Not Knowing the Future - A Trip to the Other Side

Cris J

 

What happened here? That was the question I asked that one fateful night. It all started a few years ago when I found that I liked to wear women's garments. Although up until the other day in class did I know what I could really do when I was dressed. It was in one of those boring math classes when the guy next to me passed me a note saying that my panties were showing, and to meet him later that night in his room. Well when I got back to my dorm I quickly stripped to my panties and lay in bed. My room mate is cool with me dressing since I told him a couple of weeks into the semester, and he doesn't care if I dress up. When it was time to meet the guy, who is known as Doug, I left to see him.

When I got to his room across campus he asked me to strip down to my panties. So I took of my shoes and pants where he saw my heart panties, and then took off my shirt and he saw my bra. As I was about to take that off he told me to stop. He looked at me for quite a while and asked why I was wearing panties to class.

I told him that is all that I had to wear, and that it was by choice. The choice that I like the feel of the frilly panties that holds me so close. It also makes me feel better inside my head. Doug told me not to be afraid of him or being found out more since he lives alone in his dorm. He was in the nice apartments on campus that had his own bathroom with a shower and tub. He noticed that I didn't have any body hair as he felt my legs. That gave me goose bumps all over my body. I could almost feel the tension in the air between us. Once I had calmed down a little I asked him why he had asked me to his room. His reply was that he had a fantasy about a boy like me, you know boys that like to dress up in some of the feminine fineries. He had never seen one in person, but he had seen them in his many searches on the internet. When he looked over at me in class and saw my panties he knew that I was what he had searched long and hard for, and there I was sitting right next to him for the whole semester. He asked if he could kiss me and I said yes he could. He was the most incredible kisser I had ever known. Even though he was the first male that I kissed. And my clit started to swell. He looked down after about a minute and saw this. I could feel him poke my stomach with what must have been above average cock. He sat me down and asked if I had enjoyed his kiss, I told him just looks at himself. We both laughed at this. He asked me what I wanted him to call me, I said not just yet. When I looked at the clock on the wall I saw that it was getting late and I had class early in the morning so I had to leave and walk across campus to get everything for my class. I gave him my user name so he could chat with me.

The next night he asked me over to his room again to "study" and also to bring a change of my special clothes with me. I thought it might be fun to study with someone while dressed so I got everything ready to go. Then I went to the cafeteria to get something to eat and think about what I was about to do. After finishing I took my bags over to his room where he greeted me with a beer and a hug.

After having the drink he asked me if I wanted to use it bedroom to change. How could I resist his charms tonight. So he showed me his room and I got dressed in my red satin panties and matching bra and inserting my breast forms. Then a white denim skirt and a white blouse. You could clearly see my bra through the shirt as I looked into the mirror.

I walked back into the living room to a stunned Doug with his mouth open. I then introduced myself as Cris. Doug then said pleased to meet you. I noticed myself getting excited only a couple of people had seen me dressed like this. And I just liked it for some reason. He gave me another drink before we started studying. I think he was studying me more than the book. A little over an hour after we started we stopped to take a break he asked me if I wanted a cigarette and I accepted his offer. He took one and lit it for me, and placed it in my mouth then lit his. What a complete gentleman so far this evening. While we were smoking I thought that I could lose my virginity to him, but not tonight I am just not ready.

When we had finished studying we sat there with another cigarette and beer. I didn't mind staying there later since my first class was at 1 pm. We started watching the 11 o'clock news and talking. His hand started to rub my hairless leg. I leaned over and started kissing him, he probed my mouth with his tongue. I was starting to like this and let out a little moan as his hand reached my little clit. When I came up for air I said wow that was the best I have ever had. We sat back and smoked again he asked me why my breast looked and felt real. I told them they were cheaper than surgery but can be taken off, and they were made of silicon, so that's why they feel real. I told him that it was getting late and I would see him tomorrow in class. I went back into his room to change but the thing was that he followed and said he wanted to see me change.

So I let him, he got on the bed and pulled out his cock and started rubbing it. When I got down to my bra and panties I turned towards him and kissed his cock, and said this weekend and smiled.

After getting dressed I headed back to my room and a good nights sleep. When I got into class Doug gave me a wink as I sat down and handed me an envelope that said I should read it when I was alone. So after class I was headed back to my room I pulled out the envelope and started reading it. It said that he had a good time last night with me and wanted to take me up on offer for this weekend then at the bottom it had a digital picture of him naked on the bed with a massive hard on with the caption waiting for you, be here at 9 pm ready for the weekend. My knees almost went weak as I was walking. I just couldn't wait for tonight.

As I was getting ready my roommate walked in and asked what I was doing. So I told him that I was going away for the weekend. Then he saw what I was packing since I had never packed like that before and asked where I was going.

I thought about lying to him, but told the truth that I was going to stay with a guy for the weekend leaving out who I was going to see. I picked out my friliest lingerie that I had and also my corset (I just like the way it constricts my waist down 6 inches to 24 inches. I got out my red and black baby doll nightie. My boots with the 3" heels and my in black patent leather 4" stilettos. I got many pairs of thigh high hose and garter belt. Also many other outfits not knowing what we were going to do this weekend. And then grabbed my dildo and some condoms.

When I got there, there was a note on the door to go inside and get myself ready and he would be back in a little bit. So I went inside got into one of my sexiest outfits. With my boots I thought I could be as sexy as the hottest girl in a dance club. When I was ready I went to the refrigerator and got a wine cooler. I sat down waiting for Doug to come back and smoked a cigarette. While waiting for him I thought about how good his cock in my pussy would feel, it had to be at least 9 inches long and have a 2 inch diameter at the base. I just hope that I can take it all.

When doug got in he had someone else with him that I didn't recognize. Doug introduced him as PJ and was also interested in a girl like me. Pj came up and kissed me on the cheek. And led me back to the couch he lit me a cigarette without even asking me if I wanted one, but I knew they knew what was best for me. So I smoked it and Doug got me another wine cooler saying that all of them in the fridge were mine to drink. After they had given me several more drinks I wasn't feeling anything then Doug pulled out his cock and started stroking it.

I leaned over and kissed it again and kissed him on the lips. PJ on the other hand was starting to rub my butt since it was sticking straight up in the air as I was down at Dougs crotch. PJ lifted my skirt and moved my thong to the side and kissed my pussy. I jumped at first, then started to get into the mood of the evening.

They were having their way with me since they hadn't had as much to drink as I did. Doug then had me kneel on the floor while I sucked Pj's cock and Doug got behind me and loosened up my pussy with his tongue and fingers. He then kneeled right behind me and started to put his cock head on my entrance. I was so loose that he slid right into me slowly. While I was sucking on Pj who didn't have a small cock either it had to be atleast 8 inches long and 1.5 inch diameter at the base. Surprisingly I got Pj's cock all the way down my throat with my nose being tickled by his pubic hair which was a fine brown hairs. I reached down and started to rub my clit. I was sucking and being fucked for about half an hour. I was in heaven like this. Pj said that he was about to cum so I pulled his cock out so only the head was in my mouth since I wanted to taste his love juice on my tongue and hopefully swallow it all. I really didn't care about the condoms right now it just felt so good. Pj came with the first spurt hitting the back of my throat. He came for about 30 seconds and fell back against the couch. Then I started paying attention to the cock that was pounding my pussy. He pulled out and had me lay over the arm of the couch and shoved right back in. After only about a minute Doug was cumming and I was almost cumming also. I came into my hand and put it up to my mouth and licked my hand clean.

We all lay there basking in the afterglow smoking cigarettes and drinking some wine that Pj had brought with him. After we had relaxed I decided to go into Dougs room and change and told them to stay where they were. I went in and put on my corset and red baby doll nightie with red fishnet stockings and my stilletos. I went back into the living room and both of their jaws dropped wide open. I went over and sat on Dougs lap and that is when he told me who Pj was. As it turned out Pj was Dougs Human Sexuality proffessor. I could no longer hold out and took Pj's cock and got it hard and had him lay on the couch and I directed his cock into my pussy and started to ride him as fast as I could. I bent down and kissed him on the lips and he put his tongue in my mouth and started to explore. I wish I had known that it could be this good before now. That's where this story started and went on for the next couple of months until the end of the semester. I moved in with Doug and Pj and quit school and became the personal assitant to Pj during the day and both of theirs slut during the evening.

Cris

  

  

  

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