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?