My Lifestyle Experiences 06

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Will Tom’s wife fuck another man (again).
3.9k words
3.98
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Part 6 of the 6 part series

Updated 02/20/2024
Created 12/20/2023
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Tom_Brown
Tom_Brown
285 Followers

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.

--------------------------------

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."

"A guy?" She sounded concerned.

"Yeah. You've had male masseurs before, haven't you?"

"Yeah, but only a couple times and they were sports massages at the gym." She responded.

"Just think of it as the same thing. It's no big deal." I tried to make her feel more comfortable about it.

"Let me make you a drink to relax you."

"I'm already tipsy from the booze that I drank on the plane." She said.

"You still seem uptight. Have another one." As I handed her a stronger drink from the mini-bar.

"Ok." She accepted it.

Around 45 minutes later she had finished her drink and I had another one waiting for her.

"Are you trying to get me drunk?"

She was feeling the effects of the alcohol.

"I am, so that after your massage you can fuck the shit out of me!" I teased.

"Good cus I'm already so fuckin horny. You know that massages make me even more horny, right?"

"Then I better warn the masseur that you might attack him, if he's any good." I continued to tease her.

"I might." She teased back.

Just then there was a knock on the door. Alice went to the bathroom to undress, while I let Dan in and directed him where to set up his table. Once set up Alice returned and removed her robe. Being shy and conservative, she wore black nylon, stretch t-shirt (with no bra) and matching black nylon panties. As I've stated in other chapters, her breasts are very large with prominent areola and nipples. Even though she was completely covered up, her 36DD breasts looked amazing in her stretchy top.

Dan had her lie face down and placed a light sheet across her body, then began his massage. After around 40 minutes, Dan excused himself to the restroom. He wore light sweat pants and his erection was very prominently showing, through the pants. I walked up to Alice.

"Did you see the hard-on that you gave Dan?" I asked.

"Ummm, no." She suspiciously answered.

"That was a weird way to answer." I told her.

In a whisper she responded "I felt it."

"What? How?" I inquired.

"He massaged my hand and laid it palm up on the table. When he moved to my side and reached over me, his crotch landed on my hand and I felt his hard on. I turned my hand over and after a while he reached over and flipped my hand back over. A few minutes later, his crotch was in my hand again. This time he held my wrist with his hard covered cock in my hand. I looked at him and he said how's that feel? Not knowing if he meant the massage or his cock, I said good." She confessed.

"How did his cock feel?" I asked.

Shyly, she whispered "hard."

"Did you like it?" I wanted her to admit it.

"I don't know. It felt good, I guess." She confessed.

"Did it make you wet?" I needed to know.

"I don't know. You know that I'm super horny, so anything could make me wet." She said bashfully.

With that, I reached down and felt the crotch of her panties. They were wet. I moved them to the side and slid my fingers through the folds of her pussy. She was definitely wet and excited. She moaned.

"Do you need to be fucked?"

"You know that I do!" She complained.

"Well, since you haven't had any cock in over a month, maybe you'd want two tonight?" I smiled.

"That's fucked up! You know that I need to be fucked." she complained.

"Why dont you fuck him and I'll fuck you afterwards. Hell, maybe we can both fuck you all night, to make up for your lack of cock." I offered.

She close her eyes and I could tell that she'd do anything to get fucked today.

"Well?"

"Maybe." she whispered defeatedly.

During this conversation, I had slipped a finger into her vagina and was sliding it in and out, finger fucking her closer to an orgasm. I heard the bathroom doorknob turn and quickly removed her panties, before she could stop me.

"Wait. What are you doing?" She asked.

"You won't need these." As I threw her damp panties to the bed. I pulled the sheet over her, just as Dan exited the bathroom. Dan resumed his position at her feet and began massaging her legs again. As he did, he raised the sheet higher and higher up her legs. Once he got to her ass, he saw that her panties were gone and her moist pussy was inches from him. As he massaged her ass, her pussy became more visible to him.

"Mmmm" he moaned quietly, almost in a whisper.

Alice heard him and closed her eyes in embarrassment, but did not stop him. He began pushing her ass cheeks further apart and in doing so, her pussy opened up to his view. He continued this for a while and was only inches from her moistening pussy.

"Hey guys, Starbucks is closing. So I'm gonna run down and grab a coffee, before they close."

Alice's eyes shot open, but i was already closing the door before she couls stop me. What she didn't realize was that I never left the room. Being that the room's door could not be seen from the room, I acted as if I left, but never did.

Dan continued spreading her cheeks and finally Alice spoke.

"This is so embarrassing." she said.

"What is?" Dan responded.

"Tom removed my panties and since you've raised the sheet above my ass, I'm sure you're getting an eyeful."

"Don't be embarrassed. Your flower is beautiful."

"Stop." she blushed.

"You must be pretty excited, because it's soaking wet. Are you horny?" He asked.

"It's been over a month since we last had sex, so right now I'm extremely horny." She responded.

"This pussy looks too good to be neglected." as he slid his fingers between her aroused lower labia.

"Oh fuck." she moaned.

Just then he moved to the other end of the table (near her head). He removed the sheet completely and began massaging her upper back.

"You should remove your shirt, so that I can get deep into your back muscles." he told her.

"Ok" she responded, then got up on her knees to remove her top. She looked at Dan as if to say "excuse me!" so he turned away from her. as she removed her top, he turned back around and admired her large breasts. Once the shirt was off, she tossed it to the bed and noticed that Dan was now staring at her tits. She laid back down and the massage continued.

The closer he moved towards her ass, the closer his crotch moved towards her face. As he reached her ass, he slid a hand between her cheeks and down to the petals of her moist pussy again.

"Mmmm." She moaned upon his contact of her sex.

"Nice" Dan whispered as his fingers slid back and forth, between her pussy lips. With his fingers stimulating her pussy and his crotch being directly in front of Alice's face, it proved to be was too much for her. Alice became the aggressor. She decided to tease Dan.

"Wow, did I do that?" she pointed to the bulge in his pants.

"You sure did. you have an amazing body. Your pussy is beautiful and looks very edible. Your tits are amazing. D cup?" He asked.

"36DD" she whispered as she blushed.

"Very nice. It's too bad that your husband hasn't satisfied you lately. If I had the opportunity, I'd be servicing your sexy body as much as you'd let me." he said.

With that she reached for the waistband of his sweatpants and lowered them. His semi-erect cock sprung free directly in front of her face. She wasted no time and immediately began sucking his cock. She stroked and sucked his cock, alternating between stroking his shaft and fondling his testicles. She was definitely horny.

I take that back. I'm glad your husband hasnt been taking care of you sexually." he said.

She smiled while she continued sucking his cock.

Once he was hard, he moved to the foot of the table again. He spread her legs wide open and I had thought that he was going to mount her, but instead he dropped to his knees and began eating her pussy. His tongue went in and out of her fuckhole, sucking on her outer labia, and sucking on her clit. He was a vaginal connoisseur and performed cunnilingus like nobody ever has on her. She was in a constant state of arousal and came multiple times from his oral talents.

"Stop! Stop! That's too good. I need to be fucked now. I really need some cock. Please fuck me!" She pleaded as she looked into Dan's eyes. Dan's cock was already exposed and he was already between her legs, so she knew that by saying that, he would be the one to fill that need in her neglected pussy. She looked at him, then...

"Go lock the door." she told him. Her eyes showed that she desperately needed to have a cock fill her vagina.

Dan came to where i was and locked the door, then returned to my wife, lying spread eagle, with her fingers fondling her vagina. Dan reached into his bag, grabbed a condom, opened it, then slid it onto his extremely erect cock. As he did so, I noticed that his cock was just a little longer and thicker than mine. i figured that my wife's vagina would be stretched out just a little more than if she was fucking me and it excited me.

Once wrapped, Dan moved back between my wife's legs and placed the head of his cock at the entrance to my wife's vagina.

"Are you sure." He asked her

"Yes. My vagina needs to feel a cock inside of her so bad. Just fuck me."

She grabbed his ass and pulled him to her. The folds to her pussy gave way and I watched as her outer labia slid open and welcomed the head of his cock inside of her, as yet another man's cock entered my wife's unfaithful vagina. I was in heaven again, being able to watch my wife fuck another man in my presence. He slid his entire cock into her and she moaned "fuck, I needed this."

Slowly, he pulled back and the condom was covered with the mucus-like goo of her vaginal secretions. She was extremely aroused and it was evident from her vaginal fluid glistening on another man's condom covered cock. Slowly he slid his cock in and out of her needy pussy for the next 10 minutes and she loved it. The pungent aroma of her pussy was filling my head with a need too strong to resist. As he withdrew almost completely, I entered the room. Alice looked at Dan as it saying "what the fuck. I thought you locked the door."

He just shrugged his shoulders as saying "I dont know what happened."

I walked up to the table and stopped him from re-entering my wife.

"Wait."

He stopped and they both looked at me.

"Pull out and move over." I told him.

Reluctantly, he did.

Her pussy looked too inviting to allow their sexual encounter to continue. I slid between her legs and began eating my wife's pussy. Her vaginal flavor was amazing as her pussy oozed her womanly fluid. I've always loved the taste of her pussy and this night was no exception. I slipped my tongue in and out of her partially dilated fuckhole and savored the flavor of her pussy juice. Although there was a slight scent and flavor of the rubber (that had been satisfying her needs), her pussy still tasted and smelled amazing. I ate her for around 10 minutes as her pussy continued to expel her vaginal fluid.

After getting my fill, I pulled away and let her enjoy some more of Dan's cock. He slid right in and fucked her in the missionary position for 20 minutes, before lifting her legs to his shoulders and driving his stiff cock in and out of her very satisfied pussy. She came again during his onslaught of her pussy and then he came soon after. Once they parted, I took my position between her legs and slid my bare cock into her used pussy. She grasped my face and whispered "I love you."

She came again shortly after and as a result, I pulled my cock out of her vagina and came on her belly. Once we separated, we noticed that Dan had packed up most of his stuff and was ready to leave. He thanked us and we thanked him.

"If you guys decide that you need another session, please don't hesitate to call." He stated.

"We won't. But thank you. You were wonderful." Alice praised him.

We did not call him again and enjoyed our the rest of our trip together. A few days later I had to know how she felt.

Tom_Brown
Tom_Brown
285 Followers
12