Hopefully by the end of this you'll understand that the play on words in the title.
I've been down following my forced 'breakup' and utterly failing at keeping my thoughts from spiraling this way and that. Running with my friend only compounds it since she knows every detail of my ended relationship. Binging Netflix only gets you so far.
So enter a chance encounter with my guy friend Jason this weekend. We have been friends since high school and he very quickly fell into my friendzone when we met. He's not bad looking, and i'm sure if things had aligned at the time we might have hit it off. But I was crushing hard on some boy at the time, and then in a relationship someone else later, and by the time I was single, I just knew Jason too well to even consider it. He was a friend and I didn't want to disturb it.
But disturb we/I did on Saturday. To clear my head, instead of just running around the neighborhood as is my norm, I drove to a nearby park to run there. Maybe a change of scenery would help my downwards spiral. Unbeknownst to me, Jason runs there also and we had a random encounter running towards each other down the trail. He recognized me immediately slowing and saying hi long before I recognized who was grabbing my attention, sorry but I was in the zone and I tend not to make eye contact with guys while running safety reasons. By which point I had stopped, struggled to get my earbuds out while looking like a fool, and my sunglasses off before realizing it was Jason. We greeted as expected, customary hellos and awkward questions or "what are you doing here," which is blatantly obvious, before laughing and rephrasing it as "i didn't know you ran here," and "I don't normally but," over talking each other and trying to keep our breathing under control. That's how it started, and how we ended up taking off up the trail together for a few miles before headed back to the cars.
Without thinking it through, I invited Jason back to the house to hang out. It wasn't that he had never been to the house, he had, several times. It wasn't even because of recent events with my parents, or that my family was away looking at universities for my sister this weekend leaving the house empty. It was simply that I had no plans, nor did he, and that's a recipe that ends either to boredom or something less boring if you catch my drift. Either way he accepted the invite and it was too late to back out.
At the house the inevitable occurred, we had no plans and we sat there on the sofa drinks in hand looking blanks at each other. We tried striking up a conversation, but kept coming back to a lull and silence. "Ok, 3 questions it is." Jason looked at me perplexed and puzzled. "You've never heard of 3 questions?" Again, he looked at me like I was speaking a different language. I thought this was more universal than it was apparently, it was a game my family and friends had played for years. Someone throws it out, and it's a way to strike up a conversation. You each take turns asking questions of each other, and typically a common interest is found and conversation flows. "Basically you ask me a question, then I ask you one, whatever topic of interest, we'll find something to talk about."
Jason took a sip of his sparkling water, swallowed and said "any topic?"
It was at that moment that I knew what was coming, where his mind had gone, and where these questions would lead. But why not? And maybe I had secretly wanted this intimacy anyway, and subconsciously created a scenario where this would be the result. So I leaned in, not physically, but in my minds eye. "Sure! I mean, usually the questions stay above board, but I guess, I mean, we're good friends, and we're alone, so if you want to take the filters off, i'm game." Jason smiled. "Well in that case why only 3?" I laughed. "We'll start with 3, maybe more if we're enjoying ourselves, but you have to start," I said. Honestly if he wanted this to be inappropriate, I wanted him to set that tone.
"Fine," he said while taking a sip and putting his water down. "Question 1," he smiled deviously, "I gotta know, thong or no thong under there," he paused while eying and gesturing his head at my shorts, "cause for the life of me I couldn't work it out." I laughed and we exchanged small talk about how he was checking me out while having to run behind me on a few occasions in the park, me calling him a perv out of jest. "Thong, if you must know. I never run without underwear, thats just nasty," I laughed, "but a girl still has to look cute, right?" I probably should have been blushing, but honestly that wasn't the wildest thing I had admitted to by far in recent months, so it honestly didn't even phase me. "Well no, a girl doesn't have to look cute to go for a run, but you make it look effortless," he smiled. "Aww sweet, blek" I fake barfed, "moving on, next," I said, while realizing I had to come up with a question.
I kinda felt like I needed to match his freak. Like I didn't want to progress things and lead him down a path, but also didn't want Jason to feel like he overstepped and get anxious either. I thought a few moments while we bantered as he urged me to "spit it out already" before asking, "so are you a boob guy or a butt guy, given you were clearly staring while i was running." "Oh i'm a butt guy, easy. It's like this," he smiled, "in my opinion, if a girl has a beautiful pair or, ya know, but her butt is flat, she looks imbalanced. Whereas if a girl is flat chested but has an amazing butt, she still looks incredible." He then proceeded to list of several actresses with small breasts and I had to admit I kinda understood where he was coming from. "So which category do I fall into then?" I asked, knowing my B cups are on the small side. "Oh neither, you have both working well for you," he smiled. I'm not sure why I was fishing for a complement, but he had happily obliged.
"Alright," he said without pause, "if I may, and since you brought it up, what size are they anyway, and whose had the privilege of seeing them?" Ok, now I was blushing. "Whoa, alright there Jason, I should make that 2 questions, damn," I laughed, but also felt a flush of excitement. "They're B cups if you must know, and," I proceeded to count on my fingers while listing names from my past. Not a long list, but had some surprises he wasn't anticipating. My best friend, my father, my neighbor, along with a past boyfriend. We ended up talking about how my best friend had seen them (obviously he got the whole girl on girl excitement from that not that she and I have ever fooled around), a brief history on my neighbor, and how it ended, which was also how my dad had seen them. Turned into a bit of a loaded question that he hadn't expected, but it was fun to open up and share.
In retort I bluntly asked, "go on then, have you ever shown it off to anyone, or have you been caught with your pants down so to speak?" We ended up laughing over him getting caught rubbing one out a couple times, ex girlfriends, and once when he was bored over a webcam when he was younger. From his previous question about my boobs, he knew the story of who had seen my crotch was the same answer, so thought hard a bit before asking his third and possibly final question.
"You said filterless, so i'm just gonna spit it out, YOLO," I took a sharp breath and my eyes widened not knowing what to expect, he smiled and locked eyes with me, the tension intensified, "how do you like your steak cooked?" he asked. Honestly my mind did backflips and turned inside out while trying to process this. My face a picture of confusion. "Look this is serious, it's important. And you said whatever I wanted, and I want to know, tell me," he was enjoying this far too much. "Medium, no medium rare," I spluttered as if the pressure was too much for me. "Are you sure, you don't see, sure." "Yes, yes, medium rare, what on earth, yes." Jason was all but crying at this point knowing the knots he had tied me up into.
"You're an ass," I laughed, "but i'll have my revenge," I said eyeing him and leaning forward to face him directly. "Last question," I said in a way to indicate he wasted his last shot on a joke, messing with his head. And I was upping the game and he couldn't participate just to twist the knife, "a fantasy you have lived out, and a fantasy you haven't."
He sat back almost confident in himself instead of cringing or freezing up, which was really frustrating. "Oh that's fun," he said in an agreeable way, which only annoyed my further. "Hmmm," Jason continued amping it up. "Past fantasy, [an ex] of mine and I had sex in the woods several times. Like places we would get caught if we kept it up. Always naked just to make sure we were sunk if someone came. Both always quasi hoping to be caught by a cute person who would join in. Never happened though." He paused, but we ended up talking over those experiences and how I could never do that though feeling the thrill of it. Finally Jason admitted that his uncompleted fantasy was cum play, which definitely took him a bit of effort to say. But again after talking it over he all but had me convinced. Sex is messy, why should women stereotypically have to accept either tasting it even slightly while giving head, or having it in their mouth, or swallow it, or best case, having it on their body for them to have to clean up but men were omitted from it. Shouldn't they have to experience the same thing as women? He further went on to explain that he loves watching a woman taste themselves, its sexy, so why is there such a taboo on men and cum? Like I said, by the end of it I was basically his cheerleader.
We sat back, both satisfied with the game, and honestly unashamed of any information we shared with each other. "Do I not even get to ask that same question back? Jason asked, that's messed up, he laughed. I smiled, rules are rules, I joked before relenting. "Fine, you can ask me a twist on the same question, but not the same question, deal?"
He mulled it over, "what is someones fantasy that you've been a part of with or without knowing about it?"
I paused having not expected it. It was a curious question, and certainly thought provoking. There were fantasies that I was aware of that had been brought to my attention, all from my best friend (again he enjoyed the girl on girl images in his mind as I shared them), but those didn't count as they hadn't occurred. It took some thought, but eventually I said, "i'm not sure if this counts, but when I was younger, during a house party, a neighbors son was caught snooping in my bedroom. I certainly didn't know it was happening, but is it fair to say that was a fantasy of his?" Jason chuckled, "yeah, that counts, little pervert, i've never done that, but can't say I never thought about it." We went on to talk about how I had felt after finding out, and a TV show that was sort of the same thing, a dating show were contestants were chosen for dates based on what was found in their bedrooms. I remember it, but neither of us could remember what it was called.
The conversation had lulled again and I made myself busy getting Jason a second drink, telling him not to stare at my ass as I walked towards the kitchen, him deliberately and obviously staring in protest, us both chuckling. "So do we get more questions then, you did say maybe, and we were having fun, what do you say?" Jason asked while taking the drink out of my hand. "Alright, but that last question was really my question, so again, you're up," I said. "Nice!" Jason exclaimed with excitement and launched right into it. "So if that little kid were to go snooping now, what do you think he would find that would excite him?"
The question landed with a blow, and my mind hollered at me with alarm bells blazing. Just answer it, answer it with words. It's easy. Don't do it. Don't do what you're mulling over. Just tell him. Shut up conscious mind, you're not in control right now my pent up frustration yelled back.
And before I could stop myself, I let it go. "Tell you what. Let's Zoom. I'll stay here on mute with my camera on my face, you reverse the camera so I see what you're looking at, go snoop." Jason was clearly not expecting that, having assumed I would just admit and describe the intimate contents of my room, but recreating the TV show we both recalled was not planned. After reaffirming how it would work, and my commitment that I would stay right there, and that he had full access to snoop, he agreed. We got the zoom call going, he asked if I was sure, I said I was, and he slowly left the room. My eyes turned to my phone, watching through the screen as someone walked the stairs I was so familiar with, the bedroom I had slept in for years coming into screen, and the sound of the door closing (both through the phone and in the house). Jason said nothing, though I could hear him breathing and make out movements.
I watched as he started with the obvious, the top drawer of my dresser. My underwear coming into view as I heard the wooden draws slide against each other. I watched as his right hand moved into the drawer, moving items around and holding things up. It was almost as if he were cataloging my drawer, determining how frequently I wore a thong verse not, taking inventory of what he liked and didn't. It was curious to watch him slowly work through it all, and I found myself fixated to the screen. Realizing this, I quickly airplayed it to the TV and sat back to watch it unfold.
Jason continued his search in other drawers, eventually finding a small stash of lingerie tucked into a bag at the back of my PJ drawer. My heart rate quickened as I watched him empty it carelessly onto my bed for a better look. I began to feel the eroticism escalate. It was lingerie right, most from Victorias Secret. Nothing that hasn't been on display in their store or window displays before. But no, this was different. This was my lingerie. Lingerie that I have worn before and during sex. Lingerie that is tied directly to my sexuality. My pulse was pounding in my ears as I watched Jason handling the delicate fabric that had draped the most intimate areas of my body. I watched as he lay the corresponding pieces out on my bed for a look at them all.
He looked under my bed, moving a few things around but finding nothing exciting, and then looking in my nightstand. My journal was in there, but honestly it's old and has nothing i'm embarrassed by anymore, crushes and silly fights from early school mostly. A love letter I had forgotten about, yeah, that was embarrassing and I heard Jason mocking for my benefit, knowing I was powerless to stop it, knowing he could still see me sat there holding my phone. His attention shifted to my closet, moving items around, checking boxes on my shelf, not finding anything unexpected. I took a quick breath wondering if that was his final stop, my thoughts wondering if he would search any where else or find anything else before leaving. Almost relieved, somewhat disappointed interestingly enough.
I watched as he moved my lingerie back to it's bag, and put away, what a gentleman, and just when I thought he would leave my room in peace, I watched as he laid down on my bed pointing the camera at the ceiling. What is he doing?!? I could hear movement, and then it dawned me exactly what he was doing. If I were to stash something near my bed, where would it be? Then I saw the camera move, and my heart dropped, my face flashed red. The camera returned to his right hand in view as it slid down the right side of my bed next to the wall, only to return with a small pink vibrator, and then return to pull out a larger light blue silicone dildo. One of those that is semi transparent and has a suction cup on the base. He lay there holding them up, as if a trophy was collected. Surely he was looking for my reaction, and I was at that point beat red and covering my face.
The call ended, and I heard Jason leave the room and head backdown stairs to rejoin me, smile grinning from ear to ear. My eyes immediately looking to confirm he hadn't brought them with him, relieved he hadn't. I was still blushing as red as could be. "Well that was surprisingly fun," he said and then commenting positively on the lingerie, and the apparent frequency I wear thongs, "all nice to know in a strange way," he said, omitting any mention of my toys. I was too embarrassed to really say much, though reluctantly agreed that it was oddly fun to have watched. He loved that I airplayed it, making it feel even more like the TV show. He had guessed when it was so long since I had looked at my phone.
Pushing me for how I felt, I eventually admitted it was fun watching him inspect my underwear drawer so closely, even more so seeing him lay out my lingerie across my bed. Admitting I was torn between relief that he didn't find my toys, followed by exhilaration when he did. He told me that he knew they must be there, and was not leaving until he found them, but he was shocked they weren't in my bedside drawer or under my bed, pretty impressed at the little nook I had found to keep them in sort of inside the bed frame. Then went so far as to say that he "loved handling them knowing where they had been," which made me blush. I tried deflecting by telling them they were cleaned after each use, but that didn't really matter to him much.
Another lull which this time he broke. "So when you were young you hated knowing that the kid had snooped, but now, it kinda seems like you enjoyed it. Whats different?" And honestly I didn't know. A cross between being fully known, or being forced to witness it without a say. I fumbled around trying to explain what was different and how I had felt watching. My heart was pounding, and I was breathing deep. Maybe it's just me, but when my breathing is deep with nerves, it almost feels like my chest sinks inwards with each exhale. Once again my conscious brain was screaming no, but it was pointless and it knew it. This was happening, and that was that.
I took a breath, picked up my phone from the sofa by my leg, extended it in my hand, and offered it to Jason. He took it, but with an inquisitive look on his face. My heart was pounding harder than it ever had before. "If you really want to snoop," I said softly. He sort of looked at the phone blankly, then I saw his Adams Apple move with a swallow. He flicked his thumb upwards to open my phone, pointing it at my own face to unlock it. I moved to sit directly at his side, and watched as he silently began to open my photos app. To find that hidden folder. To use my face again to get into it, only to see countless adult photos of me. The thumbnails enlarging into full photos, watching him pinch to zoom in and out of my body. "I assumed you shaved," he said as he zoomed in on my pussy.
Countless photos of me in lingerie, posing, close ups. Photos I took 3 years ago when I was playing with different pubic hair styles - he was particularly interested in those and we ended up deliberating about which he liked the most and why, and what I like, the advantages and disadvantages. Finally deciding to flick back down to a video that he had clearly seen by skipped on. A video of me with my dildo from a month ago. About 5 minutes in length, several positions, but mostly meant to serve as a way to talk dirty and moan. It was made for someone and I never deleted it. He was evidently hard and did nothing to hide it.
There were texts he could have looked through, but he was beyond satisfied with what he had seen, closed my phone and handed it back to me. "I'm not sure what to say other than, thank you," he smiled.
I put my phone down, leaned in and invited him to lean into a kiss, which lead to him laying me down and laying on top of me across the sofa. We made out for a timeless amount of time, lost in the elevation of what we had both done. Both of us clearly knowing we each were ready for this. I looked up at him as our kiss broke, a soft smile on my face, "where do you want your cum before you taste it?" I asked. His face blushed hard, as he forced out a fake 'what?' "You said you were curious about cum play, and why it was such a taboo for a guy to experience it. So where would you like your cum?" I could feel the heat radiating off his skin, being faced with the reality of facing his fantasy. "On you, I guess?
I smiled, "that's a given Jason." I realized that he didn't have the strength to commit to it, and would need some encouragement. "Do you want it in my mouth and I'll kiss you? Or do you think you can lick it off me? My boobs? Stomach? It might drip off, but you can cum on my pussy if you want." I said trying to encouage him and help him. "I want to, but," he paused, "I can't, I just know I can't bring myself to it." I asked him to let me up, which he was upset about initially, but I told him not to worry, then stood in front of him and dropped my clothes giving him a full frontal. Leaning over, I helped him out of his clothes, his cock springing out ready. I smiled, gave it a quick deep suck, listening to him gasp and almost pull back out of surprise. "Do you want this?" I asked, he nodded. "And do you want your fantasy to come true?" I asked, again he nodded.
I straddled him, helping guide his cock into my pussy, sinking down deep until it hit my cervix. Looking down at him, "it's ok, just cum when you need, don't hold it back," and with that, i began to slowly move up and down on him. He lasted a handful of seconds which made me smile, but that wasn't the point. As soon as his pulsing settled, I reached my hand between my legs, slid his cock out and guarded my pussy with my hand, and moved up his body quickly as to not give him time to think, planting my pussy onto his mouth and moving my hand away. I felt his mouth open, his tongue extend to contact my pussy. I pushed some weight down on him to secure his mouth in place and stayed there rocking my hips and pushing to encourage his cum to drip out of me into his mouth.
Reluctance, shame, or embarrassment left at the door apparently, he licked me deeply, swallowing and making sounds of enjoyment and delight which only drove me to cum quicker and harder. His tongue flicking across my clit in just the right way pushing me over the edge.
Obviously this was all followed by the customary chit chat as we came down and our brains caught up with the realities of experience. He left, I showered, used my toys thinking of him, and text him a smiley face before going to sleep Saturday night.