Dinner Date (Fm, Kinky, Taboo, Seduction and Surprise)

[phtlc]

Dinner Date

The game was tight, but we beat them. While I was not the top player on the team (although I was an OK player), this was definitely my best game. Looking out at the stands she was there. Her name was Helen, or Ms. Caldwell as she called herself. She was so hot, I always checked her out. She was in her 30’s and had a fucking amazing body. She looked so sexy in her business suit, and I couldn’t help but wonder what she was doing at the game. She smiled at me when people cheered my performance, and it made me rubbery legged. She was always so sweet to me, but I know she just thinks of me as a boy and nothing more. I on the other hand, had harboured a massive crush on her since I was in training wheels. Now as a teen, I felt like I should come across as more mature, however the fact remained, that while I was working out and it was starting to show, I still had a teens body, not a man’s body. I didn’t shave yet, and had no hair on my chest.

As I made my way off the field, I started putting my equipment in my bag, I said goodbye to my team mates and coach and started heading home.

‘Hey Rick, Great game!”

Her voice....my legs went rubbery

“oh hi...uh...uhm yeah I think....” fuck I sounded like an awkward shy boy, “Uhm yeah, thank you Ms. Caldwell....I am glad you liked it”. Fuck I sounded like a kid!

Smiling at me, as though trying to be understanding about my awkwardness she walked up to me.

“Heading home? I’ll walk with you”, she said as her hips wiggled hotly while she walked in her heels.

“OK, sure!” I cringed at how excited I sounded when I said that.

She walked home with me, talking away with me as we went. I was so excited at the opportunity to walk with her that I could feel my heart speed up.

“Play any other sports at your school?” She asked with genuine interest

“Uhm....well not right now, this is the only sport this season. I am planning on joining the wrestling team though” This was a lie. I had no interest, but I figured it would sound macho. She smiled her approval.

She made small talk for the duration of our walk, and I did my best to engage in conversation with her, while trying to sound mature. As we walked, I did everything I could to try to stick my chest out, without making it look like I was sticking my chest out. I was in very good shape, but I still had a teen body, rather than a man’s body, which made me feel shy around her. Helen on the other hand definitely had a woman’s body. She had curvaceous hips, a small waist and perfectly sized breasts for her body size. The way her body moved as she walked, combined with the click of her heels was soooooo fucking hot it was driving me insane. I sincerely hoped she couldn’t tell what I was thinking of her. As a grown adult, if she had any idea of the sexual thoughts going through my mind, she would have been highly offended and unimpressed with me.

The whole time we talked, she seemed genuinely interested in what I had to say, which was flattering to me. Don’t get me wrong, I was no geek, but I was definitely shy around girls, and was still a virgin. Most of my friends were too, but we all lied and made up stories of having scored despite the fact that we had only scored with our hands. We were still young, so time would change that.

Eventually she got around to asking if I had a girlfriend. I didn’t have anyone serious. I had fooled around with one girl, and managed to feel her breasts through her bra, but that was about it. I had kissed a couple of girls, but only managed to fondle the one. Most of my friends had gone a bit further than that. My problem was not my looks, but the fact that I was shy.

“Uh...uhm well nothing that’s....serious you know” I said awkwardly

“No need to rush into anything serious, you’re still young” she said reassuringly. I couldn’t tell if she was giving advice or just patronizing me out of sympathy. As if reading my thoughts, she spoke again.

“You’ll do fine when the time comes...you’re a very good looking guy. There are plenty of girls who would like to be with you”, she said with a genuine smile and sincerity. This made my heart speed up with excitement. Ms. Caldwell had called me good looking!!!!

“Uh..thank you” I said, trying not to sound too excited or boyish. I’m not sure how good of a job I did.

As we approached her house, more than a block before mine, I prepared to say goodbye to her when she spoke

“Rick, are you in a hurry? I have some things I need brought down to my basement, and I could use a strong guy to do some lifting. I would really appreciate your help” She asked.

‘Sure!” I said, and immediately cringed at how enthusiastic I sounded. That must have sounded like a dead giveaway. “I mean...I don’t mind helping”, feeling even more flustered at my pathetic attempt at recovering.

‘Oh excellent, thank you!” She said with a smile, “I’ll make it worth your while” she said.

I certainly knew how I would like her to make it worth my while, but that was obviously not what she meant by that.

I followed her up to her door, checking her out from behind as her heels clicked on the walkway. My mind was abound with fantasies of her jumping me when we got inside, but that stuff was the product of Penthouse forum stories, and not reality. She was fucking hot, and dated men, not boys, but still the fantasy was there.

“OK, those boxes over there need to go in the basement, and those three in the separate pile need to go upstairs.” She said, “Thanks again for doing this Rick”

“No problem Ms. Caldwell”

“Call me Helen”, she said sweetly. Holy shit!

“OK... Helen”, fuck, I could feel I was blushing.


Walking over to the first box, I grabbed onto it and realized it was quite heavy. I was determined however to look as manly as possible, so I lifted while trying to maintain a facial expression that showed total relaxation. She smiled approvingly as I lifted. I did everything in my power to flex my muscles, without making it obvious I was doing so.

Heading downstairs, I carried the first box, following her as she showed me where it was going. It was quite heavy, so I was relieved when we finally got there, but again I made a point of acting like it was easy to carry.

“Looks like you are managing just fine” she said with a smile.

I spent the next little while, lifting boxes, carrying them downstairs, always trying to puff out my chest, and flex my biceps. It felt incredible to be doing manly work in front of Helen, as she watched. I tried to imagine that she was getting turned on by this, but again this was just fantasy.

When I finished with the boxes going downstairs, I approached her to find out where the other boxes were going.

“Grab the box with the yellow tape on it and come with me”, she said walking toward the stairs. I followed, and as we ascended the stairs, I couldn’t help but stair at the bottom of her skirt, as from this angle I could get a better view. I still couldn’t see her panties or anything but the look of her lower thighs from behind was a sight for a young guy like me.

“You managing that OK?” she asked, as I looked up rapidly to see her looking back at me. I hoped to fuck she didn’t see me checking her out. ‘Please...tell me she didn’t bust me!’ I thought.

She smiled sweetly, and guided me to her den and showed me where the box went. I went to get the other box, as she waited for me. As I walked towards the den, she stepped out and instructed me to follow her as she guided me into....her bedroom! Holy shit! I’m in Helen Caldwell’s bedroom! I thought. Many fantasies had placed me in this room.

“OK, just put it over there young man” she said with a cheerful tone as I caught her smiling at me, mostly sweetly, but partly with a faint sense of amusement. I couldn’t help but wonder if my expression had tipped her off as to what I was thinking. I was blushing again.

Heading downstairs, I grabbed the other box and carried it upstairs to the hot looking goddess’s bedroom. I didn’t hurry too much when I got there. I was not likely to ever be in her bedroom again, so I figured I might as well make it last. Putting down the box, I made sure to posture myself well, but again not to be too obvious.

Standing, I looked at her. ‘So...uhm....is that..uh..it?”, I shifted awkwardly.

“Yup, that’s all. Good thing I ran into you. I never could have lifted those boxes” she said. Reaching out she put her hand on my bicep.

“For strong guy like you, I’m sure it was no problem” she said. My knees just about buckled!

‘Uhm...ahem uh yeah, it was no problem” I said, trying to seem manly. Fuck I felt awkward. I hoped she wasn’t patronizing me. I worked out, and had biceps, but it was still boyish muscle and not the beefy hard manly muscle.

“Come on downstairs. Let me make you something to eat” she said, heading out of the room.

“OK” I said, wishing we could stay in the room.

Heading downstairs, I went to her kitchen and sat down as she prepared some food. I still couldn’t believe I was here, and now going to eat with her.

“Do you want something to drink? After hard work a man could probably use a cold beer”

Holy fuck!!! She just called me a man!...and offered me a beer!!!!

“Sure please!” I said, trying to control myself.

She reached into the fridge and pulled out a cold bottle, twisting the top off and handing it to me. I raised the bottle to my mouth and took a swig, trying to look natural. I really wasn’t a very experienced drinker. There was no way I would be able to go to a beer store without getting carded. My friend’s older brother had fake ID and could get beer, but he rarely ever got any for us.

She started preparing a tray with various cheeses, spreads and meats, with some crackers and other assorted items.

“Let’s go down to the recreation room in the basement”, she said wistfully. Following her, I walked into the darkened interior of the basement, which had a combination of rustic and postmodern design. The floor was stonework, with a marble top coffee table. It all looked very expensive, and she must have paid quite a fair amount of money to get this. The couch was nice leather and there was an exotic looking recliner.

‘Sit there” she said, gesturing to the couch.

I sat quickly, almost obediently. She placed the platter down in front of me. It looked amazing.

“Go ahead, eat” she said encouragingly. I leaned forward and grabbed a cracker and cut some cheese, placing it on the cracker. Let me tell you, this was the most amazing cheese I had ever tasted. I started sampling the wares, overwhelmed by the kaleidoscope of flavours I was experiencing. The cheeses, the meats, and other treats were all so good, I found myself pigging out and immediately felt self conscious.

“Are you having any?” I asked, gesturing to the tray

“Not now, but you go ahead. I have plenty more” she said as she walked over to a door off to the right. She emerged with a bottle of red wine, and opened it, grabbing some glasses. Walking back towards me she sat down and poured herself a glass. Then she went to pour me some and paused.

“I could get you another beer instead?” she asked, gesturing towards my near empty bottle. My first thought was to get another beer, but then wine seemed more to set a romantic tone.

“Wine would be nice” I said, trying to sound cool and relaxed. It may be nothing, but sitting in Helens nicely finished basement, having wine and cheese as we sit on the same couch. I was getting as horny as hell.

She handed me a glass and raised hers gesturing to me to do the same. Raising mine, I allowed it to clink lightly against hers and then took it to my mouth and took a swig. I almost immediately gagged...it was not cold. It was almost warm. I tried to hide the grimace.

‘Everything OK?” she asked

“Uhm, it’s fine, I guess it’s just that it’s not chilled”

“Oh you don’t chill red wine dear, just white wine”. DOH! I must have looked like an idiot.

“I can get you another beer?” she offered.

“No, this is fine thanks” as I took a small careful sip. I wanted to try to appear as mature and sophisticated as possible. She seemed to smile reassuringly. Did she realize how hard I was trying to impress her. We made small talk for awhile, and she seemed very friendly. When I said something that made her laugh, she sort of slapped my chest playfully. She may have just been being friendly, but to be a teenage boy, having a hot looking mature lady like her making any physical contact caused an instant hardon. I shifted uncomfortably, trying to position myself so she wouldn’t see it. As we talked some more, she seemed to be leaning in, getting herself very close to me, really maintaining eye contact. At one point she reached out and swept some crumbs off my shirt. My mind was going crazy, imagining that she was flirting with me. Part of me, the realistic part of me dismissed that as silly. I was a boy, and there was no way a hottie like her would choose a boy when she could have any man. I was still getting as horny as hell!

As we talked she was leaning forward, and I was getting a half decent (but not perfect) view of her cleavage. As I looked through the top of her blouse, she leaned ever so slightly forward as I strained my eyes to catch a glimpse.

I caught her looking down as though wondering what I was looking at and immediately brought my eyes up, hoping she didn’t bust me. She responded by sitting up a bit straighter, so I wouldn’t have as good of a view. I blushed, knowing deep down that I had been busted. At least she didn’t confront me on it. I would have just died of she did that.

As we talked, she brought her feet up onto the couch, and I was aware of the fact that I had a half decent view up her skirt now. I couldn’t tell because I was determined not to look directly. I didn’t want to push my luck and piss her off. The problem was, she was sort of sitting with her legs curled up beside her as she sat with her side against the back of the couch, facing me. As a result, every time she shifted a bit, the opening between her knees in her skirt tempted me. It was a game of willpower for me to not look up her skirt. Eventually I slipped and reflectively cast a glance at a view of her inner thighs, but did not get a look at her panties. She smiled at me, and I felt myself blush more. Did she catch that one? It was less than a second and she was reaching for her wine. Fuck, please tell me she didn’t catch me looking up her skirt. PLEASE!

We talked some more, her filling my glass of wine again, as I continued to drink it, trying to be all sophisticated. The truth was, I just wasn’t much a wine person I guess, but there was no way I was letting her know that.

Eventually the topic of a school dance came up. She had heard one of the girls in the stand talking about it.

“Are you taking some lucky girl to the dance?”

What a terrible question. I didn’t have a date, and didn’t have the nerve to ask a girl to the dance. The last school dance I went to, I stood there most of the time with my friends, and only in the last twenty minutes did I end up dancing with a girl. She had liked me, and I had liked her, but I stood there like an idiot most of the night until my friends practically told the two of us to dance. I had no idea what I was doing.

‘Uhm, not really...I guess I wasn’t sure if I was going to go”, I answered a bit embarrassed.

“Not going to go?” she said with alarm. “Rick, you only get to be young once. Don’t live with regret for the things you didn’t do!”

“Well, uh..I don’t really have a date, and uh......”, I flustered

“So if you don’t have a date that means you can dance with several young ladies. Think of it as an opportunity” she said with encouragement.

“Well, I guess I’m just....well I’m not a good dancer”, I admitted.

“Rick, you just have to relax and go with it. Besides, you can always do the slow dances. Those ones are nicer anyway” she said.

“I guess, but I don’t really know how to dance formal slow dances”, I admitted

“And most high schoolers don’t know how. Haven’t you seen them. The guy just put’s his arms around the girls waist and she puts hers around his neck, and they simply rotate slowly in a circle.”, she said with a bit of a laugh. She was right actually, that’s all they seemed to do.

Slapping me on the thigh, missing my erection by an inch, she stood.

“Come on, I’ll show you” she said, holding her hand out to me. I really didn’t want to stand, since my boner would be much more visible. Had her slap been an inch off I would have been busted. Fuck she was hot! Why couldn’t I make this stupid erection go away?!

“Come on, take my hand” she said gesturing.

Reluctantly, I reached out and took it and she pulled gently. I stood, moving awkwardly, trying to keep my hands low in front of me to cover my erection, but not be obvious that I was hiding something.

She reached out, and put her arms around my neck, and moved in close.

“Put your arms around my waist”, she instructed. I did this awkwardly, unable to believe I was now in such an intimate position with Helen.
“Now we just slowly go in circles, making small steps...anybody can do it” she said. I followed her instructions, and tried to look like I was calm and relaxed, when I was as excited as hell. Helen and I were standing face to face, dancing in a romantic kind of way, alone in her basement. Holy shit! If my friends could just see me now!

As we danced, she started moving in closer as she gave minor instructions and encouragements. I was worried, because if she pressed up against me she would feel my erection, and I was terrified about her spotting that. I tried to keep my hips back, so she would not brush up against it, but she told me to straighten up, while smiling encouragingly, telling me I was doing fine.

Suddenly without warning, she moved her hips forward a bit, and before I could even react her thigh brushed against it and I knew right away that she felt it. She immediately paused, and stepped back.

“Uh-oh, what is this?” she said in a serious tone. I tried to twist away but she stopped me, and looked down. I could feel my face blushing insanely, and wanted to just disappear. She was being nice to me and I was just getting horny.

Looking at me with an accusing look, she asked me in a stern tone

“Would you care to explain yourself Rick?”

Holy shit this was horrible. She was a grown woman and I was caught getting all horny over her. Shit! Would I be in trouble? Would she say something to my parents? Fuck I was so embarrassed.

“Rick?” she asked, questioningly. I was staring down, fumbling for words

“Rick, look at me when you talk to me”. I looked up, horribly embarrassed, with an apologetic look on my face, as I fumbled for words. I wished I could just die at that moment.

She looked at me hard for another few seconds, then a huge smirk broke out on her face and she let out a burst of laughter.

“Relax, I’m just giving you a hard time. That’s perfectly normal for a guy your age. I should have been more careful. Any of your classmates would have had the same reaction, so don’t feel embarrassed”, she said with a reassuring smile, touching my face.

I was still having a hard time talking, as my face glowed.

“Oh, I’m sorry” she said mirthfully, “ I was just having a bit of fun with you...I shouldn’t have teased you like that” as she touched my cheek tenderly.

“Come on, let’s get you seated down so you will be able to relax” she said, taking my hand and guiding me to the couch.

“Rick, I’m not upset OK. I’m flattered to be honest, a handsome young guy like you finding a lady my age attractive” she said with a flashing smile.

‘Her age’ I thought? She was in her early 30’s not her fucking 60’s for crying out loud. And she obviously worked out regularly and watched her diet. Besides her face was very smooth, with no wrinkles.