Sometimes My Life Is Random... A Twenty-Something's Random Journey, Finding Herself After Heartbreak... For Mature Audiences Only

Vacation boyfriend, round two.

Jun 7th, 2010 by admin

I mentioned that vacation boyfriend, Tom, actually saw me the night before he met me in the lobby. He heard me laugh, turned around, saw me and knew he was into me. Then he heard me say something about living in Chicago and he said right then he knew he had to find me. I called his bullshit but then he showed me a text on his phone to his friend that read something to the effect of… If you see that brunette from Chicago at the bar, text me and I’ll come down. Weird that he just knew, right?

I hung out with vacation boyfriend for the next three nights. We did not sleep in a room together again. Here is my reasoning, I like this boy. I am fully aware that we are in paradise, on vacation and this is NOT real life… but he is moving to Chicago so there is a potential for something to possibly flourish later this summer.

After I got home, he called me one day and asked if I could come back out to the island. I had told him there was a possibility that my department would be laid off and I would have a lot of free time and I would check. That night he sent me an itinerary with flights asking how these dates looked. I called my boss and asked her if she knew when my last day would be, she told me to take the trip and not to worry. So, I called him back and said book it.

And so, the adventure begins! Here I am writing to you from the flight, somewhere over the ocean. I will see him in 2 hours and my tummy is doing flip flops. I am so excited yet so nervous. I think it is going to be a good week though.

He is very sweet, so thoughtful and just a really nice guy. I do have a hang up though, he has a child. I know, I know… say what you want about me, call me selfish or whatever, but I am 28, childless and not quite sure if that is something I can take on. I told him this outright, too. I mean, I am sure for the right person I could get over the hang up. Luckily, he is recently divorced and the last thing he wants right now is a new relationship.

We both need each other right now, for different reasons. I am the first woman he has really clicked with since his divorce and, for me, well, I need someone who will treat me the way he does. On top of that, I really like him. We seem to have many of the same opinions, like the same things, read the same books, etc.

Side note, while I was writing this the guy in front of me just asked if I would lower my shade, he is a whole row in front of me and the window shade is directly to my right, it’s my shade. I get a bit claustrophobic and really like the natural light, plus I am working and hate nothing more than a dark computer. Who does that? Get a eye mask, I travel with one… it puts me right to sleep on a plane, plus it doubles for bondage.

Tags: thoughts, travel

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The Vacation Boyfriend

Jun 5th, 2010 by admin

It has been quite awhile since I have had the chance to sit down at my laptop and write a blog post. It is not that I have not been writing, I have, just not the stuff you want to read… unless you are really into press releases.

If you follow me on Twitter you may remember I was recently in the Carribean. Jane and I were at an event in April and she won a trip for two to St. Thomas. We were ecstatic, I already had accrued vacation time and the rumor around the office was that I had better use it soon, as we were probably all getting canned anyway.

Janey and I flew from Chicago to Miami, then on to the island. We couldn’t wait, 5 days, 4 nights in paradise. We had no plans except relax in the sun, maybe snorkel or take some boat excursion and eat and drink. Perfect vacation.

It was on our second night that I met Tom, but later I would found out that he saw me the first night I was there… I’ll get to that at the end. Jane and I had purchased some rum to drink in our room, but we needed mixers. I went down to the closest restaurant just to purchase a Diet Coke. Tip: Marriott only has Pepsi in their vending machines, but they keep Coke at the bar for rum and diets, I assume.

It was on my elevator ride back up where we first, kind of, met. He was with two of his friends and truthfully, I did not pay much attention to them. My hair was wet, as I was half ready for going out, I was just wearing yoga pants and a tank, nothing special. I was not in meeting boy mode for some reason, which is odd, because… well, you know me. His friend asked me which bar is the best bar to go to, I said we just got here, I did not know yet. Then Tom and one friend got off one a floor below mine, the third friend was staying on my floor. He mentioned it was his birthday, that is why they were celebrating and I should come out. I blew him off.

Fast forward a few hours, Jane and I were sufficiently buzzed and it was time to go out. We went to the concierge and ask him where we should go, what should we do, etc. We wanted to get off the resort and visit a local bar, but one that was still safe for tourists. He directed us to one, and called a cab for us.

Jane and I go to this local bar, it was pretty touristy but still fun. We are drinking, we are talking, flirting, just having a good time. All of a sudden, I see the guy from the elevator who said it was his birthday. So, I gave him a hug, said happy birthday, then asked if he wanted a birthday shot. Then Tom comes up and says he wants in on the shot, too, and that he wants a hug. I was pretty flirty, replied that it was not his birthday, but I would make an exception this time.

We start flirting like crazy, just talking, hanging out and after I mentioned I live in Chicago, he mentions that he is starting a rotation (med student) there in the end of July. Wow, OK. So it gets fuzzy from here. I remember at one point he kissed my cheek, kind of near the corner of my mouth and then I just grabbed his face and kissed him, hard. I was pretty drunk but it was one of those movie-like kisses, the I have to have you, I do not care who is looking type of kisses.

We made out all night. I never make out in the bar. I was pretty drunk and since I have cut down immensely on the alcohol, I get pretty drunk easily. Also, we were holding hands, dancing, just being ridiculous – like you are supposed to be. I was happy; I had found a vacation boyfriend.

Jane was being a good wing woman, too. Oh, did I tell you she has a boyfriend now? Yeah, it is lame. Not the boyfriend part, but the guy. That is for another post. But anyway, I knew she was tired but she was a trooper and closed the bar with me so I could hang out with Tom a bit longer.

We left the bar about 1:30am and the boys walked Jane and me to our room. Birthday boy (I seriously cannot remember his name right now) was trying to get on Jane so hard. I went into the room and told Tom to wait outside for a minute. We must have discussed that I was sleeping in his room, or maybe it was just assumed, who knows?

I wanted to talk to Jane and make sure she was not weird about me sleeping in another guys room. Also, I wanted her to know his room number as a safety precaution, just so she knew where to find me. I also freshened up and grabbed a few condoms to throw in my bag.

I exit my room and there is Tom, but also birthday boy. Birthday boy was smashed and kept asking me to let him in our room so he could get it on with Jane. Wow. Tom was far less drunk and we walked birthday boy to his room to sleep alone.

This is all still hazy, but I know more details after talking to Tom. We went to his room and I immediately said lets wash our hands. Good to know my OCD even kicks in when I am wasted. After that, I pushed him down on the bed. I got on top of him and we were crazy making out again. It was semi-rough but the kisses were still soft. At that moment, it felt as if two people have never had to have one another more.

That went on for a bit. I remember saying, “I am not sleeping with you tonight.” He said, “Good, because I was not planning on sleeping with you either.” I laughed, fully knowing that if I wanted it to happen, it would have. I did follow up with, “But you can still go down on me if you would like.”

Wow, I have such a smart little mouth when I have been drinking, but at least I know what I want, right?

He takes my pants off, but I am fully dressed otherwise. He starts giving me little kisses in between my thighs and then comes back up to my neck and nibbles gently. I remember it being so soft, his nibbles, and they were driving me mad. He then pulled my tank top down a bit and my left breast was revealed. He flicked his tongue across my nipple and it instantly got hard. Then put his lips around it and sucked for a second, finished off with a little bite. I was running my fingers through his hair, he was switching between kissing my neck and then nibbling on my nipple. His fingers found my right nipple and he was pinching it in the same fashion in which he was biting the left.

He lifted up my tank top a bit and gave my belly kisses. When he got to my hip bone I was so ticklish and so turned on at this point. I asked him to feel how wet I was and he complied by moving my panties to the side and inserting a finger. He did not insert all the way, just the tip and then pulled it back out to taste me. That was hot.

He then kept my panties to the side and started my thigh, above my pussy, then eventually his tongue was on my clit. I remember him being very impressed that I was smooth down there. He just kept kissing and licking and mentioning how smooth I was.

Here is where it gets weird. The next thing I remember was waking up to someone walking in the room, it was his other friend. For a moment I forgot I was not in my own room (I did remember I was with the boy, though.) There I find myself, at 4am, wrapped in the boys arms. I was wearing my panties and tank top. He felt me move around and woke up for a moment, too. He asked if I was OK, and he handed me water.

I took a sip and then said, “I feel like I may have fallen asleep when you were going down on me.” He said, “Yes, you most definitely did.” I replied, “Yeah, I’ve been known to do that. Sorry.”

He then hugged me tighter, kissed my ear and said go back to sleep. I did.

I woke up the next morning to the alarm. They were going on a boat that day and had to be up early. He told me to sleep in the room as long as I wanted but asked for my cell phone, so he could call his with my number. Before he left, he gave me a few kisses, two on my forehead, one on my ear, one on my lips. Then he says to me, “I have to see you again.”

Tags: Going Down, oral sex, travel, Vacation

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So many new men…

Mar 9th, 2010 by admin

Some of you who follow my Twitter stream might know that I was in Nashville for Valentine’s Day weekend. Jane won a package to a hotel somehow, her man was unavailable, so I went with her. It was a nice break away from life, plus I had President’s Day off from work, so I even had an extra day available.

On the way back, we volunteered our tickets twice as the airlines were so overbooked due to the random snow storms in the South and East. We ended up each receiving $600 in free airfare vouchers, score. Those will come in handy, for sure. On top of it, we were put in 1st class on the final flight back to Chicago, though we were not able to sit next to one another. Which was fine with us, as we were crossing fingers for hot, first class men as our seat partners.

Well, I scored (sadly, Jane did not). The man sitting next to me was a bit older than me, good looking, nice teeth, no ring. I instantly started little chit chat conversation, things like where are you from, what do you do, etc. It turns out he does not live in Chicago full time, he actually lives part time in the UK, though he comes to Chicago about once a month. We chatted the whole plane ride, he gave me his card, I wrote him an email a few days later and now we chat almost daily via GChat. Oh and the plane guy… is from the UK originally but his accent is faint.

So, he is in town this week. I am meeting him tonight at his hotel for drinks, then, who knows? We also have plans tomorrow night for dinner and again… we’ll see what happens there. In truth, some of our Gchats & BBM conversations have become somewhat adult oriented and I have a feeling that as long as everything is smooth, I’ll end up staying at a hotel downtown the next few nights.

As for the other man I’ve met recently (two weekends ago, I think?)… The other man I met is also a Brit, weird. Jane & I met him at the gym, he lives in London full time, comes to Chicago for work about every 6-8 weeks. I have not been talking to him as much, but he comes into town the end of March, so we’ll see if that goes anywhere. I have a feeling he is loaded, just a hunch.

What is funny about meeting the two Brits is… about 3 weeks ago I posted on Twitter that I wanted to have sex with a man with a sexy accent. Just another weird example of sometimes getting what you ask.

Also, remember Jayson? He is coming to down next Wednesday and Thursday… And I need to tell the story of Big Penis guy from last week. This new job is kind of taking up a lot of my time, but I promise to start posting some of the last few weeks ASAP.

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So behind… & some updates

Jan 29th, 2010 by admin

I am, of course, behind on writing the blog. I promise to play catch up a bit but wanted to do a quick post, as something weird is happening tonight.

I know I have posted a million times how this big city we call home, is really a small city of social circles.

So, I am kind of dating Daniel now. I know I have neglected to update the blog, but we have been hanging out a few nights a week. He is really good to me and I am pretty OK with it for now. I mentioned in the past how Daniel is friends with “D.” They met after D and I dated, or whatever you wanted to call it, so Daniel does not really know that we dated, though Daniel does know that D and I are friends.

Well, tonight, a few of Daniel’s friends are going to see this band, I did not even think to ask which friends. The D wrote me an email asking if I am cool with him showing up tonight, too, with his girlfriend. Obviously Daniel invited him. I replied it might be a little weird, but it is bound to happen sooner or later and tonight might be a good night for it, as we will all be distracted by the show.

D did say that he thought it was best never to mention to Daniel that we have any sort of romantic past. I agreed and kind of breathed a sigh of relief. It is still probably going to be a bit awkward but I will just drink some beer and hope everyone else does, too.

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Inappropriate coworker?

Jan 21st, 2010 by admin

I went to an event for a client tonight. I was working so I did not drink, though I probably could have if I had wanted. I think after last night I do not need to be drinking for awhile, plus I am trying to get healthy.

A weird thing was said to me though. Even though I am not working full time at my new job quite yet (next month), I am helping with events. In additions, I have worked with this company as a client, so I pretty much know most people with whom I will be working. So, one of the guys who is very married (and has a kid on the way) said to me, “If I were single, I’d be chasing after you.”

OK, this is not my friend saying this to me (which would still be creepy), this is a co-worker. He is technically a contracted co-worker, but nonetheless it is totally inappropriate. I felt so uncomfortable after he said this and I pretty much ignored it.

I did meet a new guy that was attending the event. He gave me his card and said he hoped he could take me out sometime. He was cute but nothing special, plus I think I am going to see where this thing with Daniel might be going.

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It’s 3:34am… on a Tues night/Wed morning

Jan 20th, 2010 by admin

This post isn’t a good idea. I’ve been drinking, quite a bit. I probably won’t proofread this and who knows what I will not really mean to say. But, it is real.

I haven’t been posting lately, mostly because I have not even been home. It seems like my life is just moving so fast and I have had very little time to myself. I need my alone time, hell I thrive on my alone time. I should try to make more for myself. Yeah, I should do that.

Tonight I was out with friends. All new friends, good friends… by new friends I mean people I have met since Patrick and I split. Yes, my ex’s name is Patrick, I do not think I’ve ever wrote that before. I feel I try to dehumanize him by calling him the ex. Somehow that makes me feel better.

We were sitting and talking and my friend Charles (who is very gay) started talking about his new boyfriend. Every adjective he used to describe his boyfriend was exactly how I felt about Patrick from the moment I met him. It triggered something in me.

I miss him so much. I’ve done everything I can to put him out of my mind. I have new friends, I’m dating someone new (Daniel), I moved, I live in a new neighborhood, I live with new people, I stopped answering emails from his mom asking me to meet her for lunch, I stopped talking to him (in August!) But what the fuck?

Thoughts of him invade my mind on a daily basis. He is in my dreams maybe 2-3 nights a week? I never speak about him to my friends, I never let anyone know that I am so fucking heartbroken. My friends have absolutely no clue, I mean none. I just made it seem to disappear, by appearance only.

I worry about this a lot, and I feel… well, insane. I feel like it’s been so long and not only should I be over it, I should be fully moved on. I sometimes feel weak because I cannot get over this. Then in the same moment I get this stupid idea that maybe I am not over him because we should be together, or some stupid bullshit. If that were true, he’d call, he’d write, he’d email. Something.

This has never happened to me before, so I am not sure how to deal with it. And the truth is, I know he will not contact me. Between calls and emails, he contacted me six times and I ignored every single one of them. I couldn’t deal with it at the time, I was too sad from life events (death in my family) and couldn’t handle him on top of it.

I’ve thought about emailing him, or calling him, just to say hi. But the truth is I am a fucking pussy that is too afraid of getting rejected by him again.

My friend told me the first hurt was the easiest. I did not get it at first, but I now understand that more than I should.

Sorry this is all over the place. It’s random drunken thoughts. I’ll be fine tomorrow, upon waking up. Although, I am sometimes still in disbelief that he is not laying next to me when I wake up.

Oh is this weird. After we broke up and I moved to my new place, I could not sleep in the bed we used to share? For two months I slept on the couch because I hated laying in my bed without him. I do not really remember what got me to sleep in my own bed, but I think it was because my friend crashed on my couch after a binge night out.

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Day Two with Shaun

Jan 7th, 2010 by admin

So, I mentioned it was hard to get rid of Shaun, right? Keep that in mind.

Shaun was a cuddler. Everytime I would wake up in the middle of the night, I was engulfed by his arms. It was cute, but I really need my space when I sleep. Even though we went to bed around 4:30 or 5am, I think I was awake by 9:00am. I just could not sleep anymore. I slipped out of bed, hopped in the shower and Shaun was none the wiser.

I woke him up at 10am, and he hopped in the shower, too. After we were all good and clean, we decided brunch was next on our list. We just went to this spot that is about 5 blocks away, a place I frequent often. We walk in and a few of my friends were dining. I had to introduce Shaun but they were chuckling because they totally knew he had spent the night. Oh well, it happens.

We did the brunch thing, then he said he had to move his car because it was parked in a lot downtown. So, we walked to the El, hopped on and headed to Humbolt Park. We get his car, I think he is going to drop me off at my place, but instead he parks on my block. OK, maybe he wants to hang out more. I kind of ask him about it and he asks if I mind if he stays to watch football for a bit, because his corporate housing just has very basic cable. At this point, I was still kind of into him, so I figured what the hell. Now, I do not have my TV hooked up, but my building has a common room with DirecTV and I am sure other NFL fans were watching it, too.

So, we come to my place for a little, he watches football, I went up to my apartment and did some Sunday chores like laundry, etc. Time passed, I came downstairs, asked him what his plan was, when he was going back, etc. He said lets get dinner, so we did. By this time it’s like 7pm, and I knew at this point he was going to be sleeping over again. I figured this time at least maybe we could do it?

So, he stays through dinner, we watch a movie. We kind of cuddled while on the couch, he would lean over and give me little kisses on my shoulder, my cheek. It was cute and like I said, he was super hot so I was into him. We did talk a little bit about his situation in life. Apparently he is recently divorced, has not had sex with anyone since his divorce and by the way he spoke of it, his divorce hit him hard. At one point he called his ex-wife to try to speak to his kids, as he calls them everyday apparently, but I could hear her through the phone and she was screaming and kind of ghetto sounding. Hhhmm. I know there are two sides to every story, but he was being so nice and calm as she was literally swearing at him and screaming. I made a mental note right there that this was only going to be sex.

I went to my bedroom, put on a sheer black nightgown, I asked him if he wanted to come to bed. He knew what was going on but he seemed nervous. Maybe he was telling the truth when he said he had not been with anyone since his divorce.

He walked into my bedroom and shut off the light. He walked over to me, put his arms around me and kissed my neck. He then turned me around, sat me down on the bed and kind of picked up my legs, moved them into my bed and turned me in the same motion. He then got on top of me and he started giving me kisses on my neck and chest. He was giving me little flutter kisses and it was getting me excited.

He then moved back up my chest, leaving a trail of kisses to my jawline and then finally my lips. He was a good kisser. He has nice, thick, full lips and he uses them to his advantage. He would suck my bottom lip as he was pulling away from the kiss, which was driving me crazy in the best way.

He rolled over on to his back and pulled me with him, so I was now on top of him. I started taking off his shirt. I would unbutton one button, then kiss the newly exposed skin. Another button, another kiss until I was down to his belly, right by his belt buckle. I spread his shirt totally open, so he was still wearing it but he was fully exposed. I moved my head left and started giving little kisses, and even some small tongue lashes, to his belly. I went from the left side of his belly to his right side, letting him think I was going to take his pants off at any minute. He was a bit ticklish but seemed to enjoy it.

I moved back to the middle and started loosening his belt buckle, while still giving his tummy kisses. I unbuttoned his pants, moved his boxers down just a bit and kissed below his belt line. As I was unbuttoning him, I could feel through his pants that he was absolutely rock hard.

I get off of him, I pull his pants off and he helps me. He leaves his boxers on though, hhmm. Then he tells me to lay down and as he is transitioning he takes his shirt all the way off. Now I am on the bottom again, he is on top of me and slowly lowers the straps to my nightgown. He tugs at it for a moment and pulls it down, so the top of my night gown is right under my breasts. He gives me those little flutter kisses again under he moves to my left nipple and it goes right into his mouth. Aahh, those lips. He is sucking on my left nipple and it is literally making my body shutter.

He moves to the right nipple and does the same thing. He is taking his time with them, alternating kisses with sucking, even throwing in a bite or two. I am still wearing panties at this point and I can feel them getting more and more wet with eat kiss.

He sits me up, tells me to lift my arms and completely removes my nightgown. He then peels my panties off and there I am, naked, exposed and very milky white. He lays me back down, kisses my belly and goes to my hip bones. Because he is so new, I am a bit ticklish and I squirm a little bit. He puts his hand between my thighs and his middle finger instantly finds my clit. He strokes it a few times but then slides his finger down my slit to my opening. He does not put his finger all the way in, but more is just lathering his middle finger with my juices. He moves back up to my clit and rubs it with a bit more pressure.

He asks if that feels good and I reply with yes, but your tongue would feel even better. He says he is not ready for that yet. Hhhmm. OK, I mean, I guess I get it because I rarely go down on non-boyfriend guys… but still, that is my favorite thing ever. So, whatever, I tell him to keep rubbing my clit. He moves back up towards me and we start kissing. I grab his hand with my left hand, put his finger up to my mouth and suck my juices off of it, and then I kissed him. If he was not going down on me, fine, but he was tasting me. In truth, I was hoping that he would realized I tasted pretty good and would want to lick my clit. No such luck.

At this point I knew I would not be getting off but I just wanted him to fuck my brains out with his large cock. I knew the condom would be an issue (seriously, condom companies make NON-Latex condoms for black men, please!), but he would just have to deal. I tell him to take off his boxers, I reached into my nightstand drawer, grabbed a condom, handed it to him. He was still kind of on top of me. He put it on, it was tight, but it would work.

He lays on top of me, kisses me. I grab the base of his cock and put the tip right near my opening. He gently pushed it in, as I am still holding the base. It was slow going in, which was good, as he was a bit on the larger side. He pushed it all the way in and I told him to hold on a second, as I kind of needed to adjust to his size. Then I told him to pull back slowly, then go back in slowly. He did just that and I felt fine. In fact, I felt good.

He was still giving me his slow kisses, biting my lower lip. He was thrusting into me and I was moving my hips up to meet him. We seemed to have a pretty good rhythm going right off the bat. My friend Julie was right, too, there is something so beautiful about milky white skin pressed against dark chocolate skin. Then I kissed his ear lobe, and whispered to him that I wanted him to fuck me as hard as he could. He complied, sat up a little, put his hands on my shoulders and proceeded to do as I asked. Oh my. It felt really good. There is nothing like having a thick cock inside you that literally fills you up.

Then here is where it gets weird. I can feel him getting, well, soft. I ask whats up and he says it is weird for him, since I am the first girl he has been with since his divorce. I say to him, no worries, just have fun. So, he gets back inside of me, I start contracting and squeezing to try to make him harder when he is inside of me.

It does not really work. He pulls out and says he is sorry, but this is a bit weird for him and he needs a moment. I say it is OK, I am sure it is weird for him. He goes to the bathroom, gets rid of the condom and comes back to bed. I am still stark naked in bed and so is he. He lays next to me, pulls me close to him and kisses my neck. He apologizes again and said that he really likes me and he does not think he can handle something that is just sex right now.

We lay in bed for a bit, he is rubbing my tummy and we just talk. We talk for hours. We talk about his divorce, his life growing up, my breakup, where we grew up and just had a real honest talk. It was nice but the more I learned about Shaun the more I realized he has a long way to go before he is going to have a normal relationship.

We fall asleep, naked and he is holding me. I think that is what he needed more than anything. The next morning we woke up early, I told him that he had to go and could not stay with me any longer. He was OK with that, and he had work meetings anyway.

He has to come up here a lot for work, maybe I will see him again, maybe I will not. He did leave his watch at my house so I am sure at some point he will be coming around for that. Will I see him again? We’ll see.

Tags: fingering, foreplay, making out, sex, tickling

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The out of towner…

Jan 6th, 2010 by admin

Saturday night I met up with Janey and one of her old work friends (Julie) that moved, but happened to be in town. We put on dresses, got a bit glammed up and decided to head to this wine bar, that was new to us, as we had not been there before. We left about 10pm and one of Jane’s friends was planning to meet us there later.

OK, rarely do I say where I am at, or what bars I frequent. I mostly do this because I go to the same ten or so spots in my neighborhood over and over again. In addition, I do not want my friends, or more importantly my co-workers, to catch on. Though, I figure every now and then it’s OK for me to say where I am/have been, especially if it is a place where we (Jane and I) are not regulars and it was just us out, not our other friends, too (i.e. if any of my “real” friends happen to read this, they will not catch on.) Oh, and Janey knows about my blog now, my drunk ass could not keep it a secret. That’s OK, she is sworn to secrecy.

So, having said that, we were at Rootstock Wine & Beer Bar. It was pretty busy but two guys were leaving the bar. There was also an open seat on the left of this man that was also sitting at the bar. I was immediately excited because he was very good looking, and dark – my favorite. I asked him if he would mind moving down so the three of us could sit together, of course who says no to that?

He was alone and I sensed he was not from here. I was correct. It turns out his name is Shaun and he comes here quite a bit for work, as his company is based here. He was staying at his company’s corporate housing which was somewhere up by O’Hare, so I have no clue why he was in Humbolt Park. We probably talked about it when he was drinking, but I don’t recall.

I ended up kind of talking to him quite a bit because Janey and her friend had chatted up some other random dudes. He was pretty funny because within the first ten minutes he made it clear he was divorced and he dates white women. I replied with, um, of course you do.

Shaun was super good looking though. He’s about 6’1 or 6’2, light skin, nice build, nice smile, and just had a very cute face. No, hot, he was hot. I could tell he was a bit shy because I was kind of carrying the conversation more than he was, but the more he had to drink the more he was coming out of his shell.

We were talking for about an hour, and then it got to the point where he bought a bottle of wine, asked for an extra glass for me. Janey & Julie’s two guys left and they joined our conversation, in which the main topic was at what point is it too early to introduce anal sex into a relationship. Wow, these girls do not hold back. Julie also was tipsy and started talking about how hot it looks when chocolate skin held against milky white skin. Yeah, I was a bit embarrassed.

At some point he was playing with my hair? That’s when I knew he was going to come out with us for the rest of the evening.

After staying at Rootstock for about two hours, Jane’s friends finally showed up. They had one drink then we all moved on to the Clipper, another place I had never been, and had a few more drinks. Of course I convinced Shaun to come with us for the rest of the evening. He was very happy to accompany me, especially since Julie told him I was a wild woman in bed. Yeah, so embarrassing.

We managed to get a booth at the Clipper and I scooted in and Shaun got right next to me. He put his hand on my leg and it kind of excited me. Janey’s friends got a bunch of these grape soda drinks, as they said we must try them, I guess it’s the specialty drink at the Clipper. Oh my, so good. It’s a bit sweet, so I could not drink more than one but it was really good. After that Shaun made sure my drinks were full, Jane’s and Julie’s, too. It’s all pretty much a haze from here. There was a jazz band, Julie was making out with some older (like 50 +) guy, Shaun was rubbing my leg, holding my hand? Jane started ordering shots?

It was approaching closing time, but none of us were ready to call it a night. Someone mentioned we were right by the Continental and maybe some dancing was in order? As we were walking there I kind of remember Julie & Jane telling me that Shaun was a good person, they liked him, etc. I am not sure where he was at this point, for all I know he heard them talking. I also remember saying to them I was not taking him home with me, or if he did end up at my place, I was not having sex with him. I said something like I really liked him and I wanted to see if it would go further or something? Who knows, I was pretty plastered. I also remember telling Shaun that I would not be sleeping with him. He said something about how he did not expect me to, but he would like to sleep over and rub my back or something, then take me to breakfast tomorrow? Oh my.

We head to the Continental (Hey, Continental, get a real website, I refuse to link to a Myspace site!) It had been awhile since I had been there, and come to think of it, I’ve never been to the Continental sober. I decided no more drinks for me. Janey & Julie were still going strong and I think Shaun might have had a drink, too.

Shaun and I decided to dance a bit. Oh I LOVE dancing with black men. We were getting a little dirty, too, his hands were grabbing my ass, I started kissing his neck and eventually he kissed me. Then there we were, making out on the dance floor, which I usually loathe, but funny how drinks can change one’s mind.

We stayed at Continental for about an hour and then decided it was time for late night food? Julie, Jane, Shaun and I piled in a cab and headed back to my neighborhood. I guess it was a given he was sleeping over at this point. We went to this all night Mexican place kind of by my house and ordered so much food. Janey does that when she gets wasted, just orders a shitload of food for the table. Julie was sitting next to Shaun and he was giving her guy advice, I think. Janey and I were talking to these two guys were kind of know from the neighborhood.

Janey and Julie took a cab home (um, it was 5 blocks, are you kidding!) because it was “too cold.” I told Shaun I wanted to walk the 5 blocks, as the Mexican food was bubbling in my stomach. We got home and literally went right to bed. I did my night time stuff, wash my face, brush my teeth (gave him a toothbrush to use), put on a cute (but not revealing) night gown and crawled into bed. He was wearing just his boxers. I kind of wanted to play with Shaun a bit, but was so tired. We made out a bit, we wrestled in the sheets, I got on top of him but that is about it. I could feel his cock rub against me and I could feel it was so hard, but I could not stay awake. So, we passed out and set the alarm for 10am and planned to go to brunch.

Little did I know, I was going to have a hard time getting rid of Shaun. Ah, more to come.

Oh, and I want to apologize to @TankBoy, who sometimes DJ’s at the Continental. One of these days…

Tags: drunk, kissing, making out

Posted in Random Nights | No Comments »

Changing my mind?

Jan 6th, 2010 by admin

On New Years Day I went to brunch with a friend that ended up crashing on my couch. He is JUST a friend and it turns out that he has once fucked Jane, years ago. That is kind of funny since I did not meet him through Janey, but they are still cool.

During brunch I received a text from Daniel. While I was at my family’s home for the holiday, we had some brief communication but with the time difference (even though it’s only an hour, it still played a factor) and the fact he was spending time with his family, we did not talk much. Plus, truthfully I thought I was over it with him.

Anyway, he asked if I wanted to hang out, lay around, watch movies. I thought that sounded wonderful, as I was still a bit hungover from NYE. I dropped my couch crashing friend off at his place, then Daniel showed up about 1pm. It was actually nice to see him. He has an external hard drive with a ton of movies on it, so he brought that with him. We literally watched movies until about 5pm. Then we started to fall asleep, so we moved to the bedroom.

Well, you know how it is. You can be dead tired, fighting to keep your eyes open on the couch and as soon as you get up and moving, you are awake again. So, there we were, in bed, awake. I do not know what came over me but I just grabbed him and started kissing him. It was nice, and different than before. We seriously made out for 30-40 mins. Just making out, little kisses on the neck, etc. It did not progress further than that and yet I was so turned on.

Daniel had to leave at 6pm because he was meeting his friend for dinner. I asked him if he wanted to come back to my place afterward and he said something to the effect of, well, I was planning to leave my bag here and I packed a toothbrush. I guess that was a yes. We made out a little more and I found that I was really wet from just making out with him.

We also had a conversation, apparently he was just tested for STD’s a few weeks ago. He was kind of cute to make sure I knew. Luckily, I was, too, so I feel pretty good about fucking around with him- though I still ALWAYS use a condom.

So, skip ahead to about 9:30pm. I somehow fell asleep, my phone rings, he is downstairs. I let him up and tell him I am exhausted. We watch another movie on the couch but I did not make it, I fell asleep around 10:30. After the movie was over, he woke me up, I did my bedtime routine then we climbed into bed. We cuddled a bit, and I kind of remember him rubbing my ass, but I think I just passed out.

Next morning we wake up around 10am, which is probably the latest I have ever slept in. I woke up, brushed my teeth and told Daniel to do the same. I was feeling a little playful this morning. Maybe the reason I was so not into it before was due to stress, holiday, etc?

So, we get back into bed and I take my clothes off. Daniel is so innocent that it kind of gets me excited to do things that he might not be expecting, or used to. We’ve talked a bit about his recent ex’s and apparently they were not so into sex or being sexual. I am about to blow this boys mind with something I think is fairly normal. Ego boost.

I am under the covers when he walks into the room, I lift them up and tell him to get into bed. He says something like, wow, where are you clothes? I told him to take off his boxers and join me.

We immediately start making out again but this time it’s a bit raw. Maybe innocent Daniel is feeling a bit more comfortable with me? He start kissing my neck and even giving me little bites! I was laying on my back and he grabbed my wrist and held it down on the bed and just started attacking my neck with little kisses. Then he turned me over and said he wanted to try spanking me. He was still holding my left wrist down with his hand and he was on my left side, so he was going to spank me with his right hand. Before he did, he moved my hair off my back and started kissing the back of my neck. I’ll be honest, I was getting little chills! I felt the wetness coming and I was so excited for what was coming.

He played with me for a bit, kissing my neck, my back, tickling my sides. He let go of my wrist and told me to leave it there and not move. I know he has never acted like this, because no woman has let him, and that made me get even more wet. He said he wanted to spank me, but he didn’t know what I would like, because he has never spanked before. I told him to do what feels best and I’d tell him if I would be able to take it harder or not.

Well, the spankings were firm, but light. I told him I could handle harder, so it took about 10 good smacks before… Whap, and I let out a light yelp. He thought he hurt me but I said, no that’s perfect. He asked if the idea was a red, warm ass and said, yes, of course.

With that he took over, and he was having fun with it. Honestly, he is my FAVORITE at spanking thus far. He timed it weird so I was guessing when the smack would come, he’d do two or three quick ones in a row. I was so wet from this and he did not seem to want to stop. He spanked me until I said… I am too wet to not fuck around right now.

He flipped me back over so I was on my back and got on top of me. We started kissing again, long deep, kisses. He bit my bottom lip and sucked on it for a moment. I pinched his nipple with my thumb and finger and he actually liked it – YES! I hate when guys do not like their nipples pinched. He started kissing down my neck to my chest, and stopped at my left nipple. He asked if he could bite me, I said yes. He gave me a small bite and asked if it hurt, I said, no, I can handle harder. So, he did what I asked. I again let out a small gasp as it hurt, but also felt amazing at the same time. He switched to my right nipple and repeated while pinching the left nipple with his fingers.

It was just a few minutes later when I said to him, I want to do something kind of dirty to you. I pulled his face up to mine, kissed him, then pulled him toward me so I could whisper in his ear, “I want to rub my clit with your cock, then lick all my juices off of it.”

He backed up and looked at me and I swear I’ve never seen a bigger smile. I reached down, grabbed his cock which was so hard, like so hard. He is pretty tall, so I figured he’d be hung, which he is, but I did not expect the girth, too. He has a very nice shaped, kind of dildo like penis. I rubbed the head against my clit and then would rub it a little lower to get it full of my juices. I did this for a bit, I wanted to get myself excited while he was, too. I was really really wet and my juices were all over him. I told him to flip over and lay down, I was going to devour his cock.

I know I say I never give head, but saying he was just tested and I love giving head and it’s been awhile, so he wins in this department. I gave him a few kisses on his hip bones, then moved a little lower to his thigh. He was trimmed, so thankful for that (guys, really, I do NOT want to floss with your pubic hair) and I gave him a few more little kisses getting closer to the base of his cock.

I started by lifting his balls up and running my tongue on the area just under his balls, then licked his balls, then moved my tongue to the base, along his cock then the head. Then I just put it all in my mouth. His cock tasted like my juices, it was so hot. It took me a few up and downs before I was able to swallow his cock and put the whole thing in my mouth. My lips hit his skin and I opened my mouth a bit so I could flick my tongue on his balls while his cock was all the way down my throat. He seemed to like this a lot because he let out a loud moan.

I went up and down without my hands for quite a bit. I swallowed him over and over and he started shaking, literally shaking. I cupped his balls in my left hand and then started adding my right hand, well, just first finger and thumb to extend my lips and create a better grip. I wanted him to cum and I wanted him to cum hard.

I think I blew him like that for about 10 minutes or so. Then I had an idea. I was trying to think what we could do right now that I am sure he has never done before, plus I wanted to cum. So, I took my lips off his cock for a minute, laid on my back and told him to straddle my chest. I grabbed my vibrator from the side of the bed (yes, it was already plugged in) and positioned it on my clit.

Then I told him to fuck my mouth. He said, are you sure, and again I said… I want you to fuck my mouth. He did not hesitate after that. He put his cock right in and started sliding it in and out of my mouth. I pulled my head back for a second and said he had about 5 minutes and not to cum until I did. He had his hands on my bedframe and he was just going at it. I was moving my head a bit to meet his cock at first, but then I could not keep up with him! He told me to smack his thigh when I was ready to cum. I think I lasted a whole two minutes. The vibrator on my clit mixed with Daniel fucking my mouth, oh I just came hard.

As soon as I came he let himself cum. It only took a few more second (I am sure he was super turned on) and he told me he was going to cum. He pulled out of my mouth and came on my chest. He started moaning so loud and his legs were shaking, it was so cute. He pumped his cock with one hand and pinched my nipple with his other.

He sat there for a second and did nothing. Then dismounted my chest, laid next to me, kissed my forehead and told me he needed a minute because he almost passed out. So, he laid there for a good minute and there I was, covered with his cum.

We got into the shower together and he washed me. It was very sweet. By this time it was 1pm and he took me to brunch and then he went home and I went for a run.

Maybe my mind is changing about this boy.

Tags: biting, blowjob, kissing, making out, nipples, oral sex, orgasm, sex toys, spanking, tickling, vibrator

Posted in The Experience, Uncategorized | 4 Comments »

NYE & 2010

Jan 4th, 2010 by admin

New Years Eve was a pretty good time. Janey and I went out with some of our girlfriends to dinner, drinks, dancing. It was a girls only night and we had such a good time. I made out with some guy at New Years, then Janey and our friend Monique also made out with him after that. We probably had a bit too much champagne at that point but it was all in good fun.

Funny story, Violet emailed me and said she was wasted on New Years at some bar and handed out stickers for my blog (yes, I had some stickers made and the few friends that know stick them to things when they travel) to some random dudes and claimed she wrote my blog. She said she was pretty hammered and cannot remember what she told them, but she remembers making the one pull it up on his Blackberry and read a blog entry about Jayson out loud. She is so funny. So if you ran into “me” this week, so sorry, it was Violet being her drunk and silly self.

I am generally not one that makes resolutions based upon some arbitrary date but that might change this year. 2009 was probably the most challenging year I have had thus far. Not to get too Debbie Downer, but between some personal medical problems (I am fine now!), good friend passing away, my breakup with the ex, losing two grandparents, my company not doing well (I took a pay cut a few months ago), my mom & sister’s car accident and my cousin being diagnosed with a cancerous brain tumor things have been a bit difficult emotionally on my end. I am generally pretty good at dealing with things, but when they all come one after the other, it is almost like you cannot grieve for one without the next one coming.

So, saying that, I do believe 2010 will be a better year for my family, my friends and for me. I am looking forward to new experiences and new opportunities. With that, I have made some changes and one might even call them “resolutions.”

I am starting a new job, which should help with financial issues and provide a better outlet for my creative talents. Like most, I am getting back in shape! I’ve already started running more and am starting a new yoga program. The level of booze will be decreasing, the food is getting better and I am going to start taking time out for my emotional self, too.

And… I should be writing and blogging more!

Now, do not think with all these changes that I will be staying in and not living life. In fact, my plan is to be a little less inhibited (but of course, I am safe!) and just to keep exploring my sexuality. I feel that I’ve been a bit repressed most of my early adult life and it is time to explore what I would like, would not like and just try all sorts of new things and people. I am a sexual person, sexual creature. While I am not going out to “slut it up”, I would like to just be who I am without worrying about the relationship, being with someone, or the ramifications that often are attached to women who do like to explore their sexual desires.

So, my amazing readers, hopefully I can keep you amused and entertained in 2010! Happy New Year!

Tags: thoughts, updates

Posted in Random Nights | No Comments »

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