Posts Tagged anxious
Where’d He Go?
Posted by One Gay at a Time in Gay Dating on April 16, 2012
FraI already started my morning off with a little frisky visit and some well appreciated service. It was time to join the real festivities.
I walked out into my kitchen to find my roommate with all her college friends and my other roommate with his girlfriend. I thought I pulled a fast one on all of them sneaking my visitor in the back door, but I was wrong. My male roommate saw him come in. He and his girlfriend questioned me on it, and I was completely honest with what happened. They were fascinated by how transactional it was. They couldn’t believe it, and his girl gave me a high-five.
I celebrated myself with a nice cold beer from the fridge. It was already 1:00 and I was well behind the rest of Hoboken. Before I finished my shower, I had four down. That would be enough to scratch the surface.
I got dressed and convinced my roommate and his girlfriend to come with me to a friend’s apartment. She was having her annual St. Patty’s Day bash. I was meeting D and K there as well. I was happy D was going to be in town. Since his car got a flat, he wouldn’t be visiting his girlfriend in Philly.
When I got there, the party was already well underway. I sat on the arm of the couch and conversed with my friends. I just took in the scene. For some reason, I wasn’t really feeling St. Patty’s Day this year like years passed. I didn’t feel the need to get sloppy drunk.
Of course, since my bladder has shrunk since college, I had to go to the bathroom. Since I was somewhat bored at the party, I was chatting with a sexy man I’d been chatting with for some time on Grindr. We’d talked about getting together so many times, but never did. Things were getting very flirtatious and leading toward an afternoon hookup. When I went to the bathroom, he suggested I come over. I took the opportunity to sneak out the door when I finished in the restroom instead of returning to the party. I’m sure it was just a matter of time before my friends realized I’d gone, but it wouldn’t be immediate.
I wasn’t even slightly drunk. I’d been anxious to see this guy for some time. I wasn’t about to let the opportunity pass. I quickly walked home, grabbed my helmet, hopped on my motorcycle and sped off uptown. Before I left the party, my Grindr friend asked me how I felt about glory holes. I told him I’d never used one before. When he sent me a picture of a sheet with a hole cut in it and a caption reading, “How would you feel about this?” I became excited. He told me he’d leave the door unlocked. I was to walk in, come to the sheet, unzip and let him take care of the rest.
Warning: The following may be too graphic for some. As I entered, I noticed how nice his place was. I was a little shocked. I walked straight to the sheet hanging in the bathroom door. I hadn’t even fully unzipped before he reached his hand around the sheet and began. It felt amazing! He continued for some time before I reached my hand around the sheet and began to stroke the back of his head. I could feel him, but I couldn’t see him. Finally, my curiosity got the best of me, and I just pushed the sheet to the side. I wanted to see him. He was very attractive in his pictures and even more so in person. On top of that, the only thing he was wearing was work boots.
After a little more time, he turned around and I began grinding myself against his backside. He was extremely hot and he knew how to use his body. I reached around and used my hand to pleasure him as well. He was VERY gifted. I hadn’t felt one like that since my friend in San Francisco.
He then requested we move things to the couch. I sat down, and he straddled my lap. It didn’t take long before he finished all over my chest and without warning. I had no idea it was coming. I tried to finish as well, but it was no use. Between my morning visit and the few beers I had, I sat there for quite some time without climaxing. He was so hot and he tried everything to help me finish, but it was no use. I gave up and apologized. I could tell he was very disappointed. He blamed the drinking, and I concurred that was to fault.
As he stood in front of me, I took all of him in. He had a spectacular body, and I let him know it. I asked him about his workout routine, and he told me he didn’t since his heart attack. He elaborated and told me it was no big deal, but I was a little worried. I could only think of him keeling over in front of me.
We chatted a little bit more while I got dressed and looked around a bit. He told me he had a roommate, but he wasn’t home. Something didn’t quite line up, but for some reason, I was buying the story. While we chatted, he stood in front of me in just his boots with his large gifts swinging back and forth. He was very proud of them as well. He put sweatpants on so he could walk the dog, and I could see his large bulge. I commented on it, and he commented how he loved how people would check it out, especially the guys with their girlfriends. I was so turned on. I also learned he managed a bar in the city, and he told me I should hit it up sometime.
We talked about meeting up again sometime soon. We both thought the other was thoroughly sexy and wanted a repeat. He was particularly looking for a sequel since he didn’t get a happy ending from our first encounter.
I said goodbye and made my way back downtown to my apartment…
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Posted by One Gay at a Time in Gay Dating on April 13, 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…
Periodically I get slightly outlandish requests from men on Grindr. Some want to pay me to suck on my toes and lick my feet. Some are looking for very kinky things. Some just want to give a bl*wjob. To be honest, this was never something I have ever craved giving. It’s part of my bedroom repertoire, but it’s never something I’m just really itching to do without getting some reciprocation. This isn’t always the case with Grindr, adam4adam and ManHunt men.
On the night before St. Patty’s day in Hoboken, I received a bunch of Grindr messages from a guy who’d been asking to come over and give me a bl*wjob before work on numerous occasions. I was laying in bed watching TV and saw no harm in a little oral pleasure. As the conversation continued, he went dark, and I went to bed.
As per my usual, the next morning, I woke up horny. I had multiple messages from “The Milkman.” I conversed with him on the subject for a little bit. He apologized for dozing off the night before and never coming over. He seriously wanted to make it up to me. “I’ll make up for last night. I swear! You won’t regret it. I’m that good!” He was at his apartment waiting for his friends to wake up. They spent the night in anticipation of the local holiday. I told him I was still in bed and was horny. He immediately offered to come over and service me, but he wouldn’t be able to do it until 12:30. By then, my roommate would have my apartment filled with her friends. That would prove to be a logistical nightmare to sneak him in. Not that I need to sneak him in, but I don’t need a bunch of fresh college grad girls running their mouths about me.
He continued to push me to figure out a way to make it happen. “You can drink a beer while I do it,” he added. He had to wait until 12:30 because that was when his group was heading to the bar. He would double back and come over to my place. I explained the party and told him I’d have to sneak him in the back door. He seemed to be game with the plan. I questioned what I’d have to do for him, and he immediately told me nothing. He just really wanted to service me. He wasn’t the best looking guy, but he wasn’t ugly either. I was okay with the situation as long as I didn’t have to service him.
We started getting graphic, but also discussed safety. We didn’t really know each other. We didn’t want to do anything too risky. I was all riled up and having a hard time not finishing myself off right then and there. I told him to just come over then, but he wouldn’t sneak out on his friends. I was so horny. “I can’t. My girl is here. Wait. You’ll get it.” WHAT!? His girl? Guess he had a girlfriend. That was none of my business. If he wasn’t doing it with me, it’d be some other guy. It was obvious we weren’t going to form a relationship out of this, so it was no skin off my back. I did question him on it, and he explained it was a terminal relationship. It was already on life-support. He told me not to touch myself. “Think about baseball or grandmas,” he added. With that, I went and took a shower to pass the time before his arrival.
When he got to the door, he texted. I buzzed him in and he climbed the back staircase. It took a few attempts and close calls before I opened the door and he came straight into my bedroom and closed the door. When I told him a girl just walked past the door, he responded, “This is crazy bro.” Everyone was finally in the kitchen, and I assumed I pulled it off.
We chatted a bit about our previous conversation and our plans for the day while we shared a beer. He seemed like a reasonable guy. Very down-to-earth and realistic. He wasn’t the most fit guy, but he was a fun character. He was also very anxious to get my pants off.
Warning: The following may be too graphic for some. I sat on the bed, and he pulled my shorts down. He was very pleased with what he saw, and he went to town. I took the opportunity to use my hands to fondle him through his pants. He quickly became aroused, which further increased my arousal. He continued for some time before I moved up on the bed. He came around my side, and I undid his pants so I could really feel him. It didn’t take much longer before I was on the edge of climax. He back his head away and began to use his hand while I finished in quite a fountain show. I think we both loved every second of it. He really was as good as he made himself out to be.
While I toweled off, I asked him about his girlfriend. He told me he was ready to dump her. He also mentioned many of his friends already knew he was gay. I wasn’t fully buying any of his stories. They all seemed just a little too convenient.
The conversation then turned on me. He told me how good-looking I was. He enjoyed my strong features. I complain about my nose quite often and am seriously considering getting it fixed. When I mentioned this, he heavily protested. “You have a very strong Roman nose. Don’t change a thing about it,” he protested. I told him that was the nicest way anyone has ever described my big nose before. We both laughed. “No. But really. It’s great. That and your strong chin. You’re a very handsome man,” he added. I was blushing.
Shortly after, we snuck him back out the door when the coast was clear. Five minutes later, I received a text from him: “Thanks! You’re a pretty rad guy!… And stop picking on that face. You’re a f#ckin’ knockout!” This was the first time anyone had ever thanked me for them giving me a bl*wjob. I replied, “If anyone should be saying thank you, it’s me.” He told me any time I wanted him to come over, he’d be all over it. “I’d love to have a regular thing where I swing by in the morning before work a few times a week,” he said. He really was like the milkman.
I polished off my beer and walked out to the kitchen. I wasn’t as sneaky as I thought. My male roommate and his girlfriend noticed him come in. They didn’t care and didn’t judge me. When I told them the full story, they actually gave me a high-five. I walked to the fridge and grabbed another beer. I had a long day of drinking in front of me…
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Late Night Snack
Posted by One Gay at a Time in Gay Dating on April 3, 2012
After my tryst with the Armenian and the Asian, I decided to order some real dinner. This was the last night I was on the company dollar, so I ordered some room service. While I waited, I chatted with the guy who wanted to come by later in the night. I sat and ate my meal in bed with just the TV to keep me company. I was feeling lonely, which is such a strange emotional state to be in considering I’d just shared one of the most intimate acts with two other men.
When midnight arrived, I started texting my late night snack. I asked him what he thought his E.T.A. would be. He told me it was still up the air, but he was definitely coming by. He was out with friends and would swing by on his way home.
Finally, around 2:00am, he texted he was finding parking and would be by shortly. Ten minutes later, I had a knock at the door, for the third time in a matter of hours.
He was a very nice polite black man who was anxious to spend some time with me. He seemed very young and innocent. We chatted a bit while sitting on the bed before any action began. It was getting late, and as rude as this sounds, I was ready to get it in and go to bed. I wanted a nightcap so I could doze off soundly till the morning.
Warning: The following may be too graphic for some. We had A LOT of foreplay and prep before anything happened. He really wanted to cuddle for a long time before we could even get frisky. I was almost ready to call it quits and ask him to leave. It was getting late, and I was getting tired.
There was a lot of kissing. A lot of heavy petting. A lot of licking and sucking. Finally, he was ready and got into position for me to penetrate him. I could tell this wasn’t a guy who gave it up to just anyone. Normally, I’m really into the foreplay and making out, but I’d already had my engine warmed up earlier that evening. In fact, the car had been taken around the block a few times.
I’d saved my climax for him and quickly learned this was a big mistake. He was very bad. We didn’t go for very long because I really wasn’t getting anything out of it. Finally, I stopped and rolled onto my back. I tossed yet another condom in the trash and started taking care of myself. He laid next to me and asked me to finish on his chest. I obliged his request, and he followed suit shortly after.
I knew he was going to be a lingerer. I tried to cut that off at the pass. I humored him for a short bit of time before I finally spoke up and said how I needed to get to bed. It was past 3:00am. It was time for him to go! He got the hint and got dressed. While he did so, he asked if we could hang out again while I was in town. He told me how much he enjoyed himself. I didn’t shoot him down, but I didn’t exactly give him the answer he was looking for. I told him I’d have to see what my schedule allowed for. I told him I was trying to get the most out of my vacation in L.A.
With that, I said goodbye, shut the door, showered all the men of the night away, and climbed into bed to dream about the sunny sandy beach I would be visiting the following day.
Follow @onegayatatimeMy Adult Book Report
Posted by One Gay at a Time in Gay News on March 21, 2012
Warning: The following may be too graphic for some. It is of a sexual nature. Proceed with caution!
A few months ago, the fine folks at Tickle Kitty approached me. It seems bestselling author and sex educator, Dr. Sadie Allison published her fifth book, Tickle My Tush: Mild-to-Wild Analplay Adventures for Everybooty. They offered to send me her latest paperback that helps men and women learn the true pleasures of the under-explored “seat of love” for review on my blog.
I enthusiastically accepted the offer, and anxiously awaited its arrival in the mail. I wasn’t entirely sure what I was getting myself into, but how bad could it be? I’m gay. If I had an aversion to anal play, I’d be a very lonely man the rest of my life. Maybe I could learn a thing or two from the book as well.
I wasn’t the only one anxiously awaiting my new book. My roommates were also waiting with bated breath to see what the book was all about. When it finally arrived, we all passed it around paging though to see what exciting new tips we could learn. After we’d all had our fun like immature high school students in the locker room, I took the book back and began reading it.
Tickle My Tush is a light-hearted fun look at anal sex for mainly heterosexual couples, however, a homosexual man can learn a lot from this book. Dr. Sadie covers a lot of material in this quick read — The 14 chapters of this book cover everything from safety and heinie hygiene to toys, strap-ons, and positions of pleasure. And, Dr. Sadie takes a light-hearted approach by using playful language instead of some complicated medical jargon no one understands or uses.
This book does a wonderful job removing the stigma from anal play/sex. I can think back to when I was first experimenting with homosexuality, I wanted nothing to do with anal play. I watched it in porn, and it really just seemed like something I didn’t need. I could think of many other things I could do to satisfy my sexual urges. It was something I saw as overwhelming and uncomfortable. Frankly, I was scared of it. If you find yourself in that position, reading this book will answer a lot of the questions and will clear up a lot of the misconceptions you may have.
What I really like about this book is that it pushes straight men to open their minds and their bottoms to the idea of anal play with their female sex partners. I enjoy sex, and even as a “top,” I enjoy many of the pleasures my bottom has to offer. Having your prostate stimulated for the first time is a mind-altering experience. Many straight men don’t realize the potential their bottoms have for pleasure. I would hope books like these remove the stigma and open their minds to anal play. This book also removes the stigma for women to explore. It takes away the idea that enjoying anal sex makes you dirty or a slut. It’s simply exploring all the pleasures you body has to offer.
As you read, the book certainly gets more adventurous. It starts with safety, hygiene, anatomy and the basics and moves through finger, oral, genital, toy and strap-on pleasures.
One of my favorite chapters is 6: Sensual Booty Massage. It has always been something I’ve enjoyed. “As an often overlooked erogenous zone, those two cheeks are always eager for sensual arousal from kneading, squeezing, kissing, licking, spanking, gentle biting, father-light touching — or simply calming moments of warm-handed stillness. Why stop at the cheeks? Lustily arousing the hips, waist, small of the back, inner thighs and A-spot can add thrilling new dimensions to your lovemaking.” Some are tried and true methods I’ve been using forever, and some are a few new methods I’m dying to try.
Some of Dr. Sadie’s advise is spot on! One of my favorite parts of the book acknowledge the problem I have relaxing during sex. It’s the root of my inability to climax at times. Her best advice — UN-focus.
This book is a great read for the anal play beginner. I can think back to the guy who inserted himself with great force inside me with no preparation whatsoever. I ran out of the room in pain. I can think of the virgin who allowed me to penetrate him for the first time and how scared he was until he learned how much he loved being penetrated. I’ve been with a few newbies in my days, and there is a lot they can learn from this book. On top of it all, the illustrations that ensue are purely erotic. I think they are my favorite part of the book!
There are a few things in the book I disagree with on some level. For instance. in regard to the question, “Do you really need an enema before anal sex?” Dr. Sadie says no. But, after a few of my own horrific experiences, I HIGHLY RECOMMEND IT.
Overall, I must say, I didn’t learn a whole lot from this book I didn’t already know. That is because the first guy I slept with was a very good teacher, and I have a curious mind that has been satiated by experimentation. But, not everyone is as lucky as I am. If I had this book from the start, it certainly would have made for many less awkward situations. The thing I most learned from the book was anatomy. In fact, I often refer back to it to make sure I am giving my man the most pleasure I am capable of.
Dr. Sadie does an excellent job giving you the basic tools you need to be confident, succeed in anal play in the bedroom and know you can enjoy the untapped pleasures your bottom holds. She gives you invaluable tips that help get you in tune with your partner. She answers a lot of the embarrassing/uncomfortable things that may arise with anal play so that when you encounter them in the bedroom, you can proceed past them without the interrupting the fun. So buy it — Read it — And for heaven’s sake, try out all the new things you learn with someone you feel truly comfortable with. You’d be surprised what exciting new experiences you can unlock.
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Posted by One Gay at a Time in Gay Dating on February 21, 2012
My relationship with Smiles had come to a close. We met. We discussed. I guess you could say we had closure.
I’d already moved on to other men and began rebuilding my roster. It’d been a while since I was in the game, and I was a little intimidated. Over the three months I dated Smiles I lost my edge. It was my sister who pointed out to me, “I didn’t like you with him. You weren’t yourself. You were much more reserved around him.” I didn’t like the sound of that. I pride myself on being open and myself all the time. Apparently, I lost that somewhere along the way. I needed to find it again.
I would do so with the help of my therapist, Boston. I really lucked out in my timing. Boston was on a break from his final year of school, which meant his services were available. I was going to take full advantage. He was a good friend, and I missed him. I was really disappointed we didn’t get to meet up when he came to visit New York for New Years. It really made me look forward to the day when he graduates, and I convince he to come to New York or Hoboken so I can have him around more often.
Monday night when I got home from work, I called Boston. I wanted to give him an update on how everything with Smiles went since we’d been chatting about it a bit. I told him how everything ended and how I was moving on.
Ironically enough, Boston had a few tales of his own. Apparently, a little of me was rubbing off on him. I was very happy to hear this news. Sometimes I think he puts his love life on the back burner too much. I think he loses hope at times and engulfs himself in other ventures. I want to see him happy. He’s a great guy and he deserves this.
So, when he told me about a straight friend of a friend coming to visit and the sub sequential hookup that ensued, I was downright proud. He managed to attract a “straight” man enough that this man took the opportunity to make out in the bathroom of a club.
I was so happy to have my friend back. I loved swapping stories with him!
I also took the time to explain to him how LES wouldn’t talk to me. For the life of me, I couldn’t figure out what I could have done to him to make him stop talking to me all of a sudden. We were building a strong friendship. I had the feeling he developed feelings for me, especially since he asked me, “So what’s the deal with [Smiles]?” He invited me to his birthday, and I missed it. I apologized, and he told me it was okay. I invited him to my holiday party, but he dropped off the face of the earth and never showed. Following, I attempted to reach out to him on numerous occasions. Okay, so maybe I’m under exaggerating. I tried to text or call almost every day for a while there. I thought I was being funny, but now looking back, I could easily see my actions being misconstrued. Maybe he thought I had stalker tendancies.
In the end, things got very suspicious. He would never respond to my Facebook messages, and he never showed up as online. However, he never unfriended me. As long as that didn’t happen, I didn’t think he was all the annoyed by me. I sent him another long apologetic message on Facebook asking him to please reach out to me. When I finished writing it, I thought I’d give him a call to see if I could get through. It’d been about a month since I last texted or called. When I did, I was shocked to find out the number was no longer in service. He either blocked my number or changed his.
I couldn’t believe it. Had I really taken it that far. Maybe he wasn’t mad at me. Maybe he was afraid of me. I hung up the phone and immediately sent another Facebook message: “I’m sorry if I’ve been bothering you. Don’t worry. It won’t happen anymore.” I was mortified. Did he really think I was that insane, or was he really that mad at me. I was really hurt that someone would ever be that mad or upset with me that they’d simply cut me off. My ego was seriously bruised.I also happened to be perusing my old messages on OKCupid, and it told me LES deleted his account. When I made a new OKCupid account shedding an identity I’d used since college, I came to realize he was still on there and had an updated and active account. He’d blocked me on there as well. He really wanted nothing to do with me, and there was nothing I could do about it.
“You can be a bit aggressive,” Boston told me. That really resonated with me. I did tend to be agressive. I’m a tenacious man. When I see something I want, I don’t give up until I attain it — This goes for everything.
The interesting part was that I simply wanted a good friend back. He was a really fun guy to be around, and I wanted to introduce him to Boston. I thought they’d make a GREAT pair. I would have loved to see the two of them together. But, I don’t think that will ever happen. New York is a big city, and I don’t know that we’ll ever cross paths again.
Boston and I talked more over the course of the week. We almost had a nightly check in for a while there. We’d chat on the phone for about an hour about our dating lives and the mistakes I made with Smiles. He told me more stories about another guy he was helping to introduce to the gay world. I hope I’m not blowing up Boston’s spot, but once again I was proud of him. He was facing new challenges and having new experiences. I was happy to see my friend experiencing more of life these days. I understood how busy school made him, but at least he was taking advantage of his time off.
I was building my roster and had a friend to gossip about all the new things going on in my life. Things were getting better, but I still wasn’t happy to be back out in the dating pool. I was anxious to land another man, but this time around, I wasn’t going to just settle for a guy who was willing to date me. I needed to “find a man who will worship you like you worship him,” as my friend A so eloquently put it. I needed a real man, not another little boy. A man who could express himself verbally, emotionally and physically. I was going to find a triple threat, and once again I had one of my closest friends in my corner.
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Posted by One Gay at a Time in Gay Dating on February 16, 2012
Since deciding to end things with Smiles, I’d already been on one date and had one hookup. I certainly hit the ground running. I felt slightly guilty all this was going on before we even had the chance to formally end things, but then again, things never really formally began between us.
I wasn’t wasting any time either. I had been talking to a really nice guy on adam4adam.com and set up a date to grab drinks with him after work Friday evening. It was a bit awkward because this was truly a blind date.
He had two pictures on a4a, but neither was clear and one didn’t include a face. When I asked him to send me a better face picture, he told me he didn’t like taking pictures of himself. Of course a red flag raised in my mind, but I had nothing to lose either. If I arrived and the guy was unacceptable, I was right next to the Port Authority bus terminal. I would be home in no time with little of my time wasted.
We agreed to grab drinks at Arriba Arriba in Hell’s Kitchen. It was conveniently located between his apartment and my office, and like I said, it wasn’t far from my transportation hub to go home.
As I left my office and began walking north, I was quite nervous. I’d never been on a true blind date before. I’d at least seen pictures of their faces, but this time I had no idea what he looked like. I joked with him, “Not gonna lie. Not sure what you look like… Haha.” It didn’t take him to respond: “Sorry mate. Don’t like taking pictures of myself. We will find each other… haha. You can ask me to leave once you see me and how ugly I am. Lol.” I didn’t care all that much at this point for the picture. I was already going in blind. I replied, “No apologies needed. Just tellin’ ya you’re gonna have to find me…”
I waited for him on the street corner. I put that time in a good location to good use. I surfed Grindr in HK for any new prospects. I know some may say that is classless considering I was waiting for a date, but I’m not in HK all that often anymore, and there is more talent in that neighborhood than where I work. He finally arrived and approached me. I asked how his trek to HK was, and we went inside to find a table.
When we learned we could only stand at the bar since we weren’t ordering food, we decided to go elsewhere. I was at a bit of a loss because I hadn’t been in the neighborhood for some time. I didn’t know of a good place for us to go for a drink. Luckily, this guy was good on his feet. He suggested Eatery, and we were off.
We grabbed a seat at the bar and ordered a few rounds of drinks. We chatted for a long time about a myriad of things. The whole time, he kept his ball-cap on. Beyond the fact that he should know it’s bad manners, especially since he was an older gentleman, I was also worried there may be no hair under there. I’m not shallow, and looks are not everything to me. But, if he was balding without shaving his head, I wasn’t sure I could deal with that. (Smiles shaved his head and I was obviously okay with that).
We talked about our upbringings. He lived a bicoastal lifestyle, living in California and South Carolina. He also was shipped off to boarding school in Switzerland, where his grandparents lived. I grew up on a farm and went to public school. We had quite the education/socio-economic divide before. This is one thing I‘m not sure I am capable of getting past. I’m sure if it was the right guy, I could handle him coming from wealth, but it’s something that makes me quite uneasy. He came from money, and a lot of it.
I also learned he leads a very lavish lifestyle. He told me about his plans to purchase a house in Barcelona. He’d recently traveled there to scope out some places. He also told me about the $200,000.00 loan he gave a friend and was never paid back because the friend died and left his only possession, his apartment, to someone else. He told me about his lavish trips to the Caribbean islands recently. The list goes on.
Ironically enough, he wasn’t talking about all these because he was trying to impress me (Or at least it didn’t come off that way, which is fine). It simply came up in conversation or I coaxed them out with questions. I just felt uncomfortable with our socio-economic differences. I don’t really aspire to the position of kept man. I want someone who will share the financial burdens with me equally. I know a lot of people would love to find someone rich to marry, but money means very little to me when it comes to love. I think like I would constantly feel like less of a man if I had everything provided for me constantly, and I contributed far less to the relationship. Maybe this is something I will learn to get over in time, but for now, it makes me uneasy.
I learned how he continued to build his wealth and his professional relationship with a family in Canada. He told me about all the businesses he was involved in, and I started to worry he was another Smiles — Too much on his plate to commit to a real relationship. I also learned he wasn’t out to many people in his life, even after he’d been in a nine-year relationship with a man who left his wife for him. It ended when the man cheated on him while he was away on business. I wasn’t sure how I felt about him still being in the closet. He’d experienced too much and was far too old to still be in denial of his true self. I wasn’t sure I wanted a “project” at that age.
Drinks quickly turned into dinner. We stayed at the bar and made friends with the waitress. She was super sweet and very interested in chatting with us. Over our meal, we conversed more, and I learned we share a lot of the same morals and interests. We had similar outlooks in life.
He also became much more physical as the night progressed. He constantly had his hand on my leg rubbing my thighs and caressing the back of my knee. I started to do the same. Periodically, he would stand and give me a big ol’ bear hug. It was sweet. I liked knowing he was a passionate physical man. I needed that after Smiles constant distance.
Six hours later, we were ready to leave the bar. He decided to walk me to the bus. I thought when we exited the restaurant we’d exchange a kiss and go our separate ways. He was a true gentleman and walked me to the Port Authority. Not only that, but he walked me to my gate to wait for my bus and stood there waiting with me. It was midnight, and he was being a total sweetheart. He stood anxiously next to me as if he didn’t know what to do or how to close the date. He wasn’t really out, so I had a feeling a goodnight kiss in front of a large group of strangers was out of the question. When my bus arrived, he said goodbye and we agreed to be in touch.
As I rode home from the date, I wasn’t entirely sure what I thought of him. He became more attractive as the night went on, but I wasn’t sure if that was his personality or the alcohol stepping in for average looks.
I had a lot to think about. It was clear to me he was interested in me. The next day, he texted to see if I was interested in catching a movie that evening. I told him I had plans to hang with friends locally, but if they fell through, I’d let him know. When I decided to keep my plans, I texted him to let him know. He wasn’t all that concerned considering he had hopped on a flight to Boston to hang out with friends and go to a party. Yup, hopped on a flight that day. He obviously didn’t have a planned flight considering he asked me to go to the movies — Unless he was planning to fly me to Boston to do so…
That night, while out with my friends, I called Boston. He told me some of his new exciting war stories, and I told him of my trepidations about Deep Pockets. He told me I was nuts to write him off based on financial differences, so I decided to see where things went over the next week or so.
We texted a few times more, but interest wasn’t strong on either end as the text messages slowly came to an end. I was on to the next prospect…
Follow @onegayatatimeDinner Reunion
Posted by One Gay at a Time in Gay Dating on February 3, 2012
Smiles and I made plans over the Christmas break to share a home-cooked meal my first full night back in town. I was greatly looking forward to it after not seeing him for a week. We’d spent a week apart before, but not over Christmas. Something about it made it tougher for me to get through.
That morning, Smiles sent me a text. He was wishing me luck on my first day back in the office after being away for some time. It was a truly sweet gesture considering how out of character this was for him. Since I left him, he was showering me with attention I didn’t normally receive. I attribute this to our conversation the night before I dropped him at the airport. That was just my assumption, but the only other factor that changed was spending time apart.
Out of the blue, in the middle of the afternoon, he picked up the phone and called me. I’d told him I had to go to the office that week, but there was little chance I would actually be working, so I guess he felt I’d have the free time to chat. It was a very welcomed distraction from my Facebook status perusal and email correspondences.
He called out of boredom. He couldn’t seem to motivate himself to work. He was still in vacation mode from being away. “My head is still at the beach,” he added. I told him there was no need to dive back into everything unless it was urgent. We all have lazy days. Why not ease back into the workload?
Before Christmas, I bought two cashmere hats from Bonobos. Smiles had mentioned interest in similar hats. I bought them just in case we made a last-minute decision to exchange presents. I could ship them back free of charge and Smiles would be none the wiser, but that seemed like a waste. I got a great deal on them considering how much he paid for the last one he purchased, so I decided I was going to ask if he wanted them. It wouldn’t be a gift — I would just be facilitating the deal.
“Are you still interested in cashmere hats, and what is your price point?” I asked. He told me anything under $80 each, which was $20 more than what I paid for them. I decided I was going to show him the hats and come clean about how I came to purchase them. I was worried I would look anxious in his eyes, but since we had our talk about where we were, I decided I needed to start being more of myself. It’s very much like me to do something slightly awkward and come clean about it. I’m very honest when it comes to things like that, shame or no shame. If he didn’t like it, then he didn’t like me.
That night after work, he came over. He texted me as he was getting on the PATH. When I didn’t hear from him for over a half hour, I tried calling and texting. I was getting no response. I wasn’t sure what happened, but I was hoping the meal wouldn’t be overdone waiting for him. Finally, he told me he’d arrived in Hoboken. When he got to my apartment, he told me he’d gotten on the wrong PATH train and ended up in Jersey City. He had to switch over and come back towards Hoboken.
I filled plates for the two of us, and we sat on the couch to eat dinner while we watched TV. Smiles loved the meal. He said it was cooked perfectly and everything was delicious. I was very proud and thrilled with how much he enjoyed it. One thing I love to do is cook for a man, especially when I get such rave reviews.
While we watched TV, my attention was constantly stolen by the reflection of headlights on the windows across the street. He kept asking what I was looking at, and when I told him, he poked fun at my inability to keep my attention fixed. We had a good laugh about it.
Smiles asked if I had any ice cream to finish our meal (you know him and his sweet tooth). I didn’t have any. We had two options. We could venture back out into the cold to pick up a pint, or we could settle for a variety of candy I had stashed in my room. He settled on the candy.
After dinner, we moved things into the bedroom. I was anxious to hop into bed with Smiles, just to feel his body against mine. I didn’t even care if it involved sex. I just wanted to be close to him. But, before we hopped into bed, I decided to bite the bullet on the hats. I explained, and he decided he wanted to keep the gray hat and have me return the black since he already had one. He gave me cash, and the transaction was complete. I was glad I didn’t just send the hats back without consulting him as many of my friends suggested (I have a habit of doing what I want even against my friends’ better judgment).
We laid in bed and exchanged random stories. We discussed how he was healing after his appendectomy. Like I said before, I was going to start being myself, so I told him the ridiculous story about my belly button. For some unknown reason, when I was in college and I got drunk, I would encourage my friends to feel my belly button. I was a swimmer so I had a flat stomach, and when I got drunk, I like the way it felt (maybe the beer pushed it out a bit). I insisted it was incredibly sexy and even took some of my friends’ finger and guided it to my belly button. I also proceeded to tell him about the time my belly button was handpicked as the body shot glass for a bachelorette party when I was in Key West. “ ‘Wow! You have the Grand Canyon of belly buttons!’ one girl shouted,” I told him. He laughed and looked at me like I was from another planet as he examined my belly button.
The rest of the night was more of the same — Lots of cuddling and chatter, but no sex. I was fine with this, as I was just happy to have him in my bed. We both brushed our teeth and climbed under the covers. I was going to bed a happy man that night, and I was looking forward to waking in the morning to a sexy man in bed next to me.
Follow @onegayatatimeBack to Reality
Posted by One Gay at a Time in Gay Dating on February 2, 2012
Christmas day had passed. My time home was coming to an end. I was happy to be home, but I was also anxious to get back to normal life.
The morning after Christmas, my father and I decided to do a little shopping to see if we could land any special deals to kill time. I would also finally be in cell phone service, so I could text Smiles and wish him a safe flight. When I got into service, I got an influx of text and picture messages. He’d sent me quite a few, keeping me updated on what he was up to. I really was missing him and quite anxious to get back to see him. I proposed we do dinner at my apartment since he had to postpone it before the holidays. He texted back in agreement. I was finally going to get to make us the standing rib roast. I told him I missed him, and he responded, “I miss you too! 🙂 “ I could have melted into a puddle right there. This was so unlike him to express his emotions like this, but I was eating it up!
The day after Christmas is always spent with my father’s side of the family. We all gather together for a nice potluck meal that rotates from house to house year to year. This side of the family has also shrunk significantly. My grandparents have been gone since I was quite young. My father’s brother is in rough shape these days from his battles with diabetes. His sister died a few years ago and her husband is in a nursing home. I rarely see their daughter, my cousin since she moved away and got married. That left one sister whose husband also passed away a few years ago. But as that generation was shrinking, another was growing in leaps in bounds. The living sister has 5 children, all of which are married and have become baby making machines. They now outnumber the four of us five to one.
The gathering is always a lively one with many children running about. Christmas is one of the two times I spend with this side of the family each year (the other being an annual family reunion). We also have an annual tradition of a “Yankee gift swap” or “white elephant sale” depending where you come from. The tradition has lost a lot of its allure as my cousins have adopted a new tradition of buying crap at Wal-Mart and Big Lots the day after Christmas for half price.
My sister and I had to work the Tuesday after Christmas, so around 5:00 we hopped in the car and made our way back to Hoboken. When I got back to my apartment and unloaded all my presents from home, I picked up the phone and called Smiles. Sadly, it went straight to voicemail. I was hoping to relax after a long car ride with some time talking to him, but alas, that wouldn’t be the case.
My roommate arrived home, and we swapped all our holiday stories. We plopped down on the couch and started to catch up on the programs we saved on the DVR. After some time, Smiles called. I think if you were in New Jersey when the phone rang, you may have seen a beacon of light in the sky that was my smile.
He told me about his trip home and the ordeal he went through. When he got back to the city, he’d gone out with one of his female friends for dinner. He devised a new plan to work out of her apartment going forward so he would be more productive than he was working out of his apartment. He felt if he had a place to go to every day that wasn’t in line of sight of his bed, he would get more done. I told him I thought it was a great idea. Even though they wouldn’t be coworkers, they could keep each other on task. Either that, or it would be a complete disaster, and they would be a constant distraction for each other.
I told him about my time home, my family and how the gift swap has become a sham. He laughed and told me about the rest of his time home with the family.
It wasn’t a long phone conversation, as our phone calls never are, but it certainly satisfied my hunger for Smiles. It would satiate me until I got to see him the following night when he came over for dinner.
Follow @onegayatatimeTexts From the South
Posted by One Gay at a Time in Gay Dating on January 30, 2012
Smiles was halfway across the country and Christmas was rapidly approaching. There’s something about dating someone over the holidays that makes you really appreciate that person. There’s also something to be said about being single over the holidays that makes me utterly depressed. I was happy to be on the dating side of the fence this year, but I would certainly miss Smiles.
While he was home, he sent me periodic texts out of the blue. I got a few picture messages of him and his mother’s dog on the beach and some pictures from around town. They were sweet simple texts that showed me even though he was many states away, he was still thinking about me throughout his day.
This seemed a bit of a stark contrast to the conversation we had just before he left. He told me he couldn’t be in a serious relationship right now. If that was the case, why was he reaching out to me even when I wasn’t around. I started to wonder if maybe he didn’t know what he wanted.
As he was driving around, he called me to chat. It was a really sweet conversation. He was asking how I was doing and what I’d been up to since everyone left town ahead of me. He was telling me all about where he grew up and his old high school. We talked about his mother a fair amount and her business. He sent me a picture of some of the things she worked on.
I was getting access to mother information. You don’t share that with someone you don’t truly care about. I was getting more of him. It was exactly what I wanted. I wanted to know more about where he came from. I wanted him to open up. I wanted it all.
Maybe my conversation sparked something inside him. Maybe he realized he wasn’t appreciating me as much as he should, but there certainly was a stark difference between the time we spent together before the conversation and the time following.
As the rest of the family was arriving into town, Smiles started getting anxious. This is something he did regularly — Got worked-up over small things. He was texting me about solutions to the problem, such as drinking. I encouraged him to do whatever made him comfortable. There was no reason he couldn’t have a few cocktails to take off the edge if it would make him more relaxed. He was anxious about talking about his career. He was still working hard to get it off the ground, and I think he was ashamed about that. I told him he needed to be proud for being so brave for starting something from the ground floor. Not many people can do that. They just go work for someone who has already done all the heavy lifting. He has very low self-esteem when it comes to his job, and he has no reason to. No one finds overnight success, and I have strived to convey this to him constantly while being very supportive of all his ventures.
I think my pep-talk worked because his texts became more light-hearted and relaxed. Either that, or he took my advice with the cocktails to a much higher level.
The morning my sister and I were driving home to Pennsylvania, he texted just to see how my day was going. Again, I love these sweet gestures that show he’s thinking about me. I was much happier over the past few days than I was immediately following our conversation.
When I got home, I had no cell phone service. It makes it a little more difficult to talk without a little more effort. I made sure he had my parents’ landline number, but I knew he wouldn’t call it. He probably didn’t want to have to talk to anyone if he called and they picked up.
I had his number, but now I was settling in with the family. I wasn’t home for long, so I wanted to make sure the time I was there, I was present. I didn’t want to be running off constantly making phone calls.
It was Christmas Eve, and I was off to mass with my family. I texted him on the way to say hi and let him know I was thinking about him.
When I came back out of mass, I had a response. He told me he dodged the church bullet. I told him I wasn’t so lucky. My parents’ priest is one of the most boring people I have ever encountered. Going to church is penance in itself.
I wished him a Merry Christmas Eve just before driving out of cellphone service. We were on our way home to take our annual family Christmas photo before relaxing for the rest of the night in front of the TV…
Follow @onegayatatimeA Pointless Cancellation
Posted by One Gay at a Time in Gay Dating on January 25, 2012
When Smiles and I spoke on the phone Sunday night on his way home from a party in Connecticut, I asked him to come to my apartment for a special dinner Monday night. He told me he had to work, but he was going to leave early and we’d just eat a little later. I told him this was perfect since it would take some time to cook the roast after work.
I’d told Smiles about my standing rib roast before, and he didn’t quite get what it was. I explained to him the similarity of it what one might be served at a carving station at a wedding reception. He got a clearer picture, but it still wasn’t crystal clear.
I had a rib roast in my freezer with our name on it. I finally had a chance to cook it for us, and he was on-board. I was excited. It was a plan.
Monday morning, before work, I took the roast out of the freezer to thaw for that night. I planned out the accoutrements as well. I was very excited for our romantic night. It’d been a while since we spent time together. I wanted a night of beef, wine, couch, and bed. The thought sounded spectacular to me!
What excited me even more was the idea of my sanity back. I planned to ask Smiles that night where we stood. I didn’t need a title. I didn’t need to be his boyfriend. I just wanted to know where his head was at.
I know I probably sound like a broken record at this point, but that’s what my inner dialogue is. I get fixated on something, and it exhausts me until I get some closure on the issue.
Much to my chagrin, at 1:00 that afternoon, Smiles sent me a text with some bad news. “Looks like I have people coming tonight so I’m not going to be able to sneak out. I don’t think dinner at 11:00 would be the bet. Do you want to have an early dinner here in the city before he show?” Very disappointed, I agreed with a “Sure.”
I was p*ssed. It wasn’t his fault, but I was a little crushed since I was taking so much care to plan out the evening, and it all went to sh*t. He suggested we do it another night, but came up with a consolation prize. He suggested I come over to his apartment for dinner instead before the screening. I begrudgingly agreed to the idea since it’d been so long since I’d seen him, and I sent my roommate a text asking him to put the roast back in the freezer.
When I finished work, I made my way downtown to his apartment. When I arrived, I was shocked to be received with a nice big kiss. Maybe he missed me. Maybe I wasn’t just a seat warmer in this relationship. There was actually emotion behind that kiss. I was happy.
I was a little anxious because I was still planning to ask him where we stood that evening.
He told me he had food in the fridge to make and suggested we cook that instead of going out for dinner. He preferred that since he wasn’t feeling well, and he was exhausted. It made no difference to me. Asking him my question in the privacy of his apartment sounded like such a better idea than in a restaurant anyway.
I ended up cooking the pork chops and asparagus for the two of us since Smiles wasn’t quite himself. We sat and ate — Him at his computer chair working while he ate and me on the couch. Not nearly the romantic meal I planned for the evening. When we finished, I helped him clean up and put the leftovers away. He started getting ready for the rest of his night, and we talked about my plans. He asked if I was planning to spend the night. “Well, I guess the first question I should ask is if you were planning to come to the screening tonight,” he added.
This was the first I was hearing this. I was quite open to the idea, but I told him, “I have nothing for work tomorrow. You were supposed to be coming out to Hoboken, remember.” “Right,” he responded. I reminded him I’d seen the movie twice now, but if he wanted company, I would come with him. I asked if he actually watches the movie, or if he does other things during the film. He told me he usually watches most of it. Things remained unsettled as he made his way over to the couch to take a quick nap on me.
That was my opportunity to ask him my burning question. Every moment I tried to open my mouth, I froze. Nothing would come out. I was suddenly transported back to when I sat on the couch trying to tell my parents I was gay. The anxiety was making my heart pound out of my chest. I tried over and over to ask him, but I couldn’t muster the courage. I’m not sure what I was afraid of, but it was driving me insane.
After a half hour of this, it was time for him to get up. I asked him if he wanted me to sleep over, or did he want to get some rest alone. We made a final decision. It was better he get some uninterrupted rest that night since he was so exhausted as much as I wanted to spend the night with him. He told me, “It’s very sweet of you to offer to see the film again to spend the night with me.” I liked hearing that. He recognized the sacrifice I was willing to make to spend time with him.
With that, I said goodbye, and he made his way to the screening while I made my way to the PATH — Without my answer.
I was so p*ssed at myself for getting so worked up about a stupid question. What was wrong with me?! Obviously, I needed someone to talk to. I tried Boston, my therapist. I needed him to talk me off the ledge and help me make sense of the situation. I couldn’t do it on my own. We talked it over for over a half hour and he convinced me I had no choice but to blatantly ask him where we stood. We even helped me nail down the phrasing.
When I got to the other side of the tunnel in Hoboken, I got a text from Smiles telling me he was on his way home. His friends never showed. My blood was boiling. We cancelled our dinner plans for NOTHING. I still had no closure on where I stood with Smiles. It certainly was going to be a toss-n-turn kinda night…
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 