Erotic Bonding Vacation

As I was approaching my 50th birthday, my wife and I came to the conclusion that we were having troubles just getting along let alone being married. We just didn't seem to have that many things in common anymore.

Our situation was similar to a lot of other couples couple on the verge of becoming empty-nesters since all of our kids were grown up and out of the house, except for our 18 year old son Tommy who was in his senior year of high school. We both felt it would be an easier situation for him if he stayed in the house with my wife until he finished his senior year

We both decided that it would be a good idea for me to get a place of my own for a while until we could think things through and decide what we wanted to do moving forward. In the meantime, spring break was coming up for Tommy so he and I decided to take a father and son vacation to get some sun, play some golf and hang out at the beach and around the pool. It would be our first vacation together without his mother, so we figured we could have some and let loose.

We selected a very expensive, upscale Five star resort In Jamaica. The resort had everything we wanted including beautiful beaches, golf courses, fantastic restaurants, and an incredible pool area with lots of beautiful wives, daughters and girlfriends.

Tommy and I noticed right away that expensive resorts attract wealthy, attractive people, and this resort was no exception.There seemed to be an incredible amount of attractive wives with their lovely daughters, usually traveling with their husbands as a family. After spending the first afternoon at the pool, Tommy and I agreed that this resort was the Mecca for pussy and we were both going to try our best to get some.

On our first full day at the pool, we struck up a great friendship with a family from New York. Marcel and Jessica owned and operated an upscale restaurant in New York City. Their daughter Samantha was an 19 year-old beauty attending her first year NYU majoring in business communications. We hit it off immediately and there was reciprocal attraction between us and them.

Marcel was typical of a lot of men in their 50s who have just decided to let themselves go. He was a big overweight, hairy Italian guy, with thinning hair combed straight back and a nice pot belly. He kind of had that typical gangster look about him. His wife Jessica on the other hand was a 49-year-old trophy wife with long blonde hair, stunning, green eyes, a firm, flat belly and long tanned legs.

Jessica was wearing a black two piece spring bikini that barely covered her nipples and a bikini bottom showing a lot of ass cheek. It was also cut very low for an older woman and it was apparent and obvious Jessica was either shaved, waxed or might have a slight landing strip. Marcel had hit the jackpot.

Their daughter, Samantha was a younger version of Jessica. She had deep green eyes just like her mother and very similar blonde hair braided a beautiful ponytail. She had a well toned, 19-year-old teen bode with a flat belly, beautiful firm thighs and calves, and some very large floppy tits for a 19-year-old teenage girl. Samantha was wearing a bright orange bikini also cut very low at the bottom, showing a lot of ass cheek and barely containing her impressive floppy teenage tits.

We all spent a lot of time at the swim up bar since the drinking age in Jamaica was 18. Tommy and I found out very quickly that Jessica and Samantha didn't hold her liquor very well and became very flirtatious and enjoyed putting their hands on both Tommy and I the more they drank.

Marcel did not seem to mind at all that his wife and daughter lwere obviously coming on to us. As a matter of fact, it almost seemed that Marcel was encouraging more intimate behavior between his wife and daughter, and Tommy and I. Apparently Marcel liked to watch.

Wife Jessica was very impressed with Tommy. She was constantly snuggling up to him. She enjoyed putting her arm around his young, strong, broad shoulders and touching his well developed weight lifter arms and biceps. She was mostly fascinated with his 18 year old, flat belly with rock hard, rippling abs. She probably had not seen a hard flat belly like that for years. She loved to complement Tommy on how hard his stomach was as she slowly rubbed her mature hands across his belly.

The feel of his rock hard abs obviously turned her on, and I'm sure she could see the outline of Tommy's cock starting to press against the inside of his swimsuit. This 49-year-old prick teasing mature Milf We're starting to give my son a hard on right there in the pool. She knew exactly what she was doing and Marcel was enjoying watching every second of it.

On the other hand, beautiful young Samantha apparently enjoyed older men. She was flirting with me from the start by always touching my shoulders, my arms, and letting me put my arm around her tight firm waist with my hands getting very close to her bikini line.

I was thoroughly enjoying the attention and the feel of a beautiful 18-year-old girl's soft skin and the scent of her perfume. Tommy as well was enjoying the freedom of being able to roam his hands around the body of a stunning, mature, milf old enough to be his mother. We both knew at that moment that somehow we were going to fuck these two women. We were just waiting for the opportunity.

We finished off the day by having some appetizers at the bar and retired for the night since Tommy and I had an early teetime the next day. As we left, Jessica and Samantha gave both of us full body hugs making a point to press their hips up against us with the hope of feeling a slight bulge in our swimsuits. We did not disappoint them. Both Tommy and I had slight erections due to the alcohol and the suggestive, touching by these two beautiful ladies. Marcel could clearly see the two of us pressing our cocks up against his wife and daughter. He smiled, nodded and shook our hands for the evening.

The next morning on the golf course, both Tommy and I commented that this family seem to be a little kinky. We both agreed that Marcel seemed to be encouraging sexual contact with his wife and his daughter, and we agreed that we were going to our best to fuck both these these women. We strategized on how we can get these women alone, but we just could not come up with any type of plan. Little did we know that opportunity would present itself just around the corner.

When we got back to the resort, we decided to change into our swimsuits and head down to the pool. We immediately saw Samantha and Jessica, looking like two fuck toy models sunning themselves on their lounge chairs. As we approached them, I said.

" Good morning ladies, what a beautiful day. Where is Marcel this morning?"

Jessica replied, "Well apparently there's an issue at our restaurant that needed to be addressed so Marcel is headed to the airport to catch a flight back to New York today".

Samantha jumped in and said, "Too bad guys, I guess you will just have to put up with the two of us today".

I jokingly replied, "Well that's gonna be hard work, but I think we're up to the task".

We all laughed as Tommy and I pulled over some lounge chairs and settled in for an afternoon at the pool with these two prick teasing, potentially fuckable women. Opportunity had just knocked. We just needed to figure out a way to get into their pants.

They were both wearing different bathing suits from the ones they wore the day before. Jessica was wearing a very stylish one piece black cut very high on her legs, showing a lot of ass cheek. The neckline on her bathing suit was open down to her navel barely covering her beautiful for mature tits.

On the other hand, daughter Samantha was wearing a yellow string bikini top, barely able to hold her voluptuous teenage tits and a full thong bottom shamelessly showing her young firm teenage ass cheeks. Both Tommy and I knew we needed to get more aggressive with these women and take advantage of them while Marcel was out of the picture.

After a couple minutes the ladies asked us to help them with their suntan lotion on their backs. Tommy immediately went for mature milf Jessica and I couldn't wait to get my hands on teen daughter Samantha. Both women rolled over on their stomachs. Tommy stood over Jessica and squirted a stream of lotion on her back, looking at me and winking as if he was dumping a load of jizz on her mature back.

Jessica appeared to be enjoying the feel of Tommy's young strong hands slowly working the lotion into her beautiful skin. When he finished with her back he then squirted a line of lotion on the back of each one of her thighs.

Tommy said, I want to make sure I get you thoroughly covered with this hot sun".

Tommy was going to push the envelope And see what he could get away with. He went to the foot of her lounge chair, grabbed her ankles and slightly spread her legs causing Jessica to lift up her head and look at him.

Tommy started to work the lotion in on the back of her thighs, making a point to rub down her inner thighs very close to her mature pussy. He also made sure he covered the small exposed areas on her ass That gave him the opportunity to slip some fingers inside her suit to get a feel for Jessica's mature ass. He was definitely waiting for some type of response. Jessica did not say a word.

Tommy continued working his way down her calves almost as if he was giving her a light massage along with rubbing in the suntan lotion. Jessica was loving it, and I thought I heard her let out a slight moan of delight. Now it was my turn.

I took a different approach with young Samantha. I straddled her lounge chair, standing over and squirted a stream of lotion on her back on each one of her ass cheeks, and on the back of her legs. Standing over her I must've looked like I was going to mount her right there by the pool.

I started with her back and took the very aggressive action of untying her bikini top without asking. She was surprised and said, "Wait, what are you doing"? I respondedsaid, "Don't worry sewwtheart, I will retie it when I'm done. You surely don't want any suntan lotion on your bikini top now do you"? She said, "It's OK, go ahead". I looked at Tommy and winked. The best was yet to come.

Young Samantha laid there with a shocked look on her face making sure her top did not fall off. I lied to her. Once I finished massaging the oil into her back I did not retie her bikini top. I was setting her up hoping that she would give the entire pool area a nice show of her teen tits.

I now stood over her, looking down at her young firm, totally exposed teenage ass cheeks and felt a little bit of reluctance about shamlessly reaching down and getting to fistfuls of teenage ass with her mother watching. I didn't give a fuck, and my reluctance went away pretty quick.

Other people around the pool we're starting to watch as I put my hands on both her ass cheeks and started to slowly rub the lotion into her skin. I could clearly see Tommy starting to get boner watching me work this young lady over. I took my time making sure her ass cheeks were thoroughly covered before moving down to her thighs.

I was starting to get some thumbs up from other guys around the pool. I slightly pushed her knees apart as Tommy did so I could get in between her teenage thighs and make sure she was thoroughly covered. Her firm teenage thighs felt heavenly. She did not flinch at all as I rubbed down her thighs and calves down to her feet. When we were done we had the ladies return the favor so we could feel their soft hands on our bodies.

The sun was blazing down on us. We decided to get in the pool and grab a cocktail. I did not want to be a total dick, so I retied Samantha's bikini top so she wouldn't be have an embarrassingly moment at the pool and I did not want to ruin the vibe we had going.

As we were at the bar, a lot of young guys who were watching me rub down Samantha's ass were starting to pay a lot of attention to Jessica and Samantha. They wanted pussy as much as we did.

Since some of the other women in the pool were topless, the guys were pressing Jessica and Samantha very hard to show them their tits. Tommy and I had mixed feelings. We definitely wanted to see the titties these two women were packing, but we also wanted to keep them to ourselves. As the young men began to surround us, Jessica and Samantha was starting to feel threatened so we told the guys to back off, and they agreed.

After another hour of sunning and drinking it was getting late and it was time to head up to the rooms. To our joyful surprise, Jessica invited us up to their hotel, suite for a drink as a way of thanking us from saving them from a young group of predators in the pool. As we had it up to the hotel suite, Tommy and I fist pumped each other and quietly whispered "Game On".

We followed closely behind the ladies staring at their asses with every step they took. We had no idea what was going to happen next being alone with these two women in their hotel suite without Marcel.

Once we got inside their hotel suite it became very obvious that these ladies were not just interested in cocktails, Jessica and Samantha were also interested in cock. Jessica poured all of us a glass of wine and mediately things started to get hot and heavy.

Jessica put down her glass of wine and immediately put her arms around Tommy's shoulders and gave him a passionate open mouth kiss. Tonny kissed her right back and immediately slid the straps of Jessica's bathing suit off her shoulders exposing her magnificent, mature, firm torpedo tits that did not drop 1 inch as Tommy rolled her bathing suit down to her waist. Jessica had classic torpedo tits which stood straight out perfect for sucking, squeezing and slapping. Tommy and I intend ed to do all three given the chance.

Young Samantha held my face in her hands and also laid a deep tongue open mouth kiss n me. I reached around and undid her bikini top as I had done earlier at the pool. Her huge teenage tits flopped out of her top and to my amazement and pleasure she had the perfect teenage puffy nipples. The last time that I saw a pair of puffy nipples, I was back in high school. After a couple minutes of kissing the girls switched partners that we all have the opportunity to experience each other.

After a couple minutes of kissing the women dropped down to their knees in front of us and started to pull down our swimsuits. Tommy and I looked at each other knowing we both has a secret that neither Jessica or Samantha knew, but they were about to get the surprise of their lives.

You see, going back as far as high school, I knew that I was exceptionally well hung compared to other guys my age, and that includes all the black guys. That became very apparent in the locker room and once word got out, I was very popular with the girls and also a couple of the Milf teachers. The same thing happened with Tommy. Both Tommy and I had actually lost some relationships in high school because the girls could not handle the size of our cocks. Sometimes too much of a good thing is not necessarily a good thing.

As soon as our bathing suits got down to our thighs both Jessica and Samantha gasped and said the same thing, "Oh my God, oh my God"as we were both starting to get hard. Tommy and I could tell by the expressions on their faces they were immediately concerned that this might be a painful experience for them. Both of us had seen that expression before.

As Tommy started to grow to a full erection Jessica started shaking her head from side to side and said, "There is no way I can handle that" and started to get up. Tommy was not gonna let that happen and pushed her back down on her knees. He put his hands on the back of her head and pulled her in and ground her face in his cock. Jessica got the message and started the process of working Tommy's cock into her mouth. Jessica was gonna suck Tomm'ys cock and he was not gonna leave until it happened.

Samantha was watching what was going on with her mom and decided to go ahead and give my cock some attention. She started to slowly rotate her tongue around the head of my cock getting a taste of my pre-cum, which seem to excite her.

Both women were looking at each other enjoying watching each other suck our cocks. At one point Tommy and I pulled our cocks out and laid them on their faces so they could suck our balls. Our cocks reached from their chins to the top of their heads. They both became incredibly aroused, having the chance to suck two massive cocks and balls. It was now time for some fucking.

Oddly enough, there was only one king size bed in the master suite. We laid Jessica and Samantha on their backs in opposite directions across the bed. I pulled both of the strings on Samantha's thong bottom and was rewarded with the most amazing pure, waxed 18-year-old pussy I had ever seen. Tommy help Jessica out of her one piece bathing suit by having her lift her ass and pulling it off her legs.

Tommy and I both returned the oral favors to the women. We both started by sucking their toes, working our way up their beautiful calves, and slowly moving up the inside of their thighs as we spread them open. Samantha was in heaven as I started to lick her young pussy and her clit. She laid on her back, closed her eyes quietly starting moaning as I massaged her young pink lips and clit with my tongue.

Jessica was just the opposite. Jessica was almost crazy with lust as soon as Tommy started sucking her toes and worked his way up her legs. She was thrashing her head back-and-forth, moaning and almost screaming as Tommy got more aggressive with his tongue massaging her pussy and especially her clit. After minutes of pleasuring, both ladies, they simultaneously exploded with body twitching, screaming orgasms, and begged us to stop. That was fine with us because it was now time for us to fuck these two prick teasing ladies.

I stood up and rubbed the head of my cock against Samantha's young pussy lips to get them lubricated because I knew she was going to be in some pain. As I started to insert the head of my cock, she immediately pounded and gripped the bedspread in pain. I was totally turned on. It was a tight fit, but I was gonna work it in as far as I could eventually ending up halfway in her pussy. That was all she could take.

Tommy was having an easier time with Jessica because her older pussy was more stretched out. Jessica was still thrashing, lifting her head and her shoulders off the bed, almost as if she was doing sit ups. Tommy aggressively worked, his entire cock up into Jessica's sweet, mature pussy. He was living his fantasy of a lifetime, getting a chance to fuck a true Milf.

At one point Tommy and I picked up Jessica and Samantha and lift fucked them and carried them over by the patio window overlooking the pool for everyone to see. This seemed to totally turn the women on as we put them back to back and they both started bucking on our cocks like they were hood ornaments. We took them back and laid them down on the beds and switched partners.

I immediately buried my cock balls deep into Jessica. She was surprisingly tight for a 49-year-old woman. Samantha was now more stretched out so she devoured Tommy's cock with his balls slapping against her ass. Once again we picked the girls up and carried them over to the window to give the people at the pool one more show. We slid open the sliding balcony door so the people at the pool could listen to them moan and scream.

At one point both girls told us they had enough cock and wanted us to cum. Tommy wanted to come inside his Milf Jessica and I wanted to pump my load into the 18 year old teenager. I assured Samantha she would not get pregnant because I had a vasectomy. Jessica assured Tommy she wouldn't get pregnant because of her age. That gave us the go ahead to blow our loads full speed ahead in these two beautiful women. Tommy and I both let loose at the same time grunting, cussing and slam fucking mother and daughter into the mattress until they drained our balls.