Yesterday's real life Play play. (Patreon)

(First off, if you’re getting sick of hearing about my real-life sissy play, let me know. I don’t want to bore you. Having said that…)

Last night I had a date scheduled with my Mistress/GF. We were going to go see Pirates of Penzance at a 200-seat theater near us. We didn’t have any plans to “play” as we’d been going fairly heavy with the remote-control domination we’d been doing using the cameras in my house. So, I assumed she’d want a night off. Oh, how wrong I was, I’m delighted to say.

First off, I’m always required to be wearing panties whenever in her presence. I went for a little extra credit and had on thigh high stockings. I’m guessing this pleased her because she told me to add a bra to the ensemble. This turned me on, and partly (mostly) as a joke, I added a medium sized pair of breast forms when I came out. We both laughed, but when I started to take them out, she told me I had to keep them in.

I was quite nervous about this, but one of the things we’d agreed on (in fact, I requested it) is that I’m not allowed to pester her or beg for mercy unless I REAAAALY mean it. In which case, I give my safe word. It’s kind of an understanding that if I safe word much or too often, she’ll know I’m not totally serious when I beg her to “force” me to do things and she’ll cut back on the play. So, for us this is a  good check and balance. It’s a gentle pressure not to safe word. Even though I was fairly nervous about wearing breast forms out in public, I looked in the mirror, and it kind of looked like I was just a guy with man-boobs (all be it fairly big man boobs). I decided not to safe-word yet as I could do so in the car before we got out if I got really scared.

We had planned to go to dinner before the show, and this was my first concern. However, we hadn’t planned on where to eat, and I’m like a dog in that I’m very food motivated. I hadn’t eaten much yesterday and was really invested in where we decided to go. The upshot is, I (believe it or not) temporarily forgot about my visible breasts. We agreed on an Asian buffet, and headed in. The moment we stepped inside, it was worst case scenario. There was a huge Disneyland style line. Meaning switchbacks and close quarters with strangers.

I instantly remembered my fake tits then and panicked a bit. “Can we go? I don’t want to wait in line.” She saw through my motivation, and said no. So, I waited like 10 minutes in line trying not to seem conspicuous but scanning the people as we passed. For 100% sure I caught several eyes both in line, and later in the dining room glancing at my tits. I hoped that all of the people just thought I was an unfortunate male whose genetics distributed any excess weight into his chest, but I seriously doubt it. The proportions were off. I have to admit (for the sake of honesty) in the spectrum of sexy to humiliating, it was more on the plain old not fun variety of humiliating.

After dinner we went to the play which was really fun, and we got a little daring with our touching and caresses during the play. One highlight moment was when she started tracing the line of my thigh-high stockings through my pants making me wonder if anyone was watching, and if they could tell the significance.

Once the play was over, we headed home, and discussed our future play. (sadly, she is going to be very busy most of next week, and said she won’t have much time to enforce my femininity.) But when we got to my house, she said she had a headache, and I asked her if she’d like some pain killers and a massage from her sissy, and to my delight she agreed. I asked her if I could lose the breast forms, and she agreed. But I was horny, so when I went into my bedroom as a “joke” instead of losing the breast forms, I traded for my really heavy big and expensive pair. She walked into my bedroom, and saw what I was doing, and laughed. (She’s really cool, and we laugh a lot). She came over to me and said, “let’s compare tits” and pushed hers right up against mine. Here’s something I haven’t mentioned yet because many of you will probably think I’m exaggerating. My mistress has BIG ‘OL TITTIES. Fun enough, my fake ones and her real ones were about the same size. We pressed them together and kissed, and it really turned me on.

I asked if I could put on my French maid outfit to massage her, and she eagerly agreed. For the next few minutes, I rushed around my house getting my massage table set up, gathering massage oil etc… And by the time I was ready she’d peeled off her shirt and my eyes bulged (as they always do when I see her girls freed) they are truly awe inspiring, and I’m jealous of her. She maid a comment that she was only going to take off her shirt tonight, which again didn’t really surprise me. I’d been getting the vibe that this wasn’t really going to be a “play” night.

As I massaged her, I started getting more turned on touching and rubbing her gorgeous perfect skin, and after a few minutes of her relaxing (and yes maybe we’d each had a shot of vodka too) I asked her if I could take off her shoes and massage her feet. To my lessening surprise, she agreed to that. Now I don’t particularly have a foot fetish, but the act of massaging a superior female’s feet is still sexy to me, and I got into this.

My GF/Mistress and I have been talking for the past while about me licking her pussy for her, and the other day she’d even given me an assignment to go online and educate myself to some of the techniques. I’d spent an entire evening and was feeling confident that I could do a good job. Even though, I admit to you now, and had admitted to her previously that I have almost no experience in this. I once went down on a GF for a couple of minutes, several years ago, but that’s my entire resume of cunnilingus.

So, we were both a little nervous about this. Me because I was scared, I’d hate it, and that I would be terrible at it, and her because I might be terrible at it. As I massaged her feet, I wondered out loud why we had both seemed so eager for me to eat her out, but that it had been over a week since we first got excited about the idea.

I said to her. “Maybe I can demonstrate the “pancake” technique I learned on your feet.” She was intrigued by the name. And she agreed, despite telling me that she is very much NOT into feet play. I have tried to kiss her feet in the past, and she has begrudgingly tolerated it at best. So, when I flattened my tongue, and got it very drippy with saliva, and licked slowly from the soul of her foot up to the heel, I was prepared for her to be freaked out and jerk her foot away.

Instead, she said “Ohhhhh….” I wasn’t sure if this was a good or bad sound, so I continued. Friends, it was almost instant. She was really liking this, and that made me like it more than I typically would have. I licked the souls of both of her feet squeaky clean, and she had sweaty boot feet too. It was really degrading, and very sexy. I loved it. I decided to go for broke, and after a minute I licked between her toes, and it FUCKING DROVE HER WILD! I could not believe how horny it was making her. In fact, I was totally thinking it was a total act to humor me, but no, she was waaaay horny for this. She stated breathing fast, and moaning like crazy, and saying oh, and ahh. She told me outright between ragged breaths that this was very hot.

Her being very horny made this very hot for me, and congregation, I can tell you I’m almost a foot fetish convert. Like I seriously hope she gets addicted to this and makes me do it every time we see each other. It was so fucking sexy. And guess what. About 5 minutes into this, she said in the most adorable, embarrassed tone. “So do you want to lick my pussy?” I almost shouted “Yes Mistress, please!”

After taking her pants off (she was lying on her stomach on my massage table btw) I asked her for permission to take over, and just do what I’d read about. She eagerly agreed, and so I started the routine I’d planned out. The thing I read was tease tease tease and take your time. Make it last a really long time. So I went back to licking her feet. Then after a minute of this, I moved up to her ankle, and her calf, and verrry slowly up to the back of her knee, and her quad, and then my favorite part of her back side… Her backside. I took my time licking and kissing every inch of her glorious ass. She does have a great ass too, but it’s not her stand out feature the way her tits are btw. But it was just a fabulous cake to lick and eat.

Then I walked over to the other side of the massage, table and picked up on her other ass cheek where I left off on the first. Licking, kissing, and absolutely soaking her in drool. Folks, every part of her that I licked was glistening wet by the time I was done. So much so I had to take a quick break to get a drink of water to make sure I could keep lubing her with my saliva. And I can testify that it WAS WORKING she was moaning and thrusting so much I couldn’t believe it.

Then I gently spread her feet apart as far as they could go and still be on the table. I leaned in, and moved my face down to her inner thighs, and licked them. I opened up my eyes and looked at her pussy inches away from my face, and realized I couldn’t reach it from this angle, so I licked the crease of both of her ass cheeks and moved my face in for a nice lick in her crack. I very much want to try ass licking, but it’s new for me and I’ve never done it, and she is almost new to it, and she flinched just a bit, so I left off on that.

I asked her to turn over, and she scooted to the edge of the massage table, so her legs were completely off, and her ass sitting just on the edge. She put her feet on my back, and I went in toward the holly of hollies. I’d read to focus on the labia majora (the big flesh lips outside the inner “pussy” lips), so I did that, and her excitement ramped up even more. I spent a long-time kissing, licking, and teasing around there but making sure not to touch her vulva, or clit. But eventually, she pushed my head toward it (which crazy enough is EXACTLY what the article I read said she’d do when she was ready.

So now it was time to do “the pancake”, which is to stick your tongue out, and down, almost like you’re trying to lick your own chin, but keeping your tongue relaxed, and as wide as you can, while also making sure it’s absolutely slathered in spit. I then, left my tongue in that exact position as if it were paralyzed, and moved my head so my tongue went from the bottom of her pussy lips on up to the top. I did that very slowly over and over as she writhed and moaned. “That feels gooood!” she kept saying, and I was absolutely flying. Even though I was being totally submissive, it felt so powerful to give my mistress this much pleasure. I felt like every slave really wants to, which is useful to their mistress/master.

After a while of doing that, she grabbed my hair and said, “Suck my clit!” And lucky for me, that was the second move I’d learned all about. It’s called “the vortex” and you just gently take the whole clit, and hood in your o-shaped lips, and using a little pressure, pull back on it, like you’re sucking a pop-sickle. Well, I could tell we were coming upon Olympus by her reaction, and she had a genuine horny loss of self-awareness. “Stick your fingers in!” she demanded desperately, and I of course accommodated. As I sucked her clit, and did my best to finger in and out, she grabbed my head and absolutely jammed it into her crotch. I actually had a little trouble breathing and had to “come up for air” every few seconds. I couldn’t tell if I had her clit in my mouth or not, and fingering while this was all happening was a bit like patting your head and rubbing your belly at the same time. It was horny chaos, and for the first time in about an hour (which is about how long since we’d started with the massage) I wasn’t sure I was doing a good job, but soon enough she started moaning loud enough for people outside my house to hear, and basically fucking my face with her hips, and then a moment later, she pushed my head away.

I recognize this as her having cum and gotten very sensitive. So, I asked. “You want me to leave you alone?” She smiled, and hesitated while panting. I had the idea to go back to her labia majora and pubic hair. “I said how about this?” and she was immediately on board. As I could feel her getting closer, my knees and neck were getting quite tired, and I honestly didn’t know if I could do it again so I asked if she’s like me to use a vibrator that I had handy on her.

She agreed to that, so I stood up, and put the vibrator on her mound, just above her clit, and started fingering her again while moving it around everywhere but her clit. Yep, soon enough she wanted it on her clit, and I started fingering her faster and more vigorously, and at the same time I was turning the speed on the vibe up. By the time I was pounding her with my fingers, and the vibe was buzzing away like a bunch of sex-bees, and the squirting started. She fucking drenched the front of my sissy maid dress, and the floor, and that’s when I knew without any doubt, she hadn’t been putting on a show for my ego.

I asked if she was done, and she said she was. I was feeling so good, and high, and tasting all that pussy juice on my face. I was very horny, but also was really deep in sub-space and I thought that tonight I probably shouldn’t be allowed to cum, as I wanted this to just be about her and my serving her as my superior. And do you know what the next words out of her mouth were? “I don’t think you should be allowed to cum tonight.” Talk about being in sync. I was so excited and told her I’d been thinking that myself.

She went and jumped in the shower, and I started cleaning up our mess feeling so fucking good about my place. For the first time in my life, I actually felt like a gorgeous woman’s slave, and it was heaven.