Posts Tagged gay sex
The Grindr Fill-In
Posted by One Gay at a Time in Gay Dating on May 26, 2011
TuesGAY late night cocktails…
Single life was looking less scary every day. I accomplished 2 dates in 2 nights. I was on a hot streak (at least for me). So far, one was a incompatible, and the compatibility of the other would be determined on a second date.
On Tuesday of that week, I planned to meet a guy who lives in Weehawken. We met on adam4adam.com, exchanged AIM screennames and had been chatting online for weeks. It seemed we were never able to set a date and time that worked for both of us. When I finally got his number, it was a lot easier to plan a date. The night before, we texted and decided to meet in Hoboken after work for drinks, a bite to eat or coffee, depending on how we felt at the time. We both work in the city, but since he had a meeting in Philly, we agreed to meet on the Jersey side of the Hudson.
Midday, I texted him to confirm our plans for the evening. However, that text was met with silence. I didn’t hear back from him until 5:30 when he told me he was in a meeting all day that ran over. He and his coworker were going to hang out until rush hour died down before heading home. By the time he got home, it was about 9:00 and he was beat. He asked to reschedule. I obliged.
At the same time I wasn’t hearing a response to my text, I was cruising Grindr. I happened to find a guy on there who lived in Hoboken and started chatting him up. Through our discussion, we realized we live a block apart. He asked if I wanted to grab a drink after work. I told him I was planning to meet a “friend,” but it was looking bleak. I asked if I could give him an answer later that evening. So, when Weehawken cancelled on me, I brought in the guy from Grindr as a backup.
Don’t get me wrong, I’m not usually some big whore. I was totally new to this. I had a fear of this dating game and needed to face it head on. The only way I saw it getting any easier was by meeting a lot of guys.
So we met at a bar near our apartments (the same restaurant/bar I went to for Sunday brunch for a date). I arrived before him and grabbed two seats at the end of the bar. The second he walked into the bar, I predicted we would not be compatible. I’m not completely shallow, but you can generally tell pretty early on.
I wasn’t ruling him out by any means. I was going in with an open mind, but it wasn’t looking promising.
We began to chat about work and what we each did. The conversation wasn’t exactly flowing naturally. We talked about what we liked to do for fun. Both of us play tennis, so we talked for some time about that. As the date went on, my assumptions were confirmed. He was far too feminine for me, and we didn’t share a whole lot in common.
At this point, it’s 11:00 on a Tuesday. I asked him if he wanted to head out. We finished our drinks and I closed my tab.
We walked home to the intersection where we would head in opposite directions and said goodbye with a hug and a “European” kiss on the cheek.
When I got home, I received a text from him. “Nice meeting you tonight.”
To which I politely responded, “Likewise.”
I figured we were on the same page. We weren’t entirely compatible. I was wrong. He responded, “Maybe we can hang again?! You are funny and cute!”
I’m not sure what made me lose my nerve with this guy. He was very nice, but you should be honest with everyone. I guess I figured he wasn’t the type to hound me if I never got back to him, so I responded, “Yea, we could do that sometime.” I had no plans of ever hanging out with him again.
Needless to say, we have yet to see or hear from each other since.
Round 2
Posted by One Gay at a Time in Gay Dating on May 25, 2011
MonGAY night happy hour…
After my first failed a4a date, I was a little leary. However, I was also excited, because if I could deal with that awkward situation with such poise, I felt I could deal with whatever else was thrown at me.
I’d been talking to “HR” for quite a while. We started on a4a, and quickly exchanged numbers. We texted periodically and tried to set up a date, but it always seemed to conflict with one of our schedules. He was out of town on business, but when he came back I’d have to go away.
One Saturday, he went up to Providence to see Sara Bareilles in concert, and we texted for the majority of the day. By the time he was on the train coming home, we finally set up a date for the following Monday. I suggested Arriba Arriba for margaritas, and he quickly agreed, and we set a time.
I got there before him, so I carefully selected a two-top facing the door in the corner of the restaurant for privacy. When he came through the door, he found me immediately. After apologizing profusely for being late, and for bringing his briefcase and laundry with him (since he was doing so much business traveling), we dug into a bowl of guacamole and frozen margaritas.
The conversation began awkwardly, but we quickly became much more comfortable with each other. We talked about work for a bit, and then moved the discussion to stories from adam4adam.com and Grindr. He had his horror stories, and I was beginning to build up quite the portfolio of outlandish responses from men.
In the middle of the date, I really started sizing him up. He was a really nice guy, and he definitely had a very stable and successful job in human resources. I was also intrigued by his musical background. I never really felt strong chemistry, but he was worthy of getting to know better. We had some good laughs and continued the conversation for three hours. By then end of the date, I was staring at his lips while he spoke wondering what they felt like. I couldn’t wait to experience them with at least a goodnight kiss. Finally, I asked if he wanted to get out of there. He was heading uptown, and I was walking down to Port Authority to catch a late bus home. We said our goodbyes a block from the restaurant.
Goodbyes have always been my biggest weakness. I’m terrible at making the first move. I didn’t know how well the date went. I wasn’t sure if he was interested or just polite. So when the time came, we hugged, and I awkwardly said, “I’ll be in touch.” He looked at me puzzled, and I immediately realized what I did. I recovered quickly by saying, “Yea… I’ll have my people contact your people.” We had a quick laugh, and he hopped in a cab.
While walking to the bus, I decided to text him. “So I’m going to break dating 101 rules since that’s my style and text you right now, but I had a great time tonight!”
Coincidently, he texted me at the very same moment, “It was seriously so great to meet you! In the spirit of being honest, I found you to be incredibly sexy and attractive but was trying to behave.”
Immediately, a wave of disappointment ran across my body. Why can’t I ever muster the nerve to go in for the kiss? The only reason I was able to plant one on Boston in Miami was because I was properly lubricated. So, I immediately responded with a text, “Next time lay one on me.. I get a bit shy… Only regret of the night was not kissing you goodnight…”
To which he responded, “Please. I’m about to turn this cab around and come to port authority. Now I know for next time (and there better be a next time).”
But that’s another post for another day…
Let the Games Begin!
Posted by One Gay at a Time in Gay Dating on May 24, 2011
The next series of posts inspired me to start this blog: It’s where the name One Gay at a Time comes from.
SunGAY morning brunch…
The foot surgeon and I connected on adam4adam.com. He was one of the first guys I chatted with.
After exchanging messages on a4a for a some time, it was evident that we shared many common interests and values. So, we exchanged phone numbers.
Immediately the texting began. He texted me all hours of the day in heavy spurts. Instead of gathering his thoughts and sending one text, I would get 5 rapid fires in a row. I was enjoying the attention. It was great! I just broke up with Broadway a few weeks prior and Boston was in another state and less responsive to my advances than I would have hoped.
Timing with the surgeon was very tough. He wanted to meet for dinner or drinks early on. I wanted to play the field a bit more. I just started on a4a and was getting A LOT of responses. Many were creepy old dudes, but a lot of them were “quality leads.” For the time being, I prioritized working out and trivia with friends over dates with him. I needed to get in shape since I was now living the single life.
He intrigued me because of his profession and playful personality, but he wasn’t exactly a local. My last relationship ended because of lack of time and commitment. I wasn’t about to dive right in to something with a surgeon…
Between him going home to Illinois for a week and me traveling to San Francisco for work, we were able to finally set up a brunch date near my apartment. He arrived before me and was seated in the large dining room in the back of the restaurant. No one else was around. This made me happy because I didn’t want to be a public spectacle.
Much to my surprise, I wasn’t nervous at all. I had nothing to lose since I wasn’t all that into him; no big letdown.
About 5 minutes into the date, I realized this guy would not be a repeat offender. We had a decent conversation for an hour about our families’ dynamics over breakfast. The conversation was never forced, but there was never really any chemistry there. And, while not ugly, I was not attracted to him in the slightest. He definitely looked better in his pictures.
I decided I had enough. I asked if he wanted to get out of there. We walked back to his car (passing 2 guys holding hands — a first for me in Hoboken!). He walked right up to the driver’s door and opened it as if he was about to get in. I was happy about this because it saved me the awkward “ass-out” hug. I said thanks for meeting me and have a nice day, and I walked home.
Two blocks later, I got a text describing how nice it was to meet me. I responded, “Likewise.” Then, he asked if we could do it again.
This is when I finally grew a pair and realized I had enough confidence for the first time in my life. I responded, “You’re a nice guy, but I just don’t think we have chemistry.”
He texted back thanking me for my honesty and wishing me good luck.
On to the next guy!
Leaving My Heart in San Francisco
Posted by One Gay at a Time in Gay Dating on May 20, 2011
With my new found freedom, I was hitting the town. I met a guy on adam4adam who was interested in meeting that night, so we exchanged numbers. That Friday, while out at the bar, we managed to find each other and chat a bit. After getting thoroughly inebriated, I got in a cab and went home with him. He was NOT attractive (and would later find out very poorly endowed), but I had nothing better going on. And I was drunk. We didn’t do much more than heavy petting, but when I woke up the next morning naked in his bed, I was hustled out the door. I wasn’t planning to ever call him again, so I was fine with the early wake-up call. Irony struck when walked outside and realized I was exiting my sister’s building.
That Monday, I traveled to San Francisco for work. Grindr in hand, I planned to meet a few attractive, like-minded guys. At dinner, I started searching. Nothing turned up.
The next day, when work was slow, I managed to find a cute guy. I messaged him and told him, “Hey dude. Very sexy smile.” He responded positively. We agreed to grab drinks following work. I had no idea where he was, or what he did, but, I had nothing to lose. I knew only 1 guy out there, and I couldn’t get ahold of him.
When work ended at 4:30, I sent him a message. He wasn’t done work until 8ish. I decided to go exploring. After stumbling upon Lombard Street’s winding road, I remembered the Palace of Fine Arts is in San Francisco. I googled the address. 1.9 miles away. I had nothing but time, so I began to walk.
After snapping some great shots at The Palace, I happened upon the base of the Golden Gate Bridge. It was sunset, so I took the opportunity to snap some more quality pictures.
When I started walking back to my hotel, I got a text from Mr. San Francisco. I looked at the distance, and it was cut down to feet. Apparently, I wandered into his neighborhood.
It was a little awkward when we first met. He wasn’t quite what I expected. He was a tiny little Asian man (which I would later find out to be Hawaiian), but still that great sexy smile. We walked down the street, coming across the gym he runs and his coworker outside eating his dinner.
We found a bar to settle into, and by chance, one of the girls I graduated college with happened to be there. I walked over to say hi. Since I didn’t feel like telling her I was gay on the spot, I never introduced Mr. San Francisco.
We sat at the bar and began talking. When the conversation turned to TV, we really clicked. We both watch Brothers and Sisters and really bonded over the show. He started placing his hand on my leg periodically. I found it extremely disarming and welcomed it every time. After all, this was pretty much the 2nd time I went on a date with a man.
After a few rounds of drinks, we decided to grab dinner. But, not before we took the opportunity to steal a few kisses on the street corner. Dinner was great and the night only got better as it progressed. I was having a great time! We paid the check, walked out into the street and took another opportunity to show how much we were enjoying each other’s company.
He looked at me and said, “What now?” In my head, I was thinking how easy it would be to go to my hotel room. Isn’t that what they’re for? Instead, he asked what time I had to be at work in the morning. We worked out the logistics. He asked me to come back to his place for the night, and we hopped in a cab.
When we arrived at his apartment in The Mission, he took me up to the roof. The make-out session continued. His roof had amazing views of the entire city. When he unzipped my pants and started giving me a blowjob, I was in absolute ecstasy.
We then went down to his bedroom to continue our passionate session. He was so tender and his eyes were gentle and inviting. I felt so comfortable with him. I was a stranger in a strange land, but I felt right at home.
When I woke in the morning, he made me coffee, and we snuggled on the couch watching a little TV before heading to work. I didn’t want this to end, but I had no choice. Work was beckoning.
When I arrived back at my hotel, I stood in front of my bed and laughed. It was still pristinely made. The maid must have been confused when she entered the room, questioning where I slept.
I wouldn’t get to see Mr. San Francisco again until 2 nights later. I traveled to San Jose for a meeting, but came back for one night. I arrived back at the Hilton San Francisco Union Square. I took my laptop down to the Urban Tavern to do some work, grab an appetizer and wait for Mr. San Francisco to arrive. We shared a lovely meal, some delicious desert and hurried up to my room to finish with more desert.
From the bed to the shower, we fully enjoyed one another’s company. So much, that I swapped my ticket for a later flight at quite a pricetag. When we woke in the morning, we exchanged full contact information so we could stay in touch. I was headed to the airport, but not before dropping him at work. We savored every last minute together in the car until we hat to say goodbye.
I was very solemn the remainder of the ride to the airport. I stared out the widow aimlessly, feeling empty. We continued to exchange texts the entire time, joking about turning around or coming to the gate to stop me.
It was a very short timeframe, but we clicked immediately and we clicked hard. I knew this was a bad idea, getting attached to someone an entire continent away. But, I figured I had to give it a chance. I had nothing else on the horizon. We would give it a shot and see what happens…
The Office ‘Mo
Posted by One Gay at a Time in Gay Dating on May 19, 2011
When I myself accepted my homosexuality and came out to many of my friends, I decided I wasn’t going to come out at work. Much like my reasoning for not telling my extended family, I decided it wasn’t relevant to my work-life. Rarely does the topic of significant others arise in my department. When it does, I am probably thought of as the ambiguous bachelor.
I’m quite close with my coworkers. One of them described our department best when she said, “I love our dorm-room work environment.” Very few subjects are taboo. It’s like working in a Seinfeld episode. On the contrary, my boss is a born-again Christian. I’m not too sure how accepting of my lifestyle he would be. I’ve never given him the chance to prove me wrong, but like I said, it is not relevant.
While I was dating Broadway, it became necessary for me to tell coworkers I was in a relationship. Like my friends originally, I led them to believe I was dating a woman. I explained it as a no-strings-attached relationship to compensate for never bringing “her” around or talking about her.
After a while, I got to the point of needing to tell one of them. The lying was geting to me. On top of that, I spend 8+ hours a day there. I needed to talk about it. It’s my nature.
I have been working with my current officemate for 3+ years (at 2 different companies). She is very outspoken and lacks the filter many of us were born with (this also happens to be the reason why I love her). Many times, she said to me, “You better not turn out to be gay, or I’m going to have a lot of explaining and apologizing to do.” The first time hearing this, I asked her to elaborate. She told me it was because many of my coworkers have asked her about my sexual orientation, and she told them flat out I was straight.
While most times I appreciate her frankness, this got under my skin. I didn’t appreciate my sexuality being the topic of any conversation. So when I finally came out to a coworker, it wasn’t her.
Over the year I worked at my current company, I came to know and trust one of my coworkers. I saw how professional she dealt with her job and how she was able to compartmentalize. I knew if I confided in her, she would be a lock box. I just prayed the key wasn’t an array of mini liquor bottles like Elaine on Seinfeld. She also had a gay roommate, so I knew she would be accepting of my sexuality.
When I finally felt comfortable telling her, I messaged her on AIM. She sat 10 feet away from me, and I’m surprised she didn’t get whiplash from turning her head so fast. She became my confidant, and over time, I felt comfortable telling my office mate as well. But that didn’t stop me from explaining to her why it took me so long to tell her.
I feel that many of my other coworkers either know or suspect I’m gay. That means they’re either clueless, or they have enough respect for me not to ask. And I’m fine with that arrangement. It’s none of their business quite frankly.
I question every day whether I should tell them or not. I trust them, but I also feel the more people I tell at work, the faster it spreads. I’m afraid people may judge me or look at me differently, and I’m not ready for that. I don’t plan to stay at this company forever. Maybe when I change jobs and start fresh, I will feel comfortable being my whole self with my coworkers, with no reservations.
Single, Sexy and Free
Posted by One Gay at a Time in Gay Dating on May 18, 2011
Want to start with a special thank you shout out to Angels of Sodom, a great blog by gay student at the University of Pittsburgh. Thanks for getting the word out to your readers to visit my blog.
Check out his blog. He has some amazing coming out stories posted there. Look for mine, coming soon…
On with the show…
For the first time in my life, I was a single gay man. I had the freedom to date or have sex with whomever I wanted. But first I needed to get back to me.
Of course this meant hitting the gym big time. Coming off the winter, I was quite out of shape. I immediately began running, swimming and lifting regularly. Within a short period of time, I got my body back to something that I could feel comfortable standing naked in a room with another human being.
But there was a big problem. How was I going to meet other gay men. I hated the gay scene, and I had 1 gay friend (who is all but married – car, apt and dog with boyfriend). With no local spot and no wingman, I was on my own. So, I turned to the internet.
Casually sitting on the couch one night, I searched to find gay dating sites. Originally, I found DList.com, but that turned up no results. After sorting through a pile of trashy hook-up sites, I came across adam4adam.com. I made an account and began to check out the guys. Within no time, I realized I would never attract anyone without an attractive profile. So, I pulled back and started writing honestly about what I was looking for and added a conservative headless picture.
Easy going guy looking for more than hookups
27, 6’2″, 195lb, Swimmer’s Build, Brown Hair, Smooth Body, White
Looking for Friendship, Relationship.
Relatively new to gay world… Contrary to my picture, I’m not a whore…
Love my friends & hanging out. Active lifestyle. Travel, hit up bars, play tons of sports, go the beach, etc. Basically anything that keeps me active & holds my attention.
Work in advertising in NYC & travel a bit. When not working I stay fit.
Into masculine dudes who like to stay fit, but aren’t completely obsessed w/ their body.
If I sound interesting to you, hit me up. Always up for meeting new people!
Swimming — Lifting — Volleyball — Tennis — Running — Watching TV/Movies — Amazing Cook
HIV Neg 4.12.11
After surfing the site, I noticed a trend. Of course there were pictures of dick all over the place, but you learn to look past and ignore them. Overall, the profile pictures skewed more overtly sexual. I realized I needed to spice it up a little. Once I changed my picture to something sexier (an extended version of the picture attached to this blog) the hits started flowing in. It was a great boost to my self-esteem. I’ve never thought of myself a particularly sexy, but I was being told otherwise.
After talking to a few guys, I began building up a roster. My goal was always to move the conversation from a4a to something more permanent, i.e. a phone number or chat screen name. I started to line up dates with these guys, but got to a point where I was overwhelmed. I didn’t have enough time between staying in shape, work and life in general to schedule them in. But I was having fun. I was really enjoying dating. So much so, I’m sure my friends were so sick of hearing me talk about it.
Right in the middle of trying to juggle dates and managing to keep the conversation going with a few guys, the time came for me to go on a business trip to San Francisco. I would be there for a week and wanted to see if I could meet some guys while visiting. I heard about an app for you phone called Grindr. It locates other gay men within the vicinity of you who also use Grindr. Basically it’s gaydar.
Until then, I resisted downloading the app. But, as the cabin door was closing and my plane was pushing back from the terminal, I downloaded it. San Francisco’s gay community would be a whole lot easier to navigate when the plane touched down…
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.
Freedom in Florida
Posted by One Gay at a Time in Gay Dating on May 13, 2011
Before ever stepping on a plane to Florida, I told the friends I would be traveling with I was giving myself a hall pass. If Broadway went to Barcelona alone, possibly with a bottle of lube, then I was going to Florida with some new found freedom.
I didn’t break up with him prior to my trip. If you recall from my previous post, he wasn’t my “boyfriend” either. I never heard the phase “I love you” pass his lips. We had been dating for almost 10 months, but I no longer had any indication this was destined for the long term.
I have never been single and gay. I met Broadway, and shortly after, I came out. I needed to give myself the freedom to date. I needed to explore and experience. Is this healthy for a relationship? Was I setting myself up to cheat on the man I was dating for the previous 10 months? Maybe. But was it something I needed to do? Yes. Yes, it was.
Before heading to South Beach, Miami, Boston and I discussed meeting up. When my friend K and I arrived, we checked into Essex House and went down to the beach. I noticed a guy who vaguely resembled Boston. I pointed him out to K, and she said, “Ooooo. Go for it! He’s hot!” But when he walked down to the water with a female companion, the chemistry between them seemed more than just friends. Their body language suggested they were dating. Furthermore, this guy was wearing what I would later come to describe as “straight shorts.”
It wasn’t until I overheard their conversation as they were leaving the beach that I realized it was him. We were texting each other from 10 feet away for over 2 hours and didn’t even realize it.
Later that evening, K and I walked over to the sister hotel for happy hour. The other 2 in our party would be arriving any minute, but we were anxious to start drinking. I texted Boston and told him that if he could find us, I would buy him a drink. He was staying at this sister hotel, The Clevelander. After spotting us, he joined in our happy hour pitchers. Over the course of the next couple of hours, I drank about 4 pitchers. I was truly cutting loose.
Before this trip, I had no plans of attempting anything with Boston. He was just a solid friend. We were going to meet up for a drink or two, but after K made the comment on the beach, the possibility of more was planted in my head.
When my 2 other friends arrived, we discussed dinner plans at The Royal at The Raleigh and extended an invitation to Boston and his friend.
At dinner, I made a bit of a fool of myself. I had quite a bit to drink. When we finished eating, we walked back to the Clevelander for a night cap.
At the bar, I bought a round of beers. Boston tapped the top of my bottle to make it overflow. The only problem was I didn’t have a strong grip on my beer and it shattered on the floor. Minutes later, I retaliated, only to have the same thing repeat again.
After a short while, Boston’s friend went off to bed, shortly followed by my 3 friends. Boston and I were still sitting at the bar chatting when some guy came along interrupting us talking about real estate. Boston turned to me and told me to get rid of him. This was a window of opportunity. I was drunk and Boston is hot. I started getting a bit physical with him, rubbing his leg and petting his neck so the guy would leave. Finally, he got the hint and took off.
After my third trip to the bathroom, I asked him if he wanted to go for a walk. We strolled along the beach and found a comfortable spot to chat. We talked about careers and futures for some time before the authorities chased us. We moved our discussion to a wall at the edge of the sand. At one point, we were both just awkwardly staring at the ocean when I turned and kissed him. He immediately responded, and we proceeded to make out for what could have been a half hour. People passed by making cat calls, but we continued as if no one was there.
Things started to get hot. My hands were up his shirt feeling the chest I admired on the beach earlier that day. Finally, I put my hands down his pants and felt how much he was enjoying it. And he did the same. Me being 6’2″ and him being no taller than 5’6″, I picked him up and leaned back against the wall so I didn’t have to hunch over anymore. I was really enjoying myself. He was a great kisser and the wandering hands on both parties was rather pleasing. At one point, he pulled back and said, “But you have a boyfriend.” This didn’t stop me from going back in. Between kisses, I was able to utter, “He’s not my boyfriend, remember?” He was torn about the issue. He was obviously enjoying himself, but he didn’t want to get in the middle of a relationship.
After a while, I asked if he wanted to go somewhere more private. He pointed out we were both sharing rooms. I noticed the uneasiness on his face. I responded back, “I’m not trying to have sex with you. I’m not that easy. I just don’t want to stand here making out in public…” At this point, I could see his level of comfortability dropped significantly, so we went back to our separate rooms. I sent him a text explaining my enjoyment and my respect for him.
Stay tuned. The remainder of the trip will have to wait ’til Monday’s post.
Broadway Goes to Barcelona
Posted by One Gay at a Time in Gay Dating on May 11, 2011
Broadway is a huge fan of Kylie Minogue. In fact, that’s an understatement. Shortly after we started seeing each other he reintroduced me to her when he gave me her latest album. While a fan of a few of her songs, I would never venture to one of her concerts.
However, Broadway bought a ticket to see her in concert in Barcelona, Spain. Yes, Barcelona for a concert. He told me about this trip months in advace, but the closer to his departure, the odder I found this excursion. On top of that, we were drifting apart over the weeks leading up to this trip.
Over President’s Day weekend, we ventured to Rhinebeck, NY to stay at the Belvedere Mansion bed and breakfast. We needed to get away from the city bustle. But, for the first time in our relationship, we started getting snippy towards each other. While driving there, we argued about dinner plans. At dinner we didn’t talk much. It was almost awkward. The next day we went for lunch at Gigi Trattoria (amazing pizzas btw). He spent the entire meal taking pictures of me and other things in the restaurant and playing on his iPhone.
When we got back to the room that night, we opened the champagne and strawberries I brought in an attempt to be romantic. I was ill shortly before this trip and wasn’t quite over it, so I was having a hard time feeling romantic. We had our fill and went to bed, arguing about the sheets being tucked or untucked. He made no advances that night. I would have been a sport and tried to ignore my ailment, but the effort wasn’t necessary.
Looking back, I think that night is when I knew it was ending.
The clear sign came in mid-March while he was in Barcelona. The day he was flying out, we spent the morning together. While shopping at Bed Bath & Beyond, he purchased 2 small bottles of lube. We had used this during sex, but I found it strange he would be buying 2 the day before heading to another country… alone.
Before he left, I barely got a kiss from him. We chatted at lunch about the difficulty we would have being an ocean away but knew we would figure it out. And we said goodbye.
When I didn’t get a call from him before he took off, red flags started popping up in my head. I started talking to Boston online about my issues. He pointed out that I was raising a lot more red flags than mere coincidence. But when I received the following message on Facebook, I was livid:
– B
The following is our exchange on Facebook:
— Got your message yesterday. Have to say I was a little disappointed. Felt a bit like a mass message… Especially after not hearing from you since I said goodbye on the street Friday afternoon. (This was on Monday) I don’t doubt it’s tough without a phone. But I was also surprised not to get a call/text from the airport before taking off.
— I don’t know what to say
— Just think it’s a little odd when you’ve been dating someone for almost 10 months not to reach out before you’re about to leave the country for a week by yourself… and then when you finally do 2 days later, it’s just a rundown of what you’ve been doing followed by, “hope you are well.” Not sure if im being melodramatic, but i’m a little hurt to be honest… The content of your message was sterile.
— Yes I understand and maybe Facebook wasn’t the best way to contact you, but I wanted to let you know I was alright. I didn’t mean for it to be, but now that i look at it again you are right. I don’t know what else to say here…
We talked some more, I was very hurt and upset. It wasn’t that he messaged me on Facebook. It was what the message said. We were dating for almost 10 months, and it appeared that meant nothing to him.
I didn’t decide to break up with him immediately following our exchange. I wasn’t about to break up with someone across an ocean, especially when he was traveling alone. It just didn’t seem fair. But we certainly needed to have a discussion upon his return.
The only problem was, the week following Barcelona I was headed to Miami and the Florida Keys for almost a week. The discussion would have to wait…
Handing in My Gay V-Card
Posted by One Gay at a Time in Gay Dating on May 2, 2011
I struggled with covering this topic so early in my blogging, but it fit in the timeline now. While I never get deep into specifics, if you are uncomfortable with the topic, I suggest you stop reading further through this post…
Something that always scared me was losing my gay virginity!
I mean, I’ve seen penetration in porn more times than I can count. Still doesn’t mean I had any clue what to expect. I was also never one to play around the back door — Never really an area of thrill for me, so it remained neglected. You also hear stories of girls popping their cherries and the pain they felt — I had a feeling that it would be similar for a guy.
I can’t recall how far into the relationship we were when penetration finally occurred. A little over a month maybe.
We decided to spend a night at my place. It wasn’t planned or anything we discussed specifically ahead of time. It just sprung from the passion of the moment. He took charge since this was my first time and obviously not his.
He was a very good candidate to take my V-card. Well hung, but not something that scared the sh*t out of me.
I tried to just relax. I have to say, it went much smoother than I expected. No searing pain. An interesting feeling having your prostate poked for the first time, I must say. This is where the pleasure stemmed — not the actual insertion itself. It certainly wasn’t my favorite part of sex (I love foreplay most) but still enjoyable. I felt closer to him than ever before. The care in his eyes made me feel at ease.
The next morning, we flipped, and he let me have my way with him. Big weekend for me! Two firsts in a matter of hours… I definitely enjoyed this more than receiving. While this became the typical horizontal arrangement, we shared all aspects of sex with each other over time.
At the ripe age of 26, I came to a life changing conclusion. I'm GAY!
It took me 26 years to realize this and come to terms with it, but coming out's been the best decision of my life.
This blog is about my dating life in NYC and what happens next...
One Gay at a Time 