This dream cum true started on our trip to Maui. My wife set this trip up for my 40th birthday but really it was our stress relief vacation for both of us from a year of long work hours. We have three kids who take a lot of energy through out the year and mix that with everyday stress, it was time to get away, and what better place than Maui! Now, let me give you a mental picture of my wife. She is a gorgeous ‘MILF’.
Plain and simple! She works 40 plus hours a week with her business, takes care of three kids and herself very intensely. She is about 5’5, weighs 115 lbs. with medium length blonde hair. She has 40D breast with perfect areolas and her nipples will tell you right away if she is enjoying what’s being done to her. During the day we did the family thing with the kids, which meant lots of pool time.
Well during the fun of the day she wanted a cold beer, so she asked if I wanted one and not being a big drinker I passed but told her go enjoy her self and get one. She smiled and went to the bar which was in the pool area. I always enjoy watching her around other guys because their will always be someone who will check her out. Well it didn’t take long before a few guys at the bar started to take notice. Now, my wife is naive to the idea that a guy would find her attractive, which makes it even better when this starts to happen.
The bar was jumping with music and people having lots of fun, so after awhile I could see she was starting to relax and enjoy her self. So, she finally order her beer and sat on one of the open stools at the bar and started too talk with the bartender. Now, the guys who had checked her out noticed she had sat down and started to make a move closer to her and started a conversation with her. The guys were in there middle 30’s and in decent shape, both dark haired.
Like typical guys they bought another round of drinks right away, so she couldn’t leave quickly. I was watching her body language and could she was starting to enjoy the conversation. It was probably about 20 minutes later she walked over to me and asked if I was okay with her staying at the bar. I told her no problems; it doesn’t bother me at all. I told her to go back and enjoy herself, the kids were playing on the pool slides and I was just reading.
She gave me a kiss and grabbed my cock, which was her way of saying she is having fun, and then went back. When she got back to the bar with her new friends, there was a new player in the mix. The guys had a buddy who showed up and when he introduced himself to my wife I saw her eyes sparkle a little bit when she saw him. Let me give you a little info about my wife’s high school sweetheart.
He was a promising professional baseball player with blonde hair and was her first lover. So, you know all women will always have a soft spot for the guy who takes their virginity! Ok, back to the bar, she smiled, shook hands with him and immediately played with her hair. She was hooked. He was very athletically built with blonde hair and was a very attractive guy, so I knew physically he had what she liked in men.
The guys bought another round of drinks and I started to notice she was touching them on the thighs and forearms, while laughing. So the guys started to touch her more on the shoulder and the top of her knees. This went on for about 40 minutes and then she got up and came my way. She smiled and said to go with her to the bathroom. I jumped up and when we got to the bathroom she just walked right in the bathroom stall with me! Oh yea, I think someone is drunk and horny.
In the stall she squatted down and pulled my dick out and started to lick the head of my cock. Then she started to put more of my cock in her mouth and was playing a game of how deep she could go before gagging all the while rubbing my balls, so I reached down and pulled her bathing suit top to the side and those beautiful tits came out with her nipples in full erection. I could tell she was drunk and horny because she sucks my dick a little different than normally (you know what I mean married guys?).
She was slurping and gagging on my cock and grabbing onto my ass cheek, this gets my cock rock hard in no time! Then she made me seat on the toilet seat, stood up and took her bathing suit bottoms off. She then gave me a kiss, which was extremely wet. I realized why because my precum was all over her mouth from sucking my dick. At the same time she was kissing me she straddled my legs and grabbed my dick and put it right in her wet pussy.
It went straight to the base of my cock from being so wet. She whipped her hair around to the left, grabbed her right tit and the back of my head and crammed it in my mouth, which I sucked like there was no tomorrow. She was ridding up and down my cock and it didn’t take long before I was ready to cum but she started to tighten her pussy around my cock which meant she was going to have an orgasm.
She pulled her tit out of my mouth, grabbed both of her nipples and leaned her head back while still fucking the shit out of my dick. Her moaning got louder and stronger, then all of a sudden, she just started gushing warm pussy juice all over my lap. That made me cum in no time. I just kept pumping hot cum into her pussy every time she stroked my cock with her pussy.
She raised backed up to me, smiled and kissed me then got off my dick but then dropped to her knees and licked my cock clean! Well we got dressed and headed back to our chairs by the pool. By this time the guys at the bar were gone, they must have thought she was not interested. That was okay with us, we laid in the sun the rest of the day and relaxed and had fun with the family. Now the cool thing about these resorts is they have these camps for the kids. They can hang out with kids their own age and play video games, watch movies and camp out overnight.
So we drop the kids off and that allowed us to look forward to celebrating my 40th birthday. Back in the room while we were getting dress, my wife asked me what I wanted special for my birthday. I said the usual answer of ‘nothing’ but for some reason she won’t stop asking. I finally thought what the hell and told her I had a couple of fantasies. She got very curious and wanted to know what they were.
I had always wanted to see another guy fucked her but I knew I couldn’t tell her that because she would have shot that fantasy down in a second, so I told her I wanted to fuck her with a dildo, while she sucked my dick out on our room balcony. She looked surprise and giggled but never said ‘No’ and she never asked about the second fantasy, so I thought the dildo fantasy shocked her enough to forget. Well we decided to go out for dinner.
She wore a sexy dress, which formed to her body perfectly; showing off her big tits, high heel shoes, smelling awesome, hair done perfect and a sparkle in her eyes that makes me a lucky man! We get to the restaurant and got an awesome booth over seeing the bar action with a spectacular Maui view in the back ground. We ordered an appetizer and drinks. The waiter that served use was a very fun guy; His name was Henry.
Most of the hired help on the islands are from all over the world that come into experience Hawaii and have fun. He was no exception. We talked has he served us and found out he was from Virginia and told us of a few good nite clubs in the area. I figured we would stop by one of the clubs he told us about after dinner, but that was about to change. Our waiter Henry came over to our table to tell us he was ending his shift and would like to introduce his replacement, and I would be damned, if the new waiter was not the blonde guy from the pool earlier in the day! Boy, you should have seen my wife perk up.
She started to play with her hair like a school girl and smiling when he introduced himself has Kurt. We said goodbye to the other waiter and ordered dinner with Kurt. Like I said earlier, he had a very athletic built, about 6 feet in height and seem to have a great personality, which made my wife Jennifer very attracted to him.
So, he left to place our order and get use another round of drinks. As soon as he left, she placed her hand on my dick and started to rub it over my pants. I think Kurt may have got her excited again. I reached in between her legs and started to massage her inner thigh, which after a few minutes she opened a little more like to tell me to keep going, and that’s exactly what I did. I slide my hand up her thigh until I finally started to tickle her hairy pussy.
I rubbed her pussy lips with my middle finger, which opened her lips and I softly and slowly slide my middle finger into her. I could feel that she was extremely wet and her pussy was so warm wrapped around my finger. She leaned her head back, closed her eyes then let out a soft cry of pleasure. I fingered her slowly and she kept opening her legs more and more, which allowed me to penetrate her deeper and deeper.
But, all of a sudden, she pulled out my hand and closed her legs and took a drink of her wine and looked at me with guilty eyes! I said quietly, ‘What is the matter?’ She took another drink and at the same time looked up at the bar which was in front of us, and there was Kurt and a few bartenders getting a free peep show. You see, our table was higher than the bar and they were able to see under the table cloth and saw everything I was doing to Jennifer! Well, the guys smiled devilishly at us and went back to their business like they saw nothing.
I looked at Jennifer and smiled and told her I bet they will be jacking off to that tonight in the shower. She smiled and said, ‘Yea right.’ I told her that was the truth because I see plenty of guys eye fucking her all the time. She then said that I was so wrong that no guy is interested in someone as old as her.
I said I know other guys would love to fuck her and to tell you the truth; I would love to see it! She looked at me with her mouth wide open and laughed in amazement at what I had just said. She said, ‘Would that be your second fantasy?’ which you haven’t told me about yet. Boy, women don’t forget a thing do they? I said yea, it would be very erotic to see you get fucked by another guy. At this time, our waiter Kurt came back with our drinks and was very quiet around us.
I didn’t want the guy to feel bad because he hadn’t done anything wrong. I would have watched if it was in front of me too. I told him flat out that we were okay with everything and don’t sweat it, because you couldn’t help it because Jennifer was a gorgeous woman and to her surprise, he agreed that he couldn’t stop watching, because it was turning him.
Very good move my friend! He left again to check on our dinners and I figured there was no better time than now to try getting my fantasy to come true, so I told her we should have Kurt join us for a drink back at our hotel room. She looked at me and said, NO WAY! I know what you are thinking and I could never be with someone else but you. I said to her, you know it’s my fantasy and he would be like another type of sex toy.
Let’s invite him back to our room for drinks and if it doesn’t feel right, we just say goodnight and he goes his way and we have a new fantasy for our love making sessions, okay? She said, okay just for a drink then we have him go and we can live out your first fantasy with the dildo. You got it babe, I said. By this Kurt came with our dinners and I started to small talk with both him and Jennifer. I had to get her excited again.
I told Kurt we were going back to our hotel room to celebrate my birthday and that he should join us. He said, he didn’t know when he was getting off for sure but give him the hotel name and room number and he would try. I said sound’s good, so I wrote on a book of matches our hotel and room number plus one other thing ‘Bring Condoms!’ We finished dinner, said our goodbyes and took off.
On the way back to our room Jennifer seemed a little down and I asked her if everything was okay, she said yea no problems, but I got the feeling she was missing Kurt, has if she felt he wasn’t going to show up. We got back to the room and I poured Jennifer a glass of wine, I got a beer and put on some music, dimmed the lights and lite a few candles. Now with the warm ocean breeze coming through the sliding door, WOW! Maui is awesome… Well we were sitting at the couch just small talking, when I asked her if she thought Kurt was going to stop by.
She said, no, he used the excuse of work. She felt he was just being nice at dinner; probably to keep himself out of trouble with is boss or worst yet for a good tip. She got up and went into the bathroom, when there was a knock at the door. I answered it and guess who was standing there with a bottle of wine but Mr. Kurt. We shook hands and he came in and I told him to have a seat on the couch.
I sat in one of the chairs in front of the couch and moved the other chair over by the slider so that would make Jennifer sit by Kurt on the couch. She came out of the bathroom and saw Kurt sitting there. She smiled and turned right back into the bathroom and closed the door. We smiled at each other and I told him she is a little bashful with this whole thing but I feel she will come around if he would be slow and caring with his actions but to let me lead her to him.
He said he understood very clearly. I told him to pour himself a glass of wine and refresh her glass while I go talk with her. I knock on the door and she opened it very slowly, she acted like Kurt was going to swing the door open and attack her. She saw it was me and let me in and once inside she sat against the sink counter. I asked her if she was going to come outside and have a drink with us and she said there was no way she was going to fuck this guy.
I said no problem babe, we already have are plan set and let’s just relax and have fun, okay? I thought what she said next was weird. She said, ‘And there is no way in hell he’s going to cum in my mouth and he’s going to wear a condom if he fucks me! ‘Hear me?’ All I could say was, ‘Yea, no problem’ Well I came out of the bathroom with Jennifer behind me and I lead her to the couch, I took her hand and sat her down.
I sat in the chair and Kurt handed her a glass of wine, which she took a few quick sips of wine, to calm her self down. I started small talking with Kurt about work and his personal life on the island and that got Jennifer slowly to come around. From where I was sitting, I could lean forward a bit and touch either one of them, so I decided to take Jennifer’s foot and start massaging it.
What woman doesn’t like a good foot massage? By this time Jennifer had another glass of wine which seemed to really relax her; she and Kurt were now in a good conversation about his work. I said in general to Kurt that Jennifer loves her shoulders massaged, which he took the hint and moved in behind her a bit and started to massage her softly on the shoulders. She started to lean her head back a bit and started smiling with her eyes closed and swaying to the music.
Now, Kurt was talking about a special dish they served at the restaurant when he got closer to her ear and whispered in it with his deep sexual voice then he kissed her on her shoulder a few times. I could tell the way she shivered that he hit a sweet spot with her. So, he kept talking when with soft, slow kisses, he started at her shoulder and moved up her neck.
She tilted her head away from him like to say more, PLEASE! He moved back away from her so she could turn to him but he kept his arm around her back when she turn to him and placed her hand on his inner thigh. Now, here is my wife on the couch with another man who just kissed her neck and her hand on his thigh. What happened next is for men who only dream of seeing their wife with another man. She looked at him with an consenting look in her eyes when he reached and touch her face with his hand and brought her into him and kissed her softly on the lips,
then pulled away slightly when she reached up and touched his face and pulled him into her, were she kissed him softly then started to pull away when they both pulled each other into one another and started to kiss passionately. The chemistry seemed to grow more and more with every second that passed. The sounds of their wet passionate kissing got ever so noticeable when I witness Kurt moving his hand up to Jennifer’s shoulder and slide her dress strap off her shoulder which dropped the left side of her dress from around her breast.
He started to caress it, when I watch my wife start searching for his cock with her hand. In no time she had found his very impressive package, in which she started rubbing it in sequence with him massaging her breast I still had her foot which I let go and this let her leg fall softly which opened her legs slightly. Kurt moved his hand down from caressing her breast to her inner thigh.
He moved it slowly up her inner thigh until he reached the bottom of her dress. They stopped kissing and looked at each other for a moment. I can still picture it now, Jennifer’s hair was all messy from making out, her dress dropped off of her left shoulder with her breast exposed and oh yea, another guy was doing all this to my wife. WHAT A FUCKING TURN ON!!!! Kurt seemed to be waiting for Jennifer’s approval to continue.
Which he got, Jennifer put her hand behind Kurt’s head and leaned back on the couch which pulled him down with her, at which time they started to kiss again and Kurt started moving his hand up her dress. Has they were kissing, he finally touched her pussy with his fingers for the first time, Jennifer gasped with pleasure which made them separate from kissing. She looked deeply into his eyes when he penetrated her pussy with his finger.
She opened her legs to allow him to penetrate her even deeper. She closed her eyes once again and started to suck on his upper lip while moaning with pleasure. He got a smooth motion of fucking in and out of her very moist pussy, which was making an incredible sexy wet sound. She moved from sucking on his upper lip to kissing his neck, when she cried to fuck her with two fingers! Kurt stopped for a second to place his middle and index fingers back into her pussy, when she started to fuck his fingers.
She started to cry out pleasurably with every thrust of her hips. Then she screamed, ‘Oh Kurt, oh Kurt, I’m going to cum, don’t stop baby!’ She laid back and grabbed the couch cushions and just kept saying, ‘Don’t stop, don’t stop’ and then she would cum again. She must have had at least 3 to 4 orgasms.
Finally Kurt took his fingers out of her pussy and sat back and Jennifer sat up and started to unbutton Kurt’s shirt which exposed his much chiseled chest. She started to touch and kiss his chest. Then she all of sudden stopped and looked at me, I guess she must have realized she was not back in high school but with a strange guy and her husband of 12 years was watching all of this.
By this time my cock was rock hard in my pants which was dripping wet of precum from viewing this guy finger fuck the shit out of my wife while giving her the best orgasms she’s had in the past 10 years. I looked at her and unzipped my pants and pulled my dick out and started to stroke it in front of her and told her that she was the most gorgeous creature I have ever seen and don’t stop. She smiled at me, then unzipped Kurt’s pants and reached in for his cock. She brought it out and stared at it for a few seconds.
This was the first dick; other than mine, she had touched or seen this close in over 12 years. She had her hand wrapped around the base of his shaft, and then she moved it slowly to the head of his cock. By this time Kurt had precum oozing out of it, so she took her finger and made little circles on the head of his dick, making sure to smear his precum all over the head of his cock. She told him that his dick was very impressive and she can’t believe she was doing this.
Kurt told her that she was a beautiful woman and didn’t know how much longer he could wait before he would cum all over the place. She then slide her hand back down to the base of his cock and cupped his balls with her other hand then slowly closed her eyes, then took the head of his dick in her mouth, which made him contract with pleasure. She moaned and started taking more of him in her mouth then began a steady rhythm of sucking and stroking his dick.
She picked the pace up, and started to rub his balls very intently, like she knew something was cumming, and that’s what happened. Kurt let out a yell and told her, ‘Suck my dick; I’m going to cum Jennifer!’ She timed it just right and took all of Kurt’s cock in her mouth at the same time he unloaded his cum. He just kept sending streams of white cum into Jennifer’s mouth and she had no problem sucking and swallowing all he had to give her.
She was moaning with ecstasy while going in and out on his shaft when I started to see a little of Kurt’s cum coming out the side of her mouth. Boy, I almost blew my nuts right there and then. Jennifer kept sucking his cock until every bit of his cum was gone. She leaned back and looked at me with a smile and said, ‘So much for him not cumming in my mouth!’
They both stood up from the couch and Kurt pulled her into him and started to kiss her passionately again. He pulled down the other side of the dress strap which dropped her dress to the ground, in which she took off his shirt and undid his belt which dropped his pants to the ground, also. I was seating there watching my completely naked wife kissing another man passionately, with the head of his hugh cock rubbing on her belly.
She had her hands running through his hair while his hands where slightly tickling and massaging the curve of her ass then he slowly reached around to the front and caressed her breast and would lean down to suck her nipple now and then which made her sigh with bliss. Her nipples where completely erected and she moved her right hand down to his cock and started to stroke it. He responded by moving his hand from her breast to between her legs and started to rub her pussy.
She helped him by placing one leg up on the couch which allowed him to placing two fingers into her pussy and started to finger fuck her again, and when he did this she sent out a cry of approval throughout the room. This went on for a few moments until Jennifer turned and went to the bed where she laid on her back and spread her legs and started to rub her pussy when she told Kurt to come over here and fuck her. He started to walk over to her and she was staring at his big thick erected cock.
He asked her if she like what she saw and she responded that she had liked what she saw ever since the bar at the pool. He leaned on one knee as he entered between her legs, lowered himself to her when she grabbed his dick and put it directly into her waiting pussy. When the large head of his dick enter her pussy, she arched her back and moaned for him to fuck her. He slide right into her pussy all the way to the base of his cock, she was dripping wet.
He didn’t hesitate; he started to fuck the hell out of her. She started screaming again and again, ‘Fuck me Kurt, fuck me baby, fuck me harder damn it, fuck me baby!” In moments he was grunting like an animal, with sweat running down is back. She was crying out in pleasure while his cock was pumping in and out of her pussy.
She had her legs spread as far has they could go then grabbed onto his ass cheeks and started to fuck him has hard has he was fucking her, which meant she was going to cum and that she did. She moaned and squeezed his ass cheeks when the sound of her pussy juice mixing with his pounding cock took over the room. This must have turned him on because he started to fuck her even faster which made her more excited and she yelled, ‘Fuck me Kurt, fill my pussy full of your hot cum baby!’ Well he did just that and more.
His ass tightened up and he cummed for a second then he pulled out his cock, stroked it and shot more of his cum all over her. She started rubbing it all over her body while fingering her pussy! He dropped to the side of her on the bed and was exhausted. Well she looked over at me, smiled and motioned with her finger to come to her. I got up and she told me to take my clothes off and come kiss her. I stood up and my cock was rock hard and I had precum everywhere.
When I got over to her, she pulled me on top of her in which we started to kiss. We rubbed Kurt’s cum all over our bodies. I told her it was amazing watching her and I had never been more turned-on. She whispered in my ear that she wanted her pussy eaten, so I started to kiss her body all the way down to her pussy, where she spread her legs. Her pussy was so wet from all their cum.
Her pussy never tasted better! Jennifer then leaned her head over to Kurt, who was now on his side watching us, and told him she wanted to taste his cock again. Kurt didn’t hesitate; he placed his cock in her mouth which he started to fuck her face slowly but picked up the pace when he saw her started thrusting her hips against my face, confirming that she was going to cum. I looked up from between Jennifer’s legs and watched my wife have an orgasm while another guy was fucking her face with his hugh cock.
After Jennifer had cum, I leaned up to watch Kurt fuck her face until he cummed in her mouth and after he was done she took is dick out of her mouth and motioned for me to come up to her. When I got close, she reached for me and started to kiss me with a mouthful of Kurt’s cum. We kissed with his cum pouring out of our mouths. She smiled, looked me in my eyes and said that it was my turn.
She told Kurt to lie on his back and she started stroking his dick. I was already rock hard and it didn’t take Kurt very long before he was hard again. She got on top of Kurt and put his cock in her pussy and laid down on him with her back to him. She then smiled while pinching her erected nipples and told me to come fuck her and she led my dick into her pussy with Kurt’s. It took us a few minutes to get the timing right but we got it going.
It was so hot fucking my wife while another guy was fucking her at the same time, that I cummed right away but I was so tuned-on by it that my dick stayed rock hard. Jennifer had noticed also and cried for me to fuck her harder! She was moaning with pleasure but then started to get louder and louder until she was begging for us not to stop! Kurt and I were fucking Jennifer with everything we had until we all cummed.
I buried my cock down to the base and I could feel my balls getting soaked with all of our juices, and that made me cum again! Jennifer started to scream again and again saying, ‘Fuck me guys, fuck your dirty whore’ After Jennifer cummed she reached for me and started to kiss me as we rolled off of Kurt. He laid there catching his breath, while we kissed and Jennifer started stroking my cock with her hugh tits. She then told Kurt to go shower, the party was over.
He got up a few minutes later and we could hear the shower running as she kept my dick grow with pleasure using those tits. He came out got dressed and we stopped. He smiled and said he had fun at my birthday party, has we shook hands good-bye, but what happen next was funny I thought. He looked over at Jennifer and said, ‘Thank you’ then leaned down to kiss her good-bye but she turned her head and just said, ‘Bye Kurt’
After he left I asked her why she didn’t give him more than just a bye. She said, ‘You see, he might have made me due things like back in high school but you make me due things no man ever could’ She smiled while taking my fully erected cock in her hands then started to move down between my legs, but before she placed her mouth around my dick, I could hear her say, ‘Happy Birthday My Love’ End of story.
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