First date: Sleeping with a stranger

Submitting to my new master

Hello, my name is Anna and this is the story of how I met my Master, Jonathan. I’ve divided it up in several chapters, one for each date we’ve been on.

First date: Sleeping with a stranger

This story starts at the time I worked as a secretary at a small legal firm and was about to be promoted to personal assistant to one of the managers. The only thing between me and that promotion were some certifications missing from my repertoire.
To get these certifications and the coveted promotion, I was sent to a training center where I was enrolled in weekly classes – three days per week, after working hours – for the next two months.
The training center of course, is where I met Jonathan. He was not one of the instructors – though that could have been quite interesting – nor was he another student. He worked the front desk, enrolling students, providing paperwork, answering all your questions.
Every day Jonathan welcomed you with a warm smile, a well-meant compliment or a joke to brighten up your day. I felt swiftly attracted to the handsome, friendly man.
I replied to his good-natured quips in kind and often found myself chatting to him until I was almost late for class. We flirted eagerly and I often ended our conversations lamenting that my group was starting and would sorely miss his company.
It was my second week at the center when Jonathan took my mock malcontent as an opportunity to ask me out for a drink.
I arrived at the center about twenty minutes before the start of my class that day and arrived at an empty lobby. Most people waved Jonathan hello and made their way either directly to their classroom, or to the cafeteria. I however walked up his desk for a quick chat.
“Good morning, John.” I greeted him, for he had already taught me his friends called him by this name.
“Anna.” He replied. “Looking fabulous as always.”
I couldn’t help but smile at the compliment. “I know you say that to all the women, John.” I replied.
“That’s because you are all fabulous.” He countered. “But you most of all.”
“All of us?” I asked. “Even Samantha?” One of the instructors who, despite her young-sounding name, was in her late sixties with short grey hair, wrinkled skin and a love for ill-fitting, baggy sweaters. I didn’t usually put other women down, but Samantha and I just didn’t mix well.
“Samantha especially.” Jonathan replied. “She is a close second. If not for those hideous sweaters you might be in trouble, keeping onto that first place.”
I laughed out loud and Jonathan smiled broadly. He then asked me about my day at work and I told him all the fun gossip that went around at our little firm.
Those twenty minutes went by in an instant and I quickly found myself frowning at my watch. “I wish we could spend more time together, John.” I said. “But I have to get to class.”
“After class then.” Jonathan replied. “We could go get a drink?”
I smiled broadly. I had been waiting for him to ask me out. Part of me knew I could’ve just asked him, or even tried something more subtle like slipping him my phone-number on a piece of paper with the rest of the paperwork he handled; but I enjoy the old-fashioned dynamic of waiting for the man to ask you. “Sounds great, I will see you after class then.”

That evening’s class went by as slowly as ever – coincidentally it was instructed by Samantha – though I didn’t think about my plans with Jonathan until the end of the session. It was just drinks with a friendly guy at that point, I didn’t have too many expectations.

After class I waited in the lobby while everyone left. Our class was the last one scheduled for the day, so after everyone was gone John packed his things and we left together.
We went to a small bar for drinks and picked up our conversation were we’d left of. Most of our chats were either about work, or the classes at the training center. I decided to steer the conversation somewhere more interesting by asking Jonathan whether he often picked up girls at work.
“You are the first woman I’ve asked out since I started there.” He replied, with an emphasis on the word ‘woman’.
I grinned. I often referred to myself as a girl when talking with him. While I am in my early twenties, Jonathan was almost thirty and while the age-gap wasn’t that large, I enjoyed teasing him with it. “The first woman, eh?” I replied, same emphasis. “How many men then?”
John laughed. “No men, just you.”
“Hmm, must be that you wanted to ask me something you couldn’t ask at work. Perhaps something you didn’t want your co-workers or boss to overhear?” I teased.
John smiled. “Maybe, what do you think I would want to ask you?” He evaded the question.
“I don’t know. Ask me anything.” I dared him.
“Alright.” Jonathan agreed. “Whenever we talk, you have this little twinkle in your eyes, as if you’re thinking about something naughty. So Anna, tell me something naughty about yourself.”
I licked my lips, now this conversation was going in the right direction. “Bad naughty, or sexy naughty?” I asked.
“Sexy naughty.” Jonathan replied.
I grinned. “Well, there is one thing I think I can share with you John … I seem to be attracted to older men.”
Jonathan coughed, almost choking on his drink. “Alright, that’s enough about that.” He replied. “I’m not that old, we’re only five years apart.”
I blushed slightly. Only five? I had estimated it to be closer to seven or eight. John had my files however, so he would know. “I’m sorry.” I replied. “Was it naughty of me to tease?”
He grinned. “Very naughty. Perhaps you need to be punished.”
I licked my lips again and put my hands in my lap to stop myself from squirming in my seat after hearing him talk about punishment. “What can I do to make up for it?” I asked.
“Tell me something true this time.” Jonathan replied. “A fantasy, a sexual one. Something you haven’t told anyone else.”
I blushed slightly, the conversation seemed to be accelerating towards more intimate topics. I wasn’t too shy however, and didn’t mind. Though while there were a lot of fantasies I could share with him, you didn’t tell someone on your first date that you wanted a man who would dominate you, a man for whom you would kneel and wear a collar, a man who would own your body and do with you as he pleased, a man who would punish and spank you when you misbehaved.
I had to come up with something less intense, but still interesting. After a short silence and a few sips from my drink, I knew what to tell him. “There is this one fantasy.” I began. “It’s about sleeping with a stranger. Not sex, but actually sleeping.” I paused a moment to take another drink. “Imagine you’re at an airport and your flight gets cancelled. The next flight is the following morning, so you have to stay the night. You meet this guy at the airport and you decide to split a room at a hotel to save some money. There is only one bed, so you have to share.” I took another small pause, Jonathan was listening intently. “You both promise to each stay on your side of the bed, no touching, and definitely no sex. However, I am the kind of girl that sleeps in the nude, so I undress and climb under the blankets, completely naked. The man does the same. Our bare bodies are but inches away from each-other. You close your eyes, feeling completely vulnerable, but all you can do is trust that this complete stranger keeps his promise and stays on his side of the bed.”
A short silence followed. Jonathan licked his lips. “So how does it end?” He asked.
I grinned. “There are many different endings. Though I prefer the one where we both keep our promise, resulting in a long, rousing night of hot dreams and squirming anticipation.”
“So you like being made to wait, or even denied gratification?” Jonathan asked.
I blushed. “Only one question.” I evaded. “Now it’s your turn.”
Jonathan grinned. “We weren’t taking turns. This was your punishment for teasing me about my age. Though I guess I could be a good sport and share a fantasy of my own. I can’t promise it will be as elaborate or as arousing as yours though. I’m not as good with words as you are.”
“That’s okay.” I replied, eager to hear the fantasies of a man who teased you with words like naughty and punishment.
“Well, I’ve always wanted to tie someone up, so that I have them under my control and I can have my way with them.” Jonathan said simply.
I bit my lip, so much for my assessment that you shouldn’t divulge such things on a first date. “So, like playing with handcuffs?” I asked.
Jonathan grinned. “Only one question.” He countered.
“That’s not fair.” I pouted. “Mine was a lot more detailed.”
He smiled. “Alright, I’m thinking handcuffs, shackles, and even enough rope to have you tied up completely.”
I took a deep breath to push down the excitement I felt, knowing we shared such fantasies. “I don’t think tying me up completely would be very appropriate on a first date.” I teased.
John smiled. “No, I guess not.” He pretended to think for a moment. “What does modern dating etiquette say again? You should wait until the third date before such things?”
I grinned. “I believe so.”
“Though, if I may make a suggestion.” John said while taking a big gulp from his drink. “Sleeping together isn’t considered sex and three dates from now, we can hardly be considered strangers anymore. That is if you’re interested in ever making that fantasy of yours into a reality.”
I blushed. “We’re not strangers.” I countered, while giving myself time to think about this proposal.
John smiled. “Maybe not, though we’re the closest to complete strangers as you’ll get. Unless you’re telling me you’d already be entirely comfortable sharing a bed with me, completely naked.”
I blushed even deeper. This time I was squirming in my seat. “So what do you suggest?” I asked. “We just pay for a hotel-room and spend the night?”
“Why not?” He asked.
My heart was racing. So far this date had been going better than what I had hoped for. Jonathan and I already hit it off when we talked during day-hours and now I was sure that behind that friendly facade of the man behind his desk, was the kind of dominant partner I was looking for. The longer the evening stretched, the more positive my experience had been. It seemed stupid to cut that off now. “All right.” I agreed. “But we agree: no sex, no touching, just sleeping.”
Jonathan smiled. “Of course. I want you to know you can trust me.”
I smiled. Right, if Jonathan was the kind of guy that would tie you up, you’d have to be able to trust him. “Well then, one more drink and then we go and find a hotel?” I asked.
“One more drink.” Jonathan agreed.

We’d taken Jonathan’s car to the bar, leaving mine at the training center. He was supposed to drop me off after drinks, but instead we drove to a small, local hotel. I wondered whether anyone would notice that my car stayed overnight at the center and whether they would know what that meant.
At the hotel I waited nervously while John acquired a last-minute room for the night. We didn’t need anything special, we weren’t staying long.
In the small elevator up to the fifth floor where our room was located, I could feel a tingling sensation in my skin from standing this close to Jonathan. Yet we were still dressed and almost an arm’s-length apart, it would get a lot worse once we went to bed.
Our room was quite small, with just a narrow table, an open wardrobe and a two-person bed in the middle of the room. A quick inspection showed me it had separate bed-sheets rather than one large one. Part of me was disappointed by this, but I quickly realized a thin layer of fabric wasn’t going to be much protection if Jonathan decided he wanted to cup a feel.
I took a quick trip to the tiny bathroom while Jonathan looked around the room. As I stared in the mirror I wondered whether we should’ve dropped by my place to pick-up my toothbrush. But no, that wasn’t necessary, we weren’t planning on kissing or anything…
As I continued to look at myself in the mirror I asked myself what I had gotten myself into. How had we gone from drinks, through naughty conversational topics, to this?
I wasn’t having second thoughts however, I was just nervous. Nervous about undressing in front of Jonathan, nervous about sharing a bed with a man I hardly knew, nervous about how excited I was to do this, and nervous that perhaps I would be the one unable to constrain myself and follow the rules.
With my heart in my throat and my skin feeling like it might shed like a snakes, I left the bathroom. It was already quite late, with after-hours classes and drinks after that. There wasn’t much else to do but go to sleep.
“Ready for bed?” Jonathan asked.
I nodded and, with nothing else to say, started to undress. I had already taken off my jacket so I started with my blouse. Slowly I undid the buttons at the front, revealing the cute lace bra I wore underneath. “Aren’t you going to undress as well?” I asked Jonathan. “Or are you going to keep staring?”
He smiled. “If you met a stranger at the airport like in your story, don’t you think he would stare?”
I blushed, but conceded he was right. I finished the last button and pulled the blouse off my shoulders. The zipper on the side of my skirt came down quickly before I dropped it to my ankles. Underneath I wore nylon stockings and cute panties that matched the bra. I could feel Jonathan’s eyes on me the whole time.
I pulled the stockings down my hips and when I sat down on the bed to slowly roll them down my legs, Jonathan finally started to undress as well. I watched as he undid the buttons of his shirt, revealing his strong chest and firm abs. I looked at him, lower-lip caught between my teeth, stockings forgotten between my fingers.
Jonathan smiled and winked at me as he pulled the shirt off. I blushed when I realize I’d been the one staring this time. I quickly pulled the stockings down to my feet and got up. I turned around to take off my bra, not to hide from him, but to stop myself getting distracted while he unzipped his pants.
This of course had the added benefit that I had now presented him with my backside and I could just feel Jonathan’s eyes burning into my back, especially when I bent over to pull down my panties and bare my bottom.
When I turned around again, fully naked now, he was staring at me just like I had anticipated, trousers off, wearing just his boxers which where bulging. I licked my lips and stared at his crotch unabashed. I took a deep breath when he grabbed his boxers and pulled them down swiftly, his cock sprang out, large and erect.
I closed my eyes for a moment and shook my head. He wasn’t going to use that cock, I had to remind myself. We were just going to sleep. Yet when I opened them again I couldn’t avert my eyes. It was large and throbbing with excitement, huge veins running along the side. I imagined how it would taste, how big it would be if it filled me up…
“Ready for bed?” Jonathan asked.
I blushed. “Yes.” And turned off the light to spare myself the sight of his manhood. The room was dark, but not completely. I pushed aside the sheets and climbed into bed with Jonathan.
“Goodnight Anna.” Jonathan whispered.
I almost shivered, his voice was so close. How far would I need to reach to get to him? Would I even need to fully stretch my arm? I had to stop myself from trying. “Goodnight John.” I replied, burying my arms safely under my pillow.

It was a very silent night, especially for such a cheap hotel. The only thing I heard was Jonathan’s breathing. Every breath he took was a reminder that not only a naked, attractive man lay within arms reach, but that I lay within reach of them as well.
Like the stranger from my story he could reach out and grope or fondle my naked body. He could even wait till I slept so that I wouldn’t know of his betrayal. I had told Jonathan that this story had many different endings and the stranger broke his promise almost as often as he kept it.
Jonathan wasn’t a stranger however, even though we’d pretended he was. He was someone I liked, someone I’d flirted with, someone I’d date. Part of me wanted him to break the rules, to just grab me and fuck me. Yet I wanted him not to even more. I wanted him to prove I could trust him, so that one day he could tie me up like in the fantasy he had shared with me.
I don’t know how long I lay there awake, aware of Jonathan’s body right next to mine. I just couldn’t sleep, my heart was racing, my body tingling, my crotch burning with desire. When Jonathan’s breathing slowed down and I realized he had fallen asleep, I could finally start to relax, feeling safe in the knowledge that he was going to keep his promise. I closed my eyes and slowly drifted off.
Sleep didn’t bring much rest however. My subconscious did all the things to me than Jonathan had promised he wouldn’t. I dreamt that he grabbed me, teased me, fucked me. I dreamt of him tying me and using me for his pleasure. I even dreamt of him punishing me, spanking me until I begged for release.
I woke up sweaty and disoriented. It was hot under those sheets and I blushed deeply with my dreams still fresh on my mind. I held my breath to calm myself for a moment and listened for Jonathan’s breathing.
He sounded calm and reassuring. I wondered whether his night had been as tumultuous as mine and blushed again, imagining all the things he had done to me in his dreams.
I rolled onto my back and pushed down the sheets, hoping that the cold air on my skin would cool me down.
“Feeling hot?” Jonathan asked.
I blushed and grabbed the sheets, yet was able to stop myself from pulling them up to cover my chest. I didn’t want to seem like a flustered little girl. “A little.” I said, turning my head to look at the man in my bed. “I thought you were still asleep.”
He was looking at me, but his eyes kept sliding down to my chest and my bared breasts. My nipples were hard and erect, from excitement as well as the cold air.
“I didn’t get much sleep.” Jonathan said.
I blushed, thinking that his lack of good sleep must’ve had the same reasons as mine. “Turbulent dreams?” I asked.
Jonathan laughed out loud. “I see you know what I’m talking about.”
I grinned and used the moment when he laughed to pull the sheets back up, covering up my naked body and concealing my tits from his staring eyes.
“What time is it?” I asked, trying to sound calm and indifferent.
“A bit past seven.” Jonathan replied. “Almost time to get ready for work unfortunately. Though I wish I could stay here in bed with you all day.”
I grinned. “I think staying in bed all day would be more fun after the third date.”
Jonathan laughed out loud. “We’ll have to plan something then when we reach that stage.” He smiled, trying to look more serious. “Do you need me to drop you off somewhere?”
“Yes please, my car is still at the training center. I can drive to work from there. I guess I can wear yesterday’s outfit one more day.” I replied.
“Alright. Let’s get going.” Jonathan said and he pushed himself up. I took a moment to take in the view of his broad shoulders, strong muscled back and – as he stood up – firm buttocks. When he turned around, my gaze was immediately drawn to his cock, large and erect as it had been the night before.
“Aren’t you going to get dressed?” Jonathan asked when he noticed me staring again.
“I will.” I replied with a blush. “I’m just waiting until you have some more clothes on so that I’m less distracted.”
Jonathan chuckled, but continued dressing himself as I looked on. When he was done however, it was his turn to watch as I emerged from under the sheets. I could feel his eyes on my naked body, but did not feel the need to hurry. I dressed slowly, allowing him to enjoy the show and give him something to remember me by during his day at work.
Finally, when we were both dressed, we left the room and made our way downstairs. The elevator didn’t feel nearly as small after our night together in the same bed.
The receptionist in the lobby was different from the man who had welcomed us the night before. Unlike him, the young woman behind the desk didn’t look indifferent, but was smiling oddly. Then I realized what she must be thinking. A man and a woman, making a last-minute reservation with no luggage on them, on a work-day in the middle of the week. There must be only one thing she could think they had used that room for. I blushed deeply, though could not bring myself to tell her what had really happened. She probably wouldn’t have believed me anyway. The fact that Jonathan paid for the room didn’t make matters any better.
“Next time you can pay.” He said.
I blushed but followed him out to his car. The ride to the training center felt a bit strange. Something had changed between us. We hadn’t really done anything, yet we’d gone from flirting to something more. It was strange, but not uncomfortable.
“See you tonight?” Jonathan asked as he parked right beside my car.
I was confused for a moment, for we hadn’t made any plans together yet. Then I realized I had another class at the center after work. “Yes, see you then.” I replied.
In my car I took a moment to calm down and collect myself while I watched Jonathan enter the building where he worked. Only now was I fully able to control my breathing.
A smile broke out on my face. I wasn’t inexperienced, I’d been with a few men before and had been quite experimental. Yet last night had been the most exciting night I’d ever experienced. And we hadn’t even touched each-other yet.

 
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