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.