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.