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.
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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.