Minnesota Libido: Part 4.
Jason & Sherri are joined by a MILF friend after another Halloween Party.
Based on a post by TruthwithaTwist. Listen to the ►Podcast at Steamy Stories.
Without going into a ton of detail, the event was a great success. Everyone ate, drank, and bid in the auction. The Princesses all took a picture together, with the evil Maleficent in the middle of them all. The magician they hired was amazing and just cheeky enough to entertain the adult audience. Of course, with that many adults being out without their kids, we all took advantage of the bar. As the night started to end, we were all pretty tipsy, including Grace who was laughing and giggling with some of the other moms.
I checked out at the auction table and quickly found out that in my buzzed efforts to support the cause, I had purchased more than my share of prizes and baskets in the auction. I had to run to the lobby and ask one of the bellmen to bring a cart and transport it all up to the room for me. After close to 30 minutes, I stumbled (allegedly just in character) back into the ballroom to find that most of the guests were filtering out.
Sherri and Grace were sitting with some of the other parents as I sauntered over, taking a seat at the table.
"Avast wenches! Be there any room for Captain Jack Sparrow?"
"Only if he's going to get us all a round of drinks"
"Aye. My lady." I went to the bar where I got one last round and brought them on a tray back to the table. After handing them out we all toasted a successful night.
"Drink up, me hearties, Yo Ho!"
The group started to break up when Sherri leaned over to me, "I don't think Grace can drive."
"Is she that gone?" I asked.
"Yeah. She's been drinking quite a bit all night. What should we do?"
"Tell you what. Take her upstairs, since her stuff is up there, anyway. Let me talk to the desk and see if they have any rooms."
"Babe. I'm not sure she can afford one."
"Don't worry about it. With what I spent tonight, one hotel room won't break me." I stood up and headed to the lobby.
"Wait! What do you mean 'with what you spent'?'" she called after me.
15 minutes later, I was in the elevator feeling defeated. The hotel was completely sold out because of the events being hosted. I quickly realized that my night with an uber-sexy witch wasn't happening with a guest sleeping in our room.
When I entered our room, I saw the pile of baskets and packages stacked against the far wall. Somehow, in my inebriated state, I had collected quite the array of prizes. Sherri and Grace were looking through my treasures with amused looks on their faces.
"What in the hell did you buy?" Sherri asked. "And did we really need a kids' gardening basket?" Both women giggled as I joined them in looking though the pile of cellophane and tissue paper. As I opened one, my face lit up.
"Yo ho ho, and a bottle of rum!" I exclaimed as I pulled a bottle of expensive rum from one of the baskets. "Anyone want a nightcap?"
I poured us three glasses of the amber liquid over ice, then excused myself to the bathroom where I used some makeup remover to take off my fake beard and makeup. I removed the heavy accessories to my costume and went back out into the living room in just my baggy pirate pants and shirt.
Sherri and Grace had similarly removed some of their costumes. Sherri was sitting on the coach, still in the black and purple gown. Her boots were on the floor, and I could see her nylon-covered feet tucked under her. Grace was in a chair and had taken off her shoes, quiver and belt and was sitting with her big green dress tucked around her. I settled in next to Sherri on the couch and she leaned back to rest against me.
We all toasted and chatted about the event, the various people and all the gossip that came with an event like that. At some point, I refilled all our drinks and we continued to chat and relax. As expected, the conversation turned to Grace and her situation. She got emotional talking about what Andy had done and how much her son missed having his dad around. Sherri and I were very careful not to criticize nor comment and basically just listened. Whether it was the liquor or emotion or a combination of both, Grace eventually had a stream of tears streaking her cheeks as she talked about how lonely she was.
"I'm sorry." she whimpered. "I didn't mean to bring you guys down. I'll be right back." With that, she stood up, staggered a bit, and walked to the bathroom in the other part of the suite. Once the door closed, Sherri rolled slightly to her side so we could talk quietly.
"I feel so badly for her" she started. "Andy really fucked her over."
"No shit. I had No idea how much money he blew and how much he left her in the lurch." As I spoke, I looked down to see that when she shifted, Sherri's Maleficent gown had opened slightly up her extended leg. I could see the top of her black thigh highs and some of her exposed skin. I could see the curve of her thigh and her bare ass cheek peeking through the open slit of the dress.
Sherri must have felt me slightly harden at the sight of her because she slumped her head against my shoulder and half-whispered, "I'm so sorry babe. This isn't what I had planned for tonight. But she has nowhere else to go and I feel so sorry for her."
"I get it." I replied. "It definitely sucks, but maybe you can save this outfit for when my birthday rolls around." I shifted my hand slightly and ran my palm up and down her skin, opening her dress a little more.
Sherri nipped and nibbled at my neck, sensing my building arousal. "Up to you. I was going to go with sexy cheerleader for your birthday, but I can do evil witch instead." She then leaned up and planted a kiss on me. Just as she started to pull away, we heard a sound from the door.
"Shit! Shit! Shit! I'm such an idiot." Grace cried out. She had washed off her makeup, but her eyes were still red and puffy from crying. She was staring down at us and had a clear line of sight to my wife's exposed thigh and ass and her long nylon-covered leg. Our body positions gave away our actions and there was awkward silence for a few seconds before she continued.
"You guys had a whole romantic thing planned and I ruined it because I got drunk and can't drive! I'm so sorry." Tears were now running down her face again. "I'll get out of here and give you some privacy. I'm so sorry. Shit."
Sherri stood up and moved toward Grace, "Grace, honey, it's Okay. You're not going anywhere. You can't drive and Jason checked already, there are no other rooms."
"Fuck. It doesn't matter. I couldn't afford a room anyway. And if I go home, I'm sure my mother will give me lecture." A humorless laugh left her mouth. "Fucking perfect. 36 years old, separated, single mother, and somehow still going to get scolded by my mommy."
Sherri wrapped her up in her arms a bit tighter as she started to sob even more. "Bad enough I've fucked up my life, now I'm messing up yours. I'm so fucking cursed that even though I haven't had sex in close to a year, now I'm taking it away from others. I'm like a black hole of romance."
My wife continued to hug and stroke her friend's back in their embrace, "Honey, it's not your fault. Stop blaming yourself. You've been stronger than 90% of the women I know. Supporting yourself, digging out of debt, taking care of your son. You're an amazing, strong woman."
Grace's breath started to calm down as Sherri rubbed her back and started to stroke her long, red hair. I saw my wife glance over at me for a brief second before she continued with, "But not having sex? That's unacceptable. Turn around."
Grace pulled away with a confused look on her face, "What? Why?"
"Because the way I see it, you have two options. Lay out here and cry yourself to sleep on a pull-out sofa bed, or, " She turned her friend around and reached under her hair to the top of her zipper, "Let us show you just how attractive and sexy you are."
Now, to interrupt my own story, Sherri and I had been together for close to 15 years at that point in time. Over that time span, we had dabbled in a handful of threesomes. The first time was with her friend Linda after a party early in our relationship, another time was with a former female neighbor of mine. There was a professional escort in Las Vegas on my 30th birthday, a drunken fling with my ex, Tara, and finally a second romp with Linda when Sherri was pregnant a decade before. Until that moment in the hotel room, I thought those days were long gone. But as I watched Sherri slowly start to pull the zipper down, revealing Grace's nearly alabaster skin, my hopes and arousal were renewed.
"Sherri, I don't know. This isn't right." Grace was almost whispering as more of her ivory skin was revealed.
"Please. You and I both know how much you and Jay have flirted over the years. I know for a fact he thinks you're hot. And I also know that you would bang him in a heartbeat if you had the chance. So, I'm using my powers to grant your evil wish of having sex with my husband."
Sherri continued to unzip the dress to the base of Grace's spine before reaching back up and pushing the collar and sleeves down her body. I watched as the dress fell to her hips and I got my first look at Grace's small tits encased in a basic beige bra. Her waist was tiny, and I could see a pair of matching panties just showing above the deep green dress sitting at her hips.
"No. We can't. It's not right. You're married and a woman. I can't. It's like a sin or evil or bad or something."
Sherri then spun her back around by her shoulders, so the women were facing each other once again. Her red lips curled into a smile as she stared into the ginger's eyes. "Evil? Well, if it's evil, you can blame me, then. After all, I am the evil sorceress giving a princess to a pirate."
With those words, she pushed the dress down over Grace's full ass and let it puddle at her feet. Grace had on a pair of unappealing "granny panties" that matched her nondescript bra. Her body language showed her nervousness as she seemingly squirmed in shame.
"Sherri, I'm not sure. Should we?"
"That's enough! Jay, get your ass in the bedroom. And you, " SMACK, my wife gave her friend a slap on the ass, "will do as the evil queen commands."
I nearly leaped off the couch, stunned at what was happening but doing everything I could, not to fuck it up (especially mentioning to my wife that she was starting to mix up her evil Disney characters.) I went to the bathroom, quickly brushed my teeth and got a little blue pill out of my valise. I would sometimes use a "boost" when Sherri and I were away like this and thought this was the perfect situation to use one.
I went back into the bedroom to see my wife standing by the bed with Grace standing by her. "Unzip me, princess." She directed.
Our friend did as she was told and unzipped my wife's long black gown. The sound of the zipper seemed loud in the silence of the hotel room. Sherri shrugged the dress off her shoulders and arms to reveal a black push-up bra that showcased her tits. Grace continued to pull the tight garment down Sherri's body until she had to pull it over her hips. The lace of the garter belt appeared for the second time that night and the dress fell to the ground to show the strip of purple and long black stockings.
I was stunned looking at the difference between the two women as they stood so closely together. Sherri stood tall with her sorceress makeup and black lingerie standing out against her skin. Her legs looked long and sultry in the stockings and her shaved pussy was evident in her minuscule panties. Her chest was pushed up in her lacy bra and her lips shone with glossy red lipstick.
Grace, alternatively, was less confident. She seemed to be slumping, attempting to hide her exposed body. Her underwear was beige, nondescript and almost blended into her skin tone. Her hair was long and curly but was now partially covering her face. Sherri turned to face her friend, then gently and caringly brushed the loose hairs from her face.
"Honey, it's Okay. We don't have to do this. I don't want you to do anything you don't want to do. But, if anyone deserves a guilt-free night, it's you. And, " she added with a smirk, "You can always say I put an evil spell on you. After all, you were the one who said you were cursed. Isn't this how you break an evil witch's curse?"
I watched Grace absorb what my wife had said, before she looked up with a spark in her eye. "Fuck it. It's been a shit year. Literally can't get any worse. So, why the fuck not? If nothing else I'll know that for once, I'm having more fun than that dickhead Andy."
"That's the spirit" said Sherri, "Now, let's see what you have under there. Turn around." When her friend turned, Sherri unclasped the redhead's bra and let it slide off. Grace turned back around to show her small, bare tits, pert nipples and areola so pale and pink that they almost faded into her natural skin color. Without prompting, she reached down to her hips and slid her underwear down revealing a patch of red pubic hair that matched the flaming color on her head. Her bush was trimmed at the edges, but full and I found myself staring at my first view of a natural redhead. She saw me staring and moved to cover herself.
"I'm sorry , I haven't exactly worried about , down there. Nobody really gets to see lately."
"Oh, stop that crap." Sherri said, pushing her hands aside. "He's staring because he thinks it's hot. Right babe?"
"Definitely. Holy fuck, Grace. Your body is amazing. Andy's a moron. Just saying'."
I watched as my wife started to run her fingers through her friend's lush pubic hair while her other hand started to caress one of her tits. I heard Grace gasp when she felt fingers slide up and down her pussy lips as she shifted her hips to the sensations. Sherri's hand continued to stroke her friend and she used her other one to turn Grace's head toward her. She licked her friend's pale lips with her tongue before giving her a gentle kiss. She continued to stroke and gently kiss her until finally her tongue was met with Grace's. The two women kissed slowly and romantically, while Sherri's fingers continued their dance. Grace was slowly spreading her legs giving my wife better access to her pussy. Her free hand seemed to be moving up and down Sherri's body attempting to keep her balance. As her hand reached Sherri's lace covered tit, she worked it into the cup attempting to release it. Sherri pulled back for moment, reached behind her back, and unsnapped her bra, wriggling out and letting it fall to the floor. Her tits fell out with a bounce showing us that her nipples were erect with arousal. Grace grabbed and lifted her friend's tit feeling its heft and weight in her palm.
They pulled each other closer and I watched as their naked tits pressed against each other while they continued to kiss. Sherri worked her fingers back down to Grace's ginger pussy and began to strum along her slit. Grace gyrated her pelvis against the fluttering fingers that were flicking her clit. My cock swelled as the two friends kissed harder and deeper and Sherri's fingers pressed into her friend's pussy. It didn't take long before Grace's head rolled back and she was gasping for air. She gripped Sherri's wrist and held it in place against her pussy as an orgasm rolled over her. Her gasps and moans filled the quiet room as she bucked against the invading fingers.
When she finally stopped moving, I could see that her pale skin had flushed pink and beads of sweat had formed on her forehead. My wife pulled her fingers away and dipped one between her lips, licking Grace's juices off.
"Now, let me grant you your next wish, and get you into bed so you and Jay can have some fun."
As Grace gingerly climbed onto the bed, I stripped off my remaining clothes and settled my head on the pillows, while Sherri pulled down her panties and crawled in next to Grace. She was still clad in her black stockings and garter belt with her own pussy now exposed.
"He looks ready, but I'm thinking one of us should make sure. Do you want to get him even harder or should I?" my wife asked.
"You do it. I want to watch first."
Sherri smiled up at us both and turned her body on the bed so that her head was level with my crotch. I watched in awe as her red lips slid over the head of my cock. She kept only my head sealed between her lips as her tongue swirled around the sensitive skin. She pulled up and licked around rim again before taking me back in her mouth. She started to suck this time while she coated my cock with saliva. As my cock swelled and pulsed in my wife's mouth, I opened my eyes to see Grace's eyes glued to the scene while she stroked up and down Sherri's nylon covered legs.
Sherri opened her eyes and looked up at me with her mouth still full of my cock. I watched her give me a sensual wink and open her legs wider, inviting Grace to increase her motions. Her friend took the hint and shifted her body so that she could run her hands further up to Sherri's bare thighs. I watched as she moved her hands higher and just as she made contact my wife's shaved pussy, Sherri plunged her mouth down taking my entire cock into her mouth and throat. Her head bobbed up and down faster, sucking and licking me as her friend fingered her pussy. I felt my cock start to swell and I reached down to grip her short hair. Just when I thought I was going to explode, Sherri pulled off my cock with a wet "Pop".
"Hmm. I think you're ready, but I don't want you to come yet. I think Grace needs some of that, but not in her mouth." Sherri shifted again on the bed giving Grace and me room to get closer to each other. "What's your favorite position, honey? How do you want him?"
"I think I want him on top of me." Grace replied. "But, are you sure this is Okay? I mean, "
"We're Way past Okay. Lay down now, princess."
Grace settled into the pillows and spread her legs with her knees bent outward. I was still in shock, staring at this hot MILF, with her red hair spread over the pillows, her pink nipples standing hard from her pale skin and her deep red bush framing her wet pussy lips. As I moved over her, I felt my wife grab my shaft and start to run it up and down her friend's slit coating me in her juices.
"Here. Let me help you. It's the least I can do."
She continued to lubricate my cock with Grace's juices until she positioned my head at the entrance to her pussy. She lined me up and I pushed forward but Grace's pussy, while wet, was incredibly tight. I felt her body jolt away and heard a small grunt.
"Go slow, babe. She hasn't had anyone in her for a long time. And you" she added, looking at her friend, "just relax and enjoy."
I slowly pushed forward and felt her pussy open a bit more for me. I stayed still before pulling back leaving only my head inside her, waited again, then pushed forward. Again, while still tight, her pussy was slowly opening up for me. I repeated the action until I felt her lips gripping the head of my cock and slid forward again. There was less resistance now and her juices were coating my shaft.
While I slowly fucked her friend, my wife had moved up and started licking her small tits and nipples. Grace had her hands pulling my wife's mouth tighter against her tits as I increased the tempo of my thrusting.
"How's it feel, baby?" Sherri asked between licks.
"She's so fucking tight. Holy shit." I moaned back.
"I was talking to Her, but that's good to know" she chuckled.
"Oh, shit, it feels so good. I feel so full. So good." Grace added to the conversation.
My wife moved again and positioned herself so that her larger tits hung over her friend's mouth. She leaned down so that her nipple tickled her lips and kept brushing it back and forth.
"Sherri? What are you doing? I've never, "
"It's Okay, honey, just do what you think would feel good. I just want to feel your tongue on my tits." She leaned down a bit more and pressed her fleshy globe into Grace's mouth. Instinctively, Grace took it in and began to lick and suck. My wife was gripping her own tits and kept swinging them back and forth into her friend's mouth, getting her to lick and suck on alternating nipples.
Grace was thrashing trying to keep her mouth on Sherri's tits while I pistoned my cock in and out of her pussy. I pulled myself up so I was kneeling which changed the angle of my penetration. She moaned at the new sensation and shifted one of her legs up and out. Sherri noticed the movement and linked her elbow under Grace's knee and pulled her open more. The bed was now a contortion of limbs and flesh as all three of us tried to maintain our motion and contact.
I felt my balls slapping against Grace's ass I fucked her harder. Her moans were muffled by my wife's tit stuffed in her mouth as I felt her pussy start to grip me tighter. She used her free arm to push Sherri away as she started to shake and spasm against me.
"Fuck! I'm fucking coming. I'm coming!" Grace moaned as she rode her orgasm. The muscles of her pussy spasmed and tightened around my shaft as she shuddered through her climax. Sherri had gone back to gently licking her nipples, allowing her friend to enjoy the release. When she stopped moving, I pulled out of Grace and watched her juices leak out of her inflamed pussy lips. I was still rock hard as I watched her chest rise and fall attempting to get her breath back to normal. Even in the dim light, I could see her ivory skin covered in a sheen of sweat and her red bangs were plastered to her forehead. Her mound of red pubic hair was wet and matted against her skin while the mane on her head was wild and tousled on the pillow.
"Good to see you are still at full mast, baby. Now it's my turn to get pillaged." Sherri moved down on the bed and positioned herself on all fours with her ass up in the air and her torso hovering over Grace's stomach. Her tits hung down as she spread her legs wider for me. I repositioned and slid easily into her pussy from behind.
My cock was still covered in Grace's juices and Sherri was dripping, so I encountered no resistance as I slid and out of the familiar cunt. I watched as her bare pussy lips gripped my cock on every stroke and opened when I pushed forward. My wife's body rocked back and forth, and she dropped down slightly so her nipples were brushing against her friend's sweaty skin.
"That tickles!" Grace laughed. "Your boobs are brushing and tickling me!" We continued our motion with me gripping my wife's hips allowing me to slam into her harder, her tits dancing on Grace's stomach. I felt my balls start to tighten, preparing to release my load into my wife. She felt it too, because she pushed back and stopped my thrusting.
"I can tell you're getting close, baby. But there's something I want before you come."
She shifted a bit and sunk down so that her face was level with Grace's crimson snatch. Sherri took her tongue and licked her friend's slit from her ass to her clit. A sharp gasp erupted from our fair Merida and she unconvincingly groaned, "No. Sherri! I've never had a woman do that! You can't!"
Being the evil minx that she was, Maleficent ignored the pleas and simply buried her face into the awaiting pussy. Her tongue was buried in her friend's tunnel and with every thrust of my hips, the pressure and depth increased. For her part, Grace's head was thrashing back and forth as she pinched her own nipples. The sight of my wife's cropped, platinum hair buried in the pussy of another woman, while her ass rippled with every thrust of my hips, combined with a second MILF building to her latest orgasm was too much for me.
I moaned and dug my fingers into my wife's hips as my cock exploded into the depths of her pussy. Grace screamed out as she pulled Sherri's face in tighter, releasing into her waiting mouth. I was shocked that between the banging of the bed and Grace's screams, we didn't get a knock on the wall or a call from the hotel for excessive noise. Fortunately, nobody bothered us as I fell to the side of the bed, soaked with sweat. My cum dripped out of Sherri's cunt as she slithered her way out of Grace's splayed legs, coming face to face with her. Grace's eyes fluttered open to see a pair of deep blue eyes staring into her own green ones.
"Here" Sherri whispered. "Taste yourself on me." With that she pulled our little innocent princess to her own mouth and wrestled with her tongue. Grace could only moan in compliance as she returned the passionate kiss. As we all calmed down, we each left the bed and went to restroom one-by-one. Sherri emerged with her evil sorceress makeup removed and her stockings gone. When Grace came out, she looked tired yet satisfied with her hair in a ponytail as she crawled over me to the middle of the bed. I was the last to leave and return to the bed, having cleaned up myself a bit. When I returned, both women were sleeping soundly, covered only by the white hotel sheet. I climbed into the bed and pulled the blanket up, drifting off myself.
Somewhere in the night, bodies had shifted, and my arms were wrapped around the warm skin of our guest. My cock was pressed against her full, fleshy ass and found its way between her cheeks as I subconsciously hardened. Grace started to grind against me in response and shifted until my cock was pressing against the entrance of her pussy. I moved forward and slid in, much more easily this time. We spooned as we rocked back and forth, a slower more determined fuck than previously in the night. Our motion eventually woke up my wife who rolled over to face her friend.
I couldn't see what was happening, but I felt Sherri's hand sliding over her friend's clit and my shaft where we were joined.
"Naughty girl." My wife whispered. "Fucking him while I was asleep?"
"I'm sorry. We just, "
"It's Okay, honey. Does it feel good? My husband's cock in you?"
"Yes" she groaned. "Feels so good."
"Can he come inside you? Do you want to feel his cum in you?"
"Yes, yes, I want to feel it. Please Jay. Come in me."
"Is it safe?" Sherri asked. "Can he fill your hot pussy with cum?"
"Yes. It's safe. Please. Please fill me, Jay."
For the second time that night, my cock released a load into a hot pussy. I felt wave after wave shoot into Grace and then my own cum sloshing around my cock as I kept thrusting. The combination of my climax and my wife's fingers did the trick and Grace began to shake and shudder again. Her orgasm made the muscles of her pussy contract, squeeze around my cock, and milk the last of my seed from me. A long, low moan escaped her lips as her entire body stiffened, then went limp. I pulled out of her, allowing our juices to flow out to the sheets below. Sherri was gently stroking her friend's sweaty forehead while her eyes fluttered in the aftershock of her climax. This time, there was no encore to our activity. We each dozed off covered in sweat and sex.
One thing about a late night/all night drinking and sex session is that morning always comes quickly. Also, no matter how well you think you've closed the curtains, it is guaranteed that the one burst of bright sunlight will hit you in the eyes as you attempt to stay in dreamland. This was the case as I woke up with a line of a sunbeam shining across my face. I noticed there was more room in the bed, and I could hear movement in the bathroom. Stirring slightly, I could see that Sherri was still curled up with her head under a pillow, which meant that Grace must have been the one in the bathroom. When she emerged, I saw that she was dressed back in her jeans and top from the day before. She was obviously trying to gather her various garments and costume pieces from around the room without waking us.
"Hmm, " I heard next to me in the bed. "Are you leaving already?"
"Yeah. I have to get home to Daniel and my mother. I texted her last night, but I'm sure she's worried."
"You Okay? With everything?" my wife asked.
Grace sat on the corner of the bed as she answered, "Okay? I'm great. I'll be honest, I never thought I would do something like that, but yeah, it was definitely fun. I may have to hide an ice pack you know where though. I don't think my puss has gotten that much action in years. But seriously , thank you both. You won't , uh , tell anyone, right?"
"No, sorry." Sherri replied. "I intend to get on the school announcement system tomorrow and tell everyone that my pirate husband and I put a spell on an innocent Disney Princess and fucked her in our bed until she passed out. I'm sure that would go over great!"
Everyone chuckled as Grace gathered the last of her belongings and slipped out the door, allowing Sherri and me to drift back to sleep for a few more hours.
Epilogue:
About a six weeks later, I was flipping through the stack of holiday cards that had started to arrive at our house. I did a slight double-take when I saw the family Christmas picture of Grace, Daniel and Andy posed at a Christmas Tree farm complete with matching sweaters.
"Hey babe!" I called to the other room. "Did Grace and Andy get back together?"
"Yup. I guess so." She replied coming into the kitchen. "But I haven't really talked to her lately."
"Really? What's up with that?"
"No idea. But something tells me that our little after party freaked her out a bit. So, she got back with her husband, and everything is back to normal. She's probably avoiding me because I'm just a reminder of that whole night."
"Weird. Are you surprised at all?"
"Not really. When you think about it, it's the perfect ending. The Princess escaped the clutches of the Wicked Sorceress and Naughty Pirate, got back her Prince Charming and lived happily ever after."
Last Post-Holiday Party Celebration
After the guests leave, my wife and I celebrate together.
As was our annual tradition, my wife Sherri and I were preparing for a holiday party in our home. Every December, we would invite 30-40 friends to our house for an evening of food, games, carols, and lots (and lots) of cocktails. The house was decorated inside and out with lights and decorations for Christmas. We went above and beyond to create a fun holiday vibe for the event each year. We knew that people looked forward to the event and many people would avoid making other plans until we announced the date for our party. (What we didn't know that year was that it would be the LAST party we threw in our house for a long time because the world would shut down three short months later.)
On that night, though, the caterer was downstairs working on the food, the bartender was setting up the bar and cocktails and the servers were preparing for the guests. Our 17-year-old daughter had left for the night to stay at a friend's house. Sherri and I were up in our bedroom getting dressed in our "holiday festive" attire. I kept it simple: a pair of black slacks with a fun holiday sweater. Most of the men would dress in a similar style while Sherri and many of the other female guests tended to dress up a bit more.
I was sprawled out on the bed, watching the end of a college football game when Sherri emerged from the bathroom. In her late-40s, she was still stunning. Although she was a tall, slim blonde when we met a few decades earlier, time and age had changed her a bit. She was now a redhead, with a trendy short haircut that set off her green eyes. She was still tall (obviously) but had more curves than when we met. Her tits had filled out to a 36C, and her hips and ass were fuller thanks to the birth of our daughter. Pilates and working out kept her body firm, however, so to me she was just as perfect 20+ years later.
Sherri was wearing a bright red, form-fitting wrap dress. It de-emphasized her chest but showed off her curvy hips and ass. She had a black sash wrapped around her waist as a makeshift belt and the sequins in it caught the light, giving it a shimmery effect. Her legs were covered in basic black hose, and she was perched on a pair of bright red Jimmy Choo heels. She was still flitting around the room, putting on jewelry and tweaking her look for the night.
"You look amazing" I called out from the bed.
"Thank you honey!" she called back.
The game ended and I got up, stretched, and decided to go downstairs to see if any of the staff had any questions before the guests started arriving.
"I'm heading downstairs" I said, walking toward the door.
"Wait" Sherri called out. "I need your opinion on one thing!"
I turned around and Sherri stepped out of the bathroom. She did a quick spin to show me her entire holiday outfit. "Do you like?"
"Definitely, babe. You look awesome."
"What about this?" she asked.
She then reached down to the hem of her dress and parted the bottom of the wrap, lifting it to her waist. For the first time I saw that she wasn't wearing her usual pantyhose or Spandex, but a pair of thigh-high stockings. She lifted her dress up so I could see the exposed skin on her upper legs which led to a red satin G-string with more sparkles and glitter on it for the holiday. She gave a quick spin to show her exposed ass before dropping everything back into place as she slipped back into the bathroom and closed the door.
At this point, I should probably explain my surprise. Sherri and I have been together for over 20 years and married for 15 of them. I've shared some of our sexual adventures from when we were younger and even a few sexy traditions more recently (like our Halloween tryst I wrote about one year.). Like any marriage, we've had some rough spots. After the birth of our daughter, we went through a LONG sexual dry spell.
As we've gotten older, Sherri is less adventurous and more reserved. Like many 40-something women, her body has changed, and she is not as confident as she once was. (I still find her incredibly sexy and attractive.) I sometimes see flashes of the "old Sherri" come out again - but always in the privacy of our bedroom or a hotel. The best is still when she has had a few drinks and is feeling sexy. Then, I get to experience the "dirty Sherri" who can be positively raunchy both in language and behavior. Seeing one of these flashes on a night when our house was going to be full of our best friends was a big surprise.
Over the next few hours our house was filled with revelers, and everyone enjoyed themselves eating, drinking, singing and generally celebrating the holidays. Throughout the night, I found myself staring at wife's ass knowing what she was hiding underneath her festive attire. I was convinced that she knew I was looking, based on the extra wiggle she seemed to be putting into her hips all night.
By 11:00, most of the guests had started filtering out, but a few lingered for some late cocktails. Six of us were still gathered in the living room, with our attention focused on our friend Molly. Molly was a robust full-blooded Italian who was always a great party guest because she may be the most social person I have ever met in my life. Molly never stops talking and has a story about everything. The other interesting characteristics about Molly are her enormous tits. While she didn't do anything to focus people's attention on them, it couldn't be helped.
No matter what she was wearing, Molly's boobs stood out and when she laughed (as she often did) they would shake and jiggle. The final couple left, leaving Sherri and me with only Molly and her husband, Tim. Sherri was curled up next to me on a sofa with her shoes kicked off and was fidgety and unsettled. She kept yawning and commenting on the late hour and on the fact that the snow was starting to fall harder outside. Molly didn't let that stop her as she kept talking, laughing and jiggling. As I kept drinking, my ability to keep my eyes from her chest decreased exponentially.
At one point during the conversation, Sherri even commented on how I couldn't take my eyes off Molly's boobs. Molly simply laughed harder and held them up even more. Finally, just around midnight, Tim mentioned that the snow was really starting to come down and that they should head out. With Molly, even the goodbye took nearly 15 minutes by the time we finally closed the door behind them.
We watched out the window as their car pulled out of our driveway on to the snow-covered street. As they pulled away, Sherri spoke for the first time, "Fuck. I thought they'd never leave. Why did you keep offering them drinks?"
"I was being polite!" I replied. "Plus, once Molly starts talking, there's no stopping her. I figured we might as well drink!"
"Fucking hell!" Sherri started walking back toward the living room. "Well then make me one more drink and meet me back in here."
I went to the kitchen, poured us each a glass of brandy, and returned to the living room. Sherri had turned off all the lights, so the room was lit only by the Christmas tree and the holiday lights and streetlamps from outside. The room shimmered with the Christmas lights and the filtered lights through the falling snow. She had settled back on the couch, but this time she had unwrapped her dress giving me a full view of her semi-naked body underneath. Her stocking covered feet were sitting up on the couch with her stockings still high up on her thighs. They were followed by a pale expanse of skin to the slight g-string covering her sex. For the first time, I saw the matching red push-up bra that supported her c-cup tits. I handed her a glass of brandy, lifted her feet, and sat down, replacing her feet on my lap.
There was still a mix of Christmas jazz music playing in the house as we sipped our drinks and watched the snow fall harder outside the window. It could have a scene out of a Hallmark movie, were it not for the half naked woman lounging on the couch next to me.
"So let me get this straight" Sherri said. "Our teenage daughter is gone for the night, you knew I was wearing all this under my dress, I did everything short of grabbing your cock to flirt with you - and yet, your brain said, 'Let me keep people here longer'?"
"I have no defense" I laughed in response. "Except Molly's boobs were very distracting."
Sherri gave me a gentle kick with her foot saying, "You could have been sucking my tits an hour ago if you could have taken a hint."
Her use of the word "tits" clued me in that she had consumed a few drinks and was going to be a bit more lusty that night.
"Fuck, babe." She continued. "I've been so horny all night, all I wanted to do was get everyone out of here and go upstairs with you."
As she spoke, Sherri was rubbing her stocking-clad feet over my crotch. I could see her toes were painted in a holiday red with some rhinestones and designs on them as she rubbed them up and down my expanding length. I felt myself getting harder even though, in general, I'm not into feet! I actually think feet are kind of gross, but in the moment, with my normally conservative wife displaying herself in front of me and talking dirty, this strange sensation was working on me. Sherri could tell I was getting aroused.
"Do you like that babe? You like my feet rubbing your cock until it's nice and hard?"
"Yeah, actually it feels good."
"I know you love when I wear stockings, especially with heels, but I didn't think you'd like playing with my feet." She was now using both of her feet to run up and down the length of my shaft through my pants.
"I usually don't, but it feels really good."
"Maybe you should take off those pants so they're not in the way." Following her suggestion, I removed my shoes, socks, pants and sweater, leaving me only in boxers. I sat back down, and Sherri was able to get one foot under my shaft while keeping the toes of her other foot bent over the top. She formed an odd tunnel and began to stroke my cock more. The sensations were so different than when she would use her hand or even her mouth on me. Even the movement of her toes sent new sensations through me.
"Could I make you come like this?" she asked.
"Probably" I moaned.
"If I took off those boxers and milked your cock with my feet? Could I get you to shoot a hot load all over my toes and my stockings?"
"Yeah, babe. You definitely could."
Sherri abruptly pulled her feet away saying, "Too bad, honey. I have other plans for that cock tonight."
I let out a frustrated moan as she shifted on the couch. She put her drink down, lifted her hips, and slid her G-string down. I got my first look at my second surprise of the night. Sherri had completely shaved her pussy, something I hadn't seen in years. Her lips were puffy and completely exposed as she slithered out of her panties and spread her legs.
"Right now," she started, "I think you owe me for making me wait so long tonight. Especially after I showed you how ready I was and what I was wearing under this." Sherri planted one foot on the ground and lifted the other on to sofa, spreading her legs for me. I slid down the sofa and positioned myself, so I had access to her pussy.
Normally, I would kiss and tease around her sex before beginning any oral techniques. This time, I didn't waste any time with preliminaries. Instead, I licked the length of her exposed slit tasting her juices. I repeatedly licked from the bottom of her opening, up between her lips and ended with a flick on her clit. Sherri had one hand on my head, with her fingers wrapped in my hair, pulling me in more.
"Jay, that feels so good. Don't stop." She moaned. Following instructions, I continued with the long slow licks up her slit. As I continued, Sherri was moving her hips in a short up and down motion to increase her stimulation. I could taste and feel her juices flowing more as her arousal increased.
Sherri shifted down slightly, and I started a new technique. This time, I focused my tongue on her clit and started gently spelling out different words and phrases on her clit. After working my way through the alphabet, I started with different seasonal phrases and words, keeping in the spirit of the season. I could tell that Sherri was enjoying the new stimulation as her moans increased and she pulled my face in tighter.
"That's it, baby, lick my pussy. You're gonna make me come. Don't stop. Please, it feels so good."
When I was somewhere between "Jingle Bells" and "Rudolph" I made one final change that I knew would send her over the edge. I pursed my lips and formed a tight seal around her clit. Sucking in slightly, I started to quickly lick her clit in short strong strokes.
"Yes, Jay, yes! Faster! Lick me faster! I'm going to come!"
Breathing through my nose, I increased the suction and speed on her clit, sending Sherri over the edge. I felt her inner thighs tense and her back arched off the sofa. I did my best to keep my mouth on her pussy as she thrashed on the couch. As she rolled through her first orgasm, I was able to regain control and locked down on her clit again. A second orgasm ripped through her and I felt her juices flow out of her pussy and on to my mouth and chin. Sherri pushed my face away as she writhed and bucked her way through the dual orgasms.
As she regained her breath, I sat back up and took a long sip of my drink to recover from my oral efforts. Sherri had one hand resting on her sensitive pussy and the other squeezing one tit that had popped out of her bra. I could see her nipple was stiff and her chest was flushed.
"Hand me my drink" she requested. I handed her the glass and she took a big sip before continuing. "I think you need to come upstairs and fuck your wife."
Sherri stood up, not bothering to cover any of her exposed body. Her dress had fallen completely open as she reached down to pick up her heels to carry upstairs. I followed her up the stairs, watching her ass sway under her dress as I tried to adjust my own erection in my boxers. When we got into our bedroom, Sherri shimmied off her dress then reached behind and undid her bra. I took off my boxers and saw her starting to sit on the bed to remove her stockings.
"Stop" I said. She paused and looked up at me. "Put your heels back on and stand up."
I wasn't leaving any room for discussion or debate, so Sherri followed my instructions. She put her heels back on and stood up, awaiting more direction. I reached on to the bed and pulled over one of the Many decorative pillows we had placed there and moved it closer to the edge.
"Bend over. Chest on the pillow." Sherri bent at her waist and leaned over the bed on to the pillow, with her feet planted on the floor and her ass up in the air. "Now, spread your legs."
Sherri shifted her legs wider and opened her sex to me. The heels had her at a height that lined up perfectly with my erect cock and I could see that the muscles in her calves and legs were stretching with her position. I lined myself up with her opening and started to press forward when she spoke up, "Go in the drawer and get some lube. It will make it easier and better, babe."
I pulled back and opened the bottom drawer of the nightstand where we kept all of our "bedroom supplies." There was a selection of lubricants (yes, they do make sex better, especially as you get older), some cock rings, and a decent collection of about 10 different toys we sometimes used in bed. I grabbed our favorite lube and generously spread it over my erection. I squeezed some more out of the tube and worked my slippery fingers around Sherri's pussy lips before working two fingers inside her. Feeling that we were both ready, I lined my cock back up and pressed forward.
With the lubricant, there was little resistance and my length slid easily into my wife. I felt the warmth and grip around my shaft like a soft glove. Sherri let out a moan as she felt my hips push all the way forward and make contact with her ass, signifying that I was all the way in. We both paused and adjusted slightly as I grabbed her hips with both hands. Once our footing was secure, I pulled back and plunged back into her soft folds again.
"Fuck, Jason. That's it. I've wanted to get fucked all night. Fuck me, baby." Now that she was fully aroused, her language followed suit.
Tightening my grip on her hips, I started to slam in and out of my wife's hot tunnel. With every push forward, I was able to watch her ass thrust forward and jiggle from the motions. Because of my level of arousal and the position we were in, I knew I wouldn't last long before coming. I tried to slow my pace, withdrawing my cock until the head was just spreading her cunt lips before pushing back in until my balls made contact with her skin.
Sherri was writhing and moaning at the slower tempo, "Please, fuck me harder, I need to feel you come."
"Nope, I want this to last. I don't want to come, yet."
"Please, Jay. It feels so good when you slam into me. The pillow is rubbing on my tits and feels crazy hot. I want to feel your cock explode in me, please, please." Sherri was begging now, and she reached back and tried to pull me into her.
Against my instincts, I did as she said and increased my pace. The room was filled with the scent of her arousal and the sounds of skin slapping against skin. Sherri's ass was rippling with every thrust as I used her hips to slam into her harder and faster.
"That's it. Faster! Harder!" she cried out.
I continued my motions and felt my balls begin to surge, knowing I was about to come. I pulled one hand back and swung it down, slapping her hard on one ass cheek. Sherri screamed and I felt her pussy tighten its grip around me. A second slap in the same spot sent her over the edge for the second time that night. Her pussy spasmed and clenched around my cock as I buried it inside her and the first spurt of cum shot into her. I didn't stop the motions as I continued to come, and Sherri rode out her orgasm. When I finally stopped coming and Sherri wound down her climax, I pulled my cock out with a trail of cum and fluids flowing out of her wide-spread pussy, down her inner thighs.
Sherri didn't move at first except for her deep breaths and an occasional spasm that seemed to jerk her whole body. It was a minute or so before she spoke up and said, "Help me up, please."
I grabbed her by the waist and helped her stand back up. Her hair was a sweaty mess, and her tits were a bit red from the friction against the pillow.
"I'm going to get ready for bed, now." she said with a kiss on the cheek. "If you're going downstairs, can you grab me a nightcap?"
I grabbed a towel, wiped myself off a bit, pulled on my boxers and went downstairs. All the Christmas lights were still on, glowing through the house and the snow was picking up outside. I grabbed us a few bottles of water and a final drink each that I balanced in my hands to go back upstairs.
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.
"Hmm" 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 tits. 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, "Okay, 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 cock 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 Okay?" 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 Okay?"
"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 Okay?" 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 cock 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 Okay?"
"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.