Sissy Whisperer, Ch. 02

She blushed, "You're a doll." As I let go of her hand. "Do you think you would be coming to the next CD night? I'd love to have some help. I mean, don't get me wrong, I love being the center of attention, but my jaw gets sore from all the..." And then she made the classic motion with hand and tongue against a cheek mimicking giving head.

Keri and I chuckled. Then Keri responded, "I think Elli would make a great addition to CD night, but she is just starting to figure things out."

Brenda then leaned in and gave me a light girl-like hug and I got a good whiff of her perfume and wondered what it was. She then stepped back and said, "Well, if you need any advice or someone to talk to, feel free to reach out Honey." She paused to examine me some more. "I even know a few clean guys that would love to help you figure things out." And then she gave me a wink.

I smiled, "Thank you." She then walked by and out the door. Keri and I both watched her walk gracefully out the door causing the 'bing bong' again and I laughed a little.

"Brenda is really super great. I just love how she dresses, sort of Sexy Secretary. And did you see her bag. That wasn't a knock off." Keri paused while looking at the door and then turned to look at me. "God I'd love a bag like that someday." She sighed. "Anyway, like she said, she could use some help on CD night. I know Bob would love that too. We used to make a mint on CD night when there were more ladies here." She paused, "But, we are getting ahead of ourselves, I think you need to gain some one-on-one experience with a guy first, I mean, assuming you would like to try that."

Without hesitation, "I think, I would be interested in helping her on CD nights." I said.

"Well, aren't you just a good sister Samaritan. I think a good first step would be to get you a profile on the fetish site we use for advertising events we hold. Brenda and Red are on there as well as many of our customers. You'll need some sexy pic, so..." She noticed I was looking down at my bag. "I bet you can't wait to try that on." Keri said smiling.

I looked up with a small smile and nodded yes, but I haven't paid for it yet. "Yes, very much, but how much do I owe?"

"Nothing, it's a gift for your first visit to the Store." She paused. "All Adult Stores do that."

"Really?" I said looking up at her.

"Gawd, you can really be a bimbo sometimes." She looked slightly perturbed at how naive I was. "Well, no one else is here, so why don't you go change in one of the booths." She nodded her head toward the back.

Without a second thought, I turned to walk down the hall to the booths. I thought she might have been joking, but then I heard "Take the last booth on the right and come back up here when you are dressed."

Opening the door to the last room, the light came on and then the video screen came on. There was a slight perfume smell matching Brenda's scent with a hint of jizz. The screen in front of me was showing a porno trailer with a hot blonde on her back, legs spread while getting railed by a big muscular guy. Since being introduced to sissies and BBC, I wondered what it would be like to be her. I always found being the guy during sex to be full of anxiety and had a difficult time enjoying it while I worried about whether I was doing it right and if she liked it. It felt more like a chore than fun. But now, I found the feminine role to be more desirable and it gave me a renewed interest in sex.

I returned my focus on getting changed, I stripped naked, rolled my clothes up into a small bundle. I picked up the babydoll, detached the thong and slid it up my legs. I was completely smooth following the rules in Keri's email. The thong was soft, fit snugly between my cheeks and provided just enough material to hold my bits. Next, I slid the babydoll on like a tank top. It was a little tight around my chest but fell loosey around my waist with the faux fur trim tickling my butt. I sat down and opened the package of stockings. I never put on stockings before, but I knew enough that I needed to bunch them up and slowly slide them up my legs. It felt incredible sliding the first stocking up my leg. After I did the same with the other leg, I noticed the lace tops had silicone bands like my bicycle shorts to keep them in place. Afterwards, I placed the heels on the floor and stepped into them.

My first time standing in heels felt like I needed to reset my internal balancing system. After a couple of seconds and adjusting my balance, I then felt like my butt was higher and bigger. Looking down, I noticed my stockings weren't even and I adjusted them to look proper. I then slid my hands down each leg to even them the tone out and it felt electric. Compared to these, my socks would feel like burlap. I could feel my bits were becoming aroused and I had to nip that quickly.

I was always limp when I rode the dildo, so I thought the butt plug could help stop my little guy from growing anymore. I opened the box, inside was a little black velvet bag and inside that was hefty shiny plum size hunk of chrome steel with a little pink jewel end. It looked wider than the dildo I have been practicing with and I was concerned it may not fit. Inside the bag were a few packets of sample lube so I used that to help finger my hole a little. Then with a firm grip on the jeweled end, I squatted a little and began pressing it into me bum. As I pushed it in, it started to hurt, so I took short breaks to help things relax around it. After doing this a few more times, eventually it got past the widest point, then my butt sort of sucked the rest of it up in me. I moaned a little as I could feel it rest against my prostate. I slid my thong back into place, stood up, wiggled my butt a little and thought it felt nice. Just about any movement at all caused it to rub against my prostate and it was very enjoyable.

Then I sat down, "Oh gawd." blurted out of my mouth as the plug pushed hard against my prostate. Keri was right, I was going to really enjoy having this in me. As far as my bits go, it was back to limp and useless.

Worried I was talking too long, I stood up, placed the chastity device and choker on the chair, took a few practice steps around the sex closet to get used to the shoes. I felt like I had a more feminine stride with the butt plug reminding me with each step rubbing my p-spot. Without a mirror, I looked down one last time to make sure my outfit fit properly. Then, I gave my hair a shake, pushed it up and out with my fingers to try to make it look sexy and allowing it covered my ears, flowed over the sides of my face with the tips just curling under my chin.

I took a deep breath, opened the door to the hallway and began the long walk to the counter. I did my best model walk, heel to toe, elbows in and shoulders back. I'd need more practice, but I felt confident and the sound of each step of my heels made it clear that someone feminine was walking down the hall.

Keri heard me coming down the hall, peered out over the counter smiling, eyes widened and then her head popped back out of sight. The door opened and she trotted to me, hooked my arm with hers turning me around and quickly led me back to the booth. I had to shuffle to keep up with her and was worried I'd flip off a shoe. Luckily, I kept up with her and she pushed me into the booth and closed the door behind us. "Sorry, but another guy came in and if he saw your hot little ass, I don't think I could keep his hands off you."

"Oh wow, that was close. Thanks." I said, feeling oddly secure in a sex booth with a glory hole.

Keri stepped back to get a look at me, she smiled, "Wow, you really do look hot. Give be me a twirl girl." She grabbed my hand, lifted it above my head and twisted causing me to twirl. The babydoll spread out a little then came back to rest tickling my bum again. "Just hmmm." She saw the chastity device and choker on the chair and walked over to pick up the choker. "Here, turn around and I'll put this on you."

I turned my back toward her and lifted my hair out of the way. As she placed it around my neck, it closed the clasp, and it was snug, and I could feel that it sort of covered my adams apple. Then before I could turn around to face her, she placed a hand on each side of my hips tightly and pulled me against her while she thrusted herself into me. This caused me to lose my balance and bend over bracing my hands on my shines. "That's my girl, assume the position slut." She then thrusted again pulling me tight and grinded against my butt plug pressing it hard against my prostate. Which caused me to moan loudly. "I told you, you would love that."

"Oh ya, that feels like you're fucking me." I said.

She then let go and I was disappointed it ended so quickly, but she was focused on the last thing to complete my outfit. She picked up the box with the chastity device and sat down on the chair. "Ok, slut, let's get this fitted properly." She opened the box, pulled out a set of rings, cylinder locks with keys and the cap piece, placing all of it on her lap. With my crotch eye level, she pulled my thong down and I held my babydoll out of the way so we both had a better view down there.

"This is really ideal for you. Your thingy is so cute and small. It will be much happier in this." She took the smallest ring, reached up with one hand and pulled my limp penis thru the ring, "I can barely get a hold of your clitty." She then pushed one testicle through from the back. Normally, having a girl touch my junk would stimulate me, but then she started to push the other nut through, and it was too uncomfortable to get aroused. I had to grab her shoulder tightly as she kept pushing and the pain got worse. "Sorry, this will hurt a little, but this size ring is ideal for your little acorns. We don't want them slipping out of this." As soon as she said that it popped through and I eased my grip on her shoulder.

Next, she picked up the cap end piece shaped like a tiny vagina and placed that up against my penis, pushing it back until the cap matched the slot on the ring. It squished my clitty down like a crushing a very tiny soda can. She had me hold the two pieces together while she prepared the cylinder with a key, then married the two pieces together and locked it all in place. She removed the key, placing it in her bra, leaned back, smiled. "That looks so much better, you look like a proper sissy now. Don't you think so?"

I looked down, waggled it a little in front of her and she giggled. "Yes, it's a little uncomfortable, but it looks cute."

She then explained, "It will take some time to really get used to it. I'll hold on to this key and you can have the other one for now, but you need to wear it as much as possible. Eventually, I'd like to be your keyholder where you can only get out of this if I give you the key." I nodded acknowledging I understood her instructions.

She took out her phone and snapped a picture and pulled my thong back up and took another photo that showed a small bulge with the outline of the device, making it clear I was now a caged sissy.

"These are for your profile that I'll help set up for you." She told me, then stood up, pulled a tube of lip gloss from her back pocket and handed it to me. "Lets see how your make-up tutorials are going." I pursed my lips like last Friday and within seconds, I had pink lips. "Wow, very good Elli. Let's give your eyes a little sultry look with these." She pulled out mascara and eyeliner from her pocket. "This go quicker, if I do it, but you can have these to practice at home." After she was done and pleased with the look, "Now, let's take a few more pics for your profile."

She directed me to stand up straight, shoulder back, elbows in, feet together and I tilted my head a little to the side. It felt very demure in nature. After she was pleased with that pose, she clicked a couple of photos. The next pose involved me placing my hands on the back of the chair, bend over, spread my legs and look back at her. "Your ass is so hot." I heard a couple more clicks and then she reached for my thong, pulled it the side and had me bend over more to get a clear view of my pink heart shape jewel. She reached in twisted it, "There now it's nice and straight." Then click, click.

Her next direction had me kneel in front of the glory hole with my eyes looking at her and tongue sticking out like I was waiting for a cock to come through. Then I heard a zipper-like sound coming from the other room. My eyes widened, Keri, didn't hear it, but before she could figure out why I was so doe eyed, her mouth dropped wide open. I turned to see what caused her mouth to gap and a mere inch from my mouth was the tip a cock bending down from its unsupported weight while it was in a semi hard state. It was so much larger than mine and it wasn't fully erect. Then I noticed his aroma, musky, but with a hint of maybe Irish spring and I liked it.

I felt like I was frozen again staring at it. Keri noticed and gave me a little encouragement, whispering, "Go for it slut."

I changed my position a little, I squared up to the hole with my knees on the little pad, my butt resting on my heels, my back arched with my babydoll slightly riding up exposing my butt and thong as I leaned in closer to this amazing example of man meat. Then I reached up and for the first time, I touched a man's cock. I stroked him with my fingers, and he jumped at my touch which made me jump a little and I giggled a little. I turned to look at Keri and smiled. She gave me a thumbs up while holding up her phone filming me. "You got this slut."

So, I turned back to give him my full unbridled attention and began to stroke him lightly, sliding my hand delicately up and down the shaft while I softly fondled his plums with the other hand. His skin was so soft, and I could feel his heartbeat as it continued to get harder and wider. The head plumped up and became shiny showing that he was now at full mast. He must have been 8" and thick like a polish kielbasa with a bulbous mushroom head.

I licked my lips, flipped my hair to the side so it wouldn't be in the way, leaned in, and kissed it. I thought about all the porn I watched in the last few days and told myself, I got this. I'm going to please him with my mouth and savor seed from a real man.

I moved my head forward to get the entire head in my mouth. I licked the pee hole and could taste pre-cum which I immediately began to crave. But before I got too focused on sucking him off, I wanted to taste his balls, the home of the seed I would soon savor. I lick the underside of his shaft to his balls with his shaft resting against my forehead. Then one at a time, I kissed, licked and caress each of his plums in my mouth while lightly massaging each with my tongue.

After giving his manly gonads satisfactory oral attention, I craved to feel his cock in my mouth again. I replaced my mouth with my hand to fondle them some more. I licked the underside back up to the head, keeping my tongue on the underside while sliding my mouth over the head. I swirled my tongue around the entire head clockwise and then counterclockwise while stroking him with my hands. This made my head circle a little and my butt wiggle involuntarily. That caused my heels to rub against my jeweled end, giving me pleasure and causing me to moan energetically. I continued to hump my heel while moaning with his head in my mouth and that made me more eager to take more of him into my mouth. Moving my head forward more and more until I knew it was time to test my gag reflex. I was already breathing through my nose and moaning or humming which were both tricks I learned from the instructional videos on how to tame the gag reflex. I could feel that I was becoming wet. I removed my hand from his balls and reached down to rub my clit. I was most definitely wet.

Now it was time to give him attention only with my mouth and hopefully my throat. I wanted to feel his pubs tickle my nose. I moved my hands to place them on either side of the hole on the wall and began to slide up and down to let the cock slide deeper and deeper into my mouth. My moaning and breathing were steady as I lightly tested my gag reflex a little more each time I slid up and down his shaft. My eyes were watering from the unnatural predicament. I could feel my hair move with each bob and tickle my cheeks. His head was as big as the dildo I had been practicing with and I was confident I could swallow him. With a couple more bobs, I pushed and swallowed him which allowed him to slide down my throat until I hit my forehead on the wall which startled me. I backed off totally removing from my mouth, smiled at how it glistens from my saliva, then I quickly put him back in my mouth and swallowed him again and could feel his pubs on my nose.

I was so happy with this achievement, I gave a double thumbs up and then moved my hands to each side of my butt and gobbling his cock, bobbing back and forth faster and faster. I could hear the slurping noises coming from my mouth with each stroke, I could hear him talking and groaning, "That's it you sissy slut, you're sucking a real man's cock. Oh' yah, faster, you sissy slut." I loved hearing that he was enjoying my skills.

It felt like minutes, but I started to feel his head get even bigger and I could hear him say, "Get ready, you cock sucking sissy slut, Daddy is going to cum."

I could hear Keri cheering me on behind me, "You're doing great Elli, keep it up, he won't be able to last much longer."

I started to thrust my head even faster onto him and returned my hands to the wall so my forehead would hit my fingers instead of the wall. I was a bitch in heat, I needed his cum. His groans sounded animalistic, and I started to feel his cock pulse. I kept the pace steady, and he pushed as much of his cock through the hole as possible and my nose touched his belly. I could feel the first shot move up his shaft and then down my throat. I then slid back in time to catch the second and third shot in my mouth. There wasn't enough room in my mouth for his seed and bulbous head and some slipped past my lips on dribbled down my chin.

The taste was more manly than my sissy cum if that was even possible. I savored the feel of his cum in my mouth, it was thick like yogurt. Then I returned my attention to head and while pumping his shaft into my mouth with both hands, I tried to suck out every last swimmer I could get. I wasn't going to let one little guy go to waste.

I heard a whisper behind me from Keri, "Show me your prize."

I kept hold of his cock with my hands, then settled back onto my heels removing him from my mouth. I long string kept us connected momentarily until I turned to show Keri my open mouth full of his cum with some dribbling down my chin. She smiled, still filming me. I then closed my mouth, savored the taste one last time, swallowed and open my cock sucking mouth to show it was on its way to my tummy. She smiled again, "Good girl."

I then returned to his cock, he could feel him deflating, and his head was no longer full and plump. I knew his head would be super sensitive at this stage, so I gently licked the remaining drips of cum and saliva. I let go of him as well and he pulled it back through the hole. I placed my hands on either side of the hole with my mouth still open while wiggling my ass a little, but he wasn't coming back through. Keri tapped my shoulder, "It's ok, you'll get to suck more cock other time sweety." She then reach her hand out, "Here let me help you up." My legs were a bit weak from kneeling this whole time and I staggered a little on my heels before I totally regained my balance, Keri gave me a tight hug, whispered in my ear, "That was SOOO fricken hot. Do you know what you are now?"

I leaned back, stared her into her eyes, smiled and maybe too confidently I loudly said, "I am cock sucking sissy."