Fun with a Cherry Popper

An involuntary moan escaped my lips as I dismounted and the dildo slipped down and out of my pussy. I found and pulled on the end of my knot and my hands were again free. I decided at that moment that as much as possible, I was going to spend as much of my weekend as possible in the most femme manner possible. And as submissive as possible.

That decided, I left my cuffs on as I went to clean my prosthetic puss out and go to the bathroom. I was exhausted, it was after 10:30, and I was a little buzzed from the wine.

Once I had cleaned it up I put it back on as soon as possible, wondering if there was some way to urinate without having to take it off. There had to be something I could do.

There was still no response from Marissa, so I turned everything off in the living room, making sure to rub my legs together as I walked in my heels, and was just about ready for bed. I decided to leave my makeup and wig on while I slept but didn't want to have my heels and lingerie on. I slowly took my shoes, stockings, and bustier off, leaving the slutty crotchless panties for last. For a replacement, I selected a black babydoll nightgown with matching lacy bikini-cut panties and nothing else. I'd save the feeling of stockings for tomorrow.

To feel completely submissive, I decided that Nicole should wear her ankle cuffs as well, so I put them on, too, and crawled into bed. As sexy as I felt with the sheets caressing my bare legs and my prosthetic tits changing the way my body felt, as well as not having anything between my legs but a silicone cleft, I fell asleep quickly.

I awoke to bright sunlight the next morning. At first, I was disoriented. It quickly returned to me why I felt so different as soon as I moved my legs. I shivered at the feel of my bare skin being caressed by the sheets and by my nightie.

I got up to relieve myself and was frustrated because I had to pull my prosthetic off to do so. As soon as I had some coffee going, I set out to find a solution. Before I got there, though, I saw that I had a reply from Marissa.

"Hi, Nicole,

I'm really excited to see what your new toy is. I'll be free on Saturday afternoon. It's been a little while since I've dressed, so I'll have to get ready. Do you want to come over here, or should I come to your place?

Marissa"

I replied as fast as I could, telling "her" that absolutely, this afternoon would work and sooner would be better. I also explained that I was going to try to stay en femme the whole weekend. Except for going out in public. So my place would be far better.

I had gone out dressed a handful of times, but mostly that was late at night when the odds of someone seeing me were very low. The thrill of being out in public, dressed as a woman, with a plug in my ass, of course, was almost debilitating it was so good. But I was still far too shy to go out in broad daylight and try to pass. Although I was sure that not having to worry about a lump in the front of a skirt would help.

I pondered what I would do with myself for the rest of the day, not sure, then decided to try to figure out how to pee without having to break the illusion between my legs.

There were different types of prosthetics than the one that I was wearing, designed for that, but I didn't want to spend another $200 on another prosthetic just to pee.

I ended up on the manufacturer's website for what I was already wearing and stumbled across a tube with a condom-like attachment that rolled over the head of the penis to catch urine, which was then run through the hose and out through the opening. Perfect!

I wanted to see if I could jerry-rig something like that with what I already had. I found a foot long piece of tubing from some project or other and I had plenty of condoms. I unrolled the condom partway, and poked the end of the tube through the tip, taking great care not to tear it as I pushed it through. I managed to keep it from tearing, so I wrapped a little tape around the end, then tried to run some water through it. It worked reasonably well, so I pulled myself out of the pussy, rolled the condom partway down the length of my shaft, and guided the tube down to my labia, where I pulled it through. I snipped off the extra hose with scissors after I had it all the way back on, and checked how I looked in the mirror. I couldn't even see the tube.

Time to try it out! After three cups of coffee, I had to pee, so I sat on the toilet and let it fly. It felt amazing to not have to make any accommodations for my manhood, just urinating exactly as a woman would. I was amazed at the fact that I felt even more feminine and girly with this revelation.

I knew that my makeshift solution wouldn't hold up forever, so I ordered the urination kit from the manufacturer with the fastest shipping available, wishing I had thought of this before ordering the one I was wearing, but satisfied with the results of my improvisation.

That taken care of, I put my panties back on and looked at the clock. It was still only 11. I had at least 5 hours to wait for Marissa to arrive.

I still felt amazingly feminine. My makeup and wig had not been skewed very much overnight. I touched it up, then returned to the computer to do some more research on binding myself.

I read up a little and decided to make some ice timers for myself and test how long they took to thaw so that I would have some idea how long I'd be bound if I locked myself up in bondage.

It turned out to take about an hour for one ice cube to melt and allow the string to pass through the eyehook that I installed in the ceiling just above where my left hand would be if I was tied to it, spread eagled. I tested another one to make sure that I had the length of the string right, and it seemed good. By now, it was two in the afternoon. I had to pee again, and it felt so womanly for me to have to drop my panties and sit in order to relieve myself. I even made sure to wipe myself carefully after I was done.

Pulling my panties back on, I realized that the tube might cause complications when I was being penetrated, so I thought that I should see what affect it was having.

Before I did, I got a reply from Marissa telling me that she'd be fine with coming over to my place, that she loved the idea of me being dressed and girly all weekend, but that 4 that afternoon was the earliest she would be able to make it. Oh, well.

I got my mirror from the bathroom, some lube, and my dildo, and sat on the couch with my legs spread wide after slipping out of my panties. I put a little lube into my silicone opening, then inserted a pair of fingers. I had done a better job than I could have imagined. The tube was at the very back of the opening, and I could feel it, but it wasn't sharp or even uncomfortable on my fingers. In fact, I could only feel it if I pushed my fingers all the way to the back of my hole.

Perfect. I kept a finger in my hole as I used the other hand to guide the dildo into me. I slid it all the way in, sighing as it caressed my own swiftly hardening member, and soon it was buried all the way inside me. I could feel a little gap as I started to saw it in and out of myself, and was satisfied. I removed my finger and kept fucking myself gently. The partial condom reduced the feeling a little bit but it still felt fantastic. I could feel that I was close to coming, but forced myself to first slow down and then stop. I wanted to wait for Marissa.

That reminded me that she was due to arrive soon. I reluctantly got rid of the dildo and got up. I cleaned it off and relieved myself again, reveling in the feeling of femininity as I did. After how close I had just gotten myself, it was highly arousing.

I wanted to wear something sexy and slutty to show off my new toy for Marissa, so I got my lingerie back out. I decided on my white corset with breast cups to give me great cleavage but without highlighting that my breasts were just forms. With that decided, I picked out my white matching stockings and five-inch heels, along with a tiny satin g-string pair of panties.

I could feel some stubble on my legs, so I ran a bath and shaved my entire body again, then dried myself off and reattached the pussy and breasts that I had been so loath to remove after a thorough enema. I then put my sexy red wig back on and re-did my makeup.

Next, I put my corset on, first closing the hooks on the back and then tightening the laces so that I'd have more of an hourglass figure. Next came the panties, which fortunately could be untied at the hips so that they could be taken off without removing the garters.

My favorite part was next. I slowly slid the stockings up my smooth legs, shivering a little as they caressed my skin, then attached the garters.

Slipping into my sexy heels, I noticed that it was just a few minutes after 4. I was just heading back out into the living room when there was a knock on the door. I checked the peephole, butterflies in my stomach, then let Marissa in.

She's even taller than I am in my heels, and she had her own on. With 5" heels, I stand just under six-foot-three inches tall. I had to look up as I let her in.

We never kissed, since this part of our friendship was purely sexual, but we hugged after the door was closed. We looked each other over. She was wearing a moderately conservative maroon skirt over what I'm sure were very racy panties and matching black stockings, and was wearing black heels as tall as mine. She had on a light coat over a cream colored blouse, and her chest looked as though she was wearing her breast forms as well.

"You look great," we both said to each other and laughed.

"What's this new toy you have?" she asked.

I smiled and said, "Follow me." I noticed that even my walk was more feminine now that I was wearing my new toy.

I led her into the bedroom, sat on the bed with my legs spread wide, and pulled my panties to the side.

Her eyes goggled. After a few seconds, she asked, "Is that real?"

I giggled. "No, but it feels pretty great." She came over and asked if she could touch it. We're both (mostly) heterosexual guys who love to crossdress and who both get an urge for a little cock while we're doing it. We're both enormous fans of transgendered women and prefer the type of tgirl porn where the woman with the cock is fucking girls or guys.

So she knew what the real thing looked like and commented on how realistic it looked and felt. I glanced over at her, still standing beside the bed, and could see a tent in the front of her skirt.

While I couldn't feel it, she was caressing and exploring between my legs, so I reached over and gently fondled her through her skirt. She sighed and closed her eyes. "I guess you like it," I said softly in my most feminine falsetto.

"This is so hot..." she whispered.

"Then let's get you out of that blouse and skirt," I said. Not another word needed to be spoken. She shirked her blouse and skirt immediately, unceremoniously dropping them to the floor. I was right about what she had on underneath. Forms similar to mine in a sexy black lacy bra, a lace thong that was struggling to contain her erection, and thigh-high stockings.

She joined me on the bed. As soon as she had lain down, I pulled the front of her panties aside and took as much as I could of her hard, seven-inch circumcised cock into my mouth. She gasped and ran her fingers through my hair, being gentle so as not to unseat my wig. I was hungry, sucking while circling the head of her hard cock with my tongue as I bobbed up and down, my hand following the movement of my head. I felt some light pressure on "my" pussy, then sighed as two of her fingers entered it.

"This is so hot..." she sighed as I devoured her member. My other hand was wandering up and down her long, smooth legs. I was surprised at how fast she stopped me.

"I've got to fuck you," she whispered. She wasn't able to contain the masculinity in her voice as well as I was, so she mostly whispered while en femme.

As much as I wanted her to fill my mouth with her cum, I wanted even more to feel what it would be like to be fucked as a girl. I simply rolled onto my back. She had a condom on in record time and put a little lube on it. Then, she knelt between my legs, pointed her cock at my labia, and slowly slid in, lying down on top of me as she entered.

It felt a hundred times better than the dildo had. I moaned, the sensation of her very hard member rubbing against mine as her shaft tightened my ersatz cunt. My legs went around her waist as she began to thrust, holding me tightly. I found myself moaning as her cock stroked mine inside my twat, turning it into a combination of a clitoris and a woman's g-spot. I was astounded at how girly I felt and I could tell that I was going to climax quickly.

Marissa wasn't possessed with the stamina I had and tended to come faster than I did. And boy, did she ever. Just as I was reaching my crest, holding her body tight as her cock stroked my internal clit, our tits pressed together, her breathing went ragged and she was pounding me. I cried out as I felt my legs clench around her even tighter, totally out of my control, involuntarily trying to get her deeper as her cock pulsed and spurted inside me. She thrust a few more times as we both came, then simply lay on top of me, panting and totally spent.

After a moment or two of basking in the afterglow, she pulled out and got up to go to the bathroom. After she was done, I followed and left the door open. I simply sat down and kept my panties pulled to the side, then let the urine flow out of me.

She watched, clearly amazed, still turned on, and looking a little jealous.

After I finished up, we talked in the living room about how I had found it, its price, and how it worked. I ended up taking it off and after cleaning it, showing her how it worked and my modifications.

Her curiosity satisfied, we had a glass of wine and talked about other things. "How long are you going to be able to stay here?" I asked during a lull in the conversation.

"Another few hours anyway," was her answer.

"Can I ask you to do me a favor?"

Marissa agreed and I explained my self-bondage fantasy and how I wanted to try it but wanted to have someone nearby while I tried it so that if anything went wrong, I wouldn't be helpless.

With reluctance, she agreed. We'd already talked about bondage, and as much as she enjoyed feeling feminine, bondage did nothing for her sexually, either giving or receiving. But she understood how much it turned me on and how it heightened my feeling of being girly. I also had almost a fetish for forced orgasms. When I wasn't dressing or watching transwoman porn, I was watching bondage porn where orgasm control figured into the equation heavily.

I explained what I wanted to do and she agreed to stick around while I set it up, got myself bound, and to wait until my escape mechanism worked and I was back out again before leaving. She said that she might want to fuck me again. She didn't mind being the top, but it was exceedingly rare that I wanted to be the one penetrating while I was dressed.

I got to work preparing everything. For my first self-bondage, I wanted to keep it simple. I got my ankle and wrist cuffs on and prepared the ties to my bedposts. For this, I was going to tie my legs together, so I modified the spread eagle so that the rope for my ankles met between my feet.

Next, I gave myself another enema and got the toys I wanted to use out. I had Marissa help me insert my very large butt plug, which was almost four inches in diameter at its widest point. Almost ten minutes passed while we worked it into me, slowly thrusting it in a little farther to stretch me out, then drawing it out a little to allow the muscles some time to adjust, then repeating but pushing it farther in every time.

I gasped as the biggest part of the flared portion slid past my innermost muscles and settled deep inside my ass. I made sure that the remote for the vibrator inside it was handy, and enjoyed the feeling of my cock-shaped vibrator filling my new pussy. I waited to turn that on, too.

Then I got to work tying myself up. After getting the ice release for the key to my wrist restraints, I started with my ankles, wrapping the quarter-inch thick rope four times around them, then looping it between my ankles to make a cuff. Next, I did the same around my insoles so that my feet were totally immobilized as well. From there I took the rope and looped the rest of it around my knees in the same fashion, finally tying it off behind my knees. My legs and feet weren't moving. I tied them to the line at the foot of the bed and I was stuck on the bed at this point.

I had already made sure that I had my gag and blindfold within reach, and buckled the harness around my head, making sure that I couldn't push it out of my mouth. I had chosen the inflatable one, so I gave it a couple of squeezes, moaning with pleasure and surprise as I felt my mouth fill up. The blindfold was simple and just slid over my head, so I made sure that I knew where it was, then locked my right hand into the tie to the bedpost, the one with the emergency escape after checking to make sure that I could reach it if the ice key release didn't work. All set.

I took a deep breath, turned on the vibe in my ass and in "my" pussy, moaning with the feeling as the vibrators worked on my most sensitive areas, then slipped the blindfold on. My heart flip-flopped as I heard the padlock click shut. The only reason that I didn't panic totally was because I knew Marissa would bail me out if everything went to hell.

However, that fear also made my clit super hard, which just pressed it more tightly against the vibe in my pussy. I couldn't help but moan and squirm a little, the vibrations like little waves of ecstasy washing over my restrained body.

I was instantly so horny that all I wanted to do was to get my hand free, pull my cock out of my pretend pussy, and come right away. Of course, I couldn't, since I was tied to the bed. Securely.

My body took on a mind of its own and I kept writhing and squirming as the vibrations cascaded through my body. I was moaning like a bitch in heat, eager to come. I knew that when I did, it would be hard.

I lost track of time as the pleasure engulfed me and I just relished the feel of the stockings on my legs as they brushed against the covers on my bed, the fullness of having my ass plugged and vibrating, the way the weight of the forms moved on my chest as I moved, the oscillating in my ersatz twat, and the helplessness of being immobilized, blindfolded, and gagged securely.

I could tell I was going to come soon. I heard myself moaning more and more like a woman approaching orgasm and it was the sexiest thing I think I'd ever heard. Suddenly, like a freight train, it hit me. I screamed as my clit pulsed against the vibrator, my ass clenching shut around the huge plug. That only drove it deeper into me and pushed it more firmly against my prostate, heightening the ecstasy. I screamed again, unable to stop my body from shuddering with the release.

I didn't hear the key drop, so I knew that I was in for more stimulation whether I liked it or not after I came. The vibrations where just as strong and while they weren't quite painful, they were uncomfortable at first.

My moans turned to whining as now instead of trying to get more of the vibrations, I was trying to get away. I just needed a few minutes. Too bad. I was trussed up tight. It felt like half an hour as I lay there, writhing, unable to escape my own "trap."

Soon, though, they became pleasurable again. This time, it happened even more quickly and, I was surprised to find, even more powerfully. I screamed again as my second self-induced orgasm hit. My body was out of control, convulsing, as I thrashed as well as I could in my predicament.