Jenny Learns Her Place free porn video

His hands held my hips tightly and his very large hard cock slammed into my asshole again and again, as if he were was going to ram it all the way out my mouth. I whimpered with each long stroke while my own small dick dripped the remains of my orgasm. It was amazing that he was hard so quickly after pumping my mouth full of sweet jism, some of it even spraying onto my face.

“Oh! Oh! Oh! Ooohhh fuck me good, baby,” I moaned over and over.

I'd known Bobby since grade school and had even enjoyed a couple of jack off sessions with him during high school but I'd never thought of him in this sense. When I saw him enter the bar I'd recognized him immediately but it had taken him longer to figure out who I was since I was now dressed as a woman. We were halfway through our second drink and his hand was high up on my nylon clad thigh before I saw the light come on in his face as he recognized me. When he did his hand slid the rest of the way up under my skirt and rested on my panty covered dick.

“John?”

“Not anymore, sugar, call me Jenny,” I had replied with a smile and rested my dainty hand on the lump growing in his pants. “You know, when we used to jack off together I wanted to do so much more but I was afraid.”

“I wish I'd known back then,” he answered and smiled. “I thought you were very cute for a guy and I spent many nights lying in bed and jacking off while thinking about you.”

Blushing brightly I replied, “So did I.”

After that we danced to a slow song and before it finished we were kissing like lovers.

“I want you, uh, Jenny,” he whispered in my ear, his hand resting gently on my ass.

He lead me back to our table so we could finish our drink, all the while his hand under my dress and lightly stoking my hardened little dick.

Setting my glass on the table, I said, “We better get out of here before I make a mess.”

“Want to go somewhere and make a mess together?”

“That sounds wonderful. We can go back to my place,” I told him as he lead me to the parking lot.

“Where do you live?”

“Same place. My folks died in a plane crash a couple of years ago. I kept the house since the insurance paid it off. Of course I've made some changes, as you'll see.”

The changes, which I had become accustomed to by now, were very obvious to anyone who'd ever been there before.

“I've got to know, Jenny. How often do you dress up? I mean, on weekends or after work, or what? You know, I've always thought you'd look good as a girl and what I see confirms that absolutely. You look better than good, you look fantastic.”

“Thank you, kind sir,” I laughed in response. “But to answer your question about dressing like a woman; all day, every day.”

“Really? Cool! More than just the average crossdresser, then. Are you thinking about going all the way?”

“Oh sure, I think about that daily but I'm not sure I want that. I mean, if the right man wanted me go that far, I might, but so far I'm not planning on it. Hell, getting breast implants hurt bad enough, I can only imagine what the other surgery would feel like. But I have given some thought to having my testicles removed since I'm not even remotely interested in reproducing, especially since I can't get pregnant.”

“Real tits? How cool is that?”

“They're real between hormones and implants,” I answered, laughing.

Looking at me he smiled and said, “I'd surely love to get a taste of those babies.”

“You would? Don't you want to pinch and twist and fondle them as well?”

“You bet your sweet ass!”

Leaning over the console, I began fumbling with the zipper of his pants and before very long his cock was standing up proud and stiff. Moving closer, I could smell his maleness and it was quite intoxicating. I started off by licking the bulbous head, swirling my tongue all around it before even trying to get him in my mouth. Sucking cock was something I loved doing and I knew the guys I'd sucked in the past liked what I was doing. Slowly but surely I worked my lips around him and began doing what I knew men loved which was taking all of their cock, no matter that I was always spared the last couple of inched because of the material and zipper.

“Damn, Jenny, you sure know how to use that mouth. Why the fuck I didn't press the issue a few years ago, I'll never know.”

I looked up momentarily when the car left the freeway and I knew where we were. I only had a few minutes to get him off before we arrived but I was confidant. Before taking him back into my mouth I said, “Cum in my mouth, baby.”

Stopping at a red light, I could sense his urgency so I worked my head up and down faster and faster. We took off from the light and I kept on going even though I could hear a car driving beside us and getting a good view of what I was doing. We'd just barely stopped at the next light when I felt his hard cock trembling and his breathing becoming very ragged.

I think we sat through a green light and so did the car next to us because Bobby was busy trying to drown me with hot, delicious, cum. When I sat up and wiped my lips, the car next to us honked and drove away.

Smiling at Bobby I said, “That's what it costs you to play with my titties. I like getting paid up front.”

“What will it cost me to get in your panties?”

“A dance, a kiss and a feel.”

“Great!”

We pulled into my driveway and parked beside my little car. I'd taken a taxi to the bar just in case I was too tipsy to drive home or if I got lucky. By the time we got to my front door my dress was completely open and when I opened the door my dress fell off. Bobby kissed me long and hard, the tour of the house forgotten.

We left a trail of clothes from the front door to the bedroom, mostly his because all I had left to take off was my bra and panties. He insisted that I keep on my heels, stockings and garter belt but other than that I was naked. Several guys liked me dressed in this manner and some guys liked me nude; either way was fine with me. Even though I'd given plenty of blow jobs while fully dressed or had been bent over to get fucked with my skirt up on my back and his pants around his ankles, my personal preference was both parties fully nude.

Bobby gently lowered me to the bed and then joined me. He played with my titties, sucking, pinching, and then rolling the nipples between his finger and thumb and I was growing hotter and hotter. When he flipped me over and pulled me to my knees I was expecting to feel his big cock trying to enter me but I was pleasantly surprised. Bobby pressed his lips against my puckered little hole and began licking me before sinking his tongue into me. This was definitely a first for me and I loved it.

“Holy shit, baby, that feels absolutely wonderful!” I growled between gasps, my entire body shivering with lust. “You're driving me crazy! Oooohhhh yyyesss! Oh baby, please fuck me! I need to feel your big cock deep inside me! Fuck me! Fuck me!”

Bobby straightened up and moved closer to me, aiming his rigid cock at my tiny hole. He moved against me and began pressing forward, slowly forcing his dick inside.

“Oh yyyesss! Oh, fuck it hurts! Shit, it hurts so fucking good! Fuck me!” I squealed again and again, giving myself completely to him.

Suddenly he was buried completely in me and remained still so I could adjust to him. After a few minutes I began moving on him, pulling off his cock and then slowly pushing myself back on him until he picked up the rhythm and began moving on his own.

“Yyyesss! Yyyesss! Oh yyyesss! It's so good! Fuck me good, baby! Oooohhhh fuck me!”

Thirty minutes later he was still plowing into me, faster and harder, giving me the best fucking I could remember.

“I've wanted to do this for years, Jenny, ever since high school! You're ass is so hot, so perfect, and so delicious!”

“And it's all yours,” I responded, my words broken by gasps. I wanted him to cum inside me more than I'd ever wanted any man.

In mid stroke he shuddered and jerked, slamming his cock into me before hammering me with a lustful frenzy. My body began to shake once again but my cock had nothing left to spew. I was cumming again, but in a manner so entirely different than a regular orgasm. This time my orgasm seemed to emanate from the center of my being. When his sperm blasted into me I thought I'd died and gone to heaven. Bobby kept on pumping his hot cum into me until I felt it oozing down over my own spent balls.

We collapsed onto the bed in a mass of tangled, use flesh. He rolled me over and kissed me again, holding me close to him.

“That was fantastic!” I gasped.

“I've dreamed of this forever but I never thought it would happen. Now that it has I want to do it again and again.”

“Do you say that to every girl you fuck to hell and back?” I asked, holding him tightly. I wanted to tell him how much I wanted the same thing.

“Would I lie to you, sweetheart?”

“I certainly hope not.”

“I won't,” he said and lightly kissed my lips.

“I'll hold you to that,” I replied and smiled at him.

“Well you just go ahead, little lady,” he answered using a decent John Wayne voice. “Now get your ass out of bed and let's go eat.”

An hour later we were sitting in an all night cafe. Bobby had insisted that I go without the benefit of panties, bra, or anything else other than heels and dress. We ate and talked and while we did so his hand moved under my dress and fondled my little dick.

“I've always thought your clit was so cute,” referring to my dick in the proper feminine term.

“Thanks,” I replied, smiling broadly. “And I've always thought your cock was lovely but now I know for sure it is.”

Some men liked me being very well under endowed while a few would have preferred me being much larger, I was happy with my little tool, especially since I always assumed the female role during sex. If a guy wanted me bigger so I could fuck him, I used a strap on dildo. This was an act I rarely was asked to do and really didn't like it because I wasn't the dominant type.

By the time we got back to my house it was close to three in the morning and by then I was dead tired. However, I wanted to get to know about Bobby so I asked him if he'd like to spend the night, which he did. Very rarely did I ever ask a man to stay the night. I might sleep with a man in a hotel or at his place but hardly ever did he anyone stay at mine. Somehow we managed another session of fantastic sex before falling asleep.

The next morning I work up and put on a short robe before quietly going to the kitchen to make breakfast. Bobby met me there before I had everything ready and sat at the table drinking a cup of coffee and watching me.

“You can cook, huh?”

“Of course. If I remember correctly you used to like your eggs fried as hard as a rock and your bacon crispy.”

“Damn, you remember that?”

“I remember everything,” I said with a giggle.

We finally sat to eat breakfast and talk a little.

“Do you have any plans for today?” Bobby asked between mouthfuls.

“Not a thing.”

“Would you like to go to a movie?”

“A date?”

“Yes, a date. A movie and then something to eat and then ...”

“I'd love it; all of it.”

“Great. After breakfast I'll need to go back to my hotel and change clothes. So after a shower and a shave, I should be back in two or three hours.”

“While you're gone I'll do the same and be ready when you get back.”

I know it was just a date, but I'd only been on two dates before this and they were just driving around for a while and then parking somewhere quiet and having sex in the backseat of his car. The vast majority of my encounters had just been for hooking up and getting laid or sometimes just sucking the guy's cock. Not that it was something I didn't care for but this time I was going on a real date and I was very excited.

After eating and deciding which movie to go to, Bobby dressed to leave. Before leaving, however, he kissed me hard on the lips, his tongue delving inside and searching every niche and cranny of my mouth completely while his hands opened my robe and gently roamed over my nakedness. Even though I was excited about going on a date with him, the thought of spending the day in bed and giving myself to him over and over was equally as exciting.

“You're so smooth and sexy, Jenny. I never dared to dream we would ever be doing this even though I've wanted to for so long,” Bobby whispered.

“I know what you mean. I've longed to be in your arms since before we ever did anything,” I replied and then raised up on my tiptoes to give him another kiss. I don't know how many men I'd kissed but Bobby felt so different.

He broke the kiss and patted my bare ass before saying, “I better go or we'll wind up spending the day in bed. While I'd love to do that, I want to take you out.”

When Bobby returned he was in a nice sport suit and I was wearing a knee length, off the shoulder, white dress, nude stay up stockings, a pair of sheer white panties and a pair of pumps with four inch heels. The heels didn't even come close to making me as tall as Bobby, who stood an easy six feet tall while I was barely five feet four inches in my stocking feet.

“Are you sure you don't want to spend the day in bed?” I asked after I kissed him.

“The temptation is great,” he replied, “but I want to take you out to a movie, then to dinner, and then I want to come back here and fuck your brains out.”

Smiling, I replied, “It all sounds good to me.”

He took my hand and led me to the car, opening my door and helping me inside. The guys I was usually with just let me walk around the car and climb in on my own. It felt nice to be treated like a lady instead of the easy tranny they knew I was. When we arrived at the cinema Bobby took my hand and we walked together this way. He seemed to not care that he was being seen in public with a transvestite sissy, cock craving degenerate. Of course, I passed with ease and only anyone who knew me personally would know that I'd fuck at the drop of a hat. To be sure, I knew quite a few women who would do the same thing.

We were seated in the theater with several minutes to spare and Bobby said, “I was married for a while.”

“And you're telling me this because …?”

“I just wanted you to know. I was married to a great woman for almost two years. We broke up because I had a really hard time keeping it up for her.”

“I find that hard to believe,” I giggled, thinking about how many times, and how quickly, he had gotten hard for me.

“That's what you do to me, Jenny. You drive me completely insane with lust.”

“Or maybe you're just a bit more bisexual than you imagined.”

“I've thought about that. Even thought that I was totally gay. I've been with a few men and even a couple of trannies, and yeah, I could perform okay, but every time I was with any of them, I always thought about those times we jacked off together.”

From the way he had reacted yesterday I had a hard time imagining him as being unable to perform. I wondered what other things he might have in the back of his head and was afraid to voice them for fear of being ridiculed. I came to a decision that, unless he wanted to hurt someone, I'd be willing to do anything he wanted. I mean, when you come right down to it, I was fairly kinky and very liberal minded. I had posted hundreds of photos on the Internet and about half of them had me in various compromising positions with one, two, three, even up to six guys at the same time. Other photos were of me in various states of dress from the very nice to the very sexy, to panties and bra, to nothing at all, both in private and in public.

During the movie Bobby kissed me several times, felt my titties, sent his hand under my dress to fondle me, but all that came of it was that I got super horny. I would have given him a blow job but the movie ended before I got the chance.

From the cinema we drove to a very nice Italian restaurant and enjoyed some very exquisite food while we talked. Our conversation ranged from the movie to some more interesting and personal things.

“Have you ever had sex in a public place?” Bobby asked out of the blue.

“Yea, a couple of times, unless you want to include the backseat of cars,” I replied. I'd thought about lying but I didn't have any idea if he'd seen any photos of me online.

“Did you like it?”

“Yep. And to answer your next question; yes, I'd do it again with the right guy. Uh, that means I'd do it with you if you wanted.”

“That would be cool. My ex-wife would only have sex in bed with the lights out, not even in daylight.”

“Bummer. Was she ashamed of her body of something?”

“She thought that any one that would show their body was a pervert.”

“Well, I guess I'm a pervert,” I laughed. “I think my body is pretty nice and I'm proud of it. I walked in a Pride parade a few years ago and while I had to wear clothes of some sort, I left very little to the imagination. I wore a g-string and a super small bikini top and that's all. I bet I was photographed a few hundred times. I like to be photographed.”

“I'd like to take some pictures of you, Jenny.”

“Go for it!”

“I will,” he smiled. “Hey, when was the last time you had a spanking?”

“Oh, wow, let me think...”

“What would you do if I pulled you over my knee and gave you one on your bare ass?”

“Scream. Shout. Kick my feet if I could. Maybe cry. Maybe get so horny I'd want to fuck you,” I answered and grinned.

“Really? Interesting. How about bondage? Ever done anything like that?”

“I've been tied up a couple of times and used very nicely. One guy I dated liked to tie me up and fuck my mouth really rough and then cum on my face. He was more into the power thing and humiliation than into me.”

“Well, I'd like to tie you up and use you, but I'm not into humiliation or anything like that. Well, maybe a little bit,” he added with a smile. “Don't get me wrong, there's a lot of humiliation involved in most BDSM scenes, especially if a third party is involved or even just watching. Hell, spanking can be humiliating all by itself, which it's supposed to be. For instance, my ex sister-in-law was a dyed in the wool exhibitionist, it both excited and humiliated her to be naked in front of other people. Her husband used to make her suck his dick in front of me and my wife. She'd be totally naked while doing it. Or he'd make her go into a convenience store late at night completely nude just to get him a pack of cigarettes.”

“And she didn't have a problem with that? Wow! Well I trust you, Bobby, and if you want to tie me up and do all sorts of nasty, sexy, fun things, I'm your girl. I'm also a bit of an exhibitionist in that I love getting my picture taken nude, clothed, or doing something very naughty.”

Bobby smiled. “I know, Jenny, I've seen your pictures on the Internet but I didn't know it was you until I saw you last night.”

I blushed brightly. “Then you know I'm a slut.”

“So?”

“Well that's how I make extra cash.”

“From the website or did those guys pay you?”

“The website. I'm a slut, not a whore!” I protested.

“Cool! You know, we could collaborate on some things and maybe generate more income.”

“Yea? What do you have in mind?”

“We could give your customers variety by adding a couple of more girls like yourself. Add in a little BDSM, a few more gang bangs, some of the girls getting together, you and one of the girls, all sorts of kinky stuff.”

“Well, it wouldn't hurt my feelings any to generate more income. I know a few girls, not many, and I have no idea if they'd even consider doing anything like this.”

“How about this, a web site with all the girls in various stages of undress, all the way to full nudity and erections? We'd have to launch it with at least a hundred full photo shoots so we could have a couple of thousands pictures for the customers and add at least one per week along with videos. Yea, yea! One site for the girls in various states of getting naked, one site with definite X-rated material girls fucking men, men fucking girls, sucking going both ways and girls doing girls as well, one site with bondage and spanking and all the other stuff that goes with it. We could even graduate to chat rooms if we can get enough girls to man the place twenty-four seven. “

“Wow! You're just full of ideas. Are you planning on having sex with these girls?”

“Having sex? I hadn't even thought about that.”

“Good answer,” I giggled. “But since I'll probably have to be having sex to get things rolling, I don't see any reason for you not to have some fun as well.”

“Well, I think we have enough to think about and we've probably worn out our welcome here, so let's go back to your place and have a little fun.”

“That's the best idea you've had. I can thank you properly for such a lovely date,” I said with a huge smile.

“What do you think about a little spanking to get things started tonight? If it's too much for you, just say 'popcorn' to make it all stop.”

“All I have to do is say 'popcorn' and you'll stop spanking me?”

“That's it.”

“Is it going to hurt?”

“I'm sure it'll hurt a little, but when it gets too much, just say the safe word.”

“Okay, I'll give it a try,” I finally agreed.

“Good! Now when we get to your house we'll stop in the living room and you'll slowly take off all of your clothes and then remove mine, kiss my dick and after I sit you must submit yourself to me for your spanking. Once I have you over my knee and in position the spanking will begin. If you feel the need to scream or cry or even cum, just go ahead. For the purpose of this spanking you can beg, plead, curse, or anything else but I will stop only when I'm satisfied your ass is red enough or you safe the safe word.”

“Okay, I'm willing to try it.”

We drove in silence while I contemplated what I'd agreed upon. A deep dark part of me found it to be very exciting but the logical side was wondering if I'd taken complete leave of my faculties. But then there was the tingling I felt down there between my legs that sealed the deal. My carnal desires had taken control.

Even though many men had seen me naked or mostly so, it was still a bit embarrassing to slowly strip in front of a man, especially given the circumstances. Once I was naked I helped Bobby to his feet and slowly removed all of his clothes before I knelt and kissed the head of his dick. I would have been content to just stay there and give him a blow job but he stepped back and then sat on the couch.

I knew he wanted me to drape myself over his lap but what should I say beforehand? Then a thought suddenly came to me and I knew the path I should follow.

“I've been a naughty girl, sir. I think I may need a spanking,” I said meekly.

“How have you been naughty?”

“Um, I kissed a man's penis and I enjoyed it.”

“Yes, that does sound naughty and you deserve to get your pretty little bottom spanked. Come over here and get on my lap, you dirty little girl.”

“Yes sir,” I answered and lowered my head as I began moving toward him.

As I lowered myself onto his lap he pulled me so that I was unbalanced and had to use both hands to keep from falling flat on my face.

Bobby's hand rubbed both ass cheeks and then suddenly slapped my right cheek, both startling me and stinging me. It didn't really hurt but it definitely stung like crazy. I'd barely had time to register this fact before his hand landed on my left cheeks and then my right cheek. I barely realized my mouth was open in protest when I needed to gulp in air.

I kicked my legs and then finally screamed, “Ooowww! Oh fuck that hurts! Stop it! Stop it! Stop! I'll be a good girl!”

He stopped long enough to place his leg over both of mine and then slapped my ass six or seven times in rapid succession, bringing me to tears. “You can't be a good girl because you're slut! You love to suck cock and get fucked! Say it! Say it, slut!” His hand landed on my ass cheeks again and again while he talked.

“Okay, okay! I'm a slut! I'm a slut. Now stop!"

“Tell me love sucking dicks! Tell me how much you like having a cock in your girly asshole!”

“Yes sir! I love to suck cock and feel hot cum filling my mouth before I swallow it! I love feeling a hard cock in my tight little hole, fucking me, breeding me! Oh please, please stop!”

Twice I almost used the safe word but then I thought I could take a little more, and then a little more. When I could feel his cock growing beneath me, prodding my belly, I knew he was getting pleasure from my spanking so I wanted to let him continue.

I wiggled madly on his lap while he kept on spanking me. My ass cheeks were on fire and I was definitely turned on. When he reached around me and pinched a nipple I went wild, pain and pleasure racing through me over and over until I couldn't tell one from the other.

“Oh! Ooohhh! Oh Bobby, I'm gonna cum! Ooohhh! Here it is! I'm cumming! Oh, Bobby, I'm cumming!” I screamed as my body tensed and jerked and then found release.

“Jenny, you fucking slut! You have cum on my leg! “ Bobby snarled and spanked very, very hard while I spewed my cum. “You can lick it all off after I finish beating your fucking ass!”

I was still so wrapped up in this awesomely powerful orgasm that I could barely breathe much less form any intelligent words. At that particular moment I didn't care if he spanked me for the rest of the night. It was really a weird feeling to be crying and cumming at the same time.

I stopped protesting and simply lay across his lap, my body trembling in the aftermath of my orgasm and racking with sobs from the spanking. When he finally stopped he gently rubbed my ass cheeks, soothing me. He pushed me down onto my knees so I could lick my cum from his legs and then lifted me up so I straddled him.

“Thank you,” I whispered just before his mouth closed over mine.

Bobby stood and carried me, still straddling him, to the bedroom and placed me on the bed. He followed and was soon on top of me, pushing my legs out wide. Before long his huge, hard cock was working its way into me, slowly opening my puckered asshole. Little by little his cock gained complete access to my nether region, impaling me on him.

“Oh fuck me, Bobby! Show me how a man treats his fucking little slut! Make me cum again! I'm all yours, baby.”

He rocked my world with long and powerful strokes and my legs wound up locked behind his back once again while my head slowly moved from side to side.

“You're so fucking hot, Jenny! Damn, your ass is on fire!”

“I'm hot for you, Bobby! I've wanted to be fucked like this for years, even before we jacked off together. Oh, damn, fuck me good! Use me! Spank me more! Fuck me all the time! Do whatever you want to me!”

Right this minute we were both too involved with fucking to think about anything else. For the next half hour he slammed into me with savage forcefulness and then I began to shake all over with a different kind of orgasm, one I'd never experienced. One began deep in my belly and exploded outward, engulfing my body like nothing I'd ever felt before. I was cumming hard and yet my dick was doing nothing at all.

“Here it comes, Jenny! Here it comes! Holy fuck, I'm gonna cum!”

“Yyyesss! Do it! Cum in me, baby! Fill up my ass pussy! Oh fuck!”

Wow, did he ever! I could actually feel the thick globs of cum blasting into me, filling me so completely that I soon felt a river of cum flowing down through the crack of my ass.

Bobby finished and rolled off me, his dick popping out of my ass pussy with an audible plop and he lay on his side, breathing hard. I rolled to face him and snuggled against him. In minutes he was snoring softly, sleeping well, and soon afterward I followed. For the first time in years, I slept with a man and slept well.

I awoke early Sunday morning and quietly climbed out of bed, going to the bathroom first to relieve myself and then heading to the kitchen to brew some coffee before starting breakfast. I sat at the table and sipped coffee while I thought about everything Bobby and I had discussed. If we could get enough trannies like me to perform on the different sites we could make very good money but I also knew there weren't enough in his city to keep these sites afloat very long and that would mean searching for them in other cities. But other than word of mouth, how could we get in touch with any of them?

Still thinking, I began cooking breakfast. Bobby came into the kitchen, still completely naked, and kissed the back of my neck, making me shiver.

“How's your ass this morning?” he asked, lightly rubbing my butt.

“Sore as hell,” I laughed.

“Regrets?”

“Yes.”

“Oh, no more spanking?”

“No, no. I just regret not getting a spanking any earlier.”

“Did anyone ever try?”

“No, not really.”

“You have to be careful, not all dominates will stop even if a safe word is used.”

“Would you have been able to stop?”

“On a dime,” he laughed.

“Will you spank me again? I mean, after my butt gets to feeling better?”

“Of course I will.”

“Good, I'm sure I'll need one pretty soon because I'm such a naughty girl,” I laughed and began setting the table.

“We might try a little bondage later just to see how you like it,” he said and patted my bare ass playfully.

“I don't have anything around here for that,” I said after thinking a few minutes before I sat at the table.

“No problem. We'll go to the hardware store and get a few things and then go to an adult store for some other things. When we go you can wear a long dress and a pair of sandals, nothing else. You can try on a couple of things on the way home.”

“Cool,” I answered. “What things are we getting and what will I be trying on?”

“I'm not telling you what we'll be getting but I'll say this much; on the ride home nothing you wear will be painful at all.”

After eating, cleaning the kitchen and taking a much welcomed shower while Bobby had gone back to his hotel to get cleaned up, I slipped into a full length casual dress and stepped into a pair of sandals and then straightened up the house a little.

I heard Bobby pull into the driveway and, picking up my purse, I hurried out the door to meet him.

“Are you dressed properly?”

“Yes sir, I am,” I answered happily.

The hardware store was fairly close so we went there first. Bobby bought cord rope, several feet of chains, bolt cutters, chain connectors and padlocks of various sizes. It didn't take very long and soon we were driving across town to XXX Row where several adult stores were located. Before we went inside Bobby cut a small length of chain and put it in his pouch.

In the first one Bobby found leather cuffs for my wrists and ankles, a ball gag and a leather covered paddle with a star shaped design of metal studs on it. He placed the cuffs in a leather pouch he was carrying and left the paddle in the car.

Okay, no big deal with this stuff, I thought to myself. Well maybe the paddle but that would have to wait until later to know for sure.

The second store wasn't nearly as nice or well stocked as the first one but Bobby did find a pair of nipple clips and a video. The nipple clips in the pouch and placed the video with the paddle.

A little pain is okay, I rationalized. After all, I had survived a pretty good spanking with no ill effects.

The third store seemed to specialize in bondage gear. Bobby found a collar and leash but kept on looking at the vast array of items they offered. He finally picked out an inflatable butt plug which I knew would be something I would be wearing home. Then he found a male chastity device, one that would keep my little dick from becoming hard, or even being stimulated. In other words, masturbation would be out of the question wearing that little baby. But since I very rarely ever used my dick for anything other than pissing it was of no real importance, accept for the esthetic value.

Bobby pulled me back to the video arcade area and entered a booth, feeding the machine a five dollar bill to start a video.

“Take off your dress.”

Pulling it over my head I was quickly naked. First he placed the collar around my neck, smiling as he did so. Next he fastened the chastity device onto my little dick and snapped the smallest lock in place so I couldn't take it off. It was uncomfortable but not painful and after a few minutes I all but forgot about it. Still smiling, he reached into his pocket and pulled out the cuffs, quickly fastening them to my wrists and ankles. He placed a connector on each cuff and then fastened a length of chain to each ankle, seriously cutting down my stride.

“These little babies you can take off at any time if they become too uncomfortable,” Bobby said and produced the nipple clips.

He put them in place, one on each nipple, and I nearly collapsed with the initial pain as they bit into my extremely sensitive nipples. That was very intense pain and I fought to keep them on, showing him I was just as serious about this as him. He bent me over and worked the deflated butt plug into me before pumping it up. And that felt like someone had just parked a truck in my ass.

“Now for a little humiliation,” Bobby grinned. “The clerk knows what we bought here and he can plainly see your collar and all the cuffs. When we leave I'll be leading you with the leash. He'll be pretty certain you're my little slave girl but what did I do with the chastity device? He might think I'm wearing it, but that wouldn't make any sense. He'll know you're wearing it and that can only mean you have a dick. Do you think you can walk out of here with him thinking that?”

“Yes sir,” I answered quietly.

“Good. Now if you're a good girl and do everything I say, you may get out of a spanking tonight with that new paddle.”

“Thank you, sir,” I replied again. “I don't care if anyone knows I'm a transvestite. That's who I am. Naturally I'd prefer to be a woman but I'm not, so I try to get as close as I can.”

“Ooo, good answer,” he laughed and gave me a hug. “Okay, put your dress back on and let's go back to the car. I have another surprise in store for you out there.”

“You're just full of surprises today,” I laughed.

He connected the leash to me and lead me back through the store. There were quite a few more men in there now than there was when we entered and Bobby made sure they all got a good look at me before we went outside. He also produced a digital camera and took quite a few pictures.

I had a hard time adjusting my stride to the length of chain but I managed without falling or slowing Bobby. But I was totally unprepared for his next little surprise when we made it to the car.

“You're doing fine so far but now you can take off your dress.”

“Huh? Here?”

“Right here. Right now.”

“Yes sir,” I answered obediently and pulled the dress over my head and then proceeded to turn this way and that for Bobby's camera, giving him every conceivable angle, even though people were coming out of the store and watching, before sliding into his car. “Yes, this is all making me super horny.”

“Very good,” he said and began driving out of the parking lot and into the light traffic. “See, the humiliating part isn't all that bad. Okay, so it's not over yet. Wait until we go through the hamburger joint's drive through and they get a look at you with your nipple clips on those nice titties and that cage on you little clit, and all on display.”

“Well, sir, I'm all over the Internet, naked, sucking cock, getting fucked, with cum on my face as well as fully dressed. So someone sees me in person. I can handle that.”

When we pulled through to the pick up window the guy there began calling his coworkers over and they all got a good look. Was it embarrassing? Was I humiliated? Yes, a little bit. Would I get over it? Not a problem.

As soon as we pulled on through we began eating and driving. I'm not sure how many people could see all of me but I know several got a good look at my titties from the horns honking and drivers waving.

“I'm so horny. Will you please take me home and fuck me? Pretty please?”

“There's one word I'm not hearing. Say it and I will, rough and hard.”

I thought for several minutes, wanting my next choice of words to be correct. Then it dawned on me, “Please fuck me, Master, I'm so horny for your beautiful cock.”

We pulled into the driveway and Bobby told me to walk to the door naked. Looking around to make sure my neighbors didn't see me, I got out of the car, picked up my dress and purse, and calmly walked to the front door. I fumbled with the lock and dropped the key twice before getting inside.

After I was inside the house Bobby removed the butt plug, leaving me with an empty feeling which I knew he'd soon fill.

“You did so well, leaving your nipple clips on, letting everyone see your nudity, meeting each task without any opposition, we'll forgo an ass whipping for now.”

“Thank you, sir. How can I ever thank you for this kindness?”

“I think we can come up with something,” he said and removed one nipple clip.

The blood rushed back into my nipple and the pain was mind numbing, “Ooww my titty! Oh fuck! Oh damn!”

Then he pulled the other off and I continued to rant and rave until the pain subsided and my horny state came rushing back with a vengeance. Please, Master, please! I'm so horny I can't see straight!”

“Maybe I should spank your titties. Would that make you hornier?”

“Spank me anywhere you desire, Master, but don't deny me your dick! I'm yours, use me,” I pleaded.

Bobby smiled and took me outside through the patio doors. He fastened chains to my wrists and stretched them upward until the chains slipped over two hooks I had in the porch ceiling for potted plants. He used longer chains on my ankles, securing them to opposite posts. Then he began tickling me, under my arms, my ribs, anywhere he could. I laughed and howled while he used this sort of torture on me.

“Please stop! I need to pee! Damn! Damn! I can't hold it! Please, stop!” I screamed but it was too late. My bladder released with a gush and I started peeing but the penis cage held my dick pointing straight down and pretty soon there was a large puddle between my outstretched feet.

“Ooo, did the little girl have to go potty?” Bobby cooed.

“Yes, sir.”

He pulled down his zipper and pulled out his big dick. “Maybe I should piss on you, Jenny. Are you a piss slut as well as a cum slut?”

“Yes sir. I mean, no sir. I mean I'm not a piss slut but yes piss on me. Fuck me. Use me. I'm yours, Master.”

The words barely cleared out of me when he started pissing a long, strong, steady stream of hot urine. He struck my caged dick, my titties and then my face before it started to subside.

“Thank you, Master,” I whispered.

Bobby loosened my chains, turned me around, and then rammed his hard cock all the way up my tight little asshole.

“Aaahhh, Bobby, Master, fuck me. Let me be your whore. Fuck me. Use me.”

Bobby moved so that I was bending over, holding the back of a chair for support while he sawed savagely in and out of me, hammering me harder and harder.

“So good, it feels so good,” I gasped. Fuck me! Fuck me! Ooohhh Master, fuck your slave hard!”

Even though it had been implied on several occasions, I'd never been called a slave, now I was emphatically labeling myself, offering myself to him if he wanted me.

“I like my slave girls to have a hot, tight ass,” he grunted, slamming his long cock into me harder than ever.

“Fuck my tight asshole, Master! Fuck it hard! Ooohhh, damn, I'm gonna cum! Ooohhh, fuck! Fuck! Fuck!” I cried and felt my cock spewing onto my legs.

Still, Bobby wasn't ready yet and kept on fucking me. He plowed into me for at least another thirty minutes, taking me to the edge again.

“Here it comes, slave. I'm gonna cum in your ass! Oh fuck, here it is! I'm cumming! I'm cumming!”

His hot cum began boiling into me and I felt that weird knot in my tummy explode into a fireball of lusty pleasure again. My body shook harder than the last time and I jerked about almost uncontrollably, riding my orgasm while feeling him fill me up. He collapsed on my back and I had to hold us up.

An hour later, after he removed all the new leather gear, leaving my penis cage in place. We showered together and settled down in the den after he reaffixed the collar to watch the videos he'd purchased. Fifteen minutes into the video I was between his legs and sucking so lovingly on his wonderful cock. Fifteen minutes later he was painting my face with cum and I was happy to receive it.

“Master?”

“Yes, slave.”

“I've been very, very naughty.”

“So I see,” he replied. “Go out to the car and get me the paddle. Your ass is gonna get blistered.”

“Yes sir.”

Calmly I walked outside and got the paddle for him, knowing it was going to hurt this time and knowing I needed it. I wanted him to punish me, to wear my ass out. More than anything else I wanted to prove to Bobby that I was worthy to be called his slave.

After I gave him the paddle I knelt over an overstuffed ottoman, leaving my ass totally unprotected from the onslaught I knew was coming.

“Count them, slave,” he said as he swung the paddle.

“One!” I shouted as it struck me, filling my mind with pain and pleasure.

“Two!” I screamed and jerked, my voice reaching decibel levels I never thought possible.

He stopped at twenty and by then I was crying real tears of pain. My ass was bruised and on fire, I was horny again, I probably wouldn't sit for a while, and I had counted every stroke.

(To be continued)