No Good Deed Goes Unpunished – 8 – Another Page

No Good Deed Goes Unpunished
8 – Another Page

By Jessica C

We go a few blocks off of Time Square eating at a place in Hell’s Kitchen. I am in the mood for buying lunch. But first we look at various shops. Ashley and Marie know some good places; Erica is looking for music she likes as Enrique. She thinks she is fooling us as she does look for bargains and small items of makeup. We’re checking out where Marie and I have bought leggings, shorts and various tops. Erica is surprised when we tell her to pay for her items. Ashley would have had her put them back and we’d be taking her home. Her bill is over fifty dollars that she says she doesn’t have, but she does use the $30 she does have and will owe me the rest when we get back.

I step in her face and tell her, “Your choices were good; they now belong to Erica.” Marie has her sit as she uses the blush and eye color. She acts upset, “I don’t want to be pretty like you.”

I do not know when, but sometime in the past Erica had learned both fashion and makeup. Marie uses a touch of perfume and Erica is content being who she is today. The rest of shopping for her is trying clothes and window shopping. Ashley is not saying what she’s shopping for but she’s looking at extra nice outfits.

We’re eating a late lunch when Paul shows up. He’s talking to Ashley about some show at the art institute. She asks him to pick her up tomorrow night at 6:30. Marie asks if Matthew is coming. Paul says, “Matt is planning to ask you, hopefully it will be yet this afternoon or tonight.”

Marie, “The answer tomorrow will be ‘No’.” Paul sits and calls Matthew. Matt and Marie are soon talking. She hands me Paul’s phone saying, “Gregory Jackson would like to talk to you. He’s a medical student at Columbia. He’s very nice but socially awkward.”

Gregg begins, “Cynthia, I don’t mean for you to be in a difficult spot. I am going to a celebration tomorrow night and I’d be honored if you come with me.” He says, “It is a gathering of the third year med students and we’re having a dinner and social. Spouses and significant others are to be there and I’m always alone. I’m told I’m attractive but I’m tired of being alone.”

I say, “Do I need to dress up if I would come with you?” It’s highly suggested but not required. “Can you take me out tonight so we can meet? I hope to go with you, but I need to know you a little.” I give him the Riley’s address. We’ll be going for a lite dinner. I am twenty and I suspect Gregg is twenty-five.

My shopping goal has just changed. I head for shops just off of Fifth Avenue and the others have two stores and are heading back to Ashley’s. I call Bridgette but get Cathy. I ask for a nice store off of Fifth Avenue. Telling her the situation and that I want to look better than average tomorrow for Gregg. She says some med students have very attractive women in their life. She gives me the name of two stores and says, she’s free to do my hair tomorrow.

Cathy meets me at ‘What’a Night’, she said it is a nice up and coming women’s clothier. She knows the store manager, Jaxy. I like three dresses and end up choosing a long ivory dress with a two inch red ribbon going up where the skirt has a slit running high up the thigh. It will be my go to dress for special occasions.

Cathy giggles at me saying I’m setting a high bar for myself. I select a little blue dress for dinner and our time tonight. Cathy insists I get him to take me dancing tonight. She says the dress has enough sequins that it begs to go out and have fun. I know I am overdue for a fun night out.

We get back to the Riley’s and I get to shower and use the guest room to change. I am ready by 6:30. And though I told him I could come out to the ride. I now wait as I want to see what he looks like as he gets out of the car. He’s good looking but thankfully not a perfect stud.

He says, “I like how you’re dressed. I was thinking if you’re comfortable with me, we could do something extra. Gregory had seen himself as a doctor doing medical research. His moving through the various fields of study in med-school has found him liking to work in the area of sports injuries. He is accepted in two different residencies in women’s sports medicine.

Dinner was good as the food was simple and we talked. I find him interesting. There is something I like but I’m not sure what. When we go dancing after dinner, I like his graceful hands when we’re dancing in close. Again it is easy to talk with him, but this time he’s doing more listening. He gives me a ride to my place at the end of the evening. As we finish our goodnight kiss; I find myself inviting him to stay with me.


I am very embarrassed as I’m not sure what to do now that I have him here. We are both a bit socially awkward. I thought I knew what to do as a woman, but I have not been here yet. Gregg seemingly is not fully inexperienced. Though he says it is from women putting advances on him.

I am in the shower and have my body nice and soapy and my eyes closed. I feel a breeze and hear the door open and close. It is a moment before Greg asks, “Would it be okay to come in there with you? I could wash your back, if you’d like.”

I push the shower door to open so he knows he is welcome. His hands are warm, strong but not at all rough. He is behind me, yet his hands gracefully come up my sides and front. I fear he’ll be disappointed as my small breasts are just beginning to grow. But his delight is in the fact that they are responsive to his touch. He presses against me.

He works up a soapy lather that includes oils as he lubricates both of my lower orifices. He turns down the shower to a mist. He lines up the head of his cock with my bun crack. “Would you mind?”

I ask him, “Push!” He had bent down and lifted me up in place I am pressed against the shower wall. I am having trouble relaxing my muscles. He pushes hard and I can feel him entering me. I grab high to gain hold of the top of the shower. It has been a long time since I had Ryan Davis. I am wondering how Greg could have known, I’d like this. It takes a while before I groan with some pleasure. He says, “I wasn’t sure you were enjoying it?”

I ask, “How did you know I might like this?”

He says, “I was to your night spot the night before. There were a number of you college people there that night. I thought you might be sweet to have.” I can feel his cream explode inside of me.

I say, “I was had only once before. I imagined myself dressed as a woman, but not quite being one.”

Greg says, “We can enjoy that as well, but let’s take our time.” He lowers me so my feet reach the floor as he pulls away. I lather him up and clean him as quickly as I can. And then myself, delightfully he helps.

It is close to one a.m. and we are helping to make sure the other is clean. We dry ourselves off and make our way to bed. I put on a little satin lace, while he doesn’t have a stitch on. We had talked as well as shown each other attention before I roll onto my back and leave myself open for the taking. I place a gel on me that will become arousing as he pushes himself into me. And it is having the desired effect for both of us.

My legs are nicely wrapped around his body. I am learning to move with him in me. Making sure he stays in me is new. He likes pulling completely out and popping me again and again. There is some joy to it but it is more punishing to me than him. Once he speeds up and gushes in me as he keeps pumping until he freezes. He’s pushed against me and is kind of shivering. I realize he is holding onto his ecstasy as long as possible.

I begin to move more and keep his arousal going. He says ‘no’ until he is in a new level of enjoyment. He equated ejaculation with a male orgasm. He is now experiencing the joy of a full blown orgasm. I too have come into an ecstasy that I have not experienced before. I continue but I am not sure why. It is possibly minutes before another wave of joy crashes over me. It is like I am flowing in a sea of color with feelings like fireworks going off within my experience. I do not know how long it lasted, if and when he’s part of my experience.

It is morning when we awake. Maggie not knowing someone was with me, calls up if I want coffee and a roll. She breaks out laughing when I say, “I’m enjoying dessert with Gregg; he’s a med student.”

It is nice to see Gregg in the morning light and to experience the first morning after. It is 9:30 when Cathy calls asking when I want my hair done. It was to be around nine. She whispers asking if Gregg is still there. She is happy for me, asking, “Does the Doctor know what to do when he’s in the bed with his person?”

“More than I care to recount here.” I say, “And I will not want to share the evening with Ashley.”


I hang up and give my attention to Gregg. He is wanting to make sure I can afford a nice dress for this evening. I show him a picture Cathy had taken of me in my dress and he is very impressed.

He says, “Peggy will be so happy for me.”

“Who is Peggy and why would she be happy to see me?” Peggy is the wife of his friend Travis Davies. They’ve been through Med School together.

“Peggy appreciates me because I’m a friend to Travis and care about her as well. She always feels sorry for me. And is always watching out for me? I feel sorry for her because I think Travis doesn’t give her enough attention. She’s a beautiful young woman, but she comes from his hometown. He thinks she embarrasses him, but it has usually been the other way around.”


I get to Cathy and Bridgette’s by 10:30 and I’m in Cathy’s beauticians chair within fifteen minutes. Bridgette brings me an email she received from a Beth Powell who was at the gathering in the Hamptons. Beth apologizes for what happened there. Confessing they were insensitive to all I’ve been through. She didn’t like how far others had gone, but did not absolve herself.

Bridgette says the Powell’s are a simple group out of the Quaker background though not all are still Quaker. “We regret that you were pushed to submit to the group’s thoughts, however caring their intention. I would like to meet you for lunch and see if we can become friends.”

Beth’s, Mother-in-law Mrs. Elizabeth Powell is willing to host us sometime if we’d like to try another outing scheduled for just their family, the beach and ocean. Beth attached a picture of a big cruiser we could take out into the Atlantic.


I am concentrating on getting my hair done. My dress with alterations arrives while I’m under the dryer. Bridgette and Cathy visit with me as they’re amused that I had Gregg stay the night. “We did not know that you saw yourself as you did? Was Cynthia always your girl name?”

I said, “Claire, but then I began using the names of girls I liked especially friends of my sisters. Sharon was a nice name and that of my older sister’s friend at school. I wanted to see myself like what I wanted to be.”

Bridgette says, “I don’t want to suggest you change your name, like it is not important. I think, you need to understand to be Cyndi, Cynthia Brock is going to hold different connotations for you and others.”

“I speak to you with the experience of some who think they know me because they’ve seen or heard parts about me. If you were down in Southern Florida near my Mom, you might look at me through the lens of knowing my mother. Both my genes and much of how I see life comes through her and our family. I had three brothers all older than me. But two have become sisters: Billy was a stubborn and mean brother from the beginning. He defied all attempts. It was when he became Billi and had to live as a girl at sixteen for a year that she changed.

“My brother James has remained himself but he found it wise from living here to move to the Midwest. Harry followed in my father steps, but he followed Mom when she moved to the south away from my dad. Harry fathered my first niece while he was in high school. He married young to another woman and had fathered two more children, finally getting his son Jonathan. It was after Reba kicked him out. He was drowning in booze, anger and other troubles. That he submitted himself to our Mom and he then consented to surgery.

“Living near her and her ways, people might assume I’m just like her. That is one reason why when she moved to Florida that I came back here for university and stayed to live. She has been quite successful in her way, but it’s not mine. A majority of her male clients wrestling with anger, conflict and intimacy issues transition. I think some thirty percent who don’t change, proceed out of fear that they may need to finally deal with resolution in their lives.

With me it is only about 15% who choose to fully transition. I find for a good number; it is not even about sexuality or hormones. Getting in touch with one’s feminine side helps the vast number to relax and see their lives in new ways. I find three fourths of those who choose to transition were already transgender or transsexual before.


You Cyndi are you and whether you change your name or even would continue to see yourself now as a woman. It needs to be your conscience decision. As you see physically you can be an attractive woman, but you could be a neat man as well.”

I am yet in Cathy’s beautician chair and she’s combing and brushing out my curls. ‘I like who I am seeing in the mirror, yet I’m wondering if I’ve really chosen to be me. Had it not been forced onto me to accept this new life?’

I look away from the mirror and to Bridgette. “Isn’t it okay to like who I am? I was excited about tonight with Gregg. Should I call him up and cancel doing things until I figure all this out?”

Cathy says, and as she talks Bridgette affirms. “This is probably one of the healthier things you’re doing, because you’re choosing it. This like last night’s experience should become dear treasures of your heart and memory. Your helping Kim should be as well. But it is also good to decide if you’re Chad or Cynthia and become more comfortable with yourself…”

To be continued…

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