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.