My Third one night stand, with a guy I met on Craigslist (f/m) | 2016

On New Years Eve, ushering in 2012, I counted down the clock 'til midnight, by cruising the Internet for cock.

On one of the dating sites I'd been using, I came across a very interesting profile. Though the photograph was of a blue eyed blond (I prefer brown eyed brunettes) I was intrigued by his very creative written content. He had prepared a questionnaire, for prospective bachelorettes to complete. It was quite clever and cute. And of course, there are no qualities I value more in man, than being smart and sweet (except for the ability to, on occasion, convincingly pretend to be a Bad Ass Monster, who'll abuse me and punish me for being the bad little girl that I am ; ) I responded to his queries with humor and honesty. It was unfortunate that he and I seemed to be complete opposites: he was outdoorsy. Business man. Buttoned down. And fairly conservative. But I was compelled; I felt that I just Had to offer him something enjoyable to read, in return. He replied quickly (already off to a good start!) Having enjoyed my answers, he agreed that we had little in common, but seconded my feelings of curiosity towards the other, and an urge to delve deeper. We exchanged emails everyday for a week. The perfect correspondence: cute, naughty, sweet, and Nasty. We realized that we had a lot of sexual commonalities: both of us blessed with the ability to switch dominant/submissive roles, and enjoy each experience equally. We soon took it to the next level; exchanging phone numbers and began texting. As I Love composing naughty texts, and having them responded to; I was very pleased with the progression of our friendship. Soon we started discussing a possible Real Life meet. We shared our fantasies with the other, and what we were hoping would happen when we met. We planned every detail for our rendezvous, right down to a cover story for the restaurant, where I was to pretend to be a professional Photographer's rep, who was meeting with him; a marketing genius, to discuss how to promote and brand my client. I was asked to dress as a sophisticated businesswoman, and not to make any physical indications of my sexual desires, while we were at the table. We agreed to part at the restaurant, and meet up at a hotel; should both of us feel that the chemistry was right to continue the evening. We scheduled our date for the following Friday night. The thirteenth... Dun Dun Dahhhh!!

I spent the week fantasizing and making lists. We openly discussed our most private secret desires, and what we wanted from the other. I bought new toys for our play (including a thick black leather collar, because on the phone one night, while he asked questions expressing curiosities about my preferences, he wondered in a barely-audible-mutter, whether or not I Would wear a collar. But he shook his head and convinced himself that That would be too much; he could not ask that of me. I just listened while he rambled, and planned to make a quick stop at the pet store, for my new prop. Luckily I already had the elements I needed for my first costume at the restaurant - fitted white collared shirt (with cute white bows on the breast pockets!) black on black polka dot tie, short black skirt, black on black 1/2 inch ringed nylons, 3" heeled shiny black boots. And to finish off, a red-bow hairband, to hint at the colour scheme of the next outfit to come... The last 2 days before the meet, he wanted to keep our contact, and self pleasure, to a minimum: to build the sexual tension and enhance our encounter. I had difficulty obeying his commands (which I Told him; so that I would be in trouble, and he could punish me when he had me all alone in the hotel room).

On Friday afternoon, I began assembling the necessities for our evening together. I rummaged around my room, looking for anything that could be used for our enjoyment. We texted back and forth (confirming time, restaurant and hotel address etc.) and when I was finally dressed, packed, and ready to go, I sent him this message :

Subject - Date night

I have prepared something for you to read while you wait for me and work yourself up; as the anxious energy spins your head around...

• The fine print

Limitations : I have bad knees and shoulders (years of repetitive physical labour : ( so l may not be able to get into very elaborate positions. Or be able to stay in them for very long. Pose me as you like; and know that I will accommodate everything I Can.

Limits : I want you to push the boundaries of what's safe, and what's dangerous. Don't ask me if I'm ok. Don't make sure I'm comfortable. Just enjoy the sounds of me crying out for you to stop. But don't stop... Unless - You already know my safe word is "serious"; if I ask you to stop, and I say "I'm serious" please stop. - when shoving my long pink vibrator inside my pussy and/or asshole; meet resistance with kindness. Feel free to surprise me with a hard, deep, thrust; but just know that the deepest I can take it in, is about 6 inches. - you can squeeze my nipples, clit, and neck, as hard as you want, until I tap you 3 times quickly - this means lighten your grip; but continue.

Everything is fair game. Please enjoy yourself.

The Fun Stuff : In preparation for our date, I have made several lists. I have gathered what I think will be the perfect kit for our evening together (which will all be concealed in my fancy polka dot suitcase, which further adds to the illusion that you and I are just an average couple, spending a quiet night in a hotel; after a days' business, or travel. As per your request, for the hotel-arrival roles ; )

Some of the case contents :

• an mp3 player. I scoured my music library, and set up a new playlist for tonight. The first three songs are the only ones I have, that I think you would like, based on what you've told me about your preferences. The rest of them are songs that I like; having all been my favourite song, at one point or another, and they will give you an idea of my musical taste, and perhaps provide some insight into who I am.
• snacks and water, for maintaining my strength and hydration over a long night of getting fucked hard, and used badly.
• Of course, my secret sex-box ; ) complete with all my toys!

- a change of clothes for morning, for when you are finished with me, and I get to stumble home, weakened and satisfied.

I sent off the email, and headed out. It only took me 10, of my estimated 30 minutes, to drive to the restaurant (though I was Still late - we had originally agreed on an 8:00 start to our date. Then he had some work calls to take care of, giving me another hour. So I got sloppy with my time management and ended up arriving at 9:06 - Pretty good for Me though! I only felt bad because he had been there since 8:30)

Standing at the car, when I was shining up my lips, adjusting my skirt, and pulling my panties out of my ass, I was nervous and excited. And Cold!! It was the first real snow of the season! Thank you Mother Nature, for trying to cock-block my effing date night! I'm wobbly enough in heels to begin with; heels AND snow to contend with - you Motherfucker!!

I texted to let him know it was time to come to the front door of the restaurant to greet me, and then I made my way towards a night of sexual pleasures and uncertainties...

He came out and waited near the doors, scouring the immediate parking lot for me. My first impression : He was cute. Looked like the photographs I'd seen, and I was pleased with the over-all exterior package. He smiled and opened his arms for my hug. It wasn't at all awkward being embraced by him, and we both parted with smiles on our faces. He opened the doors for me and I followed him to the table where he already had an appetizer and ice tea waiting. I removed and hung my coat and slipped into my side of the booth. I felt super cute and sexy. He seemed please with what he saw as well, and I felt very comfortable within minutes. We small-talked about the usual things people say on a first date. As we got more and more comfortable, we started with the sexual innuendos and sly grins. It didn't take long after the sex talk stared that he was ready to call himself a cab, to go to the hotel (* he was adamant that we make our way to the hotel separately - I was later told that he was mildly concerned that I was going to abduct him, if he got in my car. He's a real sweetheart nice guy - was more afraid of me, than I was of him!) He left the restaurant first and I freshened up in the ladies room. I had a bit of a time in that bathroom stall! - peeing in a skirt is a difficult business!! And then after I'd flushed, my gloves fell in the toilet! As I was washing my hands, I longing looked over at my wet gloves in the open-mouthed trash bin beside me. It occurred to me that they are water proof ... and I Had Just flushed fresh water into the bowl ... and it was Bloody Cold outside ... So I made a decision I never thought I would, and I retrieved my gloves from the Garbage to keep my hands warm while I walked to my car, and I thought to myself: Bad Omen or not: I'm going through with this night; come what may...

When I arrived at the hotel, I texted him to meet me in the parking lot to collect my suitcase from the trunk. We carried in my load (I also had a cooler full of bottled waters, and my purse - having only brought my little black briefcase to the restaurant meet (it worked with my business-woman persona, and hidden on the bottom, was the phrase "bad girl", but I didn't show Him that until we got back to the room, promising that no one at dinner saw it ...I'm pretty sure ; ) He had already booked the room, and we went straight to the elevator.

Once the doors closed, he dropped my suitcase and pinned me up against the wall, kissing me hard and wet. I reached out to tug at his hair, and when his hand went up my thigh and under my skirt, I lifted my leg, hooking it on the hand rail, so he could rub my panties. And he did it with perfect pressure, enough to cause full-body tingles. When we reached our floor, he loosen his grip on me, stepped away to pick up the case, and exited the elevator like nothing had happened (so Hot!!). I followed him to the room, and we removed our coats and shoes, and looked around. It had a couch in a separate front room with desk and lamp, the bathroom was next to a door that lead to the bedroom. I opened my case, took out my outfit for the evening, and went into the bathroom to change. I wore, in addition to my new collar, a black & red and white-bowed neglige, and thigh-high fishnet stockings. When I emerged from the bathroom, I handed Him my red nylon leash, and he clipped me in. He immediately forced me to my knees, wrapped the leash around my neck two times, and told me to make his cock hard. And do it Well, and Fast. I gripped his dick with both hands and started stroking it, while I stared up into his eyes (as I was told). At his curt instruction, I parted my lips, stuck out my tongue, and took his cock into my watering mouth. He told me to swallow it. I gagged myself on his cock several times, causing my double coated mascara-ed eyes, to run with black tears, streaking my cheeks. He jerked on the leash and spun me around to sit on the bed. He grabbed a handful of my hair, pulled me forward, and forced his cock down my throat. He face fucked me hard and fast, I had to pull away a few times to catch my breath. And when I did, Master was displeased: he slapped my face for the insolence. I stared into his eyes with shock and shame for disappointing him. He told me to keep his cock in my mouth, and I was not to pull away again. I was unable to comply. For failure to do as I was told, he pulled on my leash to direct me into the centre of the bed. Pushed me down on my hands and knees and entered me fast and hard. He pushed my face down into the pillow, and pounded me rough from behind. I begged for permission, and was finally allowed to rub my aching clit. He let me cum, and then made me suck his dick some more before I would be granted a break. After I gagged and choked on his hard cock for a while, crying, nose running, and out of breath, he pushed me down and I was given a time-out, while we talked and cuddled.

He asked if I was enjoying myself; if he was performing well. I told him that everything was perfect (except the slaps were a little close to the ears, and made them ring. I showed him how to position his palm to catch my cheek in just the right place).

He needed a pee break, which was good timing for our second round, where HIS fantasy was about me walking into the bathroom and catching him masturbating for the "first time". I was meant to play an Aunt with her 13 year nephew. He told me that he wouldn't say much, that I was to carry the conversation, and after the admonishment he received for being discovered, I was to play teacher, and instruct him how to touch himself.

After a few mins, I knocked on the door and opened it. Walking straight in and asking "well, you've been in here a long time, what are you doing?..." I look down to see his soft dick in his hands, and up again to see an embarrassed and frightened look on his face. I ask him "What are you doing? Were you just touching yourself? ... Let me see... Let me See it! ... Have you ever done this before?" He shook his head no, and I told him to "speak up!". He whimpered a shaky "n..no", as I sat down beside him on the bathtub rim. He starred at me in amazement while I reached in and pulled his cupped hands away from his concealed penis. I asked him again if he ever touched himself before. He whispered "no". I asked him if he knew what a bad boy he was being. He lowered his head in shame. Then I asked him if he wanted me to show him how to do it properly. His eyes widened and he slowly nodded his head. I wrapped my fingers around his soft cock and pulled on it until it was hard. All the while telling him what a bad boy he was, and reminding him that his mother would be upset if she knew what he was Doing, if she knew what WE were doing. I hooked my thumb under my bra strap, as I asked him if he'd seen a woman's breast before. He shook his head and swallowed hard. I pulled down my bra to expose my chest, and he tentatively placed his hand on my expose tit. He grabbed and rubbed and squeezed at them just like an inexperienced boy would. He allowed the occasional excited smile to escape, between expressions of shame and astonishment for the unfolding events. When he was long and hard, I asked him if he wanted to fuck me. He followed as I lead him to the bedroom, and I sat him down on the end of the bed. I pushed him back and spread his legs. Then I grabbed a hold of his cock and started sucking. He moaned and whimpered a few times. At one point, I stopped and stared at the door, suggesting that I thought I heard my husband coming. He startled for real [that's how good I am], and attempted to sit up, but I forcibly pushed him back down, told him to be quiet, and continued to suck on his dick. I took his sexual awareness to a whole new level, as I spread his legs and began circling his asshole with my finger tip. He shuttered with ecstasy and cried out with excitement. Soon enough he told me was ready to explode, and asked if he could shoot in my mouth. I allowed it, since he had been such a good boy, and he filled my throat with his cum. It dripped out all down my chin and on to my tits, as I smiled my approval and satisfaction for being able to make his fantasy come true.

We made our way to the head of the bed and talked for a while, me tickling and fondling his legs and arms and chest. We chatted about anything and everything for about an hour, while we looked at his laptop porn collection, and recuperated/geared up for more. He showed me the photos he keeps of sexy women in dirty poses; we critiqued them together.

The next go around was for My enjoyment. We lay side by side and he fingered me while we made out. His kisses were perfect. Not too much tongue, rhythmic changing pressure, and wonderfully wet. He bit my bottom lip a few times, which it turns out, I Do enjoy - when done properly. He played with my pussy for a good 15 minutes while I moaned and cried out as he pushed deep inside me. When I was ready to cum, I reached down to my swollen clit and furiously rubbed out another orgasm. I shook with uncontrollable violence and then collapsed, spent, and gasping for breath - as I had asked him to wrap his hands around my throat while I came.

After, we flipped through the channels on the tv, and chatted again. We were both pleased with the evening, and tired from the activity. The ritual of getting ready for bed took about 20 minutes. I wore the white cotton wife beater that he had worn under his shirt; at my request (*he had to go out and find one for me! He went to several shops in search of it - such a sweetheart! - I don't know why, but I've got a thing for man in a white wifebeater and blue jeans.) It was 5:30 am when we finally turned out the lights. I had forgotten my ear plugs (Blast!!!) but I actually managed to sleep a bit, despite the herd of 12 year old soccer players who ran through the hall at 8:00 am. That ruckus lasted a while. At 10-ish we were both awake at the same time : his cell phone went off a few times, and eventually we had to acknowledge it. After he replied, and put the phone down, I started rubbing his crotch. His dick was reacting as planned, and we stared fooling around again. He managed the hardest erection he'd had, so we wanted to give it a go sticking it in my bum. It was a snug fit, and though it was slightly painful at first; I think I preferred the anal sex more than anything else we'd done. I was able to spin my clit with my two longest fingers, and had a very satisfying morning orgasm. I collapsed on the bed while he took a shower. I slowly got up and started preparing to collect my things from around the room. We busied about our little suite of sexual desires for about half an hour, both of us quiet non-morning people. He kept outta my way, I tried not to get into his. I offered him a ride to the train station, and he (only Mildly hesitantly) agreed. Having convinced himself that if I was going to kill him, I would have done it by now. I giggled and replied: "Silly boy! My dear, I only kill you After I've had my fun with you, of course" luckily he smiled, and we headed back to the lobby. He took care of the morning-after business with the hotel receptionist, and then neatly stowed my luggage in the trunk of my car before we headed to the station. We chatted during the 5 minute run, and parted with a hug and kiss, before he walked to the platform.