After listening to several losers tell me what a great career I could have flipping burgers, I decided to try the local newsagent for a paper delivery job. The guy who owned the shop was, according to my dad, a bit suspect. His name was Tim and he was probably in his late thirties, a little overweight and his wife had run off with some bloke a few years ago. Something told me that a job with this guy might present untold opportunities.
I wanted to test how suspect he really was. I know self-praise isn’t meant to be any praise at all, but I am a good-looking boy. I had deliberately worn my shorts because I have a great arse and legs. Tim ushered me into his office out back and asked me to fill out an employment form. I deliberately bent over his desk to fill out the form so that he could get a good look at me. He nervously asked me to sit down in a chair he had brought over. I sat down and continued to fill out the form, but slid my bum forward so that my shorts revealed more leg. My shorts were already fairly short, but this movement didn’t leave much for the imagination. Tim was standing against a filing cabinet, so I asked what a word was in the form. He had to come over and lean over me to see the word. I gently slouched back in the chair so that he could get a good look at my smooth tanned legs and firming crotch. I opened my legs for good measure. I could sense him becoming quite uncomfortable. It must have dawned on him that he was alone with me because he suddenly wanted to move the interview back into the shop. I began to feel very excited as I concluded that he was suspect. He asked me when I could start. I told him that I didn’t have a bike to ride, but could borrow one off a friend. He said he had one I could use but it was in his garage at home. I smiled and agreed to start the next day.
While I was walking home it occurred to me that I needed to give more thought as to how all this was going to help my cash flow. I needed to keep Tim off balance otherwise I might actually have to deliver papers. I decided to pay Tim a visit at his home after work. I went home. I needed to prepare.
It was summer, and it didn’t get dark until about 9pm. It was about 6.30pm when I rang Tim’s doorbell. When he opened the door, he was stunned. I asked if I might be able to borrow the bike tonight so that I could give it a wash and so on. He looked very unsure, but said I could and invited me in. He looked out the door nervously before closing it behind me. He gestured that I follow him. As we walked through the living room, I saw he had a pool in the back yard. Bingo. I stopped following him and headed straight for the pool.
“The garage is this way” he said rather anxiously. I told him I was hot from the walk and could I have a quick swim. All the blood seamed to drain from his face (probably went straight to his dick). I didn’t wait for an answer, and took off my T-shirt and dived in. He began to protest but as I slowly floated to the surface on my back, he stopped. I new he was turned on at the sight of my near naked body. He grudgingly sat down on a pool lounge. I climbed out of the pool and laid down on the lounge next to his. The water formed droplets all over my body as I made myself comfortable. For good measure, I pulled the legs of my shorts up a bit to reveal a little bit of bum cheek. Poor Tim. I had years of parental manipulation behind me and I felt absolutely in control. He appeared to be very flustered.
I began to move about on the lounge as if I was in some discomfort. Tim asked if I was all right, but when I told him my shorts were becoming too tight from being wet and could I take them off to dry, he began to look a little panicky. “I don’t think you should be running around here in your under pants” he stammered. I looked at him innocently and told him that I wasn’t actually wearing any.
An expression of realisation suddenly came over him. He sat back in his lounge and said that it would be ok if I removed my shorts. After all, the yard was quite private. He suggested that he might change and join me for a dip. He then ran his eyes down to my crotch and motioned that I begin. As I slowly moved my fingers over my stomach and began to undo the button to my shorts, I turned my head toward him. I undid the button very slowly. My heart began to race with excitement. Tim was transfixed on the workings of my hand. I needed to slow this down, so as my fingers began to search for the zipper, I asked if he might have something I could put on. At first, he said he didn’t have anything that would fit, but then he seemed to have an idea. He told me to go into the spare room, just to the left of the front door. I should find something in there. We both got up. He went off to get changed and I found my way to the spare room.
When I opened the wardrobe door, all I saw was girls’ clothes hanging up. Skirts, dresses, shoes and boots. They were too small for an adult. I opened a draw and found girls panties and other under garments. I began to feel naughty again. I quickly rifled through the other drawers and found what looked like a bikini bottom. I peeled off my shorts, to some relief, and slipped on the bikini bottoms. WOW. It felt exhilarating to have some strange girls clothes barely covering my arse and dick. I checked myself out using a wall mirror. I felt great. I closed my eyes and ran my hands over myself. I quickly found some socks and a short denim mini and put them on. All the clothes had a scent or perfume about them that was very feminine. I had worn girls’ panties and socks before. My 14yo cousin Emily had made me dress up so we could play lesbians (my idea), but this was different. I suddenly remembered Tim, so I jettisoned the mini and socks and kept the bikini bottoms.
As I made my way back to the pool, Tim emerged wearing a robe. He saw me and seemed pleased with my find. He told me the clothes had belonged to his daughter. I resumed my position on the lounge and pulled the bikini sides up over my hips. I felt really turned on. Tim noticed my bulging briefs and reminded me that I may need some sunscreen. He held up a bottle of sun tan lotion and patted the front of his lounge. I got up and sat on the end of his lounge. He moved up behind me, with one leg either side of me. I glanced over my shoulder and saw that his robe had separated. He was naked underneath and a little bit hairy. He opened the bottle of cream and began to slowly rub the oil onto my back and shoulders. He had very large hands. I felt rather small. His legs began to close tighter and I could feel the end of his penis touch the base of my spine. His hands worked their way down my back and began to move around my waist. With each forward massage, his fingers went closer to the area of my pubic bone. My cock was hard now and seemed to strain toward his ever-nearing fingers. As his hands began to touch the top of my bikini, I placed my hands behind my head and started to slowly contort my body with the movement of his hands. I asked if a paperboy such as myself earnt much money? Tim’s hands stopped. He thought for a bit and then reassured me that a boy with my talents and discretion was paid very well; maybe a bit extra if I performed well. He asked if I was a hard worker. That sounded very naughty to me and I let him know it by moving my bottom up hard against his groin. I lowered my arms and ran my hands over his legs. His hands ceased massaging me and with one hand on my stomach, his other hand gently lifted the bikini over my cock.
His big oily hand took a firm hold of my shaft and began to masturbate me slowly. I arched backwards into him and audibly exhaled. He began to kiss and nibble my neck and when the hand he had placed on my stomach began to slowly rise up to my chest and thumb my nipples, I was ready to come. As seminal fluid seeped out of my penis, Tim began using it as a lubricant, running his thumb around and over my cock head until my breathing became more of a frustrated panting. He wiped some pre cum off my knob with his middle finger and slid his hand under my bikini and down between my legs. I opened my legs wider as his finger searched out my anus. As he began to probe me, his other hand took a hold of my very hard and welcoming cock shaft. I felt great. I felt like coming. I felt like a slut.
He asked me to try and bring my knees together. This only served to put more pressure on the base of my penis and balls. His hand took a firmer grip of my cock shaft and he began to work his big hand up and down, stretching my cock magnificently. His finger stoked my anus and every now and then he would penetrate me. My penis reached plateau. I gave a cry of pleasure and told him I was going to cum. Finally, as I felt the over powering sensation of orgasm engulf me, I turned to Tim and asked if I was his little slut. As I arched my back and spurted cum all over my stomach and his hand, he whispered back that I was. I groaned and pressed my lips against his. My body jerked as I thrust my penis in his powerful hand. He began to wipe the cum over my body with his spare hand. He gently but firmly squeezed the last of it out of me and then took his hands away. I let out a deep breath and shook a little.
He managed to get up off the lounge and stood over me. “My turn” he said in a rather calm voice. I looked up at him towering over me. I began to move toward his rock hard penis. He stopped me and gently pushed me back so that I was laying flat on my back on the lounge. His hands grabbed either side of my bikini and rather roughly pulled them down my legs to my ankles. I asked him what he was up to, but he was busy using the bikini to tie my ankles. I nervously laughed a bit and asked him again what he was doing. He raised my feet up and put his head through my legs. My ankles were now resting on his shoulders. I continued to smile at him and again asked what he was up to. Tim began to kiss and lick my ankle. He began to move toward me, keeping his lips on my leg and as he did, I had to bring my knees up closer to my head. He forced my knees up so close to my face that I could nearly lick them. My arse was completely open and exposed. As he began to position his knees either side of me, I felt the head of his cock touch my anus. He ran his tongue down the side of my knee and then he gently touched my lips with his. I felt his breath enter my mouth. I whispered to him that I hadn’t done this before and that I was scared. He placed a finger gently over my lips and told me to shush. My breathing began to quicken. He must have seen panic in my eyes, because he grabbed my wrists and held them down. As his tongue began to enter my mouth, he released one of my wrists so as to guide his cock into me. I made a muffled noise. This time, he placed a hand over my mouth and began to press his hard shaft further into me. His whole weight was focused on his entry of me. He began to gently thrust back and forth. Each thrust went in a little deeper and with each thrust, Tim would groan. Slowly but surely, his movement became a little faster and a little deeper until his forward thrusts began to jolt my entire body. He had closed his eyes and started to mumble “Oh yes. That’s it. Oh you’re so incredibly tight. Oh, such a tight little tease arse, yes. Oh fuck, your so tight!”. Perspiration began to form on his forehead. He was fucking me like I was a rag doll. As his pelvis started to slap my butt cheeks, I felt his cock harden even more. He was really grunting now and as he arched his back slightly, he grabbed the base of my legs for more leverage; His thrusts were hard and violent. He moved his hands to my waist and squeezed me for more and more thrust. He was using my hipbones as fuck handles. I felt his cock reach full plateau and as it began to spasm in me, shots of cum entered my young body. He continued to push into me, straining to thrust out the last drop of cum. He seemed to go on forever. Thrust after thrust and he was panting so hard I thought he might have a heart attack.
He opened his eyes and gave me a look of surprise, as if he had forgotten whom he was fucking. He gave me a quick smile and then slowly eased his sagging manhood gently out of me. He removed my ankles from around his head and let them down onto the lounge. I won’t bore you with the pain that was engulfing me except to say that I couldn’t move. He laid down on the lounge adjacent to mine and let out one almighty sigh. “You are a great fuck” and with that he put his hand in mine. “I hope I didn’t hurt you too much, but I like it a little rough and I don’t mind the tease you’ve got!” I looked at him and said I had better get going. I didn’t think I would be able to ride a bike for a while. Tim said he wouldn’t waste my arse on a bike seat.
Over the next few months we did some pretty crazy things. Once I got dressed up as a girl, with the mini and knee high boots and lipstick. The works. We went over to a nearby town and went to the pictures. We made out through the entire screening. Tim got so horny, halfway home, he tied my hands behind my back and with my panties around my knees, he fucked me over the hood of the car.
I ended up having a really good time with him. I loved the idea that by day, I was a model student and son, but by night I was Tim’s little slut. My parents would never understand, and in the end, what did they know?