Weekend Getaway - Orgasmic Massage

I've been married to my wife for over 6 years now and I still haven't managed to give her an orgasm. This weighs on me more than you can imagine. In my previous relationships this has never been an issue -- in fact I have been known to make women quirt which is why this is such an issue for me. She tells me I have a big cock, and that I am the best sex she has ever had.... I just don't know what to believe any more.

Yes, she has issues -- she suffers from depression and anxiety, and I've always wondered whether this is holding her back from letting go and just letting an orgasm take over her body in the most natural way possible. Having wondered how I can help her get to this place of pure happiness I have broached the subject of therapy, counsellors, even other partners but she won't hear of it. That left me at my wits end and I could only come up with one idea that may work.... a massage!

The next things were how, when, where? All valid questions but with kids this does complicate things. But as I was working through my options, I began to formulate a plan that may work.

My birthday was coming up and she kept asking me what I wanted and honestly the idea of a couple of nights away alone was what I really wanted. Over the next few weeks, I was able to begin working on my plan.

I made a reservation at an upscale hotel in NYC and was able to get my mother-in-law to look after the kids for a Friday and Saturday night. This meant that once we had completed the school run on Friday afternoon, I could whisk her off for a romantic getaway. I had planned for dinner reservations on Friday night and then Saturday we would go for brunch, walk the city, and then head back to the hotel for a nice dinner. I wanted to surprise her with a nice massage on the Saturday night and I had contemplated this being a couples massage but I decided that if I were there she would never be relaxed enough, so the plan was to have dinner together and then let her know that when she got back to the room to have a relaxing soak in the bath and to expect a knock at the door around 9pm as I had organized a massage for her, to enjoy it to the fullest and just relax. I would remain at the bar and would come up once it was over.

Selecting a masseuse was not as hard as I thought. I found an app for out call massage services and then it was a simple task of searching through the many men that offer such a service and finding one that I thought my wife would find sexually appealing yet not to aggressive or obvious. I landed on a gentleman by the name of Ryan. He was probably mid-forties, white, had a well-maintained body, brown hair with graying temples and no facial hair. But what struck me was his 9" cock. It looked incredible. I messaged him and asked if he was available and what his rates were. Within a matter of 30 minutes, I had a response with a couple of follow up questions:

"Yes, I'm available but please tell me what kind of service you are looking for?"

"Will you be present?"

"Would you like the session to be recorded or would you like to hear the massage?"

The first two questions I thought were appropriate, the last one got me thinking. I thought for a moment and responded.

"Hi Ryan,

Thanks for getting back to me. In answer to your questions, I would like you to provide my wife with an erotic massage. She finds it hard to relax and I chose you as I wanted you to make her feel comfortable enough to let go of her inhibitions and yes, if she will allow it, you have my full permission to go all the way as ultimately, I would love her to have an orgasm. This is something that I have been unable to achieve myself and I simply want to make her happy and fulfilled. I will not be present at the time of the massage so you will have all the privacy you need. The final question you posed gave me a lot to consider.... but I would love it if you could record the event, but this will have to be very discrete and would be between you and me.

I hope this helps, and if you can please let me know your rate I will process payment and will text you the hotel and room number on Saturday!"

Ping.... the message simply said:

"$350 and I look forward to hearing from you on Saturday!"

With that we were all set!

On Friday morning I told my wife that we were going away for the weekend and that she should pack her bag with both sightseeing clothes and some dressy clothes as we had reservations for later tonight and tomorrow for dinner! Your mom will look after the kids, so all we need to do is do the school run and we can head down.

Around 5pm we arrived at the hotel which was luxurious. I booked a suite so there was a sitting room, separate bedroom and the bathroom had an oversized tub. It was beautiful. Friday nights dinner was nice, we ate great food, and had shared a nice bottle of red wine before heading to the bar for a quick night cap. It was the perfect start to the mini trip. At one stage my wife had to run to the restroom and while she was out of view, I quickly sent Ryan a text.

See you at 9pm tomorrow -- We are at the Nobu Hotel, Room number 237.

The rest of the evening was normal -- Not wanting to push things there was no sex we just held each other and slept!

When we awoke, the light was shining through the curtains a little and I looked at my watch -- 8:30am. We never get to sleep in this late with the kids, so it was a great way to start the day. My wife got up and headed to the bathroom, and after a few moments I heard the shower turn on and she peaked her head out and asked if I would like to join her. Not even answering I removed the covers and headed to the shower.

To me she is so sexy. We entered the shower and as she began to wash her hair, I began to lather soap over her body. Gently soaping her neck, shoulder, and down over her butt. My erection at this point was beginning to hurt a little and as she bent down to pick up the conditioner my cock began to nestle against her butt. She moved a little but never really gave me the green light to insert it into her pussy, so I didn't. She turned around and began to wash out the conditioner and I continued to soap her breasts, down over her tummy and then I cleaned her pussy and legs. As I was washing her lower legs I was kneeling on the floor and had an unobstructed view of her pussy -- I simply couldn't resist -- I slide in a couple of fingers and gently began to lick on her clit. My god she tasted amazing, and I could tell she was enjoying it as she lowered her hands and pulled my head deeper into her. We ended up having sex in the shower -- I came, she didn't but maybe that will change later!!

The rest of the day went like I had planned -- we had brunch in the city, saw some sights, and people watched. We walked hand in hand back to the hotel to relax a little before dinner. She dressed in a matching lacy black bra 36 D and thong and wore a long black dress that extenuated all her sexy curves. She has her long brown hair brushed back into a ponytail and added some makeup and dark red lipstick. She looked incredible.

We headed down to dinner and again ordered a bottle of red wine. The conversation flowed easily talking about all the things we saw during the day, and how nice it was to be away without the kids. Once dinner was ending, I mentioned that I had one final treat in store for her. I ordered her another glass of wine for her and told her to take it up to the room, take a relaxing bath and at 9pm I have scheduled for her to have an in-room massage. By the look on her face, I couldn't figure out if she was happy...I would say she was more in shock. I simply said look I will be down here and if you need me call me, but I wanted to do something special for you, so take the drink, relax, and enjoy the massage -- I'll see you in a couple of hours!

The next couple of hours were a blur. I couldn't believe that she followed my direction, left for the elevators to the room and now all I can do is wait. Thankfully during my free time -- there was a game on the tv, so I nursed a couple of drinks and watched that.... there want much else I could do. My mind was all over the place, but I kept telling myself that I did this for her and if all goes to plan it would be worth it.

Before I knew it 10pm rolled around and I was thinking about heading up to the room as the massage was booked rom 9pm -- 10pm. I wanted to give it a few mins to make sure the coast was clear. About 5 minutes later my phone pinged. It was from Ryan -- The message read:

"All done here, your wife was adorable. Video will be sent shortly. Hope we can schedule something again soon."

Ping -- The video arrived!

Now what do I do? I so desperately wanted to watch the video or at least scan through it before heading up to the room, so I ordered one last drink and opened the video on my phone set it to silent and found a corner, so I wasn't disturbed.

The video started and it showed my wife fully naked with a towel wrapped around her as she climbed onto the massage table. She laid on her front with the towel covering her butt and legs. Ryan was wearing black scrubs and looked very professional. I couldn't hear what they were saying as I had the sound off, but I could tell they were talking, and Ryan was trying his best to put her at ease.

His hands then began to massage her shoulders and upper back moving lower down to just above her butt. He was strong with firm strokes easing the tension out of her. Her arms were lying flat against the table on either side of her body. As he continued to make long strokes down her body the towel began to move ever so slightly. The stokes long and firm from the nap of her neck to her lower back. He was positioned at the head of the table and as he slowly moved to the side, I could see that he was already becoming aroused. As he moved to the side, he was a little more daring rubbing her back and gently touching her side boob and as he did that her arms move out slightly. The towel was raised from her legs and folded again over her butt. At this stage her legs were closed but as he began working on her thighs down over the back of her knees to her ankles and feet, he was able to spread her legs a little. Repeating the same process on both legs he was now at the foot of the table. He had the perfect view of her legs running all the way to her ass and he could see her beautiful pussy.

With long strokes up each leg his hands got closer and closer to her inner thigh and at times I could see his finger gently brush over her labia. Again, I could see them exchange a few words and a second later the towel was removed. He massaged each buttock and ran his oily fingers down the crack off her butt.

At this stage I was so turned on and glad I was sat in a corner as my pants were tenting with the raging hard on which I was trying hard to conceal.

After a few short moments he moved back to the side of the table and continued to work her ass and inner thigs. Her hand suddenly dropped and reached for his cock -- I could see her gasp. She was too shy to pull it out, but she was tentatively touching it through the scrubs and his cock was hard too. Even from here it looked massive.

She was then asked to turn over which she did. Ryan oiled his hands again and began massaging her breasts, running his hands down over her stomach, down over her pubic hair all the way to her feet. This massage looked magical. He then took the initiative and slowly removed his top and bottoms and continued to massage my wife skillfully, naked, with his 9" cock resting in her hand. It was at this time that she began to stroke his cock slightly and because he knew this was going to happen, he focused more on her pussy. He raised her knees, so he had better access and slowly inserted one then two fingers inside of her. With one hand on her pussy the other concentrated on her nipples. The next thing I saw was them kissing. And I mean kissing passionately, she wanted him, she wanted his cock, and all her inhibitions were lost.

He slowly mounted the table, and she guided his cock to the entrance of her pussy and slowly he began to fill her inch by inch until she could take no more. He fucked her slowly at first with long deep thrusts building up the rhythm until they were going at it like rabbits. My wife was in ecstasy -- I could see her mouthing words and asking for more, asking for it harder, her body began to writhe against his and in only a matter of seconds she was gyrating uncontrollably and rolling to a powerful orgasm like I have never seen. He continued to fuck her through the orgasm while slowing the pace down and his breathing then became more erratic -- he was going to cum. Was he going to cum in her? God I hope not. Then suddenly and abruptly he pulled out of her -- moved up the table and she opened her mouth. Ryan began to shoot rope after rope of cum deep into her mouth and she savored every drop, licking his softening cock clean.

The massage finished with them both kissing and tasting each other for one final time before Ryan climbed down and began to pack things up.

Now what do I do? I got what I wanted -- my wife experienced a mind-blowing orgasm. Will she tell me? Will she make love to me when I get to the room? Will she be mad at me? Satisfaction and uncertainly in equal amounts -- Whatever will happen next?