From a Husband to a Dutiful Sissy Ch. 11

The way this chapter turns out to be, I suggest one may need some tissues... Don't say I didn't warn you.

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Chapter Eleven: Jack and Chantel, Life's Ups and Downs.

I wake up to another new and exciting morning, It's cold out but sunny, Fall is soon moving to Winter. Out of my nightie and into the shower I am invigorated by the warm water. Getting out drying off and getting into my maids outfit for the day, I sit at my makeup table and think about things.

Jack and I have now been seeing each other for about ten weeks. It has been such a ride for me as I hope it has been for Jack. I mean not two years ago I'd be doing the manly thing and be married to Helen, keeping my crossdressing a secret and here we are over 16 months later I am a trans girl, looking good and feeling good. My relationship with Helen is also now so wonderful as we are the best girl friends and I love her as such dearly. Alan has been a great business partner and a good man for Helen.

My life has come quite a bit far away from being humiliated sissy crossdresser, maid and slut, to being hottie t-girl and my maid duties are less hard core but still provocative to my male clients. The videos I made months ago still sell online and my escort work now as a sexy t-girl goes well enough that I do maybe two dates per week on average I do ok. Being in a relationship with Jack again I no longer do anal with male clients but am still a sexy, interesting t-girl who will do oral or hand jobs on her dates. The clients I have are still generally mature men ranging from their late 30's to their early 60's.

Anyways as I get ready to do my maid calls today I am in a black maids dress, black pantyhose, black leather 5 inch pumps and all made up, my hair has full grown to where I like it, sandy blonde just below my shoulders, carefree, wispy style with bangs, I feel t-girls really can rock bangs.

My hormones have really feminized up my already pretty feminine looking body. I still have only small titties but they are firm and my nipples are very sexy and sensitive. I still may take on implants. My face has really feminized nicely with softer skin and with laser treatments no longer any facial hair. I still also plan to get my nose thinned and eyes lifted. Hormones have moved body fat to my hips, I'm still boyish but not a boy in hips anymore. As for strength well as a t-girl on hormones for near a year it is one thing you do notice. I'm a not nearly as strong as I was when I was Phil. I'm still physically strong as a woman but physically weak as a man so to speak. My healthy conditioning though is good, I love working out at the ladies gym with Helen, she has me in better condition as a chick than I was as a man. I fit in just like any other girl there. In fact the gym has three other trans girls along with me and we enjoy each other as we share a similar journey. Two of the girls are younger than me, only being in their twenties and the other t-girl is older than me with her at age 47. And yes! Helen has me now at a comfortable 165 lb. range. My body looks longer and sleeker now given I am 5'10".

I make breakfast for the three of us and Helen as well as Alan soon leave for work. I clean up and am off to my two jobs today. I still enjoy being a sexy maid and my gentlemen clients are now all regulars and fixed at twelve men, most have me come weekly and they enjoy watching me, talking with me and yes most have me do oral them that/or they like to jack off in front me.. Men must enjoy themselves as they may!

Life is good, very good I say, better than I'd imagine not one year ago. I have happily accepted that I am now a cute t-girl. I do think about bottom surgery as well but for now it's on the back burner so to speak.

Jack, well Jack and I have been having good times, dating for about ten weeks, we have come a long way, his manly company is such a great thing for me. As Phil I'd never be with a man but now as Chantel I love a man and a real man caring for me. Jack is still in infatuation mode with me, but loves me too.

We have enjoyed each other and enjoy each of our company very much, done some fun things. Such as one weekend recently he took me away to his favourite NFL team city to watch the Seattle Seahawks and we spent a weekend in Seattle taking in a Hawks game, what a blast. As a dude being Phil I'd have had a blast and would have gotten drunk with Jack having boyish sport fan fun. As a chick now I love it through the emotions of now being a female and seeing how a 47 year old grown man like Jack can still be like a 15 year old boy at his favourite sporting event. I felt emotions I could never have as a male and I love it all. We made great hotel room love at the Marriott that weekend. I think about it now and still go "Mmmmmmmmmmm."

We also went to a rock concert festival just last weekend in Toronto, Ontario, a mix of cool cover bands performing some of our favourite artists. Another hot and sexy weekend, lots of heavy love making too in our Ramada hotel room.

I have also met with Jack's two daughters, Lisa age 22 and Kylie age 18. I was so nervous as again he has been separated for now eight or more months for his wife Christine. Both girls were polite, but a bit defensive towards their dad and I understand as my daughter is now 24 and she has had to deal with a lot since I divorced her mother, gone through a second divorce with my now best friend Helen and to see me transition into a woman. That night with Jack's kids was a pleasant night and my nerves were relaxed as his girls were friendly and polite to me. It may take time to become real friends, we shall see.

[another week passes by]

Today I find out that Jack has to go out of town on a business trip for the bank he works at. He will be gone for five days. God I'm going to miss him and his manliness. Ahh a girl's life at times as her man must work at his job. I hope to make his return be worth it. But I have work to do as well. We stay in contact via texts and phone calls.

Helen and Alan have set a date for their wedding. It will be next November 17th. Alan's parents wedding day 51 years ago. I think it's sweet. As a t-girl I wonder if I will ever have said joy to be married for the first time as a woman? I mean yes, I married twice as a man and it was all great, but female hormones makes a girl think and feel odd for me now, fun but still odd. I hope maybe one day soon. Maybe it will be with Jack, but I remember what Helen told me weeks ago, "Be careful about my feelings."

These five days pass by so slowly. I get his return flight information and meet him at the airport. I am in a pair of faded tight blue jeans, a white satin camisole and a white cable knit pullover turtleneck sweater. I have a pair of black suede lace up 4 inch spike heel ankle booties with quick side zippers. My makeup is daytime fresh, my hair pulled back in a pony tail looped through Jack's Seattle Seahawks ball cap and I have a black suede over the shoulder purse. A nice spritz of Dior perfume.

I get to the airport in my still owned and enjoyed Challenger SRT 392. We decide to keep this hot car for a now hottie t-girl like me. I park and make my way inside the airport terminal. I watch the flight info boards and see Jack's flight is on time. He should be here in about twenty minutes. I pace around, sit, get back up and pace around some more with my black suede booties heel's clicking on the tile floor. I notice his flight land and watch it pull up to the gate. I am so excited, my girlie feelings are flowing. I imagine the smell of his cologne as I smile and walk to his gate.

Minutes pass like hours when I see Jack, he is in a black leather jacket, black Dickies and black Reebok's on, Mmmmm he is so manly.

I call out, "Jack...Jack... over here hun."

He sees me and smiles politely as he walks to me. I wrap my arms around him and give him a big kiss, kicking my right leg so girlie-like back, my cute spike heel, black suede bootie on display.

He looks at me and says, "Hi hun, you look great."

I smile then let go and we take hands as I choose to carry his carry on and he rolls his suitcase, walking out from the gate area and into the terminal.

I ask, "How was your flight home?"

He says, "Good, pretty smooth and quiet."

I ask, "Did you get all your business done?"

He stumbles in voice and says, "Well not all, got some things to follow up on and to work out."

He looks tired and bothered. I remain quiet as I hold his hand then pull it up to my lips and kiss it, my eyes a glow of sensual femininity look at him in his eyes. I see Jack loves it, but is bothered. I ask if he'd like to go out and eat. He says he'd rather just get home, unwind have drink and eat inside. I tell him ok.

We walk out to my car I ask, "You want drive babe?"

He smiles and says, "No, you drive honey."

The drive to his condo was a quiet, he's pretty tired looking. He looks like he does not feel well. I ask, "Are you not feeling well babe?"

He pauses and replies, "Ahhh, nothing much you can help with Chan... I'm just tired, worn out, with stuff on my mind."

I take my right hand and pat his thigh, he places his hand on mine and then pulls it to his lips and kisses it, saying, "You are such a wonderful person Chan, your life is a most remarkable journey. How can I ever think I deserve you?"

I glance at him and say as we stop at a red light, "No Jack, now as a girl how can a girl like me deserve a man like you?" I blow him a kiss, we both smile and drive off as the light turns green.

We get to Jack's place and casually walk inside, ride the elevator to the 4th. floor and make our way to his place. Getting inside he kicks off his shoes and takes off his jacket. I unzip my booties and I make him his favourite drink, Scotch on the rocks, kiss him as I give it too him. I make myself a simple rye and coke. I ask if he is hungry and he says not too much yet. He has me turn on some music and just sit beside him, we go a good ten minutes without saying a word his arm around my shoulders.

Jack asks, "Hun could you make me just some soup and sandwiches?"

I play with his hair and reply, "Sure Darlin."

I get up and head to his kitchen. About ten minutes later I set the kitchen table and tell Alan it's all ready. We both sit and a quietly eat. Jack stares at me as if he is lost in a trance, He takes his right hand and with his hand's back side brushes the left side of my hair. I cup his hand and kiss it again.

Jack says, "Chantel, in all my life I have never met a woman like you. You have made me feel so special as a man. You know what it is to want to please man, to make man feel somehow whole, you know I love you dearly."

A happy tear comes from my eye and I reply, "Jack, you make me feel like a desirable woman and never did I imagine that would happen, I love you."

We eat up and I cleanup as he rests in the living room, music playing.

I enter the room and Jack says, "Chantel, hun, I'm so beat, so tired, I'm so sorry I'm not the best company tonight, but I really just want to shower and go to bed. I have to go to the office in the morning."

I reply, "I understand hun, I want you to get your rest. Be fresh for tomorrow." I kiss him, zip up my booties and grab my purse. He walks me to the door. I tell him I will walk myself out. We kiss again and I leave.

I get home and Helen asks me how Jack is doing. I told her he's tired and not feeling well so I let him rest. Work must have a burden on him. I'll catch up with him in the morning.

The rest of the night Helen, Alan and myself relax and watch a movie.

It's now Monday Morning, we had a touch of frost today and I find I have nothing on the books maids services wise the morning. I make breakfast for the three of us and lounge in my long pink robe. I will do some house work and give Jack a call later.

Getting on to chores before I do have to dress up as a maid and go to Markus's place this afternoon. He will enjoy me in my pink maids dress, white tights and pink 5 inch spike heel pumps. But I see it's about 10:30am and I know Jack is to be at work but I want to call him and see how he is feeling.

I call his cell phone, it rings a few times and he answers in a bit of a downer voice, "Hi, hun."

I say, "Hi babe, just checkin in on ya hun, you feeling better?"

Jack replies, "Mmmm no not really, in fact I called in sick, the office will have to wait until tomorrow."

I feeling sad for my man say, "Oh honey I wish I could cheer you up."

Jack says, "Hun not much you can do about it, I just am well blah. I have to get over it all."

I reply, "I'm off from my work until 2:00pm would you like me to come over for you, make you something to eat?"

Jack says, "No hun, it's ok, just go on with what you have to do, I'll get over it all."

I say, "Ok Jack, I'll let you go and get some rest... I love you ok?"

Jack pauses and replies, "Yes hun I know, I love you too, talk to ya later ok?"

I reply with an ok and bye as we hang up. He is really feeling bummer, but I'll let him be.

I am soon off to Markus's place and put in couple of hours of maids work, Markus as usual loves to watch me and to masturbate in front of me. Often cumming on my legs, but today he wants to cum on the coffee table and have me clean it up with my tongue. Of course that turns him on.

My mind is still on Jack though, I hope he is getting better, leave him alone for now.

[Wednesday Morning]

At 10:00am my cell phone rings, I see it's Jack, I am excited as I say, "Hi hun, how are you feeling today babe?"

Jack pauses and says, "Meh, still troubled," he sighs, "I...I was wondering are you or can you be free for lunch today?"

I reply, "I do have a client this afternoon but I will change it for you Darlin, what do you want to do?"

Jack says, "Chan, I'll swing by your place by oh, say 12:30pm. to pick you up."

I reply, "Ok where do ya want to eat?"

Jack says, "How about a brunch like place, I HOP."

I say, "Ok sure, I'll dress casual babe."

Jack says, "Ok Chan... um... you know... well you know I love you to death."

I pause and reply, "I...I love you to Jack, cya at 12:30, ok?"

Jack says, "Ok cya."

I get dressed for lunch. My white lace push up bra and matching lace panty, a white satin camisole and a white long sleeve turtle neck top. I then put on as a layer a dusty pink sweater with v-neck. I pull out a long black denim skirt over top a pair of black sheer pantyhose. Then a wide black with large gold buckle belt. I put on a pair of large gold with pearl drop earrings that Jack gave me, fix my hair, touch up my day makeup with frosted pink lipstick. I pull out a pair of pink leather zip up 4 inch spike heel knee boots. Finally fill my black over the shoulder purse.

I sit and wait for Jack to come by. He pulls into the driveway by 12:35pm. I walk down stairs and meet him at the door. He wraps his arms around my hips and I wrap my arms around his shoulders as we kiss.

Jack looks me over, "You always look so good girl."

I smile and say, "Why thank you."

Jack is wearing a brown bomber style jacket, dark blue jeans and a white button down shirt under the jacket. He has brown hiking type boots on, looks divine and smells so good in his cologne. We walk to his Cadillac and he helps me sit inside the passenger side door. I watch him as he walks around, his shoulders are touch shrugged forward but he looks so manly anyways.

We drive to I HOP and we walk inside get a quiet booth. Coffee is served and soon we order, Jack has a breakfast dish of bacon, sausage, eggs, hash brown and pancakes and I order an Omelet.

Jack stares at me all quiet, I see this and blush as I ask, "What... what do you see?"

Jack smiles, "You...the most special person I have ever known."

I blush and reply, "Ahh come on hun, I ain't that special."

Jack says, "Yes, yes you are Chan. Never in my life would I have figure I'd date and fall for a trans girl. But you... jeez, you Chan... you got it."

I smile and reply, "Jack I never believed I'd fall for a man, but then two years ago I'd never have thought I'd become trans."

Our waitress brings our food and we eat quietly for a few minutes.

Jack says, as he grabs my left hand, "No matter what in life Chantel please know I will always love you."

I look at him oddly and say, "I will love you too hun."

We finish up by 1:20pm and Jack asks if I'd like to walk at park today? I agree and soon we are out and driving to the park.

It's cloudy and cool but dry as we get there and park the car. Jack helps me out, me planting my pink spike heel boots on the asphalt. Being in the afternoon there is hustle and bustle, joggers, cyclists, couples walking and such.

Jack grabs my left hand with his right and we begin to walk, my heels click clock as we go. It's quiet between us for now as Jack just breathes deep. I remain cheery and feminine. Soon Jack walks us to a picnic bench and has a seat as do I.

He stares out in space. I see this and ask, "What's up babe? Is work bothering you?"

He looks at me, pauses and says, "When I flew to Calgary last weekend it was not just for business. I...I also met with Christine, she flew out to be alone with me."

My stomach begins to get topsy turvy, "Umm...yeah and...and what?"

Jack turns to me, his right hand graces my face and says, "She wants to get back together."

My heart drops, I am speechless.

He says, "Chan, she feels we should give it another try. [a silent pause]... Did you hear me?"

I am feeling faint, I say, "Yes...yes I heard you...What did you tell her?"

Jack is silent, then says, "I first pushed back, she said she was sorry we split up. The girls have been kind of pushing her to reconcile with me."

A few tears now flow from my eyes, I look away from Jack and say, "Well...what do...do you want to do?"

Jack brushes my hair with his hand and says. "I never wanted to hurt you Chan. I never thought I'd be smitten by you, it was harmless fun at first but I fell for you...But...but I have 24 years with Christine. I have two grown daughters... I...I...just don't...don't fucking know anymore."

More tears drip from my eyes as I say, "Do you still love her?"

Jack stumbles and mumbles.

I ask again, "Do you still love her?"

Tears come from his eyes as he looks at me, "Yes...yes...we had 24 years, most good...We talked a lot last weekend, it began to make sense to me and us...God Chantel, I never fucking wanted to hurt you." He wipes his eyes of tears.

I wipe my eyes trying not to mess up my makeup but failing to not do so, and say, "Jack I...I understand...I can see why you may want to do this...If I were Christine and felt a future could be restarted with you I'd probably do the same." More tears flow as obviously I feel horrible, my first love as a trans girl is breaking up with me, it hurts so Damn much.

Jack comes close to me takes his right arm and pulls my head in tight to his chest and kisses the top of my head, he says, "I feel like shit Chan...absolute shit...you deserve better than this."

I move my head out from his chest, wipe my eyes and swallow as I say, "You...you go to her... if you feel you to can rekindle your love...you do it, tell your daughters I said so ok?"

Jack kisses me on my right cheek, takes my hand and we begin to walk back to his car. Absolute silence between us but we hold hands. Getting back to the car he helps me inside the passenger side. I try to keep together as he gets in the driver's side. The drive back to my home is silent. Parked, he gets out, walks around and helps me out, we walk to the front door, there is silence.

He says, "I'll always love you." he wipes a few tears and adds, "I never wanted to hurt you."

I look at him, my mascara has run as I say, "I know...I know...I love you and will always have love for you."