Jewel Ascending Ch. 07

Dear Diary,

I can't believe I did it. I don't know why I talked myself into it. What the hell was I thinking anyway?

**

Jewel was on her hands and knees. Kyle's fingers dug painfully into Jewel's hips and pelvis from the strength of his grip. Jewel pushed back as Kyle thrust his cock into her. She decided she would begin to moan softly to try to encourage Kyle to cum. His cock was doing nothing for her. She knew now that she just wasn't into having sex with him and wondered why she talked herself into it.

Jewel remembered her therapy sessions with Dr. Agonia and how she was always encouraging her to find someone new; to find someone to fill the void in her life since Jean Claude had died.

Jewel's protestations that she was in her year long mourning period were brushed aside, and interpreted as denial.

"There's nothing wrong with having someone to keep your bed warm while you mourn. This is also about your grieving and your recovery from your marriage." She had said.

Jewel also thought of the conversations she had with noble peers of her own age. It had come up once or twice when noble women discussed...or bragged...about their love lives. In one conversation she remembered how they discussed how many dates one should have before considering allowing sex.

There was no firm number given, but a general consensus was that not until after three dates, if a noble woman was interested in her suitor, should she consider it.

Jewel and Kyle had been on 7 dates and he had escorted her to an equal number of social functions. Jewel, reluctantly, decided to see if he was even interested in her physically.

Their date had been pleasant enough. Kyle was the ever attentive gentleman and he had not made any serious overtures indicating that he wanted to sleep with her. His proposal was more humor and innuendo than anything else.

Yet Jewel had thought she understood his intent and went ahead and encouraged him.

One thing led to another and now, sure enough, they were having sex in his bedroom.

It had started as these things always do, gentle caresses that led to kissing, and then naturally enough to gently and reluctantly...removing each others clothing.

Jewel thought Kyle had seemed especially nervous and try as she might nothing she did, no words of encouragement seemed to calm him down. Finally, after what appeared to be a moment of decision for him, he became more aggressive and an active participant rather than the passivity of earlier.

Once he had stripped her of her dress, as she stood in her bra, panties, stockings and heels before him he stopped and just...looked at her. Jewel watched him swallow hard, with nervousness she thought, before placing a hand on her shoulder and urging her to drop down to her knees.

Jewel had removed Kyle's suit jacket and his shirt and tie during their kissing. Now, after she dropped down to her knees, she pulled his belt off, unzipped the fly of his trousers, and pulled his pants down to his knees. Jewel reached into his boxers and pulled out his semi-stiff penis. With a kiss, followed by a soft lick from her tongue, she began her blow job.

Kyle was conflicted. Jewel was not attractive to him. Kyle knew that she...he...made a beautiful woman, and was amazing in her passion for social justice and possessing a raw, intense yet underdeveloped intellect. But try as he might she was just...just...too feminine.

Knowing she was really a male bride forced to dress as a woman didn't help as much as he thought it would. When he stripped her of her dress it became entirely too apparent just how feminine she was...

Her breasts were perfect, firm, and high, upheld by a bra she didn't seem to need.

Her narrow waist and hourglass figure were perfectly proportioned...for a woman.

Her full bottom covered by her lace panties...also too perfect.

Her penis, barely visible as a bulge in front of her panties offered little in the way of reassurance for Kyle's own homosexuality.

Kyle had closed his eyes as Jewel blew him. When he did that and focused only on the sensation of her warm mouth on his cock, things were better. At least she was good at giving head!

Damn, she could even give lessons, Kyle mused uncharitably.

Kyle quickly grew fully erect under Jewel's warm oral ministrations. Her head bobbing up and down on his cock was exquisite. She used just the right amount of saliva for lubrication and pressure for stimulation. She regularly teased his taint and the crown with her daring tongue, lashing at his most sensitive areas.

Kyle held Jewel lightly touching her shoulders. He had to work to ignore her long full luxurious brunette hair. Kyle preferred the men in his life to have short, masculine hair cuts and her long hair brushing against his forearms was a distraction.

Once fully erect and hard Kyle stopped Jewel and his cock slipped from her lips with a soft, warm, wet, popping sound.

Kyle opened his eyes and was disconcerted again by how feminine she looked with her full lips and soft features smiling shyly up at him from her kneeling position before him.

He moved to pull her to her feet. Jewel, sensing his intention, removed her panties. As he brought up and back to the edge of the bed he push her gently onto her back.

As Kyle positioned himself between her legs he tried to ignore her thigh high stocking clad legs and high heels as he aligned his cock with her anus.

Jewel had Kyle wait for just one moment as she retrieved the small bottle of water based lubrication from her purse. Squeezing out a small dollop of lubrication onto two fingers she carefully spread the lube onto her anus, slightly penetrating her anal ring with lube, and then applying the rest to Kyle's saliva slicked cock.

Jewel didn't have to use much compared to her former husband. Kyle's dick was probably only 7 inches compared to Jean Claude and his 10 incher.

Jewel wiped the last of the lube from her fingers onto the sheets before wrapping her long legs around his waist and placing her hands onto his shoulders.

Kyle for his part slowly pressed his firm cock against Jewel's ass and was glad that despite losing some hardness while she applied lube, he managed to penetrate her easily. She even gasped ever so slightly as his 7 inch cock slipped fully inside her.

Kyle noted how easy his cock slipped in, and looked to make certain his cock was clean when he withdrew. Kyle didn't want to get any shit on his dick and it looked clean. Kyle assumed that Jewel must likely still maintain her anal hygiene as a feminized male bride. He had to admit that would be desirable if he wanted to pursue additional intimacy in the future.

Kyle was trying to distract himself again from how feminine she looked. He tried to simply look her in her eyes he was put off by her perfect eye make-up. Her soft and subtle eye-shadow, lush lashes from mascara, and perfectly sculpted brows were...yet again...too feminine for his tastes.

Kyle looked down her body and finally concentrated on her small penis. Surprised that it was still soft he reasoned it must simply be how a feminized male bride usually was.

Jewel and Kyle lay entwined; their bodies pressed tight to each other as Kyle slowly thrust into and withdrew his cock from Jewel's ass.

Kyle didn't want to lie against her body and feel her large soft boobs against his chest. He closed his eyes, went stiff arm to the plank position, and fantasized as he drove his cock in and out of Jewel's ass.

Jewel was first confused, then annoyed when Kyle closed his eyes. After a moment she was slightly relieved. She figured that her presentation as female was at odds with her possessing her male anatomy and he may not have fully considered it before having sex.

Still, good for him for giving her a go, she supposed.

Kyle was having trouble finding the right fantasy. He had a few lovers from the past he tried to bring to mind but was unsuccessful. With his arms growing weary and his abs starting to burn from holding the plank position for so long to avoid pressing his body against Jewel he needed to change position.

Kyle opened his eyes to see Jewel studying him. He didn't want to disappoint his mother by not satisfying Jewel and seducing her as his mother expected. Her femininity was still such a turn off he was having a hard time maintaining his erection. Kyle pulled out from her ass.

"Turn over...onto your knees..." Kyle commanded softly.

Jewel decided to simply let Kyle lead and set the pace. She was doing this for him after all. Her only interest was in satisfying what she perceived was his normal male lustful desires. She rolled over and got up onto all fours, Kyle positioned behind her.

Kyle got up onto the bed behind Jewel and again aligned his cock with Jewels ass. His earlier penetration allowed for easier entry that when they first began. Gripping each of her hips with his hands he gripped as tight as possible; her full round woman's bottom was not the firm muscular masculine ass he preferred for his partners.

Kyle was a switch and he could either top or bottom with whomever his lover happened to be. But Jewels femininity was off-putting and he couldn't ever imagine being a bottom with her. It was an aspect that was certainly something to consider when he finally...ugh...marries her.

Kyle just hoped his mother was right about this. He would never have picked Jewel for his wife. He would rather have chosen someone like Roderick for a husband.

Kyle closed his eyes as he fantasized about Roderick...

As he did so his cock became harder...Kyle imagined that Rod was topping him, his firm muscular body...Kyle was pleased with his fantasy. He was going to cum...

Jewel was on her hands and knees. Kyle's fingers dug painfully into Jewel's hips and pelvis from the strength of his grip. Jewel pushed back as Kyle thrust his cock into her. She decided she would begin to moan softly to try to encourage Kyle to cum. His cock was doing nothing for her. She knew now that she just wasn't into having sex with him and wondered why she talked herself into it.

Suddenly his cock got harder.

His pace increased.

His thrusting lap was slapping into her bottom.

Jewel moaned softly in encouragement

"Shh!" Kyle shushed her. He was so close!

Jewel was nonplussed at being shushed and simply knelt quietly as Kyle pounded her backside, her body being pushed forward, then pulled back by his grip on her waist as he slammed into her, her firm full breasts jiggling fore and aft with each thrust.

Kyle suddenly ground down against her ass and groaned loudly.

Jewel could feel a slight splash of warm wetness inside her ass.

Kyle immediately withdrew his cock and flopped down onto the bed next to her.

Jewel rolled off her hands and knees onto her side looking at Kyle. He was breathing heavily as he recovered from his orgasm.

After a few moments he opened his eyes and looked at her.

"Was it good for you too?" He asked.

"Oh...yes...it was great." Jewel said and nodded her head yes.

Kyle closed his eyes again and rolled onto his side facing away from Jewel.

"Thank god that's over." He thought, happy that at least she had enjoyed it as well. Kyle had been dreading the day she would ask for intimacy and sincerely hoped that would satisfy her for awhile. The amount of effort finding an effective fantasy alone was exhausting.

Jewel got up and out of bed to make her way to the shower. She wanted to wash out his cum before it started leaking out and soaking into and staining her panties.

While she was glad she had acted to satisfy him and his male lust she hoped it would be enough to hold him over for awhile.

**

Kyle and Jewel just finished with the informal luncheon among charitable business groups where once again Jewel had presented her plea for support in ending the practice of arranged marriages. Once again she was disappointed by the lackluster response her audience gave her.

After the meet and greet, her speech, and socializing after it was getting late in the day. The sun had set and it was just after dark when Kyle suggested to Jewel they go for coffee at a nearby coffee shop. Jewel accepted eagerly. She rarely ever drank coffee but it was rapidly becoming one of her favorite hot beverages.

Arriving at the trendy shop Jewel found a table for the two of them in a quiet corner while Kyle went to the barista to place their orders. He returned quickly with two cups of coffee before he sat across from Jewel.

Seemingly from out of nowhere Kyle presented Jewel with a Red Rose.

Jewel politely accepted the rose and fawned over its beauty and fragrance just as she had been trained before she realized exactly what flower she held.

The flower was a single long stem red rose...a symbol of love and romance. Jewel knew it was currently fashionable among the young nobles of the Allegorian court to present roses as a declaration of intent. It was an ancient practice that they had recently revived, much to the approval of their elders.

Was Kyle seriously declaring his intention to court her? Why would he give her a red rose?

Jewel suddenly realized that Kyle wasn't acting as her escort and chaperone anymore. He seemed nervous and uncertain. Jewel knew that she had just been set up.

"I feel that I cannot continue with this charade. I have to tell you the truth."

"Of course Kyle, what truth?" Jewel was nervous. First a red rose and now a cryptic opening statement. Her pulse was racing.

Kyle took a long pause. He took a deep breath, and then spoke from the heart.

"Honestly...feminine men are gross...but you pull it off well."

Jewel truly believed her hearing must have failed her. She took several moments to process his statement and backhanded compliment to compose a response.

"Are you neg'ing me?" Jewel asked uncertainly.

"Neg'ing?"

"Making negative comments to induce feelings of insecurity with intent to exploit those feelings for personal reasons." Jewel stated.

Jewel was amazed at the gall Kyle was displaying yet proud of her ability to rattle of a definition as if straight from the dictionary. Her time spent as a student and a teaching assistant at a private all girls' school had to be good for something.

"I want to be honest, open and aboveboard. I have to confess to you that I am not attracted to you. Mother has insisted that I must go through with it to satisfy our family honor. I know you too must maintain appearances, so if you are willing and able to at least maintain appearances as a feminized male bride I am willing to make the necessary sacrifices to mollify my family."

"To be blunt, I do know that you want to have...relations with other men." Kyle looked meaningfully at Jewel. He took her silence for assent and continued.

"To continue to be blunt, I am gay. I too desire to pursue relations in accordance with my orientation."

Jewel just sat there...stunned.

"I proposed that you allow me to be your sole escort during your time of mourning..." Kyle swallowed hard and took a sip of coffee before continuing "and that allows me to court you as your suitor afterwards. In a month or two we can marry and each of us will assume the roles society expects of us, me as husband and you as wife."

Jewel's shock had transformed into stupefaction.

"And naturally, we can both continue to pursue relationships according to our orientation, both of us with other men. Men we would each find for ourselves. Attractive men...or concubines' maybe." Kyle mumbled, and then paused to let that bit of information sink in.

Jewel was suddenly extremely glad that she was still within her year long period of mourning for her husband. His implication that she was unattractive stung.

Jewel was astounded to hear him say so bluntly exactly what he really wanted. She carefully considered what she knew of Kyle's intentions. He wanted her for the appearances of propriety and her status as countess, nothing more.

Wait...Lady Oldsworth...she put him up to this. With a flash or insight Jewel received an epiphany. Lady Oldsworth wants Kyle to marry her...for her money...

Another thought burst into the fore; I can't believe it...I let him sleep with me...I had sex with him...that we had sex...Jewel felt cheap and used. She blamed herself for letting her therapist convince her to explore sexual intimacy with another man.

"I do not find cross-dressers attractive. The thought of intimacy with you repulses me. But a marriage to each other gets us both where we want to be; you safe to pursue your fetish as a cross dresser and...uh...submissive...while I can have relationships with men who look like men."

Jewel carefully mentally summarized what he had just said to her.

He was willing to marry her for family honor and public perception. His family honor, not hers.

Jewel also knew that as a woman of independent means, if she were to marry again she would basically be giving Kyle her wealth and when that happens she would be expected to resume her previous lifestyle of leisure while Kyle would manage their combined marital assets.

But most galling were his ulterior motives. He didn't even pretend to love her. He had been her escort and friend all this time just to be close to her; to position himself near her and be seen as her...protector and...sleep together...

Aaauugh...her mind screamed in betrayal!

He would be free to take male lovers and he expected that she would do the same! Gross!

Jewel was thankful that the black mourning veil draping perfectly from her fascinator helped to obscure the astonishment that would otherwise certainly have been evident across her face.

Her fascinator's veil, coupled with years of self discipline and the stern training by her governess to control her emotions allowed her to maintain her neutral expression...but just barely.

She eventually forced a small smile and responded noncommittally.

"That idea..." She paused politely despite the anger that was bubbling up and burning deep inside her "may be worth considering"

Kyle smiled.

"But," Jewel continued "I am still mourning for my deceased husband and am in no state to begin considerations of such momentous importance during this painful time in my life."

Jewel lied with a frank face and a deceitful heart. She had no intention of ever marrying a man again. Did everyone really think that she was gay and that she actually enjoyed dressing and presenting as a woman? And hell no would she ever marry Kyle Oldsworth.

Kyle's smile never faltered.

"Of course; and I would never presume to impose upon you in such a way during this difficult time. But I can continue to be here for you now as you continue to grieve and provide a shoulder for you upon which to lean."

Kyle knew that he needed to keep his position as her companion so other suitors would be dissuaded from pursuing Lady Jewel, and to satisfy his mother's ambitions for him.

Jewel was grateful by the momentary distraction as the barista at the counter called for a customer.

"Tya...Taya....Tina?" She asked the busy room.

Jewel glanced toward the barista and was caught unprepared. Her breath caught in her throat as she recognized the woman.

She was beautiful...It couldn't be...

She was alive and well...

Donna!

**

Donna Hancock handed off the latte and a hot chocolate drink to the customer. A young woman took the drinks and returned to a table where her daughter waited patiently coloring books.

As Donna stood behind the counter she quickly surveyed the shop and the customers at their tables. Her attention was drawn to a young woman who moved to stand up and was in fact staring intently at her

Dressed all in black the woman appeared taller than Donna was although Donna was wearing her flats for comfort and the woman wore high heels. She had a perfect figure if the way her dress was flattering her was any indication. Donna was unable to make out her face through the black veil she wore from her fascinator hat; just that her long brunette hair hung loosely behind her.