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Drake’s Story

Category: Anal Sex
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Drake signaled to change lanes, listening to Frank’s voice on the phone. It had been a good internship, and he had learned a lot from Frank. Truth be told, Drake had a bit of a man crush on Frank. From his stories of adventure in the military and as a contractor to his smoking hot girlfriend, he was almost like an action movie hero. More Clark Kent than Bruce Wayne or John McClain, Frank had become a good friend and trusted advisor.

Drake struggled everyday with his shyness, and appreciated Frank’s efforts to make him part of the team at work. Stopping by his house would be an opportunity to express his gratitude. It might also be an opportunity to see his girlfriend Fiona, although Frank usually referred to her simply as “The Roommate”. She was without a doubt the sexist woman he had ever met. For Halloween she had dressed as Cat woman in a leather outfit that looked like it was painted on. Drake had been dressed as Hulk, mostly because he closely resembled the characters broad, muscular build.

The phone rang, it was Frank confirming his arrival time. About halfway through the conversation Frank seemed to lose focus, uncharacteristically stuttering and dropping words. He abruptly ended the conversion when Drake was only a few minutes from his house.

A few minutes later Drake was knocking on the door. Somewhat to his surprise, Fiona answered the door. She was wearing daisy dukes and a tight white T shirt with a plunging neckline. The shirt did not leave much to the imagination.

“Hi Drake, it’s good to see you. I even like you when you are green and angry, “she said with a smile.

“Hulk smash,” Drake replied, feeling like a dork almost immediately. He noticed Frank sitting on the couch, looking a bit drained. Drake also saw some luggage, and recalled that Frank had just returned for a few days out of town on business…

Fiona continued with small talk, asking him for some assistance with a task. She took him by the wrist and practically dragged him down the hall. Drake glanced at Frank, who just smiled and waved.

As soon as they were in the bedroom Fiona kicked the door shut and walked up to him, stopping about an inch in front of him. He could feel the heat of her body. Drake could feel his penis start to get hard.

Her hand brushed against his face, and his heart jumped into his throat. He could not believe what was happening. It just wasn’t possible that Fiona, who he had lusted after since the day he saw her, was coming on to him. It had to be some kind of cruel prank that everyone from the office was in on. Drake looked around the room. He noticed that Fiona had not only kicked the door shut, she had locked it as well. The windows in the room were high, and blocked by landscaping. He knew Frank was pretty serious about security, so the bedroom seemed an unlikely place for a bunch of people to burst in. Fiona’s voice interrupted Drake assessment of the room’s security.

“Do you want to kiss me?” she asked.

“Yes, of course.”

“You should know that five minutes before you walked in the door I was sucking Frank’s cock, and he came in my mouth. Still want to kiss me?”

“Yes,” Drake replied. He realized his infatuation with Fiona was more than he originally thought.

Drake felt her arms around her neck, she pulled him down and pressed her mouth to his. Her tongue penetrated his lips. He wasn’t sure if he tasted any of Frank, or if it was just Fiona. It did not matter, it was ecstasy. Fiona broke the kiss and looked at him.

“No need to turn red, do you want me to stop?”

“Well, uh, I don’t know. I thought you and Frank were…” Drake stammered.

“Frank and I are fine. He accepts that I will do what I like. And right now I like touching you. Do you like it when I touch you?”

“Of course, it just kind of surprised me. I mean, Frank’s just down the hall.”

“There are going to be a lot of surprises, and Frank is going to stay put, trust me.”

“Uh, okay.”

“Frank said you listened well. Do you think you can listen to me? Can you do what I ask you to do?

“I imagine so.”

“Good. Then take off your clothes.”

Drake hesitated. Fiona stared at him, tapping her foot. He repeated her words in his head. He looked at Fiona, standing in front of him. She had her hands on her hips, and continued to tap her foot impatiently. She had a wicked smile on her face, hinting at where this was going. Drake let his eyes drop to her chest. Her nipples were protruding noticeably though her skin tight T Shirt. Slowly he began to unbutton his shirt. He knew this was a chance he had to take.

He unbuttoned his shirt, then pulled it out of his pants and dropped it to the floor. Clumsy, he struggled with the buttons on the fly of his jeans, then pulled them and his underwear off. They landed in a pile on top of his shirt.

“The socks too,” Fiona said.

Drake balanced precariously on one foot, then the other, pulling is socks off. Finally naked, he stood motionless in front of Fiona, unsure of what to do next. Her T shirt hugged the curves of her breasts, and her nipples stood out distinctly. If he could just touch them, well, it would probably be the best day ever.

“I have a few rules, “Fiona said as he looked Drake up and down. She walked around him.

“That, “she pointed to his throbbing erection, “will not be inside me. Not in my mouth, not in my pussy and certainly not in my ass. At least not today. Do you still want to be here?”

Drake nodded.

“And I am going to do things to you that might make you uncomfortable. Someday you might get to do the same things to me, it all depends on you.”

She continued to walk around him.

“Just to make things a little bit fair, I will take off my top or my bottoms, your choice.” Fiona said to him.

Almost without thinking he replied “Bottoms.” He already had a very good idea what her tits looked like. If she took her shorts off, he would be able to imagine her naked quite vividly. He watched intently as she unbuckled her belt and unbuttoned her shorts. As she slid her zipper down and pair of lacy black panties revealed themselves. Drake began planning on a way to take the panties with him when he left Fiona slipped her thumbs against her thighs and pulled her shorts and panties down together. As she did Drake looked down her shirt, admiring her full, round breasts. All he could think about was pressing his cock between her tits.

“Like I said, I think hard work should be rewarded.” Fiona cooed, walking closer to Drake.

Drake froze. His brain was trying to put every second of this experience into the longest term memory possible. He never wanted to forget this day. He looked at taut skin of her belly, with a neatly trimmed patch of hair. The lips of her pussy were just barely visible, and glistened with moisture.

“Am I doing something wrong?” she asked, “Should I stop?”

“No, no, please don’t. I… I’m not sure what I should be doing,” Drake stammered, feeling a bit out of control.

Fiona wrapped one hand around his throbbing cock. “If I want you to do something, I will tell you. For now, just stand still.”

She circled his cock with her thumb and forefinger, then slide her hand off the end of his penis. Drake watched her hold her hand up to her pouty lips, comparing the girth of his cock to the width of her mouth.

“It looks like a perfect fit, “she said. Then she slid her entire hand into her mouth. Drake could only stand and stare, his eyes fixed on her lips and they stretched around her dainty wrist. He quickly imagined her soft pink lips wrapped around his throbbing erection. Just watching her was a bigger turn on than any blowjob he had experienced. Just when Drake thought he could not take any more, she pulled her hand out of her mouth and walked over to her nightstand. She bent at the waist and began sorting through one of the drawers. His eyes were drawn to her tight round ass, and her pussy splayed out below it.

Five steps. He was five steps away from grabbing her ass and fucking her. But that wasn’t going to happen today. He wondered what she had planned for him. Fiona pulled something out of the drawer. She stood up and turned around. In her hand was a riding crop. Drake felt a cold sweat all over his body. He tried to think what he had done that would warrant the need for the short wand with the leather tip. Fiona sat on the bed, and placed the riding crop across her lap. Her legs were just far enough apart to show off her wet slit.

“Kneel in front of me,” Fiona instructed. Drake did as she requested, settling about a foot in front of her. His cock felt like it was pulling him towards her. Any forward momentum he had was stopped when she put her foot on his chest.

“Take my foot,” she whispered to him. Drake took her foot in his hands. It was smooth and soft. He caressed it softly. His eyes crept up her leg, stopping at her vagina. He could just barely make out her clitoris.

“Suck my toes.”

Drake raised her left foot to his mouth. Carefully he pressed down on her toes with his fingers. When only one remained he put it in his mouth… As he wrapped his lips around it, he focused on her clit, imagining he was taking that little pink bud into his mouth. When he heard Fiona sigh Drake felt a bit of a thrill. He gently sucked on each of her toes. As he put her left foot down and reached for her right, Fiona stripped off her shirt. Her breasts were even more spectacular than he imagined. As he slowly swirled his tongue around her toes Drake stole quick glances at Fiona’s tits. She had dark pink areola slightly bigger than quarters. Her nipples were swollen and erect, protruding at least a half inch above the smooth round curve of her breast. Drake avoided eye contact. He was not certain he should even be looking at her. When he finished with the last one he set her foot back on the floor. He wanted to slide his hands up her legs until his fingers pressed into the wet pink flesh of her sex.

“Stand up,” she said. Drake stood. Fiona spread her legs apart, placing her hands on her thighs.

“Now watch me.”

She move her left hand on to the handle of the riding crop, so it rested on her pubic hair. Her middle finger hovered right over her clit. Fiona’s other hand moved slightly to the center, pressing into the wet folds of skin between her legs. Drake moved his hands slightly towards his aching cock. He wasn’t sure if he was supposed to, but the temptation was unbearable.

Fiona grabbed the riding crop with blinding speed. Before he even realized what she was doing Drake felt the stinging bite of the leather on his thigh.

“No!” she barked at him. “Keep your hands at your sides. I want you to watch me play with my pussy.”

Drake dropped his hands to his side, rubbing the red welt that was beginning to form on his leg. The pain rapidly faded as he watched Fiona hands. It was her right hand that drew his interest. It was the one between her legs. She slipped her index finger between the lips of her vagina, quickly pushing past her second knuckle. Drake stole a quick glance at Fiona’s breasts. He wasn’t sure if looking at her tits would incur another whipping, so he only looked up for a second. It was difficult not to watch her tits as they rose and fell. Drake tried to focus on her command to watch her play with herself. The bed under her was getting quite wet. He wanted to touch her, but dared not violate her order to stand still.

Drake felt some relief when she released the riding crop and put her hand on her breast. Even though her eyes were closed, Drake still just made quick glances at her tits, trying to comply with her instructions. Her thumb was covering her clit now, rubbing circles on it. She was tugging on her nipple. The sight of the taut pink skin made his cock ache and his mouth water. He noticed her eyes opening, and quickly shifted his stare from her heaving breasts to her soaking wet pussy. She had inserted a second finger.

“Don’t you dare come until I tell you to,” she whispered to him. Drake felt like she could sense the enormous pressure building inside him. He wondered what his punishment would be if he lost control. He gazed at the riding crop laying on the bed next to her. How many times would she strike his bare ass with it if he came before he was told to? Drake imagined himself braced against the wall, waiting for Fiona to administer his punishment. The more he thought about it, the less of a deterrent it became.

Fiona’s moan brought his attention back to her. She had all four of her fingers inside herself. The hand on her breast was squeezing it roughly. She cried out as she came, then relax, all her limbs going slack. Drake breathed a sigh of relief. His knew he could not have watched her much longer without coming himself.

“Now, what can I do with you?” she asked.

Drake remained silent, unsure if he was even allowed to speak. Fiona had walked back over the drawer and was looking through it again. She put on what appeared to be a large wristwatch.

“Close your eyes, “she instructed.

Drake shut his eyes, wondering what she was doing. The noise stopped, and he heard her walking towards him. He knew she was standing in front of him.

“You can open your eyes.”

Drake looked at Fiona. She had a sex toy in each hand. In her right hand was a small red dildo with a wide base. In her left hand was a much bigger purple dildo. The purple one was some sort of double dildo. One part was very realistic looking. The other part was smooth, and tapered a bit where the two joined.

“You are going to find out what it’s like for a woman to have sex,” Fiona said with a naughty grin.

“I don’t understand.” Drake replied, starting to feel like he was in over his head. Maybe there was a limit to his lust for her.

“This,” she said holding up the purple toy, “is my cock. You are going to suck it, then I am going to fuck you in the ass with it. If you agree, I will make it worth your while some day. You just have to trust me.”

Drake looked at her. She was still the sexist woman he had ever seen. His eyes slowly took her in. Somehow the riding crop did not seem like much of a threat anymore. He gazed intently at her firm round breasts. Drake imagined wrapping his lips around her swollen nipples. He wondered what worth his while meant, and how soon someday would be.

“Are you in? “She asked.

Drake took a deep breath. If he said no he would probably not see her again.

“Okay,” he whispered, “I will do it.”

Fiona let out a squeal of delight and smiled broadly. Then she dropped to her knees in front of him. Her hands lightly stroked his cock. Drake recoiled in surprise.

“I’m not completely heartless, you get a hand job before I fuck you. I mean a cock like this, it would be a shame not to have some fun with it. But there is one little thing I have to do first.”

She picked up the small dildo.

“Turn around,” She instructed. Drake did as he was told. Under his breath he repeated his new mantra “Totally worth it someday, totally worth it someday.”

He felt her dripping lube onto his ass, the dildo. First she pressed it lengthwise against him, rolling it back and forth. When it was coated in lube, she pressed it into him. Maybe it was the excitement of being naked with her, but it was not as unpleasant as he thought it would be.

She put her hands on his hips and turned him back towards her.

“Now where were we?” she asked.

Drake felt a shiver pass through his body as her fingertips rubbed against his cock. She leaned forward until her lips were less than an inch from the head of his dick. He could feel her hot, moist breath. The temptation to thrust his hips forward and bury his cock in her mouth was almost overwhelming.

Her fingers stroked him from behind his balls all the way to the tip of his cock. Drake’ eyes darted back and forth between watching the hand job and her tits. Fiona’s nipples showed she was quite aroused. The sight of her naked, on her knees in front of his was intoxicating. He could see beads of sweat forming her cleavage. She put one hand on the toy in his ass and wrapped the other around the shaft of his penis. Slowly she moved both hands back and forth.

“This is making me really wet,” Fiona said, speaking to his dick like it was a microphone. The vibrations of her voice felt exquisite.

“Someday I’m going to have your cock inside me. I want you to think about fucking me. I want you to imagine the lips of my pussy stretched around your thick hard cock.” She said, looking up at him.

Drops of pre-cum appeared on the tip of his dick. Fiona smeared it all over the head of his cock.

“Do you want to fuck my tits?” she asked.

Drake grunted and nodded. He no longer had the capacity for speech. Fiona cupped her hands around the outside of her breasts, wrapping around Drake’s erection. Her tits were wet with sweat. It combined with the leakage from his cock, and Drake slid easily between her firm globes.

“That’s it, fuck my tits. Hard and fast. I want to feel you’re hot cum on my breasts,” Fiona shouted. Drake complied, thrusting his hips back and forth. Between her dirty talk and the sensation of having his dick between her tits, he did not last long. Drake moaned as the thick liquid spurted out. Fiona pushed her breasts up, trapping the head of his dick in her cleavage. When his cock stopped jerking, she released her tits and leaned back. Drake looked at what he had done. Streams of cum were running down her breasts.

Fiona picked up the purple dildo and rubbed against her skin, covering it with cum.

“A cock should taste like a cock, not like silicone.” she said, standing up.

Drake realized it was his turn to be kneel. Slowly he lowered himself in front of her. He watched as she slipped the rounded end of the dildo into her pussy. He was glad it was purple, it reminded him that he was not with a tranny prostitute.

“Now suck my cock,” Fiona said.

Drake looked at Fiona, and at the dildo. It was dripping with his cum. He opened his mouth and leaned forward and let the toy slid past his lips. He put his hands on her hips, focusing his eyes on the neatly trimmed strip of hair just above her pussy. The toy filled his mouth, and he heard Fiona moan with pleasure. As the toy pressed against his tongue he tasted himself. It definitely did not taste like silicon. The sound of her voice aroused him. Drake put one of his hands on Fiona’s breast. It felt electric. His fingers pinched her nipple, pulling it taut. Fiona put her hand on top of his. Drake moved his head back and forth, sliding the toy in and out of his mouth. Fiona moaned again. He doubled his efforts, and rewarded with another moan. He looked up at Fiona. She was staring right at him. He kept eye contact with her and continued to suck on her toy.

“That’s it Drake, make me come. Suck my cock.” Fiona moaned.

Drake watched the other end of the dildo sliding around in Fiona wet pussy. He could feel the heat from between her legs, and he watched the purple toy bumping against her clit. Despite draining his cock on her breasts only minutes earlier, he felt his penis beginning to swell again. Drake felt Fiona’s fingers pulling his hair, forcing his face against her. She thrust her hips forward, ramming the toy down his throat. Fiona’s hands clamped down on his head as she came. As her moaning and whimpering became faint she released his head, and the toy slipped from his mouth.

“I see why guys like that so much. I just wished this thing would shoot out cum, that would be awesome,” Fiona said breathlessly.

“I kind of got the idea what its like,” Drake replied.

He watched as Fiona stroked her toy. She picked up the bottle of lube and began to spread it all over the purple cock. Drake suddenly felt butterflies in his stomach, and a few other places.

“You still up for this? ” Fiona asked.

“Totally worth it someday, totally worth it someday,” he muttered under his breath, nodding to Fiona.

“Get on the bed, and spread your legs.”

Drake slowly lay back on the bed. He looked at Fiona, focusing on her breasts.

“Look at me,” she said to him.

He looked into her eyes. All he could see was pure lust. At the edge of his vision he saw her arm move, pulling the smaller toy out. He was so lost in her stare that he did not even feel it. Drake felt the bed shift as Fiona climbed onto it. He pulled back on his legs, spreading them apart. Fiona’s thighs pressed against him, and he felt the toy pushing against him.

“Keep looking at me,” Fiona commanded, “I want to see your eyes when I start fucking you.”

Drake met her stare as she began to fill him. She leaned forward and her breasts brushed against his chest. Drake let go of his legs, wrapping them around Fiona. She pressed her tits tight against his chest as she thrust into him over and over. Her fingernails dug into his shoulders. Drake pressed his lips to hers, thrusting his tongue into her mouth. She tasted sweet and intoxicating. She tasted like obsession. She stopped thrusting and hugged him tightly. A soft moan escaped her lips as her orgasm surged through her body. After a few moments she lay beside him.

“You are my first.” she said.

“First what?” Drake asked.

“First guy I have fucked like that.”

“You are my first too.”

“First woman that has fucked you, or first person that has fucked you in the ass.”


Drake noticed Fiona looking at him. He followed her gaze to his erection.

“You seem to like it,” she commented.

“I like you, no matter what you are doing to Me.” he replied.

“Well, it would be wrong to waste it. Stand up.”

Drake put his feet on the floor and slowly stood. He felt a little sore, but not enough to prevent him from following Fiona’s instructions.

“I want to watch you jack off,” Fiona said, sitting on the edge of the bed. She bent down and picked up the bottle of lube. Drake simply stared at her. His eyes were drawn to her naked body like a moth to a flame. He watched as she poured the lube into her hand, then smeared it on his throbbing cock.

“I want you to look at me while you do it. How do you want me? Bent over a chair? On my hands and knees? On my back with my legs spread? I want to give you something to remember when you are alone and stroking your dick.”

“The last one, on your back. That’s what I want,” Drake managed to stammer. He had already put his hand on his penis.

Fiona reclined on the bed, spreading her legs wide. She had removed her toy and set it on the floor. Fiona rotated her hips so Drake could see her ass and her pussy. Slowly Drake began to slide his hand up and down. Fiona put her hands on her breasts, pinching and tugging her nipples. Drake felt his orgasm building already. He met Fiona’s eyes, and his arousal increased even more. She licked her lips, the formed them into a circle as if she was giving him a blowjob. Her tongue rested on her bottom lip, then end curled up slightly. Drake imagined feeling it on the bottom of his cock. The pressure built up even more.

Fiona was moving her hips up and down. Her pussy was wet and stretched out from the toy. Drake looked back into Fiona’s eyes.

“I want you to come all over me Drake, I want to feel you.”

Drake groaned loudly as the jet of hot liquid erupted from his cock. It seemed to move in slow motion as it arced over her body, finally landing on her left breast. The milky stream covered her nipple completely. The remaining spurts landed on her groin, and dripped onto her pussy. Fiona cupped her hand under her breast and pulled it towards her mouth. Drake watched as she slurped the liquid off her tit, finally swirling her tongue around her nipple.

“You will have to clean up the rest, I not that flexible, at least not yet.” she said.

Drake wasted no time dropping to his knees. He started at the top and lapped up every drop. He ran his tongue over the lips of her pussy. She was warm and soft. As Drake licked between her legs Fiona moaned approvingly. He wrapped his arms around her thighs and pressed his mouth against her. Drake explored her silky smooth skin with his tongue. She bucked her hips against him.

“Don’t stop,” Fiona panted, “make me come?”

Drake doubled his efforts to comply with her request. He could feel her getting wetter and hotter. His tongue alternated between thrusting inside her and lapping at her clit. He felt her tense as she climaxed. When her body went limp Drake released her, staying on his knees. He took another long look at her naked body. She was covered with a sheen of sweat, and her breasts were heavy up and down.

Fiona sat up and looked at him. She had a smile on her face. She leaned down and kissed him.

“Do you do this a lot?” Drake asked, not sure if it was a good idea.

“Do what?” Fiona replied.

“Have sex with someone besides Frank.”

“Yes, well, Frank is usually part of the fun. He was too jet lagged today, maybe next time he will join in.”

“So it won’t be weird to go chat with him after all we have done.”

“Not for Frank. I’m sure you are going to be a little freaked out.”

” You got that right, “Drake said, pulling on his pants.

“You get used to it after a while.”

Fiona walked up to him, she was still naked, but had her panties in her hand. She tucked them into Drake’s pants pocket.

“Thought I would save you the trouble of swiping them. I expect them back next time I see you.” she whispered in his ear.

Drake finished dressing and looked back at Fiona. She was putting away her toys, still naked. He opened to door and walked down the hall. Frank was reclined on the couch.

“Grab a drink from the fridge, then come in and sit down,” Frank said.

Drake selected a soda and settled onto the couch across from Frank. He stumbled through some small talk about his internship. The entire time Drake wondered how Frank could be so calm about Fiona. He noticed Frank was staring at him, expecting a reply to some question.

“Did she tell you she would make it worth your while someday?” Frank asked.

“Yea, yea she did. What does that mean?” Drake replied.

“Just what it sounds like. Every time she made that offer to me I have been amazed. She will probably just show up at your door someday. You better be ready for her, she does not like to be disappointed.”

“Really, any suggestions?”

“She sees something in you that interests her, you have to figure out what that is, and turn it up to 11.”

After that they said their farewells, and Drake walked back out to his car. As he drove away he wondered how long it would be until someday happened.

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