Initiation to Sexual Adventure

I must thank you for the good times we had when I returned to Wellington. I have always liked masquerade parties; wearing a mask brings out the wild side in people, including me. I also liked your Roman theme, because fixing up a toga is not much effort and there is great latitude if you want to use your imagination.

I am not sure I expected to find an absolutely gorgeous vestal virgin giving a blow job to a suitably well endowed gladiator in your lobby as I entered the house, but it certainly set the scene for the night and the next forty eight hours. Finding later that the vestal virgin had a nine-inch appendage was a very pleasant surprise.

Needless to say, your vestal non-virgin, made a huge hit with me. We spent a fair bit of time together during my remaining days in the City. Thinking of her has brought back some memories of my youth, and I thought I would tell you about my first time with a man, and his degradation of me.

As a youth, I was of just above average height, slim, fair, involved in every sport possible and blessed with a relatively clear complexion. While I played a lot of sport, I wouldn't really describe myself as a team man, and I liked to spend time alone, reading, riding my motor-bike, and so forth. I have to admit that, from the age of thirteen, I also had a close relationship with my male member.

I had two older sisters, three and five years older than me. At the time of this story, both sisters lived away from home, one working and the other studying. Both my parents worked and I spent a large amount of my time unsupervised in my teenage years. Because I was doing well at school, was 'socially well adjusted', and involved in sport, I was no concern to my parents or anyone else, and the free reign I was given was a consequence of that.

My story starts when I was eighteen. After school one Friday near the end of the spring term, I was bored and went hunting fashion magazines in my sister's bedroom closet, as I had found some of the photo-spreads lent themselves to becoming erotic stories in my imagination, and with gorgeous women and a vivid imagination I could easily sate my teenage stirrings for a while. I had another two hours before my parents came home, so I could ramble through any part of the house quite freely.

I knew where the magazines were kept, and quickly located the box on the floor and hunted out the editions that experience had told me had the best spreads to satisfy my imagination. Less than twenty minutes later I, sated, was returning them to the same place in the box and pushing back in the right place. This time, however, the box did not slide neatly into the slot it came from.

I got to my knees and groped around to find what was causing the obstruction. I found myself pulling out one knee high black leather boot, with three-inch heel. I vaguely recognised it as a boot I had seen my older sister wear the last time she had been home, and groped to find where it's pair was so I could restore it to the space from where it had come. The other boot was hidden in the far corner, and it too had fallen over. I pulled it out, intending to put both back immediately.

As I put them together, I noticed that the second boot was stuffed with something, shiny and black. I pulled out a black lace bra, panties, suspender belt and stockings. These were not the type of clothes my sisters ever seemed to wear – perhaps I had misjudged them! As I went to stuff them back, the shiny, slippery, light feel in my hands proved irresistible. The feel made my cock start to grow again.

I undid my jeans, pulled out my member and ran the panty material softly across the head. I had to wear these! I quickly pulled off my trousers and shorts and pulled on the pants. My cock poked above the waistband, still glistening from the remainder of my recent activities. The panties felt great as I tucked my cock sideways into the lace fabric. I slowly rubbed myself through the material, feeling the smoothness of the nylon and the roughness of the lace. I was close to coming again, and pre-cum liquid seeped out through the black of the panties.

I was mesmerised by the experience. I left the pants on as I figured out how to fasten the suspender belt. I knew enough from the fashion magazines and the occasional Penthouse to work this out fairly quickly. I unravelled one of the balled up stockings and tried to pull it on like a sock. I soon realised that this was not the way it was done and then bunched it up so I could get the heel in the right place and pull it on gradually. My cock was like concrete as I pulled the stocking up my leg, gradually adjusting it as I went so it was straight. By the time I had the second stocking up, I was achingly hard.

I loosened the suspender straps to their fullest extent (my sister is shorter than me) and fastened them up. As I straightened I got the first delicious feel of stockings being tightened by the pull of the suspender. I rubbed myself through the material again. This was a real turn on.

I looked at the boots. I undid the zipper, and placed my stockinged toes into one of them. They were quite narrow compared to my foot, and I thought that I wouldn't be able to put them on. As I pushed a little harder, the ball of my foot went through the opening and into the boot. I had the same trouble with slipping my heel down, but once it was there I felt my foot to be very tightly held but not too constricted. My toes were at the end of the boot, but they didn't seem too tight for the pleasure I was getting.

I slowly tried to do the zip up. It was a very tight fit around my quite muscular calf and there was no way it was going to do up. I realised that, in standing in the boot, my muscle was tight, and so I sat on the floor and managed to do the zip up over a relaxed calf. I remained sitting while I pulled the second boot on and zipped it up.

The feeling as I stood was amazing. The tight constriction of my calves and the precariousness of the three-inch heels was very exciting. I looked down and examined myself, before standing in front of the mirror on the closet door. The view of my bottom half was not too different from those I had recently been masturbating over in the fashion magazines, but now I was living it. I walked to and fro, watching my legs and butt and cock encased in stockings and panties in the mirror. I tried walking with a hip sway, which is difficult when looking over your shoulder at a mirror, but easier walking towards the mirror.

As I stood watching myself, I rubbed myself again, and soon had unleashed another load. I stood watching myself and my growing wet spot, when I heard my mother's car turn into the driveway. An hour early! I quickly unzipped and pulled the boots off, shoved them in the closet and shut the door. I pulled my jeans on and fastened them before the front door opened. Looking around, I picked up my underpants and the black bra and desperately put them in my pockets. Then I slipped into the hallway and into my room, calling out hello as I sat at my desk and opened my study folder.

There was a muffled hello from the other end of the house. I got up, pulled a pair of socks from my dresser and pulled them on over my stocking clad toes. I got a tissue from the box and stuffed it into the panties to try and soak up any remaining liquid. I sat down at the desk and let the luxury feel of the clothes against my skin inside the jeans build while I pretended to study. About five minutes later my mother came down the hallway.

She asked if I would be ok if she and my father were away for the evening, there was a business function in town and they thought they might as well make a night of it and stay in the city (about an hour away) with friends. She was just collecting some spare clothes for them both. I said I would be fine, that I might go for a ride on my bike, grab a burger on the way back, and either visit some friends, watch TV or study. Not that I intended going out on my bike just yet!

My intentions were changed when she said I could save her some time. She had to deliver a package to a customer who lived just out of town, I could take it for her and that would give me a ride on my bike. It needed to be there within the hour. If I took it now, she wouldn't have to worry about rushing through the shower. Telling me the package was on the back seat of her car she went to get ready.

I put on my bike boots, thinking about the difference between those and the ones that had encased me earlier. As I readied myself, I remembered the bra and underpants in my pockets. I threw the shorts into the laundry basket and contemplated the bra. It was more like a bikini top than the bras I had seen in the laundry. It had the fastenings at the back like a bra, but otherwise was shiny straps of black that connected two shiny black triangles of material edged with soft lace. The triangles were sewn so they formed a shallow pocket and had a more solid bottom edge.

As I examined the bra, I started to stiffen inside my jeans. I quickly decided to see what it felt like on. I stripped off my tee, and put my arms through the loops and struggled to pull it tight around my chest. It was high up above my nipples by the time I fastened it, and when I pulled it down it seemed too short. I worked out the shoulder straps and slowly slid it down. The inside fabric was cool on my nipples and felt very good. I was surprised it sat in place so well, slipping back down after I had raised my arms to pull the tee back on over it. I pulled on my leather jacket and headed for my bike.

The bra didn't seem all that great a turn on, but the way the stockings felt against the jeans, and the panties against my cock were. I yelled goodbye to my mother, pulled my helmet on, grabbed the package and headed up the street. Twenty minutes later, I had delivered the package and was headed home along one of the many winding backcountry roads around town.

To tell the truth, I was so caught up in the riding that I forgot about the clothes, only the walk to door to deliver the package served to remind me of what I was wearing. Caught up in the twists and turns of the road I was on, I would have soon forgotten about them again if it wasn't for the feel of the fabric each time I moved my weight in anticipation of a corner.

That feel was on my mind as I powered out of one turn, making my reactions a split second too slow at the sight of a tractor pulling into the middle of the road to turn into a gateway. As it was, I had pressed hard into the corner and was a little too far into the middle myself. I could have altered my line and braked to avoid it, but because I was a bit preoccupied I was too late for that so could only straighten and head for the grass verge, hoping that I could run back onto the road a little further on. As I hit the grass I let off the brakes and gently tried to coax the turn before I hit the wire fence.

I almost made it. Although I had slowed considerably, things seem to go on forever, but in reality it probably only lasted five or six seconds. I came to rest in the grass, by the fence, on my back. I was mentally feeling my arms and legs etc for pain when a shadow fell over my helmet and an upsidedown face peered down at me. I became aware of a voice asking if I was OK. I pulled legs up and shifted arms and shoulders and said that I thought so. I rolled over and got to my knees. There didn't seem to be any severe pain anywhere, although experience told me that might not be the case in the morning. I reached up and fumbled the strap and took my helmet off.

We both said sorry at the same time, then laughed. The man was tall, about 6'2", and broad shouldered, with a tanned face and tousled dark hair. I recognised him as Mr Thomas, the father of twin girls who had been two years in front of me at school. The girls had been friends with the younger of my sisters, and we had sometimes come to the farm to pick them up or drop off my sister. Mr Thomas helped me to my feet. I was a bit wobbly as the effects of the adrenaline wore off, but I didn't seem to have hurt anything at all. The bike was lying on its side, stalled. He helped me heave it up and I examined it – nothing showed any real damage except for a broken clutch lever.

I mounted the bike and sat on it, intending to try to start it. As I sat down, the shakes hit me. Mr Thomas had to hold the bike as my legs and arms went to jelly. He told me I might be taking things a bit too quickly. He suggested putting the bike onto the tray behind the tractor, and we would go up to the implement shed where I could rest and recover while he found out if a farm bike clutch lever might be a temporary substitute for mine. I agreed and travelled up the farm track with the bike on the tray.

The implement shed was a long high building, one end of which served as a barn, with an office next to it, then a series of six or seven bays for machinery and implements. He parked the tractor in the bay next to the office, and after I helped him offload the bike he told me to sit in the office while he attempted to fix the bike.

The office was a bright room but only half the height and not as deep as the rest of the building. A set of stairs led to a closed door that must be entry to an attic room. This didn't dim the light from the window to the yard across the front of the building. The lower floor had a large desk, some filing cabinets a table around which there were some chairs, and a couch by the windows. I sat on the couch and stared out the window, not really seeing anything at all.

After twenty minutes or so Mr Thomas came into the office and asked how I was. I told him that I felt a lot better and thanked him for his help. He said he had managed to fit a spare lever to the clutch with a little filing, so if I was ok I could probably ride it home. He offered to run me home if I didn't feel up to riding. I said I felt ok, and nothing seemed damaged at all so I should be ok.

He asked me to get up and walk around the room, I guess so that he could see that I wasn't hiding a broken leg. As I got up I felt the stockings against the jeans again. While I was walking he said I had some pretty serious grass stains on my jeans and my leather jacket had a few new marks, and asked if I had checked to see everything was ok underneath. I said I hadn't but it all felt ok, so I would be cool. In truth, I couldn't see anywhere private where I could check and there was no way he was going to get me to take my jeans off in front of him.

He looked at me, then explained that he felt a bit responsible and he didn't want me riding unless he knew I was ok. I nodded and stripped off the jacket to show that there were no grazes or cuts on my arms. There were none, as the accident had been at a low speed so I felt safe. I was about to put the jacket back on when he said to leave the jacket off. His voice, which up to now had been concerned and soft, had changed to something quite different. It was hard.

I turned to him, and he moved right in front of me. To my surprise, he reached out a hand, and poked me on my left nipple. I had forgotten about the bra – it would show very clearly against the tight tee shirt! I was really embarrassed, I looked down and watched his hand. It came up and lifted my chin so I looked into his eyes, he had a sort of a smile on his face, but the eyes were cold. "Take the shirt off." His voice was an order. I tried to explain but nothing came out – I just stood there. He reached down, grabbed the bottom of the tee and pulled it up forcefully over my head, my arms rising involuntarily with the force of his movement.

"I will only ever tell you to do something once" he said, "and if you don't do it, I will make it happen. That's the way any sissy boy gets treated." His voice was very hard. I tried to explain about not being a sissy but just trying something once and my mother coming home with jumbled words amongst a bunch of almost hysterical sobs. He slapped me. Not too hard but enough to rock my head, shut me up and take the edge off my emotions.

"Any boy who puts women's clothes on is a sissy, and deserves to be treated like one. Take the jeans off so I can see just how much of a girl you are." I looked down, I could see the top of the suspender belt up around my waist. I have always been quite determined and stubborn, it is part of what makes me good at sport I guess. I shook my head and bent to retrieve the tee shirt from the floor where he had dropped it. I was going to get out of this place - I would even fight him if I had to.

He caught my arm at the hand and squeezed down with his thumb just behind my thumb. I was in agony and it took most of my strength, if not my determination, from me. He took the tee from my other hand and threw it on the couch. He dragged me across to the desk and, still holding me, opened a drawer and pulled out a Polaroid camera. He let go my hand and I pulled it back to me and rubbed it with my other hand. He laughed, and as I looked up, he caught me with the flash of the camera.

I watched as the picture spilled from the camera, knowing what I was going to see once it developed.

"I can hurt you a lot," he said "but not all hurt is physical. You're a bright sissy, you don't need me to explain – do you." It was a statement, not a question. My world revolved in my head, I saw photos plastered across school, being laughed at by everyone, no friends, the disappointment on my mothers face and the loathing on my fathers. He stripped the paper from the picture. In the back of my mind the faint hope that it wouldn't turn out exploded. It was worse, the look on my face, the angle of my head and the way my hands were crossed in front of me made me look like I was doing a come-on to the camera. The bra and the suspender belt showed clearly.

"The camera never lies, you are a true sissy boy slut." His eyes moved from mine to my jeans, the message clear. Ashamedly, I sat on the edge of the desk and undid my boots, slipping them off. Then I undid the jeans FLASH, the zipper FLASH, and slowly pulled my jeans down FLASH, before standing before him with my jeans in a pool at my feet FLASH. The photos pooled on the desk. Somewhere in the turmoil of my mind was an urge to see how they came out.

"Take the pants off." I looked at him, really fearing what was going to happen. "You have them on the wrong way, the pants go on the outside of the suspenders." I didn't think. I undid the suspenders, took the pants off, refastened the stockings FLASH, and then put the pants back on FLASH, FLASH. I stood in front of the desk, head down.

He peeled paper from the developed shots. I watched as he placed them in a line, out of sequence but telling a very damning story. I looked at myself, the shots of me fastening the belt to the stockings and pulling up the pants covered from my navel down and showed my cock, shrunken with fear, surrounded by the lingerie. The full-length shots with the bra and my face looked somehow male and ridiculous.

He turned and I watched as his hand reached for me. My arms instinctively moved to cover myself, but a barked "Stand still" stopped the movement. I was totally in his power, and I felt helpless and wretched. His hand found the pants and cradled my cock and balls, gently squeezing and rubbing with a circular motion. Despite myself, my cock started to grow with the stimulation. It was the first time anyone had played with it other than me, and I reacted in the way of any teenage boy – but at the time I was alarmed.

"A real sissy. Dresses in girls clothes and likes it when a real man fondles him. I wonder what else you like, sissy?" I looked helplessly, probably pleadingly, at him. But there was no mercy in his face. "The cum on your sissy panties shows me you know how to play with your boy toy, let me see how you deal with a mans one. Take my cock out sissy." I couldn't believe it – he was asking me to touch his cock. I immediately went totally limp, but as I hestitated he started to slowly squeeze my balls. As the pressure grew I knew I had no choice and reached out toward him.