Sissy Whisperer, Ch. 03

Sissy Whisperer-Chapter 3

Orally pleasing a man was something until a few days ago, I would never have contemplated. But I did it and it was so exciting. Dressed as a feminine submissive sissy in a pink babydoll, white thigh highs, pink slides, my pathetic clit in a cute chastity cage with a fat filling butt plug in while being filmed by Keri as I worshipped a real man's cock which made sex go from feeling like a chore to a delightful bliss. Without Keri helping nudge me in the right direction, my path would be a continuation of depressing relationships with women for years to come.

While still having the taste of his cum in my mouth, meeting bob after I sucked him off was an odd experience. Simply standing with my hands behind my back, looking at his feet afraid to make eye contact like a shy demure Gisha. Bob stepped in and gave me a hug, smacked my ass and thanked me for a great blow job. Blushing was my only response. We then walked down the hallway to the door to the counter. Keri and I entered the employee bathroom while Bob manned the counter until Keri returned.

Keri was giddy and started playing the 20 questions game by herself, "What was it like? I bet it was amazing. Did you love it? Of course you did. Did you swallow? I know you did." She kept going, then picked up a pack of makeup whips and handed it to me, "Use these to clean off your make up and Bob's cum. You sissy slut." She smiled, gave my butt a hard slap, "I need to get back to the counter."

Changing back to Elliot was a bit disappointing, but underneath, the chastity cage was still locked in place and the butt plug was still snuggly in place. Elli's things were neatly placed in the pink shopping bag. Picking up the bag, I joined Keri at the counter and gave her a side hug. She stood up and gave me a hug strong enough to asphyxiate a goat. Then she released enough to lean back and inspected my face for any remnants of my make up. Her face was still, then she laughed, let go of our hug, moved her hands behind my neck to unbuckle my "SISSY" Choker.

Whoopsie I thought.

Keri placed the choker in my bag and said, "I know you are officially a Sissy after blowing your first man, but I dressed as Elliot, you have to be less obvious." She placed the choker in my bag.

"Sort of like Superman." I said.

She burst out laughing, "Well, yah, if there is a multiverse where Superman is a cock sucking sissy, then yes I guess." She then reached up to adjust my hair tucking it behind my ears. "Try to wear it like this more often, it's a little androgynous, but it looks really cute on you."

We chatted briefly before a customer came in and she whispered in my ear to go home, get something to eat and that she was going to upload some photos to my fetish profile.

At home, my grumbling stomach let me know what my priority was. Bob's cum although very tasty, was enough, but a salad and with some chicken would do the trick. While eating, my thoughts were focused on recalling blowing Bob's cock. My phone buzzed; it was a notification I had a message from the fetish site. Then the phone buzzed multiple times and more there were notifications from the fetish site. Curiosity got the better of me and since I didn't have a 'no phones at the table' rule in my home, I logged in to see what all the fuss was about.

The notifications were related to photos and a video Keri posted of me in my sexy pink lingerie and of me blowing Bob. My profile photo changed from nothing to me kneeling on the floor in my pink babydoll holding a man's balls in one hand and cock in my mouth.

Glancing over the photos it was fun to see me in various poses and then a strategic series from the video of me blowing Bob's cock thru the glory hole. Reading the comments on the pics and video were mostly from men wishing I would blow them next. A few were kudos from others like me and even Brenda complimented me on my skills. It was making me very horny. After dinner, the plan was to change into my 'Daddy's girl' top and my white thigh highs. For what was going to occur, bottoms would not be required.

After tidying up the kitchen, I picked up the pink shopping bag and took it with me to my bedroom. After changing, I attached the new larger black dildo to my bed post high enough I could back into it while on my hands and knees. A towel was placed on the floor to catch my sissy drippings. The tablet was set up just in front of me and logged into the fetish site. Normally, I did this every night while watching sissy hypno with the smaller version of blacky, but this would be way hotter watching myself star in my first sissy porno.

Keri texted me, "You're a porn star now!"

After reading her text, my butt plug was removed and I pushed myself back onto the new larger toy I would nickname Bubba. It was clearly bigger and with determination and grit, I got the wider head to pop in and then slowly pushed back as far as I could. As it hit my p spot, it gave me shivers and sissy juice began to leak from my cage.

Keri texted again, "Busy?" with an eggplant emoji.

After glancing at the text, my concentration returned to moving up and down on Bubba until I was able to feel those big hard balls against my caged nuts. Then I began a slow rhythmic fucking enjoying the girthiness of the new toy. This size didn't just press against the P-spot, it smashed it with every back thrust, and I now had a long string of sissy drippings dangling from chastity cage. Placing the phone below me, I took a pic of bubba buried in my ass and leaking pre-cum. Satisfied with the photo, I texted it to Keri, then scoped the pre-cum to savor the taste.

She replied, "So, she is busy." With a wink emoji. Then texted, "Good girl backing that ass up on that BBC."

Smiling while taking long deep pushes on Bubba, I continued to read comments on the photos. Similar to the comments on the video, most wished it was them being sucked off. Feeling desired was a super turn-on. In the photos, my little clitty looked so cute in the little pink chastity cage and of course, the stills of my mouth wrapped around Bob's cock confirmed I was a submissive sissy that craved cock. Then I watched the video from the beginning while riding Bubba and denied orgasm until the video showed my mouth full of cum. Then I picked up the pace and force. The back of the bed began to hit the wall. It only took a few hard thrusts before I felt the need to pee, then I spurted a load unto the towel. I reached back to catch the remnants and savored them.

The next day I went to work looking like a normal guy on the outside, but my brain was swimming with thoughts of sucking off Bob and craving to do it again. My butt plug didn't help when I shifted in my seat and being caged denying me to get hard, just kept me is cycle of lust and denial all day.

Later in the day, Keri sent me an email basically saying she was coming over Thursday night and that she wanted Elli to make dinner. My response was a simply smiling emoji and was super excited to be Elli with her and to make us dinner.

After work, I couldn't get Bubba in me fast enough and I deliberately rode it for over an hour while watching sissy porn. This time, I denied a release and went to bed feeling even girlier sleeping in my babydoll. The rest of the week was the same cycle of going to work, struggling to concentrate on work more than cock and then going home to get Bubba in me as soon as possible.

After work Thursday, getting home to prepare dinner was my first priority. Next would-be getting Elli ready. So far, I only had two outfits, the "Daddy's Girl" outfit and the pink lingerie, I didn't exactly have dinner attire for Elli. But in the pink lingerie, I could sort play the role of a cute doting housewife.

By 6:30pm, dinner was ready, and I was completing my finish touches to my hair and makeup. I still only had lip gloss, mascara and eyeliner, but it was enough to give my face more femininity. I turned to get a glimpse of my backside in the bathroom mirror with the babydoll just exposing a glimpse of my bottom and the tops of my white thigh highs. From the front the babydoll darted up to my chest revealing my midriff and panties with the tiny bulge from my caged clit. Happy with the look, I gave myself a little kiss and blow to the mirror before returning to the kitchen.

Halfway to the kitchen, the doorbell rang, and I trotted to the door, checked the peephole, and it was Keri wearing black leggings with a cute lavender crop top sweater that revealed her belly button. Her make up was always perfect, this time her eyes seemed smokier, and the dark red matte lipstick was not her usually pinker shade. Her hair was in a high ponytail which was rare for her but looked hot when she did. She had a back shoulder bag and pink totes in each hand.

Then I realized I was taking too long to open the door. Turning the doorknob, I whipped the door open, then ran my hand up toward the top of the door, while slide my foot up my leg, then winked. I was trying my best come-hither type of pose. She initially was startled and after viewing me from toe to head, her initial expression was of shock with her mouth agape and eyes wide enough to see white around the entire iris. Then she squinted, gave me a devilish smile "That's my sexy home maker slash porn star."

I moved to the side inviting her in and closed the door. With my back to her and before I could turn around to face her again, I heard her drop the bags and then she pounced against my backside and pushed me into the back of the door. I could barely get my hands out in front of me to brace myself. She began sliding her hands around my waist. Her breast were pressed against my back and her hips were humping my ass aggressively. Her hands began to slide up under my baby doll and to my breast where she squeezed what little bits of titty I had until it hurt then she realized and rubbed my nipples. I could feel her breath against my neck, and she started to lick and bit the side of my neck. I was completely helpless yet moaning at everything she was doing. "I'm going to tear you apart slut." Then her hands slid back to my panties, and she slipped a finger under the top on each side and slide them down to my thighs. She reached under to push against my butt plug and would hump me each time she did that. At first, I yelped as the plug pushed against my p-spot, but then moaned enjoying the aggressive humping.

Just as I submitted and relaxed letting her have her way with me. She stepped back, ordered me to pull panties back up and grabbed my hand taking me through the kitchen where she briefly stopped noticing dinner on the island waiting for us with just a wisp of steam coming off each plate.

She then turned to me, smiled and continued pulling down the hall to the bedroom. She was walking faster than I could which made me trot/scoot to keep up and not flip out of my heels.

When we got to the bedroom, she pushed me onto the bed, spread my legs, stepped between them, placed a hand on each side of my hips, pulled herself tight against me and began kissing me vigorously while grinding herself against my caged clitty. She then took each of my hands, slide them out away from me causing me to fall onto my back and the weight of her was now fully on me. All I could do was submit to her and she returned to kissing me aggressively. Her tongue would not let mine move as it invaded my mouth and claimed it as her own.

Then again, just as I was starting to really enjoy her dominance and control, Keri broke the kiss and stepped back. I was left in mid kiss with my eyes closed, mouth open, legs spread before realizing we stopped, she smiled reach out her hand offering to help me up and said, "Let's have dinner before it gets cold."

She held my hand as we walked back to the kitchen. On the way, she said, "I needed that more than you know."

"I'm glad I could help." I said wondering what she meant, then added, "I've never been ravished like that." I paused, then said, "I don't think I've ever said 'ravished' before."

She chuckled and gave my ass a hard slap when we entered the kitchen, "So what did my little homemaker make for dinner?" She paused and before I could answer, "It looks great."

"It's grilled salmon and pasta." I showed her the wine and poured each of us a glass. She took a seat on one side of the island while I placed a hand over my dish. To be safe, I gave each dish a quick nuke in the microwave. I warmed her dish first and she waited until mine was ready before trying it.

She smiled, "Thank you." She took a sip of wine, "It looks delicious."

"Thank you." I said and added, "It's actually one of my favorite dish to make, but since I got dumped, I haven't felt like cooking until you requested I make us dinner."

She tried some of the salmon, nodded with approvement, "This is fantastic. You would make a quite the little housewife." She laughed a little and I did as well. "I have to confess. I haven't been able to stop watching the video I filmed of you blowing Bob Monday. It has had me riled up all week. Then seeing you dressed like that to greet me at the door, I just lost it."

"Well, I admit, it was the beat greeting I have ever received when opening my door." I said, then took a sip of wine. "Maybe I should dress like this when a Jehovah Witness stops by."

"Dressed like that, you could make any guy call out for God." We laughed and then she continued, "There is a bit more to my confession." She didn't look at me, just down at her food. "I have fantasized about you becoming a sissy for the past year." She said starting to blush. It was unique to see her bashful.

"Well, it's something I would have never thought of trying without your little 'stress relief' plan after exams." I then thought for a second, "How did you know I would take to this. I mean, I don't think I ever put out any feminine vibes. In fact, because I've always been less than hunky, I think I actually overcompensate to make sure I seem like a dude non one should mess with."

She chuckled, "Well, that's the thing, sometimes you tried too hard, but you don't act like the other guys around women with their gross overly sexually innuendos thinking that will make girls go nuts for them. You are quieter and shyer around women and sort of let them control the situation." She ate more of her pasta waiting for me to respond.

"Ok, I agree with that, but what made you think I like to dress up girly and blow men? I'm pretty sure I didn't put out that vibe." Then I continued to eat while waiting for her to respond.

Keri finished what she had in her mouth and continued to explain. "Well, one night Brenda came in with someone of your stature, thinner, maybe a runner like you. She was dressed like a schoolgirl with the plaid skirt, black knee highs, white button up top with a V neck sleeveless gray sweater. She never looked up and it was hard to see her face with the bad black wig she was wearing. No purse, just holding her hands in front of her. Brenda explained that this is her new friend Jenna, and she needed her help. They walked back to the booths, and I was curious what she meant by 'needing her help.' Later, after a few guys went back there and came by smiling on their way out the door, I decided to go see what was going on. I knocked on the door they were in, and Brenda let me in. Jenna had cum on her face and was scooping it up with her fingers and licking them clean. Brenda smiled and explained she helped Jenna with her first blow job. Without hesitation, Jenna responded, 'I'm a Sissy cock sucker now.' Which caused Brenda and I to laugh a little. Then I said, 'Good for you.' Then returned to the counter."

"But how did you know I would be into that? I never even thought about wearing girls' clothes or doing stuff with dudes before." I said after a enjoying my dinner.

"Well, it wasn't too long after that, that you got dumped and when you told me what your ex-girlfriend said as she dumped you and that you weren't manly or aggressive sexually, I immediately thought of Brenda's friend. Brenda later explained that some guys are scared to let themselves be who they really are. Her friend Jenna contacted her on the fetish site and asked if she would help her and Brenda knowing how hard it was for herself to come out, was more than happy to help her out." She took a sip of wine and then continued, "I tried coaxing you by bringing slightly gay things from the store when we hung out to see if there was any interest. I thought maybe being with just me, you'd be comfortable enough to try things, but you always refused. That stupid inbreed male ego wouldn't break. I thought, I'd try one more time after finals by convincing you to watch BBC porn with me. Even Brenda said, no sissy whether they know they are or not, can resist reacting to Big Black Cocks, its our kryptonite so to speak." She sat back and had a proud look on her face. She was proud of the fact she was right, that I was after all a sissy as she suspected. Then she took a long drink of her wine. Like a big shot executive just closing a huge deal.

My head sort of dropped a little and I just played with my food a little with my fork before responding. "Prior to Friday, I would automatically get defensive that I was manly and that I've been with many women." I paused and chuckled, look up over her head to the cabinet behind her, "Well three to be honest." Then looked at her admiring her top, instead of wishing I could see her boobs, "But it was way more satisfying sucking Bob's cock Monday, then any sexual experience I have ever had as man. It still feels a bit odd, but I can honestly say it felt more natural and I'm not going to even think about denying that I loved every second of it." Then I looked at her beautiful eyes, wondering how long it will take for me to master the skill of the smokey eye and said, "I'm truly grateful to you for helping me figure out that I'm a sissy."

"I'm glad I got to help you find yourself." She stopped, then changed the subject. "So, I brought you some hand me downs to help Elli expand her wardrobe." She looked over her shoulder to the door at the totes she left on the floor before jumping on my back Steve Erwin on an alligator.

I looked over at the totes and wondered what she brought me. "Thank you. I can't wait to see what you brought me. I'm sure I'll love everything. You always dress very stylish, even in scrubs."

"Aww, thanks." She paused, "Some of my things won't fit you well and it's critical that Elli has some essentials of her own so you can continue to explore this side more. I know we both have tight budgets being couple of college lackies, but I'm taking Elli shopping Saturday."

At first, I was happy at the thought of having more girly things, but then quickly went to feeling shocked at the thought of going at in public as Elli. "Wait, do you mean, you are taking Elliot? shopping?"

"No, I mean Elli. You will love it. You haven't lived as a girl until you shopping as one. Don't worry your pretty little head. With my skills, you will look perfect. We'll hit the mall and have a blast. Besides, the mall is dead these days. It's not like the old days when it was crowded, and you'd punch a girl in the tit for the last skirt on sale in your size. Trust me, you won't have any problems."

I nodded that I trusted her.

Then she blurted out, "OMG, I totally forgot to tell you about how much Bob and been asking about you."

"Really?" I said a little too eagerly.

"Oh' ya, A LOT. He really fancies you and wants us to come over to his place Sunday. You game?" She said trying to hide her excitement knowing she would get to see me with a dick in my mouth again or maybe in my virgin ass.

"Yes, absolutely." I said uncontrollably bouncing on my seat.

Before I could get control of my eager sissy side, Keri smiled and said, "Ohh, that is so cute. Ms. Elli is excited to see her Bobby."