Bucket List

Roger sat in front of the computer in his attic office. The room was dark with only the light from the big monitor illuminating the room. It was still early, only 8:30, but his wife had already gone to bed. The past few years her health had gone downhill and they hadn't had sex in a very long time. At 64 he still had a need for sex and lately it had been by himself, masturbating as he watched some porn on the computer. His wife knew he did it and was OK with him getting the pleasure she could no longer give him. She had even told him he could be with someone else, if he felt the need because she knew he still loved her and they were still best friends.

Once, a couple months back he had gone and got a massage with a happy ending from a pretty oriental lady and that had been nice. Having a woman's hand on his cock had been good. He thought perhaps he should go back and see her again, but other cravings had taken over his thoughts in recent weeks.

Roger had found shemale porn and he had become obsessed with watching these beautiful women with cocks. It had started one night when he had been looking for a good blow job video and one that popped up was a mature man giving a gorgeous shemale head. Something about watching it stirred cravings that he had thought were long gone from his memory.

He thought back to that one time, when he was in his 40's and travelling for business that he had ended up in a 20 something guys hotel room and things got quite hot. At the time he had a great sex life at home and certainly wasn't looking for anything, especially with another man. But then he had met Rick in the bar and they hit it off talking about sports, politics and life in general. Rick had suggested that the price of single malt was a bit much in the hotel bar and offered to share some from a bottle of Glenmorangie that he had up in his room. One thing led to another and both of them were a bit tipsy when Rich leaned in and kissed him. Although shocked, he didn't pull back and soon they were kissing and his hand was rubbing Rick's cock through his trousers. Clothes came off and soon he and Rick were naked on the bed and Rick was sucking his cock. His own hand was stroking Rick's cock and the excitement of the new experience took over and it didn't take long until he was blowing his load down Rich's throat. He had moved and leaned down and had kissed Rick's cock and even had run his lips along the underside, but for some reason he held back and didn't suck him off. He did get Rick off with his hand and got a nice load of cum on his belly as a reward. There had only been that one experience but for years he had regretted not sucking that cock.

And now twenty some years later, here he was fantasizing about making up for what he had not done those many years ago. And he had decided that it was going to be with a shemale. Tonight he was searching the ads for shemale escorts and came upon a photo that he couldn't take his eyes away from. She was a cute brunette with glasses and a beautiful smile. The ad said she was 32 but she looked younger. He read the writeup in her ad: 32, 5'7", 145, curvy, 6.5 cut, fully functional. If you want a GFE I'm your girl. First timers a speciality. I'll make it a time to remember.

He scrolled down and looked at the several photos she had posted. He was smitten and knew she was the one. He had looked at lots of ads and this was the first one that made him feel like he did. He knew he wanted to be with her.

Typing her number into his iPhone, he sent her a text. He asked her if she was available tomorrow evening and what her rates were. He pushed send and waited. He didn't have to wait long as his phone dinged and he saw she had replied.

"Hi hon, yes available tomorrow evening. I ask a $350 donation for an hour and a half of my time. But I am not a clock watcher and I like to make my dates feel relaxed. Tell me about yourself."

Roger's hands trembled a bit as he typed. "I am in my 60's and in good shape. It would be my first time and I am a bit nervous. - Roger"

Her next message made him smile. "Don't worry darlin' I will be gentle with you! I can both top or bottom but we can discuss when you cum by. BTW I do BBBJ, CIM, and give a great massage if you need it. How about 7 tomorrow?"

I quickly replied. "Yes! I will be there." and got a reply with her address and "see you tomorrow hon! - Alexis"

Roger went back to her ad and the more he looked at her photos the more aroused he became. He couldn't help himself and took out his cock and stroked himself to a nice cum. He closed his eyes and thought, less than 24 hours to fantasy time.

The next evening he told his wife he was going to a friends place. He knew she would be ok if he told her he had a date, but didn't want to get into the details of who the date was. He drove to Alexis' neighbourhood and parked his car down the street from the apartment block and pulled out his iPhone and texted her." I'm just down the street, a little early".

She replied quickly, "No problem, buzz 2841 I'm in 841"

Roger hesitated for a moment. Did he really want this? He nervous as hell and almost started the car to drive away, but something made him stay and he got out of the car and walked to the apartment complex. He punched in the code and was quickly buzzed in. It was a nice clean complex and as he stepped into the elevator and pushed 8 he thought to himself, 'now or never'.

When he got to Alexis' door she was waiting because it opened before he knocked. He stepped in and saw it was a tastefully furnished apartment with a nice view of the city. Then he saw Alexis and his breath caught. She looked stunning in a tight black dress that clung to her curves. She was wearing a pearl necklace and had on stockings and heels.

She could obviously sense his nervousness and she quickly put him at ease by giving him a hug and a soft kiss on the cheek and led him into the living room. "Lets sit for a minute and get acquainted." she said, "You're my only date tonight so I won't rush you."

They sat and chatted and he told her about himself, and about his experience with Rick those many years ago and his regrets. She smiled at him and said, "Well hon, I'm here to fulfill your fantasy, so just relax and go with the flow." With that she leaned close and her lips met his.

Her lips were so soft and Roger returned the kiss. His arms went around her and he pulled her close. He could feel her curvy body against his and if felt wonderful. They just sat on the sofa and kissed for a bit, He slipped one hand to her breast and she did not pull away. He felt Alexis' hand rub the front of his trousers and her touch felt so very good.

They broke the kiss and she took his hand and led him into the bedroom. Alexis gave him another kiss and then turned and said. "Unzip me darlin' lets get comfortable."

He slid down the zipper of her dress and stepped back as she slid it off her body. Still facing away from him she looked so hot with black bra and matching panties and a garter belt holding up the dark stockings. She walked to the closet and hung up the dress before turning and asking, "Well, will I do?"

He had just stood there, unsure of what to do, his eyes roaming over her, the full breasts that spilled from the top of the bra, the black panties with a nice bulge in the front and those gorgeous legs. She moved to him, giving him another long kiss and saying, "Don't be nervous, just enjoy our time together."

Alexis' lips were soft and sweet and her body pressing against him got him totally aroused. His hands roamed her body and when he caressed the front of her panties with his hand and felt her cock through the silky material, he was so glad he had not chickened out when he was having second thoughts.

"You like?" Alexis asked as his fingers traced the outline of her cock.

"Oh, yes," he responded, "You are perfect!"

"Then let's get you out of these clothes, sweetie, you are far too overdressed."

She took the initiative and unbuttoned his shirt, pulling it open and leaning in to kiss his chest, her lips finding a nipple and sucking it, something he had not experienced in many years. Her hands found his belt and unbuckled it as he took his shirt off and tossed it aside. Deftly she opened his pants and ran her hand over the bulge in his briefs.

"Mmmm, you have a nice package yourself, already nice and hard for me!"

She quickly divested him of his pants, briefs and socks and he stood there naked before her, his erection bobbing free in front of her face. She smiled up at him and gave the fat head a kiss, her tongue darting out to push lightly into the little hole. His hands instinctively went to her hair, caressing it as her mouth opened and she slid her lips slowly down his shaft. Then she pulled them up and let his cock pop free. Standing up took his hand and led him to the bed, saying, "I think we are going to have a good time Roger."

On the bed they kissed and caressed one another with their hands. Alexis' bra came off and she pressed her enhanced breasts into his face. They felt a bit different than the natural ones he was used to, but he did not care, he was just enjoying the experience.

His hand found her cock and he squeezed it through her silky undies. "Alexis, I really want to suck your cock!"

He saw her smile, and then she slipped off the panties, freeing it and then rolling on her back beside him, "Enjoy, it is what you wanted. Take your time and just enjoy!"

He took her shaft in his hand, slowly moving his fingertips up and down. Leaning in he kissed the tip, as a wee bit of apprehension took over, but soon dissipated. Holding the shaft, he began running his tongue around the head, around the well defined ledge.

"Mmmmmm, you're doing great baby, explore, enjoy, just do what you are comfortable doing."

Her reassurance made him think that he had made the right choice by picking her, he felt totally relaxed and wanted to enjoy this new experience. He took her into his mouth, his lips tightening around the shaft as they slid down her hard shaft. He was only able to take about half in his mouth, but it felt wonderful. His head bobbed as he licked and sucked, lost in the moment.

"Do you like it baby," he heard her ask, and his moan around her flesh gave her the answer.

He was really into it now, sucking this beautiful cock, then letting it slip from his lips as he licked up and down the shaft. The first tastes of precum tantalizing his tongue. He knew what he liked when a woman gave him a blowjob, so he mimicked it with Alexis and it seemed to have the desired effect.

"Are you sure you haven't done this before Roger, you are a natural cock sucker!"

Being called that, spurred him on, his mouth engulfed the head again and he began jacking the shaft with his hand. He wanted her to cum, he wanted to taste it, savour it, enjoy the feel of a cock spurting into his mouth. He could hear Alexis making soft little whimpers of pleasure and could sense she was close. He had a quick thought of pulling off and not letting her cum in his mouth, but that was quickly overridden by his desire to experience everything.

Then he felt her hands grip his hair, her noises get louder and then felt the pulse of her cock as it began spurting into his mouth. It was thick and creamy with a bitter sweet taste and the feel of it on his tongue was exhilarating. He sucked and swallowed, amazed at the amount of cum. His own cock was rock hard and leaking onto the silky bed sheets. His mind was racing, processing what had happened, realizing he had just sucked a cock. He kept sucking a bit until he felt Alexis gently guide his lips away.

"I get sensitive after I cum, I hope you don't mind, but you were amazing Roger, like I said, a natural. Do you want me to take care of you?"

"Yes, please, I am already throbbing!"

With that Alexis moved around and found his cock with her lips. She was not tentative and swallowed his shaft, deep throating him like he had never experienced before. It did not take long, and he was spurting his own load down her throat. She took every drop, and kept sucking after until he began to soften. Then she showered his cock and balls with kisses before moving up and finding his lips with hers.

"Did I fulfill your fantasy Roger?"

"Oh yes, it was just what I was craving, you were wonderful."

"Well, we still have almost forty minutes left, would you like a nice massage?"

"That would be so nice."

She took him by the hand and led him to a massage table in an adjacent bedroom. He lay on his stomach on the table, she oiled her hands and they began gliding over his body,. She had a beautiful touch and by the time she told him to flip over, he was already hard again.

"Oh my, look at you, do you want me to get you off a second time?"

He nodded the affirmative and she put more oil on her hands and then began massaging his balls and shaft. Her hand glided up and down his cock and he felt the sweet sensations build again.

"Suck me again, I need your mouth!"

She was happy to oblige and sucked him until he blew his load a second time in her mouth. Again she swallowed every drop and kept sucking until he softened. Then she took him by the hand and led him to the shower where she cleaned him up completely and then left him to dry off telling him she would be in the living room.

He dried off and found his clothes and dressed. He took the envelope from his pants pocket and added an tip of fifty dollars. She had definitely earned every penny.

When he got to the living room, Alexis was in a full length robe. He handed her the envelope, which she just put on a side table, not bothering to count it.

"I hope your dream was fulfilled Roger, you are a nice man and I enjoyed our time together."

"You were perfect Alexis, just perfect, I know I will see you again."

"Good, and who knows maybe we can get beyond oral, I am told I have a nice tight ass!"

With that they kissed and he headed out the door, He was elated to have finally ticked off this box off his bucket list. And he knew he would return for more.