Dating an Older Man Pt. 01

I am writing this at the request of another member, who wanted to know more about a past relationship i had with a much older man. I have changed some names and details to protect the innocent. Before I begin, some background about me at the time: 23 years old, 5'8", brunette, probably around 125lbs or so, green eyes, of Irish/German descent, outgoing and flirty

When I was 23, I was working a retail job in a department store while I finished up my degree. It was fun, and I spent most of my time there working in the men's department. The hours were great, and I will admit, I met a few cute guys there...some of whom I ended up dating. One of them was an older black man named James, who came in to get sized for a suit. Turns out, he was 52, but looked really good for his age: tall, great build, shaved head, beautiful eyes, very friendly and very flirty!

We had one of our on-site tailors take his measurements and I brought back some suits for him to try on. We started chatting and I was immediately turned on by his confidence and his flirty ways...he was really funny. Looking back, he had me from the start and he knew it! I was giving him all the right responses—playing with my hair, smiling, and giggling at his jokes. After the tailor finished his measurements he left to take care of other customers, leaving me and James(as I soon found out) alone to go over his options. He immediately started complimenting me on what I brought him to try on, and he also complimented me on my own outfit (I was wearing a plain black sheath dress with my store-issued blazer over it). And although they were kind of uncomfortable, I had on 3 3/4" pumps and very sheer nude nylons. He ended up asking me to dinner that night, but I had plans, so he asked about the next night. I told him I was free, but I had classes that following morning, so if I went out with him, it might be an abbreviated date. He did not mind and told me he was taking me to a nicer restaurant. So, we exchanged numbers and he left with his items.

He called me that night, and we talked for about two hours. He was quite charming and very mature, which appealed to me. He kept complimenting me on my looks and how I was dressed at work...he said he wanted me to wear a dress that "showed off my long and sexy legs" on our dinner date.

Well, working at a department store has its perks! I ended up finding a really cute, long-sleeve, black, lace dress that was just about to mid thigh. I had some cute dresses I could have worn, but I wanted to wear something new that would get his attention.

I should say, that by this time I had dated my share of black guys, but not someone this much older. I was only 23 and here he was, 52!! He was older than my father! The immediate difference I noticed between James and others was his maturity and smoothness. He had no problem giving me compliments without sounding dirty or creepy, like so many guys can sound. He was also very sure of what he wanted...especially when he told me to wear a little dress for him...that was a big turn on!

So, our date was Wednesday night...I rushed back to my apartment from my last class, changed and started laying out my outfit. My roommate (Sarah) was really excited for me because it had been a while since my last date. I told her about James and how amazing he was, and she immediately asked if I was thinking about sleeping with him that night...she wanted to know if she needed to leave the apartment for when we got home. I told her I had class in the morning so probably not. She kept telling me that I should sleep with him, as I sat, putting on a new coat of dark red polish on my fingernails and toes. When I told her he was taking me to one of the nicer restaurants in D.C. she started freaking out, saying I was going to want to fuck him after going there. I was thinking about it more and more...he was hot, and I did just buy a cute dress and I did shave all the important places, and I was going to be wearing a really cute bra and thong under my dress...which I thought he might like—should he get to see that much. I had black pantyhose to complete the look, but Sarah had even convinced me to wear stockings and a garter belt, which I only wore when I was sure I would be having sex! So having longer legs, my dress barely covered the tops of them! I thought that if James saw them he would think I was after more than just a fun night out...so i was going to try my best to keep my hemline from riding up!

So, I put on my lingerie and stockings, did my hair and makeup, put on my dress and a pair of 4 1/2" black pumps (with a little platform). I think I looked good, and Sarah was giddy for me!

When he arrived to pick me up he was dressed in a beautiful blue suit. He hugged me and he pulled me in tight to him (almost lifting me off the floor) and said I smelled amazing...(so did he!). I thanked him and gave him a friendly peck on the cheek.

We walked out to his car and he opened the door for me...it was a little sports car that was really low to the ground. And, of course, as soon as I tried to sit to swing my legs in, my dress rode up just enough so that he saw the lace from tops of my stockings! I was mortified!...so much for keeping that a secret! He gave me a big smile and closed the door as I frantically tried to adjust my hemline! He got in the driver's seat and told me how good I looked and how much he liked my dress. We talked about just about everything...our work, working out, my school, and he told me some funny stories and jokes—and all the while shifting his eyes between the road and my legs. Twice more on the ride he mentioned how much he liked my new dress and how good it made my legs look. He said it all so matter-of-fact, but so flatteringly...I never felt like he was trying to do anything except give me a compliment. Like I said, he was very smooth.

We got to the restaurant and he opened my door for me and got another long look at my dress, which I was trying my hardest, again, to keep in place as I got out. He apologized for my now obvious "wardrobe malfunction" but told me he didn't get to drive that car as much as his everyday car, and thought it would be a nice occasion for it. Looking back now, I am pretty sure he drove it because of the short dress he wanted me to wear. Men can be so devious! In my head I was cursing Sarah for convincing me to not wear pantyhose...now I was sure he would be trying to have more than a nice dinner date. He gently put his hand on my back and guided me towards the restaurant doors.

To be continued