Jess and Tim. And me.

Now that I had spent two evenings with my best friend’s wife, Jessica, while Tim was out of town for business, the third week rolled around and I knew Tim was home. The weather forecast looked iffy, but I set out for the mandatory weekly beating regardless, hopeful that I could make it home this time. I certainly wasn’t confident that I wanted to face Tim after fucking his wife in every hole and showing her the basics of bondage sex the week before. Leave it to Mother Nature to press the point. I started driving into freezing rain 20 miles from the exit to their house, and it was quickly apparent that I wasn’t going to get home that night either. As before I stopped at the exit and called my house to let my wife know, then called Tim’s number to make sure the couch was available. Tim was only too happy to invite me to stop, so obviously Jessica hadn’t told him anything.

They had some dinner ready for me, and we ate, talked and played with their son. While Tim and I talked together, Jessica got the little guy ready for bed. Tim asked me what I’d said to Jess the previous two weeks, because she seemed more sexually open with him. I admitted that we’d talked, and somehow managed to hide that we’d done quite a lot more than talk. Tim didn’t press the issue, and he was quite grateful that Jess had started to open up to some things he’d wanted to try. How could I tell my best friend that I’d insisted she try them so I’d allow her to fuck me? Telling him didn’t seem a good idea.

When we’d tucked the little guy in for the night Jess came in to tell us that she was going to get ready for bed and went upstairs. That was when Tim mentioned that he was very happy that Jess had finally shaved all her pubic hair off, had encouraged him to do the same, and they were having more oral sex than ever before. Jess came downstairs to get Tim, gave me a quick kiss, then took Tim by the hand. She was wearing the same robe as the previous week, and I was willing to bet that there was nothing but Jess under the robe again. Just the thought gave me a hard-on while I got ready to sleep on the couch.

When I came back out of the bathroom I could hear Tim and Jess’ voices from upstairs, and I thought there was an argument, but I couldn’t tell for sure what it was about. Then things got very quiet, and I was just about to stretch out when I heard Tim say, “If that’s what you really want, I’ll get him.”

I thought I heard a very quiet “Yes.” From Jessica, but wasn’t certain.

Tim walked into the living room, wearing nothing but a pair of silk sleep shorts and an obvious erection, and sat down on the chair across from me. He stared at me for a minute, then finally said, “Jess told me everything. Well, I assume it was everything. It certainly explains why she’s more open since I got home. And where her pubes went.” Tim smiled. “I wanted to be pissed, and I tried to be, but truth is, I was getting bored again, and there was a danger with me travelling, but it seems you’ve turned her on to a lot more things, and if that keeps up I can wait for her when I’m away. So, well, thanks.”

I wasn’t sure quite what to say so I just said, “You’re welcome.”

“But there is one more thing.”

“Yes?” Truth be told, I was a bit nervous at that point.

“Jess wants you again tonight. Or more specifically, she asked me to bring you up to join us in bed for the night. Since she was washed up, perfumed, freshly shaved, and naked under that robe, I assume she doesn’t mean to sleep much.”

“Do you have a problem with that, Tim?”

“Let’s see. My best friend comes over to my house to stay the night, twice, to get out of the storms. He fucks my wife both nights.” Tim smiled. “And turns her into a maniac who can hardly keep her hands and mouth off my cock, unless there’s no one around and it’s buried in her pussy. Do I mind?” He shrugged. “If you can keep her like that, you can have all you want. And tonight she wants you.”

“Then I don’t see how I can say no.”

When we walked into the bedroom Jess was standing between the door and the bed, waiting. She was naked, and trembling. Tim went to her and she held him, then reached out to me. We hugged her between us, Tim at her front, me behind. She looked at Tim and kissed him, then looked back over her shoulder and kissed me too. “I was afraid one or both of you wouldn’t come up here.” There was a tear in her eye. “I love you.” She looked from one to the other of us, “Both of you.”

Tim looked at me, but I wasn’t quite sure what he was thinking. I wasn’t sure what I was thinking. My best friend’s wife had just told him she loved me too. This could end badly.

“Rich, Tim is the father of my children and my husband, and I won’t change that, but you are my sexual teacher, and I love you for what you’ve given me.” She squeezed Tim’s chest and looked into his eyes. “Us.”

“Tim, Rich has shown me things I’d never dreamed I’d allow myself to do, and taught me to enjoy them so that I can share them with you. I can’t explain why, but he can get me to try and then I can do them with you. I want him to keep teaching me so I can share more and more with you. Tonight I want him to show me how to have sex with two men.” She looked between us again. “With MY two men.”

Tim smiled. “I’m good with that.”

“I can’t say no.”

“Good.” Jess said and pushed Tim’s shorts to the floor. Then she spun around so that Tim’s cock was pressed into her back and whipped my t-shirt over my head. She slipped her hands into the waistband of my shorts and slid them to the floor too. “Should we start on the bed?”

Tim said, “Sure.” Gripped Jess across the chest and picked her off the floor. I stepped back and climbed onto the bed, centered myself, and Tim flipped Jess’ legs out for me to catch. When I had her legs pulled to me, Tim climbed onto the bed, still holding her tightly, while I let her slide down along my body, so that she was kneeling on the bed between us with Tim’s arms wrapped around her chest and my cock trapped between her legs.

I slipped my mouth to Jess ear, cupped my hand and whispered, “Are you sure you’re ready for this.”

Jess nodded. “Same rules apply. Do what I say?” Nod. “No question?” Nod. “Okay.”

I slid back a bit. “Hands and knees, Jess.” She complied. “Get Tim’s cock in your pussy, but make sure I can see the love in your eyes while you do. Tim, slowly. Make her show me how happy she is to make love to you as you enter her. I want to see the lights come on in her eyes.” I stretched out on the bed and took Jess’ face in my hands as Tim started slipping his cock into her. It was easy to see that she loved him. Loved his cock in her pussy, maybe even more than me. Loved pleasing him. I could see the moment she had him fully sheathed, even before Tim said, “In.”

“Love her slowly Tim.” Tim started stroking in and out.

“Jess,” I whispered. “I’m going to slide up here in a moment and I want you to suck me until you’re ready to put my cock in your pussy. When you are, I want you to pull Tim out and get yourself on mine. Then I want you to invite Tim to take your ass.”

Jess nodded. I slid up on the bed so my hips were under her face and she dropped down and engulfed my cock with her mouth, pulled back and wrapped one hand around my shaft while she licked and sucked. I stroked her face and hair and watched her attention to my cock. My god that woman had talent. It took only a couple of minutes until Jess paused and took my cock out of her mouth. She held the tip in her hand and smiled at me, looked back over her shoulder at Tim, then crawled forward, straddled my hips, and slid my cock to the hilt inside her. If Tim had been jealous, the noises we both made as she impaled herself on me would have tripped his anger. All he said was, “Hey! What about me?”

I whispered into her ear, “Ask him.”

“Fuck my ass, Tim.”

Tim just knelt there, his erection waving in the air. I whispered, “Ask him again.”

“Fuck me in the ass, Tim. Please?”

I stretched and reached for the bottle of oil and held it towards Tim. “You may want some of this.”

Tim took the oil, put some on his hands, rubbed part of it on his cock, then added some and started rubbing at Jess’ anus. I could feel him pushing oil into and around her ring and could feel her relaxing and preparing to admit him. “Now Tim. Please.” Jess sounded almost urgent. Tim shifted on the bed. I could feel him kneeling between both of our legs, then pressure when he pushed against Jess’ anal ring. I wrapped my arms tightly around Jess’ chest and Tim pushed. Despite her best efforts she resisted a little, then she opened up to him and her husband’s cock was buried in her ass for the first time ever. I could feel Tim’s cock as he slid forward until the entire length was inside his wife’s rectum, resting against mine, equally buried in her cunt. Where she had been tight, she now felt tighter.

I looked into her eyes and kissed away the tear I saw there. “You okay?”

Jess smiled at me. “Yes. I feel so full. So full of cock and so full of love. Can the two of you hold me like this for just a little while?”

Tim leaned forward against her back and placed his face next to hers. Jess turned her face and kissed him deeply. “Yes. I’ll hold you like this. Let me know when you want more.” Then he looked at me. “Rich?”

“I’m happy. Let me know how I can help.”

We tried to lay quietly, but as expected, that didn’t work well. No matter which of us moved it did things inside Jess that caused her to gasp. She was the first one to start moving deliberately to slip us in and out of her. Then Tim picked up the rhythm. There wasn’t a lot I could do except keep my pubic bone firmly against Jess’ clit. Her first orgasm came out of nowhere, flooding my groin with her juice and making her tremble. To his credit, Tim kept up a smooth steady stroking in and out of her ass, displaying amazing self control while she was trying to milk our cocks into her. Jess pushed herself up and started rocking back harder, while Tim increased the strength and speed of his strokes. I could feel her pussy clenching on me then she started slamming back against our cocks. “Fuck,” slam, “Me,” slam, “Harder,” slam. Over and over. I held her shoulders trying to keep her from throwing me out when she rocked forward, Tim was holding her hips trying to do the same.

Jess was slamming into us and screaming to fuck her harder. Someone was going to be bruised if this kept up. Then there was one loud “Fuck!” and Jess started to shake. The orgasm hit her and locked her muscles into spasms. Tim pulled himself as deeply as he could and I felt his cock start to spasm against mine.

“Oh, Fuck. Jess! I’m cumming too!” The two of them sent me off, shooting deeply into Jess’ cunt, arching my back off the bed to get as deep as possible. Jess collapsed first, dropping onto me. Tim pushed down onto her to keep himself inside her as his cock continued to spasm. I slowly lowered myself down to insure we stayed locked together. I brushed the hair from Jess’ face and kissed her. She smiled at me, weakly. Tim just rested his weight on his arms and looked down at us. The three of us were panting in our own separate recoveries.

“Oh, my gawd!” Jess said. “I’ve never felt anything like that.” She tensed her muscles, whether accidentally or deliberately I wasn’t sure but Tim and I both jumped inside her. Jess ducked her head and went “Fuck!” loudly, shivering through another small orgasm. “I just want to lay here and enjoy the feeling of being full of my men for a little while.” Jess said.

Tim looked at us and said, “I’m not sure how long I can stay like this. I may need to rest my arms.” He started to adjust his position and his cock slipped partway out, I could feel it going.

Jess gripped his arms. “Don’t pull out yet. Please babe. Keep it inside me for a little longer.”

Tim slid back forward a little and adjusted position for more comfort. Jess turned to him and kissed him. “Thanks honey. I love you.” For myself I just lay there, enjoying the feeling of being inside Jess’ cunt, and feeling our juices dribbling across my balls.

After a few minutes it was clear that Tim was wilting and Jess was restless. She looked over her shoulder at her husband and said, “Tim, if you’re ready to pull out you can, just give me a little warning so I’m prepared.”

“It’s about time.” Tim said.

Jess looked at me, “You?” She asked.

I kissed her nose, “I’m not going anywhere until you do.” I admitted.

“Ready?” Tim asked.

Jess just nodded. I felt Tim’s cock pop from her ass, and could tell he’d rocked back. Jess looked disappointed, then a little shocked. Then she just said, “Shit.” And jumped off the bed and ran towards the bathroom. I lay quietly, but Tim looked after her quizzically. She glanced over her shoulder long enough to catch Tim’s look, and replied, “Cum enema.” As she headed for the toilet.

Tim looked at me. “Cum enema?” he asked.

“That’s what Judi calls it when I cum in her ass.”

“And how did….” He paused mid-thought. “Oh. You and Jess?”

“Yeah. I told her Judi’s name for it.”

“I see.”

“Don’t you want to get washed up?” I asked.

“Yeah, but I should wait so I don’t bother Jess while she’s..”

“Go on and don’t worry about it.”

Tim started off the bed, then looked at me. “You know that because?”

“I told her to get used to it.”

“Oh.”

I laid there for a couple of minutes while I heard the water running on the sink, then the toilet flushed. I got up and walked to the bathroom. Tim was at the toilet and Jess at the sink. I stepped next to Jess and reached for a washcloth. Jess stopped me, dropped to her knees and sucked my cock into her mouth and started cleaning our juices off me.

I didn’t even hear the toilet flush, the first thing I heard was Tim saying, “Jess!”

She turned her head to answer but didn’t take my cock completely out of her mouth. “Wha..?”

“Something else new?” Tim asked.

Jess nodded, then let my cock out of her mouth and examined it for juices she still wanted. Finding none she looked at Tim. “I realized I love the taste of our cum mixed together, and I enjoy cleaning a cock when it’s been fucking me. At least in my cunt.”

Tim shook his head. “You’re going to have to show me that one.”

Jess stood up and went to him. “I will love. I promise. I want to lick our juices from your cock too.”

I looked at them and said, “Let’s all go back to bed and see what happens next.”

We put Jess in the middle, facing Tim, with his cock between her legs and mine laying in the crack of her ass. Jess dozed and I think Tim did too. I just felt my cock stiffen so I grabbed the bottle of oil and lubed my cock and Jess’ ass. That was when I realized that Tim was erect also between her legs. I slipped my cock into her ass slowly and Jess only stirred a little, even when she was fully impaled with my erection in her ass. I nudged Tim. “Shall we wake her up for another round?” I asked.

“Can we get in without waking her first?”

“I already am.” I admitted. “If we can roll her over on top of me you should be able to get into her pussy and wake her up with another double-fuck in progress.”

Tim put her top leg over mine and I grabbed her chest and rolled onto my back. Jess’ arms and legs flopped out on either side of me. Tim knelt between her legs and studied my cock in his wife’s ass, while he stroked his. “A month ago she wouldn’t even let me touch her ass as any part of sex.” He shook his head. “Let’s see how long it takes her to wake up.”

I felt his cock slip into Jess’ cunt and slide along the length of mine until we were both fully inside her. He smiled down at her and started to stroke in and out. After a few strokes produced no obvious response he called out, “Jess? Wake up, babe.” A few more strokes produced no additional response, but she did finally start to stir.

“Oh.” Then her eyes fluttered open. “Oh. I thought I was having the most wonderful dream. But it’s not a dream. I’m waking up with both my cocks inside me. It’s way better than a dream.”

Tim was giving her a good fucking, and it quickly produced even more response. “Oh Tim. Fuck me hard. Make me cum. Fill me up. Oh gawd!” I felt the gush of Jess’ cum.

Tim looked quizzically at Jess again. She looked back, then realized what had happened. “Oh honey, don’t worry. That’s my girl cum. When you really get me off I squirt girl cum out of my pussy. Would you like to taste some? It’s yummy.”

Tim dipped his fingers and licked them. “You’re right, it is yummy.”

“Give me a taste too, honey.”

Tim rubbed his fingers in her cum again and put them in her mouth. “Thanks honey. I love the taste of my cum, but it’s even better when its mixed with yours. Fill me with your cum baby. Fuck me hard and fill me with your cum.”

Tim started fucking her hard and I started moving my cock in Jess’ ass too because I wanted to cum with them. Jess started cumming, bouncing and shaking with a series of orgasms, while Tim continued to pound her pussy with his cock. I felt the pressure building in my balls and could feel the imminent release. Then I felt Tim tense. “Oh gawd, baby. Oh gawd. I’m going to fill you up. You’re making me cum.”

“Yes Tim. Yes. Fill me up. Make me cum again.”

I felt Tim’s cock pulsing jets into Jess’ cunt and that finally got my release. My cock bounced and started sending jets of cum into her ass. “Oh gawd. Me too.”

When we had finally spent ourselves Jess was laying on me smiling up at her husband and he was kneeling between her legs with his cock buried in her cunt. I was still on the bottom with my cock firmly gripped in her ass. “Bring me your cock, Tim. Please. I want our cum in my mouth.”

Tim pulled out of her pussy and knelt next to Jess’ head, away from mine and laid his cock on her lips. She sucked it in and started licking the juices from him. When she was satisfied that she had licked him clean she took his cock from her mouth and kissed the head. “Yummy. Boy cum and girl cum together.” She said. “Now kiss me, my husband.”

I could see her slip her tongue into Tim’s mouth while they kissed. When Tim finally pulled away Jess smiled up at him. “What do you think of the taste?” she asked.

“It’s okay.”

“Will you lick me clean?”

“Do I have to lick Rich clean too?”

“No, just try some of me, at least this first time.”

So Tim went back between her legs and licked their mixed juices from Jess cunt. Jess grabbed Tim’s head and held him, her hips started bucking a bit. “Oh Tim, that feels so good.”

Suddenly I felt Tim’s tongue on my balls and I twitched inside Jess. “Umm, nice.” She said.

“Yeah, I got a lick too.” Just then Tim gave a long lick along my sack and all the way to Jess’ clit. We both jumped. Tim’s face popped up over Jess’ belly. He was smiling while he crawled up to kiss her.

“I figured if you have learned you like the taste of girl cum I might learn to like the taste of boy cum. I just might, I think.” Tim grinned. “There are some interesting possibilities down that path baby.”

Tim leaned into Jess’ mouth and they kissed long, hard and deeply. When their lips parted Jess smiled at Tim and asked, “And just what do you think is possible?”

“Well, we’ve already shared a taste of Rich, maybe we should share a taste of someone else.”

“I’m betting you’re thinking of a girl someone else. Aren’t you?” Jess asked, as Tim slipped his cock back into her cunt. “Are you thinking of someone in particular?”

“Just you at the moment.” Tim said as he stroked in and out of her. “But I might be able to think of someone.”

“Oh god. I love having both my cocks inside me!” Jess screamed as she bucked with another orgasm, arms locked around Tim’s shoulders. When she finally relaxed back against my chest she smiled at both of us, then said, “Much as I love this, I need a break, and I need to pee. Can we get up for a few minutes?”

Tim pulled out, and Jess gasped. “Oh, phoo. I feel all empty now.” Then she rolled forward and Tim helped her off my cock. “Whoops! Now I’m all empty. Be right back.”

We watched her ass wiggle into the bathroom. Tim grinned and called after her, “Cum enema?”

Jess smiled back, “Yes, again.”

“I guess I should wash up this time myself.”

“Well, I won’t do it for you.”

“No, but Jess will probably clean yours.”

“I hope so. God, I love her mouth on my cock.”

“I understand. I do too. Even if she is your wife.” I said as I went into the bathroom.

When I finished washing up Tim and Jess were locked in a 69 together and happily licking each other clean. I just lay down on the bed and watched them enjoying each other, knowing full well that less than a month before neither of them would have done that after having sex not once, but twice. I could tell they were pleasing each other and they were really getting into it. Jess came more than once, then suddenly Tim stiffened, arched his back and pulled his mouth away from his wife’s cunt. “Oh god! Jess, I’m cumming! OH GAWWDD!”

Tim went completely rigid, while Jess locked her mouth on his cock and sucked down every drop of cum he offered. Even after he relaxed she continued to suck, causing him to bounce and twitch until he couldn’t stand it any longer and he rolled her off of him and took his cock away from her. He grabbed her hips and slid her up the bed until her face was by his. He pulled her into a kiss that lingered, with plenty of tongue, then stopped and said, “I had to make you stop before I lost my mind.”

Jess twisted on the bed and brought her pussy near my head. I didn’t need an invitation and lifted her leg and slid my face to her and started licking her cunt lips and her clit. While she tried to talk to Tim I managed to bring her to several small orgasms that made for pauses in the conversation, then one larger one that coated my face with her cum. When that one passed she got up on her knees, looked at Tim and I and said, “I’m going to slide here between the two of you and I want at least a nap. No cocks inside me until I get some rest.”

We nodded our agreement, reluctantly, and she snuggled between us, this time with me in front and Tim behind. I assume they slept, I know I did. Some time later I was dreaming of the most incredible blow job, when I realized that it wasn’t a dream. I opened my eyes carefully and realized I was laying on my back and Jess was sucking my cock, while a couple of feet away, Tim was laying on his side, slowly fucking her.

“Good morning, sleepyhead.” Tim said. “We were starting to wonder what she had to do to wake you up.”

“Yeah, I was about to be insulted. I started to think you didn’t like my mouth on your cock any longer.”

I slid so that our faces met. “Oh babe. Don’t be mad. I’ll always love your mouth on my cock, any time you want it. I must have been pretty tired.”

“Are you still tired?”

“Nope. Not any more.”

“Good!” Jess pushed me flat. “Give me some breakfast cum then.” And her mouth was quickly back on my cock. Her hands were playing with my balls and my cock, and she was alternating between sucking it deep and wet and licking all the sensitive places. She quickly had my undivided attention, even while Tim continued a steady rhythm in her cunt that she was obviously enjoying. From time to time she’d pause on my cock, press her eyes shut and moan through an orgasm before proceeding. I was thinking about how good it felt and never saw her wet her finger. The first I realized what she was planning was when a wet finger found its way into my ass. It took my balls from heat to boil in seconds. I gripped her arm between my thighs and gripped her head in my hands and really started fucking her mouth. Even with a mouth full of cock it was obvious Jess was enjoying this. It only took a short time for my balls to explode. “Oh god Jess! I’m cumming! I’m cumming!”

For Jess’ part she stayed locked on my cock and drank down every drop. “Yum. Breakfast cum. Now I don’t have to eat anything else.” She worked her hand on my cock like she was hoping for more.

“I think you got it all.”

Jess pouted. “Yeah, looks that way.”

“Maybe Tim has some.”

“I hope so.”

“Why don’t I help you up so you can ride him and get it out of him?”

“Oooh. Sounds good.”

“Put your leg over Tim’s. Tim hold her hips tight to you so you don’t fall out.” I took her hands and stood on the bed. “Now, while I lift, Tim can roll and we’ll sit you on his cock.” The move worked perfectly and quickly Jess was sitting on top of Tim with her legs spread and her pussy impaled on his cock. “Jess, I can’t think of a more perfect sight than your pussy with a cock in it. It just seems like that’s the way it should be.”

“I agree.”

“Now you can stay like this and let me watch, or kneel over Tim and let him watch.”

“I want you to watch.”

I knelt in front of her, straddling Tim’s legs and watched while they fucked. Jess leaned back and rested on her arms and pumped herself up and down on Tim’s cock. It looked beautiful to see his cock plunging in and pulling back, opening her for her pleasure. I reached down and put my fingers beside her clit and rubbed along it to help her pleasure. She grabbed my other hand and put it on her chest and I pinched and pulled at her nipples. I watched her face as her pleasure built. It was a wonderful thing to watch her make love to her husband and to be so pleased by him. I leaned in and kissed her, gently at first, but she quickly put real passion into the kiss. Then she was panting and couldn’t hold the kiss any longer. “Oh god!. I love you. I love you both. Oh God! I’m cumming! I’m cumming. Tim, please fill me with your cum! Please! Oh god! Please!”

I felt the rush of her juices between my fingers then felt Tim’s cock pulse. “Here it is Jess. Here’s my cum!. Yes!” And they bucked and jerked together. When they were spent Jess lay back on Tim’s chest with her eyes closed. Tim kissed her neck and ears and she just lay and smiled. I leaned forward and kissed Jess on the mouth again, my cock dragging against Tim’s, between her legs. Jess smiled without opening her eyes.

“I love my men and my cocks. Both of you. Thank you so much. Thank you Tim for letting me explore, and thank you Rich for making me learn my lessons. Oh, God. I could just love the two of you like this forever.”

I looked down at her pubic mound thrust up with Tim’s cock still in her and couldn’t help myself. I slid down and licked her pussy lips and clit. I licked around Tim’s cock, sucking up their cum where it dribbled around Tim’s cock. Then I licked the cum off Tim’s balls, and caught the new dribbles. When everything showing was clean I crawled back up and kissed Jess again.

“Thank you. Thank you both for all this. I love you both.”

I crawled out of bed. “I’m going to get up and start some coffee and some breakfast after I shower. Trenton is going to be up soon and I’ll take care of him. I think the two of you need to stay in bed for a while and keep going until you can’t.”

Neither of them moved that I could see, they just lay there smiling.

I showered and headed downstairs. When I was dressed and passing through the bedroom they were back in a 69, licking each other very thoroughly. Jess looked up and smiled as I went by, but she didn’t take Tim’s cock out of her mouth. Trenton and I had breakfast and watched cartoons and read stories for over an hour before they finally got downstairs.

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