Date Night with Mom: Jim's Date

Jim held the phone to his ear and waited for someone to answer. "Hello and thank you for calling C.J. Enterprises, how may I direct your call?" A voice said as Jim thought of the beautiful woman he was about to talk to and he began to grow.

"Miss Flowers, please." Jim said and reached down to shift his cock in his pants.

After a short pause, her voice filled his right ear and he smiled. "Hello, this is Margret Flowers, how can I help you?" she asked with her normal soft voice and hoped this wouldn't be someone making another complaint.

Jim heard her voice, smiled and his cock jumped. "And how is Miss Flowers on this beautiful spring afternoon?" he asked with a low, manly voice and his cock grew more.

She loved hearing Jim's sexy voice and he could always bring her lonely body to life in a split second. "Mmmm, I'm getting better by the second and how about you? How are things in the city?" Margret asked, feeling her thick nipples springing to life and getting very hard for Jim.

"Good I guess. I'm not in the city, I'm here and looking for a hot woman to go out with tonight, but she has to be sexy as hell and um...up for anything!" he said in a lower voice and looked down to his fully, swollen cock and he flexed it.

Margret heard him and she giggled. "Oh really now and ahhh...what would that involve?" she asked with a sexy voice and reached up to caress her left nipple.

Jim smiled and thought of taking her to a club. She loved dancing and he loved holding her close. "How about a nice dinner, some dancing, a few drinks and um...we'll see what happens after that," he said and knew she would agree. She always did.

She smiled and her nipples were now pulsing with need. "That all sounds so wonderful, but the last part...kinda makes me worry a little." Margret said with a low voice as she started caressing her right nipple through her thin, silk blouse and slowly spread her long legs.

"Nah, you're safe with me and um...I promise to be good!" he replied with a low growl and laugh.

"I know you're good and that's what worries me!" she laughed and reached down to caress her inner, right thigh, next to her new pair of panties and Margret thought of Jim touching her sheer black stockings.

"Oh come on and go for it. How often do you have a man half your age, asking you out?"

"Well, I am what people refer to as a M.I.L.F. and I have hundreds of young men your age just begging me to go out with them and um...what makes you so special?" she teased and Margret's face turned red as a tomato. She knew why he was special.

He laughed and knew her face was red. "Well now, what makes me special?" Jim laughed again and flexed his cock, but this time, pulled it out and watched it pulse with need. He grabbed it and squeezed it hard, thinking of it deep in her body and loving her the entire night.

"Ok, sorry I asked that and let's change the subject! Where are you taking me to dinner and what club will we go to?" she quickly asked and her clit was tingling now, imagining Jim standing in front of her completely naked and fully erect for her. A scene that happened four years ago and Margret couldn't get clear from her mind, no matter how hard she tried.

Jim could sense that she was horny and knew that tonight would be great. He couldn't wait to hold her and hoped that he was right about her mood. "I like that Italian place on Fifth Street and they have a small dance floor. And...you're a chicken for changing the subject!" he replied with a laugh and waited for her.

"Sure, I love that place and ahhh...what are you up to?" she asked and figured he needed something from her, but they did like going out and being close to each other, they always did and nobody needed to know. "I'm not a chicken...I'm trying to be a good girl!" Margret laughed and it was a well needed laugh. This had been a rough week at work and she was so glad it was over. Jim calling her and asking her out was an extra bonus, making it much, much better.

"I'm not up to anything! I just need to be very, very close to you and um...I mean close." Jim replied with a low voice, squeezing his cock-shaft and gave it a hard flex. "You want me to call someone else?" he teased and heard a loud gasp.

"Don't you dare and I will beat your ass, if you try!" she growled into the phone, slid her hand under her silk skirt and it covered her aching mound. "I don't get many offers I like and I always have fun with you." Margret paused and traced a finger up the center of her blue panties, thinking of Jim and all of the things he was willing to do for her. "How close do you need to be, baby?" she purred into the phone, rubbing her finger deeper into her wet panties and wished it was him touching her.

"As close as humanly possible! I need to feel love and know it's real," he replied and felt his cock going down, just like always.

"Oh no, what's wrong?" she asked, sitting up and was ready to run to his side.

Jim knew she would see right through him and he was right. "I just missed you and we'll talk later. It's five now...how about I pick you up around seven and ahhh...wear something hot! I've been dying to see your long, sexy legs!" he quickly said and his cock sprang back to life, as her sexy legs filled his mind.

She laughed and knew tonight would be just wonderful. "You bad boy, but, I do have a new outfit and I think you'll like it." Margret whispered and wished it was seven now. "It shouldn't take me very long to get ready for our date and if you were to stop by early...we could um...catch up," she purred, spread her legs and Margret slid a finger under her panties. She gently rubbed her bare flesh and wished for Jim's warm tongue.

"Well, I guess I should get ready and hurry on over there!"

"I think you should too!" she purred, chewed her lower lip and Margret was ready to explode.

"I'll be there in an hour. I want to look my best." Jim replied and his cock was hard.

"You know where I live," she purred and hung up the phone. "Oh my god, that boy is going to kill me and make me burn in hell!"

*.

Jim pushed the doorbell, flexed his cock and he couldn't wait to see her. He straightened his tie, the door flew open and there she stood. Her thick brownish, blonde hair was wild and fluffed out like a lions mane, just the way Jim loved it and it went to the middle of her back. Margret had on a very small and very short, knit dress. It only covered her middle body, leaving her shoulders and half of her breasts bare. She had a long, thin face and big, beautiful blue eyes that could melt ice and any man she met. Her eye lashes were long, dark and she knew they drove him crazy.

She was tall; some people even said that Margret was an Amazon woman, but Jim liked her that way and wouldn't change her for nothing. Her body was also big, but not fat in any way and Margret was a solid woman. Her breasts were around a triple D or some crap, the tiny dress fought to keep her full breasts in and Jim loved when they hugged. It was as if two big, fluffy pillows were between them and they made him feel warm.

Her hips were wide, but perfect for a mature woman and they were also thick. The dress was knitted and it hugged her hips very tight. He wasn't sure of sizes or anything, but he knew every man around, loved to look at her and would give anything to trade places with him. She had thick thighs and a wide, two inch gap between them and he loved looking at it too.

Margret's ass was a little big, but it matched her large, full body to a tee and Jim loved when she'd let him touch her. It was soft, but so firm when she flexed her muscles or when she humped against him. It was also one of her 'tender' spots, as she called it and could only be touched, if she gave him permission and only then.

Her long, long legs were covered with sheer black stockings and she wore her four inch heels, giving her a two inch advantage over him and he liked it that way. Jim loved people seeing how big, tall and sexy she was.

"Damn...you could make a dead man hard!" he moaned, stepped towards her and gently pulled her into his arms. "I've missed you so much!" Jim moaned to the side of Margret's soft neck, enjoying a light scent of flowers and Jim began to grow against her left thigh. Her embrace was loving, he melted into her body and Jim wished he could stay here forever.

She laughed at him, returned Jim's loving hug and she felt him already getting hard. "You should tell Jackie that you need more sex or something!" she said, as his warm breath covered her neck, sending a wave of need flooding every inch of her lonely body and Margret's clit started throbbing.

Jim's cock grew more and he hoped she didn't mind. Margret loved to feel him after a few drinks and some close dancing. "I don't think she'd care much about that...I'm lucky if we make love once or twice a month and I'm not lying," he replied with sadness, pulled away from her and they walked into the house.

Margret heard Jim, pulled him back into her arms and she felt so bad for him. "Have you tried talking about it?" she asked with love and felt him flex.

He loved being so close to her and Jim could never control his cock. "Yes, but you know how she is, it's her way or..." Jim said and was going to say more, but Margret cut him off and laughed.

"No way at all!" she laughed, as Jim grew more and flexed again, knowing it drove her crazy and Margret stayed against this young, handsome man and she enjoyed him. "One of us is um...shall we say...kind of...stiff tonight." Margret said with a soft voice, running her long fingers through Jim's dark hair and his cock was throbbing on her thigh.

He smiled and saw her face turn a warm shade of pink. "I told you that I missed you." Jim said, leaning towards Margret and he lightly kissed her lower lip. "Now do you believe me?" he asked with a grin, kissed her once again and pulled away. "Do you have a beer or do I have to wait until we go out?" he asked, turning to see Margret leaning against the door jam, twirling a strand of her long hair, her left knee bent and her nipples looked as if they were going to exploded at any second.

She didn't want to let him go, but they had an agreement and he was sticking to it. "Yes, I have beer and it's the kind you like too. I stopped on my way home and picked some up for you." Margret paused, walked towards Jim and hugged him. "I was hoping that um...you'd come in for a drink or two, before you went home tonight or...where are you staying tonight?" she asked, took the beer from his hand and had a small drink.

"I got a room at that new hotel and it's nice. I was hoping to lure you up there and um...well you know men and the things we want from a beautiful woman!" he laughed, slid his left arm around her waist and hugged.

Margret laughed as Jim slid his arm around her body and she felt it creeping down towards the top of her ass. "Yes, I have been around a few horny men in my time and I remember," she laughed and felt her face blush, as his hand went lower and over her rounded cheek. She didn't care tonight and Margret squeezed her muscles.

Jim's hand slid down, he cupped her meaty cheek and was surprised that she didn't stop him. "We have to stop there so I can show you and afterwards...we'll come back here and um..." he said and didn't finish. He was leaving the rest of the night in Margret's hands and it was up to her, to decide what they were going to do.

She smiled and he flexed again. Margret couldn't help but let out a soft, helpless moaned and she clawed his back. "You better slow down and relax some or um...this could be a very fast dinner," she said with a grin, eased from him and fluffed her hair.

He crossed the line and was told to slow down. "I'm sorry, I always get carried away when I'm near you." Jim said as he lifted his beer and took a large drink.

"I understand, baby and don't worry about it." Margret replied and took the beer from him. "So, someone I know has a birthday coming soon and I'm having a hard time trying to figure out what to get him. Do you have any ideas that aren't dirty or perverted!" she laughed and wanted to give Jim something very, very nice, but she wasn't sure.

"Hell, I don't know. Take me out to dinner and give me a blow job...um...oh shit, that would be perverted!" he laughed, looked into her beautiful, sexy eyes and he could see her sucking his big, long cock and smiling around him.

She heard him and Margret's clit was plain out throbbing now. She would love to have him deep in her throat, gagging on his massive cock and Jim's warm cum shooting into mouth. "What am I going to do with you?" Margret whispered and took another drink of his beer. "It's empty," she whispered again and reached to caress the side of his dark, rugged face, thinking of his long cock down her throat again and she chewed her lower lip again.

His hand covered hers and Jim kissed it. "What to share another?" he asked between kisses and he pressed his hips to her, making sure that Margret could feel his need and desire for her.

"Sure and um...about the birthday...think of something, please." Margret said, kissed him and she backed away.

"I will and have I told you just how beautiful you look tonight?" Jim asked and he loved watching her blush.

"Yes you have, but I still love hearing that and keep it coming!" she said with a wide grin and blushing face.

"Don't worry, I will in one way or um...another." Jim said with a low, manly voice and he winked at her.

She laughed and knew how he would be showing her. His hard cock would be rubbing her thighs, hips and all over her meaty ass, by night's end and she couldn't wait. "I'm sure you will, just keeps things um...you know." Margret said with a hint of regret, but that's how it had to be and there was no other way.

"Would you just relax and have fun. I will be a gentleman, don't worry and we should be going now."

"Great! I'm starving and I can't wait to dance with you!" Margret said with need and a small hint of lust.

*.

Later that night, Jim held Margret close and their bodies slowly moved to the soft music. "You sure know how to get me going and I love it," she whispered in his ear, enjoying Jim's hard shaft rubbing against her inner thigh and very close to her deprived pussy. He was hard as steel, throbbing with need and it was all for her, but there was an agreement and they were sticking to it.

Jim's hands were caressing Margret's lower back, as his cock moved around her soft thigh and he wanted to take things up a notch. He shifted, flexed his shaft and Jim's cock was on her pussy. It pointed up between them, but his shaft was deep in her wet folds of flesh and she grabbed his hair. His hands grabbed her big, meaty ass, he squeezed and Margret fell against him.

He moved, Margret grabbed the back of his head and pulled Jim's hair. His hard, manly cock was on her pussy, rubbing into her excited lips and she was ready to explode. "Oh god, easy baby! Easy!" she moaned, staying glued to his young body and Margret could feel him pulsing. His cock felt wonderful and she knew it could end her lonely life, but the agreement stood in the way. "You're a bad, bad boy." Margret smiled as she looked into his eyes, knowing they were glazed over and filled with love.

He held her cheeks and quickly felt Margret's body tense up. "You like it and you know it." Jim replied pushing into her and hoping tonight would be the night. "Tell me you like it," he growled, pushed to her again and it felt like she was going to rip all of his hair out.

He grabbed her and Margret fought the urge to cum. "Oh Jim...don't make cum...here...please, baby!" she moaned, pulling his hair and pushing to him. She rested against him, panting for air and hoping he would stop. "Baby, you are a master at seducing me and you are evil!" she smiled, leaned forward, opened her mouth and Margret kissed him. Her warm tongue slid into his mouth, searching for his and once they met, they entwined and they kissed.

"You love it!" he said and when she leaned to him, Jim opened his mouth and welcomed her. He kissed Margret softly, he slid his hands under her tight skirt and they started roaming her ass. He felt for panties and only found a small string. "What's this?" he teased and gave her G-string a little tug, pulling it deeper into her slit and she whimpered. Jim caressed each of Margret's lovely cheeks exploring and savoring her bare flesh against his fingers.

She felt his hands go under her skirt and Margret shivered. She wanted him and needed him so bad. "Oh Jim, I need a little break, please." Margret said as she pulled from him and walked to their table. She sat on a chair, watched Jim sit across from her and she sipped her drink. "Why do I let you do this to me?" she asked with a laugh, lifting her eyes and she smiled at him.

He laughed and reached to hold her hands. "I don't know, but I love when we're together...like this and you let me touch you, but..." Jim said as he looked into her eyes and he wanted to crawl inside her. "Most of all...I love being with you," he smiled, kissed her hands and saw a tear forming in her right eye.

"If you keep this up, you may have to take me out for breakfast too!" Margret said and her face was red. She was so close to giving in, but she couldn't.

"Oh really, I could do that!" he smiled and kissed her hands again, thinking of being in her and loving Margret's gorgeous body all night. "A beautiful, sexy woman like you...I'm up for that!" he winked, kissed her palms and her face was glowing. She had five drinks, two hours of his teasing and tormenting, Margret was ready and Jim wanted her.

She enjoyed his sweet words and Jim's soft kisses. "I bet you are." Margret said with a soft voice and a loving smile. She was ready too and her body was on fire. "Let's go see your fancy hotel and...you can take me...home," she whispered to him and chewed the side of her mouth, hoping she could find the strength to resist him.

He kissed her hands, called for a cab and pulled her up. His body was straight against Margret's and Jim's pulsing cock was pressed into her pussy, throbbing and hard as steel. "I need you really bad and I'm not sure if I should take you to my room. If we start kissing or making out...I won't be able to stop and I don't want to do anything stupid." Jim said as he leaned to her, lightly kissing Margret's soft lips and his big hands roamed over her ass.

She heard him and smiled. "Oh, you're such a gentleman and I'm proud of you." Margret said with a whisper and rubbed her hips into his stiff cock. "Maybe we can find a way to help you with this...big...beautiful...thing and um...make him feel all better!" she moaned into his mouth and had an idea. She had two hands and he had a hard cock that needed some love.

"Oh god, that would be so nice!" Jim moaned, as he returned her kiss and wondered what she had planned for him. "Anything you do will be wonderful and I can't wait!" he added as they continued kissing and rubbing their lower body's together.

"I'm gunna help you, baby and fix it all up." Margret said with a voice that women used when a small kid was hurt and needed comforting.

"And you call me evil!" he laughed, flexed his cock and they walked outside. "I love summer time and you!" Jim said and pulled her back into his arms. "We broke up last Tuesday...that's why I'm here," he said with a grin and could have sworn he saw a gleam in Margret's eyes.

She smiled and Margret's heart raced, thinking of Jim being around her more and what they could do now. "So, you're single now and back on the market?" she teased and slowly ran her right hand down the front of his body.

"Yes." Jim moaned as her hand slid down his body and his cock jumped.

Margret's hand slid over his toned stomach, down into his pants and around his thick cock-shaft. "I better make sure that I keep you happy this time!" she moaned in his mouth and pulled on Jim's cock, feeling him growing hard and pulsing with need. "I'm not going to be stupid and lose you again!" she whispered as they kissed, she stroked his cock and Jim held her close.