The Confessor: MILF Gone Wild

Julie adored her pictures. She probably looked at herself critically in the mirror, looking for and exaggerating flaws. I didn't go out of my way to hide her flaws, but I had a knack for keeping them in context of the whole of her body.

"These are amazing," she said, "You could almost make me believe I look this good."

"I only draw what I see. I don't lie when I do this," I said.

I took the drawings from her hand and put them safely on the desk. I returned to the bed. I pulled her in for a kiss and my hands started all over her body. It had been a torturous time for me sitting there, drawing her whole body, but not being able to enjoy it fully. But it was the good sort of torture, the denial and temptation. It wasn't like I was being teased or used. I could have stepped in at any time and she would have welcomed me. But discipline is the key to my role, and now that we were both wound up, it was time to show her how desirable she was.

I took charge, of course, as that is what she needed. I kissed her deeply and took her in my arms.

"Unbutton my shirt," I commanded, playing with her ass while he undid my shirt.

She stripped the shirt off me, then lifted my undershirt. Her hungry hands fumbled with my belt as she anticipated unleashing my cock from its confinement. She unzipped me and pulled down my pants. I kicked them off, leaving only my boxers.

"Lick it through my boxers," I said.

This is a trick I'd learned, and I guess a kink of mine. The thin wall of fabric dulled the physical sensation of her oral play on my cock, but it more than made it up with heightened anticipation, especially on her end. Even through the fabric she could feel my cock throb, and a small wet spot of precum started to form, mixing with the light moist saliva she left. I reached down and undid the button fly in one quick move, exposing the underside of my cock. She quickly pulled it out and started sucking and licking my shaft and tip.

After a few moments her fingers found her way to the waistband of my boxer, wanting to pull them down, but wanting permission. I took a handful of her hair, then pulled gently so she was looking at me.

"Pull them down, then lick my balls," I said.

She did, pulling my boxers down to my knees and kissing and licking my balls, while one hand stroked and played with my cock. This was a great feeling, and I knew I could push her further than I figured she had ever gone.

"Have you ever licked a man's ass?" I asked.

She looked up at me, the expression signaling that she had not. But not that she would not. I looked at her and she looked at me. I said nothing, and didn't even bother to give a look of begging or cajoling. I just waited with quiet confidence. And she finally looked down, lifted by scrotum, and gave my asshole a lick. And not a tentative little one, but a full lap. Then another, and another. Her hand continued to stroke my cock. A leaned back and let her go to work on that. She was game for anything I asked. I wouldn't even need to use my commanding voice. She was bought in for whatever tonight. Not just with me, but with Harper as well.

After a few minutes of asslicking I felt satisfied, and moved her up. I played with her tits for several moments, enjoying them with my hand and mouth. I then told her to wrap her tits around my cock, and started titty fucking. We hit a rhythm together, Me thrusting and her going up and down. Her tits were warm and enveloping my cock. I wanted to yell our "Dear God", but held my tongue. This was no time for a callback.

I felt myself nearing climax and stopped. I wanted to finish so much, but that would be a sexual favor for later. Now it was time for the show.

We moved up on the bed, and I slid a pillow under her back to arch her pussy in the right angle. I kissed her pussy and did a few minutes of oral to get her nice and wet. I stuck my finger deep in, pulled it out, and put it by her mouth. She sucked my finger clean.

I slid inside her and started slowly thrusting in. I felt up her breasts and started kissing her neck as I built up speed. As I started going faster her legs wrapped around me.

"Tighter," I ordered, and her legs tightened.

I liked the tightness of her grip. I only wish she was still wearing her high heels so they could dig in my sides a little. I know, a small kink of mine, but it was too late right now. The rhythm was going, and I couldn't interrupt it.

Within a minute she was building to climax. I thrust harder, and took one breast in my hand and pinched the nipple. Her back arched and I knew she was on the edge. I went straight for her neck and kissed the spot I knew was getting her most horny. Her neck bent toward me and a final loud moan came out.

"OOOOHHHH!" she climaxed.

She came, and for several moments lay there, giving small grunts as I continued to thrust inside her. Her eyes opened in the post-coital haze. A hand reached up and touched the side of my face. I felt a surge of adrenaline in my body. I'd finished her off, now it was my time to come.

I let the restraint I held go, all attempts to delay orgasm. Now it was time to culminate the night's flirting, foreplay, and romance in one big go. I grabbed her head and pulled her deep in for a kiss. My tongue went deep in her mouth, and I breathed in deep, taking the air out of her lungs. This caused her legs to tighten up again, after having gone limp after orgasm. Her fingers dug into my back and the air left her lungs. I held on for a second longer, then let her face go as the orgasm hit my body.

I never really know what I sound like when I come, I am usually so lost in pleasure I can see or hear almost nothing. But I did hear Julie's gasps for breath after I let her go, and those deep breathes excited me as the second, third, fourth, fifth pumps of cum came out of my cock.

"It felt like you were trying to suck my soul out," Julie exclaimed as I pulled out of her.

I didn't answer that, just put my cum-and-pussy juice soaked cock by her face, and she sucked it clean.

"Come," I said.

I walked her to the shower, giving her ass a smack. She showered and cleaned off our bodies.

"You're good," she said.

"Thank you," I said, kissing her.

"I mean it. Like, men my own age, the ones that aren't married, they don't have what you have," she said.

"So date men my age," I said, "Though not before our date with Harper."

"How is it that I get two young people into me after years struggling dating post-divorce?" she asked.

"We hadn't met before tonight," I said.

"I don't want to be just another lay for you after what you've been to me tonight," Julie said.

"We still have a ways to go to make this memorable," I said, "We've got our date with Harper."

"Which you arranged," Julie said, "You're doing so much more for me than I could do for you."

"Trust me, Harper has something she wants to do that she can't do without you. She and I couldn't do what she is going to be able to do with you and I," I said.

Julie smiled. I knew she didn't believe it yet, that she could play the role of a sex goddess tonight. But at least now she was beginning to believe that it could be possible. And the truth was this was memorable. I might have had more, and certainly more exciting sex, than most, but a generation-bridging threesome with a Girls Gone Wild model and a part-time OnlyFans was a first for me (and as of this writing, still the only time for this very specific scenario). And that threesome would lead to even more adventurous sex.

But let's not get ahead of ourselves. We still have the date with Harper to attend.