Two Nights in Paradise Pt. 02

Author's note: Dear reader, please read Part I before reading this part. It will make more sense.

*

The date came and I was walking up the stairs again to Diane's bedroom. Again, there was music from our college days playing softly. Again, she was all but nude wearing only a sheer nightie and a smile. I moved toward her but stopped.

I told Diane that I had enjoyed 'her day' very much, mainly because I could tell she enjoyed it so much. I said that the things on my bucket list were not things that she'd enjoy or even be able to pretend to enjoy. Diane smiled a shy, yet sly, smile. She said she had been doing her homework. And she said she had been doing some shopping. She led me to her bedside table and showed me the array of sex toys she had prepared. Butt plugs, vibrators, dildoes, and a strap-on dildo that she made sure to point out.

She began unbuttoning my shirt and soon we were laying beside one another kissing, petting, and groping as we had a week or so earlier. I kissed her warm mouth and pushed the tip of my tongue in. Diane sucked on my tongue sensuously, then released it, offering me hers, which I hungrily sucked. I could see things would be different from the way 'her day' had gone.

I kissed my way down to her bountiful breasts and began to nuzzle, fondle and suck on the twin orbs. Diane positioned herself and me so that she was breastfeeding me like an infant across her lap. One of her hands cupped a massive boob and my chin, the other caressed my face, my chest and moved down to stroke my achingly hard cock. Her finger found pre-cum dribbling from its tip and used it to lubricate her stroking.

As I sucked on Diane's big tits, she cooed in my ear, "That's it. My big baby was hungry. That's it, baby, get all that milk from Mommy's big boobies. Suck harder on Mommy's nipples, bite them a little. Oh, I feel how hard Mommy's big boy has gotten. It does feel good when my big baby suckles his Mommy. Even Mommy feels warm and excited. Mommy's pussy feels very warm and very wet from your sucking. Here, suck on the Mommy's other big tit."

She shifted me over to her other massive tit and I continued to enjoy the combination of sweet mother love and fetish-come-to-life. I could tell from Diane's ragged breathing that she was becoming increasingly aroused. She kept shifting her hips and moving her thighs like she couldn't get comfortable. I knew just what she needed.

I rolled on to my back and pulled her legs to me until she was on top of me in a 69. Diane hadn't been lying about how wet she was. Her muff was as fragrant as ever and I buried my face in the soft nest of curls and rubbed against the soft flesh below. My tongue tip probed her slit to begin to work it open, but it found her pussylips engorged and gaping. I didn't want to move too fast. So I simply sampled her pussy's juices from her clit down to her pussy and further south still to her tight little rosebud virgin asshole.

I felt Diane's mouth kissing up and down my cock before the warmth of her mouth engulfed was felt like a lot of my length. She had gotten my cock and her lips and her hand or hands so wet that it all just felt like a warm, wet, pumping on my unit. And as if that wasn't enough to get my balls boiling, Diane's big hanging tits were draped upon my chest and belly. Every chance I could, I would glance down and see those two huge masses swaying and jouncing up and down, slapping together and against me.

As I enjoyed eating Diane's warm, wet pussy, sucking on her delicate little labia, running my tongue between the gossamer wings up to her clit, emerging from its hood. I was seized with the desire to tongue-fuck Diane's cunt and moved lower to get access. This pulled my cock from her lips and she tucked it between her flesh pillows and grabbed my asscheeks in her hands and squeezed them tightly.

"Fuck my big tits, big boy," Diane cooed. "How long have you dreamed of tittyfucking your old cumslut Diane? Pump your cock between my big tits, stud."

I reached down and pushed her mams together around my cock and pumped some long, slow, strokes. Her titflesh seemed endless. I could feel my balls aching with their load. But I was even with her pussy hole and plunged my tongue into it deeply and pumped my face in and back against her wet mound, my tongue flicking all around, hit and miss against her g-spot. My hands moved to grasp her round asscheeks and pull them apart. That allowed me to tonguefuck her more deeply. I heard Diane moan and felt her spasm as I hit the right spot.

But as I felt Diane responding to my tongue in her pussy, I felt her fingers moving around and across my asshole. I looked up at Diane's tight virgin rosebud an inch from my nose and moved my slurping tongue from her warm, wet, pussy to her little anal button. I attached my lips to her anus and ran my tongue tip across her tightly clenched sphincter. I sucked on her asshole. Her body shuddered and I felt a wave move across her body and I felt her asshole relax and open to my probing. At the same moment, Diane had worked the tip of her index finger into my virgin asshole and when she shuddered, she drove her lubed finger knuckle-deep up my ass.

The sensation washed over me like a wave. I drove my tongue into Diane's rear and pumped it in and out vigorously. She twisted and pumped her finger in my ass and pushed her tits down against my cock. Diane must have reached over to the nightstand because I felt her hand me something. It was a 4-inch butt plug. I rubbed the purple rubber toy on Diane's asshole and pushed on it until it pop in. At the same time I felt Diane's finger being replaced by a plug in my ass.

She told me it was time to fuck and I agreed. I moved around and mounted Diane and buried my cock's full length in her warm, wet, snatch. I could feel the plug in her ass through her pussy walls and I could feel the one in mine every time I pumped my meat into her. It wasn't long before I could hear Diane's breathing become labored and she quaked with a full-body orgasm. I leaned down to suck on each big breast as her climax shook her. The sight of her was amazing. Her face was flushed and we were both sweating from the hard fucking. I'd never felt like this.

I was ready to blow my wad and I was considering bending Diane over and blasting her pussy when she moved from under me. She stood next to the bed and reached for a black leather and rubber harness that held a dildo about the same size as my cock. She grabbed my legs and positioned me at the edge of the back, on my back, legs raised and spread, like a baby about to be diapered. Diane pulled the butt plug from my asshole and inserted two fingers applying lube generously. She stroked her big rubber cock to lube it and she bent it so the big tip was against my shitter.

One sudden thrust pushed the whole thing all the way in. I struggled not to scream but groaned instead. Diane began fucking my asshole with a strong, steady stroke. It felt incredible. It hurt and it was so deep in me, but at the same time my cock had never been harder. She reached down to stroke my cock as she fucked my ass. I looked up at her. Her eyes were focused on my ass and her face cock fucking it. Her face was a study in concentration and she was working hard pumping me. Her big tits jiggled and bounced with every thrust into me. The sight of those big jugs bouncing in time to the pounding my asshole was getting along with her lubed hand pumping my achingly stiff cock was almost too much for me. I was ready to have her jack my cock off all over her big hanging titties, but Diane had one last surprise for me.

She pulled the dildo from my ass and slipped the harness off. She got on all fours in front of me and held open her asscheeks. I removed the butt plug from Diane's tight little asshole. I lubed her up and, kneeling behind her, positioned my cockhead at the little rosebud of Diane's sphincter and pushed in. I felt her tense and I knew she was feeling a little pain. I loved knowing she was putting up with it. I pushed in harder. She grunted and started to cry out when the head popped into her ass. She moaned instead as I pushed my full length slowly into Diane's asshole. I grabbed her hips and began to slowly fuck her ass as I had dreamed of doing so many times before. I love the way she kept moaning. I could tell it was a mixture of her lust, pent-up desire, her wanting to be the woman of my dreams, and the pain and pleasure of feeling a cock pounding in and out relentlessly.

A change seemed to come over us both. I had been close to cumming when Diane had been fucking my ass. And I was ready to pop when I entered her tight asshole for the first time. But now, it was like I couldn't even find that feeling of needing to cum. My cock felt harder and bigger than it ever had before. Diane's ass was so very warm and so tight. And Diane had been confident that she would not feel much, if any pain from having my cock pushed into her ass if she was warmed up enough. But when she felt that anal invasion it had hurt her unexpectedly. She felt a stabbing deep inside and wanted to scream for it to stop. Glancing back over her shoulder she saw me, my eyes glazed, ramming into her savagely and she suddenly wanted it all and more.

Looking to the big mirror on her dresser, I could side a perfect side view of the two us. I could see Diane grimacing in pain, her face twisted as she gasped for breath. And I saw myself behind her smiling and slapping her round asscheeks hard. Diane was crying out but her cry seemed to express both pain and pleasure. She was loving both. And I was enjoying inflicting pain on her. I loved hurting her. But my sadistic pleasure was tied to her masochistic joy. It was too good to stop.

I caught sight of Diane's big, heavy tits hanging down from her chest as I ass-fucked her. They were glistening with the sheen of sweat that covered us both. I cupped the two prize melons, kneaded them roughly, pinched and twisted those beloved nipples, and began slapping and spanking each big tit in turn. Diane cried out for me to beat her tits. And I began to pump huge blast after huge blast of my cum up into Diane's ass. We were both screaming, tears in our eyes, as our bodies quaked and collapsed in a heap. I held her tightly from behind, spooning her.

She had given me my day. But now that I had tasted what the sex I had always wanted was like, how could I never taste it again?