She walked into my room with restraints and flogs scattered everywhere, “Ew oh my god what is all this shit” she says with clearly an intrigue in her eye but acting like she’s appalled as she picks up a leather flog. “That’s not for you, put it down” I respond and she immediately drops it. An hour later, as I turn her over on my bed to see how many fingers I can fit in her tight ass, I grab the flog and run the leather strips across her ass. She immediately turns her head around, “Nooooo stooop” in an almost childing tone. I slowly start to give her slaps with the leather strips, barely even slapping her, “Noooo oh my god stoooop!” she moans in the same whiney childish voice. So I stop. “FUCK, please, please do it again and harder, I was teasing. Please? Please?” she looks at me with these puppy dog eyes so I give her two good hard slaps on each cheek before I put it down on her back. “You better fuck me, god damnit” she exclaims.
(Skip to **Sexy fun begins** if you don’t care for the buildup and back story)
Sydney’s hair is long, completely natural. A couple inches taller than me with just the right curves. She always wears tight clothes to expose her breasts and ass she loves to brag about. She doesn’t ever wear padded bras, and loves to brag how her breasts simply naturally hold themselves up, she only wears a bra because she doesn’t want to look like a hippie.
I’ve had my eye on her for about a year. She’s a regular at a bar I frequent, and I’ve always got a very odd vibe from her. She’s never directly flirted with me, but recently my friend Brittany and I have gotten to know her really well. In the past few months, Brittany and Sydney have become quite good friends, and I hang out with them together from time to time. I’m very honest and completely comfortable telling her how beautiful Sydney is. Sometimes random conversations about sex or kink come up. She’s super vanilla and always seems intrigued about Brittany and I’s knowledge of kink, while acting like she finds it appalling. But she always keeps asking questions and wanting more details. Sydney and I had already discussed the fact that we won't fuck because she’s friends with Brittany. So it’s fun to say it knowing she doesn’t think I’m just dreaming and wanting it. I mean, I am constantly fantasizing about fucking her, but she doesn’t seem threatened that I’m acting like I’m trying even though she doesn’t ever reciprocate.
On this particular night, I had spent the day going brewery-hopping with Brittany. After a long day of drinking and incredible sex with Brittany, it’s time for me to head home, but I stop off at the bar we frequent for a night-cap. I walk in and see Sydney sitting at the end of the bar alone. At this point I’m practically sober because I knew I needed to drive home so I hadn’t had a drink for a couple hours while we had dinner and relaxed. I sit up at the bar right next to her, at this point luckily we’re good enough friends that I know I can just prop up right next to her without asking if I can join. I look her up and down admiring her typical really tight black outfit as she catches me checking her out and shakes her head with a slight smirk.
We begin our usual banter about whatever is on TV, her ‘boyfriend’ (they’ve been dating regularly, are mostly exclusive but not technically together. Complicated bullshit). We have great conversations about dating, relationships, monogamy or in my case non-monogamy. We start to discuss sex and she tells me how vanilla her boyfriend is, who we’ll call Miles. He has a small penis, which she doesn’t mind at all, she only really climaxes to clitoral stimulation so she likes his size, and recently learned how much she loves anal so that helps. The random conversations continue and at this point I’ve had a few drinks - I intended on 1 but she was really fun to hang out with, lovely eye candy aside, and I rarely get to chat with her just 1-on-1.
As we are on our last drink, she gets a bizarre phone call from a blocked caller ID. I don’t know why, but for some reason at 1am she decided to just answer it, assuming it was some random booty call. She said she didn’t want a random hook up but thought it would be funny to see who it was so she answered the call. Turns out it was an extremely creepy stalker she has had for years, and she even has a restraining order against him. This really rocked her, she started sweating and kind of shaking a little. I tried to console her and chill her out, but I have never had a crazy stalker so it was really hard to relate and know what to do to calm her down. Finally she just looks at me and says, “we’re doing shots”. I tell her there’s no way I’m doing shots, especially that late at night, but she insisted. As her friend, I did feel kind of like it was my duty to join her and see if I could help calm her down, she still looked like she saw a ghost. At this point I had 0 of intention of the night turning out to be worthy of a sexy story and legitimately want to make sure she’s okay.
As we’re taking our shots, the moment the tequila goes down she switches gears and manages to not continue to be freaked out. We went outside to smoke and that’s when things started to get interesting. She was very touchy feely all of the sudden and was bragging about her body as usual. She was flexing her arms and legs, asking me to feel how tight she is. Then we got to her ass, oh her perfect ass. I’ve been wanting to feel her ass since the moment I met her. At this point we basically just have our hands all over each other, and for the first time ever she finally hits on me. Granted very easily could have been the tequila talking, but I’ll take it! She’s running her hands through my hair and looks me in the eyes with her piercing dark eyes, “Have ever told you how fucking sexy you are? My god” as her hands slide down my body to my ass. That gave me an instant erection.
**Sexy fun begins**
Two very drunk guys invite her to come over to their place and have some drinks and they tell me I could tag along. The idea of the three of us fucking her was pretty erotic, but we were really drunk and the idea of walking home late or early the next morning sounded terrible, and I’m not sure I could handle the blue balls I would have if she fucked one of them. So I convinced her that the best idea would be just to head back to my place - she was really scared to go home because of the stalker guy, she just needed a night away so she could sleep, and I had a spare room in my apt. Even with our hands all over each other, I still genuinely did not intend on doing anything physical with her, nor did I think she actually would. Until she responded, “but I know I’m going to want to fuck you if we go back to your place, and I’m not sure that’s a good idea” she says as her hands pull my body in against hers, pressing my half-hard cock to her warm mound. My dominant side takes over, “You’re right, that’s a terrible idea” I say as I lean into her ear and whisper, “And what makes you think you deserve to feel my cock inside your tight, soaking wet little pussy?” I say as I see her melt. “Fuuuck” she moans as I can see what I think is a little shock that my comment turned her on.
We start to walk to my apartment and can’t keep our hands off each other as we stumble down the road. She continues the banter and teases, “only truly special guys get to see my perfect body, I’m really not sure you make the cut” she says as she grabs my hand and moves it to her breast, “Don’t they just feel perfect? Notice the bra isn’t padded?”. I grasp her breast fairly tight, but not sure how easily she bruises so I don’t go too hard and respond, “Oh Sydney, you really think I need to see you naked? With the tight outfits you wear it’s not like you leave much to the imagination. And yea, you’ve told me at least 10 times you don’t wear padded bras”. “Fuck you” she responds with a beautiful big smile as I give her nipple a light squeeze before I let go.
We make it into my apartment and walk into the kitchen to grab a beer. Before I open the fridge I grab her hair and force her against the counter and begin to slowly kiss her neck, sliding my hands up her body to her breasts. “Yea, I think this is the only skin I really need to see” I tease as my lips trail her low cut top. We finally get around to grabbing beers and head to the living room. At this point we somehow seem relatively coherent and go back to just normal casual conversation, but still can’t keep our hands off each other. My hand slid from her breasts down to her mound. Her pussy was so warm I could feel it radiating. I started to rub her through her tight yoga pants as she slid down on the couch and opened her legs welcoming me to continue. She instructed me to rub a little bit higher. I move up and she starts to moan lightly. I move my other hand to her breast as I see her nipples getting harder through her tight top and begin to lightly tease, just sliding my fingers across lightly. “You fucking tease” she says as she looks at me with her intense eyes. “I’ve been trying out anal lately, you should definitely fuck my ass”. At this point neither of us have taken a single article of clothing off. “I don’t know Sydney, I’m still not convinced that I need to see you naked” I say as I take my hand from her swollen clit and squeeze both of her rock hard nipples until she tells me it’s too much. “Fuck you, you better fuck me god damnit” I grab her hand and stand up, “We’ll see” as I lead her to my bedroom.
We get into my room and it’s that moment I realize all of my bondage and toys from my kinky date the night before are spread all over the floor, bed, and night tables. Empty condom wrappers spread all over the night stand. The curse of not having planned on a date, my place was a mess. There were wrist restraints, ankle restraints, rope, a ball gag, and two leather flogs spread randomly all over my room.
I take off my belt and remove everything from my pockets so she can straddle me uninhibited. I lay down on my bed and guide her to straddle me. She doesn’t skip a beat. I grasp her hair and force her head to move around guiding my lips from one ear, down her low cut shirt and back up to the other ear, then back around her neck, slowly and lightly kissing every inch, then a light peck on the lips which is the first time I saw her hesitate. I push her up and grab her big rock hard nipples again as she begins to grind on my hard cock through my jeans as my hands move down and grasp her as tight. I can feel her warmth through my jeans, I don’t think I’ve ever felt a woman get that warm. “Ok fine, I guess I’m curious” I say as my hands move from her as and I lift her top up and expose her skin. I sit up and start to kiss her slowly as I slide her shirt off. She get’s impatient of how slow I’m moving and grabs her shirt to take it off herself and it rips right down the side seam. We both laugh, “That’s what you get for being impatient. I’ll be in charge of taking your clothes off from now on”.
The bra she has on is a see-through lace, perfectly fitting, covering just about ¾ of her breasts. Her breasts are dreamy and definitely seem to be as good as she bragged about. They were much bigger than they seemed. The tight top was restricting them a bit, they were impressively full. And sensitive, very sensitive. I started kissing her breasts through the lace. She started playing with my hair and attempting to control where I kissed, so I grabbed her hands and pulled them behind her back and held them down as I continued to tease. My lips wondering up her cleavage to her neck and then back down. At this point I pull her off of me and lay her down. I grab her hands and hold them above her head as my other hand teases her clit above her pants. “Harder please?” she asks as I start to rub a bit deeper and more intense as my lips meet her breasts and I begin to nibble on her hard nipples as she begins to moan louder. “I like it but not too hard, Miles cannot know about this, no marks!” she says. While she said she wouldn’t consider this cheating because they’re not technically official, cheating a huge unfulfilled fantasy of mine so that remark really turned me on. “Well then maybe I shouldn’t fuck your tight little ass, he might notice a bigger cock than his used your tight ass”. “Fuck my ass, now!” she responds with an almost evil look in her eye. I let go of her hands and move down to her hips, slowly peeling her tight pants off, kissing slowly as I make my way down. “You fucking asshole, your teasing is getting ridiculous” - which really turns me on, knowing that I’ve had my eyes on her for this long and she has known how into her I am but she’s never reciprocated attraction, I don’t think I’ve ever had such a fulfilling teasing session. .
Now it’s time for her breasts to finally be exposed. I moved up and straddled her, put my hand behind her neck and slowly pulled her closer to me and kissed her cheek, at which point the hesitation of kissing on the lips went away and she kissed me deeply and intense. I reached my hand around and unclipped her bra with one hand, apparently something she’s never had a guy do judging by her response, “Did you seriously just do that with one hand? Fuck that’s so fucking hot” she moans. I sit back and look at her with a teasing evil eye and my hands push her shoulders hard and fast down onto the bed. I grab her hands and we link fingers as I hold her down. I start on the bottom of her breast and slide my tongue around her breast, slowly making circles around to her nipple. Once I approach the round pink sensitive nipple, I stop licking and give her rock hard nipple a light kiss, then repeat on her second nipple. “You’re lucky I’m liking this or I’d be fucking pissed you’re taking so long” she slowly moans. I stop what I’m doing and take my shirt and pants off, “I’m still not convinced I want to fuck your tight little ass” I tease as my pants slide down, exposing my throbbing hardon. I’m not huge but clearly bigger than Miles, the moment she sees the outline of my cock in my tight boxer briefs she remarks, “Fuck, theres no fucking way my ass will handle that, you’ll have to start with your fingers”.
I drip lube down her tight asshole and onto two of my fingers, slowly teasing her ass until I slide in slowly. Her little asshole is so fucking tight my fingers barely fit as she lets out a “oh fuck yes” as I enter. I slide my two fingers in and out and it almost hurts my fingers she’s so tight. “Give me your fucking cock, please, I can take it!” she claims. I stand up and slide a condom onto my throbbing hardon. The head of my cock meets her tight asshole as I add more lube and attempt to slide the head of my cock in. “FUCK!” she screams. “There’s no way that’s fitting, fuck fuck fuck goddamnit!”.
I back up and she turns over to me. I pull the condom off and she does not waste any time pouncing on me with her mouth wide open as she takes my cock in her throat. She begins to choke but she’s in control and doesn’t stop. She takes every inch down her throat. She kept sucking deep as I grasped her hair, “don’t fucking stop” I moan as she does as she’s told. She pulls off of my cock and looks up to me, with her big puppy eyes, “please fuck me. Now. Please!” she begs as her hand strokes my soaking wet cock. “Nope, you’re going to have to see me again for that. Lose that little dick prick you’re dating and we’ll talk” She doesn’t debate, but the disappointed look on her face is hard to handle, I almost gave in. But she goes right back at it, in potentially the fastest blow job I’ve ever received I quickly unload in her mouth, warning her I’m about to release I loudly moan, “Are you going to take every drop like a good girl?” It’s a surprisingly large load as she struggles to take it, but expertly takes every single drop. “Wow” is the only thing she could manage to say as she gargles my warm cum before she takes a big gulp and swallows every drop. I stroke her hair and thank her.
We lay back down and cuddle, continuing to tease each other and randomly bring up non-sexual subjects and slowly drift to sleep. We talk about how annoying it is to sleep in the same bed as someone and I offer her the bed I originally intended her to sleep in but she declines. Slightly annoyed because I know I’m not going to get any sleep, but also really happy that she stayed so I can continue to live out this bizarre fantasy in reality. She demands that we spoon so she can feel my cock against her ass. I debate her because I really want to sleep, but eventually concede because I’m so tired I’m positive I can sleep no matter what as we spoon each other to sleep. We eventually drift to sleep, this was at about 5:30am.
We only get about two hours of sleep and I wake up before her with a raging hardon. To get back at her for demanding we spoon to sleep, I slide my hardon that’s soaked in pre-cum between her thighs, teasing her ass and clit as I reach my arm around and tease her breasts. She slowly wakes up and the first thing she says is “you fucking asshole” as she grinds into my cock. “That’s what you get for wanting to spoon so bad!” I respond.
We cuddle and kiss the morning away until we eventually decide a few hours later that we should really go our separate ways for now. She gets up and struggles to find her clothes as we attempt to get ourselves together. As she’s searching around the apartment she says, “where the fuck is my underwear, oh there they are!” as she picks up a sexy pair of lace panties. “Wait, I wasn’t wearing any last night I could have sworn” she says. “Sorry, those aren’t yours. My date last night left those. I don’t think she would mind if you borrowed them but only if you return them by having a threesome with her and I”. “Tempting” she replies but drops the panties back to the floor.
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