Vegas Birthday Weekend

As my name indicates, all my stories are based in truth and the events have actually happened in my life. That being said, I do want my stories to be entertaining, so I add a little "twist" or "spice" to the reality. I always appreciate feedback and comments at the end. Bonus if you can guess what's "truth" and what's the "twist".

For this multi-part story, each chapter will fall under a different category as that's how the actual weekend in Vegas played out. For new readers, I should probably explain that the reason we were in Vegas was to celebrate my 30 th birthday. Sherri had a plan to give me a different "sexy" card and gift on each night of the trip.

Chapter One was about our first night in Vegas (Exhibitionist) in front of the large windows of our hotel suite. Chapter Two was our playing around with a bit of Bondage (BDSM). Chapter Three was a poolside interlude (EC).Chapter Four had us playing with a remote vibe (T&M) all of which leads into this, the penultimate chapter.

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Sherri and I were on the couch in our suite where I was recovering from one of the most epic blowjobs of all time. Earlier in the evening she announced my "Daily Birthday Gift" with a card inscribed "Tonight, is about the BUZZ". What followed was a night of erotic tension as I controlled a remote-control vibrator in her panties that she wore under her demure sundress. When we returned to the room, she used her mouth and the toy on me until she swallowed my creamy load. I thought my gift was complete when Sherri got up and returned with a second card.

I opened the envelope and saw the exact same card as earlier in the evening. For the second time, the artificial voice sang Happy Birthday while a balloon spun above the card. My eyes traveled down to read the inscription, which this time, was written in red ink: "Tonight, is about the BUTT."

I took a moment to let the words register as I looked back over toward Sherri on the couch. With a smile on her face, she sat up and leaned over the arm of the couch. Lifting her dress over her hips, she exposed her naked ass to me before using her hands to spread her cheeks open. There, in the center of the cleft of her ass, was a dark blue gemstone glimmering in the subtle light. Her inner cheeks were wet and shiny with lubricant around the plug.

"Hope you can recharge, baby." She said with a smile. "Time for your real present tonight."

I sat there, visibly stunned while she gave a subtle wiggle of her ass. In the few years that we had been together, Sherri made it clear that her ass was off-limits. I got the message early on, when I would subtly try to work a finger toward her backdoor, only to have her move it away. There were a few times we did give it a try, however. Once was after a night of sharing "past experience" stories during which I talked about how much my ex-girlfriend, Tara, loved anal sex. Sherri seemed to take it as a challenge and returned to the sofa with a bottle of baby oil. The experience just reinforced her dislike of anal. The few other experiments always involved copious amounts of alcohol and day-after regrets on her part.

So, to see her bent over the arm of the sofa, her sundress pulled up to her hips with a gleaming anal plug inserted, I had a million thoughts running through my head.

"Oh shit, babe." I said. "That's fucking incredible. Have you had that in all night, too?"

"No, I don't think I would have made it with this thing and the vibrator. I put this in when we got back to the room, though. You like?" She wiggled her ass a second time as she smiled over her shoulder looking back at me.

"I think I'm still in shock. You never let me play with your butt. Why the change?"

"If I didn't know better, I'd think you're trying to talk me out of this idea. I just knew I wanted to do something special for your birthday this year and thought this fit the bill perfectly."

I started to run my hands up her bare legs to her ass cheeks as I continued to stare at her. "You are incredible."

She had used a decent amount of lubricant which had spread to the cleft of her ass. As I ran my hands over her skin, the lube coated more and more of her flesh. When my fingers brushed against the plug, I felt Sherri jerk slightly and emit a groan. Because I had just exploded into her mouth minutes earlier, it was taking my cock some time to return to form and she saw what was happening. She shifted down and swung off the couch reaching for my hand.

"Let's move to the bed where it's more comfortable. I have an idea while we wait for you to recover." She led me to the bedroom where she instructed me to undress and lay on the bed. As I did, she looked at herself in the bedroom mirror. She was still in the demure sundress with her long blonde hair in pigtails. She had removed her ballet slippers and her painted toes fiddled on the carpet.

"I was going to put on something else, but I was thinking that I kind of like this look. All sweet and innocent while I get my ass fucked by your cock. How's that sound?"

Once again, she had nailed the perfect erotic scenario. As much as I loved her in lingerie, or naked, or dressed in a sexy costume, there was something about her innocent vibe that made what was about to happen even sexier.

"But before we get to that, how about you give me a little treat and I'll tell you a story?" She walked over to the bed and straddled my head while she faced the headboard. Her recently waxed pussy was wet and swollen as it hovered over my face. I extended my tongue and gave it a lick.

"Mmmmmm" she moaned. "So, I've been planning this for a while but unlike all the other times we tried anal, I wanted to be ready." As she talked, I gripped her hips and brought her pussy closer to me. I ran my tongue up and down the length of her slit as she continued to tell her tale.

"So, went online and read some articles on 'anal for beginners' for some tips. The biggest thing they all mentioned was lube...lots of lube. I kept looking and found out they make some that are made JUST for anal. I liked the idea of something that would be slick enough but had some numbing agents in them, too."

Her words rang true as I started to lap at her pussy and felt a tingling on my tongue and lips. Whatever was in the lube was also slightly numbing my mouth as I serviced her cunt. It made the tactile sensations more difficult to manage as I was being more aggressive with my actions than usual. The results were that Sherri was starting to grind even harder as she rode my face.

"I also read that it helps to sort of build your ass up to the real thing and you can do it progressively. So, on the same site where I found the lube, there was a set of anal plugs that increased in size you can 'train' your ass over time." She went quiet for a few seconds as I flicked the tip of my tongue over her clit, which swelled from the sensations. My hands crept up her ass and for the first time, I gripped the jeweled plug with my fingers.

"Fuck, yes." She groaned. "Play with it. Don't pull it out, baby. But turn it and move it while you eat me."

Her breaths were getting labored as she neared an orgasm but tried to continue the story of her anal journey.

"When the set came in, I tried the smallest one first. It was thin and sort of rubbery, so it didn't hurt too badly when I put it in. Even though it was small, I felt so full, I ended up using my vibrator to get myself off while it was in there. I kept using that every couple of nights until I felt like I could take the next one which was bigger, but still sort of soft and rubbery."

I was struggling to keep track of the story with her thighs wrapped around my head as I focused on licking her. Her juices were flowing as I worked to swallow them without breaking my motions. I was twisting the plug in her ass and pulsing it in and out without letting the bulbous end emerge from her muscular ring.

"Oh, FUCK!" Sherri's entire body spasmed and a flood of juices hit my mouth. She bucked on my face a few times as her orgasm overtook her. She grunted a series of expletives before her body slumped forward and she took in a few deep breaths. She kicked her leg over my head and laid next to me. My cock was rock hard and ready while my face was covered in her scent.

"Looks like you're ready" she said looking at my dick. "But now I need a minute."

"Finish the story, then." I suggested.

"I will." She said as we both leaned against the pillows and reached for our drinks by the bedside. "So, I kept increasing the size of the plugs until I got to the one that looked to be the same thickness as you."

"When were you testing them?" I asked.

"It depended. Some nights when you weren't around and I was horny, I'd try one. I knew I wanted to be ready for this weekend, so there was a bit of a timeline, too. I managed to find different times. As a matter of fact..."

"What?"

"Remember the night we watched that stupid Keanu Reeves movie, and you kept asking me if I was feeling ok?"

"No way..."

"Yup. I told you was having some stomach cramps, but I really had a plug in my ass all night."

"Wait, I remember that night. You came back out to the living room and practically jumped me."

"Yup. I was soaked all night. When I went into the bathroom and took out the plug, I fucking came bent over the sink. If the movie had been any quieter, you probably would have heard me."

"When you came back out, you pulled my pants down and rode me on the couch. I sorta assumed you had gone to the bathroom and...uh...."

"Well, you were sort of right" she laughed. "I cleared out something and just needed some dick. Speaking of which..." She reached over and started to stroke my cock, bringing it further back to life. "I think I'm ready for this boy in me, now."

She shifted on the bed and adjusted some of the oversized hotel pillows, creating a sort of ramp for her to lean over. Spreading her knees wide on the mattress, she pulled the bottom of her dress up and over her hips, exposing her bare ass. The blue gem between her cheeks once again caught the light of the room and glimmered in the night.

"Ok, Jay. First, I want you to take it out of me."

"I will. But I want to remember this." I replied, reaching over to grab my phone. I positioned myself behind her and took a few snaps of her bent over with the jeweled plug in her ass. For the last couple of pictures, she turned her face back to me and gave the camera a sultry smile.

"What do you want me to do?" I asked.

"Grip the plug and give it a few twists without pulling on it, yet." I reached between her cheeks and gently gripped the base of the plug. It was already slick from the lubricant she had used, so it rotated easily inside her.

"Yes...just like that" she groaned. "Just keep doing that." Her hips and ass were slightly shifting and gyrating as I moved the toy inside her.

"Ok, now pull it out slowly." She emphasized the last word, making it clear that this would be a slow and calculated process. I got the base of the plug between my fingers and started to slowly pull it from her orifice. A deep moan was muffled by the pillow as Sherri buried her face into it. I was staring at her ass, watching the fleshy opening stretch wider as the girth of the plug widened.

"Fuck. Fuck. Fuck." Sherri was muttering into the pillow as the plug continued to stretch the muscular ring of her ass. I could see her fingers sort of clawing at the sheets as the toy expanded and enlarged her opening. Her pink asshole continued to enlarge around the shiny metal until it reached the tipping point. When the largest part of the conical toy emerged from inside her, the rest of it popped out quickly and easily.

I don't remember Sherri's reaction at that point because I was transfixed with the site of her asshole, still gaped open even with the absence of the plug. The muscles of her ass pulsed and throbbed as if searching for something to fill it again. I looked down at the toy in my hand and saw that while it was short and compact, at its widest point, it was wider than my cock. If Sherri's ass was able to stretch around it, I felt like I wouldn't be as difficult.

"Holy shit" I heard her say as she sat up. "I felt so fucking full with that in me, I can't even begin to think what your cock is going to feel like." She reached over to the nightstand and picked up two small bottles of lube. She examined each and handed the first one to me.

"Here. Coat your dick with this one. Use more than you think you'll need, then use a bit more." I poured the slippery liquid into my hand and started to stroke it up and down my cock, completely coating it. I took a second squirt and slathered it around the head of my dick until it was dripping off.

"Perfect, now take this one." She handed me a second tube and continued. "I want you to take a finger and spread more of this around my ass. Make sure you get the entire area and inside if you can."

"What's the difference?" I asked as I poured the liquid on to my fingers.

"This one has a numbing component in it. It will help make it less sensitive and painful."

I took my slick digit and for the first time in years, felt the tight ring of her anal opening. The flesh was tight and wrinkled and I could feel every bump and ridge as I spread the lubricant around her pink circle. I added more lube to my finger and started to gently probe the dark opening.

"More" was all I heard as I danced my finger over her asshole. I added more lube, made a few more rotations and gently pushed forward. Her muscles resisted at first, then relaxed and allowed my finger to slide inside her.

"Unnngh. Oh, fuck. Add more lube and finger my ass." Without removing my finger, I poured more lube onto our junction and as it coated it, I started to gently move my finger in and out of her. After a dozen or so strokes, my finger was sliding easily in and out of her anal passage.

Sherri shifted up on to her elbows and looked back at me over her shoulder, "You ready for your birthday gift, babe? I think it's time for you to fill my ass up." I positioned the head of my cock at her opening and pushed gently against it. Her ass flexed slightly but still resisted letting my dick penetrate it. I gripped my shaft to better line up and keep it from flexing from the resistance. I used my hand to move my head around her asshole while still pushing it slightly forward.

As I pushed, I felt her ass start to stretch and open around the head of my cock, watching as it expanded and felt it tightly gripping my sensitive skin. It stretched out as I pushed until my head cleared the muscular opening and it closed around the top of my shaft. A long sustained hissing sound left Sherri's mouth as I pused my length into her tunnel.

"Ohhhhh.....my fucking....ggg.....you feel so big. You feel so big in my ass, Jay." Sherri was literally screaming into the pillow. Were it not for the fact that it was muffling her cries, I was sure a neighboring room would have heard her and called security thinking she was being murdered. "It's so full, Jay, and I'm stretched so fucking wide, Jay. Fuck. Fuck."

She was babbling at that point as I entered her ass for the first time in years. I paused and stayed in that position as she writhed under me. She was taking deep breaths, controlling what I assumed were the painful sensations of having me in her back passage.

"Ok" she panted. "Push forward a bit more. Go slow."

I did as instructed, and slowly started to push more of my length into her. While her pussy was normally tight, her ass was like a vice grip on my dick. With every small motion, I could feel her tight tunnel grasping my cock. The muscles of her anal ring stretched and pulsed as I pushed further and further into her. When my hips met the flesh of her ass, she let out a long hissing sound feeling my cock filling her ass.

I didn't move as she took several deep breaths, adjusting to the foreign sensations. With each breath, I felt her ass grip and milk my shaft, squeezing it with her muscles. I held steady, allowing her to set the pace for the experience.

"Go slow, baby, but I want to feel you fuck my ass, now."

I gripped her hips and pulled back, feeling my lubricated cock slide out of her ass. When my head pulled against the muscular ring, I pushed back in. I was able to start building a slow, steady rhythm of sliding and out of her. Sherri's grunts and groans were deeper and more guttural than when we normally had sex.

"You like your gift, babe?" she muttered back to me. "Being buried in my ass?"

"Holy fuck, Sher. You're so tight. You feel incredible. Are you ok?"

"Baby...don't worry about me. This is for you. It burned when you started, now I just feel so full."

I was slowly building up the pace as I stroked back and forth in her ass. Because I was still concerned about hurting her, my pace was still slower than it would have been had I been fucking her pussy. Still, the flesh of her ass rippled every time my hips slapped against it. We were matching each other with the sounds grunts and groans filling the room. My hands were slick with sweat and lube trying to keep my grip on her hips as I plowed into her. As I continued to thrust into her rear tunnel, I felt her shift and then the slight sensation of her fingers where we were joined. She was flicking her clit, giving herself an extra level of stimulation while I fucked her.

"Dammit, Jay. I'm gonna come. I'm gonna come with your fucking cock in my ass" she moaned. "But I want to feel you fill me up, too. I want your cum in my ass, Jay."

Her words were cut off when a combination moan and scream left her throat and were lost in the depths of the hotel pillow. Her hips bucked up and down as the orgasm ripped through her. I was close to my own explosion when I felt a splash of fluids coat my upper thighs. For the first time in years, Sherri had squirted from her orgasm and had coated me with her juices. That, combined with her asshole pulsing and squeezing my cock, caused me to shoot a creamy load into her ass.

My cock pulsed and shot streams of cum into her bowels. I let go with a loud moan of my own as we both fell forward onto the bed in complete exhaustion. Neither of us were able to utter a word or sound as we struggled to regain our collective breaths. Lifting myself off her lifeless form, I shifted to the side, my shaft sliding out of her tunnel. As I did, I watched her hole gape open for a few seconds and the white, creamy load leaked from her. It pulsed, open and closed as her body continued to slightly spasm, forcing more of the fluids to flow out.

I lay, face up on the bed, covered in sweat, basking in the glow of Sherri's gift to me. After a few minutes passed, I felt her shift next to me as she slid out of the bed.

"Fuck" she uttered as she gingerly got to her feet. "Your cum is leaking from everywhere right now." Her dress from earlier was a wrinkled mess, bunched around her waist with her breasts, ass and pussy all exposed. Her hair was a knotty, disheveled mass of ruined pigtails and her makeup was messy and smeared.

"You ok, though?"

"Yeah" she replied, using her balled-up dress to wipe the various fluids from herself. "I'm a bit sore, but it's better than I thought it would be. The training definitely helped a bit."

"Thanks babe. Best. Birthday. Ever."

"I love you. Happy Birthday." She moved toward the bathroom in the semi-darkness of the room. "I am going to grab a quick shower before I fall asleep, though. I'm feeling sort of...dirty."

"Gotcha."

"You are welcome to join me in a couple of minutes. We haven't enjoyed the shower together yet. Besides, there's no way I'm letting you sleep all slick and slimy in our nice sheets, either. And who knows, if you have it in you, maybe there's one more round in store?"