Days 5,6 and 7

Mostly more of the same. There was one response that caught my eye, from a guy named Steven. He sounded fun and interesting, but he didn't attach a picture. I'm kind of skeptical about that, but I sent a response asking for one. We'll see what happens with that.

In other, non craigslist related dating, I did get two requests for dates this week. One from a much older guy at work.  He's a friend of mine, we sometimes have lunch together and I hang out in his office listening to music when I'm bored. He called me on Saturday and asked if I'd like to go out sometime. I felt sort of bad turning him down, because I do enjoy his company, but I know that I'm not interested in dating him. It caught me totally off guard,  I was not even sure how he had my phone number. Anyway, I stuttered out an awkward reply about not really wanting to complicate things by dating and then lied and said I had a boyfriend. I said we were on and off again all the time, so I didn't talk about it because other people couldn't keep up with the drama. 

The other request was more promising. I met this very handsome, tall, dark research scientist at a holiday party Saturday night. We ended up flirting for a lot of the night and he asked me for my number at the end of the party. I do hope he calls.

I'm also wishing I had someone around to spank me for lying yesterday. ::sigh::

Day 3: The pain drags on.

The first couple were more explicit than I would be comfortable with. I really think that I may post an ad again after the holidays thats a bit more specific about what I'm looking for. One of the guys even sounded nice, but his email was something like "hardspanking69," which seems a little excessive to me. He actually had to go to the email server and sign up and be like "yeah, I think hardspanking69 pretty much embodies what I want the world to know about me."

One of the guys sounds like a sad sad sack, he's like "kids don't scare me! Crazy exes don't scare me! I just want someone to love me!"

Then more mid to late 40 year olds. I have nothing against 40+ men, but I am looking for someone to be my partner now, I'm not opposed to being more serious in a few years and I know I don't want to start a life with someone who's so much further along in it than me. Plus, my mom married someone just 13 years older, and he passed away and left her a very young widow. I know we don't control everything, but I'd like to take the chances of that down.

I also got a 4 page (at least!) long fantasy.

And the last one is a germ freak. A self described germ freak.

Great. Now that Rob has moved to Denver, my options are looking even more dismal. 

Day 2- 10 responses

I checked my email again tonight, and had 10 new responses.

The first one is all misspelled and illegible. Pass.

The second one says simply "Get in touch." 

The third one is pictures of a guy and babies. This makes me think he has children. Not what I am looking for.

Fourth one is hoping I am Jewish. I am not.

Fifth one is a classic. From "Old Dad." That's actually the moniker that pops up on my screen. He's 65. Oh my God, I don't even think my grandmother is 65.   His email is actually quite nice though, and he calls me brave for pursuing what I want. Now I feel a little bad for making fun. Okay, but I'm 26 and that's a hell of an age difference. Anyway, at the end he adds this note that says his focus is as a dad and not a daddy. I don't know what this means. All this strange new slang! Can anyone offer any help?

Sixth one wants to let me know that older daddy's spank better,  asks if I'm free during the day, and tells me he doesn't want any commitment. To me, this screams MARRIED.

Seven, eight and nine are all explicit fantasies. I mean, I knew I was going to get these, but its frustrating because its not what I'm looking for. 

Ten is shorter than me. That's one thing I just can't compromise on.

Day 1- 25 responses

I checked my email after work today, and already had 25 responses.

Okay, lets take a look through them.

First response: 30 year old Indian guy, no picture, boring response. NEXT

Second response: 25 year old, cute-ish picture, not my type. I'm picky I guess.

Third Response: 33, 6'2", Andrew (love andrews, for some weird reason)

And then... wait for it... this sentence 

"I am just out of a 10 year relationship and need to spend some time with someone that can make me forget her…Also going through final exams process right now and need to distress."

Great. I would just love to be your rebound girl. Thanks. 

Fourth response: Argentinean/Egyptian , 6'4"... then sadly, the pic is not my type.

The next 10 responses are all from men in their 40s. Too old for me! 

Here's a gem: 

"ive never done what youre looking for ,but i wouldnt be against trying it you could teach me, how to be specific with you"

This one confused me 

"It's not really so odd at all. I like being slapped in the face. And I look like such a quiet, good-natured kind of guy."  

Um... does he want me to respond to him, or does he just want to tell me what turns him on?

I also got a 30 line poem. I'm pretty sure Pablo Neruda wrote it though.

I got some pretty explicit stuff too. No cock pictures though. I really thought I would get some cock pictures. 

Here's a classic

 "No its not odd at all. Everyone has their thing in bedroom. Don't wanna talk about these thing very much but I have to tell you that I am open minded. Anything can happen between two people. And I mean two people. No third or fourth ones. If you can limit you open mindedness on this particular thing that means we have a base to start with"

Limit my openmindedness on threesomes and orgies. Hold on, I'll try to rein in my fantasies. What the hell? 

Hitting the Heartbreaks

I forgot to mention that Rob broke it off with me. When he was here, we talked about me going to visit him in Denver over New Years. I travel so much for work that I have a ton of  miles and didn't have to worry about making arrangements right away. Then, last week he sent me this email:

I've been thinking about you coming to visit me for new years. I'd like to see you, but I'm not sure its a very good idea. I think you feel the same ways as me about continuing to date long distance... but we haven't talked about it so I'm not sure. I've been in a few long distance relationships and obviously, they all went pretty badly.  The thing that worries me is

that they both happened slowly, and kept going until we ended up hating each other. You coming to visit seemed like a good idea but I'm afraid that it will complicate things in a way that I'm not comfortable with. This is a hard thing for me to say because I like you and usually that's as deep as my thought process goes. Anyway I'd love to know what you think about it.

I'm kind of heartbroken. I mean, I know it wasn't really possible to do the long distance thing, but its so hard. I've never really had a boyfriend who was into spanking. I think it can be kind of rare to find men who are as into as I am as you can;t really ask people it when you first meet them. I already liked Rob, I would have dated him even if I didn't know he was into spanking, and to find out that he was, was like the best thing ever. And now I am sad, sad, sad. What happens if I never find someone like him again?

Looking for more...

After I came home from Ben's, I felt kind of strange. I like it when Ben spanks me, but I don't like how I pretty much just go over there for a spanking. I like it rough, but sometimes I like to be cuddled and treated like a good girl too. I really am looking for a relationship, not just an on going fuck buddy (or, as in Ben's case, a non-fuck buddy)

So I decided to put my own ad up on craigslist today, just to see what kind of response I would get. I had no idea how to start so I just threw something together:

Do you think this is Strange?

I'm 26, tall, cute, normal weight, intelligent, outgoing, charming and a little silly. In the past I have been approached in bars, clubs, or subway stations, and have even managed to go on dates with attractive men. So why am I posting on craigslist?

Its because I'm shy about one thing. I have a thing for being spanked. In my experience, not everyone thinks this is so amazing. I'm not usually so forward about this, but I'm sick of wasting my time dating people who aren't interested. That's not all there is to me, and thats not all I'm looking for, but I figured it was someplace to start. 

It is now up for 7 days. I am interested to see my responses.

Ben takes off his belt.

I left work a few minutes early so I could be at Ben's place by 5:30. I, of course, was running late, and at 5:31 I get a text message telling me I'm late, and that every minute late I am equals two spanks. 

I was 10 minutes late. Ben was not happy with me. I walked into his apartment and bolted the door. I took off my sweater, then unbuttoned my white collared shirt. I unzipped my skirt and let it fall to the floor. Then I slipped off my bra and tights, so I was in just a little black mesh thong. I left my clothes in a little pile at his door, and he was touching himself.

I walked over to him and knelt at his feet, "Is this the part where I apologize?"

"Yes"

"I'm sorry" His cock is in his hand and he directs me to lick the shaft. Then to take it in my mouth. 

"So you have a boyfriend?"

"He's not really my boyfriend."

"What would he say if he could see you now, sucking me off?"

"He'd think I was a total slut."

"You are a slut. Look at you, how often are you going to beg for my cock while you're dating him?"

"As often as you want" He then forced my head down and fucked my mouth. 

"You like that you little slut? You like gagging on my cock? You like it when I hit you in the face with it?  Stand up. Turn around" Then he starting spanking me, hard. I was sort of jumping around, crying out, flinching. He threw me over the chair, and out of the corner of my eye I could see him undoing his belt. I wasn't sure if he was taking his pants off, or if he was going to whip me with it. He doubled it over and let it rest against my ass for a second before winding up and smacking me across the legs. It didn't hurt as much as I expected, but I still moaned and squirmed and whined every time it hit me. He counted to 20 and told me not to be late again. Then he made me lie down on the floor and masturbate for him. He kept shoving my legs apart telling me to spread wider. 

He had me get on all fours and continued spanking me. Then he came on my face. 

Ben, the hookup that just never ends

So I haven't heard from Ben in like 2 months. Today I get this text message.

Have you been a good girl lately?

It might be kind of strange, but I like telling him sexy little lies that turn me on.

I've been seeing this guy. He wants me to see only him.

Does he know what a slut you are? Does he know you suck my cock every time I want it?

No, he doesn't know. I shouldn't even be responding to you...

Does he know how you like being over my knee? 

No. and I've been thinking about it.

I think you need a spanking soon.

How soon?

As soon as possible. you deserve it.

Its true. I haven't been punished in a long time. I need my bare ass spanked raw.

I'm going to turn it bright red so you know what a little tramp you are.

My boyfriend treats me like a good girl, but I need to be treated like a dirty slut.

You are a dirty slut, and I'm going to show you just how dirty. When do you want your spankings?

 

Tomorrow. Please tomorrow.

Come to my apartment tomorrow right after work. As soon as the door closes behind you I want you to take off everything but your panties. I'll be sitting on the couch, I want you to get on your knees in front of me and wait to be told what to do next. I want your hair up and a thong. 

Yes Ben

I"m not going to come tonight so I have a larger load for your face tomorrow. 

The Solution

Well, Sean and I found a way to hook up.

Here's how it went down.  We had a full house- two aunts, two uncles,  six kids, my mother, one grandmother, my sister and my sister's not-boyfriend (he is obviously her boyfriend, but she refuses to call him that). The kids (my sister, Lily, and I count) got control of the basement.

My family decided to have a big make your own pizza and margarita night. We also just put in an above ground hot tub. So I asked Sean if he just wanted to hang out with my family because it sounded like tons of fun. He was a little reluctant (remember, he's not my mother's favorite) but agreed to. My sister actually loves Sean, the two of them, and we ended up playing silly board games with my little cousins and hanging out. Then, we got my 17 year old cousin to agree to drive me, Lily, Sean, and Adam (Lily's not boyfriend) to the local pub. In exchange for driving us and picking us up, we told him we would we would let him drink with us when we got home.  

At the bar, Sean leans over to me and is like "Rose, do you think we'll ever live in the same place?"

I laugh, trying not to think about how much I want to say "yes! tell me where to move and I'll do it!" and reply "No"

"Why do you say that?"

"Because I don't want to live in Chicago right now. You do, and you're planning to move to a small town in a year and I doubt we'll end up in the same small town"

"Thats not for sure Rose. That could change"

Sean wants to be a teacher in a small town, he's teaching now, living at home and paying off his student debts.

So we go back to my house. My cousin has built a fire in our fire pit and we're hanging out in the hot tub. Sean has his hands on my legs under water. Around 3 or so we're watching TV on our big comfy couches and everyone is falling asleep. Sean has a blanket over us, and is rubbing my pussy. He leans over and whispers, "I want you to come." He slips his fingers in me and finds how wet I am. I tell him "Not here. we have to go back into the study." 

"Oh Rose, you have no idea what you bring out in me."

 We have a little private room in the basement with a desk and a couch. Once inside the room has my pants off and tells me I need to come before he'll fuck me. I beg him to fuck me anyway, but he refuses. I am kind of drunk and its hard for me to come when I'm that drunk, so I actually fake it, which isn't my favorite thing, but sometimes it's necessary.  

He fucks me on my back, then bends me over the couch, then has me on the floor. Then he has me ride him and says he wants me to come on his cock. I don't have to fake it this time.

"You know what I want?" He asks.

I nod.  I know what he wants, and I'm drunk and turned on.

"What do I want"

"You want my ass." I respond.

"I want to be your first. I want your virgin asshole. I'm going to make you my whore. I'm going to push you down, and make you cry, and take your slutty asshole. I'm going to make your virgin asshole into my slutty hole"

Then he pushes me on the floor, and I'm so turned on that I'm ready to give it to him.  He spreads my ass cheeks and pushes the tip of his cock in.

I think I'm going to die. He is going to split me apart and I'm going to die. So I do the same thing I did the first time I ever had sex- I totally panic and think of everything that could go wrong. I tell him to stop. He says please.  I tell him to stop again. He tells me to relax, but he's stopped. He makes me please him with my mouth to make up for it and swallow his come. 

I tell him that I want him to take my anal virginity, just maybe I'm not ready yet. 

Then he pauses, and turns to me seriously and says, "Rose, I know I'm with a lot of girls now. I know I chase girls all the time. but I only want them right now, while I'm young. I want you till I'm 80"

"Shut up" I playfully hit him

"No I'm serious Rose. We have fun together, we have fun when we're fucking and fun when we're not. I can see us together when we're old, with kids and everything."

I think about this for a minute. I would have probably reacted differently if I hadn't been so drunk. I turned to him after a few minutes and said, "Okay, but if you want to be with me forever you're going to have to learn to like spanking me. Thats non negotiable"

I can't even begin to think about what I think about this yet.

Thanksgiving

So, Sean wants me to come and see him while I'm home for the holidays. He's told me to clear my schedule for the day after Thanksgiving because he's coming to pick me up. He asked me if I had been good since the last time I saw him. I said I hadn't, I'd been a very naughty girl and had been having all sorts of slutty thoughts about him. I could hear him starting to breath more heavily on the other line when I asked him how he was going to punish me.He told me the first thing he was going to do was push me down on my knees and make me give him head.

I had quietly taken my vibrator out as he'd been talking and had been rubbing it over my panties and I'm so hot for him that I actually came just thinking about his cock in my mouth. I'm getting so excited writing this right now I think I might have to go grab my vibrator again when i'm done. I want to fuck him so badly, just thinking about it distracts me at work! He's so wrong though. I know he doesn't want to actually date me, and even if he did he's so far away.  

I seriously think I would let him do anything he asked no matter how dirty. But here's the thing: He is teaching school in the suburbs and moved back in with his parents for a bit. I'm going to be with my parents. Where the hell are we going to do all these dirty slutty nasty things? The back of his car? I kind of want to be like "so lets get a motel room" but I don't want to sound like some hooker. I feel like it should happen more naturally, like "oh here we are at this bar. haha we're getting a little tipsy and his hand is on my leg and now he's kissing me in the corner"  What to do, What to do?

Rob came in Thursday night, so I called in sick Friday to spend the day with him. Rob looked at me, all naked in my bed, very disapprovingly as I lied to my boss about how sick I was feeling. I knew I was going to be in trouble for that.

Both my roommates left by 11 am. Rob had me over his knee by 11:01. seriously. The first spanking I got from him that morning started with a lecture about lying to my boss. I made a big show of kicking my legs, but within  a few minutes I was rubbing against him. I parted my legs, and his blows were reverberating to my pussy. I came just from his spanking. He was so excited by that. He talked about it all morning.

My second spanking was the hardest one I've ever gotten. By the end, I was whimpering submissively and rubbing my bottom and actually really seriously meaning it. I almost had stopped him in the middle because it hurt so much. I don't have a ton of experience with spanking. Obviously. This was the first time I've seriously been in any pain. I whimpered through the sex afterwards, which was really gentle and sweet. He focused on me and was such a sweetheart.

My third spanking was just kind of ridiculous, because it was clear we were trying to jam as many in as possible. I swear I got like 5 spankings between 11 am and 7 pm when we left to meet up with my roommate for her birthday.

It was my roommate Liz's birthday. She was turning 27. The party started at 8, but she wanted me to be early so she wouldn't be alone. Thank God we were early because only two people showed up between 8 and midnight. Okay, don't feel too bad for liz yet, because about 30 people showed up between midnight and one.

Rob picked up the tab for me AND Liz. And he didn't even say anything about it. He found the waitress and just told her. Cute!

My friend Maggie came in and was like "um did you get laid. I've NEVER seen you looking so relaxed." hahahahahahah

I liked the way being a couple with Rob felt all night. Almost all my friends have boyfriends, and sometimes its nice to be part of a pair. Even if just for a night.

Rob left early the next AM. Sad sad :(

ROB IS COMING

I am so excited. Rob's coming to visit me this weekend. Says he knows I've been a naughty girl and it would be wrong to let me get away with it. I'm sooo excited! 

Email from Rob

So I was pretty sad about Rob not living in New York. He sent me a text when he left Sunday morning. I sent him one back, but didn't hear back. I'm more the mope around and hope he calls than the caller.

 He sent me this email this morning:

I hope you are doing well. I've been thinking about my time in New York quite a bit. I had a lot of fun, and I'm glad we got the chance to hang out for a few days. The truth is that I've never had someone be as straightforward with me as you were . I can just appreciate the memory or whatever, I'm also still really intrigued. Anyway, like I said, just felt like sharing 

I asked him if he wanted to come and visit me. Now I'm just waiting for a response.

Rob Saturday Night

When Rob and I came back from Brunch, both my roommates were conveniently gone. He grabbed my upper arm and said, "I think you know what that means, naughty girl."

He put me over his knee and pulled my skirt up. He pushed my panties down to my knees and stroked my bottom. I begged and pleaded with him, but it wasn't any use. He spanked me and he was good at it. I wouldn't have guessed it was his first time if he hadn't told me. 

I'm not really feeling like sharing the details. I wish he wasn't moving to Denver.

Rob- Saturday Morning

So the next morning Rob and I woke up and started fooling around again. I let him tell me what to do and be forceful, I let him choke me a little, and be rough. It was clear that he was so into it. 

As I've written before, I have trouble bringing up to my partners that I want to be spanked. For some reason it is so embarrassing. I even found it hard with Rob, who basically told me that he wants to spank a girl.

So we fucked the way he wanted in the morning. My roommates were both home, and being that I live in a tiny apartment, the walls are too thin for spanking anyway. We were laying in bed, contemplating what we wanted to do for brunch. I asked him if he remembered the brunch where Sam talked about the nun who wanted him to spank her. He did, and I told him that the second I knew I wanted to hook up with him was when he responded to Sam and said he would definitely spank a girl. I told him I had some serious spanking fantasies and wondered if he might want to spank me some time.

Kid in a candy shop. He's always fantasized about spanking but never done it. I told him he could, but we'd have to wait for my roommates to leave.

YES! someone I actually like, who likes me to is into spanking. I was so excited. 

And then I remembered. He's moving to Denver.

Fucking Denver. I hate my life.

Rob (Friday night Part 2)

I decided to make my move that night. Of course, my making a move isn't very forward. It's more putting myself in a position where he can make a move. I was paying a lot of attention to him, laughing at his jokes, letting him touch my lower back at the bar.  I pulled Katie aside, and asked her if she would mind if I made out with him. I didn't want to, but my friend Tricia told me I had to.

After the party we all decided to go get food. Rob and I conveniently lost everyone else (whoops!) We got into a cab and went back to my place. We were all over each other in the cab and he kissed me. Then his hands were everywhere which made me giggle. The cabbie (poor guy!) dropped us off at my corner, and it was a struggle to even get Rob to come to my apartment because he was definitely trying to fuck me on the street. Not seriously, but he was saying he couldn't wait until we got back and kept pushing me up against the wall.

We finally made it back to my bedroom and started fooling around. It was going great, he had a condom and I opened my legs for him. I probably wouldn't have normally had sex with him so fast, but he was moving and I knew I wouldn't see him again for a long time. So he entered me. and it was great.

But then he lost it. Completely  lost his erection.  ARGH! I know he was super drunk, and so I was really sweet about it  and told him that it was only because he was drunk. He was like, "Its not you. i think you are so hot" and I said, "ummm I know its not me." which made him laugh and I think feel more comfortable about it.

So then he started getting excited again, and hard again, and we started having sex again. and he lost it. AGAIN. 

We were laying in bed talking, and he asked if I wanted anything. I know he was asking me if I wanted him to go down on me. I turned to him and said, "Actually Rob, I kind of like it rough."

His head snapped around and he said, "Really?" I nodded, "Really? You're not just saying that to turn me on?"

"No, I wouldn't say it just to turn you on." And he was suddenly on top of me, pinning me down, shoving his dick in me. It was a fantastic moment. He had his arms pinned over my head and was thrusting into me, we were half way off the bed and  and HE LOST IT AGAIN. 

He basically got kind of pissed off and said, "I can't believe that just happened Rose. That was about to be the hottest sex I have ever had in my whole life."

At this point its like 5 in the morning, so I promised him we could have the same sort of sex when we woke up. He told me he really liked cuddling and I fell asleep with my head on his chest.

Rob (Friday Night Part 1)

Rob is a friend of mine I've always thought was really attractive. He's lived in Boston the whole time I've known him. I met him through my former roommate Katie about two years ago. They were friends in high school, and they actually briefly dated when they were 15. Katie now has a fiancee that she lives with, but her and Rob are still close and he comes to New York to visit her every few months. Katie's fiancee is kind of a jealous guy, even though there's nothing going on between them, so when he comes, he usually stays with me and my two roommates. We also have a much bigger apartment.

When he comes, he usually comes with his best friend Sam. I adore both of them, but Rob caught my eye especially this summer. In June Katie, Rob, Sam, my roommates and I were all at brunch and Sam started telling this story. When he was in college he knew this girl, Sarah, who wanted to be a nun.  Sam was really attracted to Sarah, and he thought that Sarah liked him too. She was devoted to becoming a nun, so she would never let anything happen. About a year ago, she started to have some major doubts, and asked Sam to come an visit her. She wanted to hook up with him, but not have sex. 

They were hooking up when she started begging him to spank her. Sam said that he was totally taken aback and had no idea what to do. He said he didn't want to hurt her, and he thought it was too weird so he got up and left. As he was telling the story, he was like "Isn't that the weirdest thing? Why would anyone want that? I could never hurt someone I was with"

So Rob who's had his face in his breakfast, looks up and shakes his head, "Oh I definitely could. I would totally be into that. If a girl asked me to spank her,  I would fucking love it."

Of course, everyone at the table starts disagreeing. I've been sitting pretty quietly, probably blushing deep red through this whole thing. So I pipe up "You know, I think everyone has something they're in to that they don't always announce. And this is probably why, because we're all sitting around here, talking about how weird this girl is." Which I think shut everyone up pretty quickly.

I was already pretty attracted to Rob, I actually kind of thought that if he moved to New York in the future, we would date. That pretty much did it, and I decided that I wanted him. But he's a good guy, and he had a girlfriend. I actually would want to be serious with him later, so I wouldn't want him to cheat on anyone with me.

Well, he always had a girlfriend until last weekend. Sam and Rob are moving to Denver. They've always wanted to drive cross country and move there together. They're moving after Thanksgiving, but Rob already quit his job and is staying with his family in upstate new york until they leave. The two of them came down for a visit. Usually I would know if they were coming to New York, but I've been out of town on business a lot lately, and have been out of touch with most of my friends. So I got into town Friday morning from Washington DC. I had taken a questionable "travel day"- my favorite move to pull- and showed up at a birthday party. 

I didn't realize I was unexpected, but when I walked in Sam ran at me and lifted me in a huge hug.  "Rose! We had no idea you were going to be here!" I saw Rob at the bar, and he looked so cute. I ran up behind him and gave him a flirtatious hug. He was also very excited that I wasn't still out of town.

I was sitting with Sam having a beer, and he was telling me that he and his girlfriend were staying together even though he was moving. I asked about Rob and his girlfriend, and Sam laughed and said, "Yeah, they broke up. Thank God, I never liked her."

"Really? I liked her."

"Maybe because I'm his best friend I'm more protective, but I never thought she was good enough. Wait, when did you meet her?"

Now over the summer I made a kind of dumb decision to go visit this guy I had been seeing in New York before he moved to Boston. We had only really been on two dates before he moved. He had begged and pleaded for me to come down and see him, and said he missed me. I'm kind of impulsive, so even though I didn't know him that well, I went to see him. He turned out to be a huge asshole, and it ended with me leaving his apartment in the middle of the night. I don't know Boston at all, I have a cousin who lives there but was out of town, so I had a suitcase and I was standing on a street corner. I called Rob crying and he and his girlfriend came to pick me up. I was kind of embarrassed about the whole thing. I don't like talking about it at all.

"When I was in Boston this summer. Didn't Rob tell you he had to pick me up crying from a street corner?"

"No. No he never told me that" Sam looked kind of concerned, "I can't believe he didn't tell me that, especially because I know he's such a huge Rose fan, and if he saw you I can't believe he wouldn't tell me."

Hot and Discreet. Open to Spanking. What more could I ask for?

Sean Comes to New York for a Day

Yes, Sean came to New York. He was on his way upstate to see his grandparents. He stopped for a night in the city and stayed with me.

I was his naughty girl. I did what he asked, and I did it enthusiastically. I sucked on him. I talked dirty to him. I rode him. I got on all fours for him. I got on my knees and begged for his cock in my mouth. He pulled my hair, spanked my ass (was slightly more enthusiastic than last time), called me his cumslut. spilled his come on my breasts, then my face, then my ass. He fucked me every which way. I had more orgasms than I've had before (6!!!)

He told me he wanted to take my anal virginity. He put a finger up my ass. I struggled a bit, but he had me pinned down and I submitted to it. I've never been with anyone who wanted anal. I've always been a bit curious about it but it made me so nervous. I liked his finger and I didn't like it. 

He still had me pinned and I whined a bit saying it hurt. He told me it was a good hurt as he stuck his second finger up. I got a little panicked, and he whispered to me to relax. I tried to, but I was so nervous. He pulled his fingers out and told me that I probably shouldn't try anal because I was so tight and nervous. I was sorry, but he stroked my hair and told me not to worry.

"Rose, I didn't come here to fuck you in the ass, I came here to see you." He said it so sincerely, I felt a little guilty that it made me burst out laughing. 

I know I'm the best sex he's ever had. I know I'm one of the best friends he's ever had. He calls me on my birthday and every holiday. He sends me presents in the mail sometimes.

He should admit he loves me.

What I'm thinking about

I'm thinking about my two nights with Sean last week. About a couple things. First off, Sean has more sex than anyone I know. Seriously.  In high school and college he always always always had a new girlfriend. Then came of Senior year of college when he was hooking up with everyone. He was hooking up with my roommate. He was hooking up with my friend from studying abroad. He was trying really hard to hook up with my other roommate. 

Then after college, he's had one serious relationship and dated a million girls. The serious girlfriend was this girl named Margaret.  He told me that one thing he loved about Margaret was that she was always up for having sex and for letting him do whatever he wanted. 

After spending these two nights with him, doing "whatever he wants", he tells me its the hottest, dirtiest sex he's ever had. And the first time he's done a lot of things he's always wanted to do. Was he lying to me about Margaret? Or is he just as shy about his kinks as I am?

If Sean, the most openly sexual person I know, won't even talk with his partners about his real desires, how do people ever end up having kinky sex? I mean, I've read the internet. I know people are having this kind of sex, but how do they find each other?

Sean Spanks Me (AKA the culmination of my fantasy life since the age of 16)

In a word: Disappointing. 

Haha so it was a little much to live up to. I should take it easy on the poor boy!

There we were, Saturday night, my hotel suite in downtown Chicago. I basically told Sean that if he wanted me to blow him, he was going to have to spank me. He reluctantly agreed. 

Maybe I should have given him more instruction. He was like "uhhh I don't know what to do" which was ruining the fantasy for me. I was like "throw me over your damn knee and hit my ass. this is not so hard.... you can do it harder you know... you aren't going to hurt me... give me a lecture about how naughty I am or something."

He did try valiantly. And then we had some hot dirty sex. He dirty talked to me, I masturbated for him, he masturbated on me, he bit me and pinned me down. He's more of the "I'll punish you with my huge cock" type. So at the end he was trying to come and asked me to recount to him everything we'd done.

I told him about the things he'd said to me and the various positions he'd fucked me in.  Then I said, "And you spanked me, and you liked it more than you thought you would."

"Uhhhhhhh" was his only response. A negative "uh" at that.

"You are not the only one trying to get excited here. Can't you at least pretend?" I begged.

I have failed to convert him. If he's so damn dominant, why doesn't he want to spank me???

Business Trip to Chicago

I was in Chicago on Business last weekend. I told Sean I was coming. He told me it was over with Andrea, and that he would love to see me. 

I came in two days early to see my mother. Now, my mother does not like Sean. She still hates him for breaking my heart when I was 18. Even though it is stupid, I sometimes lie to her about hanging out with him. So my conference starts Thursday, and Wednesday night Sean picked me up and drove me to my hotel downtown. 

So we get to the hotel and I invite him upstairs. I tell him we can watch a movie and order room service on my company's tab. We're barely inside the room before I've leaned in and kissed him. Before long I'm straddling him on the bed and we're furiously making out. "Rose you are so much fun." he whispers as he pins me down on the bed. He bites my ears and it kind of hurts, actually it hurts a lot, but I want him to hurt me. His teeth are on my breasts and then my nipples, which hurts so much I want to cry out but I don't want him to stop. I want him to make me his. 

Its kind of pathetic how in love with him I am.

"Can I really do whatever I want?" he whispers as he's kissing down my stomach and starts to unbutton my jeans. "Will you be my submissive little slut?"

I nod, because he can have whatever he wants. He's licking me now and biting my inner thighs.  

"Show me how you touch yourself when you think about me" I slide my fingers down and start to rub myself. He's kneeling in front of me, between my legs watching. I've never done this before and I'm a little self conscious. Its hard to bring myself to orgasm with someone watching. He starts licking up my inner thigh, but I push him away with my leg. He pins my leg down and tells me that I don't tell him what to do. I am so excited that his little dominant command makes me come (well, that and the fact I'm stroking my clit).  

He's laughing and on the bed and tells me he doesn't like to be told what to do as he forces his cock in my mouth.  This is why I'm so in love with him, here we are, trying out some new sex roles that we're both not totally comfortable with, and he's giggling while doing it, but still being forceful. He's pulling my hair, hard, as he thrusts his cock down my throat. Then he comes all over my face. 

He's a gentleman, so he runs and gets me some kleenex to wipe my face off, and we're cuddling in the bed. He tells me that he's never seen a girl masturbate to orgasm and that it was super hot and that he's never had anyone tell him that its okay for him to be dominant. He says the closest he's ever come is that one girl asked if she could whip him. 

"I'm so naturally dominant that I think if she had tried I would have just grabbed the whip away from her, thrown her down on the bed and fucked her." He pauses for a moment. "I've also never called a girl a slut in bed before. I didn't realize how much I would like it." At this point I can feel him getting hard against my back. "Tell me what a slut you are for me." he says in that throaty voice he gets when he wants me. 

He's pushed me onto my stomach and fucks me from behind while pulling my hair and calling me his slut. Then he tries "whore" out. 

After he comes I tell him that what I really like is being spanked. I am blushing as I say this. Yes, I'm naked, in bed with someone I've known for years, who I know wants to be dominant, and I can barely tell him what I want. 

He hesitates. "Thats not something I've ever fantasized about." He says.

"Don't worry. You'll like it" I say back.

"I don't know. I wouldn't know what to do. I've never actually tried out someone else's fantasy."

"Sean. I told you you could do whatever you want and you won't do anything for me? It doesn'twork like that. And you'll like how much it turns me on."

He agrees to try next time. He spends the night in my hotel room, but we're both tired so we fall asleep pretty soon after.  He leaves the next morning as I'm on the way to my conference. I'm in Chicago for 4 more days, but have a bunch of work stuff. We decide to meet up again on Friday night.

Ben- I guess it's not over?

So the next day Ben texts me. "Was that you last night"

So I texted back, "yes, sorry I wasn't expecting to see you, I was so surprised I forgot to say hello"

"I thought it was you. So you were out with your friends last night. Were you good?"

"No."

"Did you do something slutty?"

"Yes. I went home with a guy I used to work with. I sucked his cock." 

This was a lie. I don't know why I did it, but it turned me on.

"Was he big? Where did he come?"

"yes. big and thick. he came on my tits"

"you are such a slut. you are a dirty dirty little slut"

At this point I'm in a museum with my friend but I'm so turned on.

"come over to my apartment."

"Can't now."

"When?"

"Tomorrow?"

"No. you need it today." 

And I did need it. I needed it badly. So I left the museum about an hour later, said goodbye to my friend, and took the train to his apartment. When I got there Ben bolted his door and sat on his couch. He asked me to take off all my clothes and as I did he masturbated. Then he had me stand in front of him, completely naked and ask for my punishment. He had me tell him in detail about what I had done the night before. This time I was more ready and had some good fake details to throw in. Then he ordered me over his knee. He played with my bottom a little while I rubbed up against him, so excited for my spanking. Then he hit me again and again, calling me his little slut and pulling my hair. He had me get up and go to the kitchen and find him something to spank me with once his hand grew tired. I brought back a thick wooden spoon. I'd never been spanked with anything but a hand before. It hurt for longer than a normal spanking, and I was rubbing my ass while I blew him afterwards.

A friday night sighting

So Ben and I have been exchanging emails since our second date, but like I mentioned, I've been out of town on business. 

When I came back I sent him an email saying that I had been a naughty slut in Toronto, and how would he punish me? He told me I had to tell him what I would want him to do, and then he would let me know how I would be punished. He told me he was definitely going to give me a spanking and make me please him.

So I wrote this dirty email about being over his knee with my skirt up and my panties around my knees.

He wrote back saying I liked being spanked too much, and he was going to have to find something that would be a punishment. he told me that he was going to spank me naked while he was fully dressed, and that I would have to go to the bathroom and get a hairbrush and bring it back to him. (I'll admit this has featured in my fantasies for the last three days). He said he was going to make me beg for punishment. 

and then....nothing.  Nothing at all.

Then last night I was out by his house at some bars, and walking down the street with 4 friends. I passed by him. I couldn't believe it. I passed by him with a girl and another guy. We didn't even acknowledge each other.

I guess thats over :(

Kinky Sex with Colleagues

So I'm not much one for hooking up with my coworkers. 

Haha. That was a lie. I think I've only had one job that didn't lead to me hooking up with someone from the company. In high school, I was a naughty naughty girl and hooked up with my college age boss in the basement of the bookstore I worked in. We would shut down the computer at 4:15 and it took 45 minutes to run all the programs (ohhh remember what computers used to be like?) And we'd fool around, sometimes I'd let him unbutton my pants and slip his hand in. Once, after months of begging, I gave him a blow job. It was my first one and also the last shift before we both went back to school. 

In college, I fooled around with the other waiters at the restaurant I worked at. At my first job out of college I fucked the summer temp. Yes, on his last day I let him buy me drinks and then bend me over his dorm bed. (he was still in college *blushes*). 

So now I can't remember the one job where I didn't hook up with someone. Maybe my first job as a camp counselor at 14? that must have been it!

Now I have a massive crush on a guy at my office. I think he is at least attracted to me. I want him so bad. But I want to date him not just sleep with him! 

So what about that? What if I start dating him? How open can I be about my kinky desires? I suppose I could test the water, but what if things went horribly awry, and he told everyone?

Toronto

I just got home from Toronto where I was on business, which is kind of exciting. It was my first international business trip. I was there with some insane coworkers working a convention. There were 5 of us. Usually when i travel I'm by far the youngest person there. My boss doesn't like to travel and has a young baby, so  I go on a lot of trips that she would normally go on.

This time, I was with my counterpart. Our company has offices all over the world, but our main offices are in New York, Sydney and London. So there are two other people with my job- one in London (Karen) and one in Sydney (Matt). The three of us have a monthly phone conference (hard, with the time zones, to get us all together!) and email constantly, but I've never met them.

For some not-so-clear reason, the company sent Matt to Toronto too. Matt has always sounded very cute on the phone, but I know nothing about how he looks or how old he is. One time, we had a video conference with the Sydney office, and I thought there was someone who could be him. (there were about 50 people on  the conference so it wasn't like everyone was introduced, they were just making a big announcement) So I kind of figured he was about my age, but I think that it was just the accent that made him sound cute.

So I *must* admit that I went to the conference hoping he would be hot. Luckily, he was attractive (I"m not going to say hot, but there was something distinctly sexy about him. his accent? His sense of humor?)

I think we both really really wanted to like each other, because we hit it off immediately. Also, we were a good 15 years younger than anyone else there. He's also mischievous, like me, and we enjoyed sneaking out every lunch time for cocktails. 

(as an aside, my behavior on this work trip was unacceptable, someone needs to take me over their knee and remind me how to be a good employee. Or maybe Matt and I both needed some discipline to remind us how we ought to behave. Interesting thought there...)

And we were both clearly attracted to each other. In fact, everyone at the conference, from our company and the other people we were hanging around with, was making constant jokes about us being a cute couple. We went out every night, in fact, we closed down bars every night. We were there Thursday through Tuesday. 

Monday night we were completely hammered.  We had been out dancing at this awful awful club- we'd taken some customers out, and one of them was hitting on me. Now, I'm a flirt. I'm a huge flirt actually. And so I'm sure in some ways I invite these sorts of situations on myself. But it happens a lot that I'll flirt with people I'm not interested in going home with, but they'll become really interested and aggressive. This client kept whispering in my ear and putting his hand on my lower back. I always get hit on at these work functions, probably because I'm one of the few unmarried women. So I walked over to Matt and told him what was going on, he laughed and said, "Don't worry you're coming home with me."

I am? 

The two of us were at a different (cheaper) hotel than everyone else. So we got in the cab together and then, at the elevator in the hotel he said, "I don't mean to be too forward, but can I come up and see your room?" 

I know I shouldn't have let him because he's my colleague, but he also lives on the other side of the world. So I did. 

We were pretty good, we mostly just spooned and kissed and rolled around on my king size bed. He had a great body and he pinned me down a few times, which was as kinky as it got, but thats okay.

Which leads me to this thought: Kinky Sex with Colleagues. I'll expand in my next post.

(I'm also still thinking about what it might have been like if Matt and I had been punished together.)

More texts from Sean

So Sean has been continually texting me with dirty little messages. But they're also kind of sweet, or, they start out sweet. He starts by texting something like, "I miss you" or "I've been thinking of you." Then within a few exchanged texts they're all like "You won't believe what I've been doing to you in my head at night" or "tell me about how you make yourself come."

I, of course, love playing along. But honestly, I really want him to come and visit.  By the way, he broke up with his girlfriend. I don't want to press it too hard, because I want him to WANT to come see me (oh, and be my boyfriend, but whatever...)

#3- Date 2

Ohhhh dear, I really am a slut and deserve everything I get. 

So there we are. date #2. I guess now we've been on two dates I should call him by his name, Ben. So Ben and I meet up, and its not even two hours before we're back at his apartment. He's deadbolted the door and has me over his knee. I'm kicking and moaning and he's got me firmly by the hair with his left hand and spanking my ass with his right.

So we're at a bar getting a drink. Conversation is going well, his hand brushes my leg. Its 5:30, we've both just left work. At 6 he gets a phone call from his roommate. His roommate says he's still at work, and should be home in an hour and a half. Ben's hand slips up my leg and we make this hot eye contact. "So we'd have my apartment for the next bit, " he whispers, "and I think you've probably been a naughty girl today."

My ass starts to tingle and all I want is for him to bring me to his apartment and teach me a lesson. He finishes his beer, so I take mine in a gulp and stand up and walk out with him. 

We're sitting on his couch and he's rubbing my legs. Then he makes me tell him what I want him to do. I can barely speak. I'm so embarrassed. I am stuttering and nervous, and I don't know why. I whisper that I want him to force me over his knee, push my dress up, pull my panties down and give me a spanking. He's coaxing me along and telling me how hard I'm making him. 

"Then what?" he asks

but I can't even answer. I can't even think of how I want to answer.  I'm suddenly feeling so shy.

"Do you like sucking cock?"

"yes" I whisper with my eyes downcast.

"do you like it hard"

"yes. yes, and I like getting my hair pulled" Then he's got me over his knee, he starts spanking me over my panties. I'm trying to get more into it, but I'm still feeling a little odd about the whole thing. He's another one into being verbal. But he wants to hear all about my fantasies. He wants me to tell him all the naughty sexual things I've done. This is kind of weird though, I mean, why does he want to hear about me with other men? Does he really think I'm a slut or is he just saying it for fun?

So he's spanking me and demanding that I tell him all about what a slut I am. So I try to pull some old stories (because lets be honest, I'm really not getting that much action right now).

When he's finished punishing me I get on my knees and give him head. He's quite forcefully shoving his cock down my throat. Luckily I like it. Then we kind of collapse in mutual exhaustion on his couch, and I'm still feeling shy. I never feel shy! I am not a shy person, but I'm a little embarrassed about the whole thing, so I kind of run out of his apartment. He's all, "when are you free next" and I respond, "ummm I'm going out of town for a little bit. I'll be back in like 6 days. Give you a call when I'm back in New York?"

Bachelor 3- post date

Well, maybe I was wrong. I got an email from him a few hours later saying that he was really attracted to me and hoped I wanted to meet again.

I, of course, do.

Bachelor #3

So after a month of missing each other we finally met up for a drink today. The Verdict: Totally cute and nice.  Interesting also. He's someone I would definitely meet and be interested in dating. 

Now, I'm not so sure he was interested in me. He kept looking away when I was speaking.  What? Like I'm boring or something? Let me tell you, I am not. or at least I hope I'm not. We met really quickly, because I had to be home early. I told him he could call me. We'll see what happens.

Sean 2- Post Weekend

I got this text this morning from Sean.

"Are you at work?"

I am, but I'm in a meeting so I don't get it for a few hours. 

"Yes" I text back

"Oh" he responds "I was in the shower early and wanted to distract you with naughty pictures"

"Sean! how many times do I have to tell you I do I don't want pictures of you naked. Have some self control"

"I had some until the bar. Then you were just there asking for me to dominate you.  That was torturous!"

"I did NOT ask you to dominate me."

"You just about did. I haven't stopped thinking about it since."

"Yeah? Are you going to come see me in New York?"

"Do you want me to come and dominate you? Or do you want me to come and drive you around all day like your chauffeur?"

"You say you're so dominant, but I think you might be all talk."

"If I come to New York, I'm going to make you my little slut. Is that what you want?"

"I'll be such a little slut for you"

Now at this point I'm sitting at my desk going crazy. So innappropriate for work.

"Are you thinking of what you would do for me if I came to New York? Am I getting you hot at your desk?"

"yes"

"you're naughty."

"Are you going to punish me?"

"Oh yes. what are you wearing?"

"all dressed up for business. Tight sweater. pencil skirt. stockings, heels"

"nice. I like that."

 I didn't respond because I want to be the one in control this time.

My Ex- Sean

This weekend I saw my first boyfriend from when I was 16, Sean. Sean and I dated in high school for about 4 months. We had a rough breakup and didn't speak to each other until we were juniors in college. Since then, we've become friends again.  

We were really young when we dated, and we never had sex. I was still in the phase where I thought I was going to be a virgin until I got married (HA). Sean had lost his virginity a year before, but he didn't ever try to pressure me. 

So we became friend again when we were juniors in college. Two weeks before graduation we hooked up on my couch. Again, we didn't have sex. Then, about two and a half years ago he came to New York to visit me and we ended up banging for the whole weekend. It was hot. Really really hot. Mostly because we  never lost the attraction that brought us together in the first place.

I saw him while I was home for the long weekend.  He's living in Chicago now- near my parents. We decided to spend Saturday together. I met him in the morning and we just hung out driving around. He is dating this girl that I kind of know, but the chemistry between us was pretty obvious. He even started playing this game with me where he would pretend he was  doing all sorts of sexual things to me whenever I was on the phone. Like he would get down on his knees and start kissing up my leg, or pin me down and rub up against me, or pull me onto his lap and bounce me up and down. It was really exciting because I didn't know if he was actually going to do anything, but it was clear we were both into the idea that he might.

Did I mention that Sean is one of the most attractive men I have ever known?  He is charismatic and could have any girl he wanted. Literally, every time we go to a party together every girl in the place drapes herself all over him. He is tall and thin with curly brown hair, he's got great arms and these dark blue eyes that make me want to take all my clothes off.

So around 5 pm he asks if I want to go to a bar. So we find this totally shady dive bar- like no one there has teeth!- and order some budweisers. He starts talking to me, and since we're both obviously thinking about sex the conversation quickly turns to that direction. He tells me that Andrea, the girl he's dating, is totally boring him in bed. He confesses that he's into being really dominant and she'll never let him do anything. He says that he's asked her to do a bunch of things, but she's always really uncomfortable and its just not any fun for him.

Dominant? Really? Where was that side of him when we were dating? Seriously, I've known since I was like 7 years old that I like being spanked and dominated.

So then he turned to me and asks, "Well, what about you Rose? Are you kinky or do you like it just kind of normal?"

I laughed and decided to take a chance. I paused, then blurted out, "Ohhh I'm really submissive. I love being dominated"

He paused and I could see him getting really excited, "Really?" he asked.

"Oh yeah."

 

So he wanted details, but I was feeling shy.  He said that he wouldn't have guessed that I was so submissive. I told him I always have been, but am really shy about telling people because they might think its weird.

Then it was time for us to go meet Andrea for a movie. And we were drunk. And very much wanting to have kinky sex in the back of his car. 

But we were good and went to go catch the movie. 

Craigslist Bachelor #3

Okay, one more response to a craigslist ad. I got an email back. This one says he is 6'0" (and you can't THAT blatantly lie about height, so this one must be taller than me!), thin, brown hair, looking for more than a one night stand. Oh, and he attached a picture and looks totally cute.

 He likes books (I like books!), skiing (I love skiing!), and good restaurants (we are clearly getting married). One caveat- I disbelieve men who say they are looking for a long term relationship. I mean, how do you know? I thought everything was just short term unless you really liked the person. That's the problem with online dating I think- you are all of a sudden on a date, you don't get any time to figure out if you like the person, don't like the person or just like them as friends. I don't know  that I could seriously date someone on the interest. I WANT to, because, God knows, I'm not satisfied in the relationships with the men I just meet, so why not? If I already know that they can (and are willing to) sexually satisfy me, well, then I can just concentrate on getting to know them. I don't have to be all stressed about whether they think its weird I like to be spanked. I don't have to wait and wait and wait for the moment that I'm comfortable enough with my partner to be like "hey, it would be awesome if you dominated me when we have sex." 

You know, sometimes people you love say no, and then what the hell do you do? Do you stay with someone you love who leaves you sexually unsatisfied? Is it okay to break up with someone because they aren't as kinky as you?

I'm sick of not being sexually satisfied!

Craigslist Update

So as for the two guys I went on dates with- i realize I forgot to tell the ending.

Date #1 (the old dude). Definitely called me two days later. I didn't pick up. He asked if I wanted to get a drink on my message machine. I sent him an email saying I didn't think it would work out.

Date #2 (the lawyer). Never called. I know! I was totally shocked too! 

Seriously though, it made me feel kind of bad that he didn't call. I was sure he was going to. Oh well, like I said, I wasn't crazy attracted to him, and its bad to start dating someone you don't think is quite good enough for you. But still, did he not think that I was attractive? Was I too tall? I know its stupid to ask all these questions, but I can't stop myself.

I am considering putting up an ad on craigslist myself (in the not casual encounters section) so I can be the one who gets to choose.

Craigslist Casual Encounter Part 3: His Apartment

And so there we were in his apartment. He asked me how long I had been into spanking and I was like, "forever." He asked, "since you were a little girl?" and I nodded shyly. He looked so turned on that I felt almost a little uncomfortable. He told me that his exgirlfriend had been into it, and had been into him "making" her do things afterwards and looked expectantly at me as he slid his hand up my skirt. He leaned his mouth in like he was going to kiss me, but instead he started whispering in my ear, calling me a naughty girl and a dirty little slut. Now, I kind of thought someone I didn't know at all calling me a slut would be offensive, but it totally turned me on. After all, I was kind of being a slut!

 He started rubbing me all over and whispering more- it made me so hot. Then he pushed me over his knee and pulled off my tights and my panties.  When he started rubbing my ass I thought I was going to come. The whole time he kept whispering in my ear, calling me all sorts of embarrassing things, and I was so into it. I was bucking up and down, fighting back a little until he spanked and rubbed me into submission. When he was done with my ass, he pushed me onto my knees, stood up with his hand on his zipper, cocked his head to the side, and asked how I intended to apologize to him. I love sucking cock after a spanking. I especially love doing it on my knees in front of whoever just punished me. Its such a feeling of submission. 

I licked and sucked him while looking up and making eye contact, that drives men wild. Then he pulled me off the floor, bent me over his couch and spread my legs. He thrust his cock in me as I groaned. It had been awhile since I had sex, and he had such a big dick. He was tugging my hair and making my back arch. All while telling me how naughty and slutty I was. 

He was so verbal the whole time, I couldn't get over it. He talked the whole time he was spanking me, the whole time I was on my knees afterwards, and the whole time he had me bent over his couch (or his chair, or his bed...). And then afterwards he wanted to talk about it all again. That made him want to spank me again, so he pushed me over his knee. This time he pinned my arms to the small of my back. I still had my skirt on, since he'd wanted to fuck me while I was wearing it. He pushed it back up and made me count each time he slapped me. No one has ever done that before.  I came on number 8. It was fucking hot.

Him being so verbal  made me really verbal too. Maybe it was because he was so cute and after he punished me I really just did want to please him. Maybe its because I'm more into talking dirty then I thought. But wow, what a hot Monday night! Definitely the first time I've EVER come with someone who wasn't my boyfriend. (or exboyfriend haha)

Then at about 1 am I asked him to call a cab for me, he teased me and told me I was such a dude for coming and then running out. I looked at him and said, "listen, I'm not looking for a boyfriend, but if you want to do this again I would be really into it." 

He looked at me rather strangely and was like "well, you know, I just got out of this long relationship and I"m not looking for a girlfriend either" To myself, I thought, no shit, you were looking on the fucking casual encounters list!

So I continued, "seriously, I'm not, but this was really hot, and I'd like to do it again. I hope you would too." 

For me this would be perfect, someone who was attractive, normal, able to hold a conversation, and really dominate... and also, not going to kill me!

Now, to me this seems like the perfect situation for him, you have this cute girl, willing to come over to your house for you to spank and then do what you like with, am I wrong here?  

But when he looked back at me and said, "yeah, yeah I would like that" I could see in his eyes there was no way he was calling me - and yet he continued with the dirty talk until I got into the cab by myself.

Did I do something wrong? I mean, I know he was into it and I know he wanted me from the second we sat down in the bar. So why wouldn't he be into a casual occasional thing? 

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.