Born to Be Ch. 03

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Ashley tries on his first dress for Selena.
20k words
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Part 3 of the 12 part series

Updated 10/06/2023
Created 03/07/2019
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A.N. Chapter three! Finally, sorry for taking so long to upload.

More of these lovely two beauties is on the way, and hopefully at a quicker pace! Lol, I've had a bit of a rough patch lately with moving, truck troubles and MOST RECENTLY a heartbreak x( so I hope you guys bear with me while I try to pick my life up again because it's been very hard.

The Following Contains: Pegging strap-on sex between a tall amazon black woman and a little girly white femboy. Also crossdressing and gentle sissification.

Thank you for your patience as always and I hope you enjoy my work.

*****

Selena smiled, her fingers slowly and carefully traced up along the figure of her sound asleep boyfriend Ashley. After they had the best sex she's had in a while, and same goes for Ashley, the two of them spent the rest of the day in bed together. Even though the minor collapse from the weight of their movements caused it to be a little lopsided on the side, but neither of them minded too much. It helped slope Ashley closer into the wall, and with Selena spooning him, it was like he was encased completely in a warm blanket of safe.

They cuddled and she teased him a bit about the Daddy comment, but didn't get too into it, not wanting to push a sensitive subject and possibly ruin her chances of getting him to say it again.

After that though, Selena actually talked to him seriously about the yoga job, telling him that he didn't need to get started right away, they could take their time training until he was perfectly comfortable and confident enough to start giving the lessons. Plus Selena had taken the help wanted ad down from both the store and her website. So no pesky chicks were gonna come prancing in trying to snatch up Ashley's job. Besides, she wasn't exactly in DIRE need for more help around the gym. She originally put up the add because she wanted to give Vanessa a little extra help really, the other job positions were really just to attract more attention.

People were more likely to respond to job offerings if there was more than only one position available.

But until he was ready, he did still need to get started training for his other position as well which would be the receptionist spot. Selena knew the girl currently working there for a long time and considered her a good friend, so she knew she would take good care of her boy toy while Selena had to go about her daily responsibilities.

That's what they were going to do today, once they were up and ready, Selena was going to take Ashley to the fitness center for him to start Shadowing Vanessa at the front desk.

She loved the idea that they would be working so closely together, and hoped that he would take to the job. Ashley professed a strong aura of wanting to prove himself, despite him clearly rocking a body that more than made up for his need to ever have to do anything on his own. If he flashed that booty a bit more, and learned how to work his hips, he'd have men and women clambering to service his every need.

But alas, he was sweet, shy, innocent little Ashley, who was fighting a battle to prove he could do it on his own. He didn't want help from his parents, he stressed that profusely. The last thing he wanted to do was go calling them for assistance after only being out here for a few days. Even though Selena was sure they would understand given his crappy situation, but still Ashley was adamant about it.

This thought caused Selena to glance behind her and take another look over his empty apartment. After some naked conversation between the couple, Ashley eventually confessed to her that his furniture most likely wouldn't be coming in a day or two. But was supposed to be showing up in several weeks.

Of course, he assured her that was fine and seemed quite determined to stay here and wait it out without even a simple chair. But this made Selena feel awful, the idea that he had such an empty place to live in and was all alone here. It made her heart hurt, hence why she didn't leave him all day yesterday. And was content to just roll around on the floor with him, tickling her naked lover after discovering he was in fact, quite ticklish. Laying in bed with him on her phone watching silly YouTube videos, or opening his laptop to watch a few examples of yoga sessions to help familiarize him with the process and tactics.

Now that a new day had arrived, she was worried that she'd have to leave him soon, of course they were going to the same place. But after they were finished at the gym, she'd have to drop him back off here and return to her house.

She didn't want to though, she wanted to just take Ashley with her, bring him to her home so he didn't have to be alone and snuggle the life out of him. She looked back over him again, the blankets quite low on his body since she had sat up and caused them to fall a bit. The supple swell of his ass creating a hill in the comforter, the slight curve to his figure, pretty pink nipples that had gone soft in the warmth. Long dark hair framing his serene face, she was definitely going to encourage him to keep growing it. Even though it made it to his shoulders already, she wanted it to be nice and long, both because long hair would look amazing on him, and it would give her more leverage when she needed something to grab onto as she railed him.

Selena chuckled a bit at the thought, he was so perfect for her. She knew it, and she felt that deep down Ashley did too, even when she teased him about him caving during sex and calling her Daddy. Oouff, did she love being called Daddy, especially by his sweet, little high-pitched voice, wracked with pleasure and desire. She could easily get addicted to that, but she didn't wanna get too carried away. She liked Ashley a lot, and wanted to make it work with him, no rushing into the kinky stuff and possibly scare him off.

It had only been three days now, but she was falling hard for this boy, and wanted whatever was going on here to last a good long time.

Her hand went back up to his shoulder and once again slowly slid down along his body, feeling the silky-smooth surface of his skin. Perfectly clean, not a single body hair in sight, and so soft to the touch. She smiled, the pink lips, the little dick, the quick adjustment to anal sex, there was no question in her mind that Ashley was going to make the perfect girlfriend for her soon.

Just needed to figure out a way to get him to wear less...boy-ish clothes. The yoga job was a step in the right direction, so hopefully she could seduce him into even girlier stuff soon as well.

But that was something to worry about another time, right now she wanted to help him in whatever way she could about his furniture problem. And at this moment as her hand reached below his ribcage, Ashley slowly started to stir. Softly shifting about and mumbling something into his blanket with a little, sleepy, almost mewling voice.

Selena's smile widened and she spoke in a quiet whisper. "Good morning pretty face,"

"Mmm..." Ashley hummed, "Mmmgmorning..." He replied, not opening his eyes and practically slurring the words together with a gravelly tired tone.

"You know sweetie...you can't live without furniture here forever right?" Selena asked, trailing her fingers over Ashley's hips. The couple still spooning after falling asleep to old Vine videos, she ran her digits over the swell of his ass.

"Hmm?" Ashley mumbled still sleepily.

She rolled her eyes and reared her hand back to give his plush booty a good wake up call.

'SLAP'

"AH!" Ashley reared up, jolted from the sudden shock to his system, now very awake. Head whirling around and his locks of bed head hair whipping about as he searched for the source of the striker.

Selena chuckled, "Oh good you're awake! Good morning again beautiful, now what are you planning on doing without your furniture?"

However Ashley only seemed to process some of her words, blinking repeatedly as he had been torn from his cozy slumber by his rude girlfriend. "...Ow..."

"Ohhh come on I didn't smack it that hard." She scooted down in the bed, slinking a bit under the sheets and lowered her head to his bottom where she quickly planted an apology kiss. "Mmmmwah! There, better?" Her hand also spent a few extra seconds giving his bottom a good long rub down, just to make sure it was okay of course.

Ashley sighed, "Jerk."

"Heehee! Well rise and shine, and tell me, what are you planning to do about your furniture taking forever to get here." She sat up in the bed, the blanket pooling half-way around her side, while Ashley took a few extra moments to shift around and face her. Rubbing his eyes a couple of times from the residual sleepiness.

He almost wanted to giggle when he noticed that Selena had slept with the strap-on and harness still on her, she did the same last time they slept together as well and wore it all night.

But pulling himself slowly into the waking world, Ashley sat up across from her, "Uuuum...I don't know?" He answered, yawning a little in-between words.

Selena slumped a bit, "Come ooon, you can't actually plan on just waiting it out in an empty apartment for weeks! This was bugging me all night and it's still bugging me now."

Ashley shrugged, "There isn't much I can do though." He answered, already having come to peace with the idea that he would be sitting on the floor while he ate supper for the next few weeks unless he wanted to blow money on expensive furniture. It cost almost fifty bucks just to get a decent looking chair for damn sake! He shifted a little, playing with the blankets absentmindedly. "People have faced worse problems and made it out alive though so I know I can deal with a carpet sofa for a few weeks."

"Baby..." Selena gently reached out and touched his arm, "Really I can't stand the thought of you being stuck here like this." She looked at him with a genuine concern in her eyes, "I mean I'd come over as often as I could but still that doesn't solve the lack of stuff problem."

Again, another shrug from him. "I know this sucks, but I wanted to come out to the big city and prove that I could live on my own. And I knew it would throw me some curve balls along the way and I was prepared to face them, so I look at this as just a ball to the face that I have to take."

"Wow, phrasing babe." Selena said with a grin, but Ashley still seemed to be pulling his entire consciousness out of the dream world and into his waking one. So the joke flew over his head a bit, "But seriously though, I wanna help."

That seemed to wake Ashley up a bit more and he shook his head, "No, no, no. I don't want you buying furniture for me, I told you this last night." He gathered up some of his fluffy blanket in his arms and held it in his lap. Almost like he was being defiant. "I'll live with what I've got. Besides, I'm not living in decrepit conditions or anything. I like this place, I've wanted to live in my own place for a long time."

But Selena shook her head, "No I know that and I'm not saying I'll furnish your apartment for you. I mean, not that I'd be against it, that sounds like fun, especially since we'd get to christen every piece of furniture with our lewd antics." She snuck in with a snicker and earned a comical eye roll from Ashley. "But...what if instead of that you maybe just...stay at my place for a bit?" She asked, getting Ashley's undivided attention immediately. "Temporarily of course."

He stared at her for a few seconds at that, "Oh I um...I don't know..." He curled his legs up from under the blanket so his knees were near his chest. "Your house is nice and everything, and you're incredible but...I don't wanna impose and..."

"Well why not?" She tilted her head, "I mean, you said it yourself when you saw my place for the first time, it needs a little tender loving care. If you come over for a while, maybe you can be the TLC that I apparently lack" She continued to smile at him.

Ashley though seemed to be very unsure of how to reply, seeming to take the invitation to crash a little more seriously than she was. He hugged his knees a little closer to his naked body, "But...I just got here."

"I'm not asking you to move in with me dummy." Her smile softened, becoming less joking and more gentle, reaching out to sift her hand underneath the blanket and to stroke the side of his legs. "But I won't be able to sleep at night knowing that you're laying on a broken, makeshift...Posturepedic mattress when I've got a big ass kicking bed all to myself."

But still, the uncertain look in his eyes remained. Rattling his brain for any reason at all for if he should say no other than his stamped in belief that he needs to prove himself or something. "I guess I just...I've been looking forward to living on my own for a while. So...I'm not so gung hoe ready to having a roommate. Even one as incredible and awesome as you!" He quickly added.

Selena giggled, "Ohhh come oooon..." Her hand trailed down to his ankle where she took hold of it and tugged it up closer to her. "It'll be soooo much fuuun! You can help me decorate and we can practice yoga together! And watch Netflix until we pass out!" She trailed off, excitedly going on like an eager child while holding Ashley's foot in her hand. Her fingers playfully trailing along his ankle bone, rubbing the sole of his feet playfully.

Her enthusiasm was infectious, and as she went on about all the positives things they could experience, he couldn't help but smile.

But still he wasn't sure if he should agree, he had been so excited about this little apartment just a few days ago. To abandon it now for what could possibly be two week seemed like it was a lot of hype and excitement only to just end in a fortnight long whimper.

"I...I don't know..." He said, not pulling his leg away and allowing her to continue to play with it. "Plus I don't want to be a burden on you, I know you say you don't care but it still matters to me. And it's so sudden too..."

"You wouldn't be a burden! Not at aaall, pleeeeeeease! It'll be sooo much fuuuuunnn!" She started childishly, "Like a long sleepover! And again it's not forever I promise, just long enough for your stuff to show up then you can come right back here!" Selena practically begged Ashley. "I'll do anyyyything you waaaaant!" She tugged on his leg again and brought his foot up to her face, then began to kiss along the side of it.

Ashley giggled suddenly, since she learned how ticklish he was last night, she had been taking full advantage of it ever since. "Selena! Stop thaaat."

She ignored him, pulling his leg further, up to her face, he was so short though it was practically extended all the way out to reach her even though she was just across the bed.

Her lips smooching his ankle, followed by her tongue coming out and licking along the very side of his foot up to his toes. "Aaaaanyyythiiiing..."

"Ahah! Seleeeenaaah!" Ashley giggled, now with him being the veeeeeeeery ticklish type, she was quickly switching up his nervous, uncertain mood with a giggly laughing one. She licked over his toes and along the ball of his foot eliciting more little laughter from her boy toy. Reflex tried to get him to pull his leg away or at least flinch back. But her grip, while not being tight or forceful was strong enough to maintain a hold on his leg and kept it in place. "Stoooohhp!" He bundled up the blanket in his hands, bringing the comforter to his face to try and hide his quickly getting more visible red cheeked shyness.

Even though they had done the dirty three times now, when she kissed him or licked him in such a taboo way, it still made him feel so embarrassed.

Her lips smooched his slender leg, moving up very quickly from his ankle to his calf, lips closing down on the soft skin and clicking on it before moving up higher. "Aaaanyyythingg..." She repeated, her tongue poking out to lick along his inner thigh as she got higher.

As she travelled up further and further, Ashley's giggles suddenly softened, and transitioned to gasps rather than laughs. "Selenaa...what are you...ohh..." Her lips sucked in a particularly sensitive spot on his thigh, taking it between her teeth in a little love bite and sending a 'whoosh' through his abdominal region.

When she made it down far enough, she looked back up at his face, the blanket moved down just far enough for her to see the light pink blush already beginning to form and she crawled up to be face to face with him. "Plus, if you stay at my place...it'll be much easier for the two of us to have fun..."

Only now did Ashley remember that she hadn't taken the strap on off from last night, as the large, black rubber cock tapped his thigh from her closeness.

"I...I forgot about that..." Ashley shyly admitted as she drew closer. Only inches from her face.

Selena chuckled, "Oh sweetie, that's the first thing on my mind when it comes to you." She told him, "Well...that and you're absolutely adorable eyes, God you could melt a billion hearts with those things."

That made his blush go even deeper red as he tried to bring the blanket up once more and hide his easy to change color face.

But Selena didn't allow him to hide, she took hold of the blanket and started to pull it away. And after a brief, playful tugging match between the two, she eventually one and pulled it out of Ashley's little hands. The pouty face he gave her after it came free was even more adorable than the blushing smile.

Rather than lean in for the attack though, Selena surprised Ashley by actually leaning back a bit, "I mean...think about it. We both come home from work...we have a little supper and relax..." She braced her hands on the carpet just below the mattress so that her back was reclined and her pelvis was puffed out towards Ashley. Her big black strap-on pointing up excitedly at him. "Then maybe...you could hop on this big girl and bounce all your troubles away." She wore a wicked grin as she said this.

Ashley's eyes went wider than saucers as she brought out the sudden dirty talk. "Selena..." He said her name as if he was disapproving of her lurid innuendo. But it came out in a bit of a shaky gasp rather than scolding. It seemed like this woman was always horny, how she always managed to turn whatever conversation they had into some type of pervy remark or flirtatious wit. It was just a natural skill that radiated from her.

Not that Ashley was complaining of course, he just felt like he was going to be dealing with a lot of this were he to accept her offer.

She continued to bare her teeth at him, "I mean...are you gonna tell me..." She looked over her shoulder to where her purse was laying on the floor. The bottle of lube she threw last night laying closely beside it. "That you wouldn't like..." She outstretched her hand to pick up the small clear bottle, and flicked the cap open with her thumb. "To play with this..." She held the bottle almost comically high above the dildo, and squeezed the sides, squirting the thick, sticky liquid out and sending it down in a waterfall over the black strap-on. "Whenever you wanted?"

The clear substance drizzling and oozing all over the rubber phallus, Ashley's eyes following it like a cat staring down a red laser pointer. Its slimy, slick consistency coating the cock on all sides. Selena then set the bottle down behind her and brought her hand back around to her front to take hold of her now lube covered cock, and started to stroke it.

Rubbing the fluid up and over the head, and jerking the rest of it along the shaft, slicking it up and making it glisten in the light from Ashley's one and only window.

The boy was mesmerized, Selena's hand motions along her dick seeming to spell bind him in place. "I...I..." He attempted to speak, only managing to squeak out a few little noises that slightly resembled words before Selena shuffled forward on her knees, crawling closer to him.