So Friday came and I made sure I got off work early, in time to be home and watch her get ready. It's something I've always loved to do, especially when she's getting ready to go out with him. This time was even more exciting to me because for one, it was a real date and two I knew she would be getting fucked by said date (the previous dance class dates that wasn't a known thing). So it was all extremely exciting to me.
She had planned to get off a little earlier than normal too but she had a last minute (long time client) she couldn't say no too. So it had her running late. She came home in a rush, hurrying around and acting somewhat frantic. I tried to stay out of her way for the most part but still hung around trying to watch and chit chat when she would allow it. I know she knew what I was doing and she tried to humor me but at the same time she was under the gun somewhat so not as flirty or fun as she would normally be. He came around 7:30 to pick her up and she was still doing her make-up when he arrived. I let him in and we sat in the livingroom and talked while we waited on her. Once again he was relaxed, calm and cool which was very good. We talked about our weeks and what had happened in our lives recently, just normal stuff. At some point she yelled down stairs that she was almost ready, she'd be down in just a minute. He looked at me and smiled and asked if I was sure I didn't want to go too. He said we'd have fun. I just laughed it off and said thanks but no thanks. I was tired and wasn't up for any loud nightclub action or anything. Then I told him "She's all yours tonight, ya'll two have fun." I smiled real big when I said that (loving my own little private thoughts saying that gave me). He looked a little uneasy when I said it but it seemed to pass almost right away. Maybe I pushed too far jumping in with that comment but it was fun to say and kind of just came out anyway.
I flipped channels on the tv and we continued to chit chat. Nothing "date" or Jenna related, just normal guy chat. So around 7:45 Jenna came downstairs looking every inch the little hottie on the prowl. Make-up and hair done perfectly. She had her eyes done really dark and alluring looking, extremely sexy! She really had the "date night" look going on. The dress was a silvery color and very form fitting. I don't think it was technically a mini but it was close. Just a one piece short short dress with the whole top of her chest exposed, lots of cleavage. And of course the matching strappy heels that made her taller than me. We both stood and I snuck a glance in his direction and saw he was wide eyed and impressed. I assume he toned his response down for my benefit, but he told her she looked very nice and he complimented the dress. She giggled and told him he paid for it so she hoped he liked it. He laughed and said he did, allot. She walked to the kitchen to get something and I noticed he snuck a quick glance at her ass as she walked away. I was smiling inside as I realized he couldn't help himself, even in my presence.
She came walking back in smiling and said she was ready to go. Damn guy's she looked so hot. I was excited over the whole thing and wouldn't have changed anything about it. But I did feel a tad jealous knowing it was all for him and he was the one fixing to escort this hot lady out for a night on the town. He would be the one walking her into the club and holding her tight when they danced. Maybe stealing a kiss or two during some of the slower numbers. His hands holding her soft sensuous curves and feeling her melt in his embraces. Smelling her sweet and sexy perfume while she laid her head against his chest and swayed to the music. Very hot and romantic thoughts but like I said, laced with a tiny bit of envy and jealousy on my part. She picked up her purse and walked over and gave me a little kiss (barely touching) on the cheek, so as not to smear her lipstick. Once again I was aware of her tallness and as she walked over towards him it made me feel even smaller seeing that they were the perfect look of a couple. She could wear her high heels and still have to look up at him, while she had to look down at me. Very humbling but strangely erotic and very exciting. They both said their goodbyes to me and started towards the door. I followed behind telling them to have fun. I watched as they walked out the door and I stood for a few seconds watching them walk down the hall of our condo. They walked side by side and he placed his hand on the small of her back as soon as they entered the hallway. After I closed the door and went back inside I tried looking out the window to see if I could see them in the parking lot but he hadn't parked in my view so no sighting there.
So that was the beginning to their date. Very very exciting stuff to me. Something hard to explain to someone who hasn't been there and done that but I'm sure some of you know the feeling well. I could get very used to that sort of thing though. The slight humiliation of it all, the half hard cock hidden away in my pants, the funny butterfly feeling in my stomach, very weird but very arousing stuff for me.
Oh shit! I forgot a big something . Earlier while she was getting ready and I was hanging around watching I suggested a possible plan for her if she decided she'd like to maybe sleep over at his house. I had thought about it all day and I really hoped it would excite her and she would use it. I suggested she text or call me to tell me they both had had a little too much to drink so she was going to just stay over at his house, so they wouldn't risk having an accident or getting pulled over or anything. She seemed a little unsure about it but said she'd see what happened and "Maybe." I knew I was probably overstepping again but it seemed a great idea to me and I had convinced myself she was going to love the idea and jump all over it. Didn't happen but I tried

Maybe next time.
Ok that's it for tonight. Got a late start on it all. I'll try and get the rest posted tomorrow night or the next. Hang in there friends and thanks for your continued support!