Maybe I Really am a Sissy Slut

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I try out my new toys and they blow my mind!
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FemBoyLew
FemBoyLew
47 Followers

**This is Chapter 2 of my fantisized Self-Realization story. To truly understand the whole story, please read Chapter 1: "The Sex Store and my Self-Discovery" before continuing. Thank you!!**

The entire drive back home, I kept thinking about the note. Why does she want me to call her after I cum? Why would she even care? And who is she? Thinking about this kept me in a constant state of arousal, I did not even try to keep my cock in my panties, I could feel the tip rubbing against the inside of the jeans. I so wanted to pull over and rub it out but I knew the added pressure would be well worth it in the end. Through my many hours of researching anal play, I knew an enema kit was a must have, so I ran into the grocery store real fast and picked one up. After what seemed like forever, I finally pulled into my garage.

I slammed the car door close and ran upstairs. I didn't even bother locking my car, I wanted to get started. I emptied the contents of the bag onto my bed and took a second to plan the evening out. As much as I wanted to cum right now, I figured it was best in the long run to slow down and slowly build up to it. I took off my shirt and looked in the mirror. The very top threads of my lace thong were showing over my jeans. This did not help my already aching penis basically crying for attention. I unzipped the jeans and pulled them down, leaving me in only my pink panties with my cock sticking out the side. At that point, I looked at the chastity cage sitting on the bed.

I thought to myself, "How could someone lock up something so important and fun?" I looked back into the mirror and admired myself again. I always thought one of my best traits was my ass, how it sticks out, and the thong only exemplified it. I could not wait to buy more panties in the near future.

I remembered the enema kit so I walked into the bathroom and started that. It felt very strange to feel so full the way an enema makes you, but after a couple of cycles, I finally got the water running clean and I felt clean and empty inside.

I wanted to get into the full scene, so I waited a few minutes for my cock to finally retreat and I could try on the babydoll lingerie. I held it up to my body and the bottom of it came down to the bottom of my panties. I slipped it on and once again, that feeling of silky lace rubbing against my smooth body, makes me wish my whole wardrobe was made of lace and silk. I swear I have never felt sexier in my entire life. The black lace went so well with the pink thong that can still be seen through it. The top part where boobs would normally be looked a bit funny but I could still see my nipples though it, so that was hot. I squeezed and pinched them a bit. I turned around and the back of the babydoll ends about half way up my butt, so the lower half of my cheeks were still naked. I lifted the back up to reveal the thong still tucked away. I felt so feminine at the time and yet had the greatest self-love for myself that I had not felt in a very long time. I think I just discovered something new about me. It brought a tear to my eye that I could finally look in a mirror and be happy about myself.

I posed for some sexy pictures on my bed and was finally ready to get down to business. I laid out the butt plug set, prostate vibrator, and both the 4 inch and 8 inch dildos. I opened the butt plug package and grabbed the smallest one. It was made of metal and was a bit cold. It had a pink rose on the base as well, conveniently matching my panties. I laid on my stomach with my feet in the air and pulled up my babydoll lingerie. I cracked open the bottle of lube and put some on my finger and used my other hand to pull my thong to the side and pull my ass cheek. The feeling of the cold lube against my asshole made me gasp, as I circled around it. I then slowly stuck my middle finger in and out, slowly opening myself up. The inside of my asshole felt tight and smooth, but the feeling of just my finger felt incredible. I wiggled my pointer finger in there as well, so I had two fingers inside me. I moved them in and out, feeling my asshole grip on all sides. I could not believe it, I was fingering my own asshole and yet it felt so good.

Once I felt like I was well lubed up, I put some lube on the butt plug and pressed it against my asshole. It felt about the same size as my two fingers but had more girth to it. I slowly started to press it into me, I moaned and crossed my legs in the air, as I reached the widest part. Then, almost like my ass wanted to swallow it up, the rest got sucked in and all that was left was the base still sticking out.

Even though it was the smallest size, my ass still felt so full, as I pulled it out and pushed it back in. After a couple more times, my asshole loosened up because I was basically fucking myself with the butt plug. I wanted more, so I grabbed the medium sized plug, lubed it up and applied pressure to my anus. This one was decently bigger and it started to hurt a little trying to push it in but the pain just turned me on even more. After a little longer, I got the plug in up to its biggest circumference and now the stretching started. I moaned loudly into my bed sheets and dug my fingernails into my ass cheek trying to open my ass up further. Then it popped in and the pain instantly turned to pure ecstacy. I thought I was full with the small plug.

I did the same as before, slowly pulling it out and hearing my hole pop, then slowly putting it back in. My moans continued into my bed sheets as I looked up at the mirror infront of my bed and no longer saw myself. The 22 year old young man who went into the adult store, left as a sissy slut who likes it up the ass. My cock was agreeing, as it was fully hardened against the bed, I hadn't even touched it yet and I was so turned on. I could feel the puddle of precum that began pooling below me, slowly being smeared around by my pelvis from me squirming.

I pulled it out and put it back in one more time and left it there for a minute to recollect my thoughts. I was in bliss but still wanted more. I looked at the dildos. I stood up and grabbed the 4 inch dildo. It was a bit thicker than the butt plug and certainly longer. Plus the veins on it looked so real. I went back to the bed and resumed the same position, but now with my ass more in the air.

Instead of putting lube on the dildo, I opened my mouth and started to suck it. The closest phallic shaped thing I've ever had close to my mouth was a breadstick or a banana. Never did I think that I would be sucking on a dildo. But I continued to get it all wet, dripping with my saliva. I slowly pulled the butt plug out and felt the rush of cool air enter me. I aimed the dildo towards my backdoor, ready to fill that empty space. I pushed in and could instantly feel the difference. The pain was telling me to stop but my dick and ass wanted me to keep going. Once I got the head of the dildo in, the rest seemed to slide in. I pushed it in about halfway then pulled it all the way out. Everytime I pushed it in, I felt so incredibly full, and so empty when I pulled it out.

Then I pushed it back in and this time went further. I moaned so loud as I felt the veins rub against my sphincter.

"Oh yeah," I moaned, in a slightly higher pitch than normal.

It felt so good, I started to pick up the pace. I was fucking myself at a decent rhythm and each thrust of the dildo kept adding to the pressure. I rolled on my side and lifted my leg up to get deeper. I started to stroke my cock to the same rhythm. By this time, the moans were starting to sound more submissive and higher pitched. Every thrust into my ass caused a whimpered moan to come out of my mouth.

The pressure was something I had never felt before. I felt like I was close to coming so I laid flat on my back with my feet on the bed and knees straight up. I kept fucking my ass and vigorously stroking my dick. By this time, I was moaning and whimpering like crazy, my neighbors would have thought I brought a woman over but no, it was just me and my new favorite toys.

Finally, the stimulation was too much and I could feel myself reaching that point of no return. I stroked my dick as fast as I could while shoving the dildo in even further. I could feel the convulsions of the orgasm starting and then the streams of cum erupted out of my cock. My asshole clenched around the dildo and spurt after spurt of cum came out of me. My eyes were closed and back arched and body shaking, almost screaming out of pure ecstacy as I rode the intense orgasm all the way to the end.

I laid there, still shaking, my whole body feeling electrified with every move. Without opening my eyes, I could feel my entire hand covered in cum, now beginning to cool. It was the most I had ever seen come out of myself.

After the orgasm subsided, I stopped with the dildo, leaving it still shoved in my ass. My cock was so sensitive I stopped stroking it too and looked around. My eyes were a big foggy and I was breathing steadily. There was just cum everywhere, on my hand, all over my lingerie, and even on the wall behind my pillow, a spurt made it that far. I spent a couple of minutes laying there, feeling totally used and loving every second of it.

I came to my senses and pulled the dildo out, leaving my ass gaping, wanting more. I grabbed a couple of tissues and started cleaning up my mess. I still could not believe what I just did.

I got up and readjusted my thong. This is probably the first time my cock was flaccid while wearing them. I looked at myself in the mirror, still in the lingerie with cum all over it.

"This is who I am now," I said to myself. "And I bet that was why Kate wanted me to call her, to let her know how it went."

With that thought in mind, I grabbed the receipt and entered her phone number into my phone. It rang a couple of times and I was worried she was not going to pick up until I heard a hello.

"Hi Kate, I came into the store today and I saw your note on the back of my receipt." she could probably still hear my heightened breathing.

"Oh, you must be the anal slut. So how did you like the toys?" Kate said teasingly.

"You know, I have a completely different perspective on masturbation after tonight," I said, still slightly winded, I could feel my heart rate still elevated.

"Good, good. I knew you were going to like it. Did you use all the toys?" she asked.

"Not all of them. I only used the first two sizes of butt plugs and the 4 inch dildo. I guess I kind of forgot about the other ones and got carried away,"

"Let me guess, you wore your panties and the lingerie dress as well right?" Kate asked, sounding like she already knew the answer.

"Oh Kate I've never felt sexier. I've never loved my body before but with the panties and babydoll on, I'll definitely be back in for more..." I said before Kate interrupted me.

"Let me tell you the real reason why I had you call me after you came. If I had told you this beforehand I would have scared you away from the idea but now you should be like putty in my hand. Aside from working in the sex store, I am also a mistress who specializes in pain and pleasure while helping people find their true identity,"

I couldn't believe what I was hearing, my heart rate was increasing again.

"When I saw you walk through the door I read you like a book. A young boy who thought he wanted a bit of fun but in reality you wanted so much more. You wanted to reach into your kinks but never fully embrace them. You want to be used and abused by someone of a dominant gender, someone who has the tools and methods to make you weak and moldable. You had better start rethinking your fantasies now because you're in them....if you accept,"

"Accept w..what?" I said, fear in my voice as I felt scared but also becoming aroused again, as being owned by a mistress was at the top of my fantasy list.

"I can offer you an escape into your reality and make tonight look like an average jerk off session. Agree to become my slave and you will never need to jerk off again," Kate said, her voice already sounding strict.

I ran what she said through my head a couple of times. It is what I have always wanted but the way she speaks sends shivers through my spine. But then I remembered all the times I was laying in bed alone jerking off to femdom porn and thought I was not likely to get another opportunity like this.

"Well slut, what is it going to be?"

I took a deep breath in. "I agree Kate, I will be your slave."

"Looks like you will need more training. Already you have kept me waiting for an answer and you have already forgotten to call me Mistress Kate. That will require extra discipline," Mistress Kate said, teasingly but with a serious tone.

I must be dreaming. A real mistress talking about punishing me? I had always dreamed of it but never thought it would come true.

"I'm really sorry Mistress Kate. I am still so surprised and excited. I won't let it happen again," I said, talking so fast from excitement and fear.

"Good. I will text you my address and expect you here at 8pm next Saturday night and not a minute late or this whole idea will be over. Do you understand me slave?"

"Yes Mistress Kate, I will not disappoint you," I said.

"Excellent. Bring your pink panties and the babydoll. I have some more items we can add on to you. Bring your toys too, ALL of them. Last thing, do NOT cum again until then. I want you nice and full for when I have my way with you. Goodnight my sissy slave," Mistress Kate hangs up.

I put the phone down and lay back on the bed looking at the ceiling. I still cannot process that this is real. I look down at my babydoll dress, still with dried cum on it. My cock was rock hard again.

"This is going to be a long week."

Keep following my fantasized dreams in Chapter 3 "My Dreams Quickly Become Very Real"

FemBoyLew
FemBoyLew
47 Followers
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4 Comments
AnonymousAnonymousover 1 year ago

Tell her to go to hell. Not who he is.

AnonymousAnonymousover 1 year ago

I had to stop and fill my hole as I read this story

ChloecrossedChloecrossedover 1 year ago

You were describing me when you described your sissy masturbation session. So hot, so wonderful, there’ll be no turning back now! Xxxxx

FailedscoutFailedscoutover 1 year ago

This seems like a fun story so far. I look forward to the next chapter.

Thank you for writing and posting here.

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