Tom's world had been drastically altered. His sex life at home with his wife of thirty years had dwindled to a point of non-existence. She never initiated sex and when he asked for it, she routinely turned him down. She was too tired, busy playing spades online or watching a show on her tablet.
The very rare occasion she did relent and agree to sex, it consisted of her turning on her side, pulling down her bottoms and telling him to be quick. It was like she was doing a chore that no one wanted to do, such as cleaning the toilet. While Tom fucked her, she would be either playing cards online or watching the next episode of her latest series.
Tom usually fantasized about one of his online playmates while plunging his big cock in and out with no variation. She would not allow alternate positions, oral sex or even playing with her breasts. Tom was a breast man at heart and loved tweaking nipples and sucking on them. He no longer got to enjoy these aspects of sex. The intervals between any sex became longer and longer until Tom rarely if ever even asked for this vanilla sex anymore.
The day after Tom's encounter with his new playmate Kianna, Tom sat at his desk and pondered his new situation. He had met Paisley and the connection was strong. He loved her spirit. Physically she was his type. Petite, but not fragile, she had the body of an athlete. She had played soccer in high school.
She also lived up to her screen name, BigBreasts22. He had seen two pics of her body. One was a straight view of her nude upper body, which highlighted her full breasts. Tom estimated that they were between a D and DD with a Playboy like shape.
The typical Playboy breasts were fully round at the bottom, with a gentle slope from the top. Every girl looked like she had her breasts sculpted by Hef's masters. Other magazines would feature girls with realistic breasts that may be large or small but had slight imperfections that all humans had. No one really looked like the Playboy girls, right?
Tom mulled this over in his mind while the next consult waited on his desk for his undivided attention. But Paisley's breasts had that Playboy aura. The second pic of her pulling her breast away from her chest by the nipple had been the object of many masturbation sessions.
He had sent her a video of himself masturbating, in hopes of getting one from her in return. After viewing it, she had told Tom how much it had turned her on and that she was amazed at the size of Tom's cock. Then she abruptly left, citing a lunch date with a friend as the reason. He had not chatted with her in four days now. Before this, they had not missed a day of chatting in the month since they first met.
What happened? Was she okay? Maybe she had decided that things were getting too intense and that she didn't want to continue down the path that they were on. But she had said she loved his cock and wanted it. Was this just her being nice? Tom couldn't be sure. Doubt played in his mind.
Tom then thought about his other new playmate, Kianna. Physically she was not his usual type. Also petite like Paisley, she was thinner. A runner, she had a great ass and lithe, strong legs. Barely exceeding one hundred pounds, she had A-cup breasts with pointy little nipples.
After their voice masturbation session, they had exchanged pics. Kianna was a fiery little redhead with a personality to match. She had many male admirers on Lush that she played with, but none like Tom. She manipulated those other guys, while Tom had been the master of their encounter.
Kianna and Tom had chatted for several hours later that day and he really liked this girl. She was just nineteen-years-old and in her second year at Oregon. She didn't have a boyfriend, as the few guys she had dated were immature. Like most girls her age, she was far more advanced than the boys. Tom chuckled at this thought. Young guys were stupid. They may have no body fat, but they were mostly immature and could barely hold an interesting conversation with girls their age. It wasn't surprising that Tom met so many young women on Lush that wanted to talk to older men for this very reason. Kianna had told Tom at the end of their chat that she would be unavailable for the next two weeks. She had a major project that she needed to concentrate on and playing with Tom would distract her. When Tom had expressed his disappointment, she promised to make it up to him after it was completed. So Tom was back to his prior state with no one to play with.
Later that evening, Tom was back in the chat rooms. His curiosity was piqued by a screen name of SouthernGal. He checked out her page and discovered her name was Roxanne. She was originally from the South but now resided in Southern California. She was thirty-two-years old. Sexual preference was listed as bisexual. Tom decided to approach her in the room. Hey there, how are you tonight? Tom waited for her response. He really hoped she would be amenable to chatting as there were no other prospects in the room. There was no response for several minutes. Tom thought she was ignoring him.
I'm doing fine, how about yourself?
Tom was surprised at the response. He was sure after this amount of time she was not interested. I'm doing well. Trying to find someone to chat with that can hold up a decent conversation.
Well yes, that can be difficult in the rooms. Most guys here are very uninteresting. They cannot hold my attention for more than a minute. I checked out your page, hence the delay in my response. So far you have passed the initial test to keep my attention. But there are more to come. Have you read my page? Roxanne smirked as she typed this. So many guys were scared away by her vetting process. But it had the desired effect. Those who passed her tests were worthy of her time.
Tom was a bit taken aback, but also intrigued. Here was a very confident woman who was obviously intelligent and did not want to waste her time with boorish men. Yes, I have. I am guessing that I will now be quizzed?
Very astute of you. Yes, there will be several questions bout me that you should have gleaned from my page. If you pass, our conversation will continue. If you fail, then I wish you a good evening. Ready? Roxanne leaned back from her keyboard and waited. Many guys asked if she was serious. Some simple left the conversation. Others attempted the test and failed. She had not found one that had passed in a long time. She was hopeful with Tom.
Yes, I am. Fire away. Tom had read her page and even looked at the albums. He was confident he would pass.
Roxanne asked Tom three questions: What were her mother's favorite movie and character? What was her political affiliation? What was her favorite weapon?
Tom looked at the questions and smiled. He knew the answers. He typed the correct responses. Gone with the Wind. Scarlett O'Hara. Conservative Republican. From the South. Smith and Wesson MP Shield 9mm.
How did I do? Tom waited for her grade.
Roxanne read the answers and was pleasantly surprised. He answered all three correctly. In order to do so, Tom had to read her bio, open her albums and then make a determination about her political ideology based on the information gleaned from her page. This meant that he was intelligent as well as thorough. She was impressed. You did very well. Now to continue our chat, let's move offsite to Trillian. I do not like to chat here.
Tom agreed and they both went to Trillian. It was a messaging site Roxanne used for her business and personal conversations. She was a stickler for confidentiality as well as security.
The next two hours flew by. They talked about anything and everything. Tom told her all about his situation at home. Roxanne felt a strong attraction to Tom. She was drawn to him, was the way she phrased it to Tom. She felt bad for his situation and decided on a bold move to brighten his evening.
Tom, I am going to send you some pics. I want you to open them and tell me what you think. Ok?
Ok. What kind of pics are you sending? Tom hoped they would be revealing, based on their long conversation.
Ones that I hope you will enjoy them and they will brighten your evening. Tell me when you have received them.
Tom agreed. He saw them appear in his inbox. He opened them and was pleasantly surprised. They were pics of Roxanne nude. Closeups of her pussy, with the lips glistening wet. Her breasts were full with stiff nipples and dark areolas. There was a short video as well. It was a large cock plunging in and out of a pussy. Tom assumed it was Roxanne's. Her lips gripped the shaft as it penetrated her dripping cunt. After a few minutes, it pulled out and shot a load of hot cum all over her breasts, painting each nipple with the sticky fluid.
Now go and masturbate while you look at the pics and the video. I will wait for you to finish. Come back and tell me all about it. Tell me how you liked my pussy and breasts and how they made you cum. I also want a pic of your cock right before you cum.
Tom was shocked, but also incredibly turned on. He agreed and grabbed some lotion, tissues and his phone. Following her instructions, he stroked his cock while looking at her pics. He settled on the video to finish. Right before he climaxed, he grabbed his phone and took a pic of his engorged cock, with the head a dark purple and the veins prominent along the shaft. He put the phone down and continued stroking. After only a few more, he shot a massive load into the tissues. He cleaned his cock and returned to the conversation.
Wow, Roxanne, you are stunning. I shot a massive load. I just sent the pic of my cock, per your request.
Roxanne opened the attachment and gasped. She had seen her share of cocks, but this one was almost perfect. It was quite large. Long and thick, it was bigger in her estimation than most of the cocks she had encountered. The large mushroom head was in perfect proportion to the thick shaft. Her pussy started leaking fluid as she admired Tom's cock. Mmmmm, that is some cock you have there. I didn't know you were that large. And almost perfect proportions. I'm getting wet just looking at it. I'm glad you enjoyed what I sent. I hope you were able to relieve some tension. I must say, I am drawn to you. In a way that I have not been in some time.
Thanks. I find myself drawn to you as well. Besides the obvious physical attraction I have towards you, I mean I just shot my wad while looking at your amazing body, I feel an emotional and intellectual pull from you.
Likewise. So I am going to be bold here and do something I rarely do. I think we should meet. If it goes well, I want to fuck you. I want to give you all the sexual experiences that you have been denied for so long. And introduce you to some you have not yet enjoyed. What do you say? Roxanne sat back and waited for Tom's response. She had only done this once before with someone online. She kept the image of Tom's throbbing cock in her mind while she awaited his reply.
Tom was not expecting Roxanne's offer. He thought for a moment. Was he ready to cheat? His cock stirred at the idea. He paused, then typed his reply. That sounds amazing. I have an idea. I have to teach a class in Long Beach in two days. I have a large suite reserved for two nights. Meet me in the bar on Wednesday night. I am staying there Wednesday and Thursday night as my class is four hours on Thursday and Friday morning. If you approve of me, then you can stay with me for as much of the time I am there as you like. If after we have a drink at the bar you do not want to stay, then you can leave with no ill will on my part. Is that acceptable?
Roxanne was surprised. She did not expect Tom to be so bold and decisive, but she liked it. Her intuition was again proven right. Tom would be an impressive addition to her stable of lovers. Agreed. I am impressed. This will be an experience you will not soon forget. I will meet you in the bar of the hotel. Send me the address and the time for our rendezvous.
Tom and Roxanne both logged off. Tom's head was spinning. He had just made plans to meet and fuck someone he had just met online. Was he crazy? Maybe, but it felt right. He could not wait for Wednesday.
The sound of heels clicking on the hardwood floor snapped Tom back to reality. He had been deep in thought. Here he was, sitting in a hotel bar waiting to meet a woman he had just met recently online, and if things went right he would soon be upstairs in his room fucking her in a matter of thirty minutes or so. Wasn't this crazy? He was a married man, although not really happy. Friendship was good, but the sex was non-existent. They were like friends with no benefits.
His gaze followed the sound of the heels. She was blonde, a little over five-foot-six inches, he guessed. Stunning would be the word to describe her. She was clad in a tight, red, sleeveless dress that left little to the imagination. It clung to her voluptuous frame like a second skin. Tom could see every curve and he liked what he saw. Her full B-cup breasts jiggled with every step she took. She was headed straight for his table with a smile on her lips.
Was this Roxanne? Might be, since she checked quite a few boxes. Although Tom had seen her breasts, gaping pussy and a video of a cock fucking her up close, with a finish on her amazing breasts, he really did not know enough to recognize her fully clothed. She directed a smile and a wink in his direction as she passed his table, headed for the booth in the back occupied by two other beautiful women in similar attire. Most guys were sneaking glances towards that booth. None figured they had a shot, as the bar was full of tired, older businessmen who just wanted to get buzzed or even wasted after a hard day. Two other guys were not like the rest and they were dressed in jeans and t-shirts.
The next person to enter the bar was another tired businessman. He looked like he needed several drinks and Tom did not envy him his life. A modern-day Willie Loman came to mind. Tom took another sip of his scotch and drifted back to his thoughts. His watch read 4:05.
Once again, the sound of heels clicking brought him back to the present. He glanced up and saw another blonde enter the bar. This one was even more stunning and he had not thought it possible. Blonde hair, cascading down to her shoulders with a few slightly darker tan streaks that gave it a depth that most blondes did not have. Elegant and sexy heels, almost fuck-me heels but not slutty looking. Tom guessed Louboutin. Navy slacks that hugged her perfectly round ass and flared slightly at the ankle. A white button-up blouse, made from a silky fabric that was diaphanous. He could just make out the dark circles of her areola and nipples. It was subtle, not obvious and extremely erotic. She obviously was not wearing a bra. Her ample breasts bounced ever-so-slightly with each step. Not a garish jiggle, just an ultra-sexy shake.
Her piercing blue eyes were fixed on Tom as she strode straight to his table. "You must be Tom." It was more of a statement than a question. She exuded confidence and overwhelming sexuality all wrapped up in elegance. She was several steps out of his league, at least the way he thought back in college.
"Yes, I am. How did you know?" Tom's voice was steady and even, despite the uneasiness he felt in the pit of his stomach.
"You were the only man worth talking to in the entire bar. If you were not Tom, then I would have turned around and left." Roxanne took in his appearance. Light brown hair with just a touch of gray and cut by an expert, not a hack at SuperCuts. A navy blazer that was obviously Italian and custom-tailored to his fit torso. This rested on a pair of broad shoulders. A white button-up with only the top button open. Charcoal slacks fit his muscular legs perfectly and he sported a pair of walnut monk-straps. The latter showed a bit of flair. Oxfords would have been the safe choice, but monk-straps are just edgy enough to impress but still be classic. A nice touch and showed her that Tom knew men's fashion. He earned another point.
"Please, have a seat. Let me get that for you." Tom smoothly rose and pulled out her chair. It was a move of experience. It was automatic, as he did this out of habit, not just to impress her. Being of Southern heritage, Roxanne greatly appreciated small gestures of chivalry. It was a disappearing quality and one she held very highly. Two more bonus points that Tom didn't even realize he had earned.
"Thank you, kind sir." Roxanne flashed him a smile as she sat down.
"What can I get you to drink? I am having a very nice Lagavulin 11. It is my new favorite for when I want something complex with a bit of peat."
"That sounds marvelous. I love a good scotch and I too love a bit of peat at times. Other times I love a big sherry bomb, but tonight, peat sounds perfect." Score again, for Roxanne had found that a man who appreciates and knows a good scotch is likely to be a cut above the average beer-swilling troglodyte. Another point on Tom's ledger. Tom motioned subtly to the barkeep to bring two more scotches. Kudos again, Roxanne thought, as most guys made such a public gesture getting any waitstaff's attention that it was embarrassing. Another point. Tom was racking them up and he had not really spoken much. Actions speak louder than words, especially in this case.
Fifteen minutes later, Roxanne looked up from her scotch and said matter of factly, "Take me upstairs and fuck me. You have passed." Tom was admiring her cleavage at the time. Three buttons undone revealed the rounded inner breasts that were begging to be touched, at least in Tom's mind. He could clearly see her dark areolas and her stiff nipples poking through the thin fabric. He looked up and smiled when he realized what she had just said.
"Well, then, I must have passed the test. I must say, I am relieved and excited." Tom's cock stirred, thinking about fucking this gorgeous creature in about twenty minutes.
"Well, to be honest, I knew I would be fucking you tonight after two minutes. The rest of the time was simply to make you sweat a bit." Roxanne gave him that Cheshire-Cat grin.
"Shall we, then?" Rising, they both made their way to the elevators and the top floor. As they walked out of the bar, every guy gave Tom that You lucky bastard look. In the elevator, Roxanne stroked her hand up Tom's thigh as she shifted closer to him.
"My, Tom, that is some cock you have there. You never mentioned how well endowed you were. Just modest?" Roxanne's hand grasped the shaft of Tom's aroused member. She marveled at how thick it was and was imagining it stretching the walls of her pussy and how good it was going to feel. She was getting wet at the thought.
Tom blushed at her comments. "Well, I imagine it is big enough to do the job."
"Mhmm, and more than big enough." Her hand remained on his cock for the remainder of the elevator ride. On the top floor, she let go and they exited.
They entered the room and Roxanne looked around, taking inventory of the executive suite. "Nice, Tom. I expected just a regular room, but this is first class." The suite was quite large, with a very large couch that was also quite deep. Roxanne had plans for an encounter on that piece of furniture. A large balcony with a view of the harbor and a very large bedroom with a king-sized-bed were next on her list of positives for the accommodations. A large bar area and a walk-in shower completed the tour.
Roxanne began unbuttoning her blouse. It fell on the floor in a pool of soft, white fabric. This exposed her breasts fully to Tom's gaze. "Lose the clothes, Tom. Now, please." She had that smirk again.
Tom removed the blazer and unbuttoned his shirt. Gazing at the perfection that was the globes in front of him, he thought that they were like overripe fruit, begging to be plucked. So round yet firm, he reached out and grasped her left nipple. Rolling it between his index and middle finger, he tugged on it, pulling it away from her chest. He paused, and then released it, letting it hit her chest with a soft slap of flesh against flesh. He loved that sound and visual and it drove him crazy with lust.
"Mmmm, that felt really good, baby. I know you want to suck on them, so go ahead."
Tom needed no further encouragement. He latched on to the left nipple and flicked his tongue over the tip. Roxanne moaned. Tom then bit her nipple and pulled back. This elicited an unexpected squeal from Roxanne. She grabbed his head and said, "Ohh, you naughty boy. I want you to lick my pussy. I know you haven't done that it a long time. Take your time and savor it. Make me cum."
Roxanne removed her slacks but left the luxury fuck-me pumps on. Tom had only seen that in porn films, but it excited him. Rosanne was porn-star sexy. Not the artificially inflated versions commonly found in many sites, but like Victoria's Secret meets Vivid Video. Their love-child got the best attributes of both parents.
She leaned back on the deep couch and spread her legs. Tom was faced with the sight of a shaved pussy, one of the most beautiful he had seen, in person or online, with swollen lips that glistened. He moved closer and encountered her intoxicating aroma. A sweet and musty blend that made him have to taste her. He leaned in further and lightly licked and kissed her left thigh. Tom shifted and repeated the process on her right thigh. Roxanne enjoyed the attention but was dying for Tom to kiss and lick her pussy. "Fuck, Tom. That feels really good, but I want your mouth on my lips. Now please!"
Tom chuckled to himself. Roxanne wanted things on her own timeline. He decided to make her wait just a bit longer. He nibbled just outside her swollen labia. He licked up the side and got just to the edge of her now extremely wet lips, but then retreated. Roxanne squirmed. Tom finally ended the torture and ran his tongue up her lips, from her anus to her clit. Roxanne murmured something that Tom couldn't hear. She was pleasantly surprised that Tom licked her anus. She planned on letting him fuck her ass later, as he said he loved anal but had not done it in over twenty years. Tom continued his assault on Roxanne's pussy. He lapped her lips and sucked on her clit. Two fingers were inserted deep into her sopping wet cunt and Roxanne's head lolled back and her eyes closed.
Roxanne was impressed with Tom's oral skills. For someone who had not licked pussy for nearly twenty years, his skills were impressive. She stopped thinking about that as he circled her clit and flicked his tongue rapidly over the tip. Tom then gently sucked it into his mouth and ever so lightly bit it with his front teeth. This sent shock waves of pleasure coursing through her body.
"Mmmm, fuck, Tom that feels so damn good. I am getting close, baby. Don't you dare stop!"
Rubbing her G-spot and tonguing her clit, Tom could feel her impending orgasm. Her breathing became husky and ragged. Her juices were flooding his mouth. She panted, "Oh fuck, OH FUCK! I'm gonna cum..." Roxanne's pussy convulsed and spasmed as Tom's tongue continued to lap at her copious juices. "Unnnggghhh! Oh, SHIT! I'm cumming!" Roxanne shouted. Her thighs clamped hard and trapped Tom's head from moving. He rode out her massive orgasm by grabbing her toned thighs and holding on for dear life, as Roxanne thrashed on the couch. After a few minutes, she released her grip on Tom and opened her eyes. "Mmmm baby, that was amazing. How did you do all that when you haven't licked pussy in decades?"
Tom smiled, her warm juices still coated his face. "I may not actually lick pussy, but I think about it all the time. I do the same thing in my shop."
"You think about pussy in your shop?" Roxanne was teasing him, and slowly rubbed her swollen clit.
"Yes, even there. But when I do a project, I do each step in my head over and over, trying all the different ways of doing it until I can see in my mind the perfect way to do it. Then when I actually start the project, it goes smoothly. Same thing with sex, I guess."
"Hmmm, that sounds unusual but actually makes sense. Here's to your brilliant and slightly different mind. And to my amazing orgasm..."
Tom looked up at Roxanne. She was smiling. He gazed at her breasts. The round globes were slightly flattened, and the nipples were stiff. They were still so perfect that Tom felt his cock throb. He had not cum yet and all this activity had made him as hard as a rock.
"Ordinarily, I would take that cock in my mouth and tease and torment you until you begged me to let you cum. I am very good at it, I even have references...hahaha. But I must have that magnificent cock in my pussy right now. I will let you cum in my mouth after dinner, call it my just desserts. So get over here and fuck me. Please."
Tom couldn't resist and wanted nothing more than to sink his stiff member into her soft, warm pussy. It felt so good when his fingers were inside, he could only imagine how good it would feel with his cock inside. He rose from his kneeling position and crawled forward on the couch. Roxanne spread her legs and he could see her swollen lips, puckered from his ministrations, inviting him to sink his stiff rod inside.
Tom leaned in and kissed her. Her lips were soft and warm, with the slight taste of the scotch they were drinking earlier. Their tongues danced back and forth. He reached out and grasped her right breast and gently massaged it. Tom couldn't get enough of the feel of her firm yet pliant flesh. His thumb rubbed her nipple, feeling it react to his touch.
He lined up his cockhead with her wet entrance. Roxanne moaned into his mouth, their tongues still interlocked. Tom pushed, gently at first, He knew his cock was thick, despite the modesty he proclaimed before. He knew she needed time to adjust to the girth. She gasped as his cock spread her lips and entered her. Because she was so aroused and wet, his cock slid into her without the usual discomfort. A strong push and Tom's cock was all the way in. Tom looked into Roxanne's eyes. She moaned and returned his gaze, with that little smirk on her lips. He began to thrust, slowly.
Roxanne was so full of cock. She had not been this full since the porn star, but he was not gentle or very skilled. She was bludgeoned with his tool. Tom had given her an amazing orgasm orally and now had gently slid his massive cock all the way inside her sopping wet cunt. She raised her legs to allow him to go even deeper.
"Ahhh fuck, Roxanne. You feel so fucking amazing! So tight and wet. Ungggh..." Tom grunted as he began to fuck her pussy in earnest. He could hear their flesh slapping together with every thrust. Roxanne grunted in reaction to each deep thrust. Tom could feel his orgasm getting near. "I'm gonna cum soon, baby. You are so tight, it is driving me to the edge..."
"Cum in me. I want to feel you cum deep inside my pussy." Roxanne grabbed his neck and pulled him in for a kiss. As their lips met and tongues resumed their dance, Tom quickened his pace. After less than a dozen quick thrusts, Tom stiffened and roared, "Ohhhh! Fuck, I'm cumming!" One last thrust and he erupted deep inside Roxanne's soaked pussy. He felt ropes of cum spurt repeatedly into her hot cunt.
Feeling waves of cum shoot inside her sent Roxanne over the edge again. Her orgasm overtook her as Tom shot load after load into her.
They both regained their senses after several minutes. Tom was lying with his full weight on top of Roxanne. "Are you okay? Am I too heavy for you?"
"No, baby, I'm not exactly a fragile flower. I like the feel of you on me."
"Good, I'm not sure I could move anyway." Tom was exhausted but felt incredible.
"I am starving, though. Let's order room service and break out those bottles of red you brought." Roxanne felt tired but was in that post-orgasm glow. This is not exactly how she thought things were going to go, but she was not complaining. Tom was not a charity case, but might be her new favorite lover.
Tom got up and she watched his tight ass as he walked over to the phone to order their food. She was already planning the rest of the evening's festivities...
to be continued...
