Four Finger Combo

It is quite common when you're down and out and craving sexual contact to lower your standards a little. It's a mix of desperation and having to re-examine your particular likes and don't likes. I've been known - on more than one occasion - to hook up with someone out of my normal type simply for the story; once in a blue moon it's out of sympathy.

One of my coworkers, Lance was a senior in high school when he hired in. Although he was a nice enough kid, he was incredibly lacking when it came to common sense and general life experiences. He was open about his desire to be pegged by a girl, his bisexuality - I had to explain to him that he couldn't go around saying he was gay, that bi and gay are different - and the fact that he was a virgin at nineteen. I wouldn't say that Lance was ugly, but he wasn't anything special to look at: with frizzy, semi-curly hair, incredibly round, well-defined cheekbones, and a slim physique. If I had to describe him, I'd say a mix between Sid from Toy Story and Slap the Dummy from Goosebumps. If his naivete wasn't enough of a turn-off, then his chronic halitosis got the job done.

Lance enjoyed agitating me, though he couldn't take it when I reciprocated. One night, we were taking out the trash when he said something that annoyed me; in retaliation, I pushed him face first into his car, careful not to actually hurt him. I was surprised when a moan escaped his mouth, but I assumed that he was just playing the part, since he was trying to figure himself out and longed for acceptance. It wasn't until the next time that we worked together that he told me the truth: he had had a butt plug in when I pushed him. Apparently, he'd gone home for a few minutes after school, put his butt plug in, and then forgot about it. As an anal virgin, I couldn't imagine how someone could forget that they had a butt plug in - for seven hours - especially when sitting in a car running deliveries. Lance often bragged that he could get three quarters of the way down on his ten-inch dildo; I found that impressive. If I had found Lance attractive - and felt certain that he wouldn't grow attached - I might have made a move on him.

After many months of working with Lance and having to hear about how unaccepting his family - specifically his dad and brothers - were about his alleged bisexuality, I didn't want to hear about it anymore. At one point, I discovered his profile on Grindr; I tried to help him make it better so that he could actually get laid, but he didn't listen, too shy to be out. He swore up and down that the guys he exchanged nudes with enjoyed his body immensely.

One particular night, he was whining about how he wanted to get laid but the guys in our area were not his type; I could relate, especially when I'd been closer to his age. As we were walking out of the back door, an idea came to me: what if we hooked up? While it definitely wouldn't be a highlight in my sexual history, it would relieve my stress and might give him a little bit of what he wanted.

I pushed him up against the wall of the building, leaning in close. "Want me to do it?" I asked, my voice husky with lust.

"D-do what?" he stammered, his eyes as wide as saucers. I could practically feel his heart thundering.

"You know. Show you what it's like."

"I-I haven't shaved down there..."

"I don't care."

He swallowed nervously and I started walking down the block to my apartment, knowing that he was following me without having to turn around and double check.

As soon as we were inside, I pushed him against the wall again. "Let's see what you've got in here," I said, trailing my hand down his flat stomach to the front of his khakis. I unzipped his pants, undid his belt, and tugged them - and his boxers - down to reveal a decently sized cock. I was surprised that he had let his pubes grow out - he was always talking about how he hated pubic hair and liked to keep things nice and neat down there. I reached down and touched it, smiling when I heard his sharp exhale. He hadn't been touched at all in over a year, since his last high school relationship.

I pulled back and led the way to my bedroom, leaving Lance to shuffle along behind me, his pants around his ankles. He quickly stripped and got on my bed, practically trembling with nervousness. "It's okay," I assured him, sitting next to him. "If you don't want to do this, we don't have to."

"I want to," Lance insisted, licking his lips. "I'm just really nervous."

"I get it. I've been there," I assured him, trying not to look at his dick. I didn't want it to feel like I was pressuring him into anything; while I was okay with taking the lead, he needed to tell me what he wanted. "So... what do you want to do?" I asked.

"I don't know," he admitted, shrugging. "I've never done anything with a guy except kiss. I'm a bottom..."

"Do you want me to finger you?" I asked, already reaching for the bottle of lube on my nightstand.

"Yes," he croaked, getting into the downward facing dog yoga position. I squirted lube into the palm of my hand and spread it around, making sure that my fingers were nice and slick. Casually, I climbed onto the bed and knelt behind him. I pressed a finger against his hole, amused that it slid right in - no resistance. "Fuck!" he sighed, relaxing.

I moved my finger inside of him, making sure to massage his prostate. "How's that?" I asked, leaning around to see his face so that I could gauge his reaction. He was beet red from his face down to his chest.

"You can do another finger," he said, his eyes closed in delight.

I slid another finger in, feeling his hole stretch to accommodate the second digit. Before long, he was begging for another finger; I happily obliged, enjoying his eagerness, how welcoming his hole was. I had never gotten more than three fingers in a guy before, but once again, Lance surprised me by asking for another. I slowly worked another finger in, basically doing the stereotypical Italian hand in his ass. Lance moaned, bucking against my hand as I worked it inside of him,

After a couple of minutes, my hand started to cramp, so I pulled my fingers out of him. A wave of fecal matter odor wafted over to us, making us both stop and look at each other. "I'm not cleaned out!" he protested, wide eyed, somehow growing even redder with embarrassment.

"That smells more like cat shit to me," I assured him, but just to be safe, I got up and went into the bathroom to wash my hands. When I came back to bed he was laying - still naked - on his back.

"I'm really sorry if I..."

"It's fine," I assured him, crawling onto the right side of the bed. I looked down and noticed that his penis was flaccid, hanging limply between his legs. "You're not hard?"

"The shit thing kind of killed it for me" he said, swallowing shamefully.

"You didn't shit on me," I assured him, already past it. "Here, let me help you."

I scooted down the bed and slid his penis into my mouth. I didn't particularly want to suck his dick, but I didn't want to feel like I was raping him; if we were going to do this, I wanted there to at least be a happy ending involved, to make up for the awkwardness that would no doubt exist when we worked together next.

I felt his dick start to harden in my mouth, but it didn't get as hard as I wanted it to. I popped him out of my mouth, stroking him as I looked up. "Everything okay?" I asked. I knew it wasn't me; I'd blown plenty of guys who had extolled how talented I was with my oral skills.

"I think I'm too nervous," he said. "Like...it feels good, but I can't relax and enjoy it."

"Maybe you're not bi, after all," I suggested, stroking him absentmindedly.

"I don't know...I guess I'd consider myself more bi-curious...."

I abandoned my endeavors and laid back against the pillows. Hookups were always uncomfortable for me, but I had done this to give the poor kid something; I knew how frustrating it was when you wanted to get laid, but there weren't any viable options. Even though I wasn't overly fond of him, I didn't want him to risk the danger of meeting a potentially dangerous stranger on Grindr; at least we knew each other.

Lance pulled his phone out and started scrolling through Reddit. He started touching himself, idly stroking his cock as he looked at his screen. "I'm just trying to find something to get me hard," he explained, not looking at me.

"Do what you have to do," I replied, unbothered. Had I been into Lance I would have been offended that my mouth hadn't rocked his world, but as it was, this was just one of my mitzvot for the year. I absentmindedly caressed his naked thigh, watching as he started to grow hard. As blood flooded to his cock, I quirked an eyebrow; it curved to the left toward the tip. "Do you want me t0..,?"

"I'm already about to cum," he gasped, eyes glued to the trans woman on his phone screen.

I took over for him, giving him a few strokes before he came all over his stomach.

After a moment, he laughed nervously. "Well, that happened," he said, avoiding my eyes.

"It certainly did," I agreed. "Feel better?"

"A little. I was really into it when you were fingering me. I was ready to risk it all and let you fuck me."

I'd be lying if I said the thought of my dick exploring the ass that had so greedily devoured my fingers didn't excite me, but I knew that had I fucked him, it would ensure nothing but awkwardness at work; I'd have taken his virginity, possibly endearing me to him. I didn't want to kiss him, didn't want to date him.

"I don't have any condoms," I said, hoping he didn't see how closed off I was quickly becoming.

"It's fine, after that shit smell..."

"I'm pretty sure it was from the litter box," I explained. "My cats have some volatile shit."

"Oh, right!" I saw him visibly relax, his shoulders dropping. "I didn't think of that. I was sure it was me; I was so embarrassed."

"It's all good," I assured him.

A few seconds later, he stood up and got dressed. "I should probably get going," he said, once again looking anywhere but at me. "If I'm not home by the time my parents go to bed I'm fucked; they lock the door and I don't have a key."

"No worries. I have to take a shower and stuff anyway. And scoop the litter box apparently."

As soon as Lance was gone, I threw myself back onto the bed. What the fuck had I been thinking? Hadn't I already learned my lesson about hooking up with coworkers? It never ended well. I needed to learn not to shit where I eat.

Thankfully, things didn't get weird between us. For the most part, we pretend like it never happened, which suits me just fine. Lance doesn't want me to tell anyone about it, swearing me to secrecy. To date, I am the last person that he did anything sexual with; I've been with quite a few guys since that night. Lance has met Zane and thinks he's cute; I often joke that they should get together since they have more in common than Zane and I do, plus Zane wants to top and I'm firmly against it.

I don't know why or how I always seem to find myself in the most bizarre, random sexual experiences, but I guess everyone has their lot in life; mine just so happens to be sex-related. I try to look at the bright side: if nothing else, it at least makes for some great stories.