Last Post-Holiday Party Celebration

When I got back into the room, Sherri had changed into a different holiday-inspired outfit that while not as revealing, was equally sexy. She was now barefoot and her stockings were gone. She had on a long-sleeved flannel shirt in a red, white, and green holiday plaid. The shirt had a deep button-up V-neck that was open showing some cleavage and the hem of the shirt was just long enough to cover her ass cheeks but short enough to give a peek beneath it when she bent over slightly.

We settled in and sat up in bed sipping our drinks, talking about the night's festivities and watched the snow fall outside the window. I was running my hand up and down her bare leg that was exposed by the short shirt. I noticed that she still wasn't wearing any underwear which was unusual for her at night.

"Mmmmm" I said. "No panties?"

"No. I know sometimes you are up for a second round after a bit and since we don't have to wake up too early, I thought I'd be prepared."

"You liked that pillow under you, huh?" I asked.

"It was crazy. Something about the fabric on my nipples felt like they were being rubbed and tickled while you were pushing me forward. I'm not usually into that much sensation on my tits, but it felt incredible."

It was clear that Sherri was still horny as her language and sexual willingness were still in full gear, even after coming a few times already. She was right, though, and I could feel my cock regaining some energy.

"Put your drink down and roll over on your side." I said. While Sherri did that, I removed my boxers for the second time. We moved into a spooning position, and I lifted the short hem exposing my wife's ass to me. I squirmed over and positioned my cock so that it was in the cleft of her ass, not pushing into her but running up the length of her ass crack. Even though we had both cleaned up a bit, there was still enough residual lube and fluids that our skin was still slick.

"Jay, no. Not there." Sherri said sternly.

"I'm not putting it in. I just like the way this feels."

I then continued to move my cock gently and slowly up and down the channel between her ass cheeks. I pushed her cheeks together to give me a bit more friction and resistance to increase the sensations. It felt like a combination of a titty fuck and being buried inside her, but different enough from both that I felt like I could come just from the feeling. I reached around with one hand and slipped it inside the gap in her shirt to start fondling one of her breasts. Sherri was rocking her hips back against me, as she started to appreciate the strange position and motions.

"Stop for a second" she said, suddenly. She pulled away and I heard her open the nightstand drawer again. She shuffled around in there until she slid back and repositioned herself before saying, "Ok, keep going."

As I started my slow movements again, I heard and felt a buzzing sound. Sherri had gotten one of her toys out of the drawer and had it pressed against her clit. It was the shape of a pink dolphin that had three different attributes. The dolphin's head vibrated, there was a ring of rotating beads on its body and its dorsal fin bent up and wiggled against her clit. She had it positioned so that just the tip of the dolphin's nose was in direct contact with her exposed button, and she started rocking back and forth between the toy and my cock.

Her hips moved back and forth and then in a circular motion as she tried to intensify the sensations on her clit. Even though my cock was enveloped by her ass cheeks, I could still feel the slight vibrations from her toy. Despite all the sensations, I was trying to stay steady and just maintain the motions I was making. A few times, when she would move suddenly or jerk her hips, my cock would rub against, and slightly press on, her asshole. Every time it did, Sherri would moan or jerk away.

My wife's breaths were coming deeper and faster and she seemed to be approaching another climax. I was quickly realizing, however, that I wanted to be inside her again. Just as I started to shift lower to get access to her pussy, Sherri pulled away the dolphin and grabbed the bottle of lube again.

"Fuck it." She said, handing me the bottle. "Use a ton and see if you can slide in my ass."

I was legitimately shocked. In our entire 20 years, we had done anal maybe four or five times. There were some special occasions where Sherri would let me try, but even my modest dick was too uncomfortable for her to try repeat performances.

"Are you sure?" I asked.

"Consider it an early present. Now, shut up, lube us both up and see if we can do this."

I opened the bottle and poured a decent amount of the silicone lube into my hand and ran it up and down the length of my shaft, coating it in a thick layer of the slippery fluids. I poured more and began to coat the outer rim of her puckered hole. Rather than pulling away, Sherri pushed back toward my fingers and put her vibrator back on her clit. I took my middle finger and pressed forward, sliding through the ring of outer muscle. Sherri grunted and I felt her jerk away slightly.

"You ok?" I asked.

"Yeah. More lube, and use your finger to get me slippery inside, too."

I did as I was instructed and added more lube until my middle finger was easily sliding in and out of her ass. I used my index finger to continue to spread as much of the lube around her outer ring as I could. I used even more lubricant and was able to slip a second finger just inside her opening. She was now taking short, quick breaths as she got used to the feeling of two fingers inside of her normally forbidden hole. I was making very small circles and slight thrusts with my two fingers as I tried to stretch out her hole as best I could.

"Do it. Now." she ordered. "Stick your cock in my ass."

I pulled out my fingers, put a few final drops of lube on the tip of my cock and lined up with her ass. As soon as I made contact, I felt a lot more resistance than I did with my fingers. Sherri grunted again and I was worried about hurting her. We were still in the spooning position with me pressed against her back.

"Want me to stop?"

"No. Go slow. Let me take a few deep breaths and relax a bit."

I kept up the slight pressure while Sherri took a deep breath, then another. I felt her ass pucker, then relax, and the head of my cock slipped through the rim of muscle and was inside her.

"Fuck. Fuck. Oh my Fuck. It's so big. Holy fuck!" At this point, it was probably good that we lived in a house with some land around us because otherwise Sherri's scream would have woken up everyone near us. I started to panic and started to pull out, but Sherri stopped me.

"No! Don't pull out! You're fucking in my ass. Push in .... But slowly."

I pushed forward and felt her ass open for more of my shaft. I had forgotten just how tight it was and I thought I was going to come immediately. Fortunately, because I was moving so slowly, I was able to control myself and resist climaxing too early. I moved as slowly as possible, and I could feel the muscles of her anus gripping my cock with every centimeter of movement. Every muscle in Sherri's body was tense as she rode out the initial discomfort.

"Jay. I feel so fucking full. Are you all the way in yet?" she groaned through gritted teeth.

"Almost, babe. Are you ok?"

"Yeah. Do it, let me feel all of you inside me."

I pushed forward more and felt my balls come in contact with the bottom of her ass cheeks, burying me completely inside of her. I paused as we gently rocked against each other so she could get used to feeling. She had stopped using the vibrator on herself as she took deep breaths adjusting to me inside her.

"You ok?" I asked again.

"I feel so full, Jay. It stings, but I feel so full. I can feel you everywhere. My ass is so full and even my pussy feels full."

I felt her shift and move the vibrator back to her pussy. This time, I could feel the vibrations more distinctly. As soon as she made contact, Sherri started to move again, which forced my cock to begin sliding in and out of her ass. Grunts, moans and a long hiss came out of Sherri's mouth as I started to slowly fuck her ass in a steady motion. She was working her vibe up and down her slit expanding the area of its effects. Meanwhile, the tightness of her anal tunnel was gripping my cock and pushing me closer to my own explosion.

"Don't move for a second." she ordered as my cock slid in to the hilt.

All of a sudden, Sherri lifted her top leg and spread herself open wider, which caused her to clench on my cock even more. I felt pressure at the base of my cock and then a slow and steady increase of pressure up my shaft. The vibrations had increased tenfold as I could feel them through the thin wall between her pussy and her ass. Sherri had inserted the vibrator and was double penetrated with my cock in her ass and the vibe in her pussy.

She was full for literally only seconds before she exploded in a tsunami of ecstasy. Every muscle in her body seized as she moaned and thrashed from being so full. A string of expletives flowed out of her into the night. I felt a wave of fluids flow out of Sherri's pussy as she squirted and flooded for the first time in years. She pulled the vibe out of her pussy quickly and that fast motion sent me over the edge. I gripped her hip, pushed into her, and felt my cock explode in her. Shots of cum filled her ass as she bucked against me.

"Oh fuck, I can feel your fucking cum in my ass! Fill up my ass, Jay! I'm a fucking ass whore for your cock, baby!"

I hadn't heard Sherri act or talk like this in years and I probably would have gotten hard again, if I hadn't already come repeatedly that night. But nature took its course and my dick slowly deflated and slid of her ass, bringing with it another pool of cum and lube. I rolled on to my back and Sherri was barely moving. As I regained my breath, I put a hand on her naked hip.

"You ok?"

"Holy fuck. That was unreal. I can barely move."

"Want a towel or washcloth?" I asked.

"No. I'm going to get up and use the bathroom for a minute." Sherri slowly got up and walked gingerly into the bathroom. A few seconds later I heard the shower start. I must have dozed off because the next thing I remembered was her coming out of the bathroom, with her nightshirt on, her body a bit flushed from the shower.

"You coming to bed?"

"That bed is disgusting." She replied. "I'm sleeping in the spare room." I looked down and saw that the sheets were twisted and soaked. There was cum, juices and lube everywhere. Even her vibrator was laying halfway down the exposed sheet. "If you want to join me, take a shower, first."

"Fuck it. I'll just sleep here." I replied looking at the clock which read 2:10am.

Sherri leaned over and kissed me on the forehead, "Good night. I love you. Happy early Christmas."

Epilogue (4 months later):

Like so many others, Sherri, our daughter, and I had been locked up in our house for about a month during the pandemic. Also like many others, we were trying to occupy ourselves with any sort of tasks we could and that week we decided on a "deep clean" of the house. I was moving, cleaning, and vacuuming everything in the living room when a glimmer of something caught my eye. Under the cushion of the couch, tucked into the frame was a small flash of red with something shiny glittering in the light. I reached down and pulled out the piece of fabric to reveal a bright red G-string with sparkling snowflakes on it. I stuffed it in my pocket and felt myself stiffen slightly as I remembered the best, last, holiday party celebration we had for a while.

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