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HomeStraight Sex Stories Ch. 6 Tom And Claire and Brenna

Ch. 6 Tom And Claire and Brenna

Series: Finding Paisley

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Claire calls Tom to have another session and break in her best friend Brenna

Tom and Kianna plan to meet, but a call from Claire takes precedence...

Tom looked at his screen. It was a Monday morning, like most Mondays. But was it? Yes, he was sitting at his desk working and checking Lush to see who might be online. But he had just experienced the most amazing encounter with Roxanne and her young protege. He had fucked them both. He had taken Claire's virginity. The experience had been otherworldly. He had gone from cybering with young women via typing to voice chatting to real-life fucking.

These thoughts bounced around his brain, making concentrating on work almost impossible. Luckily, he was almost done. He saw the black box in the corner say that a friend had logged on. Kianna? He sent a quick message. Hey, how are you?

I'm doing great, how about you. Kianna typed as she sat in the cafeteria at school. Her project was complete and she wanted to reconnect with Tom. Sorry for not being around, but I am totally free now. No more school projects and I have some time off for the break. I was wondering something, and I am not sure how to ask you about it. She bit her lip and watched the screen on her laptop.

I am just glad you are done. I missed you. What is it that you want to ask me? Different scenarios flashed across Tom's conscious mind. He dismissed the most fanciful of them.

Well, I think we should meet. Kianna nervously awaited Tom's response. She tapped her foot and twirled a lock of her hair.

Tom was not expecting this. He had thought about it. More so since his rendezvous with Roxanne had shown him how amazing a real-life encounter with a Lush partner could be. Really? What makes you want to meet in real life?

Well, if you don't want to, I understand. I thought that you would want to... Kianna was disappointed. She had expected a more positive response.

No, I'm sorry. I would love to meet. I am just surprised, that's all. Tom sat back in his chair. She wanted to meet? He assumed that she wanted to have sex.

I am glad to hear you say that. Let me just lay it out. I want to have sex. I want you to be my first. What do you think?

There it was. Tom reeled. She wanted to have sex. And she wanted him to be her first. He knew she was a virgin and that she was disillusioned with the guys at school. Images of her pale skin, freckled and waiting for him flashed in his mind. He was a dirty old man and she was young enough to be his daughter. His cock stirred despite his conscience.

I would be honored. I would love to shove my big cock into your tight, young pussy... Tom chuckled, waiting for the response he knew was coming.

I am counting on that...but don't get too cocky there, mister. I can always change my mind...hee-hee! Kianna was getting wet just thinking about Tom's cock actually thrusting inside her, filling her cunt and making her cum. But was this smart? No, her brain told her that. But her libido told her brain to shut up and let her get laid. The libido was winning the argument.

So how would we do this? Tom had ideas but didn't want to be too aggressive with Kianna. Let her take the lead.

Umm, I was hoping you would have some good suggestions. Kianna was giddy. She was worried that Tom would politely decline. Fantasy scenarios were running through her head. Her brain was taking a beating in the argument.

Ok, how about this. You are off from school for a break. We meet in Santa Barbara. I know a little boutique hotel that would be perfect. I'll be in the lobby and we can meet there. Two nights. One night won't be enough, I know you. One taste of real cock and you will be insatiable. How does that sound?

Mmm, sounds pretty good. Wow, I can't believe we are really going to do this. Seriously though Tom, you will be gentle, right? Butterflies were buzzing her stomach like Kamikazes. That lock of hair twirled some more.

Yes, of course. You are in good hands. Tom leaned back in his chair and ran his fingers through his hair. Was this really happening? Was he going to meet this young woman for sex? He wanted to. The image of his cock penetrating Claire's womanhood, the slick walls gripping his member and seemingly objecting to the presence of his flesh. Then yielding, opening up ever so slightly to allow his thick shaft to slide further into her womb.

He wanted, no he needed to feel that again. The last decade or more was a mind-numbing routine of sexless nights and jacking off to porn. His wife had become a roommate. What passion they had, in the beginning, had faded to nothing. She seemed ok with a platonic relationship, but Tom hungered for physical contact, flesh-on-flesh, tingling skin and shared orgasms. What he had experienced with Roxanne and Claire. What he now hoped to share with Kianna.

Ok. I will trust you to make the reservations. Just give me the address and the time to meet. Kianna stared at the screen; a bit numb. Her brain screamed at her that she was making a huge mistake. Her libido fired back that Tom was perfect and that his cock was what she needed. The wetness between her legs was evidence of which aspect was winning the debate.

"Tom, I'm off to meet my client. We will be checking out paint samples and looking at furniture. She is very demanding and particular. I will be gone all day, most likely." Monica, Tom's wife was talking from downstairs. Tom's office was just right of the landing on the second floor. It was open, with only a pony wall separating his desk from the expanse above the first-floor entryway. At first, he thought it was too exposed. But now he loved it. He was like Kirk on the deck of the Enterprise. He could see and hear almost everything in the house. It also left him exposed when he played, so he had to be careful that he was alone.

"Okay, sweetie. Have a good time. Let me know if you are going to be late." Tom did care about her. At first, they were madly in love and couldn't keep their hands off of each other. Blowjobs while he drove, sex in movie theaters that were mostly deserted, fucking in the passenger seat of his hatchback in a parking lot. This is what his sex life had been when they met. He was twenty-two, she was eighteen. they were married and it continued. But after several years, the passion dwindled. Tom tried to keep the flame lit, but Monica seemed to lose interest. They enjoyed each other's company, but sex became an item that was not on the menu very often.

"I will. I'll text you later." Tom heard the door close as Monica left. He looked back at the screen to continue with Kianna, but she had logged off.

"Ok, let's make reservations", Tom mumbled to himself. He quickly found the site for his favorite hotel in Santa Barbara. His phone rang. "Hello, Tom speaking."

"Uh, hi, Tom. This is Claire..."

"Claire? Is that really you? Uh, how are you? How did you get my number?" Tom leaned back and ran his fingers through his hair. This was out of left field. He wanted to see Claire again and soon, but he thought that it would be at Roxanne's discretion. He never thought Claire would contact him directly.

"I, uh, well I found it on Roxanne's phone. She asked me to find a contact for her and I saw your number there. I wrote it down." Claire nibbled on her fingernail, a nervous tic that she had since she was in seventh grade.

"How did Roxanne get my number?" Tom was still confused.

"Really? You know Roxanne. She always gets what she wants and she knows how to get it. I assume that she did a little digging and found you." Claire's voice had a level of confidence now. Explaining about Roxanne getting Tom's number was less stressful than telling Tom why she was calling. "So I was wondering..."

"Yes. What were you wondering?" Tom felt like he was back in high school, waiting for a girl to answer him when he asked her out.

"Well, I was wondering...I have a friend...my roommate, actually. She is like I was, you know, a virgin."

"So let me guess, she doesn't want to be a virgin anymore?"

"Exactly. I told her about our encounter with Roxanne. I told her how you were gentle but forceful. And...that you had a really big cock!"

Tom could hear her giggle, like a little girl when she said the last part. He remembered that he was talking to a nineteen-year-old. She was so young. And firm. Wow, he was a dirty old man, he thought. Well, she was an adult. If she wanted to have sex with him, who was he to deny her? He laughed at the logic, which was clearly concocted by his little head and not his big one.

"And..." Tom waited for what he anticipated was her request. She wanted him to fuck her roommate. Like he had fucked her with Roxanne.

"Could you, would you want to, you know, do to her what you did to me?" Claire bit her lip. She waited for Tom to respond.

"What did I do? Tell me what you want, Claire. I want to hear you say it." Tom pressed her, knowing that she was uncomfortable, but wanting her to say it out loud. As he waited, he reached down and rubbed his growing erection through his shorts.

"Umm, well, she wants you to fuck her. Like you fucked me." There was a pause. Claire gathered herself and continued. "Please Tom, she had a  boyfriend but he did not treat her right. He was only after sex. He was grabby and demanding and she never felt right. So when she didn't put out, he broke up with her. Dick, he was just a dick!!"

"Hmm, so does Roxanne know you are calling me? We both know that she likes to be in control. And she is very protective of you. Is your roommate one of Roxanne's special friends, like you?" Tom was now concerned. The last thing he wanted to do was jeopardize his new relationship with her. But the chance to be with Claire and her roommate was so damn tempting. Tom debated what to do.

"Call Roxanne. Now. Tell her to call me, as she has my number and I don't have hers. I'll wait."

"Okay. You sure you want to do that?"

"Positive. I'll be waiting." Tom hung up and sat back in his chair. He tried to finish the last two consults, but the words on the page were just gibberish. He gave up and moved over to the couch in the adjoining sitting room of his office space. He clicked on a sports talk show. He watched the host and saw his lips move, but he heard nothing. Then his phone rang.

"Hello, Tom speaking." It was his standard greeting since most calls were business.

"Mmm, Tom, so nice to hear your voice."

"Likewise, Roxanne. I hope you are well." He tried to sound nonchalant, but he was nervous. He hoped it didn't transfer across the line.

"I am, thanks for asking. Tom, you have passed another test. Claire wanted to see you again and wanted to involve Brenna, her roommate. She asked me if it would be okay. I said yes, but only if she called you herself. I wanted to see if you would agree to meet them without my consent. If you had, she was instructed to give you a false address and never contact you again. And of course, we would be through. I value honesty and loyalty." Roxanne's voice was cool and measured.

"Hmm, okay. I just figured that since Claire was so special to you, that it would only be right to get your consent. I assumed her roommate would fall under the same conditions. I would never do anything to hurt you, Roxanne. I don't want to jeopardize what we have started. But I would love to see Claire and her friend Laura. With your blessing."

"I'm touched. You continue to surprise and impress me, Tom. Yes, I approve. I know you will show Brenna the wonders of a proper fucking. I wish I could be there to watch and participate, but I am with my designer all day. I have been redoing my condo for the past several months. When it is finished, I want you to come over. There is a special playroom that you must see. I expect you to show them a good time, lover." Roxanne hung up. She smiled. Tom was special. He had all the qualities that were sorely missing from the many men she had been with. It was the main reason she had concentrated on women with men being the occasional change of pace.

“Do you think this color is too dark?” Roxanne held up a paint chip and tried to catch the light in the showroom.

“No, I think it would be perfect. Remember the mood you are trying to set.” Roxanne’s designer came up next to her and placed her hand on the small of her back. Ever so gently, like a lover’s caress, her fingers traveled down Roxanne’s back and came to rest on the swell of her firm buttocks.

“You just want me to make a decision.” Roxanne chuckled. She was a demanding client and she knew it. Good enough wasn’t. Fortunately, this designer understood her. Intimately. “I think you are right though. Done.” She reached out and took her hand from her ass and clasping it, they walked to another part of the showroom.

Tom waited. When his phone rang, he swiped and answered, “Yes?” Not his usual greeting but he knew who was on the other line.

“Sorry, I had to do it that way. I told Roxanne that I wanted you to initiate Brenna like you did me. She said okay, on one condition. That I test you. I’m so sorry, but I’m really glad you passed. Roxanne was positive that you would. I thought it was a bit mean, but she insisted. She said in case you didn’t pass, then you were not the man she thought you were. Something to that effect.” Claire shifted her weight from her left foot to her right. She hoped Tom would not be mad. Tricking him sucked, in her opinion, but she dared not go against Roxanne’s wishes.

Tom was not happy being the subject of yet another test, but he did at least understand where Roxanne was coming from. She had obviously been with many men who were less than honorable. Claire was her jewel. She was very protective of her. Was this the final test? Would she now trust him and his motives? These questions danced around in his brain like spinning tops, banging against the sides and shooting out across to the other side, only to hit again and repeat the process.

“Tom, are you still there?” The sound of Claire’s voice, timid and questioning, brought Tom out of the stupor he had fallen into and back to the here and now.

“Sorry, got lost in thought for a second. Yes, I’m here, sweetie. It’s okay, I know why Roxanne did what she did. You should be flattered. She thinks very highly of you and would do anything to make sure you are not hurt by guys who are selfish pricks. I’m sure that goes for Brenna as well.”

“I’m so happy that you aren’t mad at me, Tom. So…does that mean you will come over now?” Claire bit her nail, hoping the answer was yes.

“Text me the address. I’m sure you and Brenna will make it up to me.” Tom hung up without waiting for Claire to reply. The address appeared on his phone. He pulled on a pair of black joggers, a fresh black t-shirt and slipped into his grey knit Allbirds. He grabbed his small bag in case he wasn’t able to drive home tonight. He planned on breaking Brenna in as well as doing things to Claire he had not done yet. Two bottles of Chardonnay and a half bottle of scotch joined the other items in his bag. Yeah, he thought, I’m definitely not driving back tonight.

 

The female voice of his GPS told him that he was at this destination. Tom swung the black Q8 into the driveway. A young guy, maybe twenty was banging his fist on the door and yelling. Putting the car in park and switching off the engine, Tom jumped out of the driver's seat and strode towards the commotion.

"Brenna! Open up! I want to talk to you. Goddamn it, open the fucking door!" He pounded his fist over and over as he yelled.

Tom sized the man up. Blonde hair, short on the sides and long on top. Clean-shaven. Young. Average height, no more than 5' 7" and about a buck forty. Torn jeans, the on-purpose kind, and a white t-shirt. "Hey there, what seems to be the problem?" Tom approached the frustrated young man with his hands outstretched.

"What fucking business is it of yours, old man. Get lost!" The guy stopped hammering his fist on the door only long enough to glare at Tom and then continued his assault.

"Go away, Brad, I don't want to talk to you. Ever. Just go." The voice was stressed. It was not Claire's so by process of elimination, Tom deduced it must be Brenna.

"Hey, man, she obviously doesn't want to talk to you, so why don't you just leave, okay?"

The guy turned to face Tom, with fire in his eyes. They were bloodshot. "I told you to fuck off, old man." He moved in close and swung at Tom.

As his right hand lunged forward in a big arc, Tom leaned back to his left. Every guy throws a big looping left, Tom mused as he avoided the errant blow. Grabbing the wrist with his right hand, Tom squeezed Brad's neck with his left. A quick motion and Tom had his arm locked behind him as he pressed Brad's head towards the front steps.

"Now this old man could break your arm, you little fuck. I asked politely, but you insisted on taking a swing at me. Didn't mommy teach you to respect your elders?" Tom pressed harder on Brad's neck as he wrenched his arm to the limit, right at the edge of damage. He heard the younger man grunt and gasp. Tom towered over the slight frame and lowered his voice.

"Get the fuck out of here. Do I make myself clear? And don't ever come back. If you do, or if I even hear of your bothering Brenna, I will break your arm." Tom released his arm but pulled on Brad's neck, bringing his face close to his own. Tom looked down into the blood-shot eyes, which were now moist with tears. "Capuche?"

Brad stumbled towards the street as Tom abruptly released his grip on his neck.

"Yeah, well, she isn't worth it. Stupid bitch!" Brad looked back at Tom and flipped him off, but Tom could see the fear in his eyes. Brad walked quickly to a blue Prius, got in and drove away. Tom turned back towards the house. It was a nice, small cottage style with a small front yard and two steps up to the door. The beach was two blocks away and with no traffic noise, you could hear the ocean.

The front door opened as Tom reached it. A brunette jumped into his arms and gave him a huge hug. In the doorway was Claire, with a big smile on her perfect lips. The girl released him and stepped back.

"Oh, sorry, I'm Brenna." She looked up at him, now a bit more reserved after her initial physical demonstration of gratitude.

Tom smiled. "Nice to meet you. I guess Brad wasn't invited?"

"Uh, no. Can we go inside? I don't want him to come back." Brenna looked nervously over Tom's shoulder in the direction Brad had driven.

"He won't be coming back, I'm pretty sure about that. After you, my dear."

Tom took inventory of Brenna's assets as she walked into the cute little beach bungalow. Thick brown hair. A plump ass that jiggled as she moved. Not fat, just round and firm. Shapely legs. A cute face with big brown eyes. But her crowning glory was a pair of tits straight out of Tom's teenage masturbatory fantasies. D-cup on a petite frame. Round and firm like only young breasts can be. Large nipples. Before she turned around Tom noticed them poking through the thin t-shirt she wore. In a few moments, Tom knew he would see and feel them. His cock twitched in anticipation.

Brenna stopped and turned, facing Tom. "Sorry about Brad. He is such a prick. I can't believe I ever was with him. Thank you for getting rid of him." She looked up at Tom.

Tom found himself staring into her eyes. Brenna returned his stare. Claire broke the ice. "Okay, so what do we do now?"

"Be right back." Tom went back to his car and retrieved his bag. He opened one of the bottles and poured drinks for the girls. "This ought to loosen you up a bit."

Brenna told Tom all about Brad as they drank. He could see her loosen up and become animated as she described her relationship and eventual breakup. Claire was mostly quiet, adding a few details and in general just supporting her friend. Tom could see how deep their bond went. Brenna and Claire shared poor decisions in the two guys they dated in high school. Brad was the virtual twin of Dean. Both egotistical pricks. Popular and selfish. Each wanted desperately to fuck Claire and Brenna. In fact, they would have been happy to fuck both of them. At the same time. Ironic, since they all attended a strict religious school. The girls bought into the morality taught there, the guys…not so much.

Tom sat next to Brenna as she bared her soul. After the second glass, she talked about more than her ex. Her eyes lit up when she described how Roxanne had come into her life after Claire had taken a position with her. Claire smiled and rubbed her friend’s shoulders. She explained her sexual awakening and the joys of female sexuality. What was missing, she said as she looked deep into Tom’s eyes, was the joys only a cock could bring. But with someone she could trust and who knew what to do. With that, she reached out and caressed his cheek. It was a simple gesture, but it spoke volumes.

Grasping her hand as she touched him, Tom said, “I’ll show you pleasure like I did Claire.”

“That is what we are counting on, Tom.” Claire looked at Tom and smiled, ending with a wink and a kissing gesture.

Tom leaned in and kissed Brenna’s cheek. Her skin, soft and warm, felt good on his lips. Turning her head to face his, their eyes met for a second. It felt like minutes. Tom moved in and lightly kissed her. Brenna’s lips were moist and Tom could taste the alcohol. His tongue gently pried her lips open and explored her warm mouth. He felt her tongue join in the gentle dance. Her hands pulled the back of his head as her kiss became more urgent.

Tom broke the kiss after several minutes and while never breaking eye contact, grasped the hem of her shirt and pulled it up over her head. Brenna’s breasts moved up with the motion and as the fabric rose above her shoulders, fell naturally to her chest. The gentle pull of gravity resulted in the firm globes bouncing against her chest several times, each reverberation smaller than the previous one. The nipples were swollen and pointed straight at Tom, begging for attention. He removed his shirt.

Cupping her left mound, Tom flicked his tongue lightly over the tip. Brenna shuddered and air escaped her lips in a hiss. He sucked the entire nipple into his hungry mouth and bit down. Brenna squealed.

Brenna marveled at how gentle yet forceful each of Tom’s movements was. Brad had simply pawed at her tits. He stated they were his to do what he wanted. He tugged and pulled at them, squeezing without any regard for her pleasure. Tom was gentle. He played her body like an instrument. No man had done anything like that before. Only Roxanne, Claire and a few other females in the circle had shown her the pleasure she had been missing. Now Tom could join that exclusive group.

“Oh god, Tom, that feels so good.” Brenna cooed as Tom sucked and nibbled on first one nipple, then the other. She could feel herself getting wet. Her hands caressed his face during Tom’s assault on her breasts. He cupped and gently massaged each globe.

Tom stopped. Brenna looked at him with that same hazy gaze that Claire had in the hotel room. Tom lifted her hips and tugged the bikini bottom off, exposing her wet cunt for his inspection. She was shaved. The gentle swell of her outer lips led to a pair of inner lips that were stunning. Like petals of a flower, they were gaping slightly. A darker shade of tan, they framed a bright pink orifice that glistened with dew. He leaned in and experienced her scent for the first time. Intoxicating, a mix of sweet with just a hint of musky elements. Remarkably like Claire’s, but unique to Brenna. Tom licked his lips in anticipation.

“Oh, oh, oh fuck!” Brenna reacted to Tom’s talented tongue as it stroked and probed her tender folds. “Ahh!” Brenna gasped as it flicked her clit. Round and round, flicking her clit, sucking on her lips and forcing his tongue deep inter her cannel, Tom assaulted her pussy. Her juices flowed. His hands grasped her ass and raised her petite frame up to meet his mouth.

Claire had removed her clothes and sat naked on the far end of the couch. She tugged on a nipple as her other hand rubbed her clit. She longed for Tom’s attentions, but waited her turn. She knew what Brenna was experiencing and was happy for her. But in a small part of her mind, she was jealous as well. She was anxious for her turn.

“Ah, Ah, Ung…” Brenna’s moans intensified as Tom focused on her clit. Two fingers slid into her sopping hole and found her G-spot. In moments, she succumbed to the dual stimulation and fell off the cliff she had been walking like a tightrope. She tumbled into her orgasm. Waves of pleasure washed over her body, starting at her center and radiating out to her fingers and toes. She lost all sense of time. She was at one with her climax and she was her climax.

Brenna’s thighs clamped Tom’s head in a vise grip, surprising him. He did not think she had that much strength in her little frame. Lapping at a furious clip, he could not capture all of her nectar. The excess ran down his face and chest. His fingers gripped her ripe cheeks as he rode out Brenna’s orgasm. She thrashed and bucked for well over a minute, although it seemed longer to both of them. Feeling her motions ease in intensity, Tom relaxed his grip. He looked up, finally releasing his mouth from her womanhood. Brenna’s eyes were closed and her lips were pursed intently. Yet she seemed so content.

“How are you doing, baby?” Tom ran his hands up her stomach and gently caressed her breasts, rubbing her erect nipples.

Brenna opened her eyes half-way. A smile played on her lips. “Mmm, fuck that was good. Claire said you could eat pussy almost as good as a woman. I told her ‘No Way!’ I was wrong. That was amazing!”

Claire came over, grasped Brenna’s hand and grinned. “I told you. Just wait until his cock is inside you.” She pulled her up to a seated position. “Let’s take this to the bedroom.”

Tom stood up and leaned in, cupping the back of Claire’s head. He pulled her in for a kiss, covered in Brenna’s juices. Claire licked his lips with her tongue before pressing her lips to his and thrusting her tongue deep into Tom’s mouth. It was not a gentle kiss, but one filled with urgent need. “God that was so hot, but I need to cum. After you fuck her, your cock is mine.” She bit his lower lip, ending the kiss and sauntered, naked into the bedroom. Her ass hung like a ripe pear in front of Tom, tantalizing and just out of his reach. He kicked off the black joggers and hurried into the bedroom.

“Umm, mm, ung…” It had taken only a minute to shed his pants and briefs, but as soon as he entered the room, he was greeted by Brenna’s ass, arched in the air as she furiously licked Claire’s cunt. Moans and ripe aromas of sex filled the room. Claire’s back was arched and her fingers tugged at her erect nipples. Claire was already primed since she had been frigging her clit while Brenna’s orgasm wracked her body. So, Tom watched, slowly stroking his shaft while Claire hurtled towards her impending climax.

Brenna’s finger snaked into Claire’s steaming folds and found her G-spot. Moments later, Claire erupted.

“Aw fuck! I’m cumming, damn it…Unngghh!” Claire’s body stiffened and then spasmed as her orgasm ran its course. Juices flooded Brenna’s face, soaking her and the sheets.

“Wow, that was hot. Brenna, come here, please.” Tom motioned for her to join him.

Kneeling in front of Tom, Brenna looked up at Tom. “Have you had a cock in your mouth yet, baby?

Brenna shook her head. “Brad wanted me to, but my mom always told me that was not what good girls did.” She placed her hands on Tom’s thighs.

“Okay. Just relax and we will go slow. Grasp the shaft and stroke it.”

Brenna did as instructed and slowly ran her hands up and down.

“Don’t grip so tight. Gentle, that’s it. Now lick it.”

Brenna’s tongue lightly touched the tip. Tasting the precum that oozed from Tom’s cock, she smiled and took the head in her mouth. Tom groaned as his cock slid into the soft wetness. Her tongue swirled around the shaft just under the head.

“Fuck, you are a quick study, girl!”

“Mhmm,” Brenna mumbled with her mouth full of Tom’s throbbing member. She continued to stroke the shaft as more of his stiff cock worked into her throat. Stifling her gag reflex, she let the tip glide into the back of her mouth and enter her esophagus.

Tom thrust slowly, fucking her pretty face. Her mouth was stretched wide, lips thin as the shaft pistoned in and out. Saliva dripped from her lower lip.

Feeling that he was on the edge, he pulled out. Brenna gave him a puzzled look. “Did I do something wrong, Tom?”

“Oh no, sweetie, you were too good. I almost lost it and I want to cum in your sweet pussy.”

Brenna giggled and stood up. She moved back to the bed and lay down, spreading her legs. “Fuck me, Tom, please. Fuck me, but go slow. I’m really tight.”

Tom moved between her legs and lined up the tip with her swollen and dripping lips. He pressed forward. The head parted those lips as it sank in. God, was she tight, Tom thought. After a slight pause, he pressed harder.

“Oh shit. Stop, it’s too big! Oh god…” Brenna’s eyes were wide and her eyes were tearing up. Tom paused.

“Relax, baby, it will feel so good. Just give it a few seconds.” Claire spoke in a soothing manner as she stroked her hair.

“Is this how it felt when you did it?” Brenna looked at Claire, pleading for reassurance.

“Yes. Then it felt so good, I asked if we could do it again…hee-hee! Here, put your legs up higher.” Claire guided Brenna’s knees up higher. She nodded at Tom.

Tom pressed again and his cock slid further into the incredibly tight space that was Brenna’s cunt. She moaned, but this time it had just the hint of pleasure in it. Encouraged, Tom pressed on with the assault on this virgin pussy.

“Um, ohhh, ahhh…”

“Starting to feel better?” Claire brushed a lock of hair out of Brenna’s eyes, which were closed.

“Uh, oohhh, yeah. Is all of it in?”

“Almost. About three more inches.”

Tom had remained silent. He figured that Claire was doing just fine. He concentrated on getting his cock into Brenna’s impossibly tight vagina. Claire had been tight, but not this tight. It felt amazing, but he did not want to cause Brenna too much pain.

“Give it all to me, Tom. Fuck me.” Brenna reached out and pulled at Tom’s hips, trying to get the last few inches inside her. Tom obliged and with a quick thrust, went balls deep. Brenna gasped.

“Oh fuck, that is deep. And thick! God, I feel so stretched out.”

Tom grabbed her knees and pressed forward, allowing him to go just a tad deeper. Pulling almost all the way out, he slid back in, slapping his thighs on Brenna’s ass.

Squish…

Slap…

Squish…

Slap…

“Oh god, oh god!” Brenna gasped as her formerly virgin pussy accepted Tom’s pummeling.

Tom increased his tempo.

Squish…Slap

Squish…Slap

Squish…Slap

Tom glanced up. He had been staring at his shaft sliding in and out of her tight pussy. Lips gripping like they didn’t want to let go of the cock invading its space. Brenna’s tits bounced with each thrust. This visual was like kryptonite to Tom. He loved to see firm, ripe female flesh move in this manner. His cock got even thicker as he watched. Reaching out and tugging on a nipple elicited a squeal from Brenna. She opened her eyes and grinned at Tom.

“God, you’re tight, babe. Fuck, I’m not going to last much longer…” Tom moved forward. He was now above Brenna with her legs hooked over his shoulder. Her hips rotated forward, allowing Tom’s massive cock to plumb the depths of her sopping wet hole.

Squish...Slap...Squish...Slap...Squish...Slap...Squish...Slap...Squish...Slap…

At this pace, Tom had only moments before he came. Claire’s hand reached out and rubbed Brenna’s clit. That pushed her off the ledge and into the void. Brenna screamed as she tumbled.

Oh god, FUCK!...I’m cumming!” Brenna’s body was wracked by her second orgasm.

Tom’s time had run out. He erupted into her, spewing hot cum deep into her tight pussy. Her spasms gripped his shaft, milking every drop from the turgid flesh.

When conscious thought returned to Tom, he looked up to check on Brenna. Eyes closed, hair damp with sweat, nipples erect and dark, areola crinkled and bumpy.

“Hey, when is it my turn?” Claire winked as she crawled over to the mass of sweaty flesh and playfully slapped Tom’s ass.

“Fuck, let me catch my breath! I’m not twenty anymore…”

“Could have fooled me. You just fucked her better than any young guy could.” Claire began playing with Tom’s semi-erect cock. “I bet I can get you hard again.” She slid her hand up and down, using the juices from Brenna’s pussy as lubrication.

“Come here,” Tom growled. “I need a few minutes.” Tom grabbed Claire’s hips and bent her over so that her ass was sticking up and her head was on a pillow. He spread her cheeks and pressed his face into the warm space between. His tongue lashed at her tender folds. Gentleness was not on his mind as he furiously nibbled her lips and thrust his tongue deep into her nether region.

“Mmm, unh, unh,” Claire groaned and moaned as her cunt absorbed the onslaught from Tom.

Mhmm, Tom is more aggressive than he was the other night, Claire thought. God, he is hitting the right spots. Roxanne was the best orally that she had ever had, but Tom was a close second. And different. Her pussy was flooding juices all over Tom’s face.

Tom moved up and licked the little puckered star in front of him. It spasmed, then after some coaxing let his tongue in. He thrust deep, eliciting a guttural sound from Claire.

His cock now fully erect, Tom moved up and aligned the angry, purple head with Claire’s swollen lips. He impaled her with a single, deep thrust. His thick shaft slid all the way in as his thighs slapped against her firm cheeks.

“Ung, fuck…” Claire was surprised that Tom did not ease his massive tool into her but instead, stuffed her tight hole with one mighty plunge. It hurt just a bit, but now the fullness was washing her pussy with waves of pleasure. Her body rocked with each thrust as Tom bludgeoned her, slapping her cheeks with his powerful thighs.

Slap, Squish, Slap, Squish, Slap, Squish…

There was no gradual increase like there had been with Brenna. Tom started at top speed. Claire had to brace herself using the headboard.

Sweat dripped off Tom’s forehead and landed just above the top of Claire’s ass-crack. It flowed down and joined the juices lubricating Tom’s fleshy battering ram. Tom licked his finger and pressed it into Claire’s puckered hole. Brief resistance, then it opened and sucked his digit in.

“Ungh…ah that feels good.” Tom’s finger wriggled inside Claire’s ass.

“I’m gonna put my cock there. Are you ready for it?” Tom pulled his thick dick from her dripping pussy and rubbed the tip around her lips, coating it with a layer of juices. “Brenna, baby, toss me that tube of lube.”

Tom squirted a large glob of lube on his finger and worked it into Claire’s puckered hole. Grunting, Claire moved her hips back.

Another glob was slathered over his cock. When finally ready, Tom lined up the tip with Claire’s virgin asshole.

“Uh, please be gentle. Your cock is so fucking big…”

“It will hurt for just a bit, then feel really, really good. Are you ready to take it like a big girl?” Tom rubbed his purple and swollen tip around her brown hole. He resisted the urge to just ram it in. Knowing it would hurt like hell, he massaged her cheeks instead, prepping her for the brief pain she was going to experience.

“Uh-huh.” Claire was hot. Her pussy was stretched and dripping, thanks to the vigorous pounding she had received. Her ass was relaxing, due to Tom’s digital preparation. But she knew his cock was much thicker than his finger. Was she ready? She wanted his cock inside her ass.

Tom pressed forward. Resistance, then with a pop the head was in. Claire gasped. “Ow, ow…”

“Good girl, the head is in. Now breathe and relax.” Brenna moved over, curious to see Tom ass fuck her best friend.

Claire took several deep breaths. She thought of waves lapping on the shore.

Tom’s shaft was spreading Claire’s sphincter as it slid deeper into her anus.

God, this is so fucking tight, thought Tom. He wanted to fuck her hard and fast, but knew he had to go slow.

“Doing okay, baby?” Tom slowly, inch by inch, worked his massive member into her depths.

“Uh-huh.” Claire took another deep breath and blew it out slowly.

With a final push, Tom’s thighs touched Claire’s ass. All eight inches plus were now buried inside Claire’s gorgeous ass. Looking down, Tom could not remember a sexier sight. After a brief pause, he began to pull back out. He reversed when he was almost out and then began to slowly fuck her.

“Uh, uh, uh…” Claire grunted with each thrust. At first, it was a pain to be endured. Her ass was on fire and she almost begged Tom to stop. But Roxanne had told her that anal was a few minutes of hell followed by a lifetime of pleasure. It would always be a little bit uncomfortable during the initial penetration, but the more she did it, the easier it would get. The orgasms achieved via anal were unmatched, she had told her. Claire hoped she was right.

“God, you feel so good, baby. You are doing so well, taking all my cock up your sexy ass.”

As Tom picked up his pace, Claire’s pain subsided, replaced by waves of pleasure. “Uh, uh, uh, oh fuck…”

Brenna reached under Claire and her nipples rubbed her shoulder. They were so hard, like bullets. She found her clit and rubbed the exposed nub. Claire’s groans increased to a fever pitch.

“Oh fuck, oh fuck, oh fuck… don’t stop, either of you…I’m gonna cum soon…”

Tom grabbed her hips and rammed his cock deep into Claire’s bowels. Sweat dripped from his forehead and splashed on her back. His cock was swollen and hyper-sensitive. He knew his climax was imminent. He wanted Claire to cum first.

“Shit, shit, SHIT! I’m CUMMING!” Claire roared. Tom had never heard her be so vocal. It pushed him off the edge. He thrust deep for a final stroke and his own orgasm erupted in ropes of cum, shot deep into Claire’s ass.

Tom collapsed onto Claire, his thighs no longer able to support his weight. In a tangle of sweaty limbs, they landed in the middle of the king-sized bed. Brenna rubbed Claire’s shoulder.

Tom’s phone rang. Dazed, he reached over and answered it. “Hello.” He was still catching his breath.

“My dear Tom, that was an excellent performance. I hope I looked that good when you fucked my ass…”

“Roxanne? Is that you…what?” Tom’s brain was in a fog post-orgasm. Blood rushed back to his brain.

“Of course, dear.” Roxanne smiled to herself.

“What the fuck?” Then it hit him. He suddenly knew.

“Smile dear, you’re on…”

“Fucking Candid Camera…” Tom looked up at the opposite wall and smiling, blew a kiss…

 

To be continued…

 

 

 

 

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