Coach Daddy Ch. 02

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"Don't mention it Joey. This has been a special day for me too you know. Not only am I helping create a woman like you're my daughter, but I also hope I am creating a lifelong friend." She said with tears in her eyes as she pulled me into a hug and continued, "Thank god we are having this emotional time now instead of later. I'd hate to ruin your makeup after we get it done."

The rest of our time at the spa was all a blur. My makeup was styled to perfection to where smoky eyes, rosy cheeks and pouty, shiny pink lips stared back at me from the mirror. On each finger my new fake nails now extended half an inch past the tip of my fingers and were painted the same shade of pink as my lips. It was all so wonderful and I wasn't thrilled with the idea of ruining it by putting back on my tshirt and sweats when we were getting ready to leave.

"Don't worry dear, our next stop will fix that little problem," Beth reassured as we headed out the door after thanking Gertrude for her time. Luckily the mall was right next door so we walked over and started yet another adventure for me.

We spent at least two hours with Beth picking out and me trying on dozens of blouses, skirts, shoes and dresses that I apparently had no say in whether we bought it or not. Finally Beth decided that I would wear a short cotton summer dress with a flower print and buttons up the front, and a pair of flat sandals then assured me that I would be wearing heels soon but we didn't have the time to teach me to walk in them now. Underneath the dress I still had on my tighty whities.

Leaving the dressing room wearing my new dress Beth called me to stand before her so she could inspect me saying, "Oh yes, this is just perfect for you. Do you like it dear."

"Yes very much. I didn't know wearing women's cloths would feel this...Um...intoxication." I reply, running my hands down my sides from my breasts to my hips.

"It is isn't it?" She agrees. Then, cocking up a perfect eyebrow at me she continued, "Hmmm, well somethings not right here. What are you wearing under that dress Joey?"

"Just my underwear Beth." I answer.

"You mean your old ugly boy underwear? Ok, lift your dress and show me." She demands cocking a hip. I turn to head back to the dressing room when she stops me by saying, "No I mean here dear. Lift your dress and show me here."

"Here?" I ask confused, "But what about all these people?"

"Yes, well I guess they will get a little bit of a show." She replies without a care.

"But..." I say unsure.

Beth stops me and asserts, "That was not a suggestion Joey! I told you to lift your dress. Now do it young lady!"

Reaching down with shaking hands I begin to lift my dress as I feel my face heat up with humiliation. Slowly my unsightly white briefs, with my little bulge, came into view. I close my eyes trying to forget that there were other people all around me.

"No, no that just won't do take them off," Beth exclaims assertively.

I turn again to go back to the dressing room but again Beth stops me before I could and says, "Here. Just slip them off under your dress and hand them to me."

With my face a blazing shade of red and feeling completely exposed I reach under my dress and yank my underwear down over my hips and they fell to the floor. Stepping out of them I bend over at the hip to pick them up and I hand them to Beth.

"Thank you dear," she says laughing, "But we are going to have to teach you that ladies bend at the knees to reach the floor. You just blatantly gave all these people a view of your tiny ass and your little clit bending at the waist like that."

I blanch at her remarks and glance around to see if anyone was looking at me. Thankfully no one was and I return Beth's giggle.

"Now come along dear, we can't leave your little clit waving in the breeze for long. You might catch your death a cold," she exclaims as she drops my old underwear into a trash bin and makes her way to an exit leading out to the rest of the mall.

Self-consciously I follow and despite myself I feel my little penis, or clit as Beth had called it, harden under my dress. We made our way to a store that I have always been conscious of but had never been in. Victoria Secrets. As we entered the store, I took in all the lacy and soft things that women hide under their cloths from all but the lucky few they choose. My clit twitches with excitement at the sights and smells of this store. It was all so feminine. Browsing the racks Beth picks out a Burgundy lace thong and a matching push up bra in my size and says, "Here dear, go into the dressing rooms, take off that dress and try these on."

I make my way into a dressing room and pull my dress off. I first slip the thong up my thighs. The feel of the lace on my skin and the thong sliding between my cheeks was not helping the state of my hardened clit as I pulled them into place. My clit bulged the front of my panties, its head was just peaking above the waist band. Next I took the bra. Having no idea how to put on a bra I stand there confused for a few minutes when there was a knock on the door.

"Are you doing alright in there Joey?" Beth asks from outside the door, "do you need some help?"

"Yes I think I do." I reply cracking the door to allow Beth's entry.

I smile at her as she's closes the door behind her and ask giggling, "How do you work these things?"

"Oh yes, well you wrap It around your waist and fasten these hooks," she says as she directs me, "Then you turn it around and slide your arms into the straps and pull them up onto your shoulders and affix your breasts into the cups. Perfect!"

I jump as she flicks the head of my clit still straining above the waist band of my panties. "Well, we are going to have to do something about this." She states as she drops down to her knees and pulls my panties down to my thighs. Looking up at me she says, "Now dear this is the one time I am going to do this for you. From now on I want you to learn how to control this and I don't expect this to be a problem in the future. When you are ready to cum I want you to catch it into your hand so that it doesn't get all over. Do you understand?"

"Yes ma'am." I reply and moan as she takes my entire clit into her mouth in one swoop, her tongue circling the head. Being that this was my first blow job I am completely overcome by the feeling. My eyes close and my head drops back.

Continually bobbing her head on my pulsing clit and flicking the head with her tongue she forces my legs to part as far as my panties around my thighs will allow. I feel her hand reaching between my legs expecting her to play with my testicles but instead she pushes further and I feel her moist finger slide between my cheeks and put a circling pressure on my twitching star. This pushes me too far and I start to thrust my hips as she pushes her finger deep into my hole.

"Oh god Beth, I'm going to cum!" I mutter as she pushes against something inside me the sends me completely over the edge. She backs up, releasing my clit from her mouth and grasps it with the tips of her fingers and thumb.

"Now catch your cum!" she reminds me as she continues to finger fuck my ass and jack my clit with her fingers.

I reach down and cup my hand in front of the head of my clit just in time as my twitching clit spurts forth what tiny load of cum I had stored within my testicles. Despite the meager amount of cum this is by far the hardest orgasm I have ever had as I feel my knees go weak and I am gasping for breath.

Removing her finger from my ass and standing she demands, "Now lick your cum off your hand."

With humiliation I comply.

Pushing her finger that was just in my ass between my lips she says, "don't forget to clean this."

A distasteful look crosses my face as I suck the fowlness off her finger and swallow.

"Yes that isn't very nice is it? We will have to take care of that when we get you home. We obviously can't present your Daddy with his new little girl with a dirty boi pussy now can we?" She states as I shake my head in agreement.

"Cleaning your Daddy's cock after he stretches your pussy will be much more enjoyable then." She exclaims as my eyes widen and my mind is a whirl with the thought of Daddy forcing his extremely large cock into my virgin ass. Taking in the look on my face she reassures, "Don't worry dear, by then we will have your pussy well prepared for Daddy's cock. Oh and from now on you are not allowed to cum without something in your boi pussy. You need to get use to cumming that way and eventually you will not even need to stimulate your clit to have a true sissygasm."

As I take this new command in, she looks down at my now soft clit and confirms, "Now that is much more manageable. Turn around and we will get you situated." I turn and she reaches between my legs pulls my clit between my legs forcing my testicles to flatten against my body and affixing my clit between my legs. Then she motions for me to pull up my panties securing my clit in place.

"Now look at that, no more unsightly bulge!" She exclaims turning me towards the mirror on the wall. "See? You can't even tell there was anything there. The boy is completely gone and all that remains is this beautiful girl." She points out.

Tears fill my eyes as I take in the girl before and say, "Thank you so much Beth, I couldn't have done this without your help."

"Oh now don't ruin your makeup," she says pulling a tissue from her purse to dot the tears from my eyes, "And don't thank me yet. There is a lot more to being a woman then putting on panties. Now let's purchase all this stuff I picked out for you and then get you home and ready to be presented to your Daddy.

With dozens of bags and my heart soring we strut out of the mall and to Beth's SUV, two girls whom had just had a marvelously girly day. Also, one thing was for certain, I could not wait for tonight, to be on my knees before Daddy again.

12
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8 Comments
MichaelfantasiesMichaelfantasiesover 1 year ago

All this attention, pampering going on in this chapter is definitely something I'd enjoy! I'd be nervous though, knowing I was about to change my life!

AnonymousAnonymousalmost 4 years ago
Damn!!!

I so want this little sissy in my lap right NOW!!!!!

cdCindy1cdCindy1about 7 years ago
my fantasy exactly

I wish I had a Master who had a wife to help me dress and become the woman I feel like. I can't wait to read the next chapters.

loverofintersex1loverofintersex1about 8 years ago
Another boss....

Too many for me. Just fuck her and get her to suck you! The oftener the better. No need to have a boss-lady as well as a boss-man! What is this need to be bossy, with a sissy who wants ro go along and get fucked and suck, ibn the first place? The sex is pretty well done -- right? -- so who needs the S&M window-dressing ? So distractibng!

AnonymousAnonymousabout 8 years ago
a sports bra is much different the an actual bra.

a sports bra is much different the an actual bra. Generally sports bras do not have clips like regular bras.

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