Bob Roberts

By Calperniaus

 

I met Bob online in yahoo clubs. He or I should say we were reading messages in Washington Crossdressers. He told me my physical profile caught his eye. 6’, 135lbs, shoulder length brown hair, green eyes and a love of trying to pass. Of course I don’t pass if you’re paying attention. But if you just glanced at me on the street you wouldn’t notice anything. I dress kind of sexy but am careful to avoid too much attention. Although, those fucking little teenage sluts always clock me.

So one evening, Bob IM’ed me. He was going on about how hard it is to find a fun guy who knows his role. I was flattered when he said he loved the pics he’d seen. Nothing trashy, just a few nice looks; a short skirt with knee boots, A sexy secretary in heels in a suit with a too short skirt, tight jeans and a silk blouse.

I’m very careful with my clothes and like them to fit perfectly so I only stuff a C-cup, giving me a sexy but pleasing profile. To give an illusion of hips I’ve tried pads but they work best in pants, so when I wear a skirt or a dress I tight lace a corset dropping my already slender 29 to a 24. The difference between my waist and hips looks very feminine. It does leave me a little breathless though, but that helps with my voice.

Speaking on the phone is the only time I pass 100%. At home I often answer the phone in as Janice it fools everyone. A couple of guys I know think that I have a girlfriend named Janice because of it.

I chose the pictures in my profile carefully to show off my ability with Make-up. I usually do an 80’s Donna Mills look. I learned it from a video she made called "The Eyes Have It" it shows how to create dark smoky eyes, kohl rimmed with heavy dark shadow. It can be a little sleazy looking for daytime, but shit, fun with make-up is a big part of being a T. Tapes are how I learned to do most of my make-up and hair. Its not like most of us guys spend our teenage years putting on our faces everyday, the way breeders do.

After several weeks of IM’ing and leaving messages in the forum, Bob asked if I would like to get together. I was a unsure because he’s very into bondage and wanted me to try it. I relented after he had me look at several different sites. I learned about negotiating the whole scene ahead of time, "Safe" words etc. Still, I was pretty nervous. I’d never been with a man and he seemed really into the whole BDSM thing. Up till now all my dressing had been for my personal pleasure. Sure I loved it when I turned heads, but I never did things with anyone. I always went home and masturbated by myself.

We agreed that we would not have sex, I agreed to the use of leather ankle and wrist cuffs. He also talked me into a leather collar. We talked a lot about what he wanted me to wear. His idea was to have me wear jeans and a baby style t, black pumps with a 3" plus heels and lots of jewelry (queer huh?).

I tried several variations of what he asked for, but it was just too boring for a meeting like this. It would be great for an afternoon of playing around town, but for a first meet it seemed too plain.

I was nervous because Bob kept telling me that the first time was the best for the sub something about fear of the unknown. But he kept telling me not to worry that he would respect my "Safe" word. In our case we decided that I would use a simple gesture tapping my thumb and fingers together rapidly.

Bob had insisted on having a few surprises for me that were not negotiated. A big mistake for me. But with my "Safe" gesture he insisted it would be fine. I have to admit that I was really excited by the whole idea of being surprised or I never would have gone through with it.

I decided to go all out for him. Screw his idea for an outfit, way too boring. I took the second half of the week off and got some gorgeous long nails. They were a deep metallic purple. With green eyes you’d think purple is be a bad idea. But for some reason I’m lucky that any dark color seems to go well with my eyes. The purple color scheme went well with the black of the my suit. A dark purple blouse with a low neck showed off my tits to great affect. The whole outfit was new and had cost me almost $500.

I had learned how to create great looking tits on a site that explains how to use tape to push up all the flesh under your arms and breast that gives you real beauties when done with a Wonder Bra, I still have to used pads below the flesh to fill the bra. All of my lingerie was dark purple satin to go with the rest of the outfit, unfortunately my corset is black, but it looks really good with the purple lingerie.

Bob had told me he was over 6’, but I wasn’t sure how much over. So I decided against wearing heels. Instead I wore a pair of knee high boots with low heels. I thought it would feel wrong to be taller than him. I was looking like one hot fucking sexretary.

On the appointed day I drove over to Bobs house and walked up the steps to his porch. The house was nice looking, it looked expensive. I knocked on the door like we had discussed but practically before my hand dropped to my side, the door swung open and a very tall cop was staring down at me his eyes hidden behind mirrored cheaters. He looked like a motorcycle cop with tall boots and riding trousers, the only thing missing was a helmet.

"What the fuck? You’re wearing flats" This guy scared the shit out of me. I had never seen Bob before, but this couldn’t be him. This guy was at least 6’4" and I was sure Bob would have told me he was a cop.

I stammered out "Excuse me is this Bob Roberts house?" He didn’t even bother to answer jerking me inside the house by my arm. "Look you little bitch, you didn’t do what you said you’d do." Again I started to stammer my question, when he grabbed me roughly by my arms and spun me towards the wall. I could hear the door slam shut behind us but couldn’t see it my face was against a wall. "Spread your fucking legs perv." With that I felt his hand at the back of my neck and my feet being kicked wide. What the hell was going on here? Was I being arrested? Where was Bob?

I was extremely scared. What had I gotten my self into? Had Bob been arrested? The cop quickly frisked me and turned me around. "Hold out your hands!" I don’t know what I was thinking but I just held out my trembling hands no attempt to say anything or resist, I just did it. He put handcuffs on me and then turned me back around forcing me to bend over putting my now cuffed hands on the floor. From behind me he attached cuffs to both of my ankles over my nice boots.

I was freaking out, a cop wouldn’t be doing this. He jerked me upright and spun me back around to face him. "Typical, you stupid little bitch. You were told to wear heels." With that he slapped me hard causing me to stumble, a little blood trickled out of the corner of my mouth and my eyes were tearing up. I didn’t do anything to protect myself. My cuffed hands stayed at my waist not making any move to protect me. The fear was beginning to overpower me.

"Hold your hands straight up" With my hands over my head he attached them to a small chain hanging down from a beam in the ceiling. Again he kicked out my feet leaving me dangling from the ceiling by my wrists alone, causing pain in my shoulders and arms. He quickly attached a metal bar to the cuffs on my ankles, it held my legs so far apart that it was causing cramping in my hips, my skirt had ridden up my thighs to an obscene position, the toes of my boots were barely touching the floor because of the chain holding my hands. When he was satisfied with my position he placed a leather collar around my neck, there were several rings riveted around its front and sides.

I was horribly frightened, but somehow the pain and fear were turning me on. I could feel my dick stiffening in its satin prison, normally it doesn’t get hard when it’s pulled back between my legs. But right then it’s trying to get free was causing more pain. Starting a vicious cycle of pain causing more arousal, more arousal causing more pain. The humiliation I was feeling with the mixture of emotions; fear, pain and pleasure was intense, my mind was bouncing all over the place.

"You do look hot in that outfit." He was standing behind me when he said it. Suddenly I started to blubber for him to please stop. I completely forgot about the "Safe" gesture. Besides this guy wouldn’t know about it anyway. From behind I felt his hand grab my hair in back and hold my head still. I was sobbing even more, my shoulders shaking. He was ignoring my pleading.

I could see the both of us in a mirror on the opposite wall. He was so much bigger than me. He leaned into me and held my head still with his arm pinning it to his chest. With both hands now free he shoved a metal contraption into my mouth, there was a bar that held my tongue down and a pair of arms that held my mouth open with this stuffed in my mouth he pulled a leather strap around my head and buckled it into place. I could no longer talk I started to cry out but with my mouth open and my tongue held down it wasn’t very loud and sounded incoherent. In the mirror I could see myself, my mouth open making an O.

He was smiling saying "It would have been better for you, if you’d only listened to directions. Now look what you’ve done to yourself." My fear was now so great that my erection completely disappeared. I could feel it shriveling between my legs, some pre-cum soaking through my panties and running down my leg.

"Lets see have we forgotten anything? Oh that’s right the clamps." Again he spun me around grabbing the front of my blouse and ripped it down to my waist leaving it hanging over my skirt. "I think we’ll have to remove your breasts." He roughly tore out my breast forms and tossed them aside. I still had a weird looking cleavage because of the tape, but my cups were now half empty. I was surprised at the look of the clamps they were complicated looking things with screws and arms. How could he possibly attach those to my nipples.

For the first time since I had seen him, he was gentle as he reached into the cups and started pulling and kneading my nipples. The feeling was erotic. All the pain and fear had made me extremely sensitive. Finally he managed to raise enough flesh to attach the clips. At first the pinching wasn’t bad, but as he screwed down the clamps the pain become intense. I noticed my breathing had become shallow and rapid; my corset was making it even worse. Somehow he realized I was getting turned on again, although this time my penis was behaving and staying soft between my legs.

He started running his hands over my stocking clad thighs, playing with the garter straps, snapping them into my legs. He pulled my skirt a little higher exposing my crotch "How cute you’ve managed to tuck away your privates." The sight of a knife appearing in his hand was frightening. He quickly cut away my panties letting my dick drop free from between my legs. "You have a nice little dick, why would you want to hide it?"

He put the knife back into his belt and pulled a nylon cord out of a pocket. "You’ll really like this, that little dick will never be bigger than today. The cop grabbed my balls and pulled them down and forward stretching every thing. With his free hand he wrapped the cord around the base of my dick and balls.

As he pulled the cord tighter it started to hurt more than anything else he had done to me. It was more pain than I was feeling from my arms and hips. I was crying again. "That’s nice, you’re so happy you’ve started to cry. Careful though, your make-up is starting to run." While I was looking down at my dick it started to grow, it was much bigger around and longer than I had ever seen it. The head and shaft were turning shades of blue and purple almost matching my garter belt.

The pain had me sobbing with saliva running down my chin because of my inability to close my mouth. "We’ll have to do something about that drooling." From a table I hadn’t noticed he picked up a thick dildo that looked just like an erect penis only shorter just several inches in length. Roughly it was shoved into my mouth filling it there were clips that attached it to the mouth appliance. He attached a small pump that filled the penis until it sealed itself against my lips. "That’s much better no more drooling. I just knew you were a little cock sucking perv! You can’t get enough can you?"

I was shaking my head no, but he didn’t react at all. I had started shaking all over which he noticed and said "This could have been much more nicer but no, you had to blow it." I was crying with tears streaming down my cheeks but the only sound coming from me was a gentle sob.

He spun me around again and I could feel his hands on my ass cheeks. His fingers were spreading them and I could feel something cold pressing against my anus. My hips jumped a little when I felt something cool being squirted around the whole area and into my rectum. "You’ll need all the lube you can get when I start fucking that virgin hole of yours." When he said that I started wildly jerking around trying to get free. I wasn’t going to let some guy fuck me, Cop or not.

"Careful you’ll hurt yourself. With that comment I heard him walk out of the room. The pain in my shoulders was becoming intense and I was starting to lose the feeling in my cock and balls. My hips had cramped up and were stiff. How could I get out of this? Who was this lunatic, had he done something to Bob?

He returned to the room wearing just the boots and cheaters with a huge hard on. At seeing him I started franticly trying to get free. "Janice you’re going to hurt yourself stop it." He knew my name, what the fuck? "

"Now how do you feel? I’m so glad you like the gag; it keeps you from disturbing the neighbors. I’m going to release your hands, but first let me put this belt around your waist. It will fit right over that pretty outfit of yours." He wrapped a wide stiff leather belt around my waist and buckled it in back.

He grabbed my wrists and released them from the chain and pulled them down to my waist I fought with all my strength but it was nothing to him. Quickly they were attached to the belt with metal fasteners. I noticed that there was no feeling in my arms below the shoulder. I was now standing on my feet, but it was difficult because of how wide my legs were spread.

"Don’t worry I know how hard it is to stand that way. Here’s a little help." His hand grabbed one of the rings at the front of my collar and pulled it up so that my head was held chin up. I could no longer see anything that was lower than my head. His other hand was above my head and held a leather strap with a attachments for the rings on my collar on both ends. The top was already attached to the chain that had formerly held my hands. He snapped the other end to my collar.

"Watch your self, if you stumble, you’re likely to choke." I could feel his hands holding first one of my mine and then the other. "You’re nails are a really nice touch, but with talons that long you could scratch me and we don’t want that do we?" I couldn’t his hands but there was an odd sensation, I could feel leather on the fronts and backs of my hands. When he released the leash from the chain and I could look down. I saw that he’d put my hands in shapeless leather mittens.

"So, what was that safe gesture? Oh that’s right you’re supposed to click your fingers together, with those nails that would be very effective the sound would be quite loud. I’m so glad that you didn’t use your gesture" He said grinning. He continued, "The mittens are a great idea aren’t they, of course now I can’t see or hear your "Safe" gesture. But it was nice of you to agree to do away with it.

I started to cry again as I realized what he was saying. He had no intention of letting me stop him doing whatever he wanted. "Now sweetie, you do know that the "S" in BDSM stands for sadism"

One of his hands flashed out and slapped my balls hard. The pain was incredible my stomach shrieked in pain. My knees buckled and I fell to the floor. "We can’t have you falling like that, you’ll hurt yourself. The only person that’s going to hurt you is me."

He pulled me to my feet and dragged me to a chair and sat down, while pushing me over his knee. My ass was sticking up in the air and my balls were being crushed on his leg. "You really must be punished for something like that. A little OTK spanking is the least that you deserve. I heard the whoosh of air as something struck my ass. The pain was intense; with each whack my hips humped his lap, crushing my dick still more. He kept this up for several minuets. The pain had me crying into the gag uncontrollably.

Just as swiftly as the blows started they stopped. "You’ve been so good, how about a little reward? Would you like it if I masturbate you? He stood me up facing away from him. With one arm he pulled me back wedging me between the chair and his arm. His other hand was squirting a cool liquid onto my penis and balls. He put a little bottle down and started to jerk me off, very slowly the feeling was great, with the slick liquid creating incredible sensations as he pumped my shaft and reached around with his other hand and began fondling my balls. This was heaven. I was mewing with pleasure.

He dropped my balls and I could feel something pushing into my rosebud. "And now with something that virgin ass can handle? You like this don’t you?" I could feel something being pushed into my rectum I was surprised at the lack of pain. He was moving it gently in and out of me, slowly picking up speed. I noticed that my hips had started unconsciously humping back and forth to meet the thrust of the dildo.

What was happening to me? I was enjoying the feelings of being fucked, while he masturbated me. He stopped running his hand up and down my shaft. Again I herd the swoosh just before the slap. He slapped my balls just as hard as before. This time as my knees buckled I fell back towards him and his tool. "You see, you do like being fucked. I knew this would be a turn on for you. And now look, a little pain and pleasure gets you humping yourself."

I couldn’t believe what I was hearing. He sounded so delusional. But it was true the pain really was turning me on and I loved the feeling of the dildo pumping in and out of my ass.

"Now Janice, I want to ask you. Would you like me to make love to you? I was shaking my head yes. His treatment was driving me out of my mind. Could I really want a man to fuck me?

The End

 

 

 

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© 2002 by Calperniaus. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.