From Date Night to Day Trip

(Disclaimer: All participants in this story were over the age of 18 and fully consented to all activities and play that takes place.)

Something I’ve mentioned before about the website I work for is that it’s mainly a kinky dating site. One of the services we offer besides kinky BDSM dates is a sort of rent-a-date service. You can hire out a girl to act as a girlfriend or date. I’ve done these a few times and I normally decline them, not because I don’t like them, but because I am painfully awkward in public trying to pretend to be someone’s date. 

I can ensure a lot, but for some reason, I feel like I am a painfully awkward and cringe person when in a non-bondage dating situation. I don’t know what to say or how to act without feeling like I’m some weirdo. So to save everyone some time and embarrassment, I usually decline those requests letting everyone know, I’m just not a good fit.

Of course, because my requests are 99% male, they often don’t read my profile all the way through and still decide to make requests that I either don’t take or don’t provide. I tend to let them off gently with these men, letting them off with a reminder before denying their request. 

However, sometimes a request can catch my eye and maybe, just maybe, be accepted by me. One such request fell in my lap this past September. A man requested I attend his company gala as his date, with the promise of a bondage date in a hotel afterwards. The details were laid out simply and with even context that I understood my role and instructions to a comfortable degree. 

He asked that we meet at the hotel he was staying at so we could leave and arrive at his gala together. He asked that I dress sexy for the bondage side of things and beautiful for the gala. I decided to bust out two outfits that had never seen the light of day, one because it was far too sexy and the other, because I’d never know if I needed it. 

I used a lot of mascara and black eyeshadow while curling my hair into a wavy elegant texture. Red lipstick to accent my lips and bring the sexiness together. I decided to arrive at the hotel in the sexy outfit, as a treat for my date, and switch to the dress at the hotel before we left. I asked my date if I could arrive a bit earlier to do so and he agreed. 

I packed my things, bagged up my dress, put on my outfit, and got in an uber which would take me to the hotel. I wore a coat over my outfit for the sake of my driver and any passerby’s on my way to my date room. I’ll do my best to describe this outfit, as it is something I love but you can’t get it just anywhere. 

This outfit is all a one-piece, black, nylon, off the shoulder, gloved, glossy, bodysuit. It goes from my toes, all the way up to just above my breasts, curing back down to the tips of my fingers. It’s a sight to behold and accents my curves very well. I decided to wear a black face mask as well. I do this to help bring my mind at ease and hide my identity when with doms and in public spaces. 

I arrived at the hotel and took my things with me on my way to his room. I got some stares but I moved fast and with the help of my coat, no one could tell how provocative I really looked, my black heels clacking on the tiled floor as I made my way to the elevator and up to my date. The elevator was quiet and luckily alone. As the doors dinged and opened, I arrived in an empty hallway, and made my way to the room I was needed in. 

I approached the door and knocked. No response. I waited for a few seconds and began to look around. Maybe I had the wrong room? I dropped my bag and dress on the floor next to me and pulled out my phone to confirm if I was in the right place. I was indeed where I needed to be. I put my phone back in my bag, picked my things back up and knocked again. This time, a sound came closer to the door and opened it. 

My date was looking more or less disheveled. His suit was barely on, jacket missing and tie undone. His hair was a mess and he looked tired and maybe a bit sad. He turned and waved me in as he made his way back to the edge of the bed inside the room. I awkwardly shuffled in as the door closed behind me. I moved further into the room and placed my bag and dress down on a table near the TV, opposite the bed. I turned to him and removed my jacket, revealing my outfit. 

I was hoping by removing my jacket, I’d cheer him up, but he barely looked at me, only sulking and looking downward at his own feet. I stood there for a moment, confused and maybe even embarrassed. I decided to sit next to him, and see if talking would be more helpful. 

“Are you okay sir?” I said very softly. I looked around the room and could see that he was clearly having a bad time. Clothes and items laid out everywhere, the bed was a mess. I almost wondered if I should cancel this date and leave. Clearly he wasn’t in the mood for any kinky or “romantic” experiences. I sat there for a while and something came over me, causing me to sandwich his right hand in between mine.

He looked over at me, finally making eye contact. He let out a small sigh and finally spoke saying, “I’m sorry. I’ve just been having a hard day and my confidence has been at an all time low.” I leaned in closer to him, trying to be attentive and caring. “I only did this because I knew I couldn’t show up alone again and just needed someone to have so they didn’t judge me.” I don’t know why, but my heart was breaking for this complete stranger.

We talked a little more. He did most of the talking for the most part. He talked about how financially successful he has been in his life, but socially, he always felt like an outcast or inept. In a way, I understood how he felt. He spoke about how he inherited a lake house from his father, but has barely used it on account that he has had no work friends or friends in general to invite. I felt bad for him. The worst part was, there was nothing wrong with him appearance wise. He was older than me, by about 10 or so years. Combed brown hair, well kept facial hair. He was tall, had some good muscle and weight. His voice was toned and deep. I guess he was just a very emotional person. Maybe his personality was his weakness. I wanted to help him.

I stood up, and moved in front of him. I reached out my hands and waited for him to look up and eventually take them. He surprisingly did, without much convincing. I pulled him up and placed my hands on his chest, moving my body closer to him, basically squeezing my boobs against his chest. “Screw them“ I said while pressing up against him. “You have so many amazing qualities, you are being wasted around people like that. You are successful. You are strong, handsome, and in touch with your emotions. Screw that gala, screw those people who ignore the good parts of you. Let’s just leave them. You and me. Let’s go away for a while, somewhere you will be appreciated. I’ll appreciate you. I’ll be yours for a while. I’ll show you that you have power and you will have respect.”

I don’t know what came over me. I was acting very confident but also extremely submissive. I told him I had to be home by Sunday evening, and that I would be at his side and prove he was more of a man than he thought he was. I guess it worked because he slowly moved away from me, turned to a bag he had on a chair in the corner, unzipped it, and took out a bundle of red ropes.

He then took my waist and pulled me close. He peered down at me, before turning me around and forcing me to lean over the bed. He quickly and carefully tied my wrists, my elbows, my chest, and my shoulders into a tight and strict harness. My arms were pulled and secured to my back, I couldn’t budge. He added a tight crotch rope, it dug into me without much pain, but plenty of pleasure. He removed my face mask, showing my lips and full uncovered face. I opened my mouth and stuck out my tongue. He smiled before taking a wad of white cloth (it looked like wadded up panties he bought) and shoved them in my mouth, piece after piece until my mouth was properly filled, he took a large roll of what looked like four inch black PVC tape and started applying strips to my lips and face. He pressed each piece firmly into place and made sure I was more quiet with each piece of tape.

He then reapplied my face mask and my coat. My bondage and gag were now hidden. He packed up his things, and took my things as well, before grabbing me again by the waist, this time from behind me, and ordering me to start our way to the lobby. He shoved the sleeves of my coat into the front pockets, to give off the impression I was wearing it normally, but underneath, I was being kidnapped in broad daylight. While we waited for the elevator, I got a good look at myself in a mirror and was surprised to see just how normal I looked. It was as if I had entered and exited the hotel the same way. 

We got down to the lobby and he kept me close to his side. He forced me to stay by him as we walked up to the front desk so he could check out early. He paid the fee and the conversation was normal. I could tell the manager was looking at me a lot, and I was praying I didn’t have to communicate. Being gagged three feet away from a stranger who has no idea is very thrilling but also very scary. Luckily, we were able to avoid unnecessary conversation and we moved to the car. He first placed all the bags in the trunk of his car. It was a nice black sedan, a more expensive looking model and make. He then turned to me and I thought he was about to put me in the trunk, right here in the open and public parking lot. Thankfully, he opened the back seat of his car and had me step inside. He took that roll of tape he used for my mouth and tape my ankles and legs together once I sat in the car. He buckled me in, added a pair of sunglasses to my face, and closed the door. 

He got into the drivers seat and explained he would take me away for a bit. He told me I was right and that he didn’t need those people at his work. He’d been more successful then they’d ever be. The car left the parking lot and never made its way to the dinner, instead, the car entered the highway and slowly left town, towards the man’s lake house where I’d become his captive guest.

The evening sun was slowly setting as our drive took us down highways further and further from civilization. I wondered why he put sunglasses on me. Was it to stop me from using my eyes to call for help? Maybe as the sun went down, it’d be harder for me to tell where we were going? I didn’t really know because a blindfold would have just been more effective. Maybe he was supposed to tape my eyes and then put the sunglasses on me, but forgot that step. Regardless of my vision, I wasn’t really paying attention to where we were going. He played soft music on the drive, just loud enough to drown out my muffled moans and grunts through my gag. I struggled a bit to see if I could escape but found no slack anywhere. My arms didn’t ache too much just yet but the crotch rope was slowly driving me crazy.

The highway roads turned to pavement. The roads got smaller, less occupied. Eventually the roads got smaller, covered in a thick layer of trees and very little light from the slowly rising moon with the sun nearly fully set. We drove past multiple homes dotted around the lake. We must have been nearly two or so hours from the hotel and city by now. The car moved along the winding road, carefully turning corners and moving along the darkened path. We finally reached our destination with the way he turned the car in front of a decent sized home and put it in park. 

He took the bags from the trunk and made his way into the house, leaving me alone in the car. I decided to shake and struggle in the backseat, pretending like I was trying to escape my kidnapper one last time before I was officially kept in my new home and or prison. Of course, the ropes were never going to budge or slip, so I caught my breath and waited for him to return. Once he returned, he cut the tape from my legs, removed my coat, and escorted me towards the home. It was a two stories home with a log cabin exterior. It had a porch that wrapped around the front and back side out the house on its right side. 

I knew we were alone and unlikely to see anyone drive by or enter any of the neighboring lake houses, but I was still tied up in a sexy bodysuit and was hoping we could move inside a bit faster to avoid me being seen. Though it was challenging to walk in my heels, we got up the front steps and entered the home. It was decently furnished and decorated on the inside. It entered with a spare bedroom on our left and a staircase on our right. We walked past into a high ceiling living room. On the left side was what looked to be the door to the master bedroom and on the right was a dining room, with the kitchen adjacent to that. The screen doors lined the back wall opposite of us, letting out to the back patch which stood high on a hill, overlooking the boat house and big dark lake. 

He showed me the upstairs as well, more spare bedrooms and a loft area. Nothing too exciting. He seemed very nonchalant about it, but I was very impressed with what he owned. I kinda snuggled by his side as he walked me around. He finally felt more confident and started to wrap his arm around me and fondle me. We moved to the couch and he continued to feel me up. I think he appreciated having me here with him. This continued for a while. His karate hand stroking my thighs, lightly grabbing my neck, squeezing my breasts and firmly grabbing my ass. He had me completely at his mercy. I moaned and enjoyed his firmness through my gag and mask, which he finally noticed and removed. I could breathe a little more clearly now and enjoy his hands even more. 

He realized I was promised dinner and with our change of plans, that was now a bit up in the air. He left me on the couch to investigate his fridge and freezer in the kitchen to figure out what he had and quickly realized he needed groceries. It was only 7pm and he knew a local grocery store just 15 minutes away, and asked if he could leave me here while he got food for us for the weekend. I agreed and pointed at my bag with my feet. He picked up my bag and opened it, asking what I wanted? He asked if I wanted to be let go and I shook my head ‘no’ he pulled out several items, all resulting in a no from me. Eventually he pulled out my vibrating wand, and I nodded my head yes excitedly. He knew exactly what I was wanting to do in his absence and accommodated me. He took a chair from his dining room and asked where I wanted to sit while I waited. I decided to be brave and wanted to sit on the porch outside, overlooking the lake in the moonlight. 

 It took some time and a lot of ‘yes’ or ‘no’ questions for him to fully figure out the kinky idea I had cooking up. He placed a chair on his porch facing towards the water. He sat me down and taped me to the chair, keeping me still tied up in the red ropes but now adorned in black tape securing me in several places to the chair. My legs were taped to the front legs of the chair, with the vibrator taped in between, pushed firmly against my crotch. I looked up at the moonlight shining down on the water. I looked around and saw that no one was home anywhere nearby, maybe across the lake from us, but not close enough to hear or see me. He plugged in the wand to an outside outlet and moved back to me. He asked me again and again if I was sure of this, and I nodded and confirmed that this was what I wanted. 

He clicked a button on the wand two times and moved past me, entering the house and eventually, leaving out the front to go get groceries. I was alone. Normally I don’t recommend leaving anyone alone in bondage, but I am a professional and am quite the escape artist. While he was securing me to the chair, I was able to pick at the ropes binding my arms and with enough finesse, pulled them loose enough to where if I pulled them further, the ropes would loosen and I could shimmy my arms free and eventually work on my wrists. 

But I didn’t need to escape, I was too busy escaping into pleasure. The feeling of being bound, grabbed, tortured, and exposed out in the open was exhilarating. I was secretly hoping someone would be home nearby to add to the experience. I squirmed and resisted the bondage and vibrator as much as I could, but they were starting to over power me, and within the half hour, I achieved climax. 

He returned mere minutes after I had finished in the chair, noticing my moans and squirming, realizing I was ready to be let go. He untied me and told me my bag was by the front door. I was allowed any bedrooms in the house to use and change inside. I jokingly asked about his bedroom but he politely declined. I was honestly surprised by this but not upset or offended. I took a bigger bedroom upstairs that had a little patio and a bigger bathroom. I had my own little rocking bench and shower, best of both worlds. I got cleaned up and changed into some booty jean shorts, a pink t-shirt, and white socks. I removed a good chunk of my fancy makeup and kept things simple. 

He cooked us a nice chicken and pasta dinner. We talked about our careers and how we got into kink. By then it was late and we decided to call it a night. I took off my bra and kept my pink shirt, took off my shorts revealing my fresh pair of white panties, took off my socks and removed all remaining makeup. I crawled into bed and fell asleep faster than I thought I would. I remember waking up in the middle of the night to use the restroom. Once I finished my business, I got an odd feeling and locked the door to my room. Not that I didn’t trust my dom, but you can never be too careful. 

I woke up to the smell of breakfast being made and finally decided to sit up straight in bed. My hair was a mess and my pajamas had shaken loose in my sleep, exposing my left shoulder and looking incredibly disheveled. I didn’t feel the need to change and decided to go investigate the smell and be presentable later. When I got downstairs, I was greeted by my dom (whom I will finally give a name: Eric) who had plated some bacon, scrambled eggs, and the choice of orange juice or water. I went with juice because I can occasionally be childish and this was a fair opportunity. We ate and again chatted before deciding what to do for the day. We agreed we both needed to be back in town Sunday so today was our only day to have fun and fool around.

We decided we’d save some of the more advanced bondage play for the evening and maybe do something light during the day. I came up with some simple lounging bondage that seemed to peak his curiosity. The sun was out and the weather was in the high 70’s so there wasn’t much risk of sunburn or heavy tanning. I offered to let him restrain me to a pool bench down by the boathouse while we relaxed and enjoyed the sight and sounds of the lake. It was a dead weekend so not many people were out and about or on the water. You could maybe see a boat pass once an hour or so.

He agreed and we both went to our own rooms to change. I always pack an assortment of things when I go on bondage dates because I never know what to expect or where the roleplay will take me. I also like having a bathing suit in case I need to shower in a hotel or something and don’t want to risk getting peeped at. I got incredibly lucky with my bikini choice because it was so cute and perfect for a lake day. It was a two piece pink swimsuit with a frilly skirt and frills along the bra straps. It was more of a light pink color and would look really good with a light pink ball gag I had at home. Unfortunately I didn’t bring it in my bag which was such a shame. 

I threw on some white sandals and white-rimmed sunglasses and met him down by the back patio. He had changed into swim trunks and a black shirt. His muscles kinda bulged out of the shirt and shorts a bit and he caught me staring. What can I say, I like women with curves and men with muscles. I’m no better than most people in that regard. We walked down all the steps and all the way down the hill to the boathouse and dock. The orange wood spread out from the boathouse, creating this open dock with lawn chairs and a picnic bench, the boathouse itself was simple, featuring a boat that was held above the water by some sort of metal platform. Eric told me that the boat was low on gas, so it was unlikely we would be taking it out on the water. Probably for the best, though the thought of being kidnapped on a boat was an interesting idea. 

I applied sunscreen and was generous enough to let Eric apply more on the hard to reach places like my back. I’m flexible but a girl has her limits and when I have a hunk of a dom near me, I’m going to take what I can get. We settled on some simple restraints, tying my two ankles together and securing them to the bar at the base of the pool chair. My arms were then held above my head, tied together and connected to a bar at the top of the pool chair. I was stretched out to a comfortable position before the finishing touch. He took some clean socks I had brought down with me and rolled them into a wad before shoving them carefully into my mouth. He then took some clear tape, the size was about 3-4 inches in length, and applied several strips. You could see the socks through the tape, but from a distance, I don’t think anyone could tell.

Eric laid out closer to the shade the roof of his boathouse provided. He angled himself in a way that he could see me to his right while I soaked up the cool sun all tied up. I sat in my chair, sunglasses still on, slightly adjusting and struggling in my bonds while enjoying how nice the day was. I realized how I had nothing planned for Saturday and was grateful because in a weird way, I was getting a tiny vacation out of all of this. Eric had headphones in so I doubt he could hear me moan or grunt through my gag unless I really yelled.

Hours passed and I hadn’t grown tired or sore from my position. Some boats passed by during that time and I wondered if they could see me, or the predicament I was in. What would they even do? Even if they did see what we were up to, wouldn't they just think we were some weirdos not bothering anyone? I thought about it, but in the end, there was no point in worrying about it. At some point, lunch must have come and gone, because I could tell it was past noon. I guess I was too busy sucking on my own socks tape into my mouth to notice. Funnily enough, I wasn’t hungry, maybe due to the decent breakfast I had. 

Eventually, Eric must have had enough and was ready to turn in, but didn’t want to leave me alone outside again. I wanted to stay, but in his defense, I didn’t have the night sky and trees to hide me this time. I agreed and he first took out my gag and gave me some water to drink. He untied me and we both went up together. I think he was going to get dinner and the night's festivities in order while I showered and got dressed. I got up to my room, locked the door, entered the shower and kept my bathing suit on. I trusted him to an extent, but I like to be somewhat careful. 

Dinner came and went, I can’t even remember what we ate on account for the bondage activities taking over my memories. My outfit for the night was a black lace teddie. It’s basically a nightgown with a lot of silk and see-through fabric. The fabric would hang from my bra down to my upper things. I accompanied the night gown with black panties and no socks or gloves. Wanted to keep things simple and since I had already shown him skin, it made sense to dress lightly. He started by tying me up with the red rope he’d been using since yesterday by placing me into a frog tie. My arms were pinned horizontally behind my back, with a make-shift harness used to keep everything in place and accented. My breasts were starting to be squeezed out of my nightgown bra, so I tried not to adjust too much, not wanting to risk them spilling out and exposing me. Not that it was a bad thing, I was trying to be somewhat put together looking.

He had me sit on my knees in front of him. He sat in a leather loveseat and poured himself a drink. He took a blindfold I had brought with me and applied it to my eyes. He played with my mouth and lips using his fingers for a little bit, lightly slapping me and placing his hand lightly around my throat. Eventually he must have gotten sick of my whimpers and moans, because I felt more clean socks being pressed into my mouth. He took a dark blue piece of  fabric I had in my bag and began tightening it over my mouth. Pulling as much as he could to keep the socks in place. If I was doing it, I would have taped my mouth and then applied the fabric but what would I know right?

I continued to sit in front of him, feeling his hands caress my breasts and run down my neck and face. He continued to lightly slap me, never actually hurting me, but definitely making me whimper and yelp through my gag. After a while, he picked me up and placed me, laid across his lap. He continued to feel me up, squeezing my butt and breasts. I was kept as an object for his pleasure, no sight, feeling, or sound. I kinda slipped into a subspace for a while, only reacting to the feeling of his hands. I zoned in and out, eventually feeling his hands wrap around me and lift me off of him. I felt the thud of every step he took as he carried me, too many steps to be his room and too many to be the car…where were we going?

Suddenly, I was placed on a bed, with my back leaning against a wall of pillows. My legs were spread apart and I began to worry. I thought he was going to try and have sex with me, despite my contract saying against it. But the thought of the night prior where he denied my joke of sleeping in the same bed as him crossed my mind and my confusion only furthered. But to my surprise and enjoyment, the vibrator from the night before was pressed against me, held by my dom and used against me. He tormented me for what felt like eternity, but was really an hour or so. Keeping me on edge and close to climax over and over again, always pulling the wand away right when he could tell I was about to cum. Rude. 

Eventually, he gave me the release I was begging for  through my tight gag and left me there, to wallow in my ecstasy while I caught my breath. I could feel his hands on me, caressing and folding me while the ropes began to loosen. Before I knew it, my hands and arms were free and he had left the room. I removed the rest on my own, showered and used the restroom before reapplying my pjs and going to bed once more. 

Eric was kind enough to drive me to my townhouse neighborhood the next morning. I actually rode shotgun while gagged under my mask and my wrists taped in front of me in my lap. I wore some black booty shorts and a light blue tank top with my white sandals from the day before.. I would squish my arms together to push my cleavage upwards and make my boobs bigger. He would occasionally grope them during the drive. When we got back, he put my coat back on me, placed my bag over my shoulder and allowed me to walk back to my townhouse by myself. I was once again walking while still captive in public but nobody was around or nearby enough to see me. I dropped my back at my door, fiddled with my bag to get my keys, and safely entered my house. I was home but there was one problem I forgot to consider.

How was I supposed to untie myself now? Guess I’ll go find some scissors, and be extra careful.