Another Confession: James

I originally decided that I was not going to write about this encounter because I again have to confess going over to the dark-side. Because, I literally thought for an entire weekend that I had fucked up and would lose everything that I had worked so hard to achieve. Because it involves someone that I work with and I usually only write about tricks that I will likely never see again. Because I still do not fully understand why I took the risk I took and why I became so angry with the person who was just trying to tell me that he too is gay.

Over the years I have worked with him on several occasions on several different assignments. From the first time we were assigned to the same project team, there was something between us. I absolutely hate the term “Gaydar” and refuse to call it that. It was just something about the way in which we interacted…the way he would catch me staring at him and he would refuse to look away until I did…yet still, nothing was ever said.

James falls perfectly within my wheelhouse of what I like. He is in his early 40’s, dark brown close crop almost military hair cut. Probably and even 6’ tall and somewhere between a 36” and 38” waist depending upon the cut of the pants. He as a slight mid-section but he also has muscle definition in his arms, shoulders and chest. Having had seen him several times changing and in the shower, his hairy chest with a “happy trail” leading into his groin and slightly above average cut cock has always provided me with ample jack-off fader.

Even though there has always been this unmistakable…thing…between us, neither one of us ever acted on it or said anything that was in anyway unprofessional or inappropriate, at work or elsewhere. One reason for this…on my part anyway… was the bright gold wedding band on his finger. From common chit chat I knew that James was married and had a kid…a daughter I believe.

All of this changed several months back. Originally, I heard through the work grapevine that James was taking a transfer to the Seattle Office. Then a few weeks after that I happened to see James at one of our mandatory meeting, which was strange if he was now working out of Seattle. I asked a buddy of mine next to me about it and he had heard that that all fell threw for some personal reasons. Later that day, I noticed that James was no longer wearing his wedding ring. Putting two and two together I figured that the personal reason was a pending divorce.

A few months ago, James and I were assigned to a short project with a few others. When I had the chance I asked him

Me: “How is the family…well I hope”

James: “Yes, but my wife and I have divorced and she has taken a new job on the West Coast”

Me: “I am so sorry to hear that…must be hard on the little one”

James: “Well she seems to be coping well. She says she likes having a home on each coast”

Like most guys when talking about sensitive subjects, this entire conversation took place with minimal eye contact, but when I said:

Me: “Well we will have to get together for a beer… or something soon then”

As soon as I said this, James looked me straight in the eyes saying nothing for a moment…just looking at me as if he were trying to decide if I was just talking and being polite, or if I were making a loaded statement. After his silence had be come somewhat awkward, he said

James: “Umm Yeah we will have to do that some time”

And then he walked away.

Actually, I was just being polite, but his reaction gave me pause and I once again began to wonder…is he…or isn’t he?

A couple of weeks later I ran into him at work on a Friday afternoon. I made a snap decision to go for it and asked him if he had plans that night. He said no, so I invited him over to my place for pizza and beer since the house mate was gone for the weekend. Again, he paused giving me that nervous look before saying

James: “Okay…about 1900 hrs?”

Me: “Perfect…I think we should get to know each other better”

Pause…

James: “Umm Okay… see you later then”

I don’t know folks… you tell me… I thought I was pretty direct and struck an appropriate balance between being cordial and suggestive. I mean I think most would see that invitation as something more than just drinking buddies hanging out… or maybe not.

True to form, James showed up right at 1900 hrs. He brought some high end beer and was looking very sexy in just a plain t-shirt and blue jeans…just your average regular hot man.

I directed him to the couch and gave him a beer. I made a point of making eye contact with him and holding it. We did not say anything for like a full minute…just stared at each other…AGAIN FOLKS, yet another indication that he knew exactly what was going down.

At this point I was hard as a rock and it was obvious. I looked down at my crotch so that he would do the same… and he did…but said nothing, just returned to staring at me though his legs were spread a part and he held his beer bottle with both hands in the middle of his crotch…I think to hide his own boner.

Still without saying a word, I stepped between his legs and began to unbuckle my belt. I swear he looked like the proverbial deer stuck in the headlights. Just as I was pulling down my sipper James snapped back out of his trance…jumped up off the couch and said

James: “You have the wrong idea about me…I mean I am straight dude… I’m not….ya know”

He said all of this while he made a beeline for the door.

I literally kicked my own ass for the rest of the night. How could I be so incredibly stupid? Coming on to a Straight guy…that I work with!!! All that night and all the next day, all I could imagine was James telling everyone at work what happened. I envisioned be fired for sexual harassment and brought up on charges. Without a doubt, it was right up there with the worst 48 hours of my life.

I repeatedly called James’ cell leaving messages apologizing for my huge mistake, although my pride would not allow me to ask him to keep it between us…I mean…I own my actions and accept the consequences for those actions.

At 1000 hrs Sunday morning I am sitting in my robe in front of the tv only half watching Sunday Morning with Charles…whoever…and there is a knock at my door. I have to admit, I had a moment of panic…I thought I would have at least one more day before the shit hit the fan and all hell broke lose. When I opened the door, there stood James in that same t-shirt and jeans from Friday night. I stood there holding the door open…staring at him… prepared for the barrage of insults…anger…threats. All he said was

James: “May I come in?”

Me: “For what… to make me feel even more like a shit-head?”

Whit that, James stepped in the door, carefully closed the door behind him, turned back to me and kissed me full on the mouth…tongue and all. To say I was in shock does not even begin to cover it.

When he broke the kiss he said

James: “I have thought about doing that for about two years now”

After a moment or two, my shock was replaced with rage!

Me: “DO YOU HAVE ANY FUCKIN IDEA THE SHEAR HELL YOU HAVE PUT ME THROUGH THE LAST TWO FUCKIN DAYS!”

I swear my fists were balled up and I was about to through a punch. Sensing this, James put his palms up and slowly stepped back saying

James: “Yes I do, but give me a break…You have to remember what it was like when you first…finally admitted to yourself that you like guys! That shit aint easy…so I have been going through just as much fuckin shit as you!”

I was not appeased and I had now backed him into a corner

James: “Look, we both know why I am here…so you can either beat the shit out of me or fuck the shit out of me…but you are not going to do both…so which is it?”

I have to give James credit here…in our job we are all trained and highly skilled at defusing tense/aggressive situations…this was straight out of the text book and it worked. I snapped off my robe revealing a fat black cock that was…I kid you not…as hard as fuckin steel. I don’t know if it was the attraction, the emotion of the situation, the shear relief of what I had been stewing about all weekend or all of the above, whatever it was I was crazy horny and hard.

As my robe hit the ground I issued a one word command

Me: “Follow!”

I led James to my bedroom. Once there I went straight to the night stand and pulled out my cock-ring and the high end lube. I had no idea if James had ever been fucked before, if he was clean or dirty or what…at that moment I could give a flying fuck…I was going to take out all of my frustration and emotion on his ass. The cock-ring is significant. A cock-ring on my fat cock simply makes it a battering ram…for a long time!

By the time I turned back to James, he was down to just his white gym socks and a 6.5” hard-on.

As I pushed him down on the as yet unmade bed, he saw that look in my face… he saw the dark-side and he started to say something like “Please don’t hurt me” or “Please go slow”, but he was cut of half way through the word “Please” as I slapped him hard across the face.

I waited for a response… I waited for him to swing back…I wanted to fight… I wanted to fuck him up…then fuck…him up the ass! But instead of swinging back he held my gaze for a moment and then simply turned over offering up his very hot and slightly hairy hole…Just like he said downstairs “…you are not going to do both!”

Again, like a true pro, this simple act decelerated my aggression a bit more. Oh I am still pissed off, but now I am again focused on fucking rather than fighting.

I swear I dumped a half a bottle of lube in his ass and took a good ten minutes just work my way up to three fingers in his ass. It usually take four fingers to open a hole large enough to take my fat cock, but I wanted this to hurt. I lined up my battering ram and with one hard thrust was able to get about half way into him. Needless to say, this hurt him a great deal and all measures of decorum and defusing went out the window. At this point we were fuck-fighting.

After that first thrust, James did everything he could to get away and he almost did a couple of times. But, after a minute or so I was able to regain leverage and thrust again…this time making it about three quarters of the way in. James was yelling at the top of his lungs in pain, throwing elbow back trying to knock me off him but I rode him like a bronco. With my dick as hard as it was and fortified with tight cock-ring all I had to do is keep the pressure up. With every squirm and attempt to get away, my cock sunk a little further. After about a full two minutes of this, I was balls deep in his ass and the fight in him was dwindling so he moved less but his mouth picked up the slack calling me every name in the book…I was particularly proud of

James: “Get that Nigger Dick Out Of Me…You killing me you Black Son of A Bitch!”

And this one a bit later

James: “Don’t you dare shoot that Monkey Juice In Me!”

But by this time he uttered that last one, the racial slurring had become part of the scene…in that we were both egging each other on with the most vulgar and demeaning language that we could come up with. Normally I am not down with such language but some how…for some reason…it fit here and made the fuck incredibly hotter!

Me: “Who’s the Nigger!...Who’s the Nigger…you the Nigger after I fill you white belly full of my black babies”

James: “Oh…Fuck Yes…DO IT…DO IT!”

I swear I shot a pint of cum up his ass

Me: “Uunnnaaa…Unnnaa…Unnnaas Yeah…Yeah….take that Nigger load you filthy White Bitch”

With the cock-ring I stayed hard and well after I was done dumping my load up his ass I kept fucking him and rolled us both over onto our side so that he could get to his cock.

Me: “You hear that…You hear me churning all of that cum up in your ass…hear how wet you are with my cum bitch”

That was all it took…James shot a massive load…I mean MASSIVE…as in he must not have cum in a month, all over my bed sheets.

Needless to say, we were both extremely exhausted. I don’t think either one of has slept all weekend. Once my cock finally slipped out of his ass, I reached down and pulled the sheets and covers over us and we promptly fell asleep.

I woke up around noon to find James already awake and staring up at the ceiling. Again, I am no psychologist but I know a man who needs to talk some things through when I see one. I got up and fetched us a couple of bottled waters from the upstairs frig and we stayed in bed and just talked until about 4:00. I am not going to go into that conversation here…all of you reading this who have “Come Out” already know the conversation chapter and verse. At 4:30 we fucked again but in a much more tame fashion.

Under the umbrella of full disclosure, I only decided to write this story last night after watching my first episode of …I hate to admitted it but after so much pressure from all of the gay people I know, I finally watched my first episode of “Glee”. Okay Okay it was not bad…not great and I don’t think I will make a habit of it…but not bad. Anyway it was the episode where the gay kid confronts his bully oppressor and the bully ends up kissing him…basically revealing that he too is gay.

After watching that show I was sitting there thinking about how hard it is for us to really be who we are especially after we have invested so much in trying to convince others and ourselves that we are something that we are not. At that point I decided that I am ready to write this very true story. To this day I still do not know why I was so angry when James basically said “Hey, I am just like you.” I know this is a very long story, but if you have any thoughts…please share.

Oh Yeah, before you ask…no James and I have not fucked again…I think the first fuck ruined the potential for fuck buddies, but we are very good friends.

Lil-bit

A few months ago, I was at work on a Friday and wanted to be just about anywhere but there. Not because I don’t like my job… love my job in fact…it was just a slow Friday and I was so ready for the weekend to begin.

Since it was such a slow day, I pulled out my personal computer and wireless internet and quickly went through my various hookup accounts. When I got to Manhunt, I was instantly pinged by this guy I will call Lil-bit. I call him that because he is only 5’7” tall and I am guessing a 31” waist. If you have been following this blog you know this is not my type, however, Lil-bit is in fact a Red Head, which makes up for a lot with me as you know. The other thing about Lil-bit is his persistence. This guy pings me every time he sees me come online for over a year now. We usually have some very polite chat ending with him asking me to come out to his place and fuck him. That chat would always end there because the other negative about Lil-bit, is that he lives over an hour away from Washington DC. As a rule, I am not willing to go that far for a fuck…at least not a “First Time Fuck” which are always unpredictable. However, on this particular Friday I was actually considering it given that work was slow and that it was a very nice day outside.

When I told him that I was considering making that drive it caught him by surprise and he owned up to the fact that he had been chatting with someone else at the same time, and that the guy said that he would be there in forty minutes. I could tell from the tone in his voice that he thought that this would be a deal breaker and that he had missed his chance with me. He was wrong.

I proceeded to ask him a couple of key questions

Me: “Have you played with this guy before”

Lil-bit: “Oh yeah, we hookup about once a month”

Me: “White guy or black”

Lil-bit: “Black”

Me: “What do you usually do with him?”

Lil-bit: “Used to be just sucking him off, but he has fucked me a couple of times, but he is always a quick visit so he will be long gone by the time you get here so…”

Me: “What do you think you two will do this time…I mean…is he going to fuck you?”

Lil-bit: “Probably…yes”

Me: “Does he fuck you Safe or bareback?”

He paused before answering.

Lil-bit: “He fucked me Safe the first time, but bare the second time.”

Me: “Will he breed you?”

Another pause

Lil-bit: “Probably”

Me: “Listen to me very carefully, you are to send me a text when he gets there, and another text when he leaves.”

Lil-bit: “Yes Sir”

Me: “Let him breed you, and do not shower or clean up…I want your cummy hole…is that clear?”

Lil-bit: “Yes Sir”

It took me about ten minutes to get out of the office and on my way to Lil-bit. I was not even out of DC yet when the first text came through saying that Lil-bit’s friend had arrived. Approximately fifteen minutes later I received a second text that it was over and that his friend was in the shower.

I arrived at Lil-bit’s house in exactly one hour and ten minutes. The house was in one of those cookie cutter developments where each house was one of three or four model design, but big…four bedroom and three and a half bath big.

Lil-bit answered the door in a t-shirt, gym shorts and white gym socks. I have to say that Lil-bit has a very average look. His nose is a little too big for his face, but his short red hair and tight body made up for that…especially when he was naked. Naked he had the body of 25 year old instead of his actual 43 years, and for a little guy, he had a gorgeous 8” partially cut cock sprouting from a sandy red bush.

As soon as I was inside the house a few things were obvious…he was partnered. Pictures of him and his partner of several years were hung all over the place. It was also obvious that they had some money, I put the value of the house around 600K and I got the distinct impression that his partner was either a Doctor or Lawyer and that Lil-bit was a House Husband…working on taking care of the house and dogs while hubby brought home the bacon.

In that moment when you make small talk before sex, Lil-bit proudly showed me through the downstairs pointing out the elaborate crown molding, wall papering, and electrical work all done by him.

As we made our way up to the guest bedroom I asked him about his partner

Me: “Obviously your are partnered and in an open relationship?”

Lil-bit: “Yes, but it is more don’t ask don’t tell…although he had an 18 year old up here the other night while I was watching tv in the basement”

At hearing this I found myself a bit irritated. This was seeming more and more like a revenge fuck…Look, I am fine with fucking a guy in an open relationship, but otherwise, I don’t want to be caught up in someone else’s shit.

When we got to the spare bedroom, everything was in its place and immaculate…but shouldn’t the bed be messed up if he was just fucked in it an hour ago…especially if I told him not to clean up? A little more irritated.

Once in the room, we wasted no time getting naked. As soon as my cock spring free from my underwear, Lil-bit was on his knees taking it deep in his mouth. That was all good and well, but I did not drive over an hour for a blow job. I literally picked Lil-bit up and tossed him on the bed. I then pushed his very cute little legs up to his chest and dove my tongue into his very pink, but very clean hole…Now I am really irritated….no…at the discovering that there was no cummy hole, I was pissed. Either Lil-bit lied, and there was no other guy…or he lied when he let me believe that he took the guys load when he really did not…or he lied when he said he would not clean up but actually did….either way you cut it, I was lied to and now I am pissed, and I instantly when to the dark side.

After licking his totally dry and clean hole for about a half a minute, I stood, pulled his butt to the edge of the bed, took aim with the head of my fat black cock, and jammed my hips forward. Lil-bit had started to say something but he was not able to finish it as the pain of a nearly dry penetration racked his little body.

On that first stroke, I could only get the head of my cock past his sphincter. He was tight…too tight for someone who supposedly was just fucked and hour ago.

Through gritted teeth, Lil-bit attempted to let me know that hurt only to be cut off by the second full hip thrust which pushed my fat cock another inch in to his protesting hole. Upon this second thrust, I held it there keeping maximum pressure against his hole. With gritted teeth and eyes squinted shut, Lil-bit said

Lil-bit: “Please…please .Sir I cant take it…please Sir”

I abruptly pulled my cock out of his hole and said

Me: “Don’t…Move!”

I then reached over to the bed stand where he had set out some lube and poppers. I poured lube into my hand and massaged it into his hole and then on my cock.
Lil-bit: “I need the poppers Sir”

Me: “Shut the fuck up…what you needed to do was tell me the truth…you don’t have cummy hole…and no one fucked you an hour ago…did they?

After a brief pause he acquiesced

Lil-bit: “No Sir…he called back and said he could not make it…I was afraid that you would not come if I told you…I am sorry Sir”

Me: “Never lie to me…liars have no honor...you are going to get fucked now and trust me, you will remember this for a long time”

With that, I re-entered Lil-bit, going balls deep on the first stroke. His head flew back against the mattress, the veins running along his neck became visible and both fists were clutching the covers.

I had his legs hanging over my forearms and my hands held his forearms down as my hips settled into a quick and aggressive thrusting rhythm. The tightness of his hole lasted for the first twenty to twenty-five strokes. After that, his hole was completely open and my cock moved freely within him. By this time, his pain was subsiding and his demeanor was changing from one of struggle and defense to one of acceptance and pleasure.

I continued to fuck him in this position for a sold fifteen minutes non-stopped. The only sound in the room was the thwack-thwack of my thighs and balls slapping against his upturned butt. We were both completely coved in sweat. By now his body had adjusted to me and he no longer gritted his teeth and squinted his eyes in pain…rather he was staring me straight in the eyes like he was in some sort of trance. His mouth was still open with drool dripping out of the corner and running down along his chin. His cock, no longer hard but very full laid on his belly and there was a sticky stream of pre-cum flowing form the slit.

I worked him over hard for fifteen minutes and then felt the urge to cum. Without warning, I slammed deep in him one more time and let it go. I stopped counting after the fifth pulse of cum shot from my cock into his guts.

When I was done, I kept his legs pinned to his chest as I pulled. This caused his hole to stay open and as my cock came out so did a huge glob of very thick cum, creating a huge wet spot on the covers. I scooped some of it up on my fingers and brought it to his mouth. He eagerly licked my fingers clean.

I laid on the bed beside him for a moment to catch my breath. He sat up on the edge of the bed. His shoulders were slumped and his head hung low. Clearly there was a ton of emotions going on inside of him. I suspect it had something to do with his partner fucking and 18 year old while he was in the house…in short, it was clear that there is some serous trouble in paradise.
Me: “Do you want to talk about it?”

There was no response for almost a minute, then he sat back on the bed Indian style and proceeded to bare his soul for the next thirty minutes. I wont share the content of our discussion here but I was correct…it had everything to do with the changing relationship with his partner. A by-product of his emotional distress was that he had not been able to have sex to the point where he could get off…he would start thinking about the problems with his partner and lose his hard-on.

Now let me be very clear here….I am not a psychologist, psychiatrist or anything of the sort. I am just a guy who has been through some things.

Me: “Go get a picture of your partner…that one in the hallway downstairs will do”

He was very reluctant…he did not know what to make of me…just a bit a go I was literally a beast humping his ass like a rabid dog…now I am like this guy whom he can talk to about personal shit…I understood his confusion and reluctance but with some prodding he went and got the picture.

When he came back in the room with the picture, he saw me standing by the bed lubing my hard cock again and he froze.

Me: “Relax…and just work with me…okay? Come over here and lay that picture face up on top of the wet spot”

Lil-bit: “What…are you crazy?”

Me: “Maybe” I said with a smile “Just humor me… you got nothing to lose”

With that he came over and placed the framed picture in the middle of the wet spot. As he was doing this, I rubbed some lube into his ass. He shivered at the touch of my slick fingers on his tender hole. I made him bend over the side of the bed so that his head was right above the picture of his partner and the wet spot, and I slowly entered him.

Under the umbrella of full disclosure…all I wanted was to fuck him again…and yeah, it is pretty evil me to use his emotional distress to make that happen. I truly do feel bad that I did that for that reason. However, as I was slowly fucking him and gently stroking his back, he began to stroke his very hard cock. He did not take his eyes off the picture of his partner and before long he was pushing back onto my cock and racing to his own orgasm.

When he came, he clamped down so hard on my cock that it instantly sent me over the edge and I dropped a second load into him. Understandably his orgasm was nothing short of an earthquake! He shot ribbon after ribbon of cum onto the bed covers and he had whole body convulsions.

I helped him lay down on the bed where he buried his face in the pillow and quietly cried. I simply gathered my clothes and left the room.

I was about a mile from home when I received a one word text message from him…”Thanks”