The Strange Request Date
At first I figured there was less than a 50-50 chance that “the date” would actually happen. After two “I’m not sure about this” and two more “promise me you won’t go too far” conversations we had the “promise me you won’t let me go too far” discussion. After the last I knew it definitely would happen. The plan was relatively simple. It would be after work. Her excuse would be in after-hours meeting with clients; a not too unusual occurrence. I didn’t give her too many details. I just told her to me at this particular hotel bar. I’m sure she was a little hesitant and may have thought I would go back on my promises, but she didn’t say anything and met me without question. I was waiting for her when she arrived. I picked a quiet table in the back well away from the happy hour food table. I took the liberty of ordering her a glass of red and fought through the blue hairs to get a small plate from the hors d’oeuvres table. I wasn’t too worried about what was there I just wanted some nibbles available to judge her comfort level. If she is nervous she will pick at the party mix, if not she will ignore it.
I hadn’t made any recommendations on what she should wear. I knew it would be attractive and suitable. In all the years I have known her, I have never seen her wear anything risqué or overly revealing in public. Naked or partially clothed while having sex in public places where we could get caught, yes, but never actually wearing anything trashy. She has a few bedroom play costumes she occasionally breaks out, but never where others, especially kids, could see. She is typically in skirts or dresses. Short, but not immodestly so. They might be fitted, but never skin tight. Classic and classical elegance is pretty much her style of dress. Even her casual wardrobe is fairly conservative. Still I was taken aback when she walked in the door. She was wearing the quintessential Little Black Dress. It was striking. The neckline gave just a hint of cleavage and the hem was high enough above the knee to get your attention, but not high enough that anyone, other than the most puritanical biddy, could find fault. She set it off with a simple string of pearls and a black cashmere wrap. She has a fondness for matching bra and panty sets so I was sure that top and bottom matched. Probably black lace, but there was the off chance that she may have worn an animal print.
In my mind she doesn’t need much makeup. I have seen her with and without makeup but have never seen her actually applying makeup. I am not allowed to “see how the magic happens.” So I don’t know what all it entailed, but it was obvious that she had refreshed it before coming over.
She usually goes bare legged except for special occasions when hosiery elevates the outfit to the next level. This was one of those occasions. She had on very sheer black hose with a subtle design woven into the fabric. These were not dollar store or even department store hose. If they weren’t Wolford’s they were in that league. As she got closer I realized that the design was a climbing vine. While looking at her legs, I had a realization. The pantyhose, and I was positive that they were pantyhose, not stockings, were not just for the added elegance. They provided another layer of defense or barrier to keep us from going too far. I stifled a laugh at the thought.
I stood and held her chair for her. She looked amazing, and I told her so. She replied that I didn’t look too bad either. I was dressed for the occasion too in a jacket and tie. That is something I don’t do too often so she did appreciate the effort.
She held herself well. There was no sign of any apprehension in her manner or deportment. The fact that she was constantly fiddling with the items on the nosh plate was the only sign of her nervousness. We settled in and I was able to get her talking. It took a little bit, but I got her talking about all sorts of things. Talking about her day, the news, gossip, music, art, movies, just a bunch of odds and ends. It seems that living with someone 17 years younger has a lot of advantages, but stimulating conversation is not one of those. I interjected only enough to get the conversation moving again when it started slowing down. We talked about everything except her boyfriend and why we were meeting there.
About half way through the second glass of wine, the plate of snacks long since forgotten, the band started up. It was a decent 3-piece combo that played light jazz and easy listening. It was the primary reason I picked this place to meet. They played “belly rubbing” dance music. I stood and held my hand out for her. She was a little hesitant. She never thinks that she is coordinated enough to dance properly at least not to waltz, but I was insistent. She took my hand and let me lead her to the dance floor. I pulled her close to me and we proceeded slowly work our way around the small wooden section that serves the dancers. I could hold her close and smell her perfume and before two dances were over she nuzzled her face into my neck letting me guide her around as I liked. We danced a little more and when I led her from the dance floor she didn’t resist. We went to the table where I grabbed her bag, helped her into her wrap and we walked out the door.
It was a little past twilight when I took her through the hotel garden. It was a series of small dimly lighted paths that meandered through groups of local and exotic foliage. We got to an area that had a little bit of relative privacy I stopped and took her into my arms and held her close. Again she nuzzled into my chest and wrapped her arms around me. I lightly massaged her back working my way from her hips to her shoulders. She’s always had some sort of back issues and responds well to a good massage. While we were there in the dim light, she raised her face to me and kissed me deep and with more than a little passion. I pulled back and looked at her. She dropped her head then raised it and said “maybe kissing on the mouth is okay”. So I kissed her deep and soft and long.
After we broke our kiss I took her hands and let her down the path. The only sound was the clicking of her heels. I’m still not sure if she was disappointed or relieved that I didn’t take her to the elevator banks that led to the rooms. I did take her on out to the parking lot, walked her to my vehicle, and helped her in to the front seat. I have a full-size SUV that has a very large front seat and I parked in an area that gave us a lot of privacy. I got in on my side and found her facing me with her back to the door. I smiled and said “I made you a promise and I don’t intend to go back on it now”. I reached out my hand, she placed hers in it, and I pulled her toward me. We kissed. We kept kissing. Lightly at first, then progressively deeper and more passionate. After we broke for air I started kissing her neck, her ears, anywhere I could get to skin. Each time it was a little less than what she wanted me to do. We were back in game mode. I was teasing her. Giving her a little taste but holding back a little bit, always making her want a little more. My hand brushed her across her breasts. Lightly at first then a little more. I grabbed her behind, again starting out lightly then getting progressively more intense. I was very careful to stay above her clothes and resists overwhelming temptation to go further. For about a half an hour we were just two teenagers making out in the front seat of the car.
The windows were completely steamed up when I reached down and started massaging her legs and thighs. The hose was ridiculously silky and sensual feeling. Before long I ran my hand up the back of her thigh and caressed her shapely ass under her dress but still above her hose and redundant panties. We continued to kiss while I explored the other areas covered by pantyhose, careful to avoid her pubic area. But just like the teenagers we were imitating, things started getting a little intense. When we moved a little she opened her legs so I ran my hand down the inside of her thighs again avoiding her mound and lips with my fingers putting my hand back on her butt. What this did was cause my wrist and lower forearm to rub across her lady parts. It was almost like a switch went on. She rolled into it and started rubbing herself on my arm. I could feel her wetness. Her panties had to be soaked. I pressed back against her and felt her hand rubbing my cock through my slacks.
The rational part of my brain wasn’t getting much blood at the moment so it was tough, but I realized that we were going farther than I intended and definitely farther than promised. We were both panting when I broke the kiss. I was trying to collect my breath as well as my thoughts but before I could do that she pushed me back and started going down on me. While I was realizing we needed to stop she had managed to get my zipper down and my cock out and now had it in her mouth. Stopping her from sucking on me was one of the hardest things I have ever done, no pun intended. I admit I was very slow in stopping her, but in my defense she gives wonderful head. I lifted her head and looked into her eyes and kissed her. The next decision was hers. I had kept my promise (for the most part) so anything after this I was free of my obligation.
She obviously thought about it then pulled back and started straightening her clothes so I did the same. When she was ready I walked her to her car and opened the door for her. Without another word she wrapped both arms around my neck, pulled me to her, gave me one more long passionate kiss, then got in her car and drove off. Watching her drive away, I thought about what was in store for her boyfriend tonight. At first I thought “Lucky Bastard.” Then it was “you dumb ass bastard, you could have what you are getting tonight, every night if you just put forth some effort.“ Finally I thought “no, I don’t think he could do to her what I did tonight even if he tried.” That gave me some solace as I took my blue balls home.
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