(unfortunately it is completely based on my imagination rather than anything that has actually happened to me!)----------------------------------------------------------
As a single 30yr old in London, I spend a lot of my spare time in transit - like many in my position - swiping left and right on Tinder. Sometimes we do get chatting away, and on the rare occasion one gets the odd date.
It was a grey January morning, and the office was still in a post-Christmas holiday slumber. I was mindlessly thumbing away on the app as I was waiting for IT to bring back my computer after it decided that it wasn't going to work today. I got a match with a rather nice-looking girl - her name was Sophie, she had blonde hair and was wearing a nice summer dress. Amazingly, within two minutes a message came through...
"Hey handsome! How are you? x"
"Hi Sophie! Thanks for the message
I'm good thanks, not in the mood for work today though!! You? x""Yep bored out of my head. Look I don't want to faff around, had a bad start to the year - I want to be a bit crazy and have a fun blind date tonight, and you were my first match today. You free? x"
This is the first time I've ever had this kind of message...
"I'm free tonight indeed! What do you have in mind? x"
"Its been ages since I've been able to entertain someone, fancy coming over to mine for food? x"
"That sounds great. Where and when? x "
"Let's meet in my local pub first, just to make sure you're not a psycho first
Its the Queens Arms in SW5, 6pm? Is there anything you don't eat? x""Oh I eat anything, just not beans - my friends make fun of me when I pick them out of stews. Otherwise anything! Do you want me to bring anything? Any dessert? x"
"No I'll provide dessert. What do you like? Just bring an open mind
x" "Oh I eat any kind of dessert, no problem
x"I felt a tinge of excitement at this rather unexpected blind date, and I did of course wonder what Sophie had in mind - was it simply a desire to entertain someone and have a fun night, or did she want to go further than that? Indeed I wasn't entirely sure that SHE wasn't a psycho, but meeting in the pub first should allay fears on both our sides. I'm traditionally the typical awkward Englishman, so I decided to ignore the last comment about the open mind and see what transpired. I daydreamed for a couple of minutes, when Mick the IT boy came over to give me my computer back. The day was going to be a slow one...
Come 5pm I left work and with no time to go home first, I headed straight down to SW5. I texted Sophie again to make sure that she was still serious and on time. She cheerily replied saying she was at the pub already, and sat in the far right corner.
A few minutes later I arrived, and could see Sophie sat in the corner with her face looking just as it did in her profile picture. She had blue eyes and a cheeky smile, sat amongst slightly wavy blonde hair that fell just to the inside of her shoulders, hiding the straps on a fairly revealing black evening dress that looked very out of place in this pub. I tried to hide the fact that my eyes were wandering over her cleavage as I went over to give her a kiss on the cheek, and I offered to get a drink. She asked for a glass of white wine, and I returned with that and a pint of beer for myself.
She looked at me quizzically. "Is that how you dress for dinner?" I looked down at my admittedly old shirt and dark jeans, the kind of clothes I normally wear to work. I gave a nervous laugh,
"Oh, erm, well I just came from work and had no time to go home... hope its OK?"
She smiled slightly. "For a man who for all he knew could be getting laid later tonight, I'd have thought you would have made more effort?"
I shifted uncomfortably, again my awkwardness taking over. "Oh I wasn't even thinking about that, I don't like to be presumptuous. I'm happy with an evening chatting to a lovely girl" I thought charm might defuse this slightly unnerving turn of events. There was a pause, and from her smile I could tell she wasn't exactly being serious so I felt quite relaxed still. She got out a bag and pushed it over to me.
"You know I said keep an open mind? Humour me with everything I ask of you and you will not regret it." She kept her hand on the bag, and cocked her head to the site intimating that I should say yes. The mystery of all this was completely intriguing, and becoming quite a turn on. I nodded, and she released her grip on the bag on the table. "Go to the bathroom and put these on."
I picked up the bag and looked inside. There was a pair of frilly satin knickers. Was this girl for real? I had never cross dressed before, but I got a buzz inside at the thought of this. I went off to do as she said.
I came back with the soft feel of the knickers snugly holding my 'bits'. I put my normal underwear in my coat pocket. Sophie had drank half her wine and was looking even more stunning now my hormones were in full flow. We chatted for about half an hour about mutual interests, our recent holidays, our boring jobs - just like any other date. Then she paused, and said "Put your hand under the table, I'll pass you something." I did so, and felt a box in my hand. I looked down and opened it, and inside was a very squishy cream bun. "Put this down the front of your knickers" she hissed.
I immediately got a slight erection, and her intense look told me to do it quickly. So I pulled out the front of my jeans and the band of the panties, and pushed the bun down the gap. Next thing I knew her foot was in my crotch pushing down as I squirmed in my seat. I looked around the pub nervously, to which Sophie said "Don't worry we are going back to mine now; down your drink."
I waddled out of the pub, looking down making sure nothnig was leaking out of my front. She led me down the road to her house, and we walked in. "Stay here" she said after she closed the front door. She took off her coat, and it revealed the full extent of her lovely black dress, just coming down to the knees and complimented with some sexy heels. Then I decided I would just do whatever she asked of me - I was smitten. And she knew it from the look she gave me.
I waited there as requested, and she came back with a bag. From this she took out a black bra, a pair of sheer stockings, and a red satin evening dress. "When I invite someone over, I expect them to dress up for it. So now I'm going to dress you up for you. Take your clothes off and put these on." I dumbly followed her orders, and took off my clothes. She helped me get the bra on, the clasp tight on my back. The stockings went up to my thighs and fit tightly, and finally I put the dress on. The material admittedly felt great on me and I ran my hands down my bum feeling its smoothness. Sophie looked disapprovingly and pointed at the front. "Tut tut" she shook her head, "you've already got cream on that nice dress I got you". I looked down at where some of the bun had leaked out from my knickers.
"Sorry" I replied meekly.
She grabbed my hand and led me through to what appeared to be her living room. There was no table in the centre though, just a chair in the middle of what looked like a small inflatable paddling pool. This was confusing, and she pre-empted my questions.
"If you were expecting a sit down meal with me then you were wrong. But I did invite you over for food and this is what you will get." Still holding my hand she led me to the seat and motioned for me to sit down. I sat, and she then leant over and kissed my forehead, slightly rubbing her breasts on my face as she stood up, and said "Relax and trust me". Despite this being completely weird, I was relaxed although definitely in a heightened state of arousal. Next thing she did was take each of my wrists and secure them to the chair's arms with duct tape. She took a step back and looked at me with an excited smile, and took a picture on her camera phone. "Aw so cute".
"Is this a ransom photo or something?" I replied dryly. But deep down I just knew she was trying to humiliate me.
"OK so although you won't be getting dinner, I did promise food. You were very vague on your choice of dessert so I've got you a selection to try." She left the room, and came back with a big carboard box. I peered in and it was full of different foodstuffs.
"First, I need to make you fit that dress better." She pulled out a can of squirty cream. "You need boobs". She then lent over, pulled out the top of the dress and the bra cups and pressed the button. A cold stream of cream went onto my chest, pressed against it by the elastic. She squirted until it nearly overflowed, then let the dress slip back. She patted her handywork "Hmm nice tits!" she exclaimed. "Now, do you like trifle?"
"Erm yes" I replied.
"Do you like it so much you want to be a trifle?"
"I can't say I've thought of that-"
"Well you don't have a choice now!" She pulled out a big bottle of strawberry sauce and started squirting it over my head, then my shoulders then all down the dress. It felt sticky and slowly ran down my shoulders. It smelled good though, and I licked some off my lips. After depositing most of the bottle from me, she reached back into the box and got out two cartons of custard. "A good trifle has lots of custard!". It oozed thickly over my head, dripping onto my legs and over my eyes so I couldn't see. I couldn't tell how much she was pouring, but it was at least the entirety of those two cartons. I then heard the familiar click of the squirty cream again and felt it falling all over me this time. The onslaught of mess stopped, and I felt Sophie step back and again I heard the shutter sound on her camera phone. Oh I was glad we had no mutual facebook friends....
She came back over and wiped my eyes so I could see again, and then she picked up two cans. "Trifle not your thing?" Before I could answer, she tipped the contents on my head "Maybe rice pudding is!" This was never something I liked to eat, but the texture running down me sent my arousal into overdrive, with my bulge pushing the knickers as far as they would allow. Sophie noticed this "Oh you like that then?" She pushed back the hem of my dress as far as it would go, and pulled out the knickers and deposited another can of rice pudding in there. She rubbed it in with her hands, but withdrew as she could tell I was near a climax of some sort. "Naughty boy, I need you to save that for later." I gritted my teeth. Her black dress was covered in flecks of cream and custard, her cleavage was becoming ever more revealed and all the textures running down me were sending me into overdrive.
"Sorry, this is exciting me like crazy" I said.
"Well I have a solution for that". A blue bucket was on the other side of the room, and she brought it over and put it under my nose. The smell was unmistakable - I looked down and there was a huge mass of baked beans, quietly floating there but waiting to unleash their horror on me. I gagged slightly at the smell - I really hated these things. My erection subsided. "That had the desired effect" Sophie said, "If you look like you will climax, this is going over you". I sniffed the bucket again and gulped.
"Now we are going to have a game" Sophie said. "I am going to throw six custard pies at you. Three have chocolate in them, three just normal custard. If you guess them all correct, then you can mess me up with the four chocolate gateaux" She pointed to these boxes of gateaux, looking extremely chocolatly and creamy. "But if you're wrong, you get all the gateaux and the bucket of beans for good measure. Deal?". I thought for a second, and with the evening being so ludicrous and me feeling completely helpless and humiliated tied to this chair in this mystery girl's house being covered with food, I thought any chance of getting my own back should be taken. "OK, deal" I said.
She lifted up the first pie. "Chocolate or banana?"
"Banana" I replied. She smashed it into my face. A mass of distinctly banana tasting custard forced its way into my mouth and fell with an almighty plop onto my legs.
"1-0 to you" she said, "But the odds are in my favour". She picked up the second pie ."Chocolate" I guessed. She walked over and smashed it face-down on the top of my head, rubbing it in my hair. Some large dollops went down my back, the cold making me shiver. She lent over and pulled the back of the dress out, making sure it went down. It was chocolate.
"2-0. Next?" She stood back, and I could see now her lovely black dress was getting even more streaks of dessert all over it from the leaning she had done over me.
"Chocolate again, I think." I replied. She smashed this one in my face with force again, left it there for quite a while, pushing in. The moment the lack of ability to breathe felt uncomfortable, she withdrew and let the plate clatter to the floor. Now chocolate was all down my front and up my nostrils. This was going well. I thought of the odds as she picked up the next pie, and thought what the hell. "Chocolate" I said confidently. Sophie came over with the pie and flicked the straps of the dress off my shoulders. "Are you sure?" The dress fell down off my chest under the weight of the mess, revealing the smeared black bra full of cream. I nodded. She pushed this into my face again, and guided the plate down my chest, all the way to my lap. It was an utter mess, but to my delight it was leaving a brown smear.
"Yes!" I gasped. "I won with two pies to go!". I gave Sophie a defiant look "A deal's a deal, its your turn for the hotseat!"
She giggled and gave me a look of resignation. "Indeed, well done". She brought over a pair of scissors and cut the tape from my arms. "You won, but you still look pretty pathetic". I stood up and the dress slid off my body. I was there in the filthy bra and the goo running down over the frilly knickers.
"Stay standing for a sec Soph" I said. She looked at me dumbly, as I picked up another carton of custard the was laying on the floor. I ripeed the top open and quickly threw it all over her chest and down her lovely black dress. I rubbed it in, feeling her boobs under the front. "Well you can't be wearing that now its all messed up. Take it off!" She slid the straps from her shoulders, undid the zip on the back and it slid down, revealing her slender body. Her skin was so far only slightly messed up. She worse a thin satin thong. This was perfect for what I had in mind.
I picked up a gateaux and placed it on the chair. "Sit on that". Sophie let out a whimper of mock protest, but I took her hand and led her there, firmly pushing her down as she sat. There was a splurting sound as the cake spread out from underneath her. "Oh I am so getting you back" I said as I taped her arms to the chair. I scooped up some of the gateaux from the seat and shoved it down the front of her thong and tapped it. She moaned. "Eugh!" then started giggling.
"Oh I can stop you laughing". I picked up the two remaining pies, one in each hand, and clasped them round each side of her head. The cream and custard spattered everywhere, getting tangled in and flattening her hair then running down to her breasts. I pulled out the bra cups and let it run in. I put my hands on my hips and grinned. "Lovely!" I turned and picked up the next gateaux and prompty shoved it in her face. I let it fall on her lap, and picked up some of the detritus and smeared it over her chest.
"Ick!" she exclaimed again, "You're mean"
"Oh I'm just getting started". I reached behind her and unclasped her bra. It fell down, exposing her breasts which hung pertly from her chest. The nipples were hard; she was aroused. I picked up the final gateaux and put it upside down on her head, smearing the chocolate over her shoulders and down her arms slowly. She wriggled but there was not much she could do. I went back to the box and saw the rest of her items - I squeezed syrup all over her head, let it drip in big dollops on her breasts, and then emptied the final can of squirty cream into her thong, and all down her arms. It was now my turn to pick up her phone and take a photo.
"Don't accidentally text this to your boss" I joked. Sophie sat there silently, whimpering but clearly being aroused by the feeling of everything dripping off her. I then remembered her threat from earlier. I turned to the blue bucket and picked it up.
"You wouldn't!" she exclaimed. "I was fair to you, you can be fair to me!"
"But you said the punishment for arousal was the bucket. Its only fair surely this applies to you too?" I looked at her writhing in her seat, and the erect nipples straining from behind all the goo. "A rule's a rule!"
She shrieked as I poured the contents over her head. She gagged as the beans ran down, colouring the yellow and white surface with a nasty orange. I recoiled at the smell.
"You bastard!" she shrieked. But behind the falling beans there was still a smile, even as I was laughing my head off at her pathetic sight. I scooped up some of the run-off from her feet with the bucket and poured it over her again. She spluttered again and sighed.
"You could indeed have got lucky tonight, but that stunt has put paid to that" she looked up at me "But you have earned a second date. Untie me and the shower is upstairs" She winked.