Crossingover

I have already decided to start at the beginning however I ran into one of my ex's and remembered the times we had. This is the first one where things became depraved. Please I do enjoy feedback. I hope you enjoy my memories.

* * * * *

Have you ever had one of those relationships where you could tell your other half everything? I do and I still can't decide if it was a mistake. Of course it starts off small. Like things I liked. I have my hair long so it was great when she ran her fingers through it. As our relationship progressed and became sexual, we began to trade fantasies.

She liked watching gay porn, dressing guys up in drag and oral sex (giving that is). She loved to swallow. Hell, I couldn't complain about that. She was also Voyeuristic. She loved to be watched and to watch. She was on the kinky side.

I on the other hand was quite content with the constant sex. Then one day I opened my mouth.

"That looks like fun." I said as I was on the couch with a porno film on the TV She turned to look behind her since she was on her knees in front of me. I loved that. She was so sexual. The scene on TV consisted of the guy getting thrown around by a woman. Tina's hand kept jerking me of as we were watching.

"So you like that? You want to serve?" It was such a turn on I nodded.

"Do you want it rough? Do You want to be raped, lose all control?"

"Yes..." I said weakly.

At this point her hand quickened the pace. The sensation increased. The way her hand moved as it closed and rubbed over the tip of my dick.

"Good." She replied as I came. I came all over her shirt and face. It was intense. She took off her shirt and whispered in my ear. "You'll get your wish."

She walked off to the bathroom to clean up. My mind wandered thinking about being dominated by her. She wasn't big, or that strong. SO I knew I'd have to lay along. I didn't mind. My mind began to slip back to my past (story for another time) and my dick was getting ready to go. Tina came back from the bathroom ready for bed.

"This is the way it will be. No sex, no blow jobs, no nothing. When I tell you to do something you do it. Understood?"

Stupidly I nodded I understood. With a loud slap that surprised me, she yelled "I want an answer. Do you understand me?"

"Yes."

" Yes, what?"

"Yes... Mistress." Another slap.

"I want answers immediately or you will be punished! Understand?"

"Yes, Mistress."

"Good. Now get ready for bed. I laid out your clothes." I walked to the bed room thinking 'I actually wanted this'? Apparently my dick did because it was begging for attention. I entered into her bedroom surprised at what she laid out.

I knew I was going to have a very interesting time. She laid out a pair of her black thong panties and a black chemise. I started to wonder if she picked the movie out, or if she did.

" You better wear it or else!" He voice echoed to me. I stripped quickly, happy that she laid clothes out for me. I've worn my mother's lingerie in the past and have worn previous girlfriends, never Tina's though. She always took and brought her clothes when she came to my place and I was never alone at hers. So, sitting on her bed was something I was dying to wear.

I put the thong on first. It was tight and squeezed my balls. I endured. My dick was peaking out the top, straining against the smooth silk. I put the chemise on over that. It was tight and I could feel it rip if I moved a certain way.

"Are you ready?"

"Yes, Mistress."

She entered in and looked me over. She stepped closer hugging me. Her fingers worked at my ponytail and took it out so my hair flowed freely. My erection was still aching for attention. Her room was the typical girls room. Everything was frilly. I laid down in her bed as she directed me.

"I love you... Bitch!" She said.

"I love you too, Mistress."

The night continued in silence and I fell asleep wondering how this would end. I woke up that Saturday morning to find Tina already up and dressed with a grin on her face.

"Get dressed. Time to go shopping. "She said and left the room. I got my clothes out of my bag and changed wondering what was in store. After dressing I met her in the kitchen.

"Are you ready?"

"Yes."

"Yes..What?"

"Yes, Mistress." I would have to get used to that. Hell, my dick didn't mind. He was already at attention. We went to all kinds of clothing stores. She bought thigh highs, crotch-less panties, chemises, night gowns, all stuff she bought I was imagining being able to wear. Our conversation was normal but my imagination was not. At the end of our trip she had two skirts, 5 pairs of thigh highs, 2 garter belts, 3 chemises, seven bras, 2 crotch-less panties, 5 silk panties, 7 thong panties as well as 2 nice evening gowns. Also 3 silk night gowns and 2 pairs of high heels. She drove me back to my house leaving me to go in. I exited the car and started in. The horn stopped me.

I went over to the drivers side window to question her,

"Don't forget your clothes." Surprised I must have looked stupid. Why would she buy all this stuff for me just for a fantasy of her dominating me?

"Oh, and here." She handed me a card. A plastic credit card... MY plastic credit card.

"Go on honey. I know your dying to try them on. Get used to wearing it. My fantasy night is coming soon and I want you to play the part." I kissed her happily as she giggled. I went to the trunk and took out all the bags.

I made it into my house and spread the clothes out on my bed. She picked everything out in my size. As I undressed I remembered she said "her" fantasy. Now I knew she would like it. For the next few hours I tried everything on. It was sensual heaven. The phone brought me back to reality. I was wearing a red pair of thong panties, the red garter belt and red stockings. Tina loved red. I also had on a chemise. Also red. Reluctantly I picked up the phone. Paranoia came over me. Like the person on the other end could see me.

"Hello?" The voice said.

"Hello" I replied. 'Oh shit!' I thought. It was my Mom.

"I just called Tina's. She said you were home."

Oh shit. What do I do now? Then the other line rang. I thought I was saved. However that was not the case.

"Hello?"

"Hi, Honey! What are you wearing?"

I replied.

"Good. Listen, your Mom just called. She should be calling you."

I swallowed hard. "She's on the other line." It felt like an exciting kind of fear. My chest sank as my dick grew hard.

"Good. This is what I want bitch." My dick twitched quicker. "Go back to talking to your Mom. I want you to jerk off as you do. Get dressed and meet em at the mall. Understand?"

"Yes, Mistress."

"Oh, and make sure you tell her the truth to every one of her questions she asks. And I will know. We talk.

SHIT! SHIT! SHIT!

I went back to the other line. "Sorry about that Mom."

"That's OK dear. Is everything OK?"

"Yeah. Everything's fine." I stuttered nervously. I started to feel my dick though the fabric. Stroking it. Having pre-cum soil my panties.

"What are you doing?"

"What am I doing?" I thought ' Well, Mom. Tina told me to get dressed in feminine lingerie and jerk off to your voice. Would you mind talking dirty to me?' What I said was. "Just trying on some new clothes and seeing how they feel. I wondered how much more Tina knew about me and my past.

"Could you come over and help me out. I need to do something in the garage."

"Well, I told Tina I'd meet her at the mall."

"Oh." Her voice sounded disappointed. I stroked faster knowing Tina wanted me to jerk off while my Mom was on the phone. Not after.

"OK. Well, I'll let you go."

"um...." I had to stall her. I wasn't even close.

"Yes?"

"Can I ask you a few questions?"

"Sure."

"What are some things a woman likes?" I asked stupidly.

"Like what baby?"

"Sexually." What the hell did I just say? I couldn't believe I asked that.

"Well, honey, this is a subject we haven't talked about in a long time." Her voice was broken up. Like she was blushing.

"Are you and Tina sexually active?"

"Yes, Mom." I continued stroking.

"Do you go down on each other?"

"Yes." I can't believe I had asked my Mom this question.

"Well, listen to her fantasies. Play along with her." My Mom;s voice drowned out as I thought I heard a moan. Was it me or her? Was she touching herself while thinking of me? I started thinking when I was younger and I felt it and began cumming. The panties felt good touching the tip of my cock. Oh God, I was thinking about my Mom while I was jerkin off. I thought I was cured of that Guess things really do come full circle.

"Uh...Mom" I said" I have to go."

"That's. Oh. I understand. "She said. "Will you still help me with the garage?"

"I'll have to ask Tina but I don't see why not." I hung up the phone and looked down and saw my panties all wet. I felt...well, I felt slutty. I began to get dressed when the phone rang again. I picked it up shaking.

"Hello?"

"Hello Bitch. Was it good?" It was Tina. She never hung up the phone. "How was it?"

"How was what?"

"Don't be stupid! Did you enjoy thinking about your Mom while jerking off? Don't lie!"

"It was OK." I lied. It was great. If Tina only knew what I did when I was younger she would see herself a nun. She didn't know my Mom and I were sexual (that's a story for another time) . "Should I meet you at the mall?"

"Make sure to wear your outfit underneath." I finished dressing and headed out. I was horny still. I started thinking of fucking my mother again. About the one-first time I saw here with a man. How I used to jerk off thinking of her. My dick stretched my panties and I felt the cum stick. When I got tot eh mall, I looked around for Tina. I was paranoid. I though that people would know I was wearing female underwear. I finally saw her and greeted her as I normally would. She smiled and told me I had to ask permission from now on. Then she broke character and was giddy.

"Wait till you see the outfit I got! I rented a room across town so I can have my fantasy night and no one will know." I agreed immediately. We went back to my place to change. Little did I know what she fully had planned. We took a shower and she teased me. It was great. After the shower she put out my clothes. I dressed in all black. Grader belt, thigh highs. panties, skirt long enough to cover my bulge. She even stuffed my bra and did my hair. She even picked me up a blouse when she was at the mall.

'Be right out." She said going into the bathroom.

I looked into the mirror. 'Holy Shit!' I thought. I looked like a woman. I only needed make up now. It was an instant turn on. I started to think that maybe Tina wanted to be with a girl. If that was the case, I would happily do that one.

She came out of the bathroom dressed to the nines. She was wearing a one piece leather outfit. It zipped form crotch to neck. The heeled shoes were even past of it. Exiting like that with her wild hair defiantly made her look like a dominatrix.

"Time to fix you up." It took her no time at all but now I could pass as a woman. "Time to go." The looks we got from the neighbors where comical. They were checking Tina out like crazy. Then I realized. They were checking me out too! I laughed to myself. We drove to her place. We parked and went in. Apparently Tina had this planned this as I was playing dress up. We got in and I was ready.

"Lets go for some drinks." She said.

"OK."

We walked there. My feet were killing me in those heels. But she looked like she could go dancing. Guy after guy came up to us and she kept turning them away. As the night continued we drank and drank. She still turned them away. There was this one guy that was quite persistent.

"Come on baby. Let's go have a good time."

"I don't think you can take me and I know you can't handle my friend." With that she got up and walked out of the bar with me following soon after. It took longer to get back to the motel. Those damn heels! When we finally got back she stopped me in front of the door and just kissed me, Hard!

"Are you ready to be a bitch? Are you cunt?"

"Yes, Mistress."

"Oh, boy are you going to get fucked tonight!"

Unfortunately I was too fucked up to do much about what happened next. I felt a cool cloth cover my face. The fumes were knocking me out cold. I wondered if this is what chloroform was like. The last thing I heard was Tina's scream.

"Hello Bitch!" I heard. I was groggy but it was a man's voice. I felt myself sit up. My hands were tied around my back. I looked over and saw my girlfriend being tossed off the bed. She looked like she was fucked royally. They both were wearing masks on but they were full undressed. They placed Tina in the other seat and tied her up. She looked drugged.

"Your friend put up a fight so we drugged her. Will you put up a fight?"

I looked how bad Tina looked and I shook my head no. I needed to be OK to fight these guys of. They were in for a surpass.

"I don't believe you. Drink this."

I refused. They put a gun to Tina's head. I drank it. It tasted sweet. Immediately I was feeling the effects. I was loopy and light and being untied. I threw a punch. It sounded like a light slap. I was slammed on my knees and I saw a cock in front of me. It was shoved in my mouth.

"Suck it cunt!"

His hand gripped my hair. I glared at Tina and saw the gun. What could I do? I licked the top of his cock, trying to remember how Tina did it. I placed my hand at the base and slowly bobbed my head. It seemed he was quite large. Larger than me anyway. Here I was on my knees like a whore. My dick was even hard. I actually was turned on by it. He must have noticed. He saw my enthusiasm mount. However fear was still on my mind. If he saw that I was a guy, he'd kill me for sure.

"Can you lie on the bed?" I asked waiting to be hit. I figured this way I could keep in control somewhat. His cock was huge. I didn't need him fucking my face. He complied. I climbed up on all fours and I started blowing him again. In moments he was cumming.

"Swallow it all!" He cried as his rhythm became faster. I gulped and deep-throated him humming to myself to give him a pleasant sensation. This also helped me. This way I wouldn't have to taste his cum. It all shot down directly into my belly.

"Oh wow, this bitch is good! You have to try her!" I sat on the bed trying to look beaten. I didn't want them to know I actually liked it. I was bent on my knees with my hands in front of my dick.

"I wonder what she tastes like?" I looked at Tina's blank stare. It seemed she would have to go to therapy about his. The sad part is I started to think about Tina being fucked by them? I had to stop these thoughts but it was too late. I was cumming. I stood as still as I could. I felt the cum be stopped by my panties and it dripped below to my balls and ass. Tina spoke. It almost sounded like defiance.

"I don't think you'll like the taste. She's ragging."

"Is that right? I guess your friend is going to get fucked up the ass then. Lay on your tits bitch!" I did as he said realizing how happy I was that I came. My dick was now in my panties and no where near as obvious as it was. The one guy I sucked off went over by Tina. They switched places. He was closer to my size. I watched as the gun switched hands.

"Are you ready for a fucking bitch?" It seemed like I didn't have a choice. He was already pulling down his pants. He was closer to my size. I felt as he pulled my panties down just to reveal my ass. He left my skirt on to cover it though. A finger slid up quickly.

"Damn Bri.. This bitch is wet even in her ass!" I couldn't see the other guys reaction but I was now guessing his name was Brian. Now my skirt was lifted and my ass got smacked. "Damn, she looks tight. Is your ass a virgin?"

"Yes." I said what he anted to hear.

"Not anymore!" and he slid himself in and started fucking my raw. It took a while for my ass to get used to it before it started to feel good. The whole time though I was hoping I'd get shit on his dick. Two minutes later and it was over.

"Damn, that was the best ass fucking I ever had." I could only think to myself that it was piss poor. Then I realized what I was thinking. I was being fucked and passed around by two guys and liking it. Well, maybe not the smaller one. Still, I wasn't done yet. I wanted to be fucked and fucked good. I felt wasted though. Still feeling the drugs I rolled onto my back. I wasn't thinking but apparently I was still covered.

"Thanks for the night ladies." They first covered Tina's face with a small white towel. He head stumped to the side. It was what they used to knock us out last time. Then It was my turn. Everything went black.

When I awoke I felt my ass getting fucked. My eyesight was still hazy and blurry.

"Good. Your awake bitch!" a woman's voice said.

"Wha? What's going on?"

"You looked like you needed a serious ass fucking. It didn't look like you were taken care of" I sounded like Tina.

"Tina?" I was fucked faster. My dick was hard again this felt good.

"I am Mistress you fucking cunt! All the things I do for you. I got you clothes. I take you out. I got you laid and this is how you repay me?"

"What are you talking about?" I didn't even have to ask that last one to know the answer. I knew all her fantasies. She liked dressing guys up. She like guys fucking guys. I was had. This was her fantasy not mine.

"Did you like?" she asked no longer dominating. She kept fucking though.

"well..."

"Don't lie!"

"Yeah. It was fun."

"Good." She said smiling. "Jerk off while I fuck you!" I did as she asked while she lifted my legs into the air. When it was all over she handed me a bag with clothes in it. We changed and got dressed. We drove in silence, but when we got to my house I turned to her and said "So, next time its my fantasy, understand?"

"Yes, I do."

I kissed her good-bye. Walking up the steps I pondered what I could possibly do to her. A plan started forming in my head. I just needed a week or so to set it up. Oh yeah. This would be good. If I could just make it work.