Chapter 1
"First Date"
I received an email from Debra late in the afternoon. "Hi Hank, Thanks for lunch. I cleared Friday with the Dean who seemed quite pleased that I was going out. He even said, 'Debra, I hope you may find a way to spread your wings. You're too sweet and smart to be bound up like you've been. I want to hear how it goes, and I don't think there's a better person than Hank for you to go out on your first date with.' Imagine that. I wear a size 4 dress. My underthings aren't what most girls wear these days. Daddy has to special order them. Can you buy me something?"
I replied, "Delighted to hear and yes, I can buy some underthings what I imagine you may look gorgeous in were I to be able to see you in just them. Is that all right?"
I didn't expect to hear back from her again this afternoon because it was past five. My mind went on overdrive. I had to do something or I might not get anything done so I went shopping.
I know the owner of a dress shop on the island, so I rode my motorcycle over and asked for help. I told Jasmine that my friend was from a very conservative background and I needed something in that order but not too much so.
I was so turned on by the idea that my cock was hard as a rock. Did I mention that it also was the whole time I was at lunch with Debra or that I had jacked off almost as soon as I got to my office. Jasmine noticed my erection and said, "She must be some kind of woman, Hank."
"I guess or my imagination just has me so juiced I can't think straight."
"So let me see." She went exploring as did I. I found a few dresses I liked, and she came back with three or four more. I looked through them and picked a shirt wasted dress that had a scooping neck line but nothing too radical and scalloped sleeves. It was striped navy blue and white. Jasmine thought it was beautiful and any girl would look good in it and, "It's not too short." I hadn't even thought of that.
"I'll take this one, then."
"OK, but does she have any jewelry?"
"I doubt it and I know she is not pierced for earrings."
"OK, let's see what we can do."
She went to the displays with necklaces, earrings and bracelets. After some time, she says, "OK, should you approve, I think these would look quite nice on a young lady for her first date."
The necklace was a very pretty beaded one with bits of gold chain between the beads. There was a matching bracelet, and Jasmine had found earrings that clipped on that had a simple bead dangle.
"She may not be able to wear the earrings long. Clip ons can become painful. You may want to suggest that she remove them in the movie. Anything else?"
"Yes, this is sort of an odd question at this time. She says she knew her underwear would not be appropriate for these clothes. Where can I go for that and what do you suggest?"
"Hank, panties are no problem. If she is size four, you can get her smalls. A bra is sized for her chest and cup. Any idea about her breasts."
"It's hard to say. Under her clothes it's hard to tell if she has any. If it weren't for a slight swell beneath her jacket, she may have none."
"OK, can you find out what her chest measures beneath her breasts?"
"I guess I can email her."
"OK, find that out. Go to Soma out at the outlet mall and then buy three bras for her chest size: one each of B,C, and D. It's not likely that she is a D, but you never know. They do not carry A cups because few women wear A. She can then pick the best fit."
"OK, thanks. What's the damage?"
"I'll tell you what, since this is a young woman's first date and her man is being so nice, I'll give you 25% off." She then rang in the numbers and said, "Make it $70.00."
"Thanks, Jasmine. You're the best."
I paid and went home and laid the things out. I had no idea how we would make changing the clothes possible, but I was turned on by just having bought the dress. Tomorrow, I was going to buy her lingerie. My cock twitched at the thought.
I emailed her and asked for her chest size not expecting and did not get an answer until the next morning. She wrote, "(: So you are on the case? I'm 34 chest, 26 waist and 34 hips. Is that enough? :) :)"
I wasn't sure how to take the more info than I had asked for or all the smiles. However, I was pleased to get more than the number. I thought she was flirting.
Friday couldn't come quick enough. I jacked off four of five times on Thursday thinking of what I thought may lie beneath Debra's clothes. Then I did so again twice on Friday morning in anticipation of our date. I had dropped her dress and lingerie off at her office and figured she may get some help with it. I had bought her not particularly conservative or sexy bras. They were white as a color would have shown through the white on the dress but they were also somewhat tiny cupped as were the straps. The panties, also white, were pretty and lacy boyshort with slight legs. I figured they'd be sexy as hell to see on.
I learned later that she got one of the female colleagues, Gladys, to go to the bathroom and help her with the unfamiliar clothing. Little did she know that the woman she chose is a lesbian and may have gotten as much of a 'charge' out of doing so as I may have. She helped her undress noticing that she was nervous about it. They put her regular clothes in the shopping bag I had brought the things in and Debra expressed delight and some consternation over how revealing the clothes were. She said she thought she would feel naked under her dress. In fact she did, but she also felt naked with the dress on.
Gladys did not tell her that the outline of bra and panty were revealed in a shadowy sort of way through the white stripes of the dress. The dress was made of very light nice material that clung to her quite nicely. Debra had never worn jewelry so putting it on, according to Gladys got her in quite a state to the point Gladys thought she may cum, but as far as she could tell, she didn't.
Gladys had her makeup with her so she put some eyeliner on, some rouge and some lipstick. When Debra looked in the mirror, she was astounded that she was now staring at a beautiful woman. "Wow!" was about all she said. Then she ran her hands over her body feeling the softness of her dress and the shape of herself as if she had never done so. "He'll be able to tell what I'm wearing underneath, won't he?"
"Not unless he gets a bit naughty. He'll probably be respectful though if I know Hank, so don't worry."
Debra took another look turning one way and then the other and said, "I've never seen my breasts showing so much except when I'm naked and I'm not supposed to look at myself then."
"You don't look at yourself in the mirror?"
"No, it is considered vain to do so."
"Oh, my God, really!" laughed Gladys. "I look at myself a lot. I like seeing my boobs, my stomach, my pussy. I've even used a mirror to look down there, if you know what I mean."
"You touch yourself there and look at it?"
"Oh, God, yes, Debra. It feels so good to play with my boobs and my pussy. You haven't done it."
"I only touch myself to bath. Touching for any other reason is simply sinful."
"I'd say—sinfully delightful."
Debra was sort of horrified or at least that's what Gladys thought.
I went at 12:15 to pick Debra up because she thought that would give her plenty of time to change. However, it was more like 12:40 when she appeared. I hardly recognized her. She was gorgeous, nearly radiant. The dress was not fancy, so that sort of diminished the affect, but her innocent beauty was evident and her shyness only added to her attractiveness.
I was nearly speechless and finally responded to her perplexed look with, "Oh, Debra, you look good enough to eat." I'm sometimes clueless socially and was fortunate she had no idea what the double entendre was. I stammered a bit and finally said, "Debra, you look stunningly gorgeous."
"I feel a bit naked but thank you."
"Well, you are not naked, you are properly clothed for most any situation in my world."
"I sure wish it were mine. Thanks for the clothes and the jewelry."
"We better get going, we are already a bit behind. Is a sandwich for lunch OK?"
"Sure, Hank."
