Jessica Part 1 My Best Friend’s Wife

Jess & I, First Time for us

Background: My name is Rich. My wife, Judi & I have been married for 25 years and all our children are grown. Tim & Jessica are close friends of ours. I work for a company whose home office is about 120 miles away. Tim & Jess own a house in a town about half-way between our house and my company’s home office. I have to go to the office for meetings almost every week. A couple of years ago Tim & Jess had some serious problems in their marriage, and they almost split up. We helped them work things out, and the four of us have become very close, in part due to the amount of time and attention Judi & I have devoted to their darling young son.

Jess is 30 years-old, a tiny little brunette, about 5’3” tall, and just over 100 pounds. She has long slim legs, nice firm breasts and a tiny tight butt. She has deep grey-green eyes, fine features, and a beautiful sprinkling of freckles across her shoulders. She recently lost her job and started back to school to finish the education she interrupted when she & Tim married and started their family. Tim is 38, about 6’2”, about 225. He was muscular when he was younger, but a lot of years at a desk have taken their toll. While he’s still in good shape, it’s not as good as it was. He has dark hair and eyes, and is absolutely devoted to his son, and since Jess caught him a couple of years ago, to her. Due to training requirements for his job, Tim often has to be away from home, sometimes for weeks at a time. This past winter was particularly bad, both because Tim was gone quite a bit, and because the weather was awful.

Judi is 58, 5’8”, about 165, with blonde hair and blue eyes. She had some health problems when we married, and they have continued to get worse. On the plus side, Judi is very bi, and she’s always been willing to share her girlfriends with me. I’m 5’9”, about 220, with brown hair and blue-grey eyes. I’ve worn a mustache since I was 18. While I’m not in the condition I was 10 years ago, when I worked outside and did a lot of lifting and running, but I’m not in bad shape at all for my age.

Several months before the events detailed in this story Tim and I were talking over a couple of beers while Judi and Jess were shopping. I’d commented a couple of times about how great Jess looked so Tim asked me, “Would you try to fuck my wife while I’m away?”

“Let’s put it this way, Tim,” I said, after thinking about it for a minute, “I think Jess looks terrific, but you’re also one of my best friends, and I’d be hard put to risk that even for a chance at a woman as fantastic as Jess. So I guess, IF Jess were to offer to fuck me, AND promise me that it wouldn’t be a “revenge fuck” to get back at you, but would be because she actually found me attractive, and if she agreed to do whatever I wanted, the way I wanted, and you know my kinks, then, IF she agreed to all that, I’d honestly have a damned hard time telling her “NO.” I’d try, but I can’t promise I’d succeed.”

Tim thought about that for a moment, took a long pull on his beer, then looked at me and said, “That’s an honest answer, and I respect that. I know Jess well enough to know that even any one of those is extremely unlikely, and the chance of more than one is almost nil. So here’s what I’ll tell you; If she ever makes that offer, and agrees to those conditions, then do whatever you want. You’ve got my blessing and permission.” He thought about it for a minute more then added, “Hell, it might even loosen her up a bit with me. God knows she could use it. She’d get one hell of a surprise before you were done, that’s for damned sure.” Then he just grinned at me.

“Deal? Friend?” And he stuck out his hand. I took it.

“Deal. My friend.” I said. “ I can’t imagine she’d ever agree to that, but I wouldn’t lay a hand on her without all three, so I doubt it will ever come to that.”

Boy, was I ever in for a surprise. Several months later the following begins.

Since the bad weather this winter happened to coincide with the days I had to travel to the home office, and since Tim had to be gone so much, Jess invited me to stop and stay with her if the weather was too bad to risk trying to finish the trip home late in the day. The first time I stayed Tim had just left the day before, so I slept on the couch, helped her shovel herself out, and went on home early the following day. The second time was much different, and that’s where this story picks up.

I had been driving since early in the morning, then in meetings all day, and was only half-way home driving in snow and ice when the highway patrol closed the interstate for a major crash down the road. I diverted onto the old back road, which happens to go within a block of Tim & Jess’ house, so I called Judi and stopped for the night. Jess was very glad to see me, as the lights had been flickering from ice on the overhead wires, and she wasn’t comfortable plugging in and starting the back-up generator. We got the little guy fed and played for a couple of hours, until it was finally time for him to go to bed. After he was tucked in for the night, Jess and I watched the news and weather, and the later it got the closer she sat, until she was leaning on my shoulder and holding my hand. Finally she stood up and said she was going to get ready for bed, and when she went upstairs I started to do the same. When I came out of the bathroom she was sitting on the couch waiting for me, but it was what she was wearing that about dropped me in my tracks. Instead of the demur flannel gown she’d worn the last time she was dressed in a tiny and sheer pink baby-doll nighty, with a tiny pink g-string beneath. I stopped dead, but she patted the couch beside her, indicating that I should sit next to her. I’d always known she was beautiful, but when she was nearly naked she was stunning. I sat.

“I know you and Tim are good friends, but I need something from you, if you’re willing.” She started. “I’m okay when he’s home, but these weeks away really get to me.”

It was obvious what she wanted, even without the clothes she wasn’t wearing, her little pink nipples were pulled up into two .30 caliber bullets atop her firm, pert breasts. “Jess,” I started, “I’m not going to be used as a ‘revenge fuck’, especially since Tim and I are friends. If that’s what this is about then I’m going to have to say ‘No’, no matter how much I want not to.”

“No, it’s not that. Well, mostly not that anyway. I’ve been attracted to you from the first time I saw you, but with Judi and I friends, and you and Tim, and all that, I couldn’t do anything. But he’s been gone, and you’re here, and I need a man to hold me, and I really like you, so I’m offering. If you’re interested.”

“Interested?! I’d have to be an idiot and blind to not be interested, but I won’t risk the friendships or the relationships with you and your son for sex.” I said. “Besides, if anything went wrong, Judi would kill me if I drove you guys out of her life.”

“I won’t let that happen. I promise. I just want you to come upstairs and make love to me and make me feel good. I won’t let anything happen to jeopardize our friendships, but I need you. And I want YOU.”

“Jess, I will do this, but there’s going to be one thing you must agree to, since Tim and I have talked a lot, and I know you have some hang-ups about sex, so I’m going to put a condition on this before we start. OK?”

“What condition?” she asked.

“We’ll do what I want and enjoy, the way I want to do it, and the way I enjoy it, and you won’t tell me ‘No.’, because the first time you tell me ‘No, I won’t do that.’ I’m going to get out of your bed and come back down here and sleep alone. I got Judi past those hang-ups years ago, and I’m not going to deal with what Tim does. I don’t have to. We’ll have the sex I enjoy, and I’ll make it memorable for you, too. But I won’t take ‘No.’ for an answer, or I’ll come downstairs. Is that clear and agreed?”

I saw the flash of fear in her eyes, and then she looked down at her hands. When she looked back at me she’d made a decision. “Agreed.”

“Agreed to what?” I asked. I wanted to be sure she understood.

“I agree that I won’t stop you or tell you ‘No.’ even if it’s something I don’t normally do, as long as you don’t hurt me.”

“I won’t hurt you, I promise. Or at least if it hurts for a moment, it’ll be a lot better soon.” I reached across and pulled her close and kissed her mouth. She was so sweet. The second kiss was much longer and more passionate, and our tongues were dancing before we parted. She was nearly out of breath. I slipped my arm beneath her legs and held her close, picked her off the couch, and stood up. She curled her face into my chest. I could feel her heart racing as I held her.

“Let’s go upstairs and continue this.”

When we were in the bedroom I stood her next to the bed. I held her tight and kissed her deeply again. When I pulled back she looked up at me and smiled, “I haven’t even kissed another man since Tim and I have been together. I’d forgotten how exciting it is, the first time with someone new.”

I reached up and untied the baby-doll and slid it off her shoulders. I cupped her face in my hands and kissed her deeply, tasting her and drinking in her breath and her sweet scent. I kissed around her face, her nose, eyes, cheeks, and ears. I nibbled down one side of her throat, went across and back up the other side. By the time I got back to her mouth she was panting. I held her arms to her sides until there was a puddle of pink cloth at her feet. I could feel my erection jabbing at her belly, and I knew she could too. She reached down and held my cock and stroked it.

“I’m glad to see you want me.”

“I’ve wanted you since the first time I saw you. I’ve just never had a chance to show you how much.” I said. She slid my pants past my erection and they dropped around my ankles. I kicked them out of the way with hers.

I dropped to my knees so that my mouth was level with her breasts and sucked one then the other. Then I slowly slid down, nibbling and licking until my mouth reached her slit. She was intoxicating. I parted her legs and slipped between them far enough to lick the juices that dripped from her pussy lips. My god that woman was sweet! I pushed her back so she fell onto the bed and dove forward to devour her pussy. I alternated between her clit and licking the juices that dripped from her lips. She clearly wanted me to make love to her, but I couldn’t get enough of her juice. I slipped a finger inside to stroke her g-spot, then added another. I trailed a third along her little rosebud pucker behind, but didn’t try to push yet. She was quickly loosing control and I worked to get her over the top.

Suddenly her hands were pulling my face into her pussy and her hips were bucking into my face.