📚 bisexual conundrum Part 1 of 5
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Bisexual Conundrum

Bisexual Conundrum

by Fantasizeandrealize
19 min read
4.74 (35300 views)
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Bisexual Conundrum Ch. 01

By Fantasizeandrealize

Life was great and it was only going to get better! I just didn't know how much better. I was twenty-one years old and in my senior year of an Industrial Engineering degree at a prestigious university. My grades were good and I found the subject matter of my degree fascinating. I was naturally slim but my body was muscular from a childhood of hard work, growing up on a farm. I was charismatic, unlike a lot of my geeky classmates and had been dating a really hot girl named Alison, for the past two years. She was an accounting major and was two years behind me in college. Life would be great for us!

I had just finished the first round of midterms of my last semester. I felt like going out drinking. None of my friends could come and Alison had late classes, so I went to higher end bar, that I had known about, but never went to before. I usually went to the college bars, where in those days, I could get drunk for five bucks.

Walking in I felt sophisticated and took a spot at the bar. The place was not packed but had a nice professional crowd. A lot of the people were either wearing suits or button-down shirts, with the ties removed. This place was very different from the ratty college bars that I frequented. It was classier, the patrons were older and the drinks were more expensive.

All the stools at the bar were taken so I stood in an unusually big space between two stools and waited for the bartender to come. To my right a couple were sitting in the two stools and they seemed to be in a deep conversation. To my left a big guy in his mid forties was sitting by himself.

As I was waiting for the bartender, the guy to my left says, "Hello, I have never seen you in here before. My name is Albert."

Albert extended his hand and I shook it letting him know my name was William, and that this was my first time in the establishment.

"If they don't know you here, they will take care of all the regulars first." Albert stated, "Let me get this drink for you as a welcome to the place."

Albert held up his hand and the bartender came right over. Albert pointed to me and I asked for a Guinness Extra Stout.

"Put it on my tab, Eric." Albert told the bartender.

"Guinness Extra Stout is an unusual drink for a young guy." Albert stated.

"I don't get to drink it often." I replied, "None of the college bars have it, I only get a six-pack in the grocery store on special occasions. I usually can't afford it on my college budget."

"I see." Albert said, "What are you studying and in which college?"

I told him I was studying Industrial Engineering at that this would be my last semester. Albert let me know, that he owned a mid-sized window frame manufacturing plant. He had built it up from nothing and was very proud of it. There was so much to talk about with him. I went into Industrial Engineering because I wanted to do my part in making America more competitive in manufacturing. Albert was already doing it.

Before I had even finished my Guinness, Albert had already called Eric over and ordered another round for us, telling him to put it on his tab, once more.

I thanked Albert and he just said sure and patted me on the back like an old friend but his hand just seemed to linger too long. I noticed it but didn't say anything, because our conversation was so good and he was paying for my expensive beers.

Our conversation got even more interesting, as he explained about some of his manufacturing processes and machinery. He also knew how to make me feel important by asking for my opinions and if I had studied such things in my classes. His hand also frequently found its way to the small of my back as we were talking.

It felt weird, but in a way his hand touching my back felt complimenting too. As our conversation progressed, Albert's hand inched its way lower, until it was fondling my left ass cheek. I was really weirded out by this, but once again kept quiet because I was enjoying the conversation and beer so much.

Eventually Albert was just kneading my left ass cheek and pushing his fingers right into the crack of my ass. The ironic thing, was that I was getting a stiffie!

I saw Albert looking down my front and smiling knowingly, when he saw the bulge, in my pants. I felt humiliated but for some reason I couldn't bring myself to tell him to stop. We had another three beers together. Albert put them all on his tab and the whole time he fondled my left ass cheek as if he owned it. I felt like Alison must feel like when she is with me. I always love grabbing her firm round ass!

Three hours after I had arrived, I shook Albert's hand and thanked him for the beers and great conversation.

He proposed that we continue it at his house. I politely refused, stating that my girlfriend would be waiting for me.

I saw the look of disappointment on his face as I mentioned my girlfriend, and took off.

When I got back to my apartment Alison was already there and I mauled her. I was so worked up and horny from Albert caressing my ass. Now however, I was playing Albert's part, and couldn't take my hands off of Alison's ass cheeks. I laid back in our bed and she rode me as I grabbed and fondled her fine globes. We both came hard, but I was thinking of Albert as I came and how great it felt when he fondled my ass.

Alison and I made out for a while, showered, and went to bed. That night I could not let go of her fine ass and kept thinking if she felt like I did, when Albert fondled me.

That following day, all I could think about in classes, was how good it felt when Albert fondled my ass. At five thirty after my last class, I went back to that same bar, looking for Albert.

He was not there but Eric came right over and brought me a Guinness Extra Stout. He smirked at me, as he served me, as if he knew something I didn't.

I asked him if Albert had come in this evening, Eric replied, "He usually comes in about twice a week around six." I thanked him paid for the beer and left a nice tip.

For the next week I couldn't stop thinking about what fool I had been to pass up on Albert's offer to go back to his house. I was aroused all the time and Alison and I were fucking every night. She even asked what had gotten into me lately.

I just told her that I love her and squeezed a firm globe of her perfect butt.

I had been to the bar four times now and had not seen Albert. I was becoming a regular. On Thursday the following week I saw him sitting at the bar. There were two empty stools to his right and I sat in the one closest to him shaking his hand.

"It is great to see you again, William." Albert praised, as his hand patted my shoulder and slowly worked its way down to my butt. "It is not every day that I meet a guy who I can talk engineering to."

"Our conversation last time was fascinating." I replied. "I want to hear more about your factory."

"Albert ordered a round and we resumed our conversation from the past week. He told me about new machines that he was buying and processes that he was implementing. He talked about labor problems and I could feel his big hand on the top of my ass.

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Man, was I a moron. How could he fondle my ass if I was sitting in on a stool?

I stood up and pushed the stool back, saying, "I have been sitting in class all day. I need to stretch my legs out a little."

Albert smiled at me in a knowing way. He glanced down, and once again noticing my tenting pants.

"I know exactly what you mean." He replied, "For me it is the opposite. I am on my feet most of the day at the plant."

He hadn't even finished saying it by the time his hand was resting on my now exposed ass.

Once again, the conversation was great. I listened with genuine interest, to what he was explaining.

Two rounds and so much ass fondling later, Albert asked straight out, "You know that I am gay right?"

I just nodded my head, "Yes." My heart was beating so fast.

"You have been a mystery to me." Albert went on, "You seemed to enjoy my fondling, last time you were here, but then at the end you told me that you had a girlfriend. I was surprised by that and then Eric told me, that you had been coming in asking about me. What's up?"

I explained to Albert. "First of all, I so enjoyed your conversation, last time. I was weirded out when you started touching me, but it just felt good."

"You felt like you were desired. Right?" He asked.

"Exactly." I replied, "I love grabbing my girlfriend's gorgeous ass, and you kind of let me know how she must feel, when I do it to her. I couldn't get it out of my head all week. I have been thinking about you, when having sex with her. It's crazy, but I feel that I have to get it out of my system."

"Let me warn you that you are treading in dangerous waters." Albert warned, "What if you really like it?"

"I don't know, but I have to at least try or I will never know and it will haunt me forever." I replied.

"Well then why don't we leave this place and find out?" He asked.

"Sure." I replied, "Just let me call Alison, to let her know I won't be coming home tonight."

In the early 90's cell phones were not a thing yet so I went to the bar entrance and called from the payphone. I told Alison that I was going to be working late on a project and would be staying at a classmate's place. This happened on a regular basis so she bought it with no questions asked. She would stay at her dorm room and hang out with her friends.

When I hung up the phone, Albert was behind me and mentioned that he covered the tab. I followed him out to a nice Maserati and we got in. Ten minutes later, we parked at a nice mansion on a hill overlooking a lake. Albert had been rubbing my thigh the whole way over when he was not shifting gears. I was tenting like a circus.

We entered his gorgeous house. Albert grabbed my ass and tried to pull me in for a kiss. I turned my head away and told him that I couldn't kiss a man.

"I get it." He replied, "You just want your ass played with. Correct?"

I nodded, "Yes."

He motioned for me to follow and we walked through the living room and down a hallway into a room that had a massage table in the center. Albert asked me to undress and jump up onto the table.

I did so, leaving just my tented underwear on.

"How am I going to play with that fabulous ass if you keep your underwear on?" He asked, with a smirk.

I know I turned red, when I removed them and laid back down on the table with my hard on under my stomach.

"If you were wearing some lacey French cut bikini panties, I would have let you leave them on." He said with a chuckle, "Oh my, look at that ass! So fresh and so ready for the taking!"

Albert now just grabbed both of my cheeks in is big hands and just held them. I felt the warmth of his palms and it was so comforting. He just stood holding them for a few minutes. He then pried my cheeks apart and let out a little whistle of appreciation. It was a good thing my face was buried in the hole of the massage table because I was burning in shame from having him look at my now exposed pucker.

"That is just priceless!" Albert said in awe, as he bent over and kissed my asshole. I almost leaped off the table I was so surprised. It felt like I was shocked.

"Calm down." He ordered, "A little kiss never hurt anyone."

My heart was racing like a train, I was so nervous. Albert once again pried my cheeks apart and planted another kiss right on my exposed hole. This time he frenched it, and lightly rubbed his tongue over it. Sparks of pleasure seemed to emanate from the contact. I had never felt anything so erotic before in my life.

Albert removed his face from my ass and I subconsciously raised it up looking for contact again.

"See." He said, "Your ass wants more! All in good time my young friend."

Albert spent the next ten minutes just squeezing and fondling my cheeks. He loved to push up on them towards my lower back and let go. This would cause the globes to bounce back into place and he seemed to get great satisfaction from watching them do so. He caressed my upper thighs paying close attention to the creases between my glutes and the backs of my thighs. He squeezed my cheeks lovingly and ran his fingers through my crack countless times. It was so erotic. It just felt so forbidden but so good. Albert made me feel like my ass was the most desirable object in the world. My cock was so hard it was beginning to hurt.

Albert once again pried my cheeks apart in his strong hands. He leaned in and kissed my pucker. This time I did not jump in shock but let out a long moan of pure pleasure.

"There we go!" He exclaimed, raising his head out of my ass and then reinserting it.

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He ate my ass out for over ten minutes. He explored every crease of my shutter with the tip of his tongue as I squirmed in pleasure. I could feel a large wet sticky spot forming under my stomach, from all the precum I was leaking. I was now moaning like a whore.

I almost panicked at the loss of pleasure when Albert removed his face and stepped away. I raised my head and was relieved to see him returning with a bottle of oil. He squirted some over my ass and started massaging it in. It was heavenly. He kneaded every square inch of my round ass. Occasionally he would run his fingers through my cleft and sparks of pleasure seemed to fly every time his fingers grazed my pucker.

I was now raising my hips off the massage table, raising my ass up trying to get more of that heavenly contact.

"We got an anxious one here!" Albert exclaimed, as he noticed how I was raising my ass.

I just moaned deeply in pure lust. I was jelly in his hands and could not form a word,

Albert now held my cheeks apar with one hand and started tapping on my rosette with the soft pad of a finger. Oh, it was divine and I arched my back, until it almost hurt, to expose my hole as much as I could.

Albert poured more oil into the cleft of my ass. I could feel it pooling on my hole. He ran his fingers through it a few times and then just stuck the end of his index finger gently into my hole.

I kind of felt violated and trapped but in an amazing way. I arched my back even more to try and get more of that finger inside. The friction from its intrusion was so gratifying. Like scratching a mosquito bite that itches but exponentially better!

"Calm down!" Albert ordered, "You will experience everything in good time."

He now wiggled that finger tip some and I groaned, clenching my ass as I did. I was fighting to not arch my back, to raise my butt onto that finger. It was teasing me so cruelly. I needed to be impaled by his digit now. I grunted in frustration as Albert just wiggled the tip.

I had to control myself, so as not scream in frustration when Albert removed that fingertip. I felt its loss. I felt more oil being poured into my crack and then that fingertip was pushed back in. I moaned in relief but it went in farther this time. It felt so much better now that the hard fingernail was past my clutching sphincter. Albert twisted it some and the friction from the rotation caused new sparks of pleasure to emanate. He then started sawing it in and out slowly. This felt better than the rimming. I was a mess of emotions and just moaned through the massage table hole that my face was resting in.

Albert worked that index finger in and out for a few minutes and replaced it with his thumb. I was confused. His thumb was not as long but it was fatter. I didn't know what I liked more. His finger reached deeper parts of my rectum but the extra width of the thumb stretched my poor hole out more and exposed more nerve endings to the friction.

How had I never tried sticking something up my ass before? This was phenomenal. I would have to get Alison to do butt stuff with me!

It felt especially nice as Albert cupped the bottoms of my cheeks in his palms and fingers, as that thumb worked its way in and out.

Albert withdrew his thumb and slapped my right cheek playfully, stating, "My oh my! What a greedy ass you have! It feels like it is trying to swallow my thumb like a piece of candy!"

I could only moan in agreement and frustration of not having that thumb inside my ring of pleasure.

I would not be disappointed for long as I felt two fingernails at the entrance to my hole. This time it hurt some when they popped in and I humped my hips into the massage table clenching my rectum hard around those invading digits.

"Relax!" Albert commanded.

I did and he rested just the tips of those two fingers in my hole for a minute while massaging my left ass cheek with his other hand. Albert felt when I was relaxed and started gently pushing them deeper. It still hurt some but the friction was also providing tons of pleasure. I let out a moan of pleasurable discomfort as they slowly worked their way deeper. My cock was sliding around in the sticky puddle of precum and I knew that I had found heaven.

A few insertions and withdrawals later, there was no more discomfort only increased pleasure from the extra stretching of my hole. Albert sawed those fingers in and out while massaging my left ass cheek. I felt desired and never wanted it to end.

Eventually Albert took out his fingers and wiped them off on a towel.

"You are now ready for the real thing." He calmly stated, "Sit up, so you can see what I am going to be putting into you."

I sat up and watched in awe as Albert removed his shoes, socks and slacks. I could see a huge bulge in his boxers.

"I have been tested for STDs since my last relationship, and am negative." He declared, "If you want, I can put on a condom but it will feel much better without one."

I trusted him and replied, "This will be my first time ever having sex without a condom."

"Good Boy!" He exclaimed, "You are going to love this! Up till now, it has just been a warm-up! Now lay back down. I am going to climb up over you. It will hurt when I put the head in. More than with the two fingers, but don't worry. I will go slow and you will feel the most intense pleasure of your life!"

Albert took off his boxers. His cock was a good seven inches long and much thicker than mine. It was nicely shaped and circumcised. I shuddered uncontrollably, as I laid back down on the table.

I resumed my position on the table with my face in the hole. I felt Albert climb up over me. I could feel the warmth of his knees on the sides of my knees. I also felt more cold oil being applied to my hole. My hole must have been gaping some, because none ran down my taint onto my balls, like before. It seemed to all go inside this time.

I then felt Albert's left forearm on the side of my ribs and his gut on the small of my back as he leaned forward and guided his cockhead to my pucker. It felt velvety soft, but behind this softness was an iron hardness. He guided it up and down a few times with his right hand until we both felt the head nestled at my opening.

I felt a blunt pressure and then some soft thrusts but it didn't go in yet.

"Relax and push out." Albert advised.

I did, and then the head popped in. I let out a surprised squeal of pain. The pain was much sharper than when he had put both fingers in.

"Shhhhh." Albert calmed me, "Relax. It will pass and the best part will come."

I took in some deep breathes of air and the pain did start to dissipate. Albert noticed and started humping ever so gently. Each rocking motion buried his cock in my poor hole just a little bit more. I could feel a pressure building up in my bottom, like I needed to take a big dump. It was uncomfortable but pleasurable at the same time.

Albert continued with his gentle humping for a couple of minutes before I felt his pubes starting to tickle my ass cheeks. Then I felt the warmth of his lower abdomen on my ass.

"Thank God! He is all the way in." I thought to myself.

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