Posts Tagged challenge

Fast Forward

Sunday morning, I woke to find myself sleeping next to a gorgeous man once again. How lucky was I – Two nights in-a-row spent in the arms of Clark Kent.

The night before, CK asked me to promise to get him up and on with his day at an am hour. I agreed. When I woke, I glanced at the clock. It was 9:00am. My alarm wasn’t set for another forty-five minutes. I rolled over and pulled CK into my tight embrace, cradling his entire body with mine. We fit together like intricate puzzle pieces. We became so entangled in each other, we jokingly called it forking. I didn’t fully wake him. He let out a tiny groan of pleasure when I pulled him in tight.

This, of course, wasn’t enough for me. I wanted more. No, not sex – Body contact. I began to remove his briefs, and he willingly aided my attempt. I followed suit and removed my own boxer briefs so our bodies would be pressed against each other skin-to-skin. I enjoyed his touch so much. He felt amazing. I fell asleep in this position until my alarm woke us at 9:45. He asked me what time it was, and I told him. His only response was, “Too early.” He grabbed my arm, rolled to his other side, and pulled my arm around him fully engulfing him.

He was such a sweetheart. We cuddled for quite some time. Periodically we’d switch positions when one of our arms would lose feeling. This was always accompanied with a myriad of kisses.

I hadn’t completely fallen for him. Why was this time different? There was nothing holding me back this time. Nothing, except myself. I was protecting myself. I didn’t bring my baggage with me on this trip, but I did bring my smarts. I knew it was too early to dive in with him. I wanted to build this the right way. If you rush the foundation, the building will collapse in due time. If you take the time to build a strong base, it can last a lifetime. I wanted to take my time. I was in no rush. Sure, I’m 28, but I still had a lot of my life in front of me to love, lose, and find love once again. I was proceeding with cautious optimism.

I think my caution goes back to our early interactions in which he propositioned me to come over for sex. I knew then and there I was dealing with a different kind of animal. Maybe he could be tamed. Maybe not. Only time would tell, but until I knew he could be tamed, I would protect myself.

The cuddling and kissing continued for some time. When my alarm rang again at 10:30, we were both a little more awake. Warning: The following may be too graphic for some. He began, as he did many times, orally pleasuring me. He loved worshiping me in that way. I certainly wasn’t about to complain. I also made sure to return the favor. I know I’m pretty good, but it wasn’t as easy for me – He was a definite challenge. He was well endowed, and at times more than I could handle. He would get a little overzealous with his hands and my head, and I would find the need to pause to ensure I didn’t suffocate.

We continued to play in bed until there was a natural pause in the action. I suggested we hit the shower. I attempted to find a way to toss him over my shoulder. I knew I could pick him up, but tossing him like a sack of potatoes was a different story. I failed. I told him I was holding up my end of the bargain to get him moving before noon. He protested and said, “Not yet. Just two more minutes,” and pulled me in to cuddle more.

Warning: The following may be too graphic for some. We started to kiss again. Finally, he said, “Shall we?” I replied, “We shall.” With that, I scooped him up and carried him to the bathroom. We hopped in the shower, and I took the bar of soap and washed his entire body. I used my own body to build up a lather as well until I found myself grinding on his backside and him bending over moaning in pleasure. Things never escalated from there to full penetration, but the didn’t need to. What we were doing was hot enough. He took the opportunity to wash me as well, and while he was crouching, he also took the opportunity to orally pleasure me. We then continued to rinse ourselves off before drying off and getting dressed for the day.

I had small plans for us that morning. I knew he’d be thrilled to take a ride on the bike. It was a gorgeous day outside, and I also knew a money saving breakfast would also be welcomed. I used all my eggs the day before, and the only real option I had left was cereal. I had a Living Social deal to use up at Sonic. What a perfect way to use it. It was a five-minute ride away, and it would be nearly free.

We hopped on the bike and off we went. We ordered our breakfast and sat. While we waited for the food to arrive, he asked if it was alright that he call his mother back. She’d been calling periodically over the weekend. They talked about his apartment search. He also mentioned me by name and told her how amazing I am, especially since I cook. I was shocked. He’d already been talking to his mother about me!? What else did he tell her about me? His mother put his nephew on the phone and they chatted for a minute. It was incredibly adorable. I was so turned on seeing his reaction to talking to his nephew.

When the food arrived, he hung up and ate. We shared our ice creams, feeding each other periodic spoonfuls. While we ate, he shared his tweeted comment on his Foursquare check-in with me: “Meal: cost-effective + tasty, but the company I keep: priceless + delicious.” He got a phone call from his friend who was just released from the hospital. After more than a few times of trying to end the conversation he was finally successful. His whole mood changed. When we finished eating, we stood, and he said, ”So I wanted to fully discuss what it was I said I wanted to chat with you about.” I was under the impression we’d already done that. Now, I was worried.

“I really enjoy spending all this time with you. You’re amazing. I really enjoy being with you. And, if I had to put a label on it, I’d say we’re dating. That being said, I think we should still be able to date other people. And, I should recognize you probably noticed I blocked you on Grindr, and that was by design. It’s a policy I have because if you try to call me, and I don’t pick up. Maybe you see me on Grindr and your mind will start to come up with scenarios.” At this point I acknowledged my awareness of this and told him how I felt about it. He continued, “I’ve done it, I’m sure other do too. And, I also should tell you, there’s a friend I’ve also been seeing since the beginning of the year. We see each other about once a month, go out to dinner, and then, well, we’ve done more than friends things.” I stood there not speaking through this whole thing. I just listened and nodded in my own confusion. “This is only going to work if we have communication and are honest with each other. I just wanted you to know,” he added.

I thanked him for his honesty, and he added, “Once again, please just be patient with me.” I assured him I was in no rush. Again, I had no idea where this was coming from.

He then pointed out how one of his loyal followers liked his comment on Twitter. He explained to me how he was kinda a hero on Twitter. He’d received comments from guys who found the confidence to change their lives based on some of the things he’s said. This was my moment. I told him I had a similar situation, and I had a secret I was waiting until the right time to tell him about it. I explained how I had a blog and received emails of a similar nature. I told him one day I’d share my alter ego with him, but it was like reading my diary, so not just yet. He seemed to be happy about the idea and accepting of my delayed full explanation.

I was still a little taken back by what he said. Part of me appreciated the honesty and part of me was confused by it all. Regardless, we hopped on the motorcycle, and I dropped him off at the PATH to head home. As I said goodbye, I told him to call me later to tell me how the search went. I didn’t think too much about what he said the rest of the day. There would be plenty of time for all that.

That night, as I was climbing into bed, I got a text from CK: “Are you awake?” Seconds after replying, the phone rang. He did call as he promised. I’d begun to think he’d forgotten. He really just called to say goodnight. He’d fallen asleep and napped most of the evening. He was tired and ready for bed as well.  I told him, “Now I will be going to bed with a smile on my face.” He replied, “Aww, baby, that’s sweet! Me too. Sweet dreams!” With that, I laid my head on the pillow with a smile across my face.

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Late Night Quickie

Sunday night in LA, I took quite a blow to my heart. I tried to prepare myself for the inevitable goodbye, but I didn’t get to say goodbye. I’d driven all over LA trying to connect with The Navigator, but he wasn’t responding.

I faced facts and drove to the airport. I had no idea what else to do with my time, so I just drove to the car rental lot and returned my car. I figured I could at least use some time at the airport to blog a bit. I sat int he airport diner and ate my dinner alone.

My flight home was awful. First off, it was a redeye. I was set to land at 6:00am Monday morning. I had to go to work later that day so I tried my best to sleep on the plane. It was also awful because I was crammed in a widow seat towards the back of the plane. My airline status with United got me nowhere. I barely fit in my seat, and I wasn’t able to stretch out and walk around because the two men next to me were sleeping the entire flight.

I managed to sleep for two hours, but woke up after that. I had no feeling in my ring and pinky finger of my left had. Apparently I slept on it funny. When a fair amount of time passed, and I never regained feeling, I became worried. Maybe I had a blood clot or maybe I’d done some nerve damage. I tried to think about other things and distract myself, but I really started to get worried. I took out my laptop and did some more blogging, but even that was a challenge with two numb fingers. I was really starting to worry, but the feeling didn’t return the rest of the flight. (Four weeks and a doctor appointment later, and I finally regained feeling — I had a nerve impingement — Cubital Tunnel Syndrome).

I was exhausted all day at work Monday. I’d only gotten a few hours sleep on the plane and about one hour in my own bed before work. When I got home after work, I was still horny from my rambunctious trip. I was on Grindr, and a cute guy from the city wanted to come over for some fun. I didn’t turn him down since he was hot and said he’d wear his jockstrap.

When he arrived, I realized he was a redhead. He also had a slight Hispanic accent. He was also quite a presence clocking in at 6’4″. He was not born in America, but had been here a majority of his life. He was decent on the eyes, but nothing you’d run to your friends about. When he arrived we went straight to my room. He slowly got undressed and comfortable until we were both laying on the bed, me in my boxer briefs and him in a jockstrap.

Warning: The following may be too graphic for some. I found the jockstrap very sexy. I’ve always been attracted to the athlete types and find locker rooms to be one of the sexiest places. They just turn me on. Always have.The jockstrap really gave him the leg up in my book. He was looking for a hot top, and I agreed to fill the position, literally. I broke out the condoms and lube, and we have a good time. Sometimes it was a little weird and awkward, but sex is never perfect! He really seemed to be enjoying himself. I did as well, but I could already tell this guy was going to linger. He was a gentle spirit. This would be no wham bam thank you man. I was going to have to sit through some pillow talk.

He started talking about his grandmother and how she is sick. He was flying home the following day to see her before she passed away. It wasn’t looking good. I started to feel bad for him, but then my emotions became distracted when he mentioned things like sleeping with her in her hospital bed. He looked like he was ready to cry, but all I could think about was this strange layout in a hospital room. I understood he was close to her, as she was responsible for raising him, but some of the things he was saying with his accent seemed very strange to me. There was obviously a cultural divide.

After we chatted some more, and he asked if he could use my shower. Now he was really pushing it! I obliged the request, but after that, he was gone.

He showered and toweled off. He began to get ready to go home. He talked about getting together again when he got back. He mentioned how heartless a lot of the other guys he’d hung out with were, and how sweet I was. He said how much he liked me. He wanted this to be an ongoing thing of friends with benefits. He told me his real name and that the name he gave me, Keith, was completely made up. Someone was a little paranoid. I felt like I found a stray puppy who wanted to follow me home. There would never be a next time, but I told him to hit me up when he got back from visiting his grandmother. After about three weeks, he did of course text, and I of course did not respond.

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Juggling Act

Over the course of time, I began talking to a guy who’d been in and out of my life for almost a year. I think I started talking to him on Grindr first. We then found each other on Finally, we became Facebook friends.

You would think with all this contact, we’d be best friends or lovers by now, but that wasn’t the case. Whenever I was between guys I was dating, I would once again hit him up. He was very attractive and seemed to have a very level head on his shoulders. I really wanted to get to know him better, but I got the feeling I was going to have to pursue this one. I wasn’t going to win him over overnight.

For some reason, this time around was a little different. He was much more receptive to my advances. When the conversation would die down, I would prod him about losing interest. He would deny it and pay a lot of attention to me. He was constantly asking for me to send him pictures of myself and sending me compliments. It was nice to have a man tell me I was attractive.

We spent many evenings chatting on a4a and Facebook. I got to know a lot about his sexual side through those conversations. They would start innocently enough about our typical lives and somehow they’d always segue into our sex lives/desires. I was okay with this because I wanted a good man with a healthy sexual appetite. This was something I’d come to learn as of late. I needed to stop sacrificing good sex for a decent guy. I needed both.

I was also trying to juggle him in with the other guys on my roster. It is always such a challenge to get gay men to commit to anything. They never seem to want to be locked down to anything. I would schedule a date, and sure enough they’d always cancel or postpone. I was really getting tired of flakes running my social life. When my Friday night date cancelled, I tried to see if he was free for a drink.

I wasn’t able to meet him when he was free. He already had plans to go to Sugarland, a gay club in Brooklyn with a friend. He reported to me about his night with texts and pictures. Apparently he wasn’t having the best time and told me it was “Indian night.” Not his cup of tea. Since we couldn’t meet on Friday, we agreed to try for Saturday night.

It was going to be tough however. I was supposed to be attending my sister’s birthday gathering at a local bar. He had plans to go into the city. We agreed to try to meet up later, but who knew if that would come to fruition. He said, “I may head into the city, but we’ll both probably be out late… Let’s keep in touch and see where we are at later.” Of course, we’d never find each other that night. He still insists he sent me text messages to meet up, but I never received them.

Instead, when I got home, I texted my new “friend with benefits” to come by. I even volunteered to let him spend the night so he wouldn’t have to walk in the cold. He agreed and came by.

We had a great night together. He was really a passionate lover. It’s too bad he was so old. Instead, we’d simply just take care of each other’s physical needs.

At 6am, we woke and fooled around some more. Again, we never had sex because we are both tops, but he did mention the possibly of bottoming for me in the future.

At 8:30, he left to go home to get ready for church. I stayed in my bed and went back to sleep.

When I woke up later, I told him and my new southern friend about my upcoming work trip and how I really wanted to meet them before I went away. The southerner had to pass because he was helping move a good friend into her apartment. We agreed to grab dinner Monday, Martin Luther King Day in the evening. Hopefully this date would finally come to fruition…

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Rallying Friends

Every year, for the past four years, I’ve hosted an annual holiday party. Ironically, I started it with a First Annual Holiday Bash because I wanted it to become one of my holiday traditions. It would be the one time of year I gathered with my closest friends and spent time with them around the holidays to show just how much I truly appreciate their friendship.

From its first year, it’s been a big hit. An invitation one year is no guarantee of an invitation the following year. I always make sure I surround myself with the people in my life I care most about. If within the following year I fall out of touch with someone, I don’t extend an invitation.

Earlier this year, my friend reached out to me to plan weekends in December. She knows of my party and wanted to make sure I wasn’t hosting it the same night she was celebrating her birthday. We both picked dates and put it to bed.

Months later, I found out I was being evicted from my apartment since my landlord finally sold it. Our eviction date was November 30th; eleven days before the planned date of my holiday party.

This was one tradition I was not ready to relinquish, not matter what it took. Some of my friends look forward to the party a full year in advance. I make an incredible spread (not allowing anyone to bring any food of any sort), and everyone fasts for an entire day leading up to the party.

This posed a serious challenge. I would have to move into a new apartment, get it settled and cater for about forty people in ten days — A near impossible feat. However, my determination is not to be underestimated.

When I sent out my Evite, my sister immediately criticized the invitation of N. She was shocked to see I would invite him, but she also didn’t have the full story.

Apparently over the course of my short relationship with N, I mentioned my annual holiday party. As the holiday season was drawing nearer, he asked for the date of said party: “When is your holiday party so I can put it in my calendar? I’m trying to attend as many holiday parties as possible without missing one.”

Did he just invite himself to my holiday party?! I mean, he was on the maybe list, I’ll admit that. But I had no intention of inviting him in the first round of invitations.

This isn’t because I was holding a grudge over our failed relationship. It was mainly because I was disappointed in him. Considering we lived across the street from each other, I thought I’d at the very least be seeing him periodically. However, since our last discussion about our failed relationship, I hadn’t seen him once. I still had never been to his apartment considering I basically walked past it every day. He never put in an effort to be my friend following our breakup, so I no longer felt the need to attempt myself. I’d given up.

When he invited himself, I had to quickly think of the best and most dignified way to deal with the situation at hand. I started with honesty. “Oh.. Are you invited to my holiday party???” I quipped. “I’m …. just gonna go… f*ck myself…” he responded. I successfully made him feel uncomfortable, but then lightened the blow. I couldn’t do much. My hands were tied. I’m not rude enough to tell him he can’t come, but I wasn’t sure I really wanted him there either. “HAHAHA. Just giving you sh*t. Sending out the Evites today…”

When others friends learned of his attendance, they weren’t happy. I was confused by this. I didn’t think anyone would care. When we were dating, my friends loved him. Everyone approved and expressed this to me. He was a very charismatic guy to be around and played nice with all my friends. It was one of the biggest things that attracted me to him.

However, when he crushed me at the end of our relationship, everyone’s opinion of him quickly shifted.

I have to admit, I don’t know if my opinion wouldn’t have shifted so drastically. If he didn’t do anything to hurt me, I would see no need for malice toward him. I wouldn’t be his best friend, but I would certainly be civil.

This wasn’t the case with my friends. In an overwhelming show of support, they all rallied against him and attempted to convince me to retract my invitation.

I was blown away. I never experienced anything like that before from my friends. I was truly touched.

However, I would not be able to fulfill their requests. I was not capable of uninviting him. I also felt it gave him the satisfaction of thinking he still had an effect on my life. I’d completely moved on. It took a long time, and I went through a lot of turmoil to get to that point. But, I didn’t need him to know that. (Not quite sure if he’s still reading the blog…)

One friend, J, was particularly poignant in his disapproval. “I’ll crack his head open.” I told him I was going to be civil, but I wasn’t going to pay much attention to him when he arrived. “Honestly, I think its risky having him there. Especially since he is a drama oriented person.” He pointed out that N may bring up the blog in front of Smiles just to p*ss me off. “Good point… Going to have to tell him not to mention the blog,” I added. “He may leave early since no one really wants him there.”

K and some of my other friends expressed their lack of interest in interacting with him, and he didn’t really know many others. J responded, “If I have anything to do with it he will leave early.” I couldn’t believe how passionate J was getting about this. He’d never even met N. “Look I’ll be civil… but if he gets out of line you let me know.”

One of my other friends who witnessed my rebound in Martha’s Vineyard, Shorty, made the following suggestion: “You should warn him that your friends aren’t really fond of him so he doesn’t feel bombarded if people are mean to him.” “No one will be mean to him, but they’re not going to go out of their way to be nice,” I speculated. “Haha. I might be mean if I happen to end up talking to him :),” she finished.

I couldn’t believe how much my friends were rallying behind me. To be honest, I thought they all thought I blew things out of proportion when it ended. I thought they all looked at me like I was crazy for being so emotionally broken up after dating someone for a month and a half. He really did break me down a little bit, and I still feel some of the lasting effects of that relationship, as much as I would like to put it in the past and forget it. But, I thought they all thought I was being melodramatic. Apparently, they validated my sentiments.

On another level, N wanted to bring his new boyfriend. I’m sure he’s a sweet guy, but I’d never met him. I didn’t want him at my holiday party. It wasn’t the time or the place to meet him. Selfishly and childishly I also wanted the upper hand. I wanted N to see me happy with someone else, Smiles, while he didn’t have his security blanket to hold onto. I know that is very immature, but in the dating world, I am still a teenager. I’d like anyone to disagree with me they wouldn’t want to do the same thing.

So, I told him he couldn’t bring him. I explained he situation, and I think N accepted my reasoning. It was going to be an interesting night regardless. Many variables were bouncing around, and no one could predict the night, even if some of my friends wanted to start a pool of bets on how early in the night N departed…

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