That Side of the Fence

Chapter One

I had known Taylor for almost a year before I took action. 'Known' is rather a strong term, though. Acquainted is probably more appropriate.

I serve breakfast to some one thousand people in a building that has the capacity for four thousand. Not all thousand eat everyday, but I do see about two hundred regulars at least once a week; a good one hundred on a nearly daily basis. Taylor fits somewhere between these two groups.

Our banter is generally good natured, mostly jibes, but once in a while we call a truce and try to be nice to each other.

Around Halloween the previous year, I found out that he was partial to...well, he walked a side of the fence that I only walked in my fantasies. He is gay. He isn't overtly so. What I mean is that he doesn't go around making sure everyone knows that he is gay. Nor does he hit on every male he talks with. But through our playful banter, I felt a small connection with him and I wondered what it would be like to bring my fantasies to life.

One more thing that I should explain here: I enjoy anal sex. I have only had four live penises in me, ever, and three of those were brothers during that awkward experimental phase and only one of them ever ejaculated in me and only once. The other was of a neighbor kid, I forget who he was or where he lived, and he only did it on a dare, in and out sort of thing.

But I have enjoyed many other things in my anus: fingers, pens, markers, toothbrush handles, plunger handles, broom sticks, candles, pop bottles, carrots, cucumbers (my second favorite) and my favorite - a piece to a toy that was nearly five inches in circumference and twelve inches long. Its girth only fit in me with a little bit of effort and lots of lubricant, but when I was loosened up and it was well lubed, I was in shear bliss.

I had my first anal orgasm when I was twenty-five. I became addicted to them in my early thirties. I realized my addiction in my early forties and had to cut back when I was forty-five. I had visions of being found naked in a bathroom somewhere, a cucumber sticking out of my ass, dead of a heart attack.

It was about this time that I decided that I wanted to have an affair. More exactly, a gay affair. I had been hetero for nearly all my life, the only exceptions being those same experiments with my brothers. And they don't really count. (Well, okay, the times with my youngest brother were really close to having an affair. It was he, by the way, who came in my ass. He was also the only one I had ever given head to and I even swallowed.)

But how to approach this? I had been married for over twenty years. I hadn't dated anyone besides my wife for even more time than that. And how to keep it from my family? Besides, all the gay guys I know, knew that I was taken. Even Taylor.

After some thought, I figured out a pretty good plan. It would take a little time, but I hoped it would work.

Through discreet inquiries, I found that I could email Taylor at his work email. I set up an anonymous email address through Yahoo! and sent off my first email.

Dear Taylor,

You know me, but I don't want you to know who I am just yet. I am interested in having a fling or affair or whatever. I know that you are currently unattached. I was wondering if you would like to hook up or something?

Me

The hard part for me was trying to keep a straight face and even demeanor when I saw him. I overheard him the next day talking to a coworker. He said that he had received the email and that he was very curious about who had written to him. He started naming off people that he thought it was, but of course he probably wouldn't even consider that it was me. He said that he had sent off a reply and was waiting.

I hurried home that afternoon and logged onto my anonymous email. Taylor had indeed answered.

Dear Me,

I'm not saying that I would definitely go out with you, but I am interested in talking to you. Will you IM me? Use Yahoo! Messenger, since you are using a Yahoo! email.

Taylor

I opened Yahoo! Messenger and sent him a request. Ten minutes later he replied.

Taylor - Hi

Me - Hello

T - Who are you?

M - Not just yet.

T - Why?

M -????

T - Whatever. Listen, I am interested in getting to know you.

M - Okay. I won't lie to you. I'm not good looking. I'm middle aged, out of shape and as far as I'm concerned, rather ugly. But since when are looks necessary for a relationship?

T - Are you just being modest? I am a bit unnerved by your mysteriousness but okay. When do you want to get together and talk IRL?

M - I'm still working on that. I need to keep some amount of privacy as I don't want some people find out that what I am doing.

T - Are you attached?

M - To be honest again, I am married. I have been hetero for all but a few experiments with my brothers when we were young.

T - So why me?

M - IDK. I guess it's because I know you're gay and that you enjoy it.

T - Who the hell are you and how do you know me so well?

M - Sorry, guy, but not just yet.

T - God, you're annoying.

He signed off the conversation and I sighed. I also had a raging hard on just thinking about the fact the he was interested. I jerked off, spewing hard and long.

The next day at work was even more difficult. When I saw Taylor at breakfast, he looked agitated.

"What's up?" I said, nonchalantly.

"Nothing, I am just a bit frustrated."

"Why?"

"Interrogating me, huh?"

"Yep."

"Well," he said leaning closer across the counter, "I've been talking to a guy through email and IM and he wants to hook up with me. I can't figure out who it is."

"Wow, cool. Didn't you just break up with what's-his-name?"

"Josh. Yeah, the bitch."

"Careful."

"Yeah, whatever. Anyway, I really want to hook up with this guy. He says he's ugly, but I think he's just being modest. I'm also getting rather, well, horny. I haven't had sex in nearly a month and my fist doesn't count or do the trick." He winked at me.

"TMI, dude, TMI."

"Sorry, anyway, thanks for breakfast."

"De nada."

Knowing that he was intrigued and interested, I figured I would take a stab at meeting him. But where? I figured that a somewhat public site, with plenty of exposure as to not have anyone assume I was making a pass at this guy. Well, anyway, I noticed he was signed into his IM so I messaged him.

Me - Hey Taylor, how's it going?

Taylor - Okay. God it's annoying not knowing who you are.

M - I know. I'm ready to fix that. I'm still not sure I'm ready. Okay, I want to be with you, but I need to be discreet, yet, hell IDK.

T - Listen, going gay isn't the easiest of decisions. If you're not sure you want this, then......

M - Taylor, I want to be with you. I really do. But if I do this wrong, I will hurt a lot of people. Okay, here goes. Why don't you meet me for dinner tonight? Some place public. I'm thinking Golden Corral.

There's a short pause. I watch the screen, the seconds, then minutes passed. After ten minutes I got a reply.

T - Okay, I'm game. What time?

M - 6:30, but I'll wait until you're in and seated. I will come and join you at your table. I'll greet you as if it is a chance meeting.

T - Fine. I reserve the right to end this at any time.

M - I understand. I hope that you don't. You will be surprised at who I am though.

T - Why don't you just tell me now and end the suspense for us both?

M - Can't, won't. don't want to risk....anyway, I will give one more thing. If by chance I chicken out, don't wait more than fifteen minutes. I will make arrangements to pay for the meal in advance so that there will be no risk, monetarily, to you. Just tell the manager your name.

T - If you think you won't come, just say so now and we'll end this now.

M - Sorry, Taylor, I didn't mean to sound so wishy-washy. I'm just leaving an out. Sorry.

The next couple of hours were intolerable. I called the restaurant and talked to the manager. He took my credit card number over the phone and gave me a reference code. I then headed up to the shower.

I told my wife that I was going to meet a new friend for dinner. She was surprised, but she trusts me. I explained that he was a guy from the building I work in, and we have lots in common. She was then excited as I have been somewhat of a recluse in the friendship department for most of our married years.

At six o'clock I headed for the restaurant and arrived with fifteen minutes to spare. I found a spot where I could watch the front door yet remain unseen by Taylor.

He arrived a couple of minutes before the appointed time. He was hesitant to go in, stopping just outside the door. He scanned the parking lot, then stared out to the road. He shrugged then went in. I carefully walked to the door and watched as he passed through the pay station, turned left, and headed to the tables. I moved in through the doors and watched him take a table in a secluded area. At first, he sat facing the food service, but then moved to have his back to the food. He wanted it to be a surprise as much as I did.

His server took his tray, and he scanned the restaurant one more time before turning back to wait. I passed by the pay station and looked back and forth through the dining room as if looking for an empty spot. I then moved to Taylor's table and stood behind him.

"Don't turn around," I said quietly. He started to turn but stopped. "Close your eyes," I said.

"Whatever," he said, resigned.

I slowly moved around him, watching to make sure he wasn't looking. I sat down across from him and took a deep breath.

"Okay, open 'em up," I said, trying to smile.

He opened his eyes, and they went big as saucers.

"You," he said loudly.

"Shsh," I said putting my finger to my lips.

"I would never have guessed," he said, lowering his voice and looking around.

"I know."

He stared at me for long minutes. "Well," he finally said, "shall we eat?"

I nodded and we went and got our food. He didn't leave and he didn't seem too uncomfortable. I was shaking like a leaf in a mild breeze. We returned to the table with our first plates full.

We started to eat in silence. He then looked up at me. "So, what do you have in mind?"

"Well," I felt my face turn bright red, "as I explained, I am interested in something. Mainly, I am interested in sex. If something else comes about, well, I'll deal with that later. I don't plan on leaving my family, but I want more in my life."

"So, I'm just a diversion in your life."

"It sounds cold, but....okay, basically that's it. Does that change the way you feel?"

"Not really. Josh and I were together for so long that I was starting to feel smothered. An unattached relationship will be just what I need right now. I assume that this will be open. I mean if I decide to see other guys, there won't be a problem."

"Actually, that would be more than fair. I don't plan on ignoring my wife in all this."

"That's what I figured. So do you really know what you're getting yourself into?"

"I think so. Listen, there are things I would like to tell you, but this isn't the place. Now that we have met and I am feeling more comfortable with this, can we set another date...god, I haven't used that term in a long time...anyway, how about another date."

"Sure. When?"

"How 'bout a movie? Say Saturday, at 5:30."

"Early enough for less prying eyes?" he said, coyly.

"Yeah, I guess so."

"Okay, but tell you what, let me pick it up. Actually, let me take you someplace different."

"Where?"

"You'll see. Meet me at Albertson's over there about 5:00 on Saturday."

I smiled and nodded. We finished eating, then left together. We separated to our cars and went our separate ways.

The next two days seemed to drag. Taylor kept his demeanor well when we saw each other at work. But my work companion noticed that I was being nicer to him. Taylor and I had always teased each other; but now, as my fellow worker noted, we actually were civil to one another. I just shrugged it off.

On Saturday, I excused myself from my family again. I drove to the Albertsons near my house and waited. He pulled up next to my car and motioned for me to join him in his car. I shrugged and stepped out of my van. I looked at his car. He was driving a low-riding Honda Civic. I opened the passenger side and looked in.

"How in the hell do you expect me to get down there?"

He laughed and called me an old man, which of course I agreed with. Somehow, I was able to fold myself into his toy car. He roared off, smiling at my discomfort.

"Well, it's better than going out in your piece," he said, laughing.

"Whatever," I said.

He headed to the freeway and then barreled towards the downtown area. He drove rather fast and quite recklessly. I was scared to say the least. He just laughed at me as he exited off the freeway. He headed further into the downtown area and then pulled into a parking garage near the outdoor shopping center on the west side of the downtown area.

He laughed as he literally had to pull me out of his car. He led me to the elevator. He stood near me, but I could tell he was still a little doubtful about our relationship. Just before we reached our stop, he bent over and kissed me on the cheek. I looked at him and he smiled, shyly. He led me out of the elevator and down the walkway. We walked for a little and then he stopped in front of the store. I gasped quietly as I noticed that it was a sex shop. He smiled and held the door open for me and then followed me in. He pointed to the back of the store and then led me there. At the back of the store was a counter next to a black door.

"Hi, Jake," Taylor said.

Jake turned to face us. He was wearing heavy makeup and a blond wig. I then noticed that his clothes were feminine.

"Oh, hello, Taylor, glad to see you again," Jake said reaching out to touch Taylor's hand. "Who's the big guy?"

"A friend," Taylor said, a little shyly. "Two please."

Taylor paid Jake a twenty and Jake smiled, then bent and hit a button under the counter. A buzz sounded from the door and Taylor reached out and pulled the knob. He held the door and ushered me in.

We entered a small theater, with only about thirty seats. There were only two other male couples there. They turned and smiled, waving at Taylor. Taylor waved back and pointed me to seats at the back of the theater. I settled into one and Taylor sat next to me. In the next ten minutes, three other people entered the theater. As they settled, the lights dimmed, and the screen flickered to life.

A nice-looking young man was walking down the street. In the background, 70's style music was playing. The opening credits played as he walked through a downtown scene and then jumped on a bus. The camera stayed on him for a few minutes as he rode through town and then followed him as he exited to a suburban neighborhood. He walked briskly, looking around. He walked up a long sidewalk to a covered front porch. He knocked, then shuffled his feet as he waited. An older man, mid-fifties, dressed in a bathrobe, answered the door, and smiled. He let the younger man. The camera followed them into the living room.

"Well, Mr. Jives, you said on the phone that you were looking for young men. What is it that you want me to do?"

Mr. Jives smiled. He stood and moved in front of the young man, letting his robe fall to the floor. The young man gasped at Mr. Jives' nakedness.

"Um, I don't understand." The young man said, watching as Mr. Jives began to stroke his penis. It lengthened to about eight inches and was about three inches around.

"I like young men, see," the older man said, "they're so vibrant and horny. Come now, Marcus, let me show you what a real man is."

Mr. Jives took Marcus by the hand and pulled him up, he leaned to Marcus and kissed him on the lips, whilst his hand moved Marcus's hand to his now hard member.

Marcus pulled back with a look of shock on his face. He looked down at the thing in his hand.

"I..I...I've never done anything like this before," Marcus said as the old man's hand moved back and forth, stroking the taut flesh.

"You will enjoy it," Mr. Jives said. He then took Marcus by his free hand and led him into a bedroom.

I felt a hand on my lap and looked down. The hand grabbed my now hard member in my shorts and began to stroke me slowly. I followed the arm attached to the hand and looked at Taylor. His face was riveted to the screen. He kept stroking me as I followed his gaze to the screen.

Mr. Jives now had Marcus undressed. Mr. Jives sat on the bed and looked straight at Marcus's now hard member. It was lengthy nine inches long and Mr. Jives eyed it expectantly. Mr. Jives leaned forward and kissed the tip in front of him. Marcus jumped but didn't move away. Mr. Jives then took the member in his fist and began to stroke it slowly, smacking his lips as he watched the flesh extend another inch.

Taylor's hand moved to my waist band I felt it move inside my shorts and briefs. I sighed as I felt his hand engulf my hardness. I shivered; a man was touching me for the first time in years. I felt coolness around my lap and looked down to see that he had pulled my penis into the open. I scooted down a little to give him more lap area. He turned to me and smiled.

"Not very big," he whispered and giggled. He looked back up to the screen.

Mr. Jives had moved his mouth to engulf the young buck's dick.

Marcus hissed as Mr. Jives took his whole member into his mouth. Mr. Jives began to move back and forth, pumping the long meat in and out of his mouth while massaging Marcus' balls with his fingers. Marcus moved his hands to the back of Mr. Jives' head and began to pump with his hips.

Taylor was now pumping me in time with Mr. Jives on the screen. I could feel the build in my balls and hissed quietly. I noticed that I could only see some of the heads of the couples in front of me. I felt myself nearing the edge.

Marcus grunted loudly and Mr. Jives moved his head back. A long stream of come shot out of Marcus and coated Mr. Jives tongue. Mr. Jives then moved forward to take Marcus deep again.

I felt myself hit the edge. Taylor leaned down and took me in his mouth. I shot hard as his tongue licked across the top of my head. I shot three more times into Taylor's mouth. I forced myself to watch the screen.

Mr. Jives had pulled back again and began to pump Marcus' dick, milking out all that Marcus would give him. Marcus just grunted and spasmed as each wave of ecstasy flowed through him.

I felt myself shiver again as Taylor licked me, getting all he could out of me. He then moved up and looked me in the face. His lips moved to mine, and I met him willingly. He wrapped his arm around me as we mashed together hard. I could taste my come on his lips and tongue. We kissed for long moments. Taylor then moved away and looked back at the screen.

Mr. Jives and Marcus were now on the bed together kissing and caressing each other. Marcus moved his hand to Mr. Jives' hard member and began to slowly stroke him. Mr. Jives hissed as Marcus began to stroke him faster.

"No, boy," Mr. Jives said, pulling the boy's hand away, "I want to use him."

Marcus looked confused for a moment. Mr. Jives moved his hand to Marcus's hind side and began to massage his anus. Marcus's eyes shot open wide in surprise.

"You want to....," he said quietly as Mr. Jives nodded his head.

I took my chance now and moved my hand to reciprocate to Taylor. He moaned as I pulled his hard member from his pants. It was at least eight inches long. I smiled as I looked at the viral young man's hardness. It reminded me of a time when I had others just as long.

Mr. Jives moved Marcus onto his knees and had him bend his head to the bed. Mr. Jives put some lubricant on his fingers and began to massage and insert his fingers into the bright pink spot between Marcus' buns. Marcus moaned with delight. Mr. Jives put a condom on his long member and then placed the tip at Marcus opening. He gently pushed in. Marcus gasped and cringed with pain. Mr. Jives waited as Marcus became accustomed to him. He then pushed gently in. Feeling no further resistance, he plunged in hard. Marcus arched his back and gasped as Mr. Jives hit full into him. Marcus then laid his head back down and began to whimper with excitement.