From a Husband to a Dutiful Sissy Ch. 10

This next chapter has Chantel being a higher class t-girl escort for about 4 months. Her work is going very well, good gentlemen clients enjoy dates with her. She normally works Friday and Saturday evenings. Her day time contracted maid's work is also going well, numerous bachelor, divorced and widowed male clients.

This chapter will have a romantic element. It will start with Chantel actually having a more than maid type work relationship with one gentleman. His name is Jack, he is 47 years old, white male, divorced just for the last 7 months. He is a local loans officer and enjoyed Chantel enough to be smitten by her as his contracted maid. Chantel has been a weekly house maid of his for 3 months. They have been dating for about 6 weeks, going slowly but nicely.

As I write this chapter it is writing in my mind and I am not sure how long it may go so please follow through.

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Chapter Ten: Jack.

Helen asks, "Chan, you going out with Jack tonight?"

I look at her from my makeup desk, "Yes Helen, he has planned a nice Sunday afternoon dinner and time together."

Helen steps in my room and sits on a sitting bench a couple feet from me sitting in my chair at my makeup desk and says, "You two really have a thing going huh? It's been close to what two months now since you moved from just being his house maid to his little honey." as she giggles with approval.

I look at her, half my makeup done and say, "Yes Helen, it's been magical, I've never felt like this, well not as a woman before. He has been so kind and so um, oh manly... I love it. My girlie side is all hot for him."

Helen takes her left hand and runs it through my now grown out sandy blonde hair, wispy and long now just past my shoulders, my sexy bangs frame my girlie face that I now have.

She says, "Hun, I am so happy for you, but I want you to be careful, this is a first for you to be in love with a man. Yes, Jack has been very kind and a gentleman to you, but please go slow, it's new to him to be with a t-girl."

Helen stands up and behind me as we both look in my makeup mirror her hands both play with my hair and then rest on my shoulder, "I do not want you to get hurt, he after all only broke up with his wife, what seven months ago?"

I look at Helen's reflection in the mirror and my right hand reaches her left hand on my shoulder and I say, "I know Helen, I will try to be careful, but he is so wonderful. Being a new girl it's...it's so great, but I will try to be careful."

Helen kisses the top of my head and says, "Good, you know I love you very dearly Chantel, we have a very special relationship now."

I say, "I love you too Helen, always will."

Helen leaves and I get ready. It's a casual Sunday so I dress up in a pink button down cotton blouse, dark tight, blue jeans, my pink Nike trainers with my cute white frilly ankle socks showing. I put on a white cardigan sweater and grab my white leather over the shoulder purse. Out to the front room with Helen and Alan as I wait for Jack to pick me up.

Alan almost like a nervous father, says, "Looking good Chantel, what are you and Jack planning to do tonight?"

I smile and reply, "We are going to a Sunday buffet and then a walk along they city park's walk way, enjoying the cool fall sun set and with leaves turning, it should be romantic."

Jack says, "Sounds nice, looks like you two will have a good time."

I reply, "Yes Alan it should be nice."

Helen hears Jack's Cadillac ATS park in our driveway as she looks out the window and says, "Jack's here."

I get up, grab my purse and head downstairs after I say cya later to Helen and Alan. I open the door and beat Jack to him ringing the door bell.

I giggle and say, "Ha ha I beat you to it." step up on my toes, put my arms around his tall shoulders and reach up with my creamy pink lipstick coloured lips to him, all 6'4" of him and I then run my fingers through his blonde Ken doll styled hair.

We finish a kiss and he says, "Whoa hold on girl... let me catch a breath and get a look at you. Damn hun you look so girl next door sweet."

I say, "Thank you babe."

Jack is wearing a long sleeve blue polo style shirt and black Dickies with black Reebok's. He has a denim jacket on and he smells so sexy in his cologne. We walk hand in hand to his car. Our neighbours Jill and her husband Frank are across the street and walk over to Jack and myself.

Jill says, Hi guys, how you two doing?"

I smile and say, "Great Jill and you and Frank?"

Jill says, "Good, you two going out?"

I say, "Yep, gonna get an early dinner and just walk the city park's walk way, it's such a beautiful fall Sunday."

Frank says, "Jack nice car, first chance I got to talk to you about it, it's a what 2016?"

Jack says, "Yes, Frank a 2016 ATS, a great car, I love it."

Frank says, "Yes Cadillac is sure putting out some great cars now."

Jack says, "Yes, my first and it won't be my last."

Jill says, "Well we better let you two get going, you both have a nice time... and Jack you be good to our girl."

Jack arm around my shoulders squeezes me and says, "I will, Chan is a special lady." as he pecks my left cheek with a kiss.

They walk on and Jack opens the passenger side door as I get in. As I watch this lovely hunk of a man walk around to the driver's side I think, 'Girl, your life is so very different now than not two years ago. You are in love with man... a real man.. a stud.. a doll... it's so great.'

We drive off to a simple Sunday buffet, get there around 3:45pm and walk inside hand in hand. Find a table and kiss as we both then walk up to the buffet and fill our plates. Well Jack does, I'm a girl now and I must watch my t-girl weight so I go light. It's casual busy, couples and mostly families. People nod and we say hi here and there. You can tell Jack and I have 'young love' as our relationship is still only six or so weeks old. Older women love seeing this in us.

We sit at our table eat and chat small talk, mostly we stare at each other in that young love state of mind. I play with my hair.

Jack says, "I love it when you play with your hair Chantel."

I smile and say, "I love your small talk to me hun."

We carry on chatting and eating as we enjoy a pleasant Sunday late afternoon together. By about 4:30pm we finish up and then leave. Jack walks me hand in hand back to the car and again holds the door open for me... I love modern male chivalry. Living most of my life as man and now as a woman I love being treated like a lady.

We get to the park, it's late, the Sun will set in oh probably 35-40 minutes, but it's dry and crisp as we just walk hand in hand. Others walk by, joggers, cyclists, families, couples young and old. We both stop at the pier to the park's lake and lean on the railing, a breeze blows my hair as I swipe it from my face with my right hand. Jack and I stare at the geese then at each other and back at the geese. We chat small talk as an older couple in their sixties come near by us with a bag of bread crumbs to feed the geese. Jack and I look at them and see a happily married mature couple.

Jack asks, "Do you see that in your life one day Chan?"

I step up on may toes in my pink trainers, peek past Jack and at them and reply, "I don't know, it looks sweet and nice, but time will tell I guess."

Jack stares into my feminine eyes, leans forward and kisses me. The older couple see this and smile.

As we finish our kiss, the lady looks to me and says, "Deary, that looks very sweet and lovely."

Her husband nods and approves.

She adds, "Young love... young love... is there anything better than young love?"

I smile and reply, "A long happy marriage ma'am."

They smile and the man says. "It's been 43 years dear... 43 wonderful but also at times stubborn years. But mother and I would not have it any other way."

We all say our good byes and Jack and I walk down the walkway. It takes us about 30 minutes to slowly finish our walk and back to his car. The Sun has set and he wants to take me to his Condo. I agree. We get there by 6:00pm and soon make our way inside. In the elevator to the 4th. floor he can't help but hold me, hug me and kiss me with big tongue... I'm breathless but love it all.

We get inside Jack's condo and we go to his living room, I have seat and Jack offers me a drink. I ask for a simple Screwdriver and Jack gets himself a Scotch on the rocks. He gives me my drink and I take sip and tell him it's good. He sets his drink down and goes over to his hi-fi and puts on a classic rock station not too loudly as he comes back and has seat beside me on his leather sofa.

He says, "Mmm, feels nice Chantel, are you comfortable?" as he puts his left arm around my shoulder and I snuggle up close to him.

I smile and reply, "Mmmm, yes it feels wonderful Jack, so cosy."

We both kick off our shoes and place our feet up on his coffee table. The radio D.J. cues up Foreigner, Waiting For a Girl Like You and somehow it feels appropriate for the two us. Jack plays with the back of my hair as we snuggle. I move my head closer to his chest and hear him breathe as we sip our drinks. We carry on chit chat about us and how we feel. We both feel very comfortable.

About twenty or so minutes pass by and Jack is getting worked up as he adjusts himself and kisses me again with tongue, it's intoxicating. We keep kissing and soon his hands feel me up and I am all quivering with the feeling of such.

Jack says, "You are turning me on girl."

I reply, "Mmmm it feels so good to be cozy with you."

Jack says, "Do you know what I want to do with you Chan?"

I look up at him and ask, "What?"

His excited reply, "I want to so badly go down on you. I've been wanting do this since we first started seeing each other."

I sit up and say, "Mmmm really? I'd love that Jack if you are into it."

Jack replies, "Yes! really, I have been fascinated by the thought of sucking your t-girl dickie."

I then lay out on his sofa my legs lay over Jack's lap and we both undo my tight blue jeans and pull them down my thighs, my white satin panty is next and once pulled down my t-girl dickie is open and growing hard. Hormones makes it less strong than when I was a regular male but hard it goes as Jack takes his hand and plays with it.

I ask, "Are you ok with this Jack?"

Jack all excited says, "Oh fuck yeah, I want to please you babe."

He bends down and takes my girlie dick in his mouth and he is excited but also feels odd as he does have a cock even it's a t-girls cock in his mouth, but he soon gets past this as he begins to suck on my dick and his tongue plays with my cock. I am feeling so damn good as this is the first time as a t-girl I have had a person suck my t-girl dick. I moan with increasing joy and Jack really is getting off on doing this. I can't help but run my fingers through Jack's hair, my pink finger nails hi-lighting in his hair.

Jack goes on in what his fascination lust of him to suck his t-girl's dick. He senses I am working up to an orgasm and I moan with greater joy. It's oddly the same feeling as when I was man but also different as my hard ons are just not as strong, my drive to cum is weaker but my emotional mind is so much more feminized by the hormones. I do enjoy this sensation for what it is. Finally I reach my orgasm and I sigh and moan as my hands pet Jack's head and I dribble out my cum into his mouth.

He pulls off my dick and looks at me and asks, "Did you enjoy that Chan?"

I moan and my eyes roll back as I then look back at him and say, "Yes, it was great, a very special feeling hun." I breathe deeply and ask, "It is your turn babe, what would you like to do with me now?"

Jack sits up has me stand up and he pulls my tight jeans off my legs, then my panty as he gracefully walks me to the kitchen table. He pushes me forcibly which is a submissive turn on for me into a bent over position on the table.

He says, "Just stay there ok?" as he runs and grabs a tube of lube.

Now back he squeezes some lube onto his fingers, sets the tube down on the table, me bent over sans my jeans and panty, only in my pink cotton blouse and my frilly white ankle socks, he take his fingers and begins to lube my butt hole. I moan in pleasure as he carries on. Once we are confident the lube is well enough, Jack and his now very erect 7 inch cut cock moves into position.

He begins to open my butt cheeks and begins to insert his cock slowly inside me, working past my sphincter. I grunt and moan a bit but I do relax and let Jack control he situation. He gets his cock inside and holds my hips firmly with his strong hands as he moves slowly into his rhythm.

Jack begins to moan, "Ahhh...ohhh...ahhhh...fuck...yeah...you..feel...ahhh so...good... Mmm God Chan...your ass..is ...so..f...fucking... tight... Ahhhh."

I also moan and sigh, "Umm...ahh... you are... ohhh such a stud... pin me babe...fucking pin me ... to this... ahhh table... Ohhhh God take... my ass... make it...yours...ahhhh."

This gets Jack so hot and horny as he begins to thrust harder and deeper which throws me into his kitchen table. My body quivers at the feeling of his 7 inches probing inside me. My eyes look up at the ceiling and back down at the table. I close them only to pant and sigh as I open them up and moan over and over. Jack is like a sex machine now he bangs me with a desire to reach his mission goal to fucking dump his load of hot cum inside me.

We go on together as if we are one, each push of Jack's cock inside me, drives me wild with wanting him to cum inside me. He forces my back down on the table with his left hand and he holds my hip with his right as he grunts and groans in wild animalistic lust. I can sense he is getting closer and I coach him on.

I call out, "Fu...fuck... take me... I'm yours... make me yours Jack... you animal and stud... give it ..ahhhh... to me... fuck... fucking... now... Ohhh God, now Jack... Mmmm please."

Jack is in a frenzy as he cries out, "Mmmm fuck yeah girl...ohh... ahhhh... fuck... I'm close... fuck Chan... jeez... ahhhh... ohhhh fu...ucking... close... My... ahhh gonna ... ahhhh.. get it... Ummmm ahhhh... now, now, now." as he shoots his man juice inside me and he sighs and breathes with desire, letting go volley after volley of his hot cum inside me. He slows down, sighs and slowly pulls his cock out from my back side. I sigh and lay on the kitchen table, knowing Jack gave me what I wanted, his hot cum inside me.

Jack leans forward and kisses the back of my neck as I moan. He steps away, puts his briefs back on and walks to the sofa. I lay bent over the table as I say, "You are the man hun... that was fucking great."

I get up and pick up my panty and then walk to his bathroom. I wipe up and freshen up. I then walk out in my pink blouse, white panty and white frilly ankle socks as I sit beside Jack and put my arms around him. He is lying back and listening to the music on the radio. I kiss him sensuously and thank him. He looks at me and his left hand plays with my hair. We are then just quiet for a few minutes.

Jack then says, "You know what I love about you Chan?"

I ask him, "What?"

He says, "I love how you willingly changed your work routine for me once we began to date. I know your work has sex with men as a part of it and you all make good money from it, but I love how you changed once we dated by stopping to take anal from your clients, they had and have to live with only you doing oral or hand jobs on them."

I reply, "Well work is work and life outside of it is for me. Helen, Alan and myself decide a relationship with you was worth closing off me taking anal from my male clients. It's not too bad as most dudes are ok with a sexy t-girl like me giving head or hand jobs anyways."

We talk about us and stuff for a few more minutes and then we decide it's time to call it a night. We both get dressed back up and we walk out from his 4th. floor condo to the elevator and again kiss with tongue inside as it gets down to the lobby an Alan walks me to his car. He drives me home, gets out once parked and opens my door, his hand taking mine as my pink Nike trainers place my feet on the ground and we kiss as he sees me to the front door. We say good night and he is on his way as I walk in, kick off my shoes and make my way the up stairs. Helen and Alan are enjoying a comfortable night together but ask how my date went. I tell all and they are very happy for me.

I'm tired, I excuse myself, go to my bedroom, take off my clothes, sit on my bed in my white satin bra and satin panty and think about my wonderful day and night with Jack. I lay back on my bed and relive the blowjob he gave little me and the wild sex we had after. I'm on cloud nine. I grab my big white teddy bear whom I named Charlie and like a school girl in love hug and hold it, telling Charlie that I'm so in love as I kiss Charlie in his teddy bear snoot.

I make my way to the shower, enjoy an invigorating hot shower, dry off and go to the kitchen in my fluffy pink robe, get a glass of O.J., sit and chat with Helen and Alan for a while, then excuse myself to my bedroom, check on my phone and my emails. I get a text message from Jack. [ U r the best :-) luv ya, have a gd nite, kisses. ]

I text him back [ U r my man U r a stud the best lover one can have, cya sweetie. ]

I listen quietly to music but then fall to sleep. It is all so great.

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Chapter Eleven to follow soon