Hotel date 2

This took place a number of weeks ago already, and it had taken a good amount of planning and preparation. In the end we met in the middle of the day in front of a hotel. I was much earlier and paced around in nervous excitement.

We entered the hotel through a courtyard, went upstairs with the camera-filled lift, and navigated the mazelike corridor to our room. Inside we immediately started french kissing lustily.

 

Before we got any further we closed the curtains to avoid giving the neighbouring buildings a free show. I made her undress for me, and then get my hard, shaved cock out. But I didn't let her enjoy it, we went for a quick shower first.

Both of us shaved clean, our boipussies included, were freshly clean and we could get dressed up properly. No more male disguises for us. I got my red-black chemise on with a tattoo choker, and put on a cute lace-trimmed thong. My hardon barely fit inside and I truly loved how good I felt and how sexy I felt I looked like. She got in her whore-red lingerie, exactly what I had wished for.

Maybe I won't bore you with long details or detailed descriptions. You all know what kind of things we crossdressers love to do together. This time some photos were taken while cuddling, frotting and french kissing.

 

One thing I had been having fantasies about was to lick her tight asshole. Her boypussy barely covered by a lace thong. Just writing it turned me on again. And I pushed her on the bed, told her to spread her legs for me and went close. I had never done it before, not even close. I teased her hole with my fingertips, then leaked some saliva onto it. Spat more. She moaned like a whore in heat. And I gave her rim a careful quick lick. Then another, and another, longer one. I did that for a while, it was arousing and exhilarating.

She wanted to get my cock in her pussy, she craved and feared it. I'm too big for her to just ram it in, she had a couple of dildos to open up with first. In the end it didn't work, she tried to be too quick. Maybe next time.

My date was a very, very obedient and a good girl. She did everything I wanted her to. She just accidentally came without my permission while she was sucking my cock in front of the mirror and she was slowly stroking her tiny clit. My punishment for that was pretty gentle, some strong buttslapping and nipple twisting and tit-pulling. She also loves that. Begs for it, even.

We had gone on for a couple of hours in the end, and ultimately we just lied on the bed, in deep french kisses while she gave me a good, long handjob. I moaned lustily and when I finally came all over her, I guess I shot some cum onto the wall as well. Oops.

The next hotel date can't be here soon enough!

Porn shop meeting 2

Second serving

Before we both headed to our respective summer vacations and the challenges that brought to our affair we wanted to hook up again. There was no time for hotels and it wasn't the weather for outdoorsing and maybe getting caught. We decided to repeat and improve our previous date in the gay cinema because it was the easiest and most rapidly implementable plan.

 

On her last work week only one day worked for us both so that's when we met. For a lunch break.

Before I left I changed at work into my black lace thong and put only the necessities into my pocket. 10€ for the entrance, a black tattoo choker and some condoms.

While walking to the meeting point we kept each other up to date in bdsmlr's chat. I could feel the thong licking my boipussy on every single step and it aroused me. It felt like everybody saw and recognized my thong butt and bulge, most likely no one gave a fuck about me walking around the city, but the feeling was both scary and hot.

This time I was there first, she came a couple of minutes later. I asked out loud but quiet enough so no passer by actually heard if her thong was feeling properly tight already. Yes it was and that aroused me even more.

We went in, paid our entrance, and entered the dark cruising area. Just inside the turnstiles I put my choker on, grabbed her hand and we walked around to check what there was. This time we spent more time looking around but the place was pretty much the same we cursorily checked before: corridors, one larger room with a sofa, lots of square-meter-sized wanking rooms.

We entered one and got making out. I told her to get a shemale channel on, I wanted shemale porn in the background. She got all her clothes but the black lace thong off, I just took my shirt off and dropped my pants. More making out, groping, french kissing and frotting ensued. We were in heat.

I squeezed her tits around my cock and had her lick the tip. Sadly she's not a proper gurl with actual tits, so it wasn't as easy as in the pic here, but it felt naughty. I'll demand more of that in the future from her!

 

One of the things I enjoy is feeling her hard tiny dicklet against me so I demanded her to grind it against my butt and poke my thonged boipussy with it. Felt so fucking good and sexy. The environment just didn't encourage me to get riding there and then. She wanted to see if she could get my tip inside, so we put a condom on mine and poked around a bit. Nervousness and the extra noises from other patrons didn't encourage us so we didn't get far and I tossed my condom to the bin.

Instead I had her also put on a (tiny) condom on her dicklet so she wouldn't make a mess when cumming. For my greater enjoyment I had her suck until I felt closeish to orgasm, then told her to stop and just kiss my clean-shaved balls instead. When I felt the danger had gone, I had her continue and allowed her to take my full load. Clean and obedient gurl swallowed all, made no mess whatsoever.

I actually had intended not to allow her to swallow without explicit permission but forgot in my lust. When she had licked me clean, all the last drops too, I allowed her to rub one off into her tiny condom. And of course in the post-orgasm buzz I forgot to give some instructions I meant to so I didn't make her eat her own sissy slime from the condom. Next time, then.

 

We had spent almost an hour there so we left satisfied. Back in our meeting corner we chatted a bit about the future and then went our separate ways. I walked back to work, still feeling or fearing everyone could see I was wearing a lace thong under my male trousers.

Sexy date planning

Hotel or cruising?

It had been a way too long since we met in the centre of Helsinki for a bit of afternoon shenanigans in darkness. We wanted to meet again.

She especially wants to get railed. Over an obscenely short time she's gone from a strict "buttsex with condom only" to "fuck me bare, babe!"

I also wouldn't oppose to riding her dicklet into a condom-covered orgasm so I could feel her pulsating inside me. And then I could feed her freshly sourced sissy juices back to her. You know these romantic things, and more time to cuddle, kiss, fondle and grope around.

Most likely we'd meet in the same place as the last time for a new round. Setting up a date in a hotel is much more complicated for closeted folks like us.

As I'm writing this last paragraph we're actually planning on meeting in a couple of days! Summer is challenging with the vacations, so if we don't get to meet now, next time it'll be possible is weeks or months later. And for horny pervs like us that's way too far away.

Porn shop meeting

Some weeks ago we met again, this time for a lunch break, in a centrally located porn shop. It's one one those places with a cruising area, full of dark gloryholed booths with porn running. Gay cinema could be another euphemism. You know, right?

We met in the next street over, walked chatting to the place. I asked her at a semi-low voice but not whispering, in the middle of the streets if her thong was feeling tight. Oh yes it was and you could see the shock of me asking that in public, in a way that someone could have overheard!

I'd been in that place once before, some years ago, and for some reason I wasn't feeling shy or anything. My date was much more nervous. I guess all she could think of was how everyone knew what we were going to do in that place. Duh. That's what the place was there for!

We entered through the turnstiles, the place was damn dark and there were a couple of dudes walking around. The two of us looked around, then I decided that one of the wanking booths was ours and pushed her in, went in after and locked the door behind us. I pushed her against the door and thrust my tongue into her throat and groped madly.

The screen was showing us some gay porn, I flicked to a shemale channel. Not that we had time or interest in watching porn there, but having some proper stuff on just in case eyes wandered that way was good. We both only had our lace thongs under our male disguises, which wasn't too bad considering the confined dark space. In my pocked I had my cockrings and a pair of condoms, just in case.

I made her watch me put my cockrings on, she was obedient and just squirmed lustily and struggled against her desire to suck my hard cock. Good girl did as I told her to, so as a reward I spat in her mouth for extra lubrication and allowed her to start her worship.

 

Of course I didn't want to cum yet so I told her to get up and bend down a bit. I let her hear how I spat on the tip of my dick and rubbed it against her boipussy's lips.. She was moaning and squirming. While I was poking her with my hard cock I gave her a quick and determined reacharound. Feeling her tiny clit twitch when she reached climax was pretty damn hot. Some of her cum leaked on my fingers so I had her clean them up for me while still teasing her pussy lips from behind. That tiny locker just wasn't the place where I wanted to mount her properly for the first time, so I just teased her a bit and then had her suck again.

I didn't last long and came in her mouth. She swallowed every single drop and kept sucking longer than I could stand. Mmmmmm.

Based on a quick and not really a thorough walkaround the place wasn't good for much more than a quick blowjob. At least we didn't feel like that tiny closet would've been enough for a nice afternoon ride or doggy-style fucking. We could be wrong, though, and might visit again for a lunch break or an afternoon coffee. Or we'll check the competitor just down the street, as they, too, have a cruising area attached to a much larger porn store.

disclaimer: none of these photos are mine or of us 😄

Secret sissy slave lover

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.