Lori ensured I was always appropriately dressed by picking out my sissy girlie things for me everyday; school girl, cotton, bikini panties with support to make my bum round, my padded training bra with built-in forms and knee socks; all white. Lori selected high heeled Mary Janes for me to wear around the house.
When I was allowed out or had to go to work, Lori allowed me to wear my boy clothes over my sissy girl clothes and normal dress shoes.
Lori taught me how to apply my make-up. My make-up was very understated, almost naked looking with a very thin but dark eye liner and light mascara when I was out. People would look but could not figure out what was different. But on the weekends, it included heavier make-up and eye liner with long false eyelashes.
"How's my sissy girl today?" Lori asked me. Lori always refereed to me as "sissy girl" when we were at home.
"I am fine, thank you for asking, Lori." I replied as I always do. I was waiting for Lori to select my clothes for today before I left for work.
"I think my sissy girl has earned some extra privileges." Lori told me. "I've laid out some special things for you to wear to work today."
I looked over at my things. No training bra, cotton school girl panties or white knee socks. Instead, there was a completely different style of clothes. A white silky camisole but no bra padding. I slipped it on. It came down to my waist. There was a pink Rosette between the soft lace cups which were empty.
"Oh, wait." Lori exclaimed. She opened a package and handed me the contents. I took it from her. They were soft, skin coloured gel packs weighing about a couple of pounds each.
"They attach to your chest without any glue." Lori explained to me. "Put them on under your cami!"
There was a left and right one. Each stuck on to me and hung slightly. The bra part of the camisole supported my new B sized tits. My new nipples were big, hard and poked through the thin material.
The panties were matching, white French cut and was just big enough to control my "ugly boy-thing" as Lori referred to it.
My eyes light up as I spotted and put on a garter strap. They were white with matching pink Rosettes at the end of strap. Stockings were a translucent white with a pink tint and reinforced heels and toes.
The feeling of the stockings gliding up my smooth hairless legs was indescribable. My ugly boy-thing was hard and aching. I could feel some pre-cum fighting its way out of my pee hole. This did not go unnoticed by Lori. "You better not soil your new clothes!" She warned as she handed me my shirt and pants. The shirt was white, silky soft and thin, not like the men's heavier cotton shirts I normally wore. The buttons were stitched on the left side. It did little to hide my new breasts. My nipples easily poke through the soft material.
The pants were a little more tapered than I was use to especially around my bum and crotch. My garter straps and Rosette bumps were easily noticeable. My shoes were lady's pointy toed ankle lace-up boots with a low 1-inch heel. They looked similar to man's shoes and the pants were long enough to cover them.
The jacket was tailored and closed right over left. At least it hid some of my feminine assets.
Lori escorted me to work. I wasn't sure of my feelings. Excited to wear my new attire but frightened to be caught. Luckily I mostly worked alone and behind a desk.
Things were going well for the most part and no one suspected anything untoward. Suddenly my cell rang. It was Lori video calling to check up on me as she often did randomly during the day.
"Hello Lori." I answered.
"Let me see." Lori ordered.
As normal, I moved to an empty office and closed the door. There was no lock on the door. I propped the phone on the desk with the video on so Lori could watch.
"Well?" Said the voice on the phone. "I'm waiting!"
I unbuttoned and removed my jacket. My breasts were obvious and were proudly on display. But Lori wanted to see me in my imitates.
I removed my blouse and placed it atop my jacket.
I could overheard a voice from outside the door "I'll be in here." The door opened.
Standing there was Leah my manager. Leah was a BBW with long blond hair and huge bosoms. Initially surprised, her mouth was agape before entering and closing the door behind her. She said nothing nor made any noise.
"Well? I'm still waiting!" Came over the phone.
Leah's eyes were open wide. She had a big grin on her face.
I timidly undid my pants and let them fall around my ankles. Both Lori and Leah were looking at me in my panties and stockings.
"Good sissy girl. I'll see you tonight at home." Lori said. "You'll have to take the bus home."
Lori hung up, but Leah remained. "Sissy girl, eh? I like that!" She said. "These offices sometimes really need a lock."
I started to bend to pick up my pants. "Uh-uh!" Leah warned. "Not until I say so." I actually still have a huge crush on Leah. It's not that I have a thing for big women, but there was something that just made me smitten from the moment I met her. That was part of the reason I took this job. Of course Lori had no idea about how I felt.
Leah stood just over 6 feet in her 4-inch high heel stilettos she loved to wear. Long eye lashes extended from her baby blues. Her make-up was as always, perfect. Today Leah wore a tight fitting, knee length, summer dress with 6 buttons down the front; the top three undone showing off her huge and deep cleavage. The bottom one was also undone.
Leah eyed me carefully, taking in every detail. "Well, your clothes are certainly nice. Did you pick them or did Lori?" She told me. "I like the stockings and garters." She lifted her hem and showed me hers. Leah knew Lori from the office Christmas party.
"Lori picked out my attire as she does every day." I replied. "Thank you. I like your stockings and garters too."
I went on to explain how I good caught in her underthings when she pulled down her sweatpants that I was wearing. And that she got rid of all my boy underwear and made me wear only girl underwear since then.
Leah stood beside me as her hands caressed my body through my underthings. My ugly boy thing grew.
Leah was now directly behind me. She pulled me into her body. I could feel her ample breasts press into my back. Her left hand slipped under my cami and played with my gel breasts as her right hand reached inside my panties and started masturbating me. I could feel pre-cum leaking out. She was going to make me cum.
"No please Leah! Don't make me cum!" I begged. "Lori will be angry and punish me for soiling my panties!"
Leah did not relent. "How does Lori punish you?" She asked.
"She will spank me!" I informed her.
"I will stop if you promise to be my sissy bitch at the office. Do you agree?" Leah asked, but she increased the intensity of her jerking me off knowing I would have to submit or blow my load.
"Oh please stop! Yes, I agree." I cried. "I agree to be your sissy bitch!"
Leah stopped immediately. My knees were trembling. A few more seconds and I knew I was going to cum inside my panties. Pre-cum had already stained them. Lori would not be happy.
"Tell Lori you need to work late and then come to my office after everyone has left." Leah ordered before leaving.
She departed the office and left the door open. Anyone going by could and would see what I was wearing. I quickly did up my pants and blouse just in time. Leah's assistant Lexie walked by. "Have you seen Leah?" She asked. "I thought she was hiding out in here?"
I was slightly hunched over to try and hide my breasts. "I think she went back to her office." I nervously answered still shaking slightly.
"Okay, thanks." Lexie paused. "Are you okay? You seem kind of... I don't know. Just something wrong."
"No, I'm okay."
I managed to calm down a bit before I called Lori. "Hi, it's me. I was just told to work late tonight but I'll be home later..... No, I'm not sure how long I'll be... Yes, thank you. Bye."
I was sweating. Lori really didn't sound convinced of my excuse. There was a questioning tone to her response. The rest of the day was a blur. As everyone started to leave, panic started to build inside me. My heart was pumping blood a gallon a second or at least felt like it. Finally with everyone else gone or so I thought; I knocked on Leah's closed office door.
"Come!" I heard her respond.
I opened the door and entered. Sitting in front of Leah's desk was Lexie. I wasn't sure what to do and just stupidly stood there.
"Close the door." Leah ordered. I complied.
I was nervous. My knees were shaking. My palms were sweating. My head was spinning.
"Show us." The tone in Leah's voice was not a request. "Show us what you are wearing, sissy bitch!"
"How could she say that especially in front of Lexie?" I thought. "I can't!"
"Lexie, maybe sissy bitch needs some reassurance. You show him first." Leah said.
Lexie immediately stood. She took off her jacket and undid her blouse. Underneath she wore a heavily stayed corset, tightly drawn about her ribs. I doubt she could easily breathe. Her large tits were naked. Her cherry nipples were full and hard.
Lexie dropped her skirt. She wore stockings and garters but no panties. Instead she wore an 8-inch strap-on.
Lexie knelt between Leah's legs pushing up her dress as she did so. Leah too did not wear any panties. Lexie started to tongue Leah's shaved hole making sure it was sufficiently wet before plunging her "cock" into Leah.
"Okay? Now take off those ugly boy clothes and show me your pretty undies." Leah smiled.
Lexie continued to fuck Leah as I stripped down to my cami and panties.
"Oh, what lovely shoes. Leave them on." Leah said. "Look Lexie. Look how excited sissy bitch is." Pointing to my hard, ugly boy thing inside my panties.
Leah pushed Lexie away and then beckoned me between her thighs. She pointed at her gaping cunt. I was about to pull out my ugly boy thing. "No, you haven't earned the right to fuck me. Use your mouth." Leah reprimanded.
I began to drop to my knees. "No, standing. Again you haven't earned the right to be comfortable."
I wasn't allowed to use my hands to support me. Bent at the waist but I couldn't keep my balance. I spread my feet slightly hoping it would help but I fell face first into Leah's soaking wet cunt. My tongue attacked it with vigor.
I felt my panties being pulled down but only to mid-thigh. A wet tongue pierced my ass hole penetrating as deeply as it could. Lexie had shown me her tongue on previous occasions, it was extraordinarily long. I felt her tip wriggle inside of me. "Mooh, phuck!" Was all I could moan with a mouthful of pussy.
I felt empty as she withdrew her tongue from me, but she was soon to fill that void. A firm pointed objected pressed at my rear hole. Lexie slowly pushed her strap-on dick into my ass. Being already well lubed, Lexie easily slid in and out. Each stroke was full; I felt her hips pressed against my bum.
Trying to concentrate on Leah's cunt was impossible. It turned out more that my face mashed into her when Lexie thrusted her hips forward.
Lexie pulled my face away from Leah's cunt and stood me up. As she fucked my ass, her hand reached around and started to jerk me off. She was going to make me cum!
I was still between Leah's heavy thighs, less than a foot away from her vee. There was no place for me to move.
With a few more well timed powerful hip thrusts and strong hand jerks, I started cumming.
"Ohhh....!" Was all that came out of my mouth.
Lori had not allowed me to cum in a while. My balls were overflowing with seminal fluid. A huge gush of white goo erupted from my piss hole. The first splashed over Leah's belly. Lexie continued fucking me and jerking me off. She aimed my cock directly at Leah's cunt covering it with my heavy cream.
After six or seven blasts, nothing came out other than a few dribbles. Lexie continued to milk me until Leah was satisfied I was empty.
Trembling, I opened my eyes to view Leah soaked in white milk. Her eyes made a downward move.
Lexie pushed my head over. "You don't expect Miss Leah to clean up your fucking mess, do you?"
Lexie pushed my face into my own sperm. I licked Leah's belly until there was no trace left. Then Lexie pushed my face back into Leah's cunt. I sucked and licked until Leah came. Her pussy gushed.
"Oh yes! Fuck! Suck me, sissy bitch!" Shouted Leah.
After Leah had cum and calmed down, Lexie allowed me to stand up. She finally withdrew her cock that was still in my ass. "God, I wanted it back inside me again!" I cried in my mind.
Leah picked up my blouse and wiped any remaining cum and goo I had missed licking up. She handed it to Lexie who wiped off my face and body with it.
Leah pulled up my panties hard making sure to wedge it tight up my ass. Lexie used her hand to mash my ugly boy thing soaking up any of my remaining goo. "Get dressed and you can go home now." Leah told me. "But don't forget, at the office, you belong to me."
I looked at my blouse. It was no longer pristine as Lori instructed me to keep it. Neither was any of the other items Lori had me wear.
I put on the blouse and pulled up my slacks both soaked in cum and Leah's cunt juices. I tried to pick up my jacket. At least I could cover myself up for the bus ride home, but Lexie was standing on it and refused to move. I left the office.
Stunned and confused, I walked to the bus stop without cleaning myself up. The cum on my face started to dry up even though I had wiped most of it off. The stench of sex reeked from me.
I got on the bus which fortunately wasn't crowded. It was a short ride home. The female bus driver gave me a smirk as she looked at me. My stained blouse was obviously feminine and my camisole was easily seen through the light material. It also did nothing to help cover my sized B tits.
I paid my fare. I moved to the back and hid.
We passed by the local college campus. Two girls got on. I recognized them from previous trips. I named them Cindy and Mindy although I don't know their real names. They were boisterous and always teased me whenever they saw me. And they saw me. Today wasn't going to be any different; probably even worse.
Somehow I ended up seated between them. Both of them started pawing my body. Mindy's hand went under my blouse while Cindy's snaked into my slacks.
"Oooh! He's wearing panties and garters too." Said Cindy really loudly for the entire bus to head.
"His tits are nice." Mindy added, just as loud. "And his cami is so cute."
"No, please leave me alone." I meekly begged. "Let me go home in peace."
"Well... Okay." Said Cindy. "But you look so messy. Maybe we should help you clean up a bit." Mindy nodded get head in agreement.
The reached into their bags and pulled out some make up. Cindy mounted my lap and was rocking her crotch into mine as she applied some eye shade and mascara on to me.
Mindy then took her place on my lap and slapped on a heavy coating of dark red lip stick.
Then they were laughing as they both got up and got off the bus at the next stop.
Even though I could not see myself, I felt I looked like a clown.
I straightened my clothes as best I could. As I got off at my stop, I just knew Lori wasn't going to be happy. I was right.
As soon as I opened the door, I saw Lori waiting for me. She was dressed stunningly in pink lingerie. With hands on hips, she glared at me.
"What the fuck, sissy boy!" Lori yelled at me. "You come home late. You look like a slut. What's that shit all over your clothes?"
She made me move to the centre of the living room.
"Take off your blouse and pants." She ordered. I complied.
"Why are your camisole and panties all stained? Your stockings all laddered? And you smell like cum!" Lori demanded.
Knowing better than to lie, I told Lori everything; about Leah and Lexie and Cindy and Mindy. Lori listened without interrupting me.
When I finished explaining, Lori moved behind me. She placed a blindfold over my eyes and tired it tightly. She used her foot to spread my legs wide apart and pushed my head over.
"Grab your ankles." Lori told me. I prepared for punishment."