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.