Fun In The Serenity Room

PART 1... My best friend Kevin was the best man for my second marriage and is a great guy, but maybe a little more shy than I am.

Over the years, we've talked about everything from investments to the women I was with between marriages, even the 'asian massages' I'd occasionally get. He was always keenly interested and even went to the massage place a couple times himself.

Kevin and I try to get out and catch up every 3-4 weeks at a local bar or restaurant. We'll usually end up having just enough wine or spirits to 'loosen the conversation some'. At one of our last outings, the topic of massages came up more than usual.

So I figured he brought it up so I'd add to the discussion... besides, talking openly with someone about what the masseuse did or how she looked was a bit of a turn on.

At that same outing, I reminded him that I have been going to the home of a massage person off and on for a couple years. This woman, Jen, is awesome... she's super friendly and does the massages typically wearing only her thong panties. She has rules that include only mild touching of her, and certainly no blowjobs or sex for me. Which is fine. But the massage always ends up very happy & it keeps me coming back.

So at that outing, I told him that I could send him some pictures from some of my sessions with Jen. He perked up and I was loosening up, so later when I got home, I went thru the dozens of photos from my sessions and grabbed some that were, say, 'R rated'. Pictures showing her topless and fondling me "just out of the camera's view" (I didn't want to freak him out with some dick pix... at least not yet).

Once I knew his email was secure and he was good with getting some pics, I sent him maybe 5-6 of the photos. Kevin seemed pretty happy and said that the photos were great and he really enjoyed them. "They were fantastic!". I now felt like I was safe maybe taking things another step.

A day or so later, I mentioned that I have some other photos and some 'less cropped' pix if he was interested in seeing more. It was a resounding 'yes, please!'

So I went thru some of the more risqué photos, and sort of 'uncropped' some of the ones I had cropped and sent earlier. The resulting pix had ones of Jen holding my cock, me caressing her breast, her rubbing my hard dick with a vibrating pen, and one with her sliding a leather riding crop across my cock. All were pretty open and graphic compared to the first set I sent.

He was appropriately pleased with the new set of photos. I texted: "I trust the 'X minus' pix were okay... I don't want to flip you out or anything.". He came back with 'No, all good. No issues!'. I mentioned to him that I have many more and have a couple videos that I'd have to cut down to email-size. He texted two thumbs up. I actually have some pix that are a bit over the top for him at this point... pix of me solo, of me shooting my load onto Jen's tight belly, and even some of me with other 'curious' guys that Jen set up. But those may be for later...

PART 2:

After a couple weeks, Kevin and I met back up for some wine and the convo eventually turned to the photos and Jen's place. I asked him if he'd consider going there for some sessions. Almost to my surprise, Kevin said 'absolutely'. He asked me to send the address. I told him that Jen would be more comfortable if I brought him there the first time (ok, so I fibbed). He said 'yeah I don't have any issue with that'. So, smiling, I told him to think about some good potential dates and get back with me.

Once we necked down on some dates, I contacted Jen and set up a time the next day. I picked Kevin up at work and we headed her way. He seemed pretty calm, more so than I figured he'd be. What Kevin didn't know is that I asked Jen to play along a bit and that I wanted to be at least partially involved in the fun... but hat we'd probably have to ease into it. She was happy to help!

When we got to Jen's, we went inside and I introduced them. Jen brought us all some wine and we chatted for a bit. She mentioned for Kevin to get comfortable and strip down to whatever level he was good with. So I started to excuse myself to the other room. That's when Jen went into 'support mode'. She looked at Kevin and said 'would you mind if he stays here on the chair? I'm just always really cautious the first time with a client'. The politeness in Kevin wouldn't let him say no, and he looked over to me and said he was fine with that. The bait was taken, Lol.

Kevin then took off all his clothes and stepped up to the massage table and laid face down. Jen starting doing her thing with the oils and softly began caressing Kevin from the ankles, moving up to the calves, and then across his butt and on up to his shoulders and neck. I sensed Kevin was really enjoying things. We were all talking a bit and things were very loose and comfortable. Kevin spread his legs a bit as she started rubbing the insides of his thighs and slowly running her fingers into his ass. I was starting to get hard and very horny watching this, and snapped a few pix here and there...

PART 3:

When she had Kevin flip over, there was really no hesitation. I'm not sure what I expected, but having him flip without concern, knowing I'd be just a few feet from his now hard cock was interesting at the least. That's when I decided to stand up and go to the far side of the table.

As Jen was rubbing his legs, chest, and brushing against his cock, I took the risk that he'd take it badly, but reached up and started massaging his arm and hand, rubbing the inside of his palm and his fingers. He kind of moaned, so I figured I'd just keep going. I started rubbing one leg as she did the other. I went up and massaged his shoulders as Jen would more assertively stroke his cock. At one point, I asked 'you good?' and he said 'definitely!

With that, I pulled my shirt off, then my jeans and then slowly pulled off my boxers. When I went back to the rubdown, Jen was now rubbing Kevin's nipples and leaning down to kiss them. At that point, I lifted my hand off Kevin's thigh and moved it over to his cock. I gently closed my hand around him and softly stroked. To my surprise, the next thing I felt was Kevin's hand closing around my dick, and gently fingering my balls. Hesitation completely out the window, things began to get more intense and heated.

At one point, I bent over and put the head of his cock in my mouth and got a great 'selfie' to share with him later. At another point, I walked over behind Jen and rubbed her ass with my cock, while putting one hand on her right breast while rubbing Kevin's nipple with my other hand. Finally, I hopped up on the table with Kevin and started rubbing my cock on his, to the point of complete frottage. It felt so good to know that this best friend was now even closer, with our new experimentation and secret.

As Kevin got closer to climaxing, I went back down on him, sucking and tonguing his swollen dick. When I knew he was close, I moved off the table and Jen took over stroking him and pushing her finger into his ass.

Kevin twitched and moaned and shot a nice cum stream up onto his belly and Jen's hand. Meanwhile I was jerking off like mad at this sight when Jen reached over to finish me off as well.

After cleaning up and sitting down to rest a bit, I asked Kevin if he liked the massage and the experience. He said it was one of the best things ever. I asked if this was a 'do over' sometime, and he said yes, for sure, and that he may want to be the one at my side the next time. I nearly got hard right then just thinking about that next time.