u/girlonormal

This is the true story of my first real sissy experience. 
One night I was rolling on a little molly. I was cleaning with enemas and looking on Grindr for some fantasy material. Someone had tapped my profile with the username, “letmeeaturass.” I messaged him and invited him over! I paid him $20 for an uber! I dressed up in a cute cute cute cute cute outfit. Muted pink sports bra with the false breasts inserted underneath my crop top bold pink polo midriff shirt. I want to get my bellybutton pierced. Then I had on that adorable flouncy pink skirt with the ruffles that felt so nice to wear. Beneath that I had on a bright pink Victoria’s secret thong that framed my ass perfectly. Underneath the thong I was wearing this amazing black garter belt and stocking combo that made me feel so sexy. It’s important to put the stockings underneath the underwear so it’s easier to take them off. I just moved mine to the side. I also put in my smallest metal butt plug with the bright pink jeweled base. 

I put on a little bit of makeup- just some sparkly amber eyeshadow and pink lipstick. A quick spritz of perfume and I was feeling confident. Then I put on my heart shaped collar and pink wig. I quickly set the mood by lighting candles and putting on a sexy playlist. I took two pillows and placed them near my door. I texted the Grindr guy to just knock on the door and I would leave it unlocked so he could walk in and immediately eat my ass. I assumed the position of face down, ass up on the pillows and it felt right. The excitement I felt while I was waiting was genuinely electric. My entire body was buzzing with energy and I was nervous, excited, scared, incredulous, unsure, and incredibly turned on. My lust levels were high. My horniness was approaching maximum levels. The sexual excitement was over 9000. 

Finally the knock at the door came. I called out, “Come in,” and the door opened. He came in, closed the door, slowly lifted my skirt up, pulled my thong to the side, took out my buttplug and then began to passionately eat my ass. It was amazing. I felt like a complete and total slut. His tongue was doing wonders for me as I moaned and writhed under his oral assault. I was completely overwhelmed by pleasure and came in powerful waves of ecstasy. 
Eventually my hips buckled and I collapsed to the floor in pure bliss. I flipped over and finally looked at my male visitor. I told him it was amazing and would he please follow me to the bedroom for more? We briefly exchanged names and pleasantries.

I instructed him to bring the candles to the bedroom and then I sat on his face. It was a dream come true. I gyrated and moaned and enjoyed every minute of it. It was so erotic and naughty to be dressed up like a slut and having my ass passionately eaten! I could have stayed there forever! I came again and the shaking from my legs was so extreme that I had to slide off and lay beside him on the bed. 

My memory of the entire encounter is slightly hazy because I was drinking a little bit that day and I had taken a good amount of MDMA also. But I think what happened next is that I gestured to my nightstand that was occupied with my sizable dildo collection. I requested he pick one and he selected my lovely 7” clear boy and proceeded to slowly penetrate me with it. My bliss reached previously uncharted territories. I laid on my back and pulled my stocking-clad legs up high into the air. He gently slid the toy in and out of me, I bucked my hips wantonly to activate my deepest pleasure buttons and I lost myself in the passionate throes of lust. 

At some point I asked him to switch to my black and red alien dildo and said some silly high shit like, “take me to your leader” and he still went along with it! We had crazy amounts of fun with the toys, I retrieved my wand vibrator and was using it too. I should also add that I had been wearing my pink chastity cage this entire time! That added to the overall feeling of being excited by the ‘degenerate’ nature of that evening’s events. 

I love being an adult that buys fun toys. I brought out my lovense and made him hold it while I opened the app and demonstrated how to control the vibration. He may be dumb enough to eat a stranger's raw butt, but he caught on quickly with the concept of teledildonics. I invited him to play with me while I rolled us a joint and really exaggerated my moaning. I am incredibly thrilled by the advent of teledildonics and I think the interface of computers and robotics and pleasure and software and orgasms is incredibly hot. I really want to make a robot cum. I’m adding that to my bucket list. Lol 

Ok anyway we’re smoking some weed, I did a quick outfit change into that little orange bodysuit that is so fucking sexy. I was dancing around a little bit, bending over and asking to be spanked, it was insane. I didn’t tell him that I was rolling on molly but I think he might have possibly been able to tell based on how much I was grinding my fucking teeth lol. I thought that I was playing it cool but in reality I was probably absolutely unhinged and buzzing and embracing the situation. We smoked a little bit on my balcony and I asked him if I could grind my ass on his crotch. I really loved dancing on him, bending over, feeling his cock get hard and grinding on his dick. 

We’re back in the bedroom and I tell him that I want to ride his face again, “but this time take your pants off.” I went into the bathroom to apply a new coat of pink lipstick and give myself a quick pep talk. I stared at myself in the mirror and was overwhelmed with incredible feelings of love and lust. I felt desirable. It was a powerful feeling. 

Then I went back in and rode his face some more. Josh’s grindr profile was called, “letmeeaturass” and so I let him. I was loving the way his tongue was exploring my sacred depths and vocalizing my pleasure like a true slut. It was amazing and my hands were tightly grasping his strong legs. He had told me at some point that he was a roofer and I appreciated his working-man aesthetics. My hands played across his body and I adjusted my posture on his face while I caressed him higher and higher. I finally touched his penis. It was… great. I enjoyed it. I grabbed him, stroked him, played with him, squeezed him, and he grew hard and expanded in my hands. It was intoxicating, it was magical. I could hear him groan in appreciation as his organ grew. I leaned down and gave it a very slow kiss on the shaft. It was a very nice size. Not small, it was bigger than mine, but not unmanageable. I was so turned on I had to take another break and lay down beside him again. 

I lay next to him, panting and trying to recover my breath after my analingus-induced orgasms. I was feeling incredibly grateful as my left hand lazily explored Josh’s body next to me on my mattress. My hand eventually made its way to his pubic region as I idly stared off into the distance. My thoughts were rapid and scattered as I languidly stroked his hard cock. What would xyz think if they could see me now? I rubbed and squeezed his balls. Am I going to regret this? I pulled back his foreskin and relished a satisfying drop of pre-cum. What are you doing Greg? I gently jacked him off. 

There were so many thoughts going through my head and I struggled to align myself. “I am breathing in, and I know that I am breathing in. I am breathing out, and I know that I am breathing out.” I silently repeat this mantra as my heart gradually regains a normal rhythm and my breath slows. I realize that my hand is still idly stroking this man’s cock and I start to turn my mind to what to do next. He has given me so much pleasure, I should return the favor. 

I sit up off the bed and take a few pumps of lube in my right hand and apply it to his naked cock. What a seminal moment! I begin to stroke him using my years of practice as a cock-owner. I know what feels good when I grasp him and apply different pressure and swirl my fist and tapdance my fingers along his shaft and tell him how amazing his dick is and and and and and and and and! 

I’m flustered and overwhelmed again and lay back to catch my breath once more. Can he tell how fucking hard I’m rolling? My teeth are grinding audibly and I’m sighing in pleasure constantly. I am also allowing myself to feel a lot of conflicting emotions all at once and trying to quietly contain my powerful buzzing inside. Eventually I can’t hold it and I decide to use an incredibly powerful technique. I read about this in an important text and it has stuck with me due to its revolutionary teaching. I allowed myself to say out loud the feelings that I was experiencing! I know. It is an insane proposition, but wow it feels so good. I spoke out loud that I was feeling confused, excited, guilty, high and definitely horny. And I was thinking about asking Josh to reach over into the bedside night stand and to grab a condom from the top drawer and then put it on his cock so I could sit on it. I have never said anything remotely similar to those words before so it was truly a unique experience that I had never even imagined that I would have during my time on planet Earth. But I had said it and the words hung heavy in the air. But only for a moment before Josh lunged for the night stand. I grabbed his arm and asked him to wait because I said that I was only thinking about saying that! To his immense credit, he stopped and let me stroke his cock a little longer while I pondered and rolled face. I really actually lucked out by snagging this chill dude for a night. 
You can probably guess what happened next. 

I straddled him in reverse cowgirl and spread my ass open. I twerked to the best of my ability and rubbed his cock on my ass to make him rock hard. He warned me that it would make him cum. I said yes please, that’s the idea. He put the condom on, I applied some lube and then put him in. It was heavenly. I rode him hard, I rode him fast and it was fucking incredible. His dick was so hot inside of me, I couldn’t hold anything back. I was leaning forward and bouncing my cute pilates ass on him as best as I could. Then I leaned back and really increased the tempo while he hit me deep in my prostate. 

He came. I came.

Yes. It was tremendous. 

I put my full weight onto his dick and ground it around in a circular motion and milked every last drop of cum out of him that I could. I did it. I felt accomplished, I felt satisfied and I felt great. I told him to spoon me, we hung out a bit and talked some. We smoked a little more weed, and I changed into another cute girly outfit. He fixed my sink also lol. 

Then I told him it was time to go. He left and that was that. 

Hope to try it again soon.