A Different World Aftermath

A Different World Aftermath

Heloise woke up with her ass pussy full of Tom's cock. His arm was across her waist, slowly stroking her cock. She lazily pumped back, burying his cock deeper.

"I love waking up with your cock in my ass," Heloise said sleepily.

"Good morning!"

"Anytime I wake up with you fucking me is a good morning!"

Heloise wriggled her sumptuous ass tighter against Tom. They were several weeks into their relationship and comfortable with each other. They were not exclusive but rarely slept alone, with one usually staying at the other's apartment.

Although he used them, Tom felt uneasy using terms of affection with his transsexual lover. He never called her darling, sweetheart, or any other name that lovers called each other. At a visceral level, he feared that using intimate names would take their relationship to a place he wasn't sure he wanted to go.

Tom considered himself a heterosexual man who had sex with a transgender woman. At best, he figured he was bisexual.

When he met his neighbor, Heloise, she was a free-spirited transsexual living a libertine life. She had many and varied lovers and, given her modeling profession, was always at one of the many avant-garde parties in her San Francisco area social set.

Most were mere excuses for wild sex parties, where A-listers and wannabes indulged their sexual deviances in private. She had been fucked and fucked male and female superstars.

Since meeting Tom, she had spent most of her free time with him. She was deeply and completely in love with her neighbor. She was aware of the limitations of such a relationship and Tom's reluctance to commit to it fully. However, she was prepared to risk it because he was so special to her.

"Do you want bacon and eggs or to suck my dick and have cum for breakfast?"

"Bacon and eggs," Tom laughed and smacked Heloise on her full peach butt. "As much as we sucked and fucked last night, there wouldn't be enough cum from either of us for a decent breakfast."

Heloise shivered as she slid forward, and his dick fell out of her ass. She turned in the bed facing him and kissed him while grinding her semi-hard cock against him. She felt him stiffen as they kissed. Mentally, she sighed. She was committed to him but knew he had reservations about their relationship.

"How about we go out for breakfast? We could go to Addie's Café; I crave that scrumptious. spinach omelet."

They rarely went out because she knew Tom was uncomfortable being seen with her. It made her sad, but she was the one whose actions defined the connection as sexual. You can't blow a guy in the laundry room on your first meeting and expect a strong emotional attachment.

"I've got that Zoom meeting with Karen Allen, the vice president, at 9 am."

Tom rolled to his back, and Heloise followed, nestling her head against his hairy chest with her leg between his; her thigh was against his cock and his against hers. Tom caressed her butt, running his hand from her waist, over her butt cheeks to her thigh, and back up.

"I'd forgotten about that. Have they decided to bring everyone back into the office?"

Heloise partially raised her upper body, and her hormone-enhanced breasts slid across his chest, sending a shiver through her body. She looked at his unshaven face and felt the intensity of her love for him.

She knew loving him wasn't a good thing. They agreed early on their relationship was about sex and friendship. They even dated others to maintain the illusion.

"Karen says the corporate bean counters have crunched the numbers and that this is a better model for the business. They planned on operating remotely for the foreseeable future."

"Ah, okay! I like that. I enjoy coming home to you after my modeling assignments. But you're a lousy cook!"

Tom playfully smacked her ass, eliciting a feigned scream of pain.

"You said you were looking for a BBC when we met, not a chef! "

Karen Allen was Tom's senior manager, business travel companion, and sometime lover. She was a painfully thin woman with long, spindly arms and legs and a body like Olive Oyl in the old Popeye cartoons. Unlike Olive Oyl, she had respectable large C-cups and a wet, tight pussy.

She sawed her wild oats in college, attending the wild sex-imbued frat parties and having a long-term affair with her married female college advisor.

In the fifteen years since she graduated college, she became a type A personality, eschewing casual sex and becoming career-oriented. Tom Moore was the exception to the no casual sex rule.

Initially, they only had sex when they traveled together; even then, it was more of a physical release than a show of affection. He was a great fuck, with a nice size cock, and that's all she needed.

Since his divorce, she had become clingier. It was still a no-strings-attached relationship, but she was vying for something more permanent. She knew of Heloise and suspected that they were more than friends. However, her ego said no woman or transsexual could compete with her when she decided she wanted a certain man.

Karen and Tom's affair began before his divorce and continued through and after it. To Heloise's chagrin, Karen has lately sometimes spent the night at Tom's place.

Initially, Heloise was indifferent to what they did. She had a black cock right next door she could suck and fuck and was in hog heaven. She wasn't sure when he changed from a BBC to a man she cared about.

She cried the night he described his relationship with Karen as similar to theirs; it was about sex and friendship, nothing more.

"Come on! Let's take our shower," Tom said.

"Sounds like a plan!"

Tom pulled her to her feet, embraced her, and squeezed her butt. He was ambivalent about his relationship with Heloise. He cared for her but was concerned about what their relationship had become. It was like they were dating!

His cock plumped, watching the delicious roll of her heart-shaped ass as she led him to the shower. There were two sides to Heloise, he thought wryly. There was this side, the very fuckable ass. Then there was the other side, her very suckable dick!

He recalled the first time he sucked her dick. It was several weeks after she blew him in the laundry room of their building. They had fucked a few times, and Tom discovered that a tight anus was as good a fuck as a tight pussy.

They were sitting on the sofa in her apartment, toking and mutually masturbating each other while watching old movies on television. These sessions usually ended with Heloise either getting fucked by Tom or sucking him off. That night, his inhibitions lowered by the THC, he leaned over in her lap and took her cock in his mouth.

Heloise was surprised but delighted. She had developed a genuine affection for this large black man and wanted to continue their relationship. After gently instructing him in the fine art of cocksucking, watch your teeth being the first instruction; they settled into sharing cocksucking, even 69ing.

Over time they graduated to fingering each other's assholes while they 69ed. However, Tom drew the line at being fucked.

He was having trouble reconciling his feelings for what was essentially a feminized man. Adding to his ambivalence, Karen was pushing for a commitment.

Chapter 02

The dress for the weekly Zoom meetings was casual. Since he would only be seen from the waist up, Tom shaved, wore a polo shirt, and nothing else. He suspected the other attendees dressed similarly. He knew Karen did since they sometimes had Zoom sex after the meetings. It was the post-pandemic version of phone sex.

For this meeting, Karen wore a freshly pressed, starched blouse with a lace demi bra, matching panties, and nothing else.

She was a hard-driving, no-nonsense corporate type. The isolation of the pandemic and her affair with Tom exposed a submissive exhibitionist side of her she didn't know existed. She learned to get off on playing with her pussy while conducting company business by video.

Throughout the meetings, Tom would DM Karen. He would tell her to finger herself and then suck her fingers clean on camera. It titillated them to be conducting business with the staff while sexting each other.

Tom Moore had unexpectantly exposed her and that side of her personality on one of their power lunches.

Rather than having video sex this time, Karen sexted Tom to meet for a lunch meeting at a small park up from Fisherman's Wharf. The park was semi-secluded or as secluded as anything was in San Francisco. It was a hot day, and after the Zoom meeting, Karen had merely taken off her panties that were soaked with her pussy juice and put on a mid-thigh skirt.

She understood that the power dynamic said she shouldn't have sex with a subordinate. However, the exigencies of the pandemic and the mental and physical dislocation of being under quarantine for nearly two years redefined relationships.

Besides, she had fucked Tom a few times on business trips prior to the pandemic and his subsequent divorce. He was not the fabled BBC but an adequate lover. She fucked many black men during her college slut days, and she decided BBC was like the unicorn, often sought but never seen.

"Pull your skirt up so I can see dessert while I eat lunch."

"I'm not going to do that! What if someone sees me."

"Then they'll know you're a closet slut who gets off on being exposed in public."

Uncharacteristically, the hard-charging Type A personality giggled. She recalled him making her ride his cock in the hotel's jacuzzi on one of their business trips. It was her first experience with public sex and she was hooked. From that event, they slowly evolved into a D/s relationship.

In the weeks since his divorce, something changed in Tom. He became more dominant, seemed more sure of himself, and was more sensual. Karen couldn't put her finger on any specific change; he just seemed sexier.

She sat her Mission Burrito on the bench beside her, nervously glancing around the park. As usual, the park was busy with locals taking advantage of the unusually warm day. She raised her butt and wiggled her skirt up around her hips. The wooden bench felt cold against her bare ass.

"There! But what would I say if someone I know sees me?"

"Tell them you're freeing your inner slut!"

"I feel so exposed!"

Tom reached over and stroked her cleanly shaved but dripping wet cunt.

"And you love it, don't you?"

Karen froze but didn't stop him as his index finger sank into her cleft. She glanced up and down the path, terrified but more turned on than ever.

He glanced around as he ate his sandwich with one hand and fingered Karen's pussy with the other. Privately, he was amazed at his forwardness and attributed it to his relationship with Heloise. Though ambivalent about their relationship, Heloise was exactly what he needed after his divorce. She helped him restore confidence in himself, and Karen was the beneficiary.

Tom was raised in central California in the permissive atmosphere of Santa Cruz County, with its nude beaches, permissive marijuana policies, and where sex was a full-contact team sport. However, he and his ex-wife were not part of the liberal group.

They toked and occasionally hot tubed nude with close friends. But aside from that, they were very conservative. The marriage counselor they tried before the divorce told them to loosen up. She suggested that some recreational fucking might help their marriage, but they never did.

Tom began to loosen up when Heloise entered his life. The first time he met her, she sucked him off in the laundry room. She was bawdy, out there, and ready for anything! Her attitude about life and sex rubbed off on Tom. Eventually, at 40 years old, he sucked her cock, his first, and found it wasn't so bad.

He attended a few house parties with her. At one such party, Tom had the mind-blowing experience of fucking and being sucked by a married power couple. In one scene with them, he fucked the husband's ass while they were 69ing, and the wife was sucking his balls. He was cumming in the husband's ass when his wife pulled his cock out and had him finish in her mouth.

It was surreal to see the same couple featured on the local news as recipients of awards at charity events or holding fundraisers for the mayor.

His growing dominance of Karen directly results from his relationship with Heloise and his experience of her lifestyle.

"Stop, Tom! I'm getting so wet, and people are watching us!"

Karen was stunned but incredibly aroused when Tom removed his finger from her pussy, stuck it in his mouth, sucked it, and put it back in her pussy.

"Have you ever been watched while having sex?"

Her sandwich was forgotten; Karen placed her hands and palms on the bench and pumped her hips against Tom's evading finger. It was terrifying and exciting to be so exposed in a public place.

"No! Well, yes, but I was at a frat party in college."

In fact, Karen recalled very little from that night. Her roommate convinced her to try shrooms, the mind-altering mushrooms. Everything was hazy after that. She seemed to remember being passed around like a party favor, sucking dick, eating pussy, and being spit roasted, but she wasn't sure.

"How did it feel?"

"I was so high I don't remember most of it. But it was exciting."

"Sit on my lap."

"NO!"

"Then we should eat up and get out of here. I need to get home and finish the coding on that project we're working on."

Tom astonished Karen by wiping the juices from her pussy on his sandwich. He took a big bite and winked at her.

"I knew it was missing something."

"You're terrible," she giggled.

This new, more assertive Tom entranced Karen. He was much different from the casual fuck he was when married. He was enticing, commanding, and fascinating.

He was pushing her boundaries, and she was terrified about how far he might go. It was like the time they were traveling for work and going out to dinner after a client meeting. While sitting at a table in a posh restaurant, he told her to take off her panties and hand them to him.

"I can't do that," Karen protested. Who the hell do you think you are, asking such a thing?"

"I'm the guy who made you suck my dick on the elevator and who fucked you in the bathroom of an airplane. You know you like your buttons pushed, so hand me the panties."

He reached his hand across the dinner table with a smug smile, waiting for her to comply. She did as he asked, beginning her journey into submission. She got so wet she stained the fabric on her chair.

It was liberating for this hard-charging, self-sufficient executive to submit to this handsome black man. She began to fantasize about exhibitionist sex and to live out those fantasies.

"If we hurry, we can get a quickie before anyone notices," Karen said, straddling him in a reverse cowboy.

Tom lifted her skirt, positioned his tool at her entrance, and sighed as he sank into her pussy. They fucked slow and long with the warm afternoon sun beaming down on them.

They fooled no one about what they were doing. Some passersby smiled and nodded; others were outraged, but none reported them. One of the aftermaths of the pandemic was that people became more tolerant.

"You are so fucking wet! You like fucking in public, don't you?"

"I feel so strange! At once terrified of getting caught and at the same time willing to risk it for the excitement."

A man in a business suit carrying a McDonald's bag sat on the bench across the path from them. He smirked and nodded his head toward them.

Karen felt the heat of embarrassment flush her body. The man knew what they were doing and would eat his sandwich and watch.

"You're being impolite. Say Good Afternoon."

"I can't do that," Karen hissed.

"Why not? He can see you're a slut, and he obviously likes to watch. Say Good Afternoon."

She struggled weakly, giving token resistance when Tom raised her skirt so that the man could see Tom's dick in her pussy.

"Say it, you freaky bitch! You know you want to."

Karen's pussy was spasming continuously as she watched the man watching them. This was the new side of Tom that excited her, the part that pushed her outside her comfort zone. She was a senior vice president with a multimillion-dollar internet portal, and he had her acting like a streetwalker, and she loved it!

"Good afternoon," she said hoarsely. She cleared her throat and repeated her greeting.

"Good afternoon," the man said. "Nice show!"

"Good pussy too! Would you like some," Tom offered

Karen opened her mouth to protest, closed it, and waited for the stranger to reply. She knew in that moment that the power dynamic had changed. She was still Tom's boss, but now he was in charge of her body. If he wanted her to fuck this stranger, she would.

"It looks like good pussy, and I'd love to. But I'm married and afraid of getting caught. That would destroy my marriage."

Karen's head was spinning as she slowly rose and fell on Tom's cock. The unimaginable excitement of offering to fuck a stranger was well outside of her comfort zone. But she would do it in a heartbeat.

"Oh fuck," she moaned.

A massive orgasm shook her body. Her head dropped to her chest, and for several moments, she forgot where she was as rotated her spasming pussy on Tom's cock.

"Did you just cum," the stranger asked.

"Yes," Karen gasped.

Her orgasm was almost continuous, like a series of electrical shocks roiling her body

"She's cumming so hard," Tom groaned," she's making me cum too."

Tom arched his back, trying to keep his cock in Karen's spasming pussy as he came pumping seeming quarts of jizz in her pussy. Her convulsions were so intense that he thought she was going to pinch his dick off.

The stranger's sandwich lay on the bench next to him. He used his open palm to stroke the huge bulge in his suit pants as he watched the white foam build on Karen's pussy and Tom's black cock.

He could see the lips of Karen's cunt spread tightly around Tom's cock with her enormous clit slid up and down his shaft. The contrast of pink shaved pussy and Tom's black cock was mind-blowing.

He was tempted to walk over, kneel down and lick her pussy and the black guy's cock. He hadn't tasted a cock since college twenty years back.

He moistened his suddenly dry lips and looked furtively up and down the asphalt path. Although no one was close to them, there were people further down the path and on blankets in the grass. He ruefully shook his head. There was no way he could do it.

"Thanks for the show," he said, standing up. He walked over and tweaked Karen's nipple, then hurried down the path.

"We had better get away from here," Tom said.

"Why? Somebody else might come by and take us up on our offer."

He slapped her firmly on her heart-shaped ass. "Get up, slut!"

Karen stood, and Tom's cum ran out of her pussy like water over a waterfall.

"Oh my God! You've never cum this much. Do you have any tissue? I need to clean up."

"I have a better idea. It will confirm your slut status."

Tom gripped her waist, spun her around, lifted her skirt, and covered her pussy with his mouth. Karen's skirt fell across his head, covering it and trapping the aroma of her arousal. He sucked her, drawing his seed from her vagina.

"Stop! Stop, people are watching!"

Initially, she tried to push his head from under her skirt. However, when he took her clit in his mouth and sucked it like a small dick, she gripped his head, holding it tight to her pussy.

"Oh fuck! What are you doing to me?"

"Letting you be what you always were," Tom chuckled. " a slut who likes kinky sex."

Karen stepped back, and Tom sat back on the bench. Her legs felt like water, and she could sleep for a week. She turned bright red when she heard a smattering of applause from some people on blankets in the grass.