My Boss and Me Ch. 01

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My head was spinning as I slipped beneath the bedspread and sheet in what I knew would be a futile attempt to fall asleep. I lay there in the darkness, my eyes wired open, and blamed the beer for keeping me awake.

My boss, Tommy and I had gone to yet another bar, struck out with the girls we met, and retreated to his apartment for beer that didn’t cost us six-dollars a bottle.

As usual, our conversation turned into a ‘what-the-hell-is-wrong-with-women’ bitchfest.

“We’re too nice…” he said. “women like bad boys – not guys like us.”

“Yeah,” I agreed, “they do seem to prefer the loud-mouthed neanderthals that slobber all over them. I don’t get it – all those guys do is brag about themselves, and they treat the women like pieces of meat.”

“You know, John, there seems to be one more thing that women seem to like about them,” he said.

“What’s that? They all have more money than us?” I asked.

He smiled and replied, “Well, yeah, that’s part of it…I hate to say it but most of the guys at the bars we go to make you and I look like little boys. They’re all over six feet and outweigh us by forty-fifty pounds.”

I frowned and nodded my head in agreement. “I know, but that’s not our fault – we are who we are…”

I am 5′ 6″ and weigh 130 pounds. Tommy is three-inches taller and maybe 30 pounds heavier. Women giggle and call me ‘cute’ but being ‘cute’ doesn’t get you laid.

“Not only that, it seems like all the guys these days are brimming with self-esteem and confidence – two key ingredients for picking up women…how can we compete with that?” said Tommy.

I chimed in and said, “Yeah, and they all probably have six-inches or more, if you know what I mean.”

Tommy immediately replied, “Nah, that can’t be it – I’m over six-inches and that doesn’t help me.”

“Gimmee a break, we’re practically the same size…how can you be that big?” I shot back.

He held up the palm of his hand, and said,”C’mon, put your hand against mine – I’ll prove it to you!”

When I didn’t move he took my hand and placed it on his. I was startled by the difference in size.

“That’s an old wives tale – you can’t measure it by that!” I said defensively.

He gave me a wry smile and said, “We can whip ’em out and compare…hell John, I’m sure most guys have over six-inches!”

I blurted out, “No, I looked it up – the average length is 5.2 inches!”

“So are you above or below average?” he asked with an even wider smile on his face.

A furious blush spread across my cheeks. I needed to change the subject.

Quite honestly I couldn’t believe here I was hanging out with my boss talking like this. He is 8-9 years older than me, very good-looking, and I found it difficult to imagine him having trouble with women.

“You know Tommy, we’ve talked about this a lot – you and I are quite a bit alike…our only goal is to have sex with them…other than that…” I said, my voice trailing off.

His face lit up and he finished my thought.

“I know, they’re frivolous and petty…self-centered and bossy – always wanting to change who you are…we have to pay for everything on dates and at the end of the night we almost have to beg them to put out…guys on the other hand, especially you and me – we can talk about anything going on in the world…we keep informed…yes, you and I talk sports, but we also talk about so much more,” he said excitedly.

“Damn, Tommy” I said then laughed and quipped, “…it would be so much easier if we were gay, wouldn’t it?”

He gave me an odd, pensive glance I hadn’t seen before and I became suddenly sorry I’d said that..

“John, how many times a day do you jerk-off?” he suddenly asked me.

What the hell – where did that come from? I looked at him like he was crazy. I didn’t know what to say.

“I do it at least twice every day,” he confessed. “Once when I wake up and then when I go to bed at night, of course, a lot of days I’ll do it more than twice.”

My ears felt hot. I couldn’t believe my boss was talking about jerking-off, much less admitting to me the number of times a day he did it. He was talking more like a frat boy than the owner of a successful business.

He continued: “Johnny, let me ask you this – how long has it been since you felt someone else’s hand on your dick? It’s been a long, long time, hasn’t it? It feels sooo much better too, don’t you agree?”

Now my whole face was on fire. Sure, I love discussing everything with Tommy, but not THIS subject!

“Tommy, what are you talking about? Are you saying what I think you’re saying?” I asked him.

“I’m not ‘saying’ anything,” he countered, “you’re the one who said it would be easier if we were gay.”

“We are NOT gay!” I said as calmly as I could. “We like sex with women!”

“Face the facts, my friend,” he said with a snort of derision. “Not once in the six-months we’ve known each other have I seen you go home with a woman!”

“Yeah, well, antalya escort it’s not from lack of trying,” I said defensively.

“Yeah, and I’ve seen you ‘try’ and fail, how many times? You and I are the same, John, neither one of us can put together a coherent sentence when we talk with a woman…we make fools out of ourselves – the women end up laughing in our faces and we slink home to our beds and masturbate!”

“But that doesn’t make either one of us gay…sure, talking to women in bars is not our strength – we need to find different ways of meeting them…but I’m positive giving each other handjobs is NOT the solution!”

“Oh my hell, John – have you been thinking about giving me a handjob? That’s a great idea! You do me and I’ll do you! Think of all the time and money we would save staying home instead of going to bars!” he said excitedly.

My brain wanted to explode. Was he serious or making fun of me? Tommy can be so good at twisting and manipulating my words I don’t know how to respond sometimes.

“I didn’t say that, Tommy!” I protested. “WE-ARE-NOT-GAY!!”

“You don’t have to be gay to lend a ‘helping hand’ to a friend in need,” he calmly replied.

“What the hell are you talking about?” I asked incredulously.

His voice and face suddenly softened. “You’re nine-years younger than me and rather naive, aren’t you John? Haven’t you ever heard the phrase ‘friends with benefits’?”

Good grief – my face grew beet-red once again.

“Of course I’ve heard of it,” I said again playing defense, “…the problem with that Tommy is it involves a girl and a guy – not two STRAIGHT guys!”

“I never knew you were such a prude, John…straight guys do that for each other ALL THE TIME! It’s called ‘lending a helping hand’ and it’s perfectly normal and healthy for guys like us who can’t get lucky with women…Jesus Christ, John, you don’t have to be gay to help out a good friend!”

And once again I thought my head would explode.


Laying on my back and staring into the darkness, I unconsciously reach beneath the waist band of my briefs and fondle my semi-hard prick.

C’mon John, I told myself, don’t be so weak. You can go one night without jerking off, can’t you?

Of course, I knew I was fighting a losing battle. I wouldn’t be tired enough to sleep without ‘stroking one out.’ I sighed and pushed my briefs to my knees and caressed myself until I was fully hard.

As always, my fantasy began with me and my high school sweetheart in the front seat of my car kissing and petting.

I loved feeling-up her boobs and she’d finally allowed me to open her blouse and remove her bra. I imagined her running her hand over the bulge in my slacks driving me crazy until she opened my pants and took my throbbing prick in her small hand.

I pretended it was her hand stroking me up and down and not my own. I worked it fast and hard. I wanted to cum before the image of ‘him’ took over my fantasy again.

I groaned and my hand moved faster and faster. I was so close to orgasm I felt my balls begin to rise.

Then it happened: I heard Tommy’s last words to me tonight and the image of him standing naked under the shower was the only thing I could see in my minds-eye.

His last words had been: “When you jerk-off tonight, think about what you saw when we showered together last week!”

My face again turned beet-red from embarrassment.

We had showered after working out at the gym. He on one side and me on the other about five-feet from him. His back was to me and I thought (non-sexually) that he had a nice ass – one that I would like to have.

He suddenly turned around and there it was – it was at least six-inches and hard as a steel rod. Yes, I know I had earlier expressed my doubts about the size of his manhood but that was a bluff – I didn’t think he’d seen me staring at him but now I knew he’d caught me.

Worst of all, now when I masturbate the image of his hard cock pops into my head. Does that mean anything? I am so confused.


The next day at work in the lunchroom, we ate our sandwiches and made small talk about politics. Tommy suddenly changed the subject.

“You know Johnny, I’ve been thinking about your problem with women…” he said.

I flinched and immediately wondered, MY problem with women?

I was still feeling rather defensive from his comment last night: “Not once in the six-months we’ve known each other have I seen you go home with a woman!”

I should have replied that I’d never seen HIM go home with a woman either and was about to say it when he added: “Maybe we’re going about this the wrong way.”

Okay, he had my attention. I asked him, “What do you mean?”

“Well, when we get to a bar we’re so nervous we can’t even look women in their eyes much less talk with them…maybe we should have our own little happy hour beforehand…we have two-three drinks at my place then go out…we’d be way more relaxed and confident when we get to the bar!”

I lara escort liked the idea instantly and replied, “That would be a huge help – and cheaper too…but you know, we’ve been pressing our luck quite a bit lately drinking and driving – neither of us want to get busted doing that!”

“We’ll walk to the bar…we’ve been to ‘The Meet Market’ a couple times – it’s only two blocks from my place and you said you liked it…want to try doing that tonight?” he asked.

I smiled thoughtfully and answered, “Sure, that’s a good idea.”

“Okay then – Happy Hour at my place begins at seven!” he said.

“I’ll see you at seven!” I replied.

I still could not get over my stroke of luck that the owner of the company likes me and wants to hang out with me. How rare is that!?


A minute after I arrived at Tommy’s place he handed me a bucket glass filled with lemon flavored vodka over ice. He had the same drink. We sat on the sofa and talked.

“Johnny, if you don’t drink any faster it’ll take you forever to get a proper buzz going,” he said with a smile.

I saw his drink was almost gone and began taking bigger swallows until I’d finished mine.

“That’s better,” he said as he took my glass and his to the kitchen to refill them.

The liquor was working already. I began to feel a pleasant glow. One more drink and I’d be in my comfort zone where I knew I could converse with women.

When he returned and handed me the drink he sat down directly beside me which wasn’t unusual. Early on in our friendship he explained he had suffered some mild hearing loss when he’d worked in a loud factory and needed to sit close to hear what I have to say.

I didn’t mind. I knew he was all-man and didn’t mean anything by it.

He began telling me a lengthy anecdote about his high school days. He’s a wonderful story-teller so I always listen carefully.

One more thing about Tommy: he is one of those touchy-feely type of people when he talks.

It took some getting used to, but now when he gently squeezes the back of my neck, or rubs my shoulders and back I don’t think a thing about it. I’ve even quit flinching when his hand squeezes my leg.

At one point though, it did make me a little nervous when he placed his hand on my leg just above the knee and left it there. It made me drink faster and when I swallowed the last of the vodka, instead of giving my leg the usual squeeze, he ran his hand lightly back and forth before he removed it.

He took my drink, stood up and offered me his hand. I was a little tipsy so I held on and he helped pull me to my feet. I could have sworn he glanced at my crotch but I probably imagined that.

It’s about half-a-block from his place to the corner of a busy street. I was pretty steady on my feet but he kept his hand on my back to make sure.

Uh oh, I thought when we approached the corner.

‘The Meet Market’ is around the corner and on the end of the next block. To get there you have to walk by ‘The Leather Vest’ which is a queer bar. I don’t know why, but my heart began pounding.

Now don’t get me wrong, I am not the slightest bit homophobic. I support gay rights and all that stuff and I don’t care what two people do in the privacy of their homes – it is THEIR business not mine so sometimes I wonder why I get an uneasy feeling around queers. Oh well…

Before you get to the corner you have to walk by the back parking lot of the bar. There were small clusters of guys standing and talking. I could see puffs of smoke rising and knew they were passing around joints.

Suddenly the back door of the bar swung open and out came two guys about my age holding hands. They walked quickly to a car then SURPRISE instead of getting into the front seat they opened a rear door and climbed into the back seat.

Tommy chuckled and with his hot breath in my ear whispered, “What do you think those boys are going to do?”

I don’t know why – it was an involuntary reaction, but my prick twitched and became semi-erect inside my briefs. I tried to walk faster but Tommy’s hand pulled me along at his speed.

We turned the corner and when we came to the front door Tommy asked, “Want to go inside for a drink?”

I couldn’t believe he asked me that question.

“Uh, no, uh, that’s okay,” I mumbled.

He chuckled and we continued down the street.


“The Meet Market’ was about half-full and we easily found stools at the bar. I do like the place. It is rare to go anywhere these days and see so many women in skirts and dresses.

I reached for my wallet but Tommy said, “Tonight is on me!”

I don’t remember the last time Tommy let me buy a drink. I rationalize that he and I both know he makes a lot more money than me.

I was going to switch to a ‘safer’ drink than straight booze on the rocks but Tommy ordered me another lemon flavored vodka before I could say anything. He ordered himself a beer.

We sat in silence for awhile and scoped-out manavgat escort the women around the bar. There were quite a few pretty girls giggling and talking in hushed, conspiratorial tones. There were also a lot of buff-looking guys standing around them preening and posturing for their attention.

When I get nervous I tend to drink faster. The bartender brought me another drink as soon as mine was empty. Tommy must have said something to him. Tommy still had over half his beer left.

Tommy launched into another long story. I never seem to tire of them.

He squeezed the back of my neck, stroked my back then placed his hand on my leg. There was something different this time. His hand rested much higher on my leg than usual.

I stared into his rich, brown eyes as I listened to his oft-times funny story. Our laughter calmed me down until I felt entirely at ease and relaxed.

It took awhile before I realized his hand was gently stroking higher and higher up my thigh, and to my complete chagrin, I had sprung a full-fledged boner. I thought about removing his hand but didn’t want to offend him.

Calm down, I told myself, this is Tommy, he does this all the time and it doesn’t mean a thing.

By the time Tommy finished his story I was laughing so hard I snorted vodka out of my nose.

He then excused himself to go to the men’s room and when he stood I swore his hand lightly brushed the bulge in my slacks.

He smiled at me and said, “I’ll be right back!”

“Okay,” I said to him.

As soon as he disappeared into the crowd the strangest thought I’ve ever had in my life came to mind. I wondered if his six-inch cock was as hard as mine is right now.

I quickly forced that from my mind and scanned the girls sitting at the bar.

Straight across the bar from me sat a pretty blonde, all by herself. She caught me staring at her and smiled. I smiled back and quickly downed the rest of my drink. Sure enough, the bartender was right there with another one within seconds.

I felt the pressure building. It was time to take the first piss of the night but I didn’t really want to start. Once I begin, for the next forty-minutes or so I have to go every five-ten minutes. It’s embarrassing; and besides, have you ever tried to take a leak with a hard-on? It’s not easy and sometimes painful.

I decided to wait until Tommy returned to save our bar stools. I began squirming on the seat. When I have to go to the bathroom there isn’t much margin for error.

I stood and motioned to the bartender we’d be back and he nodded ‘okay.’

I expected to see Tommy on my way and to my surprise, I saw him on the dance floor with a pretty brunette.

Good for him, I thought and hurried into the men’s room.

Thankfully they have partitions between the urinals so I had the privacy to release my raging hard-on and pee in solitude. For the life of me I could not understand why my dick would not go down.

I washed my hands and on my way back to the bar I searched the dance floor but did not see Tommy. I did see, however, the girl across from me was still looking at me and since I had drunk enough ‘liquid courage’ I decided to ask her to dance.

I made my way around the now-crowded bar. I had to snake myself through all the taller guys talking with women. It never helps ones confidence when you are face to face with other guys chests and armpits.

I finally reached the pretty blonde and said, “Hi, my name is John – would you like to dance?”

She turned to stare at me and in a voice dripping with contempt asked, “Aren’t you in the wrong bar, little boy? Shouldn’t you be down the street?”

I was stunned.

Suddenly the red-head who had been sitting next to her returned and was beside me shrieking, “OH MY GOD, HELEN – the little pervert has a hard-on and he’s leaking cum through his slacks!”

To which the blonde immediately remarked, “Well no wonder, his boyfriend has been playing grab-ass with him since they got here!”

The red-head looked across the bar. Tommy had returned to his stool.

She said, “You better get over there, cutie, your boyfriend looks mad enough he won’t let you blow him tonight!”

Even in my alcoholic haze I’d never felt so totally emasculated and humiliated. I hurried away from them with their laughter ringing in my ears.

When I returned to Tommy I didn’t want to sit. Instead, my unsteady hand trembled and shook as I picked up my drink off the bar and guzzled it down.

Tommy angrily said, “C’mon, let’s get away from these godawful cunts!”

I wanted to crawl in a hole and die but I quickly followed Tommy out the door. It was by-far the lowest I’d ever felt in my entire life.

Instead of his hand on my back, Tommy put his arm around me and pulled me close to him. We slowly walked down the street like that and I didn’t care who saw us.


We walked in silence until we approached ‘The Leather Vest.’

“Do you need to take a leak?” he asked.

I hadn’t until he mentioned it.

“I can wait til we get to your place,” I softly replied.

“Are you sure?” he asked pointedly.

I knew what he meant and became awash with a fresh embarrassment. I had recently pissed myself after saying ‘I can wait.’

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