Caelin's Job Interview
Caelin is a nineteen year old, but when he dresses up in girls clothing he looks just like a thirteen year old girl. His hair is pulled up in two ponytails that bob when he walks in his skimpy short dress and tanned legs. I went to a night club and while I was there I thought about Caelin and as I sat with the music pounding in the darkend corner while people danced and the lights strobed I reached down and unzipped my pants so I could touch my cock. I was already getting hard long before I had done that since I had been thinking of Caelin's beautiful lithe body, and wondering what it would be like to touch him, to have him. Once while going to the swimmers sphere I chanced to see him in the mens shower as he washed himself off after swimming. He was standing with soap in his hand and running it over his chest and then down to his penis where he soaped it as well as his balls. I wanted him and thought about that moment more than once. The music pounded and my cock stiffened as I thought of Caelin showering. It occured to me that though I had seen him naked I wanted more and I fantasized about Caelin as I sat running my hand along the length of my long hard tool, feeling the precum as it beaded in the opening of the head.
In my fantasy Caelin had come looking for employment at my residence. I had been seeking a secretary and when he arrived I recognized him as the young man in the sphere pool locker room immediately. I asked him about his skills as a secretary and he said he could manage. Then I acted rather dissappointed, pointing out that I was hoping to have a secretary that was female, in a dress, and maybe very young looking. I knew from an encounter that he could dress the part... Then I dared to ask if he thought he could pull off the part of being a young and girlish looking as my clients appreciated this. He nodded and I then asked if he would be willing to show me. Caelin had offered that he did not have the right clothing, so I suggested that he return the next day and show me. In the morning Caelin appeared at my home with his hair in two beautiful pony tails and wearing a pretty little dress. I asked him to come in and follow me to the back yard. "Caelin, you do look the part but can you act the part?" I questioned. "Watch me." he said and came to sit on my lap and place his arms around my shoulders. "Can I have a lollipop?" his voice said in a femanine tone of a young girl. I looked at him feeling a veracious hunger.
Some might have called it a Lolita Complex, and yes he did look all the part of a young lithe girl. "Well, only if you will sit on the swing with me..." I said and Caelin jumped up making his way to the swing that hung from a large tree. I walked over and sat in the swing and waited for Caelin to climb into my lap, holding one side of the rope and wrapping the other around the lower part of Caelins body. I pushed off with my feet and held him swinging while he sat on my lap, my cock growing steadily hard as his bottom pressed against it. I wondered if he were teasing me on purpose, and wanted to test for myself. I slowed the swing and let it lightly drift then reached my hand that was holding the rope around Caelin and touched his chest, finding his nipple and squeezing it. "Hey, what are you doing?" he said but his voice remained very girl like. "Well..." I said, "I just was wondering.... Would you like a lollipop little girl." and I kissed at his neck, and licked it. "Yes, do you have one." he said almost teasingly. I pinched at his nipple and reached under the short dress feeling his cock which was hard. "Come with me, I'll get it for you, okay." I said and he skipped toward the house his ponytails bobbing and little dress slighty hiked up showing part of his ass. I wanted to touch his firm ass and run my hands around it.
I led him to the kitchen and looked through the cabnets, the maid had a child that liked lollipops so I supposed that somewhere there might be some. I found a jar with assorted candy and lollipops. Pulling one out I held it above my head. "Do you want this?" I asked. "Yes, I really, really want it." he said and came in front of me pressing up against my front and reaching up for it. "Ah, but not here dear." I said, "I'll give it to you if you'll sit on my lap again...." "Okies!" he said and waited for me to lead the way to my study. I told him to stand by the door a moment and I went to my office chair, unzipping my pants and parting them behind the desk, then placed the lollipop inside my pants. "Okay you can come in." I said. "Can I have the lollipop?" he said and I motioned him over to where I sat pointing down toward my opened slacks. His eyes had a look of 'What the hell do I do now, if I refuse I'll lose the chance of the job...' I waved him closer speaking, "Come now, don't you want to lick it? I think you'll love it!" I said and wiggled it slightly next to my hardened cock. He pulled up his resolve and came closer, standing next to me and spoke, "But you said I can have it if I sit on your lap, but it's in your lap so how can I." I smiled slightly and agreed, "You know your're right, well then how about this, I'll hold it until you sit on my lap and then you can suck on your lollipop in my lap?" I pulled the lollipop up and patted at my knee slightly. Caelin cautiously sat on my knees and sucked at the lollipop batting his beautiful lashes, like a young little girl. I put my arm around him and pulled him in, and he struggled against my pull, but I wouldn't let go. "No! Come on! It was an interview right?" He said and I kissed at his neck and groped his cock. It was hard and even though he was saying no, struggling I knew he truly was turned on by my little game.
His bottom rubbed against my cock and it was unbearably good feeling the firm skin against my hardness. I reached around pulling at his dress, pushing it upward and leaned slightly reclined in the office chair. I smoothed my hand over his right nipple and pinched it lightly, rolling it in my finger tips. "Don't you want to please me? You're being bad, I might spank you." I said in a parental voice. He leaned in against me and his breath was slightly quickened. I stroked my hand along his hardened penis. It was full and long and the precum was dribbling out of the end. As he leaned back I could smell his clean ponytailed hair. I wanted to spank him. I wanted to throw him across my lap and spank him. Being larger in stature and strength I pulled him around and he lay over my lap, and I brought my hand down on his ass. "No! Stop it!" he whimpered. I smoothed my hand across his lovely bottom and I knew that he was such a tease. He wanted this job and he wanted me as well. I could only imagine the hours in my office having the pleasure of his company.
I wet my fingers with my tongue and I ran my hand between his ass finding the soft tight hole where I pushed lightly against. I pushed my finger in and moved it gently about, exploring the tight hole. Caelin moved and I held him still. Then I held the lollipop in front of his face as he lay across my lap. "Here, suck on this and don't be so bad." I said and he reached up to take it and began sucking. I stood him up and looked at him as he teasingly sucked on the lollipop. Then I knelt down and took his hard cock and licked it similarly to the way he was licking the lollipop. He shuddered and I placed my mouth over the head and sucked on him and squeezed his ass with my hands pulling the cheeks apart and then I stuck my finger inside his hole. He moaned and sucked on the lollipop. I tugged at his hand and pulled him closer to me, shoving his cock into the far reaches of my throat and swallowed as I touched his balls lightly with my free hand while my finger moved in his asshole. Then I stopped and pulled my finger loose and looked up at him as he smiled with the lollipop in his mouth like a little girl, with the acception that his cock was quite the mansized kind matching his age of nineteen.
I pulled Caelin down to the floor and then straddled his face hanging my cock above his mouth which was still sucking the lollipop. "Suck me Caelin, suck -my- lollipop..." I said and felt his mouth as it came near to my cock. He had the lollipop next to the head of my cock and licked at both using the lollipop like an extra tongue to run over the head of my cock. He rolled it over the opening and down the full length, and then put both the head of my cock and the lollipop in his mouth and sucked hard against them. Then he did something that surprised me, while he continued sucking my cock he reached his hand around and stuck the lollipop up into my ass. I jerked with excitement because it was even more kinky than I had hoped for. I leaned forward and sucked his tool, moving my head up and down, sucking hard against each pull-back and opening my throat with each push inward. He pulled the lollipop free as I stopped and moved away from him. Then I grasped him and carried him to my desk, shoving the papers wildly but I didn't care. I pushed his legs above his head and spoke, "Hold your legs Caelin." I was anxious and he was as well. He held his legs high in the air as I took the head of my cock and pushed it hard against his tightened ass hole.
His eyes tightened with pain so I pushed quickly and hard, entering his ass and ramming my cock until my balls touched against him. The I shoved my cock hard several times slapping against him and feeling him rock as I placed my hands on his legs holding them for him as he reached down to stroke his cock. "I'm going to show you a secret Caelin, I hope this will get you to work as my secretary." I said this pulling my cock slightly outward and bending forward until my mouth opened next to his cock and I licked it. Caelin jerked with pleasure and held his cock towards my mouth and I took the head inside and began to suck him while I shoved my cock into his ass. He lay there fighting an orgasm that was going to happen. I wanted it to happen, and I shoved harder as my mouth sucked and my tongue flicked at the head of his cock. I could feel his cock expanding and getting hotter and my own cock ready to spew out the white fluid into his ass and I let myself cum. When I did I moaned slightly with relief and drove my cock in holding it in one place feeling the spasms of cuming.
Caelin's cock exploded shooting cum upward into my throat and into my mouth and I allowed some to run back down his head and then sucked hard as his cock spasmed and he jerked tightening his own body with pleasure. When we had both cum I stood letting his legs down and I kissed his mouth deeply and pinched at his nipples. "Caelin, I want to hire you, and I think you'd be the perfect secretarial assistant for me." I said panting and kissing his mouth again. "If you don't, I'd be greatly disappointed and you'd be stupid to give up the income." I said this baring my weight down against him pushing him against the table. He nodded lightly and smiled that girlish smile and I leaned back to shove my finger into his ass. I wanted him once more before he left, maybe this time I would fuck him in the ass as he sat in the swing outside in his little dress and ponytails.
If I every have the chance I will ravage Caelin and shoot my cum up his pretty little ass. But as this was a fantasy in the nightclub I sat masturbating at my table and feeling my hard cock spasm when I came under the table cloth. I will have Caelin in his dress and ponytails and I will put a cock ring on his nice cock and suck him off in the shower perhaps as well.....