Pam - Trans Escort Ch. 01

SUNDAY

Pam Wilde was lost in thought. She didn't know exactly what brought it on, but nonetheless, a flood of images came rushing to her that she couldn't tune out.

Pam was 22 years old, stood 5'8", weighed 125 pounds, had brown eyes and brown hair that fell to her mid back. Her breasts were a perky 34C cup. She felt sexy enough but thought her one prominent feature that put her in the "hot" category was her 10.5" cock.

Pam thought about her hometown; Woodbridge. She knew that most transsexual women left their hometown as quickly as they could so they could start fresh where nobody knew they had a girl cock. But for Pam, the people in Woodbridge had embraced her transition. She had never felt embarrassed about it so she never felt compelled to leave.

Woodbridge was a typical small town that might have dried up and disappeared if not for a start up tech company that picked the outskirts of the town to build their factory. After that two rival tech companies did the same and now 90% of Woodbridge citizens had good paying jobs. Life in the small town was good.

Pam herself had a tough childhood. She lost both parents early in her life. She was raised by her aunt Tilly. She knew from an early age that being a boy was wrong for her. By the time she was 18, even though she was on hormones, her cock grew to it's full size of 10.5". She didn't mind because at the time her plan was to save up the money and have the surgery to fully transition.

Pam's best friend throughout school was a girl by the name of Mel. Pam had always been a computer geek and Mel always teased her about it. When Pam became a girl, their friendship solidified and they became almost inseparable. Pam often had sleepovers at Mel's and, with the help of Mel's mother, Eve, showed Pam how to dress and do her makeup.

Mel's graduation party was another sleepover since Eve allowed the girls to drink alcohol during the party. Mel slipped away to be alone with her boyfriend and Eve, tipsy herself, hit on the now 18 year old Pam. Pam lost her virginity that night to the MILF. Several times.

Pam found that she could stay hard for multiple rounds and always came just as much. Her recovery period was short, if she even went soft after cumming.

One year later Eve convinced Pam that she could probably make a lot of money being an upscale escort. Eve had apparently researched the ever growing trend of the transsexual "fetish" in the area. Both men and women seemed to be constantly searching for transsexuals to scratch that itch.

Pam designed a website and an app that worked in conjunction with the site and within two months she was up and running. Her charge was steep at $1,000 for a 30 minute session and $1,500 for a full hour. But a day later she had her first date and she never looked back. After a month she found herself with $20,000 in the bank which changed her mind about a full transition. She decided to keep her cock.

One year later, at the age of 20, Pam found herself with a Mustang GT fully paid for. A very nice house that she had half paid off. A steady client list which also allowed herself the luxury of being picky and not needing every potential client that came along. Life was good.

Pam had a huge smile on her face as she remembered all of this when a voice broke her reverie.

"Um, excuse me," Mel said. "As much as I love when you pound my pussy, you know it's not what I really pay for when we're together. And I've only got like five minutes left."

Pam snapped out of it and grinned. She smacked Mel on the ass then pulled her cock out. It glistened with Mel's pussy juice. "I know," she said. "Sorry." Pam motioned with her finger and then stood at the edge of her bed. Mel quickly laid on her belly at the edge also and opened her mouth.

Pam grabbed Mel by the back of the head to hold her steady and in one motion shoved her cock fully into Mel's mouth. Mel instantly gagged and spewed out saliva that splashed against Pam's pubic area and slid down to coat her balls. Mel shook her head wildly back and forth and Pam pulled her cock out.

Pam grinned and said, "Baby, that's how you like it."

Mel answered, "Yes but you can't surprise me like that! I gotta know it's coming!"

"It's coming," Pam said then shoved her cock fully back into Mel's mouth. Saliva coated Pam's cock again from Mel's gagging.

Pam had had this back and forth with Mel several times and she knew just when to pull out and give her air. She then pistoned her girl cock hard and fast into Mel's mouth, face fucking her. The gagging soon changed to just sloppy wet sounds as Mel settled into the rhythm herself.

Pam felt her balls cinch up tight and she tapped Mel on the head. Pam yanked her cock out and Mel spit heavily on it one final time before Pam gripped her cock and stroked it until she shot her cum. Six heavy ropes of jizz spurted out to cover Mel's face completely, one even hitting the bullseye of Mel's open mouth.

"Jesus fuck," Mel gasped. "I think you cum more and more every time you fuck me."

"Just trying to please my clients," Pam said then laughed. She went into the bathroom and emerged with a wash rag and tossed it to Mel.

Mel started to clean herself off. She asked Pam, "Hey, do you think if I wouldn't have teased you as a geek back in high school that I would be getting this treatment for free?"

"Probably not. But school is the only reason you get it for $500 instead of my full rate."

"Does my mom get the discounted rate?"

"I fuck your mom for free." Which, Pam thought, was true enough. She fucked everyone else for money and it was all about them. With Eve, it was for pure satisfaction and they had become close lovers, trying different things because they wanted to, not because someone was paid.

Mel finished cleaning and got dressed. She kissed Pam deeply then left. Pam headed to the bathroom to shower, her cock still only half soft. She decided against masturbating and just thoroughly cleaned. Pam hopped out of the shower, dried sufficiently, then put on her plush robe.

Pam had just opened the fridge to grab a drink when there was a knock at the door. She closed the fridge and headed for the door. When she opened it she saw Sheriff Pat's cruiser in her driveway and the Sheriff standing on her porch.

"Hi Sheriff," she said. "What can I do for you?"

"Hey Pam," Sheriff Pat said. "We got a report of some suspicious activity and I had to check it out. Can I come in?"

Pam held the door open. "I guess if you think you must. But really, I haven't seen anything odd."

Sheriff Pat entered and looked around. Pam headed to the kitchen again but she was stopped by the Sheriff's voice. "Just stop Pam. You know what I'm talking about and why I'm here."

Pam turned and saw the sheriff with his hands on his hips, almost too close to his tazer. "Ok sheriff. I see you're not playing and yes I know why you're here." She undid the sash on her robe and the front slid away. Her naked body now revealed and her soft, but still 7" girl cock which hung impressively between her legs.

"But sheriff," Pam said slyly. "You know what you need to do first." Sheriff Pat was her only cash client as he couldn't let his wife see the card charges. Besides, having the law on her side in the profession she was in was just smart business.

Sheriff Pat withdrew a wad of cash from his pocket and tossed it on a coffee table. "You want to count it?"

"No need. The usual?"

"God yes," Sheriff Pat said and quickly dropped his gun belt and pants. Once naked from the waist down he got on his knees and spotted Pam with her cock in one hand. They met halfway and the sheriff immediately took her cock in his mouth, his only goal was to get it somewhat hard.

Pam hardened almost immediately with the sheriff's warm mouth on her cock. She only let him suck it for a few seconds, then spun him around. The sheriff spun and assumed the doggy position and waited.

Pam got in position behind the sheriff and pressed the head of her cock against his asshole. She applied enough pressure to allow the head of her cock to slip inside. The sheriff moaned instantly. Then without warning, she thrust half her cock inside. The resistance was too great at that point so she pulled out, reset, then plunged in again, half her cock buried inside the sheriff's asshole again.

Pam leaned forward and grabbed the sheriff by the shoulders and started a rhythm of slow withdrawals and greater pressure with each forward thrust. After ten thrusts she was balls deep in his asshole. Sheriff Pat's body tensed and he couldn't hold it; his dick erupted cum all over the floor.

Pam now amped up her thrusts, each forward push ended with an audible flesh on flesh smack. She continued fucking him hard and eventually heard him moaning heavily again. Pam shoved her girl cock in one last hard thrust and held it there while she felt the sheriff's rectum squeeze her cock shaft again. With a grunt he dumped another small cum load onto the floor.

Satisfied, Pam pulled her cock out and held the base stiff while Sheriff Pat turned and took the head of her cock into his mouth. She then proceeded to stroke the shaft vigorously until she felt her balls cinch tight again. She slowed her strokes as jets of hot cum exploded into the sheriff's mouth. He wasn't great at swallowing and only got about half of her cum down his throat; the rest of it escaped his mouth to drip onto the floor.

Pam stood, her cock still raging hard. She looked down at Sheriff Pat and said, "I'm going to shower. Clean that up before you leave." She headed towards the bathroom but still spotted Sheriff Pat on his belly desperately slurping the cum collected on the floor.

Pam cleaned thoroughly in the shower for a second time and by the time she headed back to the kitchen for some water, Sheriff Pat was gone, the floor was clean of any cum. Pam smiled evily at this then headed to bed. Tomorrow would be another busy day and she needed her sleep.

MONDAY

Pam woke early and dressed. Since it was already warm out, she opted for a sundress with no panties. She always loved how her tits looked in a sundress anyways and even when flacid, her girl cock hung low and didn't show. If and when Pam did sprout a hard on, she delighted in the stares she got when her dress tented outwards.

Pam arrived at the coffee shop around 7 A.M. to start her daily routine. She sipped on her coffee as she opened up her booking app. After deleting the bulk of emails that only wanted conversations, it left her ten emails to actually sort through, although she knew some of these would require deletion as well. Some people just couldn't follow the guidelines listed on her website.

Guidelines were spelled out early and often at her site. There was a bio written as to what she offered as well as G rated pics so a customer would know what she looked like. A potential customer was to sign up with a username and password, offer a brief email with a description of themselves and what specifically they wanted. They had the option of uploading a pic but it was not a requirement.

From that, if Pam was interested in taking on the client, she would respond with a link and verification code which would unlock her X rated folder and access to her calendar. If the client then wanted to book a date all availability showed on the calendar.

A first time client would always have to book a face to face meeting, free of charge, so they could see if there was compatibility. A simple cup of coffee and some conversation did wonders.

When the client booked a date time, Pam received an email notification. She then would send the payment information and requirements. She had to have the client prepay because she had learned the hard way that some people got cold feet and that left her an open time slot that she could have filled otherwise.

When the payment was made there was a more comprehensive questionnaire filled out as to what the client wanted. She was open to most things and strived for her clients to be ultimately satisfied with her service. She always allowed a cancellation with a full refund as long as it was 24 hours in advance.

In the beginning stages of her endeavors, there was a learning curve as to how to conduct business. But ever since perfecting her current process, things usually went smoothly. Except for the aforementioned emails of "I'd love to fuck you" came through.

Out of the ten emails she kept, two didn't seem like the client would be a good fit for her so those were deleted. Four were returning clients so the verification email was sent out. That left four possible first timers. Those were always her favorites.

There was one from a married bi male in his 40's whose wife actually wanted to provide the experience for him as a birthday gift. Pam thought this had potential so she sent the email with the link.

There was one from a recently divorced woman in her 50's who had only ever known her husband as a lover, who she described as "the tiniest dick in America" and was referred to Pam by a longtime client of hers. Pam sent the link.

There was one from a woman she'd known in high school, Sara. Sara stated she wanted no strings attached sex, because she 1) Never had time to go find it; 2) Had always been insecure about her weight and didn't want the embarrassment of being turned down; and 3) Had always had a crush on Pam after her transition and secretly desired her cock size from seeing her in the gym showers. Pam sent the link.

Lastly there was an email from a man in his 20's who was admittedly straight, but had watched a porno where a transsexual was given road head and he wanted to try. Pam almost deleted it but she also wondered about getting her cock sucked while driving. And who said you couldn't live out your own fantasies just because you were an escort? She sent the link.

Pam finished her coffee and was about to leave, she had a client in an hour, but her email notification buzzed so she checked it. Sara had responded already and wanted to book her face to face immediately as she was going to be too busy the rest of the week. Pam figured she'd have the time since her client was meeting her at her home and that was only a five minute drive.

Pam sent the response and told Sara to book the face to face on the calendar and if she could get to the cafe in ten minutes, they could have their meet. And if she didn't make it, to just cancel it and they would just have to do it another time. Almost immediately the notification of a booking time came through.

Pam was shocked when only a few minutes later Sara walked in the door. Pam thought she hadn't really changed at all. Sara was about 5'3" with long blonde hair and yes, she was bigger at about 180ish, but Pam thought she looked pretty good. Sara's tits were huge and were trying their best to burst out of the T-shirt she wore. Sara's thighs were shown off rather well in the cotton shorts she was wearing and suddenly Pam couldn't stop wondering what she'd find with her head buried between those thighs.

Pam thought Sara's best features were her skin, which glowed and seemed flawless. And the way she shone with her sexuality. Pam didn't care what size Sara was, every inch of her fiber screamed "Woman!".

Pam stood and hugged Sara and the two ordered coffee. When they sat, Pam said, "Wow Sara. You haven't changed a bit. You look gorgeous!"

"Thanks," Sara replied. "You look hot as hell yourself. I couldn't believe it when Mel suggested looking you up. I was surprised, but I understand how lucrative your business can be with your body."

Pam grinned. "Mel referred you, huh?"

"Yeah. To put it bluntly, I just need cock. And, well, you've got a good one and you've never made fun of my weight."

"Nothing to make fun of. I think you look sexy as hell."

The two women small talked a bit more, Sara laying out what her ideal date with Pam would be. They parted ways with Sara confirming she would be booking a date. Pam sent her the booking link since the face to face went well, then hopped in her Mustang and headed back home.

Pam arrived home with 15 minutes still to kill. She had to set up a homemade glory hole before her client arrived. This particular long time client liked to suck her off through a hole anonymously. They had never laid eyes on each other even though he'd been a customer for two years.

Pam had had a three sided box made that slid in front of her back door. It latched in place on the sides so it wouldn't tip. The thought of a glory hole always excited her and she had to think bland thoughts so as not to get hard. This client preferred her cock to flop through the hole soft at first.

Pam still had time to kill so she checked her app again. Three more emails of "I wanna suck your cock" got deleted. The divorced woman submitted her questionnaire email though. She opened the link and read the bio first. The woman's name was Shelly and she was 53, 5'9" and 165 pounds, long brown hair with brown eyes and a 36EE chest.

Shelly had submitted a clothed and nude pic and Pam found her attractive enough. The tits were overly huge and sagged but Pam always found beauty in all shapes and sizes. Pam swiped forward to read through the "into" part of the questionnaire.

Shelly was into cunnilingus, blow jobs, straight fucking, anal, tit fucking, being cum on, swallowing cum, analingus, and toys. Her comment on desires stated she just wanted a long fuck session with an experienced professional. "It'll be nice to finally feel cock" was also listed and was an obvious reference to her small dick ex husband.

Pam was interested so she then forwarded the link to set a face to face coffee meet. She heard the car door close just as her app buzzed which indicated her client had hit the "I'm here" button on her app. Pam set her phone down, stood and pulled the sundress off. She was pleased that her cock had obeyed and was soft but still hung low.

Pam heard her door close and then a knock on the wooden partition. She moved into place and let her cock slip into the hole. A low moan from the other side let Pam know her client was pleased. She felt his warm mouth gulp every inch of her soft girl cock into his mouth.

It was Pam's turn to moan as the client held it there and let it grow hard in his mouth. Once it was fully hard, he expertly began to give Pam what she always thought of as the perfect blow job. This guy was good. He sometimes bobbed up and down, sometimes licked the shaft and head. He never used his hands and only orally serviced her cock.

Each time her balls would cinch up tight, he sensed it and relaxed his grip to stop her from cumming. He almost always had Pam last the entire 30 minutes he paid for. With five minutes left his head bobs became faster. This triggered Pam to fuck the hole and essentially his mouth.

This time as Pam's balls tightened, he made no move to stop. Pam exploded a gush of cum inside her client's mouth. Her first cum of the day was always the heaviest and the man swallowed every bit. Eight or nine heavy ropes of cum were swallowed by the man. When Pam stopped cumming she pulled her cock from the hole and she heard the man simply walk out the door again and close it.

Pam flopped onto the couch and picked up her phone again. There was a first meet request from Shelly for 10:30. She checked the time and it was only 10:00 with her next appointment not until Noon. She sent the confirmation to accept the appointment.

Pam slipped into her sundress again, her girl cock, still half hard, tented her dress outward. First meetings of potential clients was always her favorite part of the job and excited her so she wasn't sure if she'd soften up before the meet. If not, she hoped she didn't scare Shelly off.

Pam got to the coffee shop on time and was happy to feel that her cock had softened enough that it didn't tent her dress and hung between her legs again. She spotted Shelly right away and noticed that she was way prettier in person.