My 1st Sissygasm On A Real Cock free porn video

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Last year I was locked up in chastity for around 6 months and the rest of the time I simply chose not to play with my at all. So I was pretty confident that for 2020 I could stay caged 100% of the time. Being locked up doesn't mean I couldn't masturbate, far from it. I pretty much masturbated every day, just the way a girl would do it, dildo in my fuckhole and moaning like a whore. Over the course of the year it got easier and easier for me to sissygasm (I.E hands-free anal orgasms). It has reached a point where I find it harder Not to cum when my ass is filled full of dildo. Of course, being caged kept me horny almost 24/7 and I did go and get myself lots of real dick, it was inevitable. And although I loved every last second of it, I had not been able to sissygasm on a real cock yet and I desperately wanted to ask for permission to cum like a girl on some random guys dick. All that changed this year and Im delighted to say that the first guy who fucked me this year made me cum on his dick like a girl and I'm here to share it with you.
So 2020 began with me locking up my useless sissy dick in a pink chastity cage and sending the keys to a friend on the promise I could only have them when I needed to shave( cleaning with the cage on is pretty easy). Fast forward a few days into January and I met up with some guy who let me suck him off in a dark back street close to my place. Although I begged shamelessly for him to come to my place and bend me over he refused. I still got to swallow his load so it wasn't too disappointing and obviously I thanked him as he left. The next 3 encounters all went the same way, 3 different guys who were all just happy with a quick blowjob followed by me swallowing their load. Then I got talking to a local guy who lived almost in the next street and we flirted and texted until I finally convinced him to fuck me. When the time came I was fully shaven, plugged and caged with a tiny pair of panties underneath a short black mini dress. As the time was pretty late I decided to risk the 2 minute journey to his place dressed as a girl. When I knocked at his door and he let me in I cant describe just how excited I was, I had pre-cum dribbling down my smooth shaven thighs when he made me remove the dress. The guy in question wasn't anything special, just another stranger to me and his dick was pretty average to be honest. Still, I got on my knees and sucked it hard like i'd rather have cock in my mouth than breathe. In between taking his hardening cock down my throat I managed to beg and plead with him to fuck me. He simply laughed at how desperately pathetic I sounded and made me suck him some more. Finally he told me to get on the bed, lay on my back and pull my panties to one side. I did what I was told, then slowly popped the plug out of my sissy fuck-hole straight into my mouth. I pulled my cheeks apart as he knelt between my thighs and pressed the wet tip of his cock against me. When my hole swallowed it up I moaned like a whore and he pushed it all the way inside me. I gasped out loud as I realized I was almost about to cum right away. "please may I cum on your cock" I managed to squeal as he began thrusting into me. Again, he just laughed and told me he didn't give a fuck what I did. I hardly had time to say thank you before my ass clamped tight around his shaft and I started to sissygasm on his cock. I couldn't even speak as I shuddered and emptied my load all over my stomach and thighs, a minute hadn't even passed since he put it in me. The guy didn't even bother to look up as I came like a bitch on his dick, he just continued using me however he wanted. When I finally caught his eye, I scooped up the sticky spunk that had puddled on my stomach and deliberately, messily, licked my fingers clean. He flipped me over and i got on all fours with my ass hanging off the edge of the bed and he stuck it back in and gripped my waist to pound me hard and fast. Not much later he told me to get on my knees quickly and he pulled out of my ass and started to cum. It caught me by surprise and the first few squirts splattered all over my face before I got my mouth open and tongue out to catch the rest. I still had his load in my mouth when he told me to get dressed and fuck off. I quickly swallowed his cum and showed him my empty mouth then got bundled out of the door before I was fully clothed. I stood in the cold night air and straightened my dress before I walked home, cum on my face and panty-less. The moment I was home I went for my fav dildo and fucked myself silly thinking about what a slut I had been.
To be continued...

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I didn’t see much of Emma during the next four days as we both work and I usually don’t get home until about eight o’clock in the evening. When I did bump into her she was very quiet, moody and definitely not her usual chirpy and chatter self. I didn’t know if this was a reaction of embarrassment to me following our lovemaking or if it was just her having one of our standard female mood swings. She was never impolite to me during those few days, she still smiled and said hello but there was no...

1st time at a sex club

Whilst working in England, I came across a ‘sex’ club that according to the website was in a house with many amenities and lots of othe sexually active crossdressers. I sent them a message and got a reply with the next meeting date and a request for a ‘donation’ to help with the website/club expenses. As a crossdresser I was promised plenty of sex from the other patrons – there were plenty of gangbang photos on the website:-) The ‘sex’ day arrived and I prepared very carefully with an enema to...

1st Kiss How I Became an Exhibitionist

I love being an Exhibitionist. I love everything about it. Even now, my clit is twitching as I tell you how turned-on I get when I’m naked and being watched….OMG…my nipples just popped-up…I know that I won’t make it through writing this without having to stop to vibrate myself into an orgasm or two… Anyway… I was, of course, not always like this. There was a time when even walking around the house naked, in front of my husband was something I would never do. Sex was for the bedroom, and...

1st time for Emma Part 3

Sorry it’s taken so long for me to write part 3, I’ve been very busy and not at my computer much for a few weeks… I quickly took off my top and skirt and moved onto the bed on all fours, moving over Emma and gently pushing her shoulders down so she was positioned underneath me. I looked at her directly in the eyes then brushed my lips against hers. She responded by gently kissing me back and pushing her tongue into my mouth. We kissed in this way for a few minutes playing with each others...

1st time and loved it

He kept working his dick into me deeper and deeper, back and forth, till finally he had it all in me. He stopped for a little bit and asked if I was OK. I said I was and to keep doing what he was doing; it was starting to really feel nice. He squeezed my nipples harder. I couldn't believe I was being fucked, I had a man's dick in me and I couldn't believe how good it felt. After several minutes, Jim was starting to fuck me faster and faster. He said he couldn't hold it any longer and started to...

1st time

So a few yrs ago, I was sitting in my hotel with a sexy red pair of lacy thongs and a red lacy bra on looking through hamster, as I was very horny and imagining someone grabbing and rubbing my ass. I recieved a message that someone wanted to come by and suck my cock. I was hesitant to meet a complete stranger, after a few messages I gave him the room number. Roughly 30 mins later I heard a slight knock on the door, I turned off the lights and slowly proceeded to the door. I opened it up and he...

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