Craigslist Casual Encounter: Part 2 the Meeting

I was late. Of course I was, I'm always late. I called when I was a block away and asked him to meet me outside. How awkward it would have been to walk into a bar and just walk up to someone hoping it was him. 

The whole way over on the bus I had just felt kind of numb. Was I really about to meet someone I didn't know and let them spank me. Really? That is just not me. But then at the same time there was this total rush associated with it. Like I had this secret life that no one knows about, that my friends would be SHOCKED to know about.

And what a relief. He was cute. He was SO cute. freckles (love them), dark hair, a nice smile and eyes. We sat down at the bar and I could barely make eye contact. I was so nervous. The first thing he wanted to talk about was the responses I got. So I told him. A lot of older guys (including one who introduced himself by telling me about his kids- WHO WERE OLDER THAN ME), a few cock pictures, and a surprising number of cute boys. Okay 3, but I was expecting none. He asked how many I had responded to, and I said only him. He didn't believe me, and I shrugged and told him I didn't really care. Then we talked about was music, as it turns out, we're both pretty interested in it and have similar tastes. We had a beer, the conversation flowed pretty easily. I know he wanted to take me back to his apartment right away, but I had to be comfortable.

His eyes were all over me. Especially on my legs. When men want something they get this cloudy look in their eyes. Its like desire clouds everything else in the world. So after a second drink, I told him I was convinced he wasn't a serial killer, and he invited me back to his apartment

Craigslist Casual Encounter: Part 1 The Posting

So after a few weeks of being a bit of a lurker on craigslist, I thought I might want to post in the casual encounters. I'd been talking to the few guys I mentioned earlier looking for more of a relationship. If you're starting a relationship with someone you need to wait a bit before you put out, but I needed a spanking and I needed it soon.

This afternoon I was so bored. I was so bored and craving some excitement. I checked out the casual encounters page, but quite frankly, the thought of answering an ad purely for sex made me feel dirty (and not in a good way). Plus, I was wary of making any sort of promise for sex to some guy I had never met. What if I showed up and he was ugly (it happened before)? What if I showed up and he was creepy? What if I felt pressured?

I thought to myself, I could post something. I wouldn't have to answer any of them if I didn't want to, and hey, they might turn me on a little.  So I posted. 

Want to spank a bad girl?

I was naughty girl at work all week, and hardly got anything done. Need  a lecture, over your knee, skirt pushed up, panties down. Interested? 26, cute, fit. pic for pic.

The responses started rolling in immediately. Craigslist had removed my ad within 30 minutes- maybe they thought I was a prostitute? ouch!- No matter, I still got about 23 responses. I was pleasantly surprised by the lack of cock pictures- I only got 3. Seriously though, do dudes really think we ladies go for that? you could have the biggest dick in the world, but if its not attached to a cute face/body its not going to happen.

My favorite response was from this thugged out dude that said "I'd spank dat ass girl." haha! not my type, but  valiant effort! Most of the guys were much older then me (I'd say between 38-45 and thats what they said in the email so who really knows?), but I was  surprised by the number of cute younger guys- there were 4 emails that I saved. What? where are these cute boys when I'm at a bar or a party?

I thought, what the hell, lets respond to the one I like the best. So I looked through them and one stood out- cute with a hot but not creepy response. It was  the only real full on face shot- so I could tell he didn't just choose a picture looking off to the side- I mean, anyone can look cute in a picture like that. So I wrote back. Over the next two hours we sent a few flirty emails back and forth. I told him I'd like to meet in public to make sure he was not a serial killer. He seemed to appreciate that.

We made a date for monday night. He had his own place, I have three nosey roommates and thin walls. I told myself I could back out if I wanted to.

First Time Part 2

So after Andy and I collapsed in a sweaty mess on the floor we were cuddling and spooning.

I decided for the first time in my whole life to tell someone I wanted to be spanked. my heart was pounding, but he had kind of brought it up first.

"So you know when you spanked me?" I whispered.

"Sorry about that.. I won't do it if you don't like it."

"No, thats not it at all. I actually did like it. I've.. I've always kind of had a fantasy about being spanked. I've been so embarrassed to ever tell anyone." I was blushing bright red and stuttering, "Could we maybe try it again sometime?"

He flipped me over and playfully swatted my bottom a few times. "Like this?" Then he sat up and threw me forcefully over his knee, "Or like this?" He pinned my arm to the small of my back.

"Andy!" I protested and struggled a little bit to get off of his knee. I was completely naked and he wouldn't let me up.

"Which one?" he teased rubbing my bottom with his free hand.

I stopped struggling for a minute. "This one," I whispered quietly, a little bit humiliated. He slipped his hand down and started fingering me. 

"You are a naughty little girl aren't you." He gave me a few light smacks, then put his fingers back. "Look how wet you are." 

"Andy, I really don't want anyone to hear" My legs were sliding open and I was kind of bouncing up and down on his knee, rubbing myself against his leg. I was starting to pant. I'd been sexually excited before, but I'd never had an orgasm.  All of a sudden my body was so hot and frenzied. I hadn't ever felt anything like it before. At the same time I was so horrified that someone in the next room might hear me. 

"Okay" he leaned down and whispered in my ear. "But tomorrow I'm going to spank you twice as hard to make up for right now." He let me go. I stood up and kissed him and smiled. Then I turned around and spread my legs as I bent over my desk. He came up behind me and slid inside. He pinned my hands to the desk and fucked me as he kissed my neck. Then he started softly spanking me as my ass bumped up against his thighs and stomach. He reached around and played with my clit with his left hand and kept slowly, quietly slapping me with his right until he came so hard he almost fell on top of me.

The next day we were out at a nice lounge bar with some of my friends. We were all joking around and I started teasing Andy about the jeans he was wearing. and seriously? They were bad jeans. I told him that I was going to have to take him shopping for some jeans not out of 1994.  When he bumped into the hallway coming out of the bathroom he was laughing as he slid his hand over my ass. "Think you can get away with teasing me like that?" He was still sort of laughing  as he kissed me. "I'm going to teach you a lesson naughty girl."

We got into a cab to go back to my dorm room. The whole way he was stroking my legs and my hair and kissing my neck. We were both kind of drunk and stumbled into my room. We were giggling and rolling around making out. He was on top of me pressing me into the mattress, he pinned down my arms and started kissing me more frantically. Then he jumped up and turned on my stereo

"Ready bad girl?" he sat down on my desk chair and ordered me to walk over to him. I sat up and  walked over. He grabbed my thigh and pulled me closer. "You're in so much trouble. What do you have to say for yourself?"

I jutted my lower lip out and whispered, "Sorry"

He put me over his knee and pushed my skirt up around my waist. I wore my cute little grey skirt with a light plaid pattern. Then he pulled my panties down to my knees. There I was with my little ass in the air, just like I had always imagined.  He started rubbing my ass and then he raised his hand and brought it down hard. He rubbed for a second, then did it again. Then he did it again and again. I was too afraid to fight back too much because I thought he would stop. I wanted to struggle so he'd have to pin me down, but I didn't want him to think he was hurting me. So I just laid over his knee, but I couldn't stop myself from rubbing up on his legs. My breath was coming hard and fast and that frenzied feeling I had felt the night before started building up in my whole body. He kept slapping me and asking me when I was going to learn to behave.

Then all of a sudden it happened. I came for the first time in my whole life. It left me sort of weak and shaking. It left Andy really really excited. I was sort of out of it, so I just kind of fell back on the bed. I lazily opened my legs but he shook his head and told me to get on my hands and knees so he could see how red my ass was. Then he grabbed my hips and thrust into me.

"Thats my good girl" he told me as he came.

First time

My first spanking was from my boyfriend when I was 22. I had just graduated college and was about to move to the Czech Republic in the fall.  I met him the second week of summer at a concert in Chicago. We met in the parking lot when he offered me a beer from his tailgate and then we hit it off.  We got separated a little while later in the crowd, which made me a little sad. But then, as I was walking back to my car to go home, there he was! He asked me for my number, which I willingly gave him.

We started dating, but about 2 weeks later I left to do a 3 week summer course in St. Louis. So about two weeks in he drove down to see me. The walls at the place all the students were staying were so thin, and I explained we were going to have to be quiet. The bed we had was so squeaky, that we ended up fooling around on the floor of the dorm room.  It was the first time we had had sex. I was wearing this little black pleated skirt. When he started to take it off, I begged him to let me leave it on, because I love getting fucked wearing a skirt.  When I told him that he got so excited that he pulled me right onto his cock. He reached over for the light, but I stopped him and told him I liked to see what  I was doing.

I thought his head was going to explode he was so excited. I was on top, rocking back and forth getting really excited.

"You better stay quiet" he warned playfully. I love being a little dramatic so I made a big show of trying to be quiet. 

Then I turned around on him, so I was in the um "reverse cowgirl" position. then I made a couple of moaning noises and looked back at him mischievously.  I then teasingly lifted my skirt  bit to show him my ass. 

"ohh" he whispered, trying to stay quiet, "you're going to show me your little ass?" he moved his hands to cup the cheeks as he drove his cock into me. "How about I spank it til its red?"

I'm glad I wasn't facing him because there was a look of shock on my face. I don' t think I've ever been so anxious and excited in my life.

"Why, have I been naughty?" Then I purposefully moaned a little louder.

"Didn't I tell you to stay quiet?" Then he slapped my right ass cheek. the crack of his hand against my skin was so loud I was immediately really embarrassed. He raised his hand to slap again, but I batted it away.

"Andy! I don't want anyone to hear" His right hand was rubbing the spot where he had just slapped me, making me drive myself harder into him.

His hand fell away from my behind and I heard a sort of disappointed sigh, "okay"

I wanted so badly for him to continue. After all, I had waited my whole life to be spanked. I had subtly tried to drop hints to every lover I ever had, always crawling over their lap to reach for anything, always hoping one of them would take the opportunity to push me down and give me a couple of swats, even playfully. And here the opportunity was right in front of me, and I was too embarrassed to take it.

Don't worry, the story has a happy ending, I'll finish it tomorrow :)

Craigslist Date 2: The Lawyer

So I've been corresponding a bit with the guy who looked completely guido in his pictures.  He seemed totally nice and cool though, and I couldn't reconcile what he looked like with what he sounded like. So I agreed to meet him for a drink. Before the date I didn't want to meet him at all, but I convinced myself that I could leave after a drink.

We met in midtown for happy hour. I waited for him outside the bar, and he was late. I almost just left, because I hate waiting for people, but then he showed up and apologized. Ahhh, no chin strap beard! It was clearly just a poorly lit picture because even though he did have a beard it was not shaved into a line on his chin.

 Not my normal type, actually a bit short for me, but not unattractive. He did have a bit of a lisp though, but not too bad. 

We sat down and he got me a drink. He's a lawyer and was sort of take-charge in the way you think a lawyer would be. nice. I like a little (but not too much!) aggression. He had an interesting cadence when he spoke- a bit slower with unusual pauses. And he fascinated me. He had the most interesting stories about his clients.  We ended up staying for two drinks and three hours! We got along really well and there weren't any awkward pauses. As I left he told me he'd call me after he got back from his trip.

So yes, I wasn't crazy attracted to him at first, but he was so interesting  I would go out with him again. I went home and fantasized about what it might be like to be over his knee. I wondered how it works when you meet someone and you already know you share this interest.  With someone I just met it would take me a long time before I could broach the topic of spanking. With him, well, he already knows it. But that doesn't mean I want him to take me back to his apartment right away and throw me over his knee. Okay, I did kind of want that, but as I've always believed, if you actually are interested in someone you have to take it more slowly and establish something other than a purely physical connection.

So how long do you wait with someone you know wants to spank you? I would think that it would be a couple of dates. But then, I've also never been spanked and then not fucked the guy. So if it was like 4 dates, would that be sort of slutty? And what if on the second or third date we were kissing and he started rubbing my bottom and whispering that I had been bad. Would I be able to say no? even thinking about it is getting me hot as I type this. :) Spankings have been so few and far between in my life, I don't know that I could say no, even if saying no increased the likely hood that when it actually did happen it wouldn't be a one or two time thing.

because my date went so poorly I responded to another ad. We'll see how this goes.

First Craigslist Date: The old (OLD) dude

37 is such a flexible age for me. I mean, there are definitely 37 year olds I know that I would date. I don't think big age differences are a problem once you hit 25- but maybe I'm biased, my parents are 13 years apart. They met when my mom was 25 and my dad was 38. 

So I met bachelor number 1 from craigslist. We made plans to meet in front of central park, right across from Columbus Circle. We'd been emailing for a few days. He seemed quite nice. He looked tall and skinny in his pictures (VERY much my type). He was a little formal in his emails, but I find thats common in people who are older than me and didn't start emailing in their youth.

He texted me in the afternoon and told me he was wearing a brown shirt. After work I headed over to the park and sure enough there was this old ugly dude in a brown shirt mulling around in front of the entrance. He had not seen me yet. Would it be so horrible to just slip away? I mean, this guy was old. He had to be at least 45. It would be completely acceptable to not meet someone who had lied so horribly.. would it?

Then my phone rang. As it turns out, my date was running late and calling to say he wasn't there yet. ::phew:: saved! Guy in front of park was someone else's date!

I thought about what a funny story that would be to tell when my real date arrived. Like hahah look what just happened.

Then my date arrived.

1)okay, man was definitely not 5'10". MAYBE 5'7" MAYBE. And thats how tall I am. Shorter or equal to my height= not attractive to me. Sorry, its just the truth.

2) I'm pretty sure he was older than 37. Or maybe just an old 37.

3) in his emails he said they were bad pictures. They were not. They were amazing pictures of a rather unimpressive looking fellow.

We went for a drink. He was perfectly nice, but he had a tick. yes, he had a facial tick. Maybe his nose was itching or something, but I'm pretty sure it was just a facial tick.

Oh and did I mention he was practically drooling all over me? Of course he was. But wow, I'm used to having guys want to take me home, but there was this edge of desperation, like he hadn't gotten laid in months. In a way, it kind of disgusted me, but in a way I wanted to let him push my legs apart in the alley behind the bar, just because he would be so damn happy about it. But as he leaned in to talk to me in the crowded bar I just couldn't stop myself from leaning away. I was practically doing a backbend.

Like I said, he was perfectly nice, even interesting, but I was just not into it. I thanked him for the drink and told him I had to meet friends back in brooklyn. He kissed my cheek good-bye and put his hand on my waist as he did so. His hand was practically shaking and his eyes were sleepy with desire. It felt pretty good to be wanted that badly.

But yeah, not going to see him again. Not sure what I'm going to do when he calls, and he is obviously going to call.

Second Response

Guy #2 responded. Also sent a picture. Looks kinda like a stanton island guido, no offense, not my type. Not ugly, but no one I would look at twice in a bar. But then I read his email. He was funny, smart and obviously well educated. I looked back at guido picture. It looked like he had a chin-strap beard. A chin strap beard! I went back and read his email again. he sounded SO normal and nice.

Oh, and he obviously thinks I'm fat because I didn't send a picture. He was all, "okay, you didn't send a picture. Maybe you could tell me a bit more about your body type- curvy? bbw?"

Maybe I should give him a chance. Also, I kind of want him to know how hot I am. haha.

First Response

I got a response in my inbox Saturday with a picture. The guy was 36, 5'10",  and looks like someone I would think is cute. He's from the west coast, and seemed nice in his email. Of course everyone seems nice at first. Isn't that what the neighbors always say about serial killers? I sent 2 pictures back. One is a nice shot of my face where you can see how blue and pretty my eyes are. The other is a full body shot. I assume there are lots of fat girls on craigslist. Not that I have anything against that, but I've got a body. Curvy in all the right places- Large chest, smaller waist that curves out to my hips. 

I am still feeling really shady about this whole thing. 

What I did the day after my 26th Birthday

I went onto craigslist.  Where else do you find people into spanking?  you can't meet someone and know, you can't put it on match.com or nerve.com with your picture up there for the whole world to see. so where do you go? I guess Craigslist? But that feels so sleazy too!

I went into the m4w and searched "spank" and "spanking" and came up with a bunch of hits. A bunch of CREEPY hits.

No, I don't want to come over to your house right now. No, I don't want to read your sexual fantasy. (okay, maybe I'm a little curious, but I'm certainly not responding to it). No I don't want to send my picture to some dude I've never met! and no, I don't want to (immediately) submit to your every desire.

There were two that were not creepy. I sent responses. no pictures. now I'm waiting.

First Steps

So this is what I did on my 26th Birthday.

1) I bought myself a vibrator. Never had one before. Never been much into masturbating, but hey, people seem to like it, right?

2) went home, discovered why people like masturbating.

3) Went out. Obviously, its my birthday. I"m not going to stay in my bed all night.

My 26th Birthday

On my 26th Birthday I decided that I was sick of not being satisfied.

 I've been dating for ten years and I've met anyone who has satisfied me. Okay, I've been in relationships that are emotionally satisfying and intellectually stimulating. I was even in one relationship that was physically exciting... but never one thats both.

And here's why: I'm kinky. I'm really really kinky. I'm submissive and I especially like to be spanked. I like a lot of other things too... and I've never been able to say anything.

And this is my quest to find fulfillment.