Not in his Wildest Imagination

PRELUDE

It was a Friday the week before my administrative assistant and part-time lover left for a three week vacation in Europe. Connie and I have been carrying on a torrid affair for the past two years and she was the ideal mistress. We had sex in the office, at hotels, at romantic interludes, in the car and some risky places. She was the best piece of ass that I ever had as she loved to do everything. She gave superb head, loved anal especially foreplay and she was a great fuck.

We did the things together that she didn't get from her husband. We even had a threesome once with another woman. That time Connie was introduced to dildos and sex toys. Sometimes we would incorporate the toys when we had sex. A business day did not go by when I didn't have my cock in her mouth, pussy or ass. Some days I had it in all three of her orifices. The sex was the best ever.

Now I was facing a three week period without her and I would miss her desperately. I still dated and chased pussy on weekends but no one ever held a candle to Connie. I was sitting at my desk when Connie came in and introduced me to the temp who would be covering for her while she was on vacation. The temp had come in that Friday for orientation. I was quite surprised to see it was a guy.

"Pete this is Michael, he will be filling in for me the next three weeks. I'm just showing him the ropes."

I stood up and shook his hand which I found to be very soft and somewhat feminine. "Pleased to meet you Michael, Connie will fill you in."

"I'm looking forward to working with you," he replied in an effeminate tone.

I studied him as Connie walked him through the administrative duties. He was about the same height as her 5'5" and looked to be not much heavier. His hair was dark brown and long, covering his neck and ears. When he had his back to me, he could have passed for another woman. Connie had a great ass but next to her his also looked as shapely and curvy. In fact in his tight slacks it looked every bit as appealing as hers.

As they discussed things he would shift the weight to one leg emphasizing his curvy ass and tilt his head to one side. He acted very much as a woman. He also had an ass that many girls would die for. His narrow waist further emphasized the enticing bottom. I laughed at myself for looking at a guy's ass and returned to my reading. Minutes later Connie stuck her head in to speak to me.

"So what do you think of the temp?"

"I'm surprised it is a guy. He seems a bit effeminate; do you think he is gay?"

"He might be but at least he seems very efficient and you have some bimbo around to distract you. I won't worry about you fucking some temp chick while I'm gone."

"I will miss you."

"I know but then you will be hungry for this when I return," she teased as she turned toward me and patted her ass.

"That I will," I agreed.

I looked past Connie and noticed that Michael was standing just outside my office and witnessed the exchange. Connie excused herself and told me she had more to do with Michael before she left that day. I returned to reading the report on my desk. About 3:00 PM, Michael stuck his head in and told me to have a nice weekend that he would see me Monday. He turned his back and walked away swishing his curvy ass and I had to admit it caught my eye again.

Connie came back in before she left and hugged me. I told her to have a safe trip and have fun. She groped my cock through my pants and whispered in my ear.

"I will miss this. Your cock is so much bigger than Jerry's, I love it."

I grabbed her buttocks in both hands and replied, "I will definitely miss this."

Connie left my office and I realized that I had a boner. Sitting down at my desk I arranged my erection in my pants. I knew that I would definitely be clubbing that night and Saturday hoping to line up some dates for the next several weeks.

A TEMPORARYS FILLS IN

The weekend turned out to be a bust in terms of getting laid which was disappointing because I usually scored with the ladies. I did get a few phone numbers from some cute girls. There were others that I could have scored with but I am somewhat selective about with whom I sleep.

I returned to work Monday and found that Michael was very efficient and picked up on the work quickly. I had a crazy schedule and was in and out of meetings most of the time the first three days. When I was in my office I could not help but stare at Michael's curvy ass. Each time I looked at it, I realized how much I missed Connie's ass.

He caught me checking him out a few times and he smiled at me. I was embarrassed that I was drawn to his bottom and I wondered what he looked like naked. He was always wearing silky long sleeve shirts and tight fitting slacks. I was convinced he was gay and suspected that if I came onto him he would go for it. I scolded myself for thinking that way and tried to stay focused on my work. I did make it through the week until Friday.

I hadn't called any of the girls who gave me their numbers as I planned to go clubbing again on Friday night. If that didn't pan out then I might call on Saturday.

Friday after lunch Michael came in my office and closed the door. It surprised me but he definitely had something on his mind.

"What is it Michael?"

"I saw you watching me all week. You're pretty impressed with me aren't you?"

"I'm not impressed with you Michael. I was staring because sometimes you look like a girl and you make me think of Connie."

"I know that you miss Connie. She has a great ass on I know you must love fucking it."

"How do you know that?"

"I heard you two talking last Friday when I was right outside your office."

"Okay, busted, yes I do miss her."

"I bet you were thinking about fucking me, weren't you. It's okay everyone does?"

"I can see that you're humble too. No I wasn't thinking about fucking you, I was thinking that many a girl would love to have an ass like yours."

"If I was a girl, I bet that you would like to fuck me wouldn't you?"

"I probably would if you were a girl but you're not and I have never had sex with a gay guy."

"Why not give it a try? I bet that I will surprise you. Does Connie give good head?"

"Yes she gives great head and she keeps me satisfied."

"But she's not here now and I am. I'm told that I give great head too."

The he locked my office door, dropped to his knees, opened my pants and pulled them with my underwear down to my ankles. I didn't stop him because I was actually turned on from the conversation and I hadn't had sex in a week. I was also intrigued to see if he did give good head as he said..

My rock hard 7+" cock sprang free and bobbed in his face. He began kissing my cock and running his tongue up and down the full length of it eventually taking it in his mouth. He gave me the most incredible blow job ever. He would bring to the edge and then slow down delaying my ejaculation as long as possible. He tested his gag line deep throating me as he handled my balls lovingly. He didn't just suck my cock; he made love to it and worshipped it.

I couldn't hold it any longer and I warned him that I was going to cum. He went right on sucking me as I blasted volley after volley of cum in his mouth. He kept swallowing rapidly and he did not miss a drop. He continued to suck me draining and cleaning my cock of any trace of sperm. When he started to nibble on my dick head my knees got weak and I had to push him off me before I collapsed. I was drained. I was speechless as I had just let a gay guy suck my cock in my office.

"That wasn't so bad, was it?"

"No it wasn't. You give great head but you caught me at a weak moment."

"You came pretty quickly. I knew you needed that. Can I come home with you this evening?"

I was actually still horny and thought about Michael's talented mouth. I decided that I could handle another blow job. However, I wasn't ready to have a gay back to my condo so I booked a room at a hotel that Connie and I used often. I told Michael to meet me there and use the house phone to call me. After work I drove over to the hotel and checked in. I waited for Michael's call and when he did, I gave him the room number.

It was odd because all of a sudden I felt nervous about getting another blow job. Michael entered my room and this time we both undressed. He was lovely with a virtually hairless and flawless body. His ass was to die for and I actually thought that I could probably fuck it. His cock looked small and slender and even fully erect it couldn't have been more than four or five inches long. He was well tanned except for his buttocks which really emphasized the shape of his killer ass.

"Do me a favor Pete and call me Michelle instead of Michael."

He sat on the edge of the bed and drew me in toward him. He caressed the back of my legs and cheeks of my ass as his warm, wet, wonderful mouth began sucking on my cock. I was so horny that I almost shot my second load right then and there. He was massaging the head of my cock against the roof of his mouth. He circled my cock with his tongue and scraped it lightly with his teeth. I felt the light scraping of his teeth. This blow job was even better than the first one. My cock felt as hard and long as it ever had been in my life and I felt I was going to shoot.

Michael took my cock out of his mouth and looked up at me as he stroked the entire length of it and massaged my bloated balls. He put it back in his mouth and then took it out again then he gently blew on it as his fingers continually massaged my balls. He tickled my cock head with his tongue and teased my pee slit. He was bringing me up and down and I was close to cumming few times. He seemed to know when I was getting close, and he would do things making me last longer, torturing me in the process.

"Ready to cum again?"

I just nodded with my eyes closed. Michael then took my cock all the way into his warm wet mouth. He swirled his tongue around the length of my shaft, nibbled on my cock head and sucked me hard. He reached under my balls and rubbed the hardness between my balls and anus. I could feel my cock thickening and I knew I was going to cum. He grabbed my buttocks with both hands as I exploded in his mouth. I fired round after round of cum into his mouth and he sucked and swallowed as fast as he could. The force of shooting my load was so intense that it weakened my knees. I lost track of time and just held onto his head as he milked my cock for every drop.

My legs were weak and I had to sit down. I sat on the edge of the bed and Michael knelt down between my knees keeping my cock in his mouth. He massaged my balls as he continued to suck my cock clean until it shrank and left his mouth. He continued to lick and kiss my cock sending chills and shivers through my body.

"That was incredible, thank you."

"So I guess you liked it."

"What was not to like? I have to take a leak."

Michael lay back on the bed and stroked his cock as I went into the bathroom. I took a much needed piss and then washed up before returning to the bedroom. I was embarrassed again and felt awkward that I had a gay in my hotel room. It would be rude to send him on his way so quickly so I decided to order some room service. Michael liked wine so I ordered a bottle along with some snacks. We got dressed and waited for room service. As we did we got better acquainted.

He wanted to hear about my affair with Connie which I shared with him since he already knew we were having sex. The room service arrived and then we enjoyed the wine and snacks. As we ate I asked him about being gay and he told me when he realized it in high school. He was 18 when he had his first gay encounter.

THE RECOUNT OF MICHAEL'S STORY

It was that fateful day in the city that shaped Michael's future. He was walking the streets when he came upon a gathering of people listening to an older man speaking to the crowd. Michael stopped to listen to what the man was saying. More people gathered around and soon Michael had people standing behind him as well as in front of him. Bodies were pressed together as the size of the crowd grew. Michael then felt a hand rub over his crotch but he dismissed it as accidental. But the hand returned and this time it became more insistent. No one had ever touched his genitals before and it made him nervous that someone in public would do so.

Michael moved to the side to avoid the hand but it returned and stroked his crotch with even more urgency. This time he did not move away. Although he was confused by the act he found it exciting and his cock hardened in his pants. Michael had an average size cock about five inches but at that moment it felt larger. The hand rubbed up and down his stiff shaft through the fabric of his pants and he stood still as if he were fastened to the ground. Then he felt his zipper being lowered and the hand reached in to grasp his erect cock. Michael gasped at the touch as no hand other than his own had ever touched his cock.

Then Michael felt the hand move up and down his shaft but his cock was still in his pants. He moaned softly as the hand stroked him and he was sure that he would cum any moment. Then the hand left him and Michael was confused. He wanted the hand back on his cock. He wanted the hand to jerk him off and finish what it started. He looked around and he spotted a man walking away from the crowd looking over his shoulder. Their eyes met and Michael somehow knew that he should follow that man. He walked behind the man who he was convinced was the one who had stroked him. The man walked down an alley and Michael followed. When he turned the corner he ran into the man who apparently was waiting for him.

"What's your name?" the stranger asked

"Michael," Michael answered.

"I'm James. Did you like what I was doing to you?" the stranger asked.

A confused and bewildered Michael could only answer, "Yes."

"Good then follow me," the man said.

He followed the man for a few more blocks and then the man stopped at an apartment building. He opened the door and invited Michael in. As if in a trance and not knowing what may happen next, he entered the stranger's apartment. The man took off his coat and turned toward him. Then the man dropped to his knees and unfastened Michael's belt and pants. He got hard again as the man fondled him and then the man lowered Michael's pants and underwear to his knees. Michael gasped aloud when his erect cock caught in the waistband of his underwear and bobbed in front of the stranger's face.

He thought that the man would stroke his cock some more and was he not prepared when James took the cock in his mouth. Michael was so turned on that he came in James's mouth almost immediately. James sucked down every drop of Michael's cum and he drained the cock dry. Michael couldn't believe that he had just cum in another man's mouth. James then stood up and kissed Michael allowing him to taste his own cum. James then dropped his trousers and underwear baring his own erection. He pushed gently on Michael's shoulders and Michael realized what was expected of him.

"Suck it," James ordered.

"I've never done this," Michael whispered.

"No problem, just do what I did to you," James replied as he pressed down on Michael's shoulders.

Michael sank to his knees and his face became level with James's cock. Michael had never seen another hard cock until today. James pulled Michael's head toward the erect cock and Michael instinctively took it in his mouth. Michael actually liked the feel of the hard shaft in his mouth and he sucked on it tenderly. James's cock was longer than Michael's in length about 6" and a girth of more than 4" around. James guided Michael's head back and forth until he got the hang of it. Michael then bobbed his head up and down on the cock until James stiffened and fired a barrage of cum into his mouth. Michael instinctively swallowed the first jet of cum that hit the back of his throat and then he continued to swallow each additional volley. He surprised himself with his reaction to James cumming in his mouth. Michael thought that he would have been repulsed by it but he had just the opposite reaction. He actually liked the taste of the semen and that he had a strange sense of power over James making him cum.

Michael was hard again and he hoped that James would suck him off once more. But James surprised him when he turned Michael around to face away from him. James then reached under Michael and cupped his balls and stroked his cock. Michael groaned as his scrotum was fondled. He felt James's tongue slide over his perineum and up between his ass cheeks. He flipped out when James licked his ass and rimmed his asshole. Michael didn't know that people did that to each other but the feeling was sensational.

James worked his tongue back and forth over Michael balls to his asshole. He thought that he would cum again at any second if James didn't stop tongue probing his ass. Then he felt a cool liquid enter his asshole and it almost seemed to numb his anus. James then stood up and coated his cock with the same lubricant unbeknown to Michael. James bent him over slightly as he lined his cock up with Michael's asshole. When Michael felt the cock at the entrance to his ass he panicked briefly but he was afraid to protest.

James pushed his cock into the virgin ass and Michael almost screamed out in pain. He muffled his cries with his arm. James worked his cock into Michael's ass and the pain eventually subsided. He felt bloated for a while and then he just felt full. James began to saw his cock in and out of the curvy ass. Michael's ass was extremely tight and James did not last long even though it was his second orgasm. Michael felt James stiffen and hold onto his hips. James plunged his cock all the way into shapely ass and then he unleashed a torrent of cum into the boy's virgin asshole. Michael felt the seed flood his ass and he instinctively used his anal muscles to milk James's cock dry. Michael at that moment decided that he liked the feeling of cum filling his asshole.

As quickly as it happened it was over. James sent a confused Michael on his way with his ass full of cum. Michael wished that he could have stayed longer as his cock was hard again and he desperately wanted to cum again. Michael raced home and went straight to his room and jerked off. He got naked on his bed and stroked his cock as he thought about his afternoon encounter. Michael came quickly and cum shot from his cock and covered his body from his neck to his pubes. Then he jerked off two more times shooting on his body as he fingered his asshole.

AN ENCORE

I was amazed by the story and my cock was rock hard again. Michael smiled at me and stood up to remove his clothes. I also removed mine in anticipation of another blow job. To my surprise Michael got in bed on all fours with his curvy bubble butt stuck up in the air. I could feel a tingling in my loins as I looked at his hot ass. Michael's body was delicate, hairless and flawless. He really did look like a girl in this position. He was tanned except for his ass and the contrast in skin color really emphasized the shape of his curvy ass.

"Pete, I would like you to fuck me. Do you think that you can do that, fuck me?"

In those years there was no known threat of aids and sex without a condom was commonplace. My cock was hardening and I approached the bed. I knelt behind Michael and I begin to caress his beautiful ass. He handed me some lubricant that he had brought with him and asked me to get his ass ready for my cock. I put an ample amount of lube in my hands and rubbed it all around his anus. I inserted first one finger then two fingers preparing him for my cock. I was no stranger to preparing Connie for my cock but this was the first time I was preparing a man's bottom. However as I sawed my fingers in and out of his anus I was getting turned on by the thought of burying my cock in his shapely ass. I moved closer to Michael and lined up the head of my cock with his anal opening and began to ease it into to him.