Sissy Whisperer, Ch. 02

Thanks for the all the comments and ratings. It really was very sweet and appreciated. FYI, I have plans and ideas for at least a few more chapters, so stay tuned boys and girls.

Sissy Whisperer-Chapter 2

After agreeing to Keri's plan on how to de-stress from exams, it led to me finding that I have a sissy side and genuinely enjoyed getting pegged. Keri stayed over to make sure I was ok in the morning after I had less alcohol swimming through my veins.

It was mid-morning when I slowly woke up feeling her spooning/humping me and squeezing what little titties I had. We were still in our 'Daddy's Girl' outfits and although it felt nice, my overwhelming need to pee was too strong to stay enjoy it any longer. Sitting up caused an unmistakable throbbing in my head and walking helped remind me the ass pounding I received. I thought she would make a great nurse for a proctologist.

After peeing, medication for my headache and electrolytes were next. Then I started to make some bagels, cut up some fruit for Keri and me to share for breakfast. Keri came in a few minutes later still rocking her outfit and the sexiest bed hair I have ever seen. She gave my ass a hard slap, "That's my girl, making me some breakfast."

We talked a little about how I was doing, and except for the hangover, I was good and thanked her for introducing me to the sissy life. She was pleased to hear that and would help me with anything I needed to explore this side of me more.

After breakfast, we took turns taking a shower. Keri was first and smiled when she came out in a towel snuggly wrapped around her chest and just covering her butt. She said she left a surprise in the shower. Stuck to the wall opposite of the shower head at about ass level was the black dildo she used on my ass with a bottle of lube next to my bodywash. This will certainly make shower time way more entertaining.

After my shower and brief dildo riding, I cleaned the dildo, then placed it back on the wall of the shower. I didn't let my hair get too wet knowing a blow dryer wasn't an option with my headache. I brushed my hair out and lightly gave it some volume. It wasn't super feminine, but it gave my hair a hint of a brunette Rachel.

I was a bit stumped about what I wanted to wear. My 'Daddy's Girl' outfit was a bit too dirty to wear again and I wished I had something else feminine to wear, but I settled for a pink tank top and some black running shorts. I felt feminine on the inside although I probably still look like a skinny, androgynous bloke getting ready for a run.

Pleased with my look, I stepped into some flip flops and scuffed my way to the living room where Keri was sitting on the couch fingering her phone. She was wearing the outfit that she originally arrived in, black leggings and a college sweatshirt just long enough to cover her bum. I sat in my spot on the couch and mentioned I felt much better after my shower. She smiled, "I bet you did slut. I was worried you'd never come out of there." Then she handed me my tablet, "Elli, unlock this for me, I'll add some bookmarks for you to check out." I unlocked it and handed it back to her, "Cute hair, I like it like that."

Referring to me as 'Elli' was something she did sometimes when we hung out. It was short of Elliot, but obviously more feminine. It never bothered me; I just considered it her nickname for me.

We talked a little more about what we each had planned for the break between semesters. We both were going to work extra hours at our jobs with her at the Adult Store and me at my boring insurance agency. But we would make time to hang out when we were both free from work. She requested that I stop by the store after work sometime this week and that if I did, she would give 'Elli' a gift. I was intrigued to know what, but she would not say and that I had to come to find out. Since I always recanted that I would and never did stop by, I think she thought propositioning me with a gift would help sway me to visit.

Soon after Keri finished with my tablet, she gave some instructions to check out all the sites and to check my email where she sent a list of things I should start doing on a daily basis. She asked me to walk her to her car, gave me a hug and soft quick kiss, gave my buttock a squeeze and told me to go explore the sites she bookmarked. Her affection toward me was nice, but I didn't feel like we were now an item, but more like good girlfriends.

Back inside, I immediately hopped on the coach and first checked my email. The list was titled, 'To become a good sissy slut' and including yoga with a link to a video 'Yoga for sissies', to shave all my body hair which I didn't have a lot to begin with, but I always enjoyed freshly shaved legs for cycling or triathlon events. The list included a diet, a link to foods high in natural estrogen and supplements to help with nail and hair care. Skincare tasks that included a weekly facial mask, moisturize after I shower and to use women's deodorant. To watch at least 30 minutes of sissy hypno each day and practice both my oral and anal skills afterwards or during these sessions. To watch links related to makeup and nail care tutorials. Lastly, no more jerking off and pee like a girl.

I then checked out the bookmarks which included sites to help learn how to become the perfect sissy, porn sites that specialized in transgender related theme, BBC porn and my new favorite, sissy hypno. A couple of the sites contained written erotica, sissy apparel, sex toys and a fetish social site.

I was very intrigued by how feminine many of the girls looked and even naked, they were so beautiful, and I started to feel envious of them. When I wasn't on my tablet studying my new obsession, I was in my bedroom playing with the dildo practicing my oral skills and then giving myself pleasure anally.

Monday came quick and going to work was tough. At first, I was less than enthused about wearing khakis and polo, then I was a frustrated it would be hours before I could play with my dildo or watch sissy hypno again. But after hearing a couple of the girls talking about their weekend, I joined them to get coffee and I found that I was more sociable than usual. That helped give me some confidence and the day went by surprisingly fast.

After work, I was in a good mood and instead of heading home and going for a run, I decided I would see if Keri was working. I sent her a text asking what days she would be at the store. She responded that she was there now, followed by the nights she would be working. I simply responded thanks. She texted back asking what day I would come in. I didn't let her know I was on my way to her store of debauchery but responded with 'we'll see.'

The parking lot had plenty of parking, but only three vehicles were parked near the store entrance. I was a bit nervous, and I took a deep breath before I stepped out of my car. The door to the store was nearby, but it felt like a much longer walk. Opening the door to the store, I heard 'bing bong' and it reminded me of the dry cleaners on a Family Guy episode. With a little chuckle, I recalled the episode in my goofy brain.

My first impression was that it reminded me of Spencer Gifts with black wire racks containing various things that weren't immediately identifiable, and my main goal was to locate Keri first. A brief shriek to my left helped find her quickly. There she was at the counter leaning over smiling. As I walked up to the counter, she came down and through a door that separated her from the main floor of the store. She jumped at me, gave me a tight squeezing hug, then leaned back before giving me a short kiss on the lips.

She stepped back and greeted me, "We'll see. You cheeky monkey! This is such a pleasant surprise."

Then from another part of the store, "You never greet me like that."

Looking over my right shoulder, there was a tall guy with a reddish gray beard with a red and white trucker hat peering over a rack. Keri tilted her head looking toward the guy, "Red, I thought you were in the back. Brenda has been back there for over an hour, and I bet you have something she is craving for." She, then looked back at me beaming, "Let me show you around." She hooked my arm and started to lead me on her tour. Red seemed to wander off toward the back of the store.

Keri pointed to her counter and explained she spent most of her time behind the counter. Then we walked to a rack of videos, and she pointed out the porno we watched together. She then provided some recommendations and her favorites, but then joked, that the internet basically made this section a dust collector.

Next, we walked by the magazines where I think Red was before. She picked up a BBC one and handed it to me. I started to flip through it and was astonished that dicks could be that big and the guys were fit with washboard abs. Each flip of the page made my mind race wondering what it would feel like to just hold a cock that big in my hands. They looked so heavy, and I joked, "This magazine feels lighter than it should be."

She looked at me with a quizzed look, then laughed when she got my joke and responded. "I have always been curious on what it would be like to take it from a man with a massive cock like that. I feel like I would worship it up close, feel every inch with my hands and be in awe at the weight of it. Then I would try to see how much I could get in my mouth while fondling his massive plums in my tiny hands. I would love to feel it between my breast too and see if I could wrap them around his girth..." She paused and sort of shock her head, "Sorry, I was somewhere else for a second."

"Yes, you were, but I admit, I had similar thoughts." I said.

She smiled and then took the magazine from my hands, put it back on the rack. "I'm glad we have similar interests."

Then we walked a few feet to another set of racks and shelfs with various type of sex toys. She led me to a shelf and pointed to the box showing an illustration of a black dildo that looked like the one she left at my house. Next to it were two more, each larger than the next. Sort of a S, M and L of the same version. Then I looked around at some of the others and they were in different colors, shapes, some looked like arms with small fists, some were oddly shaped like tentacles, and some were so huge I thought it was a joke or maybe a statue. It was shocking, "Do people really use these?" As I tried to wrap my hand around one that was wider than my thigh.

"You'd be surprised, but here, hold this one." She handed me the next bigger size of the one she used on me. On the box, it had some measurements, 2" girth, 9" from tip to the balls. "This is the next size up like the one I left at your house. I assume black is still your favorite color in a cock."

I nodded, smiled, and held onto the box while she moved us around the other side of the rack where there were a variety of butt plugs. She picked up a box with a picture of a silver plug with a pink heart jewel on it. "You'll really enjoy this." Then handed it to me. "It will feel amazing pressing against your P-spot, plus it helps keep you relaxed for when you want to play with your dildo or maybe get fucked by a real man."

She then turned to a shelf with male chastity devices and picked up a box with a pink device shown on it that looked like a pink ring with a capped end that looked like a really small vagina. "This is also an essential item for a sissy. It keeps you from jerking off, so you only desire pleasure anally. Since I got a peek at your thingy the other night, this should fit you perfectly and I'll help fit this on you maybe when I come over sometime this week. My initial thought was that it looked very uncomfortable, but she was the expert, so I was game to try it.

My hands were full carrying the three boxes and I shifted them around to make it easier to carry them. She noticed, "Wait here." Within a second, she was back with a plastic tote, and she placed the boxes in that, then handed the tote to me to carry.

She grabbed my hand and pulled me to the next area which included apparel. There were racks bags of varies costumes for role playing, wigs, shoes, boots, various leather garments and some clothes on circular racks like skirts, tops and lingerie. She again showed me the outfit we wore which was in one of the little bags, then led me to the circular rack and started to slide items side to side. When she came pink lingerie, I paused her to reach out and feel how soft it was. I slid my hand down to the bottom of the cute negligee and it had faux fur trim, Keri said, "That is a babydoll, it would HOT on you, and it comes with a cute little thong." She then took one from the rack, placed it in my tote, then turned to a rack of hosiery. "You'll need these too." She showed me a package of white thigh high stockings, then placed that in the tote too.

She turned to another section that looked like dog collars and picked up a pink one and presented it to me. It had 'SISSY 'in what I guess were rhinestones across the collar. Smiling, she placed that in my tote.

She walked toward the shoes, and I followed. The variety was amazing, so many different styles in various heights and colors. She walked over to a pair of pink heels that looked like sandals but with a 3" clear spike heel and a small pink satin bow on the strap over the middle of the foot. She looked at them, then at my feet, "You're a size 10?"

I looked down than back at her, "No, a 9."

She rolled her eyes, "You're a women's size 10." She scrolled down until she found a box in my size and picked it up and placed it in my tote which was getting full. "These will go great with your outfit and a good height for you to practice walking in." She then led me back to the counter, took the tote and placed it on the counter, "We'll take care of that later, now onto the pièce de résistance of the store."

She took my hand and led me down a long red hallway with black silhouettes of women in various provocative poses. At the end of the hallway were a series of doors, four on each side of the hallway and each had a red-light bulb above the door. The lights were on above the 3rd and 4th doors on the right side. Quietly, she started to explain, "These are the video booths. If the light is on above the door, it means they are occupied. She opened the first door on the right side, and we walked in, most of the light in the room came from the video screen playing trailers of pornos, but there was one dim ceiling light as well. In front of the screen was a folding chair and the overall size of the room was maybe 4' wide and 6' from the screen to the back of the door. She quietly began to explain, "This is where the magic happens. Mostly guys come in here to bust a nut. Some watch the porn to jack it and some...." She then walked over to the hole in the wall and sort of presented it like a model on Price is Right. "use the infamous glory hole." She chuckled. "There is even a pad on the floor for your knees. We like to give our orally gifted costumers a little comfort so they can concentrate on pleasing a manly cock."

I laughed a little staring at the hole, and it was pitch black on the other side. She explained the light comes on when there is someone in the next room. Then I heard a grunt in the distance and Keri did too. Keri's eyes widen looking at me while placing her hand over her mouth, then came closer to me, "I think Brenda just got Red off." Then she gave me a wink. "Good for her and good for him too. I like it when our customers mutually get what they desire."

I was curious, "So do women come in here often to blow guys?"

She then led me out of the booth and while walking back to the counter she explained, "Women? No, not very often, Ladies like Brenda used to come here fairly often."

I was confused, "I don't understand."

She briefly looked at me then continued to explain, "Oh' Sorry, Brenda is a bi-crossdresser and I use the term ladies for those like her."

Back at the counter, Keri punched in a code to the door that led her behind the counter. She mentioned how Bob, the owner, valued security and wanted all of his employees to feel safe here.

She rang up everything, placed the things in a pink shopping bag and handed it to me. "You are going to look hot in this. Please text me a photo later tonight."

I reached up to take the bag from her and I was smiled, then I heard "Me too." I turned and it was Red coming up behind me. We didn't see or hear him approaching, but he definitely heard enough to figure out I was likely more feminine than I appeared in my current office attire.

"Jesus Red, we need to get a bell on you." Keri looked over at Red, while I just sort of froze and stared toward Keri. I was trying to pretend he wasn't there, but I could feel his eyes on me.

Then Red walked around to the other side of me, a step closer to the door, "Too bad I gotta go, I'm eager to see this one in whatever that pink frilly thing is in that bag." The nighty and faux trim were visible as they were on top of the other items in the bag.

I remained frozen and Keri continued to control the situation, "Maybe next time Red." She said like she was my agent. I began to blush feeling a bit embarrassed.

"Great, I look forward to it. Brenda is great, but it would be nice to have some variety like we used to have here." Red said and then walked out of the store. The 'bing bong' brought me out of my frozen state.

At that moment, I relaxed and tried to brush off my nervousness. Keri could tell I was a bit scared having Red eye me like a piece of meat. "Sorry about that Hun. Red really has a thing for the ladies."

"That was a bit unnerving." I paused looking at the door then back at Keri, "It was sort of creepy, but sort of hot at the same time." I said feeling a bit more comfortable that Red wasn't ogling me anymore.

"Welcome to girl-power. It's a gift and curse." She said, then added, "You'll get used it and even grow to like it."

Then there was the distinct sound of heels coming down the hall. Looking toward the sound, it must be Brenda, she was tall maybe 6' 2" with slightly broad shoulders with a slender waist and long spindly legs. If she were a woman, I'd guess she played rugby or was a swimmer. Her outfit was elegant, yet sexy with a nice leopard print sheer top and I could see the outline of a corset underneath pair with black slim fitted skirt with a wide black belt providing a narrow waist. Her black leather knee high boots had maybe a 3" spike heel and there was hint of black hosiery between the tops or her boots and the hem of her skirt. Her gold chain black purse hung delicately at her side.

Brenda stopped a couple of feet away from me and began to check me out in the opposite way Red just did, then asked with a smile, "You are heading back there stud?"

I looked at her with wide eyes and just shook my head that I wasn't.

She then took a compact from her purse and checked her make-up. "Too bad, I could use some more protein. I'm on Atkins you know." She said checking me out. "I bet a young stud like you can cum multiple...." She then noticed the bag, the visible garments and looked at me then back to the bag again. "Cute bag, are those things for you?"

I nodded in affirmation while I continued to admire her look. Her brunette hair was curly bushy, came down to her breast and her bangs just covered her eyebrows. I assumed it may be a wig, but it looked very nice.

Keri noticed my silence and thought I froze up again. "Brenda, meet Elli, she is dear friend of mine and recently discovered herself so to speak."

Brenda reached her hand to me, "Nice to meet you, Elli. I think you will look gorgeous in that." She said with a wink.

I looked at her hand, she had multiple bracelets on her wrist, a couple of rings, and her nails were almond shaped and painted in a glittering dark red. "I like your nails." I blurted out.