That Boy from Target

This is a different story from my Marc and Diana series, written in what i hope is a more light hearted vein. I try to inject sweetness and light into everything I write, and I think I have succeeded her. Hopefully you will agree, reader. I love feedback.

When I saw him across the store my eye was immediately drawn to the pink silk of the shirt he wore, as it glimmered a bit under the fluorescent light. I had only stopped by Target for a few grocery items but, as I do, I took a moment to wander through the women's clothing aisles to see if anything caught my eye. I tend to be a bit shy when I'm shopping, and I love the self checkouts at that store. So much better than the questioning eyes of a young clerk, although I've grown somewhat used to that. I have always loved the look and feel of the different fabrics on the racks, and I fingered a few, feeling the textures, keeping an eye on the current styles that were displayed. They didn't really do it for me, but again, I was at Target. The clearance rack was always worth a check, and it was as I stood there that he caught my eye.

His hair was cut in a feminine bob that just brushed the neckline, and below the pink open collared blouse, styled like a man's dress shirt, was a slim grey skirt, just a bit too long to call a mini. It came to just above his knees, below which I could see that he was wearing brown pantyhose. On his feet were a pair of black patent leather pumps with a small heel. Resting his weight on one leg he stood looking at a display of winter sweaters, and then, glancing my way so that our eyes met for a moment, he drifted out of my sight in the direction of activewear.

I was in boy mode, as I usually am, but under my khakis and hoodie I had on a pair of high cut black satin panties and a cute matching bra. I could feel my cock stiffen a bit against the softness of my panties as I decided that another look at him wouldn't do any harm. And I could use another pair of leggings anyway, so I started towards activewear myself. As I passed the sweaters I paused and reached out to touch them, tilting my head a bit as if contemplating purchasing one.

"They feel lovely don't they," a voice sounded behind me. Turning with a bit of a start I saw the boy, and met his eyes.

"They do..." I said, "but I'm not really a fan of the patterns that seem to be in vogue this year."

"Oh I don't know, I kind of like them." He reached out to the one before us, a black and white patterned cowl neck with a flared out waistline and 3/4 sleeves. "It's the styling I'm not sure I like. I like more a more form fitting sweater myself...." As he stood there I took him in. Beneath his full but shapely brows a blue shadow highlighted his eyes, and his fullish lips were a pale pink that reflected the shade of his shirt. The top buttons of his shirt were undone so it was open at the collar and it's looseness as it fell to where it was tucked into his skirt was broken by the curve over his small breasts. He saw me take him in, and a hint of a smile played along his lips. He was confident. I liked that.

"You're thinking I'm contradicting myself, " he grinned. "Except for this blouse, of course," he said touching it, "I make an exception now and then, especially for the slippery stuff." Again he gave a soft smile, and looked up at me as he lowered his eyelids a bit. He was totally flirting, confident in his attractiveness.

He was somewhere in his 20's, so I was a good 20 years older. He was slim, in good shape but not skinny. The curves of his body suited his feminine attire and I again admired the courage of the young and their openness. It was a different time when I realized I was a crossdresser, and I still struggle with the shame it can bring on.

My cock grew a bit more at his boldness, and I too began to feel a bit flirty.

"Like those, maybe," I said, nodding at something behind him. Target's intimates selections are a bit limited, but they did have a small display of loose fitting silky nighties, and it was in view a few aisles over.

He turned. "Oh yes, those can be fun at times, and definitely comfortable to sleep in." We wandered towards them, a display of bra and panty sets coming into view.

"These are my preferred sleepwear," I said, pointing to high cut set with a lacy brassiere.

"Really?" Turning to look at me his tongue emerged to run its tip along his upper lip for a moment. His eyes lit up a bit.

"Or for running over to Target." I smiled, openly flirting now, my cock pushing at my pants. I hadn't bothered to tuck it, since I was just running to the store, and it had made its way out of the panties. Women's underwear sure feels good, but it is, after all, made for women.

"I see..." he glanced down. I'm not particularly large, but there was a definite bulge showing below the bottom of my hoodie. His eyes came back to mine and held them for a long moment.

"Sarah" he held out his hand.

"It's nice to meet you Sarah," I said. "You can call me Samantha." Our hands met, and I gave his a squeeze. "And I love your outfit today."

"Well thank you, that's awfully nice of you to say." His eyes flashed at mine. God he was cute. "Yes, it's very nice meeting you. Maybe I could buy you a cup of coffee over there and we can continue this conversation sitting down. We don't want to attract attention do we?" His eyelid flickered and he again looked down at my crotch. Again the small, confident smile.

"That sounds really nice." I said. As he turned to walk in front of me I followed, checking out his butt as it moved the skirt, his calves shapely beneath his hose. The shoes flashed reflections of the light and clicked softly on the floor.

He went over to the in-store Starbucks while I paid for the items I had in my basket, and when I joined him he had sat down at one of the small tables. In front of him were two cups of coffee. I put my bag down on the floor.

"I went ahead and got you the brewed coffee" he said. "There's no point in giving Starbucks money for a badly made cappuccino." We laughed. At least we shared one opinion.

"Do you take anything in your coffee?" I asked as I reached down for my cup.

"I like a little cream." He smiled mischievously. I cocked my head and smiled. This boy...

"I think I can take care of that." I said with a grin. He shifted slightly in his chair. I raised my eyebrows. "Maybe you're also glad we are sitting down?" I asked, my eyes holding his for a moment.

He flushed a bit, color rising into his cheeks. "Um...yes, yes I am, Samantha." Now I laughed out loud as I turned to walk to the bar, where I poured half and half into each cup, and returned.

I placed the coffee in front of him and sat. "I really do love your blouse", I said, reaching out to feel the end of his sleeve where his arm lay on the table. "I bet it's a dream to wear."

"Oh it is. Like I said I've definitely got a thing for silk. It's so soft and slippery on me. I...we share some interests, I guess. I love all the fun clothes I can wear. Boy's wear is so...boring." I now I flushed as he took in the hoodie and khakis. "Do you ever dress up? Or is the lingerie under the clothes more your thing?" I couldn't help but admire the way he got straight to the point.

"I do, sometimes." I said simply. "Honestly, I just enjoy the simpler, kind of stay at home stuff- leggings, an oversize top, maybe a skirt now and then. But I've been told I clean up nice. I'm a bit of a homebody really, but I've been known to go out. I always admire those of us-like you- who can face the world day to day. Of course, you have the face and body...I'm not sure I want to be seen as an old man in a dress."

"Oh I bet you could be pretty cute too- but thank you." He looked at me, his head tilted. "Yeah I just do what feels right, and sometimes I need to be all girl and head to the mall. Today is one of those days. I was only starting here- I mean it's Target after all. I'm planning on hitting Macy's in a bit, and H&M, and maybe Victoria's Secret or the shoe store later -unless something else comes up."

Again he gave the mischievous smile as he raised his cup to his lips. As it drew away he left a smudge of lip color on it.

"I could probably provide that distraction." I said seriously. "I don't mind telling you I think you're smoking hot." I love to flirt as much as the next girl, but I also believe in just laying it out, and anyway he had seen the bulge in my pants. If this boy could be bold so could I.

"I can tell, honey. And if you were just another middle age dude hitting on a hot boy in a skirt we wouldn't be having coffee. But I'm intrigued." He trailed off and resumed "...I kind of need to see just what your bra looks like." He laughed.

I smiled and leaned across the table slightly, lowering my voice as I said. "It's a black satin underwire, with a little strip of lace along the top of the cups and a cute tiny bow in the middle. Victoria's Secret - I forget the model. And I'd love to show it to you." I was close to his face now. He shifted again in his chair. I toyed again with his sleeve, and drew my fingers across the back of his hand.

"Shit" he muttered, shifting again. I could tell he was trying to arrange his cock in the tight hose.

"Problems?", I said, arching my brow and smiling. "At least my khakis are baggy enough..."

He flushed again, the color rising into his cheeks, and laughed. He took a sip of coffee.

"Why don't we just drink our coffee and chat about the weather?"

Again he winked, and settled back, crossing his legs. I did the same, and felt my own cock moving around in its satin and lace. And khaki, damn the boy.

Instead we talked music. I admit it, I'm old, but I do listen to some of what the younger folks listen to, and he had an appreciation for the 80's British New Wave that had formed the soundtrack of those ugly teenage years that I had had.

It had been, I guess, a small consolation to see those stars try to normalize eyeshadow on men, and begin what I see as the gender bending that allowed this beautiful boy to be comfortable openly walking around in a skirt and heels. That had started earlier of course (Bowie, of course, and Freddie, among others), but for certain boys of my generation there was a great power in seeing Ian McCulloch, Robert Smith, and all the rest be comfortable both in dark eye liner and a football shirt. Sarah appreciated my thoughts on that and other more musical ideas, and added his own, and the cups were soon empty.

"So," I said " are you going to continue with your shopping or..." I trailed off. It was Friday afternoon, I had no real plans for the weekend, and it had been awhile since I had played dress up with someone. And again, I believe in being direct.

"Well now," he said, and he traced his nails down the back of my hand. "There are a few things I'd like to look at, yes, but I could be hungry in a few hours if you're offering dinner." We stood up.

"That sounds fun." I admitted, mentioning a local place that served beers on tap and offered a selection of menu items. "I'll see you around 7:00?"

He held out his hand and I shook it, our palms lingering just long enough for a flush to rise into his cheeks again, and probably mine as well. I watched his ass briefly as he walked away, and then grabbed the stuff I had bought and headed for the car. The few hours I had would give me time to get ready, but just barely. Driving, I considered my closet.

Once home I hopped in the shower right away. I keep my legs shaved, so I didn't have that to deal with this time, though I did touch up around the strip of hair that runs from below my belly button to the base of my cock, making sure I was nice and smooth on either side. That sort of grooming always turns me on a bit, so as I toweled off and started to apply moisturizer I was about half hard, and I took a moment to touch myself as I thought about Sarah and what was under that slim skirt of his. And then I was rock hard. A bit annoying, actually, though of course it felt good. I had decided on my outfit in the shower, and the erection wasn't going to do me any favors. I had to do my nails first though.

I thought a deep red would go. I keep my nails short, but they do have a bit of shape, not so much you'd notice when I'm a boy, but enough so that once they're painted they look nicely feminine. And I take good care of my feet, having been blessed by genetics with reasonably small ones. I did my toes to match my fingernails. That got my heart racing again.

However, the practicalities of painting my nails had distracted me enough to soften my cock, and I was careful to avoid any arousing thoughts as I waited for them to dry. Although I did admire my feet once or twice, down there at the end of my decently toned legs. I've managed, blessed by genetics and regular exercise, to keep my body reasonably in shape.

Once they were dry I opened up the underwear drawer and picked out a pair bikini cut panties, in white. I grabbed a white bra, this one an underwire with sheer nylon cups. It felt great as I pulled it around my torso and clipped the back, and then turned it and shrugged my arms into the shoulder straps. Into it went some breastforms. I could see their pinkish nipples through the sheer panels, and as I stepped into the panties I had to tell myself to keep it together. The ritual act of transformation has always been a huge rush for me, and it's always there, whether if I'm just slipping into a pair of leggings, or going all out in lingerie and a sexy cocktail dress. Tonight the real fun would come later.

I needed to be soft for what was next though, or at least semi soft, as I pulled on a pair of form fitting jeans. The fabric was stretchy and tight over my legs. The jeans were fashionably torn here and there, and showed off the soft skin of my thighs. As I pulled them up over my bottom to button them, I pushed my softish cock down and back a little so that it lay against my leg. It worked, and anyway the long waisted tunic style top I was planning on would hide anything that might happen.

The top was a black smooth heavy cotton weave with an open neck. Loose fitting, it draped off my boobs nicely and ended just below the curve of my ass. It rode on my right shoulder and exposed my left, with its pretty white strap. I keep my hair longish, and as I brushed it out it quickly changed from old dude in his 40's pony tail to a cute style that framed my face. It's a trick my hairstylist was able to incorporate into it (he knows my secret) and believe me I pay him well to do it.

I wasn't going full stealth-mode tonight. Sarah already knew who I was, and actually the idea of not being in complete disguise while in the company of such a beautiful boy was intriguing, and a bit exciting. So I applied some color from the contour kit, and some simple dusky eyeshadow. My lips I did to match the dark red of my nails. A few silver bracelets went onto my right wrist where they jangled together nicely. Around my neck went a silver chain with a small polished green stone. It fell to my breasts, where it helped to emphasize the cleavage between them. It was a reasonably warm night, which is why I had opted to do my toes, and I showed them off in some black strappy sandals with a flat heel. I'm all for comfort. And heels didn't really go with this look, I felt. Casual milfy was what i was going for tonight.

A last check in the mirror and I threw a few essentials into a small black purse that I hung over the shoulder. Believe me when I say I was feeling good.

When I got to the restaurant I saw her at once. She had nabbed a booth towards the front and was looking as delicious as I remembered. She was scanning the room, and I liked how her eyes lit up when she spotted me, and then narrowed to assess my outfit. She shuffled out of the booth to stand as I approached, and gave me a peck on the cheek to say hello.

"Well don't you clean up nicely." I heard. "I like the outfit- dressy casual. I've been considering some jeans, tried some on today. Nothing grabbed me though. I'm really a skirt kind of girl. And I love the off the shoulder look." She reached up to rest her fingers briefly on the exposed strap of my bra, ran them lightly over my skin. "That's not what you described." She met my eyes and smiled. It was all I could do to keep from grabbing her right there.

"Thanks. I can't sit down yet so...let's keep it light please." She grinned. "Have you been here long?"

"Long enough to have half a beer. But I got here early." She shrugged. "I haven't ordered food."

I've been calling this a restaurant but it's not, really. It's a small local space done up in the latest in interior design. Lots of horizontal wood here and there, polished concrete floors, exposed ductwork up above. You know the kind of thing. They served a selection of locally brewed beers, and a variety of "small plates" as they're called. But I liked it- and the food was good. You ordered at the counter and they brought it out to you. Later in the evening the hipsters were sure to descend, but for now the place was quiet.

"Well I'm going to get a glass. Are you hungry? Did the shopping wear you out?" I asked. There were a few paper shopping bags on the seat she had risen from.

We walked up to the bar and ordered. Like I said the place was quiet, and the girl behind the bar was friendly and suggested I try a hazy IPA that she said was good. She took our order for a plate of empanadas, as well as some tacos. Sarah asked for another glass of what she been drinking, and we returned to the table. Small talk ensued of various sorts- we were getting to know each other better.

I steered the conversation to him: what did he do? How could he be so comfortable navigating the world as he was? It fascinates me, how comfortable and confident the younger generation can be in their fluidity. I'm jealous, I admit, and I told him so. I was 20 years too late to be able to be a beautiful boy in a dress. And pass while I did it.

He answered with an easy grace, telling of his first realizations, the acceptance of his friends when he announced it (well, most of them anyway) and his gradual transition from a boy who occasionally wore eyeliner to a young man who often went out, and passed, as a young woman.

"But you knew-" he said, his head tilted again. That look was growing on me. "How?"

"Ah- chalk it up to the experienced eye of age, I guess," I said "but it was also the way you were dressed-there aren't that many young women wearing hose anymore, at least to go shopping."

"Very true." He said. And I could tell he was running his fingers along his leg to feel the silky texture of his hose as he spoke. "But I love the way they feel on me. I couldn't resist today. And I felt the rest of the outfit had to match. I could have gone shopping in leggings and a sweatshirt I guess. Would you have looked twice at me then?"

"Well, at least at your butt." I joked- "but I don't know if I'd have clocked you, honey. You're definitely a natural." Reaching across the table I took his hand in one of mine and turned it up. Putting out the index finger of my other I traced small circles on his palm. We held each others eyes for a long moment.

"I'm not always a girl, you know," he said. "But I do so enjoy it. I still use the male pronoun though-I like being boy too."

"Your food, ladies" I looked up to the waiter, a husky Hispanic guy who spoke with that lilt to his voice that told you everything you needed to know about who he slept with. "Enjoy!" He turned to go with a twitch of his hips, and Sarah and I both watched his butt appreciatively as he walked back to the kitchen.

Soon dinner was over, the beers had been finished. The place was starting to fill up and get louder. Conversation became harder. I suggested we pay our tabs and take a walk, and Sarah agreed.