21 comments/ 143915 views/ 50 favorites Valentine's Day Threesome By: silkstockingslover NOTE 1: This story was written for a fan. Hope you enjoy, Dani!!! NOTE 2: Thanks to Estragon for his copy editing. NOTE 3: This is a 2012 Valentine's Day Contest story...so please vote. * Valentine's Day Threesome It started so innocently, like I things often do, I suppose. Linda and I were having our monthly visit at our usual Wednesday coffeehouse, when our conversation veered to her new relationship. "He is so amazing," Linda glowed, continuing, "I have never met anyone like him." I was thrilled for her. It had been a while since I had seen her even remotely happy, never mind ecstatic. "I am so happy for you." In the next five minutes I learned everything there was to know about him. She finished, by adding, "And he is insatiable in the bedroom." Frank discussion of our sex lives was nothing new, when there was something to talk about. "He is, is he?" I queried. "Fuck, yeah," she smiled. "For a forty year old he still fucks like he's twenty. Every time I think he has shot his last load in me or on me, he shoves his cock back in my mouth and we are back at it. After a night with him my mouth, pussy and ass are aching." "Ass?" I questioned. That's something both of us have always believed was a one way passage. "I know, I know," Linda replied, reading my mind, "but you got to do, what you got to do to keep your man." "Really?" I asked, my look of disbelief impossible to hide. She smiled, "Don't judge, Dani, until you've tried it. I was surprised at how good it eventually felt. I actually came from getting my ass reamed." "Ass reamed? Really, Linda, you can't be serious! What has gotten into you?" She joked. "Lorenzo's cock, over and over. Plus, I am forty. Finding a good man at our age is like finding a needle in the haystack, so I opened myself up sexually and not only am I keeping my man, I have never been so sexually satisfied in my life." "OK, OK," I said, admitting defeat, and deciding to have fun with it, like we usually did about everything. "Hey, I have not seen you this happy since...well I can't remember when. So if taking a cock up your ass is what it takes to make you happy, I say ass-fuck away." "Now you are just making it sound dirty," Linda replied, with a smile. "Slut." "Cat-loving loner," she retaliated. "Hey, cats are cute and never leave me," I defended. "True, but when was the last time you got laid?" "Too long," I sighed, "maybe I am the cat-woman." "Well I do have a proposition for you." Linda smiled, provocatively. "This sounds interesting," I replied, instantly curious. "Lorenzo's fantasy is a threesome," my best friend announced. Silence lingered as I processed this information and concluded she was implying I be the third. "Are you serious?" "Yes. At first I didn't love the idea, but concluded if it is going to happen, I want to control it." "Oh," was all I could say. My best friend of twenty years was suggesting a threesome with her boyfriend, a guy I had never met. It was so surreal; I was literally at a loss for words, not something that usually happens to me. Silence again lingered, before she asked, tentatively. "So, is that a yes?" "I don't know," I paused, a mixture of excitement, trepidation and nervousness tossing and turning in my brain. I hadn't been laid in a while and this was a sure thing. Yet, there is no going back after a threesome with your best friend...it is kind of like dating a co-worker; if things go astray it forever changes the relationship. "Trust me," Linda purred, her smile the troubling one that landed us in loads of fun situations back in the day. Without any real thought, I answered, "Fuck it. Why not? I'm in." Linda was thrilled. "Awesome. I will make the arrangements ASAP. I should warn you." Suddenly worried, I asked cautiously. "What is it?" She leaned in and whispered, "He has a fucking huge cock." "How big is big?" I asked, a bit worried, a bit curious. "Almost ten," Linda informed me proudly. "And you took that in your ass?" I gasped. "Not all of it...originally. I'm not a slut." "Oh God no, you are not a slut," I mocked, having been the audience for her very detailed and lengthy accounts of her numerous sexual conquests. "Takes one to know one," she countered. "Touché." "Oh and there is one more thing," Linda added, the house of cards seeming to keep getting higher and higher. "What?" I asked. "He's Italian," she revealed. "Oh no!" I mocked again, "the deal's off." "I'm just saying he is not really good with the whole social graces thing in the bedroom. He is the man and I am the woman and that is very clear." "Hmmmmm," I purred, "A rugged man." "A dominant man," Linda corrected. "Well, at least he won't be asking for directions," I joked. "Definitely not. He will be giving them." "Still in," I replied, looking more and more forward to the event. "Wait, you must have a picture of him." She reached for her phone and handed it to me. He was in a suit and tie and was very good looking. "Oh my, he is a handsome one. He doesn't look 40." She smiled, clearly happy with my assessment. "And he doesn't fuck like he is 40 either." "Together we can wear him out," I confidently predicted. "We'll see," Linda replied, "I haven't been able to yet." "So when do you want to do this little rendezvous?" "Valentine's Day," she replied. "Really?" "Really, really. It will be a great present for Lorenzo and you won't be alone or on some disastrous blind date." "True." I pondered, realizing it was actually a good day. The last two Valentine's Days had been utterly fucking depressing. "Ok, Valentine's Day it is." "Awesome," Linda said, reaching over and giving me a hug, which she had done thousands of times, yet this time it seemed different. "So, here is the plan. Lorenzo and I are going out for supper at The Brooklyn and then to a Broadway show and lastly to Duelling Pianos for a night-cap, before going to the hotel room we rented at the La Capri. I have booked a table for you at The Brooklyn, and got you a ticket to the show already." "Wow, you have really put some thought in this, haven't you?" I replied, impressed before a sudden realization hit. "Wait. How did you know I was going to say yes?" Linda smiled, "I'm your best friend, silly." We went through the logistics and times before finally going our separate ways. That night, I fucked myself with my biggest dildo imagining the night that lay ahead. A few days later...Valentine's Day 2012.... Through the days that followed, I flipped back and forth between going through with this crazy idea and backing out. But in the end, I decided to do it for two reasons: 1. I desperately needed to get laid...my insides were shrivelling up from lack of use, quite frankly. 2. I didn't want to back out on Linda. I had always followed along during her many crazy adventures in high school, college and adulthood; there was no reason to back down now. I dressed up for the part. I wore a red lace bra and matching thong, mocha thigh highs, four-inch heels and a black cocktail dress that made my blonde hair really stand out. On the outside I looked elegant and proper, while underneath I was dressed to tease and please. A supper for one on Valentine's Day would usually be a humiliating ordeal, but knowing what lay ahead made it tolerable. I had two glasses of wine and flirted shamefully with the waiter, who was young enough to be my child. He flirted back, which only enhanced my desire to be fucked. The play was an amazing local production of Guys and Dolls. I had a great seat at the front, but could not see Linda or Lorenzo anywhere. I also had two more glasses of wine. Any last minutes doubts faded as the wine lubricated my need to get laid. I made it to Duelling Pianos a little after midnight, and Linda and Lorenzo were at a table with a bottle of wine. I sat at the bar, in clear view of the couple, and made sure to position myself so they both got a good long look at my silk stocking-clad legs. A fifth glass of wine went down smoothly and I ordered a sixth when my best friend, dressed in a fire engine red cocktail dress, black pantyhose or stockings and five-inch heels, sauntered over and sat beside me. "Fancy meeting a girl like you in a place like this," she greeted with a playful smile. "I bet you say that to all the girls you want to fuck your boyfriend," I quipped back. "So you are still game, I see." "Six glasses of wine worth, and if I don't fuck your boyfriend, I will probably end up fucking every guy here." "Even that old dude checking you out?" "Sure, my pussy doesn't care who fucks it right now. It just needs to be fucked, hard." "Fuck Dani, you are getting me wet. Follow me," Linda said, grabbing my hand. "By the way, for tonight your name is Brittany." "Really? Brittany? All Brittanys I know are mindless bimbos," I protested. "Exactly what you are tonight," Linda replied. The statement confused me, but I eagerly followed her and was soon at the table with her even more handsome in real life boyfriend. Linda said, "Lorenzo, this is Brittany." Lorenzo smiled, took my hand, and said, "Nice to meet you, Brittany." "Likewise," I replied, trying to sound sexy. Linda explained, "Lorenzo, this is your Valentine's Day present." "What is?" he asked, confused. "She is," Linda said, pointing to me. I smiled, attempting to be provocative. "She said your fantasy is a threesome and she offered me two hundred bucks to make that happen." He was speechless. Which I am guessing doesn't happen to him too often. Linda grabbed him by the hand and said, "Let's go back to our room." Lorenzo recovered quickly and took control. He stood up, tossed a hundred on the table, wrapped his arms around both of us, like some studly pimp, and led us out of the bar, across the street, and to the hotel. Once in the room, Linda opened the complimentary wine, poured us all a glass and, when handing me mine, ordered, her tone surprisingly dominant, "Do as I say, Dani." I nodded in agreement, confused by her tone, but horny nonetheless. Linda sat with her boyfriend on the couch and demanded, "Do a strip tease dance for us." I looked at her, surprised, but her don't-mess-me glare prevented any questioning and I began to dance for her, awkwardly. After a couple of minutes of staggers, I sauntered over to her and she unzipped me. Standing still, I allowed the dress to fall off me. "Nice," Lorenzo grunted. I smiled at the caveman compliment and spun around to continue my dance. I squeezed my breasts together and leaned forward, giving both a lengthy look at my 34b cleavage, although they were much smaller than Linda's large d-cup breasts. I spun around and in one quick flash unclasped my bra. Spinning back around, I tossed it at the couple. I sauntered over to Lorenzo, and trying to do my best Olivia Newton-John from Grease attitude at the end of the movie, I asked, "Can you help me out of these...stud?" He put his big strong hands on my hips and ruggedly pulled my thong down and off. I lifted my leg to Linda and Lorenzo ordered, "Keep the stockings on, slut." I flinched at being called a slut, but obeyed, surprised at the tingling down below. Linda stood up and demanded, "Unzip me." I stood up and slowly unzipped her dress, attempting to make it sexy. She allowed it to fall to the floor and instructed me, "Unclasp my bra." I obeyed, unleashing her massive and still stunningly firm breasts from their restrictive barrier. She turned around and her fully erect nipples were in full display. Although I'm not a lesbian, my mouth watered uncontrollably. She looked directly into my eyes and opened her legs, and demanded, "Get on your knees and take off my panties, slut." Her name-calling surprised me, but I again obeyed falling to my knees and again felt a tingle down below. My hands quivered slightly as I slowly pulled off her thin silk panties. I tried not to look, but like when you drive by an accident you always glimpse or gawk curious to see I don't know what, I took a quick peek at my best friend's vagina. It was completely shaved, unlike my trimmed pussy and it already had a slight shine to it. She noticed and asked, "Like what you see, dyke?" "W-w-what?" I stammered, looking up into her eyes. "You were salivating looking at my pussy. Obviously you are a dyke," she sneered, her smile a warning to not blow this. Being drunk and horny, I figured fuck it and continued to role play the slut she wanted me to be. "Your cunt looks delicious, ma'am." "Ma'am. I like that. Well why don't you find out?" she offered, falling onto the couch and spreading her thigh high covered legs. Already on my knees, I barely had to move to obey her suggestion. Moving between her legs, I paused. Not because I was suddenly having second thoughts, rather because I was suddenly feeling like a lesbian and wanted to please her. I wanted to lick her pussy. I wanted to get her off. I wanted to get him off too. I leaned forward and extended my tongue onto the pussy of my friend of over twenty years. The taste was subtle sweetness and I slowly licked, enjoying the pleasant taste. Within seconds of pleasing Linda, her moans began as did her dirty talk. "That's it slut. Eat my pussy." A couple of minutes later, she asked, "You love my cunt, don't you?" I moaned an affirmative reply, each lick getting me more addicted to her sweetness. She demanded, "Tell me how much you love my cunt, slut." I was surprised how turned on my pussy was by her demeaning treatment of me. Wanting to play her game and keep her happy, I looked up and answered, rather submissively, "I love your sweet cunt, it is so fucking delicious." "I have heard that before," she smiled at me and winked to Lorenzo. I watched her flirting until she demanded, "Well, get back at it, dyke." "Yes, ma'am," I replied and returned to pleasuring my best friend. Determined to get her off soon, my knees a bit sore, I slid a finger inside her very wet pussy and began licking her puffy lips faster and faster. Her breathing increased, and a couple of minutes later, sensing she was close, I added a second finger and began flicking her clit with my tongue. Each flick had her twitch and her breathing got heavier and heavier until the scream I was anticipating and working towards burst out of her. "Aaaaaaaahhhhhh, fuuuuuck,that is so fucking good. You are such a good little cunt-muncher." Oddly, I felt a chill of a thrill go up my spine at being called a good cunt-muncher. I felt giddy with excitement at pleasing her. I quit flicking her clit and moved to cleaning her pussy of the flood of juices I had caused. Once Linda had recovered from the orgasm, she stood up and instructed, "Wait here." "Yes, ma'am," I replied, remaining in my subservient position. I watched as she went over to her suitcase and I gasped when she pulled out a strap-on cock. A big strap-on cock. I watched in stunned silence as she put the strap-on on her body. Her devious smile, one I had seen so many times before, was this time aimed at me. Once on her, she walked over to me and asked, "Ready to get fucked, slut?" As my muddled mind tried to comprehend what my best friend wanted to do to me, my very needy pussy spoke for me. "Yes, ma'am, I am dying to feel your big cock in my cunt." Smiling, she ordered, "Get on the couch and spread your legs, bitch." Thrilled to be off my knees, I scurried onto the couch and eagerly opened my legs. I didn't care anymore who or what fucked me, as long as I was fucked hard. Linda moved between my legs and rubbed her plastic cock head up and down my already wet pussy lips...teasing me ruthlessly. I moaned, and pleaded, desperate to feel my pussy filled, "Shove that big cock in me." "Are you my slut?" my best friend asked. "Yes, dammit, now shove that big aaaaaaaaahhhhh fuck...." I agreed and demanded, before being rewarded with one big thrust that filled me completely. Her cock buried in me, she just sat there and I began to bounce back on the cock, literally fucking myself. She purred, "That's it slut, fuck yourself like the whore you are." I moaned in agreement as I began to fuck myself faster, the desire to orgasm overtaking my every thought and action. I bounced back, taking the whole cock inside my fiery hole, my ass bouncing onto my best friend's legs. Soon I was huffing and puffing and I screamed as I came all over my best friend's long fuck-toy. I quit fucking myself as I enjoyed the orgasm spreading through me and felt a hand slap my ass before Linda began fucking my still pulsating pussy. The sensation was enthralling and my heavy breathing continued. I looked up and saw Lorenzo, who had apparently filmed my first lesbian experience with a camcorder. It should have mortified me, yet somehow it only made the night hotter. I moaned into the camcorder, "When am I going to get your big cock, stud?" He promised, "Soon, slut, very soon." My orgasm long gone, Linda pulled her strap-on cock out of me and shoved it roughly in my mouth. She face-fucked my mouth demanding, "Clean your whore juice from my cock, slut." I had no choice as she violated my mouth with the toy. My juices tasted sweet, but the plastic toy was less than thrilling. Finally, she pulled out and before I even had time to close my mouth, I was staring at the biggest cock I had ever seen. Ten inches and thick; I stared at it like I was looking at a foreign object. His sexy Italian voice got me wet. He demanded, "Don't just stare at it, suck it like the fucking whore you are." I didn't need to be told twice. Again incredibly enjoying being treated like a slut, I leaned forward and engulfed my best friend's boyfriend's super-sized cock. He instantly moaned, "That's it cocksucker. Faster." I obeyed, bobbing up and down as fast as I could, eager to get his first load out of him. It wasn't a fancy blow job and I didn't do any of my feminine tricks, instead I just sucked and sucked like I was fucking him with my mouth. A few minutes of this hardcore sucking and I suddenly felt his hands on my head and he pumped his cock in and out furiously for a few seconds before coating my mouth with his cum. He kept pumping long after every drop of his cum had slid down my throat. Shockingly, his big cock stayed erect, unlike the last few men I had been with. He pulled out and lifted me up upside down and began licking my pussy. The blood rushed to my head, but the overpowering aggressiveness of Lorenzo and the unique position was exhilarating. I grabbed onto his legs and his erect missile was staring me in the face, so I did what any good, horny slut would do, I took it in my mouth. Although incredibly awkward, I slowly sucked on his big stick as he licked my pussy like a man does...random and lacking focus. After a couple of minutes of this unique position, he lowered me on the couch, sat down and ordered, "Straddle me, slut." Desperate to be fucked and feel his big cock in me, I didn't hesitate a second as I climbed on top of him and slowly lowered my pussy onto his stiff cock. Only half his cock was in me when he suddenly thrust up, filling me completely. I let out a scream, "Aaaaaaaaaaaah fuuuuuuuuuck." "Now get riding slut! We are not making love, we are fucking," he ordered. Obliging, his big cock filling me so completely, I began to ride his cock like one would ride a bucking horse. Each bounce down filled my pussy like it had never been filled before. It was only after a few minutes of bouncing on his delicious cock that I came. As I leaned forward, allowing the orgasm to spread through me, he began thrusting up into me, enhancing the orgasm, and I screamed, "Oh-oh-oh-oh-oh-fuck-yes-yes-yes-God." Valentine's Day Threesome As he continued thrusting, he shocked me as he said, "Dianne get the slut's ass ready." "Of course," my friend, who knew of my no-entry backdoor policy, replied, walking over to me, a thinner strap-on already around her waist. "No, I don't do anal," I began. Linda reached me and demanded, "Shut up slut." Lorenzo held me in place and shoved his tongue into my mouth as I felt cold lubrication between my ass cheeks. I whimpered into his mouth realizing my best friend was about to deflower my ass. I broke the kiss and begged, "Linda, please don't." Linda slapped my ass and ordered, "Tonight, I own you, slut. Don't you dare question me!" "W-w-what?" I stammered. "You heard me, slut," my friend replied, the tip of her strap-on cock now between my ass cheeks. "Beg me to fuck your ass, slut." Realizing my helplessness and somehow turned on by the humiliation I was currently feeling, I heard myself speak, "Please, fuck my ass, and take my anal cherry. Get it ready for your boyfriend's long, big cock." "Good girl," Linda purred, leaning forward and slowly penetrating my ass. Lorenzo went back to kissing me, I assume to distract me from the pain, and I moaned-screamed into his mouth as my best friend's cock slowly filled my ass. Once all the way in, she leaned forward and whispered in my ear, "You needed this baby, now lean back and enjoy." She nibbled on my ear, wiggled a bit with the toy in my ass, her boyfriend's cock still buried in me. As the pain began to fade, a subtle pleasure began to rise. Slowly she began to slide the thin cock in and out of my ass and much to my chagrin the feeling was amazing. Maybe it was the six glasses of wine, maybe it was the fact that it had been so long or maybe I really was the slut Linda had created, but soon I felt my ass backing up to meet each of Linda's thrusts. This continued for a few minutes until Linda suddenly pulled out of my ass. I moaned, "Nooooooo." I felt her hands spread my cheeks apart and her tongue licked my ass. The feeling was so bizarre and yet hot. She continued doing it as Lorenzo pulled his cock out of me and slowly moved from underneath me. A few seconds later, Linda quit licking my asshole and moved around to look into my eyes. She smiled, whispered into my ear, as her boyfriend's cock split my ass cheeks, "You are so beautiful, Dani." Lorenzo's cock began to penetrate my ass, as I moaned, my eyes wide. "Thaaaaaaank yooooou." She leaned in and kissed me passionately as her boyfriend's cock slowly filled my ass. Lorenzo's cock was a lot bigger than the strap-on Linda had just used on my ass, and the pain returned. Breaking the kiss, I whimpered and Linda comforted me, "Just relax, the pain is only temporary...what comes next is fucking amazing." "Kkkkkkkk," I moaned, not sure I believed her, Lorenzo's cock tearing me apart. Linda moved on the couch, opened her legs and ordered, "Lick my cunt, slut." I leaned forward to lick my best friend's pussy again as Lorenzo began to slowly slide his cock in and out of my ass. As promised, the pain did begin to subside and a feeling unlike any other began to emerge. A couple of minutes into my first real ass-fucking and I was moaning and screaming bloody murder, but in a good way. I was soon sucking on my best friend's clit with reckless abandon while Lorenzo's cock pumped in and out of my ass fast and hard. He never got his whole cock in me, but he filled me in a way I never could have imagined. I couldn't believe it, but I felt an orgasm building within me. Linda, somehow sensing I was close, moaned, "Come for me, slut. I want you to come having a cock deep in your tight ass." Moaning, I let go off Linda's clit, and screamed, "Oh God, yes, fuck my slut ass, make me your bitch." Lorenzo sped up the pace and my orgasm exploded through me, an orgasm more intense than any I had ever had in my life. It pulsed through me, refusing to leave, as Lorenzo continued his assault on my ass. Linda grabbed my head and pulled me back into her wet pussy and I eagerly lapped her juices, determined to get her off again. My orgasm still lingering, Lorenzo didn't slow down, and soon he grunted and I felt his seed fill my no-longer virgin ass. Seconds later, Linda screamed too and my ass was coated with her boyfriend's cum, and my face was coated with her juices. All spent, the three of us collapsed onto the couch, cum leaking out of my ass. After a few seconds of silence, Lorenzo demanded, "Linda, retrieve my cum." "Pardon?" she asked. "Clean your friend's ass," he ordered. "My friend?" she questioned. "Oh, I know this is not Brittany. You have a few pictures of her on your wall and one even says Dani and I. How oblivious do you think I am?" "Oh," she replied. "But, that doesn't mean I didn't love it," he smiled, kissing her. Breaking the kiss, he ordered, "Now go retrieve my cum." Without another word, my very strong, independent, best friend, submissively fell to her knees and sucked her boyfriend's cum out of my ass. It was surreal and fucking to think of her licking my ass, feeling her tongue in my gaping asshole. Once done, she gobbled his cock up whole and got his semi-erect tool fully stiff again. Once erect, she straddled him, both legs still on the floor, and devoured his cock between her wet pussy lips. I watched them fuck a marathon session. They switched positions over a dozen times and eventually he slid into her ass, filling all his massive cock inside that tight hole. Eventually he came, and as soon as he pulled out, without instruction, like the crazy animal I had become, I crawled between my best friend's legs and sucked the cum out of her ass. It was so deliciously nasty that I felt my pussy tingling for action again. Linda purred, "You are one insatiable slut, baby." "As are you, baby," I purred back. Lorenzo ordered, "Get into a sixty-nine, sluts, while I recover. You'll be thrilled to know I still have at least one load left." We obeyed, and lavishly licked each other for an eternity. A while later, Lorenzo was ready for another round and he fucked both of us silly for almost a full hour before shooting his final load all over our faces. Once spent, Linda cleaned the cum off my face and I returned the favour, cleaning hers. Once all the cum was gone, Linda smiled at me and said, "Happy Valentine's Day, Dani." I smiled back, "I hope this wasn't a one-time deal." Linda laughed, then became serious, "Oh no, you are my slut now." "Forever," I replied, hoping she was serious. Lorenzo yawned, "You know, Dani, my brother would love you." I looked up from the floor to him and asked, "Is he as hung as you?" He shrugged, "I imagine so, we are twins." "Fuck off," I replied. "Fuck on," he retorted. Linda purred, "Well maybe we can make this threesome a foursome." But that is an entirely different story. The End