The next day, at 11:30, I went to the boutique Dami had an arrangement with. She had told me to ask for Ugo, the owner. Though he was running a busy store, he waited on me personally and, over the next three hours, we picked out material for 5 suits and 3 tuxedos as well as a dozen pairs of boxers and boxer/briefs, a dozen pairs of socks, ten button down shirts and a dozen ties, all conservative patterns.
We chose four pairs of shoes, all Italian designers, and some jewellery pieces such as tie pins and clips, cuff links and even a cigarette lighter. We talked while we selected patterns and fabrics, and while he fitted me, he told me he always took care of the young men Dami sent personally. He clearly knew what was going on, and he didn’t seem to care either way about her business. He was making a lot of money through her, and he wasn’t about to judge her.
In the end, he told me he could have a tuxedo and three suits, plus all the extras, in 5 days. and the rest within 2 weeks. The total bill almost made me gag; Dami might be paying it up front, but I would be responsible for paying her back. Her two million naira estimate was far off.
At least she was letting me pay it off from my earnings, 50% of each week’s pay. It took a few weeks to fully pay it off. I would be available to start working the night I got the first of my new clothes.
The next few days were nerve-wracking. I did a lot of studying online, brushing up on the music and art scenes, what was fashionable in current literature in the city, as well as being up to date on local politics and Who’s Who among the ‘upper crust’. Dami called me the day before to make sure I was ready, and I assured her that I was. She promised to set me up with an ‘easy’ client for my first night, easy as in non-demanding.
Then she gave me a name, Mrs. Ugo Chiwendu, divorced, very rich with her own family fortune. She was 55, and when I looked her up online, her picture was of a woman who looked 5-10 years younger and a little overweight. Overall, I thought she was attractive, a woman I wouldn’t have any trouble being able to function for and please her. Dami gave me a time and a street to meet Ugo. She would pick me up there in her Mercedes AMG SUV.
We were starting the evening at a fundraiser at the Harbor Point, VI, dinner included. Definitely a tuxedo evening. She told me I didn’t need to collect any money; Mrs. Chiwendu had an account with her and paid her bills monthly. That actually made me more comfortable. I could, in my mind, just think of it as an evening out with an older woman.
I may have felt confident that day, a Wednesday, but as I dressed Thursday, I was scared stiff. Scared of not being actually smart enough to talk my way through the evening, not being charming enough to impress Mrs. Chiwendu, and of being obviously a paid escort, though I assumed that was known for being over 20 years younger.
I knew it wasn’t uncommon for women to have a paid escort for events, but she was also paying me for sex, and I was afraid that part would be obvious like it was tattooed on my forehead. I thought about having a glass of whiskey, but I didn’t think the client would be happy if I had even a hint of liquor on my breath before our date.
I left my apartment early, and I was at the right corner twenty minutes early, and Ugo Chiwendu picked me up promptly at ten minutes to 7. I climbed into the car, and I was officially on the clock, starting my new ‘career’.
“Hello, Mrs. Chiwendu. I’m Kayode, and I’ll be your escort for the evening.” I smiled with more confidence than I felt, and I shook her hand, not like I would with a man but gentler, though not with a limp wrist. I wanted her to know I was a man who knew how to behave with a lady.
“Hello, Kayode. It’s a pleasure to meet you.” She greeted me with a radiant smile with perfect teeth. She was more attractive than her picture led me to believe, and she wore a beautiful gown.
“The pleasure is mine, Mrs. Chiwendu.” I was trying to be charming and respectful.
“Oh, please, don’t call me “Mrs Chiwendu”. It’s Ugo, please. Calling me Mrs. Chiwendu will make me feel like an old woman.”
“Ugo, you’re hardly an old woman. You’re older than I am, but so are most women. You’re actually a very lovely woman.”
“My, aren’t you the sweet talker. Don’t worry, Kayode, I’m still going to tip you tonight.”
“Gee, and I was hoping to get stiffed at the end of the night.”
“Ummm, no, that’s ME who’s supposed to get stiffed!” And that broke the ice, a silly joke that made us both laugh heartily. It let us both let our hair down, so to speak, and the rest of the evening, we were completely at ease with each other, whether we were engaged in conversation or when I graciously asked her to dance a few times between courses. Ugo was very pleased by my courtly manners when I held the various doors and when I led when we danced.
And I also had a nice evening with her. She was very smart and well-versed in politics, especially. We even talked a little about her ex-husband and her grown kids, who never seemed to have time for her. I could see the hurt in her heart, and I took her hand and gently squeezed it. I didn’t say anything on the subject; I just offered her comfort in public, and I could tell she appreciated the supportive gesture.
I stuck to the guidelines Dami had given me: two drinks limit, don’t talk too much about yourself (“the ladies are looking for a man to listen to them and take interest”) and be kind, courteous and charming. That last part was especially easy from the way I was raised and from the fact that Ugo was a kind woman. The dinner went very well. She enjoyed showing off the handsome younger man on her arm to her friends.
Outside, we got into her car (the driver, of course, held the doors for us) and in the back seat, we kissed lightly. Nothing had been decided for afterwards in advance. The decision was totally hers.
She leaned forward a little and touched my knee. “Kayode, I’ve had a lovely night, and if you’re amenable, I would like you to come to my penthouse with me. You’re not obligated, and I would gladly use your services again for another night out. But if you would like to come home with me…with this old lady….”
I clasped her hands in mine and hushed her there. “Ugo, first of all, I had a great night as well. You’re fun and funny, sweet and kind. And you’re very bright. And….you really are a very attractive woman. You’re far from an old woman. You’re older, and that’s all we’ll say about this tonight.
It would be a pleasure for me to escort you home and from there…. well, we can see what happens. I doubt you’ll end up disappointed. And I know I won’t be.” I kissed her again, a more passionate kiss.
She looked up at me, making sure, in her own mind, this wasn’t going to be some sort of pity fuck. It wouldn’t be, not from me. I really did like her as a person, and she was a looker. Yes, I was getting paid for this, but I could see myself sleeping with her in different circumstances.
I kind of have a thing for older women. My first sexual experience was with one of my mother’s good friends, something mom never knew about, and it was amazing.
She told her driver to take us home, and a few minutes later, we were in the garage under her building so she could enter her penthouse with more discretion. She even had a private elevator to whisk us up the 48 floors to the top, where she had the entire floor.
That penthouse was everything you can imagine. Floor-to-ceiling windows all around, in every room, with drapes that could be closed for privacy. The rooms were all huge, almost all bigger than my entire apartment. And they were decorated professionally in a classic yet comfortable style. There was no question whether she could afford Dami’s prices. Ugo was the definition of Lagos ultra-rich.
I helped her off with her wrap, and she asked if I wanted a drink with her. I told her I would make the drinks, and she sat down while I poured us each a short drink. We sat on the couch, taking in the view south from her windows all the way to the lights of the city.
She picked up a remote control, and some soft music came from hidden speakers. She wanted sex, no question, and she wanted romantic sex. She wasn’t looking for a man to dominate her or vice versa, no kinky fantasies. Dami had told me my first night would be an easy one, and she was right. Ugo just wanted loving sex. She wanted to be desired.
After talking a little and after the alcohol helped us get rid of our nervousness, Ugo, anticipating what was about to happen, said, “Kayode, you don’t have to do this. I know I’m not young and beautiful like the women your own age. I would be happy to have a man to hold me all night.”
I felt bad for her, for her lack of confidence in herself. But I wasn’t going to pity her. That would have been the worst way to treat her. “Ugo, I know we don’t have to do anything. I would love holding you in my arms, if that’s what you really want. But if you want more…I would love that too. You say I don’t have to do this. But what if I want to? I’ve already told you, I think you’re a beautiful woman. I meant it before, and I mean it now.” I leaned a little closer and kissed her lips.
She didn’t move her lips for a moment, making her final decision. Then she leaned to me, and we were joined in a great kiss, all authentic passion and heaps of desire. Ugo didn’t want to do anything considered kinky, no fantasy role-play. She didn’t want to be submissive or dominant; She just wanted to make love with a man, and I wanted her too.
After kissing for a while, and after our hands barely started to explore each other’s bodies, Ugo whispered, “Kayode, please take me to bed. I really need to be loved.” There was a definite hunger in her eyes, and I kissed her over each eye.
I stood up and held out my hand, and Ugo took it as she stood with me, both of us still dressed in our formal wear. “Gladly. Just show me the way.” Leading me by the hand, she led me to the corridor, which led to the bedrooms in the back, all three of them. We stepped into the master bedroom, and I closed the door behind us.
She was starting to get some doubts again, so I just walked to her with a smile I hoped was seductive. I took her face gently in my hands and kissed her deeply, and she let me probe her mouth with my tongue. Then her own tongue sought mine, and that was it. All doubts were gone, replaced by an overwhelming desire.
We kept kissing, over and over, getting hotter for each other with each kiss. Ugo turned away and asked me to unzip her gown. I held her hair carefully away from the zipper and pulled the little metal tab down slowly, a sound that was very sensual under the circumstances.
When I kissed the back of her neck, and down her spine, Ugo audibly gasped her approval. The gown was falling from her, and I went to gather it to hang it up, but she said breathlessly, “Never mind that, Kayode. I don’t care about the gown now!” She was wearing very expensive lingerie, a nude bra and low brief panties in lace. They gave her some control under the gown. I thought she was a damn sexy woman. and by then, I had a very obvious erection, which caught her eye.
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