Adriana Learns to Love Again

In late September, Adriana was aimlessly scrolling through a dating profile she had made but had zero expectations of landing a man that was as sophisticated and smart as she was. She paused on the profile of a much younger man who was attractive but lacked an age suitable for her needs. She still playfully reached out and messaged, "You are very good-looking Brad but super young for me" bemoaning a 14-year age difference. A few days later Brad responded, "Don't write me off yet, we haven't even met ;)". Adriana immediately took the opening to set up a coffee date and exchange phone numbers. Adriana was not aware that this little flirtation would occupy her fantasies and wet dreams for years.

Brad had always had an interest in older women. They embodied the maturity, intelligence, and sense of direction in life that he craved. He had a busy job and could not handle an immature and needy younger woman. He was also attracted to her aggressiveness and forthrightness to initiate the conversation. She was also a stunning redhead with a toned body and pictures that conveyed her active lifestyle. There was something about the age difference that turned him on; it had played into a MILF fantasy for Brad.

She set the date she was available, and Brad recommended the restaurant. It was a cute little Italian restaurant in San Diego near the outer edges of Little Italy. Brad picked the location as it was close to his apartment and within walking distance if they enjoyed the wine a little too much. Adriana lived on the outskirts of San Diego so any date would involve her driving. Adriana got in her car and drove down to meet him. She was running late and apologized profusely by text. Brad responded calmly, told her to drive safely, and playfully informed her that he was "the hot stud in a blue polo shirt sitting outside alone". She eventually got to the restaurant and parked before heading up to the restaurant. Brad immediately recognized her as she walked up the sidewalk. She looked incredible. He stood up and held her seat, allowing her to sit at the table. She again apologized to which Brad told her to stop apologizing.

She was wearing a long dark floral pattern dress with the setting sun accenting her freckly skin and red hair. As Brad grew more emboldened by their engaging conversation and the bottle of red wine, he moved his hand under the table to touch her leg. At first, he was struck by the fabric's softness before becoming distracted by her thigh. He could not stop staring into her eyes as she regaled him with tales that reminded him of a frontier woman. She was raising bees, operating tractors, running a farm, and managing a stable of horses, all the while raising a large family of children. Juggling all of this as a single mother had entranced Brad. Her toned thighs, athletic body, and gorgeous smile did not hurt either.

Dinner had ended and they had both stood up to leave. Adriana offered to give him a ride back to his apartment which Brad gladly accepted. He hoped that there was a long-shot chance of inviting Adriana up to his apartment, but he would have settled for just spending more time with this captivating woman. Brad was taken aback when the valet brought up a Range Rover. Brad immediately knew that Adriana was also wealthy which intimidated him as he knew she was above his class. Brad hopped in and gave her directions. He reached out and touched her hand. She gladly accepted his hand and they held hands for the short drive. They reached his parking lot and she declined his invitation to go up but she did agree to a kiss.

They locked lips and they both felt that spark. Brad started slowly before pushing his tongue into her mouth. He gently caressed her cheek as they kissed. He teased her tongue sucking on it while also caressing her thigh. He had managed to push the fabric to the side and was toughing her soft smooth skin that sent waves of energy throughout his body. She pulled back from him and said, "Let's move to the back seat." There was a youthful naughtiness to it. They re-engaged in the back seat of her SUV in the mostly empty parking lot of his condo complex. Brad, always a rule follower, worried they would be caught by the condo's roving security guard. Adriana could not care less. She was distracted by Brad's sensual touches and muscular body. He had managed to convince her to slip off her panties. He slowly slid down her black lace Victoria's Secret underwear dropping it to the floor of the car. He pushed her right thigh apart from her left thigh exposing her mound. His hand was met by warmth as he moved in. They locked lips as his hands slid up her thigh to her pussy. He touched her warm wet mound eliciting a groan from Adriana. Her clit had hardened with excitement and Brad began rubbing it before sliding a finger inside her. Her pussy was soaking wet as her desires released her juices. She eagerly accepted his finger by pushing her hips forward to meet his hand. He slowly worked his finger back and forth rhythmically as she moaned.

He adjusted her body so she faced him. He moved on top of her keeping his finger deep inside her while using his other hand to tease her breasts. He played with her hard nipples and cupped her breasts as he increased the pace of his finger. He slowly pulled it out before she moaned, "put it back inside me." Brad had other ideas. He licked his finger so he could taste her before allowing Adriana to suck on it. He again pushed her thighs apart and began moving his head down slowly kissing her thighs starting at her knees and working his way up. He licked up her juices that had run down her thighs before making his way to her smooth mound. His tongue now replicated the actions of his finger. His tongue slowly pushed her lips apart before he pushed it deep inside her with his lips engaging her now throbbing clitoris. He attentively pleasured her as she pushed the back of his head down and arched her hips to meet his tongue.

Brad gorged himself on her juices and taste. He was eager to please Adriana. She gladly accepted his efforts and draped her legs over his shoulders giving him unfettered access. After allowing Brad to have Adriana's sweet little dessert, she pulled him up to kiss her again. His hard cock pressed against his jeans which pressed against her pussy. She felt his cock and wanted to release it from being trapped in his pants. She slowly undid his belt and button before unzipping his jeans. She slowly worked it out of his tight boxer briefs. She grabbed it in her hand marveling at how big it was. It was thick and hard with veins throbbing. Adriana immediately began to wonder about what she would love to do with it. She spit on her hand and rubbed it on his shaft before she began to stroke him. Her strong grip and their other activities were bringing him close to climax repeatedly before she would squeeze his scrotum releasing the urge to cum. She was enjoying teasing him and also could not get her car dirty.

She was exhausted from this little romp and had a long drive ahead of her. She playfully kicked him out before sliding on her soaked lacy panties and getting back in the driver's seat. She rolled down her window as Brad wanted one last kiss before he headed up to his condo. He had to walk in a way that attempted to conceal his still throbbing cock past the front desk attendant. After reaching his apartment, he immediately headed to grab some lubrication. He rubbed the lube around his cock thinking of Adriana and imagining what he would do to her. He came immediately shooting wave after wave of cum everywhere. He lay down in bed but could not stop thinking of her.

After a series of texts that had included pictures of the latest lingerie she had purchased, she agreed to meet up again. But this time they would spend the night together at a hotel in a trendy area of the Gas Lamp District. She picked him up and they excitedly kissed before making their way to the hotel. After checking in, they headed up to the room. Adriana wanted to freshen up before getting some dinner. Brad had other ideas. Adriana was in a cute little sweatsuit, and he reached in to kiss her.

He picked her up and threw her on the bed. He slid her pants down and she had a gleam in her eye. She had been wanting this for a few weeks and now her fantasies would come to life. She unzipped her top exposing her matching black lace lingerie. Brad teased her pussy by tracing his fingers over her fabric before sliding them off. They were already covered in her juices. Brad was excited that he could make a woman this turned on so quickly. He was eager to taste her again, so he buried his face in her pussy using his tongue to explore her. This was more comfortable than the car, so Brad focused all his attention on pleasing his goddess. She unclasped her bra and lay back cupping and playing with her breasts while enjoying Brad's efforts.

Brad had his fantasies to play out. He begged her to sit on his face. He undid his pants and slid off his boxers before laying down on his back. Adriana worked her body to straddle Brad's chest before inching closer. Her pussy now hovered above Brad. He grabbed her ass and pulled her in. He rubbed her thighs and ass before pushing his tongue inside her. She grabbed the headboard for balance and worked her hips to control his tongue while moaning out directions to him. Adriana enjoyed controlling his voracious appetite for her pussy. She teased him by pulling back as he wanted more and then giving him more than he could handle as he gasped for air. She grabbed the back of his head pushing him towards her as she was grinding her clit against his tongue. She reached back to grab his cock. It was thick and hard and begging for attention. Her strokes distracted him before she reminded him that her pleasure was his priority. She gently caressed his scrotum giving attention to each of his balls before she dismounted.

She knew she was ready to be fucked now and Adriana usually got what she wanted. Brad begrudgingly got up and slid a condom on before coming back to the bed. Adriana begged for him to start slow, and Brad did not want to see her in discomfort, so he slowly worked the head of his cock against her mound. He used the head to tease her clit before slowly pushing her lips apart. He waited until she adjusted to the girth and for her juices to coat his shaft. He inched his way in filling her up. He gave her the last thrust to fully insert himself inside her and she grunted struggling to accept it all. She slowly relaxed and gave him the cue to start pumping. Brad slowly worked his cock in and out, pulling his cock out so the head almost left her pussy before plunging it back it causing Adriana's tits to bounce. Her eyes rolled back as Brad took control fucking her. Brad was propped up on his hands over her, so she alternated between cupping her tits and rubbing his chest and back.

With beads of sweat dripping off his muscular body and the pace slowing down, Adriana knew she needed to take over. Brad accepted her offer and lay down on his back. Adriana mounted him before gently kissing his stomach. Her tits pressed against his torso and her hair touched him. He pulled her hair back and she looked up at him playfully and smiled. She sat up on him and worked her hips back. She grabbed his cock and began angling it inside of her before sitting down on it. She had already loosened up a bit, so she took it more easily. She bounced up and down taking him inside her with her tits bouncing. He rubbed her thighs enjoying the view of his goddess taking control. She closed her eyes getting in tune with her body, but he could not stop staring. He grabbed her waist and ass to help her bounce up and down. Her ass hit his balls making a beautiful sound. Both were ready to cum, but Adriana wanted one more position.

She slid off of him and begged him to take her from behind. Brad agreed and she got on all fours. He grabbed her hips and pulled her to the edge of the bed. He pushed her thighs and knees apart so her hips would be lower. He entered her slowly grabbing her hips and pulling them back towards him. He loved seeing her ass shake with every thrust. He felt so big inside her, and Adriana loved the lack of control she had after ceding it all to Brad. He graciously accepted her moans of "faster" and "harder" as he worked to satisfy her. She screamed "I'm coming" as Brad had found her g-spot. He felt her clench her pussy and her thighs began to quiver. Relieved that his princess had cum, Brad worked on his situation. He pulled her hair back and quickened his pace. He used his other hand to cup her tits as he pounded away. He moaned, "I'm coming babe" to Adriana and she squeezed her pussy. He exploded shooting wave after wave of hot cum inside her.

He left his cock inside her for a few seconds to regain his senses before slowly pulling out. He collapsed beside her. Both were panting but Adriana wanted one last thing. She got off the bed and got on her knees. She slowly slid off the full condom before throwing it in the trash. She grabbed his still thick shaft and began to lick the cum off it. She swirled her tongue around the head before pushing it to the back of her throat. It was still too sensitive for Brad, and he struggled with how good it felt and how sensitive it was. He started to push himself up from the bed, but Adriana wanted more so she pushed him back to the bed before licking off every last bit of cum before licking his scrotum.

Now satisfied, Adriana took her younger partner to the shower to rinse off before dinner. Brad marveled at Adriana with her intelligence, smile, amazing body, and insatiable sexual appetite. How could he concentrate on food when he was only thinking about round two?