Late-Night Window

My father works for a large Fortune 500 company, and they hold a week-long convention every year. The entire trip is paid for by the company, so my father enthusiastically attends. Our family tags along, but I can not remember a single time we all attended because of conflicting schedules. This year, I am the only family member attending.

I always loved coming to these conventions. Every year guaranteed new memorable experiences. The last time I attended was four years ago, right after graduating college and before starting my new job. I arrived at the airport on Wednesday, midway through the convention. My vacation time flexibility and work responsibilities prevented me from taking off the entire week. While waiting in line to pick up my rental car, I formulated a response for when people would ask, "Where have you been these past four years?" I figured I would just respond with something along the lines of "I am a working man now. I have bills to pay now that I am out of my parents basement. I needed to save up money to afford one of these fancy rooms. Vacation time with my company is more flexible now. Etc."

Ever since committing myself to attend a few months ago, I have been growing more nervous every day. After all the things that have occurred over the years, who would not be was nervous. "Who is attending this year? Will any of my previous flings be there? Does anyone know what happened in the past?" I knew all this uneasiness would peak and then disappear once I met up with everyone tonight at the Mid-Week Mixer.

Before driving over, I decided to check into the hotel and drop off my luggage. The hotel website showed that my room came with a mini-fridge, so while at the airport I stocked up on some snacks, Gatorade to fight hangovers for the next couple days, and some bagels for morning breakfasts. Once situated in the room, I showered, shaved, and dressed in casual business attire. The event was from 4:00 - 9:00, and being held less than a mile away, down on the waterfront. I decided to take my rental car rather than pay more money for a cab. Plus, the rental car gave me a quick out in case things got dull. From experience, I know things can get boring when a bunch of company people interact with various levels of management during business/social functions.

I arrived at the event, and the first hour went incredibly smooth. Indeed, all my nervousness faded. I saw many old faces. None of my previous flings was there, so the coast was clear; I was unsure whether they would show up, and if I would have to face the drama that would ultimately ensue. A few of the friends I made over the years were also in attendance. I did not take long before we were all gathered around like old times. It felt like four years ago was only yesterday. Everyone commented how good I looked. I had gone on a big workout push about a year ago, and have been training for a half marathon for the past 6 months.

Everyone at these events always acted very "proper", my friends and I included. The adults always considered me the party animal of the bunch. They knew that I lead the pack, and were content with us having fun. Nothing ever got out of control and we never caused any trouble. My point being, these social events definitely needed life to them, and I was happy to oblige. When we were younger, I was always the one that found us alcohol and weed. While the parents would be out drinking, we would all be hanging out partying just the same.

Rachel is one of my friends, several years younger than me, and just finished college. Her family has been coming to these conventions for over 10 years. Her step-father is a big-shot with the company, and friends with my father. I remember when Rachel's parents stayed at our house one week a long time ago, mainly because I had to give up my bedroom so they could have a place to sleep. I will admit, Rachel is not the most attractive person, taking on most of her biological father's features. There is no sexual attraction between us. Although, she was curious about giving her first blowjob years ago when we were much younger, but that story is for another time. Believe it or not, we were still able to be friends afterwards.

Back to the mixer. During the course of the evening, Rachel came up to me and asked if I still smoked weed. I knew where this question was headed. She knew me well enough that I probably would still smoke once in a while, and she was right. Rachel's next question however, took me completely by surprise. She told me that her mother, Janet, wanted her to ask me.

One moment I thought all is well, no drama this convention, and the next moment I get this thrown at me. I looked over Rachel's shoulder towards her mother, where she was mingling with her husband, my father, and all their friends. Chills ran down my spine as I saw Janet looking at me smiling. I immediately began thinking, "Why in the world would she ask Rachel this sort of question?" The only reason I could think of, was to check and see how much trouble our group of friends would get into this year.

I would be lying to say Rachel and her step-father had a good relationship. I would go as far to say it was because she was only his step-daughter. This is probably the reason Rachel and Janet were so close. They shared the same free-spirited personality. I knew that Rachel would most likely tell her mother I still smoked weed and that Janet would never tell her husband, because he would make a big deal out of a harmless situation. Knowing their mother-daughter relationship, I just smiled back at Janet and she looked away resuming her conversation. I felt my reaction to this surprising situation was satisfactory. Out of curiosity, I asked Rachel, "Why would your mother care if I still smoked?" I smirked, sarcastically adding, "its not like I brought any with me on the plane". Rachel laughed at me, seeing right through my bullshit. She knew that I would have definitely brought some weed if I still smoked, and she was right, I did bring a few joints along.

Rachel's next statement was a bombshell I was not prepared for. "My mother just turned 42 and has been doing all sorts of midlife crisis types of things with her friends recently. She even went skydiving, can you believe it? It like she has been trying to get some sort of reaction from my step-father lately. Of course he disapproves, so I make an extra effort to encourage her. You only live once right? Anyways, I am not sure, but I think she was asking because she is curious to smoke again. She probably hasn't smoked since forever ago." I just stood there in shock, open mouthed, and speechless. "Did I just hear what I think I heard? Janet wants to smoke weed?" I am an adult now, and the thought of smoking with one of my parents' friends, yeah why the fuck not!?" I looked back over to see Janet speaking to my father, and thought to myself "I guess her and my mother are not much alike after all." I laughed with Rachel and said, "Sure, yeah, let her know I still smoke and brought some joints, and if shes interested to let me know". Rachel nodded and smiled as she walked away. Judging from the tone of Rachel's previous statement, she made it seem like her step-father kept Janet locked in a cage. If your wife wants to go sky diving, why not? Go do it with her. Nevertheless, this was Rachel's idea of helping her mother and getting back at her step-father at the same time. I was game.

My impression of Janet over the years was that she was artsy and eccentric compared to her formal and reserved husband; he tucks his t-shirts into his jeans, and I believe has a fanny-pack collection. Rachel and Janet looked nothing alike to the extent that when we were younger I would joke with Rachel by asking if she was adopted. Janet was tall, and with heals comes up to my chin. Her hair was shoulder length, very curly, brown with a lot of blond highlights. Janet always wore unique designer dresses, which earned her praise from other women at the events. I am no fashionista, but to describe the dress she wore that night, it was spaghetti strapped, flowing down over her knees, was blueish green, having an almost jungle-like appearance. With her short curly hair, the back of the dress showed off her long neck, with the opening going down to the middle of her back. She had a great figure for her age; definitely a looker.

About 15 minutes later Janet walked up to me. She greeted me with a hug saying, "Hey there Blue-eyes, long time no see". Janet always called me by that nickname, and I would always respond, "It's the Irish in me". After a few pleasantries, I saved her the trouble by cutting right to the chase, "I talked to Rachel, so did you want to get out of here for a while? The buses won't be coming to pick everyone up for another few hours, and your husband will stay until the end, guaranteed". Janet blushed a little at my forwardness, but laughed saying, "Yeah I was thinking about it". I told her that I was going to take off in a few minutes, but not before I say goodnight to everyone, and if she were interested to let me know.

While heading back to my friends, I reflected on what just transpired and laughed, "Not even one day at the convention and I am already getting myself into trouble. It must be because I stayed away for a few years. Oh well, I need to make up for lost time!". I ended up telling everyone that I was tired from working this week, the flight, and just wanted to rest up for fun tomorrow. While saying goodbyes, Rachel's step-father came up to me and asked if I would mind escorting his wife back to the hotel because she was not feeling too well. I replied saying "Of course!", while at the same time thinking to myself, "I guess it didn't take her long to make up her mind". Standing there behind him I see Janet trying to fake a stomach ache, and Rachel with a ridiculous evil grin on her face. What had I gotten myself into?

Just before leaving, Rachel's step-father came up with the great idea of taking a quick few family photos while everyone was dressed up, to use for the annual Christmas card. Janet tried to delay it for another day, but her husband would not take no for an answer. In order to speed things along I suggested that I use my phone, and could text the pictures to Rachel after. Their family lined up together for the first photo. Then Janet and her husband, posed alone, facing each other, pecking a kiss. It was cute.

As we drove, I turned and reached for my bag behind the passenger seat. Janet commented saying that I smelled nice. My reply got a laugh out of her, "Its this new cologne I am wearing. Apparently, it works as advertised". While she was laughing, I was presented with the perfect vantage point to admire her cleavage without her noticing. Her breasts are not very large, a B cup at most. Watching her breasts move while laughing indicated they were still firm and supple. From my vantage point, it was evident she was not wearing a bra.

I must have been a little too distracted, because Janet then asked, "Are you having any trouble back there?". She began to turn around in an effort to help. As she twisted around, she placed her hand half way up my right thigh for support. If she moved her hand any further up my leg, should would have gotten a handful of my cock. I could only respond to her question with a stuttered, "Yeah, everything good, just trying to find the stuff in my bag". She had to notice the growing bulge in my pants.

I finally found a joint, and handed it to Janet with a lighter, asking her to hold onto it until we got out of the parking lot. It was also a way to test her, just to be sure she was comfortable with it. She replied with, "Its been way too many years since I've done this, can you light it to get it started?" I took a few puffs and passed the joint back over to her, and watched her do the same. I found myself thinking, 'I guess she really was free-spirited back in the day".

The thing about weed, it seems like the instant you smoke with someone, its like you become good friends. Any tension about the taboo situation disappeared like smoke out the window. I told her to smoke all she wants, and in a macho voice I spoke to an invisible crowd saying, "It is my main mission to properly ensure this fine young woman gets to her destination." Janet looked at at me, laughed, and smiled saying, "Oh? And how are you going to properly ensure such a thing?" I caught her sexual innuendo, but refrained on responding in-kind, instead joking, "Staying sober enough to remember how to get back to the hotel!". All she could do was continue to laugh and shake her head.

Janet began telling me all about her recent skydiving trip. "You can not even describe the experience. Standing at the plane's door, looking down. It is surreal. For the first time the clouds are beneath your feet and the ground far in the distance. As you are falling, you feel the weight on your shoulders, down there on Earth, getting caught by the clouds and both swept away together in the wind." I remember that description, because it was the one and only statement, made by someone stoned, that I thought was poetically brilliant. Janet went on, "Thank you for letting me smoke with you. You have to let me give you some money to repay you. God this brings back memories of the things I did when I was your age, back in college."

Be it the weed, alcohol or fate, with an innocent expression on my face, I immediately and without thinking came back with "All you are missing now is the sex.", The look on Janet's face was priceless. All the barriers between us, created by social formalities, was now shattered. Janet gasped, and laughed, "Sex? When I was young I was not so easily fucked. I would just mostly give blow jobs." Now it was my turn to be shocked. Did I just hear what I think I heard. Not letting her casual disclosure go without response, "Hey men of all generations will always accept that which is offered." Janet then brought the conversation back out of the gutter with a laugh, "Hey now young man, what kind of suggestions are you making to this old woman".

We got back in the hotel and things felt like they were slowly becoming awkward again. Janet was quiet and I was not sure what she was thinking. The only person we ran into was a young bellhop getting out of the elevator. We looked at each other, and immediately noticed that we were both stoned. He and I both laughed as the elevator closed. He seemed to avoided eye contact with Janet, probably because she is much older, thus probably my mother.

I presumed Janet and I would part ways, and I could go back to my room for a masturbation session while the image of Janet's cleavage was fresh in my mind. I had been single and sexless for several months prior to the convention. I spent most of my time working and training. It had been a long time since I laid back and blew off some steam. Needless to say I was very horny.

Once on the elevator, Janet pressed the button for her floor. I assumed this was where we parted, so I pressed the button for my floor. She immediately asserted, "Where do you think you're going? You're not leaving me stoned in my room all alone." Taken aback, I quickly reassured, "Never. I just wanted to head to my room to drop off my bag so it doesn't smell up the room". Janet replied, "Good idea. Alright then, we will stop at your room first." I was at a loss of words. I mean, what is going on in this woman's mind?

As the elevator started it accent her phone started to ring. Janet irritably dug into her purse to see who was calling. It was her husband. She looked at me sternly, and whispered "Shhhhh". So I stand still, and salute. Both of us were trying our best to stop laughing and regain our composure. Stoned and lying to your husband. Priceless.

I stepped towards Janet to eavesdrop on the conversation. She read my mind, and offered her right arm bringing me against her. She held the phone in her left hand, and brought it across her body to her right ear so I could hear. Being so close to Janet was intoxicating. I could smell the vanilla shampoo in her hair and the slight scent of perfume. The way she held the phone pushed her breasts up and together, giving me a spectacular vantage point of her cleavage again.

The phone call started as expected. He wanted to check up on her, make sure she had got back safely, and to see how she was doing. Janet then took the conversation in a different direction. "I am doing alright... I just got back to the hotel a moment ago... I am just going to take a shower and anti-acid and head to bed... No I don't mind you hanging out with the boys... I'm not sad, just a little upset... I wore this dress tonight hoping to exite you.. Well, it was not just the dress, but also what is underneath... Oh, you ARE interested huh? Ok I will tell you, I am wearing nothing underneath."

I stood silently listening to this impromptu phone sex session, too afraid to move. It was not like I could go anywhere, stuck in an elevator with Janet's arm holding me close. Maybe she does have a deviant side to her that she does not let anyone see? As the conversation escalated, so did my cock. This could be trouble, as when I get hard, my cock is strong enough to use as a coat hanger. Standing up against Janet at this moment was very precarious. I strained to think of anything else. I tried to look away, but in vain. I forgot the elevator walls are covered with mirrors. Last option was just to look straight up, but reflecting back at me was a great view of Janet's breasts. Fuck my life. I could feel the blood rushing to my cock, and I knew Janet could feel it as well. Just then, the conversation changed, and she stepped away.

"Seriously, we were just starting to have fun and you ruin it... Yes, you did... I just think as your wife, your worrying about such a thing is pointless... No, its ok... I am still just not feeling well and in a cranky mood... Yeah its ok. Love you too"

I knew that I was in the wrong place at the wrong time, and I was not sure what to say, so I said nothing. I will admit, although my earlier masturbation plans were foiled, those minutes up against Janet provided me with sufficient fuel for many future fantasies.

As we walked the hallway to my room, I had a reinvigorating epiphany of greater possibilities. I thought to myself, "when I get back to my room, I will put on more comfortable clothing, and then, I am positive she will want to do the same when we get back to hers. Befriend this woman for the slight possibility of seeing more skin when changing? Consider it done." I also figure that I might end up hearing another fun phone conversation.

Being a gentleman, I opened my hotel room door for Janet letting her in first. She entered and walked straight towards the window, which went from the floor almost up to the ceiling. She spoke up, "Oh wow. Your room has an amazing view of the city compared to ours. You can even see where we were all down at the waterfront. The city lights are like fireflies. You have to see this." While Janet was at the window I was putting my bag in the closet and grabbed a change of clothes. Walking into the bathroom I responded, "Hold on a few, I am just going to change out of these clothes quick". I did not want to make her wait long.

When I was done, I turned off the bathroom light and exited to a dark room. I just now realized that we never turned on the lights when we first came in. Temporarily blinded, I turned facing Janet at the big window. As my eyes readjusted, I stood there awestruck by Janet's beauty as she stood silently staring into the distance. First, only her silhouette appeared. Then, I started making out features of her dress and the curves of her body. The lights from below contrasted with the darkness of the room, illuminating her dress to near transparency. As she leaned over, my head tilted following suit.

I was in a mesmerized stupor. Janet stayed there, silent, until she called out my name. I immediately came out of the trance, and the gravity of the situation began to hit me. I am alone in this dark room with a woman I fantasize, who is a family friend, and happily married. I have a photo in my phone of Janet and her husband kissing after all. I should not be thinking these things, especially at this time. Again, Janet called out my name, this time turning to face me.

"I had been thinking about what you said in the car, and you are right." Unsure what she meant, I was confused. Janet took a step towards me, "These trips I go on, trying to relive my youth, you were right." I stammered, desperately trying to remember the conversation. Then she blurts out, "I need sex." Janet then reached up, and slid off the spaghetti straps on her dress. It fell down to the ground softly, just like tissue paper. "You have what I need Blue-eyes, and you're going to love giving it to me."