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40 and Holding Part 2
Ron, Salemanager
Annie, Older sister
Pat, Middle sister
Jen, Golf partner, Date
Kathy, Date
Ron manages several sales offices for a small company. He travels to the different offices, and is always on the road. He has never had a serious relationship, just casual friendships with girls at most of the offices. He recently met an older woman, whom he has known for a few weeks; her name is Jen. He golfed and spent a few nights with her.
The girl he knew at this office was named Kathy. He called her, she was glad to hear from him, all she remembered was that he was polite and a great lover with a big package. He said he was in town for two nights, would she like to have dinner, she laughed and said it would be fun.
Kathy remembered that Ron didn’t drink but didn’t mind if she did, she could pick any restaurant. She had been out with him three times in the last four months, he was goodlooking, always fun, and was an accommodating lover.
Ron picked her up and they had dinner, she was about 30, a thin blonde, not tall. He met her when he was out with the crew from the office. He never dated any of the office workers, too tricky.
Kathy wasn’t athletic, just thin, Ron remembered her as being healthy and fun and didn’t want to know his life story. She let him talk about things he was interested in, she was a realtor, she had great stories, her interest was making money.
They ate dinner, during dinner his phone rang, he asked Kathy if she minded, it was his sister, she called him often. Tonight, she wanted to see who he was with, they talked about the family and then she said, ‘s let me say hi. Ron just smiled and switched to Facetime, something he’s never done.
He turned the phone towards Kathy, this is my sister Annie, my oldest sister. Kathy introduced herself and said this is a pleasure, and added, is your whole family beautiful, you and Ron looked like you walked out of a magazine.
Ron laughed, turned the phone so Annie saw her. Well, I think we have given you enough time, are you finished? Annie said stop, let me see Kathy, she’s sweet, Ron just handed Kathy the phone. They chatted, Kathy was taken by Annies’s beauty, Kathy said goodbye, and added my date is getting bored.
Annie said goodbye, and added, thank you for letting me intrude, Ron said, is your recon mission over? Annie responded, “You know mom likes me to tell her I talked to you”, Ron smiled, thank you for calling. Ron was close to his family and Annie was a sister that he cared most about.
Kathy had no place to be, so they ended up spending the evening at his room, Ron always had accommodations at very nice hotels. She kicked her shoes off when they walked in, she looked at him, you only kissed me once, he smiled, wrapped his arms around her, he bent his head, and gently kissed her.
He turned her around and unbuttoned her dress, it dropped to the floor, all she had on were panties, she turned, do you remember me? Ron always was quick, I remember there are no folds, and how y you looked. Kathy said, you have to strip while I get a drink, their timing was perfect, they finished together.
She walked up to him, he was in his underwear, she knelt in front of him, put her drink on the floor, she smiled up at him, let me see if I remember you. He looked down at the top of her head, in one motion his shorts were down and his cock was jutting out from his crotch.
Kathy leaned back, I don’t remember you being this enormous, did you grow? Ron laughed, no, I am over my growth spurt, it must have been dark last time we were together.
Kathy said lay down on the bed, Ron said why, am I getting an exam. He was on his back, Kathy sat beside him and his erect cock, she wrapped her hand around the base, she had long fingers.
Ron put his hand on the back of her head, her mouth automatically moved to the tip, her eyes darted to his face, she stood up and knelt between his legs. Both hands went to the cock, she bent it toward her mouth, Ron said wait, I need your pussy over my mouth, Kathy pulled her mouth off his cock, she stood up.
She walked towards his head, straddled his face and squatted, her knees were on the side of Ron’s head, he could see her tiny petals, they were wet. Ron’s tongue licked along her slit, Kathy gave a small MMM. Ron was very slow and only slightly pressed into her, he used his hands to control her hips, she tried to press her crotch against his mouth, he wanted to be sure she wanted him.
Her mouth covered the tip, her lips tightened and she forced her face down onto the cock, she tried to wiggle her hips but Ron’s strong grip kept her from moving them.
She stood up, and positioned her pussy above his cock, she lowered herself, Ron said, we should take our time, Kathy felt the tip against her lips, she leaned forward and put her hands on Ron’s chest.
Kathy told Ron not to move, she dropped her hips and her mouth opened, she lifted back up, he looked down, the tip of his penis was wet and shiny. Kathy rolled off of Ron onto her back, please kiss me and be gentle.
Ron was between her legs, her hand went down and guided the head, she moved it along the slit and wrapped her legs around him, make me take it, said Kathy.
Ron kissed her and pushed his cock into her, the head popped into her, she smiled. She tightened her legs and started pumping her hips, you feel good, Ron was trying to match her hips, he kept pushing harder, his cock was in her.
Don’t stop, said Kathy, I’m cumming, Ron pumped faster, her pussy felt like a tight fist, he felt her shudder, he kept pumping. Kathy’s arms and legs dropped, Ron kept , all Kathy could do was moan, Ron started cumming, Kathy’s body was jolted every time his pelvic hit hers.
Ron finished and rolled of off her, Kathy curled up next to him. She draped her arm over his chest, her hand held his face, that was a great fuck, you were warm and loving last time, this time you jumped my bones, thank you. Ron looked at her, you felt tight. Kathy looked up at him, I told you you’re bigger.
Ron laughed, the night is still young, Kathy responded, OMG, let me see if I can walk, she stood up and walked to the bathroom, she looked over her shoulder, you’re in luck.
Kathy was surprised, cum was running down her thighs, she looked between her legs, she was happy when she didn’t see blood mixed in. She made it to the bathroom and started to clean up, she sat on the toilet, cum was running out of her.
Kathy prepared a drink and returned to bed, she sat on the bed next to Ron, she was smiling, Ron’s mind wandered, no call from Jen, he was in a quandary, women are usually predictable, Jen was not.
Kathy asked him if he was in a stupor, he smiled, no, I was thinking how out of character this was. Kathy sipped her drink, her hand reached for Ron’s limp cock. I can’t believe I didn’t remember this, her hand squeezed the limp cock. I need to take a picture, Ron laughed, no, don’t do that.
Kathy finished her drink and went for another, she was feeling mellow, the tired her out, the drinks set her mood. She sat against the headboard, sipped her drink, Ron looked at her, thin legs, tiny waist, y.
His hand went to her flat stomach, she opened her legs, she pulled his mouth towards her small breast, the tip of his tongue teased her nipple. She watched his hand move to her slit, his finger moved to her protruded lips, he teased her clit.
Kathy enjoyed displaying her y pussy, she liked being teased and played with, it relaxed her and Ron was an expert. She made little sounds, she was enjoying the attention but didn’t know how she would satisfy him, she could see his growing erection, maybe he’ll want her ass, she would let him try, she may need a few more drinks.
Ron continued to play with her clit, he could see it swelling, he pinched it. Ow said Kathy, she reached down and put a finger between her lips, she wanted to cum, her finger moved in and out, Ron sucked her nipple, and played with her clit, Kathy spread her legs and inserted another finger, her orgasm started, she was very vocal.
Ron watched her finish, she relaxed, Ron quit touching her, he asked her to roll over, Kathy smiled at him, let me get a drink, she stood up and went to the bar, she finished her drink and poured another, she downed it.
She just stood there, she was y and she knew how good she looked, Ron had a raging erection, Kathy laid in the middle of the bed on her stomach, the liquor was working. Ron cupped her ass, she buried her face in the pillow, she lifted her head, looked at him and said, “don’t be gentle”.
Ron’s finger moved down her ass crack, he pushed the tip into her dry asshole, she reached behind her and spread her cheeks, he felt her body clinch, he pushed it deeper. Her ass was tight and dry, she grabbed his hand and pushed his finger deeper.
Ron asked her to kneel down, Kathy jumped to her knees, Ron moved his mouth to her asshole, his tongue pushed in. Kathy was smiling, his finger slid into her pussy, it was tender but felt good, I’m ready.
Ron pressed the head against her crinkled hole, his mouth had lubed her tight ass, his cock was wet from being in her other hole, in her, Kathy smiled.
Ron grabbed her hips, he pulled her back and pumped his hips. Her face was buried in the mattress, he stretched her asshole, he could hear her muffled squeals, finally, he finished in her ass hole. Kathy fell forward, Ron rolled on his side, she felt his cock pull out of her ass.
Kathy dozed off, Ron watched her as she slept, Ron covered her with the sheets, he left the bed, cleaned up and fell asleep next to her.
He woke the next morning and didn’t bother her, he wanted to take a picture of her sleeping, she was beautiful, but as rule never took pictures of sleeping women, he thought it was creepy.
Ron finished work and left early, he called Kathy, she answered, she spent the day in the room and the pool in his Tshirt, Ron always had extra shirts. She kept the last one she borrowed, maybe it kept him linked to her.
She was in the room when he arrived, she hadn’t eaten all day, thought they should have a meal, Kathy said I don’t have anything to wear, Ron pulled a pair of shorts out of his bag. Kathy looked at him, where would I go in those, he pulled another tshirt out and he said this is perfect for a poolside late lunch, she smiled.
Kathy put on the shorts and shirt, tied the waist tight, no makeup, fluffed her hair and she was ready, let’s go. Ron followed her out, she was the y, elegant and hot.
At the table Ron asked her if he could take her picture, she looked at him, you haven’t yet? Ron answered, never without asking, Ron took her picture, Kathy said, we can do a photo shoot in the room, Ron smiled, I’ll have to leave soon. Kathy looked up at him, with a grin, I hope I get a little alone time.
They ordered and finished their meal. They walked back to the room, Ron enjoyed following her, everything moved perfectly.
In the room she gathered all her clothes and shoes and put them in a laundry bag, can I borrow these, I’ll bring them back, if you call me next month. Ron answered, it may be a little longer but I will call you. Ron drove her home and they said their goodbyes.
Ron made it home, he was traveling again next week, so he spent time with his family. Annie cornered him, am I going to meet all of your girlfriends, Ron smiled, I’m not sure how you’re getting your timing, but it was luck, but you know, you can call me anytime.
Annie was a great big sister, she loved her brother, she showed concerned but respected the boundaries they set. The fact that he Facetimed his date was a surprise.
His next trip was a little farther, he left on Sunday, he wanted to be in the sales office early Monday morning. It’s been a couple of months since he visited this office, he never has issues with this office, so he doesn’t visit it often.
He had dinner alone, near his hotel room, he was tired and wanted to have a quiet dinner and a quiet evening. Ron finished, and went to his room, he decided to swim before he went to bed.
When he was back in his room he checked his contact list, there were a few names he could call, but decided he wouldn’t be good company.
There was another sales office on the way home, he stopped I, he would normally plan his stops but there were a few things he could finish and he would not have to visit them for a while.
Ron wanted to golf, he knew the course, it was where he met Jen and the other girls, he called the golf course and asked if he could join the three girls he golfed with before on Saturday morning, it was not a problem.
He arrived at the golf course, he dropped off his clubs and then parked his car. When he walked up to the three girls, he said hello, Jen looked up and was quiet, then said hello, he spent a couple of nights with her.
They hugged him, they were all elated, Jen kept her head down, Ron wasn’t sure if Jen told the other girls that they spent the night together, so he didn’t show Jen any special attention, he did try to catch her eye.
The girls immediately cornered him, what’s your handicap? Ron laughed, he said, I’ll play whatever rules you set, but you can’t take any clubs like our last match. The girls circled him, what if the three of us played best ball against you. Ron looked at them, I’ll agree but you have to hit from the men’s tee, they agreed.
He put his clubs on Jen’s cart, Ron smiled at her, can we talk or do you not want to bother? Jen said, I’d like to kiss you, she put her hand on his knee, maybe later.
Ron was confused, and asked, did I miss your call? Jen looked at him, no, I didn’t call you. It got quiet, they drove to the 1st hole, the girls told Ron he’s first on the tee, Ron laughed. The girls wanted to win today, they wanted revenge, Ron wanted to make them suffer.
He knew how to play the first nine, he allowed them to win a few holes, but won the majority, and then he chided them into raising the stakes. He wanted to play winnertakeall, whoever wins, has to give all the money in their pocket or purse to the winner, the girls all agreed.
Jen was quiet but finally said to him, I hope I didn’t hurt your feelings. Ron looked at her, “I don’t mind being a onenight stand”.
Jen stared at him, he laughed, just kidding, we had a great time and you weren’t interested, that’s life. Jen didn’t respond. Ron said to her, boy against the girls, U are going to lose all your money, and smiled.
Jen just looked at him, how much do you have, he pulled a wad of cash, I can cover the bet. Jen looked at him, want a side wager? Ron laughed, whatever you want, Jen smiled, is there anything you want?
Ron smiled, If I win you have to hand me your underwear in front of the other girls, Jen smiled, not a problem, she added, don’t sniff them, they’ll be sweaty, he laughed, I make no promises.
Ron had already won most of the front nine, he started asking the girls if they wanted to quit, they all turned and said no. He asked, do you want to spice up the bet? They looked at him, well you’ve seen what we have to offer, let’s see if it’s a fair wager. Jen spoke up, let’s golf.
Ron beat them on the tenth hole, the girls got worse every time they lost a hole. Ron was consistent, he tried not to smile, but walked away a couple times laughing.
It was over, the girls lost, Jen sat next to him in the cart, pulled down her shorts and removed her thong, let’s go, Ron said wait, I was not serious, Jen kept walking, Ron followed. When they were with the other girls, Jen let her thong hang from her finger, she gave it to Ron, he blushed and put them in his pocket.
The other girls asked was this part of the bet? Jen said yes, Ron said it was a joke. Ron started to walk away, the girls grabbed him and gave him a handful of cash. Do you mind if we come over, the jacuzzi felt great, Ron smiled, my pleasure.
Ron called ahead, and like last time had wine, towels and robes delivered to his room.
Jen drove with Ron, she reached over and put her hand on Ron’s thigh, should we talk? Ron smiled, I’m a captive audience but, let me start. I wasn’t going to ask you to marry me, I wanted to spend time with you, I don’t need a commitment.
Jen looked at him and said, stop. When I saw Ann, I couldn’t believe it, we were the same age, I didn’t think past that, I didn’t think I’d ever talk to you again. Today was a real surprise. When I saw you today, I blushed and my thong started getting wet, you really pulled off a good one. Ron pulled her thong out of his pocket, I was wondering why these are soaked. Jen blushed.
Ron looked over at her, “another one night stand”? He smiled at her, Jen smiled back, did you enjoy the last one?
They arrived at the hotel, ahead of the girls and went to the room, Jen stripped, Ron just watched her, her body was beautiful, she started towards him, he backed up, we aren’t alone, Jen stopped. The two girls walked in, they stripped immediately, both of the girls handed him their thongs, Ron felt very uneasy, I told you it was a joke. The girls said, you won, pick a thong, or maybe all of them, Jen stared at him.
They went to the jacuzzi, they all went in, the girls were drinking wine, Ron ordered dinner and they ate at a table near the pool. Jen talked to the girls, they laughed and after dinner they dressed and left. Ron was surprised, he was expecting a long night, with three women, maybe his first.
Jen walked to the room with Ron, holding his hand, I told the girls we had to have a short talk and maybe a long night of . Ron smiled, I hope the talk isn’t too painful.
When they were in the room, Jen dropped her towel, Ron put his hands on her shoulders and pushed her to her knees, Jen knelt down, she pulled his shorts down, Ron guided his half hard cock to her mouth. Jen was surprised but opened her mouth, Ron pushed the tip past her lips and into her throat. His hand went to the back of her head.
He guided his cock with his other hand, he forced the cock into her throat, she didn’t resist, she wrapped her arms around his hips.
Jen’s throat was filled, Ron pushed deeper, she wasn’t expecting a throat fuck this soon, Ron was big but she let him force his cock farther into her throat.
She pushed away from him, are you punishing me? Ron smiled, “No, I was trying to keep you from talking, Jen knew what he meant and laughed.
Jen stood up, she kissed him, there are a lot of ways to keep me from talking, she led him to the bed, she pulled him down on top of her, she spread her legs. Ron nestled between them, he put his weight on his elbows and looked down at her. He kissed her, she opened her mouth, he teased her with his tongue.
I’m ready, he just smiled, she wrapped her legs around his hips, she felt him against her crotch, he teased her, the tip of his cock was pressing slowly into her. Ron, I want it, he kept teasing her. She looked up, I’ll be a good girl.
Ron pushed into her and then pulled back out, “What does that mean”? Jen answered, you’ll find out after you make me cum. She grunted when he filled her, she wrapped her arms around him, he started pumping his cock into her. She moaned into his mouth, your big, she said, then started cumming.
Ron lifted up, he pushed her knees against her chest, he looked down she was smiling. That was very nice, he slowly pulled out. What do you want me to do?
Ron started trailing kissed down towards her crotch, Jen said, “come back up here”, Ron didn’t listen. He enjoyed eating pussy, he knew he could make her cum again.
His lips kissed clit, then his mouth covered it, he pressed his tongue hard against it. Jen’s hips were grinding against his mouth, her thighs tightened, her hands were holding onto his head, he felt her body tightened, her orgasm started.
Ron let her finish, she pulled him back on top of her and kissed him, she felt his cock pressing into her wet pussy, wait, let me catch my breath. Ron ignored her, his hips pumped and his cock was in her, Jen said, “Oh God”.
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