"Resort Dares Part 2!"
TJ - 1
September 8 2023|
Part 2 of TJ Resort Dares
TJ was very excited to discuss the idea of returning to the beach for another "massage" the next morning. The thrill of being nude on the beach, along with the fact that a total stranger had just had his hands all over her body was obviously a turn-on for her. Me too, but that's not as relevant right now, lol.
As we made our way back to the main hotel, it was obvious that her mind was racing with thoughts about what might happen the next day. Her main focus was on the fact that the 'old guy' that gave her the massage seemed to be about 70 years old, and she was curious about whether he would become sexually aroused, and whether he would be expecting any "action".
I speculated that he was probably hopeful that she would be "open" to some additional play, and that he was probably suggesting the morning time-frame because the beach would be empty, AND because it might be easier to 'get it up' in the morning versus the late-afternoon. She laughed at that, and I then dared her to "make his day" by offering to suck him off, or potentially even fuck him if he could get her off first. A challenge!
She was a bit worried that he might not actually have "that level" of sexual interaction in mind, but I was daring her to find out!
The conversation then switched to our plans for the evening and I reminded her that we had another cocktail reception to start preparing for soon. Back in the room she showered and then slipped into the outfit she was planning to wear that night; a long flowery skirt and a tight white tank top. She immediately was concerned that her nipple ring was VERY obvious, and we discussed options. The previous night she felt like her nipple ring got a few too many stares, and THIS top made it even more prominent. The fact that she had agreed to not bring any bra's or undies made for an interesting dilemma.
The nipple ring came out and the top went back on.
During the reception we spent quite a bit of time with another couple that I'll call Julie and Karl. They were very attractive and VERY fit. Gym rats is what they called themselves. There were also two of my friends that were pretty constantly hanging out with is also; Sean and Lee. I'd known then both for many years and they were both very cool. Neither had brought their wives along for the trip, so we sort of adopted them. They both had also met TJ at a previous conference that had been held in Aspen (another long story).
The six of us hung out together for a while, and then all went to the hotel bar together when the official reception ended. The main bar connects to an outdoor bar overlooking the pool deck, and it was interesting to look up toward our room and see that everyone would have easily seen TJ on the balcony naked if they had been looking up.
... so TJ told our little group about the fact that she had been up there naked, as a dare, and the group was thrilled to talk about their own truth-or-dare experiences.
Eventually Sean and Lee wandered off, and it was just Karl, Julie TJ and me. Karl pointed toward the pool and suggested we take our drinks and go put our feet in the pool.
The pool was totally empty, but we heard voices and the sound of a hot tub, which we soon realized was nicely tucked away, down a few steps from the main pool level. There was an attractive couple enjoying the bubbly water and they seemed ok with having us intrude.
The woman suggested that we join them in the hot tub, but we were obviously all completely dressed, so instead the girls slipped off their shoes and sat on the edge. I went and got pool towels from the kiosk and when I came back I heard Julie, Karl and TJ discussing the options for getting all the way in the water. Karl and Julie stripped down to undies, but TJ was explaining that she was naked underneath, and was worried that she'd offend someone.
Long story short. She stripped, everyone commented on her amazing body, then I joined while keeping my boxer-briefs on. The other girls also removed their tops, but frankly the bubbles were concealing any opportunity to see the boobies.
The conversation turned to the "nude beach" and TJ described the experience of being fully nude, and even gave some details of the massage. I was getting hard hearing her describe all of that to these strangers, and I suspect the other guys were hard as well.
The other girls expressed interest in going to the nude section the next day, which was great, but I made note of the fact that TJ had NOT told them that she was planning to go in the morning. She told them we'd see them in the afternoon! She clearly wanted to have private time with the 'old guy'.
I know Karl was playing with Julie under the churning water, and I'm confident that all of the couples were playing discreetly. TJ's legs were spread and I was fingering her pussy. My arm angle was certainly a give-away. No one minded. The other guys were doing similar. The conversation about pro's and con's of having sex in a hot tub were discussed, but everyone landed on the side of 'pro'.
There was no 'swapping' that night, but all three couples clearly had sex right there in front of the each other. Staying mostly underwater was the protocol, and being worried about being caught was obvious for all of us. It wasn't an orgy, but it was definitely visually fascinating.
We had plenty of chances to catch glimpses of the girls bodies, and TJ was not at all shy about riding me reverse cowgirl style with her magnificent boobs clearly visible to everyone.
When we saw shadows of someone coming, the girls scrambled for their clothes, but TJ had no choice but to stay underwater. The shadows turned out to be Sean and Lee! They had come looking for us.
They obviously saw that their were clothes piled all over the place, and apologized for intruding. No one had a problem, and in fact, everyone joked about the timing. Sean suggested that maybe they'd have better timing 'tomorrow night'. Yes, everyone agreed we should all get together the next night.
TJ grabbed a towel and got out of the water, letting everyone see her as she dried herself off.
We went off to the room alone. We had great sex while talking about all of the others. In the next two days, we would definitely have more interaction with both of those couples and the two married men! More about that later.
The next morning TJ was both anxious and excited to go to the beach for her "massage". I proposed that she go solo, but she definitely wanted me to be there too. She explained that the 'massage guy' had told her that the beach does not officially open until 11am, but we could get access by taking the "staff shuttle" as early as 9am.
She wanted to be there by 9:30 and so off we went.
When we arrived the 'old guy' was already there, wearing the hotel uniform, and had the massage table all set and ready to go. TJ wasted no time heading over to talk with him while I went to set up our towels and chairs. As discussed, I would keep my distance and allow 'the massage' to occur semi-privately, but I did pick a spot where I had a pretty good line-of-sight to the area where the massage table was set up.
She stripped out of her bikini, and he got naked also. He appeared to be semi-erect already. I suspected he had a good dose of sildenafil (viagara) running through his veins.
The massage portion of the interaction lasted 20 or 30 minutes, and then became much more of a sexual event! I could see that TJ had flipped onto her back and he had been obviously rubbing her breasts and her crotch, but then she pulled her knees up and spread her legs to give him full access to her pussy. He was taking full advantage of the access and seemed to be attempting to get her to squirt.
After a few minutes of playing with her g-spot, his head went between her legs and stayed there for quite a while. Then she turned over and got on her hands and knees which allowed him to eat her out from behind. At that point I could see him stroking his cock, which wasn't exactly hard, but was obviously enlarged. TJ pulled him around to stand in front of her and she sucked the thing into her mouth.
I love watching TJ give head. She's very effective, lol. Guys don't last very long.
This old guy stopped her from sucking him, and I could see them talking, and both glanced my direction before TJ flipped back onto her back and slid down to the far edge. He held her legs up and wide while she helped guid his cock into her pussy. I couldn't see clearly, but it was obvious.
I was so excited for the guy!
He didn't last terribly long, and soon he was obviously pulling out and it turns out he came on her belly. TJ rolled off the table, gave him a hug and a peck on the cheek, then started heading my way.
Yes, I enjoy seeing TJ have sex with other people. Guys or girls, or both, lol. She's sexy AF, she knows it, and she likes to share! So do I.
She asked me if I wanted to take advantage of the privacy and 'mess around' for a few minutes also, and of course I said yes. She went into the water to briefly 'rinse off' then we went back up to the shaded massage table and had sex in some of the exact positions that she had just been in with 'the old guy'. He was nowhere to be found. He had disappeared into the brush shortly after fucking TJ. We 'jokingly' talked about him probably having a heart attack and dying a happy man. While I was fucking her, I saw him lurking at the edge of the shaded area with another 'old guy' right next to him.
The beach was ours for the next 30-45 minutes, so we took a few pictures after having sex.
I'll write up more of the details of the next 48 hours at the resort, but I'll also start up a post of the details of a few other dares that TJ has accepted. I don't have pictures from many of the dares, but I'm confident you'll be able to use your imagination to fill in the gaps (so to speak). As a head's up, you might want to google nyotaimori, because it'll be the subject of a dare that I'll tell you about soon.
Based on the initial responses, I'll continue to write details of the various times when TJ has sex with other people (sharing is caring), but also will throw in some of the times when it is "just" exhibitionism. Thanks for all of the positive feedback and stay tuned; we're just getting started!
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