Dakotas Surprise Pt 01

Dear Readers, I hope you find this story interesting. This is somewhat of a change from my previous story line, mainly a romance tale that features a transgendered person. As one of my reviewers said "I must admit I went into the story not expecting to enjoy it especially because of the transgender nature, but I was totally wrong. You handled the character with care and depth." I hope you give this story a chance and enjoy it. Special thanks to my reviewers (DirtyWhispers & those who wish to be anonymous) who helped identify many errors, but I am sure a few still exist. If you would like to be on my team of editors, please let me know. I do read your comments as I want to improve as a writer and any CONSTRUCTIVE criticism is always welcomed.

~mfan2112

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Dakota's Surprise: Part 1 - Making Friends

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Celebrate the moment

As it turns into one more

Another chance at victory

Another chance to score

Neil Peart, One Little Victory

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Dakota dashed off to his car and drove home. His heart was racing. He wanted Hailey to come over, but he needed to pick up his small apartment. Since high school, Dakota had enjoyed slipping into a dress. Now that he lived alone, he spent most evenings in dress and had started to wear makeup. It made him feel totally different, like a new person. He quickly grabbed the dress that was on the back of the chair in his living room and another hanging from his bedroom door and jammed them into his closet. He also did the same to his box of makeup. Just in time as Hailey called and said she was outside. He opened his door and called her to come up the stairs to his place above the garage.

It was a spur of the moment decision to invite Hailey over to his place to study, spurred on by the fire alarm going off in the library of Central State University. Dakota marveled to himself at the situation. He was having a hard time accepting the fact that he was spending all this time with such a beautiful girl. Here he was scrawny, 5'5" and 110 lbs, who had never had a date in his life, interacting normally with a girl. What he didn't realize was that Hailey was having similar thoughts. Although she had a few dates between high school and the first couple of years of college, she was a shy girl and never had a second date before. In the first two weeks of the school year, the two had hit it off. The two commuter students figured since they had the same set of classes, they were natural study partners and had been spending every day in the university library with each other.

"I parked on the street, is that ok?" Hailey bounced up the stairs to Dakota's place, her chestnut hair bobbing up and down in its ponytail.

"Perfect, Mrs. Campbell doesn't go out much on her own, but I try to never block her in. I should probably have her meet you at some point. She likes to know who is coming around."

"Makes sense. Nice place." It was a small apartment. Dakota had a couch with a TV nearby on a couple of crates. A small table with a couple of chairs. A small ¾ bath was off the tiny galley kitchen if you could even call it a kitchen. An overgrown wet bar was more like it. A single basin sink, with an old refrigerator, a small microwave, a two-burner electric stove, and toaster over. And Dakota's coffee pot. A small bedroom that was barely big enough for a twin bed, a folding chair, and a dresser, was opposite the bathroom.

"Small but gets the job done. Kind of like me." Dakota said dryly.

"You're not that small Dakota."

"Thanks for being nice, but I am small. Stupid Klinefelter's"

"Klinefelter?"

"Yes, Klinefelter's Syndrome. I have an extra X chromosome. So, it messed up my growth and I'm like a total freak." Dakota was so embarrassed. He couldn't look up and missed the caring look that Hailey had on her face.

"I don't think you are a freak Dakota. I think you are rather nice."

"Thanks, Hailey, but I AM a freak. I'm pathetic, I'm short, 110 pounds on a good day, I have girly hips and it gets worse..." Years of being picked on and put down were weighing on Dakota and the emotions began to pour out. He sat on the couch with his face in his hands. "Do you mind Hailey" he whispered, "I think I need to be alone for a bit."

Hailey sat down next to her friend. She could see that he was hurting. She put her arm around him and leaned her head next to his. "What you need is friend Dakota," she whispered back. She squeezed him.

"Thanks, Hailey, ugh...I'm acting like a girl again..." Dakota said with disgust.

"Hey, I resemble that remark mister."

"Sorry, I meant I don't do manly well. I have been picked on my whole life, and it is just ..."

Hailey put her finger on his lips. "Shhhh." The two misfits, a runt, and shy introvert, just sat there a minute looking into each other's eyes. Then it got too much for Hailey and she looked away.

Dakota broke the silence, "How about we get back to those problems?" The opened up their books and began to work on their studies again. But neither one was really into it right then.

"Oh my, look at the time," Hailey noticed a clock, "I should probably get going for dinner."

"You don't have to go if you don't want to Hailey. You can have dinner with me if you like."

That caught her a bit off guard. "Ummm." It took her a few moments to process this. "Yeah, I would like that. Let me text my mom and let her know I won't be home for dinner." Dakota heard a big sigh. "Living at home sucks. I see these other kids living in dorms, or Greek row, all the parties, but it is hard to do any of that from home. My folks say they want me to get out and have a life, but I still have to let them know if am going to be home for dinner or not."

"I hear ya, the last 5 years it was some of the same, but mom and I rarely ate at the same time. We were on two different schedules. I worked during the day and took community college classes at night, she mainly has had night shifts since I was in high school to get the extra money. Well, that and most babies are born at night so there are more shifts then. She is a labor and delivery nurse."

"That sounds fun, getting to see babies being born. Probably better than other departments I bet."

"Mom said things like that in the past, so probably true." Dakota began to take a mental inventory of his pantry and fridge. "You like pesto chicken?"

"Sounds yummy."

They put their books and notes away and moved to the kitchen. It was tight having two in that small space, but both enjoyed being close to each other. Hailey was impressed by how well he could cook on the limited setup.

"You got to be careful here, if you have both burners going, you can't also have the microwave on otherwise you will blow the circuit."

But in short order dinner was ready and they sat down. Dakota pulled out a bottle of white wine and opened it up. He hoped that it would calm his nerves around her and give him a bit of courage. Both could feel the sexual tension building as they ate their dinner. Both clueless about how to proceed. They finished up and as he cleared the table, she refilled their glasses and sat down on the couch.

Dakota joined her and they looked nervously at each other. The tension was thick as each wanted the other, but neither had the confidence to take the lead. Finally, the boy leaned forward while the girl closed her eyes. Their lips met for a moment and they stopped. Dakota looked at Hailey, first her eyes, then her lips. Looking for confirmation he had not overstepped a boundary. She responded by pulling him closer, this time their lips did not break so quickly. Dakota was surprised when a tongue forced its way into his mouth and he quickly reciprocated. The two quickly became entwined in each other, years of sexual frustration and recent desires intermixed and started to be released.

Hailey leaned back on the couch pulling Dakota on top of her as they continued to embrace. Timidly, he began to explore her body with his right hand, while his left was wrapped around her holding her close. She moaned as it reached her breast, still clad in layers of clothing. He could feel its softness through her sweatshirt. His first boob since he suckled on his mother's tit as a baby. She directed him to give just the right amount of pressure as he squeezed it.

After enjoying her breast, he started to move his hand lower. As it approached her waist, she whispered to him to stop and stay above.

"Not tonight, this is as far as I am ready to go ...for now."

The boy consented, happy to have gotten as far as he did. The two continued to embrace and enjoy being close to each other.

"Thank you, Dakota, that was lovely. Um, how about I come over tomorrow and study here instead of the library?"

"I'd like that. Are you going to head home now? You can stay as long as you like."

"Yeah, I probably should get going."

He watched her put herself back together a bit and grab her stuff. They kissed as she got to the door and he watched her head to her car and leave.

Dakota headed to his bedroom and stripped. He went to his dresser and pulled out his favorite underwear, a red satin thong, and a matching A cup lace bra. One of the side effects of his Klinefelter's is that he had a pair of very small tits. They did not fill his A cup, but still gave him something to rub and enjoy. He pulled on a garter belt and a pair of black seamed stockings and then pulled on one of his favorite A-line dresses. A pair of four-inch pumps completed his outfit. He looked at himself in the mirror and did a little twirl. The endorphins of that evening still coursing through his veins. He lay down in his bed and hiked his dress up and pulled his thong to his side. His boner barely held in place by the thong sprang forward and pointed to the ceiling.

Dakota looked at his tadger and sighed. How much bigger would it be if he were "normal" he thought. Still, four and a half inches is not bad. The average male is just over five, so in his condition, he felt he was doing ok in that area.

He began to stroke his cock and think about Hailey and the softness of her breasts. He imagined taking her shirt off and kissing them and playing with her nipples. He wondered if she had pubic hair and what it would be like to stick his cock in her pussy. His orgasm snuck up on him and he barely grabbed a towel in time to shoot his load into. Fortunately, it was handy since it was used daily for such events. He removed his dress and carefully put it away and climbed back into his bed in just his lingerie. He slept deeply that night dreaming of Hailey, her wavy chestnut hair, and how her but looked in her tight jeans.

The next day the new couple continued to explore each other. Hailey had worn a skirt and a tight sweater. She enjoyed her lover's hands caress her bare thighs and panty-clad ass. Dakota was careful not to touch her pussy since she had asked him not to yet. But he was incredibly happy when she removed her top and bra and allowed him direct access to her chest.

As they made out, she climbed onto his lap and began to grind her pussy on his groin. Dakota wrapped his arms around her and held her as her hips thrust back and forth. Their lips were locked together as she panted. He could smell her passion as her slit became moister. It didn't take long to toss her head back and let the waves of orgasm roll over her body.

As Hailey began to come down from her bliss, Dakota pulled her body tight to his. She laid her head on his shoulder and the lovers snuggled together.

"Oh, wow thank you, Dakota, that was fabulous. WOW."

"I'm glad you enjoyed that."

Hailey began to lift his shirt to explore his chest. He grabbed her wrists.

"Hailey, we need to talk before you go further."

"What's wrong?"

"Well I don't want you to be surprised, but one side effect of my "issue" is that I have boobs, small ones, but well, I don't want to freak you out."

"I don't care, I want you" and she lifted his shirt and began to rub his hairless chest. There was a pair of small boobs, much like a girl in the initial stages of puberty. She began to gently feel them and then started to kiss them gently.

"Oh god Hailey, that feels so good." She climbed off him and began to unbutton his jeans. "Wha..."

"Time to return the favor." She continued to undo his pants and released his cock. She looked it over since it was the first time, she had ever seen a cock in the flesh. She began to stroke it up and down and watched her lover close his eyes and revel in the sensations he was feeling.

His eyes flashed open, "hang on a moment," and got up and went to his bedroom. A moment later he returned with a bottle lube. It didn't take long, once she had put lube on his cock, to wank him to completion. She loved the look on his face as his nuts exploded and cum shot high into the air.

Hailey went to the bathroom and returned with a wet washcloth to clean up where the cum and landed, mainly on her skirt and the carpet.

"That was intense, wow, I never knew how much came out."

"That was pretty good for me too, normally I don't shoot that much."

They cuddled and kissed for a while, each basking in their post-orgasm glow.

"So, Hailey what are you doing this weekend?"

"Unfortunately, I have to go over to my grandma's house and help her with a bunch of stuff. You?"

"Yardwork for my landlady mostly. And a few finishing touches on my costume for the Springfield Comic-Con next week."

"You're going to Comic-Con? Oh, I would love to go. Can I join you?"

"Re..re..really? You want to go to the comic con with me?" Oh, shit, he thought, little does she know what my plans are...

"Yeah, it would be fun. I have a cool Elvin Ranger costume I could wear. I wore it a couple of years ago when I went. What's your costume?"

"Um... can't tell you...it's...it's...a surprise."

"Oh, come on, tell me."

"No, you will just have to see it."

Hailey gave him her best pouty lips and a sad face. "Please, are you embarrassed by it?"

"Just promise me you won't laugh and hate me."

"I promise, but please just tell me?"

"Nope, you have to wait."

"When were you planning on going?" Hailey wondered.

"Well, I have a hotel room for Friday and Saturday night there, nothing fancy, sort of a cheap place. But I was going to leave Friday morning and come back on Sunday."

Hailey placed her hand on his chest and got snuggly with him. "How about we share the room and split the costs?"

"Um, fine with me. I'll be a total gentleman, ok?"

"I know you will."

The two made finalized their plans for Dakota to pick up Hailey Friday morning and to make the six-hour drive. She let her folks know she would be gone the following weekend. Parents being parents were curious and had figured out there was a boy in her life. The permanent smile on her face, the shifting away from jeans and sweatshirt to skirts and a bit more makeup, and having dinner at a "friend's place" along with coming home later than normal had clued them in.

"Hailey, Honey, can we talk a minute?"

"Sure mom, what up?"

"You have been gone from dinner a bit lately, which is fine, and your father and I have noticed you've been a lot happier as well. Is school going well? Is there anything you want to tell us?"

"Well...I have been spending time with my new friend Dakota."

"What is she like, where is she from?"

"It's a he, mom, a boy."

"Good for you honey." Mom listened intently as Hailey told her about Dakota.

"And mom, don't judge, but I am going with him next weekend to Springfield for the Comic-Con convention."

She gulped, "Ok honey, are you ready for that?"

"Yes mom, I'm 21 you know, I can make my own decisions."

"I know, just it's my job to worry for you."

"You do that quite well mom," joked Hailey.

"Can we at least meet him before you go? Maybe have him over for dinner some night?"

"Sure, probably any night works, maybe Tuesday is better for you and dad?"

"Let me check with your father, but yes, that will work."

"Thanks for being cool about this mom. I wasn't sure how to tell you."

"We, your father and I are here for you honey. Come to us anytime, ok?"

"Ok, mom. Oh, one more thing, Dakota has a bit of a condition, he is short, just a couple inches shorter than I am and skinny. Something about having an extra X chromosome. I forget what it is called. But anyhow, he is self-conscious about it so don't bring it up ok unless he does."

"Sure thing, honey, I make sure your father is aware as well."

The dinner the following week went well. Hailey's parents liked Dakota (who wouldn't) and felt that their daughter had picked out a nice young man. Her dad did take a moment to pull Dakota to the side and said that it is not his or her mother's business what Hailey did anymore, but if they could, be careful if possible. He expressed his concern that she was not ready to get pregnant and Dakota told him not to worry, that he wouldn't be a dad anytime soon.

On Friday morning, Dakota picked up Hailey and loaded her bags into the back of his car. She had a small overnight bag and a duffle with her costume in it.

"Don't try and look in the black bag there Hailey, I locked the zipper to keep you from nosing around."

"Who me?" she said with a faux surprise in her voice, "I would never peek," of course she had already tried to open the bag to see what his surprise was all about.

She was back in her skinny jeans and sweatshirt for the drive over. She pushed the seat back in his car and put her black Vans up on the dashboard as she held a textbook in her lap. She read sections out loud of the book to review concepts together and get some studying in during the long drive. But that only lasted a bit until they started to talk about the weekend and what they were going to do.

They arrived at the hotel just before 4 and checked in. Dakota pushed the cart with all their bags into the elevator and down to their room. It was a nice room, with a small sitting area and a king-sized bed. As Hailey was unpacking her stuff a bit, she looked over to her boyfriend and with the best innocent girl look she could muster, batted her eyelashes and asked him to get some ice in the ice bucket. The moment he walked out the door she grabbed a small bag from her suitcase and ducked into the bathroom.

When he came back in, he saw the door to the bathroom was closed.

"You in there Hailey?"

"Be out in second, don't leave without me."

"Don't worry, I ain't going anywhere."

She came out a moment later. "Good, 'cause I don't want you to miss any of this."

Dakota turned around "Holy SHIT Hailey!"

She walked up to her man and wrapped her arms around him. "You like?"

Of course, he did, she had put on a red corset that was pushing up her girls very nicely. A matching g string was over her garter straps which were holding up a pair of black seamed stockings. A pair of red 4-inch stilettos gave her a look to die for.

Dakota wrapped his arms around Hailey and pulled her tight to his body. The two stood there drinking each other in as the realization of what they were about to do entered their minds. He brushed some hair that had fallen in front of her face out of the way and pressed his lips to hers. She could feel his hardness through his pants just waiting to get out.

He took her hand and led her to the bed. She sat on the edge and began to help him remove his clothing. As she dropped his boxers, his prick sprang forth eager to do his duty.

"Are you sure about this Hailey?"

"Yes, take me. Make love to me, please?"

He guided her back on the bed and spread her legs. He had been looking forward to this day for a long time. Although this was a first for him, he had a good idea of what to do. He lay down next to his girl and began to kiss her and with his hand began to caress her inner thigh. Slowly he made small circles with his fingers on her skin and moved the closer to her pussy. He could feel her body quiver as he approached, and she anticipated what was about to happen.