Getting more comfortable (MFFM) | 2016

Stephanie and I had a pretty interesting relationship from the first time we slept together. She knew I slept with Jeff and Craig (and occasionally Don). She didn't have a problem with it, other than she wasn't allowed to watch. I didn't ask if she slept with anyone else. We'd meet at the coffee shop, or I'd pick her up at her apartment, or she'd come over by mine. It was casual and it was without pressure.

We had sex a lot...and I mean A LOT. After the first time, I can't recall a time we got together where we didn't have sex of some sort. She wasn't the biggest fan of anal, but there were a few days out of the month she was OK with it...or in the shower. Sometimes it was oral, sometimes it was just a handjob, but there was always something sexual going on.

It was about four months in...late August, '01 when she got up off of me, on the couch and said, "I kind of want to see you and another guy together."

I chuckled and mentioned that the only ones I slept with weren't big on having a girl around. She followed with, "OK, if I find a guy, could we do it?"

When one of the best pieces of ass you've had in years asks you to have sex with her and someone else...I'm pretty sure you say, "Yes", so I did.

And that was it. I didn't hear anything about it again, for a while. In late September '01, after things had a chance to stabilize a bit and people could start acting human again, she asked me if I would still do a guy in front of her. I told her that I was still game for it, if that's what she wanted. She told me that she'd be over on Friday with some friends.

"Some friends?" I thought, but I gave it a rest. Part of her allure was that nothing was ever set in stone.

I got out of work on Friday and went home to chill out. I'd just finished a particularly messed up project and wanted to take a bath. 8:45, there was a buzz on the lobby intercom. "Hey, It's me. Can we come up?"

"Sure" I said.

A few minutes later, in walked Stephanie with a heavyset girl she introduced as Marie and a guy who was heavier as well. He said, "Hi, I'm James."

James was probably 22, maybe 23 years old. A few inches taller than my 5'9", but he had 40 pounds on me, easily. His reddish-blonde hair appeared to be thinning a bit, but he smiled big and had a warm, friendly air. The kind of guy you like being around, I could tell immediately.

Marie was pretty big. She was probably 5'7", and to this day I'm terrible at guessing weight on women, but she was definitely big. At that point in my life, bigger than I would have looked twice at. Not fit for /r/BBW...more /r/gonewildplus.

Stephanie had come in with one of her "outfits" on. Like I said, we always had sex when we met up, but there were a few outfits that she wore when she was concentrating on sex, like sex was the goal of meeting.

Vinyl pants, tanktop under a jean jacket. Doc Martin 8 lugs. She really enjoyed keeping those on during the occasions she wore them over. We all talked for a bit. Steph and Marie were in a class together, and they'd struck up a conversation. At some point, Steph had mentioned she was 'seeing' a bi guy. Marie had mentioned her boyfriend was bi as well. One thing led to another, and we were in my apartment.

Steph must have figured she'd waited long enough for this night, as she wasted no time after opening up a bottle of wine to get mostly naked. By the time she'd stripped down to her panties, I was in my boxers, James was naked and Marie was in a bra and panties as well.

Surprisingly, with everything going on, I found myself sideways glancing at Marie more than I thought I would. Her breasts were immense. It looked like her bra had more material that Steph had worn to come over.

James stood up and asked if we should go to the bedroom. He'd been glaring at Steph like she was lunch since she took off her shirt, and I didn't blame him in the slightest. I got a good shot of his groin as he stood up. It gave me the idea that maybe the powers that be were compensating the guy for his premature balding by strapping him with a gorgeous cock.

Steph walked into the bedroom, followed closely by James. I ushered Marie in and followed.

On the bed, we chatted while taking off the rest of our clothes. Marie was self-conscious as she pulled off her panties first, then her bra. I watched as the huge globes let gravity take control, one resting on the bed as she lay on her side, the other slightly on top and slightly south of the first.

I reached out and touched Steph's upper thigh. She swung around, putting her hot, wet slit at my face. I lay back and let her straddle my face. She had enjoyed this massively the first time she did it, and it had become a regular addition to our time together.

A second or two later, I felt a hand wrap around my hard 6". At first, I wasn't sure if it was James or Marie, but only a moment later, a foot was on either side of my head as James lined his prick up with Steph's face. She enveloped him, slobbering with gusto at his equipment.

I'd been working with her on her technique. I wasn't an expert, by any means, but I had sucked a few cocks myself, so it was something we could do to work together.

I could look up along the lines of her body, between her 34D's and see her working on James' manhood. It had looked to be about 7" prior to us getting started. Now, it looked every bit of 8" and thick as any I'd ever seen. Stephanie worked on the 4-5" or so she could fit in her mouth.

The hand on my own cock was replaced a moment or two later by a mouth. Scratch that, an amazing mouth. Marie was soft and relaxed while she mouthed me, you could tell instantly that she saw it for what it was, foreplay. She didn't work on me like she was trying to get me off, only that she was trying to get me going. Her hand stayed near the base of my shaft, using my skin's tension to aim the tip where she wanted it. I could feel one of her giant tits rub against my leg as she worked on me.

I could hear a bit of dialogue going on between James and Steph, and after a moment or two, Steph unlocked her mouth from James, got up off my face and turned around. I glanced down at Marie, who was intently working on me, her eyes closed, her long hair hiding the sides of her face.

Steph re-straddled my head, this time facing the other way. I began working on her again, only to see a sight I was unfamiliar with. Immediately above my head, James' condom-clad cock lined up with her inner labia I'd just been working on. Less than an inch from my nose, the head of his prick found her small opening and pressed forward, entering the area I'd prepared for him. As he pushed in, his scrotum hit my forehead, sliding down my face, my nose and finally my lips as he pushed all the way into her.

I didn't skip a beat. I kept licking and nibbling her, but also alternated to him now and again. He apparently loved it, and he groaned as he slowly fucked her, back and forth, over my face.

The mouth that had been working on me stopped, and I felt a condom go over me. My rhythm on the sex above me went choppy as I thought, "Marie's not going to fuck me, is she?"

That was when I felt the weight of her legs first on my left, then swinging over to my right. Her hand went down between us and aimed me at her. I glanced down, James' sack hitting my forehead to see me vanish somewhere between her thighs.

My god was she tight. As she sat down, I went all the way into her and I heard her gasp slightly. She began rocking her hips over me, the in-and-out motion being created not by a vertical but by a horizontal movement.

And it was almost too much for me. I tried to concentrate harder on what my head was doing, and went nuts on Steph's clit, which was exposed on every back-stroke from James. This was her undoing though.

She began to buck backward, hitting my lips in a not-comfortable way as James tried to keep up with her. When she started to hit her orgasm hard, I felt his smooth sack begin to wrinkle, and two strokes later he buried himself until his strawberry blonde pubes smashed against her mound. From my vantage point, I saw his perineum pulse as he filled his rubber.

The sight above and the feeling of Marie's extraordinarily tight pussy on me caused my own violent orgasm to start. I reached down and grabbed her upper thighs, on either side of mine, and pushed up hard into her. She gasped again, along with a tiny whimper. Minutes later, we all lay side-by-side on the bed.

Steph turned at me, slapped me on the chest and said, "You didn't fuck him".

James looked somewhat shocked, "Who told you 'I' was going to be getting fucked? I'm the one who does the fucking!"

This would possibly be bad.