Chapter 3: Shopping For Lingerie

I took my bag and headed for the lingerie department. Most of my underwear was either too risqué or too conservative for what I had planned. I seldom wear a bra and when I do, it’s for one of two reasons - to tease a man or because I have to. If it’s for teasing, then it’s certainly something sexy and lacy, revealing and easy to take off. Then there are those times when society says a girl has to wear a bra - like when I was teaching at a Christian elementary school. Nobody was going to be seeing it, that was one thing that was for certain, so if I had to wear one, it may as well be comfortable - something most sexy lingerie is not.

Needless to say, neither style was going to work for the look that I was shooting for. I needed something that was just a little revealing without looking like it came from Victoria’s Secret so my home collection wouldn’t do. I needed to shop for just the right thing...

The lingerie department appeared to be as slow as the rest of the store with two ladies standing around looking totally bored. Both looked to be in their late thirties or forties, neatly dressed and attractive. As I approached the bra section, one of them came over and asked if I could use some help. I politely declined which she took graciously enough but then asked if I had been fitted recently. Well, the truth is that I’ve never had a formal “fitting”, just buying what I had before and then changing size as it seemed necessary. In any case, it wasn’t like I wore one that often anyway and so long as they didn’t hurt, what was the big deal?

“Oh it’s up to your dear,” she smiled, “it’s just that most women don’t get fitted properly and you might be amazed at how much better a proper bra can feel.”

First, why do all older women like to call me “dear”? No matter, she meant well I could tell. Now she had me curious. Exactly what was a “fitting” anyway? I shrugged and said OK.

“Well, we need to go in back ... don’t want all those bored husbands watching now, do we dear,” she said with a wink. Not that I could see any around, but I knew what she was talking about. Nothing more nosey in a store than a poor guy being force to follow his wife around like a whipped puppy as she spends forever looking for an outfit.

Once in back by the dressing room, she motioned for me to go in a dressing room saying, “With that heavy sweatshirt on, you really need to take it off so I would imagine you’ll want some privacy.”

It was all I could do to stifle a giggle. If only she knew what I did for a living! She seemed really sincere though, and I could tell she meant well. There was absolutely nothing in her demeanor to indicate it was anything but what she said. Now if it was a MALE salesmen...

Inside I slipped off my sweatshirt and I think I surprised her a little when she realized I had nothing underneath.

“Oh,” she let slip out a little as she glanced at my bare chest and then looked away.

“Sorry, I usually don’t wear one,” I said, trying to sound apologetic for surprising her with my bare chest.

“Oh don’t be silly dear, I just wish I could get away without one and look as good as you,” she replied wistfully, as if recalling days long past. From what I could tell under her dress, she didn’t look too bad herself and I imagined she probably still had a nice set of boobs herself. “Now let’s get you measured up...”

She had me stand straight with my arms out just enough to be able to wrap her measuring tape around my chest. She measured under my boobs to get my chest size and then around the fullness of my breasts to get the cup size. My nipples were still semi-erect from my recent masturbation and the feeling of the cloth tape against them stimulated them once again, making me jump slightly.

“Sorry, you must be really sensitive,” she apologized.

If she only knew WHY they were so sensitive! For just a moment I had a vision of her reaching out and cupping my boobs in her hands, telling me she needed to check their firmness. Of course that was unnecessary and she never did anything even remotely outward towards me, but I wondered how she would have reacted had I taken her hands and placed them on my bare boobs.

“Hmmmmmm, looks like we have a 36C here,” she concluded, “Was there any particular style or brand you were looking for?”

I hesitated, wondering what I should tell her. “Well, it’s for my boyfriend and he has this fantasy about an old teacher of his...”

I let my voice fade out, as if saying, “and you know what he wants to see.” She got the picture and I smiled as she swallowed a little bit harder than normal. Then she smiled at me, as if I had just told her the weather outside.

“Well, I think that’s sweet. He’s a lucky boy to have a girlfriend think so much about him ... Wait here for just a second - I have just the thing.”

She checked to be sure nobody was outside the door and then exited, shutting the door behind her, leaving me standing there topless. A few minutes later she was back, carrying a couple different bras in her hands.

“You know, I have to admit, I’ve always loved these,” she said softly in a conspiratorial tone, “I don’t think my husband would know what to do if I wore anything like this these days.”

The first was sheer black with rear snaps and deep plunging front. The top edges were all lacy and it looked quite sexy.

“Here, let me help you get it on,” she offered. She help it out by the shoulder straps and placed it over my boobs, letting me put my arms through the straps and then moving around to the back to do the latches.

“Now I bet you just wear them off the shelf like this, don’t you dear,” she asked rhetorically, continuing on as if she already knew the answer - which she did. “I don’t know why so many girls don’t take the time to get them properly fitted.”

As she was talking, she was adjusting the shoulder straps and tugging on the cups to seat my boobs properly. “Do you mind?” she asked politely, as she cupped my boob and held it up a little as she adjusted things some more. For whatever reason, feeling her hand under my boob, cupping it gently but firmly, was more erotic than I would ever have expected. All I could think was how I wanted her to just squeeze it a little - oh PLEASE massage it! Alas, she was being professional and once she was done, she released me as my pussy was feeling hotter and wetter by the moment. Had she ever been with a girl? Had she ever cupped a girl’s boobs in her hand and then reached down and sucked on her nipples? Had a girl ever touched hers? What would she say if I reached for hers and began to touch them?

“There ... how does that feel now?”