Dakota's Surprise Pt. 03

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Dakota begins to make her transition.
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Part 3 of the 6 part series

Updated 12/15/2022
Created 09/02/2020
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mfan2112
mfan2112
164 Followers

Dear Readers, I hope you enjoy this piece. If you like it, please check out my other works.

By the way, the dictionary defines a chapter as:

a main division of a book, treatise, or the like, usually bearing a number or title

or

an important portion or division of anything.

So, dear reader, if you have not read the first two chapters yet, what is stopping you? Go read them and come back. This chapter will still be waiting for you. ~~~~ What, do you want Dakota's mom to come and bring you milk and cookies while reading the first two chapters??? We all know that is not going to happen, so just get on with it.

Special thanks to my reviewers, both to he who wishes to remain anonymous, and NaughtyDragon, who helped me slay many beastly errors. I am sure a few errors still exist, and those are all on me. If you would like to be on my team of editors, please let me know.

I consider feedback a gift, so I do read your comments and PMs. CONSTRUCTIVE criticism is always welcomed.

~mfan2112

____________________

Dakota's Surprise: Part 3--Hailey's Surprise

Like a force of nature,

Love shines in many forms,

One night we are bathed in light,

One day carried away in the storms.

Neil Peart, The Speed of Love

____________________

"Hi, Hailey," Dakota mumbled and looked at her feet.

"Dakota, um... I wasn't expecting... you look good... as a woman!"

"Are you ok?" Flashing through Dakota's mind was the regret she had been born male and didn't have the experiences of hanging out with girls as a youth and having girl talk. Even if he had found an opportunity to have had a female friend in high school, it would have helped the awkwardness of the moment. Instead, she mumbled, "We need to talk."

"Yes, we do... but first, can I get a kiss and a hello?"

Dakota wrapped her arms around her girlfriend and gave her a passionate kiss. The two sat on the couch.

"So, Ummm."

"Yeah?"

"How do I say this, Hailey?"

"Well, first you can tell me, do I have a boyfriend or girlfriend?"

"I'm not sure, to be honest," Dakota explained what she did the previous day and that morning. "So, as you can see, I think I enjoy being a woman, but I don't know what that means yet. All my life I was picked on for being small and girly. I was, as you know, just a wallflower to scared to do much of anything. But when I put my girl face on, it is like someone has flipped a switch, I am a different person, and I can just go do things and talk to people."

"Wow, this is a lot to take in."

Dakota put her hand on Hailey's thigh and began stroking it. Hailey leaned forward, and the two kissed. Dakota felt her girlfriends' hands beginning to explore her chest and feel her boobs.

"I like your boobs Dakota; these are a good size for you."

"Thanks, so you came over wanting to talk about something?" Dakota caught the pensive look in Hailey's eyes. Her fingers began to idly play with a few strands of her long chestnut hair.

"Yeah. Well, um, so my Nana and I were talking. I do that with her. So much easier than my mom. Anyhow, we were talking about you and us. And well, um, I came to an important realization." Hailey paused and looked into Dakota's eyes. "Dakota, I love you," she blurted out. "Oh, that feels good to say, Nana was right."

"I love you to Hailey," the skinny Dakota climbed onto Hailey's lap and the two began kissing again. After a couple of minutes, Hailey laughed uncontrollably. "What's so funny?"

"You have lipstick smeared all over your face."

"You too, girlfriend." Hailey grabbed Dakota's hand and pulled her into the bathroom. The two girls had a laugh at their faces as they washed up. "Now, where were we?"

"I was about to make you take me to your bed and fuck me."

"I was hoping you would say something like that."

Dakota grabbed Hailey's hand and led her to the bedroom. Clothes flew in all directions. Hailey pushed her girlfriend onto the bed. She lay down next to her and rubbed her hands all over her body. She placed a trail of kisses down her body until she got to Dakota's cock. She gently stroked it as it got hard and spent a moment just gazing at it. She stuck her tongue out and used the tip to trace a vein on the top of her cock. Hailey continued around and licked the underside of Dakota's shaft. Her cock throbbed and twitched in Hailey's hand. Lips found their way over the top of the mushroom-shaped head and Dakota let out a moan.

"Oh yeah, babe, just like that. Oh, your lips feel SOOO good." Dakota reached out and grabbed her girlfriend's hips and pulled her closer so she could reach her pussy. She used her fingers gently to rub up and down her folds.

Hailey moved over so the two were in a 69 position. Dakota lifted her head and tongued her clitoral hood and slipped a finger in her pussy.

"Mmm that's it, baby, oh that's the spot."

"Mmmmmphfff, oh, keep sucking my dick."

"I need your cock in me now!" Hailey spun around and impaled herself on Dakota's cock.

"Oh, that is what I was missing this weekend."

"Ride me, baby, ride that dick!"

Hailey placed her hands on Dakota's chest and bucked her hips back and forth.

"Your cock feels so good inside me, oh I love your cock. I love you, Dakota Wallace, oh fuck yes!"

Dakota loved the sight of her girlfriend's tits bouncing up and down as they fucked. She could tell Hailey was running out of steam, so she rolled her onto her back and slipped her dick back into the sopping wet pussy. Now it was Hailey's turn to watch her girlfriend's tits bounce.

"This is kinda different," as she reached up and played with the glued-on titties.

"I'm going to cum Hailey!"

"That's it baby, cum in my pussy. Fill me up with your juice!"

"Uuuggggghhhhh!" loads of sperm shot into the waiting womb. She collapsed on top of Hailey; her dick was still planted in the creamy pussy. Eventually, she got the energy to lift herself a bit and kissed her girl.

"Hehe, your boobies are tickling mine."

"Sorry, I wish I could feel your titties through mine."

"Yeah, I bet you would love the feeling of soft squishy booby touching soft squishy booby."

"Maybe someday."

"So, are you serious about being a woman?"

"Right now, I am not sure, maybe after I graduate. I don't think I could go to class as a woman. It would just be strange. Everyone there knows me as a man."

"I can see that. What about when you are not in class?"

"I enjoy being a woman. Is that weird?"

Hailey looked at Dakota and then looked away. "Honestly, yes. I never felt interested in a woman before and never even thought about a trans person before. But I fell in love with you, Dakota. With whom you are, and not what is between your legs or on your chest. But you are going to have to bear with me here a bit. This is going to take some time to adjust to."

"Not just for you, I am also adjusting."

"I can imagine."

"Have you told anyone else yet?"

"No, just you."

"I'm a little mad at you though."

"Why?"

"You went shopping without me! We must go shopping together. A girls' day out!"

"I hated shopping as a guy, but yesterday was fun. But it would be more fun with you." Dakota showed Hailey all she had picked up. Hailey was envious of a couple of her thrift store finds and threatened to steal them. Dakota's only saving grace was that she was a little smaller than Hailey and many items wouldn't fit her.

____________________

The school term continued with Dakota showing up to class as a male and being a man when he helped his landlady around the house, but otherwise would be in women's clothing. For Thanksgiving, Hailey had invited him over to join her family for dinner, which worked out well since his mom had picked up a couple of shifts at the hospital and said she would just join another nurse for a small dinner in between. But he and Hailey went down on Black Friday to have dinner with his mom so she could meet Hailey. The two hit it off and Dakota got her vote of approval on his girlfriend. He thought about bringing up being trans with her but just couldn't get it out.

As classes hit their home stretch the two backed off on the sex and hit the books hard. One day after class, Prof. Schulman asked if she could see Dakota and Hailey after class.

"Hailey, Dakota, I have an opportunity for the two of you. You might have seen a few of the posters around the building for the big accounting conference in Chicago in January, right before the term begins. I was wondering if you two would be interested in going. There is a special promotion for students, only $25 for the registration. I will be presenting a paper and we could carpool there to save on gas. I know the two of you are more than study partners so you could share a room if I understand your relationship correctly." The two nodded at that.

"I would love to go, professor," said Hailey, "but my grandparents are taking my entire family on a cruise over the break and I will return just before class so I will be out of the country."

"That's too bad. Dakota, are you interested in going? It would be a great way to learn some things and network to land a good internship."

"I think so, but I will have to think about it."

"Ok, just let me know soon."

After the two lovers had lunch in the student union, Dakota excused himself and went back to Prof. Schulman's office, since she had office hours then.

"Got a few minutes, professor? I have some questions about the conference."

"Sure, come in Dakota, what is on your mind?"

Dakota set his backpack down and sat in a chair. He looked around her office a moment and noticed a picture of the professor and the lady he had seen in the supermarket. They were both in wedding dresses, so he figured the rumors were true.

"Delightful picture, is that your wife?"

"Um, yes Dakota, now your questions about the conference?"

"Do you mind if we close your office door?"

"Dakota, I have a policy I never close my door when a male student is in my office."

"Ok, um, how do I say this." He looked down at his feet. Whispering, he said, "Professor, I think you might understand what I am... going through." Dakota's gaze darted around the room, settled for a moment on the wedding photo, and then back at his professor. He breathed deeply to calm the butterflies in his stomach, mustered some energy, and blurted out in a frenetic stream of consciousness "I'm trans I'm wondering if it would be ok if I went as my true self as a woman." He gasped for air and then let out a sigh as if a giant weight had been taken off him.

"I think we need a bit of privacy with this conversation." Professor Shulman stood up and walked over to her door and closed it. She rubbed the palms of her hands on her suit pants as if to collect her thoughts. She looked at her pupil and gave Dakota a reassuring smile. "I understand what you are saying, Dakota. First, look up and be proud of who you are. Being trans is nothing to be ashamed of. Is this something that you have known about for a while?"

"Well deep down, yes. I wore dresses throughout high school and community college, but only at home when I was alone. Now when I am not at school, I am a woman and I have gone out several times as a woman, both alone and with Hailey. I saw you one time when I was presenting as a woman. I saw you and your wife at the supermarket. I walked right past you a few times, and you didn't notice me."

"Wow, sorry about that, and at the same time, good job. I bet you pass very well as a woman then. So, you said Hailey knows then right, and she is ok with it?"

"Yes, she is the only one who knows and now you."

"Wow, ok. To answer your question, yes, it would be fine if you come as a woman to the conference. Any reason?"

"Well, I have been thinking I would like to transition to being a woman when I get a job after school and it might be easier to start when I have an internship and just always be a woman in their eyes. Never let them see me as the man Dakota, they will just know the woman Dakota."

"You go by the same name?"

"Yes, I never thought about changing my name, since it works both as a boy and girl's name."

"That will make it easier. Less paperwork that way. Say, what are you doing for dinner on Thursday? Would you and Hailey like to join my wife and me for dinner? I think we can provide you with some detailed insight into what you are going through."

"Um ok, I can ask her and let you know."

Dakota found her in their normal spot in the library and told her about the dinner offer. She gladly accepted since Prof Schulman was one of her favorite professors. He emailed their professor letting her know it would be the two of them and got directions to her house. On Thursday, Hailey help Dakota pick out a nice skirt and top and helped her with her hair. It had grown long enough that it reached her collar and Dakota felt she could forgo the wig now. The two went in Dakota's car over and rang the bell. Prof Schulman opened the door and invited them in.

"So glad the two of you could come over." She led them to the kitchen where her wife was working on dinner. "This is my wife Karen; this is Hailey, and this is Dakota. Oh, and since we are off-campus and this is not school-related, please call me Leslie."

They made small talk while Karen finished making dinner. "Would you like something to drink? We have some red wine, water, or some iced tea." Leslie ended up pouring three glasses of wine for each of the guests and Karen but poured herself some water. They all helped Karen take the dishes to the table in the dining room.

"Nice place you have here," Hailey said admiring the antique dining room set.

"Thank you. This is all Karen's work; she is an interior decorator."

"One perk of the job is that I can find some great deals. This came from an estate sale. I had to refinish it but look at it. This will last for another 100 years if we take care of it."

Dakota was admiring the quality woodworking job when Leslie spoke up. "Dakota, I like your look, you look fabulous."

"Thanks, Leslie."

"Well, I can see how Leslie didn't recognize you at the supermarket a few weeks ago. If she hadn't told me you were trans, I wouldn't have known. I have a trained eye for trans."

"Thanks, Karen, well I had a red wig on that day. But I was also in leggings and a sweatshirt, my first casually dressed outing."

"So, you don't just always go all dressed up, but live life as a normal woman. That is a good sign."

"You sound like you know a lot about being transgendered, Karen."

"Well, I was born male."

"That's why I invited you over to dinner Dakota, I thought you and Karen could talk and she could help you as you make your transition. Hailey, if you have questions for me as the wife of a trans woman, please let me know. I don't know what your relationship status is, but I am here for you."

"Thanks, prof... err... Leslie. We have only been dating since the start of the school year, but I am in love with this woman here, so I am looking forward to where we might go together."

"That is a good thing, there are a lot of challenges for Dakota coming up. Having someone by her side will be a big help. This is a tough time to do it alone," said Karen. "It was hard for me, and then I met Leslie...."

"So, how long have you two been together?" Dakota asked, "If it is ok to ask?"

Leslie smiled. "You can ask anything you want Dakota, Karen and I talked about this before you came over and we both felt like you needed to get answered any question you might have. Even the more, um, intimate questions. We might not answer them all though." They all smiled at that. "So, to answer your question, we have been together for 10 years, and we got married 5 years ago."

"What was it like telling your family?"

Karen spoke first. "I thought it was going to go ok telling my folks, my older brother had already come out gay. But I was closer to dad than Matthew was, and he took it hard. Blamed himself for his two boys being 'faggots,' as he put it." Dakota noticed Leslie flinch at the sound of the derogatory term. "Mom dealt with it somewhat better and got us all around the table later that year at Thanksgiving. It was dicey at first. None of us knew what to say, and keeping the conversation going was rather difficult. But Matthew and I broke the tension after dinner when we both put on our Packer jerseys and watched the game with Dad. He realized we were still his football-loving kids and now things are going ok between us. He even walked me down the aisle at our wedding." Karen looked at Leslie and smiled.

"Yeah, it took my folks a while to come to grips with me being a lesbian, but then Karen entered my life and they took to her well. It was a bit of shock to them when we told them that Karen was born male. I think it was easier when they put it together that they still might become grandparents. I think they had looked forward to that for a while.

Dakota and Hailey nodded their heads in understanding.

"But..." Leslie continued and looked at Karen. Karen placed her hand on Leslie's, "well, they won't have to wait much longer." She patted her belly.

"Way to go, Leslie!" squealed Hailey. Dakota just smiled politely. "When are you due?"

"Ten days after graduation. I don't think we could have timed it any better. I already set my schedule for the fall, so I am only teaching one class that term."

Karen noticed that Dakota was rather glum-looking and just moving her food around her plate.

"Are you ok Dakota?"

"I guess... Congratulations, I'm happy for you."

Hailey placed her arm around her girlfriend. "Karen, you need to understand. She has a condition where she has an extra X chromosome, and the doctors have told her she can never father a child."

"Oh, I'm so sorry dear, here we are all happy expecting parents and.... Oh, honey..." she wrapped her arms around Dakota.

Hailey leaned over, pulled Dakota to her, and kissed her. "I love you my sweet Dakota, no matter what you can or cannot do. You are my Dakota." Dakota almost lost it there, the love and care being sent her way was more than could ever remember experiencing. It took her a minute to be able to sit fully upright again.

"Thanks, Karen, you didn't know. It just kind of hit me now." She pulled a handkerchief and dabbed a tear away. The three gave Dakota a moment while she composed herself again. "Thanks, sorry for getting all emotional there."

"Hey, what are girlfriends for? Right?" said Karen.

"Dakota," Leslie looked at her, "have you had any counseling at all? Visiting a therapist is a good idea while you are making these big changes in your life. There are some good ones at university."

"I agree with my wife, you should get some counseling. Mine has been helpful, pushes me in ways I would never push myself." Karen curled her top lip under her lower one and furrowed her eyebrows. I'll tell you what was hard, coming out at work." Karen closed and eye and scrunched her nose recalling the pain.

"Hon, you don't have to tell this part if you don't want to," Leslie reassured her wife.

"No, I need to, Dr. Mitchell keeps telling me to let it out when I can safely." She drew in a deep breath and paused. Dakota gave her a smile. "So, I thought coming out trans in the furniture store I was working in would not be that big of deal. The owners were a gay couple, who I thought would understand. Nope, they were more bigoted than my dad. It really hurt. I think they thought I should have been gay and not be trans or something. They started giving me all the bad shifts, sabotaging me in small ways. I hate to say it, but I let them win. I quit two months later. I was in a terrible funk for months until a friend invited me over for a dinner party and I met Leslie. She encouraged me to get started on my own and helped me with my business."

mfan2112
mfan2112
164 Followers