My Wife Helps out a Friend Pt. 01

It all started when I met a guy named Jim on a website we were both interested in. Early on we realized that we lived about 2 hours apart. Now, we communicate almost daily using a private messaging app and it turns out that Jim and I have many other common interests besides the website we met on. We talk about all kinds of things, including our many shared interests, our families, our wives and sometimes, our sex lives. Over time, I have learned that his sex life is dysfunctional. (His wife rarely put out anymore) Meanwhile, I have been bragging about mine!

Early on, I occasionally mentioned my conversations with Jim to my wife and after time, I invited Tammie to join us in three-way conversations. We talked about all kinds of things. Over time, they struck up a friendship of their own. They joked with each other and do a lot of flirting online. She found that she loved his sense of humor, but it wasn't all about clowning around and one of the serious things they talked about was Jim's dismal sex life. She felt awful about it. My wife and I had a few conversations about how we couldn't understand how Jim could put up with his wife's sexual problems and how much Jim seemed to love her in spite of it. We also joked about my wife giving Jim a "helping hand" with his sex life. My wife has had a bit of a past and I love hearing her stories. They turn me on, but they are way in the past. She isn't proud of the things she's done and they happened at a very low point in her life.

Anyway, Jim and I eventually met one day at a "cigar bar" and had a great time, bullshitting over expensive cigars and really good bourbon. Later, I told my wife that I thought she would really like him. He was a good talker, funny and seemed genuine. She was intrigued and so about a month later, the three of us met up to go bowling. My wife and Jim hit it off, just like I promised her they would. They laughed and joked and flirted like they were old friends. When it was time to part, they even kissed goodbye. I could tell Tammie really liked him.

After that, Jim became a topic of conversation more often, even while we were having sex. Tammie brought his name up often in bed. She even asked me if I was serious about the "helping hand" part. Intrigued, I said yes but I joked that he'd probably appreciate more than just a hand! I told her that I had been bragging to Jim for a long time about the blow jobs she gives and I knew it had been years since he'd had one, so I told Tammie that she should show him how talented she is in that area. We had some serious talks about it and set some ground rules. I knew that this was a perfect situation- Jim was (mostly) happily married and so were we, so we all had a vested interest in keeping it between ourselves. Besides, Jim was a friend and he needed help. We talked to Jim about it. He was all for it and agreed to approach it slowly and carefully...kind of a "Let's just see what happens."

We planned a couple of times to get together again with Jim to socialize and let the chips fall where they may, but it's been hard. Since he is married, the only time he can get away is during the work week when he is supposed to be working. My schedule allows me to take Fridays off and since he is a sales rep and manager, he can sometimes get away from his desk to visit his customers and/or drum up new business. Unfortunately, he also has to manage the office sometimes so things change quickly and he has had to cancel on us a number of times. We understand why it happens, but it still sucks.

The other day, while I was out of reach, Jim couldn't reach me, so he messaged Tammie and told her that he could get away from the office for a whole day on the thirteenth and promised there would be no cancellation. He wondered if we could meet and go do something. Unfortunately, the thirteenth was a Thursday and I had to work. Tammie excitedly messaged me later and asked me if she could go and asked me what I really thought. I told her that I had no problem with them meeting up for dinner and a matinee or something, but every scenario I had imagined was between the three of us. Tammie and I had never really discussed the two of them getting together without me but I knew she was excited and so I said Ok. She and I discussed where to go and what to do. She decided on a picnic in a park.

I knew that Jim and I had recently talked at length about my wife's oral skills and that he was dying to experience it for himself, so I thought that a blow job in his car or somewhere else equally private was a real possibility. I asked Tammie what she had planned and she said that she wanted to have a nice picnic and get to know him better and if the day went well and she felt comfortable, a BJ wasn't out of the question.

Then I asked her, "What if he decides he wants more than a BJ?"

She exclaimed, "I don't see that happening! We're going to a public park and I'm not a teenager who can climb into the back seat of a car anymore!" I was happy with her answer.

Then she turned the question back to me.

"How far do YOU think I should go?"

Imagining the possibilities, but realizing the truth of what she'd just said, I shrugged my shoulders and answered, "Whatever you're comfortable with."

The weatherman predicted a hot, humid day for Thursday and I went to work knowing it was going to be a tough one for me. At 7:30 AM, I got a message from Jim telling me he was already on his way to the park. At 8:30 AM I got another, telling me that he had arrived but he was in the wrong lot and couldn't find the right one. Meanwhile, I got a message from Tammie telling me she was leaving for the park herself. Tammie had problems with her phone's data connection and couldn't contact Jim to let him know she was running a little late. She also couldn't receive Jim's messages informing her of which lot he was in. Jim was very worried that Tammie wasn't there because she had changed her mind about meeting him. I could reach Tammie by text and Jim by messenger, so it was up to me to calm him down and get them together. And just in time, too because I was about to go to a meeting where I'd have no service!

I never heard from Jim again but I heard occasionally from my wife. She left cryptic messages and tantalizing clues:

"Having fun." or, "He sure is 'grabby'!" (She later said kept grabbing her breasts through her blouse!)

Here is a short conversation we had:

Tammie (10:20 AM): "We are all sweaty...from the heat. Lol! No internet "

Me (11:07 AM):"In that case, I'm surprised you're still there."

Tammie (11:10 AM): "Maybe not for much longer"

Me (Thinking she wasn't enjoying herself) (11:11 AM): "Looking for an exit strategy?"

I really thought it wasn't going well. I heard nothing further until 30 minutes later.

Tammie (11:42 AM): "At the house"

Tammie (11:43 AM): "Just got here. Lost him. He zigged and I zagged. He has the address"

I was confused. Did she ditch him at the park? Was she worried that he'd follow her home? This wasn't looking good at all.

Me (11:52 AM): "You lose him?"

Tammie (11:52 AM): "No"

Me (11:53 AM): "I was thinking that if He had an issue, he would have contacted me but I haven't heard from him."

Tammie (12:09 PM): "Trust me, no issues. Lol!"

Suddenly it was clear to me that the heat had gotten too much for her, so she had invited him back to the house! Here I was worried that things were going south but, in fact, things were going so well that she felt comfortable enough to bring him back to the house where there was air conditioning. She said it herself...there were no issues at all! Tammie told me that they were going to spend some time in the man cave, playing darts.

Finally, I heard from Jim.

Jim (12:10 PM): "We're cool, but hot as hell! Lol!

Me (12:10 PM): "You good at darts?"

Jim (12:11 PM): "I'm not bad. I'm getting good with pointy things!"

Me (12:11 PM): "I hope she kicks your ass!"

That was the last I heard from either of them for quite a while. I had another meeting so I couldn't message either of them, but I checked my phone often, to no avail. I got out of my meeting at 1:30 PM and messaged them both but got no answer. My anxiety shot through the roof! I imagined all kinds of scenarios now that they had complete privacy! Was it going well? Were they having fun without me? Was he getting the blow job I was always bragging about? Oh, shit...were they taking it even further???

Finally, at 2:30 PM, I heard from them!

Tammie (2:38 PM): "Jim just left."

Tammie (2:38 PM): "He is REALLY good at darts. Dammit!!"

Me (2:39 PM): "LOL! How did it go? Did you enjoy your day?"

Tammie (2:39 PM): "Yes. It went fast..."

Tammie (2:39 PM): "He enjoyed his day!"

Me (2:39 PM): "Oh boy. You can tell me all about it tonight after work."

She actually called me a few minutes later and gave me a synopsis of the day. I'll write about that conversation in a bit..

At almost 3 PM, I finally heard from Jim:

Jim (2:50 PM): "Sorry got tied up LOL! I just left"

Jim (2:50 PM): "HOLY FUCK!"

Me (3:31 PM): "Lol! Did you guys have a good time?"

Me (3:31 PM): "I know you're driving, but you gotta tell me all about it."

Jim (3:32 PM): "Holy shit did I ever!!"

Jim (3:32 PM): "OMG you were so right!"

Jim (3:33 PM): "My head almost spun around like Linda Blair in The Exorcist!"

Me (3:33 PM): "Good. She said she enjoyed spending time with you, too. LOL! You guys went back to the house, huh?"

Jim (3:34 PM): "Let me tell you, that was some time we spent. Wow!"

Jim (3:34 PM): "Dude she blows like a champ!"

Me (3:35 PM): "I talked to her for a few minutes. I was shocked when she said she actually gave you a blow job!"

Jim (3:35 PM): "I was shocked the whole damn time!"

Me (3:35 PM): "I think she's gonna need a nap now! Lol! She said you were "grabby" at the park."

Jim (3:36 PM): "Lol yeah I was quite ready. She's got incredible tits!

Me (3:36 PM): "Did she show them to you? She said she'd tell me all about the day later tonight."

Jim (3:36 PM): "I had to be a little bit assertive to take the lead role to pull her top down."

Me (3:37 PM): "I love her nipples!"

Jim (3:37 PM): "They are amazing!"

Me (3:37 PM): "She said you have pics and vids."

Jim (3:38 PM): "Yes I do! I took them for you"

Me (3:38 PM): "Awesome! Send them later. I'm still at work."

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When Tammie called me at work at 2:40 PM, she quickly told me that they had walked around and talked awhile. It didn't take long before every time they paused, Jim would hug her from behind, nuzzling at her neck and caressing her breasts. (She was wearing a tank top under a light blouse, no bra.) There wasn't many people around because the heat was oppressive even though the morning was young and being so hot, she knew they wouldn't be able to stay long. We had discussed the possibility of them going to lunch and then a movie but she remembered another conversation where we had talked about playing darts at our house and that is what she decided on.

Tammie went on:

She said that by 11:30 or so they couldn't take the heat anymore so she suggested going home to a game of darts where they could enjoy the air conditioning along with some privacy. Jim was happy to agree and so they left. Somehow, they got separated on the short drive and Tammie arrived first.

Jim finally arrived and Tammie showed him to the man cave which is attached to our garage and separate from the house. She left him alone and went into the house to change into something cooler. She put on a long top that clings to her breasts and hangs down to mid thigh. She usually wears pants with it but it was so hot that she shrugged off the shorts, leaving just her panties on. She said she rejoined Jim in the man cave and they began to play darts. She said she "tried to be careful" every time she had to bend over to pick up darts that occasionally fell to the floor, but she was sure she gave Jim a show every time she bent over! She said that as they played, Jim fondled her breasts through the top she was wearing so much that she had to keep pulling it up.

They played for a little while and even with all the distractions that Tammie was throwing at him, Jim was beating her so badly that Tammie forfeited the game. Jim decided he deserved a reward for winning the game and pulled her top down, exposing her breasts to his view! She left it that way and just stood there and let him stare and fondle her naked breasts.

She sat down in a chair and Jim came and stood in front of her. She mumbled something about him still having his pants on. She unbuckled his belt and he dropped his pants to the floor. Then she pulled the waistband of his shorts down and exposed his cock. As she pulled his shorts down his thighs, she began to suck on his cock.

Tammie has amazing oral skills and before long, Tammie said Jim's legs were trembling. She eventually stopped sucking on him because she was afraid his legs would give out and also because she didn't want him to cum too soon. She got up and made him sit on the chair. Then she sat on the floor between his legs and began again.

Tammie told me over the phone that this went on for quite awhile and he really enjoyed it. Suddenly, I could detect that she had become hesitant to say more and it dawned on me why...

"Did you go any further than a blow job?" I asked.

"Yes"

"What happened?"

"I asked him to fuck me", she said quietly.

There was silence on my end. I was trying to process everything.

"I remembered that you said, 'Whatever you are comfortable with."

It was true. I had given her the "Golden Ticket" and she had taken it.

She told me that Jim took her from behind and fucked her hard, pulling out when he was almost ready. He moved around, sat her down on the chair and stood in front of her again. She sucked on the head of his cock again as he pumped the shaft until he came in her mouth and on her face. She said she didn't swallow. Instead, she allowed it to dribble out and onto her breasts. They talked a little, cleaned up and then Jim left.

This was not the way I had imagined it happening and I am disappointed that I was not there to be a part of it all but I am not mad. I am glad that my wife (and me by proxy) could help out someone who has become a good friend to both of us. I know my wife enjoyed it and although my buddy dealt with a little guilt right afterwards, I know he enjoyed it too. I am hoping that it continues, but only when I am there to be a part of it!

Part 2 is coming!