Anna Gets a Ride to Work

Anna and Joe were an unlikely couple. They met while working at the same restaurant. Joe was the Executive Chef, and Anna was the Banquet Coordinator. They worked closely together for three years forming a strong bond of friendship while supporting each other through each of their divorces and career advances.

Anna was petite, young and beautiful with a vivacious personality that made her popular, even when meeting new people. Her medium-sized breasts looked larger on her small body. She loved to wear dresses and chose other clothes that showed off her beautiful breasts and tight buttocks. Combined with the fact that she never wore underwear, Anna was imminently fuckable at any point during the day, especially while on a cigarette break. She embellished each inhale with a French snap, and directed her exhales for the benefit of any audience she acquired, being sure to toss her long brown hair in the process.

Joe was much older, bald, and a pear-shaped man. The man of his early forties wore on his physique the hint of a muscular, athletic, and energetic 20-year-old, plus fifty pounds. He displayed his extra weight in his over-sized gut and thick as tree trunks legs. It slowed him down but did not keep Joe from being very active. He loved to mountain bike and played on a city recreational league softball team every Thursday night. Joe was sweet and lovable once you got to know him. Too commonly, Joe earned himself poor reviews when in social situations with new people for being a cocky prick, but never on purpose; though this bit of self-awareness never helped him from repeating the faux pas. His best tactic usually was to let Anna take the lead and gain favor through association with Anna.

Having fourteen years of age on Anna, it was not difficult to surmise that he must bring something special to the relationship for having someone as awesome as Anna be his girl; as unlikely as it would seem. True; Joe had a cute and adorable way about him. His self-effacing brand of humor, an accommodating spirit, and cherub smile usually afforded him a comic likeability amongst friends new and old. Joe liked to think this side of his personality held a wide lead in time of possession over the "Ya come off like a dick" side. And Anna, who knew him better than anyone, found the good side of his personality ran genuine to his core as he frequently sacrificed his own needs for hers, and took pleasure in facilitating Anna's enjoyments and successes. Joe simply felt lucky to be chosen by Anna and needed only her company as sustenance for their love.

Anna loved to have sex, and so did Joe. Joe's age, lack of desirability, and small penis made him a poor lover. Anna had many suitors and always had many different options when it came to sex. And to spare Joe's feelings, and to avoid an onslaught of his sexual desire, she never told him about her current sexual adventures. Anna did love Joe as he fulfilled all the other requirements that a woman would want from a devoted, loving, and supportive life mate. She just did not want his cock. Joe, of course, had his suspicions about Anna's behavior despite her continued, and sometimes angry denials of any sexual activity especially during the most recent few years of their courtship. The fact remained that Anna was a person who enjoyed sex, and while she rarely expressed any physical desire towards Joe, many instances of Anna's expression of sexual desire towards others in Anna's past were often revealed. Joe was certain that Anna was currently having sex with other men. This was a far likelier reality than Anna going completely abstinent over the previous two years; during a time when Anna and Joe drew more close and more intimate than ever.

"Yeah, I like to flirt," Anna would defend herself. "But I'm not having sex."

Joe loved Anna despite his suspicions and maybe even because of them. Now Joe and Anna were on the cusp of moving in together. A last concrete step before marriage. Joe wondered if the dynamics of his relationship with Anna would change. He did not expect that instances of sex would increase. Though he did expect the opportunities to have sex with Anna would increase. As would his suspicions about her having sex with others if she frequently adjusted her routine, or changed her plans unexpectedly. Joe anticipated that he would be spending more time wondering what Anna was up to and beating off to all the possibilities that his perverted brain could imagine.

Joe had an intense smoking fetish that he developed as a child in the 1970's exposed to the last throes of tobacco advertising on billboards and in magazines. He also learned from his first marriage that he had a fetish for being cuckolded. Anna, knowing everything there was to know about Joe, was mostly turned off by his sexual preferences and would indulge him with stories about old flings, while Joe frantically tugged his wiener like a pubescent boy. These stories from her distant past would excite Joe, then a couple of puffs on a newly lit cigarette and Joe would have his five minutes of fun. So the routine began during courtship, and Anna did find some unexpected amusement in rewarding her faithful partner from time to time. This kept Joe delightfully ensnared without much expense in effort or time, which suited her perfectly since she only found it mildly amusing at its best, and downright disgusting at its worst.

"I am not ashing in your mouth!" Anna would scold any time Joe tilted his head back to hold his mouth agape while kneeling at his cigarette smoking queen's feet.

Joe knew that he would be asking Anna to marry him soon. He only had one reservation. He wanted proof that Anna was having sex with others and he wanted that proof to come from Anna's own lips. It was Joe's desire to hear Anna's confession. To finally hear the words spoken in his love's enthusiastic girly voice.

"I fucked him," was going to sound like sweet music in Joe's ears. His cock ached for it.

Anna wanted no part of it. She did all that she could to avoid any kind of sexual contact or conversation with Joe. She saved it for those brief instances when he would jack off next to her while she smoked and she let the tension build until she couldn't handle his pleas any longer and she's do it for him again. That was about all she could muster against her overwhelming feelings of meh towards Joe sexually. Conversations with Joe leading up to their move-in date made it clear to Anna that Joe definitely had sex on his mind and Anna told herself that she'd figure it out.

"He'll be at work at predictable times," Anna told herself. "I'll be able to maintain."

Joe banked on his predictability as an asset in his quest to learn of his love's indiscretions. He was no longer a Chef and was working on a Master's Degree in Education to become a school teacher. While going to school, Joe substituted for the local school district and needed to work every day that school was in session to make ends meet. Before moving in with Anna, he hatched a simple plan. He would pick a day when he thought it would be most likely that Anna would have someone over while he was at work. Then he would leave for work as scheduled, then park the car nearby but out of sight. Then he would return home when Anna took her son from her failed marriage to school, and hide, and wait.

After moving in with Anna, Joe kept to his plan. He did not pressure Anna at all sexually. Though he did encourage her to tell stories about the young men with whom she worked at a local gourmet pizza parlor. While Anna's experience as a restaurant manager meant that she could have run the whole restaurant herself, she enjoyed her low-responsibility position as a server that afforded her more time to be a mom to her seven-year-old son. Indeed, Anna was the "old" mom at the pizza parlor compared to the teenagers and young adults that she worked with. Joe would listen intently to Anna's stories about what a cook said to her, or how a boy server reacted seeing her out of her work uniform when she showed up in a pretty dress. Joe could tell that a boy named Jacob, just barely a senior in high school, was the one Anna was most likely fucking or would fuck. Her eyes would glint with extra excitement and a wider smile would accompany any recollection of her interactions with this boy. Without a car, Anna relied on Uber, friends, and family to get her son to school and to get herself to work when Joe was unavailable. And when Anna told Joe that Jacob would be picking her up to take her to work on Thursday mornings, Joe knew that Thursday would be the best day to get his proof.

Joe gave Anna a couple of months to get comfortable in her routine. He never brought Jacob up in conversation and would not ask about him when Anna indulged him with a cigarette and a story from her past. Sometimes Joe would ask Anna in passing, "Are you getting to work ok?" as if relying on the teenager might cause problems, but really Joe was listening and watching for any hint of infidelity that would make his cock jump. He noticed that Anna spoke of Jacob less, but whenever he did come up in conversation, Anna would pause in her retelling of events as if she were trying to remember exactly how she wanted to relay how something happened, what he said, and what she said in response. Joe longed to see for himself what was happening when young Jacob picked up his bride-to-be on Thursday mornings.

Joe could wait no longer and put his plan into action. Joe left for work in typical fashion; discreetly pecking Anna on the cheek while she got breakfast ready for her son.

"Love you bye," Joe muttered his compulsory goodbye to which Anna gave her standard, "Love you" reply.

Her Uber driver would be there soon to take her and her son to school and Anna back to the apartment. Joe waited in an out-of-the-way corner of their apartment complex's parking lot and watched the house until Anna and her son climbed into an SUV and headed off to school. Joe quickly rushed back into his apartment with his heart pumping blood into his cock with every step. He changed out of his work clothes, then put on some loose fitting basketball shorts and a t-shirt. He grabbed a stack of jack cloths, which were nothing more than tattered old t-shirts that he only used for masturbating, and took up his hiding position in the corner of his room. In the three bedroom apartment, Joe and Anna each kept their own room, for the purposes of maintaining some decorum until Joe and Anna made a final commitment to each other.

Anna's son and Joe's son from his failed marriage shared a room when Joe and Anna had their custodies. Joe allowed Anna to have the master bedroom which she needed for the extra closet space and a girls only toilet. Joe left the door ajar to his room, as he always did in anticipation of this day, to make sure that any sounds would not be muffled by a closed door, and that Anna's suspicion would not be raised by a slightly ajar door. Because of careful study and preparation, Joe knew he could not be seen from the hallway from his hiding spot and knew that it was unlikely Anna would enter his room. Ever self-aware, Joe also brought with him a super big gulp cup as a surrogate toilet, as the need would surely arise.

Joe waited with heart-pounding anticipation which resulted in a vigorous tenting of his basketball shorts. He delayed the gratification of touching himself and only listened as he heard Anna return to the apartment. Dressed in leggings and a sweatshirt, Anna quickly went to work cleaning up after breakfast, tidying up the boys' room, and getting a load of laundry together. Of course, she smoked her cork-filtered, Marlboro Blend 27's, 100's next to the open patio sliding glass door, which happened twice while she performed her chores. Joe listened intently. After the clothes washer was started, Joe could hear her footsteps return to her room, but did not hear her door close. The next few minutes passed like hours as Joe wondered what she was doing. He could not deny his curiosity and he quietly opened his door beyond ajar to agape. Quickly, he strode down the edge of the hallway without making a sound, past the boys' room and stood just outside Anna's open door.

He could hear the sound of her camera shutter on her phone. He knelt down in preparation to peek in. He figured he would be more out of the line of sight if he peeked inside her door at floor level. Joe quickly peered around the corner of the door frame and returned back to his spot to assess what he saw. His cock already processed the scene by fiercely pulsing up and down in his shorts. Anna laid on her back on her bed, arm extended, and taking selfies with her cell phone. Best of all, with Anna facing the opposite wall on her bed, Joe would be able to stand, peek through her door, and not be detected. Joe couldn't wait to see what Anna was wearing or not wearing in the photos. Because of his low angle, he couldn't tell from his initial glance. Joe stood up in the hallway and peered again around the corner of the doorframe. His cock nearly exploded.

He saw Anna laying on the bed and was immediately shocked to see her wearing her old plaid skirt. Anna kept her uniform plaid skirt from a bartending gig she worked three years ago. The bright red tartan pattern of the enticingly short skirt caught Joe's eye first. Anna's free hand worked her snatch under it, pulling her pussy lips open, then "click" went the camera. Joe begs for Anna to wear the skirt again for him, but she always refuses. A fact that reflected in Joe's purple, erect cock that began oozing pre-cum.

"I don't even know where that thing is," she would ponder, as if that were the only thing that prevented her from giving Joe a sexy show in the plaid skirt.

Next was the thick, black rimmed glasses on Anna's face that gave her a naughty student look that made her look even younger than she was. Then Joe noticed her ruby painted lips well practiced in the sexy smiling and lip biting poses she gave the camera. Next was Anna's hair that she wore in pig tails coming off the side of her head, which were long enough to be brought forward to cover her bare breasts. Lastly, Joe noticed what was between Anna's breasts, rolling back and forth in her gaping cleavage was a single, unlit Marlboro 27, somewhat concealed among the ends of Anna's pig tails. Was Anna finally taking the smoking fetish photos that Joe had been asking for?

Joe peeked again and could tell Anna was done taking pictures because she was now using her phone with both thumbs in the obvious texting motions. Joe quickly decided that whether the pictures were for him, or for someone else, he was very happy with the outcome of the day so far and he scurried back into his room and returned the door to the same ajar position. He did not want to ruin anything and was very satisfied thus far with the results of his clandestine operation. He went to his muted phone both hoping that there would be and hoping there would not be text messages with image attachments from Anna waiting for him. If so, Anna finally fulfilled Joe's request for a smoking fetish selfie. If not, there would be proof that Anna was at least sexting other men...other men with smoking fetishes. The notion made him squeeze his small, but fierce erection. He quickly let go when his nuts pulsed in preparation to cum. Alas, no texts from Anna were on his phone. Joe's cock ached to be touched, but Joe knew better. He wanted to wait until Jacob arrived to take Anna to work. Was Jacob receiving the texts?

Joe knew that Anna had to be at work at 11 am on Thursday mornings and he figured the two hours he'd be waiting in his room would be the worst part of the day. Joe got comfortable in his hiding place, played games on his cell phone, and listened carefully to any sounds Anna made in the apartment. It was all he could do to distract himself from how hot it was to see Anna taking selfies and apparently sending them off to someone else. And Joe relished in how hot she still looked in that plaid skirt. She would wear it to her bartending job with no underwear and show off her pussy for tips. Of course, it also provided easy fucking access to whomever she wanted to fuck. Joe did his best to limit his imagination and save his hard-on for when it mattered. Mercifully, he did not have to wait long. It was only fifteen minutes before there was a knock at the door. Joe perked up in his hiding spot and his flaccid penis was immediately rock hard. He heard Anna walk aggressively toward the door.

Joe stood up, pulled his shorts off, and grabbed a jack cloth. He stood right behind his slightly ajar door and listened. Anna had already answered the knock at the door and greeted a man. Joe could tell it was a male voice but could not make out what Anna and her guest were saying. Then he smelled the familiar aroma of Anna's cigarette.

"Oh my god she's smoking for him!" Joe realized. It was a realization felt by every nerve in his body, especially in his cock. Joe's small wiener pulsed up and down with his racing heartbeat. He grabbed it, but dared not stroke it for the fear of cumming too fast.

Joe heard the sliding glass door open and knew Anna would be smoking near the opening to air out the apartment. He figured he'd have at least five minutes while she smoked. The door to the patio was on the opposite side of the living room from the hallway that led to the bedrooms in the apartment. The patio was small, but fenced in and afforded privacy, so he knew Anna would not have to be discreet. Joe snuck out of his room again and all the way down the hallway, past the boy's room, past Anna's room, and right to the edge before the hall opened into the living room. Joe calculated his risk. He never knew Anna to smoke anywhere inside the apartment, except next to the wide open sliding glass door, and that was only when the boys were not around. If the boys were home, she only smoked out on the patio, or out front with the doors closed. Joe figured Anna would stick to her "no smoking in the house" policy.

Regardless, his racing heart, raging boner, and overwhelming desire to be cuckolded meant that Joe really had no choice but to get as close to the action as possible.

Joe listened just out of sight of Anna and her guest. He could hear their voices clearly. Anna was giggling girlishly.

"Oh, you like that?" He heard her say seductively. "You're such a naughty boy!"

Then it went quiet and Joe could hear kissing sounds. His faced beamed with joy as he finally got what he wanted. His cock was ready to cum at the slightest caress, but Joe continued to delay his gratification. This could be just the beginning. Anna was obviously smoking while making out with her guest, something that Joe had always dreamed of doing with Anna. Awkward attempts were made on more than one occasion when Anna always refused and rejected Joe's "gross" advances. Anna understood the effect smoking had on some men and wielded its power adeptly. She just didn't feel sexual towards Joe, so she only did the minimum to appease Joe with a smoking fetish exhibition when she felt like it. And that never included making out. Joe's cock compelled him to peek around the corner.

Joe ducked down and adjusted his head level to be below the couch level so that he could slowly creep upward and tell if he would be in the line of vision. As he came upward in his crouch he saw Anna taking a drag of her cigarette inches from a boy's face. Joe figured this had to be Jacob; a full two hours early to take Anna to work!

He looked very young. He was taller than Anna, but had a skinny frame that had not yet reaped the rewards of puberty which may have come a little late for this young man; indicated by his chubby, baby-fat cheeks. Yet he was old enough to serve alcohol. His sandy blonde hair was loosely styled, but not well coifed. His youthful exuberance gleamed in his eyes and expressed through his hands which were going to work on Anna's bare bottom underneath the plaid mini school-girl skirt. As Joe rose from his crouch while remaining out of sight, he could see Anna still wearing the skirt, black framed glasses, and pony tails as the only covering for her beautiful tits. Jacob held Anna close to him while she smoked, pushing his hard-on into her abdomen. Anna French-inhaled her drag, then blew her smoke directly up into Jacob's lipstick smeared face with a smile and then started making out with him more. It was clearly evident that this was not their first time being intimate.