Self Esteem

Henry was on his way to the coffee shop his old friend Cynthia had asked to meet up he hadn't seen her in a few months and he was excited to catch up. He got to the café and ordered a plain coffee for himself and a frappe for Cynthia. She arrived a few minutes after him and took a seat at the table with him.

"How have you been?" he asked, "it's been a while since I've heard from you."

"I know I've just been going through some things," she said, "but I really wanted to talk to you again, how have you been, any new ladies."

"Nothing long term," said Henry, "a few flings here and there, how about you, any guys?"

"Not in a while," said Cynthia, "I've been trying to get right with myself."

"What's been bothering you?" asked Henry.

This was news to him, Cynthia had always been outwardly happy. She also always had at least one guy trying to get with her or actively dating her.

"Just feeling uncomfortable with my body," said Cynthia.

"Why?" asked Henry, "Cyn' you're beautiful."

He wasn't just saying it either, she had a tight body and a great ass. She had long flowing brunette hair and seductive smile with eyes to match.

"I know you think so," said Cynthia, "but I needed to feel it for myself, I invited you here because you always made an effort to make me feel beautiful."

"Always Cyn'," said Henry reaching across the table to take her hand, "you know I'm always here for you."

"Then can you come with me," said Cynthia.

"Of course," said Henry.

Cynthia took him back to her place. Once they were inside she turned on the thermostat, it was late autumn and there was a strong chill in the air. She wore a black sweater and kept a large scarf on as she took a seat by him on the couch.

"I know you have a type," said Cynthia, "you tend to go for busty girls and I'm not at all."

"But that's not everything," said Henry, "I've always been attracted to you."

"You have," said Cynthia, "that's why I want your help with this."

She pulled out her cellphone and opened a photo album before giving it to Henry. The picture was of Cynthia in a pink tube top and booty shorts.

"Keep scrolling," said Cynthia, "I did a photo shoot for myself, kind of erotic."

The pictures were of her in various revealing outfits, bikinis, lingerie, as well as tight shirts and pants. He was getting aroused but Cynthia was more focused on seeing him keep scrolling through.

Suddenly a picture came up of her naked curled up on a bed, her breasts and pussy blocked by a sheet. The next image had her laying on her stomach her perfect ass, the on he'd fantasized about was on display. The next image though was the winner, she was on her back laid out her small perky breasts and shaved pussy were in clear view.

She took her phone back and put it on the table.

"I showed you mine," said Cynthia, "show me how hard you are."

Henry didn't hesitate, he slid his jeans and underwear off. Cynthia reached out and grabbed his erection and stroked it a few times.

"Now close your eyes," said Cynthia.

Henry did as he was told. He heard clothes hitting the floor and her jeans being unzipped.

"Open," said Cynthia.

He opened his eyes and saw Cynthia standing naked before him, she was flawless, but her tits, they weren't the small perky A cups from her photos these were a large C cup maybe even a D.

"They're Cs," she said, "I had them done a little while ago. I wanted to, they were the only part of me I was unhappy with."

"Whatever makes you happy," said Henry.

"Do you want to touch them?" asked Cynthia.

"I don't just want to touch your breasts," said Henry.

"Let's start with that," said Cynthia, "I haven't been with anyone since I had them done and I don't know how they'll feel."

Henry got off the couch and cupped her breasts in his hands. He gave them a gentle squeeze and she gasped.

"Are they sensitive?" asked Henry.

"Yes," moaned Cynthia as he gave them another, firmer, squeeze, "no one used to pay attention to them before."

He cupped one of her breasts and sucked on her nipple. She grabbed the back of his head and held him to her before pulling him off of her.

"You like tits don't you," she said as she walked away from him and took a seat on the couch, "it feels so good to have them played with."

"They're amazing," said Henry.

"You probably want to go to town on them," said Cynthia.

"I would love that," said Henry.

"Ok," she said, "take a seat next to me."

Henry did and she climbed onto his lap and pressed her breasts into his face holding him between them. She finally let him free of her breasts.

"They're all yours," said Cynthia.

Henry grabbed her breasts squeezing them and licking one of her nipples. Cynthia reached down between her legs and slid two of her fingers into herself. He flicked his fingers slowly over her nipples and Cynthia bit her lip moaning as she fingered herself quickly.

Cynthia was on the verge of orgasm and Henry pinching the nipples on her new tits put her over the edge.

Cynthia collapsed onto Henry who was as turned on as he'd ever been.

"Do you want to fuck my tits?" asked Cynthia, "do you want to cum on them?"

Henry nodded and Cynthia laid back on the couch and Henry climbed on top of her putting his dick between her tits. She pressed her breasts together and he started to slide his dick between them. Watching her orgasm on top of him had him on the verge of busting after a few moments. He gave a few last thrusts and shot his cum onto her neck.

"That was so fucking hot," said Cynthia as cum ran down the side of her neck.

After they cleaned up she showed him out and said she'd be in touch.

About a week went by and he couldn't wait to see Cynthia again, as much as he liked her new boobs he wanted to actually be with her.

Finally she texted him and told him to meet her at a bar near her.

He got to the bar and had no trouble finding Cynthia, she was surrounded by guys checking her out. She wore a blue silk top with a plunging neckline, her nipples poking through the thin fabric. She motioned for him to take a seat with her and the guys dispersed.

"This is great," she said, "people can't take their eyes off me."

"I can see why," said Henry.

"You won't be able to take your hands off of me," she said grabbing his thigh.

She finished her drink and he drove her back to her place. They got inside and Cynthia immediately lost her top, skirt and panties. As Henry took his clothes off Cynthia procured a bottle of lube. She poured the lube onto her breasts and rubbed it onto them before getting to her knees in front of him.

"Fuck these titties," she demanded.

This was surreal, it felt like a porno but he did as he was told. The lube made tittyfucking Cynthia even better than the first time but he was determined to make it last.

"All those guys wanted to fuck my big breasts but you get to," said Cynthia.

"I'm a lucky guy," said Henry as he continued to slide his dick between her soft breasts.

"Before I had big tits I always got compliments on my blowjob skills," said Cynthia, "would you like that?"

"Yes," pleaded Henry.

He had heard from her exes that her blowjobs were the best. She took him in her mouth and immediately tried to get him all the way in succeeding after a few tries. After holding him in for a few seconds she released his lube and saliva soaked cock before licking at his nuts.

"You're going to squeeze my titties," said Cynthia, "and play with them while I blow you, if you can hold out until I finger myself to orgasm I will let you have me however you want."

She started to rub her already wet pussy while she licked up Henry's dick sucking the tip for a bit before taking him in her mouth. He grasped her breasts squeezing them hard as bobbed her head on his dick. He rubbed his fingers in circles around her nipples as she again took him all the way in her mouth. Her nipples were getting hard from the attention and he gave them a pinch as she took him out of her mouth before sucking on his balls.

He cupped her breasts squeezing them softly as he dragged his fingers towards her nipples.

Cynthia moaned leaning against him as she rubbed her clit. As her orgasm subsided she grabbed his dick with both hands and stroked him furiously before taking him into her mouth. She stroked and sucked him as he held the back of her head in his hands. He pushed himself further into her mouth and she let him guide her doing as he willed.

He finally let her go and she resumed stroking his dick.

"You're going to cum on my tits," she said cupping her breasts for him.

Henry stroked himself looking down at Cynthia before shooting strings of cum onto her boobs.

After they were dressed she showed him out, in one week he was to see her, she would be wearing an outfit of his choosing.

He got to her house and she let him in she was wearing the same outfit she had worn to the coffee shop that day.

"So how do you want me?" asked Cynthia as she pressed her body against his, "you want to dominate me, you want to deny me, you want my ass?"

He pulled her in and kissed her holding her waist. Once their kiss had ended he kissed her neck and grasped her ass with both hands.

"This is really what you want?" moaned Cynthia.

"Yes Cyn," said Henry.

He got to his knees and unzipped her jeans sliding them and her panties over her ass. He kissed her ass cheek as he got her out of her pants before licking her pussy softly. She was already soaked and he wanted to give her at least a little one with his mouth. He squeezed her ass as he licked her making small circles around her clit with his tongue. He felt her shiver as she orgasmed and clung to him for support.

"Take your scarf off," he said before sliding two of his fingers into Cynthia who replied with a moan before tossing it off.

He got to his feet and led her down the hall to her bedroom. He pushed her down on the bed, pulled his clothes off and climbed on top of her. He entered her slowly as she gasped, slowly he pushed himself all the way in.

He grasped her breasts which remained covered by the tight black sweater she was wearing and kissed her as he slowly pushed himself in and out of her. He quickened his pace a bit drawing a moan from Cynthia who grasped his back.

"Do you want to take your tits out?" asked Henry.

Cynthia nodded and she slowly slid her top off before burying his face between her breasts. She pushed them against his face, he flicked her nipples a few times before driving himself deep into her again. Henry alternated between going quickly and driving himself deep to slow his own orgasm.

"You like to be on top right?" he asked.

She shook her head yes and he laid on his back letting her climb on top of him. She slid slowly down his dick before leaning forward so her breasts were in his face. He grabbed her ass and held her as he started to thrust into her while licking at her nipples.

"This position is even better now," she moaned at him.

Cynthia sat up and started to grind her hip on him moving between going back and forth and making circles. She took his hands and put them on her breasts, he squeezed her breasts as she quickened her pace. He pressed her breasts together and rubbed her nipples with his forefingers and within a few moments Cynthia was cumming on top of him.

He grabbed her waist and started to thrust into her as hard as she moaned on top of him.

"I'm so close," groaned Henry.

"Cum however you want," moaned Cynthia.

Henry grabbed her ass and gave her a few last thrusts before busting deep inside her.

"Fuck," moaned Cynthia as she collapsed on top of him.

"Cyn," gasped Henry, "you're amazing."

He spent the night with Cynthia and she woke him in the morning by sucking his dick. Once she realized he was awake she stepped up her game taking him deep in her mouth. Every time he felt about to bust she would slow but as soon as he was settled she would take him deep again. On the eighth time when he couldn't stand it anymore she took him full in her mouth and let him bust.

About a week later he got the call to come over. He got to the house and found a camera set up and another woman with Cynthia. Cynthia was wearing a black tank top and no bra as well as tight jean shorts.

"What's going on?" asked Henry as he took a seat next to her on the couch.

"You know the photo shoot I did?" said Cynthia.

"How could I forget?" he said.

"Well Miss. Hart here took the pictures," said Cynthia, "but she also does videos."

"So you're making a video," said Henry.

"I was going to," said Cynthia, "but I wanted to know if you would be in it with me."

"Who would see this video?" asked Henry.

"It would just be for the two of you," said Miss Hart, "once I edit it I will give you all of the film, I pride myself for my discretion."

"I always wanted to do something like this," said Cynthia, "but I wasn't ready," she touched his thigh and looked into his eyes, "but now I have you."

"I'll do this with you," he said putting his hand on her cheek, "just tell me what to do."

"She has an idea of what she wants," said Miss Hart, "I'll ask a few questions and then we'll start with some touching, she wants oral, she wants sex and she wants anal, oh and of course, she wants you to titty fuck her beautiful breasts."

"Are you ok with all of that?" asked Cynthia.

"Yes Cyn," said Henry, "I've always told you I'd do anything for you."

Miss Hart got the camera set up and started filming.

"So Cynthia," said Miss Hart, "how are you feeling?"

"Nervous," said Cynthia, "I've been with Henry before but never on film."

"And how about you Henry?" asked Miss Hart, "Have you ever been filmed?"

"Twice," said Henry to Cynthia's surprise, "not with Cyn though."

"Care to elaborate?" asked Miss Hart.

"A girl I had been with for a while set up cameras in her house, I didn't know until after when she emailed me the video," said Henry.

"And what did the video consist of?" asked Miss Hart.

"Pretty normal stuff, oral and sex in some basic positions," said Henry.

"And what about the second video was it with the same sneaky lady," asked Miss Hart.

"No actually the second girl hated the first," said Henry, "I lent her my laptop one night and she found the video. After she watched it she told me she could do better so she set up the cam on my laptop and I took her from behind, switched between her ass and her vagina."

"So you've done anal before," said Miss Hart, "and tell me about their tits, were they as perfect as Cynthia's, were they fake."

Henry hesitated unsure of how to answer.

"The first girl had big breasts, they were D-Cups and they were natural," he said, "the second girl had A-Cups but her ass was much bigger then the first girl's."

"Cynthia," said Miss Hart, "may I call you Cyn, Henry did and it's positively sultry, sounds like he's saying sin."

"Sure," said Cynthia, "it's especially sexy when he says it while we're fucking."

"Now have you done anal?" asked Miss Hart.

"Yes," said Cynthia, "a few times with some different guys."

"What made you want to start Cyn," asked Miss Hart, "do you enjoy it?"

"I didn't the first time," said Cynthia, "so I didn't do it with that guy again but I guess I tried it because I was always happy with my ass and guys including Henry always complimented me on it."

"And did you ever let Henry try your ass Cyn?" asked Miss Hart.

"I was never with Henry until I got my breasts done," she said, "I wanted them to feel better about myself but once I had them I wasn't sure how guys would react but Henry always made me feel sexy so I called him."

"I think it's about time," said Miss Hart,

"let's see those new tits you're so proud of."

Cynthia slowly slid her tank top up revealing her perky tits.

"Wow Cyn," said Miss Hart, "I would like to motorboat those so I know Henry must want the same."

"Come here Henry," said Cynthia pulling his face into her breasts.

He licked her nipple drawing a moan from Cynthia who cupped her other breast with her hand.

"I think we need to see your ass too," said Miss Hart.

Cynthia stood up and Henry slid her shorts and panties off over her ass. He squeezed her ass with both hands and buried his face between her ass cheeks licking her anus.

"You picked one dirty boy," said Miss Hart, "why don't we see his cock."

Cynthia turned to Henry and helped him to his feet before undoing his belt. She undid his pants and got to her knees as his dick sprang free of his pants. She took him in her mouth stroking him with one hand as she bobbed her head back and forth.

"Take him all the way into your mouth," said Miss Hart.

Cynthia took him all the way in and held her mouth there for a while before pulling off and taking a deep breath while stroking his soaked cock.

She took him back in her mouth and he reach down giving her breasts a squeeze before massaging her nipples.

"My tits," moaned Cynthia as she stroked his dick, "too sensitive."

"They're very sensitive?" asked Miss Hart, "Henry maybe you should fuck her tits instead."

She handed him a bottle of lube which he poured onto Cynthia's breasts. Once they were covered she leaned up and Henry slid his dick between her mounds. She pushed them together holding his dick steady as he started to hump her breasts.

"It's so hot finally being able to give a tit job," said Cynthia, "I've made him cum like this a few times."

"Well Cyn," said Miss Hart, "let's let him cum somewhere new, not yet of course, I think we should see you orgasm."

Cynthia got onto the couch and laid back spreading her legs for Henry. Her pussy was already soaked and Henry's finger slid right in. He ran his tongue around her anus as he fingered her pussy.

"Henry seems to like your ass Cyn," said Miss Hart, "has anyone ever licked your ass before."

Cynthia shook her head no as he moved his tongue up to her clit and slowly pushed his finger into her ass. Henry sucked Cynthia's clit as he slid his finger further into her ass. He knew she was close and he reached up to her breasts with his free hand and gave one a squeeze drawing an immediate response from Cynthia who moaned and shivered as she came.

"That was a nice orgasm," said Miss Hart, "got me all worked up but it's time for some down and dirty fucking."

Henry pulled Cynthia to the edge of the couch and took the bottle of lube pouring some onto her anus as well as rubbing some on his dick.

"Looks like he isn't waiting," said Miss Hart, "I guess you shouldn't have kept your ass from him Cyn."

Henry pressed the tip of his dick against her anus. Henry pushed slowly until his whole tip was in. Cynthia moaned as she looked up at him. He slowly pushed himself further in.

"More?" asked Henry.

Cynthia bit her lip and shook her head yes as he pushed himself deeper. Her ass was tight around his cock he was afraid he'd cum before he was all the way in. He pushed himself on stopping to rub Cynthia's clit with his thumb.

"I'm gonna cum with that big cock in my ass," moaned Cynthia.

He got his dick all the way in before pulling out a little and driving back in. Henry pulled back almost all the way out before slowly pushing himself back in. He started to hump her a little more quickly Cynthia knocked his hand away from her pussy and started to rub it quickly as Henry continued to enjoy her ass.

Cynthia cried out as she came, her whole body shivered and her ass tightened around Henry. He slowly pulled out of her ass and leaned over to kiss Cynthia.

"I think it's time for you to fuck her pussy," said Miss Hart.

"I just need a minute," said Henry, "her ass was so tight."

"Well when you're ready," said Cynthia, "my pussy is all yours."

Henry helped Cynthia up off the couch. He grasped her breasts from behind giving them a soft squeeze.