Third Night, Three Holes
by Jimmy Lee
Copyright© 2026 by Jimmy Lee
Erotica Sex Story: Continuing our weekend together, Pamela is initiated into anal sex, followed by ass to mouth.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual Fiction Cheating Anal Sex Oral Sex .
When we first got together, Connie (my first wife) hadn’t even liked going down on me, but over the years she became used to it. A few times I’d cum in her mouth without warning because if I had let her know, she’d have pulled her mouth off and finished me with her hand. At first it disgusted her, but I think she eventually came to expect it. I’d also kept giving her tastes of herself on my fingers and dick, going from pussy to mouth, with similar results. She claimed to not like it, but over time I’d noticed whenever we would do that, she would cum with much more intensity, so I figured she secretly enjoyed it.
One day Connie surprised me by mentioning the flavor of my cum. Right out of the blue. She said she’d gotten used to the texture and the heat of it when it squirted into her mouth, but the flavor usually made her want to puke and she couldn’t wait to spit it out. “Have you ever tasted yourself,” I recalled her asking. “It’s nasty.” I could still see her scrunched up face. “I’ve been talking to Andrea,” a woman she tended bar with who seemed to be such a party girl that I could see her sucking and swallowing any meat that swung between two legs. “She says drinking pineapple juice will make you taste better.”
The prospect of her finally enjoying it enough to maybe even swallow was exciting, and I’d drink gallons of pineapple juice if that would make it happen. “Well, I’ll pick some up,” I said.
“I already have. It’s in the kitchen. Start drinking it, please.” Oh, fuck, yeah!
I did and after a while Connie said she noticed a difference. One evening she was on her back with her head turned toward me as I knelt beside her, fucking her mouth and fingering her clit. “I’m ready to cum,” I said, wondering if she’d keep sucking or switch to her hand. She pushed her head forward, sliding her mouth down my shaft to indicate what she wanted. Oh, crap, that was it. I blew a load into her mouth and watched her throat work as she swallowed it down. Gripping the base of my shaft with her thumb and index finger, she milked the last drops out, then pulled her mouth off me. “Ahhhh. Did I suck you dry?” she asked with a smile. There was never a problem with me cumming in her mouth after that.
Over the following months we both sought ways to enhance my flavor even more, experimenting with various fruits, veggies and spices. We also experimented with other activities such as anal, ass-to-mouth, rimming, even swapping and multiple partners. Once the swallowing cum had been overcome, she turned into a sex fiend with few inhibitions. We were so perfectly matched in bed that it was a real shame when I had to leave her because of her lifestyle. She was a speed freak who was busted too many times and turned narc to stay out of jail. That made her a target and too dangerous to be around. I was young and had tried to get her off the stuff, so I just bailed to protect myself. I’d searched in vain for decades to find another partner like her. And now...
Roger, Pamela’s husband, was on a fishing trip, as she put it, “drinking beer and doing macho asshole stuff”. It was morning following an amazing fuck the night before. That had been our second time together, the first being in my tent during a camping trip as Roger slept in their trailer. While we were swimming earlier that day, Pamela had accidentally brushed against my cock which was hard from looking at her delicious body in a bikini. She realized I was sized like her first lover, larger than her diminutive husband. She loved Roger dearly, that was obvious, but he could not satisfy her as her first and only other man had. Apparently, I’d made her happy that night because she’d invited me over for the weekend of the fishing trip for a more extended and in-depth (pun intended) experience.
It was warm enough that no covers were required so we were laying there naked, her on her back with one hand on her stomach, breasts rising and falling as she slept. I was on my side marveling how a woman in her mid-50s with two grown kids could still look so good. Not just in her face. Sure, her breasts sagged to either side, but they were still full with no stretch marks, pink areolae only slightly larger around than her darker pink nipples. Her belly was almost flat and only slightly wrinkled from the pregnancies. Bush neatly trimmed. Thighs still firm. I couldn’t see her butt, but I knew it was still shaped nicely with only a bit of cottage cheese look. She could seriously rock a bikini. My dick stirred at the memory of her breasts and belly glistening with water as she walked up from the river, nipples pressing prominently against the fabric of the top. God, I wanted to fuck her right then. Her eyes opened and she smiled at me.
“Good morning.” It was barely more than a whisper. “Did you sleep well?”
“After all that exercise? Oh, yeah,” I replied. The scent of the previous night’s sex still lingered. I was half hard, and it wasn’t from needing to pee.
She turned onto her side facing me and lightly stroked my cock with her fingers. “I see you’re recovered nicely. But I’m hungry and we both could use a shower.” Well, I couldn’t argue that since I had a hole in my belly, too. Leaning over she gave me a peck on the lips. “Come on. Let’s wash each other’s backs.” She rolled out of bed and headed toward the bathroom. When she reached the door, she turned back. “You coming?”
“Just admiring that mighty fine butt of yours,” I replied.
“Let’s shower and have breakfast, then you can do more with it than admire.” Oh, fuck, yeah. I jumped out of bed and joined her in the bathroom. They had a large garden tub with plenty of room for two (maybe three) people, and a shower head on a hose to allow spraying everywhere. We scrubbed each other down, first she cleaned me, then I cleaned her. I was surprised when she slipped a soapy hand into the cheeks of my butt and scrubbed me well there, then moved on to the area behind my balls. Then she stroked my cock just enough to get me mostly hard before handing me the soap so I could do her. I repeated the procedure, making sure her ass was clean after what she’d said. We dried each other off and went to the kitchen where she fixed us eggs, grits, and ham. Then I washed the dishes which she dried and put away. With all the chores done, I said to her, “I’m really wanting to play some more. Are you ready to be filled up again?” That was a reference to my size vs her husband’s, something she’d said on our first night in the tent.
“Let’s go back to bed,” she replied, turning toward the bedroom. Knowing I was watching her “mighty fine butt” she gave it a wiggle and laughed when I slapped it lightly. She lay on the bed on her back with her legs spread slightly and I lay to her right side, propped on my arm, looking down upon her deliciousness.
“I can’t believe how hot you are, Pamela.” I placed my hand on her belly, lightly massaging her stomach before moving it up between her breasts, across her neck, to caress her facial features. As I ran my fingertips across her lips, they parted and her tongue flicked out to them. I brought my fingers down, pulling her lower lip down a bit, across her chin, down her throat, and over to her left breast which I lifted toward me and began squeezing and massaging. As I released it, she moved her hand up to support it from the side, holding it where it had been when she was younger. Using the flat of my palm I lightly rotated my hand over her nipple, feeling it harden under my touch. Her right hand found my growing cock and began stroking it, her fingers feeling like feathers on it.
Lowering my head to her right breast, I surrounded her nipple and sucked as much breast into my mouth as I could. Flicking her nipple with my tongue, I could tell it was growing and hardening to match the other. My right hand left her breast and trailed fingertips to her navel where I delved in slightly, as if it were a vagina. That brought a gasp from her. Something she’d not experienced before, I guessed. After “fucking” her navel a few times my fingers continued their trail down to her pubic hair, on across her woman’s slit, and down the inside of her thigh, almost to her knee where my reach ended.
Lifting my right leg, I pulled her leg between mine, then lowered my leg trapping it there. This opened her, regardless of what she wanted, and it would stay that way until I released it. She was mine. Then I pushed her left knee away, indicating I wanted her spread further. She complied easily, completely opening herself to my touch. Her breath was becoming ragged, and her left hand still held her breast where it had been, as if she’d forgotten about it. Her eyes were open, staring at the ceiling.
Watching her face, I lightly brushed her slit from top to bottom, continuing to the crack of her ass until I reached the sheet. Her eyes went wider, and she sucked in air through her parted lips. I felt a quiver in the leg I had trapped. Pressing my middle finger firmly against her ass crack I moved it back up, across her perineum, up to her woman’s well where it slipped easily into the hot, liquid silk beginning to ooze out. That brought another intake of air and even wider eyes, still fixed on the ceiling. I wondered if she was seeing anything through them. Without entering her well, I drug the nectar up along her slit, between her inner lips to her clit. When my finger stroked that little nub of pleasure, she gave a gasp/whimper and her hips bucked slightly. The quivering of her trapped leg increased. I circled my finger on her clit with light pressure a few times, then moved it back down. Some tension eased in her body with the loss of contact with her clit.
At her well, my ring finger joined my middle one as I worked them in a circular motion around the opening, spreading her juices around and encouraging her to open more. Her breathing became ragged with little whimpers and squeaks as her hips began to rotate, too. I slipped the pair of fingers into her to the second knuckles. She groaned and lifted her hips to meet the penetration. I pulled them out, then sank them in all the way, pressing the heel of my hand against her clit. “Ahh, God, yes,” she sighed. Leaving the heel of my hand pressing on her clit, I pumped my fingers in and out a few times, wriggling them around in there, getting them well soaked.
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