Posts Tagged risky

The Milkman

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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The Navigator

In my Grindr surfing, I’d hit up more than a handful of guys. I struck up a few conversations and blocked a few I wasn’t interested in, but since I don’t pay for Grindr Xtra (I refuse to pay for the service on principle), there were a lot of guys floating around my screen in no man’s land. I casually kept a conversation going with a handful since I’d be there a few days and wanted to keep my options open.

On in particular didn’t really stand out from the crowd. We had weak conversation going — Just the pleasantries. “Hey. What’s up? What brings you to Grindr?” etc.

When I woke, I called Hertz and confirmed they would be picking me up that morning to take me to the lot. A woman drove me while I chatted some more on Grindr. Of course, when I got there they upsold me: “My only compact is at the car wash. You can wait, or for $10 more a day, you can take the convertible.” “Sold!” I exclaimed. I was like a kid in a candy store. I immediately put the top down and sped off back to my hotel. I couldn’t wait to hit the beach!

While I ate my breakfast in the hotel restaurant, I continued to poke around Grindr. I had plans to go to the beach that day, but I would be returning in the evening. Maybe I could find someone to hang out or hit up the bars.

The guy I’d briefly chatted with the previous evening messaged me once again and said, “Good morning.” We talked about what we had planned for the day. I mentioned my plans to hit up the beach when he replied, “What time should I be ready.”

A huge smile lit up my face. “How bout now?” I quickly shot back. Much to my surprise, he was just as serious as I was. “I have a few errands to run, but I can be ready at 11:00,” he added. That was in a half hour. “Perfect. I just got back from picking up my rental, and I’m eating breakfast now. Shoot me your address, and I’ll swing by around 11:00 to get you,” I said.

I gathered my beach things, hopped in the car and sped off to pick up my beach buddy. When I arrived in front, I called him, and he came out. I had only seen a few pictures, but was pleasantly surprised that he was a masculine good-looking man. This was going to be a good day!

We introduced ourselves, and I thanked him for joining me. I immediately asked him if he knew the area and told him my plans to go to Manhattan Beach. He agreed that was the best idea, but told me he had no idea how to get there. I told him he’d be playing navigator while I drove.

We talked casually about our different and similar Grindr experiences. This guy was real. He was very open about things and seemed very smart and very savvy. The longer the conversation drew on, the more I liked this guy. It was an extremely risky move to pick a stranger up in a car and spend the day with him, but it was really paying off. For once, luck was in my favor.

I learned a lot as we drove to the coast. He told me all about his job and what he wants to be doing in the future. I told him about my job, and he asked a lot of questions. He really wanted to know the intricacies of my day-to-day. It was quite apparent we were both really digging each other, and the conversation was so casual like we were friends for years.

On top of it all, he was chivalrous and super sweet. Everything he said came with a gentleman’s tone. He wasn’t self-centered, and from the stories he told, I could tell he was a popular, well-liked guy.

This was turning out to be a pretty great trip, and I was just getting started…

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Rallying Friends

Every year, for the past four years, I’ve hosted an annual holiday party. Ironically, I started it with a First Annual Holiday Bash because I wanted it to become one of my holiday traditions. It would be the one time of year I gathered with my closest friends and spent time with them around the holidays to show just how much I truly appreciate their friendship.

From its first year, it’s been a big hit. An invitation one year is no guarantee of an invitation the following year. I always make sure I surround myself with the people in my life I care most about. If within the following year I fall out of touch with someone, I don’t extend an invitation.

Earlier this year, my friend reached out to me to plan weekends in December. She knows of my party and wanted to make sure I wasn’t hosting it the same night she was celebrating her birthday. We both picked dates and put it to bed.

Months later, I found out I was being evicted from my apartment since my landlord finally sold it. Our eviction date was November 30th; eleven days before the planned date of my holiday party.

This was one tradition I was not ready to relinquish, not matter what it took. Some of my friends look forward to the party a full year in advance. I make an incredible spread (not allowing anyone to bring any food of any sort), and everyone fasts for an entire day leading up to the party.

This posed a serious challenge. I would have to move into a new apartment, get it settled and cater for about forty people in ten days — A near impossible feat. However, my determination is not to be underestimated.

When I sent out my Evite, my sister immediately criticized the invitation of N. She was shocked to see I would invite him, but she also didn’t have the full story.

Apparently over the course of my short relationship with N, I mentioned my annual holiday party. As the holiday season was drawing nearer, he asked for the date of said party: “When is your holiday party so I can put it in my calendar? I’m trying to attend as many holiday parties as possible without missing one.”

Did he just invite himself to my holiday party?! I mean, he was on the maybe list, I’ll admit that. But I had no intention of inviting him in the first round of invitations.

This isn’t because I was holding a grudge over our failed relationship. It was mainly because I was disappointed in him. Considering we lived across the street from each other, I thought I’d at the very least be seeing him periodically. However, since our last discussion about our failed relationship, I hadn’t seen him once. I still had never been to his apartment considering I basically walked past it every day. He never put in an effort to be my friend following our breakup, so I no longer felt the need to attempt myself. I’d given up.

When he invited himself, I had to quickly think of the best and most dignified way to deal with the situation at hand. I started with honesty. “Oh.. Are you invited to my holiday party???” I quipped. “I’m …. just gonna go… f*ck myself…” he responded. I successfully made him feel uncomfortable, but then lightened the blow. I couldn’t do much. My hands were tied. I’m not rude enough to tell him he can’t come, but I wasn’t sure I really wanted him there either. “HAHAHA. Just giving you sh*t. Sending out the Evites today…”

When others friends learned of his attendance, they weren’t happy. I was confused by this. I didn’t think anyone would care. When we were dating, my friends loved him. Everyone approved and expressed this to me. He was a very charismatic guy to be around and played nice with all my friends. It was one of the biggest things that attracted me to him.

However, when he crushed me at the end of our relationship, everyone’s opinion of him quickly shifted.

I have to admit, I don’t know if my opinion wouldn’t have shifted so drastically. If he didn’t do anything to hurt me, I would see no need for malice toward him. I wouldn’t be his best friend, but I would certainly be civil.

This wasn’t the case with my friends. In an overwhelming show of support, they all rallied against him and attempted to convince me to retract my invitation.

I was blown away. I never experienced anything like that before from my friends. I was truly touched.

However, I would not be able to fulfill their requests. I was not capable of uninviting him. I also felt it gave him the satisfaction of thinking he still had an effect on my life. I’d completely moved on. It took a long time, and I went through a lot of turmoil to get to that point. But, I didn’t need him to know that. (Not quite sure if he’s still reading the blog…)

One friend, J, was particularly poignant in his disapproval. “I’ll crack his head open.” I told him I was going to be civil, but I wasn’t going to pay much attention to him when he arrived. “Honestly, I think its risky having him there. Especially since he is a drama oriented person.” He pointed out that N may bring up the blog in front of Smiles just to p*ss me off. “Good point… Going to have to tell him not to mention the blog,” I added. “He may leave early since no one really wants him there.”

K and some of my other friends expressed their lack of interest in interacting with him, and he didn’t really know many others. J responded, “If I have anything to do with it he will leave early.” I couldn’t believe how passionate J was getting about this. He’d never even met N. “Look I’ll be civil… but if he gets out of line you let me know.”

One of my other friends who witnessed my rebound in Martha’s Vineyard, Shorty, made the following suggestion: “You should warn him that your friends aren’t really fond of him so he doesn’t feel bombarded if people are mean to him.” “No one will be mean to him, but they’re not going to go out of their way to be nice,” I speculated. “Haha. I might be mean if I happen to end up talking to him :),” she finished.

I couldn’t believe how much my friends were rallying behind me. To be honest, I thought they all thought I blew things out of proportion when it ended. I thought they all looked at me like I was crazy for being so emotionally broken up after dating someone for a month and a half. He really did break me down a little bit, and I still feel some of the lasting effects of that relationship, as much as I would like to put it in the past and forget it. But, I thought they all thought I was being melodramatic. Apparently, they validated my sentiments.

On another level, N wanted to bring his new boyfriend. I’m sure he’s a sweet guy, but I’d never met him. I didn’t want him at my holiday party. It wasn’t the time or the place to meet him. Selfishly and childishly I also wanted the upper hand. I wanted N to see me happy with someone else, Smiles, while he didn’t have his security blanket to hold onto. I know that is very immature, but in the dating world, I am still a teenager. I’d like anyone to disagree with me they wouldn’t want to do the same thing.

So, I told him he couldn’t bring him. I explained he situation, and I think N accepted my reasoning. It was going to be an interesting night regardless. Many variables were bouncing around, and no one could predict the night, even if some of my friends wanted to start a pool of bets on how early in the night N departed…

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