Rob and Jenny’s First Date
Rob: Hi Jenny, I have booked a table for 8pm at Rico's Steakhouse. It's downtown, 6th and 47th so shouldn't be far from your work. See you there!
Jenny: Hi Rob - that sounds great, see you there. I'll wear a red dress as you asked.
I read about sugar daddy sites in the Financial Times and got curious one night whilst on a business trip. After some browsing and skulking, eventually joining and paying, I set up a half decent profile and contacted some girls I liked the look of in New York. I picked the Big Apple as I travel there fairly often on business and I figured it would have plenty of girls. I wasn't wrong about the latter. I had to work on it a bit, send a few messages out but Jenny responded fairly quickly and felt quite genuine and fresh - some of the other girls only wrote in sentence fragments, mostly about how busy they were. Not Jenny. Full sentences, and very quickly basic stuff about her parents and heritage (German, Finnish, Swedish and Irish). Nothing detailed or traceable for sure, but it made her seem like a more real human being. Of course it helped that she looked great in her pictures, although those too were real rather than posy. One even included a girlfriend who was named in the blurb.
So although I was plenty nervous about meeting up, I had a good feeling about it and was excited as well as nervous. We had discussed money over text, basic details - how much for the date, me paying her Uber home. I rather kindly offered that she could stay the full night as she had told me she worked downtown, where my hotel was. Ulterior motives aside, it seemed rather practical to me but resulted in some temporary tension to our chats. But we got over that. Beyond those basics, we hadn't discussed anything else, including whether or not sex was actually on the table, which I'm sure felt as legally sensible to her as it did to me.
After finishing my meetings for the day, made sure I showered, changed and got my call back home to the UK over with. A quick drink in the hotel bar and I was on my way to Rico's. The hotel itself was nice; which means very nice for New York (but certainly not the Ritz!). I'd been stuck in plenty of rather tired and out of the way places on previous trips, but managed to swing a better hotel this time. For some reason, I felt I needed to impress my date. Funny how the mind works. I had tried working girls, professionals, before, and generally felt better being based in a decent hotel and this was a similar sentiment, albeit heightened.
* * * * * *
I arrived at the restaurant five minutes early. Not by accident... I had decided that I didn't want to be too early, sitting solo at a table waiting a long time, but also I wanted to be able to see her arrive and ask for my table. I had booked the table under the fake surname I gave Jenny, only keeping my real first name.
The plan worked after a fashion as she arrived at the same time as me. I recognized her from her pictures, and the little red dress sealed the deal. She was striking. Blonde hair down past her shoulders, blue eyes with pretty round face, full lips and beaming white teeth that smiled at me as I said "Hi Jenny, I'm Rob" and leaned in to plant a kiss on her cheek.
We asked to be seated, and being the gentleman I am, I let her walk in front of me. This gave me a good look at her figure from behind. It didn't disappoint: upper body tapering to a slim waist and out again to perfectly proportioned hips and ass. The dress covered about halfway down her long legs and matched her shiny black and red high heel shoes. I remember the shine as my visual trip down her figure had just arrived there when she turned around and said: "Which side do you want to sit Rob?". I smiled back and took a seat.
The front view was no worse than the back, now that I had a proper look. She was very pretty and her stated age of 22 seemed accurate enough. The red dress was nicely fitted around her chest and revealed a little bit of firm looking flesh. I moved my gaze upwards and said: "It's nice to finally meet you Jenny - your pictures really don't do you justice!" and then "I hope you like this place, I've been here a couple of times and always enjoyed it". She smiled and I noticed in that moment some nerves. Understandable, I was nervous too - and I was the 44 year old man, not the young lady hooking up with a stranger.
I tried a more direct approach: "Did you have a good day at work?" Which did make me wonder how she had managed to get changed out of work clothes into evening wear, with no time to go home to Queens. "It was okay” she said “I managed to finalise a trip for a group of dentists to Thailand." I knew from our chats that she worked in the travel sector, in some sort of travel agency start up. "That's cool." I said, immediately regretting the middle age man usage of the word 'cool'. "I've never been to Thailand myself, but I hear it's amazing. Are they going to Bangkok or travelling around?". That was enough to get her relaxing and talking. A caipirinha and some wine kept it going. We talked about the dentists' trip to Thailand, and another trip she was working on for a couple's honeymoon in Kenya. I told her a bit about my work, although I was conscious of not saying too much - not mentioning the manufacturer I work for by name or the bank I had been visiting.
I was also very careful to not mention money at any point. I was here, putting the work in to this deal because I didn't want a straight forward transaction with a hooker. I didn't want to pay up front for a service delivered, perhaps robotically, perhaps with flair, but fundamentally timed. I was paying, but wanted to keep control - whilst giving her the cash she felt she needed and making her feel like she was not a hooker either.
As we finished our deserts, I knew I needed to make the next step clear. There was no room to make mistakes here. Bring it up the right way, presumptive but not arrogant. In charge, but friendly. I had thought about this moment in advance - this was not a done deal. She could decide to back out and might already have second thoughts. Whatever I said, I could not give her an easy opening. So I said: "I'll ask for the bill and then we can continue back at my place." She licked her lips gently and said, quietly "Okay, let me visit the rest room quickly."
I must admit that in that moment I feared she would simply make a run for it. I certainly had been careful not to visit the gents myself! And as she picked up her handbag I knew she would leave. I should have picked the chair facing the exit! But I said nothing, just nodded and waived the waiter over. My mind was working overdrive. Perhaps I could pay and ambush her at the exit, give her no chance to leave. Then I noticed her shawl draped over the chair. Maybe she'd leave it, but I figured not, and as I finished paying she came back, lipstick refreshed, and we left.
* * * * * *
My hotel was two blocks away, so we walked. Silence wasn't an option, so I told her a meaningless anecdote about a taxi ride gone bad on an earlier trip to New York, involving a lost phone and wasted hours tracking it down unsuccessfully. As we arrived at the hotel lobby I felt like I was herding her in, towards the elevator and holding her prisoner as we ascended. "The view is great from the room" I volunteered, to no reply. I had thought through most of the date, how to keep it smooth, but somehow keeping the conversation going walking side by side and stuck in a metal box was more than my prep could cope with. What to do when we got into the room was another story. Set the tone immediately was the order of the moment - set a momentum, not time to talk practicality.
So I opened the door and showed her into my hotel room, put my hand around her waist and suggested we look at the view, which was nice enough. I then leaned in for a kiss, which she reciprocated and we moved into an embrace. I moved her hair aside to kiss her neck, moving down to her shoulder while I unzipped her dress from behind.
Once unzipped, with my mouth against her neck I removed the dress and let it fall to the floor as my hands moved down her back and to her waist. I moved back to kissing her on the mouth, tongues meeting and my hands grabbing her naked ass. She had kept her hands on my back, stroking it casually. I guess I didn't quite have the treasures to open that she did.
I decided that the bra would need to come off before I moved her to the couch, and, using both hands, undid the clasps. She made a little shy gasp, but didn't protest, just moved her head slightly back from where our lips were kissing and looked at me as if seeking reassurance.
I removed the bra and looked down at her breasts. Sizes are not something I can identify at a glance, but I would say they were a pert pair of C cups, with beautiful round areolas and erect little nipples. I grasped one in my hand and moved to lick the nipple with firm but gentle flicks of my tongue. She moaned appreciatively - I didn't care if it was real or not. This was going fast. Clearly the deal was on and the last thing I wanted to do was to blow my load in the next five minutes and have to worry about what happens next. So I grabbed her buttocks and lifted her up and lay her down on the couch in the room, and lay down next to her. We continued kissing whilst I explored the curves of her body, with my hands and mouth.
So far she had simply gone with the flow, reacting to my actions and letting me do what I wanted. I decided to test if she would take instruction. This was delicate. How far to go? I decided for: "take off your panties", said calmly and confidently. She wriggled her hands down and slid her panties off. Now she was naked, wedged between me and the back of the couch, with me still fully dressed. I slid my hand between her legs to feel her pussy, which was shaved with a small landing strip above. It was gratifyingly moist and her lips came apart to let my finger slide over her clit and down towards the hole. I slid my finger in - because I could rather than to finger her at this point - then put it gently against her lips. "Lick". I said it firmer, but not as a command. She complied and stuck her tongue out to lick around my index finger, wet with her juices.
At this point I had two thoughts in my mind. I fancied having my own taste of her pussy, but also wanted to up the ante on being in charge. I was sorely tempted to stand up and tell her to suck my dick, ideally in those very words. But again, I wanted to set the tone rather than finish too quickly.
So I chose my words carefully. I stood up and said "Lie down on the bed and spread your legs." She stood up compliantly and I enjoyed the view as she took the handful of steps to the bed and lay down, legs spread, pussy on full display. "I changed my mind, turn around, ass in the air". Again she complied and turned around, chest and face to the bed and her firm ass in the air. I casually spanked one cheek lightly, then the other, with a light grab of her cheek each time. The slaps made a satisfying sound, but were light and not intended to mark - again just to set the tone.
I silently stroked around her ass cheeks with my hands, slid a finger between her pussy lips and towards the hole, but not in this time, and used the juices to draw a barely visible circle around her butt hole. I wasn't planning to go there that time, just marking territory. I finished with a single, firmer slap against her butt cheek and said "turn around again and spread your legs". She went back to her original position with a simple "okay".
I grabbed hold of her legs just under the knee where she had bent them and lifted her pussy up towards my mouth. It wasn't the most comfortable of positions for me, but it was dominant and let me taste her pussy for myself. She moaned enthusiastically as flicked my tongue against her clit and ate her pussy greedily.
I adjusted her legs over my shoulders, calves and ankles on my back, so that I could move one hand to first squeeze her ass, then around the front to those glorious breasts. I finally reached my fingers into her mouth, which she opened and let me penetrate, first with my index finger, then as I added two more and slid them in and out.
By then I was bursting out of my trousers, and as much as might have planned to delay the moment, my cock simply demanded attention at this point. I put Jenny down on the bed, wiped my mouth and said: "My turn. Kneel on the floor".
She quickly scrambled onto the floor and kneeled in front of me, where I had taken a couple of steps back. While she was moving, I had unzipped my trousers and I pulled my cock out just as she looked up at me from her kneeling position, hands casually in her lap. "Open your mouth" I said breathlessly, less cool and in control than before. She obliged and I guided my dick into her waiting mouth.
I decided to leave the next steps to her, to see what she would do. She didn't disappoint. Leaving her hands where they were, she moved her head up and down my shaft, licking aggressively with her tongue. When my cock popped out, she simply licked it where it was and took it back in, sucking up and down at a perfect pace. "Slow down" I told her, though, not wanting to blow my load just yet. She did. "Let's see how deep you can take it". I'd like to think I'm well endowed, but no giant by any means, but have heard the right compliments from ladies over the years. Like a champ, she tried, hands still on her lap. I decided to help her along, using one hand to push her gently and slowly closer.
To my satisfaction, she tried hard and didn't panic, only the gentlest of pushes back against my hand told me she needed a breath. I counted silently to five and used her hair to pull her head back. She took a deep breath, mouth open and wet and looked up at me expectantly. "You can probably go deeper, don't you think?" I said, back in control of my breathing. She made a small nodding move with her head and licked her lips, took a deep breath and, again using only her head, guided her mouth back around my cock. I let her push her own way again this time, and she got all the way down. At this point she tried her best to look up at me with her big blue eyes. I stroked her head gently, "good girl" I said. I put both hands around the back of her head and made gentle, short thrusting motions. I counted seven thrusts and then pulled out again. She panted again, mouth open as I wiped some of her saliva off my dick using her chin.
So far everything had exceeded my wildest expectations. We had gotten on well enough chatting a bit on the Sugar Daddy site and later texting, but never discussed details of sex. Only ever how much money she expected to receive (no more than I would have paid a professional frankly). I had fantasized about being dominant but never before had a sexual partner so clearly submissive. My mind raced as to how to continue. At this point I doubted she would leave after one go, and in any case no money had changed hand. She had not mentioned money once the whole evening, nothing about time and I had all the leverage. I'd assumed I would be naked as well pretty quickly, but decided to go with where we were. So, still fully clad, bar my throbbing hard on sticking out through the fly, I told her to "get back on the bed on all fours". Perhaps the safe thing at this point would have been to wrap up, but I was far beyond that.
She got back into her position as before, face and tits against the bed, butt sticking up, legs apart. I stepped up to her and guided my dick in, gently. She was still moist, so a couple of gentle pushes had me fully inside. She felt good. There was none of the aggressive massaging that a professional puts on to make you come quickly. Just a soft, wet and somewhat tight pussy.
I took in the scene. Stunning girl, half my age, bent over on the bed naked. Her amazing figure on full display, from the long legs, round hips and arse, slim waist and down to where I could see her breasts pushing against the bed covers. Her face was buried in the covers, so I told her to move her head so I could see her. She turned, hair now a bit messy, and big blue eyes looked back at me where I stood, fully clad - not even a single shirt button undone - with my dick buried deep inside her. I started thrusting at a steady rhythm, enjoying the picture and the situation and her silky pussy and looked into her eyes, thinking "I'm in charge". There was no response to my thought, obviously, but I felt like a king in that moment and kept eye contact.
Eventually Jenny looked down with her eyes, along the bed and bit her lip. I kept up the deep and slow thrusts for the time being, knowing I would cum quickly if I increased the pace. I took a moment to think through what my moves would be on finishing, how best to keep control and enjoy this beautiful young woman before the next round of sex. As I thought through those next steps I increased the pace, still going deep. I spanked her butt cheek, firmly. Then harder a couple of thrusts later. Then the other cheek. I increased the pace and fucked her harder. I kept going longer than I expected and let go completely. I fucked her like I'd never fucked before, hard and with no care in the world. She started to moan loudly, somewhere between pain and pleasure. Finally I pushed her hips down and thrust in deep as I came hard, grabbing and groping her now red butt cheeks.
I stood there for some moments after, my softening dick still inside her, catching my breath. I remember so vividly how I couldn't stop groping her butt cheeks at this point, marveling at how perfectly full and firm they were. I was like a teenager grabbing his first handful. Eventually I stopped and pulled out. "You should go to the bathroom. Clean yourself up and fix your hair. It's messy."
Before the date my idea at this point would have been both of us naked in bed, cuddling and spooning, a bit of groping and kissing, getting ready for round two. Somehow it felt wrong for me to undress now. Instead I watched her walk to the bathroom in all her naked glory. I waited for the toilet to flush, then went to watch her.
She only acknowledged me with a brief glance towards where I stood and a nervous smile. Luckily she had a hairbrush in her handbag, and I watched her from the side as she brushed through her hair with both short and long, soft and hard strokes. I'd never have planned this, or fantasized about it. But the view of her breasts as she worked through her hair was quite something to behold. "Do you have any hair bands?" I asked. "I think so - - - yes" she said, rummaging through the purse. "Put your hair back in a ponytail. I want to be able to see your face and neck properly." She expertly did as I had told her and turned towards me asking "like this?" as she turned her head left and right, her hands demurely behind her back. "A bit higher" I replied. When had I ever cared! I thought to myself, but higher was right and again she followed instructions without hesitation.
Of course I had plans for that ponytail, but that could wait a bit. I have always been tactile with women, can't get enough of groping a good set of tits or a nice ass; legs are a solid third preference, and Jenny's were quite something. I decided I would go full perv on Jenny now.
"Stand over there Jenny" I said, pointing to the floor space between the couch and the little hotel desk. I followed her, and took a half circle around so that I stood behind her. "Stand straight, but relaxed, arms by your side." She did and I took another couple of steps around her, looking her body up and down.
At this point there had been no real conversation between us since we came to the hotel room. Just my short commands and her shorter replies. I wanted to keep it that way. I wanted to continue this relationship with further dates where the chatting could stay in the restaurants or cafes, but in the bedroom I would tell and she would do. So I told her, in a neutral voice: "fix your eyes on the picture on the wall over there." This way she wouldn't be watching me staring at her body and groping my way around.
I started behind her, following the curve of her right hand side from her breast down towards her hip. Just a gentle stroke. I continued around the back over her buttock, but resisted the squeeze. I then repeated the move on the other side, slowly and gently. Moving to the side a little, and getting down on my haunches, I cupped her buttock and moved my hand down the back and inside of her thigh, all the way to the ankle.
I stood up, moved behind her and cupped her breasts, one in each hand. They were heavy, and firm. I placed my hands over her nipples, taking both nipples between my respective middle and ring fingers, rolling them; first gently, then more firmly. She shivered a little. Keeping my left hand in place, I moved the other hand down her flat belly towards her groin. I stroked her landing strip a bit, then slid my fingers over her pussy, ring finger inside the lips, little finger and middle finger either side. I rubbed up and down whilst I had my way with her breast, squeezing it, pulling the nipple. She was as wet as before, so decided to give her another taste of her own juices, moving my ring finger to her mouth. She parted her lips and I inserted the finger, moving in and out whilst she sucked.
I moved my hand back down to her pussy, my left hand changing breasts, and started playing with her clit. I was probably a bit rough and she certainly didn't cum during the couple of minutes that I kept this game up. Rubbing her clit, sliding into her hole, massaging her breasts and playing with her nipples.
I didn't need to say anything really, could have spun her around physically easily enough, but decided nevertheless to say: "turn around". And she did, while I kept my hands attached to her body, sliding along while she turned. Pussy became ass, and tits became back as I leaned in to kiss her. Whilst we kissed I continued exploring her body, although the ass got more than its share of attention. She was a good kisser, active and enthusiastic - never over sloppy or lazy. My hard on started complaining and decided to put that ponytail to good use.
I took a couple of steps back. "Get on your knees Jenny", which she did. "Grab your wrist behind your back and hold on until I say otherwise". Again she complied, maintaining a good posture and keeping her head up but eyes down. "Look at me" and she looked up and I looked into her eyes as I said "I'm going to fuck your mouth again and I want to you look at me the whole time". Without me asking, she opened her mouth, her gaze locked to my face and eyes as I pulled my cock out again. I left it to her to guide it into her mouth and get to work.
Her technique was again quite good and I was content to let her do the work for now. A couple of times I moved so that my dick would fall out of her mouth, just to watch her get it back in her mouth without the use of her hands. Then it was time, and I grabbed hold of her pony tail firmly and started guiding her head back and forth. There was a bit of resistance in her, so I told her "relax" and "I'm in charge of your head now".
She immediately relaxed and I continued using her pony tail to guide her mouth back and forth along my hard on. Then deeper, one thrust at a time. "Open big" I said as I moved all the way in and wriggled around a bit. I counted to ten and pulled out, still holding her pony tail. She was quite out of breath, but her eyes stayed up so that I could look in them.
Wordlessly, I went back in, this time using my hand to guide my dick. Again working through some thrusts until I was fully in and counted to ten and pulled out. She was more out of breath this time, but kept her gaze on me. There and then I decided I would cum in her mouth this time. "Put it back in" I ordered, quite sharply. She got me back in and I started thrusting again, using the ponytail to keep her head steady.
I fucked her mouth, with some short deep throats but mostly not forcing it. She sucked like a champion and before long I couldn't hold it in any more. I must admit that I had hoped to drench her in cum at that point, but as it was my second round within an hour there was no chance of that. Still, she got a good taste in her mouth and some on her cheek, which I rubbed around with the head of my dick.
I continued holding hear pony tail and moved to stroke her head gently. "Good girl" I said. "I think you deserve a treat. But first clean your face". She stood up and walked to the bathroom. I swear there was a glint in her eye as she rose, but I was soon distracted by the rear view of her naked body.
I sat down on the couch while she cleaned up. She walked back into the room and stood facing me, hands by her sides, just as I had told her to earlier. Enjoyed the view for a moment or two, then said "you can sit next to me". She sat down next to me, like the little mermaid, feet tucked under and to her side as she leaned her body into me. I put my arm around her shoulder and held her tight, and leaned in for a kiss. We kissed for a while, my hands finding familiar and luxurious places to fondle. I then pulled away from the kiss and said "kneel in front of me". She looked surprised, but did as she was told.
I looked at her where she knelt. "You have done even better than I expected Jenny, well done", I smiled fondly at her. "You do deserve a treat. After all I've cum twice and you haven't at all". I really wanted another taste of her pussy, but this wasn't the time. "You can lie down on the bed and spread your legs. Show me how you make yourself come". She stood up and went over to the bed, lay down on her back, legs open and started to play with her pussy and breast.
"Turn around, butt up!" I said sharply. She re-positioned herself quickly. "Arms out in front, palms down on the bed!", I said, again as an order rather than polite instruction. She complied quickly again, positioned as if praying to an ancient deity. "A good girl would say 'thank you' when her Master allows her to cum. I'll have to punish you now."
She remained motionless on the bed. I walked over and put my hand on her ass, giving it a pinch. Then stepped back. I undid my shirt buttons and removed the shirt, then noisily took my belt off, making sure she could hear, then my trousers. I slapped the belt down on the bed, close to her head - she was clearly startled, but stayed in position. I grabbed hold of her ass again, squeezed the left cheek with my left hand while the right hand came down for a spank. This time it was the real deal and three slaps later a red mark had spread. I switched cheeks and repeated.
"What have you got to say for yourself now, Jenny?" I asked. "I'm sorry Master" she said, calmly, "I will remember to be grateful in the future." I stroked her back and butt for a couple of moments, then "you can touch yourself now, but keep your left hand where it is". She obeyed with a simple "yes Master" and started playing with her pussy.
I rolled the office chair over to the bed and sat down right behind her, legs crossed lengthwise and casually on the bed, and watched her masturbate for a bit. "Fuck yourself with a finger" I said, back to calm voice. Again the "yes Master" came and she complied, and demonstrating attention to detail fucked herself with deliberate speed.
"Two fingers", this time there was no verbal response, just the addition of the middle finger alongside the index finger. She kept going for a while until I told her to "go back to as you were, make yourself cum" and she went back to masturbating her clitoris. Then she came, with a cliched 'oh god, oh god', and shuddering body.
Although she stopped masturbating, she stayed in position. "Did I tell you to stop?" I said. Her hand moved back to very gently masturbate, but a quiet "but I...." escaped from her, almost too quiet to hear. "Keep going, surely you like it firmer than that!" I said and she seemed to put a bit more effort into her moves again. "Here, let me help you" I said, and casually smacked her butt. First right, then left, then again, and again. That seemed to get her going, and she started up again until she came a second time, this time without stopping - although she was clearly tender.
"You can stop now and relax". With a content sigh, she removed her hand and relaxed, laying flat on the bed, face down. I let her relax for a bit, then stood up, removed my boxers and moved round the bed to where her head was. "Look who's back" I said as I used her ponytail to manoeuvre her head to face my erect cock. She opened her mouth and I put it in, leaving her to start sucking. I was in no hurry, so let her work for a bit at the blow job.
"Lie down on your back" I said and moved on top of her when she had complied. I slid into her wet pussy and started fucking her again. I kissed her as we fucked in the perhaps second most traditional of ways. It was quite casual, both of us tired, and I knew this would not be quick as I was already asking a lot of my middle aged equipment.
Eventually I had a thought and lifted myself up off her and went to my suitcase. She watched me with curiosity as I rummaged around, and then showed her my collection of ties. "I think we can have some fun with these" I said with a cheeky smile. She bit her lip nervously, and I decided to not give her time to think.
I tied one tie to each of her wrists and the other end to the bedpost, which was handy for the purpose. It wasn't the most elegant bondage, and the ties not too well suited for the job, but it also meant she perhaps felt more comfortable, knowing she could probably get out of it.
I had her lying on her stomach again, flat with legs spread. I knelt next to her and put my hand between her legs, finger almost straight into her pussy. I used some of her juices to draw circles around her anus, which she purred at but also said "Please not there. I've never done it".
I immediately spanked her, to which she said "Please Master, not there". I smiled to myself and said "I'll leave it for today, but you will never say no to me again". She waited a second or two, then replied "Of course Master".
I silently positioned her again for a doggy style and entered. It seemed the hormones were back in full swing and I fucked her hard, spanking occasionally as I went along, admiring the view of this stunning girl tied up in front of me. And so I came the third and final time for the night.
* * * * * *
Worn out I untied her and lay down next to her on the bed. We kissed for a while. I realised that even now, she showed no signs of wanting to rush out. Deciding to enjoy this post-coital moment I said "I'm back in town middle of next month. I should take you shopping then, get you some nice things". She looked at me thoughtfully and said "That would be nice, Master". I smiled back, "in the hotel room always call me Master, but outside I'm just Rob. Unless i say otherwise, of course". "Of course Master", she replied.
"You can stay a bit longer, until morning if you like. Otherwise you are free to go". She snuggled up next to me and said "I'll stay for a bit longer please Master". Needless to say, we both fell asleep and slept a couple of hours. Then, in the early dawn I sent her home in an Uber, my mind already filling with plans for next month.