Forty and Holding

40 and Holding (Ron)

Ron turned 40 celebrating with friends and family. His sisters organized a gathering at a bar that they frequented. It was well attended: two sisters and a brother, his parents, friends, and friends.

Ron was the youngest. He was outgoing, friendly, and a non-drinker, always the designated driver, always ensuring everyone made it home. His sisters would call him when they were partying, and he would be their designated driver, even when he wasn't with them. He would usually pick up a car full of girls and drive them home. The drunk girls would invite him in, but he was never foolish enough to accept.

Ron enjoyed life and work. He led a large sales team that covered three states, was methodical and a great trainer, and led everyone in his sales teams to success.

Ron was a jock. He played basketball, touch football, and was a golfer, he filled his life with things he enjoyed, but long-term dating and commitments were not one of them. Ron traveled and always found female companionship. He was athletic, intelligent and never hid the fact that he traveled.

Even when he was home, he golfed at all the local courses around him, played ball all over the city, and though he didn't drink, would socialize after games.

His sisters' girlfriends were always trying to get close to him. He knew that would be a mistake. Ron wasn't interested in long-term relationships; he was too busy and traveled often. His sisters would not like him pissing off their friends, Ron loved his family, and he would never cause any friction.

On one of his sales trips, he was having dinner with a few of the guys in the office. He was hiring people and had to stay longer than a week; he could drive home or spend the weekend. He found a golf course he had never played and spent the weekend.

He made a tee time for Saturday. He arrived at the course early and liked hitting a few balls out at the driving range. When he arrived, he checked in and was informed that he was put in with a threesome. He would be teeing off early.

Ron always went with the flow; he enjoyed meeting new golfers, and he would get tips about the course since he had never played it.

They called his name, and he was paired with three women, all slightly older than him; this was a first. He introduced himself; all three were physically fit, wore short skirts, had long legs, and were real golfers; Jen was his cart mate.

The big disadvantage was that women's tees were in front of the men's, and he would have to hit first. The first hole was straight and not too long. Ron let one of the girls drive the cart since they knew the course. He didn't have a choice; he was the guest, and things would move faster.

Ron hit first. He used a 5 wood; he wanted to be sure to hit straight; he swung easy, the ball and went straight, not as far as a driver but straight. The girls commented on his well-hit ball, and he just smiled. Jen drove their cart; she asked him if he was holding back; he laughed and said, "No" It's been a while, and I didn't get a chance to go to the driving range; I'm tight.

The lady's tees were 20 yards in front of the men's. This was a huge advantage; it gave them a better view of the fairway and green. All three women hit down the middle and farther than him; when he got into the cart, Jen looked at him. We bet $10 a hole, no handicap. Are you interested?

Ron laughed. Are you trying to take advantage of the new guy? Jen answered, yes, we are; we figured your ego wouldn't let you say no.

Ron reached into his pocket and counted out $120, I would let you take advantage of me, but I can't cover my losses. Then Jen smiled at him and said, maybe the girls will let you hit from the lady's tees.

Ron chuckled; if I won, you would chide me for hitting off the lady's tees; if I lose, I tell everyone in the clubhouse, and I still can't cover my losses.

Jen looked at him; there has to be a way to make this interesting; Ron smiled from ear to ear; I really don't mind losing; maybe on the back 9, we'll make it interesting.

Jen yelled over to the other cart; he'll take the bet on the back 9. Ron hung his head, I'm doomed.

All three girls flashed a lot of leg, they were single, attractive and confident. Ron hit first again, hole 2 was a dog leg, he studied the card, he came off the tee with a 5 iron, he bent the ball around the curve. All three ladies were wowed; this hole he won.

Ron looked at the card, the back nine was much longer, this was to his advantage, but he didn't comment.

After the 9th hole, they stopped at the clubhouse, had a snack, and they filled Ron in on the bet, $10 a hole, winner take all. Ron wasn't nervous; he kept quiet and hit his first drive off the men's tees; he used his driver.

He stayed in the fairway and out of trouble; he tried to keep his head down and not smile. Every time he had a nice drive or a nice hit, the girls would start on him; you are a ringer; who put you up to this? Ron remained quiet but smiling; the girls were trying to get under his skin.

Ron won every hole, and when it was time to collect, they all had their money out; Ron said, why don't you just buy me dinner, and we'll call it even? All three girls responded, no, and pushed the money at him,

Ron tried to keep a straight face, don't be sore losers, I don't want the money but I did like winning.

They all started talking at once; he had to start laughing.

Jen said, ok, we'll go to dinner and maybe even play tomorrow. We have a standing tee time at 10, maybe tomorrow you'll bring more cash. The girls agreed to dinner, and they'll have another round tomorrow.

Ron followed the girls to the restaurant; he walked in with Jen, and he made her promise, no Ron bashing; she just laughed; he watched her walk in front of him, long legs, a slight sway to her ass; he couldn't even guess her age.

Dinner was going well; the girls were drinking, but Ron was not. Jen looked at him, "Are you recovering, Ron just smiled. No, I've never started drinking. One of the girls said, does it offend you? Ron explained he is in sales and was out almost every night; it didn't bother him. He explained about his sisters and how they called him for a ride when they had too much to drink; sometimes, he would have to bring his date with him.

This made points will all the girls, baby brother took care of his older sisters, they all smiled at him. Ron was a good-looking guy with a great personality; all three girls were impressed and liked looking at him.

After dinner, they talked about the golf game; Ron said, I usually play better the 2nd time I play a course; I'm a little more aggressive. They all looked at Ron; you were sandbagging; Ron stayed quiet, and the girls ganged up on him, but he didn't try to defend himself. His only response was, I'm just tagging along, playing my game; you guys are just making excuses for your golf game.

Jen threw a napkin at him; one of the girls stood up and said, guys? Ron knew he plucked a nerve; they knew they looked good.

The next day, Jen drove the cart again, and they had great conversations; Ron was impressed; Jen was intelligent, but he was still mystified about her age. Maybe she was his age, but maybe she was much older; you couldn't tell looking at her body.

Ron took the first hole. He still didn't use his driver, it was a short hole, and he knew where to hit.

Ron knew the girls were talking about him; they all had smiles when he was on the tee box.

Finally, after Ron had taken the first four holes, one of the girls took his five iron out of his bag, she looked at him, we're handicapping you. Ron was quiet; the girls did not like losing, and he stayed reserved.

On the next hole, he asked them how he should play the hole; they knew he was rubbing their nose in it; Jen walked over, removed another club out of his bag, and put it in hers; he watched her; she had great legs.

He won the next hole; when he was walking up to the cart, Jen pulled away, and he had to walk to the next tee box. The starter pulled up and gave him a ride; he asked Ron if they were his friends, and Ron laughed, no, I was placed with them. The starter laughed; no one will play with them; they are good golfers and like to win.

Ron walked up to the girls and said, ok, let's call the bet off; I don't want this to get out of control; I don't mind walking, but it's slowing the game. Jen laughed and put her arm around his waist and said, you tricked us; you're a sandbagger. Ron said wait, you made all the rules, we could have used handicaps, but you thought you could beat me.

Let's call the bet off, give me my clubs back, I'll buy dinner, and we'll just have fun. Jen said nope, we take a club every time you win a hole, and you can still buy dinner. Ron laughed, I'm a good sport, you can make all the rules, but you can't take my putter or wedge, the girls agreed.

At the 18th hole, Ron had 4 clubs in his bag; the girls were having a great time; Ron was still beating them and asked them where they wanted to have dinner; the girls were tired from trying to beat him, and they wanted to call it a day.

Ron protested and suggested they eat at his hotel; they could sit in the Jacuzzi and relax.

Jen said it sounded good, and the other girls were wondering what they would wear; Ron laughed, they have large towels, robes, and I have extra tee shirts; I'll make sure you are all decent; the girls smiled; they liked being catered to.

They finished and followed Ron to his hotel. Ron called ahead and had robes, towels, and a couple of bottles of wine delivered to his room.

Ron had a suite, so there was plenty of room; Ron went to the bathroom, put on his swimsuit, he gave the girls time to change and have a glass of wine.

Ron came out of the bathroom, and they followed him to the Jacuzzi. The girls had stripped down, and wrapped the large towels around their bodies; he was surprised; no one wore underwear to the pool area.

There were tables in the pool/jacuzzi area; the girls had towels and robes and were ready to relax.

The 1st bottle of wine was gone, and Ron ordered another and snack food. The girls were impressed at how organized he was, the Jacuzzi worked wonders, or maybe it was the wine. Jen sat next to Ron in the Jacuzzi; she put her hand on the top of his thigh. You're a good sport and a good winner.

The girls would take a dip in the pool to cool off and come back to the Jacuzzi; Ron ordered another bottle and more snacks. The girls were getting loose, and the towels kept sliding down; Ron would remind them they were in public, even though the pool was empty.

Eventually, they were in the water naked; Ron tried not to stare; he commented on their bodies, and they all stood up and flaunted. Ron smiled.

Ron asked them if they were relaxed; it was unanimous, and everyone was relaxed and happy. No one wanted dinner, and Ron kept ordering appetizers and wine. They were all laughing and enjoying themselves; Ron was surprised at how they had changed from their cutthroat golf game.

Finally, they wrapped their robes around their bodies, and all started to Ron's room; Ron offered the use of his shower to get the chlorine off.

The girls all showered, they walked around naked and left the bathroom door open, Ron tried to leave the room, but Jen stopped him, don't be shy. We'll be leaving soon. One of the girls invited him into the shower; she wanted to wash his back; Jen said we better get dressed and head out before this gets out of hand.

Jen was the last to shower; the other girls dressed and said goodbye; Jen walked out of the bathroom naked, pointed to the shower, and your turn.

Ron was tiding up; Jen came up behind him, wrapped her arms around his waist. He turned around, her arms wrapped around his neck, and kissed him. Ron responded; he kissed her, and his arms went to her waist. They kissed; Ron's hand went to her bare ass, and he cupped her ass cheeks; she pulled her head back, looked at him, and said, you made this a fun day.

Ron led her to the edge of the bed and sat down; Jen sat on his lap. She took his face in her hands and kissed him slowly, her tongue in his mouth, gently probing; she finally pulled back and smiled at him; you made this a very pleasant day. She kissed him again; Jen had been watching Ron's movements all day; she knew he was watching the girls and enjoying their bodies.

Jen could see the outline of a nice package; Ron had an erection in the Jacuzzi; how could he not with three naked bodies surrounding him?

Finally, she stood up, pulled him up, and asked him if she could take off his swim trunks. He started to pull them down, and she grabbed his hands, "No, let me."

She unbuttoned his suit; her hands slid around his waist and down his ass cheeks. She pushed the swimsuit down; she was facing a large cock, the biggest she's ever seen. Her eyes moved to his face; she was smiling, her hand wrapped around the base, her other arm wrapped around his neck. She pulled his face down for a kiss.

Jen took over; she pushed him backward onto the bed and straddled him; she pressed her crotch against the big cock. Ron pulled her down and kissed her; his hand moved down her back to the crack of her ass, and he rolled her over onto her back.

He kissed her, and started moving his mouth down her chest; his hands went to her breast and pinched her nipples, and he heard her moan. Her hands went to his head; she pushed his mouth towards her crotch, and Ron grabbed her wrist. Ron didn't want to be used; he held her hands behind her back.

He kissed the top of her mound; Jen started to struggle; Ron was too strong and kept her hands behind her; he teased her lips with his tongue. Jen was enjoying Ron's mouth but wanted to be filled with his cock; she tried to break free. He pulled her against his mouth; his tongue slid into her; Jen squirmed and ground against his face.

Ron felt her shudder; she had an orgasm. Finally, Ron released her hands; he knelt between her legs, he looked down at her; she was recovering from her orgasm. Ron leaned over and kissed her; her arms went around his neck, she tasted her pussy in his mouth, and she said thank you.

Ron's cock was between her legs; he pushed forward; Jen reached down and guided him; the head of his cock pushed past her lips, and she moaned. She raised her hips, "go ahead", said Jen.

Ron raised up, he slowly pushed into her. His hand went to her mound, he started to massage her clit with his thumb.

Ron wanted to please her but wanted to be in control, just the head of his cock was in her, his thumb gently massaged her clit. Jen wanted to fuck, she wrapped her long legs around his waist and started pumping her hips.

Ron slid into her slowly, his thumb massaged slowly, Jen pumped her hips faster, but Ron was in control.

Another orgasm started; Jen pumped her hips harder, and her legs tightened around Ron's waist; Ron pumped deeper and faster but watched her face for pain. Jen said, "fuck me" Ron pumped deeper.

Jen was wet and tight, Ron tried to control his thrust, but he was close to cumming; her legs tightened, and Ron spurted deep into her; Jen felt him; she was having her own orgasm.

It only took moments; Jen's legs dropped; she rolled on her side, and she couldn't control her legs. Ron stood up; he went to the bathroom to wash up. He came back with a warm washcloth and a towel; he rolled her on her back.

Jen looked up and smiled; Ron placed the warm washcloth between her legs; Jen felt the warmth and opened her legs.

Ron cleaned her thighs and pussy, his hand holding the cloth over her sloppy pussy; Jen was amazed at how soothing and relaxing it felt; Ron used the towel to dry her pussy.

Jen sat up; she looked at him; you beat me in golf, buy me dinner, show me a relaxing time in the Jacuzzi, and then fuck me into submission. Ron looked down at her; how are you feeling? Jen responded, was it the Jacuzzi or your big dick?

Ron laughed; the night was still young; he knelt beside her head, and he used his hand to place the head of his fat cock on her lips; Jen turned towards him and opened her mouth; Ron pushed it farther into her mouth. Jen was glad he wanted her mouth.

Everything progressed; in moments, the cock was growing, and Jen was having her throat stuffed with the large cock. Jen was hoping he would cum in her mouth, but soon, her mouth was sore, and she was gagging.

Jen could only think to roll on her side; she reached behind her and guided him to the wet pussy. She pushed back; Ron shoved half his cock in her, and Jen let out a moan. She reached behind her, her hand grabbed his ass, and pulled him to her.

Ron tried to be gentle, but Jen pushed her ass back hard; she needed him to take her. Jen had more orgasms with Ron than all her lovers these past months. Jen wanted to reward him; she wanted him to cum in her.

Ron was a gentle lover, but Jen wanted to be taken; she rolled onto her stomach, and Ron stayed in her. Jen moaned, Ron, fuck me, I want all of you. Ron was on top of her and started pumping hard; Jen grunted and moaned; Ron was pumping his whole cock into her, and Jen tried to keep pace.

She buried her face in a pillow; he could hear her grunting; he finally pulled out and rolled beside her. Jen lifted her head, cum in me, Ron said I'm okay.

Jen put her arm over his chest; what can I do for you? Jen looked down. He was still hard.

Ron just smiled at her, don't worry about me, are you happy? Jen laughed, you made me happy many times, you rode me hard.

Ron laughed at her; you kept your legs open, and I tried to keep up with you; Jen laughed, and you buried me.

Jen reached down and started stroking his half-hard monster; Ron turned on his side and put his hand on her ass, his fingers following the crack till he felt the crinkled butt hole. She looked at him; I think that you're too big; Ron wet his finger and pushed the tip of his finger into her, and she threw her leg over his hip.

I can't say no; if you want my ass, you have to be gentle. Ron said I just want to tease it. Jen pulled his finger out of her ass and pulled it up to her mouth; she wet three of his finger and moved them back to her ass. Ron has stretched a lot of assholes.

He worked his fingers into her; he was slow and gentle, and she enjoyed the probing. Finally, she sat up, she bent over, and swallowed his cock; it was in her throat; she was getting it lubed.

Jen laid on her side, reached behind her, and grabbed the cock; he was hard. Jen liked anal; she pulled the cock to the puckered hole, and she rubbed and teased her ass hole. She placed the tip at the entrance and pushed back. She wiggled back and forth and finally pushed the head of his cock in her ass.

In the past, she lubed her ass, and her partner would just fuck her; Ron was a considerate lover, and Jen enjoyed sex and was usually in charge; today she was giving in to Ron and giving her body to him; Ron was the best lover she has ever had.

The head of his cock was in her ass, and Jen never quit moving; Ron grabbed her hips and pulled her onto his cock; Jen enjoyed what Ron was doing, and Ron was ready to cum in her ass.

His cock was only partially in her; her ass was burning; she felt him pump faster and then cum, and she was relieved.

Ron finished in her ass; Jen couldn't believe his huge cock was in her tiny ass; stay in me, she said; Ron pulled her tight against his crotch; Jen could feel him shrinking; he felt good.

Jen moved his hands to her breast; she wanted to stay in his arms; Ron was in no hurry and cuddled with her, his deflated cock still in her ass.

Jen had never felt so good after sex, she wanted to kiss Ron, but she didn't want him to move. Ron squeezed her tighter, is this okay, he asked.

Jen had never felt this satisfied; she was smiling, and she thought, maybe this is it; she knew he was traveling and wasn't sure where he was from; all they talked about was golf.