From a Husband to a Dutiful Sissy Ch. 12

Chapter Twelve: New Days, New Times, New Possibilities.

As in life the Sun still rises and sets, days will pass by, tears will dry, life will go on...Over the last few days, I have kept myself busy as I can to keep my mind off of Jack. It is hard not to think of him to sense him and to want to be held by him. He was my first love now that I live as a trans girl. Helen has been especially wonderful helping me get over Jack. Ladies at the gym all feel for me and they know this type of love lost is new to a girl like me.

I get back to my daily contracted out maids duties, serving and house cleaning for my clientele of gentlemen. Word gets out that Jack and I have gone our separate ways. The gentleman are all nice to me, they treat me well. As to my escort work, it goes on, the men I meet and spend good time with most Friday and Saturday nights is actually quite therapeutic for me. I am treated as a wonderfully exciting lady and for now this is what I need.

[three weeks have now passed by since my break up with Jack]

I'm at home lounging around our house as Helen comes to me about an up coming date for this Friday.

She says, "Hey Chan, I've got some interesting news for you for your upcoming Friday night date."

I reply, "Oh, yes, what is it?"

Helen smiles as she sits on the sofa beside me, tablet in hand and says, "He has booked you all night... I mean that is $1000. He has you from 6:00pm. till midnight."

I sit up and ask, "Wow, that's pretty serious stuff, any reason why?"

Helen reads his supplied bio and says, "His name is Mikel, interesting spelling, he is 48 years old, white and widowed... Lets see, he has two children a boy age 22 and a girl age 20. He works as a...business man in a partnership with three other longtime male friends. He lives closer to the down town core about an 1 hour away from us."

I interject, and say, "Wow, sounds pretty interesting, did you say he was widowed?"

Helen sits up and says, "Yes, here is his picture?" as she shows it to me.

My eyes light up and I reply, "Hmmm pretty cute, very cute, you say he's 48, any info on his height and weight?"

Helen scans the bio and says, "Yes, he is 6'3" and 210 lbs. Not bad, proper weight range I'd say."

I look at the pic and say, "Cute brown hair in a classic male's style, nice eyes, looks fit."

Helen says, "He writes and I will read, 'I have been following you Chantel for over a year, your blog and your pictures online are all very engaging to me. I find you very captivating. I have been very shy to want to meet you but I have finally asked to have this Friday night as a date with you all to myself."

I am excited as I say, "He sounds like fun, boy he's is ready to put up sizeable cash to have a date with me."

Helen asks, "So do you want me to confirm your date with him? It's a long night, what if you do not enjoy it?"

I say, "Helen something tells me I will. Mmmm he's quite dreamy and sounds well grounded, so yeah, yeah book his date. Ask him to tell us what his plans are and any ideas of how he may want me to dress and look for him?"

Helen clicks away and sends off the confirmation as she says, "Honey looks like a fun date, a date that I feel you can really use." as she gets over to me and pecks me on my cheek, then she is off to her thing. I lounge around and watch some t.v. for now.

[Friday afternoon]

At home I am finishing up things and getting ready for my date with Mikel. Helen tells me he plans to have me meet him at 'The Wind Surf Restaurant' at 6:15pm, he has reservations for two and will be there before I show up. That is a pretty high end place in the down town core. So I will dress very formal but sexy too as that is something he said he likes in me. Helen and Alan will drive me there as I feel a bit of drinking may happen and I will not want to chance driving home. I can take a cab but Helen and Alan are also going to go on a date of their own in the area anyways. They will pick me up when my date ends, probably around midnight.

I am going through my wardrobe and I find a Royal Blue dress that is above my knees and has a deep décolletage, [V-neck] in a front wrap style. The skirt section hangs loose but straight. I will need a black satin slip with lace detail around the décolletage area. It should be politely appealing to Mikel. I will wear black garters and black sheer stockings, a pair of Royal Blue suede 5 inch spike heel pumps. I'm going to wear my black faux-fur shrug, after all it's now late November. My waist will have a Royal Blue suede belt with gold buckle. Gold drop earrings with zirconia clusters and a gold and zirconia necklace and a matching bracelet. I think I should look sophisticatedly yummy for Mikel.

Off to the shower I go and relax under warm water. My hormones have made me quite happy with my still small but oh so perky breasts. I feel my nipples an "mmmmm they feel good." my t-girl dick goes hard, so I back off and finish my shower. Once done a big fluffy white towel wraps me and another towel wraps my wet sandy blonde hair. I brush my teeth and look at my reflection as I think, 'Hmm this date with Mikel could be fun, he certainly wants to meet me, Hmm maybe we can have more than just a one off escort date? I feel as if he wants more... Hmm I don't know, I don't want to put the cart before the horse, we shall see.'

I am now sitting at my makeup table and begin my look. Being trans has made getting the basics down more easy than when I just crossdressed. My skin is much more soft and womanly, so some concealer, a nice smooth foundation and a light pressed powder. My eyes will be towards the blue side. A light iridescent almost white-blue base up to my brows. I then take a blue-dark grey colour and from mid lid outward in a soft wing up to the outside of where my brows end I smoke blend the colour. I soft blend this colour under my eyes too. Finally I take a mid blue metallic and fill in my lids from the nose to the mid point. Dramatic for a classy Friday night date. I run some blue-black liner, and two light coats of mascara and my eyes are done.

My face takes some contouring with hi-light and shadow powders and I then take almost purple blush and with my very nice blush brush I sweep my blush from behind the apples of my cheeks tastefully back. I also line my lips a deep purplish liner and lip colour. I look pretty darn hot. I see myself in my makeup mirror and say to my reflection, "Mikel, I'm gonna rock your night and you don't even know it yet. Mmmmmm."

I get dressed up in my picked out dress, step into my pumps, spritz on some Chanel No.5, grab my black clutch purse and my black faux-fur shrug. I walk out to the living room where Alan and Helen are dressed nice for their so sweet date too. They tell me I look great, Mikel will surely be pleased. It's about 5:35pm, we need to get going as the restaurant is a good 40 or so minutes away with traffic.

As we drive out the the restaurant where Mikel is waiting for me, we enjoy small talk as we drive and I hope Helen and Alan have a nice date for each of them too. Pulling in to 'The Wind Surf Restaurant' I see on the stereo's clock it's 6:16pm. Alan parks near the walkway to the Restaurant. I open the door, step out and plant my 5 inch high heel, blue suede pumps on the asphalt. It's a tad frosty so I need to be careful. Helen asks if I have my clutch? And I tell her yes, they both wish me a fun evening. I close the door and watch them drive off. I walk up to the front door an enter the restaurant. Standing I wait as a hostess comes and greets me.

She asks, "Hello, my name is Kayla, do you have reservations tonight?"

I smile and say, "Yes, actually I'm here to meet a gentleman who has reservations by 6:15pm the name is Mikel."

She replies, "Oh yes, yes I see, ok please follow me."

Kayla walks me to the table where Mikel is sitting at and waiting for me. As we both near his table I see him and soon he notices me, a big smile comes over his face as he stands up and out from his seat. As I get by him he extends his right hand to grasp my right hand and he says, "Hello."

I smile and say, "Hello."

He comes and holds a chair out for me to sit and I do, thanking him. Our hostess leaves two menus and asks if we would like something to drink. I ask for a Banana Daiquiri and our hostess smiles, Mikel asks for a Manhattan and our hostess leaves to get our drinks.

Mikel is sitting speechless and stares at me, he soon says, "It is a pleasure to meet you Chantel, you look ravishing."

I smile and say, "It's nice to meet you to, Mikel."

Mikel is dressed in a black button down shirt, coincidentally a Royal Blue tie, pressed black dress pants and black lace up dress shoes. His jacket is a leather jacket already taken off and on his chair.

Mikel is a glow with joy as he says, "I have been following you online for oh over a year, been infatuated with you, sorry to sound school boyish but wow to be here and to actually meet you is well great. You are unbelievably gorgeous Chantel."

I blush and sheepishly say, "Ahh come on Mikel, you are embellishing things [as I smile]. I will say though you are very handsome. I thought you were very cute when I saw you picture."

Mikel says, "You are the first trans woman I have ever um well dated. Sorry girl but to me in my mind something about you attracts me, like a moth to a flame. Your online presence and yes I have enjoyed your blogging well it's so captivating."

I smile and say, "Well thank you Mikel, I find you manly attractive too. I was interested in you by you wanting a whole Friday night with me."

We take a few moments to look at the menus. Kayla brings our drinks and we thank her. Our waiter soon comes and asks if we are ready to order? We ask for another minute, he gives it to us. I choose a roasted breast of chicken with rice and vegetables. I relay this to Mikel so that he can as a man place my order for me.

Our waiter returns and he introduce himself as Claude. Mikel orders for me and then orders a New York steak, medium rare with rice and vegetables. He asks for French bread and the house spread as an appetizer. We both toast to fun night with our drinks.

Mikel says, "Your dress is stunning Chantel and your shoes are killer, your legs are stunning.. Jeez look at the ogling pig I am?"

I giggle and say, "Not to worry Hun, I love looking feminine and sexy."

He says, "Good, I love your hair too and your makeup is wow, hot."

We go onto to chat and Mikel tells me about his business, his partnership with three life long buddies they run an automotive technology business, supplying service equipment and software to auto companies. I am fascinated as he says they are quite successful and have been doing it for about 20 years. I ask about his adult children. He tells me his 22y.o. son is name Nicholas and his 20 y.o. daughter is named Angelina. Both are in school, local but live with roommates. They do seem to spend a good amount of time at home, bumming food off dad though.

Mikel, does tell me about his late wife, Nicole, she passed away in a car crash about four years ago. I feel sorry for Mikel and his kids as such. He was married about 22 years when she passed away. Of course he misses her and so does the kids. I tell him a bit about me, things he may not know, my daughter is near 24 and though lives out of the locale she has begun to repair my estrangement since my divorce near nine years ago. She is fascinated by my transition as she wants to start a new. I tell Mikel my first wife is still a bit stand offish, but knows about me being trans and is happy for me. Helen my second wife and now best friend is happy with Alan and will get marred in about a year, next November 17.

We eat up, enjoy our drinks and Mikel tells me he has tickets for us to go to an improve show at 'The Comedy Club' a few blocks away. I'm all ok with that. We enjoy some dessert and soon it's time to go. It's 7:30pm and he asks if I'm ok if we just have a slow walk the few blocks to The Comedy Club, or would I like a cab? Since it's dry but cool I say I'm ok with walking. He asks if walking in my tall heels will be a problem, I laugh and tell him this girl never has problems in her heels. I've been rockin' heels going back secretly dressing as a teenager. That makes him laugh.

He helps me up and helps put my black faux-fur shrug on as we walk out. Claude thanks us as we leave. Mikel asks if it's ok to hold my hand? I happily agree and we slowly walk down the sidewalk with the crisp dry November air rushing around us. There are a few others walking here and there as Mikel makes sure I navigate the sidewalk in my heels well enough.

About 10 minutes later we arrive at The Comedy Club, get inside find a table order a couple of drinks and relax before the show begins. Mikel places his hand on mine and rubs it with his warm manly hand and then picks up my hand and kisses it as he then smells the perfume on my wrist.

He asks, "Mmm nice perfume, what is it Chantel?"

I feel totally over joyed by his action and say, "It's Chanel No. 5."

He goes on to tell me why he is infatuated with me and why he is interested in a t-girl. He has not dated much since Nicole passed away but has had in back of mind a thing for t-girls all his life. He use to think it was sort of gay but he is not into dudes, but loves the general strong femininity of t-girls and sexy cross dressers. He was so nervous building up to date me. When he found out reading my blog that Jack and I spilt up he cried for me, but figured maybe it was time that he met me.

We enjoy the improve show for the next two hours. By 10:00pm it's done and we decide to get up and move on. Both of us are a bit tipsy so Mikel tells me he actually rented a hotel room up the street for us to well be together. I am welcome to join him for a bit of private time before we conclude our date. I agree and we walk up the block and inside the hotel. He picks up the key for the his reserved room and we walk hand hand to the elevator. His room is on floor number five. Inside the elevator, both of us feel well er good, he asks, "Chantel, can I kiss you?"

I am a bit turned on and I wrap my arms around his shoulders and say, "Go ahead Mikel."

He kisses me a short kiss but his arms wrap around my waist and mine still are around his shoulders, I pull closer to him and we passionately kiss, my right leg and high heeled foot kicks back like a sexy girl would.

Mikel after we stop our kiss says, "Umm wow...wow...wow. That...that was great."

I say. "Yes I enjoyed it too." and we plant another long kiss. The elevator door open on the 5th floor and guests see us in our kiss as the door opens. We both stop, cough and put ourselves back together as we step off and two other couples step in the elevator. We giggle as we scamper to his room number 515. Once inside we sit on the sofa and relax. We are doing fine booze wise. We snuggle together and Mikel puts his left arm around my shoulders. I feel so good, yes I have had a couple of business dates since Jack and I split up, but Mikel is different, he is man who has been following me online for about a year, he so wants to be with me.

We sit and snuggle as we both kick off our shoes and chat. I sense Mikel wants more, he is entitled to more but his gentleman ways backs him off. I ask if he is apprehensive? He says that he is not but wants to savour what we have had tonight and not just be well about getting down. I appreciate that in a man like him. We do begin to kiss and hug, French kiss and feel up our bodies. It's quite hot and I'm ready to go deeper. But Mikel backs off.

He says, "Chantel I can't do it. I just can't do it. I have had a thing for you for months, just meeting you tonight was a high, I fear spooling things. You see girl, I don't just see you as a paid date. I want to build well maybe something. I will understand if you do not see it like that, but I so hope you do." as he runs his fingers through my hair and looks into my sexy made up eyes.

I says as I tap gracefully his lap, "I understand completely Mikel. I agree too. I also don't just see the as paid date. I feel something between us and will agree not too spoil it. It's your date though honey."

He says, "I do so bad want to make love to you Chantel, real bad! and not just have sex. But I want more, I want another date... A real date... yes..yes I know we are on a date but I paid for this one and I am not trying to welch out as you have a right to your business. But Chantel I really, really, like you, you drive my male mind wild. I think you are a hot and sexy woman, t-girl or not t-girl. Do you see what I mean?"

I kiss him and say, "Yes I do...I want a real date too. I want to see you again and have this date."

He suggests we end our date here, I call Helen and Alan to pick me up. While waiting, we chat, he agrees to pay me and demands I take it. I choose to give him $500 back as I enjoyed tonight not as a paid escort. We walk out to the lobby, Mikel will spend the night at the hotel. I see Alan's car pull up and we kiss and I begin to walk out. I tell him to call me when you want to have a date, a real date as I wink and he smiles.

I get into the car and tell Helen and Alan I gave him $500 back as he was such a gentleman and we are going to see each other on a real date next time. They are ok with this and Helen is thinking I may be getting new boy friend. I fill them in about Mikel as we drive home and once home we all head off bed. I end a text to Mikel, [ I had fun, u r a stud and Iuved my time, call me for our nxt d8t, with a happy face emoji.]

Minutes later Mikel texts me back. [I had fun to, loved being with ya I so want u, with a sexy emoji, will call u soon.]

I go to bed pick up Charlie my big white teddy bear and hug him telling him I feel wonderful and feel on cloud nine.

Saturday morning I'm up and dressed as maid as I do maid duties around our house. I enjoy this part of living still I love my cute maids dresses and maid look in my heels. Helen and Alan get thrill out of it too. I no longer am forced into such but do it as apart of living in the house as room mates.

My cell phone rings and check to see it is Mikel so I answer. "Hi. Mikel, how are you this morning?"

Mikel happily says, "I'm well, I'm calling you to tell you that you were on my mind all night last night. I could barely sleep. I had to call you. I want a date tonight if possible. I can't stand not being with you tonight Chantel."

I say, "Well you got this girl all hot, um ok I will have a real date with you tonight. I did not have anything booked so I'm free."

He says, "I'll be by to pick you up up about 8:00pm, we will go to a favourite pub I like, so go casual, but .. but still, um sexy ok?"

I reply, "Ok hun, look forward to it, I will be casual but will still make you hot." as I giggle.

Mikel says, "Great. I can hardly wait to see you tonight, girl."

I tell Helen and Alan I'm going out on a real date with Mikel tonight, he really wants to see me and have such a normal date. They are both very happy for me and rib me a bit for maybe finding a new man... Wow I think, 'I am into men and I am all about being as much woman I can be. How far I have come in less than two years.'

After a light Saturday dinner with Helen and Alan, I get ready for my real date with Mikel. I take a soothing shower, and once washed, dried off and a sensuous body lotion applied I get to doing my makeup. A standard fare, I go with a bronzy colour in a smokey effect over a light mauve base to my brows and a medium mauve on my inner lids. Liner, mascara and a nice brownish colour on my brows and I finish with a deep red blush and lip liner and lipstick.

Dressing, sexy black lace bra and panty and a black camisole with lace trim in my breast area. I pull on a pair of black fishnet pantyhose and I put on a red satin long sleeve blouse opening it to reveal my camisole's lace trim. I grab a pair of black tight jeans, distressed in the thighs and such my black fishnets show through. I feel so naughty and so sexy. I fill my red leather over the shoulder purse with my necessities and grab a black denim short cropped jacket. I pull my sandy blonde hair into a pony tail and pull the tail through the back of my black MOPAR ball cap. I hang some silver hoop earrings and a set of silver hoop bangles on both wrists. I pull out my red leather lace up with quick zippers 4 inch spike heel ankle boots and put them on.