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..."
