Girl’s Night Out - 4 On a New Path

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Girl’s Night Out - 4
On a New Path

By Jessica C

Cortney had gone to change, I was soon up looking around the room at pictures and then gazing at the view outside. Cortney had silently entered the room behind and had begun massaging my shoulders before wrapping her arms around me.

“It looks like you can enjoy a quiet moment as well as being up and having a good time”. I felt warm and relaxed in the arms of Cortney. We were soon slowly dancing to a tune playing in the background. It was my first time as Dara to be alone with another woman. I thought I had the experience with Nera, but there’s something inside says. ‘This is different there’s a mutual caring. She’s accepting of you. There’s even the feeling that I’m loved.’ I mutter, “This is my first time, it’s so different.”

Cortney pulls me in closer as we stop dancing. “Thanks for coming home with me. I even sense you had feelings for Nathan and it must have been a nice time last evening. It makes me feel blessed you’re here.” Her kiss was gentle.

Led by her hand I followed her into her kitchen. She pulled out a bottle of wine and a plate of cheese. There was the smell of warm bread she had baked and still warm from the oven. “I hope you are one who can enjoy a quiet time.”

We went back into the living area, each with a glass of wine, the plate of cheese with the warm bread rolls. We clinked our glasses in a toast to being together. I looked at Cortney and she was beautiful in her flowing negligee.

Before I sit down she asked, “Could I help you to be more relaxed?” Before I could respond she was undoing the top buttons of my blouse. “You looked so beautiful tonight. Have you practiced a lot in being a woman or do you find it so easy to wrap yourself in the spirit of being Dara?” My blouse was off and my skirt loosened to drop down. Cortney nicely places both to the side.

“I think you will nicely fit into this kimono. You can choose if you would like to slip off your bra and panty before or after to have it on.”

I roll down my stockings and then turned away from Cortney. I take my panty off and unhook my bra from behind. Cortney helps me to put on the silky kimono and bring the belt loosely around. With wine glasses in hand we sit looking at each other on the love seat and in front of the fireplace. Cortney offers me a bite of cheese that she’s holding on a crusty bun. I take a small bite as she does as we lean back.

She says, “You give me the feeling a special girlfriend I can relax with.” It is a scene one rarely gets to paint even in their mind. I am gazing at how beautiful Cortney is, trying to think if it is more a sexual magnetism, how she looks. It feels like it goes much deeper and more sensual. I am glad when Cortney says, “I hope you can stay around tomorrow maybe into Monday.”

“Thanks,” I say, “I wasn’t thinking of that it would give me more time to enjoy being with you. It helps me in being Dara.”

I ask, “You said you do therapy and healing with women and families. What exactly is it you do?”

She said, “I sometimes work one on one with a woman as she works through hurts that can be physical, emotional or sexual anywhere from abuse to traumatic events such as the death of children or the loss of a caring spouse. Sometimes when people are coming out of broken relationships, healing is needed before they can go on and build healthy relationships.”

I giggle, half seriously asking, “So do you see me as a case of yours to be solved?”

“Not at all. I wouldn’t be intimate with someone who I saw as a client. One can hurt while quite healthy in working through their broken past. I see myself totally being a friend hoping we might have a romantic relationship.”

She goes around turning off the few lights that were still on. I notice there are candles as well as the fire in the fireplace gently crackling. I’m lying against comforters and big pillows. Cortney is sensually beginning to play with me. Her hand takes mine to a place she finds. A spot just above my penis. She’s helping me to rub there like something should be happening and it is. She says, “I call that the female clit of a trans-woman. Most other men don’t experience anything. Whether it’s something physical or just part of your female psyche, it is real for you. My intention is to bring you to an orgasm as a woman, and be your lover… Enough of talking.”

I’m not sure how much time passes, but I never thought I’d feel an orgasm come over me without going into a woman or like last night a man making love to me. I purr and moan from the sensations of being loved.

I am doing Cortney, she has guided me in using one or two fingers or my tongue. It has been awhile since I made love with Nera with anything even close to this. Cortney helps me find where she is most sensitive. More or hard is not always best during the time we take. I’m finding her spots. Even listening to her, I hear when I should take her deeper into her own orgasm or when just to help her to keep the experience alive. It is the first time I’ve ever experienced lights, colors and euphoria in such a profound way. The truth is I never seen color and light sensations before while having sex or anything else.


We’re in the dark of morning and we’re taking a shower together. It is nice and warm and we are washing each other as well as ourselves. Afterwards, I get a nightie that I brought with me. I’m invited into Cortney’s bed of satin sheets and an overstuffed comforter.

Come morning I wake up and a clock indicates it’s after 8:00 in the morning. I hear a noise coming from the kitchen and notice Cortney is not with me in bed. I roll out bed and put on little footies and wrap a robe around me. Quietly I sneak to the kitchen. There’s Cortney huddled in the kitchen trying to stop herself from crying.

“I’m here Cortney, what’s the matter?” She tries to wipe away her tears, as she says, “Nothing.”

I say, “It’s not nothing. Something has you crying.”

With a look of frustration she exclaims, “I’m in love. It’s not supposed to happen to me like this.”

I hug her and say, “Does this usually happen quite easily like this?”

“No! And it wasn’t that easy this time!” she kind of snorts in a grumbling voice. She takes me by the hand, saying, “Come here.”

We are soon back in bed and she’s passionately kissing me and doesn’t let up until we’re both in the midst ecstasy washing over us. She says, “Did you feel that? I usually don’t do that. I was crying because I need to let you go home today or tomorrow, and I don’t want too.”

I started to giggle, but she said, “Don’t laugh, I’m serious. I know what we need to do.”

I try to diminish my wanting to laugh in agreement. “Yes, I couldn’t help but feel the euphoric feelings come over me.” I ask, “Are you saying we can’t be together ever again? Or is it that we need to take time and not rush into things?”

Cortney says, “It would be nice if we could take our time. But with you finding yourself, needing to get divorced and care about your girls. I don’t know if you could do that with me around. That could easily take a year or more. Men, even transgender women aren’t too good at taking the needed time.”


Cortney drives me to the hotel to get my belongings and to check out, I have agreed to stay through Monday. We’ll have a late breakfast and then I’ll leave for the community I live in.

Physically it was easy enough to pack all my clothes in the luggage I purchased. Now we’re on our way back to Cortney’s. We spend much of our time telling more about ourselves. I told her about Teresa 4 and Katie 2 and showed her some pictures of them on my phone.

Cortney said, “Do you know that your daughters look a lot like you?” It was something I had not realized before. It took me dressing as my Dara persona that it became so evident. She said, “I suspect your wife will be a little upset in the future when others point out that fact. If you don’t mind it might be helpful that I go with you when they’re to see you as Dara. It will also be helpful for them to know you are still Heath their Dad.” We continued our talk when another concern came to me. “How am I going to explain all this to my parents?”

“Where do your parents live? If it is not too far, it might be better to speak to them in person.” I like that idea, plus the possibility of Cortney going with me. My parents live near the ocean. I assured Cortney that my parents knew of my feminine side though my Dad got himself to believe I had grown out of it.

She said, “That is easy enough to explain and document. If they knew it was part of your personality for such a long time in growing up. It is understandable that a dad especially had the desire to think of you growing out of being you. Coming to accept yourself is a more mature and healthy understanding on your part.”

I felt good to be talking about my daughters and continuing my life in general. She and I were going to make some omelets for dinner. But decided instead to go visit my parents with me as Dara.”


It was a seventy minute drive to my folks. We had called ahead as Mom was home and Dad would be home by five thirty. He technically had sold his hardware business but was obligated to help run the store for the new owners. It kept a familiarity to the business as customers came to know the new owners and them their customers.

We arrived to their home after six fifteen, My Mom, Elizabeth Martin, was pleased to see me looking so well. “Honey, I like this look for you. It is kind of ironic that Nera helped you to achieve the look. And that she also planned to dump you for her friend Elvira.

Dad began to greet me with a handshake before changing to a hug. “Well did I hear you say, you’re going to take your time being both Heath as well as Dara? …Wasn’t there a Dara at college a year ahead of you? Personally I liked her far more than Nera but Nera already had her claws into you and you on a short leash. Then she became pregnant.”

I ask, “Mom and Dad did you really see it that way? Why didn’t you tell me?”

Mom says, “We did and I did again shortly after you became engaged to Nera. But you insisted we’d come to love Nera as we got to know her. We did come to accept and love her, but her spots never did change much.

We ate dinner there and stayed until after 9:00 pm. Mother quickly liked Cortney, but agreed, I needed to take a few months in finding myself. “I agree with Cortney you could easily take a year in making a healthy new start. But I agree with our daughter Dara that you should keep your connection with Cortney if possible. Even if it would not work out in the long run, I think you being friends agrees with both of you. You need a woman friend to give you perspective on growing as a healthy woman.”

Before we left my parents said they’d help me look for and finance a better car. And Dad asked if I’d be interested in managing a retail hardware store. “I thought you said you it’s all sold it to those guys. Plus I thought you use to say is was a man’s business.”

He said, “It was a more a man’s world when I said it. Times have changed. Plus you could open a new Martin’s Hardware and Landscaping company. It could be in a better location with a better layout.”

Mom said, “Those are all things to think about in the future. Right now you need to get going, and take one day at a time.”


Cortney and I headed back to her place and because of lighter traffic we were there in an hour. Cortney asked me to turn away from her for a moment, which I did. Then I felt her putting a necklace around my neck. “Your mother wanted you to have this and said, ‘You should stay the course.’ She said you would understand.”

I look up and into a mirror and my eyes water. Cortney says, “I know what ‘stay the course’ means. But your mother thought it would have added meaning for you.”

I said, “When I was sixteen, my mother was battling with cancer. She wasn’t expected to survive it. But as you see she did and regained her health. To my sister Gloria and me, it means even when it looks bleak stay the course and believe.” She said, “It didn’t guarantee you’d beat it or win. But it will give you hope and that gives you the best chance of succeeding. My mom wore this necklace, or another one that she gave to Gloria, when she wanted to look good. She said, when a woman looks good it is therapeutic to her.”

Cortney says, “It sounds like your mother even then gave you advice a mother me might give to her daughters.”

It was a half hour later that Gloria called. Gloria said, “Mom called and told me some of what happened. I wanted to call and let you know I feel for you. Like Mom said to you, your wife doesn’t surprise me. I bet she’s counting the alimony and child support she figures she’ll get.”

Gloria continued, “So its Dara is it. Show yourself on your phone screen. Mom says you’re a sharp looking woman with a nice girlfriend.” I turn on the phone camera and call Cortney over. We’re soon on the screen. Gloria talks. “Cortney, I hear you’ve come into Dara’s life at a crucial time. I don’t mean to pressure you, but I hope you’ll continue to be in his life. Opps, sorry I meant to say her life.”

Cortney replied, “I think both fit. We will have to wait and see how much will be Dara, now that she’s embracing herself. …Do you ever come this way that you might be able to personally visit with Dara.”

Gloria giggles as she speaks, “Yes, my daughters and I will be out in three weeks to celebrate with our parents. They have an anniversary and we’ll also take my Mom out for her birthday. This will be the first year Dara will be able to take part in our women’s night out.”

I speak up, “I wouldn’t think of intruding on you and Mom and your women’s night out.”

Gloria giggles some more, “Well Mom has already told me she’s looking forward to you being with us and my girls on our women’s night out. Chloe and Jana are also looking forward to seeing you.”

Cortney says speaking of me, “This sister of yours is like a yoyo. She’ll be talking and visiting as any other woman and then she’ll fall back to having no confidence or realizing she is quite a woman.” Cortney gave Gloria her contact info and they agree to visit again.


By this time I was half lying down on her couch when Cortney starts to give me a foot rub. Having worn heals part of the day, Cortney giving me a foot massage feels unbelievably great. It was the first time for me. She occasionally ran her hands up and down my legs.

I wasn’t sure exactly when she did it but my stockings were off and she was more forward in giving me attention. I had a glass of wine in my hand. Every so often she gives me a kiss.

Once again she’s making out with me and treating me as her woman lover. I remember part of what she taught me last night in pleasing her. When I ask for instructions. She says, “Love me by listening to me and my body. I think you will do very well.”

Since we were intimate for some two hours; it must have pleased her plenty. Once when I was orally pleasing her, she kept my face back between her legs. I hadn’t been thinking of myself as a man.

When we were finished she politely said, “I’m sorry, but sometimes you will need to speak up or I’ll let you please me all night.”

I thought to myself that I was enjoying myself.


I don’t know what time it was that we finally fell asleep, but I did not feel like we slept awfully long when 6:30 came around. “Come on Dara, get up. It isn’t good for a woman to get use to sleeping late. You’ll need the time to take care of yourself and remember to take care of your girls. You said, today you need to get your accounts properly set up at North Branch. You should also go home and spend some time with your daughters. If they don’t see you it will be easier for them to think you don’t care and picture you as a monster or however your wife has described you.”

“You don’t want to play her game and be like her. It may not be easy but you’ll need to set the tone of how they get to see and know you now.”


It was not a bad spring day, chilly in the morning and with wind gusts that remind me that I’m wearing a skirt. I went to my lock box and got my old passport, my birth certificate and went to the court house. I needed to get identification for me as Dara. My friend Cyndi, from my support group came to the courthouse to verify who I am. I was also able to go and get a copy of my car license with my name and picture as Dara.

Then I went to my house and walked in and greeted my daughters who came running to me. I was able to lift Teresa in one arm and Katy in the other, giving hugs and telling them I love them.

Nera came walking out to the living area where we were. She had not remember Dara’s voice. “Oh I thought you were Elva. We’re taking the girls out for supper.”

I ask, “How many home cooked meals since you came home?” Teresa said, “Mom’s been treating us special we go out to eat all of our meals.”

Nera says, “If you want to help cook and care for the children and the house you’re free to stay for a couple of days. But I want you to find your own apartment and get out when I want you out. Do we have an understanding?”

“I also want you to change and dress as Heath while you are here.”

I ask, “Do I understand properly that you’re willing for me to stay if I cook, clean the house and care for the children. And, yes, to dress as Heath.”

Nera says, “And remember you’re to get your own place and get out when I say so.”

I say, “Well I don’t mind moving into the guest room and staying there. I will cook and help take care of the house as well as the children. Right now, but I’ll usually dress as Dara and let people get to know this side of me. If everything goes right, I will move out this weekend or a little sooner or later. I need to make sure I get a place the girls can come to.”

To be continued…

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