Work Turns to Pleasure

I was about a year into my career at the Social Security Administration when I met Bobby. Let me back up and explain what I do and who I am, so the story makes sense.

After a few years of working various odd jobs after college, I got hired by the Social Security Administration Office in Philadelphia. My job title was customer service counselor. I wasn't one of the people who sat in the office answering calls regarding benefits. My job was to go out in the field and meet with and help any Americans who were on Social Security and needed further assistance outside of their monthly payment.

In other words, I was assigned a vehicle, and every day I had clients, I would have to go see in person to determine if the Social Security Administration needed to add onto their benefits or give them additional items, they needed to live their best lives.

As for me personally, I was a hard-working bright-eyed 25-year-old male, thriving for my place in the world. I was young and ambitious and I had put more time and energy into my studies, working, and making a name for myself than I had in dating or social relationships. I had always been shy, a bit of an outcast, and never had any luck with the dating life. At the time, I knew or had at least accepted I liked men more than women and had dated another closeted gay man during my last year of college. We kept our relationship secret and my friends or family never knew about my sexual preferences, because every time I was asked about any females in my life, my answer was always, "I got more important things to focus on than dating."

I had "girlfriends" throughout high school and my first year of college, none of which were ever very in-depth. It wasn't until I dated a man that last year of college, that I knew I preferred men, but I still wasn't going to put a lot of effort into dating, because I would have to eventually break the silence of who I was. And quite frankly, I wasn't ready for that.

On a Tuesday morning, my supervisor called me into her office, telling me to shut the door, after I passed the threshold. For a minute I felt my ass pucker because I thought I was out of a job.

"Sit down Matthew." She spoke, as her hands were thumbing through a file.

"Matthew, you have been doing good work and I am pleased with your progress." She followed up with.

"We have a troubled client, that no one can seem to get satisfactory results with. And since you have been doing so well, I want you to try and see if you can get his issues resolved."

"Okay," I mumbled, as she reached over her desk handing me a file.

"The client's name is Robert Flemming. He lives in those new apartment complexes down on 18^th Street. He has been an absolute pain in the ass since he received benefits." She stated.

"Why?" I asked. "What's his condition?"

My supervisor explained in short detail, that Robert had a bad back and diabetic nerve pain in his feet, so he couldn't work and the apartment complex would not provide him with any other services. She furthered, that he is demanding new items for his back, and his feet problems and wants a live-in caretaker, all provided by us. She continued by saying Robert has been verbally abusive to other Social Security Counselors and is what we like to call a constant victim. I knew my boss had given me the case because she felt confident, I could help him resolve his continual complaints and abuse towards my co-workers.

After reading the file, I decided I was going to reach out to him on his cell phone and see what day I could meet with him. After a brief conversation, I agreed to meet him on Wednesday at 11:00 A.M. at his place so I could assist him further. I could tell he was an absolute dick, just by his tone and words while on the phone with me. But I wasn't going to let the proverbial complainer beat me. I was going to handle this.

I arrived Wednesday morning at the apartment complex a few minutes early and reviewed his file again. Seems Bobby, as he likes to be called, had two major back surgeries in the last five years for his lower lumber region, L4 and L5 and after that, he had been diagnosed with Diabetic Neuropathy in both feet. Robert was 47 years of age and had been receiving benefits for just over three years. The Social Security Administration had increased his benefits two-fold since he first became a client because he could not stand or sit for long durations, limiting his ability to maintain gainful employment.

By his file, Bobby had no immediate family members listed, just a cousin in California being the only emergency contact. He stood 5'9 inches tall, weighed about 180 pounds, and had last worked as a forklift operator at a factory in Hersey PA. The file didn't report if his back problems started with a work injury or just a genetic defect.

As I entered the building, I walked into the foyer, found his name in the directory, and buzzed his room number. He answered and buzzed me through the door, where I made my way to the elevator and up to his unit.

I knocked on the door and heard him say, "One minute." When he finally answered the door, I was almost taken aback by the man who stood before me. By the definition provided by my boss, I expected some big, burly, angry man, yet I was met by someone small and thin in stature, maturing, and in desperate need of more help. I re-introduced myself to him and walked into his unit. The unit appeared fairly kept, and clean and it appeared Bobby was handling his new living arrangements as best as he could.

"So, you're the next rep they've sent me." He bellowed. "What happened to Joyce?" He asked.

"Joyce has been reassigned to a different division," I answered assuring him, that this wasn't something personal.

"Well, that bitch never did anything I asked for." He touted. "I hope you can solve my problems, with your organization and this building."

"I'll do my best. What is it I can assist you with?" I inquired.

Bobby rambled on for about 15 minutes regarding the litany of complaints he had about my administration as well as the buildings. Things like, not enough money every month to support his lifestyle. Lack of a supportive back brace, a better walker, coupled with the fact that no one will bring up his Amazon packages, or his groceries when he orders them. The building supervisor refuses to send the maintenance men to fix his window frame. The building won't upgrade him to a three-bedroom unit, so "we" (The Social Security Administration) can provide him with a full-time caretaker, along with a bunch of gripes about the "Faggot ass doorman" who teases him, when he goes down to get his mail.

I almost laughed aloud, when he said "Faggot Ass Doorman", and Bobby could tell, I was laughing inside.

"What's so funny?" He barked at me.

"Well, you said, Faggot ass doorman. I guess I was surprised you said that. But I have to ask you Bobby, what's his sexuality have to do with anything?"

"Because I'm gay". He snapped loudly, "I know a cock sucker when I see one."

I could tell Bobby was an angry man. I don't know if it was because of his lot in life, or if he felt outcasted because he was gay, or if he was just one of those people in the world, who are just mad at everyone and everything.

I stayed with Bobby for about an hour, walking through things, I could try to help him with and promised him, I would stop at the main office on my way out to discuss any issues he had with building management. But something odd happened while we were conversing and after he calmed down and talked to me like a human being. I surprisingly found myself attracted to him. Maybe it's because I had reached a reasonable level of conversation with him. Or the fact that he said he was gay, or because of all the clients I have dealt with, he wasn't as physically challenged as others.

But I assure you while sitting at the table with him, some very deep, erotic thoughts passed through my head. Suddenly my lack of desire and ambition to not date flooded over by thoughts of sucking dick and being fucked like I had done some years ago, while in college.

I assure you I kept it professional and had stooped downstairs as I had promised, but as I got back into my car to head to my next appointment, I was horny and felt utterly strong urges to suck cock again. I could still smell Bobby's cologne in my nose for the remainder of the day and wished I could have hinted my sexuality to him.

After returning from my fieldwork and completing my follow-up reports, my supervisor asked me, "How did the appointment with Robert go?"

I told her it was good, and I was going to look into some additional items for him and hopefully, he won't be calling us any further.

"Good" She replied. "I am so tired of him calling here."

But secretively I was thinking in my head, I hope he calls and I hope I can make another trip to his place to see him again. Something about him had my attention. I did feel sorry for him. He wasn't mentally challenged; he wasn't missing limbs or had some defects. Unfortunately, he had a bad back and some nerve pain, not caused by anything but nature, and as I said, once I had him calmed down and spent time trying to help him, he became more receptive to me and spoke to me as if I were a friend. Maybe something no one had ever done for him before.

That night, as I lay in bed, I thought of him further and feelings and desires for sexual pleasure crept into my mind. It wasn't long until I was rock hard and my ass was tingling. I started thinking about Bobby pulling out his cock and making me suck it. Guiding me onto my knees as he slid up behind me and pushed his dick deep into my ass. Of course, it wasn't long until I was stroking my cock, mouth open, moaning out his name as I could visualize him sucking me off. I came quickly and just shook with the pleasure of getting off, as I had done many times before. But this time it wasn't some odd made-up gay fantasy or memory of my college boyfriend. This time it was Bobby and how much I wanted him.

I worked on Bobby's case for weeks gathering the items I could get for him and the next time I went over there, I had a few items he requested. And even though I was getting what he requested, he was still an absolute asshole to me, like he had been the first time I was there. I started to wonder what I had to do or ask him to get him to look at me and maybe hit on me. Time and time again, I would ask leading follow-up questions like; What else can I do for you? What else can I assist you with? Is there anything I can personally do, to make you better?

I guess in some ways I wanted him to make some kind of gay, homosexual deviant remarks like; you can suck my dick. Or, you can rub my balls. Something... anything... So, I could reveal who I was and my interest in him, without being unprofessional and crossing over the client/provider line.

It was my fifth visit, some two months later, that I got my wish. Even though Bobby trusted in me and was calming down with his vile, obnoxious phrasings, he still had the occasion zing that he'd throw my way. But this time I was ready.

On this day I had brought him some better light bulbs for his lamps, which I bought with my own money and a government-provided, foot massager to help ease his nerve pain. Bobby thanked me. I think he knew I had gone way out of my way to get him items previously denied and spent money for the bulbs he wanted. His rapport with me was much softer and more normal and he said he appreciated my visits and my hard work for him. However, seconds later, he got all riled up barking about my failure to negotiate a three-bedroom apartment in the building, which I had nothing to do with. But I guess since I had resolved several of his wants and needs, I guess he thought it handle that for him too.

As we bantered back and forth and as I got ready to leave, I cut his belly aching off and said; "Bobby is there anything I can do for you today, to make things better?"

Being pissed off and agitated as usual, he barked out; "Yeah, you can suck my dick! That'd make me feel better."

Now, what I should have said was, not my job, or no thank you. But the words, "Well." Crept from my lips.

Bobby stopped his rant and looked at me as if he was shocked, I said "Well" instead of denying his request.

"You want to suck my dick, Matthew? Is that what you like?" He bellowed out aggressively.

I raised my eyebrows and kind of lifted my shoulders as if hinting... like well... if it helps you.

"Are you a fucking faggot?" He barked out.

"Well," I muttered again. "I like men, Bobby. Yes."

"Huh," He groaned out. "I didn't take you for a cock sucker."

But then I got defensive because I wasn't going to let the gay guy, rip me for being a gay guy. "Is that what you need Bobby? Would it make you happy if I sucked your dick?"

He froze. It was like a glorious victory over the bully. I was calling out his bullshit, and putting him on the spot. If he wasn't serious about me sucking his dick and was just being vile, I had him. If he was interested in me and wanted some form of a physical situation, he was going to have to admit it. Either way, it was a checkmate moment.

"Well?" I inquired. "What do you need Bobby?"

He was like a deer in headlights, sitting there on his couch, looking up at me, as I stood next to his dining room table.

"Well, I guess we will have to figure this out once and for all Bobby," I said as I took off my coat and hung it over the back of one of his dining room chairs. "Do you want your dick sucked Bobby?" Is that it? "Or are you just being an asshole?" Because to be honest Bobby, I haven't had a boyfriend in a while, and

I do suck dick. So, I can suck it if you like.

I stared down at his as I walked towards the couch. He sat there speechless, watching my every move. As I got closer, I stood over him looking down upon him. His eyes twinkled, my body tingling with excitement that I was calling him out. The big, bad, mouthy gay bully was being quieted by my strong actions.

"Well, Bobby?" I inquired. "Do you need to suck a dick too? You said you are gay right? Do you need some dick? Do you want to suck my dick?"

Oddly enough, the bully in him is what turned me on. And I wanted to suck his dick even if he didn't suck mine. If he would have just barked out, "Suck it," or put me on my knees and pulled it out, I would have blown him. But suddenly being in control; calling him out, and maybe about to do something I never would have imagined I would have done with a client, engaging in oral sex, was beyond stimulating.

I knelt down in front of him, as his legs spread open slightly. No words were said, but I could see the excitement in his eyes as my hands rested along the outsides of his knees and were slowly rubbing up and down over the blue, with white striped jogging pants he had on.

"Bobby, you never answered me. Would sucking your dick make things better?" I spoke out.

Bobby didn't say a word, but he nodded his head and licked his lips as my hands were now further up his thighs and heading for the inside of his legs.

"Do you have an interest in me Bobby, or do you just need a blow job? Or are you just being a prick?" I asked.

"An interest." He groaned out.

"You do?" I asked curiously.

Bobby nodded his head up and down, indicating yes.

"Why haven't you said anything then?" I asked.

"I didn't want to lose you help." He replied.

"Good." I moaned out. "Do you want to suck my dick too?

"Yes." He groaned out.

"Good," I replied.

Do you want a boyfriend Bobby, or are you just horny?" I asked.

"I want a boyfriend." He replied. "I'm so alone."

My hands were as far up between his legs as they could have been when I worded out my next question; "Do you want me as your boyfriend Bobby?"

"Yes." He replied. "I have thought about you a lot." He furthered. "I really like you, but I thought you were straight."

Before he could even finish those words, the palm of my right hand was rubbing over his bulge. I could feel his hard cock in his pants, waiting for someone like me to pull it out and suck it, until he came.

"No Bobby, I like men more, just like you. But I don't play games. I want a real man, a real lover. Is that you Bobby?" I asked him.

I do not doubt that Bobby was stunned I was there on my knees rubbing his cock hidden deep in his underwear. Bobby lifted his hips as I reached to the sides of his jogging pants, pulling gently downwards to pull them off. He sat there in the white fruit of the looms, his dick sticking up straight inside of them, his white polo shirt tails just covering the top of the underwear.

As we looked deeply into one another's eyes, as my hands still gently massaged his cock, I could tell Bobby was for real. This wasn't going to be some one-night thing, he needed love and attention and I needed that also.

My heart was racing as I reached to the sides of his underwear and I was rock hard as his dick and balls came into view as his underwear came off. His dick was perfect, just under six inches long, not too thick, nice round mushroom head. A bit hairier than I liked it, but surely wasn't something I was going to complain about. I edged in closer and grasped his shaft with my hand holding his hard cock deep in my palm. I stroked up and down softly looking up at him, wondering how long it was going to take me to make him cum, considering I hadn't given a blow job in about 4 years.

"It's been a while since I've done this Bobby," I spoke softly. "So, bear with me."

With that, I lowered my head and slid the tip of his cock onto my lips, softly kissing the tip. Bobby's hands came to rest on the back of my head gently, just holding them there, not forcing me down.

I opened my mouth and slid his whole cock into my mouth feeling his hard boner slide across my tongue and towards the back of my throat. My dick was pulsing in my pants and I was in heaven that I was sucking cock again. I bobbed up and down, getting his shaft soaking wet with my saliva, as I felt his hands guide my head and heard his light whimpers and moans.

I slid his cock in and out of my mouth, just feeling the excitement of giving head again. It had been so long, that I kept wanting to suck it so hard, that I would pull it off his body, make him cum in seconds. But I wanted this to last, as I wanted to please him. My mouth watered and I could hear the distinct sounds of giving head, as I bobbed up and down. When I opened my eyes again and looked up, Bobby had lifted his shirt to his neck and was rubbing across his chest, passing his nipples, as his head was cocked back, mouth open, enjoying this moment.

I could hear his soft groans, as I slobbered up and down his cock, my left hand rubbing over my dress pants, feeling my hard cock pulsating. I wasn't sure how long I had been sucking on him, but I felt both of his hands come to rest on the top of my head again. This time his hands pushed down with slight force, as his breath got heavy and his groaning increased. Bobby shifted his ass further down the couch and spread his legs further open a I continued sucking his exceptionally hard cock.

"Oh yes, Matthew." He groaned out. "Just like that, right there..."

Big breaths in were followed by long slow groans as his hands jammed my face downwards and his cock deeper into my throat.

"Oh Matthew, I'm gonna fucking cum. Ummm." He gloated.

I wanted him to cum, but I was so hard and so ready to be sucked, that I needed my time to. I pulled Bobby's cock from my mouth, and swallowed down all my saliva as I grabbed his cock with my hand saying; "I want to make you cum, but not just yet."

I stood up, pulling my dress shirt from my waistline, and fumbling to get my belt open and pants unzipped. Bobby pulled his shirt over his head, as he edged further to the end of the cushion, as I finally got my pants open and was pulling down the top of my blue boxers. Bobby grabbed my hard cock with his hand pulling it towards his face, leaned down a bit further, and slid my cock deep into his mouth.