The Ex's New Toy Pt. 03

Story Info
Dana Continues to take control of Matt.
8.6k words
4.62
51.7k
34

Part 3 of the 3 part series

Updated 06/07/2023
Created 08/02/2015
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Urtoy2be
Urtoy2be
568 Followers

Wednesday afternoon and work was slowing down for the week. Sitting in my office bored staring blankly at my monitor waiting for 5:30 PM so I could cut out. I need a drink went through my mind.

The weekend had been a blur. The events with my ex-wife and her new man had been crazy. Fantasies and thoughts had been awakened and now I was wondering who I really was inside. Was I really the sissy cock lover Dana had made me into?

Replaying memories I recalled her saying they would be back in town this Friday. And maybe bring a friend. Am I ok with that, is this to much?

As I was lost in thought my cell chirped with an incoming text. Only half coming out of the visions in my mind I picked up my cell, entered my unlock code, and glanced to see who the text was from.

Dana's face appeared on my screen. I sat right up. Why would she be texting me at work? Was it about this upcoming Friday? Was something up with one of the kids? I clicked the message to see if it was good or bad news.

I read the message three times being sure I had read it correctly. Dana's message stated that she and Rick would not be coming into town this Friday as Rick had been called out of town on business. Instead she instructed me to plan on coming there instead.

I was to arrive Friday evening after work and set myself up in a Hotel She named the hotel informing me that she had made reservations in my name for a suite. She included that I had 24 hours to call them and confirm with my credit card to secure the reservation.

After reading the text I felt a rush of excitement. For a fleeting moment I contemplated texting Dana and saying I could not make it. In the back of my mind I knew she would not accept that. I also knew I would be going even if my mind was screaming to stop this now before it got any farther out of hand.

Picking up the phone I tapped in the number for the hotel she had given me. After giving the receptionist the reservation number I followed with my credit card information. It was done, I had a suite for Friday and Saturday night.

I couldn't help but wonder what this devious woman had in store for me. Whatever it was I was certain I was in trouble. I also felt confident that even with my hesitations I would love every minute of it.

The more I sat at my desk thinking about it the more I noticed I was becoming aroused. My dick was getting hard at work. Unable to stop myself I texted Dana and asked what she had in mind for the upcoming week end?

I had barely hit send when my phone chirped. The incoming text read, "Don't worry Sissy you will love what I have planned for you." I could almost see Dana's devilish grin.

My texting her only enforced her knowledge that she had me right where she wanted. "What's wrong Bitchboy you having trouble concentrating at work now?" came Dana's next text.

I should have said no I am fine but without thinking I returned a text saying, "Yes I can't think about work thank you very much, my damn dick is hard." Hitting send I thought maybe I should not have sent that, to late.

Dana responded very quickly, "Prove it, go to the restroom and take a picture and send it. You better be full on hard too slave. And once you send me the picture DO NOT put your little cock away."

I couldn't believe what Dana was ordering me to do at work. What's worse, I couldn't believe I was going to do it. I walked briskly to the restroom hoping no one would notice the front of my pants sticking out from an obvious hard on.

Once in the seclusion of the restroom I closed the door to the stall and immediately dropped my pants. My hard on sprang out pointing straight up. I grabbed the shaft and gave myself a few quick strokes, damn it felt good. I needed to cum badly.

I quickly snapped a picture and hit send, while continuing to stroke my aching dick. Precum was starting to ooze and the head was slick and shiny. Without even thinking I licked the precum from my fingers.

My phone chirped. "Haha, you really are a slut. Just thinking about me using your sissy ass this week end has you like this at work," was Dana's reply to the picture.

The next chirp from Dana brought, "Sit your phone on something with the video running. Stroke your little dick and cum in your hand. If some one comes in the restroom you will not stop stroking. When you cum I want you to eat your cum out of your hand. Make sure your face is in the video when you lap up that cock juice sissy boi."

Dana knew how paranoid I am at work about any aspect of my personal life being known. I think she was making me do this hoping some one would come in the restroom while I was stroking myself, I only hoped no one would enter.

I sat my phone on the toilet paper dispenser with the video recording, a perfect view of my hard dick. I quickly started stroking faster knowing that no matter what I was going to do as Dana commanded. I wanted to hurry before some one came in.

Standing in the stall facing my phone with my stiff cock leaking copious amounts of precum my stroking started to make an all to familiar squishing sound. Fuck my hand felt good, and the kinkiness of recording myself jacking off at work was really turning me on.

Just as I was about to cum in my hand I heard the restroom door come open, Fuck. If I stopped Dana would see by the video timer that I stopped if I paused the video. Trying to be quiet I kept moving my fist up and down my rigid shaft.

Out of no where a little moan escaped my lips and sounded very loud in the quiet restroom. Trying to stifle my moans the squishing sounds didn't really work. The sounds only seemed to echo in the silence.

Just then there was a soft tap on the stall door. My breath caught in my throat but the hand on my cock never stopped moving.

"Matt are you ok in there?" came my bosses voice. Fuck me. Am I caught?

Wait, how did he know it was me? I was so worried about being caught I never gave that question a second thought. I should have. I tried to reply calmly but the shakiness in my voice was obvious. "Yes Sir Mr. Shire, I am fine, just a little stomach issue."

"Ok Matt, well come see me in my office when you are done," directed my boss.

Shit this could not be good. Hopefully it is about the project I am working on and not my restroom escapades. The restroom door opened and closed. I was alone again.

I had not stopped stroking my dick the entire time Mr. Shire was in the restroom. I noticed that for some reason I was even harder than before. If that was even possible.

Thinking I need to cum before some one else enters I squeezed my cock shaft and stroked as fast and hard as I could. I had all but forgot the camera was filming with sound. Dana would hear the exchange between me and my boss, great!

A few more strokes and cum erupted into my hand. My hand was so full I was starting to think it wasn't going to all fit in my cupped palm. I looked at the camera and could see the view of my full hand was perfect.

As my orgasm ended I knelt down on the dirty restroom floor so my face was right in front of the camera and started licking the hot cum from my hand. I continued to lick my palm and fingers until they were completely void of any remnants of my cock juice.

As I stood up and stopped the video I realized I had just stroked my cock off in the restroom at work and eaten my cum. All on video and even with my boss coming in. What was Dana turning me into?

As I returned to my desk I sent Dana a text informing her I had done as she required. Her immediate reply was to send her he video. Somehow I already knew that was coming. I attached the video to a message and sent it.

Even knowing the entire time I was only farther sealing my fate to be Dana's bitch for as long as she chose. She and I both knew I would do anything she ordered me to in order to keep these secrets from the kids.

"You really love eating cock cum you little sissy slut. You will be receiving instructions tonight on how to prepare for this weekend bitch. Now go see what your boss wants, I have work to do," Dana replied in text.

Shit, I had forgot Mr. Shire asked me to come to his office. I put my phone in my desk drawer, locked my computer and headed to see what my boss needed. Please be about the project.

I knocked on Mr. Shire's door before opening it and entering which was standard entry procedure for Mr. Shire.

My boss was on the phone when I entered but he indicated I should sit with a wave of his hand. Mr. Shire swiveled around his chair so that his back was to me and continued his phone conversation.

Mr. Shire was older, around 60 I would guess. He was still in very good physical shape for his age. I would guess around 185 lbs. or so. A full head of dark hair with only slight graying at his temples. I knew he played a lot of golf and racquet ball so his fitness was not surprising.

I sat quietly while Mr. Shire finished his business. As he turned back to face me he placed the phone back in it's cradle. As my boss looked at me my eyes caught sight of something that didn't seem right. I looked and my heart dropped. Mr. Shire was sitting there looking at me with his cock out of his pants.

Until that point in time I had never really thought about my bosses cock. I couldn't break my stare away. His cock wasn't overly huge but it was well above average I would say. Maybe 7.5" long and fairly thick, He was circumcised and had a fat round head topping off that fat cock.

"So Matt I don't think we have to pretend that we don't know what you were doing in the restroom earlier do we?" inquired Mr. Shire breaking me out of the cock trance he had me in.

I mumbled an almost unintelligible "No Sir" and lowered my eyes to the floor. At least I tried to look at the floor but my bosses cock pulled my eyes back to it. I saw Mr. Shire's cock twitch and start to move. I was shocked, he was getting a hard on right in front of me.

Mr. Shire went into a spiel about how we can't have that kind of behavior here and that he feels he must send me to HR for dismissal. Having his cock out and growing told me where this was going already.

Mr. Shire just needed me to be the one to say it, so I did. There was no pretense that I wouldn't so why fight it.

"Mr. Shire please don't fire me. It was the first time I ever did anything like that at work. I promise I will never do it again. I had a moment of weakness. Please I will do ANYTHING if you let me keep my job," I replied.

Mr. Shire said that if I were to obey anything he said and could keep it between us that he may have a way for me to save my employment. Of course I agreed to anything he wanted.

"Get on your knees Mattie and crawl over here between my legs," commanded my boss. I immediately hit the floor and crawled over to where he had indicated. I remained on my knees mere inches from Mr. Shire's fat cockhead with my eyes glued to his incredible meat.

As I stared hungrily at my bosses rapidly hardening cock he began to stroke it to full erection. Mr. Shire grabbed my hair and tilted my head back. He started rubbing his fat hard fuck stick all over my face.

"You will not say a word Mattie, you will just take whatever I hand out and accept it willingly or we both know what will happen," commanded my boss.

I nodded my consent as best I could with my hair being pulled back holding my head. Mr. Shire rubbed the tip of his now leaking cock on my lips smearing them with his precum.

As he did this he let go of my hair and forced two fingers into my mouth. As his fingers went deeper his hand started forcing my jaws apart. I gagged as Mr. Shire pushed both fingers into the opening of my throat.

"Take those fingers you kinky little slut, open that throat for what is coming next," said Mr. Shire.

As my throat adjusted to the intrusion and my gagging subsided my boss added a third finger determined to see my throat swell from his forced gaping.

As my gagging resumed tears began to form and run down my cheeks. I could tell this is what my boss was trying too achieve. He pushed all three fingers as deep as he could and twisted them back and forth.

Mr. Shire was hell bent on stretching my throat and testing my willingness to accept any abuse he wanted to inflict on me. For my job I had no choice but to take it.

In my mind I kept telling myself this is to keep your job and I knew it was. But the realization that my cock was hard as granite made me realize that I loved how Mr. Shire was abusing me.

Mr. Shire jerked his three fingers out of my throat quickly and they were followed by a torrent of spittle and mucous from the gagging and stretching of my now open throat.

Just as quickly as he pulled his fingers out my boss jerked my head forward and rammed the entirety of his manhood down my throat. As my bosses cock bottomed out in my throat and my face was buried in his pubic hairs

Mr. Shire pushed down hard on the back of my head. Refusing to allow me to breathe he moaned at the convulsions of my throat around his cock as I gagged and struggled for air.

While continuing to hold my face hard against his pubes Mr. Shire stood up pushing me back upon my haunches. When he was completely vertical my abuser released the back of my head and grabbed two handfuls of my hair.

Wasting no time at all Mr. Shire pulled his cock all the way out flooding the front of my shirt with spit up. Just as quickly he rammed all the way back in.

It was a brutal face fucking with me gagging and jerking and my throat spasming around his thick meat. Mr. Shire seemed determined to destroy my throat. I haven't even seen a slut get face fucked this hard in porno's.

Spit and slime was coating my face and chest as my boss pistoned his engorged cock in and out of my throat viciously. How could a 60 year old man fuck like this? Mr. Shire was a master at fucking my throat. He knew what he wanted and he didn't care if I liked it or not he was taking it.

The face fucking I was receiving was draining my strength. Maybe it was the lack of air as I only got a quick breath about every third or fourth stroke. I heard my boss start to moan and I felt his cock start to swell even larger in my throat.

Mr. Shire shoved his cock deep and worked his hips in a circle making his cock rotate in the depths of my aching throat. He did this for what seemed like minutes but truthfully probably just seconds before pulling out and ordering me to tilt my head back and hold my mouth wide open.

Mr. Shire pulled his pulsing cock out of my sucking mouth and started to stroke fast and furious. I closed my eyes as he started shooting shot after shot of hot man cum on my face and in my open waiting mouth. I don't know how many shots there was but this man literally coated my face and almost filled my mouth with his salty bitter love juices.

As my boss slowly stopped cumming he used his cock to push all the cum off my face and into my mouth. Once his slimy cock had fully rubbed his slime all over my face and pushed all of his cum into my cocksucking mouth I was allowed to swallow.

Mr. Shire released my hair and I collapsed in a heap on his floor. He did all the fucking yet I was the one exhausted from it. My boss sat back in his chair looking down at his handy work.

"Fix yourself up as best you can cocksucker and go home for the day. Use my personal exit bitchboy. I can't have you in the office looking like the cock eating slut you are right now," ordered Mr. Shire.

As I was about to leave my bosses office and head home for he day, I was still in a stupor from the incredible facefucking and massive load of cum I had received. Mr. Shire said, "Oh, and say thank you to your ex for me. Dana called me and told me you were in the restroom playing with your little cock. I didn't believe her until I went to see for myself."

Dana had set me up with my boss. Was there no limits to what my ex wife was going to put me through now that I was her sissy slave?

Mr. Shire also informed me that he has parties from time to time at his country cottage and now that he knows I will do ANYTHING he orders me to, he will call on me from time to time to attend and entertain his guests. I wasn't sure about that but I knew it didn't matter. I would go when called upon.

On the drive home I thought about my current situation. In less than a weeks time I had gone from a normal everyday guy to a sissy cock sucking slave to my ex wife. And now apparently to my boss as well.

My thoughts went to the upcoming weekend. Dana was obviously planning something crazy. Little did I know it was going to be more than I could imagine at the time.

Arriving at home, the days events had tired me out so I took a quick shower and fell into bed for a nap. I was awakened at 7:00 PM by the belligerent ringing of my phone.

Of course it was Dana's face looking at me when I checked the caller ID. I forgot she had said I would receive instructions this evening. I pushed the talk button and put the phone to my ear.

As soon as Dana heard my hello she started right in. "So how was that cock lunch cum eater," she asked? I could hear the amusement in her voice.

"Yeah, thank you for that. That's my job," I replied sarcastically.

"Relax cumslut, your boss loved your throat. Your job is cemented in stone for as long as you want it now. Well as long as you service his cock that is," Dana laughed.

After a little more back and forth I was instructed to log onto my Amazon account and order some things. There were links in my email for the items I was to purchase. Also I was to order overnight delivery and bring the items with me Friday.

Before I was permitted to hang up I was instructed to turn on my Skype video and jackoff for her and eat my own cum again. While using my laptop for this Dana remained on the phone calling me more nasty names than I even knew that she knew. Where did she learn to be so dirty mouthed?

Logging onto my email and Amazon I found I was to order a full assortment of feminine attire. Panties, bra, stockings, fake tits, makeup, heels, and a blonde wig. My first insight as to what the weekend held in store for me. With a heavy sigh I placed the order and requested overnight delivery.

The rest of the week was uneventful. Friday came and I left work at half a day to start my week end. At home all the packages had already arrived and were waiting for me. I showered, packed, and headed out for the two hour trip to Dana's.

I arrived at the hotel shortly after 6:00 PM and checked into my suite. As I was unpacking Dana called. I was instructed to shave my entire body from the neck down. She also told me to go to a local sex shop and buy a 6 inch by 6 inch anal plug and an enema kit. I was to give myself an enema then force the huge anal plug into my sissy boi pussy and leave it in all night.

She also wanted me to buy a baby doll nightie with matching panties at the sex shop in pink and sleep in it. Under no circumstances was I allowed to take it off before Saturday and I also was not allowed to wear a robe over it.

The sex shop was actually close to the hotel so the trip there and back went relatively quick. I had told the clerk the items were for my girlfriend. The amused look on her face as she rang up the items was more than enough to let me know she did not believe a word I had said.

Back in my hotel suite I took out the enema kit and proceeded to give myself a cleansing as I had been instructed. I repeated the process three times just to be sure I did it well.

When I completed the enema task I grabbed my razor and shaving cream and stepped into the steaming spray of the shower. I shampooed and soaped my entire body then rinsed myself clean. Next I applied shaving cream to my arm pits and chest. I began the arduous task of voiding my body of hair. It took quite a while as several areas I had to shave twice.

Urtoy2be
Urtoy2be
568 Followers