I've got two dates with a very submissive sissygirl now, in the real world. We've chatted online for ages and had a good number of video calls with heads hidden. This year I finally got enough of just talking about meeting in person and started working on it, checking places for the meeting and things like that.
Time was the biggest problem as all this had to be done without getting caught. The gay cafes in Helsinki open way late or are located in areas where I know too many people for comfort.
First date
Our agreement was that this first meeting was going to be a chaste one, no shenanigans. I still wore my black thong and I sent a quick pic before I left. Walking to the metro wasn't anything, I felt nice and happy. In the metro, as the station came closer, I noticed being more and more scared but still left on the actual stop and walked to where we had agreed to meet. All this time we sent messages, I didn't know about her but for me it was a way to make sure I didn't panic out 😅
I was early so I had the time to walk around and even check out the bathrooms, just in case.
We met, went to the quietest area for a calm walk because all the cafes were packed full at that early afternoon hour. Instead of sitting in the middle of people we walked around, chatted. After a while she asked if I wanted to go a bit further and my question was how much further are you thinking about? A kiss, she repied.
We exchanged some passionate french kisses in a barely hidden place. I was so hard and asked if she wanted to see. Of course she did. So I opened my pants up to show my bulging thong and, well, my cock escaped and slapped her face. With a permission she sucked a bit, quickly, but I didn't want to cum in her mouth in such a dangerous place so I had to stop it... getting caught really wasn't in my plans.
So that was the first, "chaste coffee date with no shenanigans". No coffee, but a good nice chat, french kissing, spitting in her mouth, a bit of cocksucking, and tit-teasing. Not bad at all! Afterwards I still pretty fucking horny because I didn't get a release.
Second date
A stroke of luck came along pretty soon after the date, and I had a few easy days coming. I let her know and we started planning a hotel hookup in lingerie. Finding a suitable date for the both of us was a bit more complicated than expected but that's adult life for you. We met in the centre of Helsinki in the early afternoon and proceeded to the hotel.
We managed to behave in the lift, and obviously in the security camera -riddled corridors, until we got into the room. Immediately after closing the door behind us I pushed her into the door and kissed long and deep. She was almost in a trance, submissive as fuck. More french kissing and groping. Then we undressed and I shoved my hard, shaved cock bulging my white lace thong. I loved to see the cocklust in her eyes. While she was dressing up as my whore in black lace, I took a quick shower, and then put on my red-black chemise and black lace thong and my new red tattoo choker.
I felt sexy as fuck and I was horny as fuck. You can imagine, I bet.
We kissed, groped, I spanked her and teased her tiny tits, she's heavily into that. I made her rub her tiny, hard, leaky clit against my boipussy but didn't make her fuck me this time. Instead I had her eat my ass, it was a peculiar sensation. Not sure if I'd tell her to do it again or not.
Some 69 was enjoyed as well, of course, and when I felt I couldn't take any more I told her to kneel in front of me and suck me properly. That she did, dear readers, that she did. Not a single drop of cum was wasted. I was drained.
Afterwards we played a bit with positions, me moving her around as I pleased, as if she was just a fucktoy - which is exactly what she is. There wasn't going to be any fucking that day anymore, but she was getting more and more hot about getting railed even though she's afraid of my cock fitting inside her.
I have been in control of her orgasms this year and I felt magnaminous and I stroked her clitty and slapped her nutsack until she shot her load on her face and chest. Of course I had her eat her cum so none was wasted.
A part of this experience for her was that I made her a whore, so I packed my chemise away, pulled my boy clothes on (kept the lace-trimmed black thong on because I love thongs), dropped 50€ on the table for her services and left. She was my sissy whore now.
Next date
We've been talking about the next hotel session again. Setting it up is much more difficult in the normal schedule, so we have been thinking about a morning fuck instead of an afternoon. Yeah, she's been begging me to fuck her. Thinking of my cock entering her boipussy both scares and arouses her.
Truth be told, anal hasn't been that much of a thing for me, I'm heavily an oral girl myself. But if fucking her is a big thing, I'll do it. I also did cum riding a cock once, so I can't say I'm all against taking cock myself. But it wasn't that special somehow, anyway. We both have agreed on that and would be just happy if our follow-up dates revolved around french kisses, groping, fondling, gentle spanking, 69 and blowjobs. Sounds awesome to me!
This or the next week had been thought about as very possible weeks for the third date, until she got some events making it either difficult or impossible. This week got blocked for me as well at the last moment, so if her next week clears up, then we can still do this. Or we do it a bit later, we've got time.
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