Deb meets a new friend on vacation


Well-Known Member
May 30, 2020
Deb meets a friend on vacation

For those of you that have read about our previous adventures, all of them have been with either people we know or an arranged scenario – we recently had our first “random” encounter while on vacation in Florida.

We snuck off to a quick few days on the Gulf Coast earlier this summer, renting a condo on the beach and looking for a little relaxation and sunshine. We hadn’t had much away time over the summer so this was something we were both looking forward to and was deserved! After arriving at our condo, we unpacked and put on our swimsuits for a little time on the beach after the trip. As you may recall, we are both in our late 50’s, but Deb has a great swimsuit bod, even though she’s a little thicker in the middle that she wants to be.

After a couple of hours (and several drinks) on the beach, we cleaned up and decided to walk to a little restaurant down the street. Deb just put on a nice pull over on top of her swimsuit. We got a table and there were several people at the bar, including a guy that kept looking over at us – he looked to be about 40 with salt and pepper hair, and in good shape. I started teasing Deb that she had an admirer and she looked at him and smiled, then turned back to our table. After a couple of drinks I decided to make a trip to the men’s room, and had to walk right by this guy on the way there. I stopped and introduced myself and found out his name was Rod – told him I was taking a break but to go over and say hi to Deb. He laughed and said he might just do that and I moved on.

I took my time at in the men’s room to give him a chance to do it, and returned about 15 mins later to find another chair pulled up to our table and Rod and Deb talking – not expecting it, but I was starting to see this as an opportunity!! I sat down and she said that Rod had stopped to say hi and that he owned a condo in the building we were in. While she was talking I saw that his eyes were devouring her body (her pullover was tight across her boobs and rode up high). I don’t think he realized I saw it, but I know he was finding her hot. I told Rod to stay and have a drink with us, which he did until they delivered our meal – he excused himself and went back to the bar while we ate.

Deb seemed unusually interested in him since she had just met him and wondered if he was married, what he did for a living, etc. – I had no idea but told her if she was interested in that she should go have a drink at the bar with him. We finished our meal, and Deb said, “well, I’m going to have a drink at the bar…care to join me?” I told her I was comfortable at the table, but to go ahead and go talk to Rod.

Deb went to the bar and touched Rod on the shoulder and asked if she could sit down – when she’s had a lot to drink she can get very friendly and flirty. He eagerly pulled a chair up and ordered her a drink. I sat about 50 feet away with a good view, so decided to just watch and see what transpired. They talked quite a bit, with him leaning into her due to some of the bar noise and tending to stay in close. When Deb ordered a second drink I knew it could be an interesting evening. After about 45 mins of them talking, Deb came back to the table and said that Rod had invited us to his condo to have a drink on balcony – he had a larger unit on the corner of the building with a wrap-around balcony and she wanted to see the unit (at this point I’m thinking “Rod” and the “unit” could turn into an event!!). We walked back to the condos together and rode up in the elevator with Rod – Deb was very chatty and leaning into me, which told me she was pretty sauced up.

Once we arrived at his place, Rod gave a us a tour of the rooms including his master suite that had a door to the balcony, with underlighting on the bed and large mirrors on the closet doors – seemed like a bachelor pad to me, and I was starting to feel like this was a normal night with Rod and the tourists.

Rod told us to go out and get comfortable on the balcony and went in to mix us some drinks – we sat down outside and enjoyed to ocean view and the breeze. After Rod came out, we all talked for a while about our everyday lives and he told us his wife had left him two years earlier and that he decided to move to the beach and enjoy being single for a while – his job allowed him to work from home, so it was a perfect fit for him. Deb seemed to be hanging on every word, and I noticed that her nipples were very hard under her top and pullover – I imagined she was also wet between her legs.

Deb excused herself to freshen up, and Rod and I sat nursing our drinks – he commented that she was quite a lady and that I was a lucky guy. I stated that I was luckier than he knew, and if he played his cards right he might get lucky as well – Rod laughed and said, “what does that mean?” I told him that I had shared Deb within some friends and some acquaintances, but that she had never been “picked up” or had a one-night stand since before our marriage. Rod was very interested by this time, and I told him that if he could talk her into it he could go as far as she would let him – I could tell he was ready to take that challenge!

Deb returned and sat in her chair, but her back was slightly turned away from the view – Rod told her to come sit on the couch where the view was better, and she moved over to get comfortable. We had another drink and talked, and somehow the conversation turned to getting older and surgeries to look young. Deb had a boob job about 5 years ago, as well as a tummy tuck – I was surprised when she told him about her surgery, and he asked a number of questions about it…he had wanted his former wife to have it done, but she was scared of the pain and wouldn’t do it. She talked at length about the pros and cons and how she was glad she got it done. I decide to put a little edge in the conversation….

I told Rod, “her tits are great and look so natural, which isn’t always the case.” He jokingly said that they definitely looked natural and good! Deb blushed a bit but thanked him. I told her that Rod had surely seen his share of womens breasts, and that she should show him how great hers turned out. I thought she would just take off the cover she had on as she still had a bikini top under it. After a minute’s hesitation she pulled the cover up off, and he could see about 60% of her boobs with cleavage, side boob, etc. Rod joked that maybe it was the swimsuit top that was holding them up, and Deb slowly pulled the top up exposing her breasts in full glory to Rod – he was very complimentary of how firm they looked and how they stood up with her now VERY hard nipples. She turned side to side, but didn’t really get closer to him…just giving him a view. I stood up and walked over to the couch and sat down behind/beside her and told Rod, “what I like about them is they FEEL natural and not fake”, and then put my hands around her and gently massaged her tits and nipples showing him how soft they were – Deb didn’t resist but leaned back against me while I kneaded them. She turned to say something to me and I gave her a little peck on the lips, which she turned into a longer kiss!

She broke off the kiss and we all just sat there not saying anything in the sexual tension. Again, I decided to push a little and said, “Deb, why don’t you let Rod feel them as well so he doesn’t think I’m a liar?”. I stood up and motioned to Rod to come sit behind her, which he did – and he slowly put his hands around her sides and cupped her breasts. Deb let out a little moan while he massaged them and used his thumb on her nipples. After a minute she did the same thing to him that she did to me…she laid back against his chest. Rod said, “they feel incredible!” and she turned her head toward him to say something…but that head turn resulted in him kissing her on the lips lightly, and then plunging his tongue deep into her mouth – and I was sitting in the chair watching my topless wife make out with this stranger on his balcony!

After some pretty hot making out, Debbie pulled away and sat up – Rod was pretty flush, and said, “we could take this inside where it would be more comfortable?”. I looked at Deb and said, “why don’t you two take it inside….I’ll sit out here and enjoy the breeze and the view”. That was the invitation that Deb was looking for, and she stood up with Rod, gave me a kiss, then took his hand and headed into his bedroom. I was interested in what was going to happen, and fortunately neither of them felt a need to close the sliding glass door or turn the lights off. I was sitting at an angle to the bedroom but could hear them talking and laughing as they headed to the bed. It gotten suddenly quiet, and my guess was the make out session had started again. I found out that if I pulled my chair around slightly I had a clear view thru the door at the bed and the full mirror closet doors – I had the second best seat in the house!!

Rod and Deb were sitting on the bed kissing – Rod had Deb’s top off and was slowly massaging her tits while kissing her, and then moved his head down to her nipples and gently sucked and licked them both with Deb’s head back and eyes closed. She was rubbing his shoulders and his upper chest as he leaned into her and she lay back on the bed. With nothing but bikini bottoms on, it didn’t take him long to get her naked and she was laying there in her glory while he massaged her tits. His hand moved down her stomach and towards her wet spot and she spread her legs slightly to give him access – I could hear her breathing quicken and see his fingers rubbing her pussy and inserting fingers into her wetness. Without wasting anytime, he lowered his head and kissed her stomach working his way down between her legs – he slowly spread her legs and Deb gave him full access as his tongue replaced his fingers on her pussy. I could hear him working her clit, and Deb moaned as he repeatedly hit that spot that got her closer to orgasm. He spent 5 minutes devouring her before she sat up and told him she wasn’t ready to cum yet!

Rod had his shirt off (and was in pretty good shape for a guy in his mid 40’s) but still had his jeans on, and Deb grab his button and zipper and had them off quickly – I could see where the name “Rod” came from, as he jumped out of his underwear a full 8 ½ inches erect! Deb looked like she was about to have another meal, and grabbed his cock and started stroking it slowly. Rod stood there next to the bed and was between my view of Deb….however I could see clearly in the closet doors that she was stroking his cock and kissing his belly, while slowly moving down to him. I saw a side view of her licking the side of his member, running her tongue up to the head, where she took it in her mouth. I saw in the mirror her slowly moving her head back and forth as she sucked his dick, stopping occasionally to tongue his head or move down to his balls. I could tell Rod was in heaven as Deb swallowed him in a slow and steady motion. This must have gone on for 5 or more minutes when Rod pulled away and sat down next to her on the bed.

As they kissed, Rod turned her slightly so he was coming up behind her – Deb got up on her hands and knees on the bed and Rod came up behind her and slowly slid his cock into her from behind…there was no issue penetrating her as she was sopping wet. I watched eagerly as he slowly and then quickly began driving his full cock into her. Deb was moaning and pushing back on him – I am about 6 ½ inches and thick, but she had no problem taking him! I realized about then that he didn’t have a condom on, but couldn’t focus on that with the view I had. Rod pulled out of her and asked her to ride him as he lay flat on the bed.

Deb turned around and climbed on top of him and I could see her slowly sliding down on his cock – normally when she rides me cowgirl she moves her whole body up and down, but she was sitting straight up on Rod and fully using her hips forward and backward to ride him. This was such a sexy view, as her titties bounced and moved with each thrust she had on his dick and I could tell he was enjoying the view and well as the fuck.

Deb’s breathing increased quickly and I could see she was rubbing her clit with one hand and her nipples with the other – she let out a gasp and began to shudder and I knew she was cumming in waves. She kept riding him until she was totally spent. Rod rolled Deb onto her back and climbed on top of her – I could tell he wanted to come and this was going to be his time to control. He reached down and kissed Deb and then slowly lowered himself onto her, sliding his cock deep in her via the missionary position. He started to pump slowly as Deb rubbed his back, grabbed his ass, and wrapped her legs around him. Rod’s pumping increased quickly and I could tell he was there…without any hesitation, he started to cum in her and fucked her for what seemed an eternity while he dumped his full load in her pussy. Deb rubbed his ass cheeks while he came down, and he climbed off of her to catch is breath. I stayed outside and just listened as they talked briefly, then both got up to get dressed.

Once they joined me back on the patio, I told Rod that I hoped he enjoyed that as much as I did – and all he could say was “wow!”. I could tell Deb felt the same way. It was late and we needed to get back to our place to sleep, so we told him thanks for the evening and left his place for our own.

After a shower, I took full advantage of Deb and her now used and sore pussy in our bed – telling her how much I enjoyed watching her be pleasured. We had drinks again with Rod the next evening but didn’t repeat the visit to his place…and he had to leave for a trip the following day. We told him we would be back, and he told us we had a place to stay when we visited again!