Posts Tagged skype
Sticking to the Plan
Posted by One Gay at a Time in Gay Dating on May 4, 2012
I had a Friday to myself, and I wasted it on hookups. I could have been doing something productive like going to the gym or grocery shopping, but instead, I spent the day inside trying to line up sex.
There was one man in particular who I’d exchanged messages with on adam4adam.com. He was a well-built guy with a sexy body. He had a nice amount of body hair, great muscles and a spectacular behind. We’d talked about hooking up a few times, but we’d never seemed to line our schedules up. I messaged him, but he didn’t respond.
I continued to search for other guys on the computer when he finally responded. He didn’t read my message until it was too late. We exchanged phone numbers, and he called and told me he had a lot of errands to run before his mother’s birthday the following day. He wasn’t able to see me until later, but suggested we Skype in the meantime. I had nothing to do, so I agreed.
He was even good-looking with bed head on the computer. I couldn’t imagine how sexy he was in person. Seeing him on the computer was just making me hornier, if that’s even possible. I tried so hard to convince him to come by before his errands and do them later. All he needed to do was time-shift his day. He kept telling me the only way it would work is if I came to his apartment. I couldn’t because it was raining, and I don’t ride the motorcycle in the rain. We pushed back and forth for some time to no avail. Of course there was some teasing with body parts on camera while all this was going on. I couldn’t wait to feel his sexy body. Alas, he had to go, so I said goodbye and we made tentative plans for later. I told him when I came by, he’d certainly have to wear his jockstrap for me. He gave me a disclaimer. He was up for almost anything, but he was not up for full penetration the first time meeting me. I was a little disappointed, but understandable.
That’s when I turned to the Mexican guy in the previous post. He was willing to come by right then, and I needed a release. I had immediate regret after that encounter.
Later in the day, my old roommate texted and asked if I was interested in meeting up for happy hour. After being cooped up in my apartment all day, I thought that sounded like a spectacular idea. No one ever invites me out for drinks either. It’s usually me doing the inviting, so it was a special treat. I texted the burly man from my morning Skype session to tell him I’d have to postpone. He called immediately protesting. I told him other things came up, and I wouldn’t be able to come by. He didn’t stop persisting to try to persuade me otherwise. I told him he could have solved the whole thing had he come by earlier in the day.
The clock reached 6:00, and I hadn’t heard from my old roommate. I reached out to burly man to see if he was still available. Indeed he was. I agreed to come to his place a few miles from my apartment. He told me he would be waiting for me in bed wearing nothing but a jock and would leave the door unlocked for me to just walk in.
I drove over there and texted him when I got to his neighborhood. I tried the door, but it was locked. I called him to tell him, and he said his upstairs renter must have left and locked the door behind him. He told me to back away so he could unlock the door. I did as I was told and gave him a minute to get back to his bed.
Warning: The following may be too graphic for some. I came in, undressed down to my boxer briefs and began kissing his back while pressing my body against his. It was as great as I imagined. His a$$ looked incredible in that jockstrap! I could barely resist him. We had a lot of fun together. There was a lot of groping, heavy petting, kissing, sucking, licking, biting, rubbing, etc. It was great. I was really enjoying the jockstrap as well. I was grinding on his backside, almost penetrating him, but never fully entering him. He really enjoyed it and was pushing me further, but in the end, he stopped himself.
He was begging for me to finish, and he brought me to the edge many times. He started orally pleasuring me. He thoroughly enjoyed this, and it was turning me on since he was enjoying it so much. Eventually, I finished in his mouth and all over my abdomen, and he loved it. He began to use his hand to pleasure himself. I helped by applying pressure to different areas until he finished all over his abdomen. We’d chatted about how each of us shoots on Skype, and it was interesting how different and how similar we were. His description was pretty spot on for what actually happened.
We both just laid there a minute and enjoyed the feeling pulsing through our bodies. I still couldn’t get over how amazing his a$$ was. I wanted to penetrate him so bad, but I knew that would have to wait for another day. He hopped out of bed and handed me a towel to clean up. While I stood there, I met two of his cats. They were very cool. This guy was quite into animals. He had a huge saltwater fish tank as well. He ran to the restroom while I got dressed. I also took the opportunity to snap two pictures. He came back and got dressed as well.
He walked me outside and chatted a bit while he smoked a cigarette. He didn’t live in the best of neighborhoods. An old woman so strung out on something walked by, and he engaged her in conversation for quite some time before finally offering her one of his cigarettes and sending her on her way. He told me about how his mother lived next door and his family’s ties with the city. He was a really nice guy. I could see myself seeing this guy again some time. He told me he was also kinda seeing some guy, but it was very casual and nothing serious. He mentioned the desire to see me again sometime, but we didn’t set up anything concrete.
I sped off on the motorcycle back home to shower and get ready to go out and meet up with friends. The only friend interested in going out was P. We agreed to hit up one of my favorite local spots where I know the owner, and he takes good care of me, Cooper’s Union in Hoboken. We had a relaxing night drinking and sitting at the bar. I told her about how I was getting out of control, and it was then I decided I was going on a Grindr diet. This had gone on far too long. I was realistic enough to know I couldn’t quit it cold turkey, but I also knew it was a great temptation for me. I was going to try to steer clear. I would only go on to see if someone messaged me. I would no longer cast out a net and would no longer have it running on my phone all day. I needed a break. I was addicted, and it was time for me to ween myself off the drug…Follow @onegayatatime
Goodbye to a Closer Long-Distance Friend
Posted by One Gay at a Time in Gay Dating on March 2, 2012
Today is another Fast Forward Friday!!!
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…
On Friday, my last night in San Francisco, I made plans with Swinging D*ck to come to my hotel. We talked about grabbing dinner before staying in for the night. However, he casually invited me to come out with him and his friends when he realized he had to go out for a friend’s birthday. I was apprehensive since it was a torrential downpour outside. It hadn’t rained for three months prior, but now it was raining for three straight days. This trip was turning out to be an epic fail.
I graciously accepted his invitation and waited for his call to tell me where to meet them. Hours passed, and I didn’t hear from him. I was all dressed up with nowhere to go. I decided to run out to grab dinner at In-and-Out when dinnertime passed by. That’s when I finally got a text. He told me they were going to Lookout in a bit. He would text me when they were leaving, and I could meet them there.
I ate my burger in my hotel room and made my way outside to hail a cab. Luckily I wasn’t out in the rain too long.
When I arrived, I made my way to the second story bar and began looking for him. After two minutes, and noticing a lot of men scoping me out, I found him in the crowd on the other side of the bar. I walked over and said hi with a big hug. He introduced me to his friends. They were all very nice. I wasn’t sure exactly how much they knew about me.
I ordered a beer before I was told we would be moving on for the night. It was back out into the rain. Apparently, we were headed to a house party for the remainder of the night but not before popping into a liquor store for some beer. We hopped in a cab and made our way to the party.
It was slightly awkward because I was now a friend of a friend of the host. I was hoping everyone would be okay with my attendance. Luckily, only the entrance was slightly awkward. After that, I was in my element. I talked with my friend, his friend, and many other men at the party. It was the biggest sausage fest I’d ever been too. I think there may have been two women there versus the fifty gay men.
I met some interesting people and one very sexy man who looked a lot like Steve Pasquale (Sean Garrity) from Rescue Me. Swinging D*ck is a smoker, and when I drink I’ve been known to smoke the occasional cigarette, so those were nice breaks where we somewhat stepped away from the group and could talk more. He really was a sweet, intelligent guy. I learned a lot about him talking to him on Skype, and I only wanted to get to know more.
The night was beginning to draw to a close. For one, I had a flight to catch in the morning. Secondly, the birthday boy/host was ready to hit up the bars. Everyone was getting kicked out. S.D. told me he had to tell me something when we got outside. We walked away from the party to find a bodega to get him cigarettes. As we did, he took the opportunity to confide a big secret he’d been walking around with.
He pointed out to me how standoffish he was the previous night, how he had to leave early and how he changed plans from coming to my hotel that night. Then he told me all this wasn’t because he wasn’t attracted to me — Quite the opposite. The reason was because he was HIV positive.
My heart immediately sank, and not in a selfish way. The compassion I felt for him in that moment was so great, I can’t even begin to explain.
Apparently I know very little about HIV. He told me he’d been “positive undetectable” for a year and a half now. I never heard that term before, but deduced its meaning from its name. I also did the math in my head and realized he contacted it just after he started talking to me on Skype. I put two and two together and realized that’s why he was so depressed when I was talking to him. My heart was breaking for him.
He explained that he is on medication, and the doctor told him he would lead a very normal and full life for the remainder of his time on this planet. I was learning a lot about the treatment for HIV. I realized I needed some education, and I was happy I had someone so amazing to teach me.
A large part of me wanted to cry and give him a big hug because I couldn’t imagine what he was going through all this time since being diagnosed. The larger part of me was upset because he felt he couldn’t just tell me outright from the start.
He didn’t know how to tell me, nor did he want to. He thought I would treat him differently or stop being his friend. I told him he needed to give me more credit than that. He was an amazing guy, and nothing changed between us.
He started to explain his strange behaviors I wasn’t even noticing. When I asked him back to my room, he was very leery because of what might happen, but he still wanted to be with me. So, he agreed. When we were fooling around, he said he was purposely taking more time to please me so I wouldn’t even have a chance to please him. When I went for it, that’s when he really said he had to get going. It wasn’t because he wasn’t attracted to me. It wasn’t because he didn’t like me. “I think you’re amazing,” he added. It was because he was scared. I understood completely.
When I asked him to come to my room a second night, he talked to his friend about it. “I don’t know if I can tell him,” he told his friend. His friend told him to do whatever he felt comfortable with. He actually invited me to come out with them that night in an attempt to set me up with his friend. Looking back, I did feel as if I was being sized up as the night progressed. However, I was not feeling him in the slightest.
When we were at the party, he encouraged me to go with the guys who asked me to come with them for some fun because it would get him off the hook. I wasn’t the slightest bit interested in them either, however their compliments were always welcome. 🙂
I never noticed all this, but I jokingly reprimanded him for going through all those charades instead of just telling me as a friend. Of course I would understand. I told him about all my skeletons. I would have hoped he’d feel comfortable telling me his.
We continued to walk to the bar everyone was heading to. He told me about how he contracted it and how bad the situation was. He admitted that’s why he was so depressed when I first started talking to him. It all made sense now.
When we arrived at the bar, it was time for me to say goodbye. I had an early flight, and it was already two in the morning. We talked a little bit more, gave each other a big hug, and made out a little bit. It was hard saying goodbye. I felt we had so much more to talk about. But I needed to go. We kept coming back for just one more kiss before we finally parted ways.
As I walked towards my hotel searching for a cab, I thought about what just happened. My heart was still breaking for him that he had to go through that. I wish I’d known sooner so I could have been there more for him. I was so proud of him for finally finding the courage to tell me. I was starting to think he just wasn’t into me a little bit, but that’s not important. What is important is that I have a friend I love dearly and will always be there for, no matter what happened to him. I just hope he knows that!Follow @onegayatatime
Finding the Piece of My Heart I Left in San Francisco
Posted by One Gay at a Time in Gay Dating on March 1, 2012
Wednesday night arrived. It was “date night” for San Francisco and I. We were meeting in the Castro to grab a drink and maybe some dinner together. It had been a while since I’d seen him last, and we were due for a catch up.
Since work was paying, and I was too lazy to learn the public transit system in San Francisco, I decided to take a cab. We arrive in The Castro neighborhood, and I witnessed the largest rainbow flag I’d ever seen in my life. The only thing I could compare it to (for the Americans in the room) is the giant American flags that adorn the poles in the parking lots of Perkins across the country. If you read my blog, you know how much I’m not a fan of the rainbow. However, I’m embarrassed to admit, the sheer size and presence of this thing actually made me a little proud.
I got out of the cab and met him on the street as we exchanged a hug and a kiss. We made our way to Badlands just up the street just in time for some happy hour specials. We caught up on the other’s dating life over the past few months. I learned San Francisco is currently casually dating someone. In the back of my mind, I’m very happy to hear this news. I didn’t want things to escalate beyond drinks for us, and this news was reassuring.
I told him the abbreviated story of Smiles and what I did on New Year’s Eve. He was a little surprised, but certainly didn’t judge.
As the alcohol flowed, his emotions escalated. He became much more affectionate, and even started to get a bit hot n’ heavy. I just went along with it. I had no emotions attached to these actions. I was fully over San Francisco. I tried changing the subject so he wouldn’t keep putting the moves on me.
He talked about the possibility of moving back to New York, but said it would be very different this time around. He’s a completely different person. Everything he was saying were basically the reasons why I ended things with him. It was as if he’d read the blog. (To my knowledge, he still does not know about the blog).
We started talking about his dream of opening a bar in Hawaii. We talked a great deal about even the smallest details in his dream. I suggested a name for his bar, and he immediately fell in love with it. He even went as far as to register the domain immediately from his BlackBerry. I told him how to do all this with my advertising background and knowledge and my recent experience of purchasing my own domain for this blog.
He then brought up the possibility of checking out a drag show that evening, but then he remembered it wasn’t my thing. Instead, he suggested we grab dinner at one of his favorite restaurants.
The meal was spectacular, and it wasn’t that expensive. I was also introduced to one of his friends who is a server there. As the night went on, San Francisco grew more and more inebriated. He wasn’t’ too much to handle yet, but he was drawing closer. He started growing louder and more indignant.
When the bill arrived, I think he thought I was going to take care of it. I think he thinks I have an unlimited expense account (which isn’t the case at all), when in reality I paid for his meal the last time I was out there because I wanted to thank him for hanging out with me that night. We split the check and made our way for the door.
The whole time, I was trying to send a pretty clear signal I wasn’t interested in hooking up that night. I was failing. He asked if we should go back to my hotel or hit up his apartment. Then he answered his own question when he realized how close to his place we were. Again, I just went with it. I’m not entirely sure why I didn’t just go home. I think I thought I could get him home and then say goodnight.
While we rode in a cab to his apartment, he asked me about the stuffed animals and orchids he sent me for my birthday. I explained that was over nine months ago. I was lucky I kept the orchids alive for six months. As far as the stuffed animals, I told him I gave the mistaken monkey away, but I still had the bear (of much more significance) at my parents’ house.
When we got to his place, I met his roommate for the first time. One had only seen me on Skype and heard lots about me, and the other had never met me. Ironically, the other share the same unique name as me and joined on as a roommate shortly following our breakup. I’m not going to lie; I thought it was a bit weird.
When we finished tormenting the roommates with S.F.’s drunken antics, we went into his room. It appeared I was spending the night. However, it was just going to be that. I was not having sex with him.
Of course the makeout session ensued. I thought to myself, “At least he’s a good kisser.” Then the makeout session morphed into more passionate actions, and I found myself with no clothes on. S.F. put me in a position to begin to penetrate me, but I wasn’t going to make it that easy for him. I kept casually squirming so it wouldn’t be possible. He kept gently trying, but I wasn’t going to give in. There was no way in hell I was going to have sex with him, but I also knew I was dealing with a drunk man. I gently whispered into his ear, “Let’s just spend the night together.”
With that, he rolled over into little spoon position. I curled up with him and went to bed. In the morning, when my alarm went off for me to head back to my hotel to go to work, I found myself with his mouth on my “morning excitement.” I had forgotten how good he is at that. It didn’t quite matter. I wasn’t in the mindset to finish with him, and we know how difficult that can be even when I am in the mindset.
I got dressed, and he remained in bed. I could tell he was disappointed, but I didn’t care. I was not going to revisit old territory.
I didn’t hear from him until much later the next day. He told me how hungover he was in the morning, proving to me how drunk he was. He asked what my plans were for the remainder of my trip, but we didn’t discuss meeting up again while I was there. I was happy to dodge that bullet.
I let things go further than I wanted, but at least I didn’t hurt his feelings too harshly in the meantime. In my mind things wouldn’t quite be the same for us going forward. No longer did I feel the urge to call him just to chat, which is sad. It appears I have collected what pieces of my heart I left in San Francisco…Follow @onegayatatime
What Doesn’t Kill You Makes You Stronger
Posted by One Gay at a Time in Gay Dating on February 10, 2012
Sunday afternoon, I tried to see if Smiles would want to do something fun the following day since I didn’t have to go to work. Sadly, he had work to do. He was trying to build up a company from scratch, and it is a lot of hard work, so I understood. What I didn’t expect was he would be busy he wouldn’t be able to find the time to pick up the phone and call or text.
Monday passed with me planted on the couch watching TV all day while surfing adam4adam.com and reactivating my Grindr account. I was just seeing what was out there, but as the afternoon progressed, I started to think toward the future while examining the past.
I realized I wasn’t happy. I equated my relationship to the struggle of Sisyphus, a king punished by being compelled to roll an immense boulder up a hill, only to watch it roll back down, and to repeat this throughout eternity. I was constantly putting work into the relationship only to find I wasn’t receiving much benefit from it.
I had given Smiles more than his fair share of chances to finally woo me, and he failed. I enjoyed his company, and he was a very nice, successful, good-looking man, but the time had come to move on. It just seemed he wasn’t that into me, and I realized I deserve better. Since I had been on the journey to this conclusion for quite some time, I wasn’t that broken up about it. I’ve had varied reactions to the end of relationships in the past. I moved on with closure after my mutual breakup with Broadway. I had slight some minor cardiac scarring after I ended things with San Francisco. I was a wreck when things went south with N — Losing ten pounds in a week (Not proud of that).
This epiphany wasn’t all that earth-shattering for me. Things had been on the decline for some time. This certainly didn’t come out of the blue, so the blow was lessened.
I actually started to get slightly angry about things. I felt used. I recalled asking Smiles on our first date why he was on Grindr, and he had mentioned he was lonely. I realized I was someone to pass the time for him. I was someone he could go to dinner with so he didn’t have to eat alone. I was someone he could have the occasional romp in the sheets when he was in the mood. I was a seat warmer. He never had any plans to forge a relationship with me, and this made me really feel used.
I wanted more. I deserved more. And I was going to find more. I started searching once again on a4a and Grindr. These are clearly not the best place to find Mr. Right, but it couldn’t hurt to try. Once again, it was just going to be a lot of work.
On top of it all, our sex-life was minimal. As a result, I was horny. I was hungry for some good sex. Over the summer when I was having my wild time, I felt I started to really hone my craft. I had numerous guys constantly hitting me up for seconds, thirds, and more. It was great for my ego, and I craved a really good romp in the sack.
That’s when I turned my efforts toward Grindr. I wanted to find a local guy with a hot body. I knew it wouldn’t be easy from past experience, but maybe some new hotties moved into the area in the three months I’d been away. I started talking to one guy for quite some time. We even started to Skype with each other while I watched TV. He lived very close and had a really nice body. He was Asian, which doesn’t quite get my engine roaring so there he wasn’t a relationship prospect, but we could at least start on a friendship. We face-time chatted most of the evening. I gave him full disclosure on the situation. We even discussed him coming over to hook up, but in the end I decided to be good.
Afterall, I still hadn’t officially ended things with Smiles yet. It wouldn’t be right. I’d already betrayed that relationship once, I didn’t need to do it again, not matter how resolved I was about its end.
I got an offer from a man I’d had a tryst with in the past. He begged me to come to his apartment, but it was cold outside, and it was getting late. I had work the next day, and I needed to go to bed. I told him I’d take a rain check.
My new friend went to bed, and I continued to figure out a way to satiate my libido. I figured I would hit up some old friends in my Skype contact list. One of the sexiest men happened to be online. He lived in South America on an island, and I wanted to do bad things to his body. It was amazing. I loved camming with him. The only issue was he had a big thing for me. He always begged me to be his boyfriend, no matter how many times I told him it couldn’t happen because we are so far away. He begged me to come visit, but I told him I couldn’t afford the flight. I wasn’t about to fly to South America for a booty call. But if he lived anywhere close, I would have been over there in a second!
I convinced him to have a little fun on camera until I finished. As usual, it sapped all the energy from my body, and I jumped into bed and dozed off without a thought left in my head.Follow @onegayatatime
Am I Broken?
Posted by One Gay at a Time in Gay Dating on December 13, 2011
The following topic of conversation is very embarrassing and very personal. It’s not easy to talk about, but I have a strong feeling I am not the only one who suffers from the issue. Warning: It may make some of you uncomfortable. I am exposing myself in this post, but I feel I need to face my demons to be able to get over them. I also feel guilty writing about this, because it’s a bit of an invasion of privacy for others, but I also feel it’s necessary if I’m being honest with myself and this blog. I wonder if someone out there may have insight to help me and others with this predicament. I feel the need to shine a light on this issue, as no one is talking about it.
My intentions were obvious this time around with Smiles. My hand was down his pants fondling him until I was pushed away with a grunt. There was no misconstruing my intentions. After being denied sex yet again by Smiles, I felt the need to consult my council.
I called Boston for his take on the situation. I explained being denied sex on more than one occasion. His immediate response was, “Oooooo. That’s not good. Something isn’t right.”
I responded, “I know, right? I just wanted to make sure I wasn’t making a mountain out of a mole hill.”
We chatted about the issue, and he told me I needed to address the issue. “Sex is an important part of any relationship, and based on what I read in your blog, sex is important to you,” he added. We discussed the best way to bring it up. The main consensus was waiting until the relevant situation arose. He suggested I don’t bring it up over dinner. If I was denied again, I should bring it up immediately to find the root of the problem.
This was the point in the conversation where I made a small confession of my own. I was worried I may have been to blame for the quantity. I explained my climaxing issue to Boston for the first time in full detail. I told him, while I’d been with Smiles a few times, I had yet to climax. This was through no fault of Smiles. This was a common occurrence for me dating back to the days I was with Broadway. In fact, I feel it was a large part of the reason we broke up. It put a lot of strain on the relationship. He took it personally, even though I assured him it had nothing to do with him. I was still quite attracted to him and still received pleasure from sex, but I wasn’t finishing.
I never was able to find the root of my problem. For a while, I hoped it would fix itself. When it didn’t I explored a number of theories. The leading one being I hardwired my brain to function in a specific way in relation to sex.
For 16+ years, my main outlet for my sexual frustrations was viewing gay porn and pleasuring myself. I wasn’t dating men, and I wasn’t exactly a lady killer either. I would go home, open the laptop, and take care of myself. I worried my brain was hardwired to react only to that stimuli.
I wanted nothing more than to “fix” this issue. For some time, I masked it by prepping myself. If I knew Broadway and I would be having sex, I watched porn before I saw him to build up a “spank bank.” I referred to this when he got me close to finishing to get me over that last hill. It worked for some time, but eventually that solution lost its effectiveness. That’s when things got really bad. I got so stressed about it, when the moment came, there was nothing I could do but think about my lack of performance. I was so wrapped up in the issue, there was no unwinding me at that point.
I had many frank discussions with Broadway on the subject. After discussing it, we agreed not to talk about the issue for some time. It was the only way I was going to be able to relieve some of the pressure I was putting on myself. Eventually it did the trick, and I had my happy ending. However, it wasn’t a 100% solution. Most of the time, I was only able to cum after he performed oral sex. A majority of our relationship, I never climax from anal penetration. The issue was still there. It was just lessened.
It wasn’t as big an issue with San Francisco because we were an entire country apart. When I was physically with him out in San Francisco, I had no issue. When we Skyped, it took slightly longer, but eventually I climaxed. After San Francisco, I slept with a handful of guys. I specifically remember it being an issue with The Trainer. I know it’s not an issue of physical attraction, because he had a body like a god! However, I had to finish myself off that time, and it took some time.
When I was dating N, it took a long time, but I almost always finished. He started noticing my “condition” as time went on. We discussed it lightly, but I think he was under the impression it just took me a little longer than most guys to finish. As I’ve said before, I had to resort to my “spank bank.” Many times, what I was imagining involved the two of us. I wasn’t even imagining porn stars. It was the two of us in different scenario/locations other than in my bed.
Over the summer, it wasn’t really and issue for me. I had no strong connection to the guys I was sleeping with. It was purely recreation and my own need to get some crazy out of my system. I had no pressure or image to keep up. I was just having fun, and it worked.
The first time Smiles and I had sex, I bottomed. No matter who I have been with, I have never finished from bottoming. It has its pleasures, but it never had that effect on me — Hence my status as a preferred top. With Smiles, there was one time when I was very close during oral sex. I was right there, but I just couldn’t close that final gap. After we had sex other times, and I still didn’t finish, I began to morph my theory.
I have a very high pain threshold. Because of this, I wonder if I am in turn cursed with a high pleasure threshold. Maybe it takes more to get me off. I also wondered if my stimulation comes from something more visual. Maybe I need to witness the penetration to climax. Again, these are all just shots in the dark, no pun intended, but I want nothing more than to figure out this enigma. However, I haven’t been able to test my theory at this point.
Smiles expressed his interest early on to work with me to figure this out. It meant a great deal to hear him verbalize this to me. I need someone who can be understanding and patient with me if I’m going to lick this thing.
After I talked to Boston, after a drunk night at the bar, I discussed in length with D my issue. This was really tough for me because I am so embarrassed by the situation. It makes me feel like less of a man. He was helpful in our discussion and helped me feel more comfortable talking about it.
I also called to Broadway. I didn’t exactly feel comfortable talking to him about the details of my new relationship, nor did I think it was fair to him. But, he had experience with this issue. He knew what was going on with me, and maybe now that we weren’t together, he could help me find the key. When I told him I was being denied sex, he immediately said, “Something’s wrong! That’s not normal. You need to talk to him about it.” Everyone was telling me what I already knew, but not what I wanted to hear. In thinking I was partially responsible for the situation, I brought up my issue. Maybe he was avoiding sex with me because I couldn’t finish.
Broadway told me I needed to stop being so stupid about it. I was stressing myself out over it, and that wasn’t going to solve anything. I needed to acknowledge to myself the issue and go see someone about it. I told him I had been entertaining the idea of going to see a therapist, but it takes a very special type of therapist for such a sensitive issue. It wasn’t exactly the easiest thing to find in the yellowpages. He again just indicated I needed to talk to someone about it if I wanted to get over it. He also reminded me I needed to talk to Smiles directly about why we weren’t having sex more often.
The next morning when I woke, I sent Smiles a message detailing my desire for him to be in the bed next to me and how horny I was. He responded positively and seemed he would have been up for morning sex had he actually been there. I was surprised considering a few hours earlier I was denied.
We made plans for Sunday, and I went on with my pondering my issue for the rest of the day. Did he think I didn’t enjoy sex? That certainly isn’t the case. Even if I don’t finish, I still thoroughly enjoy sex and still get a body high from it. Did it bruise his ego to know I wasn’t being fully stimulated by him? I can assure him, it is me, not him. There were a million questions, but no solid answers.
One thing is clear. I need help. I cannot solve this problem on my own, but maybe talking about it with my therapist, Dr. WordPress, will help me face my demons head on and conquer them. Only time will tell…Follow @onegayatatime
Skype with Massachusetts Mainlander
Posted by One Gay at a Time in Gay Dating on October 21, 2011
Since I left the island of Martha’s Vineyard, not a day went by I didn’t talk to the Massachusetts Mainlander.
Every day, we either texted or talked on the phone. One of us would text the other to say good morning, and throughout the day, we’d call each other to talk on the phone.
I liked chatting with him. I wasn’t sure where things would go between us. We live six hours apart. I tried the long-distance relationship thing with San Francisco, and we could have made it work — He just wasn’t completely compatible with me. I always have my doubts about long-distance relationships, especially with me, but I was willing to give this a shot if nothing else was coming my way. I’m the kind of guy who needs someone present. I like coming home to a man or going to a movie or laying together on the couch. Distance is not something I welcome with open arms.
I never met The Principal, so that threw in a whole other element. Face-time was important to me. If I couldn’t be with him physically, I needed the next best thing – Skype.
It wasn’t easy to convince him to come on Skype. It took a lot of arm twisting. When we started, I could tell he was very self-conscious. He was constantly adjusting and fixing himself. He wouldn’t even speak on Skype. He insisted on typing and blamed it on his roommate being home. I kept telling him to relax. “It’s just me,” I told him. Afterall, we developed quite a bond over the phone over the past couple weeks.
Our conversation was pretty standard (abridged of course), but would need to build to grow into a full relationship:
P: I’m all warm and horny now. LOL
Me: Haha. Oh really?
P: Def. LOL It’s this really cute guy in front of me.
Me: You look so snuggly right now. Like I could nestle in the armpit and watch TV with you. The real thing would be so much better, but this will do for now 😉
P: Pizza with roomie coming soon.
Me: I’m making pizza tonight from scratch.
P: When you cooking for me?
Me: As soon as you come stay with me for a weekend 🙂
P: All weekend?
Me: Yes. You come straight from work Friday and leave Sunday afternoon, so you can get home and relax before work on Monday. We can snuggle all weekend. Maybe I’ll show you New York for 5 min, and then, we’ll come right back here.
P: LOL You’ll hate me after that weekend.
Me: Why do you say that? You know it’s not true!
P: Too much of me. LOL
Me: No such thing! What… You’d come down for the day!? THAT’S DEF NOT ENOUGH TIME TO SPEND WITH YOU!
We were both laying it on pretty thick. Maybe I was getting a little carried away, but I really did like him. He seemed like a great guy. Had he lived in the same state, I’m sure we’d have been on many dates by then.
Me: See my room?
P: I dont konw what to do with you!
Me: My big bed…
P: It looks really comfortable.
Me: There’s a whole side with your name on it.
P: You are so awesome!
Me: You are too!!
P: Think about you alot… Potential of where to take this…. Never thought it would come to this level you know?
Me: I know. You’re quite the skeptic.
P: Well, I mean it was Grindr.
Me: Grindr is just the medium. The vessel.
P: I know but… Just mesh with you.
Me: You get out of it what you put into it. Doesn’t matter where you meet someone. Still think you should have hopped on the ferry and had dinner and drinks with me.
P: That time is done though.
Me: I know. I konw. So, now you should hop in the car. and have dinner with me. 🙂
P: That’s a long drive for dinner. LOL
Me: Dinner doesn’t end at the restaurant.
I also really enjoyed flirting with him. He responded very well to it, and I could tell he was very attracted to me. I was curious if he talked to anyone else about me. I didn’t broadcast to my friends I was talking to someone in upstate Massachusettes, but I did discuss it with my roommate.
Me: Have you mentioned me to ur roommate at all? Told my roommate about you. She comes home from work… “How’s Steve?”
P: I haven’t talked to anyone about you.
P: Def. takes it to another level — Seeing you and conversation. I want to feel close to you, smell you, nuzzle… I’ve only been with 3-4 guys (full intercourse), and I def def want to be connected with you bad.
Me: I love the way you describe it — Makes it romantic, sensual, passionate. I want to toss you down on my bed and treat you right!
P: I want to be tossed. 😉
The pillow talk died down a bit, and we talked more about relationship desires.
P: I want to rub you.
Me: A shoulder rub from my sexy man when I get home from work, and he tells me all about his day.
P: And, the back of your head.
Then the conversation took a turn I wasn’t thrilled with.
P: You need a great guy close to you.
Me: First, we figure out us.
P: You’re incredible.
Me: Then, we figure out the distance. Can’t let that be an obstacle.
P: Not what I meant.
Me: I need you close to me.
P: You should be dating someone close to you.
Me: STOP TRYING TO PUSH ME AWAY!
P: I want you to be happy.
Me: I really dont like when you do this!
P: K. I’ll stop.
After that short detour, we got back on track:
P: Obviously I want you for me. I’ve been wrecked by you. Not even into talking to guys right now. You fulfill so much already. OMG — You are killing me. We touch base all day every day…
Me: I want you to be my man!
P: Care about you… This.
Me: You’re adorable. I just want to hug you all night.
P: Def could get lost in those arms.
Me: This could all be yours!!! For the low low price of a car ride 😛 I don’t want to pressure you though.
P: It would be the prize of the century.
P: I just feel really good with you.
Me: And, I with you.
P: And, the sexual is like beyond crazy. LOL I can’t imagine the chemistry.
Me: We can do this again soon. Now that you enjoy it.
P: K… I really like you! 😉 Bye.
The Principal was a really great guy. I really liked him. He didn’t know it, but he was also providing me an invaluable service. He was distracting me from Smiles. I have a tendency to dive in full force, even when I barely know a guy. The Principal was giving me an outlet for this so I didn’t scare off Smiles. I wasn’t exactly using him. I did enjoy conversing with him, and I really did think he was a great guy. But, only time would tell if this relationship had two legs to stand on…Follow @onegayatatime
Breaking San Francisco’s Heart
Posted by One Gay at a Time in Gay Dating on June 14, 2011
After San Francisco’s visit, I realized we were not compatible. He had quite a few skeletons in his closet. And, it wasn’t the skeletons that bothered me most. What bothered me most was the feeling he was hiding all these secrets. So many past relationships with such a diverse crowd of men much older than I, drug use, some cross-dressing, etc. We come from different worlds, on top of the fact that he lived on the other side of the country.
After playing it cool for a week, I decided to end it, or at least find a way to morph it into a friendship. I spent the week being slightly less available to his phone calls, instant messages, etc. I was doing all the cowardly things I preach against. If I were a real man, I would have told him while he was still in New York, before he went home. Apparently, I need to grow a pair before I tell everyone else to.
Furthermore, I decided to clue him in on my feelings with a text message. I’m such a coward. I wasn’t about to “break up” with him over text, but I couldn’t bring myself to pick up the phone and say it all out loud. Pretending like everything was okay was really getting to me. I don’t do the charades very well. Especially after spending 26 years in the closet. Life’s too short to pretend anymore. So, I sent the following textwhile walking through the mall with my friend:
Hey. I think we need to talk about things. I had a really great time with you out there and when you came to visit, but I just don’t think I’m cut out for the distance thing. I ended my last relationship because I never got to see him, and it appears I’ve gotten myself into the same situation… It’s really been wearing on me over the past few weeks. You are the biggest sweetheat I’ve ever met! You deserve someone you can be with… I have no regrets and hope that you will still want to be a part of my life as a very special friend I cherish forever… I hope you understand!
I didn’t tell him it was because of all of the hidden facets of his life I discovered when he came to visit. I didn’t think it was necessary. The distance thing had already gotten to me before he even stepped foot on a plane. That was the root of the issue. The others were just what made me step into action on ending whatever it is we had.
He responded, I felt like something was up. Can you talk now?
I replied back, I figured you would… I can’t now… Out with friends, but we can talk later…
He took the opportunity to respond with his feelings and sentiments:
I understand. I always say people come into our lives for a reason… You have taught me how good it feels to love regardless of age, distance, and future. Love knows nothing, except how happy one can be. I took a chance to open my heart and have no regrets. Boo, I know distance did not change how happy you made me every time I was with you, texting, skyping or just thinking of you. We both deserve someone to be with, and I hope you find somoene who will always cherish every minute with you as much as I did. A hui ho, 😉 (Hawaiin for until we meet again).
I told him he is the sweetest man I have ever met in my life and apologized if I hurt him. To which he responded, You have a piece of my heart, and I have a piece of yours, so we will always be connected. And will cherish your friendship. Let’s talk later.
We did speak later on the phone. He understood where I was coming from, and he agreed on many points.
We still talk to each other periodically. For a while, it was still uncomfortable because he sent me messages telling me he missed me. Now, he’ll message me to ask what I have planned for the weekend or to ask how my day’s going. We’ve talked about dates we’ve gone on with other people as well. Recently, he had to find a new roommate. Turns out the new roommate’s name is the same as mine, which is not very common. I guess it’s safe to say I’ve officially been replaced.
We will forever be friends, and I do cherish his friendship. And, maybe, one day our paths will cross again…
Making It Work
Posted by One Gay at a Time in Gay Dating on May 31, 2011
When I got home from my business trip San Francisco, I was still reeling from my time with the man I met there. I couldn’t stop thinking about him and how close we grew in a matter of hours. From the moment I touched down in New Jersey, we were texting or talking on the phone. I couldn’t get enough of him.
I knew in my head it was crazy. We were on completely opposite coasts of the U.S. — Three time zones away. Him, a 34 year-old from Hawaii, and me, a 27 year-old from Pennsylvania. There were so many reasons why anything between us wouldn’t work.
But, at the time, I had no love interests in my life. There were a few adam4adam.com guys I talked to and set up dates (4 set up in 4 days), but who knew if the connections would be so strong. Subsequently, I compared every date to my first date with San Francisco.
I decided to send him flowers that Monday. I never sent anyone flowers before, let alone a man. But, I was a stranger visiting a city I’d never been to before, and he welcomed me in with open arms… and then some.
When the florist delivered them to his office, coworkers saw and flocked to his office to ask who they were from. He read the card that said, “I left a piece of my heart in San Francisco. Take care of it until I get back.” One of his coworkers wandered in and said, “Wow! Big night this weekend?”
San Francisco replied, “You actually met him. He’s the guy from the bar on Wednesday.” His coworker was impressed.
He called immediately to thank me. I could hear his smile in his voice as we spoke on the phone. He was so happy, and I was so happy he was getting all the attention of his coworkers. It was my main goal to make him the center of attention and realize how loved he was.
We talked every night since I left. He would call when he finished work, and we would talk for hours. That night, after telling him how much I missed him, I told him I wanted to try to make it work. I couldn’t believe how strong our connection was, and I had to at least put in the effort to know if this relationship had two legs to stand on. I think he was touched, and fully dove in head first with me on the venture.
Over the next few nights, I taught him how to skype. We could now see each other as we talked. Eventually, we began watching TV together. Since we shared such a connection over Brothers & Sisters, every Monday night, we would watch that week’s episode together. Anything we could do to make it a stronger relationship. We became Facebook friends, and I also taught him about gchat, so we could talk at work throughout the day. I got a text every morning saying, “Good morning.” And however we ended the day, I would get a, “Sweet dreams.”
We were both happy. The distance was a burden, but we were managing.
We started planning a trip for him to come visit New York. He lived here for 10 years. He had a lot of friends here he hadn’t seen in three years. In my head, he would come visit in May, and come June, I would trek out there again, this time for pleasure. If these trips worked out, there was no stopping us. But we would cross those bridges as they came.
I didn’t know what this was. We put no label on it. But I knew he made me happy. That was all that mattered to me. And, I couldn’t wait for his arrival!
Florida Fun, The Sequel
Posted by One Gay at a Time in Gay Dating on May 16, 2011
If you’re just joining us, read Friday’s post before continuing…
The next morning, after only 3 hours of sleep, I woke and ran a few miles with D. I gave him the full debrief of what happened after he went to bed. He was very happy I was enjoying the new freedom I was allowing myself.
We got back and relaxed by the pool a bit. I texted Boston asking his plans for the day. He was heading to the beach after grabbing breakfast. Since the girls ate while D and I ran, we joined Boston and his friend for breakfast at The Hotel Breakwater. It was very casual and not awkward, however, I was fighting the beginning of a nasty hangover. Still I soldiered on. We discussed dinner the night before and all the stories that were swapped. Boston’s friend gave us all a new term to use referring to gays. “Pickle.” It was already part of my vernacular and fully utilized during my morning run and the remainder of my Florida trip.
We strolled down to the beach and met up with the girls. I hoped to get a minute to talk to Boston. I felt we should discuss the night before because I didn’t want things to get awkward. I was very attracted to him but also valued his friendship. We never got to chat exclusively. We did, however, have a very candid group conversation with D and his girlfriend about sexual encounters, oral sex, semen, etc. I haven’t laughed that hard in a long time. I love how comfortable and open my friends are — like a breath of fresh air.
When we had to get on the road down to The Keys, we decided to take Boston and his friend to La Sandwicherie on our way out of town. His friend loved us. She asked, “Ok guys. Where’s our next vacation gonna be?”
Finally, the time came to say goodbye. We dropped them off near the hotel, and the best I got was a handshake reaching from the front seat to the back. I wanted at least a hug, but it would have been a full spectacle to get out of the car and do so.
I spent the next three and a half hours in a car with nothing to look at but wide open water. Of course, I texted with Boston the whole time. I was trying to be flirtatious without being overt. It seemed to be working… to an extent. I was having the conversation I wanted to have in person over text. Probably not the best solution.
Once we settled in at The Bahama House in Key West, D and his girlfriend went to the rehearsal dinner of a friend’s wedding. K and I were on our own for dinner. Halfway through, she scolded me to stop texting Boston. I obliged, but was in the middle of expressing to him my relationship with Broadway was over: It was just inconvenient timing to end it before my trip. He was worried that he was the catalyst. I reassured him I was having problems well before I met him, and he knew that.
We met up with the wedding party following dinner. Apparently I wasn’t the only ‘mo associated with this wedding. Everyone told me I needed to meet this great guy. Word to the wise. Not all gay men are compatible just because they are attracted men. While everyone told me we needed to meet, no one actually took the time to introduce us. This is partly my fault because I insisted I get more lubricated before I speak to him, but once I was relatively tipsy, no one made the effort.
The next night D and his girlfriend went to the wedding. K and I found a spot for dinner. At this point I curbed my texting to Boston. D’s girlfriend started texting me about the ‘mo at the wedding. She told me he was anxious to meet and we should meet them when it was over and all go out. When we arrived, he and I were finally introduced. It couldn’t have been more awkward. After a few minutes, he excused himself to go chat with friends. I have to admit, while not interested, my ego was a little bruised.
When the time came to head home, I was trying to coordinate with Boston if we would be traveling along the same route at any point. We were flying out of the same airport and his connection took him through Newark, where I would be landing. I called him to get details and tried to work it out for me to swing by their gate at the airport. Timing never allowed for it.
Days later, Boston and I were skyping. That day, I was psyching myself up to ask him out on a date. I knew it was a dumb idea since we lived in different cities, but I also didn’t see why I shouldn’t give it a shot. After chatting for a bit, he was ready to sign off. My window of opportunity was closing. I asked him if I could take him to dinner sometime. He responded, “Yea. Let me just hop on my private jet.” To which I responded, “There’s no reason why I couldn’t visit Boston some time.”
This was followed by a looonnngggg pause. I could see how uncomfortable the proposition made him. However, he graciously responded, “Sure. I’d be down for that.”
The potential of this was exciting, but certainly more one-sided than I had hoped. After talking with him more, I realized a relationship was never going to happen. At that point, I was able to step back from the situation and realize he was a much better fit for the “friend zone.” I stopped my advances and started talking to him like a true friend, and that’s when I started getting more positive feedback.
When a business trip would land me in Boston, I had the opportunity to make good on my proposition for dinner, but that’s another post for another day.
Finally, Someone Who Knows What They’re Doing!
Posted by One Gay at a Time in Gay Dating on March 2, 2012
So far my trip was turning out to be a flop. I had on traumatic experience and an ex who tried convince me to have sex. I needed my luck to turn around.
Last time I came to San Francisco, tried to meet up with a friend of mine I met a very long time ago on manroulette.com. I’d known him for almost as long as I’d known about the site — roughly two years. We exchanged Skype names and kept in touch. I can remember having conversations with him long ago. He was a great guy who had been through a lot. My heart always went out to him when he told me his story. On top of this, he was incredibly sexy. We’d fooled around on Skype numerous times, and every time I yearned for it to be the real thing with him.
I was hoping I would finally get to live out my fantasy. I made plans with him to grab a drink Thursday night after work. He asked if I’d like to meet in The Castro, but I asked if he wouldn’t mind coming to my neighborhood in the Wharf since I trekked up there the previous night. He agreed, and I asked the concierge for a good spot to grab a drink and chat with someone. He gave me a great spot to check out two blocks away — Parlor. It was perfect. We could easily head back to my hotel room after a few drinks.
While I waited for him to get ready, I excited myself with some porn. I wanted my libido revved when I met him because I wanted to live out my fantasy completely.
When he was nearby, I made my way to the bar. There weren’t many people there. It was perfect. Good music, but quiet enough for us to chat.
When he arrived, he came up to join me at the bar, and we exchanged hugs. I was very happy to see him, and I think he was equally happy to see me.
We sat and talked for hours. He’d been seeing a therapist over the past few months, and he’d really been having some breakthroughs. He has a tough time with his family as they’re not accepting of his lifestyle “choices.” I told him my coming out story, and he was very happy I for me that I had such a supporting family.
Three beers later for each of us, and the conversation was going strong. Our conversation hit the pause button when we both heard someone at the other end of the bar making a gay comment, not in reference to us in the slightest. Our ears perked up ready to be on the offensive but there was no need. When we finished our fourth round, I asked him if he would like to come back to my hotel room. He accepted my invitation, but said he couldn’t stay too long since he had to work early the next day.
He proposed we stop for wine along the way, and I agree. He paid for the wine — He was such a Texas gentleman, even if he hadn’t lived there for years. When we got back to the room, we each finish a large glass of wine before I pounced on him. We made out for a solid fifteen minutes. I was really enjoying him. He had a great body, amazing lips, and he was a spectacular kisser. One of the best I’d ever experienced. My fantasy was on its way to reality.
Warning: The following may be too graphic for some. One by one I peeled off his clothes until he was naked. I took it all in with a big grin on my face. From the first time I laid eyes on his “big swinging d*ck” as I called it, I couldn’t wait to get my hands on it. It was beautiful, and I sure as hell had some fun with it.
He immediately went for mine and started orally pleasing me, front and backside. He was very good, but also very loud, moaning as his head bobbed up and down. This wasn’t something I was used to. I wanted to finish for him. I wanted to show him the fireworks I could set off, but I just couldn’t concentrate. After some time passed, I went to return the favor, but he stopped me. He told me he had to go because he had to be at work early the next morning.
I was so disappointed. He was really good in bed, and I needed that. I also had been looking forward to that for years now. But, I completely understood. Around midnight, he got dressed to head home. As he was leaving, he told me how great I tasted and how he wasn’t going to wash his hands or face for days. This was very dirty and very sexy. I’d never had anyone respond to my body that way before. He kept coming back for more as he made his way to the door. I could tell he didn’t want to leave, which made me happy. I was also purposely teasing him with my body, as I lay naked on the bed. I didn’t want him to go, but I still had one more night in San Francisco, which means I had one more chance to take him to bed…Follow @onegayatatime
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