UMD Stories

WAM Date--Annie
Story by AJ2
Posted 2/13/24     1191 views
The following story is part of the "WAM Date" story set. All of the stories are based on real events, although the names of the young ladies have been changed to protect their privacy.

I first met Annie when we were both involved in the same show. She had amazing, long brunette hair, an attractive face and a pretty smile. She was slim and about 5'5" tall. We got chatting during the breaks and quickly hit it off.

Our first date was a daytime cinema date. It was a simple date, but we enjoyed each other's company and agreed to meet up again. We enjoyed a theatre show next, and it was great to see her dressed in figure-hugging jeans, a cute top, and strappy black heels. She revealed that she didn't feel too confident in heels, but she made them look amazing all the same. The third time we met up was at my house, again during a daytime

Annie hadn't been in a serious relationship before, so we were intentionally taking things slowly. I knew she was fun to be around, but also quite prim and proper. It's safe to say that Annie was the sort of young lady who wouldn't have played strip poker before! That all being said, kissing Annie definitely had an effect on me and I was pretty sure it was having an effect on her too! We were enjoying each other's company on the sofa when I looked into her eyes, and said as temptingly as I could, "I have a little challenge for you". "Oh? Okay!", came here response. "Your challenge is to strip down to your underwear for me!" The shock on here cute face was really something to behold! "Oh my gosh!", she giggled. "I know we're taking things slowly, and I'm genuinely happy with that" I said to soften the shock, "but I'd really like to see a little more of you, if you get my meaning". Annie giggled again, which was really cute, but I sensed that if she could talk her way out of any undressing, she was going to!

Before she had chance to say anything more, I took the initiative. "I've got a little something in mind to help convince you this is a good idea!". "Oh! And what's that?!" she asked. I gently leant over her, and slowly pulled out a silk blindfold I'd placed there earlier in the day, just in case I had the chance to use it. Annie's eyes widened, and she looked back at me to try and see exactly what I was thinking. "This is only a part of it, but I think you'll enjoy the suspension. I promise you'll be perfectly safe with the blindfold on." My heart was beating hard as I watched her process this promise as I waited for her response. "Okay, I trust you" came her reply. I hadn't thought it was possible, but my heart suddenly beat even harder! I gave her a gentle kiss on her lips before delicately placing the blindfold over her eyes and starting to tie the loose ends of the blindfold behind her head. She was smiling as I did this and brought her hands up to her face to smooth the blindfold down over her dainty nose. "Oh my gosh", she giggled again. I knew she still didn't really want to remove any of her clothing that day, but she definitely seemed to be enjoying being blindfolded. She sat with her hands in her lap, a slight smile on her face, and asked softly "do I want to know what comes next?". "I just need a moment to fetch something, then I'll be right back." I said this as comfortingly as I could, my heart still beating like mad at having an attractive brunette sat in front of my, smiling, blindfolded, and not having a clue what I had in mind for her!

I popped into the kitchen and grabbed what I needed, before heading back to the living room. "Okay, I just need you to hold your hands out" I told her. Annie dutifully obliged. I placed one item in her left hand and another in her right hand. A look of puzzlement spread across her face. I was definitely enjoying the suspense, and I was hoping that she was too. She quickly worked out the paper plate she was holding, which I took off her so she could focus on the second item. Seeing her two hands run up and down the long object was ridiculously sensual, especially as she focused on the rounded top, trying to work out what it was. After a few moments, a look of realisation and shock appeared on her face as she announced "Whipped Cream!", which I was glad to note was followed immediately by a laugh. "Oh my gosh!" she exclaimed, while I was still drinking in her reaction. "So you've worked out the forfeit if you don't slip down to your underwear for me?" "Yes! A pie in my face!" she squealed. "A good forfeit?", I dared to enquire. "Yes!", she laughed. I laughed too, and seeing that she seemed to be happy to play along, I took her hand in mine and gently pulled her to her feet. I slipped her blindfold off, gazed into her eyes, and gave her a passionate kiss. Her body responded, and we enjoyed the moment together. I was at risk of being too distracted by our kissing to discover whether she was going to undress for me or choose to let me pie her instead, but my brain kicked in before I got completely lost in her. I pulled away momentarily, grabbed my phone, set a five-minute timer, which I showed her, and with a smile as our eyes met (hers slightly wider at the realisation of a count down!), I set the timer running. Seconds later, we were kissing passionately again. As the seconds ticked by, I teased her by reminding her she only had a few minutes left to slip her top and jeans off. With her eyes wide, but a smile still on her lips, all she could whisper was "No!". I teased her more by reminding her that in a few minutes time, she would be kneeling down in front of me as I gently smushed a pie in her pretty face. This was met with a further breathless "No!", but her smile told me she was still enjoying herself. I was too, of course the kiss was amazing and we were seconds away from Annie discovering which decision she was going to make!

I don't think Annie would have chosen to be pied, but while she was enjoying being kissed and was confident that she didn't want to undress for me quite yet, our kiss continued until my phone alarm finally brought us both back to reality. We didn't break off immediately, but as soon as it felt natural, we both pulled away and gazed into each other's eyes. "Time's up!", I whispered to her with a smile. "Oh no!", she exclaimed, also smiling. "It's time for us to make up the pie" I announced. She brought her hands up to cover her face as she shook her head and whispered "Oh no!" in between more giggles. I leant over Annie to grab the paper plate and can of whipped cream. "Kneel down for me, Annie", I just managed to get the words out. She hesitated for a moment, perhaps wondering if she could find a way to escape, but a few seconds later, she knelt down, placed her hands in her lap and looked up at me in expectation. "Now hold this, please", I asked her, and she dutifully held her hands out to hold the empty paper plate. I kept looking into her eyes as I shook the whipped cream can, drinking in the tension that seemed to be building inside her. She was still smiling, but I sensed a little apprehension too. "I promise I'll be gentle" I said to reassure her. If she'd protested with any seriousness, I'm sure I would have let her off (If I couldn't have succeeded in talking her into it!), but she continued holding the empty paper plate out for me as I squirted the whipped cream in swirls all over the plate. "Oh gosh" was all she managed to say as I continued to fill it with the full can of whipped cream!

Our eyes met as I took the now fully prepared pie from her, and I was relieved that we were both smiling. My heart was beating hard again in anticipation of what was about to happen, but despite this, I wanted to draw the moment out a little bit longer. "You know I don't really want to do this to you, don't you? It's only because you insisted on keeping your body hidden from me just a bit longer." Annie sensed the teasing nature of my question as she responded "I know you're going to enjoy doing this to me!" She wasn't wrong, to be fair! But I was going to enjoy drawing it out a bit longer too. "Any last words?" I asked her? "You're so mean!" she laughed at me! There was definitely a heightened sense of anticipation in her voice too, as she knew the moment of her pieing must be getting close. "Mean?!", I protested? "How am I mean?". I wasn't quite sure how long my teasing was going to go on, but as soon as she said "You're going to pie me in the face!" I knew the time had come! In one movement, I slipped one hand behind her head and brought the pie up to her face with my other hand. I saw her scrunch up her face as I did so in anticipation of what was to come, and without stopping, I gently pushed the pie into her pretty face and smushed it around for a good few seconds. I heard her gasp and felt her shoulders hunch as she experienced the feeling of being pied for the very first time. It felt incredible to have pied her only a few minutes after kissing her passionately! As I took my hand away from the back of her head, she brought her hands up to her face and removed the paper plate, revealing a very creamy and still very pretty face. She was giggling uncontrollably, which I knew was a good sign! As she looked in the mirror, she exclaimed "Just look at me!". And so I did, enjoying her deep reaction of shock as she wiped as much of the pie away as she could and continued to giggle uncontrollably for several minutes after!
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