This story involves wife-sharing. If that offends you or not your "thing", please move on.
All parties involved are over 18 years of age.
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For over 15 years, I tried to get my wife to have sex with another man, but she always refused. Being raised in a Christian household, and being (somewhat) shy and conservative, she wouldn't even entertain the idea. She knew from the beginning of our relationship that I was into wife-watching and I had hoped that someday she would fuck another guy for me.
Over time, she went along with the fantasy talk during sex, but afterwards would always refuse to actually do it and would say that she just went along with the fantasy talk while in the heat of the moment, because she knew that I liked it. During these times her pussy was always much more moist and her orgasms were much stronger, so I knew that she was enjoying the fantasy also.
After 15 years, 2 circumstances occurred to persuade her to consider letting another man take her marital cherry. After more months of begging, She finally agreed for us to meet with man, but insisted that she would probably just "fool around" a little bit, but she would not actually fuck him. We got a room at a local hotel and the three of us went to the room to explore. We played strip poker and for the first time since we'd been married she allowed another man to see her completely nude body.
She was in perfect physical shape, with large breasts and curves in all the right places. Her vaginal opening was waxed clean and she left a small landing strip of pubic hair on her mons, just above her vulva. With moist labia that extended from her vagina, she looked extremely sexy.
After lots of foreplay, they had oral sex, but after he came, he could not regain an erection solid enough to actually fuck her.
Afterwards, she claimed to have completed my request, but I argued that it was not complete, because he was unable to penetrate her womanhood with his cock. Eventually, she agreed to try one more time. This time was a huge success. We met with another guy that she was attracted to from an adult website. In the hotel room, I watched as another man crossed that barrier and his cock penetrated my wife's once-faithful pussy. He not only fucked her, but he actually made passionate love to my wife. It was something that I didn't think that I would ever see, but I was thrilled that it had finally happened.
Afterwards, once again guilt & morals set in and although she enjoyed it immensely, she stated that she would never do it again. Watching another man fuck my wife was now etched in my memory and I vowed to make it happen again. It was like a drug habit that I couldn't kick and I NEEDED to see it again. After almost a month of me begging and repeated messages from Chris to try and convince her to do it again, she relented and agreed to one final time.
We planned for the same hotel, but before meeting, I told her that I felt that she was holding back a little (the last time), doing it with me present. So, I left them alone for an hour and when I returned, I was treated to my wife riding his cock (in the cowgirl position) and his cock was completely bare. She was fucking him bareback and experiencing unrestricted flesh to flesh sexual intercourse, with a man who wasn't her husband.
I watched them fucking without them realizing that I was watching. She was very animated and her orgasm was intense. She fucked him 5 times that time, including twice in the morning the following day and she even let him cum in her one time.
Once again, afterwards she said that she would never do it again. Her argument was that although we got together with Rob once and they did not fuck, she could argue that she never fucked him. With Chris, they got together twice, but it was still only one guy. So in her mind, she only fucked one guy and she would never do it again. Her logic was "I fucked one guy for you, now I'm done. Don't ask again."
We never spoke with Chris again and although I really wanted it to happen again, I respected her wishes to not ask again.
A year later, we had planned a trip to Hawaii. Weeks prior to our vacation, I had been working out of town and we hadn't had sex for almost a month. She constantly reminded me that she was in her sexual prime and needed to get laid, but we never did. I told her that I was perfectly fine with her getting a fuck-buddy, in fact, I encouraged her to, but she refused. Occasionally she would say that she would, but then would always say that she couldn't. I even told her to contact Chris, but she refused.
Prior to leaving for Hawaii, I decided to see if I could get her to fuck another guy while we were there. The situation would have to be perfect and decided that I would get her a sensual massage and see if could possibly lead to her fucking the masseur. She loves massages, but didn't get them often. I knew from experience that she typically got massages from a female masseuse and only wore panties during a massage, in order for the masseuse to have unrestricted access to every inch of her body, except for her pussy.
I found a local guy who said that he does sensual massages and had previously fucked wives while the husband watched.
I called the number on the ad and spoke with him. "Hey Dan, I saw your ad for massages and was wanting to treat my wife to a sensual massage."
"I can do that." He responded.
"Great. How far will you go with my wife?" I asked.
"As far as you want and she allows." Was his response.
"So, oral sex and full intercourse is ok?" Getting excited as I asked.
"Of course. I'm not really into anal or bondage, but just about anything else is ok. How far would you like this to go?" He asked
"Well, she fucked another guy about a year ago, but since then has said that she won't do it again. I think she might, if the right situation is presented to her. She hasn't been laid in over a month and has recently told me that she's extremely horny and needs to get fucked. I'm hoping that she'll let you. I constantly tell her that I want her to fuck another guy again, but she says she won't. I'm hoping that you can change her mind." I told him.
"I'll do my best." He chuckled.
Our flight to Hawaii departed at around 8am and landed around 12pm local time. We got our luggage and caught the shuttle to our hotel.
Once Alice and I got to our room and settled in, she complained about a sore back (from the plane ride).
"Perfect!" I thought.
"Hey hun, why don't I get you a massage, so that you're not uncomfortable during this whole trip?"
"Really? I'd love a massage. I haven't had one in years."
"Ok, let me check with the hotel for recommendations."
"Make sure you find a masseuse that does sport massage. I've got inner muscles that need a more forceful massage, as opposed to a soft massage." She was happy.
I called the concierge and asked for recommendations. I jotted down the numbers and pretended to call them.
"Hi there, I'm looking for a masseuse that does deep tissue massage. Do you have anyone who does and is available today...."
I waited for their response. I knew that it was such notice and even if they did have someone who does deep tissue, they're probably not available on such short notice.
"Oh. Not today. Ok, I'll keep you in mind for two days from now."
After another fake call, I called Dan.
"Hi there, I'm looking for a masseuse that does deep tissue massage. Do you have anyone who does this and is available today?"
"Hey Tom, do you think we're on?" Dan responded.
"Hmmm. I guess that'll be ok, if it's all you've got available." I told him.
Alice looked at me with a concerned look. I put up a finger as if to say "hold on".
"Ok, Sure. We're at the Hilton Hawaiian Village, Diamond Head Tower, room #618. See you in around an hour." I hung up the phone.
"What was that about?" Alice inquired.
"The owner of the company said that his employees are all booked, but he got a cancellation and can do it himself."
