New Awakening - Straight to Bi/Gay

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Divorced boss spying on hot secretary, "turns" his life.
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rimaday
rimaday
1,842 Followers

This Is the first of a 2 part story of a transformation from straight to a bi/gay cocksucker. I hope you enjoy...

*****

I am a 49 year old divorcee. After 2 years of divorce, diving into my work was not enough to satisfy me any longer. I had begun visiting more and more porn sights on the weekends and evenings. I became very familiar with satisfying myself for a little relief. The thought of entering the dating world and starting a "relationship" with someone new was nauseating to me. Jacking off seemed much easier.

I had started going to the gym and watching what I eat about a year ago, with the thought of getting in shape before getting back out there. I am about 5'9" and had gotten down to about 180.

I am Director of New Product Development of a relatively new start up software company. Our offices are in an old building on a large university campus, as part of their entrepreneurial incubation program. We were in our 3rd year in the facilities and would be able to be here for about 2 more years before needing to move out. It had been very easy to bury myself in work with all the needs of a start up company. It was beginning to pay off as we were on pace to turn a profit this year.

My Secretary/Executive Assistant is a beautiful elegant woman, somewhere in her early forties is my best guess, but looks 30. She is one of those women who never tell their age, but pride themselves on looking younger than they are. She is a smart committed team member that has put in some long hours when needed. Allison Schneider was a rare find.

I have to admit, she was the object of my thoughts more than once during my masturbation sessions. She was married and a valuable asset to the company, so that is all she could ever be is a fantasy. My impression of her husband was that he could be a condescending asshole when it came to Allison. Why is it some people don't see how lucky they are sometimes.

It was a Friday morning and our IT manager was running new high speed lines for our computer system. He was working in the drop ceiling in Allison's office. I got a kick out of hearing Matt flirting with her. She enjoyed the attention of a younger man acknowledging her beauty. Matt was in his mid 30's, about 5' 10" and rode his bike to work most days, 20 miles each way, so he was in good shape.

What was surprising to me was hearing her flirting back. I have never seen her do that with anyone in the office. I moved quietly to my office door to listen and try to sneak a peek. He had positioned the ladder next to her desk, climbed up, and moved the ceiling tile to the side to gain access.

"Pay no mind to the man hovering over you, I am really not trying to look down you top. I promise," he said climbing the ladder.

"Ok, if you say so," she said smiling, while unbuttoning her top button.

He was surprised at her response and seemed unaware of what to say next. He stood there on the ladder looking down at her, smiling, staring and drooling all at the same time. He looked up and climbed a couple more steps until his chest disappeared into the ceiling, with his ass facing her. l watched her gaze at his ass for several seconds before she began again.

"I have never seen you like this before Matt," she said, in a teenage girl voice, never taking her eyes off his ass. "Your a wrangler guy I see; real, comfortable jeans. Brett Favre would be proud!"

I could not believe what I was seeing this from her. She always exudes class and professionalism. I was envious. She continued to check him out, when after a few minutes, he turned around on the ladder, his lower half facing her.

"Wow Matt, I've never seen this side of you before," she said in a sultry porn star voice.

"Alli, you sure are in rare form today!" he said shuffling on the ladder.

"Just waiting for this mornings package delivery. You know the saying; what can brown do for you?"

"Anything you want, I am sure!" he said as his bulge began to grow.

She was now staring at his dick and shifting around to get it from all angles. She glance back over her shoulder to my office and I slinked back out of sight.

"Anything?" she asked

"Anything...absolutely anything," he replied.

"That sounds like complete customer service, Mr. Young. Are you sure you can deliver?" she said in the porn star voice again.

My dick was getting hard just listening to this gorgeous lady talk. I couldn't imagine, if she were directing that at me. His hard-on was unmistakable at this point. If anyone came by, it would not be good. Apparently Matt realized it too and quickly descended the ladder.

He picked up his tool bag, held it in front of his pants and said, "I did not bring the right tools, I will have to finish this later."

"Looking forward to it," she said smiling. "Hold on."

She jotted down a note on the sticky pad and handed it to him. He held the tools with one hand and grabbed the note with the other.

He read it and said, "It is, I can promise you that!"

He crumbled the note and tossed it in the can next to the door as he practically ran out. I was excited beyond belief seeing my dream girl use her sexuality so strongly, and jealous it was not me. When she left for lunch later, I dug the note out of that trash can and read it.

"LOOKS LIKE THE RIGHT TOOL FOR ME," it said with a smiley face.

A few minutes later he came back, and finished the job while she was out to lunch. Afterword he left a sticky note inside here drawer. When he left, I opened the drawer and read it.

"IF YOU LIKE WHAT YOU SAW, COME TO MY OFFICE WHEN YOU GET OFF AND I WILL SHOW YOU MORE."

I could hardly wait till the end of the day as I had a great plan for this. Matts office was an old Psych lab room that had a two way mirror for observation, back in the day. The observation room was now our catch all storage room. I could watch the continuing action and they would never know.

Normal quitting time is 5:00 but it was Friday, so at 4:30, I stepped into Allison's office and said, "It's Friday, why don't you head out early. It's been a long week. I have a few, things to wrap up and I will be taking off too."

My words startled her as she was looking into her open drawer at the note. "Sure that sounds great," she said trying to remain calm.

I stepped out and made my way to the storage room. The doors to the hallway in these old offices had the white smoked glass that allowed you to see a vague silhouette of a person standing close to the door. This would be good, as I could get a few second warning if someone came in while they unlocked the door.

I got in place near the mirror window and had a perfect side view of his office. The door on the left, a chair for visitors in front of his desk and at the right end of the field of vision was Matt sitting behind his desk. His oversized monitor sat off to his right and angled enough that I could actually read what was on his screen.

There was a chair in the room with boxes on it, in front of the old observation desk. I decided to grab a seat and hopefully see a show. As I moved the boxes, a book that was on the edge of the chair fell off and hit the floor. I froze in place and turned to look at Matt. I did not see any sign he heard it. Carefully, I set the boxes down and slunk into the chair.

On the desk was an old intercom system, and I found a switch labeled listen. When I flipped it, I could hear Matt's chair squeaking as he moved around. I thought I had better make sure it was only one way sound. I thumped lightly on the desk and got no sign he heard anything.

After several minutes I saw what looked like Allison's silhouette pass the door, but a full minute later she had not yet knocked on Matt's door. After three or four minutes, I thought it wasn't going to happen, and began to get up to go home for the weekend. Then a faint knock, just as my phone, dinged with a text! I plopped, loudly back into the chair and froze. It looked like Matt, glanced my way, when a second knock drew his attention.

I thought about leaving the room to let them hear the door close and hear me leave, in case my cover was blow. But, he turned his attention to the door.

"Come in," he said loudly. He continued as she stepped in the door, "Alli, let me just say, I apologies if I overstepped today. I am not sure if you know about my home situation, but it has been a difficult time lately and I feel like I used bad judgment today."

"What's going on Matt," she asked.

"It's a long story. Would you mind locking the door so we are not interrupted. I am afraid I may get a little emotional and would rather keep my situation, as private as possible," He said looking sincerely distressed.

She locked the door and took a seat across the desk from him.

"I too should apologies for taking things too far, I did not mean to upset you. I have had some issues of my own as well. Tell me what's going on," she said with concern.

"Well, my wife has suffered from ALS for sometime. She requires constant care and has steadily worsened over the last several years. When I work, there is an in home nurse that must be with her at all times. I love her to death and always will, but we have not had any sex life in years. So, I hope you can understand that my flirting might get carried away, given the circumstances.

I know your married and we work for the same company and I was being inappropriate. I built up a picture in my mind of a vibrant woman, in her sexual prime and a husband who no longer appreciates her. I pictured myself as a means to help her scratch that itch that's driving her more and more crazy everyday. That is the little fantasy I built in my mind today. Again, I apologies for being inappropriate," He said solemnly.

She took a deep breath and began to speak, tearing up, "Wow Matt, I knew there were medical issues, but I did not know how severe. You have my sympathy, and if there is anything I can do to help, like run errands, cook meals or whatever you need let me know."

"Thanks, I have a system that works pretty well for me, and we get by with the day to day, but thanks for your offer. Am I forgiven?" He asked a bit more at ease.

"You are forgiven and extremely perceptive," she said also more at ease. "My husband and I have been in a rut for a long time and I have been feeling rather undesirable lately. I too got a little to excited this morning. When someone as attractive as you showed interest, I lost my head a bit."

"Alli, you are one of the most beautiful elegant women I have ever met. Please don't ever believe you are not desirable. Smart, outgoing and sexy is a rare combination that should be appreciated. Your husband is a lucky man," he said fidgeting in his seat.

She blushed and shifted in her seat, took a deep breath, and began to speak softly, "I am at a loss as to what to say next, but my heart is beating a hundred times a minute. I love my husband and have never been unfaithful, but I want to let go with you Matt!"

"Oh God, me too Alli, but I cannot offer anything more than a physical relationship. I love my wife and could never leave her; especially with her condition. If sex is what you need, then I can say with confidence, I can scratch any itch you may have and a few you don't even know you have yet," he said adjusting his cock in his pants behind the desk.

"Matt, I think we are on the same page!" she said leaning forward in her chair. "I have not been able to shake the image of your hard-on this morning. I hope you will keep that promise to show me more."

I was in disbelief, but my cock was not. It was at full attention, as Matt was experiencing my dream! I was so fucking jealous! But at the same time, having heard his story, I was happy for him.

Suddenly, without getting up, Matt started unbuttoning his button down shirt as he untucked it. He left the top few buttons attached and pulled the lower shirt apart exposing his flat stomach. Next he unbuckled his belt as Allison, craned her neck to get a view from the other side of the desk. He worked his zipper down, spread his pants and released his overstrained underwear. He was uncovering a porn start cock. Once again I was so jealous, with my 6 1/2" wonder.

He worked his underwear down below his balls, to provide a full view. Then he began to speak to Allison who appeared to be in a trance, still straining her neck for the full view.

"Alli, I am telling you this not to brag but to state facts, I have an extremely high libido. If we do this, I will need attention almost daily. I promise you it will be worth it and you will orgasm every time, he said confidently. "If this is too much I will understand. I would insist we take it slow to begin with, and if you follow my instructions, you will be completely sexually fulfilled for as long as you like."

"Pretty, sure of yourself aren't you? I will say you have quite the right tool for the job," she said biting her bottom lip.

I was so fucking turned on I couldn't stand it. Luckily there were some old boxes of napkins opened. I grabbed a few in case I needed to clean up.

"Come get a closer look," he said smiling.

He spun his chair to his left, toward the mirror as she walked around the desk. As he turned, it provided me a full view of his package. It was at least 9" long and relatively skinny(about the diameter of a large kielbasa), which made it look even longer. He was stiff as a board, as was I, with a sexy, vibrant, gorgeous woman walking around the desk for a closer look at his throbbing hard-on.

His dick was pink and smooth, with a well pronounced head with a purple hue. The cleft was extremely pronounced as it lead to a heavily rimmed hood encircling the head. The skin looked like a stretched balloon, it was so engorged. His balls were huge and basically hairless, as they bulged from his opened zipper. His shaft arched gently, pointing the head slightly toward his body . His pubes were trimmed and well manicured.

"God, you are so sexy," he said holding out his left hand to guide her closer to his side. "Look what you do to me!" he said raising his pelvis to accentuate his boner.

As she stopped next to his side, her tasteful dress pressed against the arm of the chair. She was dressed smartly, as usual, in a form fitting black dress that ended just below the knees. It had short sleeves and all but the 2 top buttons were fastened. Her gaze was transfixed on his bulging cock.

He slowly started stoking her right leg, below her hem line, using his left hand. As he touched her skin he sighed, "Your skin is so soft and smooth, you make me so damn hard. I want to touch every inch of you."

He slid his hand up the back of her thigh, until her dress bulged out at her ass. As he rubbed her ass, she closed her eyes and gently swayed. I wanted so badly for her to looses the damn dress. With his right hand, he reached across his body and ran his hand up her inner thigh.

He was looking in the mirror, taking in the sight of himself sitting in the chair with a huge boner, a beautiful woman standing next to him lost in his caress, and apparently completely under his spell. He continued to caress her ass with his left hand, while his right hand continued its way up her inner thigh.

Taking a deep breath through his nose, his cock noticeably twitched, "I can smell your wetness; can I please touch you there?" he pleaded softly.

She gently swayed her hips and inched her legs further apart granting him access. Starting to see a wet spot on my pants from pre-cum, I decided to release my suffocating cock. It felt great as the air hit it giving it room to breathe!

As his hand reached it's target they let out a collective, "OOOHHH." His arm began to move rubbing her wet pussy, as she began to breath much louder and whimper with every stroked of his hand.

"Oh my, your panties are so wet, I hope you won't mind getting these off," he said as he hands gripped her waist band on either side of her hips.

He slid them down as far as he could reach, and then she stepped out of them, one leg at time. I wished I was on that side of the glass so I could smell her wet pussy. He brought the panties up to his face and took a slow deep breath through his nose, his cock throbbing up and down slowly. As he tasted his fingers, she bent forward to touch is cock. He gently gripped her wrist stopping her.

"Please not yet. If you touch me I will cum immediately. I am not ready yet. I want to take this slow. Can I please touch you first?" he asked softly.

She nodded and he again slid his left hand up to touch her ass and his right up her inner thigh. She rocked and moaned as he reached her wetness again. She tilted her head back with her eyes closed, letting his fingers have their way.

"You are making me so fucking hard, I can't stand it. You are so sexy, I can feel the heat pouring from your wet pussy. I want to fill you up so badly, but I am not ready for intercourse yet. Will you let me please you this way for today?" he said panted and moving his hands faster.

Biting her bottom lip and whining desperately she was beginning to let loose, "Oh yes please that feels so good, please don't stop. I love the way you touch me. Aaahhh yess!"

He began to move is left hand up and down her ass while fingering her pussy. My dick was throbbing but I knew I needed to wait. I would cum in two seconds if I started jacking off. I wished I could see exactly what he was doing under that dress.

"Oh God, Matt you are making me cum," she said pushing back against his finger thrusts.

His hand on her ass began to wiggle as she got more excited. She gasped and began to gyrate.

"You like that!" he asked eagerly.

"Yes, tickle my asshole that feels so good!" she almost screamed.

She seemed to remember where she was and put her hand to her mouth and began to bite down trying muffle her shouts, "AHH! AHH! AHH! AHH! AHH! I am cumming!"

Her body quaked as she came from his magic fingers. As her climax began to subside, he brought his left hand from her ass around the front keeping it under her dress and apparently working her pussy with it. She gasped again liking it. Then the left hand returned to her ass as his right hand began to work her pussy in small fast pulses. This caused a noticeable increase in her volume again.

"How does this feel? Do you like that?" he asked working both hands.

"Oh Yeah!" she said, stiffening her body.

"Has anyone ever done this to you before?" he asked, looking almost in pain from his hard-on.

"No! But I like it. Please don't stop! It feels so good!" she gasped.

"You want more?" he panted.

"Yes please I need two," she said pleading. "Please finger my ass!"

He shifted and picked up the pace again. He was working both hands and she began to shudder. She moaned and grunted, pushing up and down on his fingers.

"Cum for me please Alli!" he whined. "You are so sexy my dick is gonna pop!"

As if following orders she began to chant, "I am cumming! Oh God, I am cumming again!"

I grabbed my cock as she began doing tiny squats forcing his fingers deeper and harder. He was watching the action in the mirror, making it look like he was staring right at me, taunting me with his big dick; knowing I could not compare.

Watching my fantasy woman exploding in an massive orgasm at the hands of the man with the superior cock took me over the edge as I shoved the napkins over my cock to capture the hot cum erupting from me. It rocked my whole body. I came so much I had to waddle over with my pants at my thighs to grab more napkins.

As I did her orgasm had subsided, and she was looking down at him panting and composing herself. As I managed to get myself cleaned up, thankfully with out smearing cum all over my clothes, I saw her staring at the poor man's throbbing cock.

"My turn," she said stepping around in front of him and spreading his legs. Unfortunately, that blocked my view of the action, except for her shapely ass still covered by that black dress.

rimaday
rimaday
1,842 Followers