Step One:  Put Boy In Pretty Skirt

#sissyGoals

#iwannabeagirl #male-to-female 💅👠🎀

Yes please

Yes ! To the Point of Know Return ! ( Thank you Kansas 🎶! )

oh my

Fuck the Boss

I had nor been Mr Kelly's assistant long. But had worked for the company for two years now. It wasn't my ideal job but aa good stepping stone. Part of my job was opening his mail. So when he received a package I didn't hesitate to open it. I was instantly surprised and glad no one was around to see. Inside was a huge strapon dildo. I blushed and closed the box. Maybe I should tape it shut. But I just left it on his desk. I couldn't even look at him when he returned from his meeting. He went in his office and closed the door. I tried to forget about it.

When pay day rolled around there was a bonus in my check I wasn't complaining but for what? I wanted to make sure it wasn't a mistake and asked Mr Kelly.

"Sir, sorry to disturb you it's just, I got a bonus and wanted to make sure it wasn't a mistake" I said handing him the check. He didn't take just looked at me and replied

"Discreesion" is all he said. I just nodded and left. I finished the day and went to make sure Mr Kelly didn't need anything else. I knew he wasn't busy so I just knocked and opened the door before he could answer.

"OH I am so sorry" I said quickly closing the door as I had walked in in him with his pants off the strapon attached to his chair as he rode it .

I went home I didn't say a word not even to my husband, Greg. I figured I would get transferred or something Monday. He wouldn't fire me would he? I was nervous when I went to work. I had been there an hour when Mr Kelly arrived. He stopped at my desk.

"Samantha would you mind stepping in my office" he asked not even able to look at me. I followed him into his office at first I was going to leave the door open then closed it.

"Samantha I don't know what to" he started.

"If this is about Friday, forget it my mistake I should of knocked louder" I said. He seemed to relax a bit.

"Again Samantha thank you for your discretion" He said

"Of course Mr Kelly" I said turning to leave.

"Michael, I believe you should call me Michael" he smiled. He was a good looking man 10 years older then me but in shape. Shorter then my husband maybe 5'7" skinny. Why was I checking him out I thought to myself?

"Of course Michael" I smiled back. I turned to leave. I stopped I should just keep walking but didn't.

"I know it's none of my business" I started then turned "nevermind" I went to leave again.

"It's okay, what is it?" Michael asked.

"It's just, doesn't it hurt? It was so big" I asked instantly regretting it.

"Well, it does but also" he was turning red. "Have you ever?" He started. "I mean would you like to?" He shock his head knowing he over stepped.

"Michael I am happily married" I reminded him.

"You wouldn't even have to get undressed it fits over your slacks" he was obviously excited by the idea. "I would compensate you" he said then instantly "I sorry I didn't mean to imply" he was turning into a bubbling mess.

"I am going back to my desk now, and pretend I didn't open a box last week, or come in here without knocking" I turned and opened the door. I walked to my desk. I swear my panties where dripping wet.

What would be the worst thing if I stormed back in their and fucked whim with his toy? I thought this was so crazy. I couldn't though that would be cheating on Greg. Was it cheating if he never touched me?

Micheal didn't have anything important on his calender today, he was somehow related to the owners. He was a powerful man that wanted me to? I got up and walked back to his office I knocked loudly.

"Come in" he called out. I closed and locked the door behind me walked around his desk and stood close to him.

"You won't touch me" I stated it wasn't a question . He looked up at me and nodded. "I don't know how to" I said he unlocked his desk drawer and pulled out his toy.

"I have to" he stuttered as he had me step into two hoops. I realized I had to pull it up. He was careful and gentile to not touch me as he tightened the straps. It was heavy. I looked down to see a penis, a large one at that. Jutting out from my waist. I felt my juices running downn,y leg. I had never been this excited in my life. I grasped the toy. I couldn't close my hand around it. I ran my hand over it. A feeling of power of took me.

"Assume the position" I told him. He quickly handed me lube. "You do it" I told him. He applied some to "my cock" he was stroking me. I moaned a little I couldn't feel his hand but loved having him stroke my cock. He continued.

"Pants off" I told him. Quickly dropped his pants. He wore red lacy panties. He bent over and pulled down just the back. And pulled out a plug. I wasted no more time I held my cock against his hole and pushed. It gave way easily he let put a yelp as it did. And a deep moan as I slid the toy all the way in. He easily took it all. Must be 10 inches I thought as I, oved it in and out. It was awkward to be thr one fucking I laughed to myself. But tried to find a rhythm. Micheal was moaning trying to be quiet as I fucked him. I was so hot. God I wished I was the one bent over the desk. I grew tired and stopped buried deep in his ass. Then pulled out. He fell to his knees. I released the straps and let the cock hit the floor with a thud. I had soaked thru my slacks a wet spot had appeared on my crotch. Micheal leaned in just smelling he took out his hard cock and played with it as he inhaled deeply. This man was getting off on smelling me. I watched his penis wasn't bad I thought about average I guess.

"May I cum?" He mumbled. He was asking me. I pulled his head into my crotch and he did he came all over the floor. I let him go and used his private restroom. I got myself cleaned up. But was still so horny. I resisted masterbating in my bosses bathroom, silly since I had just fucked him in thr ass. I went back to work.

As soon as I got home I dragged Greg into the bedroom. I was naked in record speed.

"Fuck me, I need you right now" I told him. He didn't need any encouragement and bent me over the bed. I came as soon as he slid in me. And again before he finished.

"Wow what got into you? "He laughed. We quickly got dressed and I made dinner. Whi.e Greg helped the kids with thier homework. By bedtime I wanted Greg again. He was more then happy to comply. As I sucked his cock. He fingered me. We came together. Swallowed and went to brush my teeth. I spent the whole weekend attacking my husband every moment we had I pulled him into the bedroom, the bathroom, heck even a changing room at the mall. I couldn't get enough.

Monday morning I was excited to go to work. I packed a change of underwear. I didn't know what to expect. Was that it. Or would Michael want me to fuck him again. Could I make him suck the strapon, or spank him. I sat at my desk and started going thru the messages that had come in over the weekend. Michael came in around 9. He couldn't look me in the eye. I followed him into his office,

"There was a problem with a truck this weekend the delivery to Jasper didn't get there" I informed him he was listening but not looking at me. I walked up to him.

"Eyes up" I ordered the door to the office still open but I wasn't loud. He jumped and looked straight at me.

"Now there was also an incident in the warehouse no details but, Mr Louis fired two workers" I continued. His eyes drifted down.

"Michael, are you sure you deserve to look at my tits" I told him his eyes jumped back up. "I will give you some time to deal with this then I will return" I told him with a smile. I turned to walk out.

"Um Samantha, Mrs Jorge's? I am sorry for looking at your breasts" he fumbled over the words. I walked back up to him standing very close. I unbuttoned my button on my blouse allowing him to see the tip of the white lace.

"That's enough for you isn't it, a reward for understanding you should apologize" I smiled he was obviously excited I fixed my button.

"Now get to work" I told him and returned to my desk. I was excited myself. I loved having such power. I was worried he wouldn't respond.

It was almost lunch by the time he opened his door. He just opened it and went back to his desk. I waited. Was that an invitation? His way of asking me to come in? Some timid way, so it didn't seem like his idea. I made him wait. Only when I was going to lunch did I peek my head in.

"Off to lunch be back soon" I told him. I stopped. I opened his door fully. "I think you should leave the door open at least till I return" I told him. And left.

As soon as I returned from lunch I walked into his office and closed and locked the door. I walked up to him he stopped what he was doing.

"Pants off" I ordered. He dropped his pants he wore a pink thong. It was way to small for him straining at the waist.

"Now are you a faggot?" I asked. "Your not gay, gay men don't wear stolen panties" I said. "Little bad sissy faggots due, though don't they? " He looked at the floor.

"Shirt and tie" I motioned he quickly stood before me in just his little pink thong.

"Does Mrs Kelly know you love cock?" I asked. "Are those hers?" I asked.

"No, no Kathy doesn't know anything" he seemed panicked.

"Who did you steal them from?" I asked.

"The nanny" he said even more ashamed.

"That won't due. You need to go buy your own, ones that fit properly. Maybe a bra as well" I told him. "Not just one pair either, enough so you can wear something pretty every day. You would like that wouldn't you?" I teased. His dick was leaking a wet patch morning in front of the tiny thong. It still managed to hold him in place.

"My husband loves when I suck his big cock, all real men do. You want to be able to please a real man don't you?" I asked. He didn't answer just turned more red.

"Take out your toy and show me how you would please a real man" I told him. I was soaked. Getting off on this power trip. I wanted nothing more then to strip and sink that toy deep inside me. I watched as he tried to suck the toy.

"More tounge, more slobber" I told him. Show him what a good girl you can be" I teased. I pushed his head down making him gag. Then letting go. I watched him for ten minutes.

"Prehaps that's to big to start out, buy a smaller one to train with" I told him. "I want to see you in sexy girlie things everyday, not stolenthings. Pretty things you picked fro yourself" i told him. I then opened my blouse showing him my bra. I got close to him but wouldn't let him touch. I then lifted my skirt and pulled his head to my crotch. My simple cotton panties soaked I held him so he could smell me but not touch.

"Play with it, rub yourself thru the soft panties" I ordered him he came in under a minute. I released him. I changed my panties in his bathroom. Then rubbed the wet ones all over his face.

"Don't wash it off till you go home" I smiled and returned to my desk.

Later when I was home, he texted me pics of lingerie from a store. He was shopping. Asking if I liked this or that. I didn't respond at first helped the kids with homework and cooking dinner. Greg was working late. After about 10 texts I started to reply telling him what I thought. He told me he ordered a new toy like I told him to as well. He was looking for praise. I didn't give it.

After the kids in bed and Greg had eaten I needed to tell Greg. I couldn't continue with out him knowing it was like cheating even though I never touched him. I sat Greg down and explained everything and how it made me feel. Greg just listened till I was done.

"That's what this weekend was about?" He smiled "if I get the benefits" he laughed. Then got serious.

"Would you like me to submit to you ?" He asked.

"No baby, I love when you take me. Would you like it if I submitted to you? Would you spank me?" I asked my hand rubbing his cock thru his jeans. "Take me, pleeaaasssee" I grinned. He flipped me over lifting my skirt and yanked down my panties. He took me right there on the living room floor.

"My dirty perverted wife gets excited making men beg to smell her wet cunt" he laughed as he smacked my ass. I just moaned and he did it again. After as he held me.

"You could force him, blackmail him to promote you" Greg told me.

"I don't want to be that person, it's just." Greg just held me tighter.

"Then do it right, make him shave" he told me running his hands over my hairless body. We eventually got up and went to bed.

In the morning as I was getting dressed. Greg came up behind me wrapping his hands around me.

"No my wife is going to start wearing sexy lingerie for me" he told me. Moving my cotton everyday panties aside he picked out a pair of red lace boy shorts. I kissed him and slowly changed my panties whi,e he watched.

"As you wish" I smiled at him. He just grinned and left for work. I finished getting dressed. I definitely packed spare panties these where basically see thru.

Michael was already in his office when I arrived I marched in and locked the door he stood and stripper before I said a word. He wore an expensive lingerie set, a demi cup bra, with panties a garter and stockings. I opened the drawer and handed him the strapon he knelt and adjusted the straps. Without being told he started to suck my cock.

"On the desk" I ordered he went to bend over. But I spun him and had him lay on his back. I didn't lube it I just lifted his legs and pushed the toy into his ass. He moaned loudly. But I shoved his tie into his mouth. And fucked him. He tried to play with his penis but I smacked his hand. Then as Greg had smacked my last night I smacked him. I pounded away on his ass. And he just wanted more. I became tired and stopped I removed the toy. And left him on the desk. As I left his office. The rest of the day. Went on as usual.

As I went to leave for the day, Michael was on the phone dealing with some crisis. I walked up to his desk and placed a sticky note on his desk. It read

GOOD SLUTTY BITCHES HAVE SMOOTH BODIES.

I just left it and walked out. Again later Michael texted me. Worried about shaving. He told me how Kelly had not slept with him in months, but was worried she might notice. I let him rattled on for quite some time.not responding before I sent

"You want to be hairless for me, and happy that Kathy doesn't want you anymore. I don't want you to have sex with anyone anymore without asking me first" I told him.

Greg picked out a nightie for me to sleep in. And had me suck his cock. But then denied me any pleasure at all. Jus they'd me as I fell asleep. In the morning I found several new pairs of panties in my drawer all things in bright colors. In lace or satin. I didn't like thongs but put one a yellow one without complaint. Greg grabbed my ass as he left for work.

I was extra horny when I got to work, Michael was late not arriving till after 10. I followed him into his office but left the door open.

"Meeting with A Mr Lopez. In 15 minutes. I told him I stepped close.

"I hear he has a reputation and a big cock" I smiled "girls talk" I turned and left him standing there.

Greg was enjoying his new found power over me as well. He sent me a link on how to prepare for anal sex. We had done this a few times over the years but I didn't really enjoy it and usually just turned into a disgusting mess. He was planning on taking my ass there was no doubt about that. Mr Lopez the head of shipping arrived for his meeting I sent him right in, there where in there for almost two hours. Before MIchael called and asked me to order out lunch. I had lunch delivered adding something for myself.and bought it in to them. Mr Lopez, Jose was looking over Michael shoulder pointing out figures. I could tell Michael was excited having this big good looking man standing over him. I just smiled and left them to work.

Jose left about an hour later I went in to clean up from lunch and no Michael I wondered and opened his bathroom door, he was naked masterbating. I stormed in.

"Stop that" I ordered I had not closed either door. Michael froze.

"What do youthink you are doing? You are not longer a man" I reminded him. "Man jerk their penis, sissy girls fuck thier asses" I told him. I noticed he had shaved every inch of his body even his arms had no hair. I walked over and ran my hand down his back.

"Go ahead as a treat you can finish" I told him my hand stopping on his ass. He shot his load immediately into the toilet.

"You aren't allowed to pretend to be a man anymore, I don't even want you standing to pee" I told him. "You got so excited having Jose so close to you" I teased he got hard again. "You are such a little pervert. I bet you like it if I made you wear a dress and sit at my desk. I pushed him to sit on the toilet. And lifted my skirt.

"Hands at your sides" I told him and pulled his face into my tiny thong. I rubbed his face against me. He stuck out his tounge and I allowed him to lock my panties, he was soon sucking on my panties. I got caught up and let him. I stopped him as he moved the tiny slip of cloth to the side and his tounge touched my bare pussy. I pushed him away.

"Naughty girl, I am not a lesbian" I scolded Michael. I dropped my skirt and left hos office finally closing the door. I texted Greg. Telling him how I had been a naughty slut. Telling him he could have my ass for being such a bad girl.

I was all business the rest of the afternoon. I needed him to not expect attention to crave it. Actually the next few days I did nothing at all. Just business. By Friday afternoon he was desperate for me to show him any attention having me come into his office for every little thing.

"You been such a needy girl all week" I told him as I went to say goodnight instead I locked the door.

"I wanted to show you" he said pulling out a toy from his top drawer he stuck it to his desk and started to suck on it. He did very good taking most of it down his throat. I just watched as he did. I started to take off my clothes. I stripped down to my bra and panties. It was a matching set in red lace. Greg had bought me. I was getting used to the thongs but still found myself going to the bathroom to pick my wedgie. Michael watched as he worked harder to take the whole toy.

"Has Mrs Kelly noticed you are a faggot?" I asked him pulling out the strapon putting it on myself pushing Michael's head down on his toy. He couldn't answer with his mouth full.

I had him stop and stand bending over the desk I had him continue to suck his toy. I pulled his pants down. He wore a little yellow thong. I pulled it aside. And worked the toy into his ass. I fucked him slow taking my time. I worked his ass for over an hour. He had stopped sucking on his toy. He had cum in his panties.

"Take them off, suck your panties clean" I commanded without hesitation he pulled off his panties and stuffed them in his mouth. I was surprised. But didn't say a word.

"Would you hold my key?" He mumbled with the panties in his mouth as I got dressed.

"What?" I asked

"The key to my chastity cage, I can't stop playing with myself." He told me. I had no idea what a chastity cage was.

"Explain this to me" I told him.

"It's a cage that goes over my" he hesitated. "Pee pee. So I can't touch it" he picked up his phone and showed me pics of them. I stood and bent him back over the desk I took his belt and smacked his ass. He yelped.

"This is for touching yourself" I smacked him again. 10 times I smacked him. "I expect the key on Monday" then picked up his phone. "This one" I had selected the smallest one he had shown me. Then left for the weekend.i had arranged for my sister to take the kids for the night. I went home and made sure I had no stubble, I followed Greg's instructions giving myself an enema. I found it all strongly erotic. I even prelubed my my asshole. I dressed in a silk robe and waited for Greg. Drinking a glass of wine. Greg came in and I let the robe fall open.i knelt before him.

"I am yours do with me as you please" I told him. He just smiled and dropped his pants. I sucked his cock right by the front door. I didn't make him cum. Instead he led me thr bedroom. Where he laid me on my back and lubed his cock. He was gentile as he worked his cock into my ass. I felt free as I let him use me. I was his toy, his slut. I understood in a way how Michael needed this.

"I need more" I moaned.

"More?" Greg asked. .

"The vibrator in my bottom drawer of my nightstand." Greg pulled out and retrieved the toy. He was surprised when he pulled it out.

"When did you get this?" He asked. I blushed a little

"Years ago after the kids" I confessed.

"So you been cheating on me" Greg smiled.

"Yes, I am sorry. I am such a slut" I told him. He pushed the vibrator into my ass and turned it on full blast. Then shoved his cock into my soaking wet pussy. I moaned and begged for him to fuck and use me.

Greg fucked me stopping and starting teasing me. He finally finished by shoving his dirty cock that had been in both my holes into my mouth.

"You like being a dirty slut" Greg said as he hugged me. "I love you, this only a game" Greg told me.

"I know baby" I told him. "Would you let a man, a sissy suck your cock?" I asked him.

"Don't know, I don't think so. Besides wouldn't that be cheating on you?" Greg laughed.

"I would forgive you if you cheated on me" I told him. He just laughed we spent the night naked cuddling and making love again. Greg and I had never been closer.

Michael presented me with the keys to his cage first thing Monday morning. I fucked him with his toy for being a good sissy. I did some research and after some discussions with Michael I discovered what he really needed. I would fuck him once a week. But tease and belittle him daily. It became a routine but I kept him guessing on his toes. His wife found out and left him. Exposing him as some gay freak. I told everyone I had not witnessed any such thing but professional behavior from him. I even turned down a transfer. After I realized it would mean less time to have with Greg and the kids. And Michael was more then happy to offer me compensation.

Being a good mother and wife became so much more important. I didn't ask Greg for help around the house. Finding myself wanting to please Greg in every way possible. I submitted to him. He felt comfortable in the role. Even playfully spanking me for being a bad girl. When we went out I dressed alot more scantily then I would of liked but he loved it. But was the perfect PTA mom for family and friends. It all became the perfect balance I released any frustration and need to control on Michael which allowed me to submit to my husband.

Thank you for explaining that to me, Mistress

The far off look she gets.