Recent Cabo Vacation
Tina my wife is 56, 5-10, 160lb, 36D, we have been married for 36 years and she has been with a total of 12 guys in last 26 years since she wouldnt play with anyone first 10 years of our marriege and it has been about 4 years she has been with another guy which was a guy from her gym that she flirted with for almost a year before she hooked up with him so she really needs to get to know a guy before she will consider playing as friendship and trust is very important to her.
We started going to Cabo in the 90's and have been going almost every year since but she has never hooked up with anyone on our Cabo trips so was sure she wouldn't hook up on this trip as well, she is somewhat conservative and seems to be mostly in mom or now grandma mode as we recently became grandparents but she does enjoy wearing skimpier bathing suites and dressing sexy when we go to Cabo as she just says nobody knows us and I know how much you like it so why not.
The 1st day at the swim up bar we met 3 people, a married couple (Tommy & Theresa) and there friend (Lance) that lived about 3 hours from us that we found out was suppose to be 2 couples but Lance's long time GF and him broke up a few weeks before the trip and they convinced him to go anyways, it was there first time to Cabo so we told them all best restaurants, bars, etc and all got along great and when we left to get ready for dinner I invited them to meet us after dinner to show them all the fun little bars around Cabo which they said great, see you tonight.
We went out for dinner and wife mentioned a few times wow that it sucked for Lance that him and his GF breaking up right before there trip but he should have no trouble meeting a new friend to take his mind off the breakup as there are lots of single girls in Cabo, after dinner we went to Monkey Cave which is a great litle bar that makes the best and strongest margaritas and Tommy, Theresa and Lance where already there so we joined and had a blast, it was like we had all known each other for years. We went to a few other bars and then my wife said lets go somewhere we can Dance (she knows I hate to dance) it was close to 10pm and Tommy & Teresa said there tired so they headed back to hotel and Lance said guess I should back as I don't want to be a 3rd wheel but my wife said its ok we have been married so long your not a 3rd will so just us 3 went to an outdoor bar that had dancing and she danced with Lance for a few songs then came back to our table, she knew I was tired so we decided to go back to hotel and when we got back we just said good night to Lance and we went back to our room, she was very horny and intitated sex which she doesnt do often so I asked her wow what got into you and she just said it turned her on knowing some lucky girl is going to get to hook up with Lance so I knew she was turned on by him but she has never fucked anybody she had just met so I didn't think she would do anything except play matchmaker which she enjoys doing for single friends of ours back home.
The next day we went out to the pool and they had 2 lounge chairs saved next to them for us so we put our towels down and i made sure I put mine on chair first so Tina had to put hers next to Lance ha ha.
We all just chatted abvout how great Cabo is and everything it offers, chatting and drinking like we have all known each other for years. I went up to room to check work emails and watched from balcony as wife and Lance talk and laugh until they both got in pool and went to swim up bar together so I stayed in room for about an hour to give them time to hang out and when I got back, Tina asked what took so long I just said issues at work sorry and might have to do bit more work later and Tina said its ok Lance is keeping me company and everyone laughed.
In the afternoon Tommy and Theresa decided to walk around to do a little shopping and after they left I said I need to do a bit more work which normally would make Tina mad while on vacation but she just said I understand so I went to room and sat on balcony watching them, after I left they went to swim up bar and took a few shots and started flirting and playfully touching each other on shoulder, arm, etc as they laughed together so i knew she was interested, situation was right but not sure if she would actually act on it ?
So that night Tommy and Theresa had a romantic sunset dinner cruise planned and Tina suggested Lance join us for dinner since he was left out and after dinner we went to a few bars all 3 getting pretty drunk until wife said lets go dancing which I said you go ahead, Im tired and hate dancing, she looked me in the eye and said are you sure which I said I know you you will safe with Lance and he can get back to hotel safely so yes go have fun, she gave over gave me a kiss which was longer then normal and whispered thank you so I headed back to hotel with all sorts of naughty thoughts going through my head.
I went back to hotel and fell asleep but woke up about 2am and had a text around midnight saying they made it back to hotel and wanted to know if it was ok if she went to Lance room for one last drink but I didn't see the text as I was asleep and now it was 2 hours after she had texted so I assumed she went to his room and was having fun, I tried to go back to sleep but couldnt but didnt want to text her if they hadnt hooked up and have her change her mind.
Around 6am she came back to our room and when she walked in she had that embarrassed look on her face so I just said WOW I think someone had a great time and she just said you have no idea and got into bed with me, I just said please tell me everything. She climbed in bed and cuddled next to me saying I tried to text you but you didnt answer, I was drunk and you are always buggin me to play so I figured it was OK, i didnt ruin the trip did I so I assured her she didnt ruin the trip and it is all i have been thinking about since we all met and cant wait to hear about it, she said after I left they kept dancing and when they took a break and sat at bar he told her he sure wished she wasnt married that she is the hottest funiest person he has met in a long time, she already had a bunch of drinks so she told him that we are not swingers but that I do enjoy when she hooks up with another guy so he grabbed her arm and took her back on the dance floor and she said he started to really flirt and touch her knowing it was OK and they even kissed a few times before they headed back to hotel. once they got back to the hotel is when she texted me but I didnt respond so she was conflicted if she should go to his room but he talked her into goiing to his room saying we dont have to do anything and can just hang out and she admited she didnt want the night to end, once they got to his room he just started kissing her as they undressed each other, once she was down to her panties he sat on bed with her standing in front of him telling her she was the most beautiful women he has ever met as he kissed around her panties then sliding them down and kisisng around her pussy, she said she was so wett and turned on she would let him do anything with her at that point. He pulled her onto the bed and went down on her, she said she had orgasm after orgasm till she was too sensitive so she started to touch him pulling his underwear off, she said he was few inches bigger then me (im average 5") but much much thicker so finally he said i have to feel you and got a condom, got between her legs and she was having sex with a guy she just met yesterday but said it felt like they have known each other for many years, she said he didnt last long and was appologizing, she just told him relax as they kissed and explored each other until he was hard again and this time she said he lasted longer so she was able to enjoy it more, once they finished the 2nd time they feel asleep until she woke up and hurried back to our room to tell me about it.
After we finished I told her best part its beging of the trip and she has all week, she agreed but said that Lance mentioned they needed to be descreet around his friends Tommy & Theresa as Theresa doesnt believe in cheating, etc. I told her that will be even more fun them not knowing haha.
She said she needed sleep so I went by the pool around 10am and they had 2 chairs for us, Theresa asked where she was and I just told her too much Tequila she will be out later then Theresa appologized about us getting stuck with Lance which I assured her we have been married 36 years so we are not love birds anymore and both of us really enjoy Lances company that they could do all the adventures and tours they want and Lance can hang with us and go to dinner with us, etc, she said wow we are so happy we met you guys.
Wife joined us around 1pm and it was fun watching her and Lance talk or look at each other with Tommy & Theresa not knowing they hooked up and I know my wife was loving the secret attention, I made sure I hung out with Lance thruout the day so he knew I was cool with everything and told him have as much fun as he wanted all week week Tina, that i enjoy it as much as she does, he said after being with same girl for so many years it was nice to experience someone new and as hot as my wife.
All 5 of us went to Dinner together the 3rd night and a few bars until Tommy & Theresa went back to hotel, I really wanted to watch Lance and wife so I just suggested we all go back to our room so I could watch them which he said as long as I get to spend more time with her so we went back to hotel, we got back and I went to get ice so they could get started and when I got back they where on the bed, still mostly clothed just kissing, I grabbed a beer and sat on couch and watched, they undressed each other then he went down on her and while he was doing that I grabbed her vibrater she brought and gave it to him saying she loves this so i got to watch him watch him use her vibe on her until she said please fuck me so he got up to get a condom which he didnt have as they where in his room, wife suprised me saying im only other girl Lance has been with in years im sure he is safe which I said fine by me so I got to watch him enter her with no condom, she was on her back with him between her legs, I got close enough behind him I saw her pussy lips stretched around him each time he pulled all the way out and back in, I knew she was orgasming as he started going faster until I saw her pull his ass cheecks into her and hold him so knew he was cumming, they stayed that way kissing for a while until he pulled out and saw her pussy lips just open from his width and his cum leaking out which made me cum without touching myself. He said he better head to his room but I asked him to stay, we had 2 double beds so he took a shower and climbed into bed as we fell asleep in the other bed. I woke in the morning, Tina wasnt in our bed but, it was mostly dark but he was fucking her from behind and when they finished she just layed there and he said he better head to his room so nobody go suspicious, after he left I climbed into her bed and said I wanted to see her pussy, she was swollen and red and when I went to touch her she said she was sore so I jacked off looking at her swollen pussy as she described how he felt inside her.
Day 4th of the trip, Tommy, Thersa & Lance had a fishing trip which was good as it gave my wife a chance to recover, she slept and we had a lazy day by pool and talked about everything, I assured her I was totally cool and wanted her to be his friend with benefits the entire trip, she said since we are being honest she would prefer to be with him without me because its more intimate when im not watching which she prefers and when will she get an opportunity to be with such a cute, fun, younger guy who is so into her, I told her as long as I get ALL the details im OK with it so the last 3 nights of the trip she spent night in his room.
One of the highlights was last full day all 5 of us where by pool around lunch time when she texted me which I was suprised since I was on the lounge chair next to her and it said Lance just texted me and wants me to be naughty and sneak off to his room for a quickie without Tommy or thersa knowing who where sitting with us so I texted back thats hell yes so she got up first stating she was heading to room to call home then few minutes later Lance left saying he was going to do airline checkin for tomorrows flight and I was only person who knew which was so hot, Lance got back first saying all flights all confirmed and then wife came back about 15 minutes later, the funny part she didnt reliaze after having sex she had camel toe big time wearing her bikini especially when she got out of the pool you could see clearly her very puffy swollen pussy lips, she mentioned she felt like people knew what she just did because guys seem to be staring more then normal but I didnt mention it as I luving other guys getting to look at her swollen pussy lips that afternoon.
Since we got home we have had awesome sex rehashing everything from the trip which i really enjoy, I asked her why she enjoyed him so much, she said he is super sweet and a caring person that she had a connection to and they will be life long friends, I asked no silly sexually what did she like, she said the connection, intimacy and feeling so comfortable with him is what makes the sex so great for her along with him being a great kisser, patient lover and him being bigger then me was a big plus because she was able to orgasm during penetration which she normally cant.
Tina has been texting every day about him visting us so hopefully soon, i asked what if he cant make it to visit us would she be willing to go visit him without me, she just said if your OK yes i would enjoy it.
Stay tuned -
We started going to Cabo in the 90's and have been going almost every year since but she has never hooked up with anyone on our Cabo trips so was sure she wouldn't hook up on this trip as well, she is somewhat conservative and seems to be mostly in mom or now grandma mode as we recently became grandparents but she does enjoy wearing skimpier bathing suites and dressing sexy when we go to Cabo as she just says nobody knows us and I know how much you like it so why not.
The 1st day at the swim up bar we met 3 people, a married couple (Tommy & Theresa) and there friend (Lance) that lived about 3 hours from us that we found out was suppose to be 2 couples but Lance's long time GF and him broke up a few weeks before the trip and they convinced him to go anyways, it was there first time to Cabo so we told them all best restaurants, bars, etc and all got along great and when we left to get ready for dinner I invited them to meet us after dinner to show them all the fun little bars around Cabo which they said great, see you tonight.
We went out for dinner and wife mentioned a few times wow that it sucked for Lance that him and his GF breaking up right before there trip but he should have no trouble meeting a new friend to take his mind off the breakup as there are lots of single girls in Cabo, after dinner we went to Monkey Cave which is a great litle bar that makes the best and strongest margaritas and Tommy, Theresa and Lance where already there so we joined and had a blast, it was like we had all known each other for years. We went to a few other bars and then my wife said lets go somewhere we can Dance (she knows I hate to dance) it was close to 10pm and Tommy & Teresa said there tired so they headed back to hotel and Lance said guess I should back as I don't want to be a 3rd wheel but my wife said its ok we have been married so long your not a 3rd will so just us 3 went to an outdoor bar that had dancing and she danced with Lance for a few songs then came back to our table, she knew I was tired so we decided to go back to hotel and when we got back we just said good night to Lance and we went back to our room, she was very horny and intitated sex which she doesnt do often so I asked her wow what got into you and she just said it turned her on knowing some lucky girl is going to get to hook up with Lance so I knew she was turned on by him but she has never fucked anybody she had just met so I didn't think she would do anything except play matchmaker which she enjoys doing for single friends of ours back home.
The next day we went out to the pool and they had 2 lounge chairs saved next to them for us so we put our towels down and i made sure I put mine on chair first so Tina had to put hers next to Lance ha ha.
We all just chatted abvout how great Cabo is and everything it offers, chatting and drinking like we have all known each other for years. I went up to room to check work emails and watched from balcony as wife and Lance talk and laugh until they both got in pool and went to swim up bar together so I stayed in room for about an hour to give them time to hang out and when I got back, Tina asked what took so long I just said issues at work sorry and might have to do bit more work later and Tina said its ok Lance is keeping me company and everyone laughed.
In the afternoon Tommy and Theresa decided to walk around to do a little shopping and after they left I said I need to do a bit more work which normally would make Tina mad while on vacation but she just said I understand so I went to room and sat on balcony watching them, after I left they went to swim up bar and took a few shots and started flirting and playfully touching each other on shoulder, arm, etc as they laughed together so i knew she was interested, situation was right but not sure if she would actually act on it ?
So that night Tommy and Theresa had a romantic sunset dinner cruise planned and Tina suggested Lance join us for dinner since he was left out and after dinner we went to a few bars all 3 getting pretty drunk until wife said lets go dancing which I said you go ahead, Im tired and hate dancing, she looked me in the eye and said are you sure which I said I know you you will safe with Lance and he can get back to hotel safely so yes go have fun, she gave over gave me a kiss which was longer then normal and whispered thank you so I headed back to hotel with all sorts of naughty thoughts going through my head.
I went back to hotel and fell asleep but woke up about 2am and had a text around midnight saying they made it back to hotel and wanted to know if it was ok if she went to Lance room for one last drink but I didn't see the text as I was asleep and now it was 2 hours after she had texted so I assumed she went to his room and was having fun, I tried to go back to sleep but couldnt but didnt want to text her if they hadnt hooked up and have her change her mind.
Around 6am she came back to our room and when she walked in she had that embarrassed look on her face so I just said WOW I think someone had a great time and she just said you have no idea and got into bed with me, I just said please tell me everything. She climbed in bed and cuddled next to me saying I tried to text you but you didnt answer, I was drunk and you are always buggin me to play so I figured it was OK, i didnt ruin the trip did I so I assured her she didnt ruin the trip and it is all i have been thinking about since we all met and cant wait to hear about it, she said after I left they kept dancing and when they took a break and sat at bar he told her he sure wished she wasnt married that she is the hottest funiest person he has met in a long time, she already had a bunch of drinks so she told him that we are not swingers but that I do enjoy when she hooks up with another guy so he grabbed her arm and took her back on the dance floor and she said he started to really flirt and touch her knowing it was OK and they even kissed a few times before they headed back to hotel. once they got back to the hotel is when she texted me but I didnt respond so she was conflicted if she should go to his room but he talked her into goiing to his room saying we dont have to do anything and can just hang out and she admited she didnt want the night to end, once they got to his room he just started kissing her as they undressed each other, once she was down to her panties he sat on bed with her standing in front of him telling her she was the most beautiful women he has ever met as he kissed around her panties then sliding them down and kisisng around her pussy, she said she was so wett and turned on she would let him do anything with her at that point. He pulled her onto the bed and went down on her, she said she had orgasm after orgasm till she was too sensitive so she started to touch him pulling his underwear off, she said he was few inches bigger then me (im average 5") but much much thicker so finally he said i have to feel you and got a condom, got between her legs and she was having sex with a guy she just met yesterday but said it felt like they have known each other for many years, she said he didnt last long and was appologizing, she just told him relax as they kissed and explored each other until he was hard again and this time she said he lasted longer so she was able to enjoy it more, once they finished the 2nd time they feel asleep until she woke up and hurried back to our room to tell me about it.
After we finished I told her best part its beging of the trip and she has all week, she agreed but said that Lance mentioned they needed to be descreet around his friends Tommy & Theresa as Theresa doesnt believe in cheating, etc. I told her that will be even more fun them not knowing haha.
She said she needed sleep so I went by the pool around 10am and they had 2 chairs for us, Theresa asked where she was and I just told her too much Tequila she will be out later then Theresa appologized about us getting stuck with Lance which I assured her we have been married 36 years so we are not love birds anymore and both of us really enjoy Lances company that they could do all the adventures and tours they want and Lance can hang with us and go to dinner with us, etc, she said wow we are so happy we met you guys.
Wife joined us around 1pm and it was fun watching her and Lance talk or look at each other with Tommy & Theresa not knowing they hooked up and I know my wife was loving the secret attention, I made sure I hung out with Lance thruout the day so he knew I was cool with everything and told him have as much fun as he wanted all week week Tina, that i enjoy it as much as she does, he said after being with same girl for so many years it was nice to experience someone new and as hot as my wife.
All 5 of us went to Dinner together the 3rd night and a few bars until Tommy & Theresa went back to hotel, I really wanted to watch Lance and wife so I just suggested we all go back to our room so I could watch them which he said as long as I get to spend more time with her so we went back to hotel, we got back and I went to get ice so they could get started and when I got back they where on the bed, still mostly clothed just kissing, I grabbed a beer and sat on couch and watched, they undressed each other then he went down on her and while he was doing that I grabbed her vibrater she brought and gave it to him saying she loves this so i got to watch him watch him use her vibe on her until she said please fuck me so he got up to get a condom which he didnt have as they where in his room, wife suprised me saying im only other girl Lance has been with in years im sure he is safe which I said fine by me so I got to watch him enter her with no condom, she was on her back with him between her legs, I got close enough behind him I saw her pussy lips stretched around him each time he pulled all the way out and back in, I knew she was orgasming as he started going faster until I saw her pull his ass cheecks into her and hold him so knew he was cumming, they stayed that way kissing for a while until he pulled out and saw her pussy lips just open from his width and his cum leaking out which made me cum without touching myself. He said he better head to his room but I asked him to stay, we had 2 double beds so he took a shower and climbed into bed as we fell asleep in the other bed. I woke in the morning, Tina wasnt in our bed but, it was mostly dark but he was fucking her from behind and when they finished she just layed there and he said he better head to his room so nobody go suspicious, after he left I climbed into her bed and said I wanted to see her pussy, she was swollen and red and when I went to touch her she said she was sore so I jacked off looking at her swollen pussy as she described how he felt inside her.
Day 4th of the trip, Tommy, Thersa & Lance had a fishing trip which was good as it gave my wife a chance to recover, she slept and we had a lazy day by pool and talked about everything, I assured her I was totally cool and wanted her to be his friend with benefits the entire trip, she said since we are being honest she would prefer to be with him without me because its more intimate when im not watching which she prefers and when will she get an opportunity to be with such a cute, fun, younger guy who is so into her, I told her as long as I get ALL the details im OK with it so the last 3 nights of the trip she spent night in his room.
One of the highlights was last full day all 5 of us where by pool around lunch time when she texted me which I was suprised since I was on the lounge chair next to her and it said Lance just texted me and wants me to be naughty and sneak off to his room for a quickie without Tommy or thersa knowing who where sitting with us so I texted back thats hell yes so she got up first stating she was heading to room to call home then few minutes later Lance left saying he was going to do airline checkin for tomorrows flight and I was only person who knew which was so hot, Lance got back first saying all flights all confirmed and then wife came back about 15 minutes later, the funny part she didnt reliaze after having sex she had camel toe big time wearing her bikini especially when she got out of the pool you could see clearly her very puffy swollen pussy lips, she mentioned she felt like people knew what she just did because guys seem to be staring more then normal but I didnt mention it as I luving other guys getting to look at her swollen pussy lips that afternoon.
Since we got home we have had awesome sex rehashing everything from the trip which i really enjoy, I asked her why she enjoyed him so much, she said he is super sweet and a caring person that she had a connection to and they will be life long friends, I asked no silly sexually what did she like, she said the connection, intimacy and feeling so comfortable with him is what makes the sex so great for her along with him being a great kisser, patient lover and him being bigger then me was a big plus because she was able to orgasm during penetration which she normally cant.
Tina has been texting every day about him visting us so hopefully soon, i asked what if he cant make it to visit us would she be willing to go visit him without me, she just said if your OK yes i would enjoy it.
Stay tuned -
9 months ago
