My TS Gurlfriend Dom
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I was at my desk at work the day she came into my life, and it was all over the moment I saw her dark, voluptuous body squeezed into a body conscious dress as she sat at the Lead Admin Desk and asked who else besides the Senior Staff did she work for....Her dark smoldering eyes, pouting lips and long wavy hair made me think of Vanessa Williams and what would it take for me to seduce this incredibly sexy woman and make her mine? Well except for the fact that she used to be my male admin and was now living with me, I guess she was mine!
It all started when I got a new Admin about 1 year ago and he was a young, slender, dark, slightly flamboyant and too well dressed to be purely Het. He was drawn to my larger size, hairy body and commanding personality from the start. CaeAntone, however was very efficient and organized even if he may have been too effeminate and girly, but was still a great admin! I noted one day however that he was out of sorts and seemed to be nursing his left arm. When questioned about it he mumbled "I'm OK. just hurt myself the other night tripping down the stairs." Well that's when I started to notice a pattern of abuse on the poor guy and noted that many injuries happened on the weekends. After multiple occurrences I called him into my office and stated my concerns and that is when he broke down....Crying about being a dresser and his boyfriend was abusing him and not knowing what to do and could I help him and make his boyfriend treat him right!? That's when I told him he was going to have to choose what he wanted and if it was being mistreated or not, that should tell him his next course of action. Two days later he had to call in sick after "walking into a sign post" and I told him that if his BF had done it, to tell him you had broken up with him and that I was the new guy taking care of him ( a bit of chivalry had broken through I guess as I hated to see anyone being treated poorly in a relationship ) and if he had issues, he could see me! He sobbed his gratitude and offered to make me a nice dinner which I strangely accepted as I could tell he needed a strong leader in his life.
So when Friday came around, CaeAntone came into my office and closed the door. He then told me that dinner was going to be a simple salad, BBQ Chicken and Sweet Potato fries with Corn Bread and Southern Tea ( an alcoholic drink ) with parfait for dessert. "Simple hmm?" I asked. "Well it is for me and I actually made the Cornbread and Parfait last night. Here is my address and could you please be there at 7? Thanks again for helping me out and I truly want you to know I appreciate it!"
Well when I showed up at seven I was not totally surprised to find him in lady's tight designer jeans, low heels, a long blonde highlighted wig, make up, sporting 'C' cup breasts in a buttoned sleeveless blouse. He/she looked cute and if I did not know better, would have taken him/her as a woman easily.
She took my coat, gave me a tea and told me to relax while she set the table. Dinner was just a few minutes away from being ready. She told me her fem name was Toni and that she hoped I did not mind her being this way tonight. I responded with an "It's OK. I must say, you actually look quite pretty and not what I expected after seeing you at work!" She thanked me and finished setting the table and laying out the food. I have to admit, she could cook and I listened to her story about how she dressed for years, met a guy and started dating him as Toni thinking he knew she was a dresser but found out she was wrong after their first night of heavy petting and fondling. He kind of freaked and was just not comfortable and would end up getting mean after sex due to feeling guilty and unmanly! Well dinner was awesome, the Tea kept flowing and we ended up chatting until late at night and actually seemed to share quite a few things in common ( like Fave Foods and a love of Ballroom ) and at the end of it, Toni agreed to go out with me Saturday night for Thai and dancing at the local ballroom club, Blue Sueade Shoes.
The next morning, I wondered if it was the booze, the nice meal or if I was just crazy dating a Crossdressing Coworker, especially one that worked for me! But, decided if CaeAntone could keep his lifestyle secret it could not hurt for a dinner date, right?
Saturday, I made sure I was looking good in my favorite black dance slacks and a sharp blue shirt that showed off my hairy chest. She wore a uneven hemmed turquoise dress with a princess neckline and gold dance heels. I would love leading her around the floor during Tango and Rumba numbers. Well we had a great meal and as a dance partner she was amazing! She took a good soft lead, knew her steps well and when we did the Cha Cha, or bachatta, her hips were smokin! Did I mention her Cuban motion was almost sexual during Rumba and I found it almost impossible NOT to get hard. But at the end of a Waltz, I dipped her and when I brought her up, I could not help but to kiss her and tell her what an amazing dancer she was. She confessed to doing some exotic when she dated her last boyfriend as he really liked it, but Ballroom always seemed to be the dance of love, while exotic was pure sex! I responded with, "I would love to see that, because if she could be sexier doing exotic dancing, it would be criminal, I am sure! I thought she was wow sexy just doing ballroom!" She smiled and gave a little laugh and said, "If I played my cards right, I just might get that opportunity!"
Well needless to say we closed out the place and found us in the parking lot making out for a short time before I stopped to take her home. When we got to her place, she kissed me again and told me she would like to go out again and that she hoped it would not make work weird, or that I was OK with her double life. I assured her, I was OK with seeing her again and could keep work and Life separate. I left thinking "wow, never thought I would be attracted to a guy but she did not look like one...looked like a duck, walked like a duck...must be a duck!"
Work did not get weird as I was able to act professional and needed to keep our date discrete. Now at 6'1" 175 and being hirsute, I am not the most handsome guy, but women have told me I have a smile to die for and they love the blue eyes and dark reddish brown wavy hair. I use it to my advantage and never had to hard a time getting women. But these days, All I could think about was Toni and those incredible kisses we had and how I had to see more of her. I had to know what she was like sucking cock since I knew that sexy little sissy would suck mine if I told her to do it. So, Thursday, I called her to my office and asked her if I could take her out Saturday to the Club Astaire dance party and dinner. She sadly refused me as she had a prior engagement, so I knew she was playing the hard to get game and pressed for a Sunday brunch which she agreed to.
Saturday afternoon I got a call from a guy who said, "he was Toni's boyfriend and that I best stay away, or he would...." I interrupted with "You'll do nothing you little punk! Leave my employee alone or I will turn you in for assault, Rape and sex trafficking. You know how long you'll last in a prison little man? About 24 hours! So don't call me again. Don't call her again and bugger off or if not, I have no problem taking my frustrations out on you!" and then hung up! Neither Toni or I ever heard from him after that strangely enough!
Sunday, I dressed in acid washed jeans and a pale pink and grey polo, some dark socks and loafers so I could dance if I got her to the ballroom or just look good at the meal. She wore a body con dark blue full-length dress that zipped all the way from hem to neck and left the top undone to show off the cleavage and unzippered from the floor to about mid-thigh showing off a ton of dark leg in tan wedge sandals that put her right at my height. We ate, flirted and touched and kissed as we walked, and I knew I was getting into her panties. When we got to the car, she pushed me back, undid my pants and pulled out my cock and started stroking it and bent down and licked the head. She stuck her tongue into the eye and then bobbed quickly onto the head and down the shaft deep throating me and making me moan and move her hair out of the way and watch as she bobbed up and down on my cock tickling my balls with her nails. She stopped and looked at me and said she had been thinking about blowing me for days and just could not wait to get my big white cock in her mouth and since it tasted so good she would be glad to suck it anytime! With that she started licking up and down, fast and slow, tickling and sucking and wanking it making all those sexy slurping noises that shows a girl is really into the blow job until I unloaded into her mouth with a groan. She licked and sucked out my remaining seed and then kissed me hard sticking her tongue into my mouth and telling me she loved the taste of my cock! I could just taste the residue of my sperm on her lips and tongue but was so endorphic from the orgasm, I did not say or do anything. She told me maybe I could return the favor sometime and I told her anytime as I loved eating a woman and felt I was a master at it. She just looked at me, smiled and said, "she was not that kind of girl!" with a wink. I knew she was a dresser, but for some reason was only seeing her as a woman and knew I was going to take control of this relationship.
The next day at work, CaeAntone was back to his male self but definitely seemed happier and less stressed. I heard him gossiping at one point about how he met someone who helped him out of a bad relationship and was relieved of not being afraid anymore. The other office girls were so sympathetic and understanding and ultimately happy for him. It made me grin to myself to know that I was the one that helped him, and little did the rest know that CaeAntone was a dresser and looked much more feminine than some of them did!
One week later I had to travel to a conference and made sure CaeAntone booked everything for me, then called him into my office and told him to insure the bed was queen sized as I was expecting company. He frowned until I told him I knew this girl named Toni that would enjoy some time in the city after the conference! He just lit up and asked when she would be joining him, so he could make sure she was on the room list with the hotel. Once that was given, I knew I would have company with no worries of anyone from work seeing us and putting two and two together.
Well I flew out early in the morning and landed at the airport, got my car and drove to the hotel. My room was already appointed so I got my key and went on up and when I opened the door, I could hear someone in the room. Then Toni peaked around the rooms corner asking, "is that you Daddy baby?" Then she rushed me, throwing her arms around my neck and kissing me and saying she left early to surprise me! I noted she had on a white bra, panty and garter set with tan stockings and Black heels! She told me that she was dressing for me ....and dinner later! She helped me put away my things and then handed me a drink as she sat me down and took off my shoes. Then she knelt in front of me and started to undo my pants and provide a long slow sexy blow job. I was amazed at how good she was at sucking cock. "You really like sucking my cock don't you Toni?" I asked her. She responded with a MMhmmm around the head of my cock while it was still in her mouth. I am a fairly well-endowed guy at about 9 inches and pretty thick, so many women had trouble taking it all in their mouth, but she was able to take it with ease! Her mouth wrapped around my head and I could feel her tongue rubbing along the helmet as her hands wanked the shaft and used her extra spit to lube up the entire length. I quickly started to hear that wonderful slurping and smacking sound a woman makes when she is really into sucking cock and wanting her creamy treat. She moved up and down, licking, bobbing on the head, deep throating it and then using her throat to massage the head with a swallowing movement that drove me over the edge and made my shaft expand and squirt 3-4 shots down her sexy mouth. Then she pulled me out and opened her mouth with the tongue extended and wanked out the rest of my seed and then when she felt she had it all, popped me back into her mouth and sucked me again on just the head to insure she got it all and looked up at me and smiled with a "cat just ate the cream" look on her face. She then asked, "Did you have a nice flight baby and did you enjoy the room welcome service?"
I told her "The flight was OK, but that welcome service at this place is fantastic! We have a little time before dinner so want to get dressed and grab a drink prior to the meal?"
"That will be great! Let me slip into something nice for you while you put on your shoes back on Daddy."
Well as I redid my shoes I noted she slipped into a black pencil skirted, white topped dress with a low cleavage and long lacy sleeves. Her nails were done and she just had to touch up her make up after that greeting and she was ready. We got into the elevator and she leaned against me facing away turned her head and kissed me saying "I never had anyone treat me so nice with dinner and a stay in a big fancy hotel baby. I am gonna treat you so good, you will not want to get rid of me!"
"Well let's recall, I am here on business Toni, you're an employee and it would ruin both our jobs if this got out." I gruffly responded. "what is nice about this trip is that we ARE in the city, not a big chance we will be recognized, and I can expense this as entertainment, so we can enjoy this! I am enjoying your company though no matter what my little sissy gurlfriend." I said to soften the harshness of my original statement.
Dinner was nice, some salmon with vegetables and a nice lite chard to sip along with it. Conversation was fun as Toni talked about work, sports and how she grew up and was so happy to be with a guy who took control and treated her like a lady instead of a one-night stand!
With dinner over, we retired upstairs with another bottle of wine and some TV prior to bed as I had an early day with the conference. One thing leads to another and she is leaning against me, kissing and telling me how she is really enjoying being my girl on this trip and will it be OK if she spends the day shopping or by the pool in a little bikini? I smirk and tell her to enjoy Frisco and check out Pier 39 and maybe Ghirardelli. Toni then hikes her skirt up, straddles me and whispers in my ear on how she may need to catch her flight back prior to my finishing the conference so she wants to make the most of her time here and starts to kiss my neck and unbutton my shirt. She uses her nails to scrape my nipples and then sucks briefly on the left one and starts to unbuckle my slacks. When she pulls out my engorged cock she smirks and says "Mmm a perfect desert for my meal!" Slides down, sucks it into her mouth and bobs up and down a few times and then climbs back up and re-straddles me sliding my turgid member into her ass pussy and begins a slow sexy grinding of her hips which causes me to hold onto her hips. As she starts to hump up and down on my cock, I grab her ass and squeeze it and force my tongue into her mouth. She groans and sucks on my tongue and wraps her arms around my neck and starts kissing with increasing ardor and humping on my cock moaning about "how good it feels inside her, Oh god, Oh yessss, Oh god baby it is so good, Oh daddy, yes, fuck me with that hard cock, Oh god baby I am gonna come! Ohhh Ahhh unghgghh.........and shouted my name in a long drawn out cry as she spurted all over my belly and started to kiss me wildly all over my face saying how she had never come like that before or so quickly. She slid off with a pop and cleaned up my cock and her spunk with a quick tongue bath that was so submissive and sexy I was hard again and pulled her up and removed the dress, leaving her in her garter, stockings, bra and panty with her heels on and carried her to the bed and then took off her panties and told her we needed to get to bed, but first some fun. I rolled her over and spanked her for coming on me and told her if I was going to be her 'Daddy', she needed to learn to take commands as my submissive little sissy girl! She yelped the 1st couple of spanks and then started to squirm and moan until I stopped, lifter her up and then sat her on my lap and told her I wanted her to know I was the boss at work AND in this relationship and she needed to know that! She agreed and said "Yes Daddy. I did not mean to make you angry Daddy. I will be your good girl." I told her "Good girl. I knew you were a submissive and I know you will love me as your daddy just like I am going to love you as my sissy girl."
I started to kiss her and then slid her thong panty off and lay her on the bed. I told her she would be used as a woman and slid her legs over my shoulders and pushed into her waiting bum with just the head and held it there. She looked at me for a moment and tried to hump onto my cock but I kept just the head inside her and told her to "beg me to fuck her!"
"Oh God Daddy, Fuck me with that cock! Fuck me please! I need you to fuck me and make me your woman! Please fuck me long and hard baby!"
Well I thought that was good enough and slid all the way in balls deep and held that for a few seconds and then started a slow, long in and out, while she moaned like some cock drunk slut with her arms wrapped up around my shoulders and sometimes down on my ass pulling me into her. I felt her tense and quiver beneath me as she came again and then again in a stream of orgasmic overload which triggered me to shoot my load into her tight bum as she smiled up at me and said "oh daddy, that was sooo good. You can make love to me like that anytime you want!" With that I smiled and said, "I may have to do that multiple times in a week if you keep looking this sexy hot my little sissy girl."
When we woke up the next morning, she and I hopped into the shower, got me ready for the conference and jumped downstairs for breakfast. I told her to check us out when she was ready, gave her my house key and asked her to drop off my stuff so I could fly with no baggage and to meet me at the airport at 8pm.
The conference was a long drawn out bore with my mind on Toni all day and wondering where this was going. On the flight back, I made up my mind and when she picked me up at the airport I asked her to move in and live as my sissy gurlfriend. She accepted and became a full time female assistant. I would support her with HR and even offered to cover a breast augmentation surgery if she was a good little sissy. She signed a slave agreement to be my sissy girlfriend and I had her start dancing at the strip club on Friday nights and had her get a tattoo of an Asian symbol for Slave high up on her left thigh. I also made her wear a choker or some kind of collar necklace everyday as a reminder of her being my slave girlfriend. She would bring me coffee at my desk and kneel infront of me when she dropped it off or if another was in my office I gave her leave to drop it off and bring anything my guest needed. I would come home to her in some sexy state of dress with a cocktail waiting at the door. I would sit at the recliner sipping the martini while she took off my shoes and massaged my feet and when I told her to, she greedily sucked my cock and drank my come. It was almost magical the effect my strong discipline had on her, as she became the role model employee, a fantastic housecleaner and cook and believe me, her mouth and asspussy were better than any I had used before.
She would work Monday through Friday at the office, make me breakfast, lunch and dinner, serve me as needed, all the while becoming quite the little sexy tease and lover. Dancing like the little slut sissy she was on Fridays, to bring in extra cash, covered her breast augmentation. She grew more feminine and sexy every day till the other office girls started to get catty due to the men all paying so much attention to her. Rarely did I need to discipline her, but did so as required so she knew she was still under control. Sissy slaves so love to test the boundaries sometimes to insure they are still there. Unfortunately I also discovered that just like many others I was unable to keep the dominant / submissive relationship at that level and started to have feelings for the little minx.
Well here we are 6 months after we started living together, she has had the breast augmentation, lives full time as Toni and even has all her ID changed. I called her into my office and asked her to sit for some dictation. She looked at me and smiled and started to come close thinking I meant I needed a blow job, but I stopped her, sat her down and said, "Take a letter from me to Miss Toni Caldwell please." She looked at me kind of funny with a question on her face...I started to dictate with "It is with great sadness that I need to ask you to retire as Ms. Toni Caldwell with today as your last day of employment." She looked up at me with tears starting to form and I continued "However, it is also with great pleasure that I ask you to become my wife!" I knelt down and presented her with a 1.5 carat ring and she looked shocked and just nodded yes then softly said "yes. Yes! YES I will!" While she pulled me up and kissed me with her arms around my neck and tears rolling down her cheeks!
Hoped you like this story and while it is pure fantasy, I think it has a nice fairy tale princess kind of ending! ( pun intended! )