Polyamory Ch. 01: First Date

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."

We stopped at a sandwich shop on the way and ate the sandwiches in silence. Debra finally spoke, "Hank you look really nice. I love your sports jacket and shirt."

"Thanks, Debra. It's pretty easy for us guys. We don't have all the choices women have."

"There are lots?"

"You see the girls and other women on campus. They wear a large variety of clothes. Then what is underneath is an unending cornucopia of choices."

"If that is true, I like the choices you made and so did Gladys. She's a little strange isn't she."

"A little", I agreed.

"What is it about her? I like her but she isn't like all women."

"I don't know about all women except she is basically the same physically. I may not should say anything but if you don't broadcast it, it's probably OK."

"Say what?"

"Debra, she is a lesbian."

"A lesbian? You mean she has sex with other women?"

"Yes!"

"I probably committed a sin then without knowing it."

"How's that?"

"We are not to consort with homosexuals."

"Well, you work with a few. You'd perhaps never know, but there are several on campus both men and women. Gladys is a good person. She'll do anything for anyone just as she did for you."

"She seemed as excited as I was, uhh, am."

"I'm glad you are because I certainly am. You are simply beautiful. I think I could sit and stare at you all day and night."

"I wish you could and vice versa."

It was time to head to the theater for the 2 PM showing so I fitted a helmet on her head and helped her on with an armored jacket and said, "I'm sorry that I did not think of the motorcycle when I was preparing. I should have gotten you something for your legs."

"Oh, I'm warm enough."

"That's not the issue. It's if we have a wreck."

"Well, silly, don't have a wreck."

We drove to the theater just in time. When we entered the lobby, Debra looked dazzled. She turned in circles, as I handed the tickets to the ticket taker, and took in all the posters. "Hank, what are all these", she said waving her hand around the lobby.

"They are advertisements for upcoming movies."

"There are this many?"

"Yes, and more. They have 16 rooms here showing a different movie today."

"Wow! Which one are we going to?"

"I thought we'd go to the Angels and Demons. Just remember it is only fiction. There is no historical truth except for the descriptions of some art and architecture, and while there is a lot about religion, little of it has anything to do with what has or is happening. So let your imagination loose and enjoy the story. It's just a story."

"OK. I'll try."

I put my hand on the small of her back as we walked down the corridor. She asked, "Is that a common thing to do when out with a woman?"

"Yes, in fact, by now, having had lunch twice, having bought you both a dress and intimate apparel, having ridden a motorcycle together, and now attending a movie, we'd most likely be holding hands. I might even wrap my arm around you and place my hand on your waist."

She replied, "Well then."

I moved to wrap my arm around her. She lay her hand on it and sort of hugged herself.

"Mmmm, that actually feels good," she said.

"It does to me, too."

We entered the theater room and found a seat a couple of rows from the top and in the center. Hardly anyone else was there at this hour even though it was close to time.

As soon as we sat down, she put her arm under mine and held my hand sort of hugging my arm to her breast. I liked that and hoped it was an indication of things to come.

"Hank," she whispered, "Thanks for asking me out and for the clothes and for bringing me here. If Mommy and Daddy ever find out, I'll probably be dead but I'll be a happier dead. Anyway, I don't know what I am supposed to do, so if you expect something, please ask. Maybe I'll be all right with it."

Not giving it much of a thought, I leaned over and kissed the top of her head. She sort of shivered. "You OK," I asked.

"Never better. It feels so nice to be with you and I have never been kissed by anyone."

"Not even your parents?"

"No. They'd consider it too intimate for a parent to do to a child."

"OK, what I'd like to do is raise the arm between us and put my arm around you and have you sort of lie on my chest."

She took my arm, raised the arm of the chair and put my arm around her draping it down between her breasts. She also sort of nuzzled into me. I got hard as a rock it had been so long since I had had such intimate contact with a woman.

We sat there in reverie over the contact and only held each other. She began to caress my arm with her hand which felt nice. The movie trailers began which she watched with interest. One came up with a scene that was a bit erotic. It showed the male actor with his stomach bare and the female skimpily dressed embracing and kissing.

The next thing I knew, Debra was shaking and sighing. "You OK?" I inquired.

Seconds later but not right away, she replied, "I don't know. I don't know what happened to me. I think it's only happened a couple of times in my life. I'll tell you later what happened. Let's watch."

"OK." We fell silent for most of the rest of the trailers and then for the movie. I could feel, even hear her breathing. Once in a while I'd kissed her head and caress her arm with my free hand.

At one point, she asked, "Is it all right if I kiss your hand?"

"Sure!" I said.

She kissed it and shivered. She did it several more times during the movie.

When the movie ended, I regretted we would have to get up and leave I enjoyed having her in my arms so much. People were filing out and I moved to get up. She said, "Can we stay a few more minutes? I like it here with you."

Once everyone was out, she turned to me and asked, "Can we kiss like that couple did in the preview?"

I was surprised and said, "If you like. Please don't feel you have to. Do you really want to?"

"Is it a bad thing to do at this point?"

"Most anything is all right if you feel OK with it."

"OK, then, kiss me please."

I leaned in and began by kissing her lips lightly, then I kissed her cheeks and forehead and then went back to her lips. Once I started kissing her lightly, I pressed her lips with my tongue. She acted like she didn't want that. I backed off.

I said, "You don't have to but when couples kiss like the one on the movie, they usually put their tongues in each other's mouth and sort of explore with them."

"Hmmm, really," she smiled and kissed me pressing my lips for entry which I gladly permitted. We did tongue wrestling for a bit until the staff came in to clean for the next showing. We got up and walked out arm in arm with me thinking that things were going far better than I had expected.

I suggested we take a ride out 207 from the theater, so she could experience country driving on the motorcycle. Once on the motorcycle, she wrapped her arms around me and laid her head on my shoulder which is not easy with a helmet on. We couldn't ride long, but I thought by going west and then southeast on 206, we could go to South Beach Grill, a favorite restaurant at the intersection of 206 and A1A. When we had finished about half the loop I felt Debra tense and hug me tighter. Then she began shaking pretty hard and exclaiming things I could not hear because we were both wearing helmets without an intercom. I hoped I'd get an explanation.

We arrived there about 4:30 which was too late for Debra to get home at 5:30, so I suggested she call and alert her parents. When she returned, I asked what excuse she gave. "I said I had to finish a project before the weekend for a prospective student weekend. They seemed ok with it but I felt horrible lying."

I squeezed her hand and said, "I'm sure. Maybe it is just a little lie, you could brief me on plans."

"Actually, I am the prospective student who will be in training by you."

"What am I going to train you in?"

"I want you to train me in love and love making. I know nothing about either. Like you asked that I explain what happened earlier in the theater and on the bike. I began to feel tingling in my vagina and my breasts began to get firmer and hurt a bit, then there was like a release that made me shake and exclaim. Maybe its happened a time or two in my life but today it happened twice. Do you know what it is?"

"I can only guess", hoping she could not sense my pleasure in knowing this detail. "I think, Debra, you had what is called an orgasm. It is caused in men and women from sexual stimulation."

"Yes, but nothing was being done to me."

The waiter came and we ordered drinks. She a water and me a diet Pepsi. I also ordered calamari and asked him to return soon for our orders.

He left and I turned to Debra and asked what she'd like to eat. "I don't know. Other than on trips I've never eaten in a restaurant and then only a very few times."

"Well, this one is known for seafood. Do you like shrimp and, if so, what kind?"

"Yes, shrimp would be good. Mom fixes shrimp scampi and I like that."

"OK then lets order scampi and fried shrimp and we can share. That OK?"

"Yes, now tell me how I had a sexual thing without being sexual?"

"Well, it's hard to say what counts as sexual. For example, if I can mention something you may consider inappropriate, men have what is called an erection when they are sometimes only mildly stimulated."

"An erection? What is that?"

"Do you know anything about the male anatomy?"

"No and I've never seen any men or boys naked so I am really lost."

"OK, here goes but tell me if you want me to stop."

"OK."

"Men have a penis which looks like a tube with a helmet on it. It is usually soft unless the man is stimulated. When a man is stimulated, like I am now, it gets hard. That makes it possible for the man to insert it into the woman's vagina and have intercourse."

She looked amazed and overcome with joy at hearing this explanation. "so you say you are stimulated now?"

"I am."

"Can I feel it?"

"Well, it will have to be through my clothes. I can't take it out here."

"Will you guide me?" I do and she feels my cock. I all but cum in my pants. "Wow, so that's like that because of me?"

"Yes, Debra, when you were talking about having an orgasm, it got me turned on, which is another way of saying stimulated. It then hardened. It may stay that way through dinner."

"May I feel it again later?"

"I guess you can."

"Will you take it out for me?" she said and then clinched her teeth and began to tremble and let out a string of oohs and ahs. After several seconds, she said, "OH, my, did it happen again."

"I think so."

"So just by thinking about it, we are both turned on?"

"I guess." The calamari was delivered. "I am, at the least, and I think you can say you are."

"So how else can I have an orgasm?"

"Well, you can touch your breasts and your clitoris, insert your fingers in your vagina, which many call 'pussy'. All of that will eventually lead to an orgasm and from what I've seen you'll probably be multi-orgasmic."

"What is that?"

"Some women and all men cannot orgasm but once while making love. Once a man cums, has an orgasm, he is done for a while but a woman can have a number of orgasms in one love making session. Since you've had two already in the last few hours without having been touched, I'd say you'll be having a lot."

She looked sheepish and I looked as if to ask 'What?' and she said, "Actually, I had another before you picked me up. Gladys had just left the restroom and me when it came on. I had to lean on the vanity to hold myself up. This is so wild, but thanks Hank for teaching me. I want to learn more. By the way, these clothes are so wonderful and soft, they make me feel so good and in comparison to my other clothes I feel almost naked."