed as bras seemed to be flying all over the place. I found three that met with Alice's specifications and I walked over to her and Karen. Well, find the matching panties, silly! She didn't tell me that before I started but it made sense afterwards. I found one of the sales ladies and asked that she help me to find coordinating panties for the three bras I had in my hands. She and I walked to the panty section where we located the matching panties. Size? Damn! I'll be right back. I found Alice and asked her about her panty size. She told me to guess. I wear a size 6 or a medium and I looked at Alice as if I were sizing her as well. I thought I'd be nice and said 5. She kissed me and told me I was a doll, but told me that women have a little larger bottom than men and told me to go with a 7. I walked back to the sales lady who was working with me on the coordinating panties and we found a 7 for all three bras. It really is amazing how these women work around so many women walking through all the isles. There were a few younger girls shopping with their mothers, and I heard a couple of snickers but after all the other embarrassing moments this morning, a few girls snickers weren't too bad. "Would you mind terribly measuring Jamie here for a bra?" Karen was standing next to me and the sales woman. I didn't even see her walk up. "Not at all" was all I heard as I felt Karen take my arm and we started walking toward the dressing rooms. "I figured he'd already been measured for the bras he was purchasing panties for. Jamie, why don't you go into the dressing room and remove your blouse." I entered the dressing room and took off my shirt. I tried pulling up my pants a little as I was concerned about my panty waistband showing. I was wearing a Victoria's Secret pink cotton brief. I didn't do a good job hiding it because I could see the pink waistband in the mirror when the sales woman entered with her measuring tape. It only took a moment as she wrapped the measuring tape around my chest. 38. Karen was standing outside the door. "38-inch band" she called out. "39 cup. He's an A cup" the sales woman called out. "A-cup" Karen repeated. "Figures! I would have guessed a double or triple A. Jamie, you must be very proud!" she said as the sales woman started exiting the dressing room. "Cute panties!" she told me as she left. I quickly put my shirt back on and tucked my shirt back in. "Let's get you some bras!" Karen acted all excited and started directing me toward the young girl's section of the lingerie department. "Smaller cup sizes are in the misses section," she informed me. We spent the rest of the morning in the misses section where Karen picked out five new bras for me. Alice stood there with us, complimenting me on my new bra purchases and thanking me for helping her so efficiently with the bras and panties I'd selected for her. I was required to make all the purchases. I mean, Karen and Alice gave me cash and I ended up buying Karen three new bra and panty sets, Alice got six new bra and panty sets, and I got my five bras and Karen thought it would be a good idea to get matching panty sets as well. They didn't stand with me when I bought all the new underthings. The woman at the register made sure I understood that I was buying three different size bra sets, and three different size panty sets. She made sure that I understood that lingerie was none returnable but did compliment me on my selections. I was sure to use the coupons and she enrolled me in the bra purchasing club where I'd be eligible for a free bra with every dozen purchased. Hey - Guess what! I'm eligible for a free bra and panty. Fortunately, Karen was ready for this and handed me an additional set she was interested in. They punched out all the holes on the bra card, then started on a new one. I ended up caring a fairly large JC Penney shopping bag filled with bras and panties. Karen and Alice did help a little with the Taylor bag. We started walking toward the exit where Karen had me walk past the perfume counter. She insisted I try a certain fragrance that she was interested in, and then we walked toward the wig store. Karen, Alice, and I all sat as the sales girl fitted me with a new pageboy, which she told me framed my face wonderfully. I went with a lighter color than the one I'd seen earlier, but was happy with the selection. It took about 20 minutes to get the wig fitted and instructions on care and maintenance but the morning had been extremely successful, according to Karen and Alice. Karen read my notes on the interviews as the sales girl fitted me for the wig. Alice and Karen tried to embarrass me more by complimenting me on their and my new lingerie, but I'd been embarrassed enough and now felt pretty comfortable trying on the wig. Even when Alice pulled out my new bras and showed them to the sales girl, I felt kind of good about it. I survived the JC Penney semi- annual bra sale, got fitted and an appropriate number of bras for a sissy like me. The new panties were adorable. I got a swimsuit that any woman my age would be proud to be seen in. I liked my new shoes. I was even looking forward to trying all my new things on when I got home. Alice went on her way when we left the wig store. Karen and I walked toward her car. She opened the trunk and I dumped all my new packages into it. When we got to my house, Karen helped me to empty the car as we'd have to separate lingerie purchases. She spent the afternoon with me as I gave her a lingerie and swimsuit fashion show. We made love and she gave me a fashion show as well. She didn't take her new undies with her. She found a drawer for her intimates and I wasn't going to argue. She told me to leave her panties and bras alone, as I had plenty of my own. I did have a chance to show her some of the other women's things I'd collected and she seemed happy with my choices. If you ever have a chance to go to JC Penney's semi-annual bra and panty sale, and if you're lucky enough to have a friend like Karen or Alice, enjoy your shopping experience.