Twisted Massage

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A massage that turns into something different.
2.5k words
4.51
92.6k
79

Part 1 of the 2 part series

Updated 06/07/2023
Created 10/10/2015
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Robert was at a crossroad in his life. He had just turned forty. Sold the business that he had inherited from his father. The business was a small investment company that he was very good at, but it was also the ultimate boring job that he laughed about while in college. Then he got sucked into it, and before he knew it he was forty years old, and divorced. He was good at his job, actually, he was very good at it. The problem was Robert wanted excitement. He had spent most of his free time dreaming about adventures to go on, but never leaving the safety of his little world. That was why he was sitting in Vegas right now. His friends and family whispered that he was going through a mid-life crisis, and knew that he would be back in their world within a couple months. Robert was determined to keep that from happening. For him, the first step was this trip to Vegas.

Robert's nights in Vegas had so far been filled with one party after another, and hours of table time. Now today was going to be another first for him. He got a name and address for what was termed the "ultimate massage." Robert wasn't sure about a massage parlor, but he was assured that this wasn't like that. That was how he ended up in this limo on his way to a strange house. He wasn't sure about paying for sex, but he had already decided that he would at least get a massage if nothing else. The car pulled up in front of a nice house in a gated community that looked like all the other houses around it. When he rang the doorbell the door was opened by a stunning blond woman, and any reservations he might have had went out the window.

Standing in front of him was a woman who he wouldn't describe as beautiful, but instead as sexy. Everything about her screamed sex. Her blonde hair was just above her shoulders. She had these deep blue eyes that mesmerized Robert. Looking down he couldn't deny that she also had a smoking body. The this top she wore showed off her ample cleavage, and the short skirt brought his eyes down a long pair of athletic legs, that ended in a pair of brown boots. Without the first touch from this goddess Robert could already feel his body responding. Once she invited him in he found himself in a decidedly masculine room. The furniture was dark woods, and leather. A large bar was the center piece in the room, along with two large TVs that had some sports show playing, but was muted.

"Hi, my name is Brittney" she said as she gave Robert a hug.

Robert found his arms wrapping around Brittney and pulling her close. Her body pressing against his. "Hi, my name is Robert" he whispered in her ear as he hugged her.

She proceeded to show him to a large leather chair where he sat before she brought him back a tumbler full of an expensive scotch. When he took it from her their fingers brushed and he felt an excited jolt run down his body that only intensified when she perched herself on his lap. They exchanged a couple minutes of seemingly random small talk. All the time she kept touching him. Running her fingers through his hair. Brushing her fingers over his chest. Leaning in and brushing her breast against him. It was like she knew that this was his first time, and she wanted to tease him. At first he was nervous, but soon he found himself enjoying it, and even touching her back. His fingers brushing her bare leg. Caressing her arm. Then her cheek, before pulling her to him for several soft kisses.

"MMMMM, this is fun." Brittney whispered as she broke one of the kisses. "I think that we are going to have some real fun."

"I was just thinking the same thing." Robert said before pulling her back in for another deeper kiss. This time their tongues began to explore, and both of them moaned at the same time.

Pulling back she looked down at Robert and bit her lip. "I'm not sure f you would be interested in this, but I have an idea. How do you feel about bondage?"

Looking into those blue eyes Robert wasn't sure that he had heard her correctly. "Excuse me?" He asked.

"Bondage." Brittney whispered. "I have this massage table set up where I can restrain you, and I promise that you will love it. This is just so I can tease you. Then we really can have some fun."

At first Robert was reluctant, but then he decided that he was here to take chances, so what the hell. "Sure, that sounds like fun." Robert whispered before diving in for another deep kiss.

They then proceeded to a back room where there was a large massage table set up with restraints already there. Seeing Robert's look Brittney tried to make him feel at ease. "This is my special massage room. The other room has the regular table."

Brittney then had Robert strip and lay on his stomach. For this part she didn't use the restraints. She had explained that she would use them when he rolled over. With the lights dimmed, and the soft music Robert felt any nervousness slip from his body. Soon Brittney was helping push those nerves even further away with her firm touch. The combination of her strong fingers, and the massage oil soon had Robert in an erotic fog. So far the massage had almost been like any massage with the exception of the times Brittney would brush against him with her body. A couple times Robert felt something strange when his fingers slipped under her skirt before she pushed his hands away with a giggle. Each time she would whisper that was for later. Then she would resume her massage.

Finally it was time for him to flip over and Robert was stunned to see that Brittney had already removed her top and bra. Now he had a clear view of her tits, and he was impressed. They were obviously enhanced, but he didn't care. Robert reached up and cupped one in his hand and massaged it before moving to the other. Brittney didn't try to stop him this time. She just moaned and leaned a little closer so he could have better access. While doing so she had attached the restraints to his feet and then she leaned into him for another kiss.

"You ready for this, baby?" She whispered.

"Oh fuck yes." Robert moaned as she cuffed his right hand, before doing the same to his left.

Once he was restrained Brittney stepped back and admired him. Robert was a little over 6'0" tall, with a muscular body. Standing up in the middle was what Brittney was most impressed with. He had a solid 7-8" cock that was standing tall, and was rock hard. She then proceeded to tease him in every way she knew how. Running her fingertips down his body. Along the inside of his thighs, up over his broad chest. She also teased him by barely touching his engorged cock. It would stand there looking at her. When she got close enough to it she couldn't help but notice it start to bob around. It was like it had its own heartbeat. Throbbing with her touch. During this whole time Brittney kept her skirt on, but she still would brush against Robert every so often. Robert still had that nagging feeling that there was something different, but in his excited state he couldn't place his finger on it.

After some very extensive teasing Brittney finally stepped back from the table and looked at Robert. "Look here baby. Look at what is going to be all yours." She whispered. When Robert looked at her she eased her skirt down and turned her back to him. That left him with a view of her perfect backside. Then she bent over and pushed her panty's down. The entire time Robert was licking his lips as he admired her body. Brittney looked over her shoulder as she slowly turned around, and as she did Robert suddenly knew what he was feeling earlier. Between her legs, there was a solid 6 or 7" cock.

"What the?" Robert muttered as Brittney moved closer.

"Oh come on Robert. As many times that I brushed against you, and bumped into you? You didn't know?" Brittney said as she stood before him stroking her cock.

Robert was stunned as he stared at the bobbing cock just a couple feet from him. He had to admit that while she had a cock, it almost looked feminine. Maybe it was her body that caused him to view it as a female cock. He didn't know. He was too stunned. Brittney eased herself closer to him and looked at him as she brushed against him with her cock. Grazing his arm. She moved closer to his head. His eyes fixated on her bobbing cock. His trance was broken when she brushed the spongy head against his face before slipping over his lips. Her first hint that he wouldn't be a problem was his tongue darting out and licking the head as she did so.

"I don't know about this." Robert muttered.

"I'll make a deal with you Robert. Make me cum in the next five minutes and I untie you."

"What if I don't" Robert asked.

"Well, then we are going to have all that fun I was telling you about." Brittney whispered.

Before Robert could answer Brittney placed her cock in Robert's hand, and without even thinking his fingers wrapped around her. A slight moan escaped her lips as Robert started stroking her with his fingers. It felt so strange to be holding someone else's cock on his hand, but it also excited him. He compared the feel of his and the way she felt. In a short amount of time Robert had forgotten about trying to make her cum, and he was just concentrating on giving her pleasure. His fingers slipping over the spongy head. Down her shaft. All the way to her balls where he fondled them as best as he could in his position. He wished that she would release him, at least this hand, just so he could please her. He also knew that was part of the game.

"MMMMM, I must say, you are very good at this." Brittney moaned as she watched Robert's fingers work her shaft. "But I must tell you there are two reasons why I'm going to get to fuck you."

"Why is that?" Robert said in a husky voice as he watched his fingers working her cock.

"Well first, nobody has ever made me cum when I have offered them the chance, and second, you are still hard as a rock. Hell, I think that you might actually be harder." Brittney said with a grin.

"Fuck." Was all that Robert could moan as he couldn't argue with her.

"Don't worry baby, I'll be gentle. I love first timers." Brittney said as she pulled away from Robert's grip. "Would you like a taste before I slip it inside you? I don't normally do this, but damn, I like you."

With that Brittney eased to the edge of the table. Her hard cock dancing inches from his mouth. "Open up baby." Brittney whispered as she edged closer. Robert slowly opened his lips and for the second time her cock brushed his lips. Ths time though, it wasn't just a brush. No, instead she paused it there and Robert opened his mouth wider and she slipped it in. A soft moan escaped her lips as she felt him close his lips around her and begin sucking. Her fingers went to his short hair and held him there as she slowly fucked his mouth. Sliding in and out of his lips Brittney was shocked herself about how turned on she was. She knew that she had to stop this, or else she was going to blow in his mouth. That was for later, but right now she wanted to fuck him.

She pulled from his lips and before she could go to the other end of the table she had to give him another kiss. With a second soft kiss she moved to the other end and stood between his legs. At first Robert had no idea how she was going to lift him up to get access, but then he saw the chain that she connected to each restraint on his ankle. Then with a push of a button a cable lowered and she connected this chain to the cable. With another push of a button Robert felt his legs being raised. Soon she had him at the perfect height and she eased up on the table. She squirted a couple squirts of massage oil into her hand and she slowly began massaging Robert's backside. He had to admit that even this was relaxing. Even when she pressed her finger into his tight hole it was more pleasure than pain.

Brittney smiled at Robert's reaction. She could tell that she didn't need the restraints anymore, but that was all part of the game, and she knew that there would definitely be another time with Robert. He was hooked, and he wasn't even complaining with three of her fingers buried inside his ass. Finally she eased her fingers out and scooted up the table so that her cock was lined up with his opening. With a slight push she felt the head of her cock slip inside him and one look at his face told her that he was in heaven. A deep moan escaped his lips as Brittney pushed deeper. As she pushed in Brittney reached around and took Robert's still hard cock in her hand and started stroking.

Soon Brittney was stroking Robert in time with her thrusts. His pre-cum was oozing out and she was using that as additional lubricant. She couldn't help but smile each time that she bottomed out and watching Robert's expression. She could feel his ring tightening around her. Trying to hold her deep inside him. They stared into each others eyes as she fucked him. His breathing almost matching hers breath for breath.

"I'm getting close Brittney." He moaned as she stroked him.

"Hold on baby. I'm almost there. I want you to cum with me." Brittney moaned.

A couple more thrusts later Robert let out a groan and rope after rope of cum shot from his cock. The first couple coated Brittney's face before she aimed it back so that the remaining coated his chest. That was soon followed by Brittney pulling out of Robert's ass and shooting her cum all over his chest. Each rope of her cum mixing with what Robert had already shot. As they both calmed down and their cum turned into trickles Brittney leaned over and ran her fingers through the cum pooled on Robert's chest and brought a finger to her lips which she slowly sucked clean. This was followed by her doing the same and bringing her finger to Robert's lips which he sucked clean.

Brittney had to smile as she thought to herself, that yes indeed, they would be having some more fun.

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6 Comments
Dark_StormDark_Stormover 8 years ago
Great start

Looking forward to much more.

AnonymousAnonymousover 8 years ago

Story sure was a pleasing read. Nicely imaginative theme. I'm sure that Britney would have many return clients had this not been a fictional story. None the less I am looking forward to a 2nd. Chapter to the story.

domehard19domehard19over 8 years ago
Made me hard.

I have dreamt about something like this happening to me for a while now. How I wish I had a good looking shemale around here to act this out.

wolf9696wolf9696over 8 years ago
5/5

Excellent intro of newbie into the shemale world

AnonymousAnonymousover 8 years ago
Female Reader

Great start I really enjoyed it, I'm soaked in my panties having read it.

I'm guessing it's a fantasy of yours?

Please write another chapter

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