In a strike of luck, in terms of my desire to turn my dating/sex life around, the timing of a family trip could not have been better planned. My parents, my sister and I were heading to Virginia to visit my aunt, uncle and cousins. The purpose of the trip was to see the cherry blossoms in Washington DC.
It was a fun trip. I got to see my cousins’ girlfriends and their children, many of which for the first time. Even though the cherry blossoms had already fallen due to an early bloom, it was still nice to get away and relax.
While driving back to New Jersey with my sister, I began attempting to line up dates with all the guys I’d been talking to before I left. As far as going on dates, the trip came at a bad time because it put a roadblock in the momentum. I kept up with the texts from the southern boy I’d gone on one date with so far. We were trying to line up a second date, as well as a few first dates with some other men I’d chatted with.
I got back to town on a Monday afternoon and tried to dive right into the dating. One of the guys I’d been chatting with was a doctor I met on Grindr. We exchanged pictures. He was very good-looking, very well-spoken and very charming. His response to my picture was, “Matthew McConaughey party of one?!” I was incredibly flattered, and suggested he consult with an optometrist friend. Although he had some promise, I wasn’t all that excited to meet him. I was going in with an open mind, but the fact that he was a doctor was somewhat of a turnoff. He would have no time for me, and I have come to realize I need someone who will be around and spend time with me.
We texted back and forth to nail down plans. As the workday was ending, I asked him what he wanted to do. He responded, telling me, “I honestly feel like I need a quiet night in. A bit drained here but would definitely like to have you over for drinks and conversation if you are up for that?” It was a bit unconventional, but I told him I was game. He gave me his address, and we set a time at 9:00pm.
I made my way into the city, bottle of red wine in hand, and walked to his apartment. I called Boston, and he shocked me by picking up. I wanted to hear how his birthday went and catch up. He further shocked me with a story involving an on-duty officer and himself that made me so proud. It was nice to hear Boston letting loose.
As I walked up to his apartment, I hung up with Boston. He lived in a very nice building. He answered the door, and we exchanged hugs. He had a gorgeous place. I came in and made myself comfortable on the couch while he opened the bottle. I felt quite overdressed when I noticed him in sweatpants and a t-shirt. I was jealous. I removed my shoes and sat Indian-style on the couch.

He was far more attractive than his pictures. His tight t-shirt showed off his chiseled body, and his face and smile looked very similar to Taye Diggs. I was slightly mesmerized.
It wasn’t long after we began talking that he let his guard down. The flamboyance came bubbling up, and it was really turning me off. I immediately lost my attraction for him. I could see us being friends, but I could never date someone like that.
We sat on opposite ends the couch talking the whole time. I learned about his job and what he does in his free time (which wasn’t much since he didn’t have much of it). He told me his specialty, and that dominated a majority of the conversation from then on out. Ironically, his specialty was relevant to me, and we got on the topic of safe sex and HIV for over and hour. It was incredibly educational on two levels. I learned a few things about HIV transmission and the disease itself, and I learned how little I know about the stuff I was so cavalier about days prior. I thoroughly enjoyed our talk, but I wasn’t attracted to him as a potential man to date. I would, however, love to keep him around as a friend.
It was late, and I needed to go home. He needed to go to bed. He walked me to the door, and I said goodbye with a kiss. He pulled back and made a comment on how he wished he’d only done that sooner. He really liked it and came back in for more. He was a good kisser too. I walked to the PATH and then walked home, and it took me a while to get there.
The next morning I noticed a text from the doc. “Off to sleep here, but just wanted to say thanks for an awesome date! I really had a great time meeting you.” I apologized for my lack of response and told him I was at the allergist to getting poked with various things to find my allergies. We exchanged small talk on the subject, and the conversation fizzled out. That was the last I’ve heard from the good doctor…
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Valentine’s Day had arrived. I managed to find myself single once again. I have yet to celebrate a Valentine’s Day. The one year it came while I was dating Broadway, we couldn’t be together because I got shipped off for work to the Midwest.
I ended my intense weeklong relationship with PR just the night before. I knew it was bad form to stick to our plans to go out for a romantic evening if I was just going to be faking it.
Just because I wasn’t going out for a romantic dinner doesn’t mean I wasn’t looking forward to the company of a man. For some unknown reason, I was exceptionally horny that day. Granted this has become the norm, and I’m starting to wonder if I may have a problem. However, I wasn’t stopping myself from exploring possibilities that day. I was single and ready to mingle.
I was all over Grindr and even pulled up the OKCupid app to see who was around my area. When this produced little results, I began to filter through all my previous Grindr, Adam4dam.com, OKCupid, and Manhunt contacts to see if there maybe something I missed or someone I wanted to revisit.
I messaged a few guys and asked what they were up to. The ones who I hadn’t spoken to in quite a while I asked how they’d been since we last spoke.
One guy hit me up on Grindr. I was pretty horny, so I wasn’t being picky. He was just offering to come over and give me a blowj*b. I at the very least had a fallback. I was really looking to get it in, but I would settle for him if no candidates produced themselves.
I wasn’t happy with who I was becoming. Once again, I was letting myself get out of control. I needed to reign in my sex life, but that day, I just wanted to get it in. Tomorrow is another day.
I started chatting with the guy I’d gone on an awkward date with. We’d already talked about trying to figure something out about getting together again. I could tell he was more interested in sex than a relationship, but there was also still a glimmer of hope there for something to bud. I don’t claim to be a pro in the bedroom, but I do think, based on previous feedback, I am pretty damn good between the sheets. Maybe I could win him over that way.
We went back and forth for some time about him coming over. He wanted to go to the gym and hadn’t left work yet. Apparently I didn’t give him enough notice, but I could tell he was very interested. We talked about the logistics, and I made some great progress imploring him to come over. He told me he’d try to get his errands done and then he’d be in touch.
In the meantime, I had the blowjob on hold. I told him I had some work to do, and I would get back to him. He wasn’t thrilled, but he accepted my proposal of postponement. I told him I’d reach out to him as soon as I finished my work.
Finally, I got a text message. It appeared we were going to have our “second date” after all. He was wrapping up a few things and then he’d be over. He informed me he was bringing his c*ckring and poppers. I told him that was fine, but I wouldn’t be partaking in the poppers.
I immediately hopped in the shower to clean up, shave and prep for his arrival. I also opened a bottle of wine so we could relax before just jumping in the sack. I wanted to seduce him a little.
When he arrived, he was slightly awkward. I poured him a glass of wine and we sat on the couch chatting and drinking. When I felt the moment was right, I made a move. I was all but on his lap kissing him. And that’s when I learned why he was still single.
He was the worst kisser I’d ever been with. I thought he was going to eat my face. All that time I spent staring longingly at his lips, and that’s how he chose to use them. It was a very sad Valentine’s Day. I tried to soldier on past it. I tried to lead him and make-do the best I could.
Finally, I stood up to take a break, took him by the hand and led him to my bedroom. We slowly undressed each other. I was enjoying peeling his clothes off one by one. As I did, I was groping his entire body. He had a very sexy body and great skin. I couldn’t stop feeling him up.
Warning: The following may be too graphic for some. We laid head to toe and began orally pleasing each other. Eventually, he stopped to put on his c*ckring and grab his poppers from his jeans pocket.
When he came back to the bed, I began orally pleasing his bottom. He had a great a$s and manscaped very well. I was enjoying myself, but it didn’t seem I was doing the best job for him. That’s when I learned he doesn’t really get anything out of it, he told me apologetically. I didn’t understand because long ago he told me he was a bottom. I also recalled how much stimulation he got from his nipples, so I concentrated on them. He went wild.
A short time later, we laid next to each other stimulating ourselves. It didn’t take long before I finished all over his chest per his request. For once it didn’t take me forever to climax. As soon as I finished, he too exploded on his chest.
After giving him a towel and we both cleaned up, we laid next to each other in bed. I wanted to cuddle, but he didn’t seem the type to I just put my hand on his inner thigh. We chatted about the most random things. He was staring at my bookcase, and we talked about some of the books on the shelf. I pointed out my only gay book on the shelf, Beaches. It’s a picture book I like to page through periodically. He told me all the gay books on his bookshelf deal with barebacking. A huge red flag went off in my brain! Was he into barebacking? I didn’t ask him to elaborate, but I wish I did.
That’s when I hopped on his back and began to give him a massage. I have very large and very strong hands. I like to put them to good use. Apparently he was a little more delicate that I anticipated. He asked me to lighten up a bit, but he was enjoying what I was doing. I noticed how he analyzed everything. He really was a headshrinker.
When I stopped, he started inspecting my skin. I recalled on our date how he wished he was a dermatologist. He was very complimentary of my skin and complexion. I appreciated the compliment, but the delivery was incredibly awkward. He was not an easygoing guy, and I started to realize how little I was attracted to him. On top of that, I was starting to get an irritation on my neck from where he was trying to eat it. I knew then this would not be a repeat offender.
With that, he got dressed, collected his things, and we said goodbye at the door. He left very unceremoniously. I had no plans to reach out to him again after that. We’d had such a long history, making it weird, but we’d only really known each other a short while. He too had no plans to reach out to me.
Ironically enough, he messaged me on Grindr the other night, but of course this went nowhere.
Now, the only question is when and if I unfriend him on Facebook and what are the consequences?
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When I arrived back at Smiles‘ apartment, we agreed upon watching a movie and ordering take-out. He was in the mood for barbecue, so we pulled up a menu online to figure out what to order. We also took the time to pick a movie to pull up on Netflix since Smiles doesn’t subscribe to cable.
Throughout all this, I started getting handsy. He was sitting in his computer chair, and I stood behind him massaging his shoulders and then his chest. I had my hands down his shirt caressing his chest in a very sensual motion. He was really enjoying it, which means I too was enjoying the moment. He commented, “This feels better than the Asian woman who gives me a massage. You’re more relaxing than she is. I should save my money and come to you.” I took this as a great compliment and continued to pleasure him.
After some time, I backed up and sat on the couch. He was going back and forth between the living room and the kitchen. I stuck out my finger and beckoned him to come closer. I pulled him down on my lap, and we sat there embracing for some time. After about two minutes of silence, just enjoying our closeness, we started to chat a bit. When he had his fill, he started to back away, but I pulled him in closer and told him, “I’m not done yet.” We both laughed and he tightened his embrace.
Our dinner order was placed, and our movie chosen. He grabbed my hand and led me to the bedroom, and we hopped into bed to watch Vanity Fair. Smiles was very cuddly throughout the entire movie. We changed positions periodically to ensure consistent blood flow and comfort, but I was really enjoying snuggling with him. He had been very sweet from the moment I walked in the door.
About half way through the movie, we realized our food hadn’t arrived. Smiles called to inquire and was told it would arrive shortly. When another half hour passed before we saw our food, he called again to complain. Just then the food arrived. We paused the movie, filled our plates and made our way back to the bedroom.
When the movie was over, we cuddled and spooned and chatted a bit. I was happy. Things started getting more playful when I pulled up his shirt and started to blow raspberries on his stomach. He went off in a fit of laughter. He then resorted to pulling any body hair I have. I told him that was just plain mean. I told him that was my mother’s defense mechanism when I would joke around with her as a kid.
This segwayed into exchanging fun stories from our childhood. I was really beginning to feel like I had a boyfriend. Yup. I said it. I just used the “b word.” I didn’t say this to him, but I began to think about it. I felt very close to him at that moment.
Smiles began to become very relaxed and slowly started drifting off towards sleep. I was gently rubbing his whole body while he dozed off. We were spooning, and I slide my hand between his thighs and started to massage his manhood. It wasn’t long before my hand was pulled away with a grunt.
I know I said I was going to bring it up the next time I was denied, but I chickened out. I was a little taken back by it. He had been affectionate all night, but when I tried to make a move, my seduction was shot down.
At this point, my ego was in the toilet. I quietly spooned a few minutes longer before we hugged and kissed goodnight. I found myself in the very familiar situation of walking home alone pondering why the guy I was so strongly attracted to was so distant from me on so many levels. I tried to think about how great the day was instead of the unhappy ending, but I’ve never been good at fooling myself. I’m far too much of a realist.
I needed a new game-plan, but it wasn’t going to be an easy one to come up with…
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Things weren’t exactly progressing smoothly in my mind between Smiles and I. In fact, things weren’t progressing at all when I come to think of it.
Instead of abandoning my relationship with him, I decided to put forth greater effort to ensuring its success. I’m not one to quit without a fight, so when Smiles texted me to ask how my day was going, I was quite elated. I told him it was going well and was anxious for work to be over. We made plans to go to dinner that evening after work. I was looking forward to it and was ready to make sure it wasn’t a repeat of our last date.
In turn, I asked him about his day, and he responded with an explanation. I explained I wouldn’t be done work until a little later, and I wasn’t sure exactly what time that would be. One of my coworkers was dragging his feet, and my day was beginning to drag on. It was a Friday, and I wanted nothing more than to see Smiles after a long day.
Smiles was running errands in my neighborhood and called when he was finished. I had a feeling I would be done shortly, but there really was no telling when I’d finish. Smiles occupied himself for some time. When he called again to check in on me, I was able to tell him I was about to be walking out the door. He was about to hit up Barracuda to have a drink with his bartender friends, but instead, we picked a place to meet.
I snuck up on him on the street and startled him with a big hug. We exchanged a kiss and started to walk towards Chelsea. We quickly found a spot to grab dinner. Smiles wasn’t drinking, but I certainly needed a drink. I ordered a glass of wine and took a big swig. I’d been talking up a storm from the time we kissed on the street. I was going to make sure the conversation flowed like a waterfall. He was well engaged all throughout dinner at Bar Baresco. I really felt very comfortable with him and was appreciating his company greater. It was night and day difference from the last date we had. I was realizing why I fell for him in the first place. No awkward pauses. No blank stares.
During my workday, I began drafting plans to build my new closet since I was moving. Smiles had much experience in this sort of thing, so I asked him for advice and to look over my plans. He gave his suggestions, and I appreciated his advice.
When we finished dinner, we hit up Barracuda. Smiles suggested it because he figured we’d say hi to his friends. When we arrived there, we found they weren’t working. Smiles ordered us two drinks. After relieving myself, we found a quiet corner to tuck ourselves in to sit and chat.
We discussed age and the ability to hang. He talked about how he used to be able to go out all the time all night long. We talked about growing older and looking forward to staying in and sitting on the couch on a Friday night.
We were growing even closer. As time progressed, I realized he was growing weary. I asked if he would like to get out of there, and he gladly obliged, but not before we played around with his scarf in about 20 different permutations around his neck and head.
As we walked outside, I proposed coming back to his place with him. He agreed. I thought I was sending a pretty clear signal of my intentions. We walked over to Seventh Avenue to hail a cab to no avail. I was not properly dressed for the weather. I was freezing. The Smiles did one of the sweetest things. He came up behind me and wrapped his arms around me to keep me warm. I reached up and grabbed his arms and brought him in closer. It was extremely romantic, and I wasn’t about to let this moment run away from me. It took a long time to get a cab, but I was relishing every second.
When we finally hailed one, we hopped in. He extended his hand beckoning for mine. He was winning me over big time! It was a complete 180. I was thrilled with his new-found affections. It painted a clearer picture of his true feelings for me. He was still interested in me. I was thrilled.
When we arrived at his place, he started cleaning. I kept yelling at him to stop. I didn’t care about the condition of his apartment. I would have liked to think of myself no longer as company, and more as companion. He sat on the couch, and I sat on his computer chair facing him while we chatted. After a while, I realized how ridiculous this setup was. I aimed to remedy it. I got up, walked over to the couch, moved the pile of papers from it, and sat next to him. He looked slightly uncomfortable by this, and I couldn’t fathom why.
He suggested we move to the bed. My goal was being accomplished. I was all too happy to move things to the bedroom. We climbed onto his bed. We talked and then began hugging each other. This morphed into spooning.
I was happy and hoping this would progress to sex, but I was sorely mistaken. After spooning for about ten seconds, he had his fill. He was ready to go to bed, and apparently I wasn’t part of that scenario. He went to brush his teeth, and was giving me all the signals it was time for me to go.
We said goodnight and exchanged a kiss at the door. Yet another night without sex. It was an enigma to me. I couldn’t figure him out. He spent the earlier portion of the night being utterly sweet and affectionate, but when it came time to end the night, the sparks were quickly doused.
I wished the night ended on a more positive note. I would have liked to go home a happy satisfied man, but yet again, I was debating in my head Smiles’ attraction to me…
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If having to work on a Sunday isn’t bad enough, following a night of heavy drinking only makes things worse. My coworkers noticed my less than human state and offered to get me things to ease my pain, but I explained I just wanted to finish work and go back to bed.
The day was long and arduous. Many of my coworkers were dragging their feet, and it was all I could do to light a fire under their asses. I was trying to be as time efficient as possible, but it was no use unless everyone else was onboard.
When I didn’t think my day could get any worse, my mother called to tell me my grandfather passed away. I was expecting the news, but I had no idea when the call would come. He had very advanced cancer, so it was only a matter of time. I know he was more than ready to go, at times basically asking the hospital to give him the “black pill,” but no one likes to see a loved one go.
I soldiered on through my day not mentioning it to anyone until I was about to leave. I needed to tell my boss I would out at the end of the week to go home for the funeral. He was very sympathetic and supportive.
Really, after such a long day at the office, I wanted nothing more than to see Smiles. He could make me happy, no matter what physical state I was in. I hadn’t seen him since Friday night, and I didn’t get to spend the night in his apartment. I was itching for more time with him.
When I was nearing the end of my workday, I texted Smiles to ask him if he wanted to grab dinner. After some time passed, he responded apologizing, “Ah shoot! Just seeing this now. I ordered pizza and I’m starring at the mess I have to clean up here.” I was a little disappointed, but I wasn’t giving up that easily.
“Mind a little company for an hour or so? Not going to be around this week really…” I texted. We had a very big pitch coming up that week, and I knew I would be working late most nights. This was my last stitch effort to see him for a while. He replied, “Come eat this pizza and hang out. It’s not like the mess is going to get any worse.”
This was my first time venturing to his apartment. I knew the general neighborhood, but not the exact location. After work, I took a cab to his apartment. I was very excited to see him and happy I was finally getting the invite to his place, even if I had to invite myself.
His apartment was not what I expected other than the mess he was describing. He was in the process of moving and office worth of things into a storage unit. I didn’t care about any of that. I just wanted to cuddle up next to him in bed.
He offered me pizza, but I explained I already ate. He suggested we watch a movie, and I agreed. We went into his bedroom and chatted while he picked a movie. I told him about my grandfather, and he lent me his sympathetic ear. We’d already talked about how he was ready to go when we discussed religion at his birthday lunch, so he was already quite versed in the situation.
In the meantime, he selected All Good Things while I snuggled up next to him. I have a thing with constantly petting guys I date. I don’t know why, but I just crave the physical connection. I was constantly stroking him gently with my finger tips throughout the movie, switching my hand positions periodically. It was all I could do to refrain from jumping his bones. It wasn’t the most romantic movie of the year, but I’d already seen it and had sex on the brain. It’d been a while since we last had sex, and I wanted more.
Sadly, that wouldn’t happen once again. When the movie ended, it was 11:00pm. He gently hinted at my departure, even going to the bathroom to brush his teeth. Yet another sexless night. I was really beginning to wonder why he didn’t want to have sex with me. I wondered if it was my issues coming between us or if he wasn’t attracted to me. He never gave me any compliments about my body even thought I made a point of complimenting his. Maybe he just didn’t find me attractive.
Regardless, I gave him a kiss goodnight and walked all the way back to the PATH station to head back to Hoboken. The whole walk, thoughts flew through my head like lightning. I was hurt and worried. Hard to admit, but I almost wanted to cry.

That wouldn’t be the worst part of my night however. In the middle of the night I was woken by violent stomach cramps. I ran to the bathroom and destroyed my toilet. At times, I had to debate which end was more priority to face the toilet. I got almost no sleep and had a full day of work ahead of me. There was no way I could take a sick day.
In the morning I was greeted with a text from Smiles: “Maybe a stomach flu? Up all night with cramps and still hurting 😦 .” I finally nailed the source. I caught some bug from him. “I shared your pain! Still sharing… Was trying to figure out what I could have eaten yesterday… And I have to work all day today… 😦 ,” I responded. To which he replied, “This is the worst!”
Karma was coming back at me something fierce. I don’t know who I p*ssed off royally to deserve such a bad weekend, but the only thing keeping me going was it couldn’t get any worse than it already was.
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