Her First Older Man

Call me a pervert, but I'm one of those husbands who enjoy hearing about his wife's past experiences. To be truthful, the sluttier... the better. One time, I asked her about her hottest or most erotic experience, and she told me about a time in Hawaii with an older man. As she says, "He taught me a lot, and I mean a LOT!" At the time she was on vacation with her family and had just turned 18.

One evening, the family went to dinner at the hotel where they were staying. The band was playing in the lounge, so she decided to do a little dancing. Her parents were meeting old friends who lived in Hawaii. For that particular trip she had borrowed a dress from her best friend. She still has the picture of her wearing that dress, it's one of my favorites to look at. It was light powder blue, spaghetti strap thing that was cut so low that it reached her navel. It was a dress where there was NO WAY she could wear a bra. Being 18 and firm with what was probably a 34B, this was not a problem.

She and her younger brother were on their way to meet the rest of the family for dinner. At the time my wife was not what one would consider sexually inexperienced, having had several boyfriends and more than a couple adventures. However, there were some things she was still pretty naïve to. On the way in, a man approached her and quietly spoke to her. She said that she was a bit confused and did not understand what he was saying. After he walked away, her younger brother walked up and asked what he said. She said that he was wanting to know if she was available for the evening. Her brother quietly explained that the guy thought she was a prostitute. Needless to say, she was a bit shocked. I can't remember this story without thinking about this incident, and wondering what might have happened if her brother wasn't there.

After dinner, she, her family, and their friends went to the lounge and grabbed a table and some drinks. Her parents were preoccupied with their friends and her brother decided to go back to the room. As the evening progressed, she noticed a man watching her from across the room. They locked eyes and were smiling back and forth. Eventually he started to come over and ask her to dance, but stopped about halfway when he realized how young she was. He turned around and went back to his table. Later on, she wandered over and asked him to dance. They danced for most of the night. I've asked for details from her about what was said and done while they danced. She told me that at first he was quite the gentleman. But after a while he moved his hand to her ass and started rubbing it. She felt his hard on thru his pants during the slow numbers. They made sure to stay away from the side of the room where her family was. He rubbed her ass slowly and gently and told her how hot, beautiful, and sexy she was. He continued on, telling her how mature she looked and that she was turning him on. He told her that he was staying here in the same hotel on business. He whispered in her ear that he's 35 and married with a family. She looked at him in surprise, but decided that it really didn't matter to her. When her family started to leave, he slipped her a piece of paper with his room number on it.

The next day, she told her family she wasn't in the mood to go sightseeing with them. Instead she asked if she could to go to the beach instead and lay out. Her dad didn't have a problem with that. She loved the beach and going to the beach alone at home was normal for her. She put on her bikini, cut-offs, tee shirt, flip-flops and headed out the door, telling her family she wanted to get there early to get a good spot. But she was really planning on going to her new friend's room before he left on business for the day.

She walked down to his room and knocked. When he opened the door, she told me that he was pretty surprised and had a huge smile on his face. She said "Surprise and I hope you don't have plans for the day." He said that he did but there was nothing he couldn't change. He let her in and then went to use the phone. She heard him talking to another woman and after 15 minutes he hung up with the other person. He was smirking as he told her that he now had the whole day to spend with her.

At this point, I'm not sure what happened but apparently my wife was all for stripping down, jumping into bed, and fucking the day away. She started to hurriedly strip, instead he told her not to rush. He slowly guided her over to the bed and sat her down. He looked at her with pure desire as he sat next to her. He kissed her very gently with no tongue, just light and gentle kisses. He put her hands together and then held her wrists with only one hand while he kissed her. He took his time as he kissed her. He took his free hand and gently stroked her arms, just enough to turn her on even more. She told me that it felt oh so very erotic, and very different from her past boyfriends who were just looking to shoot and go. After several minutes, his free hand dropped to her leg and he continued to use his fingers to touch her ever so lightly. His touch was so light that her whole body tingling.

After what seemed like an hour but was probably only 10 minutes, he stopped kissing and released her wrists. He reached down and grabbed her tee shirt by the bottom and started to lift it, she raised her arms and he pulled her tee shirt off. She now was in her cut-offs and bikini top. He slowly grabbed her wrists again, kissing and teasing her with his touch. He only touched her bare skin as he ran his fingers from her neck, going down her shoulders, along her arms, across her chest, where he flirted with the edge of her bikini top. His fingers approached but he didn't slide them under her top. He traced a line from her bikini top, down her stomach, all the way to the top of her shorts. Sliding his fingers along the top of her cut-offs. She was hoping that he would slide his finger further down but he didn't. He continued to hold her wrists as he kissed her. He then reached behind her and untied the top string of her bikini top and lowered the cups.

Her breasts were now exposed and he started lightly tracing circles around her nipples. He was teasing them and occasionally he touched and tweaked her nipples. His hand found the bow at her back and untied it, her top fell completely off. She was now nude from the waist up. He let go of her hands and continued to kiss her, both hands playing with her breasts. No rough grabbing, pinching or smashing but slow sensual touching and teasing. She told me at this point, she was so hot she just wanted to get fucked. He lowered his head started to lick her chest. Flirting with her nipples but stopping short of touching them. He moved his hand between her legs and started to rub her pussy through her shorts. At that point he started flicking a nipple with his tongue. Waves of pleasure flooded through her. He continued to rub her pussy through her cut-offs, and began alternating between licking her breasts and sucking her nipples. She felt like that if he put his cock into her now, she would have exploded in an intense orgasm.

He then leaned her back, his weight on top of her. He continued to kiss her and touch her all over when he stood up. Leaning forward he undid her cutoffs and started to slide her shorts and bikini bottoms off. She told me that she remembers raising her hips to help him pull them off her. She was now on her back, nude, in front of a man twice her age. She felt extremely sexy, not close to slutty. Not even when he took her knees, pushed her legs apart, and exposed her pussy to him. Why he was still completely dressed at this point, she didn't know. He knelt between her legs and started making small circles on the inside her thighs, working his way up to her pussy. When he got there, he slid his finger up and down her pussy lips, rubbing the outside of her pussy. This was quite different than all of her boyfriends.

If and when they took the time for any foreplay, they'd just finger fuck her before jumping on top. He did slide a couple of fingers in, but the tempo was slower and more measured. He then started kissing the inside of her legs, working his way up to her pussy. She closed her eyes and moaned as he worked her pussy expertly with his tongue while using his fingers as needed. She paused for a second in her story, deep in thought. After a couple seconds, she told me that was the first orgasm she ever had while being eaten. She opened her eyes after cumming. Her friend stood, took his shirt off, and tossed it to the side. He then unfastened his pants. Then she told me he hooked his thumbs at the waist of his pants and underwear. Pushing them down, he let them fall to the floor and stepped out of them.

He reached down and took her by the hands and pulled her into a sitting position. She was eye or rather mouth level with his cock. Sitting there, she told me he was just average but pretty hard. She knew what he wanted was more than happy to oblige. She opened her mouth, put her lips around his cock, and started to suck. After a few seconds he took her by the head and pulled her off his cock. He was panting as he told her to slow down and to stick her tongue out, which she did. He then guided her tongue up and down his cock. Telling her to lick a line under his cock, then to suck his balls and use her fingertips on his cock and balls. As she told me, he guided her through giving him a blow job. He was telling her when to suck, when to lick and where to touch. She had sucked several cocks before but this was the first time she had truly given a blowjob. He didn't cum, instead he pushed he back onto the bed and spread her legs again, ass on the edge of the bed. He stood between her legs and placed his cock at the entrance to her pussy. As he guided it in, he fucked her slowly at first, and then he picked up the pace. She said he fucked me for a bit more than five minutes before yelling out and blowing his load in her pussy.

As he pulled out, they laid there on the bed for a little while before getting up and taking a shower. They made out as they soaped each other up. She told me that after they were clean, he went down on her, slung her leg over his shoulder and ate her pussy in the shower for a 20 minutes. They finished showering and made it back bed. He went down on her again and she came even harder. As soon as she came down from cumming, he started eating her pussy for a third time, and she had an even more intense orgasm.

He then slid up between her legs and shoved his cock into her pussy. This time he was not as gentle as the morning fuck. He lifted her legs up onto his shoulders so he could get as deep as possible. She was moaning and yelling as he thrusted deep into her. After a few minutes, he pulled out, flipped her over onto her stomach, and lifted to her hands and knees. He started to fuck her from behind. While he was fucking her, he started playing with her ass. At first just sliding his finger along her crack and then later started just applying a little pressure. When she didn't react or say to stop, he slid his finger in. My wife told me, she was pretty wet and the juices from her pussy lubricated his finger. She was a bit un-nerved and a little concerned about appearing inexperienced to an older man.

As she continued the story, she said that her brain told her "who cares", so she just went with it. She started to enjoy the feeling of the finger in her ass while his cock was in her pussy. After a few, he pulled his cock out and placed it at the entrance of her ass. He paused a minute, but when she didn't say no, he just slowly started pushing it in. He took his time, getting deeper and deeper into her. He started to pull out a bit and then bottomed out in her ass. Once all the way in, he started slow. He pulled out and then slid back in. He was getting faster as she got more used to it. Eventually, she told me that he was pounding her ass better than a porn star. I asked her if he said or called her anything while he pounded her ass and she dreamily looked away but didn't say anything. I got her attention and asked her again. She just looked at me, blushed, and told me that she was ordering pizza tonight for dinner.

She stood on the deck in the backyard, remembering that day with fondness. They had fucked off and on for the rest of the day before she had to go back to her room. The next morning, she rushed back to his room, only to find housekeeping in the room cleaning and straightening it. She asked about him and the cleaning people told her that he had checked out early.