Unexpected [MFM] from a Craigslist hookup many years ago

This origins of this encounter go back a while and I don’t really want to bore you with the details (at least not this early on). Put simply, I had been broken up with and I had a lot of demands that I wanted met for my own personal gratification before I could commit to another relationship. This is the story of one such instance.

I had swapped emails with what I assumed (correctly) was a woman on the now defunct Craig’s List personals. She was looking for a guy. I could tell by the word choices that she was a real person. She used the word groovy once… that pretty much sealed the deal for me. We met, had quality sex and when I was cleaning up, I noticed she had some other condoms in the bathroom trashcan. When I came out of the shower, I asked how many others had accepted her invitation. She said it had been “worth her efforts.”

“Why not call one of them, see if they’re not too busy,” I said. I had wanted a threesome, but instead of with two women, I wanted it a woman and another man. There were certain things that two men can do that two women simply cannot.

She sent an email and before I had completely dried off, she had a suitor.

“Anything I should know about him,” I asked.

She replied that he was just a normal dude. She did say that he had cum on her breasts and then licked it off himself. I poured myself another tall glass of mallbeck.

About twenty minutes later, there was a knock on the door. She answered the door in her robe. He gave her a warm hug and kiss. He was a pretty normal looking white dude. No beard, no glasses, just a regular looking dude.

She handed him a glass of wine and he drank it quickly. She refilled it and he nursed that one.

“So, about an hour ago, I was being turned inside out by this man,” she began. “Then he gets the idea that he wants some more. So, I suggest you and he agrees.”

She was clearly lying; I thought it a good tactic to get what we both wanted.

We’re both sitting in robes. She tells him to get more comfortable. He takes off his shoes and socks, sets them by the door.

“While you’re up,” she says, “take off everything else.”

He does and he’s standing in front of both of us with a half hard on.

She turned to me and asked if that would work. I nod.

She stands up and removes her robe, dropping it to the floor. She was a woman of considerable curve. Her large breasts had nearly bruised me when she was on top of me. Her ass wasn’t much to look at, but it had rebounded nicely from the beating I had given it earlier. She got on her knees in front of him and took him in her mouth.

After a few minutes of this she beckoned me over. She was on her feet now, his cock still in her mouth. She began directing him to sit on the couch. She put her ass in the air and spread her cheeks for me. I dove right in. I licked her slightly gaping asshole until it opened a bit more. I’m almost certain some of me was still in there. I worked my way down her lips, tasting her grool, down to her clit and right to a leg shaking orgasm shortly after. I could tell by her moans that he was no longer in her mouth. I smacked her ass and she nearly fell over.

She climbed on top of him. He was still sitting on the couch. I went to get another drink of wine. From across the apartment, I could see her grinding on him, her fingers in his short hair. She was nearly suffocating him with her breasts. I couldn’t hear what he was saying, it was extremely muffled, I only heard her responses. “You want to cum on mama’s breasts, don’t you,” she said. “You want to lick mama clean, don’t you?” Rhetorical questions like that. Before I could finish my wine, she was on the carpet, him on top of her, his ass sticking up in the air, jerking himself off furiously and finally onto her breasts. He then got on his hands and knees and, as promised, licked her clean.

He was on the carpet next to her, his chest heaving.

“That was hot,” she told him.

I set my glass down and broke their spell. He looked up at me. I could see his penis glistening from his fresh cum. It shrank a bit the longer he looked at me.

I grabbed a condom and walked over to her on the carpet.

“I don’t want you to get a rug burn,” she said. “Lets go to the bedroom.”

Her bedroom had been lit by candlelight earlier, but it had since burnt out. She had what amounted to black out curtains and it was nighttime. I made sure the lube and extra condoms were still on the nightstand. She positioned me on the bed and climbed on top. I could feel her moving her hand, feeling herself. She whispered in my ear that she was still wet from me earlier.

“Put a few drops on yourself before you plunge in,” she said to the other guy.

He fumbled around a bit and then there was a silence. I don’t know if he was completely hard again.

“Don’t worry,” she said. “Just jump back in when you’re ready.”

He let out a faint “okay” before she slid me completely into her. There was a slap and the air that had been in my lungs was let out. I could feel how wet she was, dripping down my balls. She grinded herself on me, enough time having passed that there was a slight bit of stubble, a slight bit more friction for her sensitive clit to react to. I don’t know how many times, or if she came again, but my balls were probably glistening from her enjoyment.

The lube bottle clicked opened, followed by the bed moving. I could feel him positioning himself behind her. He grabbed a moved her hips so he could get a better angle before slowly sliding himself in to her asshole. I could feel her filling up, could feel the thin layer between us becoming thinner. I wondered if we hadn’t been wearing condoms, if I could feel the ridge of his head against mine. I probably wouldn’t have been able to unless he was massive.

Anyways, she began moaning more and very loudly while he was sliding into her. There was almost a ringing in my ears from all of this, so I put my hand over her mouth, my other hand on the back of her neck. She arched her back and a few seconds later came again.

“Damn, that’s tight,” he said when she came.

I held my hands where they were. He slid in further when he had the chance and she put her hands on my chest, hard. I could feel her digging her nails into me, the pleasure of the pain giving way to real pain as, I would later find out, she had broken the skin in eight spots. I moved my hands when he was completely inside of her.

We awkwardly rocked around for a few minutes before I came. I didn’t want to ruin the other guy’s orgasm, so I stayed down long enough for him to finish. I pinched her nipples and rubbed her clit. I have no idea how she was able to sustain so much pleasure in one night.

The other guy came inside her and then we took a breather.

He went to the bathroom. We could hear him peeing.

She asked me how I was enjoying the experience. I said that I was getting jealous of all the orgasms she was having.

“I’m about maxed out,” she said. “You want to cross that one off your list?”

Now, if you’ve read this far, you’re probably still wondering what it is that I wanted out of this encounter. I’d already eaten her ass, watched her suck off another dude, and double penetrated. Now I wanted a different kind of double penetration. I wanted in her ass, with him in my ass. I’m not what you would call bi-curious, I just like to be pegged every now and again, and I wanted to know what it felt like to have the real thing inside me. Maybe that’s the definition of bi-curious. If so, then that night I was.

Like I said earlier, the room was pitch black and only getting darker. I went for more wine. It’s amazing how much fits into a box. He came out of the bathroom and I handed him a glass. He drank it down and went back into the dark room. I heard the bed move, heard him slap her ass and then some movement on the bed.

My mind was considering different ways to trick him into getting what I wanted, but that all seemed dishonest and ridiculous. Surely, no matter how dark it was, he would be able to tell the different between my hairy legs and her stubbly ones, or which direction the legs were going. But I couldn’t deny that her ass and my ass were about the same size, albeit, mine much hairier. Maybe the lube could mat it down? I finished my wine and went back in. I closed the door behind me and the darkness enveloped me.

I could smell the lube and hear it being applied. Lube always has that sound and smell that are unmistakable. This is one of those instances. I found the lube and opened it. I spread a bit on my ass, then a bit more. Penetrating myself with my fingers until I could get in with ease.

“You want to fuck mama’s ass again,” she said.

“Yes, mama,” he said.

She got off the bed and moved me to where she had been. It had been that simple. I’m not sure how much the wine had helped, but it couldn’t have hurt his performance. He was hard as a rock as he slid into me. He put his hands on my hips as he eased himself in further. He commented about how tight I was. I buried my face into the bed, muffling my moans of pleasure.

Inch by inch he penetrated me until he bottomed out. I felt completely full of his seemingly normal sized cock. I wondered what a bigger cock would feel like. How much it would hurt, whether I would be able to feel it poking through my stomach.

He smacked my ass, hard, and began sliding out slowly. When he was about halfway out he slammed himself into me. I hadn’t been expecting this and it nearly knocked the wind out of me. I let out a rather loud grunt and he repeated the same motion.

She had been sitting on the bed next to me up to this point, but sometime during the penetration she had stood up. I felt her hand on my back. He began to pick up the pace, slamming into me, pulling out a bit and doing it again. He only had one speed and I wanted some variation. It felt okay the first dozen times, but it was beginning to feel like a lack of imagination.

That lack of imagination turned into realization when I heard her whisper, I imagined into his ear, “You like fucking mama’s ass?” He stopped completely. He removed his hands, but I felt her slap them back onto me, her hands over his. I heard her slap his ass with her front, his positioning changing with her large breasts pressed into his back. It’s amazing what you can feel going on in a body when someone is inside of you. I could feel his blood pressure changing, feel him pulsing as she held both our balls in her hand, could feel the uncertainty as his hands were back on me.

“Fuck mama’s ass,” she said again and he did. But this time it was more slowly. She grabbed my hips and pulled me towards them while she pushed him into me. Somehow the extra force of her behind him made it feel like he had grown inside of me, like he was bigger and hitting deeper spots than he could have earlier.

I could imagine her exploring his body while he fucked me, biting his neck, squeezing his ass, as she directed him into me. I didn’t need to imagine the pulses of pleasure going through me every time he thrust inside.

On my end, it felt completely amazing. He wasn’t hitting my prostate, but it still felt amazing and after an indeterminate amount of time, he came deep inside of me, his hot cum squirting inside me. He pumped a little while longer, until he was completely empty, before falling out of me. I heard her slurp his cock.

I stayed on the bed, I was completely spent, my heart was beating in my ears and I could feel my asshole gaping. He left the room and went pee again.

“You want him to stay any longer?”

I was breathing too heavily to give an answer.

She felt my ass, ran her fingers around my gape before feeling the space under my cock. It was wet, but wet from sweat.

“Looks like you didn’t cum yet,” she said.

Somehow I let out a no.

She left the room and I could hear her talking to the other guy. I was alone in the room for a while. I regained my sense of reality: another man had fucked me in the ass and I had a random encounter to thank for it. His cum was inside me, and I could feel it oozing around. It wasn’t like anything I had felt before. I wondered if this was what multiple orgasms felt like… I hadn’t cum, but had been enthralled in pleasure for longer than I could quantify.

I heard the front door open and close and then she came back into her bedroom. She closed the door and it was dark again. I heard the click of the lube bottle and then a cold stream on my now less pronounced gape. I jumped a bit. She put a finger inside of me, and then another. I could tell she had a glove on. She began exploring inside of me until she found my prostate. She had obviously done this before. She moved her fingers inside of me to pull my ass up into the air. My body obeyed.

With the fingers of one hand inside of me, she used the other to play with my underside. She licked my taint, squeezed my balls. I felt my cock getting hard again and she noticed too. I could feel her fingers turn around inside of me, pressing more firmly onto my prostate, her thumb pressing from the outside. She licked down my balls, down my cock, before swallowing my head. Wet gulps were all I could hear as she began the slow process of deep-throating me. I could feel her tongue on my ball. It didn’t take much longer for me to cum. She completely drained me, pressing the last bit out of my prostate, through my balls and down my cock, into her waiting mouth.

I collapsed on the bed. She smacked my ass really hard. I felt my cock wanting to get hard after the hit, but I willed it away. I’d fucked and been fucked enough tonight!

She plugged her alarm clock back in and programmed it to say 4 a.m.

“You’re joking, right?” We’d been fucking for nearly eight hours.

She laughed then asked me what I wanted for breakfast.

Source: reddit.com/r/gonewildstories/comments/9tn2o8/unexpected_mfm_from_a_craigslist_hookup_many