Posts Tagged flirt

Resolve To Overcome Your Sexual Shyness – Astroglide Giveaway

When you’re a gay man who came out at the age of 25, you look back and realize how abruptly you were faced with so many new things. Where most people experimented in their formidable years, I was sitting on the sidelines waiting for my day to shine. It’s a wonder I’m not curled up in the corner in the fetal position rocking back-and-forth. It took me some time to get comfortable in the sack, and once I felt comfortable in my own skin, there was no turning back. Or at least I thought so.

AstroglideDrYvonne_zpsc064a8f0Turns out experience can’t erase all your hangups, and when you need help, you need to turn to the sexperts. Astroglide’s Sexual Wellness Ambassador Dr. Yvonne Fulbright is came to my aid to help conquer my sexual shyness in the new year.

Astroglide’s asked me to share some of my experiences with my readers in this sponsored post.

Although I generally try to stay in shape, this holiday season, I morphed into a different kind of shape — Round. I would never let myself go so far as to let my gut get in the way of sex physically, but mentally, that’s another story. It’s hard to feel sexy and intimate between the sheets (even with the lights out) when you don’t feel sexy in the mirror. Even with my boyfriend’s advances and reassurances, I wasn’t feeling sexy. Dr. Yvonne suggests a tip:  “Boost your body image. For some, the biggest challenge to getting in a sexy state of mind and letting that be known is how you feel about your body. This also goes for those who seemingly have the “best” bodies. You can start feeling better about your form with regular exercise (as this has mental health perks as well), eating healthy meals, avoiding toxins, and shutting down negative self-talk. Do things that make you feel good about the skin you’re in.” I am already experiencing results physically and mentally through following this new prescription.


BloatedBellyI also came across some good advice I feel I’ve absorbed along the way but never put into practice. Dr. Yvonne advises: “Get to know yourself. It’s hard to express yourself or let a lover know your likes and what you want unless you take the time for self-exploration first. So take the time to masturbate. Experiment with different sexual enhancements. Read erotica for inspiration re: scenarios. Flirt with different ways to get turned on, to seduce, and begin the process of foreplay. You will feel more self-assured in providing instruction, even if it’s non-verbal.” I’m not sure I need to explore myself more often, but I should probably explore more of myself to increase the pleasure when I’m not alone.

Looking for advice for your own sexual shyness? You can submit your questions to Dr. Yvonne via the form on Astroglide’s site. And, ensure better sex in 2013 with Astroglide’s free samples! Your sex-life will thank you come next New Year’s.

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On A Sexual Roll

I have a generous amount of vacation days, as I did a very good job negotiating when I was hired at my job. I don’t, however, have friends who share the same luck. They can either take the time off and have no money to travel, or they have money, but can’t get away from work. On top of this, being single leaves me only with the option to travel – Alone. I don’t enjoy this. As a result, I build up all these vacation days and never use them.

When the new year arrives, I have until the end of March to use up all the days I carried over. As a result, I start giving myself four day work-weeks and have staycations. I decided to take Monday off after the local holiday in Hoboken. As per my usual, I woke up horny and turned to Grindr. I tried to get one guy I’d been flirting with to come to my place. He lived in the city in Harlem, so no matter how hard I tried, he was not going to come to Hoboken.

After him, I went through a ton of Grindr guys trying to find someone to come over for some morning fun. None were biting. I turned Grindr off after what I’m sure was over an hour of surfing, and hopped on the computer. I thought I would give adam4adam a shot. I had messaged a few guys, but I wasn’t getting a response. That was until I found one guy who is 26 and worked in the area.

He was a good-looking guy, as per his profile pictures. We began exchanging messages. He unlocked his pictures, and I got a glimpse of his face finally. He was a very sexy, light-skinned black man. He had this college jock look about him, and I was very turned on. His body was fit, he was clean-cut, and his smile was utterly adorable.

I asked him if he’d be free later to swing by. He had a light day at work since his boss was out of the office. We discussed logistics since he worked in neighboring Jersey City. He could either take a cab or the light rail to my place. I gave him all his options, and we made a plan for him to come by around 4:00. I learned he was usually a top, but he was willing to bottom for me. This was extra exciting to me, because I had greater hope he’d be a more masculine man than most typical bottoms.

When he arrived, I was immediately taken back by how sexy he was in his work clothes. Then I noticed his incredible blue eyes. He looked just like Michael Ealy. He was very masculine and had on slacks, a dress shirt, a tie and an incredible smile. He wasn’t nervous about this at all, which I found to be very sexy. I led him into my room, and he immediately began undressing himself. I liked his matter-of-factness — His “I know the drill” style. I sat on the bed talking to him as he undid his tie, stripped off his shirt, removed his shoes and took off his pants.

Warning: The following may be too graphic for some. The man had an amazing body. I was very pleased. I could tell he takes good care of his body, and I was ready to ravage it. I wanted to touch every inch of his milk chocolate colored skin. I was still sitting on the bed in my gym shorts and tank top when he unexpectedly took off his boxer briefs as well. If I wasn’t already excited before, now I was rock hard. He walked toward me as I stood and removed my clothes as well.

He was a well gifted man, and once we were both fully undressed, we laid on the bed with him on top of me making out for a bit. He had amazing lips and knew how to use them. He had a strong body, and I enjoyed wrapping my arms around him. It was hot! We began to fool around and explore each other’s bodies.

Ater some making out and mutual oral pleasure, he got into position for me to use some of the techniques I’d read in Tickle My Tush. I knew he was normally a top, so I took the time to make sure he was fully ready and not rush things. I was enjoying myself as well. He seemed to be really enjoying himself as well from the sound of things.

That’s when I reached over the edge of the bed to my nightstand and grabbed a condom and some lube. He was face down on the bed in front of me, and the real fun was about to begin. I really enjoyed being up against his body and feeling him. He may not have been a bottom, but he sure was passionate in the bedroom and knew how to use his body. The sex was great, and eventually he finished. Seconds after that I too pulled back and finished. It was very hot! I grabbed a towel to clean up his back and the sheets below while we exchanged a few more kisses and expressed our enjoyment with each other.

Just as he undressed like he knew the drill, he began to get dressed. I learned he was heading back to work. I was surprised because he lived in the city. I assumed I was a pit stop on the way home. I felt bad for him he had to return to the office, but I didn’t regret inviting him over. I had a great time with him and would certainly be willing to have him swing by again sometime.

I walked him to the door and gave him another kiss goodbye. He was such a polite gentleman. I could tell him momma did a good job raising him. He thanked me, to which I replied, “Thank me!? Thank you! That was great! Anytime you want to do this again, you know how to reach me.” And with that, he was gone.

In the coming weeks, we’d try to do it again, but he was having a busy week. I could tell he was more than just a hot body, so after that, I asked him if he’d ever be interested in grabbing a drink sometime, but I got no response. Perhaps he will just remain a fond memory of a day off…

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Late Night Rendezvous

I nailed down plans to meet Connecticut Cutie after work that Tuesday night. He told me he’d be in my neighborhood, so it would work out well.

He ended up running late from dinner with friends, so I stayed in the office and did a little blogging until he was ready. When I go the call that he was on the corner, I went down to meet him.

My favorite date spot in the city lately has been The Breslin, so I suggested we go there. It’s a short walk from my office, and we had great flirtatious conversation on the walk there. He joked about going to a psychologist for mother issues, and I made more than a few Oedipal comments in jest. I told him I don’t go to a therapist nor need one because I have free therapy sessions all the time. I use my friends for that service. I’m sure they all just love to hear all about my problems and issues, but hell. What are friends for?

We also talked about our days at work. I had a very easy day involving a lot of personal work with just a little professional work.

When we got to The Breslin, it was very crowded. I couldn’t believe how many people were there on a Tuesday night. We had a hard time finding a seat, so he ordered drinks at the bar while I tried to hold some ground in the corner. I was standing next to some of the most obnoxious men I’d ever met. You could tell they were a real “boys’ club” type, making lewd comments. I knew it was only a matter of time before I heard the f@ggot term thrown out. I decided to move away from the group before they p*ssed me off more.

I ordered my usual dark and stormy, and he followed my lead. He’d never had it before, and I told him it was a good winter drink. He tasted it, and was happy with his selection.

FInally a table opened up, so we jumped on it. Space was limited, so we sat with our legs intertwined. This was good body language once again and made it easy for a little leg touching. Our conversation was going very well. We were both telling stories and laughing a lot. I told him about how much I get into Halloween and started showing him pictures from Facebook. He was shocked because he never got into the holiday. It was always something haphazard and last-minute for him.

Throughout the course of the night, there was a lot of leg touching. It was nice because we could flirt in this way without making a spectacle of ourselves. The only people who had a view of this were the bartenders, and I didn’t care if they noticed. It was mutual. As much as I was rubbing his legs, he was rubbing mine.

When he needed to use the facilities, I told him how to get there. I joked about the long journey he’d have to make through the basement of the hotel. He looked at me like I was insane. I equated it to backlot Disney. When he returned, he detailed his journey through the underground labyrinth he encountered. He detailed the myriad of characters he passed on his journey and joked about how strenuous it was. I liked his sense of humor. It was all something I would say. We were meshing well.

However, I was still having a hard time getting past the flamboyance. I had a feeling he was holding back some as well. I liked the guy quite a bit, but I also wanted a real man, not a man who acted in a feminine manner. The distance thing was still in the back of my mind. The vetting process was far from over. I’d have to continue to see where things went and evaluate if it was worth the extra effort.

I hadn’t eaten any dinner, so I ordered some fries from the bar. We joked about working out and my being fat as of late. I know I’m far from fat, but there is a certain level that is fat for me. I don’t like it, and it makes me want to eat better and work out more.

After three dark and stormies, when I brought it to his attention, he realized he needed to make his way to the train. If he missed it, he’d have to wait another hour for the next. I told him I’d walk him half way — Basically back to my office. He needed to stop at the bank along the way, but we also really needed to hustle. When we got to my office, I told him I’d walk him one more avenue before heading home. When we got to Fifth Avenue, we embraced on the corner. We started kissing, and this quickly turned into a bit of a makeout session. He was a great kisser, so I didn’t mind one bit. I was starting to worry he’d miss his train. We’d already joked about how his parents extended his curfew for the evening. I knew they’d be royally p*ssed if he made them pick him up at midnight.

It was comical as we both acknowledged the other’s hardon as we pulled back. We were both really enjoying each other’s company. I said goodbye, and he sped off to Grand Central Station.

I made my way home, and made it a point to text him and tell him how much I enjoyed myself that evening. I learned he did in fact make the train and would get home at a decent hour. He responded, and I could tell he was really into me. I needed to make a decision fast, or I would risk really hurting him. But, I still wasn’t sure. I had a lot to think about. I would be traveling to Chicago for work, so this would allow me time apart and time to think about what I really want.

We talked about possibly getting together over the weekend, possibly in Hoboken. I knew once that happened, things were going to escalate fast. I already knew he had a great body from his revealing pictures on a4a. I knew he had a healthy sex drive, so that wouldn’t be an issue. I just needed to decide if the flamboyance thing was something I could get over — Something I could either look past or fully embrace. It wasn’t my style, but after all, I was constantly expanding my horizons…

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Connecticut Cutie

Since I’ve been slacking, I’m going to make it up to you this week. Hope you don’t have a busy week, because you’ve got a lot of content coming your way!

For as long as I can remember, I was trying to nail down a date with a specific guy I met on He had the cutest smile that could light up a room (in case you haven’t noticed — and I’m just coming to this realization — I’m a sucker for smiles). He messaged a few times on a4a, but nothing ever materialized.

Months passed, but I could never seem to get him to meet me. He’d show a lot of interest, and then he’d disappear for a bit. Like the ocean, it was a constant ebb and flow with him. Finally, I just flat out gave up on him, and I didn’t hear from him again. When I broke up with Smiles, I went back through my saved messages and decided to hit him up and see if this time would be different.

Ironically enough, I learned he moved out of the city. He was originally from Connecticut, and he moved back home with his parents to save a little money. It seemed now he was interested in finally meeting me, just when it would be most difficult. We discussed many evenings as possibilities to grab a drink before we finally found a good day to grab lunch. Even then, we were playing things by ear.

Of course, this didn’t happen. He had to cancel on me. However, he proposed raincheck options. He agreed to meet me for a drink one night after work on his way to Grand Central to hop on Metro North to CT. I did some research to find a bar that would be convenient for both of us. We set a time, and I told him to meet me at Annie Moran’s by Grand Central Station.

I was already having reservations about this guy. Was this how it was going to be all the time. Quick rendezvous before he went home? I finished work before him, so I decided to walk there instead of taking a subway or cab. It was raining lightly, so I broke out my umbrella, however I wasn’t walking alone. I had Grindr to keep me company while I walked. I’m such a whore. I was already looking for the next date before this one even got off the ground. But, it’s what you gotta do if you have an aversion to gay clubs. I stood outside the bar paging through profiles while I waited for him to arrive. He too was walking from work, and he worked about fifteen blocks away.

Just before he walked up, he gave me a call. I told him where I was, and when he saw me he hung up. As he walked towards me, he wasn’t quite what I was expecting. It wasn’t a bad thing; he was just smaller than I originally thought. We greeted each other with a handshake, and with that made our way into the bar. He offered to buy me a drink since I’d been waiting for him. I was in charge of watching our bags and trying to find a piece of real estate to stand/sit and chat.

He came back with the beers, and we dove into conversation. It was slow going at first, going through the standard order of questions. As he talked about his job in fashion, I noticed a bit of flamboyance coming through. I wasn’t thrilled, but it was far from a deal breaker. He was certainly cute (although he looked much cuter in his pictures before he cut his hair shorter).

We talked about family, work, his moving back home, where I live and grew up, commuting nightmares, etc. It was nice. I couldn’t quite tell if he was all that into me. I was starting to think he thought I was too “straight” for him. But, as the conversation progressed, his body language began to change. I realized he may have just been nervous. Once he relaxed, I could tell, he was flirting a little heavier. After the first beer, he asked if I wanted another. I gladly accepted. I figured he was going to dictate the end of the date since he was the one who had to catch a train. He told me all about his curfew and how he’d have to take a taxi if it got past a certain hour; his parents would no longer pick him up.

We talked about watching sports on TV and participating in them. Somehow skiing came up, and I told him my story about the first time I skied and how well I did. When the group next to us lef their table I snatched it, while he got us a third round of drinks. The date was going well, or at least I thought so.

While we sat, he took the opportunity to touch my leg periodically. I love that. It’s a surefire sign of interest. I returned the favor as well. I could tell there was a lot of sexual energy between us as well. We were both feeling it. We talked more about what we do for fun when we’er not working. He told me about his old apartment and how he still comes back into the city to do rotating dinner with friends at their respectful apartments. There were slight awkward pauses, but that can be warranted on a first date.

When he finished his third beer, he told me he had to be running for his train. I thanked him for picking up the tab, and I told him I would pay next time. “If there can be a next time,” I added. I walked him to the doors of Grand Central and said goodbye. He was lingering, and I could tell he wanted a kiss. I wasn’t sure his position on PDA, but I decided to go for it. I wanted a kiss, so I was going to get one. I leaned in with my arm behind his back and gave him a nice quick kiss goodbye. We agreed to find time to see each other again soon as we parted ways.

On my ride home, I took the opportunity to text him and let him know I thought he was cute. He told he had a great time, but also told me how he’d locked himself in the bathroom on the train. It was a really funny story, and I was happy to hear he had such a great sense of humor and easy-going personality. He told me he wanted to grab lunch later in the week, and I agreed. We would figure out a time that worked for us both. I was already looking forward to it…

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Special Forces

My time in San Francisco ended. I was thrilled I finally got to meet the online friend I’d shared so much of my life with over the past two years. We grew much closer in the little time I spent with him. I was already looking forward to the next time I would get to see him.

Early Saturday morning, I made my way to the airport. I was off to Chicago to finish out my week-long work trip. I’ve actually begun to look forward to these plane trips. It’s one of the few times I can sit and concentrate on writing blog entries without any distractions.

As I boarded the plane, I made my way past first class to my standard seat. I was happy to see it was a newer plane with slightly extended leg room. Being 6’2″, flying has become quite uncomfortable these days. I look forward to the day I get an upgrade, but those days seem to happen about once a year, even with status.

I was also thrilled to find I was sitting next to a very good-looking man with a great body. I could tell this guy was no weekend warrior. He spent a lot of time taking care of himself. I was enamored by his square jaw line and cute dimples. He started chatting me up when they announced the upgrade of six passengers to first class. Since we are both larger gentlemen, we jealously talked about their comfort levels with a certain level of “good for them.” I asked him what he does and learned he was a green beret in the Army Special Forces. I scolded him for not making that known. “If you were in uniform, you’d be first in line to get one of those seats!” He was such a nice guy. “It’s cool. I’m fine here,” he replied nonchalantly. It was such a nice change of pace not having to sit next to someone fat who stole half my seat or who smelled and ruined my entire flight.

Apparently, I wasn’t going to get through very much writing on the plane. So much for no distractions. I asked him if he was headed for business or pleasure. He told me he was flying to Brussels for an internship in defense analysis for the next three months. He told me all about what he does and how much he loves doing it. He also took the time to ask me what I do. I was proud to be sitting next to this man. To me, he was bigger than sitting next to a celebrity. I’ve always had a major soft spot for the military service men and women. Not necessarily in a sexual way. Being in the Navy was my grandfather’s proudest accomplishment. I regularly donate to the USO in his memory partly because I know how much it meant to him, but more so because I know what they have to give up to serve our country. I have friends in the service, so I’ve seen first hand what they sacrifice to keep us safe.

Through chatting with him more, I also learned his girlfriend is also in the Air Force. They were both stationed in California while he was finishing up at the Naval Postgraduate School and got to see each other on the weekends. They had it rough. They got to see each other so rarely, my heart really went out to him. We talked a great deal about his relationship and how they make it work. He realized it wasn’t ideal, but they make it work. I admired his convictions. I asked if she’d be coming to visit him while he was abroad in Belgium, but they have yet to determine if it would be worthwhile since he doesn’t know what his leave will be yet.

The more I talked to him, the more I realized how polite, cute, smart and sexy he is. I wanted to be friends with this guy. I wanted to hit up the bar and buy him a beer. It was completely in a non-sexual way too. Since I was young, I’ve craved to have “the guys.” I’ve never had a group of guys I’ve hung out with regularly. And, I’m not talking about a gaggle of gay men either. I’m talking about a group of men, gay or straight, who hung out all the time and were just real. We could rely on each other to have our backs, no matter what. He seemed like a guy who would fit that mold. He was a genuine good guy. I always try to surround myself with individuals like him, but it’s not easy.

When the flight attendant was coming by handing out drinks and asking for food/snack orders, I wanted to buy him one of my favorite United Tapas snack boxes. Had she not asked him before she asked me, I probably would have done it, however, looking back I’m not disappointed it didn’t work out. It may have made him feel awkward or uncomfortable. I just wanted to show my appreciation first-hand for what he does, however, I didn’t want to do it at the expense of his comfort. He probably had no idea I was gay, but some people are uncomfortable taking handouts. I also loved watching him flirt with the flight attendants. He was quite a smooth operator without being overt or corny.

When the plane landed, he proved once again his gentleman status. He was “Mr. Chivalrous” helping all the women with their bags. I glanced over at his boarding pass for his connecting flight to Brussels and caught a glimpse of his rank, Major and his name. He turned to me just before stepping into the aisle and wished me luck on my pitch.

As we exited the plane, I snapped a picture as he walked away (trying not to be creepy!).

When I got to my hotel, I hopped online to see if I could look him up. I wasn’t going to stalk him. I was just curious to know more about him. I found him on LinkedIn and learned more about his educational/occupational background. It is vastly impressive. I resisted the urge to add him as a connection on there and went about my day.

While I was in Chicago, I planned to visit my friend who moved there a few months prior. I hit him up when I landed because I was going to try to meet him for dinner/drinks that evening instead of dining with my coworkers. He replied telling me he had a fever and wouldn’t be able to make it out while I was in town, and we’d connect at a later date.

This was going to truly be a work trip, so I dove in full force to make sure I delivered.

In only somewhat related news…

A photo I came across in my Facebook feed over the past week makes me smile every time I see it. I dove into researching all about it. I am fascinated by it and love the media attention it is receiving. This shouldn’t be getting media attention. It should simply stand on its own as an amazing display of love and affection. But, until homosexuals are treated as equals, I welcome the attention. I hope it inspires you to be more courageous in your life, as it has inspired me.

If you’d like to read the full story of what is happening in these images, click here.

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It’s About Time

Today is a Fast Forward Monday!!!  

My apologies to those who have come to expect Fast Forward Fridays. I have been traveling for work/pleasure, and I got caught up in things. I haven’t had a chance to write the second post, so I’m making up for it today. Hope you are enjoying these. It will help bring the blog a little closer to real-time. If you’re keeping up with the stories chronologically, please skip down to this morning’s post first, then read this one. I think it’s a good one! Enjoy!

Back to your special edition of One Gay At A Time…

After missing the opportunity to finally meet my online friend after almost a years time chasing each other around, the day finally arrived when I was scheduled to finally meet him in the flesh. This was well overdue, and I was quite excited. I wasn’t about to get ahead of myself, but the suspense had been building up for quite some time.

We discussed where we would go for drinks or dinner and finally settled on Charritos, a Mexican restaurant I’ve been to on numerous occasions. In fact, this wasn’t the first date I took there. We planned to meet at 7:30. I knew the place didn’t take reservations, but it was a Monday night on a holiday weekend. I figured everyone was home getting ready for the coming workweek. It also wasn’t the nicest night, as snow was in the forecast, so I thought we’d be alright.

When I arrived, I was immediately proved wrong. I stood in front waiting for him to arrive noticing every table (all 8 of them) filled with diners. Finally, he arrived, and we attempted to go inside out of the cold. Even this proved difficult since there was nowhere to go once we were in there. While we waited for a table to clear, we awkwardly chatted.

This was surprisingly difficult. He seemed so incredibly flirty online and charismatic, and the man standing in front of me was a very shy reserved individual. I couldn’t get over it. Where was the guy I’d been chatting about my body and sexual interests in detail? Where was the flirt?

We talked about work and the weather. It was a struggle to find a topic to discuss. Everything felt forced. It wasn’t awful, but it certainly wasn’t what I expected.

Finally we got a table and sat. After we ordered, we started to chat a bit more. I asked most of the questions. He always responded in detail, but he never asked a question in turn. That may have helped the conversation flow much more freely, but it wasn’t there. I had to volunteer all my information. I feel awkward talking about myself when I wasn’t asked to. It was as if I was interviewing him for a job.

One topic we got on was siblings. I don’t know why, but that topic has been coming up more and more frequently on my dates. I’ve actually noticed it and tried curbing it. I learned about his siblings as well. It was nice to hear he came from such a similar family dynamic.

We talked about his job as well. I was very intrigued by it. He told me all about his schooling, his specialty in the field relevant to the gay community, his boss, the clinical work he does… This was really shaping up to be quite the catch of a man. He was very sweet and thoughtful. However, our chemistry was not mixing AT ALL! It was so disappointing. On paper he looked so good. Online, he seemed a sexual match for my libido. In person, he was a mouse. Night and day from my expectations.

After quite a while, the waiter basically asked us to leave. There were people waiting for a table, so they kicked us out. I was more than a little p*ssed, because I thought it was very unprofessional and rude, however, it was time for the date to conclude.

We’d already talked about him coming over to my apartment before the date. I was still very sexually attracted to him. I wondered if he’d relax when he was out of the public eye. As we walked outside, I asked him where he parked and told him I’d walk him to his car. I was hoping for a signal along the way to show his interest. I thought he’d drive me to my apartment and come up.

When we got to the car, it was the complete opposite. I hope you can understand my explanation without a diagram:

I thought we’d at least say a proper goodbye. I was hoping for a kiss considering all I could think about during the meal was how good his lips would feel. When we got to the car, I stood on the sidewalk, and he walked to the front passengers panel in front of the rearview mirror. That would have been fine. I may have even used the car as a backboard for a strong kiss, BUT there was also a chopped off parking meter between him and myself. Yes. A metal pole about four feet tall was between the two of us. I don’t think he could have strategically showed his lack of interest any more other than to simply get in the car and drive away.

We said goodbye, and I told him it was nice meeting him. He said, “Likewise.” That’s when I grew some balls and took what I wanted. I moved forward, reached my long arm over the pole, hooked it under his arm around his back, and pulled him in for a kiss. It wasn’t a long kiss or a makeout session, but I certainly wasn’t going to be satisfied with a peck.

And with that, I turned and walked home in the flurries falling from the sky. I was still a little blown away by the lack of spark during the date. I wasn’t even ready to go home. I decided to stop by my friends’ place on the way home and say hi.

I came in and we caught up on what’s going on with each other before I told he and his wife about my awkward date. He was a little baffled by it as well. He couldn’t understand what was going on. He really loved the parking meter pole story as well. I was so nonplussed.

I sulked home after saying goodnight to my friends. When I got home, I was curious to see if he was back on a4a. Surprise! I was right. I wasn’t going to get past this immediately. I needed to ask him about what happened.

“Surprise, surprise. Look who’s on here,” I messaged him. We chatted a bit awkwardly about the date. He messaged me back: “I was waiting for you to ask me to come back.” He wanted to come back to my apartment. He even brought his c*ck ring and poppers with him. I was so confused, and I made that clear to him. He wasn’t aware of his mixed signals, nor was he aware of the pole. He just thought I wasn’t interested since I walked him to his car. It was all a big misunderstanding. “I had a good time. I thought the conversation was nice,” he added. That doesn’t make up for the awkward date however. That just cleared up the mixed signals at its close.

Just to satiate my curiosity, I told him we would have to try to fix what went wrong when I got back from my work trip to San Francisco. He agreed, so we kept in touch over the next week.

I decided to see what was going on with the southern guy. He texted me to see how my weekend was, so I picked up the phone and called him. Again, we talked for almost an hour while I packed. This completely made up for my awkward date. I was really looking forward to getting back so I could finally meet him. Hopefully this one wouldn’t be as big a disappointment.

In the morning, I had a message from my new southern gentleman caller. He was asking for a picture of my “morning excitement” we’d discussed previously. I denied his request and told him he’d have to wait to see the real thing. This was my way of getting him on the ball about meeting up with me.

I also got a text message from my friend and recent neighbor. It was very sweet of him to do so. I needed to make it a priority to hang out with him when I got back to New York.

All that would have to wait on the backburner… The following day, I was headed to San Francisco for the week for work. Waiting for me were two men. One I attempted a long distance relationship with whom I would meet for a cocktail. The other, a great confident and online friend whom I was extremely excited to meet in person, especially in the bedroom…

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Highs and Lows

I had been on OKCupid only a short while before I met Smiles. I met only one person from the site, LES, and that was already after I met Smiles. I have to say, I’m not that big a fan. Every search I did produced few candidates I was willing to entertain. No one was good-looking, and no one had exciting profiles. It reaffirmed for me why I originally was so against dating sites. I felt like it was full of desperate men.

Rarely would I receive a message for a worthy candidate, but when I did, I would quickly respond and dry to stir up some dialogue.

I started chatting with a nice southern boy from North Carolina who moved to the city in the previous few months. He seemed like a really genuine guy who wasn’t into the scene or fully out. I was very attracted to that. The southern boys always brought a little extra something I always liked. They were mannered and real men.

We messaged back and forth on OKCupid for some time before we exchanged phone numbers. One night, he asked if I could chat. I asked him for his gchat or AIM name. He responded, “No. I meant on the phone.” To which I responded, “Sure.” We spoke on the phone for an hour that night. I really got to learn a lot about him. He was volunteering a lot of information about his upbringing and his company and where he is today. He told me how he hates gay bars. He even took the time to tell me about his “hetero life partner.” That’s what he calls his best friend and roommate he left behind in North Carolina when he moved up here. Apparently they were completely best buds, however, nothing sexual ever transpired between the two of them. It was sexy to hear him speak about such a masculine love with his friend. I was really liking what I was hearing, and the fact that he wanted to call gave him so many bonus points in my book. I even told him that last bit of information, which I think he really appreciated.

In the morning, things switched to texting. He was horny and asked me to send him some more risqué pictures. I was onboard. I was all the more happy he asked actually. It proved to me he had a healthy libido, especially in the morning, which is when I’m at my horniest. We exchanged a few racier pictures and went to work. We made a commitment to each other to try to find some time to go out on a date in the near future. I couldn’t wait. He was not only sexy to look at and hopefully to touch, but he was also sexy and masculine in his personality.

In the meantime, I was also talking to a guy I met on who I’d been messaging on and off for over a year. Between every relationship, this guy and I would exchanges flirty messages and pictures, but nothing would ever transpire. It was so frustrating because I found him to be very hot. He’d get very flirtatious, but never follow through or agree to meet me. Now I was making some ground. This time around, he seemed genuinely interested. I’m not sure what changed, but I was going with it. He was coming back home after a weekend away, and we were texting the entire ride back. When he got home, we continued the conversation on Facebook with a lot of banter and playfulness. He was really coming around on me. I continued to propose a date, but it wasn’t the easiest. He was open to the idea, but I couldn’t get him to lock down on a specific time and location.

A lot of our conversations revolved around sex. Again, after the dry spell I went through with Smiles, I was happy to hear it. I also knew he had a great job, as he had his doctorate and was using to teach at a college and work at a clinic. He really seemed like the full package. From looking at his Facebook pictures, I could tell he loved to travel and he loved to have a good time. He also lived close to me. I felt like this time, I had it in the bag.

That night, I found a guy on Grindr. He was visiting, and the host he was staying with was away. He knew no one and wanted to go out. I was already contemplating going out, so I convinced my roommate to join us at the bar for casual drinks. We met him on the walk to the bar, and when we did, I was shocked. He was tiny. I’m 6’2″, and he was easily 5’2″. My roommate immediately whispered a comment to me. Then he opened his mouth and the queeniest voice came out. I was so turned off, but I couldn’t be rude.

We awkwardly sat and chatted at my favorite bar that night. It was dead, so there wasn’t even anything to distract from the incompatibility. When my roommate and I had our fill, we decided to head home. The little munchkin followed us home. He asked if he could come over, and I agreed. It was a moment of weakness. I was horny, and I thought he could be fun.

BOY WAS I WRONG. He was beyond a stage five clinger. After some making out and heavy petting, he spent the night. The next morning, he told me the only way we could have sex is if I could see him the next night. Foolishly, I agreed. It was bad. No. Let me rephrase. It was awful! I couldn’t get rid of him fast enough. I kept laying it on thick how much I needed to get to work, and finally I scooted him out the door.

This was just gay karma coming back to bite me in the ass. I never should have led him on. From the bar, I should have had the balls to just send him home and take care of myself. This is where my penis gets me into trouble. Soon enough, he’ll learn his lesson…

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