"âŚyou can't be serious" I said to her in disbelief. "When I agreed to be adventurous with you, this isn't what I meant. I thought you had something sexy in mind"
But before we get to all that, we need some context. My sister has a really hot friend named Sarah that I've had a huge crush on since we were little. She's a few years older so while she thought my affection was cute, she always brushed me off as just my sisters silly little brother. Now we're all grown adults and I'd landed my dream job, so I figured it was time to shoot my shot with my dream girl. If she didn't see me as an adult now, she probably never would. My family along with a few close friends, including Sarah, took me out to dinner to celebrate me landing my dream job. The whole night I kept thinking of how I should ask her out, but it wasn't until we were out for drinks later that I made my move. I decided playing it cool and casual would give me my best shot. She's not exactly the type to go for a sweet and romantic gesture. I asked her if she remembered when I was just a little boy with a huge crush on her and she responded yes through a smile and a laugh. I told her that since I'm not so little any more she should let me take her out some time. I was a late bloomer and I'd grown over a foot since I last saw her.
"You still have a crush on me after all these years?" Sarah asked as she turned from the bar and put her hand on my arm.
"Some things never change" I said while returning her lustful and flirty eye contact.
As Sarah pulled herself closer and pressed her body against mine, she whispered in my ear "Why do you even want to be with me? Don't you remember when I told you that I'm tooâŚ.. adventurous for you?"
Goosebumps ran down my spine and spread to my arms as her lips brushed against my ear. My heart pounding and my mind was racing with thoughts of where this night was headed as I responded "I do remember but I'm not that little boy you used to know. I'm down for anything you want to do with me."
She squeezed me tighter and looked into my eyes as though she was about to say something, but instead, moved her left hand from my arm to the back of my head and put her lips on mine. After a passionate makeout that I'd only be willing to do in a bar after exactly this many years of pretext, she asked if I really meant that I'd do anything with her and of course I reassured her that I did.
"You can prove it to me tomorrow night" she said with a smile. "Wear some cozy pajamas and get us some snacks and whatever else we'd want for a cozy movie night in. We'll cozy up together and then we can find out if you're this adventurous man you claim to be, or if you're still just my friends silly little brother. Now let's get back to the party and hope nobody saw us kissing. I don't want them getting the wrong idea before you prove yourself" She gave me a kiss on the cheek, giggled, and then ran off towards all our friends.
After a whole night of cuddling, kissing, and agonizing teasing, I finally asked what she was going to make me do to prove my willingness for adventure to her. She excitedly told me to leave the room for 2 minutes, then come back in. I went to the kitchen, grabbed some water, and tried to imagine what kinds of lingerie and sex toys she was pulling out of her overnight bag for us. I was admittedly a little nervous due to a complete lack of knowledge about what was coming, hoping that I could play everything cool. Little did I know, I couldn't possibly have been nervous enough for what I was about to walk into.
While she was sitting on my bed in strappy black lingerie that accented her curves beautifully, there were two items on the bed in front of her that caught my attention and furled my brow. "Uhh what are these?" I asked cautiously.
"Well, you told me you're not the little boy I used to know, so I want you to prove it. This is an enema, and this is a diaper." She said with a tone somewhere between matter of fact and excited. "You're going to give yourself this enema, diaper yourself, and hold it for 15 minutes. Once I watch you give yourself the enema, I'm going to head out to the living room and I'll be waiting on the couch by the fireplace. If you come out after 15 minutes and this diaper is still clean, then you're definitely man enough to have sex with me tonight. If you have an accident, then you'll have proved you're still to little to be fucking a girl like me. Originally the conditions were going to be that if you have an accident we wouldn't hang out any more, but I've had so much fun these past couple days that I've changed my mind on that. Hopefully you don't, but if you do have an accident, we can still hang out as long as you know that sex is off the table."
My jaw was practically on the floor. "âŚYou can't be serious. When I agreed to be adventurous with you, this isn't what I meant. I thought you had something sexy in mind." I thought I was about to have wild, kinky sex and now Sarah wants me to put on some giant adult diaper and play Russian roulette with shitting myself?? This was completely insane and if it was anyone else I wouldn't have even finished hearing out the rules of her weird little game.
"Oh come on it's just a silly little game" she said as she pulled me on top of her and started kissing me again. She was touching me everywhere I wanted to be touched as she whispered "If you don't want to play this adventurous little game with me, or you chicken out and take the diaper off early, we can go back to being acquaintances who know each other from growing up." She took my silence as an opportunity to slide my pajama bottoms off, I'd been so distracted by the supplies she'd brought that I forgot to undress myself to match the energy of her lingerie. She grabbed my throbbing manhood and whispered "So do you want to play? âŚor should I head home?" as she let go of me without breaking her teasingly playful eye contact.
I knew what she was doing but it seemed like it was working anyway. I wanted her so badly I don't think there's much I wouldn't do to be with her. "I can't believe I'm doing this" I said in exasperation as I grabbed the diaper and the enema and went to leave to room because for some reason, it made sense to me that this should be done in the bathroom.
"Where do you think you're going? You can't leave this room until you come out to find me on the couch 15 minutes after you do your enema." she stated in a playful but stern voice. "Hopefully you'll be coming out to have fun with me, not to show me that you did something gross". She was playing with her breasts as she said this and I couldn't help but wonder which outcome she actually wanted.
"This is so embarrassing I can't believe I have to do the first enema of my life and it's in front of you!" I said with reddening cheeks as I held it in my hand showing it to her. At least it was only 15 minutes, I thought to myself. Surely whatever is in this little bottle couldn't cause me to actually lose control in such a short amount of time.
As I stood there showing her the little plastic enema bottle as if it'd somehow change her mind about this whole ordeal, she snapped me back to the reality of the situation by telling me "Well you better start believing it and get going before I change my mind about how long you have to hold it."
The second I taped the diaper onto myself I knew I'd made a mistake. The enema was making me cramp like nothing I'd felt before and as I looked up to tell Sarah I didn't want to play this game anymore, I heard the door click shut behind her as she wished me luck. I reached for the door handle to follow after her but to my horror it was locked. "Hey Sarah!" I called out. "You didn't lock this door did you?"
She laughed from the other side of the door and said "I had a feeling you'd try to cheat at our game and run off to the toilet, but there's no fun in that. I promise I'll let you out right at 15 minutes! You're not struggling already are you?!" She couldn't hide how much she was enjoying this as my discomfort turned to panic.