Best Friend Watching

Gina and Missy had been best friends since college. They met each other in a freshman political science class, and had been close ever since. Both now in their 40s, they had remained close during both girls ups and downs in relationships, careers, Gina's child, and each others families. They were each others "person" in good times and in bad. Gina now lived in Florida, and Missy was living in her home town in Virginia.

Gina had been in a relationship for years, and even had an 11 year old daughter, and living happily as a mom and significant other for quite a while. She was managing partner in a small but successful insurance company.

Missy had been in and out of a few long term relationship, as she had concentrated her life mostly on her career. Engaged once, but never married, and was now a single lady running her own accounting firm. Missy was 5'6'' and attractive. Great body, nice smile, and killer eyes.

Missy had been single for about a year after a long relationship, and was ready to get back into the dating scene. She hated the bar scene, and would never date anybody in the business, so finding compatible men was tough. So it was came down to her "girl gang" to try and find a new match.

One of her "girl gang" friends husband had a potential match. His name was Jake, and he lived in the next town over. They decided to have a double date to introduce them. Jake was about 6 feet tall, dark hair, and a past college athlete. You could tell he did not miss many workouts or days at the gym. A semi perfect specimen at 35 years old. Missy wasn't a fan of younger men, but after all, it was just dinner with friends.

When Missy first saw Jake, she was impressed. Handsome, tall, and fit. The age thing was still bothering her, but dinner went well and they all had some great conversation. After dinner Jake and Missy exchanged numbers, and both agreed they would like to see each other again.

After some texts during the week, Jake asked and took Missy out to a local restaurant. Dinner was great, and afterwards, Jake and Missy went to Missy's house to have drinks. During drinks Missy and Jake started to mess around...kissing first, then some heavy petting thru their clothes. The age thing still bothered Missy, but his nice body did not. She really was enjoying the kissing, petting, and then could not help but be impressed by the size of his growing cock beneath his slacks. She move her hand to make an innocent graze across his member, and got excited that this could be inside her soon after. But to her shock, Jake decided to be a gentleman that evening, and wanted to make sure Missy knew he was just not out for one thing. A bit taken back, but Missy was impressed by his candor, and his honesty, and his upstanding manhood. He left that evening with a kiss and a "I had a great time, I'll call you tomorrow." Missy was impressed.

He called the next day and they chatted. He nor Missy wanted to be too aggressive, and they both knew it. And although her BFF Gina was going to visit the next weekend, they still made plans to see each other. Ideally, MIssy wanted Gina to meet him to give her the good scoop on his looks, and his personality.

That Friday Gina came into town and Missy and her laughed, giggled, talked for hours, and polished off a few bottles of wine. Best times with best friends. Missy chatted a bit about Jake, but after only one date and a few texts, couldn't expand they way Gina wanted her too. But Missy did mention the size under his slacks, and couldn't help but smile when she told her about it.

On Saturday afternoon, Missy set up drinks with Jake, and drug Gina along so she could meet him. "Just to meet him and let me know, this is the dude I'd ever marry, just somebody to hang out with and who knows," Missy said. Gina agreed and was excited to meet Jake, and also hang with her best friend. She had always been a good advice monitor.

They all met up an outside bar that was not too far from Missy's house. The shared drinks and stories for hours. It was a great time, and Missy kept smiling at Jake, who kept rubbing his leg against hers. When Jake went to the restroom, Gina told her probably not the man of her dreams, and the age thing, but he was super cute and had a great personality.

After the drinking, Jake decided he should drive the girls back to Missy's house, and they could get her car later. So they all went back to Missy's house, and then started hanging out, Missy and Jake on the couch, and Gina was on the love seat across from them. Missy was a bit tipsy, and starting to cuddle with Jake, while Gina drank and watched. At one point, Jake leaned over and kissed Missy, with deep tongue and super passionate. Missy loved it, but was a bit taken back as Gina was right there when he did it. It did not bother Jake at all. Missy and Gina both turned a bit red from embarrassment. Jake again leaned over and kissed Missy with deep tongue, running his hand across the back of her neck and holding her head tight against his. Missy got goose bumps and tingles all over, and Gina just continued to turn red, but refused to look away. Jake went one step further on the next kiss, and while his tongue was in Missy's mouth, he grasp her hand and moved it down to feel how he was getting hard, and then continued to rub her hand over his pants and her growing cock.

Missy was enjoying the attention, and could feel herself getting aroused. Not moving her eyes, Gina was enjoying her best friend getting some attention which she knew she had not had in a while.

"Gina, your friend Missy seems to like athletic men with larger cocks, what do you think?" Jake asked. Gina smiled, "Yes, she has always been turned on and gotten pleasure with men who were a larger than the average bear!"

Jake turned his attention back to Missy, kissing, as she continued to rub his growing cock, and then he started to gently massage his fingers between her legs over her shorts. Hearing the short quiet moans, the kisses getting deeper, and the cock rubbing becoming more intense, Jake devised a plan in his head that would either make him a hero, or a criminal, in one fail swoop.

"Gina, have you ever watched porn before?" Jake asked while still running his fingers over Missy's crotch. "A few times with Rob, my baby-daddy...." she said. "Did you like it? Was it OK with you?" he asked. "I enjoyed watching it....." she replied.

"Good, then I have an idea....that will hopefully please Missy, and me too." Jake said slyly. Jake could tell that Missy was completely turned on, and wouldn't be able to deny his request. Jake stood up, grasp Missy's hand and then started towards the bedroom. "Come on Gina, come with us." he said, as he smiled at Gina. "Uh, I'm not really one for a threesome, and I'm loyal to Rob!" Gina sternly said. "Oh no, I would never ask you to violate your commitment to Rob...just come this way" Jake said.

Missy and Jake went into the bedroom, and Gina followed behind. The king sized bed was positioned in the middle along the long wall, with some light still peeking thru the window facing the back yard. Jake stopped next to the bed, and kissed Missy. He then led Gina to the corner of the room, and said, "Just stand here, and watch your friend enjoy life..."

Nervous but excited, Gina stood in the corner of the room, and gazed at her long time friend and her new guy.

At this point, Missy started to catch on what might be happening...."Gina, are you OK with this?" Gina nodded with a smile.

While staring at Missy, Jake took off his shoes, socks, pants, and unbuttoned his shirt halfway. Missy gazed at his young athletic body, and the large member that was showing under his boxer briefs. Jake then kissed Missy, and proceeded to slowly remove her pants, and then blouse, leaving her there in matching black panties and a bra.

Jake turned them around, and then sat on the edge of the bed. Missy kneeled down between his legs, and then started to kiss and lick the outside of his boxers as he started to grow, and the tip poked out of the waistband. Missy grasp the waistband, and pulled his boxers over his growing cock. He raised up and helped push them down to the floor. Her eyes were filled with wonderment, and her hand grasp his growing cock and started to stroke him.

Jake smiled at her, and then turned to look at Gina. Gina had her eyes wide open, and was watching intently. "Gina, do you think this is big enough to satisfy your best friend?" "Oh I think it will, I think it will" Gina said.

Missy then licked the underside of his cock until she got to the tip, then with one hand guided his head into her mouth, just the tip at first, and then slowly proceeded to take him inch by inch. A little at a time, starting to bob her head up and down, and ensuring that she lick and suck as she put him in and out of her mouth. Jake loved to watch his cock get sucked, and Missy seemed to be an expert on how she handled a hard cock in her mouth. Every time Missy took more and more of his cock in her mouth, sucking, licking and stroking. And with each time Jake grew harder and harder. Missy enjoyed looking up at Jake as she sucked, and loved that he liked to watch her suck his cock.

Gina still stood in the corner. Amazed at her friend, amazed at the size of Jake, and amazed she was enjoying this show.

After about 5 minutes of sucking, Jake was harder than he had been in a long time. He reached down and urged Missy to stand up. While she was standing, Jake said, "take a step back, and take off your bra and panties for me." She obliged, and Jake enjoyed watching her slowly remove her bra to expose her still perky breasts and hard nipples. Then he could not believe the sight of her shaved and smooth pussy lips with just a patch of pubic hair above her lips. He glanced over at Gina who was staring at her friend, whom he guessed she had never seen naked before. Missy was one hot and attractive woman for somebody her age. Closer to 50, but a body that looked like a 25 year old model.

Jake stood up, with his hard cock at attention. He moved to Missy, wrapped his hands around the back of her head, and pulled her in close and tight for a keep kiss. Missy reached down and wrapped her hand around his cock to ensure it was still hard. Like a rock.

Jake moved Missy to the bed, and had her climb on the bed on all fours, with her knees on the edge and her feet dangling off the side of the bed. The bed was just the right height, as it positioned Jakes hard cock even with Missy's smooth pussy. Jake reached in between Missy's legs to feel how amazingly wet she had got while sucking his cock. Very wet, but it could always use more. Jake knelt down and proceeded to lick up and down between Missy's pussy lips, making her even more wet, and enjoying the taste of her womanhood.

Jake then stood up, and started to move in behind Missy. Her awesome ass and tight pussy where shining up at him. He started to move in, and then remembered Gina. "Gina, come over here so you can see better." Gina timidly moved next to the bed, where she could see Jake's large and hard cock up close, and see Missy's wet slit shining in the sunlight. "Watch me slide inside of her gently, and then watch to see if she smiles" Jake said.

Gina was focused on his cock. Jake took his hard cock in his right hand, his left on Missy's hip, and guided the tip of his cock into her tight hole. Just maybe and inch at first, and then pulled back out. Then the first inch again, and back out. Jake could feel how tight Missy was going to be, and wanted more pleasure than pain for her. The third time he put the first inch in, and then slowly started to push inside her. Gently, slowly, about half of his cock in her tightness. She moaned with pleasure and excitement. "Look at her smile Gina." Gina glanced over and saw Missy's eyes closed with pleasure, but a large smile across her face. "See, we knew she would love this hard cock." he said, as he began to move in and out of Missy's warm wetness. With both hands on each hip now, Jake was still going slow, but began to push more and more of his cock inside her with each push. After a few times, he finally got deep and all the way so his abs were pushed up against her great ass.

It had been a while since Missy had sex from a guy who had a sized cock that she enjoyed having inside her. Sex she enjoyed, but Jake's cock was enough to fill her up and load her with pleasure.

Gina continued to watch Jake's hard cock gently pump in and out of Missy's tight pussy. She could not believe the show that they were putting on, and nor could she believe that she was enjoying watching her best friend get so much pleasure from Jake's big and hard cock pumping in and out of her. She liked watching him slide in and out, but she also liked watching Missy's smile and listening to her moan with pleasure.

While still moving in and out of Missy's extremely wet pussy, Jake turned to Gina and said, "What is your friends favorite position to make her cum like never before?"

"She always told me that being on top was her favorite, and her easiest way to orgasm" Gina exclaimed. Missy heard this comment and got a huge smile on her face. "Yes!!" she said.

Jake pulled out, and Missy sat up on her knees. Jake climbed onto the middle of the king sized bed, and rolled over on his back. His big cock still standing at attention from the pleasure that he was getting from Missy's tight pussy. Missy reached down and stroked his cock once.....and then moved up, put one leg over, and straddled Jake. She leaned over and kissed Jake deep on the lips, with lots of wet tongue. Then she started to glide her body up and down against his muscular abs and chest, letting his hard cock slide between her wet pussy lips.

Missy then reached down, grasp the head of his cock, and guided it in to her sopping wet pussy. She impaled herself with his cock, letting it feed deep inside her, then pausing for a moment to enjoy how he felt inside her. Then she began to ride him, up and down, up and down, randomly reaching down to kiss him, the again riding his big hard cock. The feeling of riding him made her squeal and moan with delight. Arching her back and thrusting herself down on him, knowing it would not take long for her to climax for the first time.

"I think your friend likes riding my cock, Gina!" Indeed she does, as Gina gazed on and watcher her years long friend getting pleasure from riding a big cock she knew she needed and wanted.

It did not take long for Missy to reach her first climax as she pumped up and down on Jake's cock, as Jake held her hips and felt her grinding and pumping his dick. Missy arched back, moaned, and then screamed out loud as her body pulsed with an orgasm she had not felt in a long time. She leaned over to rest on Jake's body, while Jake continued to thrust deep inside her. She had cum once, and it did not take her long to cum a second time while getting a deep hard cock from Jake.

Jake kissed her deep as she came, and then told her, "It's my turn now." Jake rolled her off him and onto her back. He moved down, spread her legs wide, and licked the cum juice from between her wet pussy lips.

As he moved up, Jake turned and smiled at Gina. "Gina, do you think Missy is enjoying my cock?" Gina smiled, "Oh yes, I can see it and hear it. I think she came twice already." "I think she did too...let's see if we can go for a third time....Come closer so you can watch her smile and cum." Gina moved next to the edge of the bed, almost close enough to touch, but still only willing to watch.

Jake pushed Missy's leg up, grasp his cock, and pushed it inside Missy's tight but still wet pussy. He began slow, as before, but each time tried to push deeper and deeper into Missy. Then faster, faster and deeper. Missy reached down and massaged her own clit with one hand, and pinched her hard nipple with the other. She was in heaven, moaning on each thrust of Jake's cock. Jake then let her legs down and let her wrap her legs around him. He began to thrust deep and hard inside Missy. "Watch her Gina, she's going to cum again!" Jake exclaimed.

Missy screamed and moaned as she came a third time on Jake's cock. Her body pulsed and jerked under his body and her orgasm traveled thru her needing insides.

Jake again kissed her deep, and then began to push harder and deeper inside her. His thrusts became quicker. He could feel his balls start to tense, and his cock getting harder than it had been all night. "Watch me Gina!" With one last thrust, Jake pulled out, grabbed his cock, and shot an extreme load of cum all over Missy's stomach and tits, while pumping out every last drop onto her.

Both Gina and Missy could not believe the amount of cum that Jake has just unloaded all over Missy. Missy reached down and ran her finger thru it, and smiled up at Gina. "Wow, never in my dreams did I imagine something like this would happen," Missy said. Gina was speechless, but could not help but staring and smiling at the cum shot and Jake's softening cock.

"Until next time, ladies." Jake said, as he got up to go clean himself off, and grab a towel for Missy.