One Weekend

I was twenty when I met Michelle. She and I didn't actually move in together, but she had a suitcase that she kept over at my place with many different clothes in it. Everything from nice panties to no frills granny panties. Her sexy black dress, jeans, bikini, lingerie, and regular stuff also like white t-shirts and pajamas. She had some cash through her family. She wasn't rich, richer than I was and still am. So her clothes were mostly higher end stuff ordered or purchased from Europe. Also in the suitcase were two dildos and three vibrators of different sizes along with some lube.

She went on vacation to New York and while she was there she called me up to tell me that she was going to stay there and that she wanted me to send her stuff to her. She didn't mention us breaking up, but she also didn't mention me visiting her or even moving there, so it was clear she was moving on. Not having the money to ship her clothes across the country, and her not sending any money (or even an address), I did not send her the suitcase. It just sat in my closet for a few months.

One Friday night, I was at home, dateless. I had a few nights prior taken to sleeping with a pair of her panties (pink and black, see thru in the front) under my pillow, occasionally sniffing them, enjoying the smell. A thought crossed my mind. My dick was instantly hard and I had to try it. I was already naked and I slipped on the panties. It was a strange feeling to say the least. But good.

I opened the suit case and pulled out the little black dress and put it on. I was enjoying this greatly. I often had bi or gay fantasies, and cross dressing was often in those fantasies, but this was the first time I had ever tried anything like it. I ended up shortly after with the dress pulled up, the panties down and me doing myself in the ass with the small vibrator. I wanted more.

After I came I went to the computer and ordered a wig that matched my hair color. I liked the shoes that were in the suitcase, but they were not big enough for me, so I, went looking for feminine shoes to fit me. I also shaved off my body hair, except for the pubic region. If anyone asked, it was because I was taking up swimming.

The week that followed was torture. The wig and shoes arrived, now it was just time to wait for the weekend. I sat at home practicing sitting like a lady and trying to come up with a female name. Finally, it was Friday. I came home from work and closed the blinds to my apartment. I removed my clothes and took a shower and shaved my face and legs. I put the wig on and applied some lipstick (I found a stick buried near the bottom of the suitcase), I spent the week practicing that also. I considered putting on one of the lingerie numbers, but instead, put on a wrap around skirt and a blouse, after putting on matching bra and panty. I looked myself over in the mirror. I looked pretty good I thought.

I sat down on the computer and went to a chatroom that was divided up by regions and sexual topic. I trolled the chatroom looking for someone, anyone, to fuck. I didn't want to cyber. I started this around seven that night. I didn't work weekends, so I could pretty much stay up all night if I had to.

It was about 8:30 when I finally found someone in my town looking for some action also. I have him my address and told him that my name was Alice. I was nervous has I waited. It was less than thirty minutes, but it felt like a day, until he knocked at the door. I opened it, and was relieved to actually find him attractive. He was in his early thirties. No gray hair, clean shaven, bi sexual who was in decent shape.

I invited him in, we talked a bit, breaking the ice. I didn't know if I should make the first move or if he was supposed to. This was completely new ground for me. He kissed me, without hint or warning. Finally, one of us was doing something. We continued to kiss, which lead to making out. I pushed him off of me and undid his pants, and reached in, pulling out his manhood. It was not quite as big as mine, but bigger than the vibrator that I had been using.

Without any thought, I took the head of it into my mouth, and then, I found myself wrapping my lips around the shaft and bobbing up and down while he rubbed my ass. The taste wasn't what I thought it would be like. I felt my skirt rising up.

Part of me began to worry about what was bound to happen next. I decided that the only way I was going to get through it was to basically let him take me and to submit to his will. I pulled off his cock and could see a trail of spit from my lips to his cock. I reached onto the floor and grabbed the bottle of lube and applied some to his dick.

He stood up and walked behind me, pulling down my panties. I was on my knees, resting on the couch with my upper body on the back of the couch. I waited. He spread my ass cheeks and slid his dick between them. I moaned as I felt the dick enter me. I bit down on the couch cushion. I closed my eyes. It hurt. He kept going. Before I noticed, the pain was gone and it was feeling good. I was moaning and grunting with his thrusts. I should have tried this sooner. His strokes changed and before I could react, I felt him stop and collapse. He just came inside of me.

He pulled out and I stood up. I asked him if he would go down on me, and he did so. Between the fucking I just got, wearing women's clothes, getting a blow job, and feeling the cum in my ass, it wasn't long until I came in his mouth.

He got dressed and left, after I told him it was a one time deal. I cleaned myself off and changed into my regular clothes. I sat in front of the tv, not believing what I just did. My ass wasn't really sore, it was a good feeling, that much was certain. I tried to watch some old movie I had seen a thousand times before, but my mind kept flashing back to what I had just done. Each time I remembered him calling me a bitch, or a whore or a slut, my dick twitched just a bit. He had made me his bitch. Enough of a slut to put out in less than an hour. The feeling of shame and disgust disappeared. I wanted more.

I changed into women's clothes again. This time it was into a pair of granny panties and her pjs. I didn't know what I was going to do next. It was payday and I thought I might get some clothes my size before I destroyed all of her stuff. I might hit that chat room again and see who was there.

Before long I was rubbing my hard cock through the pjs. The youngest was a 19 year old looking for his first time. He was tempting. I got his number and promised to call him the next day. What did catch my attention was a cross dresser not much older than I who had been doing it since the age of 16. Tabitha, the cross dresser, was willing to come over and show me a few things. I was eager to learn.

It was close to midnight when she arrived. I was just in a pair of boxers. We figured it was best to start there and work to me being Alice again. She was wearing a sundress (it was late spring) and looked passably female. We started with make up and moved up. I tried to make a move on her at several points, but she stopped me, letting me know that this was not a booty call.

After her final lesson we made small talk and had some drinks. I invited her to crash on my couch. She asked me to change into my sleep wear. I gave her an odd look. She said that it was to see if I remembered her lessons. I went to the bedroom and selected a short silky nightie and the matching panties that went with it. I figured it wasn't too forward but still girlie enough. She smiled when she saw me walk out, and addressed me as Alice.

She and I had another drink and she then said, "Okay, now that you look more like an Alice, sound like an Alice and act like an Alice, it's time to see if you can suck like an Alice."

We sat back down on the couch and she had me pull my dick out. She sucked it for a short bit, the stopped, laid back and said "Now, it's your turn." as she removed her dick.

I tried to mimic what she did. First my tongue circled the head of the dick, then I licked the shaft, even sucked on her balls before going down on her. She moaned, told me I was doing a good job and called me a slut. She said "Don't stop." and closed her eyes while I continued. It didn't take very long for me to enjoy sucking a dick. I released her dick from my mouth and kissed her on the lips before taking her hand and escorting her to the bedroom. We laid on the bed, arms and legs around each other, my dick against her's. She adjusted herself so that we were now in a 69. Not as comfortable as the ones I have been in before, but still highly enjoyable. I did everything she did to me, including massaging her asshole when she did it to me. She didn't need to do it long before I came into her mouth, and she into mine.

This was something that I had fantasized about, and now, here I was with a mouth full of cum. Tabitha kissed me, sliding her tongue into my mouth, and mixing our cum together. We went to the bathroom and rinsed our mouths out. We returned to the bedroom and kissed again. She put on some pajamas and I put back on the nightie. We kissed and went to sleep.

I woke up to her sliding her lubed dick into my ass. I welcomed it gladly. She did it slow and gently before building up to a fast and furious tempo. I had my face buried in my pillow. I felt her thrusts change. I expected to get my ass filled with cum. Instead she pulled out and came all over my face. She then reached onto my night stand and grabbed my cell phone, getting a picture of my cum covered face. I licked the cum from around my lips and she stood up.

As I cleaned my face she got dressed. We exchanged phone numbers and discussed meeting again. I told her about the 19 year old and she gave me an idea that I had not thought about, but I was going to try it that night.

The 19 year old, Derek, called me up. We made plans for him to meet me around seven. It wasn't even noon yet. I decided that I was going to spend the day as Alice. After showering and shaving, I put on a pair of loose shorts and a low cut top and a white no frills bra filled with a water balloon full of shaving cream. The panties were cotton full back, white and plain. I didn't dress up to be sexy, I dressed up because I felt like it. I painted my toe nails. Finally having small feet has paid off. I put on the wig and brushed it. I looked at the pack of press on nails. I debated putting them on. Yes they'd make me look more like Alice. But I didn't want any glue or anything to be on my fingernails come Monday. Finally I said "Fuck it" and put them on and painted them to match my toes. I looked at myself in the mirror and liked what I saw looking back at me.

I was horny, thinking about tonight. I didn't want to masturbate. Well, I wanted to, but I wanted to wait until tonight before I came. I surfed the internet, checked my email to make sure that Derek didn't email to cancel, also listened for the phone, just in case. I played some online games followed by a movie. I figured watching a movie that I'd seen a thousand times would make the day pass faster. I cooked up some dinner, nothing special and before I knew it, it was already 6:30.

"He'll be here soon." I said to the empty apartment as I entered the bathroom to apply lipstick and eyeliner. Then I went to the bedroom to change. I stripped completely naked. I put lotion on my body, save for my dick. I wanted him to taste dick and not lotion. I put on a black thong, I'm really loving those things. I put on a wrap around dress followed by a black bra. I didn't fill it with anything for good reason. I'll explain later. Derek knew what he was getting anyways, so it's not like he was going to miss out. I put on some stockings and a pair of shoes. I put on some soft music and in case things needed a little help, I put in a porn movie. I hoped it wouldn't come to that.

There was a knock at the door as I checked my cell phone. I asked who it was and it was Derek. I opened the door and he walked in. He was 19, tall, taller than me. He looked young and was fit. I smiled and ran my fingernails over his chest. His shirt was so tight against his chest.

We sat down on the couch. I offered him a drink. He turned it down and I said, "Don't worry about your age honey, I won't card you." He laughed and asked for a beer.

As he drank the first beer of his life, he explained to me that he was still a virgin. I assured him that there was nothing wrong with that (he wasn't going to stay a virgin much longer if I had anything to say about it). He came from a loving house hold, but his mother would have nothing to do with homosexuality or even bisexuality. He was still living at home at that. He being shy and too afraid to start anything kept him from doing more than just kissing girls, or so he thought. It wasn't until recently that he started to have thoughts and feelings that maybe he might be bi or gay. I said that it was no big deal, while rubbing his thigh. He couldn't keep his eyes off my legs. I eyed his groin and found that he was fully hard. It was clear that I was going to have to start this.

I finished my drink and noticed that he wasn't even half finished with his. I suggested a different drink for him. So I made us both screwdrivers and I poured each of us a shot of rum. I invited him to the kitchen as I made the drinks. My skirt wasn't short enough to ride up and show my ass, but it did show off my legs and he was liking the show and I was loving the attention. I suggested that he could make himself at home and I suggested that he was welcomed to take off his shoes, or remove his clothes, what ever worked. He laughed and I eyed him and smiled. I was going to be playful tonight. I wasn't going to the the slut I was last night. No. I was still going to be a slut tonight, but I wasn't going to bang him as quickly as the first guy.

Once I finished pouring and mixing our drinks I handed him a shot and said, "It's simple, once you start drinking you don't stop until it's empty. He asked what would happen if he stopped. I took the glass out of his hand and sat it on the counter, I pushed against the fridge and kissed him on the lips. One of those kisses that morphs into a sloppy open mouth kiss. I could smell his after shave and feel his hard cock against me. I said, when finished, if you liked that you'll start drinking and not stop until it's finished. We toasted and he swallowed it all. We then sipped out screwdrivers while talking more. He did grunt work on a construction site, which is why he was built the way he was.

I sat up on the counter. The skirt fell in such a way that one leg was hidden and the other was fully exposed. I grabbed Derek's hand and placed it on my exposed knee. I rubbed it. I asked "Like it?" and he nodded in agreement. We kissed again and I pulled him closer to me, between my legs. I ran my hand over his chest, around his back and over his ass. I think my dick was about to tear through my thong. Especially once he ran his hand from my exposed right knee up to my ass and back.

I pulled off his shirt and kissed his left upper arm, left shoulder, the upper left side of his chest and finally his nipple. His chest was also smooth and rock hard. How the hell was this guy still a virgin? All my ex-girlfriends would have thrown this man into bed, tied him down and had their way with him if he was too shy to make any move beyond a kiss. Maybe he was gay because he was having no problems with me. Or maybe he was just bi and I was the first person who wanted it bad enough.

I broke the make out session we had ended up in and I jumped off the counter. I told him to wait for me to get out of the bedroom but to be patient, and to take off his clothes. I was ready to do what Tabitha suggested I do. I closed the door removed my blouse, skirt and bra. I put on a see-through black nighty (this is why I didn't use the balloons) and looked in the mirror. The front of the thong was also see-through. I posed again, enjoying how I looked. I put lube and toys next to the bed. We might not use the toys, but they were there if we wanted that option.

I opened the door and walked through. Derek was there, completely naked, as I suggested. He looked at me and his dick jumped. That was a huge compliment I thought. I suggested that he join me, and he followed. We kissed again before I pushed him into my bed. I laid on the bed next to him and proceeded to massage his dick. There was already a lot of pre-cum. He moaned loudly. This dick was huge. I was going to need lube. I then thought about how he told me that he was a virgin and a thought came to mind. I asked, "Have you ever jacked off?" And he explained to me what I thought was impossible. He never did. He knew what it was, but while he wasn't raised in any from of a christian house hold, he was raised to never do that. No wonder he was doing grunt work at a construction site. No sex, no drinking, no masturbation, he was probably in need of any physical activity he could find. I figured. Then it occurred to me that I was probably his mother's worse nightmare. A cross dressing male who's gotten Derek drunk, aroused and about to have his first sexual encounter which was also going to be his first homosexual encounter. My dick throbbed with that thought.

As I started to pump his member, I noticed how good my hand looked while it worked the dick. Something about the nail polish, the fake nails and his dick. I opened my mouth and put just the head in. I removed it and just licked it with my tongue. He gasped as I continued this. I stopped and put more into my mouth. I didn't bob my head long, probably not even ten times until he came. I tilted my head back and opened my mouth. This really felt odd. I've seen porn videos of women doing this with cum and I was curious. I lowed my head forward, closed my mouth and swallowed the cum. He watched me the entire time.

I kissed his belly, and then made a path to his lips and we kissed again. I wasn't going to let him cum and run before giving me mine. He, on the other hand, had other ideas. He slid away from me and started for the bedroom door. He fed me some bullshit line about having to work early in the morning. As he put on his clothes I called him on it. I should have thrown his ass out in just his tidy whities. He wasn't gay or even bi. He was just experimenting and realized that getting his dick sucked by me meant that he wasn't gay. He left and five minute later I noticed that his cell was still on my couch. I put on my robe (it was also my ex's) and walked outside to see if I could find him. I did. He was drunk, backed into a cop car and had just failed his breath test. Must have sucked that he was still underaged. I walked back in. Yes I did break the law by giving him alcohol, but is he really going to tell the cops that the cross dresser he visited to lose his virginity to got him drunk?

Yes I was pissed at this point. It was Saturday night. I planned today for one reason, he gave me a bullshit excuse and was now it was clear I'd never get fucked by him, ever. I took off the bathrobe and looked down at me. I was still in the lingerie. I looked good. I was not going to waste this. It wasn't even 8:30. The night was young.

I found myself in that chat room again. Many more people in my area than last night. I had to be a little careful. Two of them were coworkers. This was a secret I wasn't ready to announce, if ever.

I found someone. He was visiting from Chicago. He was bisexual and looking for some fun. We chatted a little bit. He here on business and his company had him in a four star hotel room down town. He was bisexual, single and experienced with a thing for cross dressers. I asked him to come over and he refused. His argument was that he didn't want his hotel to go to waste. I couldn't argue with that.