This begins at a large house party with one of my good friends whom I’ll be calling Issy. Issy is a girl build like an angel: short, and thin around the waist, but with a juicy set of tits (E cup maybe?) and an ass and thighs thick enough to make a kardashian jealous, except of course that for her, it was all natural. Anyway, the party was being hosted by another one of our friends but him and his girlfriend had disappeared upstairs long ago and it was late so Issy and I decided we would leave. I offered to walk her home since it was dark and we had both had quite a bit to drink; she agreed.
On the way to her house we were chatting about relationships, crushes, and everything else slightly horny teenagers chat about when tipsy. Issy was a very flirtatious person. She was the type that could made everything sound sexy without meaning to, but when she did really mean to it was like being placed under her spell with no option but to play along and flirt back. Tonight, I was fully entranced by her magic but nothing about me wanted to escape it. As we chatted, the sexual tension between us grew and grew and she started touching more: on the arm and hand, on the face and with the occasional brush against the penis which of course got the blood flowing away from my head. Unfortunately, it didn’t take long before we arrived as she lived fairly close. That wasn’t the end of the night, however. She grabbed my hand before I could leave and said, “Hey, since you’re here and it’s so late, you may as well just sleep on my sofa…”
“Uh… yeah sure, of course I’ll do that” I replied, very aware of who was asking me and how much sexual tension there had been building up between us on the way home. “Great!” she exclaimed, her face lighting up with a joyful yet devious smile as she pulled me into her house and up to her room.
As we entered into her room, she quickly freaked out and ran over to her bed. I was confused at first, but realised that she had grabbed something off the bed and was trying to hide it – a vibrator, and a fancy one at that. She was bright red when she turned back to look at me but I just laughed and her frown turned into a cute little smile. I put my arm around her shoulder and pulled her in for a hug to cheer her up. Mid-hug she said, “I didn’t mean for you to see that, I don’t want you to think I’m some chronic masturbator who needs expensive stuff to get off.” “Don’t be embarrassed” I said, laughing, “we all need to get our release sometimes.” Issy pulled away then, and we sat down on opposite sides of her bed in silence. After 30 seconds, she looked up at me with the face I usually expect to see on her: a sexy smirk and unblinking beautiful brown eyes that seemingly said ‘fuck me’. “How’d you like to play a game?” Issy asked. Issy loved games like truth or dare; fuck marry, kill; never have I ever; and others, always using them as a gateway into more intimate conversations. “What game do you have in mind?” “Truth or strip.” she said with a grin.
“How could I say no to that?” was my initial reaction but I was a little surprised as well. We had never seen each other naked or had any sexual relationship, although I of course had desired it. A few years prior, we had both had crushes on each other and considered dating but ultimately I wasn’t ready and it never happened, that didn’t mean I hadn’t thought about her body and what I’d want to do with her in the years since, however. “Let’s play then” she said. The rules of the game were that we would take it in turns to ask each other any question we liked and they could choose to answer it honestly or have the question asker remove one piece of their clothing, whoever was naked first would be the loser. I was wearing jeans, boxers, hoodie and a t-shirt so I only had 4 opportunities to strip. She was wearing leggings, panties, hoodie, t-shirt and a bra so she had an advantage with 5 opportunities to strip. I didn’t care particularly at this point and was determined to see her naked even if it wasn’t fair.
She let me ask first since I had a disadvantage. “Since I saw your vibrator, I’m curious: how often do you masturbate?” She looked up at me, staring dead into my eyes and said “everyday, if I can”. My dick grew slightly in my trousers at the image of her sprawled across this very bed I was sitting on intensely rubbing her clitoris with the vibrator, moaning gently… my fantasy was cut off short by her question – “do you ever think about me when you masturbate?” I really didn’t want to have to answer that one but if I was going to win, then I had to be honest. “All the time to be honest” as I said it I she smiled wide and gently bit her bottom lip before saying, “I thought you might.”
I won’t go through every single question that we asked each other as there were dozens I’ll just give a summary mostly with ones that resulted in stripping. “Where’s the weirdest place on your body that you’ve asked a guy to come on?” I asked her. She thought about it for a few seconds before getting me to pull her hoodie over her head, letting her long brunette hair lie over her shoulder. Without missing a beat and whilst I was still up and close to her she asked, “What are your greatest sexual fantasies?” I drew the line about telling her about that so I stuck my arms out and show grabbed the bottom of my hoodie, pulling it off me. She got me again with, “What’s the weirdest porn you’ve ever watched” so I lost my t-shirt but I retaliated with “What’s the dirtiest thing you’ve ever done with a person of the same gender” and she didn’t want to tell. I shuffled over to her and grabbed her t-shirt, lightly touching her waist as I did so. It was fairly tight to her torso so I had to keep my hands close to her chest as I pulled it over her large breasts. The bra she was wearing was lacy and thin so I could her perky nipples poking through it, but I still wanted more. I bargained with her: “this game isn’t really fair, you know, as I’m wearing one less piece of clothing than you, I think I should get your bra for free.” She frowned at first but then resigned and sighed with a smile. “I guess that’s only fair, but no more freebies!” she said. I nodded “of course” and proceeded to unclasp her bra putting both my arms around her in a hug whilst doing so. It didn’t fall by itself so I moved my hands back round to the front to pull it off her tits, giving her a gently squeeze as I did so, something I knew she liked as she had told me before that she liked her tits being played with. And what tits they were. I always knew they were large but she mostly wore hoodies so I had never appreciated just how massive they were, and how shapely too, with beautiful perky nipples that looked ripe for sucking on. I instantly got rock hard and had to try and hide it as I moved to sit back away from her, she definitely noticed though, judging by the smirk on her face and the way she asked “do you like them?”
We now knew some of each other’s deepest and darkest secrets and desires, and yet neither of us were relenting and so a long time passed with no clothes being removed by either of us. Finally, I had a spark of inspiration: “What’s the sexiest or dirtiest photo or video of yourself that you have your phone?” She blushed a pretty pale crimson and sighed before lying back and holding her legs up in the air so that I could remove her leggings. As I pulled them up from her thick thighs, her beautiful ass cheeks were revealed to me for the first time; tempting me with their jiggling as the leggings were pulled away. I also couldn’t help but notice that even after she had put her legs back down and sat up, her panties between those delightful thighs had a growing wet patch in the middle. Although, it didn’t feel like a complete win as I was fairly curious about what must have been on her phone that she really didn’t want me to see. My lead in the game was short lived however, when she decided to ask me “What’s the most embarrassing roleplay you’ve done during sex or masturbation?” and since I really did not want to tell her about some off the weird situations I had envisioned us in, I gave in and she siddled up to me to remove my trousers. As she pulled them away, she subtly rubbed her hand against my rock hard penis in my underwear which made it throb slightly. Her soft giggle after that happened told me she liked what she saw and suggested that she probably didn’t want this game to end with her only seeing my cock straining against the fabric of my boxers.
Both of us were just in underwear now and the pure attraction to each other’s bodies was almost palpable. I wanted her so so badly and I knew she wanted me, but one of us needed to win this game first. Finally, I asked “What’s the kinkiest thing that you want to try out that you never have?”. She sighed, drooped her head and said “fine, you win” before looking back up to me with her gorgeous smile returning to her face. She lead back down against her bed and raised her wet panties so that I could more easily remove them from her. They hung tightly to her ass and pussy, perfectly showing off what was underneath without giving it all away. As I peeled them away, the inside glistened with a wet sheen that was replicated too on her inviting pussy. That was it. My long time friend and person I had desired most, Issy, was finally lying naked before me. From her face with her shiny brown eyes and full lips to her large perky breasts all the way down to her sopping wet vagina, enormous ass and thick thighs; she was beautiful. “Well then,” she was saying “since you won, I guess that means that I owe you. I want you to fuck me however you’d like. Please don’t hold back.”
I, of course, did exactly what she said. I started with those oh so delectable breasts. I sucked hard on her nipples in a way she had told me she loved, whilst fingering her clitoris hard. I wanted to hear her moan my name tonight and this was the best way to do that and, after only a minute or two of her pussy getting wetter and wetter, she was moaning my name in ecstasy – her hands moving all up and down my body as she didn’t know what to do with them. I stopped then, to let her calm down, I didn’t want her to orgasm just yet, and besides, I wanted to be pleasured too. This was when I had the opportunity to enact one of my biggest fantasies that I had imagined with her. I sat on her middle, shoving my penis between her tits and the shaft was instantly enveloped with only the very top of it and the tip poking out the top. I instructed her to suck on it which she did whilst I simultaneously grabbed her boobs and rubbed them up and down along the shaft. The wetness secreting from the tip and the spit from her mouth mixed and travelled down between her tits, providing the perfect lubricant for my cock. There was so much going on and I felt so alive that it only took a matter of minutes before I was squirting my juices all over her tits, face and some into her mouth. She moaned gently and licked her lips for more cum before she pushed me off her and down onto the bed, and she sat up saying, “my turn.” My cock did not take long to get erect again, a few seconds of staring at her beautiful cum-covered body and her grabbing my dick was all I took to be back in business. She raised herself into the air as I lead there on the bed, and aligned her tight pussy up with the head of my penis. She brought it down onto it gently and moaned loudly as she did so. Her moment had arrived. She moved her pelvis up and down, up and down around my cock, taking the full length of it each and every time. With each drop, her boobs bounced and jiggled around in a way that got me even harder, and as I got harder, her moans got louder and louder. After some of the best minutes of my life, she leaned her face down, still wrapped around my cock and we began passionately making out. I took this as an opportunity to once again fondle her tits, and I pumped my penis back and forth to help her in that area. Soon after, her mouth broke away from mine as she screamed a moan more intense than I had heard her make all night. Her pussy exploded with her juices, covering my cock. That was all it took for me too and I quickly filled her warm insides with my sweet white cum. She dropped down on top of me, exhausted, and I put my arms around her in an embrace as our juices flowed around each other and we reflected on what we had just done.
I ended up sleeping in her bed for the few hours of the night that remained after that, and returned home in the morning. That event had certainly disrupted our friendship, but in no way was it over. Neither of us regretted what we had done and so our relationship became more of a friends with benefits situation, at least for a short while before both of us had to move cities and move on with our lives.
Source: reddit.com/r/sexystories/comments/p3k94o/truth_or_strip_with_two_best_friends_mf