Happy to Help

This is Story # 38 of my series about my post-marital sexual journey. Read the first story (Babysitter Lauren) or my profile, for any background needed. You may see references to prior stories/people, but for the most part each story stands on its own.

Not everyone likes me or my stories. That's OK. My style isn't everyone's cup of tea.

I enjoy all comments.

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Jill (and Dan)

Many, many years ago, when my now ex-wife Caitlin and I were engaged, we attended a weekend long religious retreat, required in our religion to try to prepare you for marriage. It was series of group lectures and discussions, followed by the engaged couple going back to a room to discuss the lecture. Overnight, everyone shared a room with another person of the same gender and not their betrothed, of course.

Caitlin and I were paired up with another couple, Jill and Dan, and we shared some beers with them in the parking lot on the first night, since I had thought ahead enough to bring some in my trunk, thinking we might need them. The second night, we snuck out of the dorms and went to a local bar and had a blast.

When we parted on Sunday, we exchanged phone numbers and addresses (long before cell phones), and we stayed in touch with them. They came up to our city to visit one time after we had all gotten married, and they stayed in our apartment.

Jill was tiny, maybe 5'2", but she had a great body, especially her tits, which were a tad too big for her tiny body and which she loved to show off with tight sweaters and low-cut tops. She was very sexual, and she told us that during one of the breakout sessions where we were supposed to be talking about some religious topic, she instead gave Dan a blowjob.

On their visit to us, the vibe that Caitlin and I both got from them was odd, in that they seemed to drop hints about maybe swapping partners. Dan dropped it to me once or twice privately, and Jill to Caitlin. I had never considered such a thing, and wasn't sure I'd be into it. Sure, I'd love to fuck Jill, but wasn't sure I'd like to have another guy fuck my new wife. And Caitlin for sure would never be into it. So, we both kind of laughed it off as if they were joking.

We went to visit them a year or so later, but no other suggestions were made and we figured we misinterpreted.

We stayed in touch over the years with Christmas cards, but that was the extent of it after these visits, as they got pregnant right after that, we didn't, and things kind of faded away.

Fast forward many years later. Jill sent me a friend request on Facebook. It had been years since I even thought about them. I checked her out, she still looked pretty sexy. Still married to Dan it looked like, and they looked happy. I messaged her that it was great to see them so happy, explained briefly what happened with Caitlin and I, and we talked about getting together, the three of us. I took them up on an offer to host me in a few weeks.

I arrived at their house as planned, and we had hugs and laughs and reminiscing about our meeting all those years ago. We had dinner and a couple drinks and more laughs. Later in the night as we were a bit buzzed and talking freely, I brought up that Caitlin and I thought that they were trying to set up a swap.

Jill surprised me by saying, "We were."

She and Dan went on to explain that back in those days they were into swapping, and that they also enjoyed watching the other fuck or get fucked by someone else. They were secure enough in their love for each other that neither was threatened, and they had hoped Caitlin and I would try it, but they didn't push it once it was clear we weren't into it.

I asked, "Do you guys still swap?"

"Not really," Jill explained. "We stopped once we had kids, we figured that wasn't the best lifestyle to live, so we kept it pretty straight and narrow."

Their kids were gone now, one working and living on his own, the other in the military.

So, I asked, "Are you thinking of giving it another try now that you are empty nesters?"

Dan said, "Well, I kind of have a condition that really limits how much sex I can have, but Jill is horny as ever, so we have a deal that she can sleep with other guys, just as long as she tells me about it in advance, and I get to watch if I want to."

Jill continued, "Doesn't happen often, the last time was a few years ago now. I guess I'm getting pickier as I get older."

After a brief pause, Dan then said to me, "Are you interested?"

I had been expecting this as the conversation got deeper, so I wasn't surprised. I didn't respond immediately, although my cock had been springing to life inside my shorts since the conversation started. Jill noticed, and she stood up and started walking toward me.

She dropped to her knees, saying, "Of course he's interested, he always stared at my tits."

She pulled her shirt up over her head and unhooked her bra. Her tits were fantastic and just as I'd always imagined them to be. She grabbed them with both her hands and held them up for me, squeezing them together and jiggling them a bit in front of me.

Clearly this had been discussed between them. I looked over at Dan and he was watching me.

He said, "It's fine dude, do whatever you want to her. Don't hold back."

That was all I needed to hear.

"Suck my cock," I said to her.

She smiled and reached for the waistband of my shorts, pulling them down and revealing my hard cock.

"Holy shit, look at the size of his cock baby! It's fuckin' huge!!" she said to Dan as she held it up for him to look at. "I can't even wrap my hand around it."

I grabbed her head and pushed her down on my dick, and she opened her mouth to start sucking the head and licking my shaft.

Dan said, "I don't think she's ever had a cock that big. You are gonna have fun ripping her in half."

Instead of talking to Jill, I asked Dan, "Can she deep throat? Does she like to have her throat fucked?"

"Who cares what she likes dude, she's a whore," he responded. "Try it and find out. Choke her and make her gag, who gives a fuck, she'll do whatever you tell her to do."

These two clearly had a unique relationship. I pushed Jill's head forward and down on my cock, and I could feel her struggling not to not as she tried to get it all the way down. I grabbed a handful of hair and brought her back down again, more forcefully, and felt the head go past her gag point.

She gagged and coughed up some mucous as I pushed my cock further down her throat.

When I was all the way down, I said to Dan, "I'm gonna let go of her head. She better not stop."

She didn't, and kept up the deep throating while I reached down and played with her tits.

Finally, I said, "She's been teasing me with those tits since the day I met her. I'm gonna fuck those tits now."

She rolled onto her back and pushed her tits together, and I spit on them and rubbed it between her tits, then shoved my dick in between them and started thrusting. Jill's tongue would snake out and lick the head as it popped through her cleavage.

I moved myself upward and dropped my balls in her mouth for a spell, then resumed fucking her throat for another minute before moving back to her cleavage.

I was getting close to coming, and I said to Dan, "I'm getting close, where should I come?"

"Shoot your cum in her mouth and on her face," Dan instructed.

As he said those words, Jill's mouth opened and I started coming, big ropes of cum that sprayed up her nose and forehead, much of it landing in her mouth and dripping off her chin onto her tits. She eagerly swallowed what she could and scooped the rest into her mouth with her fingers.

When I was done coming, I grabbed my shorts and put them back on, and said, "I'm turning in, thanks for letting me stay this weekend. Looking forward to tomorrow. Good night."

I headed toward my room, then realized I had left my phone in the living room, and went back out to see Dan licking my cum off of Jill's chest while she fingered herself.

I woke up early the next morning, but didn't want to wake anyone, so after I used the bathroom, I just laid in bed looking at my phone. A few minutes later I heard my door creak open, and Jill's head pop in.

She said, "I heard you moving around. Can I come in?"

"Sure," I said, and she walked over to my bed, standing next to it. She was just wearing a long night shirt. She stood there next to me, silently, and eventually I got the message. I reached out to her and slid my hand up her shirt, finding her pantie-less. My thumb found her cunt, which was starting to get wet already, and within a minute I had worked my thumb up inside her.

"Was Dan able to fuck you last night?" I asked.

"No," she answered. "And I need it bad. He said I could come in here."

"Take your shirt off and sit on my face," I told her.

She smiled and complied, whipping off her shirt and revealing those great tits and a puffy pussy that was wet and ready for action. She planted her cunt right down on my mouth and I went to town on her, getting her off quickly and often. Her hands in my hair guided the action a bit, and I greedily lapped up her juices.

After about fifteen minutes of this, she slid down and took my cock into her pussy, sliding slowly down my shaft while her eyes rolled back in her head. She immediately sat straight up and massaged her tits while she rode me.

"Your dick feels so good, I can feel it in my fuckin throat. God I needed this, it's been too long. I'm going to come again in a minute. When I do, will you give me a good hard fuck? Get on top of me and just fuck the hell out of me? Please?"

I simply nodded my head while I grabbed her hips and helped her grind on me. I could sense her getting close again, and as soon as she threw her head back in orgasm, I flipped her over, mid-orgasm, threw her legs open wide and pounded her. Locking her knees behind my elbows, she was fully exposed, feet wide in the air. She was slapping at my back and pulling my hair while I pounded her, grabbing my arms and gurgling some incoherent sounds. I was able to maintain this for about ten minutes, pausing on occasion to get a little rest and alter our position and angles slightly.

Finally with her ankles on my shoulders and her head whipping side to side, I said, "I'm gonna come soon, I'm gonna flood your pussy with my cum."

"Oh God yes, please," she urged.

With a final thrust I unloaded my seed deep into her. I collapsed on top of her and she laid still, catching her breath and me mine. I rolled off of her, unsure what was next.

Eventually she popped up and said, "Are you hungry? Dan usually makes breakfast. Just give us about fifteen minutes, Dan likes to eat cum out of my pussy and I haven't had any for him in a long time."

I thought maybe I was in the twilight zone.

After a while I dressed and went down to the kitchen, to find Dan pouring coffee and scrambling up some eggs.

"Hey buddy," he said with a smile. "Sleep OK? Hope my snoring didn't wake you."

"Nope, slept fine," I said. "What's on tap for today?"

Turns out Jill had shopping plans, so Dan and I spent the day fishing, then stopped for a beer. He explained that he's not gay, has never been with a man or has any desire to, but for whatever reason, the idea of eating another guys cum out of his wife's pussy or snowballing after a blowjob, he just loves it.

Hey, no judgment here, to each his own, I told him how I enjoy my own cum but could never be with a guy either. He totally understood.

We brought the day's catch home where Jill expertly fileted the fish and served it with some rice and vegetables. We sipped wine on the patio afterwards and played a little more catch up from the last twenty lost years. I told them about Caitlin and everything that transpired, and gave them a thumbnail sketch of my sexual activities since that time.

Jill said, "With a cock like that, I'm not surprised. Will you fuck me again tonight?"

I looked over at Dan.

"Have at it buddy," he said.

Jill stood up and grabbed my hand.

"You coming?" I asked Dan.

"Nope, I'm gonna go out to watch a ball game. Remember, do whatever you want to her, she's a cunt whore and doesn't care. Only rule - you can't talk shit about me, like call me a pussy or anything, this isn't like that. You can call her whatever you want though. She'll tell me all about it later. Have fun."

She led me into she and Dan's bedroom instead of my guest room. I felt a little funny, but if they didn't care then why would I?

As soon as the door closed, I spied a full-length mirror on the wall and said, "Stop. Get undressed."

She complied and stood there naked and trembling a bit. I walked over to her and said to her, "You always liked teasing me with those big fucking tits of yours, didn't you? Fucking cock tease."

I reached out and pinch a nipple as hard as I could, and she winced in pain. With my other hand I pinched the other one, holding both in between my fingers. She was in obvious pain, but also getting turned on.

I pushed her to her knees and dropped my shorts. "Suck it," I said.

She did, eagerly, taking me as deep as she could, licking my balls, stroking me, all while watching me watch her.

I stood her up and pushed her toward the bed, turned her around and bent her over the bed.

"I hope you're wet," I said, and shoved my cock into her from behind.

"Oh God, yes fuck me, use me."

As this morning, I fucked her as hard as I could. She had a great ass too, which I had never noticed because her tits were always on display.

I brutalized Jill. I slapped her ass until it was beet red, and she begged for more. I pulled her hair by the roots and she yelled "harder!" I fingered her asshole as deep as I could, and she took it all with joy. Hell, I could have set her nipples on fire and she would have loved every second of it.

Finally, I spit on her asshole and shoved my thumb in, then pushed her forward so she was lying flat on the bed.

Pulling my cock out of her pussy, I lined the head up with her asshole and pushed forward.

For the first time, some resistance.

"No!" she yelled, "Not my ass. Please no! You're too big!"

Normally when a woman tells me she's not into anal, I back off. But remembering Dan's words telling me to do whatever I wanted to her and that there were no rules, I ignored her and pushed forward.

"Shut up" I said. "A cock tease whore like you doesn't get to make the rules. Your asshole is getting fucked, like it or not."

When I was about two inches in, she was crying, so I shoved two more inches in, and told her, "There's more. If you don't shut up, the rest is going in with one push."

That shut her up. I continued to lube us up with saliva, and reached around for some pussy juice too. Finally, I was all the way in, and began fucking her ass in earnest. Her cries of protest had turned to moans of pleasure; her lame act finally having been dropped.

I yanked her head back by her scalp and talked to her in the mirror.

"Fuckin bitch," I said. "All sweet and innocent, but just an anal whore like the rest of them, right? What kind of a dirty pig let's her husband's friend fuck her ass in their own bed? He doesn't even deserve a whore like you."

"Oh God Yes, I'm a whore, fuck my ass, I'm a total cock slut."

With a final thrust I unloaded into her yet again, my cum being squeezed out of her asshole and dripping onto the bed. I withdrew my cock from her ass with a plop, and the air and cum from her ass made a wet noise as it bubbled out.

"Take a picture and send it to Dan please," she asked as she spread her ass cheeks.

I took a shot of her asshole leaking my cum out, and sent it to Dan, with a note -- "just fucked Jill's ass. She tried to tell me no but I didn't listen."

He responded with a laughing emoji, and then "She always says that, glad you didn't listen to her. She must be in serious pain lol."

Then he texted, "Hey grab the small but plug out of the nightstand and put it in her, that will keep the cum in her ass until I get home."

"Anything else she likes?" I asked.

"She likes whatever you like. She's a cock whore, do whatever you want. You can shit on her for all I care."

We ended up in the shower a few minutes later, with her on her knees washing off my cock that had just come from her ass.

When I was clean, I pointed my half limp dick at her and said, "Look at me cunt. Close your eyes."

With that, I started pissing on her, spraying her tits and face with warm piss. She began moaning and fingering herself, and rubbing my piss into her skin with the other hand.

When I was empty, I shoved my cock into her mouth and fucked her throat, letting my cock grow to its full length while I did so. I fucked her mouth and throat violently for a while, then I bent her over in the shower and fucked her from behind, feeding another load of cum into her always hungry pussy.

After our shower, we enjoyed another glass of wine, and I went to bed while she waited up for Dan. He was gonna have a lot of cum to feast on when he got home.

The next morning was a similar repeat of the previous morning. She woke me with some easy head, then mounted me and rode me until she came a few times. I finished in her pussy after fucking her in deep missionary and then from behind while lying flat on her stomach.

She went running out of the bedroom afterwards. Dan was not in the kitchen, so I peeked into their bedroom and found her grinding on his face while he ate my cream pie and brought her to several more orgasms.

I showered and packed, then made myself some coffee and drank it on the sofa. When they appeared, I was packed and ready to go. Jill looked sad, but perked up when Dan told her to "give him one for the road."

She knelt before me, sucked me until I was hard, then got on her hands and knees, inviting me to fuck her from behind. She came twice, then spun around to finish me with her mouth. I gave her what cum I had left, which she held in her mouth and then spit into Dan's mouth, who had been watching us.

They invited me back any time, and I said I'd definitely take them up on that, maybe with a female friend or two. I offered for Jill to come visit any time, which Dan said was fine, as long as we filmed it so he could see it.

I fucked her several times after that, and Dan and Jill came to visit me and my second wife a few years later.....

Please comment, I love them all.