He was up way too early for a Saturday, but he had a pick up to make. He stopped at Starbucks for a coffee before pointing his BMW south and commencing to drive. He glanced in the rearview mirror to check the traffic behind him and then caught sight of his own blue eyes.

"You're a weakling," he said to himself as he drove.

He cursed himself along with the firm he worked for.as they were partially to blame for this situation.

"If only they had kept to their regular routine I wouldn't be in this situation," he told himself.

Blake Renolyds was thirty and had just become a full partner at the investment firm. His money increased substantially as did his net worth  It was at this celebration for this achievement that all his troubles started.

"If only we had gone to our regular hangout at the club inside the Holiday Inn and not this little place that one of the associates had told the group about. If only I had not noticed the leggy brunette in the minidress seated at a booth by herself," Blake told himself.

Brunettes were a long time weakness for him. While most of his buddies went nuts over the blue-eyed blondes, it was the dark-eyes and dark-haired vixens that always got him going.

He had seen her as they entered and his eyes kept returning to her as the evening progressed. She was stunning beyond belief and had the greatest set of legs he had seen in quite a while. He watched her as she blew off guys that approached her and that told him that she wasn't easy.

His eyes were fixed on the movement of her firm ass moving under her tight dress as she headed out the door and he felt a little depressed that she was leaving, Blake's spirits perked up when she returned and took her seat. His eyes almost popped from his head as she down and crossed her legs and the hem of her skirt rose.

Blake got a glimpse of thigh high nylons before she gently tugged the hem of her skirt back down and slid into the centre of the booth. Blake cursed himself for this weakness too. Long-legged brunettes in short skirts were another weakness. The weakness was intensified of their legs were clad in dark pantyhose or nylons and their feet were encased in high heels.

An hour later he arrived at the lingerie shop. He had chosen this place as it was far from his firm and where he lived. So there was no chance of bumping into anyone he knew or being seen. After glancing around he went inside and stayed only long enough to pick up a medium size box. The sales lady totalled the bill and he paid in cash.

"That's one lucky lady," the sales lady said to him as he waited for his change

Blake did not comment and returned to his car and headed home. Once inside he called the number that he had memorized as he didn't want it in his directory. A soft sultry female voice answered the phone and he told it that the package had arrived. The voice asked him to be here at eight and he said he would. 

"It's not like they don't have skeletons in their closets," he said to himself.

He knew that Tom Falcone was doing his private secretary whenever he could. He discovered that Richard Banister had a mistress that was as old as his own teenage daughter.

"Yes, they all have secrets. So why am I so afraid of being caught? " he asked himself.

His mind drifted back to the small club where one by one his associates departed until he was the only one left. Fueled by liquid courage he decided to make his move. He slid off his bar stool and headed toward her booth. She smiled as he approached and asked if he could join her. She nodded and she slid to one side to allow him to take the space next to her. She introduced herself as Chasity.

The liquor had loosened his tongue and he confessed to watching her all night. She surprised him by saying she knew. She then asked what drew his eyes to her and he admitted it was her legs. Then to his surprise, she tugged the hem of her dress up to reveal more of her long nylon clad leg and the bare flesh above the lace top of her nylons.

"I can assume that you like?" she asked.

"More than you know," he responded.

The liquor still coursing through his brain had him confess his love for this type of lingerie and the fact that he usually had to purchase numerous sets for his former lovers as they wouldn't. He also confessed that most never wore these sexy items more than a few times.

"I always wear this kind of lingerie," she told him.

She then suggested he get a room if he wanted to see more of what she was wearing. Blake was hesitant until she convinced him that she was not a hooker. He then flew to the front desk and returned with a room card. They left together with him slightly listing to port as they walked.

Once inside the room, Chasity tossed her purse on the nightstand and then wrapped her arms around him. The kiss was long and deep and Blake held her tightly as they tongues danced in each other's mouths.  He then allowed his hands to caress her firm ass under her tight black dress. 

Blake could not recall when he had been this excited due to a kiss but excited he was. She then had him undress and slide naked under the sheet of the king size bed. Once there Chasity began to slowly shed her dress. 

A black silk shelf bra trimmed with delicate black lace covered her breasts. A matching garter belt held up her nylons that ended at top of her silky thighs and a tiny black silk panty was between her legs. Blake flipped the sheet back and Chasity took her place next to him.

Blake took her in his arms again and they kissed long and hard. His hand rubbed her breasts through the silken cups and she moaned.

"I can remove this," she said softly.

"No, please leave it on," he asked.

Chasity then grabbed his erect cock and began to stroke it, causing Blake to moan with pleasure. She then flipped back the sheets and exposed his cock to the air.  She then moved her head downwards and began to plant kisses on it. A second later she took it between her ruby red lips.

Blake had not had a blow job like this in his life and waves of euphoria washed over him. She stopped licking and sucking long enough to whisper in his ear that she loved anal sex. Blake could not believe that this was happening to him. Here was this sexy lady dressed in erotic black lingerie that wanted it in the butt.

Chasity reached for her purse and withdrew a bottle of lube and a condom. She opened the package with her teeth and placed the condom Blake's shaft. She then took a position on her elbows and knees and slid her panties down just enough to expose her firm tight ass and handed the bottle of lube to Blake.

"Lube me up good, baby," she whispered.

Blake squeezed a generous portion of lube in his hand and gently covered her little pucker with it. The feeling of his fingers on her sensitive back door caused Chasity to moan. Blake had only met one girl that liked anal, but that was a long time ago. His most recent lovers had rejected it. 

Blake then took his place behind Chasity where he lubed his latex covered cock before he aimed his rock hard shaft at the entrance to her back door. The sight of her butt peaking over the waistband of her silky panties was almost more than he could handle. And without hesitation, he slowly pushed himself past her tight anus and enjoyed her long sexy moan.

Soon his balls were banging off her butt cheeks. Blake kept one hand on her slender waist and gently rubbed her generous tits through the silky cups of her bra with his free hand. It was when he ran his hand down her hard flat stomach towards her pussy that everything changed. Instead of finding a hot and wet pussy he found a cock. It wasn't as big as his, but it was a cock just the same.

Blake immediately withdrew and got off the bed and took a seat at the desk. His cock began to wither as he stared and he cursed his own lust that was fueled by alcohol for this predicament. Chasity pulled up her panties and got off the bed and walked over to the desk. She then leaned her butt against it and then looked down at Blake.

"I take it I'm your first t-girl?" Chasity asked.

"Yes," he responded looking up at her. "I blame the alcohol and the way you look for this," Blake stated. 

"Was it all that bad? she asked.

"No, it was great. You look and dress the way I've wanted my past girls to be," he admitted.

"It doesn't have to end tonight. All my clothing and lingerie are like this and I'd be happy to wear them for you," she admitted.

Chasity then unfastened her bra and let it hit the floor. Blake looked up to see the most perfect pair of breasts he had ever seen.

"I'm not some whore that goes out every night looking to get laid. This was my first time allowing some man to pick me up, but you were different. You admitted to staring at me and why," she informed him.

"You seemed experienced in the anal department," Blake commented in a sarcastic tone.

"I have toys and have practised. I have the same problem as generic girls when it comes to meeting someone for sex. I have to be attracted to them because I can't just give it up to anyone," she said in a logical tone.

As she spoke Blake's confidence returned and he slowly rose from his seat and placed his hands on the firm globes now before him. Standing this close he saw no trace of a male in her. The exception was now hidden behind the silky cloth of her panties. Chasity moaned at his touch.

"Please, don't start the fire if you have no intention of putting it out," Chasity said.

"You really have more outfits and lingerie like this?" Blake asked.

"Yes. When I finish paying off my doctor bills I plan to buy more," he was informed.

"Doctors bill?" he asked.

"Yes, doctors bills. I wasn't born with these," she said as she ran her hands over her generous breasts.

Blake took her in his arms and kissed her and was surprised that he was not repulsed. The kissing grew more intense and soon they were back on the bed finishing what they had started. As they cuddled in each other's arms Blake realised he had found what he had been searching for.

"Do you like black leather and thigh high boots?" he asked.

"I love them. They are however a little out of my price range at this time," she replied.

"Not mine," he responded.

At eight Blake arrived at a well maintained two-story house in the oldest part of the city that he had visited before and knocked on the ground floor door. He had been there last Saturday and dropped off a dozen pieces of lingerie from Victoria Secrets. She spent the evening modelling them of him and giving him great oral and allowing him to fuck her in the ass while still clad in them.

Clad in a black lace robe Chasity admitted him. They kissed briefly as he handed her the box and she then disappeared into a back room as Blake took a seat on the couch.

"You're a weakling and should end this affair. If anyone discovered it, this could end your career. It's not like banging your secretary or some sixteen-year-old hottie, this is different," his inner voice argued.

And once again all the arguments with himself stopped when Chasity reappeared. She was clad in a French maids outfit complete with ruffled petticoat and panties along with seamed nylons. She gave a pirouette when she stopped moving and Blake grew hard just looking.

"Do you need something, Master?" Chasity said performing a slight curtesy.

"Yes," Blake responded as stood up and approached her. Once in front of her, he undid his trousers and let them slide to the floor along with his underwear and exposing his rock hard cock.

"No, not that," Chasity pretended to protest as Blake forced her to her knees.

Bake watched with wide eyes and his cock disappeared in between Chasity's soft full lips and her talented tongue took over. When he judged it was the right time he pulled her off her knees and directed her to the dining room table where he bent her over amid her initially pleading for him to stop.

He slid down her ruffled panties and flipped up her petticoat and short skirt. A second or two later after donning a condom and lubing her back door, he inserted himself into her tight tunnel. The weight of his body kept her pinned against the table and freeing hands to rub her firm breasts   Afterwards, as they cuddled on the floor for the longest time and she fell asleep in his arms.

"You're a weakling and should end this," the voice in his head said again.

Chasity woke up and told him it was time for bed. He slipped between the sheets of her bed and waited while she visited the bathroom. She soon appeared in a black satin and lace nightie and had kept thigh high nylons on. This time she mounted and pulled the back of her thong panty to one side to allow him unrestricted entrance.

Blake donned a fresh condom and lubed it well before lubing her back door again. He moaned as she lowered herself onto him and he felt his dick enter her tight butt again and she rode him for the longest time until her orgasm took her.

"Maybe I'll end it next week. I've already ordered her leather lingerie and boots and they are en route," he told himself.

Even as he said this he knew it was a lie. He was hopelessly addicted.