The Night with A.

Our first date after many weeks of online-chatting. A., a middle-aged woman whom I’ve met on a popular dating app was making me wait for her. I kept swiping through her profile every few minutes so that I didn’t miss her when she enters the restaurant – her pictures were few (one longshot on the beach, another one from the beach just showing her back [and beautiful, long dark hair which almost covered her well-trained butt] and a last one which had to be quite old, because she was standing in front of the World Trade Center in New York) and I wasn’t sure if I would recognize here immediately in the packed venue.
8.15 PM and our rendez-vous was scheduled for 7.30, I was slowly getting accustomed to the thought of her not showing up. We had great conversations lasting until the early morning hours just a few days ago, but she was a grown woman with probably a husband and kids who was just looking for a quick fling, I on the other side was a lonely 20-something boy-next-door searching for a mommy-substitute. She must have gotten scared of my confessions from the last few days and decided to not even give me a chance – the funny thing was, this didn’t even make me mad. I could fully understand how she didn’t want to give up a happy, probably easy-going and fulfilled life as a mother of two and wife of one in the sunny Italian province.
“Hi, you must be – “ I woke up from my sad ramblings and looked up, directly at A. “Hi, yes sorry I am your date, please take a seat” I mambled out in awe of the femme parfaite who turned out to be A. She was wearing a very simple yet elegant black dress (and probably black heels which I couldn’t see because of the low hanging, red and white checkered tablecloth, typical for all the traditional restaurants in the area) with decent, but definitely not slutty cleavage and her only make-up was some dark eye-shadow and mascara which made her deeply green eyes really pop compared to her strongly tanned skin and dark brown, almost black, completely straight hair.
The dinner quickly passed and I learned a lot about A. I still didn’t know her exact age, but guessing from her looks she must have been in her early forties. She didn’t have a husband or a family, her business life (which she was strangely mysterious about) always kept her from engaging in long lasting relationships.
Her food choice made it very clear that she’s well-off financially (who else would order a shrimp salad, truffle spaghetti and a bottle of Dom Perignon to accompany those on a first date) or that A. is a golddigger aka flying-under-the-radar escort. Fortunately enough the first turned out to be true as she paid us both, revealing that she truly must have stable finances because of the black AmEx she used for the payment – which seemed rather displaced in this venue and made the waiter give some imbecile comments about the card being made out of metal (“Hehe, if it’s so heavy there’s gotta be a lot money on this bad boy!”).
After food, she quickly invited me over to come to her hotel which was quite a surprise – we haven’t made any physical contact whilst we ate (frankly it would have also been pretty weird because we were seated directly opposite of each other with a big table in between us) and she didn’t seem like a woman for the night. But her comments about the busy schedule and no longer relationships made me think that maybe she is just trying to lay-low while we’re still at the restaurant, to then unleash her true self once we are in private.
Once we arrived at her room, she poured both of us a drink. She sat down on the side of the bed and flung off her black high heels (guess I was right before). I stood still next to the minibar and awkwardly smiled, trying to hide how flabbergasted I was by her appearance. “Imagine both of us would be naked” she said with a smirking smile. I wanted to stumble out a witty response about how direct she is, when she interrupted me. “Not sexually naked. It’s a common trick to drive away nervousness. I used to do it when I would have to speak in front of a bigger audience – I would imagine all of the spectators being naked, and I remained calm without any discomfort.” Of course, everybody has heard that.
I sat down on the ottoman next to the bed, maintaining distance between us and started to ask her why she’s in town – obviously A. didn’t live here, otherwise we wouldn’t be at a hotel.
We talked for a bit about a boring convention she had to visit, but still she was being very secretive about what exactly her business was – I didn’t bother to indulge further in this topic because I didn’t really care – I wanted to feel her. Somehow the distance and casual conversation we were having was creating a weird, sexual and romantic tension between us – the fact that I was just chit-chatting with her about random stuff made my desire for her only grow, but I wasn’t able to jump the chasm.
She on the other hand was more ballsy than me – I was just mid-sentence telling her about my bachelor’s thesis which I have been working on for the past few weeks when A. got up from the bed, grabbed my head and started to kiss me intensely. And she didn’t start out with a soft, timid kiss, she started by pressing her lips against mine, opening them up and slowly stroking her tongue over my mouth until I also opened up and gave in to her. My hands covered A.’s body whilst she pushed us onto the bed, beginning our night – a night I wanted to happen and wouldn’t expect to end up as my biggest regret.
Once on the bed, she pressed me hard into the linen and told me to lay still while she prepares me. I didn’t understand what she was going to do, my only thought was that maybe she wants to start by blowing me – but boy was I wrong. A. disappeared for a moment in the bathroom and came out without her dress on, only clothed in white lace lingerie which perfectly contrasted her tanned skin and dark hair. The bra barely covered anything as it was see-through and I could exactly see A.’s deep brown and stiff nipples, the thong was made completely out of transparent lace too which allowed my eyes to dive into her trimmed bush. I felt my pants getting tight, but then I saw that she held a big gym bag in her right hand – she sat it aside on the bed and started looking for something in it. “I want you to undress, completely.” I quickly obeyed her order without even thinking about it, finishing just as she was done with grabbing her things from the bag. There I was, laying on the hotel bed of a woman I didn’t know anything about, with my cock as hard as it ever has been. A. turned around, facing me with two ropes in her hands. “Listen, if you don’t feel like accepting further orders from me, now is the time to leave. However, should you decide to stay, I expect total obedience. So, I am going to count down from five. If you are still on my bed when I come to zero, I own you. Five.” My mind was going crazy. I was so aroused by this situation but also I didn’t have a clue what she could possibly do to me. Maybe A. was some kind of psychopath, maybe she was going to kill me? “Zero.” I must have missed her counting down because of all the thoughts that were going on in my head. I have just become A.’s property, but I didn’t yet realize what that meant. “Good, I am happy that you are willing to be my slut. Open your mouth.” I did as she said, expecting her to gag me – but that was not what A. wanted to do. She spat in my mouth. “Don’t swallow. Keep it in your mouth until I am finished with tieing you up”. Her warm saliva didn’t feel too bad in my mouth, after all we did already kiss. A. proceeded to tie my legs and arms to the bedpost, forming an X with my body. “Swallow.”
She dropped her panties, on which I could see a stain from her juices – her pussy was almost dripping without the thong. She ordered me to open my mouth again and gagged me with it. I could taste and smell her, which made my dick twitch eagerly. “I see you are ready to start. I am going to turn you into my personal whore today. Tell me you want to be my whore.” – I mumbled after her but could barely get a word out with the panties in my mouth. “Good.” A. got onto the bed and immediately mounted me, without any foreplay – she just slid my rock-hard cock into her overflowing vagina and started to ride me vigorously. I felt how my sperm was building up in my balls as her hips moved back and forth, stroking my penis with the warmth and wetness of her inside. “I want you to cum.” As soon as the last word left her mouth, I exploded into her, which stopped her riding. My cum was shooting straight up into her. This was not at all what I expected – I thought she would make me beg and wouldn’t allow me to orgasm for hours, instead I got relief after just a few minutes. “Good boy. Now, after you made that mess in my pussy, you need to clean up.” She pulled the thong out of my mouth and I started to feel disgust. What was I doing here? Did she really just order me to clean my creampie from her? But my thoughts didn’t get much farther than this, because A. was already almost sitting on my face. Her cum-covered lips and hole were just a few inches above my face. “Open your mouth. Do not disobey me.” In a weird rush I did as she said. Next, I saw how she was pushing my sperm out of her pussy and shortly after the first drops arrived on my face, my lips and inside my mouth. “Good boy, but don’t swallow. Keep it all in your mouth. Now, lick me clean.” I popped my head forward, trying not to swallow the warm semen in my mouth and licked her lips, her clit and inside her hole until there was nothing white covering A.’s vagina anymore. “You are doing really well. Swallow.” I swallowed my load. “I think this is a very good start. Now we are going to slowly introduce you into more advanced techniques of pleasuring me.”

Source: reddit.com/r/eroticliterature/comments/l4kcn6/the_night_with_a