Meeting Karen Pt. 01

"I'm unable to imagine anyone hiring me, as a new female lawyer," but she was softly weeping.

"My hair. All they comment about is my haircut!" and she turned back to the dance wall mirror.

"Months ago one of the assistants suggested that my hair style recalled the pixie Ann Hathaway once wore! Now as it's longer, it's in a tail every day," Carrie smiled reaching to touch the longer hair that was nearly to her shoulders.

"I should follow my therapist suggestion, but I'm worried about standing up for," Carrie was referring to the visage of a woman they both saw.

Toni could offer only minimal support, as Carrie would not agree to her regular suggestion that she file the paperwork.

Each week Carrie would encounter several other dancers, as she had two lessons, on Monday and Thursday evenings. One person was quite attentive; a male, about two years younger than Carrie, and he was openly gay. Jon asked if she would accompany him to a dance party.

"It's at a club Carrie, and you will not be harassed, as I will be there with you," Jon was trying to convince her. Carrie liked him, and his persistent requests.

"Please consider this a non-date though. I want to dance with you Carrie, but I generally stay with the guys," he said, as Toni listened.

"Next week, we could go together, and I promise to bring you home as well, okay Carrie?"

Carrie had the weekend to consider Jon's offer, and on Sunday she spoke with Toni by phone, "He will be a good chaperone Carrie."

Later in the week Carrie called Jon, "So Jon, you can assure me that you will be my, sort of shepherd?" he understood her concern.

"I haven't been out, I mean to say that, well, and this will be my first time. Other than to dance class, I have never gone out to a club, dressed as Carrie, let alone dancing," Carrie said.

He considered her concern, but said, "Why not? You are clearly able to pass Carrie," and he reiterated his support.

Her anxiety was apparent in her voice, so he suggested, "Let's meet for a simple dinner Carrie. Just give me the address, and I will pick you up."

Carrie liked Jon's idea, "Okay, but what do I wear?"

Jon responded quickly, "Just jeans and a nice top."

He arrived and she met his car. They drove a few blocks, and Jon pulled into the Hooters lot.

"You really want to eat here?" Carrie asked.

Jon simply smiled.

"I have been here several times, and I always enjoy how over-the-top the waitress' look," and he shut off the engine.

Carrie was hesitant, but Jon was out of the car now, "Come on. You look great Carrie," and he had walked around, and now he opened the car door.

The meal was good, and Carrie relaxed, though she didn't accept his offer of a drink.

"I need to be careful Jon, as you were right, I look less vamped than any of these women," Carrie suggested.

Jon smiled, "They all work at it, and focused on making every guest feel welcome,".

On the ride home she asked if Jon was certain that he would be with her at this dance club, "I don't want to become your burden Jon."

Carrie planned and considered her outfit for Friday evening all week, and several times attempted to dress and prepare. Her experiments allowed her to make adjustments, but she was still careful. She would need many more hours, so she coordinated her Friday work schedule to allow her to leave by three, on the afternoon of the planned club visit. She eventually selected her black shiny leather skirt, with a simple white blouse. The black heels were just right, with an ankle strap, and gold detailing. She decided to wear her blonde straight wig, which fell to nearly her quite small, but budding breasts. She decided to forego a brassiere.

Once at the club, Jon was true to his word, and his presence helped Carrie to feel comfortable. She relaxed once Jon introduced her to his many friends. Interesting men and women were all around, but Jon kept Carrie away from the predatory guys.

"See George there Carrie?" Jon indicated subtly.

Carrie looked to see a tall man with a simple mustache.

"Yes, he's the one" Jon continued after Carrie acknowledged the guy at the bar.

"He loves to take on the new boys, and girls, as we know you are. He would be all over you, so recognize him, and try and stay clear, if you decided to come back without me," Jon said.

They danced to seven or eight songs, when Carrie's legs and feet were tired. Though her heels were only three inches and looked sexy, they may have been a poor choice. Carrie would eventually understand the importance of superior footwear.

"Can we stop, and maybe sit for a little while Jon?"

He escorted Carrie to the table where several of his buddies were sitting.

"Can you guys entertain Carrie while I get her a drink, please?"

The man sitting nearest was handsome and Carrie could recall his scent, "Is that Boss?" she asked.

He smiled, "I'm Jerry, yes. Are you and Jon dating Carrie?"

She quickly responded, "No, he is my friend, from our dance class, and I needed some support, well, to come out tonight," she shyly said.

Jerry and the other man told her that she looked lovely, but Carrie wouldn't believe them, "You are being kind, guys. You certainly can see that I'm a cross dresser?"

Jerry now, turned and shifted closer, "No way, Carrie," he was surprised.

"I did not, but with your sharing that, I will say you had me duped." The other guys just smiled and chuckled softly.

"I'm new to this," Carrie offered.

Carrie heard the other man offer a compliment, "I've seen them all, and you're quite a pretty girl."

Again, Jerry spoke over the guy.

"Look Carrie, we do see a few dressers here, but I thought you had somehow pulled Jon back to hetro. You do move well, and you have lovely legs," Jerry said.

She saw that Jon was returning.

"I asked you to take care of my date, not do an inquisition! Were they at all rude Carrie?"

Carrie smiled, "No they were just talking with me Jon," and she sidled up along him.

They stayed until just passed midnight, "I think we should leave now Jon, please," Carrie asked.

A second date was agreed to for the follow week, "But can you please drive yourself Carrie, as I plan to make a move on a guy?" Jon asked.

The following Friday evening Carrie watched as Jon did in fact find his lover, and it emboldened her, and she actually made-out with a woman and a man that night. Near midnight she resisted an older man's offer.

"Come on Carrie, I don't want to bed you, just suck you off!" this forty-year old man said. She quickly left, rather than deal with her anxiety.

Carrie had developed her perspective as she regarded the females she was meeting, and she now considered herself a femme lesbian at the moment, and what she wanted, what she needed was a woman, not a man. Of course, she realized that as a transwoman, she would need to be patient, as the lesbians she encountered at the dance club, were generally rude, and dismissive of her dressing and gender selection.

One night, a woman named Gloria was blunt.

"Why would I want to take you to bed Carrie, when you are, well limited? With only an arse hole. There are plenty of girls here tonight with two holes that would want me to be with them. You may be sexy, you queer girl, but I will wait and see if you can handle the world."

The super-bitch walked off, and the other nearby girls giggled and said snarky things to Carrie. She tried to be coy, and disregard the three of them, but one girl came to Carrie's side.

"I think you are kind of cute, really," and she lightly touched Carrie's left arm.

"My name is Melissa," and she turned and walked off. Carrie smiling watching this friendly lesbian move away.

Slowly, over several months, Carrie developed a group of friends at the club, some women, and other guys, who took an interest and covered for her. She still felt less than becoming, but the style she was evolving was hers. Carrie came to feel more comfortable at the club but tried to visit only twice a month. Her dancing lessons were therapeutic, and Toni had become a good friend.

One day, Carrie asked her to come dancing, but Toni seemed to be uninterested.

"No, I'm just not into that scene Carrie. I am more of a home body, but you seemed to benefit from being around other supportive people, so you should go, and send me some new students please."

A few weeks later Jon suggested someone to Carrie.

"He has a nice manner, and he could help you Carrie, you know, go all the way." Carrie had been curious about this and her and Jon had discussed the nature of his sexual encounters.

"Always with a condom Carrie, never naked, even today."

The following Friday Jon introduced Carrie to a man named Rob. Carrie found Rob exciting, but she tried to remain calm as Jon and Rob stood near, and she noticed Rob's attentive gaze. Her dress was short, and her hose' could easily become an issue, so she said when Jon left them.

"No Rob, I don't mind standing," though there were two stools empty at the bar.

Jon had explained on the ride over, that Rob was also an attorney, "He is into you Carrie, as he has seen you dancing these past few weeks," but Carrie was hesitant.

"You two will have a lot to talk about," Jon said. "When you're ready, Rob will be gentle, but remember Carrie, it's your decision, not his." Jon reminded Carrie.

Then she saw Jon's hand, "Here girl, you may not have come prepared." In his hand Jon had a package of three condoms.

"These are the best, and I assume that you have, ahh, prepared, Carrie."

Carrie had a single condom in her clutch, but she took Jon's gift.

"Will he really want to sleep with me, I mean, tonight Jon?" Carrie listened as Jon spoke of his past casual sex.

"I love sharing my body with strangers," Jon said.

"Yeah, it can be quite exciting, but then, sometimes it isn't." he said.

Carrie sighed, remembering a guy almost a month ago that was a little aggressive, after she had his semen in her mouth.

As Jon walked across the parking lot and the two entered the club Jon took her hand and spoke quickly now.

"Today it's not 'let's wait'. It is all about the sex, then the dating can follow, and then a relationship. Never mention marriage Carrie," he chuckled and then said, "Well maybe, someday,"

Carrie then offered, "As a person, a woman now, I feel somewhat uneasy about one-night stands, but yes, I do want this Jon, the experience," Carrie adjusted her dress, as it had risen well up her thighs, and she noticed Jon's eyes on her hose'.

Jon smiled, "Well Carrie, dressed like that, you are clearly interested in getting laid."

Carrie said, "I know, my dress is provocative Jon, but uncommitted sex, is new to me. I haven't been with anyone in two years, for god sake!"

Jon quickly added, "To me Carrie, you look great, and there's something empowering about casual sex. So try and go with it; Rob isn't going to hurt you," he said quietly.

Now Jon saw his friend, and Carrie still held his hand, "Here he is, Rob Jones. Please meet Carrie West."

A few minutes later she watched as Jon walked away and Rob smiled and moved closer. Rob could tell Carrie was anxious, and he took her hand, and kissed her fingers.

Now Carrie smiled, as Rob spoke, "We are just two people, meeting to enjoy the evening Carrie."

"It just all, so new to me, Rob," Carrie said. She liked him, and his neat beard, and she had noticed his scent, a bit deep and woodsy.

"I can be patient Carrie, so let's just hang, and see how this evening goes, with no need for a hook-up. It is early, and I like you, and the dress is, yeah, quite sexy."

Rob moved and now held her arm lightly as he leaned into kiss Carrie. It was a soft, gentle kiss, and Carrie responded.

She knew then that she would be with him, soon, if not tonight.

"So, can we dance Carrie?" Rob asked.

Carrie wasn't looking for a boyfriend for a night, or a girlfriend, but she was curious about being intimate as her feminine self, and Rob could be just what she needed. They danced and slowly became more comfortable, and Carrie noted that Jon was near, keeping an eye on his two friends.

Near midnight, Rob took hold of her as the music shifted, and she was held, and they kissed, and Carrie wanted what was about to happen. Rob was clearly aroused, and they both felt his stiffness as they danced and embraced.

"Shall we, Carrie? Can I take you home now?" Rob's one hand was about her back and he held her, and they kissed, Carrie was going to allow him to be with her. She reached down and boldly grasped his hardness through his trousers.

"Yes Rob, I am ready," and they moved off, and Jon smiled as he saw the two walking toward the door. Carrie saw his look and smiled back.

Outside and along their short walk Rob asked, "Do you feel as excited Carrie as I am?"

She smiled and squeezed his hand, as Rob moved to look at her.

"I like your smile, and you have great legs Carrie," Rob commented. "And you can carry that look off," he said as they began to walk along the street.

Carrie was holding his hand, and restricting the pace, as her heels were almost four inches, "I like hearing you walk Carrie, and those heels are quite sexy! Don't look, but those two guys there, are gawping at you."

Carrie and Rob continued to hold hands as they walked up to his building.

"It's not much, but I like being downtown." They had walked the three blocks to Rob's co-op. Carrie was glad she hadn't worn her platform heels.

In the elevator, Rob again kissed Carrie.

"Your lips are so gentle," Carrie softly said.

She had planned to fellate Rob first, to do what she had learned and developed, as Carrie had become a good cocksucker over the past several months. Rob opened the door and taking Carrie's right hand he entered, and the door closed.

"First, let me see you Carrie," Rob said as he spun, and he quickly dropped to his knees.

"Can I explore a little?" Rob asked, as his hand moved to lift the short hem of her dress. Carrie saw that he was respectfully lifted her red dress.

Rob now saw the white silky thighs above Carrie's nude-toned hose'.

"Two panties; that's a trick!" he said as he pushed the first thong down about Carrie's thighs. Then he slipped the other aside, and carefully removed the tapes holding her sex back. She had worn the suspender belt beneath her thongs.

Carrie wasn't big down there, but she was growing excited as Rob released the second tape.

"You know Carrie, that I haven't been with a woman, I mean like you. This will not be my first time, but looking at your body, framed by the lovely garters, well it's exciting," now Rob held Carrie, as she stiffened.

Then she watched as he opened his mouth and licked her shaft slowly, from the base to the tip. Carrie closed her eyes, as Rob continued, and she wondered if the men she had fellated felt something like this sensation. Rob was quietly licking her, and she could imagine how she might return this pleasure.

"Rob, that feels, exquisite, no one has never, ohh," Carrie now felt Rob sliding his finger along her perineum.

"Yes, oh god," then he pressed his fingertip gently against her bottom hole.

Carrie looked down as Rob looked up into her eyes, "Yes, I am enjoying your body Carrie,"

He opened his mouth and covered her sex. A minute later, Carrie was close to her orgasm and she was moaning softly.

"Rob, oh, don't stop," and he had his long finger slightly inside her bottom, then he slipped the long finger out of her body, only to insert two of his fingers., as he slowly moved and twisted his hand.

"Oh god, Rob, yes" she sighed, as Carrie tried to control her body, but she released, and Rob removed his mouth from her sex, and Carrie shot some of her semen onto her tummy and the lacy suspender belt.

As she breathed deeply, Carrie wondered how her sex might take control of her life, as Rob's attention was so special. She shifted as Rob stood, and their kiss confirmed that this was more than normal. Carrie had never felt such an orgasm.

"Can we do that again Rob," but he took her hand and kissed her again as he moved to the sofa.

"No Carrie, now we will carefully, and slowly, ahh, stuff my penis inside of you. I will be gentle Carrie, and we will both enjoy this, with some lube to aid your body."

He swung Carrie into the soft cushions and again got on his knees, but this time his focus was deep between her butt cheeks. Rob rolled her onto her hip as Carrie removed the thong still around her thighs, and she used it to wipe up the semen, just as Rob kissed her down there, licking her tight, tender flesh at her opening.

"Rob, I," but she sighed as he pushed his tongue into her slightly, and then he rubbed her with the lube. He wanted to tease Carrie and so he licked and rubbed his shaft up and along her bottom cleft for a few moments before entering her body with his finger once more.

Carrie watched, and sighed, "I am quite tight, so please be patient, as I do want to be with you Rob. I want you to fill me," she moaned as he slid the second coated finger inside her body.

"Oh god, ohh!" she moaned.

"Just relax Carrie, I have been the first before, with three or four, so I will be slow and yet, you will be filled."

He chuckled as he now stood, and he removed his belt. Carrie wanted to help him, and she rolled to sit with her knees near the sofa edge, as he released the clasp of his pants. Carrie reached to pull Rob closer, and her left hand helped Rob remove the shorts and then she held his penis.

"I'm not super hard yet Carrie, but it will grow, and you will enjoy it," but Carrie wanted to fellate her lover, and she pulled him close and kiss his rising penis.

"It is a nice cock Rob, and I like how you have removed all of your hair," she whispered, and Rob watched as Carrie licked the helmet, and then the shaft. Her tongue enjoyed licking him, and then Carrie deep-throated his penis.

"Carrie, wow, that's crazy deep!" Rob moaned.

She pulled him out and gasped slightly before again deeply eating his penis. He enjoyed her tongue, and she now held his hard dick, and he paused and covered his sex.

He smiled as Carrie measured the length with her fingers.

"Yours is so much bigger than mine Rob," and she kissed and pump the shaft with her right hand.

He was happy, but he wanted to get his stiff cock into Carrie.

"My turn Carrie, so roll backward please," and she did, lifting up off the cushion, as Rob moved close. He slowly rubbed the head of his cock across the cleft of her bottom, as his finger again slipped into her lubed hole.

"I think you are beautiful Carrie, and this tight ring is softening."

He removed his finger and now Carrie felt the pressure of his stiff cock against her opening, though he wasn't aggressive.

"Let your bottom open for my dick Carrie, it will, slowly," and she looked back at him, as he wet his fingers in her mouth.

"Just a little spit will do," and Rob rubbed it across his helmet, as he again positioned and moved against her body.

"Oh, oh," Carrie moaned. "It's just too big Rob, ahh," but then she breathed, and the tip entered her body slowly,

"Oh my god, you are huge Rob!" she exclaimed.

Rob saw her face as she turned to look at him, and he smiled.

"I know I'm not huge, but Carrie, you are now on my cock. The head is inside your body, and in a few moments, it will fill you. What do say to that?"

She continued to look over her shoulder, "I want you to fuck me Rob, I love how my body, ohh!" Rob had shifted and Carrie now knew the entire head of his dick was insider her bottom.

"Relax, Carrie you are opening to my cock, I'm just holding steady," he said as his hands reached for her face.

"Wet my fingers Carrie," Rob then removed his penis and re-entered her tight hole.

Again, she felt the cock move slightly deeper.