I didn’t ask for it, but it happened anyway. After my initial objections with the idea, I loved every second.
It began with a new customer. Charles was a nice guy, and we seemed to hit it off right away. What I mean by that, is that we had the same beliefs about life and hard work.
There was no attraction on my part. I was about as straight as they come. I’ve only ever been with and attracted to women.
I’ve enjoyed some anal stimulation from time to time, but only as a precursor to the main event. Occasionally, there was some digital penetration during a blow-job or some mutual rimming during a sixty-nine. But, I’d never even thought of anything more than that.
I met Charles through his daughter Denise. She was referred to me by one of my customers for auto insurance. I collected her information over the phone and called her back to review my findings. Denise was delighted and wanted to go with my quote.
She wanted to come by the office and sign in person, rather than e-signing. It was her first time with her own coverage, and she wanted to understand everything. We set an appointment for later in the afternoon that same day.
This was the one part of this business that I truly enjoyed. The insurance business is a necessary evil in my book, but helping people navigate it keeps me sane. Owning the business also made it a little easier, since I could deal with the companies that I tolerated.
I was on the phone with another customer when Denise and her father, Charles, walked in the door. I motioned for them to have a seat as I finished up my call.
After hanging up the phone, I introduced myself before Charles commenced with his spiel. It was evident that he was a take-charge kind of guy and very protective of his daughter. Once he realized that I wasn’t a shark out to take advantage, he settled down. That’s when Denise spoke up, “So, can we go over the coverages now?”
We all had a little chuckle before I commenced. For her part, Denise listened intently and did a great job of asking questions. That was the first of many visits and policies that I wrote for Charles’ family and friends.
Charles became a regular in my office. Often, he just stopped by to say hello and talk. We had a lot in common in our beliefs and work ethic, and we’re both in our mid-fifties and self-employed. There were physical differences between us, with Charles being six-foot and about forty pounds overweight. I, on the other hand, am five-nine and lean. I exercise daily before work, while Charles’ only exercise comes during work.
Our other differences came in the relationship department. Charles had been divorced for about fifteen years, while I am still happily married. Only once, in all the time we talked, did Charles ever mention having trouble finding another mate. He never specified female or male, just that his schedule made it difficult. The fact that he always began and ended our time with a handshake and a shoulder grip should have been a clue.
His visits would usually come at the end of the day since his profession was HVAC. Charles stopped by this Friday afternoon at about five pm. He knew that I stayed later on Fridays in case one of my customers was needing to make a last-minute payment.
It was pretty quiet when he came in the front door. Charles was obviously hiding something behind his back as he approached my desk. As he sat, Charles presented a six-pack of Molson. As he slid one out of the pack, I said, “I’m still working here, Charles. I can’t start drinking just yet.”
Charles looked a little sad as he popped off the top and asked, “Is it okay if I have one? It’s been a tough week.”
“Sure. Knock yourself out.”
As I continued with my paperwork, Charles began venting. It was unlike him to act this way. But I knew from prior conversations, that he had few people that he could talk to about his problems. As he babbled away, I did my best to keep up and comment regularly.
When Charles cracked open his second beer, his talk started to slow. I noticed that there seemed to be a sadness in his voice. As I looked up to see if he was alright, I saw that he was crying.
“Are you okay, Charles?”
“No, not really. It’s been too long since I’ve been close to someone, and I have a confession.”
“What’s on your mind?”
“I really need to hold someone. Can I hug you, and have you hold me in return?”
“Sure,” I replied hesitantly, as I stood and walked around my desk.
Charles quickly wrapped his arms around me tightly, and I returned the hug. After a minute, he started to loosen his arms, and I did the same. However, his arms slid down my back until they reached my buttocks. Charles began squeezing my ass aggressively as I tried to push away from him. As I tried to break free, I yelled, “What are you doing? Let me go right now. I’m not gay!”
“I need to feel your body against mine. It’s been so long since I’ve been with someone. Let me make you feel good.”
Before I could reply, he popped open the button on the front of my jeans. Charles then quickly slid one hand into the back of my pants and the other into the front. With no underwear to interfere, Charles immediately began to caress my ass with one hand and my cock with the other.
My inhibitions were lowering rapidly. Charles tried to move in for a kiss, but I dodged his face as I half-heartedly struggled to break free. Unfortunately, my body began to betray me. My cock began to swell, and I started to pant, from the exertion and the excitement.
As Charles’ hand moved between my cheeks, I felt a finger begin to pry at my pucker. My only response was to spread my legs a little. At that point, he must have known that he had me. Charles dared to remove his hand from my cock long enough to pull down my zipper. Then he used both hands to jerk my pants to the floor before resuming his offensive.
Charles stroked my cock flagrantly while he slathered his middle finger with his spit. I was still holding onto his shoulders when he pushed it into my ass. My reluctance was now completely gone as my arms started to go limp. I was gasping as I felt my orgasm approach. Moments later, I shot rope after rope of cum all over Charles and the floor.
As I collapsed into him, he moved me toward the desk, placing me face down and bent at the waist. Charles knelt and spread my buttocks as his tongue began to dine. Even in my delirious state, I knew what was coming. I also realized that it was something that I truly wanted.
As his tongue dug deeper into my rear-entrance, my cock began to swell again. It was up against the side of the desk when Charles bent me over, so it was evident to him now. He squeezed it like you would a cows teat, over and over. Between that and his magical tongue work, all I could do was moan and drool.
After a few more minutes, Charles pulled his face away and slipped a couple of fingers inside me. My whore-like moaning increased as did the speed of his penetration. I tried to spread my legs further apart, but my jeans held them at my ankles. Pulling my legs together, I quickly forced my jeans, shoes, and socks off of both feet. When they were free, I pushed them apart as far as I could.
Charles’ fingers were now getting deeper as he kept up full strokes. Feeling myself begin to loosen up, I shouted, “Add another!”
He stopped for a moment to lube up another before easing it into my sissy ass. With the third finger pushing my limits, I felt another climax coming. Charles was still squeezing my cock but never really touching the head. This orgasm was all about my ass, and it came on slow. It was like no other I’ve ever had as it spread throughout my body. It must be similar to what women feel.
Even after I felt the last of the semen leave my cock, the feeling continued to spread. Charles was still pumping my ass with his fingers as I moaned through a continuous climax. Unbeknownst to me, Charles had caught most of my cum in his free hand. As he stopped his digital assault, he began stuffing it into my ass.
With no penetration for a few seconds, I barked, “Fuck me already! I need something in my ass!”
All I heard was a zipper before I felt the head push it’s way inside. It was thick, but with the lubrication, it slid in until his pelvis bumped my ass. Charles was in no hurry and was enjoying every bit of his penetration. I, too, was loving it as I felt that tingle once again. His cock rubbed against my prostate like no finger ever had. I was once again a moaning drooling mess and loved every minute.
“So, for a guy who says he isn’t gay, you sure seem to be enjoying yourself,” Charles said as he slowly picked up the pace.
I mumbled back, “Who knew it would feel this good?”
“I knew,” Charles countered. “I knew that you were a natural. You were built for this, with your perfect little round ass and your thin girl-like frame. I’m just amazed that you haven’t done this before now. So, I guess you’ll be wanting this all of the time now.”
As his pounding became faster and more pronounced, I grunted, “Yes, yes, yes.”
I felt semen dribble from my cock as my third orgasm took me over. I contracted hard onto Charles’ cock as the spasms swept through my entire body. As I was in the middle of my bliss, I heard Charles groan as his cum filled my stretched rectum.
He slowly fell on top of me, breathing hard and kissing my neck. After his breathing was under control, Charles stood and let his softening cock slip from me. I felt a river of warm cum run down my thigh and calf before hitting the floor.
As Charles cleaned himself and me, I stayed face-down on the desk and enjoyed the aftermath of my reluctant butt-fucking.
