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Julia had me put my ass under a pillow as she knelt between my legs with that strapon dildo bouncing menacingly. She started applying lube—which felt cold btw—to my butthole. As a man who had never done anything remotely like this, I was exceedingly excited. But I also felt much more vulnerable than I would’ve wondered. Julia had gone through a lot of work to set this up and to talk Maria into watching, and I wasn’t gonna let her down.

Actually Maria’s presence increased my excitement. I have a bit of an exhibitionist streak and I knew she was looking at my cock. I craved having her watch Julie fuck me up the ass. Julie had said she was welcome to join, but Maria said all she might do is masturbate.

Julia’s fingers felt good inside my ass. Really good. She was lubing up the dildo as Maria positioned herself cross-legged at my shoulder. I could see her parts of her legs, and noticed her cute toenail polish, instantly feeling self-conscious about my own toenails. We’d met half a dozen times. Maria was a curvy, bespectacled 40-year-old with tight, shoulder-length dark curls. She had on an oversized t-shirt and, I assumed, panties that made her feel sexy. What made her sexy to me was the combination of her outward confidence and those endearing hints of self-consciousness.

But I was here tonight to get pegged. And I got goosebumps when I realized it happening as Julia rubbed her cockhead against my hole. After some repositioning, she told me she was going in, and to let her know if it hurt.

The head didn’t hurt. It felt like a pinch as it stretched my asshole open. It popped inside with surprising ease. She paused and I think she was gonna ask if I was ok, but saw I was smiling. She gave me a pretty smile in return.

Julia is my age, so her permed hair is graying, and I respect her immensely for not dyeing it like so many women in there 50s do. She can sometimes be self-conscious about her body but I’ve never cared one way or the other. As she pushed in another inch, her pretty boobs jiggled, and I noticed how stiff her delectable nipples had become.

She only had to add lube once, when her cock was pushing my sphincter in, rather than sliding past it. Finally she was all the way in.

Lord Jesus, I felt full, just like women say about anal sex. Now I could feel an ache in my tender rectum caused by the stretching she gave me. I began to remind her that I wanted her to replenish the lube once in a while as she lubed up her palms and fingers. “Don’t worry, baby,” she said.

The entire time I’d been focusing on the unnatural feeling dildo going up my ass, and thinking of Maria watching this intimate act. Suddenly I remembered my own cock. It was throbbing, with a stretching ache not dissimilar to that in my asshole. My cock is small and no matter how many women say it’s ok, I’ll all the time be self-conscious about it, all the time a little embarrassed when I show it to a woman. In the moment, though, I badly wanted Maria to see it—to _want_ to look at my dick which, even if small, can provide lots of pleasure. I hoped she was fascinated at how engorged it was becoming. I hope she thought if my erection had unleashed an animalistic urge to fuck the living shit out of the nearest pussy.

Julia handled my cock with one slippery hand as she slid almost all the way out of my butthole. Sorry if this is gross, but it felt exactly like it does when you finally take a big shit after having been constipated. Then she rapidly put it all the way back in and I was surprised to hear myself utter a loud moan.

She began a rhythm of fucking me, in and out, in and out, while lightly gripping my cock as it slid against her hand. Oh Jesus. I moaned again and I realized that a lot fewer women in porn are faking their moans than I’d wondered! Did it hurt? Yeah, it did, but in the best efficient way. Julia re-lubed the dildo and repositioned it in the strap. I’d forgotten that this model was advertised as “stimulating the girl” by rubbing against her clit. Obviously, she hadn’t. When she went back to fucking me her eyes were closed and she herself moaned softly. At this point, Maria began running her fingers through my hand.

There were many sights and sensations, so I probably missed it when Maria began to masturbate. She’d taken off her top too, though I didn’t know that yet. I realized (a) that I was smelling pussy, (b) that it wasn’t Julia’s, and (c) that the barely audible squack-squack noise in my right ear was her rubbing herself with her right hand.

If I hadn’t quickly pulled Julia’s hand off my cock, I would’ve cum right then. Julia laughed and explained my predicament to Maria. Two women were looking kindly at my naked body, at me being sodimized and at my aching cock betraying the fact that I was loving it.

Maria laid down next to me. I felt the warm flesh of her breast against my cheek and she positioned it for me to suck, getting pussy juice on and around the nipple. She held my head steady so I could suckle. The fact that she was this turned on led me to the point of no return. Like a ordinary male, I announced that I was gonna cum. I needed them to watch.

I lasted two more anal strokes before I started to cum uncontrollably. Julia handled my cock lightly after a first spurt, which was half precum, spilled out, and before a gigantic spurt of warm sperm made it to my chest, nearly hitting Maria, who had stopped masturbating to watch. I groaned mightily as a second big spurt onto my stomach, followed by smaller spurts of semen.

Julia had never stopped fucking me and was near her own orgasm. Maria grabbed the lube and spread even more of it on Maria’s girl cock—the closest she came to touching my dick or ass. Finally she shuddered in pleasure, the dildo rubbing against her pussy having become too much. She pulled out—Ann incredible sensation—and collapsed on top of me. Maria laid next to us, rubbing Julia’s back and ass.

Maria didn’t cum. She insisted that it was ok, that she had a great time, and that she wanted to do it again. While she and Julia continued to meet for suckling, and while Julia and I continued to hang out, get high, and fuck, another threesome never materialized. But I’d never trade one time, nor would I forget my first pegging.

___

I’m not interested in roleplay these days, but I’d love to chat with adult women (35+ please) who are interested in the themes I explore here.

You can also check out my [story starters]( and some [other scenarios]( I’ve posted.

NSFW: yes

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