Jaime's Way (Part 1) free porn video

I'd only been married a very short time when my wife came home and caught me masturbating while wearing a pair of panties and a bra. This in itself was bad enough but then she caught me again, and then again.

The first time she caught me she was shocked and appalled but the twentieth time or so that she found me wearing panties and bra and with a dildo in my ass she really lowered the boom on me.

“Are you a fucking fagot? Is that why you wear women's undies while you jack off? Do you try and pretend you're a woman getting fucked? Does that get you off?” Sherry asked.

“I, uh ...”

“I don't want to hear it! And I certainly don't want you ruining any more of my things!”

“Sherry, I ...”

“Shut up! I'm talking and you're listening. Things are going to change around here and starting right now. You've got a choice. You can either do as I say or you can just get the hell out. What's it going to be?”

“I'll do whatever you say,” I answered quietly, hoping I could weather the storm.

She smiled but it was more an evil smile than a happy one.

“I thought that's what you'd say.” She reached into her purse and brought out some sort of contraption.

“First things first. You won't be jacking off any longer. At least not without my permission,” she said so sweetly and approached me. “This little device will take care of that.”

I finally recognized it as a locking male chastity device. Sherry put it on my cock and locked it in place. Jacking off would now be impossible. Hell, getting a hard on wouldn't even be possible any longer. Something told me she may have been planning this for a while.

“From now on, you'll only get to jack off when I want you to,” she said with a smile before adding, “and you'll lick up every drop of your cum.”

“Lick it up? But ...” I'd tasted my own cum on several occasions but I wasn't about to admit it to her.

“Don't argue with me or you'll never get to cum again!” Sherry stopped me with a very harsh tone. “There's going to be quite a few changes around here. From now on you're going to be keeping the house clean and making all the meals. When I think I can trust you to go out alone, you'll be doing the grocery shopping and running errands, but that won't be for a while. Is that clear?”

“Yea, very clear,” I replied. I didn't mind keeping the house clean, enjoyed it in fact, especially since I always did a much more thorough job of it the Sherry ever did. But I at least wanted her to think she was making me do something I didn't want to do.

“I thought so.”

I began that evening, cooking dinner and then cleaning the kitchen. It helped that I liked to cook, and cleaning up, well, that wasn't so bad either.

The next morning, however, things really began to take a turn. When I awoke and reached into a drawer for some clean underwear, I found it there was none. No big deal, I just went to the laundry room and started washing clothes but then I discovered that not only was my underwear missing but I had nothing at all to be washed.

“Have you seen my underwear?” I asked Sherry.

“Yes but I think we need to get you some new ones. Those were all so nasty and uninteresting that I threw them away. I guess we need to go out and get you a few things or you'll be running around naked.”

“Okay. I'll go get dressed.”

“Wait a second. Here, you can wear these shorts,” she said and handed me a pair of denim shorts she'd just finished cutting the legs from.

I didn't mind going commando so I pulled them on. Man, they were tight. Then I recognized them as a pair of jeans I'd outgrown a year ago but hadn't gotten around to throwing out. When I pulled them on and finally got them buttoned I saw just how short she'd made them. I mean, only girls wore their shorts this short.

“You expect me to wear these out in public?”

“Of course, but not until you shave your legs. What's wrong? Are you afraid of showing your legs?”

“No, it's just that you made them kind of short.”

“Those are the long ones,” she giggled. “But don't worry, we'll get you some new jeans and some other things. In fact, you'll have your own panties by the time we get back as well as a couple of bras, some stockings, and even a dress or two.”

“A dress?”

“Of course, every girl has some dresses to wear.”

“Yea, okay, whatever,” I muttered. She had to be kidding abut this stuff. Right?

Wrong.

When we finally left to go shopping I was wearing a pair of flip flops and a pale pink knit pullover shirt that just barely came to the waist of my very tight and very short shorts. And yes, my legs were completely free of hair. This actually felt pretty good, but I didn't want to tell her that part. Sherry drove to let me know she was in charge.

At first I was embarrassed to be seen in public dressed like this, and with shaved legs, but that feeling eased away and I almost forgot that I was dressed more like a girl than a guy. Sherry brought me back to reality when we walked into the big discount store.

“You know, we should have painted your nails. What girl goes without a good coat of polish on her fingers and toes?”

“I could never go out like that,” I protested slightly. “What would people think?” The last thing I wanted her to think was that I was seriously arguing with her.

“Oh, I don't know, maybe that you're a sissy crossdresser.”

“Exactly.”

“Well, you are. Okay, maybe not a sissy, but look at yourself in your tight little shorts and cute top. Babe, you are now officially a crossdresser. Hell, you were before this. Remember wearing my panties and bra while jacking off?”

“How can I forget?”

“So are you willing to admit that you're a crossdresser?”

“Yea, I guess so.”

“Then say it out loud.”

Damn, this was humiliating. “I'm a crossdresser,” I answered with a mumbling voice.

“What's that? I can't hear you.”

“I'm a crossdresser,” I said in a voice loud enough that three people looked in my direction.

“Very good. Now that wasn't so hard, was it?”

“No,” I answered, my face still red from humiliation.

She suddenly stopped and picked up a bra just a shade larger than her own.

“How big do you want your titties to be?”

“Yours are perfect,” I answered, looking around to see how many people could see me picking out a bra.

“Good answer but I think you should have bigger boobs.” She chose a different cup size and put it in the basket before picking out another bra. This one had lots of lace and in general was quite a bit more sexy.

Next we moved to pick out some panties. Sherry chose several styles, all of them very sexy and feminine. Obviously she wasn't worried about the cost since she picked out thongs, sheer bikinis, string bikinis and some that I didn't quite catch the name of. All in all, she picked out fifteen pair in various styles and colors.

From there she picked out nighties for me, short little baby dolls and a long gown that had a slit all the way to the waist. Sherry also found a garter belt and three pair of stockings as well as three pair of stay up stockings and two pair of pantyhose.

Next we went to the junior department and she began picking out dresses which I had to try on for her. Several of them she put back on the rack but five of them she placed in the basket. Most of the dresses were of modest length, falling to just above my knees, but one of them was pretty short even by my standards.

“Now when you wear this dress you probably shouldn't wear your garter belt and stockings,” she said in a loud enough voice that I know she was heard by several people. “That is, unless you want to go for the slut look. Even your thigh highs would be better but you'll still be able to see the top of them.”

At a different rack she picked out six skirts that ranged in length from very short minis to full length and everywhere in between. With these she chose several blouses of differing materials and colors. After that she picked up three pair of very short shorts. I mean, these were short enough that my ass cheeks were almost hanging out.

“We need to get you some shoes now.”

Did she ever!

Of course, I had to try on about a thousand pair and then walk a few steps in each before she picked out any. By the time we left that department I had eight pair, most of them with high heels of four inches, some stiletto and some block heels and even a pair of five inch wedgies, which I found to be the most comfortable of all the heels. She also bought me a pair of canvas top sneakers, bright red of course, and a pair of flat leather sandals.

Just when I thought I couldn't be embarrassed any more, Sherry stopped at the makeup counter and asked the girl there to pick out the colors that would look best on me. This entailed her applying the makeup on me several times but when she finally finished I had to admit that I looked damn pretty all made up. Her efforts were rewarded when Sherry began telling her what she was going to buy for me. Naturally, Sherry insisted that I spend the rest of the day wearing the makeup the girl had worked so hard to perfect.

Before we were ready to leave the store Sherry also picked out a small purse for me, bracelets, a ring, a necklace and several pair of very feminine earrings. The jewelry had to be paid for in that department to cut down on shoplifting so Sherry whipped out her credit card and paid but only after both my ears had been pierced.

Now it was time to make our purchases and go home, which was all fine and good except the line to the checkout looked to be a mile long. By now at least a hundred people had seen moving about the store and I had received all sorts of stares and even a few smiles. Since I'd never even seen any of these people and probably would never see them again, I really didn't care what they thought about me and crossdressing in general.

After we were in line about fifteen minutes Sherry smiled sweetly and said, “I'm getting hungry. You go on through the line and pay for all this and then meet me across the parking lot at Boogie Burger.”

“Me?”

“Yes, you. If anyone asks about anything in the basket you are to tell them it's for you. Here's my credit card. Oh, and be sure you ask if anyone, especially one of those good looking guys, will help you carry everything to the car.”

“Okay, I can do that,” I smiled. I was used to everyone's stares by now and, in fact, I kind of liked the idea of dressing like a girl, especially if it meant I could jack off every now and then.

I waited in line for what seemed like an hour before I finally got to the cashier and I'd noticed more than one guy checking me out. Even though I was obviously a guy dressing more like a girl, I couldn't help but see a certain amount of lust in their eyes and that made my heart race a little. To me it was obvious what they'd like to do, and somehow I found that to be quite pleasing, and more than a little exciting.

“Wow, did you buy out the store?” the cashier asked when it was finally my turn.

“I tried.”

“Looks like you did a pretty good job,” she laughed, ringing up item after item.

“Ooo, sexy,” she crooned as she rang up the panties.

“Yours?” she asked and held of the bras.

“Yes.”

“You sure they're not too big?”

“Falsies.”

“Ah, I didn't think about those,” she said with a smile.

It was no wonder she didn't think about them, I thought after taking a second look at her very large titties.

“Um, do you think I could get some help carrying these to my car?” I asked as I handed her Sherry's card.

“Sure thing,” she answered and smiled. “Hey Mike, will you help this lady with her bags?”

“Sure,” Mike replied and began gathering my bags.

He was sure giving me the once over and suddenly I felt that all too familiar tingling between my legs. Although I liked the way he looked at me I was a little confused why I was feeling aroused by his attention.

“I can't wait to get home and try on a pair of these panties and that pretty black bra,” I told the cashier in a voice loud enough that Mike could easily hear. Damn, I was flirting with him without giving it any thought!

“You'll love it,” the girl said as I signed my name to the receipt.

“New wardrobe?” Mike asked, carry the majority of my new clothes while I pushed the basket.

“A whole new me,” I laughed and found myself putting a little extra swing in my ass.

When we got to the car Mike handed me the bags while I leaned in and placed them. Of course, my tightly clad denim covered ass was just waving at him, distracting him quite a bit. I knew he was watching me and even wiggled my butt a little for him.

After everything was put away in the car Mike went back inside the store and I stood watching him. Funny that I noticed he had a very fine ass. When he was inside I locked the car and walked across the parking lot to Boogie Burger.

“You are such a flirt and tease,” Sherry laughed when I was in the restaurant.

“Huh? Me?”

“Don't even pretend you didn't know what you were doing, shaking your ass at that poor boy and bending over like that so he could get a good look. You were all but saying, here it is, take it.”

“Is that so bad?”

“No, not really, I do it all the time.”

We ate our burgers and left the place after Sherry took me into the ladies room to freshen our lipstick. Because of the chastity cage I was wearing I had to sit to pee, just like a girl.

“One more stop,” she said with a smile and pulled into an adult book store.

“You want me to go in there dressed like this?”

“Get used to it. Your days as dressing like a man are over with, buddy. Now come on.”

“What are we getting?”

“You'll see,” she laughed.

The first thing she picked out was a video about transvestites having sex with me or with each other. Then she began looking at sex toys and I was starting to get a sinking feeling because she was looking at strap on dildos and I could just imagine what she was planning on doing with it. The one she finally decided upon was ten inches long and at least three inches around. Not only did the size concern me but it also came fully functional with a squeeze bulb that actually allowed it to shoot its own cum.

Sherry picked up a set of leather cuffs and asked. “When I fuck your asshole with this thing, am I going to have to restrain you? If you even remotely think so, then we'll have to get two pair of these.”

Of course there were a couple of guys within hearing range so they knew I was going to get fucked with her new dildo.

“Uh, no, I'll be good,” I answered quietly.

“Oh, go ahead and smile, baby, you know you'll love it,” she exclaimed. “Besides, whether or not you love it, I'm going to love fucking your pretty little ass tonight.”

Sherry gave me her credit card and once again I made our purchases. The cashier gave me a very knowing look when ringing up the sale. While I was busy I lost track of her and didn't realize she was making preparations for me to really expand me sexuality.

“Come on, I want to show you something,” Sherry said, suddenly at my side.

She lead the way into the arcade area and walked purposefully to one of the booths. We were inside and she fed the machine some cash and a video began playing. The girl sucking on the hard cock was obviously not completely female. I mean, she had a dick between her legs that made me jealous. I was totally mesmerized watching the long cock sliding in and out of her mouth. A part of me wondered if I could ever have the balls to do something like that. I found myself becoming very aroused, not because I wanted her to suck my dick but because I actually wanted to do the sucking.

“Oh look,” Sherry said, nudging me and pointing to a hefty dick coming through a hole in the wall.

Even though I was highly aroused, the idea of touching another guy's cock wasn't really on my list of things to do, no matter how I might be dressed.

“Go ahead, touch it. Hold it. You know you really want to.”

“Hell, I might hurt it,” I laughed, using maybe just a little too much macho.

“Touch it, silly, don't rip it off.”

“I, I can't. Come on, Sherry, I'm not a queer.”

“No, you're just a sissy crossdressing fagot. Like this,” she said and wrapped her hand around the large cock, slowly moving her hand up and down its length.

I thought to myself that if she wanted me to do this, I could probably do it, especially since no one would know about it.

“Jack him slowly. Just like I'm doing. Then after a bit just lean down and kiss him.” Which is exactly what she did. Seeing her kiss the stranger's dick and then seeing her tongue snake out and lick the head was a very erotic sight.

Then, without any hesitation, Sherry took the hard cock deep into her mouth. I knew from personal experience just exactly how good she could suck a cock. Most men probably would have been jealous to see their wife sucking a cock as she was doing but I wasn't. In fact, I was happy just to sit back and watch even though she was actually just showing me how to do it in an attempt to get me to do the same.

She pulled away from him, kissed the head of his dick, and smiled up at me, “Your turn.”

I stared at the throbbing shaft and slowly reached out, drawn to it like a moth to a flame, until my fingers made contact. There was no sudden lightning bolt striking me dead so I let my fingers wrap themselves around him. In all my life I'd never touched another man's dick and now I was holding him gently, slowly stoking him.

“You're doing fine,” Sherry whispered. “Now lean down and have a taste.”

I could feel my own cock growing within the confines of the cage but I knew I couldn't achieve an erection. Actually it was painful getting as hard as it was and then I felt myself deflating even though I was still highly aroused.

“Do it! Kiss his cock! You know, way down deep inside, you really want to suck him. Just do it!”

This was an act I had fantasized about during my many jack off sessions. Somewhere in the back of my mind, I knew I wanted to feel a man's hard cock sliding over my lips. So without even thinking about it, I found his dick directly in front of my mouth. The next thing I knew my tongue was plating over the head of the magnificent dick. That's the moment I knew I was going to suck him; that I was going to be a cocksucker; that I wanted to be a cocksucker.

I didn't kiss his dick but just opened my lips and slowly took him into my mouth. Feeling the smooth hardness of the throbbing cock sliding over my lips was absolutely wonderful.

“See? It's not so bad, now is it? Don't worry, you'll be getting lot's and lot's of practice. Before you know it you'll be a first class little cocksucker.”

What had been fighting words just a few days earlier now didn't sound so bad. In fact, I discovered that I liked being called a cocksucker. I knew that I crossed a through a door that I could never return from. Never again could I sat I was heterosexual because I had become, or at least accepted, that I was bisexual, if not gay.

I was happily sucking the cock Sherry had made available to me when I realized she was taking photos of me. But what the hell, I'd done the same thing to her many times, snapping shots of her naked or with my dick buried in her somewhere, so I figured it was payback time and just kept on sliding my mouth up and down his shaft.

When I felt him grown harder and thicker in my mouth I knew what was about to happen but I didn't slow down. Seconds later I felt the hot and creamy sperm firing out of his dick and into my very willing mouth. The taste was very similar to my own cum but maybe a little bit stronger and there was quite a bit more than I'd ever shot.

“Open your mouth and let me see it,” Sherry laughed. “Then you can swallow it like a good little girl.”

I knew she was going to take a picture of me with a mouthful of cum but I did as she requested while the cock pulled back through the hole.

“Wow, he really gave you a load,” she said and snapped the picture. “Now swish it around your mouth and then you can swallow. How do you like the taste of a real man's sperm?”

“It's not so bad,” I answered after swallowing.

“Good. You'll get to where you really love it,” she said with a smile and then nodded back to the hole.

Looking I saw that a different cock was waiting for its turn. This one wasn't as long nor was it circumcised.

“Go ahead, cocksucker, give him a blow job.”

Shrugging my shoulders, I began sucking this one. The initial flavor was different, having a slightly bitter background taste, but not bad either. I figured this was maybe a trace of piss that had been trapped beneath the foreskin.

“Tastes different, doesn't it? That's his pee. You'll like it after a while.”

I sucked him for quite a while before he began spewing his cum into my mouth. I already knew that his cum would taste different, and it did. But the bottom line was, I liked the flavor. Over the next three hours I sucked one cock after another, enjoying each one more than the one before. Then, just when I thought I was finished, the door to our booth opened and a man stepped inside.

“Okay, sissy, get on your knees and suck my dick,” the man smiled and lowered his zipper.

“Wait a minute,” Sherry said and smiled back at him. “Let the sissy cocksucker fish your dick out of your pants. She needs to learns how to do it.”

Kneeling before the man, I slipped my small hand into his pants and found him to be going commando, which was good because when I found his cock I was shocked by the size of it. The only time I'd ever seen a dick of this size was in a porno movie, and I was supposed to give him a blow job.

“Oh my goodness!” I exclaimed in total amazement when the full length and extreme thickness of his beautiful cock was on display.

“And it's loaded for bear. Just be warned, I haven't had any for three weeks so I'm on a hair trigger.”

Smiling up at him, I replied, “I understand and it's okay.” I lifted his hardened member up and leaned to bring my lips to the bulbous head so I could kiss it.

When I began licking him from tip to base I didn't think I would ever get to the end. After I did I began working on getting the head into my mouth, thanking my lucky stars that I wouldn't be expected to deep throat this monster. My mouth was stretched open as wide as possible without unhinging my jaws but I managed to get him inside, as well as three inches of his shaft.

“I can't believe he got you inside,” Sherry gasped and took three or four pictures.

“Yea, most girls can't get that far,” he laughed and placed a hand on my head. “Ooo, yea, girly, that feels so fucking good!”

Because he referred to me as girly I felt even better and tried to get more of his cock into my mouth but that was impossible. Instead I concentrated on the sensitive head of his cock, hoping he really was going on a hair trigger.

Sure enough, after only ten minutes or so I felt him shudder. This was the signal I knew came just before the reward I wanted. He held he on the sides of my head and erupted into my mouth, quickly filling me with creamy hot cum. Then he pulled out and began blasting away on my face, giving me my very first facial. I'd done this to Sherry once or twice but until today had never thought I'd really be on the receiving end.

All the while Sherry snapped one picture after the other. It want until she showed them to me that I saw how happy I looked.

“You know, it wasn't until today that this little cocksucker had ever sucked a cock,” Sherry laughed.

“Really? Damn! Well she does a good job,” he replied. “Just one more thing, baby, lick the last few drops off my cock.”

Doing as he requested, I savored the remaining drops of his cum.

“Next time you're in town and want to use her, give me a call,” Sherry said and gave the man her phone number.

“You can count on it,” he said, typing her number into his phone and then giving her his number. “I'm David, by the way.”

“I'm Sherry and this is Jaime.”

“I'm pleased to meet both of you,” he smiled and stuffed himself back into his pants before stepping out of the booth.

“Come on, Jaime, let's go home. I'm horny, “ Sherry laughed and helped me to my feet. “But don't get any ideas about using your dick on me. When we get home I want you to shower and then you can eat my pussy. Once I get off I'm going to fuck your cute little ass and if you're lucky you might get off as well.”

“Okay, I'm going back out there and I want you to count to twenty and then come out into the showroom area. Oh yea, leave the cum on your face until you shower.”

“You want me to walk around in the store with cum on my face?”

“Of course. You'll leave no doubt between your scantily suggestive clothing and the cum on your face that you're a cocksucking crossdresser. What better form of advertising can there possibly be?”

“Advertising?”

“Just in case I want to pimp you out and let you pay me back for all the things we bought today.”

“But ...”

“Be careful what you say next. They make a cage that emits a strong electrical shock. How would you like that?”

“I, er, I wouldn't like that at all.”

“I didn't think so. Now when you leave here I want you to go to the counter and tell them you need some lubricant,” she said and handed me some cash.

“You've had this whole thing planned,” I said flatly and then smiled.

“Of course I have. I've been working on this since about the twentieth time I caught you wearing my panties and bra while you jacked off. I just didn't think it would be so easy to get you to suck a cock but you really do like it. Now, thanks to my little camera, I've got plenty of proof and I'll get more proof of your crossdressing tonight and tomorrow. By this time next week you'll be very popular on the photo sharing site. How many guys do you think are going to see you with a dick in your mouth? A hundred? A thousand? No matter. You're going to be posing for the camera quite regularly, either in full drag or in full drag while having sex.”

“Having sex with you?”

“Don't be silly! Where's the fun in that? Baby, your crossdressing sissy ass is going to be having sex with so many men you'll swear there's a revolving door letting them at you. If you just keep in mind that you're giving pleasure to all those men, you'll enjoy it more. I mean, after all, don't tell me you didn't fantasize about it while you were jacking off.”

She had me there because that's exactly what I had fantasized about. Well, maybe not so much me being a guy getting fucked but definitely as a girl getting fucked by man after man after man. So I guess you could say that this was what I had been asking for and now I was going to experience it.

Sherry left the booth and I started counting. Thankfully most of the cum had either dried or run off my face. But either way, my makeup was a mess. Stepping out of the booth I looked around and breathed a sigh of relief that no one was out there watching me.

As soon as I stepped into the showroom area I saw that it was very crowded and several men looked at me, smiled, and then took in my figure. I didn't have to be a psychic to know what they were thinking, and, in fact, I found myself liking it. Even when I went to the counter to purchase some lubricant, I liked the way the cashier looked me over. He knew I had cum on my face and just smiled at me and gave me a wink.

“Will there be anything else, miss?”

“Not at this time,” I replied and smiled, “My jaws are tired.”

“Come back any time if you need something else.”

“Thank you, I will.”

When I turned to leave I saw Sherry talking to a gorgeous woman with very red hair so I walked to where they were standing.

“Oh, Jaime, I'm glad you're here. Pull your shorts down and show Melinda your cute cock cage.”

“Here?”

“Yes, right here, right now. Do it.”

Blushing with humiliation, I obeyed her and pulled my shorts down.

“Oh yes, I see what you mean,” Melinda laughed. “tell me, sissy, does it hurt when you get an erection?”

“Er, yes, I mean no. I mean, I'm really not sure since I can't get one while wearing it.”

“Perfect! I'll just have to get one of those.”

“You may want to get the one that shocks him when you need to get his attention.”

“Yes, that's a good point.”

“Well, sissy, either pull up you shorts or take them off.”

“Er, yes, of course,” I stammered and pulled up my shorts before following Sherry out to the car.

“What was that all about?” I asked after getting into the car.

“Her husband is a cheating prick and she's going to teach him a lesson.”

“Good for her.”

“Yes, good for her. After we get home I want you to put away all your new clothes and then go take a shower. Every time you shower I expect you to shave your legs and beneath your arms. No girl wants that unsightly hair and no man wants to see it. Starting tomorrow you'll put on makeup as soon as you get up and take care of your morning activities. I expect you nails, both finger and toes to be polished at all times. You'll act like a girl and look like a girl at all times. Of course, you can always refuse but when you do, pack your bags and get out. Do I make myself clear?”

“Yes, perfectly.”

“Excellent. Tell the truth, how did you like sucking all those cocks today and swallowing all their cum?”

“Honestly, at first I didn't want to even touch another man's cock, but once I got started I kind of liked it.”

“I knew you would. You just needed a little push.”

“But I'm not sure I'll like the other.”

“Oh? I think you'll like it after a while. Remember the first time you fucked my ass? I thought I'd hate it but actually, it feels pretty good. And since that's the only way a real man can fuck you, I think you'll love it after you get a few loads of cum dumped in that sweet little hole. But don't worry, before a man fucks you I'm going to fuck you so many times you'll be begging me to do it again.”

“If you say so,” I answered doubtfully as we pulled into the driveway.

Once I had all my new clothes put away I began doing the other things Sherry had told me to do. For the second time that day I shaved my legs and beneath my arms. This, I had to admit felt pretty good. Luckily I didn't have any hair on my chest or back or else she'd want me to shave them as well. When I stepped out of the bathroom in my new short satin robe, my nails were painted a very pretty shade of pink and I was wearing lipstick to match.

“Very nice,” Sherry told me, “you look good enough to fuck.”

“I'm yours to use, lover. All lubed up and ready to be fucked,” I replied to her with a smile.

“That's the spirit, Jaime,” she said and let her robe fall open to reveal the strap on dildo in place and ready.

In the back of my mind I really wanted to find out what it felt like to be fucked but a part of me was very reluctant. Maybe it was because if I liked it even half as much as I had enjoyed sucking cock I somehow knew there would be no turning back.

Sherry steered me to our bedroom, fondling my ass the entire way. We stopped just short of the bed and she opened the sash on my robe, letting it fall open. Moving closer she began playing with my nipples while her hard on pressed against me.

“Mmm, that feels so good,” I whimpered, surrendering myself to her.

When she leaned down and began sucking my extremely sensitive little buds, I nearly blew my load. I was totally in a lustful daze as she sucked one nipple and then the other. Quickly I realized just how such foreplay could get a woman in practically melt in a man's hands. I reached for her breasts but she casually swept my hands away.

“Let me suck your cock. Please!” I begged as she walked us closer to the bed.

The back of my knees came in contact with the bed and I was suddenly sitting, her monster cock in my face. I wasted very little time before my mouth was filled with the lifelike dick. I began bobbing up and down, working the base of her dick, and the nubs on it, against her clit. There was also a small piece that slid inside her, actually fucking her while I gave her a blow job.

“Ooo, yea, suck my fucking cock. Show me how good of a cocksucker you are,” Sherry moaned. “Make me cum, you little slut!”

That was exactly what I intended to do. I worked her latex dick harder and faster, grinding the nubs over her clit as best I could.

“Oh yea! Yea, baby, yea! Ooo, I'm gonna paint your tonsils!” Sherry cried, grabbing my head and driving her huge dick deeper and deeper until it was actually in my throat.

Earlier today I had learned how to avoid gagging when a cock pressed that deeply into me and it stood me in good stead now. With the dildo halfway down my throat I could really work it against Sherry's clit, which by now should be just about ready to blow.

“Ooohhh fuck! Ooohhh fuck, I'm cumming! I'm cumming!” Sherry screamed and pulled back enough that when she squeezed the bulb several times my mouth was flooded with several squirts of artificial cum.

“Yyyesss! Yyyesss! Oh fuck! Oh fuck!”

Again and again she shot squirt after squirt of the fake sperm into my mouth, filling me to the brink and forcing me to swallow. The fake cum tasted similar to the real stuff but wasn't nearly as strong and just a little bit sweeter.

“Damn, I need to catch my breath,” Sherry laughed and plopped onto the bed. “be a dear and go get me a glass of ice water. Oh, and you better lube your ass again.”

“You think you're going to be to fucking me?” I asked as I stood to leave.

“You bet you're fucking ass!”

On my way back to the bedroom I stopped at the bathroom and applied more lube. I wanted to be really slick when she pushed that big mother fucker into me.

I crawled into bed next to Sherry and snuggled against her, using my hand to slowly slide up and down her shaft. This time I paid attention to her already erect nipples, lovingly sucking on them until she made me stop.

“Don't think you're getting out of this,” she laughed and began pushing and pulling me until I was in the doggie position.

“Now just relax.”

“Is this gonna hurt?”

“I'm not going to lie to you. It's going to hurt like hell at first but after the fat head gets in and you get used to the size, you're going to love it. But even if you don't, I'm going to love it. So you might just as well get used to it because I'm going to fuck you quite regularly.”

“Well, just be gentle with me. I'm a virgin,” I whimpered as she moved into position.

“About as gentle as you were with me,” she laughed and placed the head of her monster dildo against my puckered little hole.

Just as her words were beginning to register I felt her pressing against me and even though I did my best to relax, it still hurt more than anything I could ever remember.

“Oh, Sherry, it hurts! It hurts!” I squealed to no avail.

We both knew that no matter what I said or did, she was going to fuck me. As she made her way into me I could feel my asshole opening wider and wider until I was certain she was trying to park a truck in my butt.

“It's too big! Oh baby, you're too big for me!” I cried through a haze of tears.

“Man up, bitch!” Sherry laughed and pressed even harder before pulling back slightly and then pressing ahead once again. “Remember how I cried and begged you to stop? Did you? Hell no! You were bound and determined to fuck my ass, and that's what you did. Now it's my turn.”

Suddenly the head of the dildo was inside me and then the shaft slid in easily. I'm not sure how much of her was in my asshole, but it felt like about a mile's worth of latex cock was in my butt. I gasped and cried aloud, thankful that she was giving me a few seconds to get used to her length and girth.

“You're not a virgin anymore,” she sneered. “Now I'm gonna fuck you until I'm satisfied and you're nothing but a little crossdressing fuck slut.”

I was breathing hard from both the pain and the excitement. My ass was sore from being so stretched, but it was also quite thrilling knowing what else was to come. When I looked back between my legs I could see that my caged cock had shrunk down to an extremely small state, but at least there was no pain from getting an erection.

Then I felt Sherry pulling back and that was quite erotic. When she pushed back in I really loved the way it felt. Slowly and steadily she was fucking me, gradually building up more speed and then finally settling into a hard rhythm.

I didn't realize I was moaning with pleasure until Sherry laughed and said, “You love it! You're a little fucking whore!”

“Ooohhh, fuck me, Sherry! Please, please, fuck me! It feels so good! I love it! Fuck your whore! Hard!”

I couldn't believe what I was saying. I was actually begging her to fuck me hard. What's more, I loved the way it felt and needed to find out what it would feel like when she dumped her heavy load into me.

Holding my hips, Sherry began thrusting harder and faster and deeper into me. “Take it all, you little slut! Take every inch of my dick!”

“Yyyesss! I want it all! I need it all! Oh please, please! Fuck me! Ooohhh, baby, I'm yours to use! Give it to me!” I begged over and over.

I have no idea how long Sherry fucked me. Maybe ten minutes, maybe two hours. The only thing I know for sure was that I was helpless to stop her if I wanted. Without any warning, and without being hard at all, I felt my dick spilling my load. I kept on cumming while Sherry slammed her cock deep into me.

“I'm cumming! Ooohhh, baby, I'm cumming!” I squealed.

Sherry never slowed her assault on me, pounding my asshole harder and harder even though I knew she had cum at least twice. Still she withheld her load from me, making me beg for it; wearing me out.

After what seemed like years I felt her begin jerking, he cock simulating how a real cock would react inside me. She started pumping me full of fake cum, and rammed herself all the way inside me before collapsing on my back and pushing me down to the mattress. As we lay together I felt her cum oozing out of me and flowing over my balls.

“How do you like taking a cock in your ass and getting cum up there?” She asked, her lips near my ear.

“I love it,” I gasped.

“I knew you would,” she giggled. “And when a real man fucks your ass, you'll thank me for this. You really are a sissy cum slut.”

“Yes, I am,” I answered as she rolled off me. I couldn't remember ever feeling this way after making love to her and could only imagine that it was because I was now in the feminine role and I never wanted to go back.

I slept against her that night, more content than I ever was after sex. Even sleeping in the wet spot, which I had previously avoided, seemed natural.

For the next six weeks I wore nothing but full female attire, including heels, no matter what we were doing. I kept the house clean, cooked, did laundry, and got fucked by Sherry almost every night, or at the very least, I gave her a blow job. My makeup skills were getting better and better and so was the way I carried myself. Even my gestures and speech patterns were becoming more feminine. And to top it all off, I loved every second of it.

“I've got a date tonight and I'm planning on bringing him back here and getting fucked. He's a real man and he really delivers a big load. I know because he's already fucked me several times. But tonight, after he cums in my pussy, I want you to lick me clean. Oh, and one other thing, lube your ass because after watching you lick my pussy he just might want to fuck you. Oh yea, when you're going down on me, I want you to wear spike heels, garter belt, black stockings and a bra. He already knows you're a sissy crossdresser and he said he'd be glad to show you what a real man's cock feels like in your ass.”

Funny how I didn't feel a bit of jealousy that another man had been fucking my wife nor did it bother me to be called a sissy. After all, I am a sissy and a crossdresser, so call a spade a spade. In fact, I was a little relieved to know she was getting laid by someone she cared for since I couldn't do anything with my cock in a cage even if I was so inclined. To tell the truth, I really didn't have a whole lot of interest in putting my dick in any woman's pussy.

But cleaning out her pussy after some guy dumps his load in her, well that's an entirely different matter, especially if he just happens to be fucking me while I do so.

“Where are you going tonight?” I asked.

“Out to eat and to a movie and then back here for sex. That should give you plenty of time to get all dolled up and ready for your first cock. Oh yea, I want you to suck him and get him really hard before he fucks me. Then do it again before you clean me.”

“Mmm, I like sucking cock,” I laughed.

“Don't I know it,” she replied with a laugh while getting ready to go to work.

I noticed she was wearing anything at all beneath her dress and asked, “No panties or hose or anything? Does he like it when you're so natural?”

“He insists on it, especially at work. Did I tell you he's my boss? Oh well, he is and he's been fucking me at work very, very regularly. I mean, my first day at work he had me naked in his office and had his big cock pumping cum my pussy and we've been having fun ever since.”

“So you were fucking your boss before we were married?”

“Yep. I stopped for a while, well except for blow jobs, until I started coming home and catching you jacking off while wearing my things. He's the one that suggested that you were a closet crossdresser and had secret desires to have sex with men. You reinforced that by always insisting that I get on top. Then that first time at the glory hole, I didn't have to work very hard at all to gt you to suck that first dick. And then when I fucked you for the first time you actually blew your load. Face it, babe, you're not a real man, you're a sissy fagot crossdresser that loves being a woman.”

“You're right. I love wearing a dress a whole lot more than jeans,” I admitted. “And as far as sucking cock, I'd rather do that than eat.”

“Then consider this just the next step. After he fucks your sissy ass tonight you'll be totally committed to being all the woman you can be.”

An hour later I was soaking in a luxurious bubble bath and preparing myself for the evening's events. I was looking forward to actually taking a man's dick inside me and coaxing his sperm into my ass while I was licking his sperm out of my wife's freshly fucked pussy.

After I was dressed in the manner Sherry had ordered there was nothing for me to do except sit and wait and think about what was going to happen in a short while. I did have to admit that I was a little uncomfortable to be sitting in next to nothing while waiting for my wife and her lover to come home.

When I heard her key in the lock I stood and made sure I was still presentable and very well lubricated.

“Ah, Jaime. This is Robert,” Sherry said, making the introductions.

Robert stood around six feet three inches and I couldn't see an ounce of fat on him. He had close cropped sandy blonde hair and was built solidly. Then he shocked me by stepping closer to me and taking me in his arms. He kissed me deeply, his tongue invading my mouth and exploring, showing his dominance.

“I'm happy to meet you too,” I giggled when he broke away and patted my naked ass.

“The pleasure is mine,” he said with a smile. “I get two lovely ladies tonight.”

“Shall we adjourn to the bedroom?” Sherry asked, unzipping her dress and shrugging it off so it fell to the floor as she spoke. “I can't wait to get your cock in my very, very wet and hot pussy.”

While she spoke she was busy taking off Robert's shirt and motioned for me to begin on his pants. “And your going love banging this sissy's tight ass, baby.”

I got his pants down and was impressed by the size of his cock. He wasn't as big as the strap on Sherry had been using on me but close enough and already beginning to grow.

“Go ahead, Jaime, give him a sample of your cock sucking skills. But don't you dare make him cum!”

She didn't have to tell me twice. My mouth was already salivating just thinking about his beautiful cock. Never in my wildest fantasies did I ever think I might be on my knees in my living room sucking my wife's lover's cock, and yet, here I was. It was absolutely wonderful to be feeling a real cock in my mouth again. I think I would have kept on sucking his dick until he blew his load if Sherry hadn't stopped me.

“That's quite enough, he's plenty hard enough to fuck me now,” she said and pulled him away from me.

Just a few minutes later they were in bed and he was balls deep in her dripping pussy. I, of course, was sitting there with a front row seat, which I found much more fascinating than any porn movie. I mean, this was real fucking and I could even hear the noise his cock made as it slid in and out of her.

“Ooohhh, baby, it's so fucking good,” Sherry moaned, her legs wrapping around him. “Fuck me! Fuck me hard! Oh shit, I'm gonna cum! I'm gonna cum!”

When I saw her grabbing and holding on to him for dear life I knew she was in the midst of a very good orgasm.

“Yyyesss! Yyyesss! Give it to me! Cum in my pussy!” Sherry squealed loudly.

Robert buried his thick shaft into her and began twitching, telling me he was filling her with his cum and it was almost my turn. He pulled out of her and moved so I could get between her legs.

“Eat me, sissy! Oh fuck, make me cum again!”

His cum was already slipping from her when I started eating her, savoring the flavor of Robert's thick, hot cream. I remained in place, licking and sucking all his cum, driving my tongue deep into her and getting every last drop.

“Yea, yea, sissy, eat my pussy! Ooohhh, yyyesss, that feels so damn good!”

After watching us for several minutes Robert moved between my legs and placed the head of his hard dick against my asshole. He pushed forward and then pulled back. He'd push a little and then back off. Slowly but surely he gained entrance and when he finally plopped inside I nearly exploded while I kept on eating out Sherry's sloppy wet pussy.

“Fuck her sissy ass, baby! Show what a real man can do!”

Surprisingly he was gentler than Sherry had been and I was soon in heaven while he steadily moved in and out of me.

Sherry moved away from me so she could see her lover fucking me.

“Yea, fuck her good! Cream her sissy ass, baby!”

Robert stepped it up, slamming his sizable hard cock into me.

“Ooohhh, baby, I love your cock in me,” I moaned again and again. “Please give me your cum! Ooo, I need it deep inside!”

“Sherry's right, you are a cum slut,” he laughed.

“Yes! Yes I am! I crave cum! Ooohhh, fuck me harder! I'm such a fucking slut! I love it! Fuck me! Cum in me! Use me however you like!”

Robert started fucking me harder and faster. I knew he had to be getting closer to cumming and so was I.

“I'm cumming, baby, I'm cumming!” I screamed as my body began convulsing with pleasure, signaling a huge orgasm. Not only was this the biggest orgasm I could remember, spilling a huge amount of cum onto the bed, but it continued on even after my balls were empty. My orgasm spread throughout my body, making me feel as if it would never quit. Of course, the fact that Robert was steadily fucking my ass only served to spur on my orgasm.

“YEA! YEA! Here it comes. Oh fuck, I'm gonna cum!”

And did he ever. I thought that Sherry's dildo carried a full load but it was a drop in the bucket by comparison. Just the heat of his sperm in my ass took me to newer heights. But when I felt his cum sliding over my balls I almost lost my mind. Just as I'd discovered when I started sucking cock, I knew I was hooked and Robert would only be the first of a countless number of men to fuck me.