Blue Collar Blowjob

One of the greatest things about being in the dating world in the present day is that people are so much freer in their sexuality than in previous decades. In the twenty years that I have been playing the field, I have watched as bisexuality has become less taboo. It seems like more and more people are coming out as bisexual, when really, it's just that society has become more tolerant toward things that are deemed as "other," so more people feel comfortable embracing their sexuality. In my opinion, being bisexual is like having your cake and eating it, too; limited yourself to one gender can be restricting. I wish that I was into women as well, as my experiences with men tend to end badly.

Back in the early spring, I started talking with a guy named Jack on Grindr. He's engaged to a woman, they're swingers and both bisexual. Jack told me that he had been bi-curious most of his life but had never had the nerve to act on it until recently. He and his fiancée had had a threesome with a friend of his and the friend's girlfriend. He did go down on the guy a little bit, but having two extra sets of eyes watching him had made him nervous, so it hadn't lasted long.

Jack and his fiancée, Karla, came to see me at work; we chatted and got to know each other. I'm not the type of person who can just hookup with a total stranger, and Jack is the same way. It was adorable how nervous he was just talking to me, knowing that nothing was going to happen that night. James and I had exchanged nudes previously; apparently, he shared the pictures with Karla, and she liked what she saw. Jack was given permission to do solo hookups with me, but eventually she was hoping that the three of us could get together.

They live about forty minutes from me, in a small farming town, with no neighbors. The goal was to get me to drive out some night when the children were away (both Jack and Karla have kids from previous relationships,) and we would commence with the threesome. Even if I didn't have extreme driving anxiety -- especially when going somewhere new that I don't know --- I wouldn't do it. I'm a huge horror movie fan; I've seen too many movies where being isolated in the country leads to disaster. Not that I think Jack or Karla are psychopathic murderers, but for the sake of my well-being and anxiety, I decided it was best to meet at my place.

Jack and I are both extremely busy people, so we lost touch for the rest of spring and most of the summer, except for sporadic messages when he was horny for a guy. Once I told him that I was talking to someone and that we were planning on going on a date, Jack decided he really wanted me to be the first guy he gave a blowjob to, so we scheduled a night where we both were free, and he came over.

Jack is a blue-collar guy, very country. Aside from his day job at a machine shop, he also has a farm that he tends to. When we met the first time I started referring to him as Farmer Jack. While very sweet -- and adorably shy -- Farmer Jack is not really my type; he is taller than I am, which is a huge plus for me, but he's heavy-set and not conventionally attractive. If you're into bears, you'd be into him, but they are not my usual type.

Farmer Jack was extremely nervous when I let him into my garage. Although he was smiling, his face was flushed a bright red, and he couldn't manage to stand still for more than a few seconds. Normally, I'm the nervous one, so being in the position of power was a turn-on for me. We made small talk at first -- about work and our personal lives -- before we grew silent and just looked at each other.

"I don't really know how to start this," I admitted. Every hookup I've had was always initiated by the other person. I am not confident enough in my attractiveness, nor my sexual appeal to be the seducer. Considering that this was Jack's first time though, I decided that I was probably going to have to deal with the awkwardness and just get it started.

"I don't, either," he replied with a chuckle. "I didn't wear underwear, so it would be easier for you."

"I have underwear on." Before I could lose my nerve, I dropped my sweatpants. Jack's eyes immediately went down to my crotch, and his tongue darted out to wet his lips.

I walked closer to him and grabbed his penis through his black sweatpants. I had seen it before in pictures, so I already knew that he was not huge. I actually prefer smaller penises -- for oral -- they're easier to get off and they don't hurt my throat. My theory is that because it's smaller, it's getting more stimulation coverage; I'm no doctor of Dick-ology, but that's my thoughts on the matter. He gasped a little, and I could almost immediately feel him growing hard.

"Can I touch yours?" he asked quietly, not looking away from the front of my black boxers.

"Of course." I pulled his sweatpants down enough to free his hardening cock, and started stroking it, watching as he bit his lip again.

"You have a really great dick." His voice was husky with lust.

"Thanks. I've been told that before, but I feel like it looks better in pictures. It always looks smaller to me, in person."

"Not to me. It's pretty big."

"Thanks."

"Can I suck it?"

"Of course."

As Farmer Jack started to get down on his knees, I felt nervousness set in. It's not uncommon for me to not enjoy getting head. There are a few occasions where the guy has been so good that I'm panting and pulling his hair, but most of the time I'm squeezing my eyes shut, and trying to mentally force myself to cum. I don't want to have to make an excuse to jerk myself off until I'm about to finish, and then have the guy hurriedly latch on so they can get the load in their mouth. Hookups aren't really my thing, so I don't know if it's because I'm uncomfortable, or because some guys just don't give great head -- gay or bi -- but I'm very self-conscious about it. I want to be able to enjoy head as much as I should.

Thankfully, it wasn't bad. It's certainly wasn't the best mouth I've ever had, but it was better than the vast majority -- and it was only his second time. I grabbed the doorframe as I watched his head bob back and forth, his eyes peering up at me. Normally when a guy has facial hair, it pricks my dick and makes it hard for me to be aroused, but somehow Farmer Jack manages to keep his moustache off of my sensitive bits.

After a few minutes, he stopped to take a breath. "How it is?" he asked, panting for breath like he's been running a long distance.

"Good. It's honestly better than most blowjobs I get." He smiled proudly, making me decide to show him what I can do. "Can I suck you?"

"Sure, if you want."

I got down on my knees and started to work on him. For me, the disadvantages of Farmer Jack's smaller penis were that there wasn't enough there for me to fully grab in my hand, and his belly was so big that I had to go from an odd angle to be able to get it in mouth.

As I got going, I could taste his sweet pre-cum and heard his throaty moans. I figured he'd last a minute or two and then be done, but after about two minutes, he stopped me. "I really want to suck you," he said. I stood up and let him continue on me.

He started deepthroating me, and the sick part of my mind reveled at the tears streaking from his eyes as he tried not to gag on my member. For someone who claimed he could not deepthroat, Farmer Jack did it again and again that night; the more he did it, the better he got at it.

I don't know how long he was at it, but sweat started to trickle down his face, and had to remove his glasses. The head felt good, especially once I started moving my hips so that my thrusts into him synchronized with him moving toward the head of my dick. Most guys I have been with haven't like to be face-fucked, but the control it gives me really turns me on.

Eventually, he stopped to take a breath again and I asked if his jaw was getting sore. "Kind of," he replied, taking quick, shallow breaths. I loved that I was giving him such an intense workout.

"I can just jerk for a bit," I offered, knowing that I would orgasm faster with my own ministrations.

"That's fine."

As I started giving myself the good old fashioned, he stayed on his knees and started sliding his hand under my shirt and up to my nipples. I had not told him this yet, but nipples are my Kryptonite. Biting my lip, I pulled my shirt off and moaned as he started sucking on my left nipple. If he had had two mouths -- one for each nipple -- I probably would have cum immediately.

I forgot I was jerking myself off as the pleasure shot through me and my horniness grew to a crescendo. "I'm about to cum," I gasped, not wanting his mouth gone from my nipple, but wanting him to get exactly what he wanted. Immediately, he darted down, and I finished in his mouth.

After a minute or so, the world stopped spinning and opened my eyes to see him standing up, grinning at me. "Was it good?" he asked with child-like innocence.

"Very good." It would have been even better if I had been attracted to him and had had an emotional connection with him, but I figured I'd keep that to myself. He had done a superb job and wasn't to blame for my personal anxieties.

"Good enough that you'd call me again?" There was a hopeful lilt in his voice that I found incredibly endearing, but I knew that I had to be honest with him.

"If things don't work out with that guy, yeah. Honestly, I like him, and I want to make that a priority."

"I understand! Congrats on that, by the way." There was no ill-will in his voice, which made me feel a lot better. I don't ever want to hurt anyone else; I know what it feels like to be treated without any thought to my feelings.

I offered to finish giving him a blowjob, but now that he had gotten what he wanted, he was too nervous to get hard again. We made small talk for a bit before I had to kick him out so that I could make dinner and start my weekend the right way -- with an edible and a pizza.

In retrospect, I'm glad that I helped bring Jack's fantasy to life; it wasn't a life altering encounter for me, but it is a great story, and I was able to make someone else giddy with happiness. It's a shame that the sparks weren't there for me; Farmer Jack and I could have been a regular thing. I'll have to keep looking for the alchemical connection that changes my life for good.