Shopping with Lynn

Lynn and I have talked about going shopping together for her lacy things, so I thought I'd describe what I think it could be. I hope she, and you too gentle reader, enjoy it!

I drove my car up the driveway of Lynn's house. It was in a newish development outside of Charlotte, one in which there had been several builders, each with several plans to choose from, the result of which was that all the houses were different. I drove a dark blue Lexus ES which I had bought at the tail end of last year, so it still had that "new car smell." She must have seen me pull up because she was out the door barely after I turned the engine off and stepped out.

"Hello, you!" she said, using the greeting I always used with her.

"Hello yourself, you lovely girl," I replied. I use the feminine pronoun with her because that is how we met and continue to meet, as a man and a woman, even though she is not a continuous dresser and to the outside world today looked like a guy, albeit a pretty one. It was our secret, she insisted, until (if ever) she was ready. But she was dressed androgynously, with a pair of slim women's jeans and a black cashmere V-neck sweater. At the base of the sweater's Vee, you could see a hint of cleavage. No doubt she was wearing a black push-up bra. She also wore light eye makeup, and this morning wore her hair in a pixie, like Audrey Hepburn. Although I am partial, I thought she was hot.

I opened the passenger door for her as a gentleman does, and as she settled into the car, the front of her sweater opened slightly, confirming for me the pushup bra. I might be in my sixties, but I still try and catch a down-blouse every chance I get. "I guess I may not be entirely a gentleman after all," I thought to myself.

"And what are you looking at, Jim?" She had caught me! I was tongue-tied. I had never been caught and didn't know what to say. "That's alright," she giggled, "I understand."

I got into the car and pulled out of the driveway and headed out to the development exit. "Where are we going?" she asked.

"It's your birthday coming up, so I thought I'd take you shopping at Nordstrom's" I told her. It was something we had talked about, but maybe she thought it would never happen, more like something a guy would say when he was still trying to get into a girl's pants. As we had already crossed that threshold, maybe it was a surprise to her.

"Ohhhhh" she smiled at me.

"I called my personal shopper there in men's and asked her to recommend one for you"

"You did WHAT?" she gasped. I pulled the car over and put it in park. Up until now, it was only I that knew of her cross-dressing, and I was about to let someone else into her secret life. I turned to her and asked her "Lynnette, do you trust me?"

"Yes of course I do, but..."

"Listen, to the girl at the store you're Lynn. That's all she knows, it's no different than when you shop by yourself at Kohl's or Target, right? She is just making it more convenient for you by pre-selecting things in your size and preferences," I told her, "Please don't be upset. I promise you'll enjoy it."

Due to the nature of my job, I buy a few Canali suits from my own personal shopper Lysa each year, so we know each other pretty well. I told her about Lynn and explained what I was trying to do for her, and she told me she knew just the shopper in Intimates that could help us. "We girls do talk, you know Jim," Lisa had told me, "And Jennifer will do a great job for Lynn." Lysa had never steered my wrong, and I'm sure she wouldn't now.

We drove up into the mall parking lot in front of Nordies. Lynn had been quiet most of the way, and I could tell she was anxious. "Relax!" I asked her, "Remember, they are working for you."

The valet opened the door for me, "Good morning Mr. Roberts." He greeted me as the other valet opened the door for Lynn. "Are you going to be having lunch here too?"

"Yes, thanks" I replied as I gave him the keys and after Lynn and I pulled on our facemasks, went into the store.

I had deliberately booked a time with Jennifer during off-peak hours so the store wouldn't be at all busy. In fact, it was indeed slow. We ascended the escalator wishing we could hold hands, but we did keep our fingers touching on the escalator rails. Off to the right, past Point of View and Designers was Intimates. "I think we're over there" I said to her quietly.

We walked over to the section and asked the woman at the counter for Jennifer. "I'm Jennifer, and hello, you must be Lynn."

"I am, thanks." Lynn admitted as she blushed. "Well, right this way then," as Jennifer took Lynn by her hand and led her into the dressing rooms along the back wall. "There's a chair here just outside the dressing room if you want to sit," she told me looking back over her shoulder "We'll send her out for you to look if she wants to show you." And into the gynaecium they went, store clerk and a tall, thin man with a pixie haircut and shapely girlish figure.

"Lynn, let me just tell you right off the bat that I'm so happy to be your personal shopper today. I've got some very nice things selected for you that I hope you'll fall in love with. Can I let you in on a secret of mine?" Jennifer asked. "Sure" Lynn replied.

"My boyfriend is a cross-dresser too. It's a benefit of mine to get a nice discount on all the merchandise, so I'm able to buy him all sorts of things. They never check the sizes when they write it up, so never even suspect that my Jason is like you. But one of my besties is Lysa down in Men's Wear. She knows about Jason, so when your boyfriend asked her for help, she knew I would love to help you."

"Oh, thank you so much," Lynn said, "That is such a relief," as she thought to herself "This may really be fun!"

"Now," Jennifer said, "Jim gave me what he thought were your sizes, but you know men, so I selected some things a couple of sizes down and up."

She showed Lynn into the rear changing stall. "Did you wear anything under your boy clothes? Something to start with? Just take those off and let me see what we're looking at."

Lynn complied with the salesclerk's request and stripped off her cashmere sweater down to her bra and her jeans down to her panties. "You're wearing a push-up bra I see, Lynn," Jennifer said, "I think we have something a little more sexy in that style."

"Thanks" Lynn replied and began to blush. Lynn's cheeks were flush, and the blushing continued down her neck to her bra.

"In fact, have you ever worn a bustier?" she asked.

"No, but I do have a corset I like to wear"

"Oh, then you'll like this." Jennifer told her, showing her the first item she had selected for her. "See? It has a zipper going up the front and a zipper in each bra cup too. Now let me step out and you can try it on."

After Jennifer had let the swinging door close behind her, Lynn undid the clasp of her bra, exposing her breasts to the cold air of the store. Her nipples immediately hardened and darkened as the warm blood rushed into the areolae, filling the void made by the swelling nipples. She slipped the bustier on and zipped up the zipper along the front. It was a little snug but looking in the mirror, she was pleased with it.

"What do you think?" Jennifer asked. Lynn opened the door to let her see. She no longer was blushing as she grew comfortable with Jennifer seeing her. "Oh, I like it on you. Do you fill up the cup?" she asked.

"No, but I never do a B-cup. I'm bigger than an A-cup though" Lynn told her.

"Let me check the fit and see" Jennifer said as she matter-of-factly opened one of the zippers to the cup and put a finger inside, gauging the distance from nipple to cup. "Yes, I can find some padding to fill it in, if you want, but that would defeat the purpose of the cup access zipper now, wouldn't it?" she smiled.

"Now, let me see on the bottoms," Jennifer continued, "This bustier already has straps that hang down for hosiery, so you don't need a garter with it."

"I brought in some panties that will go with it, and they're from the same company so the lace matches. Would you like to try them on?" she asked.

"Could I?" Lynn responded. "Of course," the clerk replied, "Although I see a sizable bulge. Are you in chastity full time?"

To that question, the blush returned to Lynn's face, neck, and chest. Her mouth was dry as she replied, "No, but I like to wear it."

Jennifer matter-of-factly replied "Okay, then try these on while I look for the same one with a slit in the crotch. They sell both kinds, but I don't know if we have the one with the slit in stock."

Away she went to check while Lynn peeled off her panties exposing her genitalia, snug inside the CB6000, the pink clittie bound cruelly at a permanent downward angle. She had the key in her jeans pocket to be sure, but if she were to release it, the swelling she was already experiencing would be uncontrollable, and then she really would be embarrassed in front of Jennifer.

She tried on the panties and, except for the bulge, fit perfectly. The manufacturer obviously did not account for a penile bulge in its panty line. There was none of Lynn's pubic hair poking around the sides of the panties; she shaved down there every morning.

"Knock-knock," Jennifer lightly tapped on the door of the fitting room, "Oh, those look perfect, and yes we have the other style. They fit the same, so you don't need to try them on unless you want to. Of course, if you were to wear them with a skirt, well, you know."

"Ha! I already caught Jim out there looking down my blouse. I can imagine what he'd do if he saw this when trying to look up my skirt!" "Boys will be boys."

"Okay then. Would you like to try on a dress?" Jennifer asked.

"Sure!" Lynn sparkled in her reply.

"Do you have a Little Black Dress already?" She asked. "Yes, I do," Lynn replied.

"Good on ya' girl," Jennifer said, "I'm sure it looks fab. So let me show you this dress. It will come about halfway up your thighs, is that OK?"

Jennifer stepped out of the stall and came right back in with a silvery fringe wrap dress. "What do you think? This will add a little glitz to your closet, and you can dress it up with stilettos or you can give it an edgier look with some tights and chunky boots even."

"Oh my god, it's perfect!" Lynn replied, "But it must be too expensive "

"It's not," Jennifer interrupted, "and I was told this is all for your birthday anyway, isn't it?"

She helped Lynn try on the dress, fitting it over the black bustier and closing the wrap in the back. "There!"

"Oh my god. This looks wonderful." Lynn could not believe her eyes.

"You, know, let me run down to shoes and get a pair of shoes. What size?"

"Ten in men's, eleven and a half in women's" she replied, "but nothing too high- I'm already tall."

"Got it, and here are some black nylon hose you can put on. Girl, we are going to fix you right up!"

"Jennifer sure is an enthusiastic shopper," Lynn thought to herself. She ogled herself in the mirror of the dressing room. She could not believe how shapely the bustier was making her figure. She had always been a runner, which meant her legs and bum were already well-toned. She took the hose out of the package and, sitting down, unwrapped them up each leg "like a condom," she thought naughtily.

"Here you are then" Jennifer replied as she came back. "Got you 11, 11-1/2, and 12."

Lynn was still sitting on the bench as Jenn knelt in front of her with the first of the shoes. She helped them on. "I normally don't work in shoes. Sorry."

"There you are, Lynn" she said, finishing the last strap of the not-too-high heels. "Up you go."

Lynn stood up on them and looked in the mirror, turning her hips to look at her whole backside from her bum down her legs to the new shoes. "I love the look. Thank you so much."

"Now, can I suggest one more thing?" Jennifer asked.

"Sure, you haven't steered me wrong yet."

"Well, you have such a pretty facial structure and yet you only wear eyeliner. Let's put our masks back on and go down to cosmetics and sit you down for a makeup."

Lynn was high on the moment wearing her new girl clothes, but this was another step. She hesitated.

"Listen, the makeup salesclerk I talked to is trans, totally. Even the store doesn't know! And if she can fool her them and the customers all day, trust me, with what you have to start with, you can too!"

"Okay, let's do it" she declared and donned her mask.

They walked right out of Intimates, past where I was sitting, and straight down the escalator to all the makeup counters. Because of the mask over her face and her cute pixie haircut and drop-dead clothes she was still wearing, no one was the wiser.

Jennifer left her there at the Bobbi Brown counter as Madeliene went to work. She came back up to where I was sitting.

"She looks great!" she told me.

"Thank you so much Jennifer. She'll never forget this, and I think she'll want to keep using you." I told her. "Can you just bag up her clothes in the dressing room instead, and I'll carry them out for her."

She did just that and we settled up. "Thank you again, you were just perfect, Jennifer." I told her once more as I was leaving her department. I headed down the escalator, and seeing Lynn still in the makeup chair, I went over to Men's to see if my shopper Lysa was there.

I spotted her and went over. "Lysa, thanks for the steer to Jennifer upstairs. It worked out perfectly."

"Yeah, I could tell. I saw them come down the escalator over to Makeup to see Madeline. She's very pretty, Jim- you've latched onto a good one there!"

"Aww shucks, Ma'am" I replied. Of course, now she knew I liked gurls, but I knew my secret was safe with her.

I looked around the men's department until Lynn was done at the makeup counter. She must've spotted me because she came over, COVID mask back up. "Well, hello there, kind sir" she said, "What's in the bag?"

"Oh, just some jeans, a cashmere sweater and some unmentionables." I replied. "I've made some reservations for lunch at the café here if you're hungry."

"Oh, I am hungry, sir, but it's nothing that they have on the menu." She smiled through her mask. I could tell the makeup and the new girlie clothes had really affected her. "Can we go back to my place?"

"Are you kidding?" I told her, smiling, trying to think of a quip about birthday clothes to birthday suit, but I just wasn't quick enough.

"I can't wait to show you my birthday suit" as she beat me to it.

As we drove to her home, her high continued. She told me all about her time in the dressing room with Jennifer, how she relished her new bustier and new dress and shoes, and how the makeup artist applied the makeup, first making her comfortable and more like a "real woman."

"Did you know that the makeup artist is trans, and that Jennifer's boyfriend is a cross-dresser like me?" Lynn asked me.

"Wow Lynn, it sounds like your world opened up a bit today" I replied. "Actually, it sounds more like the real you, if you really want to know."

"I guess it does, doesn't it?" she mused. She pulled down the sun visor of the car and looked at herself in the mirror, shifting her head left and right.

We pulled into her development, and up into her driveway. I think then that some reality came back to her a bit as she looked around for any neighbors. She was of course, still made up as the beautiful woman she was, and still in the pretty silver dress with heels.

"Well sir, can I ask you in for a bit?' She looked at me with longing eyes.

"Lynn, you know I want nothing more" as if I had to tell her.

We went into the house and walked over to the living room, where she lit the gas fireplace. "Well, it may not be as romantic as you building a wood fire, but it is just as warm and soooo much more convenient," she said as we sat down on the couch. "Thank you so much for all of this. You really didn't have to."

"Oh I know, and it's not like I could send you flowers here on your birthday, could I?" I said as I put my arm around her and pulled her in for a kiss.

It was a deep, heart-felt kiss. I held her face in my hands as I eased my tongue into her mouth, probing it, feeling for hers. She responded, matching my tongue's movements with her own.

She broke the kiss, asking me "Would you like to see more of my birthday present?" She stood up, stepped out of her shoes, and unwrapped the dress from around her waist and stepped out of it, showing me the bustier. "See the zippers here?" she said, pointing to the cups. She sat back down on the sofa. "There's nothing under them" she whispered.

How could I refuse such an open invitation? We continued our kissing as I zipped open one, then the other cup and opened up the cups, exposing her breasts and nipples on each. I reached inside of both and started to rub the nipples back and forth, causing them to harden. I pulled aside the panties over bulge there and looked down at her clit inside its chastity. It was clearly responding to the stimulation of her nipples, swelling against the hard, clear plastic. I lowered onto my knees and licked her sac, further adding to the clit's discomfort. "Ohhhh" she muttered. I probed the slit in the end of the device with my tongue and just could lick the clit's piss slit through it.

"Oh, no you don't!" she said as she stood up, pulling herself away from my face. "I'm the woman here, it's my house, and I want to service my man!" She rearranged her chastity-encased womanhood back into her panties.

I stood up and we locked in an embrace, probing each other's mouths with our tongues. She was such a good kisser, even her tongue was passive towards mine. Without breaking our kiss, she undid my shirt buttons and took off my shirt, allowing her access to my own sensitive nipples. She started tweaking them in the same manner I had done hers earlier, taking them between her thumb and forefinger, rubbing the areolae in between light pinches. This went straight to my cock, which by now had hardened significantly. I knew she could feel it rubbing up against her hips. The way it was sitting in my underwear was preventing it from erecting upward as it wanted to do.

"Uh-oh," she said looking into my eyes, "Someone down there is uncomfortable."

Lynn knelt before me and undid my belt and pants button. She unzipped them and slipped them down as I stepped out of them. Then she reached into the brief's elastic waist band and pulled them down and over the cock, which immediately recognized its freedom and sprung up hard. She looked at it admiringly and gave it a kiss, then looking up at me said, "I want to service my man," then sucked it into her mouth, never breaking eye contact with me.

It was a beautiful sight, a gurl in a sexy bustier sucking her man's cock into her mouth, the intimacy of it generating feelings between us that we shared only between ourselves and no other. Yet it was not the wet warmth of her mouth that I wanted but the back of her throat, so I pushed it further inside. She swallowed around it as she progressed in her first lesson in throating. We had talked about this and even had watched a video together of another cross-dresser throating her man, so I knew this was what she was thinking. She pulled it out of her mouth, the thick saliva found only at the back of a throat streaking in thick milky translucent ribbons between my cock and her mouth and chin. "I'm doing pretty good so far?"

"Oh baby, you know you are," I leaned over and whispered in her ear, and we looked at each other and smiled as she said "god, I love your cock," as she started to lick my scrotum, then sucked one testicle into her mouth, then the other, then licked her way up my shaft. She held my balls in one hand as she held the base of my cock with the other and went down hard on it.

She made love to my cock, looking up at me with her tender eyes beginning to moisten from the mild gagging she was experiencing. I had told her I didn't want to gag her, but some mild reflexive gags were to be expected and really didn't seem to bother her. When they occurred, she simple backed off a bit and licked at the meaty head. I believe she really did love my cock.