Why Am I Doing This? Ch. 03

I woke up to the radio alarm playing soft jazz. I always set it early so I could relax in bed for a few moments. As I did so, I thought about the evening before and all the lingerie I had purchased as La Senza. I also thought about Tisha and Bonnie and how they managed to get themselves off but I was unable to. I threw off the covers and looked at my caged cock between my legs. Frustrated by the fact I was unable to orgasm or ejaculate, I got up and had a cold shower to try and thwart my sexual tension.

After, I wrapped a large bath towel around my body and a smaller one wrapped in a turban for my growing hair before I returned to my bedroom to dress. Without any inhibition, I picked out something from last evening purchases. An apple-red satin bra and panty set with white lace trim. The bra was a demi-cup and would cradle the gel breasts I also bought. The panties were cute, low-rise bikinis that just covered my backside and showed a good portion of my bum crack. They also had dangly straps to hold up the white opaque stocking I would wear. The stockings had reinforced heels and toes and a thick white seem running up the backs for my legs. It took me a little while to make sure the seams were straight. I was pretty sure I would need to check them constantly during the day.

I pulled my hair back into a pony-tail that tickled the nape of my neck before I bound it with a pink bungie. When I buttoned up my white linen shirt, my new bust pushed out the front proudly. I tied a closely clour-matching, red silk Armani tie into a full Windsor and inserted some opal studs into the button holes of the French cuffs. It was unfortunate I covered-up my sexy wear with my black Boss double breasted suit and shoes.

Oh and the shoes. Black patent leather, lace-up ankle booties with a two inch Cuban heel. Men's shoes but enough to look feminine to the casual eye.

I left my place and walked towards the bus stop. As was my habit, I stopped off at Timothy's for a Chai latte before hopping on the public transport. Charlotte had my bevy ready and handed it to me. "Hi Charlie. Thanks."

"Morning Jerrod!" And then nothing as I took the cup and noted her slightly gaping stare.

"Oh. It's Jeri now, not Jerrod." I corrected her and went on my way. "See you next later!"

I arrived at the bus stop and waited with the regular crowd. When the bus arrived and we all filed on, and as was typical, no seats were available so I had to stand for the trip. For some reason, the other riders gave me weird gazes. I thought proudly. "I guess they really like my suit."

My cell phone started vibrating and playing a short guitar intro before hearing the Stylistics' lyrics to "You're a big girl now!"

I retrieved the phone from my breast pocket and swiped the green icon. "Hello? This is Jeri speaking."

"Hi Jeri." I recognized Cheryl's voice. "Tell me what you are wearing."

"I am wearing my Boss suit and Armani tie." I answered in a normal phone voice. People around kind of looked at me a strangely.

"What about underneath?" Cheryl asked. "Tell me what underwear you're wearing."

In the same vocal volume, I said. "I am wearing my new La Senza bra and panties that are holding up some reinforce white stockings."

"Very nice!" I was excited by Cheryl praise. "You'll have to show me when you bring me the Bosco contracts."

Immediately, there was a pang of pleasure between my legs that made me wince slightly.

"Oh, and I'll need to see the Zigflow contract too." I nearly doubled over. "And the Apple contract as well. I'll need to review their contract."

Every time I heard Cheryl say the word "contract" I would get more and more sexually aroused. I was bent over and squeezed my groin as my penis engorged with blood but only to be constrained by the cock cage locked in place.

When I got off at my stop, I could barely walk properly to the office. Sarah the receptionist for the executive office suites was already sitting behind her desk. She was talking with Julia the other receptionist who had probably just got in and was standing beside her. It was Heather's day off.

By this time I was almost able to stand erect. I managed to squeak out a greeting. "Hi Sarah. Hi Julia."

"Hi Jerrod." Sarah smiled a reply back to me.

"Oh, hi!" Julia looked up towards me and then gave me a funny look. "Are you okay?"

"I'm great thanks." I automatically answered back but still struggled to walk to my office.

I unlocked my office door and entered. Since the window faced the rising sun, it was pretty warm inside. I started to unbutton my jacket when Julia rapped on my door.

Julia was the youngest of the three receptionists, maybe 19 years old. She had full, curled, light brown hair that was tied back into a thick pony tail. Her pretty face needed little if any make-up. Her five foot four frame was slight with nice pert breasts.

"Sorry. Should have given this to you when you came in." Julia began.

By that time, I had removed my jacket and placed it on the coat rack. Of course standing erect made my breasts prominent. My bright red bra showed through the shirt material. I thought nothing of it, but Julia just stared at them with her mouth agape. "Uh... You have something for me?"

Julia shook her head. She handed me a thick package. "Y..yeah. Sorry."

Julia quickly scurried away.

"Bring... Bring!" Went my desk phone before I managed to open the delivery. The display showed it was Cheryl calling from her office.

"Hello, Cheryl." I answered.

"Jeri. Where's the Bosco contract. And the Zigflow contract. And the Apple contract." Cheryl asked abruptly. "And did you just get a package? Bring it to me too."

I basically collapsed back into my chair as the tsunami of pain and pleasure smashed into my groin. "I just got in. I'll bring them over in a minute. And yes, I'll bring the package I just got."

Heavy breathing managed to ebb the sensation, so I could gather everything Cheryl ask for and go to her office.

I walked into her office and placed everything on her desk. I sat down in the chair in front and my eyes were instantly drawn to the Paraiba Topaz pendant hanging around her neck. My mind went blank and begged for directives.

"Jeri. You have been a good girl." Cheryl's voice sounded like it was coming from afar. "As always, you will continue to get sexually excited each and every time I say the word 'contract'. Each time I say the word 'contract' your sexual excitement will increase double. You will be unable to orgasm or ejaculate regardless of the how much you are sexually stimulated. However you will only be able to orgasm and ejaculate when I say the command 'love craft'. Do you understand?"

"Yes, I understand." I repeated her instructions verbatim.

"Good. Now take this to the board room and wait." Cheryl handed me the package and some file folders. "Ms. Lawson is coming in soon."

Laurie Lawson. A relatively new client signed up by Cheryl. Ms. Lawson had an eight figure portfolio. She was an extremely attractive woman but her personality seemed to always be coolly professional especially with Cheryl.

I quickly retrieved my jacket and then took everything to the board room. I waited. And waited. And waited. Finally I heard voices approach. Cheryl led the way.

Cheryl was wearing a dark blue skirted suit with a white silk blouse. I could make out that she too wore a red bra beneath.

Laurie Lawson followed. She stood about six ten in her five inch spiked heels and was a number of inches taller than Cheryl even in her four and a half inch stilettos. Perfect auburn hair but in a short bob framed her very attractive face. Other than her red painted lips, she wore very little make-up. She was smartly attired in a fitted red skirted suit. The jacket strained to remain buttoned due to her full breasts.

"Ms. Lawson. You remember Jeri." Cheryl introduced me. "She... He is my assistant."

"Nice to see you againg Jeri." Ms. Lawson smiled warmly and offered me a firm hand to shake.

"Yes. Thank you. It is very nice to see you as well, Ms. Lawson." I managed after she nearly crushed my hand.

Ms. Lawson took a seat and crossed her legs. The high spilt in her skirt fell open and I could just make out the edge of a stocking welt.

"Jeri! Didn't you order coffee?" Cheryl said. "Go downstairs and order some immediately."

I was confused and thought. "How was I supposed to order coffee when I didn't even know there was a meeting?"

"And some Danishes too." Cheryl added. "Sorry. Sometimes she... he's so unthinking."

"That was the second time Cheryl referred to me as 'she'." I wondered to myself as I left the room and called down to the coffee shop so the order would be ready by the time I dashed down.

They were just finishing filling the carafe when I arrived. I charged it to our account before grabbing the refreshments and returning upstairs. Back in the board room, I set everything out. "Ms. Lawson. How would you like your coffee?"

"With cream." She instructed.

I poured the coffee into the supplied China cups and prepared it as she requested. I already knew how to make Cheryl's. After setting the cups saucers, I sat and joined them at the table. It was then I noted the package I had brought earlier was ripped open and emptied.

The meeting went well as expected. Cheryl was a great sales person who could sell ice in the Artic. It was incredible to watch her work as she talked and flirted with Ms. Lawson. By now, both had unbuttoned their jackets and proudly displayed their bountiful breasts. I didn't see it, but Cheryl somehow undid a fourth button on her blouse; her red bra clearly visible as well as her deep cleavage.

"Jeri, hand me the consent contract." Cheryl said.

I winced.

"Jeri. Contract!" Cheryl repeated. "Hand me the consent contract now!"

I struggled to rise and bring Cheryl the forms. As I rounded the big table, I noted Ms. Lawson's legs were no longer crossed. Both feet were on the floor and her knees were parted.

Cheryl used her thumb and index finger to dangle the hypnotic charm in front of me. "Jeri, take off your suit. Let us see what you are wearing underneath."

Compelled to obey, I dropped my jacket onto the floor. My pants followed quickly. My dress shirt was like a short dress. I removed my tie and unbuttoned my shirt, but was instructed to leave it on.

Ms. Lawson rose from her chair. Facing me, she pushed me down to my knees. My eyes were barely at her crotch level. She reached behind my head and pulled the binding to free my ponytail. She inserted her fingers into the slit of her skirt and slowly pulled it apart confirming that she was wearing stockings and garters. As she exposed beneath more, my eyes popped when I saw something I wasn't expecting. It took a second to realize she was wearing a fire engine red strap-on dildo.

My mouth gaped slightly. Ms. Lawson took the opportunity to push it passed my parted lips. Slowly at first, she pumped her hips until most of it was inside and down my throat. When I didn't gag, she used both hands on the back of my head to force the rest of her cock in. With it down my throat, I couldn't breathe and started to cough. Or at least tried to cough. Ms. Lawson held it there for an extra second before releasing her hold. I gagged and hacked for air but before I could recover, Ms. Lawson stuck it back down my throat. She repeated this sequence five or six times; maybe more since I really lost count.

I felt woozy and disorientated as I found myself lying on the big wooden board room conference table. Ms. Lawson had my legs over her shoulders with her big dick dildo slapping the insides of my thighs.

"She's very cute." Ms. Lawson smiled at Cheryl. She squeezed handfuls of my gel packs. "Although she could use some real breasts instead of those ugly fake gel packs. And bigger nipples too."

I looked over at Cheryl. She was seated with her legs spread; her skirt hiked up with a hand inside her panties and was obviously masturbating. I looked back between my spread legs towards Ms. Lawson. She had removed her jacket and opened her blouse. The bra she wore was a demi-cup, underwire that supported her perfect breasts but left her cherry sized nipples exposed.

Ms. Lawson started to push and poke her cock into my ass. Of course my panties albeit small, did not allow her to penetrate me. Ms. Lawson had lust in her eyes. She took hold of the leg holes and ripped it open so she could access my ass. Ms. Lawson placed the round tip against my puckered hole and pushed but met with more resistance. She spit on her fingers and rubbed it along my crack before she reattempted entry. This time as she pushed, it breached any opposition.

"Oh god!" I moaned and pleaded. "Oh my god! Yes! Please Ms. Lawson. Push it in... Fuck me!"

As she entered me more and more, I could feel my rear hole stretch to accommodate her. Finally I felt her hips against my butt cheeks. She was totally inside me. Ms. Lawson used her hands and pushed my knees to my chest before she started to fuck me harder and harder. I started humping my ass to match her fucking motions; she was pounding my ass as hard as she could.

It was the highest state of sexual arousal I had ever experienced. Yet, without Cheryl saying those magic words, I wasn't able to climax. My body started spasming and shaking uncontrollably. Incoherent babble came from my open mouth. My mind saw images of psychedelic shapes and colours.

"Fuck! Fuck! Fuck!" Screamed Ms. Lawson as I swear I could feel the tip of her cock back in my throat. Good thing the conference room was mostly sound-proof. "Oh fuck I'm coming! Aaaahhhh...!"

Totally spent, Ms. Lawson collapsed on top of me between my spread legs panting for breathe. "Oh my god, Cheryl. Yeah, that was worth giving you the contract."

I looked over at Cheryl who had also managed to make herself cum. Her panties were entirely soaked and dark red from the massive female ejaculation she must have had. "And she's yours whenever you want."

Ms. Lawson extracted herself from me before she unbuckled the strap-on harness. I didn't realize it was a two-ender as she pulled the other sizeable end from her soaked cunt and threw it onto me. Sticky clear liquid dripped from her gaped hole and onto the carpet below.

The whole room stunk of sex. While the ventilation system would take care of the stench, I wasn't sure about the wet carpet.

After that, every couple of weeks or so, Cheryl had me deliver sealed papers for Ms. Lawson to sign. Each time, I found myself being used for Ms. Lawson's sexual gratification while I remained disappointedly unfilled (metaphorically).

Later I found out by accident that the papers to be signed were just blank sheets and Ms. Lawson's signatures were just scribbles. But I found myself unable to cease the delivery process.